A founder can successfully negotiate their dream purchase price, but if they accept the wrong deal structure, a sudden market shift can destroy their enterprise value.

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

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

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