In this episode of the ASYMMETRY® Podcast, Tyler sits down with Jackson Payne, an M&A advisor and managing partner for the Georgia and South Carolina offices of Viking Mergers and Acquisitions. Jackson shares his journey from collegiate basketball coach to the CFO of a family-owned oilfield manufacturing business.

He breaks down how his family survived the 2008 financial crisis by taking a 50% pay cut, and the harsh lessons he learned when they sold the business unrepresented in 2014—just months before oil prices crashed from over $100 to $26 a barrel, crushing their rollover equity.

Today, Jackson uses that experience to protect founders from making the same structural mistakes.

We discuss the two primary reasons businesses fail to sell, the complexities of navigating Net Working Capital during due diligence, and why creating a competitive buyer environment is the ultimate leverage.

Listen to the full conversation to learn:

• [00:44] Introduction to Jackson Payne and Viking Mergers and Acquisitions.
• [04:07] Scaling a family oilfield business and navigating extreme cyclical markets.
• [08:21] The 2014 Exit: Why negotiating unrepresented led to getting the right price, but the wrong terms when the market crashed.
• [09:55] How the company survived the 2008 financial crisis through shared sacrifice and gained massive market share.
• [18:42] The two biggest red flags that prevent a business sale: Owner dependency and poor financial records.
• [26:24] Price vs. Structure: Understanding earnouts, seller notes, and rolled equity in lower-middle-market transactions.
• [29:14] Demystifying Net Working Capital ("the oxygen of the business") and post-close financial true-ups.
• [33:38] The ROI of an M&A Advisor: Why dealing with only one buyer destroys your leverage, and how to combat deal fatigue.

Listen and Subscribe:

• Apple Podcasts: https://podcasts.apple.com/us/podcast/asymmetry-podcast/id1880814763
• Spotify: https://open.spotify.com/show/0
• YouTube: https://www.youtube.com/@ShellCapital

Further Research & Blueprints: Subscribe to our Substack for episode notifications and research: https://asymmetricexit.substack.com/

Learn more about Shell Capital Management: https://shell-capital.com/

Learn more about Viking Mergers & Acquisitions: https://www.vikingmergers.com/

Selling a business requires executing a highly complex transaction against professional buyers who do this every single day.

If a founder takes their eyes off the daily operations to manage due diligence alone, the business often suffers a dip in performance—opening the door for buyers to retrade and adjust the purchase price downward.

In this episode of the ASYMMETRY® Podcast, Tyler sits down with John Marsh, founder and managing partner of Marsh Creek Advisors.

Leveraging his background as a former medical device CFO who executed over $360 million in transactions , John deconstructs the structural mechanics of a successful sell-side M&A process.

We discuss the critical importance of running a competitive, structured auction , how to structurally de-risk your enterprise years in advance by addressing owner dependency and customer concentration , and the reality of navigating complex deal structures like earnouts and rolled equity.

Timestamps:

[00:00] Introduction to John Marsh and Marsh Creek Advisors.

[07:58] Lessons learned from executing $360M in transactions and seeing the private equity playbook from the inside.

[11:50] The step-by-step mechanics of running a competitive M&A process.

[18:42] The asymmetrical risk of negotiating alone and how operational dips during due diligence lead to price retrades.

[21:40] How to structurally prepare your business for market by minimizing owner dependency and customer concentration.

[27:10] Navigating post-sale mechanics: Earnouts, seller notes, and rolling equity.

[31:41] Why conducting sell-side due diligence on your prospective buyer is critical.

Subscribe to our Substack for episode alerts and research: https://asymmetricexit.substack.com/

Learn more about Shell Capital Management:

https://shell-capital.com/

What is the true cost of negotiating the sale of your business alone against professional buyers who execute complex M&A transactions every single day?

In this episode of the ASYMMETRY® Podcast, we sit down with Mordecai Evans, Lead Advisor at Business Acquisition Advisors. Mordecai shares his unique entrepreneurial journey—from selling grit magazines at 10 years old and working in animal health sales for Pfizer, to taking the massive, calculated risk of jumping into a commission-only M&A career with two young children at home.

We dive deep into the ultimate asymmetrical advantage for exiting founders: creating structural leverage. Mordecai breaks down the critical difference between the "list and wait" approach of Main Street brokerage and the highly competitive, structured auction process of lower-middle-market M&A.

If you are a business owner navigating private equity offers, trying to de-risk your enterprise value, or building your ultimate deal team, this episode is your blueprint.

Key Takeaways from this Episode:

• The Professional Imbalance: Why a business owner selling their only company is at a massive disadvantage when negotiating directly with professional buyers (PE, Search Funds, Strategics).

• The Multiple is a Measure of Risk: Why high customer concentration or heavy owner dependency will immediately compress your business valuation.

• Main Street vs. M&A: The stark operational differences between selling a $2M business and structuring a complex, multi-million dollar liquidity event.

• Creating True Leverage: How time pressure, competitive bidding, and a blinded CIM (Confidential Information Memorandum) force buyers to submit their best price and terms.

• The Complete Deal Team: Why your CPA and attorney are not enough to maximize value, and the specific role an M&A Advisor plays in the negotiation process.

Episode Timestamps:

[02:12] - Main Street vs. Lower Middle Market vs. Investment Banking .

[08:44] - The critical communication lessons learned from Pfizer pharmaceutical sales .

[10:17] - The asymmetric risk of jumping into a commission-only career .

[11:39] - The difference between Main Street "list and wait" and complex M&A .

[19:44] - The professional imbalance between one-time sellers and professional buyers .

[24:57] - The step-by-step M&A timeline from engagement to wire transfer .

[37:05] - De-risking the business and why your multiple measures risk .

[42:10] - The specific roles of the ultimate M&A deal team .

[46:56] - The Asymmetric Insight: Taking care of people and living by the Golden Rule .

Links Mentioned: https://baallc.biz/

What is the true cost of treating your business exit like a sudden 30-day transaction, and how do you build the structural readiness required to actually maximize your enterprise value?

In this episode of the ASYMMETRY® Podcast, we sit down with Mark Girouard, founder of Stage Right Ventures. Mark shares the unglamorous reality of leaving the highly structured, pristine world of corporate finance to dive into the unpredictable and chaotic landscape of lower-middle-market business transitions.

Key Takeaways from this Episode:

• The Illusion of Being "Deal Ready": Why founders must stop treating an exit as a rushed legal event and start treating it as a multi-year structural transition with clean books.

• Navigating "No Man's Land": How to survive the operational gap between where you are now and where you want to be when you eventually exit.

• The 5 "D's" of Forced Exits: Why you must be deal-ready today to protect your wealth, as 50% of exits are forced by death, disability, divorce, disagreement, or distress.

• The 75% Regret Rate: The psychological reality of exiting and why personal, post-exit planning is just as critical, given that 75% of owners profoundly regret selling within 12 months.

• The "Whole Cycle" Advantage: Why enterprise value is not created by a single explosive score, but by the consistent execution of fundamental structural improvements day in and day out.

Episode Timestamps:

[00:42] - The "Whole Cycle" approach to business transitions.

[02:24] - Moving from corporate finance to lower-middle-market realities.

[10:53] - Decision-making and identifying systematic risk. [17:52] - Navigating the operational "No Man's Land". [22:45] - The illusion of being "deal ready" and the need for clean financials.

[25:00] - The 5 "D's" of forced exits.

[27:27] - The 75% exit regret rate and post-exit planning. [32:41] - The Asymmetric Insight: Consistent execution over single transactions.

Links Mentioned: https://stagerightventures.com/

What is the true cost of scaling a business while ignoring your own internal chaos, and how do you build a culture that allows you to confidently hand over the reins?

In this episode of the ASYMMETRY® Podcast, we sit down with Brandon Syler, founder of MP Parts and the OneBridge Experience. Brandon shares the unglamorous reality of starting a manufacturing company in his basement during the 2008 Great Recession, consolidating his family into a 1,600-square-foot house to survive, and doing the intense, personal "story work" required to survive unbounded organizational growth.

We dive deep into the ultimate asymmetrical advantage: structural leadership and emotional optionality. Brandon reveals how implementing strict Standard Operating Procedures (SOPs) and deeply connecting with his team allowed him to completely replace himself, eventually promoting his assistant to President of the company. If you are a business owner navigating the complexities of scaling, building an elite culture, or preparing to decouple your time from your enterprise, this episode is your blueprint.

Key Takeaways from this Episode:

• The "Glass of Beads" Reality: Why unmanaged personal trauma acts as a hidden liability on your balance sheet, bleeding into your culture and enterprise value.

• Maneuvering Growth Risks: How Brandon navigated the shift from a chaotic 25-employee operation to implementing EOS and weekly 1-on-1 development meetings.

• The Power of Story Work: Why chaos at work and chaos at home is almost always a direct result of unmanaged chaos inside the founder.

• Creating Optionality: How building strict structural clarity and psychological safety gave Brandon the ultimate leverage to step away and launch a nonprofit.

• The S.O.S. Framework: Why Seeking wisdom, Owning your story, and Serving others is the exact formula for expanding your leadership capacity.

Episode Timestamps:

• [01:06] - Shifting the metric of success from revenue to culture.

• [03:19] - Risking a $40k 401k to start a basement business during the 2008 financial crisis.

• [08:54] - Hitting the 2016 growth wall: Surviving utter chaos and deploying the E-Myth.

• [14:58] - The "Glass of Beads" analogy and doing your internal work.

• [21:31] - The structural ROI of flying employees in for quarterly development meetings.

• [27:51] - The S.O.S. Framework and the ultimate rotation event: Promoting an assistant to President.

• [34:56] - Building OneBridge and writing Sacred Impact for the "1% founders".

• [38:50] - The Asymmetric Insight: Why priority mathematically determines capacity.

Links Mentioned: https://onebridgeexperience.com

What is the true cost of scaling a family business, and how do you know when it’s time to cash in your chips?

In this episode of the ASYMMETRY® Podcast, we sit down with Tom Sheldon, former business owner and current Executive Producer of Northeast Georgia Business RadioX. Tom shares the unglamorous, 24/7 reality of taking over a legacy pest control business, overcoming the "boss's kid" stigma, and taking the calculated risks required to triple its size.

We dive deep into the ultimate asymmetrical advantage: optionality. Tom reveals how starting a voiceover career three years before his exit gave him the leverage to negotiate his sale from a position of power. If you are a business owner navigating the complexities of scaling, managing employees, or preparing for an eventual exit, this episode is your blueprint.

Key Takeaways from this Episode:

• The Reality of the Family Business: The 24/7 demands, locking the office door on Friday, and dealing with employees showing up at your house unannounced.
• Maneuvering Growth Risks: How Tom navigated the shift from a small crew to managing 20-25 employees and taking on the necessary debt to lease equipment.
• The Power of Walking Away: Why being willing to pack up your portfolio and walk out of a negotiation is the ultimate leverage when selling your business.
• Creating Optionality: How Tom’s side venture into voiceover work removed the desperation from his exit strategy.
• Leadership 101: Why simply "showing up" and leading by example is the most important standard you can set for your team.

Links Mentioned:

https://businessradiox.com/

When his son Christian was diagnosed with autism, Michael Pereira's understanding of risk and security changed overnight. The "American Dream" of his corporate enterprise software career—and the standard employer benefits that came with it—suddenly looked dangerously inadequate for his family's long-term reality.

In this episode of the ASYMMETRY® podcast, Michael shares his journey from traveling 80% of the time in corporate America to founding the Autism Voyage, a platform helping families navigate long-term planning for neurodivergent children.

He discusses the terrifying realization that standard employer disability and life insurance policies fall extremely short, and why no single financial planner can solve the complex puzzle of special needs planning.

If you are a business owner or professional, this episode delivers a masterclass on building a professional ecosystem, using insurance as a true risk transfer, and securing your child's future without jeopardizing their government benefits.

Key Takeaways from this Episode:

• The Employer Benefit Trap: Why relying solely on corporate short-term/long-term disability and standard life insurance policies is a massive risk for families with special needs.
• Building a Professional Ecosystem: Why you cannot rely on a single professional, and how to connect the dots between attorneys, CPAs, and specialized advisors.
• Protecting the Business and the Family: How entrepreneurs can utilize buy-sell agreements, key man insurance, and business overhead expense coverage to protect their legacy.
• The Truth About Life Insurance: Understanding that life insurance is a transfer of risk—not an investment—and how to use it as a funding mechanism for a Special Needs Trust.
• The Power of Adaptability: Michael's advice on getting comfortable with uncertainty, staying flexible, and remaining consistent, drawing from both his corporate background and his traditional Hispanic upbringing.

Links Mentioned:

• The Autism Voyage: www.theautismvoyage.com

Many businesses fail not because their product is bad, but because it is so good that the founder becomes the ultimate bottleneck. When a company grows but every single decision still has to go through the owner, the business isn't actually an asset—it’s just a highly demanding job.

In this episode of the ASYMMETRY® Podcast, we sit down with Kent Hepler, a former Navy helicopter pilot and the founder of Vectored Approaches.

Drawing on 25 years of experience in the military and private sector—including teaching night landings on ships and deploying to Iraq—Kent shares how he helps chaotic businesses find their way through the clouds. He explains the calculated risks required to step out of the daily operations, build Standard Operating Procedures (SOPs), and transform a founder-dependent company into a scalable, sellable enterprise.

Key Takeaways from this Episode:

• The Danger of the "Hub and Spoke" Model: Why a 10-person company where everyone reports directly to the founder is doomed to stall, and why founder dependency makes a business impossible to sell.
• Revving in Neutral: How to recognize when your team has the "pedal to the metal" but the business isn't actually moving forward because of a lack of internal systems.
• The Aviation Approach to Business: How the concept of a "vector"—getting navigational guidance through the clouds from air traffic control—applies directly to business consulting and operational clarity.
• Reframing Failure: Why failing in business is just like missing a heavy lift in the gym; it simply identifies your current capability limit so you know exactly where you need to build strength.
• The Ultimate Risk Transfer: Why delegating responsibility and accepting that your team might do things differently is the required price for gaining your freedom back.

Links Mentioned:

• Vectored Approaches: vectoredapproaches.com