Erica Jain, Co-Founder & CEO of Healthie, breaks down how a relentless customer-first mindset shaped every part of the business from product decisions to hiring to long-term strategy.

In this conversation, she shares how they got their first customers with no sales experience, why internal inefficiency is a bigger risk than doing too much, and what it really takes to maintain speed as a company scales. She also dives into rebuilding the product after early success, hiring for values, and staying in control while growing a profitable company.

If you want to build faster, stay close to your customers, and avoid the trap of internal complexity slowing you down this episode is for you.

Takeaways:

• Obsess Over Customers as Your True North Star: The single most important thing is to instill a true customer-first mindset across the entire company. Customers literally “keep our lights on” every decision, roadmap, and internal process should revolve around delivering an incredible experience for them.
• Simplify Your Values Ruthlessly: Erica and her team reduced their values from eight which nobody could remember to just the Three R’s: Respect, Resilience, and Reliability. Hire for values far more than skills, especially as technology changes rapidly.
• Profitability Equals Control: They chose to remain profitable for most of the company’s life to always stay in control of their destiny. Build a generational business and raise capital only when it serves clear long-term goals, never out of desperation.
• Mediocrity Is the Real Killer: Companies don’t usually die from doing too many things they die from descending into mediocrity caused by slow internal processes, too many meetings, and inefficient decision-making. Speed and execution velocity matter enormously.
• Hiring, Team Building, and Scaling Challenges: Hiring for values, the difficulty of identifying customer-first people in interviews, retaining talent (many team members 5–7+ years), going through a major codebase rewrite, and the constant battle against internal inefficiency as the company grows.

Quote of the Show:

• The one thing I would do is instill… a true customer first mindset. There is something incredibly, incredibly powerful about waking up every single minute of every single day and wholeheartedly focusing on making sure our customers are taken care of.”- Erica Jane, CEO & Co-Founder of Healthie.
  

Links:

• LinkedIn: https://www.linkedin.com/in/ericajain/
• Website: https://www.gethealthie.com/

Chapters

00:00 – Intro: Healthie’s growth, impact & profitability

00:56 – The power of a true customer-first mindset

03:11 – How to build with customers from day one

06:00 – Hiring for values: the “3 R’s” framework

08:53 – Evolving culture as the company scales

12:54 – Operating systems & using OKRs effectively

16:50 – Why inefficiency kills companies (not ambition)

19:35 – Profitability, fundraising & staying in control

24:08 – Starting Healthie & getting first customers

30:30 – Biggest challenges: tech debt & rebuilding the product

She opens up about the importance of core values, the challenges of fundraising as a female founder, and the lessons she learned navigating through different growth stages.

Takeaways:

• Importance of Core Values: Natalie emphasizes the transformative impact of clearly defined core values in the evolution of Winky Lux. The company started with general ideals, but crystallizing specific values became vital as the company scaled.
• Consumer-Centric Approach: A pivotal moment in Winky Lux's development was the decision to pivot from a marketplace to a full-fledged brand. This shift was entirely consumer-driven, based on insights gathered from direct customer interactions.
• Fundraising Challenges: Natalie candidly discusses the journey of fundraising, particularly as a female founder. Despite the competitive landscape and systemic biases, she underscores the importance of perseverance and strategic financial planning.
• Brand Aesthetics and Market Trends: Natalie delves into the significance of aesthetics in the beauty industry. She describes Winky Lux's vibrant, art-inspired branding, which aligns with current market trends.
• Embracing Community and Collaboration: Natalie credits a considerable part of her success to the entrepreneurial community, highlighting how networks like YPO foster invaluable support and collaboration.

Quote of the Show:

• “I don't mind swinging and striking out, but I really, really, really hate not having swung." - Natalie Mackey

Links:

• LinkedIn: https://www.linkedin.com/in/natalie-mackey-15169370/  
• Website: https://winkylux.com/  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #WinkyLux

Chapters:

00:00 Intro

01:23 Core Values and Company Culture at Winky Lux

11:28 The Importance of Customer Feedback

24:38 Challenges and Insights in Fundraising

33:32 The High Stakes of Venture Capital

35:06 The Changing Landscape of Entrepreneurship

36:37 The Role and Structure of YPO

40:00 Challenges and Resilience in Business

45:03 Future Prospects for Winky Lux

48:17 The Journey from Finance to Entrepreneurship

51:27 Mentorship and Community Support

59:11 Final Reflections and Advice

1:00:55 Outro

Nick joins host David Politis to discuss his journey from a collegiate tennis player to a tech entrepreneur. Nick examines the importance of hiring curious and passionate people, as well as the importance of transparency. He delves into his innovative all-hands meetings and how they evolved over time. 

Takeaways:

• Entrepreneur from the start. Nick had been an entrepreneur his whole life. He started reselling tennis equipment as a kid, then built an online platform to connect college athletes and alumni, and now is a Co-Founder of one of the largest leadership search firms in the world.
• A culture of asking questions. Hunt Club has been able to establish a monthly all-hands meeting dedicated to transparency, allowing the rest of the company to share their successes and perspectives, and open and honest communication within the company.
• Leading with curiosity. Nick has found that many in the executive search industry don’t come from a solutions oriented background. When hiring for their team, they prefer to hire someone who is curious and willing to better understand the problem in front of them.
• Having a passion outside of work. If an employee was ever passionate about something outside of their work, a good leader should work to recreate that passion for something in the business. Nick actively looks for passions when hiring new employees.
• Bouncing back from rejection. The economic effects of the pandemic killed an acquisition deal of Hunt Club and caused an 80% loss in revenue shortly after. They were able to cut leadership compensation, cut costs, and capitalize on the new and unique deals to be exceeding goals a few months later.
• Speed to resiliency. The time it takes to get over issues gets shorter as time goes on. What took weeks to get past when you start your business could take minutes to get over in the future. 

Quote of the Show:

• “If you don’t really build a culture where people are comfortable asking a really hard or direct question, or asking something that they don’t know, it’s impossible to actually close the gap on what you're trying to build together.” - Nick Cromydas

Links:

• Twitter: https://x.com/nickcromydas 
• LinkedIn: https://www.linkedin.com/in/cromydas/
• Website: https://www.huntclub.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Alex joins host David Politis to discuss his journey building the largest SaaS community in the world. Alex examines the importance of having an executive coach, the benefits of growing your community, and the risks of a founder led business. He delves into the significance of hiring a mission-driven team and how SaaStock overcame Covid-19. 

Takeaways:

• The Impact of an executive coach. Alex spent much of his early time in SaaStock helping other entrepreneurs, but wasn’t helping himself in the same way. Having an executive coach allowed him to navigate the company through Covid-19 and grow to be a better leader.
• Community building first. SaaStock started as a collection of blogs, podcasts, and chat groups dedicated to supporting founders. It wasn’t until he received overwhelming support and a desire for more that the conferences began and a business formed around it.
• Growing into the future. In addition to the conference, SaaStock has begun expanding to better fill the needs of founders. This includes a membership to build a SaaS focused YPO and a fund to help support founders financially as well.
• Risks of a founder led business. When a founder’s identity is closely attached to the business, the overall impact and growth potential of that business is at risk if the founder decides to step away.
• Building a mission-driven team. The work that SaaStock does, especially in events, is both hard and rewarding. Having a team that is motivated by that reward and aligns with company values is crucial in building a successful team.
• Overcoming Covid-19. Covid-19 brought in-person events to a halt and threatened the stability and cash flow of SaaStock. They were able to quickly pivot and became one of the first start-up events to hold a virtual conference, running for two days to capture the global community.

Quote of the Show:

• “When you're there and you see the smiles on the faces and you see the value that people are getting from it, it does energize you.” - Alex Theuma

Links:

• Twitter: https://x.com/alextheuma 
• LinkedIn: https://www.linkedin.com/in/alextheuma/ 
• Website: https://www.saastock.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Amish discusses his criteria for investment, the importance of understanding the 'why' behind a founder's journey, and the strategic approach to board meetings. He also sheds light on the dynamics of venture partnerships, the evolving focus of SaaS in the AI era, and the burgeoning startup ecosystem in New York City.

Takeaways: 

• The Power of the “Why”: Amish emphasizes the importance of understanding the founder’s unique perspective on their problem. The "why" behind their journey not only reveals their depth of understanding but also what drives them to pursue their vision.
• Investor-Entrepreneur Fit: Amish highlights that mutual compatibility and alignment of values between the investor and the entrepreneur significantly enhance the collaboration's success over a long-term journey.
• Adaptability and Focus as Key Ingredients for Success: While having a clear vision is significant, the ability to adapt and listen to market feedback can sometimes pivot a company to more promising directions.
• Product-Market Dynamic and Competitive Edge: Amish talks about the emphasis on distribution, data acquisition, and building unique advantages that distinguish companies from competitors who may quickly replicate similar functionalities.
  

Quote of the Show:

• “ We're not in a control business, we're in an influence business. And if you lose someone's ears, that's just as bad as not saying something at all." - Amish Jani

Links:

• LinkedIn: https://www.linkedin.com/in/amishjani/ 
• Website: https://www.firstmark.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:19 Amish’s Investment Philosophy

02:38 The Importance of 'Why' in Founders

03:40 Evaluating Founders and Their Vision

05:08 The Role of Product and Market Understanding

06:13 Challenges and Insights in Venture Capital

08:30 Investor-Founder Fit and Long-Term Relationships

21:07 The Importance of Choosing the Right Investor

21:56 The Role of Founders in Shaping Company Culture

23:09 Navigating Hard Conversations with Founders

25:54 Effective Board Meetings: Moving Beyond Sales Pitches

30:04 The Current State of AI and Market Dynamics

37:06 The Evolution of New York's Tech Ecosystem

41:26 Why Amish Became an Investor

43:47 Outro

Nick discusses critical insights on how Radar's unique product strategy, company culture, and operational practices have driven their success.

Takeaways:

• Multi-Product Strategy Innovation: Nick emphasized Radar's growth through expanding their product offerings rather than focusing on a singular solution. By catering to diverse customer requests, Radar transitioned from a geo-fencing platform to a comprehensive location service provider.
• Customer-Centric Approach: Nick underlined the importance of being customer-driven in product development. Radar has prioritized building what customers request, as long as it aligns with their overall vision.
• Modernizing Company Culture: Radar has seen increased cohesion and morale by embracing a focused mission and maintaining a workplace culture that emphasizes teamwork over rigid organizational roles.
• Leadership through Uncertainty: Leading through the pandemic, Radar faced significant challenges with clients from the travel and retail sectors. The company pivoted by redefining its strategy, focusing on delivering multiple product solutions, strengthening its market position.
• The Shift from Remote Work Culture: While embracing remote work during the pandemic, Nick advocated for in-person collaboration as a competitive advantage. By returning to office-based work, Radar has fostered a more cohesive culture and quicker iteration of ideas.
• Strategic Fundraising Tips: Nick shared valuable insights into securing investment, noting the importance of creating urgency during fundraising and finding investors who truly “get” the company's vision.

Quote of the Show:

• “Either people happen to Radar or Radar happens to them… you wanna hire people like they happen to Radar." - Nick Patrick

Links:

• LinkedIn: https://www.linkedin.com/in/nicholaspatrick/ 
• Website: https://radar.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Radar

Chapters:

00:00 Intro

01:12 The Impact of Multi-Product Strategy

03:16 Challenges and Management of Multi-Product Approach

07:43 Product Involvement and Team Structure

12:30 Customer-Centric Engineering

14:42 In-Person Collaboration and Office Culture

19:52 Founding Radar and Early Challenges

28:36 Fundraising Journey and Investor Relations

34:55 Navigating Business Through Uncertain Times

35:47 Adapting to Market Changes and Setting Expectations

38:20 Cultural Shifts and Social Issues

41:21 Future Vision for Radar

43:24 Personal Journey and Entrepreneurial Spirit

47:38 Balancing Work and Family Life

51:03 Advice for Aspiring Entrepreneurs

54:25 Outro

In this episode, Max Junestrand, Co-Founder and CEO of Legora, shares how he’s building the world’s first truly collaborative AI platform for legal services.

Max reflects on his unconventional path from engineer to entrepreneur, what it took to win over law firms as an outsider, and why ambition and adaptability matter more than experience in fast-scaling environments. He also opens up about navigating hypergrowth, hiring with intention, and the cultural values that drive Legora’s mission to reshape how legal work gets done.

Takeaways:

• Pioneering Global Expansion: Max's approach to expansion defies conventional paths. Instead of focusing solely on local markets like many Swedish companies, Max boldly decided to expand globally. 
• The Power of Collaboration: Max stresses the importance of a shared mission between stakeholders and service providers, focusing on delivering unparalleled value and continuous improvement in legal services. 
• Hiring and Culture Building: Max places a strong emphasis on ambition and cultural fit when hiring, believing these attributes are crucial for scaling a company. He maintains personal involvement in the interview process to ensure new hires align with the company’s high standards and growth trajectory.
• Learning and Growing from the YC Experience: Max’s experience with Y Combinator (YC) was transformative. Despite the complexities of maintaining operations during this period, the experience underscored the importance of mentorship and networking.
• Pushing the Envelope: Max underscores the importance of maintaining a proactive stance in innovation. By consistently exploring new pathways and pushing boundaries, he ensures the company remains at the forefront of technological advancements.

Quote of the Show:

• “ There's a real value in actually being the second mover, and the value comes from two things... You get to see what is the right path and what is the wrong path." - Max Junestrand

Links:

• LinkedIn: https://www.linkedin.com/in/maxjunestrand/ 
• Website: https://legora.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Legora

Chapters:

00:00 Intro

01:41 Founding and Early Challenges

02:42 Sales Strategy and Growth

06:40 Building a Strong Team

13:55 Global Expansion

29:43 Expanding Beyond Local Markets

31:13 Challenges of Going Global

33:40 Product Development and Iteration

37:08 Competing with Industry Giants

42:43 YC Experience and Early Challenges

49:52 Personal Background and Motivation

1:00:48 Outro

Toby shares insights on taking big risks, scaling early teams, and navigating the challenges of a hardware business in the EV space. They dive into lessons learned at Tesla, the importance of building trust with investors, and the unique market opportunity Lightship is chasing.

Takeaways:

• The Importance of Coaching: Toby emphasized the value of having a co-founder coach to strengthen the relationship between company leaders. He and his co-founder began working with a coach from the beginning, which Toby credits with helping them maintain a strong partnership and navigate the pressures of building Lightship.
• Adapting to Growth: As Lightship expanded, managing a larger team and aligning everyone with the company’s mission became a significant challenge. Toby learned that relinquishing control and trusting team experts were vital to maintaining momentum and effectiveness.
• Venture Capital Challenges: While their early seed round was successful, each subsequent round of funding became increasingly difficult, highlighting the unique challenges hardware companies face compared to software firms, as venture capitalists often favor faster software cycles.
• Creating a Culture of Ownership: Creating opportunities for team members to take ownership of projects fosters an environment of trust. By delegating responsibilities and empowering team members, leaders convey confidence in their team’s capabilities.
• Grateful of the Bumpy Path: Despite the mistakes and challenges he faced, Toby insists that changing any aspect of his journey might not have led to the founding of Lightship. Each experience, no matter how difficult, contributed to his current success and perspective.

Quote of the Show:

• “My hidden agenda is I want to know why you wanna work here." - Toby Kraus

Links:

• LinkedIn: https://www.linkedin.com/in/tobykraus/  
• Website: https://www.lightshiprv.com/  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Lightship

Chapters:

00:00 Intro

01:46 The Importance of a Co-Founder Coach

02:28 Building a Strong Co-Founder Relationship

07:15 The Tesla Connection

14:38 Raising Capital During COVID

16:20 Challenges of Hardware Startups

24:00 Demonstrating Commercial Traction

26:50 Sales and Marketing Strategy

28:22 Hiring for Innovation

30:05 The Importance of Interviewing Candidates

30:39 Understanding the Common Failure Mode

32:02 The Value of Authentic Motivation

33:38 Emotional Runway vs. Cash Runway

34:31 Challenges in Building Lightship

37:38 Managing a Growing Team

40:40 Relinquishing Control and Trusting Your Team

44:00 Future Vision for Lightship

50:03 Balancing Work and Family Life

56:41 Reflecting on the Journey

58:21 Outro

What do venture capitalists really look for in founders, and how can CEOs build strong, lasting relationships with their investors? In this episode, Chip Hazard, Co-Founder and General Partner at Flybridge, offers an inside look at how VCs think about evaluating founders, funding opportunities, and long-term partnerships. He shares the traits that consistently stand out and explains how these factors matter as much as business metrics, especially in the early stages.

Chip also unpacks the evolution of fundraising, from vision-driven early rounds to later stages where metrics and revenue quality become critical. He reflects on the dynamics of board relationships, the importance of clear alignment on strategy, and why constructive feedback and ongoing communication are vital to scaling effectively.

Takeaways:

• Ambition is Key: Chip emphasizes the importance of passion and ambition in founders. He's looking for those with domain expertise and unconventional thinking.
• Alignment on Strategy: For founders, aligning on strategy with investors is crucial. Chip notes that understanding an investor’s vision for the company can prevent conflicts and foster a positive partnership.
• Ongoing Communication: Chip discusses the importance of consistent communication between founders and investors, particularly in the early stages. Regular check-ins on strategy, challenges, and progress help maintain alignment and support.
• Insightful Board Interactions: The role of a board is to offer perspective and support strategic decision-making. Chip highlights that effective board meetings should align on strategy and not create unnecessary work for the company.
• Balancing Metrics and Vision: As companies evolve from pre-seed to later stages, the focus shifts from purely vision and team to include metrics and financial performance.
• The Value of Constructive Feedback: Constructive, honest feedback is essential. Chip stresses that a good VC relationship involves recognizing challenges, offering guidance, and maintaining trust without dictating to the founder.

Quote of the Show:

• “ Startups win on speed. They don’t have anything else other than the ability to execute fast." - Chip Hazard

Links:

• LinkedIn: https://www.linkedin.com/in/chiphazard/ 
• Website: https://www.flybridge.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Flybridge

Chapters:

00:00 Intro

02:11 The Key Traits of Successful Founders

04:09 Assessing Founders Beyond the Pitch

06:04 Stages of Investment and What VCs Look For

15:36 Working with Founders Post-Investment

22:08 The Importance of External Perspectives

25:52 Challenges in Board Dynamics

30:37 Aligning with Venture Capitalists

37:55 Geographical Differences in Startups

40:13 Reflections and Regrets in Venture Capital

43:18 The Passion for Investing

45:47 Outro

A serial Founder with multiple exits, Adam reflects on making hard pivots, recruiting top talent personally, navigating investor psychology, and why execution, not ego, is what earns the right to exist. He also shares how AI is transforming financial services and why the emotional highs and lows of startup life never really go away.

Takeaways:

• Recruiting Personally, Relentlessly: Adam still personally recruits on LinkedIn, often spending hours each day identifying talent, crafting outreach, and filtering for startup fit. He believes CEO-led recruiting cuts through noise and shows prospects the role's importance.
• A Pivot Before the Crash: Originally conceived as a crypto banking platform, Domain Money pivoted early. Adam made the call based on market fundamentals and moved decisively, even when his team was still optimistic about the original vision.
• Transparent, Yet Optimistic Leadership: During the pivot, Adam prioritized honesty with his team while maintaining belief in the mission. He communicated openly about uncertainty and made clear that success was entirely on them.
• Investor Support Built on Track Record and Clarity: Adam credits his investor relationships and clear, data-backed thinking for enabling a smooth pivot. Though they challenged him, his investors supported the shift and recognized the market opportunity in personal finance.
• AI as a Backbone, Not a Gimmick: AI plays a major role in Domain Money’s operations, especially in improving planning efficiency. Adam is enthusiastic about AI’s pace and scope of change, calling it central to his product vision.
• The Mental Game of Being a Founder: The pivot at Domain Money required layoffs and letting go of certainty. Adam talks candidly about staying objective under pressure, fighting through doubt, and surrounding himself with trusted mentors while still waking up every day to earn it.

Quote of the Show:

• "That uncertainty, that thing inside of you that forces you to figure it out, is very motivating to me and I quite enjoy it." - Adam Dell

Links:

• LinkedIn: https://www.linkedin.com/in/adamdell/
• Website: https://www.domainmoney.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #DomainMoney

Chapters:

00:00 Intro

01:25 Recruiting Strategies for Startups

07:15 Fundraising Insights and Market Sentiment

11:46 The Evolution of Domain Money

16:25 Navigating Pivots and Team Buy-In

23:07 Growth Strategies and Partnerships

26:20 Acquisitions and Exits

29:23 Strategic Partnerships and Revenue Growth

30:37 The Impact of AI on Technology and Business

35:12 AI in Financial Planning and Wealth Management

39:51 Challenges and Pivots in Business

49:09 Personal Background and Entrepreneurial Journey

57:37 Advice for Aspiring Entrepreneurs

01:00:30 Outro

Bryant shares his insights from over 30 years of interviewing leaders and exploring the paradoxes of leadership. From his framework for authenticity to understanding the "optimal band of busyness," Adam discusses what motivates effective leaders to lead and how they navigate the ever-increasing complexity of today’s challenges.

Takeaways:

• Simplifying Complexity: Effective leaders excel at breaking down intricate problems into clear, digestible priorities for their teams. Bryant emphasizes the importance of framing challenges in a way that inspires clarity and action, ensuring everyone knows where they’re going and how to get there.
• The Authenticity Framework: Authenticity is about aligning how people perceive you with how you intend to show up as a leader. It’s not about oversharing emotions but about communicating your values and the stories behind them to build trust and credibility.
• Leadership Paradoxes: Bryant explores the delicate balancing acts leaders must navigate, such as being confident yet humble or compassionate while holding people accountable. He highlights the importance of contextual decision-making to manage these complexities effectively.
• OBOB (Optimal Band of Busyness): Leaders thrive when they find their "optimal band of busyness"—a balance that keeps them engaged without overwhelming or under-stimulating them. Bryant shares how this concept applies to both leadership and post-exit planning.
• Team Trust Building: Building trust within teams starts with vulnerability and open communication. Bryant describes exercises like leadership user manuals and storytelling to help team members see each other as human beings, fostering deeper connections and collaboration.
• Why Leaders Lead: Many leaders are driven by transformative early-life experiences, whether adversity, immigrant stories, or the influence of extraordinary parents. Bryant reflects on how these motivations shape leaders’ decisions and their approach to challenges.

Quote of the Show:

• “ I always think about leadership as a series of paradoxes or contradictions or balancing acts. It's never about one thing. And I think to be an effective leader, you have to be comfortable in those paradoxes.” - Adam Bryant

Links:

• LinkedIn: https://www.linkedin.com/in/adambryantleadership/
• Twitter: https://x.com/adambbryant
• Website: https://www.excoleadership.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #TheExCoGroup

Nick joins host David Politis to discuss the importance of company values. Nick reflects on how vital it was to establish values early, as well as the most important executive roles a company should hire. Discover his insights on the importance of building community, qualities that make an effective leader, and the benefits of investing in a good Executive Assistant.

Takeaways:

• Building a community can be vital to establishing a strong and reciprocal relationship with customers. Communities and community events allow for direct customer interaction and a space to get honest feedback on the business.
• The ability to manage up, down, across, and out are vital for strong management, as it ensures a manager is able to work with and be a positive influence on coworkers, stakeholders, customers, and direct reports.
• Executive Assistants are not something to be thrifty or cheap about. An effective EA can make a world of difference for CEOs and should be well-supported to ensure retention. Sometimes they are more on top of things than the CEOs themselves.
• Being CEO means you have to be yourself. Candor and authenticity are essential qualities for successful leadership, even if it means making tough decisions or telling employees that something is wrong.
• Backchannel references are a great tool for ensuring you have a holistic view of a potential candidate. Asking a reference “what did others think of this person” instead of “what did you think of this person” is a strong strategy for getting an honest answer from them.
• Actively reinforcing company values is an important step in getting your staff to truly live up to them in their day to day. Have your values be the focus of employee onboarding, discuss them in all-hands meetings, send out consistent emails reaffirming them, etc.
• As a CEO, it’s impossible to be aware of everything as you scale. Anonymous surveys can provide valuable insights on leadership and day to day operations that a top down perspective might miss out on.

Quote of the Show:

• “What I tell CEOs is the only way to have a good culture is make it something you truly care about.” - Nick Mehta

Links:

• Twitter: https://x.com/nrmehta
• LinkedIn: https://www.linkedin.com/in/nickmehta/
• Website: https://www.gainsight.com

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

From trusting your gut to embracing constraints and building resilience, this episode is packed with wisdom applicable to CEOs, leaders, and professionals at every level. Tune in to hear insights from Tom Buiocchi, Melanie Fellay, Adam Bryant, and many more as they reflect on their journeys and what they wished they knew when starting out.

Takeaways:

• Trust Your Gut (David Politis): Trust your instincts when making decisions, whether hiring, strategizing, or pursuing opportunities. Ignoring your gut often leads to regret.
• No Need to Be the Hero (Tom Buiocchi): Empower your team rather than trying to carry the entire burden of success yourself. Great leaders build teams that can win together.
• Dream Big and Build the Right Team (Loren Castle): Give yourself permission to think big from the beginning and prioritize hiring exceptional people to execute your vision.
• Direction Over Speed (Ryan Westwood): Take the time to ensure your business is heading in the right direction. Rushing ahead without alignment can lead to costly mistakes.
• Patience and the Long Game (Ryan Simonetti): Success takes time. Commit to the process and trust that steady, consistent effort will yield great results in the long term.
• Speed to Resiliency (Nick Cromydas): Build the ability to recover quickly from setbacks. What once took weeks to overcome should eventually take only minutes.
• Enjoy the Journey (Adam Bryant): Be present and savor the process. Career success isn’t just about achievements—it’s also about appreciating the steps along the way.
• Be Yourself (Melanie Fellay): Speak up, share your opinions, and trust that the right people will align with your authentic self.
• Follow Up and Follow Through (Dan Michaeli): Persistence and reliability are essential. Always follow up on opportunities and deliver on your commitments.
• Find Your Rhythm (Howard Ting): Careers, like music, have rhythms. Know when to push hard and when to ease up to enjoy the journey and sustain your energy.
• Learn and Have Fun (Andrew Lau): Work with people you respect and focus on roles that challenge and excite you. If it’s not fun or meaningful, don’t stick with it.
• It’s All Going to Be Okay (Kathryn Minshew): Even in moments of failure, remind yourself that things will work out. Resilience and adaptability lead to success.
• The Value of Constraints (Nathan Rosenstock): Constraints fuel creativity and innovation. Embrace challenges as opportunities to build something better with fewer resources.
• Lead with Consciousness (Godard Abel): Develop self-awareness and adopt a conscious leadership approach to lead with ease, clarity, and impact.

Chapters:
(0:00) Intro
(3:50) David’s Advice
(7:11) Tom Buiocchi
(8:58) Loren Castle
(12:07) Ryan Westwood
(13:48) Ryan Simonetti
(16:33) Nick Cromydas
(20:26) Adam Bryant
(22:14) Melanie Fellay
(23:42) Dan Michaeli
(26:40) Howard Ting
(28:33) Andrew Lau
(29:17) Kathryn Minshew
(30:49) Nate Rosenstock
(33:28) Godard Abel
(35:16) Outro

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #CEOAdvice

Tom reflects on his unique journey as a CEO, including selling ServiceChannel for $1.2 billion and handing another company back to its founder for $1. He shares lessons on building resilient teams, over-communicating during crises, and making transformative hiring decisions. This conversation is packed with insights for leaders at any stage.

Takeaways:

• Executive Coaching as a Catalyst: Tom shares how hiring an executive coach early in his ServiceChannel tenure helped him navigate challenges, think more clearly, and ultimately become a better leader.
• Uncomfortable Hiring Decisions: At ServiceChannel, Tom prioritized hiring experts who challenged his thinking, leading to innovative strategies and significant growth, even though it was uncomfortable at times.
• Segment Until It Hurts: Tom emphasizes the importance of narrowing target markets to identify ideal customers. By meticulously defining criteria, ServiceChannel created a focused pipeline of less than 700 target companies, improving conversion rates and customer engagement.
• The Growth Roadmap: Beyond the product roadmap, Tom implemented a "growth roadmap" focused on pricing strategies, new revenue streams, and bundling options that directly drove business growth.
• Over-Communication During COVID-19: Navigating the challenges of the pandemic, Tom adopted a strategy of daily updates and regular all-hands meetings to keep his distributed team aligned and motivated.
• Resilience, Grit, and Luck: Reflecting on his career, Tom credits his success to a combination of skill, resilience, and timing, sharing his belief that luck often comes to those who stay in the game long enough.

Chapters
00:00 Intro
01:33 What You’d Do Again As CEO
05:15 Tom’s First CEO Experience
09:05 Lessons Learned & Hiring Strategies
15:08 Dealing With Competition
20:13 The Importance of Target Market Segmentation
26:20 Metrics and KPIs
31:40 Navigating Investor Relationships
34:08 The Growth Roadmap
42:16 Tom’s Biggest Challenge
48:20 Tom’s Background
50:56 Biggest Career Impact?
52:13 What Motivates You?
54:28 One Piece Of Advice
57:53 Outro

Quote of the Show:

• “Fish in a pond where you know the names of all the fish.” - Tom Buiocchi

Links:

• LinkedIn: https://www.linkedin.com/in/tombuiocchi/
• Website: https://servicechannel.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #ServiceChannel

Fernandez reflects on his journey leading Marketo to become one of the most successful marketing automation platforms in history. From pioneering brand-building strategies to navigating fierce competition and near-death challenges, Phil shares valuable lessons for entrepreneurs and leaders striving to make an impact in today’s fast-evolving business landscape.

Takeaways:

• Start with the Brand: Fernandez emphasizes the importance of building a strong brand presence and engaging customers early, even before launching a product. Marketo’s success was rooted in creating a community of advocates who believed in the company’s vision from day one.
• Customer-Centric Leadership: Fernandez shares his philosophy of focusing entirely on solving customer problems rather than fixating on competitors. This approach allowed Marketo to foster trust and loyalty, even during challenging times.
• Overcoming Challenges: Fernandez recounts a critical moment when Salesforce acquired a competitor and temporarily disrupted Marketo’s integration. By focusing on customer impact, the company was able to regain their Salesforce integration.
• Navigating Funding Hurdles: Despite a stellar track record, Fernandez faced resistance raising Marketo’s initial funding in 2006. He recalls the perseverance needed to secure their first $1.5 million and how he and his co-founders built momentum from there.
• Hiring for Culture: Fernandez reflects on the importance of assembling a team that shares the company’s values. He shares the story of recruiting Bill Binch over a year-long process, ultimately creating a sales organization aligned with Marketo’s mission.

Quote of the Show:

• “ All of our communications with the market was about customers, was about what we were seeing, how to be better, how to do better, how to think better.” - Phil Fernandez

Links:

• LinkedIn: https://www.linkedin.com/in/phil-fernandez-6902881/
• Twitter: https://x.com/philf1217
• Website: https://business.adobe.com/products/marketo.html

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Marketo

Takeaways: 

• Concentration of Efforts: Narrowing down the focus to one primary goal can unify and effectively drive a company's momentum. By concentrating efforts, every team member can contribute to company growth.
• Effective Communication: Regular and focused communication is key to keeping everyone aligned with the company's goals. David suggests updating the team weekly to maintain a cadence that ensures urgency and focus.
• Culture of Outcome-Based Work: Create a work culture that rewards achievements based on outcomes rather than just effort. It’s crucial for employees to understand their work's impact on the company's success.
• Celebration of Successes: Recognizing and celebrating achievements fosters a positive work environment and encourages further productivity. Celebrations can be as simple as an email recognition or a shoutout during all-hands meetings.
• Strategic Compensation: Implementing flexible compensation structures isn't limited to sales teams. Properly aligning compensation with company goals can motivate teams across the board to go above and beyond.
• Removing Distractions: Encourage leadership to stay concentrated on key goals by avoiding changes in priorities throughout the quarter. Written notes can capture evolving ideas, which can then be revisited during the next planning phase.
• Leadership Involvement: Leaders should actively remove barriers for their teams rather than changing priorities. This approach helps maintain focus and supports execution on high-priority initiatives.

Quote of the Show:

• “The less you communicate about the other things, and the more you just make all the communication about that thing, people are gonna understand this is what we're focusing on." - David Politis

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #MarchPulse

Chapters:

00:00 Intro

00:48 Q2 Reprioritization Problem

02:36 Five Cs Framework

02:47 Concentrate Efforts

04:32 Communicate With Cadence

05:55 Outcome Driven Culture

06:44 Celebrate The Wins

08:13 Compensation Drives Behavior

11:26 Stay Focused For A Quarter

12:49 Outro

From his early days at Cisco to co-founding Datarails, Didi shares invaluable lessons on startup pivoting, embracing new technologies, and harnessing AI to revolutionize financial operations.

Takeaways: 

• The Power of the Right Team: Didi highlights the importance of having the right co-founders. He credits the success of Datarails largely to the strong foundational team that shared common goals and complementary skills.
• Embracing the Brutal Truth: Didi emphasizes the need for leaders to be honest about their failures and to learn from them while maintaining a visionary outlook for the future.
• Importance of Having a Name: Drawing from past experiences, Didi advises startups to choose a product that has a recognisable name and existing budget line.
• Finding Your Ideal Market Fit: Datarails achieved success by narrowing their focus to finance professionals who love Excel, aligning product benefits with users’ existing skills and preferences.
• Strategic Use of AI: Datarails seeks to prepare organizations for AI integration, ensuring readiness for technological advancements.
• Balancing Work and Family: Didi points out that while entrepreneurship is all-consuming, showcasing the possibility of building something significant can offer invaluable lessons for family.

Quote of the Show:

• “If someone ask me, I'm not sure if I have the product market fit, I'm saying, no, you don't have it. If you had it, you know." - Didi Gurfinkel

Links:

• LinkedIn:https://www.linkedin.com/in/didigurfinkel/ 
• Website: https://www.datarails.com/   
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:21 Co-Founders Matter Most

02:28 Finding the Right Partners

05:47 Evolving Founder Roles

07:28 Five Tough Early Years

09:28 Building Tech Without Sales

13:08 Staying Motivated to Pivot

18:05 The Breakthrough Pivot

20:52 Why FP&A and Mid-Market

24:40 Scrappy Early Go-To-Market

26:38 LinkedIn Phone Number Hack

28:17 Knowing Product Market Fit

30:43 Removing Buying Friction

32:47 Zero to One Million ARR

35:26 AI and Finance OS Vision

41:38 Three Year Company Outlook

43:06 Founder Origin Story

46:25 Israel Startup Mindset

47:50 No Work Life Balance

51:02 Outro

From his prestigious roles at Pinterest and Airbnb to founding Kumo, Vanja shares the lessons learned, the dilemmas faced, and the excitement of turning vast amounts of relational business data into actionable predictions.

Takeaways: 

• The Importance of Co-founders: Vanja emphasizes the critical role of choosing the right co-founders. He stresses the importance of complementary skills and experiences that create a sustainable and successful leadership team.
• Understanding Market Adaptability: A major challenge for technical founders can be the transition to understanding the go-to-market strategies. Vanja shares the struggles of innovating while aligning with market needs and effectively communicating product value.
• The Journey From Idea to Reality: Vanja sheds light on how Kumo's idea sprouted from a simple yet groundbreaking aspiration to simplify the process of turning enterprise data into predictions without the complex machine learning cycle.
• Raising Capital in the Current Climate: Although initially easy due to Vanja's background, he warns about the “honeymoon phase” in fundraising and the necessity of making money quickly, even when resources are abundant.
• The Art of Unlearning: As Vanja continues his journey, he highlights unlearning as key to adapting to new challenges. The ability to let go of old practices and adopt new methodologies is vital for growth and evolution.

Quote of the Show:

• “It’s always easier to watch somebody do things and criticize… if somebody’s watching you from the side, they’ll always find something wrong." - Vanja Josifovski

Links:

• LinkedIn: https://www.linkedin.com/in/vjosifovski/  
• Website: https://kumo.ai/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
  

Chapters:

00:00 Intro

01:24 The Importance of Choosing the Right Co-Founders

04:44 Defining Roles Among Co-Founders

06:49 Challenges of Being a CEO

10:22 Hiring and Building a Team

12:54 Raising Capital and Investor Relations

15:21 Kumo's Product and Market Fit

18:57 Pricing Models and Strategies

24:28 Acquiring the First Customers

28:28 The Intensity of Starting a Company at 50

32:33 The Importance of Unlearning as a CEO

37:13 Challenges in Go-to-Market and Fundraising

39:14 Kumo's Vision for the Future

42:28 From Macedonia to Silicon Valley

52:54 Advice to My Younger Self

53:39 Outro

From assembling a thoughtful board to reorienting a business for profitability, John shares lessons from building a modern insurance company from scratch.

Takeaways:

• Decisiveness Around Leadership Transitions: John emphasizes making tough calls on leadership team members who may no longer be the right fit as a company evolves. Waiting too long creates compounding challenges and stalls progress.
• Balancing Founder Involvement with Delegation: He reflects on the “founder mode” concept, describing the need for leaders—founder or not—to stay close to the details while avoiding micromanagement. Clarity and context are key.
• The Decision-Making Matrix at Pie: John explains Pie’s internal framework for decision-making, which clearly defines who owns decisions, who contributes input, and how final calls are made—helping empower teams without chaos.
• Why Pie Competes in a Difficult Industry: Despite the dominance of legacy players in insurance, John saw a real opportunity: a fragmented market with outdated tech and poor customer experience. Pie’s modern, data-driven model aims to change that.
• Process Power as a Competitive Moat: Pie focuses on doing hundreds of small things better than the competition. John describes how consistent operational execution and better technology form a durable advantage over time.
• Adapting to a Profitability-Focused Environment: John details the major internal shift required when venture markets changed in 2022—from “grow at all costs” to sustainable, efficient operations. Layoffs and restructuring followed, but the business emerged stronger.
• Advice to His Younger Self: John would tell his younger self—and others early in their careers—to say yes to opportunities that offer growth. Don’t over-optimize for money or title; focus on learning and exposure instead.

Quote of the Show:

• "Early in your career, optimize on learning growth, exposure, opportunity, not on money or title or, or anything of that nature." - John Swigart

Links:

• LinkedIn: https://www.linkedin.com/in/johnswigart/
• Website: https://www.pieinsurance.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #PieInsurance

Chapters:

00:00 Intro

01:42 Key Decisions and Leadership Challenges

07:24 Building and Evolving Leadership Teams

11:03 The Concept of Founder Mode

20:58 Competing in a Highly Regulated Market

31:13 Early Days and Customer Acquisition

31:53 Early Days of Multi-Channel Distribution

34:35 Fundraising Challenges and Successes

36:59 Building an Impressive Board

42:33 Navigating Business Challenges

48:39 Founding a Company Later in Life

53:46 Personal Growth and Mentorship

57:06 Pivotal Career Moments

01:00:48 Advice for Aspiring Entrepreneurs

01:02:17 Outro

Sasha opens up about the thrill of building, the challenge of fundraising, the reality of launching with imperfect tech, and the emotional toll of shutting down a business you deeply believe in. From her days as a software engineer to founding one of the most-read blogs of its era, Sasha reflects on learning to trust herself, ask for help, and move on with grace.

Takeaways:

• The AI Aha Moment: Sasha was re-energized to found again after ChatGPT launched publicly in late 2022. She saw an opportunity to solve marketing problems that hadn’t been addressable before due to the language limitations of software.
• Solving a Real Problem from Experience: The product idea came from Sasha’s time at Tableau, where hours of valuable customer video content went unused because it was too hard to search. Elka aimed to automate finding and surfacing those insights for sales teams.
• Alpha and Beta Lessons: The team built fast and launched a beta early to help with fundraising, but users got frustrated with AI inconsistencies. Sasha onboarded every beta customer herself, but admits they may have opened access too soon.
• The Limits of Non-Deterministic Tech: Building on an LLM proved unpredictable. Despite numerous safeguards, the AI struggled with tasks like basic math and clip durations—issues Sasha says may have improved if they had more time to wait out tech advances.
• The Fundraising Wall: While Sasha successfully raised an angel round, later fundraising stalled. She reflects on her discomfort with the performative aspects of pitching and how authenticity may have hurt her in a system designed for bold salesmanship.
• Support and Disappointment: From angel investors to past coworkers, Sasha describes the surprising people who showed up to help—and the ones who didn’t. She credits her team, co-founder, and a few critical mentors with getting them as far as they did.
• Learning, Letting Go, and Looking Ahead: Sasha closes with advice to bring on a co-founder who can fundraise and a reminder to stop being intimidated by others’ confidence. She shares how the journey helped her understand her strengths and what she’ll do differently next time.

Quote of the Show:

• "They may be in positions of power right now, but they're not necessarily smarter than you. They're not better than you… Don’t waste so much energy being intimidated by these people." - Sasha Pasulka

Links:

• LinkedIn: https://www.linkedin.com/in/spasulka/
• TikTok: https://www.tiktok.com/@sashaiscooking

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #ElkaAI

Chapters:

00:00 Intro

03:07 The Aha Moment: Founding Elka AI

04:30 Challenges in Marketing and AI Solutions

09:42 Building the Product: Alpha and Beta Phases

18:07 The Struggles of Fundraising and Leadership

25:22 Navigating Luck and Timing in Entrepreneurship

27:38 Key Decisions and Reflections

31:56 Navigating AI Non-Determinism

33:01 Support System and Key Influences

36:38 Fundraising Challenges and Lessons

42:40 Gender Dynamics in Fundraising

48:47 Personal Journey and Reflections

56:01 Advice for Future Founders

01:00:05 Outro

From convincing early customers to prepay for a non-existent product to implementing a decision-making framework that replaces most meetings, they reveal what it really takes to grow a successful, remote-first company together.

Takeaways:

• Buy-In Without a Product: By focusing on real, unsolved pain points and validating ideas through milestone-based contracts, they built confidence and traction before writing a single line of code.
• Hiring Across Borders for Talent, Not Cost: Nicolas explains how they built Chili Piper by hiring globally from day one, prioritizing talent regardless of geography. They developed a compensation framework by region and job level to ensure fairness while scaling a fully remote team.
• Building Culture Through Annual Global Gatherings: The company brings its global team together once a year for a shared in-person experience—despite the cost. The cultural exchange deepens trust and unity across a fully distributed team, making it one of the most valuable investments they make each year.
• Scaling with Asynchronous Decision Memos: To cut down on meetings, Chili Piper developed a company-wide decision memo process. Each decision includes context, options, and a designated “consensus caller.” This system supports clarity, inclusion, and transparency without constant live discussions.
• Overcoming Financial Stress in a Bootstrapped Journey: Nicolas recounts moments when they had no cash in the bank—offering equity in lieu of salaries to early employees. Those shares later became life-changing, and the experience shaped their resilient, scrappy mindset.
• Community as a Founder Superpower: Alina reflects on how building community—without tracking pipeline or ROI—has been vital to learning and joy. By showing up with genuine curiosity, she’s gained clarity on what customers really care about and how to serve them authentically.
• Leading with Empathy, Curiosity, and Drive: In describing each other’s superpowers, Alina credits Nicolas for his deep empathy and organizational clarity, while Nicolas points to Alina’s intense curiosity and willingness to experiment. Together, they’ve created a leadership model rooted in trust and transparency

Quote of the Show:

• " If you go with selfish reasons… people read that. Even if you don’t say it, they can feel it." - Alina Vandenberghe

Links:

• Alina’ LinkedIn: https://www.linkedin.com/in/alinav/
• Nicolas’ LinkedIn: https://www.linkedin.com/in/nvandenberghe/
• Website: https://www.chilipiper.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #ChiliPiper

Chapters:

00:00 Intro

01:59 Early Challenges and First Customers

07:28 Building and Scaling the Team

12:59 Remote Work and Company Culture

17:55 Decision Making and Documentation

34:23 Alina's Superpower: Curiosity and Community Building

35:59 The Value of Community in Business

40:03 Nicholas's Superpower: Empathy and Human Insight

44:34 Challenges and Triumphs in Entrepreneurship

51:25 The Future of Chili Piper

54:25 Personal Backgrounds and Entrepreneurial Journeys

01:02:28 Balancing Family and Business

01:06:18 Advice for Aspiring Entrepreneurs

01:08:49 Outro

In this in-depth conversation, Alan talks about building high-performing teams, the power of clear communication, succession planning, and how to lead authentically across companies of every size.

Takeaways:

• There’s No “One Thing” — But Culture Comes Close: Alan explains that success doesn’t come from a single action but a combination of choices: pursuing winnable markets, building strong teams, and creating cultures rooted in openness, honesty, and transparency.
• Clear, Simple, & Repetitive Communication: He emphasizes the necessity of repetitive messaging to reinforce confidence and direction within an organization. Regardless of the company size, developing the habit of effective communication early is crucial for long-term success.
• Transforming Vonage Meant Facing Reality: At Vonage, Alan led a shift from residential telephony to business communications. He dismantled internal divisions, repositioned the company, and made hard but necessary cultural changes by being direct about who was driving growth and who wasn’t.
• People Follow Leaders, Not Titles: Alan emphasizes hiring smart, high-integrity people and focusing on the top two layers of the organization. He looks for utility players with CEO potential, not just narrow specialists.
• Avoiding the Trap of Over-Reporting: When he arrived at Avaya, a 77-slide weekly report deck had become the norm. Alan reduced this dramatically, advocating for consistent, actionable metrics that focus on real business health rather than satisfying a process.
• Private Equity Dynamics Can Clash with Strategy: Alan reflects on the challenges of navigating fund timelines and liquidity needs, especially in private equity-backed companies. He notes that these dynamics can often push leaders toward short-term decisions at odds with long-term business goals.
• Leadership Isn’t About Work-Life Balance — It’s About Fulfillment: Alan shares his view that if you love what you do, work-life balance becomes irrelevant. He encourages young professionals to build wide foundations early in their careers by learning as much as they can, as fast as they can.

Quote of the Show:

• " Our job as leaders is to lay that picture out clearly... 'cause all too often we ask people to achieve what they can't imagine." - Alan Masarek

Links:

• LinkedIn: https://www.linkedin.com/in/alan-masarek-1aa1a8a8/
• Twitter (X): https://twitter.com/amasarek
• Website: https://www.avaya.com/en/
  
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Avaya

Chapters:

00:00 Intro

01:43 Alan Massek's Leadership Philosophy

05:45 The Importance of Communication in Leadership

07:20 Transforming Avaya: A Case Study

10:23 Challenges and Strategies in Business Transformation

17:03 Vonage Transformation: From Residential to Business Communications

28:50 Hiring and Building High-Performing Teams

40:22 The Importance of CEO Succession Planning

41:46 Navigating Acquisitions: Strategies and Insights

48:49 The Role of Private Equity in Modern Business

54:09 Life After Stepping Down as CEO

56:20 Leadership and Mentorship: Keys to Success

01:06:02 Work-Life Balance and Return to Office

01:14:28 Advice for Young Professionals

01:17:26 Outro

Jennifer opens up about key moments in her entrepreneurial path, including nurturing team culture, expanding product lines, and overcoming financial hurdles. She also discusses the importance of community-building, the challenges of retail expansion, and the creative satisfaction that drives her forward.

Takeaways:

• Staying True to the Vision: Jennifer explains that her original idea for Fleur du Mal remains core to what the brand is today. She emphasizes the importance of holding onto that original creative inspiration while evolving with new trends and consumer expectations.
• Focusing on Team Culture: Jennifer underscores the importance of investing in team culture. She admits that early on, she was more focused on building the brand, but now she emphasizes team recognition. Initiatives like 'employee of the season' and regular team outings, such as Spring Equinox parties and personalized birthday celebrations, have helped create a strong, appreciative team environment.
• Overcoming Financial Challenges: Jennifer reveals a critical moment two years into Fleur du Mal when the company almost ran out of money. She borrowed funds from investors and had to delay payroll, which resulted in losing much of her team. Despite the setback, she managed to rebuild the company, describing it as the most challenging period in her professional life.
• Passion for Product and Brand: Jennifer highlights her deep passion for product design and brand building, taking personal involvement in every aspect from approving email marketing to attending every product fitting.
• Innovative Products and Methods: She details the challenges and strategies involved in creating and marketing new products, especially within the constraints of advertising restrictions on platforms like Google and Meta.
• Retail Expansion and Community Building: Jennifer discusses the strategic expansion of Fleur du Mal’s retail footprint. By leveraging data from their strong online business, they identify ideal locations for new stores to build community and enhance customer experience. 
• Personal and Professional Growth: Reflecting on her career, Jennifer values the importance of appreciating the journey. She advises founders to find satisfaction in their daily work and to recognize that building something meaningful takes time and effort.

Quote of the Show:

• " I think the best brands really have a very strong point of view that they stick to all the time." - Jennifer Zuccarini

Links:

• LinkedIn: https://www.linkedin.com/in/jenniferzuccarini/
• Twitter (X): https://x.com/jzuccarini
• Website: https://fleurdumal.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #FleurduMal

Chapters:

00:00 Intro

01:33 Building a Strong Team Culture

05:21 Passion for Product and Brand

06:27 Challenges in Brand Building

14:54 Expanding Product Lines

18:27 Navigating Marketing Restrictions

26:22 Engaging with the Community

28:48 The Power of Authenticity in Business

29:24 Expanding Retail Strategy

29:41 Balancing Retail and Online Presence

30:41 Challenges of Retail Expansion

31:37 Future Plans and Team Building

34:20 Overcoming Financial Challenges

37:53 Lessons from Transparency and Team Loss

42:08 Entrepreneurial Spirit and Family Influence

44:48 Mentorship and Role Models

46:58 Drive and Motivation

51:17 Advice for Aspiring Entrepreneurs

54:53 Outro

Anthony shares hard-won lessons from building, and ultimately shutting down, his company, discusses frameworks like the "Founder’s Care-o-Meter" and the "Personal Board of Advisors," and reflects on how founding has shaped his broader life perspective.

Takeaways:

• The Spark for Entrepreneurship: Anthony shares how working closely with rideshare drivers during his early startup days ignited his passion for solving real-world problems through tech, and how the immediacy of feedback fueled his love for early-stage building.
• What Drives a Technical Founder: For Anthony, the excitement lies in scaling impact, solving one user's problem in a way that could eventually benefit thousands. His love of learning and "always day one" mindset continues to push him forward.
• The Lightbulb Moment for Casa: A podcast analogy about how context transforms perception inspired Anthony to rethink how engineering workspaces could better integrate product and design teams, leading to the idea behind Casa.
• Introducing the Founder’s Care-o-Meter: Anthony explains the framework he created to check his conviction at different stages of building Casa. He tracked whether he still felt a "hell yes" about the mission and scored his emotional connection to the problem versus the solution every six weeks.
• Building a Personal Board of Advisors: Anthony stresses the importance of surrounding yourself with trusted confidants, from family to expert mentors, who can offer honest feedback, accountability, and different perspectives throughout the founder journey.
• Knowing When to Shut Down: Anthony candidly describes how feedback from pilot customers, competitive insights, and introspection via the Care-o-Meter helped him make the difficult but clear-eyed decision to wind down Casa.
• Founding and Life Philosophy: Anthony reflects on how founding has shaped his view of service, resilience, and embracing life's unexpected opportunities. His future focus is simple: prioritize the people you work with and the problems you solve.

Quote of the Show:

• " Experience is what you get when maybe you didn't get what you wanted… being able to share that with [future founders] is such a critical point, and it's super important." - Anthony Corletti

Links:

• LinkedIn: https://www.linkedin.com/in/anthonycorletti/
• Twitter (X): https://x.com/anthonycorletti
• Website: https://www.anthonycorletti.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Casa

Chapters:

00:00 Intro

04:14 Anthony's Journey and Early Career

09:10 The Inspiration Behind Casa

14:51 The Founder's Care-o-Meter

19:49 Building a Personal Board of Advisors

25:57 Facing Initial Challenges

26:57 Pivoting and Feedback

27:31 Connecting with Industry Leaders

29:28 Emotional Journey of a Founder

31:01 Reflecting on Key Decisions

33:06 The Importance of Co-Founders

33:46 Customer-Centric Product Development

36:16 The Role of Luck in Success

38:46 Balancing Life and Founding

39:42 Founder's Philosophy and Future Plans

45:55 Where To Next?

48:24 Outro

In this episode, Chieh Huang shares the raw, unfiltered story of building Boxed from a garage into a national e-commerce brand serving tens of millions of customers, and the emotional toll, unlikely breakthroughs, and market forces that shaped every chapter of the journey. He reflects on the lonely months of almost no orders, the overnight surge that changed everything, the pressure of becoming a public company CEO, and the reality that even the strongest operators can’t outrun macro cycles.

Chieh also opens up about what happens after the final chapter closes, the exhaustion, the identity shift, and the unexpected necessity of real recovery. His honesty about the highs, lows, and lessons he’s taking into his next company makes this a powerful episode for founders navigating their own versions of the broken-glass analogy.

Takeaways: 

• From Humble Beginnings to a Notable Success: Chieh Huang started Boxed in 2013 right from his garage, with only dreams and a strong will to succeed. Within a few years, Boxed scaled to become a renowned online wholesale retailer, serving millions.
• The Challenge of Maintaining Purpose: Chieh emphasizes the importance of cultivating an intrinsic purpose within a company. At Boxed, the sense of purpose wasn’t predefined but evolved over time as the team grew, particularly among the fulfillment center workers.
• The Rollercoaster Ride of Fundraising: Chieh's journey wasn't without financial hurdles. While initial investments were relatively easier owing to his prior success in the gaming industry, subsequent rounds posed challenges, reflecting the inconsistent nature of venture funding.
• Consumer Business Dynamics: Chieh discusses the unpredictability of consumer businesses, highlighting how a single viral moment or endorsement can drastically influence a company's success, unlike enterprise businesses that grow through steady acquisition of clients.
• Public Company Experience: Huang's experience in taking Boxed public via a SPAC (Special Purpose Acquisition Company) taught him that public market dynamics significantly differ from private ventures
• Handling Burnout: Chieh and David discuss the inevitability of burnout in an entrepreneur's journey and the importance of managing it proactively through short breaks, personal downtime, and stepping away when necessary to recharge.

Quote of the Show:

• “Being a CEO is like trying to be the greatest of all time in a broken glass eating competition." - Chieng Huang

Links:

• LinkedIn: https://www.linkedin.com/in/chiehhuang/ 
• Website: https://boxed.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Boxed

Chapters:

00:00 Intro

00:46 The Journey of Boxed

02:42 The Purpose Behind Boxed

07:14 Starting in the Garage

09:23 The Big Break and Rapid Growth

20:36 Fundraising Challenges and Successes

26:02 Navigating Market Ups and Downs

32:09 Reflecting on Past Experiences

33:59 Journey to Going Public

36:26 Challenges of Being a Public Company CEO

39:22 Navigating Investor Relationships

44:17 Balancing Work and Avoiding Burnout

50:03 The End of Boxed and New Beginnings

55:03 Early Entrepreneurial Spirit

57:54 Role Models and Mentors

01:01:25 Core Motivations and Advice

01:05:51 Outro

Sean dives into how simplicity became his core operating principle, the creative strategies behind building a strong team, and why bootstrapping gave him the ultimate freedom. He also opens up about co-founder dynamics, the emotional challenges of scaling leadership, and finding clarity after stepping down.

Takeaways:

• Start with Simplicity, Scale with Clarity: Sean shares how simplicity became a guiding principle across operations, sales, and product. By constantly asking “How can we make this easier?”, Industry Dive streamlined execution and scaled effectively across 30 different markets.
• The Coffee Challenge That Built Culture: To foster cross-team collaboration, new hires were given a $50 coffee stipend and a list of quirky and strategic questions to ask people outside their department. This initiative not only built early camaraderie but also helped break down silos before they could form.
• Bootstrapping with Intent (and $400K): While Industry Dive raised a small angel round, Sean considered the business bootstrapped and didn’t pay himself for 18 months. He talks about resisting early VC offers in favor of building profitably and why media businesses need time, not acceleration.
• Strategic Exit Through Private Equity: Sean shares how the PE partnership offered strategic guidance, operating support, and true alignment on growth goals.
• The Leadership Challenges No One Talks About: Sean reflects on the difficulty of maintaining culture and connection at scale, especially through the pandemic. He emphasizes the importance of transparency, weekly all-hands, and honest company-wide Q&As—even when the questions were tough.
• Letting Go and What Comes Next: After stepping down as CEO, Sean is still adjusting. He shares how he's staying engaged and how he’s giving himself space to figure out what’s next with no pressure.

Quote of the Show:

• “There’s an incredible amount of time to be successful… you can enjoy it along the way too.” - Sean Griffey

Links:

• LinkedIn: https://www.linkedin.com/in/seangriffey/
• Twitter (X): http://twitter.com/seangriffey
• Company Website: https://www.industrydive.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #IndustryDive

Chapters:

00:00 Intro

01:27 Key Strategies for Success at Industry Dive

02:31 The Coffee Challenge: Building Cross-Departmental Relationships

07:15 Maintaining Simplicity in Business Operations

10:19 Co-Founder Dynamics and Roles

16:34 Bootstrapping and Fundraising Journey

26:09 Private Equity Partnership Experience

29:00 Private Equity's Role in Scaling

30:57 Navigating the Pandemic with Private Equity

33:03 Alignment and Exit Strategy with Private Equity

37:51 Challenges and Team Alignment

47:42 CEO's Reflections and Future Plans

51:03 Advice for Aspiring Entrepreneurs

58:29 Outro

Rohyt discusses his unique business strategies, the importance of an employee-first culture, navigating massive challenges, and raising capital efficiently. Watch now to gain invaluable entrepreneurial insights from one of the leading minds in cybersecurity.

Takeaways:

• Bootstrapping to Success: Rohyt discusses how he and his co-founder bootstrapped the company to $2.5 million in ARR before accepting any external funding. They leveraged their prior industry experience and personal networks to secure their first enterprise customers.
• Implementing Employee-Friendly Policies: The adoption of policies such as half-day Fridays significantly boosted morale and productivity among staff. Rohyt emphasizes the importance of putting employees first and how this principle was pivotal in creating a positive company culture. 
• Transitioning From Services to Product: Rohyt talks about the challenges and learning curve associated with moving from a consulting company to a scalable product business. He highlights the necessity of balancing growth with capital efficiency and the mindset shift required to achieve this.
• Acquiring Enterprise Customers: The PhishMe team focused on a hands-on approach to customer acquisition, including attending numerous industry events and leveraging their expertise in cybersecurity to build trust. Expansion into new markets was approached cautiously and strategically, ensuring that initial customer wins provided a foundation for further growth.
• Investigated by the U.S. government: Rohyt recounts the hardships faced during a CFIUS investigation into a Russian investor associated with their private equity backer. Despite an onslaught of negative publicity and customer attrition, the PhishMe team managed to steer the company through this crisis while maintaining their integrity and focus on growth.
• Fundraising and Investor Relations: Initially, raising capital was a grueling process involving over 100 investor meetings to secure their first funding. However, as PhishMe demonstrated significant growth, subsequent funding rounds saw increased interest, culminating in multiple competing term sheets and better negotiation leverage.
• Balancing Innovation and Customer Needs: The importance of listening to customer feedback and anticipating future needs led to the development of complementary products, which significantly boosted the company's market standing and revenue. This approach ensured that PhishMe stayed relevant and valuable to its customers.

Quote of the Show:

• “ There's probably a hundred good ideas for any given product, and you have to be able to whittle it down to say, what are the three things we're doing over the next three to six months?” - Rohyt Belani

Links:

• LinkedIn: https://www.linkedin.com/in/rohytbelani/
• Twitter (X): https://x.com/rohytbelani
• Company Website: https://cofense.com/
  
  

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #PhishMe

Chapters:

00:00 Intro

01:17 What You'd Do Again as CEO

04:20 Challenges and Insights on Work Culture

07:16 Early Customer Acquisition

16:06 Fundraising Journey

23:26 Product Evolution and Expansion

30:15 Navigating Customer Feedback and Innovation

32:40 Defining and Evolving the Ideal Customer Profile (ICP)

33:45 Transitioning from Consulting to Product Company

36:09 Challenges and Strategies in Scaling a Product Company

41:40 Overcoming a Major Crisis: The CFIUS Investigation

47:01 Life After Stepping Down: Advising and Mentoring

48:55 Reflections on Entrepreneurship and Mentorship

57:31 Outro

Itamar shares insights on how AI can enhance code integrity, optimize developer workflows, and shape the future of software engineering. From his entrepreneurial journey to the latest advancements in AI, Itamar dives deep into the challenges and opportunities of bringing AI into software development.

Takeaways:

• From Research to Entrepreneurship: Itamar shares his journey from studying AI to co-founding Qodo, discussing how his background in machine learning and software engineering led to his mission of improving code quality.
• AI-Powered Code Integrity: AI isn’t just about generating code—it’s about ensuring its accuracy and efficiency. Itamar explains how Qodo is redefining software testing by automating code validation and catching potential issues early in development.
• Challenges of Building AI for Developers: Unlike other AI applications, coding tools must be highly reliable. Itamar breaks down the unique hurdles of building AI that developers can trust and seamlessly integrate into their workflows.
• The Role of AI in Software Testing: Traditional software testing methods are time-consuming and often inefficient. Itamar discusses how AI-driven test generation is changing the landscape, making development faster and more reliable.
• Scaling an AI Startup: Bringing an AI-powered tool to market requires balancing innovation with practicality. Itamar shares his experience of scaling Qodo, attracting early adopters, and iterating based on developer feedback.
• Ethical Considerations in AI Development: With AI playing a bigger role in critical processes, ethical concerns are inevitable. Itamar reflects on responsible AI development, the risks of automation, and how companies can build AI that benefits users.
• The Future of AI in Development Workflows: Looking ahead, Itamar shares his predictions for how AI will continue to transform software engineering, from fully automated debugging to more intelligent coding assistants.

Quote of the Show:

• “I'm not saying that technical people should give up on that. Actually that's our superpower.” - Itamar Friedman

Links:

• LinkedIn: https://www.linkedin.com/in/itamarf 
• Twitter (X): https://x.com/itamar_mar
• Company Website: https://www.qodo.ai 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Qodo

Chapters:

00:00 Intro

01:36 What You’d Do Again As CEO

06:02 Transitioning to CEO

14:27 The Role of AI in Software Development

21:28 Challenges and Insights as a First-Time CEO

32:21 Finding the First Customers

36:57 Strong Content and Alpha Code

38:22 Product-Led Growth and Sales Strategy

42:08 Fundraising Journey and Investor Alignment

51:57 Challenges and Vision for AI in Coding

54:59 Balancing Entrepreneurship and Personal Life

01:04:31 Advice to Younger Self

01:07:49 Outro

Nadia shares the challenges of building an inclusive brand, navigating venture funding, and leading a mission-driven company through rapid growth and industry shifts. She also reflects on the power of community, hiring the right team, and the lessons she learned stepping down as CEO after a decade at the helm.

Takeaways:

• The Power of a Co-Founder Relationship: Nadia emphasizes that choosing the right Co-Founder is one of the most critical decisions in a startup journey. She shares how this played a pivotal role in shaping Dia&Co and why equal economics from day one helped maintain a strong partnership.
• Building a Business from the Ground Up: Before developing a scalable platform, Nadia and her Co-Founder personally shopped for thousands of customers to deeply understand their needs. She explains why doing things manually in the early days was key to creating a product-market fit.
• Fundraising Challenges & Breakthroughs: Raising Dia&Co’s first million dollars took nearly a year, yet within 18 months, they secured over $100 million in funding. Nadia shares insights on what changed, how she navigated investor skepticism, and why the right investors can make all the difference.
• Scaling from Startup to Major Brand: At its peak, Dia&Co hired 600 people in a single year. Nadia discusses the challenges of leading a fast-growing organization, maintaining company culture, and evolving her leadership style to keep up with the business’s rapid expansion.
• The Role of Community in Brand Building: The Dia&Co customer base formed organic Facebook groups that grew into a passionate and engaged community. Nadia shares how customers turned into brand ambassadors, planned meetups, and even got tattoos to represent the brand’s impact.
• Navigating Major Business Shifts & the Pandemic: From industry-wide changes to the unpredictability of COVID-19, Nadia reflects on leading through uncertainty, making tough calls, and staying resilient in the face of evolving challenges.
• Stepping Down as CEO & What’s Next: After a decade of building Dia&Co, Nadia made the difficult decision to transition out of the CEO role. She opens up about that process, how she adjusted to life post-CEO, and what she’s exploring next.

Quote of the Show:

• “ There's a fundamental attribute of being an immigrant that you think that the locus of control in your life is inside of you” - Nadia Boujarwah

Links:

• LinkedIn: https://www.linkedin.com/in/nadiaboujarwah/
• Company Website: https://www.dia.com/
  
  

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Dia&Co

Chapters:

00:00 Intro

01:40 What You’d Do Again As CEO

08:06 Starting Dia&Co: From Idea to Execution

14:38 Building a Community and Raising Funds

22:52 Navigating Investor Relationships

27:45 Transitioning Leadership at Dia&Co

33:29 Biggest Challenge Faced at Dia&Co

36:53 Growing Up in an Immigrant Family

41:02 The Value of an MBA

49:33 Future of AI in Apparel

52:07 Advice to Younger Self

55:47 Outro

Rich shares insights on hiring with purpose, managing multiple stakeholders, and why philanthropy needs both measurable outcomes and deep human connection to drive real change.

Takeaways:

• Weekly CEO Emails for Transparency: Rich started sending a weekly email to Robin Hood staff every Monday morning, sharing updates on his week, priorities, and even personal reflections. This practice fosters alignment, strengthens internal communication, and helps employees feel more connected to leadership.
• The Power of Celebration in Workplace Culture: Robin Hood embraces celebrations, from birthdays to cultural events, to strengthen relationships among employees. Rich emphasizes the importance of fostering a connected workplace, especially in a hybrid work environment.
• Hiring for Passion, Not Just Skills: When interviewing candidates, Rich prioritizes one key question: "Why Robin Hood? Why now?" He looks for candidates who have a deep, personal connection to the organization's mission, believing that true passion is the most valuable trait an employee can bring.
• Balancing Five Key Stakeholders: Robin Hood serves five different groups: donors, nonprofit partners, policymakers, internal teams, and the communities they support. Rich discusses how managing these relationships requires tailored communication and a clear focus on measurable impact.
• Data-Driven Philanthropy: Robin Hood employs a rigorous evidence-based approach to funding, using data to quantify the financial impact of its programs, to ensure donor funds are invested in initiatives that create measurable and lasting change for those living in poverty.
• The Role of AI in Social Impact: Rich explores how Robin Hood is working to ensure that nonprofit organizations—and the communities they serve—are equipped to navigate the technological changes from AI.

Quote of the Show:

• “ What is it about your life, your work, your vision of the world that draws you to this mission? It’s the one thing that you can’t necessarily teach or train… for any job.” - Richard Buery

Links:

• LinkedIn: https://www.linkedin.com/in/richardbuery/
• Twitter: https://x.com/RichardBuery
• Website: https://robinhood.org/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #RobinHood

Chapters:

0:00 Intro

1:37 What You’d Do Again As CEO

6:05 Building a Collaborative Executive Team

8:56 Hiring for Passion and Mission Alignment

14:31 The Importance of Storytelling and Public Speaking

3:24 Navigating Multiple Constituencies

34:03 Analog Solutions in a Digital World

38:43 Challenges of Leading Robin Hood

39:41 Fundraising and Donor Engagement

43:36 Impact of AI and Technology

46:09 Rich’s Background

1:00:01 Advice to Younger Self

1:02:21 Outro

Fredrik shares how he learned to think for himself as a leader, the challenges of rapid adaptation, and the impact of global talent on the creative industry. He also reflects on AI’s role in shaping the future of professional services and his belief in continuous personal development as a CEO.

Takeaways:

• Thinking for Yourself in Leadership: Early in his career, Fredrik struggled with following conventional wisdom before realizing that not all frameworks work for every company. He shares how Superside abandoned OKRs in favor of a problem-solving approach that fosters real alignment and innovation.
• Evolving the Business Model: Superside has transformed multiple times, from a lean startup using chat-based task management to a full-scale AI-powered creative services company. Fredrik shares how adaptability has been key to staying ahead in a rapidly changing industry.
• The Role of AI in Creative Services: AI is fundamentally reshaping the creative industry, from automating repetitive tasks to enhancing high-level creative strategy. Fredrik discusses Superside’s vision to integrate AI seamlessly into design workflows without replacing human creativity.
• Leveraging Global Talent: Superside connects top creative talent from cities like Buenos Aires and Cape Town with leading enterprise clients. Fredrik explains why access to global talent is the real game-changer for creative work.
• Leading Through Crisis: COVID-19 forced Superside into “wartime mode” as they lost nearly 40% of their customers overnight. Fredrik shares how his team’s ability to pivot quickly turned a dire situation into an opportunity for long-term growth.
• Personal Growth as a CEO: Fredrik recently embraced executive coaching and personal development, realizing that great leadership requires constant improvement. He reflects on how acknowledging his weaknesses has made him a more effective leader.

Quote of the Show:

• “Cultivate joy and excitement about the future possibilities as the antidote to all your fear and worry about the things that can go wrong.” - Fredrik Thomassen

Links:

• LinkedIn: https://www.linkedin.com/in/fredrikthomassen/
• Twitter: https://x.com/f_thomassen
• Website: https://www.superside.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Superside

Chapters:

0:00 Intro

1:04 What You’d Do Again As CEO

10:19 The Evolution of Superside

20:42 Global Talent and Creative Hubs

24:52 AI's Role in the Creative Market

30:53 Running a Business from Oslo

37:43 The Impact of COVID-19 on Superside

51:27 Balancing Work and Family Life

55:08 Advice to Younger Self

1:00:20 Outro

Diego shares his philosophy on hiring for alignment, navigating the emotional rollercoaster of being a CEO, and how he successfully positioned Algorithmia for acquisition. He also provides insights into enterprise sales, fundraising, and why finding the right investors and employees is key to long-term success.

Takeaways:

• The Power of Finding the Win-Win: Diego explains his hiring philosophy of aligning company and employee goals. He prioritized candidates whose personal growth goals matched the company’s mission, ensuring stronger retention and culture.
• Managing the CEO Rollercoaster: From reassuring employees to handling crises behind the scenes, Diego reflects on the emotional toll of leadership. He shares how CEOs act as buffers, absorbing stress to keep teams, investors, and customers aligned.
• Early Customer Wins & Enterprise Sales Strategy: Algorithmia’s first customers came from a mix of content-driven PLG motion and conference networking. Diego explains how startups must “get on the field” to win enterprise deals.
• Scaling Yourself as CEO: As the company grew, Diego transitioned from closing every deal to focusing on high-impact interactions. He shares his approach to using thought leadership, content marketing, and direct customer engagement to scale influence.
• The Role of Investors & Board Dynamics: Not all investors provide the same value. Diego breaks down how he leveraged board members effectively, categorized investor types, and ensured expectations were aligned for mutual success.
• Positioning for Acquisition: Diego shares how Algorithmia’s strategic focus on machine learning deployment made it an attractive acquisition target for DataRobot. He explains how they navigated the M&A process in just 45 days.

Quote of the Show:

• “Sometimes the worst day of your life and the best day of your life are the same day, just different hours.” - Diego Oppenheimer

Links:

• LinkedIn: https://www.linkedin.com/in/doppenheimer/
• Twitter: https://x.com/doppenhe

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Algorithmia

Chapters:

0:00 Intro

1:21 What You’d Do Again As CEO

09:01 The Importance of Team Dynamics

16:00 First Customers and Go-to-Market Strategy

22:41 Scaling the Business and CEO Involvement

27:23 Customer Obsession and Tactical Initiatives

30:43 Exclusive Roundtable Discussions

32:08 Challenges with Large Customers

37:17 Navigating Investor Relationships

40:53 The Acquisition Journey

47:29 Emotional Rollercoaster of Entrepreneurship

51:10 Family Influence and Entrepreneurial Roots

56:25 Current Ventures and AI Focus

58:12 Advice to Younger Self

1:01:47 Outro

Jindou shares his journey from graphic designer to entrepreneur, discussing the challenges of hiring and firing, scaling a business, and learning the rules of the fundraising game. He also reflects on his personal experiences, from his childhood in Australia to launching a successful SaaS company, and offers candid insights on what it takes to build a resilient organization.

Takeaways:

• Culture & Core Values: Jindou stresses the importance of defining company values early. He shares how HappyCo identified its core values and evolved them over time to ensure they remain relevant as the company scales.
• Hiring & Firing with Intention: Building a strong team requires making tough decisions. Jindou reflects on his journey from hesitating to fire underperforming employees to realizing that removing a poor fit benefits both the individual and the organization.
• Lessons in Rapid Growth & Downsizing: Jindou explains how the company became more efficient while continuing to grow revenue, proving that success isn’t about headcount but about having the right people in the right roles.
• Building with the Customer in Mind: Jindou explains why deeply understanding the end user’s needs has been critical to HappyCo’s success. He shares how small design tweaks—like increasing button sizes—can make all the difference.
• Fundraising is a Game: Jindou learned that fundraising is a game with rules that founders must understand. He shares hard-earned lessons about negotiating terms, dealing with investor pressure, and securing critical last-minute funding.

Quote of the Show:

• “Fundraising is a very unfair game for founders… a lot of early stage founders, myself included, we got bullied. We just didn't know we got bullied.” - Jindou Lee

Links:

• LinkedIn: https://www.linkedin.com/in/jindou/
• Twitter: https://x.com/jindoulee
• Website: https://happy.co/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #HappyCo

Chapters:

0:00 Intro

1:33 What You’d Do Again As CEO

6:16 Experiences Shaping Values

12:31 Navigating Growth and Downsizing

20:49 The Importance of Customer-Centric Design

31:26 Fundraising Realities and Challenges

35:04 Navigating Term Sheets and Legalities

43:09 Biggest Challenges at HappyCo

47:20 Visions for the Future

49:44 Jindou’s Background and Upbringing

53:39 Career Beginnings and Lessons Learned

58:57 One Piece Of Advice

59:48 Outro

Fellay shares her experiences as a female founder and her journey to raising millions to build her current business. She provides insights on early branding strategies, overcoming operational hurdles, and the challenges of building a high-growth company.

Takeaways:

• Branding Early: Fellay emphasizes the power of investing in brand identity from the start, using distinct colors, mascots, and unique marketing to differentiate Speckit in a crowded market.
• Creative Customer Acquisition: From leveraging LinkedIn and Twitter communities to booking a booth at Dreamforce before having customers, Fellay highlights unconventional methods that helped land Speckit’s first clients.
• Leadership Evolution: Fellay reflected on learning the importance of hiring leaders with self-awareness, vulnerability, and a growth mindset rather than overvaluing industry experience.
• Navigating Growth and Challenges: Fellay shares a pivotal period in 2022 when Spekit faced product performance issues, economic pressures, and team transitions during a period of growth, and how these hurdles shaped the company for the better.
• Iterating on ICP (Ideal Customer Profile): Fellay discusses the journey of narrowing down Spekit’s ideal customer profile, focusing on enablement leaders, marketing professionals, and RevOps teams to optimize impact.

Quote of the Show:

• “ You don't want to be sounding like you're just like a marketing ad for your product… talking about the journey, the lessons I'm learning, those tend to get the most engagement. ” - Melanie Fellay

Links:

• LinkedIn: https://www.linkedin.com/in/melaniefellay/  
• Twitter: https://x.com/melfellay  
• Website: https://www.spekit.com/  

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Spekit

Rabie joins host David Politis to discuss his journey redefining convenient and healthy meals. He examines the challenges, lessons, and pivotal moments that shaped Tovala’s success, including near-crisis fundraising stories and the company's rise during the pandemic. 

Takeaways:

• Weekly CEO Emails: Rabie has sent a reflective email every Monday for nearly a decade, offering updates and key priorities for the team. This practice has grown from personal insights in a small startup to comprehensive updates for a team of over 400.
• The Product Journey: Rabie shares how the vertically integrated model of providing both the meals and the equipment to cook them has proven essential to maintaining high quality and customer satisfaction.
• Overcoming Challenges: Rabie recounts a critical moment in 2020 when Tovala faced the collapse of a Series B term sheet at the start of the pandemic. With only weeks of cash on hand, Rabie had to bridge funding to ultimately raise the round.
• Hiring Philosophy: Over time, the company shifted to hiring for high potential to hiring for experienced professionals to scale the business while retaining key early employees who grew alongside the company.
• Pandemic Growth: While the pandemic posed challenges, it also catalyzed growth for Tovala as more consumers sought convenient, healthy meal options at home. The company’s ability to meet this demand helped triple its business in 2020.
• Balancing Family and Leadership: Rabie emphasizes the importance of maintaining a healthy work-life balance, making time for family and personal well-being. He candidly discusses how this approach evolved over the years and its impact on both his leadership and company culture.

Quote of the Show:

• “To me, it's a really powerful combination where you get the ambition and the drive and the hunger, but you don't get the ego.” - David Rabie

Links:

• Twitter: https://x.com/daviderabie
• LinkedIn: https://www.linkedin.com/in/davidrabie/
• Website: https://www.tovala.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Tovala

Jeff shares how he thinks about product velocity, founder self-awareness, team dynamics, and why the individual partner matters far more than the firm logo. This conversation is a masterclass for CEOs building from zero to one and choosing who they want in the trenches with them.

Takeaways: 

• Product Velocity Matters: Jeff emphasizes the importance of product velocity, especially in the early stages of a startup. He explains that founders need to run numerous experiments to achieve product-market fit, often partnering with technical leaders to accelerate this process.
• Building the Right Team: According to Jeff, a strong indication of a founder's potential is their ability to attract a talented team. He believes that successful founders often draw in colleagues from their previous ventures, creating a "band" that's been together through various challenges.
• The Sales Dilemma: Founders with technical expertise often lack strong sales skills. Jeff looks for self-awareness in founders, assessing if they can identify their weaknesses and augment them with the right partners or co-founders.
• The Importance of Early Impressions: First impressions are crucial in the VC world. Jeff and David both agree that initial meetings often determine whether an investor leans in. Founders should craft a compelling story and use the first few minutes to capture interest.
• Aligning with the Right Investor: For Jeff, investing is akin to a decade-long partnership. He advises founders to seek investors who align with their vision and are genuinely interested in their success, rather than just providing capital.
• Preparation and Self-Awareness: Founders need to be brutally honest about their strengths and weaknesses. Jeff advises preparing thoroughly before meeting investors and leveraging one's unique strengths while addressing weaknesses to form a complete leadership package.

Quote of the Show:

• “We talk a lot about product velocity being the most critical metric we look for." - Jeff Morris Jr.

Links:

• LinkedIn: https://www.linkedin.com/in/jeffmorrisjr/ 
• Website: https://chapterone.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #ChapterOne

Chapters:

00:00 Intro

01:10 Key Metrics for Early-Stage Investments

02:37 Assessing Founders and Teams

07:51 The Importance of Self-Awareness in Founders

10:38 The Founder-Investor Relationship

14:34 Navigating the Venture Capital Landscape

19:12 The Dynamics of Fundraising

27:36 The Current Investment Climate

41:44 Jeff Morris, Jr.'s Journey to Venture Capital

44:39 Outro

Known for her pivotal roles at Palm Computing and Handspring, Donna offers a rare long-term perspective on leadership, culture, and the technological landscape that has spanned decades. 

Takeaways: 

• The Importance of Building a Strong Culture: Donna emphasizes that a great company starts with great people. She shares the crucial role a positive culture played in her companies, stating that when you foster an environment people love, they follow you from venture to venture.
• Adaptability is Key: One of the most sought-after traits in employees, according to Donna, is flexibility. She highlights the importance of hiring individuals who are not rigid in their thinking but can pivot and grow with the company.
• Challenges of Raising Capital: Donna recounts the struggles in securing investment for Palm, despite her extensive network. She faced skepticism from investors due to previous failures in handheld computing and the prioritization of internet ventures over hardware.
• Reflective Organizational Planning: Donna shares her strategic approach to planning through biannual offsites, fostering a culture of reflection and adjustment. These sessions not only solidified strategic objectives but also enhanced team camaraderie through collaborative efforts and fun activities.
• Maintaining Integrity and Respect: Donna’s overarching advice is to treat everyone with respect. This principle was foundational in building the cultures of her companies and remains a critical lesson for sustainable leadership.

Quote of the Show:

• “I really appreciated people who could deal with change. Changing circumstances, changing environment, changes within the company, as opposed to people who were rigid." - Donna Dubinsky

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Handspring #Palm

Chapters:

00:00 Intro

01:30 The Importance of People in Building Companies

03:42 Creating and Maintaining Company Culture

16:00 The Palm Story: Revolutionizing Personal Computing

37:09 Frustrations of Being an Employee

37:44 Challenges of Selling a Company

39:02 Balancing Structure in Big Companies

40:55 Starting Handspring and Product Focus

45:03 Biggest Mistake at Handspring

49:00 Advice for Fast-Growing Companies

50:28 Impact of AI and Market Dynamics

55:05 Personal Background and Career Beginnings

57:33 Big Breaks and Mentorship

01:03:06 Government Service and National Impact

01:07:49 Outro

In this episode, Jules Maltz shares the mindset that has guided him through decades of backing generational companies like Slack, Dropbox, Grammarly, MuleSoft, G2, and Buddy Media. For Jules, the brightest periods in a company’s journey are the moments to build aggressively: to hire exceptional executives, deepen product moats, and prepare for act two and act three long before the market forces the issue.

Jules also opens up about what he looks for in founders, why authenticity matters more than pitch polish, and how trust is built in the first months of an investor–founder relationship. He reflects on his own misses, the evolution of venture capital, and the emotional clarity that underpins his earliest investment decisions.  

Takeaways: 

• Authenticity and Passion are Essential: Jules emphasizes the importance of authenticity and passion in founders. He looks for individuals who have a genuine drive and a personal connection to the problem they are solving.
• Beyond the Metrics: When evaluating potential investments, Jules seeks stories that transcend traditional metrics. He recalls his first investment in Twitter, where the pitch focused more on the transformative potential of the platform rather than immediate financial returns.
• Building Trust Early On: Establishing trust during the initial months after an investment is crucial. Jules believes that consistently delivering on promises and being genuinely helpful builds credibility.
• Adapting Communication Styles: Jules adapts his communication style based on the needs of each CEO. Some prefer regular updates, while others might communicate only during key events.
• Sustaining Growth Through Strategic Hiring: Jules advises companies to recruit strong executives and think ahead about their business strategies during periods of growth. By doing so, businesses can better navigate market changes and sustain their growth trajectory.
• Nurturing Relationships for Long-Term Success: Relationships are at the heart of venture capital. Whether it's trust between founders and investors or maintaining connections with past business partners, nurturing these relationships can lead to long-term success and learning.

Quote of the Show:

• “When the sun is shining on your business, that’s a great time to recruit super strong executives and think about act two and act three." - Jules Maltz

Links:

• LinkedIn: https://www.linkedin.com/in/julesmaltz/ 
• Website: https://www.ivp.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #IVP

Chapters:

00:00 Intro

01:25 Key Traits of Successful Founders

03:52 The Importance of Authenticity

06:17 Evaluating Investment Opportunities

10:59 The Twitter Investment Story

21:57 Building Trust with Founders

27:11 Trusting Your CEO's Vision

29:31 Navigating Hypergrowth and Market Changes

33:53 The Excitement and Challenges of AI Investments

41:51 Teaching and Sharing Venture Capital Insights

47:24 The Role of Trust in Venture Capital

50:35 Biggest Investment Regrets

53:31 Outro

They open up about building cult-like culture, radical transparency, co-founder dynamics, fundraising strategies, pivots, parenting, and everything in between. With humor and honesty, the Lazerows share the unvarnished truth of what it takes to build something meaningful, and survive the chaos along the way.

Takeaways:

• Building a Cult-like Culture with Intentionality: Kass shares how she focused on creating a high-trust, high-engagement company culture through rituals, transparency, shared values, and even handwritten birthday cards. The foundation was purpose-driven work, and a lot of cupcakes.
• Radical Focus as a Leadership Imperative: Mike emphasizes the importance of choosing just 3–5 core priorities each quarter and communicating them relentlessly. He admits that his natural state is distraction, and that focus, both personal and organizational, is what drives growth.
• Fundraising Is a Relationship Business: Mike describes how he built trust with investors over time by sending updates, even to people who said no, and treating everyone with respect, from analysts to GPs. He reframes fundraising as offering a great opportunity, not asking for a favor.
• The Power (and Pain) of Pivoting: The Lazerows recount the early missteps at Buddy Media, from virtual currency to raffles, before landing on a scalable SaaS product. They stress the importance of cutting old lines of business fast and committing fully to what’s next.
• Marriage and Co-Founding: They describe co-founding as an intense version of marriage, with shared values, relentless communication, and radical honesty. Kass encourages couples to embrace their lanes and support each other’s growth, both professionally and personally.
• Startups and Parenting Don’t Balance, But They Can Work: Kass shares how they intentionally deprioritized social commitments and accepted imperfection at home to build their company. She encourages other founder-parents to aim for 80%, not perfection, and to give themselves grace.

Quote of the Show:

• "Being a founder, there’s no worse way to spend your day. And it’s awesome, right?" - Mike Lazerow

Links:

• Kass’ LinkedIn: https://www.linkedin.com/in/kasslazerow/
• Mike’s LinkedIn: https://www.linkedin.com/in/lazerow/
• Get Their Book: https://shovelingshit.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Shoveling$H!T

Chapters:

00:00 Intro

00:46 Podcast Journey and Growth

01:41 Acknowledging Sponsors and Supporters

03:56 Introducing Cass and Mike Lazaro

05:33 Building Buddy Media: Key Strategies and Insights

08:19 Challenges and Successes in Leadership

14:09 The Importance of Transparency

15:19 Husband-Wife Co-Founders: A Unique Dynamic

20:09 Fundraising and Building Relationships

27:46 Marketing and Branding Strategies

34:09 Thought Leadership and Public Speaking

36:36 Navigating Business Pivots

38:25 The Birth of Buddy Media

40:31 Challenges and Successes of Custom Apps

45:20 Balancing Family and Business

48:50 Advice for Aspiring Entrepreneurs

54:58 Building a Positive Company Culture

01:02:21 Q&A with the Audience

01:11:11 Outro

Murphy discusses his approach to leadership, the impact of meeting with hundreds of customers, and the critical role of operational discipline. Additionally, he reflects on his entrepreneurial journey, from his early ventures to his mentoring experiences and the factors driving his unyielding ambition. 

Takeaways:

• Embracing Innovation and AI: Bryan emphasizes the importance of being early adopters of AI in order to remain competitive. He recounts how Smartling's leadership team proactively engaged with AI technologies as soon as they became available. Cultivating Customer Obsession: A significant part of Bryan's approach as CEO involves a deep focus on understanding and anticipating customer needs. He actively engages with customers, often initiating conversations with questions about the primary problems they are trying to solve.
• Building a Robust Operating Rhythm: Bryan highlights the critical role of a structured operating rhythm in executing plans effectively. Weekly leadership and management council meetings at Smartling help streamline processes and keep initiatives on track.
• Strategic Decision-Making in Remote Work Setup: With over 200 employees across 20 countries, Bryan holds annual gatherings and regular meet-ups to foster team cohesion while accommodating the global distribution of the workforce.
• Clarifying Business Metrics and KPIs: To Bryan, measuring success involves defining clear Key Performance Indicators (KPIs) that are aligned with customer value. These metrics directly inform product development and strategic priorities, ensuring the company remains focused on delivering value to customers.
• Overcoming the Innovator’s Dilemma: Bryan explains the challenge of balancing innovation with existing successful practices, a common issue known as the innovator's dilemma, by systematically integrating new technologies like AI to improve its service offerings without destabilizing its well-established operations.
• Advice for Aspiring Leaders: Bryan advises newcomers to the industry to always meet their obligations first and then seek opportunities to contribute more broadly, ensuring career advancement and sustained organizational impact.

Quote of the Show:

• “[CEOs] have that latitude to run across the organization and dive down into each one of the respective parts of the organization, no one else can do that or does do that." - Bryan Murphy

Links:

• LinkedIn: https://www.linkedin.com/in/bryanmurphy2/
• Website: https://www.smartling.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Smartling

Chapters:

00:00 Intro

01:36 Embracing AI at Smartling

02:43 Implementing AI in a Production Environment

07:29 Customer-Centric Innovation

11:01 Understanding Customer Needs

24:25 Balancing Leadership and Involvement

31:37 Weekly Operating Rhythm

33:58 Strategic Planning and Key Initiatives

35:43 Balancing Focus and Resources

48:52 The Importance of Mentorship

51:40 Reflecting on Entrepreneurial Journey

54:06 Outro

Thomas also opens up about co-founding two companies with his brother, surviving a major security breach, and how he’s approaching company-building differently this time around.

Takeaways:

• Why Thomas Is Bootstrapping This Time: After raising $175 million for OneLogin, Thomas opted to bootstrap Bunny, focusing on control and long-term product quality. He discusses how this choice affects hiring, spending, and overall company culture.
• Bringing the Band Back Together: Bunny’s small but mighty team includes engineers from OneLogin. Thomas shares why working with trusted colleagues has helped them execute quickly and avoid early hiring pitfalls.
• The Grind Creates the Bond: Reflecting on the early OneLogin years, Thomas explains how hard work and shared struggle helped forge lasting relationships and why people often want to work with him again.
• Building with His Brother, Again: Thomas co-founded both of his startups with his brother. He explains how they complement each other technically, navigate disagreements, and have grown even closer through the experience.
• Remote from Day One: From commuting weekly between LA and San Francisco during OneLogin’s VC-fueled growth to now working from a boat in the Mediterranean, Thomas discusses why Bunny is remote-first and when in-person still matters.
• Lessons from a Security Breach: A major breach at OneLogin could have destroyed the company. Thomas details how transparency and direct communication with customers helped them retain trust and bounce back.

Quote of the Show:

• "It’s really hard to get a design partner… I wish every Saas or every startup could find a customer like that." - Thomas Pedersen

Links:

• LinkedIn: https://www.linkedin.com/in/tbpeder
• Website: https://bunny.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #bunny

Chapters:

00:00 Intro

01:32 Building Bunny: Lessons from OneLogin

02:39 Team Dynamics and Hiring Strategies

05:59 Working with Family: A Brother's Partnership

10:55 Remote Work and Company Culture

16:40 Bootstrapping vs. Venture Capital

23:37 Marketing and Personal Branding

28:46 Passion for Solving Business Problems

31:21 The Importance of Solving Business Problems

31:38 Challenges and Solutions in Billing

33:24 Early Days of OneLogin

33:40 Building SAML Integrations

36:20 Acquiring First Customers for Bunny

37:35 The Role of Design Partners

41:28 Handling Security Breaches

45:04 Transparency and Customer Trust

48:09 Future of Bunny

50:46 Entrepreneurial Journey and Background

54:45 Mentorship

59:13 Advice to His Younger Self

01:03:04 Outro

With over 25 years in the industry, Burton details his approach to leadership since becoming CEO of commercetools in 2024. He emphasizes the paramount importance of maintaining customer focus, building strong team culture, and aligning company goals. 

Takeaways:

• Understanding Customer Needs: Andrew highlights the importance of stepping into customers' shoes to understand their challenges and measure success through their lens. He emphasizes starting conversations by asking customers about their challenges and how they define success.
• Aligning Around an Ideal Customer Profile: A crucial step Andrew implemented at commercetools was refining their Ideal Customer Profile (ICP). He stresses the necessity of focusing on where the company can deliver the most significant value and understanding why they're uniquely positioned to serve that particular segment.
• The Role of Leadership in Team Development: Andrew believes in playing as one team and ensuring a unified direction across the organization. He discusses the importance of testing for cultural and operational inconsistencies as a new CEO and aligning the team around shared objectives and metrics. 
• Strategic Planning and Adapting to Change: Andrew shares insights into effective strategic planning by decoupling it from the stress of annual closing and starting a new fiscal year.
• Curiosity as a Driver for Success: Andrew describes how a curious approach to understanding problems and developing solutions leads to personal and organizational growth, making it a critical quality he looks for when hiring team members.
• Balancing Passion and Work-Life Integration: Andrew touches on the concept of work-life balance, suggesting that it is deeply connected to one's passion and motivation. He encourages individuals to be mindful of what genuinely drives them and to regularly assess whether their professional and personal lives are aligned with these motivations.
• Mentorship and Learning from Diverse Experiences: Andrew reflects on his journey and the importance of mentorship, emphasizing that learning from a variety of experiences and colleagues, regardless of hierarchy, contributes to a well-rounded leadership style.

Quote of the Show:

• "Anybody that's really, I would argue successful… in their space, is going to know or have an appreciation for, at the core, the customer." - Andrew Burton

Links:

• LinkedIn: https://www.linkedin.com/in/burtonandrew/
• Website: https://commercetools.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #commercetools

Chapters:

00:00 Intro

01:58 The Importance of Customer-Centric Leadership

04:21 Engaging with Customers: Strategies and Insights

09:36 Aligning Company Mission and Team Goals

13:10 Defining the Ideal Customer Profile (ICP)

17:50 Building Trust and Credibility as a New CEO

23:15 Strategic Planning and Measuring Success

31:50 Monthly Cadence and Operational Efficiency

33:05 Reflections on Planning and Offsite Meetings

34:50 Journey to Becoming a CEO

35:58 Curiosity and Leadership

43:44 Mentorship and Influences

46:24 Hiring and Growth Mindset

51:43 Future of Commerce Tools

53:36 Personal Background and Motivation

56:59 Work-Life Balance and Career Advice

01:01:48 Outro

She talks about building strong cultures, nurturing early career talent, supporting women in tech, and helping startups avoid hype in favor of real-world value. From lunch-and-learns to boardroom decisions, Ellen reflects on what it takes to grow people and companies with clarity and purpose.

Takeaways:

• How to Spot Future Founders Inside Your Company: By encouraging curiosity and inviting team members into strategic conversations, Ellen helped cultivate talent that would eventually become leaders. She looked for people who asked questions, engaged outside their lane, and showed deep interest in how the business works.
• Practical Support for Women in Tech: Ellen shares her multi-layered approach to supporting women in technology. She has a personal policy of responding to every outreach from a woman Founder or aspiring leader, offering both encouragement and actionable help.
• Building Strong Local Ecosystems: As a passionate advocate for Boston’s tech scene, Ellen emphasizes the importance of keeping post-exit Founders and big companies engaged with the next generation. She believes physical proximity and local mentorship still matter, even in a hybrid work world.
• The Value of Regular All-Hands and Real Transparency: At her startups, Ellen hosted weekly all-hands to build alignment and trust. She prioritized consistent updates, company-wide visibility into fundraising stages, and direct Q&A with leadership to keep teams connected and focused.
• Lessons from Amazon and the PR/FAQ Method: Ellen talks about her time at Amazon and how the press release and FAQ approach to product planning shaped her thinking. She encourages Founders to use writing and storytelling as a way to clarify product vision before building anything.
• AI That Solves Real Problems: Now an Operating Partner at Glasswing Ventures, Ellen focuses on “intelligent verticals” that use AI to automate industry-specific workflows. She emphasizes the importance of AI being integral to the product, not just a wrapper for marketing.

Quote of the Show:

• "Why wouldn't you wanna be the Founder CEO? That's like the coolest thing in the whole world." - Ellen Rubin

Links:

• LinkedIn: https://www.linkedin.com/in/ellenrubin/
• Website: https://glasswing.vc/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Causely

Chapters:

00:00 Intro

01:45 Key to Startup Success: Building the Right Team

03:08 Exposing Team Members to the Bigger Picture

06:08 Encouraging Curiosity and Engagement

09:45 Supporting Women in Technology

15:03 Challenges in the Tech Industry

17:50 The Boston Tech Ecosystem

21:37 Importance of Local Community in Remote Work Era

27:08 Customer Engagement and Feedback

30:07 Effective Operating Rhythms

35:23 Lessons from Amazon

37:50 Navigating the M&A Process

38:31 Deciding the Right Time to Sell

40:59 Taking Calls from Corporate Development

44:30 The AI Revolution: A 70-Year Overnight Sensation

46:00 The Role of AI in Modern Enterprises

01:01:58 The Importance of Mentorship

01:06:25 Balancing Entrepreneurship and Family

01:09:13 Advice for Aspiring Entrepreneurs

1:10:27 Outro

From taking his first client calls on his cell phone to surviving a last-minute funding failure, Todd speaks openly about scaling, leadership evolution, and what the legal world looks like as regulation and AI collide.

Takeaways:

• Finding the Right Co-Founder in the Hamptons: Todd met his Co-Founder, a former MIT engineer, in the Hamptons. They spent a year working on ideas every Saturday before launching Lawfty, combining Todd’s legal background with Mike’s technical skills.
• Building with Complementary Strengths: Todd surrounded himself with people who could help him see around corners. He emphasizes that knowing your weaknesses and recruiting to fill them is the most impactful thing he's done as a Founder.
• The Power of Shameless Outreach: Todd started the company by emailing every contact in his Gmail account. With no product and no revenue, he relied on personal relationships and a willingness to ask for help to land early clients and supporters.
• Leading with Empathy and Integrity: Todd acknowledges his struggle with letting underperforming team members go, especially when they're good people. Instead of defaulting to layoffs, he focuses on reshuffling and preserving relationships where possible.
• From Answering Phones to Scaling Teams: For over a year, Todd personally fielded every intake call. That hands-on experience shaped how he hires and builds processes today, and made him intimately familiar with every part of the business.
• Navigating Capital Constraints Without Venture Money: Due to legal restrictions, Lawfty couldn’t raise institutional equity. Todd had to get creative with structured finance, high-interest loans from individuals, and careful debt planning to scale the company.
• Legal Tech’s Big Bang Moment: Todd sees the convergence of AI and regulatory change as a generational opportunity for the legal industry. With non-lawyers now allowed to own law firms in more jurisdictions, he believes the space is finally ripe for innovation and scale.

Quote of the Show:

• "Standing up for individuals always felt right to me… so I didn’t necessarily care about the personal view that people had." - Todd Richheimer

Links:

• LinkedIn: https://www.linkedin.com/in/todd-richheimer-esq/
• Website: https://www.lawfty.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Lawfty

Chapters:

00:00 Intro

01:41 The Importance of Complementary Skill Sets

02:41 Finding a Co-Founder in an Unlikely Place

03:44 Building Lawfty: From Idea to Execution

06:19 Challenges and Strategies in Team Building

09:29 Navigating the Interview Process

12:47 Understanding Lawfty’s Business Model

16:26 Early Customer Acquisition Tactics

20:57 Fundraising Journey and Lessons Learned

26:38 Scaling as a CEO

29:31 The Legal Tech Revolution

32:09 Challenges in Legal Services

34:52 Building a Tech-Enabled Law Firm

37:14 Overcoming Industry Stigma

42:35 Fundraising Challenges and Solutions

47:01 Personal Journey and Entrepreneurial Drive

54:12 Advice for Aspiring Entrepreneurs

56:48 Outro

Michael talks about building strong boards and leadership teams, the balance between confidence and humility, and how to create connection in a hybrid work world. With decades of experience in humanitarian leadership, he reflects on his journey from journalist to President & CEO, and how staying close to mission and people shapes lasting impact.

Find Michael's Newsletter here: https://www.linkedin.com/newsletters/relentless-6990692731056488449/

Takeaways:

• Rebuilding the Board and Leadership Team: Michael explains how reshaping governance and leadership early in his tenure has been crucial to the success of every organization he has led. He emphasizes getting the right people in place who share the mission and bring diverse skills and chemistry to the table.
• Evolution Over Revolution: Describing his leadership approach, Michael shares his belief in "relentless incrementalism." He believes consistent, thoughtful progress is more sustainable than sweeping change and that small steps taken regularly are key to building lasting impact.
• Starting a CEO Role in a Global Pandemic: Michael began his job just as COVID shut the world down. He relied on daily video updates, creative communication, and a golden retriever named Izzy to build relationships remotely. He reflects on the benefits and drawbacks of trying to lead without in-person interaction.
• Creating Culture in a Hybrid Workplace: UNICEF USA has embraced hybrid work, but Michael is intentional about maintaining connection. From monthly staff engagement days to leadership meetings and all-staff retreats, he builds structured moments for human interaction and relationship-building.
• Honest Career Advice for Aspiring Humanitarians: Michael stresses that global development is a profession, not just a passion. He shares how expertise, formal experience, and training are key to entering the nonprofit space and why it is important to respect the rigor of humanitarian work.
• CEO Roundtables and Mentorship by Listening: Michael hosts monthly roundtables with staff based on anniversary dates, offering space for Q&A and storytelling. He also invited youth leaders to mentor him, flipping the script to show respect and learn from the next generation of changemakers.
• Balancing Confidence and Humility: Michael reflects on the need to balance strong leadership with the humility to listen. Early in his career, he sometimes over-relied on consensus. Today, he sees the value in trusting instincts while remaining open.

Quote of the Show:

• "When you find what you're supposed to do, doors start opening." - Michael Nyenhuis

Links:

• LinkedIn: https://www.linkedin.com/in/michaelnyenhuis/
• Website: https://www.unicefusa.org/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #UNICEFUSA

Chapters:

00:00 Intro

01:28 Key Achievements at UNICEF USA

03:18 Building Effective Leadership Teams

14:13 Navigating Challenges During the Pandemic

20:14 Remote and Hybrid Work Dynamics

29:31 CEO Round Table and Onboarding

30:48 Operating Rhythm and Annual Planning

32:18 Monthly Staff Meetings and Engagement

36:22 Public Speaking and Media Training

39:55 Managing Diverse Constituents

42:36 Biggest Challenge: Leading Through COVID-19

45:16 Career Journey and Journalism Background

51:47 Mentorship and Youth Engagement

54:32 Balancing Confidence and Humility in Leadership

58:03 Outro

In this candid conversation, Tien reflects on early team building, founder growth inflection points, strategic planning, and the leadership gaps many founders face as their companies mature. Drawing on his new book, Founders Keepers, he reveals why great founders often succeed in spite of themselves—and how to turn blind spots into leadership strengths.

Takeaways:

• Category Creation and Team Building: Tien reflects on the impact of coining the term “subscription economy” and credits early success to not just vision, but team-building. He shares how Zuora evolved through multiple “generations” of leadership, and how long-tenured team members were balanced with fresh perspectives as the company grew.
• Recognizing the Founder’s Growth Curve: Tien describes a critical inflection point when Zuora hit ~150 employees—a moment where personal evolution became necessary. That led him to executive coach Rich Hagberg and a deeper understanding of how personality traits drive both success and failure.
• The Three Pillars of Leadership: Through data-driven leadership profiling, Tien outlines the three dominant founder traits—vision, execution, and relationships. He shares that most founders score high on vision but often struggle with execution and people management, which can lead to common pitfalls.
• Owning Your Leadership Gaps: Tien reveals his own leadership profile—high vision, medium execution, low relationship—and how understanding that helped him improve in areas like prioritization, team-building, and relationship development. He even shared his leadership gaps openly with his company to build trust and culture.
• A Better Way to Do Strategic Planning: Borrowing a method from Brad Smith (former Intuit CEO), Tien walks through how Zuora moved from a 2-day offsite to a 6-month annual strategy cadence. It includes deep research, team ownership of ideas, board engagement, and company-wide evangelism—because a founder’s job is to repeat the story until it sticks.
• Letting Go Without Losing Drive: He emphasizes the importance of giving leaders autonomy and building space into his calendar—cancelling recurring meetings, avoiding over-scheduling, and giving energy to what matters most. He advises founders to avoid being the bottleneck and protect organizational focus by saying “no” to distractions.

Quote of the Show:

• "The same things that make up a founder, that make us do what we do, ultimately are the seeds sewn of our own destruction." - Tien Tzuo

Links:

• LinkedIn: https://www.linkedin.com/in/tientzuo/
• Website: https://www.zuora.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Zuora

Chapters:

00:00 Intro

02:00 The Journey of Building Zuora

03:59 Scaling and Team Dynamics

07:43 Founder's Journey and Coaching

22:12 Strategic Planning and Execution

30:28 Frameworks for Strategic Alignment

32:33 Self-Awareness and Leadership

34:10 Execution-Oriented Teams

37:03 Lessons from Salesforce

38:07 The Power of Storytelling

40:59 Advice on Managing Time

43:33 Biggest Challenges and Overcoming Them

46:24 Future Vision for Zuora

48:22 Personal Journey and Motivation

52:33 Advice for Aspiring Founders

54:13 Outro

Dane offers his personal insights on various topics, from overcoming personal challenges like dyslexia and ADHD to managing growth, profitability, and navigating a shifting economic climate. He reflects on the importance of mentorship, community, and the role of personal growth in leadership.

Takeaways:

• Building a Purpose-Driven Business: Odeko is driven by a mission to support small businesses in a business landscape dominated by large corporations. He notes a growing societal trend shifting away from large chains and towards locally owned businesses.

• Growth vs. Profitability: There is a dynamic tension between growth and profitability when it comes to startups. Startups often experience pressure to grow rapidly at the expense of profitability. As a company matures the pressure shifts to become profitable rather than grow, as sustainability becomes more important. 

• Navigating Entrepreneurship with Disabilities: Dane reflects on his personal struggles with dyslexia and ADHD throughout his entrepreneurial journey. He chooses to see them not as obstacles in his way, but unique traits that help fuel his entrepreneurial spirit.

• The Role of Mentorship in Growth: Dane credits much of his business success to the mentorship he received early on in his career, especially to those that were willing to share knowledge and help guide him through complex decisions.

• Community and Shared Success: As entrepreneurs, it is vital to support and learn from one another, as well as celebrate the successes of others. Founders should reach out to connect with other founders who have had startups and learn from their experiences.

Quote of the Show:

• “I think founders so often get stuck on the idea that I have to have the perfect idea… and that's an incredibly hard criteria to get to without data coming back.” - Dane Atkinson

Links:

• LinkedIn: https://www.linkedin.com/in/daneatkinson/
• Website: https://odeko.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Odeko

In this episode, Nick shares his experiences, the importance of selecting the right co-founder, and the challenges of pivoting a business. He also talks about the emotional toll of shutting down a company and the subsequent launch of his Substack, 'Failing Forward,' where he aims to educate and support other founders through his lessons learned.

Takeaways:

• Building a Strong Team: As a founder, it’s important to know what you’re good at and be honest about what you’re not. Take your time to find the right person, and don’t skip the reference checks. They can really pay off in the long run.
• Founder Compatibility: Choosing a co-founder or core team member is a lot like entering a relationship. It’s more than just an employer-employee relationship. You need to think about personality fit and how your working styles mesh.
• Engaging Customers Early: Start talking to potential customers as early as possible—whether through interviews or feedback sessions. This helps validate your idea and gives you insights into what customers really need. Building early relationships with design partners can also help shape your product development.
• Mental Readiness and Resilience: Being a founder can be mentally tough. There will be stress, setbacks, and tough days— that’s just part of the journey. Having a clear sense of purpose and a strong support system can help you push through the challenges.
• Transparency in Failures: Don’t shy away from sharing your failures. Almost every startup faces obstacles, and being open about them can teach valuable lessons to others. Sharing these stories fosters a culture where failure is seen as part of the learning process, not something to hide.

Quote of the Show:

• “If you're hesitant to pivot, you probably have false positives that you might be pointing to that might be holding you back, but I do think there's another part to it which is the sunk-cost fallacy.” - Nick Freund

Links:

• LinkedIn: https://www.linkedin.com/in/nick-from-workstream/ 
• Website: https://substack.com/@nicholasfreund 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #FailingForward

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #AugustCEOPulse

Chapters:

00:00 Intro

02:55 Hiring Your Founding EA

13:08 Fundraising Isn’t Fair

18:55 The Importance of Origin Stories

23:55 Outro

Despite challenges in managing teams across different geographies and cultures, he highlights the value of tying an organization’s growth to major cloud platforms like AWS, Salesforce, and Snowflake. Eran further discusses the influences of his mentors, particularly his father, in shaping his business approach, and reflects on balancing his professional ambitions with family life. Looking ahead, he is excited about expanding AllCloud's geographic footprint and ecosystem partnerships, aiming to disrupt the market dominated by large system integrators.

Takeaways:

• Emphasize Transparency with Your Team: Being transparent with your team can greatly enhance trust and alignment within your organization. Sharing both good and bad news openly fosters a sense of unity and collaboration.
• Bridge Cultural Differences: When managing a global organization, it’s crucial to understand and address cultural differences. Conducting exercises and coaching sessions can help leaders appreciate these nuances, improving communication and cooperation among diverse teams.
• Champion Persistence and Follow-Through: Consistency in communication and follow-through is key to building trust and reliability. Make sure everyone in the organization feels supported, and always honor your commitments.
• Adapt Leadership Styles to Circumstances: Be flexible in your leadership approach based on your team’s needs. Understanding and adjusting to different working styles can help maintain high performance and alignment.
• Effective Time Management Across Time Zones: Managing a global workforce means balancing time zone differences. Creating a structure that allows for key tasks to be shifted across regions can ensure continuity and operational effectiveness.
• Embrace and Address Challenges Directly: Whether facing startup challenges or multi-geographical operations, tackle issues head-on with strategic planning and strong leadership to drive the organization forward.
• Continuous Learning and Mentorship: Actively seek mentorship and learn from every leadership experience. Embracing lessons from mentors can significantly enhance your management style and adaptability.

Quote of the Show:

• “It's how you communicate with each other. Are you more hard charging or less? Is there a work life balance or not?” - Eran Gil

Links:

• LinkedIn: https://www.linkedin.com/in/erangil/ 
• Website: https://allcloud.io/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #AllCloud

He emphasizes the value in communication, transparency, and flexible leadership. Craig reflects on strategically selecting investors and how product acquisitions led to rapid growth for Dialpad. He also shares his thoughts on maintaining a balance between work, family, and personal growth, underscoring the critical role of adaptability and team dynamics in achieving success.

Takeaways:

• Jump Right In: Craig emphasizes the importance of diving into challenges directly, sharing his journey of building, getting acquired, and going on his own to continue building within the business communications industry. 
• Ups and Downs of Success: Any successful company has periods of growth and decline when you look under a microscope. Try to focus on the bigger picture when things get difficult. 
• Communicate Often: Craig emphasizes the significance of overcommunication for transparency and maintaining a strong company culture. It is important to keep everyone in the organization up to date on information, even if it isn’t positive.
• Focus on Direction, Not Speed: Strategic vision is crucial, and businesses need to select the right investors who share the long-term growth perspective. This ensures a long-term and beneficial partnership as you grow.
• Make it Delightful: Consumers should not have to trudge through a dull experience. Ensuring there are opportunities for delight helps keep user experiences positive and increases retention.

Quote of the Show:

• “ Just because it's a business B2B service, it can't have moments of delight? Like that's crazy. Of course it can.” - Craig Walker

Links:

• LinkedIn: https://www.linkedin.com/in/cwalker123/
• Twitter: https://x.com/cwalker123
• Website: https://www.dialpad.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Dialpad

Join us as Ryan emphasizes the importance of interviewing for core values, maintaining consistency in a high-growth environment, and promoting from within to nurture company culture. We also explore strategic vision, board dynamics, and the role of outsourcing in today’s workplaces. With reflections on his entrepreneurial influences and insights on leadership and parenting, Ryan offers valuable lessons for achieving long-term success and a hopeful outlook for the future. Don't miss this compelling conversation!

Takeaways:

• Interviewing for Values: Evaluate candidates for alignment with your core values, using open-ended questions that reveal character and resilience.
• Consistency Across Locations: Maintain consistent service and quality across locations to build customer trust and satisfaction, focusing on training and improvement.
• Adapt and Stay Resilient: Stay adaptable and resilient during crises by maintaining hope, making quick decisions, and staying true to your core values.
• Develop a Farm System: Promote from within to create a strong executive team by nurturing young talent and providing leadership opportunities.
• Effective Board Management: Keep the board small for quicker decision-making and ensure regular communication through transparency.
• Work-Life Integration: Involve your family in the business to instill a strong work ethic and understanding of the business world from an early age.

Quote of the Show:

• “Everything's a trust trade… and part of my trust in you is that you can manage my expectations up or down, but please just don't surprise me.” - Ryan Simonetti

Links:

• LinkedIn: https://www.linkedin.com/in/ryan-simonetti-5873887/
• Twitter: https://x.com/rwsimonetti
• Website: https://convene.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Convene

Nathan discusses the challenges he encountered, from navigating significant operational shifts during the pandemic to adapting business models and managing rapid growth. He emphasizes the importance of detail-oriented leadership, building empathy within teams, and how constraints can foster innovation. Additionally, Nathan highlights the value of continuous learning, the benefits of an executive coach, and the importance of a clear company identity when seeking investment.

Takeaways:

• Know Your Business Inside and Out: Understanding every detail of your business fosters empathy and credibility, making it easier to connect with and lead your team effectively.
• Be Ready to Adapt Your Business Model: When faced with challenges like the pandemic, pivoting from a market-by-market rollout to a platform model that integrates local operators was key to Crafty’s survival and growth.
• Build Strong Client Relationships: Nurturing close relationships with clients, even as the company scales, provides valuable insights and fosters trust and loyalty.
• Choose the Right Investors: It’s crucial to find investors who truly understand and align with your business model, rather than redefining your pitch for each and every investor. Being genuine to potential investors may not win them all, but it will help you get investors that truly understand your goals.
• Embrace Constraints: Embracing constraints can drive innovation and sharpen focus. Working with limited resources often leads to more efficient and effective outcomes, rather than spreading too thin with excess resources.

Quote of the Show:

• “If you're trying to bend your business to fit what an investor wants, that's a really slippery slope.” - Nathan Rosenstock 

Links:

• LinkedIn: https://www.linkedin.com/in/nathan-rosenstock/ 
• Website: https://craftydelivers.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Crafty

Daniel shares insights on structured hiring, the importance of early-stage learning, navigating investor challenges, and how leadership evolves as a company scales.

Takeaways:

• Defining a Clear Mission from the Start: Many hiring platforms focused on reducing administrative burden, but Greenhouse took a different approach. Daniel explains how taking the time to clarify their mission—helping companies become great at hiring—set them apart and shaped their long-term success.
• Creative Validation Before Building: Before launching Greenhouse, Daniel and his co-founder tested their hiring methodology through in-person workshops, using index cards to help companies structure their hiring processes. This early validation gave them confidence in their approach.
• Navigating the Venture Capital Journey: Fundraising wasn’t easy—Daniel and his co-founder struggled to secure their initial capital. He shares how they ultimately raised money, the challenges of pitching to 60+ investors, and why persistence is key in venture-backed startups.
• The Art of Hiring & Performance Management: Daniel reveals why great hiring is one of the most powerful management tools. He discusses how strong recruiting processes make it easier for leaders to build high-performing teams and remove underperformers without fear.
• The Evolution of CEO Responsibilities: As Greenhouse grew from a small startup to a global business with over $200 million in revenue, Daniel’s role shifted. He shares how he balances strategy, communication, and hands-on involvement to drive success at scale.
• Lessons from Tough Times: The COVID-19 pandemic forced Greenhouse to rapidly adapt as hiring slowed across industries. Daniel reflects on how they navigated uncertainty, supported customers, and came out stronger on the other side.

Quote of the Show:

• “ I'm like a bazooka… it's not the right tool for every job… but there’s some problems that only a bazooka can solve.” - Daniel Chait

Links:

• LinkedIn: https://www.linkedin.com/in/dhchait/
• Company Website: https://www.greenhouse.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Greenhouse

Chapters:

0:00 Intro

1:28 What You’d Do Again As CEO

3:10 Validating the Business Idea

5:37 The Role of Structured Hiring

12:41 Hiring Strategies and Challenges

22:54 Scaling and Leadership Evolution

25:35 Effective Communication as a CEO

30:25 Adapting Company Meetings

33:56 Raising Early Stage Investments

37:42 Strategizing for Series A and Beyond

43:17 Building a Tech Business in Early New York

49:54 Biggest Challenges Faced

52:52 Remote Work and Future Vision

58:44 Daniel’s Background

1:06:40 Advice to Younger Self

1:08:49 Outro

Kyle shares how "love" became the core principle guiding Salesloft’s culture, leadership, and customer relationships. He also dives into early sales strategies, navigating fierce competition, securing top-tier investors, and the creative marketing tactics that helped Salesloft stand out.

Takeaways:

• Leading with Love: Kyle attributes Salesloft’s success to a deep love for employees, customers, and the sales profession. This mission-driven approach helped attract top talent and build a strong company culture.
• Building Organizational Health: Salesloft focused on creating a high-performance team on an ambitious mission. Kyle explains why prioritizing leadership development and a values-driven culture was critical to scaling the business.
• The Dreamforce Marketing Stunt: Salesloft hired a lookalike to impersonate Salesforce CEO Marc Benioff at Dreamforce, creating buzz and attention. Kyle shares how creative, unconventional marketing helped Salesloft stand out in a crowded industry.
• Navigating Competition & Outlasting Rivals: Competing against well-funded competitors, Salesloft took the long-term approach of outlasting others through superior execution, customer focus, and efficient growth.
• Hiring & Scaling a Leadership Team: Kyle details how he recruited top-tier executives by positioning Salesloft as a company where leaders could make an impact. He also shares how he handled the difficult reality of outgrowing early hires as the company scaled.
• Fundraising & Picking the Right Investors: Kyle prioritized investors who would push him to think bigger and make the company better. He shares lessons from working with top firms like Emergence Capital and Insight Partners, as well as the negotiation tactics that helped him secure better deal terms.
• Stepping Down as CEO & The Next Chapter: After leading Salesloft to a successful acquisition, Kyle made the decision to step down as CEO. He discusses his motivations for transitioning out of the role and how he’s now focusing on supporting his wife's dream of revitalizing Florida’s citrus industry.

Quote of the Show:

• “ Step on the gas and learn faster than the rate of your own experience so that you can maintain your position on the mission.” - Kyle Porter

Links:

• LinkedIn: https://www.linkedin.com/in/kyleporter/
• Twitter (X): https://x.com/kyleporter
• Company Website: https://www.salesloft.com/
  
  

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

For more CEO content, uncut stories, and CEO guides, visit our substack at https://notanotherceo.substack.com/ 

#NotAnotherCEO #BusinessSuccess #Salesloft

Chapters:

0:00 Intro

3:12 What You’d Do Again As CEO

10:26 Creative Marketing at Dreamforce

17:18 Scaling the Executive Team

20:41 Navigating Investor Relationships

29:54 Building a Tech Ecosystem in Atlanta

34:51 Facing Fierce Competition

38:35 The Role of Authenticity in Business

41:07 AI's Impact on Sales

44:04 Stepping Down as CEO

49:19 Biggest Challenges Faced

55:23 Kyle’s Background

1:00:49 Life After Salesloft

1:06:02 Advice to Younger Self

1:07:39 Outro

Zac discusses the importance of structured execution, hiring for passion, and balancing long-term vision with short-term execution. Whether you're a founder, leader, or aspiring entrepreneur, this conversation is packed with valuable insights on leadership, company building, and decision-making.

Takeaways:

• The Power of a 10-Year Vision: Zac believes that thinking long-term is critical for building meaningful businesses. He explains how setting a bold 10-year goal helps guide decision-making and prioritization in the short term.
• Entrepreneurial Operating System (EOS) for Success: One of Zac’s most impactful lessons was implementing EOS to create structure and accountability within his companies. He shares how this system helped him move from gut-driven decisions to a scalable business framework.
• Execution is the Differentiator: Most companies operate at a 3 or 4 out of 10 in execution. Zac explains how simply executing at a 7 or 8 puts businesses ahead of the competition and increases the likelihood of success.
• Hiring for Passion & Curiosity: Beyond skills, Zac prioritizes candidates who show genuine interest and curiosity. He shares how small actions, like trying a product before an interview, can reveal whether someone is truly invested in a company’s mission.
• Lessons from Leading Through Crisis: From navigating financial challenges to making tough leadership decisions, Zac reflects on some of the hardest moments of his career, including when he and his co-founder decided to replace themselves as leaders to save the company.
• Building a Personal Brand in B2B Sales: In enterprise sales, people buy from people, not just companies. Zac shares how investing in personal brand-building—through speaking, blogging, and community engagement—was key to winning customers at Packet.

Quote of the Show:

• “ I don’t need to run a 10 out of 10 for a company. Most companies are operating at a 3 or a 4. I just want to be a 7 or an 8.” - Zac Smith

Links:

• LinkedIn: https://www.linkedin.com/in/zsmith

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Packet

Chapters:

0:00 Intro

1:25 What You’d Do Again As CEO

3:18 Deep Dive into EOS and Its Benefits

7:41 Building a Passionate and Accountable Team

9:50 The Importance of Vision and Long-Term Goals

13:20 Effective Interview Techniques and Identifying Passion

19:57 Communicating Vision and Values

29:33 Go-to-Market Strategies and Early Customer Acquisition

34:38 Early Users and Initial Challenges

39:22 New York Tech Scene Evolution

45:25 Biggest Challenge Faced

51:41 Rich’s Background

1:05:49 Advice to Younger Self

1:02:21 Outro

Lau shares his journey from an engineer in startups to a CEO managing a high-growth company. He provides insights on aligning leadership and culture, fundraising, and work-life balance.

Takeaways:

• Co-Founder Alignment: The Jellyfish team created a detailed vision for Jellyfish before starting the company. They established core values that emphasized culture, people, and building a scalable business. This became their North Star for decision-making.
• Engineering for Growth: Jellyfish's platform helps engineering leaders align their teams’ work with broader business objectives. The company's vision is inspired by Salesforce’s transformation of sales management.
• Early Customers through Discovery: The team interviewed over 50 VPEs and CTOs to deeply understand pain points in engineering management. These conversations led to a service-driven approach to validate Jellyfish’s product vision.
• Startup for Grown-Ups: There was a conscious effort to build a "grown-up" startup that accommodates life responsibilities. They designed their business to work with their life stages, creating a sustainable culture.
• Leadership Evolution: Andrew reflects on his transition from engineering management to being a CEO. This journey required learning sales, fundraising, and storytelling while balancing the operational and strategic demands of scaling a company.
• Fundraising with Trust: Andrew describes the importance of aligning with investors who understand the domain and trust the founding team. Jellyfish's seed funding came from building relationships within the Venn diagram of trust and domain expertise.
• Adapting to Change: As the tech landscape evolves with AI and macroeconomic shifts, Jellyfish focuses on being adaptable. Andrew emphasizes that startups have the agility to tackle new challenges, creating opportunities for growth and innovation.

Quote of the Show:

• “It’s a marathon, it’s not a sprint. And we also live lives as humans here too… We have to make this thing work for us.” - Andrew Lau

Links:

• LinkedIn: https://www.linkedin.com/in/amlau/  
• Twitter: https://x.com/amlau  
• Website: https://jellyfish.co/  

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Jellyfish

Takeaways: 

• The Compound Startup Strategy: David Karandish introduces the concept of a "compound startup," a term coined by Parker Conrad that he has effectively applied at Capacity. The premise revolves around integrating various point solutions into a cohesive platform, reducing costs while maximizing the bundle's value.
• Navigating Mergers and Acquisitions: Handling 14 company acquisitions in just three years, David shares his approach to successful mergers. He emphasizes the importance of each acquisition fitting into the broader company mission, fostering synergy rather than assembling a mere collection of brands.
• Building Machines in Business Processes: David advocates for creating “machines,” repeatable processes that enhance efficiency and scalability within an organization. 
• Impact of AI on Business Operations: The discussion highlights the evolving landscape of AI solutions. While initial efforts centered around point solutions, the trend is shifting towards platform consolidation.
• The Role of Communication Frameworks: David reflects on how establishing a structured cadence for goal setting and meetings has been vital at Capacity, ensuring alignment across 350+ employees worldwide.
  

Quote of the Show:

• “By machine, I don't necessarily mean how you think like a physical idea, but I mean more repeatable processes that scale and remove as much human decision making outta the process as possible." - David Karandish

Links:

• LinkedIn: https://www.linkedin.com/in/davidkarandish/
• Website: https://capacity.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:43 The Concept of a Compound Startup

04:09 Strategic Acquisitions and Integrations

05:41 Challenges and Solutions in M&A

09:24 The AI Revolution and Market Trends

13:01 Implementing EOS and Organizational Frameworks

17:38 Building and Operating Effective Machines

21:12 Hiring for Stage Fit and Problem Solving

27:57 St. Louis Entrepreneurial Scene

33:39 AI and Market Noise

38:53 Big Breaks and Business Models

41:28 Managing Energy and Time

43:34 Balancing Work and Family

47:35 Advice for Aspiring Entrepreneurs

48:31 Outro

Howard shares his leadership journey, lessons on building a culture of innovation, and insights into tackling challenges ranging from product positioning to team dynamics.

Takeaways:

• Weekly Video Messages: Ting introduced five-minute weekly video updates early in his tenure at Cyberhaven. These videos keep teams aligned and foster engagement across the organization, showcasing his commitment to transparent communication.
• Changing from the Start: Upon joining, Ting made sweeping changes to product strategy, positioning, team structure, and culture. This grew the company's ARR by over 120x, positioning it as one of the fastest-growing cybersecurity companies today.
• Focusing on the Ideal Customer Profile: Ting emphasizes the importance of discipline in targeting mid-market companies with high IP turnover rather than pursuing large enterprises prematurely, accelerating product feedback and company learning.
• The Role of Investors: Ting prioritizes working with investors who share his ambition, understand market dynamics, and actively help scale the company through strategic guidance and connections, rather than just governing from the sidelines.
• Hiring for Growth: Ting values self-awareness, vulnerability, and hunger in hires. He digs deep during interviews, exploring candidates’ childhoods and motivations to assess their capacity for growth and alignment with company culture.
• Life Lessons for Career Rhythm: Ting's advice to his younger self includes finding a balance between high-intensity career growth and enjoying the journey. He shares how slowing down at times could have enhanced his personal and professional satisfaction.

Quote of the Show:

• “The people who are self aware and demonstrate enough vulnerability, I think they have the best chance of growing and scaling with the company.” - Howard Ting

Links:

• Personal LinkedIn: https://www.linkedin.com/in/howardting/ 
• Personal Twitter: https://x.com/howardting 
• Company Website: https://www.cyberhaven.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Cyberhaven

He emphasizes understanding customer personas and the importance of one-on-one interactions in driving business success. Ryan also shares his approach to fundraising, building the right team, and navigating the challenges of scaling a business. He advocates for deep customer understanding, sticking to a defined ideal customer profile (ICP), and the strategic use of AI in RevOps.

Takeaways:

• Jump Right In: Don't hesitate to dive into challenges head-on. Taking decisive action is often the first step toward finding effective solutions.
• Identify High-Impact Areas: Focus on areas that have the biggest impact on your organization. It’s important to prioritize tasks and projects that drive the most significant results.
• Value One-on-One Time: Prioritize precious one-on-one time with your team. Personalized attention can foster stronger relationships and address individual needs more effectively.
• Deliver Consistently: Consistent delivery of work and results builds trust and reliability within your team and with stakeholders. Ensuring that you follow through on your commitments is a great way to build loyalty.
• Communicate Often: Regular communication is key. Whether it's calling individual team members or holding regular meetings, keep the lines of communication open to ensure everyone is aligned.
• Focus on Direction, Not Speed: While speed can be important, it's more crucial to ensure that your team is moving in the right direction. Align on goals and ensure everyone is headed toward the same objectives.

Quote of the Show:

• “It's so important that as an entrepreneur, we're humble…And I think a lot of entrepreneurs lose precious years because they don't ask enough questions.” - Ryan Westwood

Links:

• LinkedIn: https://www.linkedin.com/in/ryanwestwood/
• Website: https://www.fullcast.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Fullcast

Kathryn emphasizes the importance of being comfortable with making unpopular decisions and the impact of integrating experienced executives into a growing company. She also delves into her recent adventures in advising companies, investing in Broadway shows, and potentially planning her next entrepreneurial venture.

Takeaways:

• Accept That Not Everyone Will Support Your Choices: As a leader, you may have access to information that others don’t, which can lead to misunderstandings. Focus on acting with integrity and staying true to your values.
• Encourage Open Dialogue but Know When to Decide: Foster a culture where team members feel comfortable expressing dissenting opinions. However, there comes a time when you must make the final decision and stand by it.
• Continuously Reevaluate Leadership Approaches: Regularly assess and refine your leadership strategies. Engage with diverse perspectives through reading, mentoring, or coaching to enrich your approach.
• Adopt a Collaborative Mindset: Effective leadership involves seeking advice and fostering collaboration. Welcoming external insights can enhance your decision-making and strengthen your team’s capabilities. 
• Learn from Setbacks: Challenges and failures can offer valuable lessons. Use feedback from rejections or setbacks to improve your methods and strategies for future success.

Quote of the Show:

• “I think culturally we often still want women to be women. Really caring, really kind, really likable… but I also have to make hard calls to run a business. People punish women more when they perceive those things are in conflict.” - Kathryn Minshew

Links:

• LinkedIn: https://www.linkedin.com/in/kathryn-minshew/ 
• Twitter: https://x.com/kmin
• Website: https://www.kminshew.com/
• Instagram: https://www.instagram.com/kminshew/  

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Michaeli emphasizes the importance of predictable schedules and clear expectations in driving company performance and executing strategic objectives. The discussion also covers his growth as a CEO, his approach to hiring and building an executive team, and lessons learned in sales and disrupting an industry. He shares personal insights on maintaining a learning mindset, staying sane amidst challenges, and the importance of continual adaptation in business.

Takeaways:

• Fostering a Learning Mindset: Embrace a mindset that prioritizes identifying and filling knowledge gaps through diverse resources. Proficiency and situational awareness in various domains can significantly enhance leadership effectiveness.
• Leverage Immediate Application for Learning: Utilize real-time opportunities to apply newly acquired knowledge. This experiential approach reinforces learning and builds proficiency.
• Importance of Executive Search and Hiring Power: Consistently dedicate time and effort to personally source and recruit top talent. Engaging directly with candidates as a CEO can significantly boost response rates and attract high-caliber individuals.
• Adapting and Rebranding for Growth: Be prepared for rebranding as part of your company's evolution. Rebranding, coupled with a strategic refocus and fundraising, can catalyze significant growth and redefine market positioning..
• Communicating and Managing Change: Use established business rhythms to introduce and manage changes. Connecting change to regular and predictable events helps in gaining team buy-in and maintaining organizational agility and clarity.

Quote of the Show:

• “The first step is really understanding what the gaps in your knowledge are, and then it's really driving to plug those gaps as effectively as possible.” - Dan Michaeli

Links:

• LinkedIn: https://www.linkedin.com/in/danielmichaeli
• Website: https://www.glia.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Godard joins host David Politis to discuss his journey building multiple successful businesses. Godard examines the importance of having the right co-founders, the benefits of a dialed-in team, as well as struggles when scaling a business. He delves into fundraising experiences and managing leadership transitions. 
 
Takeaways:

• The importance of trusted co-founders. Having co-founders that are equally committed to bringing the company vision to life helped motivate Godard to continue with G2’s mission.
• Getting off the ground with reviews. After putting out G2’s alpha, Godard relied on receiving reviews at events like Dreamforce. They eventually started putting QR codes at the end of keynotes and handing out hoodies to gain thousands of new reviews. 
• Struggles with Silicon Valley. G2 struggled to gain investors initially, unsuccessfully pitching themselves to investors in California. It wasn’t until they focused on local Chicago opportunities that significant investments were made into G2.
• Indirectly flooding Accel. Entrepreneur’s pitch Accel for fundraising started including G2 Grids in their decks en masse. This constant visibility got Accel to see the value in G2 and brought Godard back from Salesforce to scale the company. 
• Giving executives space to operate. While he still has consistent communication and 1 on 1s, Godard is a firm believer of giving executives freedom and responsibility within their roles.
• Patience when hiring executives. David and Godard agree that rushing an executive hiring process is one of the easiest ways to hire the wrong person. Taking the time to find the right match, even if you have to wait for an individual, is worth the time.

Quote of the Show:

• “I'm not like imposing my operating ideas on them, but I wait for them to come and ask.  And then I try to be a good advisor, you know, but I let that be they pull… versus me pushing.” - Godard Abel

Links:

• Twitter: https://x.com/godardabel
• LinkedIn: https://www.linkedin.com/in/godardabel/
• Website: https://www.g2.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Jukay joins host David Politis to discuss his journey helping people get jobs in tech. Jukay examines the importance of having a mission-driven team, the challenges of going remote, and the importance of communal activity. He delves into adapting to change and how he sees AI affecting the workplace. 

Takeaways:

• Helping people earn more. Pursuit's fellowship program helps individuals transition from low-wage jobs to successful careers in tech, increasing the average income of their fellows from $18,000 before Pursuit to over $90,000 at their first job after Pursuit. 
• The impact of a mission-driven team. Pursuit’s mission is not one that can be achieved easily. Finding and hiring team members that share the same mission as Jukay helps keep his employees motivated and makes the payoff after successes even greater for all involved.
• Ease and struggles of going remote. While many were able to easily transition into a remote environment during Covid-19, some fellows asked to remain in person as they do not have the ability to continue from home. Jukay highlights how important it is to understand how much access to technology their community has outside of Pursuit.
• Technology changing industries. Jukay saw how technology was actively changing industries all over. He chose to focus his business on technology in order to make as big of an impact as he could.
• The need to veto experts as CEO. CEOs will often get guidance or opinions from many stakeholders before making decisions. It is important to remember that a stakeholder’s expertise in one field won’t always translate to a similar field or situation.
• People and AI. Jukay shares his thoughts on AI being introduced into the workplace. He points out that AI is just a tool and that people skills and problem solving in a business setting will be necessary no matter how much technology changes.

Quote of the Show:

• “It doesn't feel like work. It just feels like things I'm interested in and care about, and solving things.” - Jukay Hsu

Links:

• Twitter: https://x.com/jukayhsu 
• LinkedIn: https://www.linkedin.com/in/jukay/
• Website: https://www.pursuit.org/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Jeron joins host David Politis to discuss his extensive career, including selling his latest company to Salesforce. Jeron examines the importance of assembling a high-quality executive team, the benefits and challenges of using headhunting firms, and the vital role of maintaining close involvement with the product. He delves into the significance of engineers understanding their CEO’s expectations and the advantage of involving investors in key search processes. 

Takeaways:

• Build a strong executive team. It is crucial to have the right people in the right positions at the senior level. Leaders should focus on assembling and nurturing their executive team for overall company success.
• Balance short-term necessity with long-term fit. While it can be tempting to rush hires out of necessity, it’s critical to find the right fit for long-term success. Investing time upfront saves future complications.
• Get deeply involved in product development. Have a hands-on approach in the early stages of product development to ensure that the foundation is robust and scalable. Leaders should understand their products at a deep level to guide their teams effectively.
• Navigate investor and acquirer relationships. Establishing early connections with potential investors and acquirers on your terms can position your company favorably for future exits or acquisitions.
• Understand the importance of a partner in search firms. The success of using a search firm is often attributed more to the individual partner you work with than the firm itself. Leaders should seek firms with robust networks and partners who are highly regarded.
• Ask for personal feedback. Leaders should be prepared for and open to constructive feedback, even when it’s tough. Developing self-awareness and humility is key to personal and professional growth.
• Maintain work-life balance. Despite the challenges, leaders need to strive for a balanced approach to work and family life. Recognizing the need for presence at home can be just as important as business success.

Quote of the Show:

• “Companies can be bought or sold. You want to be bought. You don't want to be sold.” - Jeron Paul

Links:

• Twitter: https://x.com/jerondanielpaul 
• LinkedIn: https://www.linkedin.com/in/jeron-paul-35824/ 
• Website: https://spiff.com/ 

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Loren joins host David Politis to discuss their journey from surviving cancer in her early 20’s to being sold in over 25,000 supermarkets. Loren reflects on how her experiences led her to focus on creating sweets that tasted good, didn’t make you feel bad after eating them, and were available to those with gluten or other food allergies. Discover her insights for creating a strong core product, the importance of product quality, and the tactical brand impact of maintaining high standards.

Takeaways:

• The impact of quality. Sweet Loren’s is an allergen free brand, so mitigating health and safety risks is their top priority. By investing in and maintaining the quality of their allergen free food, they built a trust with their customers.
• Standing out in the crowd. Loren had to stand out among a sea of thousands of competing products. This drove her to focus heavily on conveying her products’ top selling points on their packaging design.
• Make it easy for your customers. Customers in the modern market demand excellence, so it is important to both provide excellence and make it as easy for the customer as possible to implement your product into their lives.
• Importance of standing by your brand. When a supplier sent a large order of contaminated flour, Loren made the decision to not compromise on her brand’s integrity and took a loss for not using any of that contaminated shipment.
• The importance of mentorship. Sweet Loren’s took off from day 1 and she quickly realized how overwhelming it could be. Having business mentors allowed her to be vulnerable about herself and the business and get constructive feedback to boost her confidence.
• Creating a strong core product first. Many in the food industry expand into new items within a few years, but Loren took 9 years to cement herself in the cookie dough market before exploring other product offerings.
• Building a team. Having a second daughter made her realize how important having a capable team around her was. Hiring a president allowed her to focus on what she was good at and step away if needed to without impacting the day to day of the business.

Quote of the Show:

• “Honestly the bigger our customer base gets, the more passion I get about it because the more we have people saying you've changed our lives.” - Loren Castle

Links:

• Twitter: https://x.com/LorenBrill
• LinkedIn: https://www.linkedin.com/in/loren-brill-castle-56887121/
• Website: https://sweetlorens.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

John and Anthony join host David Politis to discuss their journey from storage unit offices to industry leaders. John and Anthony reflect on how their upbringings affected their entrepreneurial mindsets and their struggles to find product market fit. Discover their insights for creating a strong office culture, building and maintaining customer relationships, and the impact of staying bootstrapped throughout their growth.

Takeaways:

• A company’s values evolve as the company continues to develop. You should have your values written down and communicated to everyone, but expect them to change over time. 
• Don’t let rejection slow you down. Instead, use it as motivation to keep going. John and Anthony faced plenty of rejection when starting out, but they persisted and found their place in the market without significant support.
• Bootstrapping provides freedom to grow your company how you want. John and Anthony weren’t able to secure funding, and if given the chance they prefer the freedom that it provided as there are no boards to answer to when making big decisions.
• Having a marathon mindset can be a great help to push through the ups and downs of entrepreneurship. Building a business doesn’t always go exactly how you expect, so focus on your goal’s destination rather than how you get there.
• Making Co-CEOs work isn’t for everyone. While most contemporaries have advised against it, John and Anthony have known each other for decades and were able to split duties while staying aligned on the same overall goal to become successful Co-CEOs.
• When you’re starting out, go the extra mile to build relationships with your clients. Show them you care and that their feedback is valuable, as it can lead to customer loyalty.

Quote of the Show:

• “Great companies have been built without capital, but not without people.” - John Fazzolari
•  “No matter how much we communicate something, we could always communicate more of it.” - Anthony Serina

Links:

• John’s Twitter: http://www.twitter.com/fazz
• Anthony’s Twitter: https://x.com/antserina
• John’s LinkedIn: https://www.linkedin.com/in/john-fazzolari-5b94b62b/
• Anthony’s LinkedIn: https://www.linkedin.com/in/anthony-serina-ba656121/
• Website: https://www.revivn.com/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

Tony joins host David Politis to discuss his journey turning a small managed service business into a freshly acquired top cloud consulting company. Tony reflects on how significant it was to choose a niche early and how it helped fuel his success. Discover his insights for understanding market needs, the benefits of joining YPO, and inspiring the next generation of entrepreneurs.

Takeaways:

• Establishing your business’ niche focus early is important for continued growth. When looking for a market niche, focus on underserved markets and provide a solution for that market that is scalable. 
• Not relying on external funding was a blessing for SADA’s growth as a company. Not being a venture-backed company forced SADA to be more disciplined with managing their portfolio and grow strategically within their market.
• The art of strategic decision making is one that had to be mastered over the years. Being able to identify and say “no” to business streams that spread the company’s focus thin is a major factor in being able to effectively specialize.
• Leaders must evolve with their company. It is crucial to be able to recognize environmental change and be willing to adapt to it. It is equally crucial to actively seek out growth opportunities that allow you to better align your knowledge with the market and clientele that your company is working with. 
• Meet new situations with enthusiasm. SADA’s acquisition by Insight marks a transition from operating as a private company to operating as a public company. It is important to be excited about the challenges and use them as growth opportunities. 
• A company’s early success can largely be attributed to the dedication of its employees and the culture that they work in. Focusing on hiring driven employees over experienced employees allowed them to grow with the company and become the experts that SADA needed. 

Quote of the Show:

• “Nothing is as bad as it seems and nothing is as good as it seems. So just make the most of every day.” - Tony Safoian

Links:

• LinkedIn: https://www.linkedin.com/in/safoian/
• Website: https://sada.com

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

In this episode, Artem Rodichev shares the gritty, unfiltered story of Ex Human’s near-death year. Instead of shutting the company down, that year hardened the team, shaped the culture, and created a level of resilience that became Ex Human’s defining advantage.

Now Ex Human is profitable and building empathetic AI characters capable of multimodal emotional intelligence, technology designed to see, hear, and feel in ways that help combat loneliness. Artem also discusses his path from leading AI at Replica to building a company that spans both consumer and enterprise markets, powered by millions of user-created AI characters that generate a unique data advantage. 

Takeaways:

• Persistent Belief in Your Vision: Artem emphasized the importance of having unwavering belief in your mission. His steadfast belief in the potential of AI to create meaningful human interactions kept him going through challenging times.
• Foster a Culture of Resourcefulness and Persistence: The trials that Ex Human endured became pivotal learning experiences, instilling a culture of resourcefulness and persistence within the team. 
• Be Prepared for Sacrifices: Artem candidly discussed the personal sacrifices he made, including taking a salary below market rate and making hard personnel decisions. 
• Expand Beyond Comfort Zones: Despite an engineering background, Artem knew he needed to step out of his comfort zone and learn essential skills like marketing and sales to lead Ex Human effectively.
• Data-Driven Innovation: Ex Human’s success hinges on continuously refining their AI models with data collected from their consumer app. This iterative approach allows them to stay ahead in the competitive AI market.
• Transitioning from a Stable Job to Entrepreneurship: Artem’s move from a significant role at Replica to founding his startup showcases the courage needed to leave stability behind in pursuit of a bigger vision.

Quote of the Show:

• “Every month I thought I should give up. But then the other side of me said, if you give up now, you’ll never build the future you believe in." - Artem Rodichev

Links:

• LinkedIn: https://www.linkedin.com/in/art-rodichev/ 
• Website: https://exh.ai/#home 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #ExHuman

Chapters:

00:00 Intro

01:24 The Importance of Persistence

04:33 Belief in the Vision

05:53 Personal Sacrifices and Company Culture

11:07 Solo Founder Challenges

12:29 Building a Strong Team

14:45 The Role of a Founder

18:47 Consumer AI and Empathetic Companions

29:41 Breaking Inertia: Leaving a Successful Company

32:06 Limitations and New Opportunities: The Birth of a New Venture

34:50 B2C and B2B: Balancing Two Markets

37:11 The Importance of Data in AI Development

42:28 Challenges and Competitions in the AI Market

49:41 Personal Background: From Kazakhstan to Tech Entrepreneurship

57:00 Final Reflections and Advice for Aspiring Entrepreneurs

58:39 Outro

In this episode, Shensi Ding, Co-Founder and CEO of Merge, shares her journey from investment banking to leading one of the most successful integration infrastructure companies in the market. She opens up about the company’s evolution, from a small startup in San Francisco to a category leader powering technology products and AI agents for companies like Ramp and OpenAI.

Shensi also discusses how she built Merge’s in-person culture during the height of the pandemic, what it takes to recruit top talent, and the lessons she’s learned about decision-making, adaptability, and sustaining momentum as a founder. 

Takeaways: 

• The Importance of Company Culture: Shensi emphasizes the significance of maintaining an in-person culture at Merge, even amidst the challenging conditions of the COVID-19 pandemic.
• Maintaining Quality Over Competing on Price: Shensi discusses the challenge of maintaining a premium product in an environment saturated with copycats. She was inspired by the CEO of Gong, who reinforced that a company cannot be both the best and the cheapest.
• Navigating Growth and Innovation: An integral part of Merge's ethos has been to constantly innovate and adapt, which Shensi highlights by discussing the launch of new products and their strategic shifts towards AI-driven solutions.
• Integration and Expansion as Key Growth Drivers: Shensi highlights the significance of diversifying Merge’s product offerings and expanding into new markets to drive growth. By strategically adding categories and aiming for enterprise-level clients, Merge has expanded its market reach and increased its potential for acquiring larger clients.
• Lessons in Leadership and Adaptability: David and Shensi discuss the value of learning from industry veterans and mentors, which Merge facilitates by inviting successful leaders to speak with their team.
• Navigating Fundraising and Investor Relations: In discussing fundraising experiences, Shensi highlights the importance of clear differentiation and conveying the unique value of your product to investors. While the initial seed round was challenging, securing well-known investors early on eased future fundraising efforts.

Quote of the Show:

• “You can’t be the best and the cheapest. You need to decide what you want to be." - Shensi Ding

Links:

• LinkedIn: https://www.linkedin.com/in/shensiding/ 
• Website: https://www.merge.dev/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Merge

Chapters:

00:00 Intro

01:40 Starting Merge During the Pandemic

02:50 Challenges of In-Person Work Culture

03:42 Expanding to New York and International Markets

04:50 Maintaining Work Ethic and Decision Making

06:42 Evolving Leadership and Learning from Mistakes

10:56 Bringing Industry Leaders to Inspire the Team

13:56 Acquiring the First Customers

16:38 Dealing with Copycats and Maintaining Quality

21:08 Product Evolution and Adapting to AI

27:59 The Halo Effect of New Products

29:59 Promoting AI Tools Internally

33:15 Fundraising Challenges and Successes

38:08 Moving Upmarket and Adapting

41:42 Founders' Background and Journey

47:16 Balancing Work and Personal Life

50:41 Outro

In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog.

Nikhil shares how he evaluates founders, why the “slope of learning” is the most important quality he looks for, and how he builds long-term partnerships based on trust, curiosity, and shared ambition. He also opens up about the changing venture landscape, the hype and opportunity of AI, and what it means to be an investor who has truly walked in a founder’s shoes.

• Understanding the Importance of Learning: Nikhil emphasized the significance of the "slope of learning" in evaluating founders. This refers to a founder's ability to quickly learn and adapt to evolving market conditions, especially in the fast-paced AI era.
• Making a Lasting First Impression: According to Nikhil, the first few minutes with a potential investor are critical. Whether it's 15 or 30 minutes, founders must capture the investor's attention and highlight their vision's potential.
• Pitching with Conviction: Nikhil advised founders to clearly articulate why their business has the potential to be massive. It's crucial to strike a balance between ambition and grounded reality.
• Value of Ongoing Communication: Post-investment, Nikhil stressed the importance of maintaining regular communication between founders and investors. 
• Leveraging AI for Better Investments: Footwork has been proactive in using AI to manage and analyze portfolio companies, allowing them to track company progress and trends efficiently.
• Empathy from Experience: As a former operator and founder, Nikhil shared his belief that empathy is crucial in the investor-founder relationship. Understanding the challenges founders face allows investors like Nikhil to be better partners, offering thoughtful guidance rather than prescriptive advice.

Quote of the Show:

• “In the first 30 minutes with a founder, I’m trying to assess their slope of learning… We invest in slope, not just smarts. How fast a founder learns matters more than what they know on day one." - Nikhil Basu Trivedi

Links:

• LinkedIn: https://www.linkedin.com/in/nikhilbt/ 
• Website: https://www.footwork.vc/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Footwork

Chapters:

00:00 Intro

01:27 Key Traits in Founders: The Slope of Learning

04:59 The Importance of First Impressions in Pitching

13:48 Evaluating and Supporting Portfolio Companies

19:44 The Impact of AI on Venture Capital

24:04 The Value of Thought Partnership

31:10 Reflections on Missed Opportunities and Career Choices

36:30 Future Aspirations for Footwork 

38.25 Outro

In this episode, David talks with Betsy Fore, Co-Founder and former CEO of Tiny Organics and Founding Partner of Velveteen Ventures. Betsy shares her remarkable journey from toy inventor to serial entrepreneur and impact investor, becoming the first Native American woman to raise a Series A along the way.

She opens up about co-creating Tiny Organics alongside 100 founding families, facing setbacks like her unaired Shark Tank appearance, and learning to redefine success through purpose and presence. Betsy also reflects on the lessons that shaped her new book, Built on Purpose, blending practical entrepreneurship with spiritual grounding and a values-driven approach to leadership.

Now, through her venture fund and nonprofit, Betsy is focused on investing in solutions that uplift communities, children, and the planet, showing that business can be both profitable and deeply purposeful.

Takeaways: 

• Unforgettable Beginnings and Tiny Organics' Success: Betsy's tale begins with her concept of engaging 100 founding families, transforming them into co-creators of Tiny Organics and fostering community-driven innovation.
• Embracing Challenges and the Road Less Traveled: Betsy's first entrepreneurial venture, a Fitbit-like product for dogs, taught her the significance of understanding consumer behavior and product-market fit. 
• A Unique Shark Tank Experience and Fundraising Insights: Navigating numerous challenges, including a memorable Shark Tank experience, Betsy shares insights into the traditional venture fundraising path and the nuances of raising capital, particularly as a Native American woman.
• Discovering Purpose Beyond Business: Betsy's inspiration for her debut book, Built On Purpose, stemmed from a desire to demystify the practice of manifestation and align it with business creation.
• Melding Investment with Impact: Through Velveteen Ventures, Betsy shifts her focus towards using her skills to benefit her community and the broader planet. Her investments in healthcare, climate, and solutions for children.

Quote of the Show:

• “The most important relationship a founder can have isn’t with investors or customers. It’s with themselves." - Betsy Fore

Links:

• LinkedIn: https://www.linkedin.com/in/betsyfore/ 
• Website: https://www.tinyorganics.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #TinyOrganics #VelveteenVentures

Chapters:

00:00 Intro

01:26 Building Tiny Organics with Founding Families

07:47 From Tiny Organics to National Recognition

08:34 Lessons from a Previous Venture

13:51 Shark Tank Experience

19:18 Navigating the Venture Capital Landscape

25:07 Securing Initial Funding and Building a Strong Advisory Board

26:15 Realizing the Importance of Giving Back

27:55 Founding Natives Rising and Healing Through NLP

29:20 Investing in Underrepresented Founders

31:39 Writing 'Built on Purpose' and the Power of Manifestation

35:38 Inspiring Stories from Native American Founders

38:21 Launching a Venture Fund with a Purpose

41:26 From Rural Illinois to International Success

49:35 The Importance of Self-Compassion for Founders

50:35 Outro

In this episode, Matt Price shares the remarkable story of building Crescendo, one of the fastest-growing companies ever featured on the show, by reimagining customer experience through advanced AI and deeply trained specialists. Matt’s journey has come full circle: from a technical support rep early in his career, to scaling Zendesk, to now creating an entirely new model for enterprise-grade customer care.

Matt opens up about assembling an elite leadership team in record time, creating a vertically integrated product-and-operations engine, and designing a culture anchored around accountability, curiosity, and constant communication. He also explains why outcome-based pricing changes everything, how General Catalyst’s creation model gave Crescendo an unfair advantage, and why traditional BPOs simply aren’t positioned for the AI era. This is a masterclass in speed, focus, and operational excellence.

Takeaways:

• Building a Stellar Team: Matt emphasized the importance of assembling a high-quality team quickly. He discussed how bringing in top talent, especially those with experience in related fields, has been crucial for Crescendo's rapid growth.
• Curiosity and Vision as Key Attributes: When recruiting for a fast-growth environment, Matt values curiosity and passion for the company's vision. These attributes, combined with relevant experience, are critical for innovation and progress.
• Prioritizing Outcomes Over Traditional Models: Crescendo has embraced outcome-based pricing, aligning the company’s success with customer satisfaction. This model contrasts with traditional seat-based pricing and encourages the entire organization to focus on end-to-end service quality.
• Integrating AI Thoughtfully: Matt spoke about the evolution of AI in customer care and its potential to transform the industry. By integrating AI with human expertise, Crescendo offers enhanced support experiences.
• Strategic Acquisition for Growth: The strategic acquisition of traditional BPOs has allowed Crescendo to expand its distribution and offer scalable AI solutions. Matt's approach underscores the power of mergers and acquisitions in achieving rapid growth.
• Creating a Culture of Accountability: Matt stressed the significance of having someone accountable for leading every project or initiative. In a fast-paced environment, clarity in roles and responsibilities is vital for efficiency and progress.
• Fostering Open Communication: Maintaining open communication channels, even in remote settings, is a priority for Crescendo's leadership. Matt ensures his team stays connected through regular meetings and an open-door policy.

Quote of the Show:

• “Customer care was constrained by the economics. In order to deliver customer care up to now, you have to put humans in, a lot of people in… and AI now changes that, AI puts us into a world of abundance. And we need to shift our mindsets now as CX leaders… we’re moving from being deflectors to creators and innovators." - Matt Price 

Links:

• LinkedIn: https://www.linkedin.com/in/growthspecialist/ 
• Website: https://www.crescendo.ai/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Crescendo

Chapters:

00:00 Intro

01:32 Building a High-Impact Team

03:40 The Role of AI in Customer Service

06:03 Rapid Growth and Company Evolution

07:58 Leadership and Team Dynamics

11:03 AI Integration and Product Development

21:53 Founding Crescendo and Market Opportunities

28:10 Challenges and Focus as a CEO

31:08 The CEO's Influence on Team Dynamics

35:00 Outcome-Based Pricing in SaaS

36:22 Challenges and Benefits of Outcome-Based Models

41:25 Strategic Growth Through Acquisitions

47:04 The Future Vision for Crescendo

48:34 Personal Journey and Early Career

58:33 Advice for Aspiring Entrepreneurs

59:29 Outro

In this episode, David sits down with Ryan Wang, Co-Founder and CEO of Assembled, to explore this very challenge. What started as a simple scheduling tool has evolved into an AI-powered customer support platform trusted by leading companies like DoorDash and Salesforce.

Ryan opens up about the realities of scaling a fast-growing company, balancing innovation with culture, leading through learning, and keeping mission and execution at the heart of everything. His insights offer a playbook for founders and leaders aiming to build resilient, adaptable organizations.

Takeaways:

• Understanding the Challenge of Scaling Support: Ryan Wang shares insights into the evolution of Assembled, beginning with a fundamental question: how to scale great customer support without losing efficiency..
• Wearing Multiple Hats: Ryan emphasizes the importance of diving into different roles within a company. For founders, this means deeply engaging with various functions, learning from their challenges, and understanding what excellence looks like.
• The Art of Networking: The conversation highlights the importance of connecting with top industry leaders to learn and seek guidance. Founders should prioritize genuine learning over mere networking, making it easy for mentors to share their expertise.
• Adaptability and Product Evolution: Assembled’s journey reflects the necessity of being adaptable. Ryan discusses the creation of a "new products" team to innovate without disrupting the existing structure, showcasing a strategic approach to product development.
• Facing Cultural Challenges: The transition to AI tools and methods posed cultural challenges at Assembled. Ryan acknowledges how these changes can strain company culture, advising that clear communication and integrating efforts can prevent breaking the company culture.
• Mission and Execution: Ryan and David discuss how a strong mission and purpose can act as a modern moat for companies

Quote of the Show:

• “As CEO, your job is to hold the line, even when it breaks hearts, because someone has to protect the long-term vision." - Ryan Wang

Links:

• LinkedIn: https://www.linkedin.com/in/ryanywang/ 
• Website: https://www.assembled.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Assembled

Chapters:

00:00 Intro

01:22 Deep Dive into Leadership and Management

04:25 Networking with Industry Leaders

09:12 Balancing Multiple Roles as CEO

15:31 Transition to CEO Role

23:33 Evolution of Assembled's Product

29:13 Running Through Y Combinator

30:28 Demo Days and Team Dynamics

32:16 Staying on Top of Rapid Changes

35:53 The Concept of Moat in Business

40:22 Adapting to AI and Cultural Challenges

45:09 Future Vision for Assembled

47:42 Personal Background and Influences

52:45 Advice for Aspiring Entrepreneurs

55:15 Outro

In this episode, Noah Shanok, Founder and former CEO of Stitcher, reflects on his entrepreneurial journey leading one of the earliest podcast platforms, which ultimately sold to SiriusXM for $325 million. He shares candid lessons from the early days of Stitcher, navigating sleepless nights, hiring versatile early employees, and learning from missteps along the way.

Noah also discusses how his time at Amazon influenced his approach to structured hiring, why prioritizing personal well-being is critical for long-term effectiveness, and how founders can overcome imposter syndrome. Now working as a coach to entrepreneurs, he brings a unique perspective on balancing growth with sustainability, drawing on both successes and challenges from his own journey.

• Prioritize Yourself as a Founder: Noah candidly discussed his early days at Stitcher, which were characterized by overworking, sleep deprivation, and unhealthy habits. He advocates for founders to prioritize their well-being to ensure they can think clearly in the short term while remaining effective in the long run.
• Building the Right Team: Noah emphasized the impact of hiring a versatile team early on. His advice to recruit a "jack of all trades" who can adapt and grow with the company resonates with many startup leaders.
• Overcoming Imposter Syndrome: Noah addressed the imposter syndrome prevalent among founders. He shared strategies to navigate these feelings by focusing on decision-making confidence and holding oneself accountable.
• The Importance of Timing and Market Dynamics: Reflecting on Stitcher’s challenges, Noah acknowledged the role of timing and market forces. Factors such as market readiness and timing of product launches are crucial in scaling a business successfully, emphasizing that external shifts can heavily influence a startup’s trajectory regardless of internal effort and execution.
• Leveraging Strategic Partnerships: Noah’s success in securing high-profile deals started with creating strategic partnerships. By working with seasoned advisors, founders can effectively enter new markets and secure pivotal deals that may hasten growth and establish industry credibility.

Quote of the Show:

• “ I've helped hire hundreds of people at Amazon. If I started another company I would implement a very light version of Amazon's process, and I would do it very, very early." - Noah Shanok

Links:

• LinkedIn: https://www.linkedin.com/in/noahshanok/ 
• Website: https://startupceo.coach/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Stitcher

Chapters:

00:00 Intro

01:42 The Importance of Hiring a Versatile Team Member

02:24 Finding the Right Person for the Job

07:00 Lessons from Amazon's Hiring Process

13:29 Stitcher's Early Business Development Deals

21:37 Challenges and Realities of Strategic Partnerships

26:53 Coaching Founders: Common Challenges and Solutions

32:29 Transformative Changes and New Habits

33:13 The Impact of Prioritizing Self-Care

37:50 The Power of CEO Support Systems

38:24 Dealing with Imposter Syndrome

45:24 Lessons from Stitcher: Timing and Market Dynamics

48:58 The Drive to Build and Help Others

51:50 The Importance of Mentors and Advisors

57:25 The Need for a Support System for CEOs

59:38 Advice for Founders 

1:00:58 Outro

In this episode, David Cummings, Founder and CEO of Atlanta Ventures, reflects on his journey building ten companies, including Pardot, which sold to ExactTarget for $95 million, and investing in some of Atlanta’s most successful startups like Calendly and SalesLoft. He shares the guiding principles that shaped his entrepreneurial path, from building a culture-first company to navigating the realities of bootstrapping, scaling, and liquidity events.

David also opens up about his role in transforming Atlanta’s tech landscape through Atlanta Tech Village and his ambitious project to redevelop South Downtown into a vibrant startup district. Along the way, he offers candid advice for founders on leadership, resilience, and blending work with life in a sustainable way.

• Visionary Leadership: Cummings underscores the importance of having a clear and opinionated vision. The strategy of creating a product that provides "the most bang for the buck" without falling into the trap of building every requested feature was crucial to Pardot’s success.
• Bootstrapping Success: Despite the odds against fundraising in a nascent market, Cummings attributes his company’s success to resilient bootstrapping. This allowed him to maintain control and leverage opportunities like strategic acquisitions without compromising his vision.
• Cultivating Culture: A major highlight from Cummings' leadership was the deliberate cultivation of a workplace culture that prioritizes being positive, self-starting, and supportive.
• Balancing Ambitions and Personal Life: As an advocate for the "work-life blend," Cummings emphasizes that while early-stage startups demand an intense commitment, sustaining a balanced life is about integrating passion for work with personal commitments.
• A Tech Renaissance in Atlanta: Cummings' latest venture involves the redevelopment of a historic part of Atlanta into a vibrant startup district. This ambitious project aims to transform south downtown Atlanta into a living ecosystem for innovation and growth, reinforcing Atlanta’s position as a world-class city with a thriving entrepreneurial community.

Quote of the Show:

• “All the entrepreneur styles are different. But for me personally, I'm that shock absorber style. I recognize that things can be great and things can be bad, and just modulate it for the team." - David Cummings

Links:

• LinkedIn: https://www.linkedin.com/in/davidcummings/ 
• Website: https://www.atlantaventures.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #AtlantaVentures

Chapters:

00:00 Intro

01:44 Early Challenges and Successes at Pardot

02:24 Building a Strong Company Culture

03:02 Product Vision and Customer Focus

05:55 Transition from Doer to Leader

12:49 Bootstrapping vs. Fundraising

20:34 The ExactTarget Acquisition

31:08 Reflections on Entrepreneurship and Liquidity

36:52 Understanding Startup Valuations

38:09 Building a Winning Team at Pardot

41:17 Investing in Founders with the Right Attributes

43:29 The Atlanta Tech Village Journey

51:44 Revitalizing Downtown Atlanta

01:00:56 David's Entrepreneurial Beginnings

01:06:57 Balancing Entrepreneurship and Family

01:10:36 Advice for Aspiring Entrepreneurs

01:12:50 Outro

Michael explains how he grew a single 3,000-square-foot location into a $9 million operation by modernizing systems, cutting inefficiencies from the supply chain, and infusing emotion into every part of the customer experience. He also reflects on the challenges of scaling in a traditional industry, the decision to franchise, and the importance of mentorship, high standards, and culture in building a business that lasts.

Takeaways:

• Develop a Strong Brand Identity: A major part of Jacobson’s strategy was creating branding that emphasizes emotional connection, redefining flowers as essential expressions of love rather than luxury items. 
• Listen to Your Employees: Before anything else, Jacobson prioritized understanding the needs of the staff already working in the flower shop. Their insights provided critical low-hanging fruit, such as switching outdated and costly phone systems, which paved the way for larger innovations.
• Direct-to-Source Supply Chain: By eliminating unnecessary intermediaries in the supply chain, French Florist improved both the quality and cost-efficiency of their products. Direct relationships with flower farms allowed the business to offer fresher flowers with longer shelf life at competitive prices.
• Prioritize Customer Experience: French Florist’s focus on exceeding customer expectations through personalized service has been crucial. They constantly seek ways to enhance customer satisfaction, such as offering unique video card messages to accompany floral deliveries.
• Strategic Hiring and Internal Culture: Hiring talented individuals who align with the company’s values and culture has been a priority. Jacobson emphasizes unconventional and thoughtful interview processes to ensure new hires share the company’s vision and drive.

Quote of the Show:

• “ If it ain’t broke, don’t fix it is one of my least favorite sayings. If there’s a better way, I want to find it." - Michael Jacobson

Links:

• LinkedIn: https://www.linkedin.com/in/michaelrichardjacobson/ 
• Website: https://www.frenchflorist.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #FrenchFlorist

Chapters:

00:00 Intro

01:38 Transformative Leadership and Infusing Emotion

03:22 Building a Culture of Love and Excellence

08:25 Hiring for Values and Unconventional Interviews

14:51 The Origin Story of French Florist

19:19 Initial Challenges and Early Improvements

24:36 Revolutionizing the Floral Industry with Technology

31:43 Revenue Growth and Optimization

33:15 Supply Chain Innovations

35:15 Direct Importing from Farms

37:36 Challenges in the Floral Industry

40:28 Franchising and Expansion

48:18 Personal Reflections and Motivation

1:01:01 Outro

David shares 10 of his favorite highlights from the journey so far, covering everything from guest stories and personal milestones to the behind-the-scenes evolution of the show. This episode is a heartfelt thank-you to the community that has grown around the podcast and a look ahead at what’s next. 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/

#NotAnotherCEO #Podcast #1YearReflection

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #DecemberCEOPulse

Chapters:

00:00 Intro

01:22 Reflect: Assessing Achievements

05:15 Rally: Energizing Your Team

11:14 Recharge: Taking Time to Rest

13:33 Outro

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #NovemberCEOPulse

Chapters:

00:00 Intro

03:16 Get Your Team Using AI

06:24 Get Traction With Focused AI Projects

10:42 Install A Champion To Own AI

14:00 Outro

In this special compilation episode, we highlight moments from eleven CEOs who reflected on the investors that shaped their companies’ trajectories, not just through capital, but through conviction, guidance, and belief. These clips reveal how the right investors help founders stay grounded in their mission, navigate uncertainty, and make better decisions during pivotal moments of growth.

Across these stories, one theme stands out: exceptional investors don’t just finance a business, they help founders become better leaders. They open doors, challenge thinking, and offer support that often goes unspoken and uncelebrated. As we head into the holiday season, this episode is an invitation for CEOs to pause, reflect, and acknowledge the people whose partnership made the climb possible.

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess 

Chapters:

00:00 Intro

02:17 Daniel Chait - Greenhouse

02:54 Kyle Porter - Salesloft

06:50 Craig Walker - Dialpad

13:24 Dane Atkinson - Odeko

21:11 Diego Oppenheimer - Algorithmia

24:46 Itamar Friedman - Qodo

28:43 Jeron Paul - Spiff

34:03 Nadia Boujarwah - Dia&Co

38:59 Nick Patrick - Radar

44:16 Toby Kraus - Lightship

53:30 Tom Buiocchi - ServiceChannel

54:09 Outro

From launching a Substack and partnering with Nick Freund to rethinking content distribution and recording locations, David breaks down what's working, what he’s learning, and the goals for the next quarter.

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #DavidPolitis

Chapters:

00:00 Intro

00:42 Launch of Not Another CEO Substack

03:07 Partnership Announcement: Joining Forces with Nick Freund

05:31 Reflecting on Goals and Achievements

09:58 Looking Ahead: Goals for Q2

12:26 Outro

Shaun delves into his philosophy on investing in early-stage companies, emphasizing the importance of resilience and adaptability in founders. He also discusses the intricacies of climate tech investment and the lessons he's learned from over two decades in the field. 

Takeaways:

• The Importance of "Burned Bridges": Shaun explains that he looks for founders who feel they have no option but to succeed, drawing a comparison to immigrants or those without a fallback, which can drive relentless focus and fortitude.
• Signals of Early-Stage Investment: Investing at the pre-seed stage involves identifying teams with potential through their work product rather than initial conversations. 
• Challenges of Climate Tech Investing: The difficulty in obtaining clear customer signals within climate tech is highlighted. Shaun notes that genuine customer commitment is hard to gauge and is essential for moving beyond pilot projects.
• Weathering the Storms: Shaun emphasizes that founders who persist through geopolitical challenges, like supply chain disruptions and tariffs, emerge uniquely stronger. 

Quote of the Show:

• “Portfolio math is brutal because it basically says that most companies don’t matter… it’s very easy to say, it’s very hard for founders to accept they may not be that one or two companies." - Shaun Abrahamson

Links:

• LinkedIn: https://www.linkedin.com/in/shaunabe/ 
• Website: https://thirdsphere.com/ 
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:30 Burned Bridges Mindset

03:47 Early Bets And Bad Logos

06:20 YC Founder Signal Noise

08:48 Work Product Over Pitch

11:32 Climate Hardware Realities

15:39 Lego Building To Revenue

17:29 Tariffs And Supply Chain Chaos

20:02 Founders Forged By Turmoil

23:54 Why Third Sphere Went Climate

26:29 Mission Driven Founder Support

27:26 Belief And Reality Checks

30:41 Direct Feedback As A VC

35:35 Private Credit Replaces Banks

39:15 Founder Updates And Trust

44:29 Portfolio Math Harsh Truths

49:09 Biggest Missed Deal

50:46 Next Decade Climate Bets

53:16 Outro

From her experience with early-stage companies to her unique perspective on the dynamics of venture capital, Rudina shares invaluable lessons about the importance of execution, understanding investor expectations, and the intricacies of navigating the startup ecosystem.

Takeaways: 

• The Value of Execution: For Rudina, the key trait she seeks in founders is execution excellence. It's not just about having a vision but demonstrating the ability and hustle to deliver beyond expectations.
• The Misunderstood VC Role: Many founders and employees don't understand the source of venture capital. Knowing that VCs manage funds from institutions like endowments and pensions changes the stakes and expectations.
• Importance of Strategic Partnerships: Rudina advises founders to seek investment from firms and partners that align with their stage and needs, rather than solely pursuing big names which might not provide necessary support.
• The Art of Quick Decision-Making: Efficiency in decision-making during early meetings can shape successful partnerships. Rudina values honesty in communicating why a VC might pass on an opportunity, emphasizing that a quick, thoughtful no is better than indecision.
• Sustained Support Post-Investment: At Glasswing Ventures, support continues beyond just funding, emphasizing talent acquisition, customer connections, and strategic guidance, ensuring startups grow sustainably.

Quote of the Show:

• “What have we done for them lately to deserve to expect? Yes we’ve provided capital, but that’s not enough in my book." - Rudina Seseri

Links:

• LinkedIn:https://www.linkedin.com/in/rudinaseseri/   
• Website: https://glasswing.vc/  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 
  

Chapters:

00:00 Intro

01:37 Ruthless Execution

02:32 Spotting Hustle Fast

05:38 Execution in the AI Boom

07:55 Retention and Switching Costs

10:08 AI Interest vs Intent

13:19 AI Hype and Human Loop

17:58 How VCs Decide Quickly

20:39 Giving Fast Honest Nos

22:54 Execution and Go To Market Gaps

24:21 How VCs Support Founders

27:14 Portfolio Review Cadence

28:27 Why Take Board Seats

33:30 Term Sheets Beyond Valuation

38:17 Choosing Firm vs Partner

41:29 Scaling Support With Team

43:01 Why She Became an Investor

45:14 Outro

In this episode, Ian Sigalow offers a candid, unfiltered look at early-stage investing and the founder–investor relationship, including one of the most sobering truths first-time founders often learn too late: it’s far harder to unwind a bad investor than a bad marriage. Drawing from decades of experience backing companies and founders at Greycroft, Ian breaks down how great investors actually think, decide, and engage behind the scenes.

Ian shares what he looks for in exceptional founders, why the explosion of startups hasn’t increased the number of true breakout winners, and why most board meetings fail to create real value. This episode is a must-listen for any CEO navigating fundraising or building their first long-term investor relationships.

Takeaways: 

• Master of Two Domains: Sigalow emphasizes the importance of founders who excel in both product understanding and sales, calling them "masters of two domains" who are rare and invaluable.
• Big Market Potentials: Ian points out the essential need for startups to target significantly large markets. In the entrepreneurial world, having the potential to scale a company to a billion-dollar business is vital.
• The Earned Secret: A distinctive aspect investors look for is the "earned secret."
• The Importance of Trust in Investor Relationships: Sigalow stresses that founders should only take money from investors they trust, highlighting the lasting nature of these partnerships. 
• Controlling the Board Meeting: Effective CEOs maintain control over board meetings, ensuring the focus remains on strategic issues rather than getting sidetracked. 

Quote of the Show:

• “A CEO should never take money from someone they don’t trust. It’s harder to get out of a bad investor than a bad marriage." - Ian Sigalow
  

Links:

• LinkedIn: https://www.linkedin.com/in/iansigalow/ 
• Website: https://www.greycroft.com/ 
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 
  

Chapters:

00:00 Intro

01:32 Founder's Qualities and Market Potential

03:01 The Importance of Earned Secrets

03:57 Challenges in Identifying Exceptional Founders

06:12 The Evolution of Venture Capital

17:42 The Role of Technology in Venture Capital

21:45 Focus on Early-Stage AI Investments

26:40 Choosing the Right Investment Partner

10:50 Onboarding Process at Greycroft

27:50 The Rule of Three in Communication

29:24 Key Metrics for Founders

31:21 The Role of Board Meetings

38:26 Understanding Venture Capital Dynamics

18:46 Ian's Journey into Venture Capital

48:04 Outro

In this episode, Irina Novoselsky shares the honest, vulnerable truth behind leading at the highest levels: the job isn’t about having every answer, it’s about choosing to step into roles, decisions, and moments that stretch you and reveal what you’re capable of. Irina brings deep experience from modernizing CareerBuilder and now leading Hootsuite, the world’s most widely used social media management platform trusted by millions of users.

Irina walks through the systems, disciplines, and mindsets that have shaped her career, from the 15-minute weekly all-hands that transformed Hootsuite’s culture, to her 100-day onboarding playbook, to redefining the company’s ICP in 10 days and doubling growth. She also breaks down how Gen Z will reshape every company’s go-to-market motion, why naivete is an early-career superpower, and how her immigrant upbringing forged the resilience she leads with today.

Takeaways: 

• Embrace Focus and Prioritization: Irina emphasizes the addictive nature of focus and its role in driving growth. By identifying core strengths and doubling down on them, businesses can achieve unparalleled success.
• Redefine Company Rituals: Hootsuite’s unique weekly 15-minute all-hands meeting, serves as a crucial touchpoint. It's a tightly produced session that keeps the team energized and informed.
• Foster Transparency and Engagement: For Irina, transparency is key. She advocates for open communication and regular Q&A sessions, encouraging feedback, even the uncomfortable truths.

Quote of the Show:

• “I get scared frequently. I put myself in vulnerable moments all the time… but those are the moments when you realize you can do hard things." - Irina Novoselsky

Links:

• LinkedIn: https://www.linkedin.com/in/irina-novoselsky/ 
• Website: https://www.hootsuite.com/ 
  

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify:https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts:https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube:https://www.youtube.com/@NotAnotherCEOPodcast 

Chapters:

00:00 Intro

01:10 Irina's Leadership Style and Hootsuite's All Hands Meetings

06:53 The Importance of Transparency and Feedback

08:49 First Steps as a New CEO

14:27 Identifying Key Players and Cultural Carriers

18:14 The Power of Focus and Prioritization

23:53 Communicating with Investors and Board Members

26:35 The Role of Social Media and Personal Branding

28:42 Creating a Resonant Culture

29:20 The Power of Social Media for CEOs

30:31 Understanding Gen Z's Buying Behavior

33:15 Challenges and Growth as a CEO

36:18 The Importance of Vulnerability and Mentorship

51:17 Transitioning from Finance to Operations

54:03 Final Reflections and Advice

59:04 Outro

Todd shares the values and rituals that helped him scale Pendo into a product-led powerhouse, including his unwavering commitment to customer-centricity, his direct approach to hiring, and the operating cadence that keeps his nearly 900-person team aligned. Todd reflects on the highs, lows, and philosophies that have guided his journey.

Takeaways:

• Customer Obsession as a Foundational Value: Todd emphasizes how being “maniacally focused on the customer” has guided every stage of Pendo’s growth. From answering support tickets himself in the early days to personally monitoring feedback as CEO, he’s created a culture where customer empathy cascades through every department.
• Every Hire Must Talk to Customers: Todd shares a hiring principle he’s followed since day one: only hire people you'd trust on the phone with a customer. This standard shaped Pendo’s culture, even affecting how they screen engineers, ensuring they’re willing and able to engage directly with users.
• Personally Interviewing Hundreds: At one point, Todd personally interviewed every employee… almost 800 people. Beyond vetting talent, it was a powerful tool for maintaining cultural consistency and calibrating hiring managers across the org. He also ran 90-day check-ins with new hires to ensure expectations matched reality.
• Product Leadership Rooted in Vision: Though product leadership has evolved at Pendo, Todd has remained deeply involved in product vision and strategy. He describes how he stays hands-on with design sessions, brainstorming new features, and ensuring Pendo’s tools meet the high bar of product teams building for product teams.
• Disciplined Operating Rhythm: Todd credits much of Pendo’s success to a consistent cadence of planning and communication. Annual and quarterly planning rituals, town halls, and regular team offsites help align the company around shared goals and keep stress in check during turbulent times.
• Built in Raleigh, Built to Last: Despite early pressure to move to Silicon Valley, Todd built and scaled Pendo out of Raleigh, North Carolina. He shares how the local ecosystem shaped the company and how hiring executives from outside the region helped them compete on a national scale while staying grounded in local roots.

Quote of the Show:

• "Nearly every product is like, strongly opinionated, meaning when you use it, you feel like it has a point of view that it’s trying to impart." - Todd Olson

Links:

• LinkedIn: https://www.linkedin.com/in/toddaolson
• Twitter (X): https://x.com/tolson
• Company Website: https://www.pendo.io/

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #Pendo

Chapters:

00:00 Intro

01:23 The Importance of Customer Obsession

02:34 Early Days and Customer Engagement

04:57 Hiring for Customer Focus

08:39 Personal Stories and Career Reflections

11:27 Interviewing Every Employee

18:24 Product Evolution and Ideal Customer Profile

26:19 Operating Rhythm and Business Cadence

34:53 Adapting and Planning for Long-Term Success

37:17 Biggest Challenges Faced at Pendo

43:56 Future Vision for Pendo

47:00 Early Career and Entrepreneurial Spark

53:49 Building a Business in Raleigh

56:59 Balancing Family and Business

01:02:55 Outro

He opens up about fundraising setbacks, building conviction in tough moments, keeping customer experience front and center, and navigating the pressure of rapid growth while staying anchored in purpose.

Takeaways:

• Dropping Out to Go All-In: Sean left college to pursue Stord full time, driven by a conviction that there was a better way to manage logistics in a fragmented industry. That early decision required grit and belief before traction or investor backing.
• Turning Cold Outreach Into Capital: Sean shares how his early fundraising relied on writing 150 cold emails a day. Persistence and storytelling helped him break through, eventually leading to key early checks that helped kickstart Stord’s growth.
• The Importance of Mission and Mindset: Through tough moments and early challenges, Sean and his Co-Founder stayed grounded in their mission. He talks about the psychological weight of leadership and the discipline required to keep moving forward.
• From Scrappy Marketplace to Full Stack Platform: Stord started as a logistics marketplace but pivoted into a fully integrated supply chain solution. Sean explains how that shift allowed them to deliver better customer experience, tighter control, and long-term defensibility.
• Customer Experience Is the Product: Even as a logistics company, Sean believes customer experience is the most important differentiator. He shares how Stord built systems and culture that put CX at the center of every part of the business.
• Navigating the Growth Curve Without Losing Focus: Sean discusses what it’s like to scale quickly while holding on to high standards. He shares lessons around team building, leadership habits, and making time for clarity amid the noise.
• Believe, But Be Realistic: Sean reflects on the importance of conviction, but also warns Founders to avoid believing their own hype. He recommends surrounding yourself with people who keep you honest and grounded as you grow.

Quote of the Show:

• "If we don't have a customer, we don't have employees. If we have a vision but have no customers, that vision means nothing." - Sean Henry

Links:

• LinkedIn: https://www.linkedin.com/in/shenry96/
• Website: https://www.stord.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Stord

Chapters:

00:00 Intro

01:49 The Importance of Customer Obsession

05:44 Hiring for Customer Obsession

10:19 Scaling and Company Culture

21:30 Early Challenges and Pivots

39:26 The Rise and Fall of the Trucking Network

40:23 Navigating Hard Decisions and Growth

42:50 Investor Relations and Fundraising Journey

44:11 Mentorship and Early Influences

45:33 Strategic Partnerships and Business Alignment

51:23 Overcoming Challenges and Turning Points

56:10 Future Vision and Expansion Plans

01:03:51 Personal Background and Entrepreneurial Spirit

01:13:14 Advice to His Younger Self

1:14:40 Outro

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #OctoberCEOPulse

Chapters:

00:00 Intro

02:53 The Importance of a CEO Support System

03:57 Key Components of a CEO Support System

05:10 The Role of Co-Founders and Key Executives

07:33 The Value of Executive Assistants and Chiefs of Staff

09:24 Leveraging Board Members and Advisors

14:38 The Importance of Therapists and Personal Relationships

19:16 The Power of CEO Peer Networks

21:27 Outro

Scott dives into the tough realities of leadership, from making difficult people decisions to evolving as a CEO as the company scales. He opens up about the power of storytelling in fundraising and leadership, the importance of mental well-being, and the lessons he’s learned from being an early builder in Atlanta’s thriving tech ecosystem.

Takeaways:

• The Power of Storytelling: Scott Voigt emphasizes the significance of storytelling in his role as CEO. It's not just about what you say but how you say it. Through effective storytelling, he energizes and aligns his team, creating a shared vision and purpose.
• Hiring and Building a Strong Team: Voigt discusses the challenges of hiring and the importance of finding the right fit. He stresses the necessity of moving people out quickly if they are not a good fit, even though it can be difficult.
• Navigating Investor Relations: Scott’s journey of securing funding for Fullstory involved both challenges and triumphs. He shares the importance of being strategic and deliberate in choosing investors and board members.
• The Journey of Fullstory's Market Fit: Voigt candidly reflects on the evolution of Fullstory's product-market fit. Initially, as the team worked on a different product, they faced numerous rejections. However, the pivot to Fullstory's current offering brought about an immediate and undeniable product-market fit.
• Overcoming Internal Challenges: Discussing exits, Voigt argues that the company's mission should transcend any individual's role, ensuring continued alignment and progress regardless of internal changes.

Quote of the Show:

• “When your spidey sense tells you something isn’t working with a person, make the change fast. It only gets harder the longer you wait." - Scott Voigt

Links:

• LinkedIn: https://www.linkedin.com/in/scottmvoigt/ 
• Website: https://www.fullstory.com/ 

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #Fullstory

Chapters:

00:00 Intro

01:36 The Biggest Impactful Decision at Fullstory

03:35 The Challenges and Lessons of Letting People Go

08:38 Hiring Philosophy and Interview Techniques

18:56 The Importance of Storytelling as a CEO

24:54 Fundraising Journey and Product Pivot

33:38 Reflecting on the Early Struggles

37:14 The Importance of Team Chemistry

43:28 Navigating the Atlanta Tech Scene

48:20 Biggest Challenges and Lessons Learned

51:01 Future Vision for Fullstory

57:15 Personal Reflections and Advice

01:07:53 Outro

Flint also discusses the challenges of navigating growth, what he has learned about himself along the way, and the importance of staying true to purpose even in difficult times.

Takeaways:

• Scaling Begins with Small Wins: Flint emphasizes the importance of "stacking wins" in business, where each small victory propels you forward. He believes the key to success lies in maintaining momentum and making rapid, intelligent decisions.
• The Role of Mission and Values: For Flint, defining mission and values within a company is crucial for guiding decision-making processes. These elements serve as the company's moral compass, helping employees make decisions aligned with the organization's goals.
• Navigating Executive Leadership: Flint shares insights into the dynamics of leadership and succession planning. He describes the challenging process of evolving leadership roles to meet the company's growing demands.
• Overcoming Cybersecurity Challenges: Flint recounts a severe malware attack that tested the company's resilience. He stresses the importance of investing in robust cybersecurity measures and learning from such incidents to better protect critical business assets.
• The Power of Transparency: Flint argues for fostering trust and collaboration within the organization. By openly communicating challenges and strategies with his team, Flint was able to cultivate an environment of honesty and collective problem-solving.
• The Entrepreneurial Lifecycle: Flint illustrates the different stages of a company's growth, each with unique challenges and opportunities. From startup to public company, the journey requires adaptation and learning.
• Transitioning from Software to Sports: After two decades at Billtrust, Flint embarked on a new venture with Major League Table Tennis, driven by his passion for the sport.

Quote of the Show:

• “Any business is a combination of hundreds of thousands, if not millions of decisions, millions of small, little victories." - Flint Lane

Links:

• LinkedIn: https://www.linkedin.com/in/flintlane/
• Website: https://www.mltt.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #MajorLeagueTableTennis

Chapters:

00:00 Intro

01:23 Flint Lane's New Venture: Major League Table Tennis

01:56 The Importance of Stacking Wins

04:06 Effective Communication and Decision Making

06:30 The Role of Transparency in Leadership

14:51 Hiring the Right People

21:06 The Evolution of Executive Teams

27:17 The Importance of a Strong Board

31:53 Navigating the Startup Journey

33:19 The Decision to Go Public

36:34 The Acquisition Process

39:06 Cybersecurity Crisis

43:54 Transition to Major League Table Tennis

49:33 Reflections on Entrepreneurship

56:46 Final Thoughts and Advice

57:48 Outro

What is one thing you’ve done, big or small, that’s had the biggest impact on your company and you’d do again if you’re CEO of another company in the future?

In today’s special episode, we will be looking back at the answers given to this question. Dive in with us as we hear how all 19 CEOs that David has interviewed discuss what they would do again in their next venture!

We will be starting from the top with the show’s first ever guest, Nick Mehta. Follow the chapters below to see when each CEO’s answer is.

0:00 Intro

2:14 Nick Mehta - Gainsight

3:51 Tony Safoian - SADA

7:56 Anthony Serina - Revivn

12:13 John Fazzolari - Revivn

14:16 Loren Castle - Sweet Loren’s

21:32 Jeron Paul - Spiff

22:46 Alex Theuma - SaaStock

32:30 Jukay Hsu - Pursuit

38:33 Nick Cromydas - Hunt Club

47:20 Godard Abel - G2

51:14 Dan Michaeli - Glia

1:01:53 Kathryn Minshew - The Muse

1:11:06 Ryan Westwood - Fullcast

1:18:04 Nate Rosenstock - Crafty

1:28:37 Ryan Simonetti - Convene

1:41:33 Craig Walker - Dialpad

1:48:54 Eran Gil - AllCloud

1:54:50 Nick Freund - Workstream.io

2:03:45 Dane Atkinson - Odeko

2:07:00 Thank You

Ways to Tune In:

• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• Amazon Music: https://music.amazon.com/podcasts/7c6328f0-9b42-41db-8fe2-d263b4fbb261 
• Transistor: https://podcast.notanotherceo.com/ 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 

#NotAnotherCEO #BusinessSuccess #CEOAdvice

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #FebruaryCEOPulse

Chapters:

00:00 Intro

00:51 Personal Experiences with Imposter Syndrome

03:04 Defining Imposter Syndrome

04:56 The Two Paths of Imposter Syndrome

06:48 Channeling Imposter Syndrome for Growth

09:02 Practical Advice for Dealing with Imposter Syndrome

13:28 Outro