Crushing It

Leasing vs. Owning: The Commercial Real Estate Decision Every Business Faces

Jonathan Trimble — Mon, 16 Mar 2026 12:36:29 GMT

This episode dives into the intricate world of commercial real estate, through the lens of Maury Bronstein, a seasoned advisor, broker, and investor with over 25 years of experience. Whether you're a business owner, investor, or simply curious about real estate trends, Maury's insights clarify how strategic decisions around property holdings can accelerate growth, manage risk, and shape long-term wealth.

In this episode:

The role of an advisory real estate broker versus traditional brokerage
How private equity and family offices approach real estate investing
Key considerations: rent vs buy and the importance of flexibility
The impact of remote work trends on office space demand
The strategic foresight in land purchases and developments
Long-term investment strategies of family offices
Common mistakes young companies make in real estate decisions
Risks of insufficient due diligence in distressed assets and lender scenarios
How interest rates and macroeconomic factors influence property values
The domino effect of major corporate relocations on regional development

Timestamps:

00:00 - Introduction to Maury Bronstein and his background
02:42 - The distinction between a commercial real estate advisor and a broker
06:19 - How Maury supports private equity and family offices in real estate decisions
10:44 - The evolving landscape of office space post-COVID
15:14 - The long-term investment philosophy of family offices
17:45 - Mistakes young companies often make in expanding or acquiring property
21:22 - The importance of due diligence and risks of neglecting inspections
25:17 - Lessons from distressed assets and lender scenarios during financial crises
29:07 - The future of retail malls, office buildings, and adaptive reuse strategies
34:21 - The influence of macroeconomic trends, interest rates, and geopolitical shifts
37:01 - The movement of corporate headquarters within Texas and beyond
40:57 - Implementing risk discipline and strategic decision-making in real estate investments
46:19 - How to connect with Maury for advisory support

Resources & Links:

Don’t Chase Hype. Build What Works.

Jonathan Trimble — Fri, 06 Mar 2026 13:57:51 GMT

In this episode of Crushing It, we sit down with entrepreneur and investor Jeremy Middleton, founder of Middleton Enterprises and co-founder of HomeServe — a company that began with just £10,000 on a credit card and ultimately grew into a FTSE 100 business employing 10,000 people. Jeremy shares the unvarnished reality of building a company from scratch, including early failures, financial pressure, and the tough decisions that shaped his approach to risk, persistence, and growth.

Jeremy reflects on the difference between being a founder and being an investor. While entrepreneurs often start with ideas and optimism, Jeremy explains why he now looks for businesses that have already proven their model and reached profitability. He discusses why founders frequently misunderstand investors, why raising money too early can be dangerous, and why bootstrapping or turning to friends and family is often a smarter first step than chasing venture capital.

The conversation also tackles some of today’s biggest startup narratives — including hype around AI, inflated valuations, and the belief that capital can solve fundamental business problems. Jeremy explains why investment money should accelerate a working model rather than fix a broken one, and why disciplined growth and strong fundamentals still outperform trend-driven business plans.

Finally, Jeremy shares the story of how his struggling plumbing startup nearly collapsed before pivoting into a subscription-based warranty model that transformed the company’s economics. The episode offers candid lessons for founders on persistence, knowing when to pivot, protecting equity, and building companies that compound value over the long term.

Key topics

Lessons from early business failures

Importance of proven business models before investment

Strategies for raising capital in startups

Investing in profitable SMEs and long-term growth

Impact of AI on traditional businesses

Chapters

00:00 The Need for Capital vs. Confidence

05:57 Understanding Investor Perspectives

12:04 Navigating the Investment Landscape

17:57 Evaluating Business Models in the Age of AI

23:13 The Evolution of Call Centers and AI

28:15 Investment Insights: Identifying Real Value

36:43 Learning from Early Business Mistakes

43:00 Investing in Small Businesses: A Personal Journey

Resources

Guest links

LinkedIn

Entrepreneurship, Investment, Business Growth, Capital Raising, SME, Jeremy Middleton, Startup Lessons, Business Strategy, AI in Business, Family Office

Betting Millions Before the Rules Existed

Jonathan Trimble — Tue, 03 Mar 2026 15:35:05 GMT

Join us as Ed McDermott shares his journey of building EMMAC Life Sciences into CureLeaf International, navigating regulatory ambiguity across Europe, and the future of cannabis legalization and industry growth. This episode covers risk management, compliance, investment challenges, and the potential of cannabis as a medical and recreational product.

Key topics

Building EMAC Life Sciences into CureLeaf International

Navigating European cannabis regulations and cultural differences

Risks and challenges in early-stage cannabis ventures

The importance of compliance and cybersecurity in cannabis industry

Future outlook for cannabis legalization and industry growth

Guest name

Ed McDermott

Chapters

00:00 Introduction and Ed's Background

02:14 From a Blank Sheet to Europe's Cannabis Leader

03:53 First 18 Months: Challenges and Lessons

08:00 Team Formation and Cultural Dynamics

09:56 Medical Cannabis and Patient Impact

12:03 European Regulatory Framework and Cultural Nuances

15:13 Making Decisions in Ambiguous Regulatory Environments

19:52 Supply Chain Security and Cybersecurity Risks

25:05 Funding and Raising Capital in Cannabis

29:48 Compliance, Regulation, and Industry Challenges

39:50 Future Outlook: Rescheduling and Industry Growth

50:04 Legal and Criminal Market Dynamics

01:00:13 Lessons Learned and Advice for Entrepreneurs

01:05:12 The Purpose and Passion Behind Building a Business

01:08:03 Closing Remarks and Future Opportunities

Resources

Guest links

From Chaos to Cohesion: Leading Turnarounds Without Losing the Team

Jonathan Trimble — Sun, 22 Feb 2026 02:46:36 GMT

The conversation delves into the challenges of leadership, cultural transformation, and the impact of company culture on leadership decisions. Kevin Browett shares insights on building winning teams, the role of AI in leadership, and the importance of loyalty and company culture. He reflects on leadership mistakes, the need for cultural change, and the impact of career decisions on personal growth and development.

Takeaways

Communication is key to building relationships and driving change.
Winning teams are built on trust and respect.
Leaders must slow down to analyze situations effectively.
Cultural dynamics can hinder transformation efforts.
Loyalty in organizations is a two-way street.
Leadership requires humility and a willingness to learn.
Tough decisions are necessary for team performance.
Identifying and addressing bad apples is crucial for success.
Transformational leadership involves understanding people and processes.
Technology can enhance decision-making and efficiency.

Chapters

00:00 Navigating Risk and Opportunity
01:05 Transformational Leadership Across Industries
03:02 Building Relationships in Competitive Environments
09:11 Communication as a Key to Success
12:01 Non-Negotiables for Winning Teams
14:00 Identifying Root Causes of Underperformance
15:51 Leadership vs. Management: Making Tough Decisions
20:04 The Importance of Team Dynamics
23:13 The Illusion of Loyalty in Leadership
27:32 Building Trust and Earning Loyalty
29:38 The Misconception of Leadership Success
32:36 Navigating Career Transitions and Titles
35:11 Learning from Leadership Mistakes
41:30 Sharing Insights and Continuous Learning

Keywords

leadership, transformation, communication, team dynamics, performance, organizational culture, risk management, business strategy, technology, loyalty

Responsible AI by 2030: Transparency, Trust, and the Risks We Can’t Ignore

Jonathan Trimble — Sat, 24 Jan 2026 15:19:13 GMT

Xiaochen Zheng, the chief responsible AI officer and executive director at AI 2030, discusses the concept of responsible AI, its core pillars, and the impact of AI on sustainability, accountability, and governance. He also addresses the talent gap in AI projects and the implications of AI on society and human-machine collaborative intelligence. The conversation delves into the responsible use of AI, emphasizing the need for stakeholder engagement, responsible AI principles, and data governance. It also explores the impact of AI on personal use and the global community, highlighting the importance of collaboration and the urgency of responsible AI deployment.

Takeaways

Responsible AI encompasses transparency, bias identification, and sustainability, with a focus on accountability, safety, and security.
The talent gap in AI projects requires the inclusion of social scientists, ethicists, and diverse perspectives to address bias, ethical considerations, and the impact on society. Responsible AI requires stakeholder engagement and a commitment to responsible AI principles.
The impact of AI on personal use and the global community underscores the need for collaboration and urgency in responsible AI deployment.

Chapters

00:00 Addressing the Talent Gap in AI Projects
19:57 Sustainability and the Role of AI
26:00 Implications of AI on Society and Human-Machine Collaborative Intelligence
33:05 Responsible AI and Stakeholder Engagement
41:40 Trust and Responsible Use of AI
48:52 Global Framework for Responsible AI

Episode 3 - Somil Jain

Jonathan Trimble — Sun, 11 Jan 2026 16:01:43 GMT

Samil Jain, an expert in insurance, analytics, and entrepreneurship, discusses the misconceptions about the insurance market, the growth of managing general agents (MGA), and the challenges of measuring risk in the insurance industry. He also explores the impact of AI on insurance and the complexities of liability in the age of autonomous vehicles. The conversation covers various aspects of AI, its impact on society, and the challenges associated with its use. It also delves into the insurance industry, discussing the evolution of insurance products and the challenges of distribution.

Takeaways

Insurance market is not one large market, but rather 55 small markets regulated at the individual state level.
Managing General Agents (MGA) provide a flexible and capital-efficient way to start an insurance program without the need for a large infusion of capital.
The use of AI in insurance presents both opportunities and challenges, with the need for fine-tuning and understanding the limitations of AI models.
The liability and risk implications of autonomous vehicles and AI technology are complex and evolving, requiring careful consideration and adaptation in the insurance industry. AI should be used as a tool, not as the final answer
The insurance industry is evolving with new products and distribution challenges

Chapters

00:00 Misconceptions About the Insurance Market
09:05 The Impact of AI on Insurance
25:12 AI Security and Usage
30:37 Impact of AI on Society
37:27 Insurance Industry Evolution

Episode 2 - JJ Costigan

Jonathan Trimble — Sat, 10 Jan 2026 20:10:11 GMT

J.J. Costigan, a former FBI professional, shares insights from his experience in leading security and operations for iconic golf events and venues. He discusses the challenges, strategies, and critical incidents that have shaped his approach to risk management and leadership. The conversation covers a range of security and crisis management topics, including security innovations, crisis response, mass notification systems, drone defense, crowd management, and executive support for security. JJ Costigan shares insights and experiences from managing security at major events like the Liv and Augusta tournaments, highlighting the importance of proactive planning and risk management.

Takeaways

Mass gathering risk management
Layered defense and risk mitigation Proactive planning is essential for effective crisis response
Executive support and leadership involvement are crucial for building resilience and security culture

Chapters

00:00 Introduction to J.J. Costigan's Background and Expertise
05:52 Risk Management and Layered Defense at Large Golf Events
12:02 Perception of Law Enforcement and Security Measures
18:02 Importance of Training, Communication, and Command Post in Event Security
26:33 Crisis Response and Planning
36:39 Innovations in Security and Mass Notification Systems
42:31 Building Resilience and Continuity Planning
47:43 Educating and Engaging Executive Leadership

Eposode 1 - Kate Williams

Jonathan Trimble — Fri, 21 Nov 2025 21:12:50 GMT

A hidden clause. A looming deadline. And a SOC 2 scramble that could cost a startup real money.

In this episode of Crushing It, Jonathan sits down with Kate Williams, Partner in the Risk Assurance & Advisory Practice at Maxwell Locke & Ritter and one of Austin’s leading SOC 2 and cybersecurity compliance experts. Kate breaks down why startups so often find themselves rushing into SOC 2, how a simple readiness process can prevent chaos, and why shadow AI is quickly becoming one of the biggest risks early-stage companies face.

She shares real stories from the field — including the moment a company discovered a contractual SOC 2 deadline with financial penalties attached — and offers practical guidance on training, culture, and security basics that can save young companies from disaster.

If you’re building a startup, selling into the enterprise, or navigating the rising pressure around compliance and AI, this is an episode you don’t want to miss.