The Lifestyle Investor - Investing, Passive Income, Wealth

281: How to Avoid Leaving Millions on the Table When Selling Your Business with Stephen Scoggins

18 snips

Mar 12, 2026

Stephen Scoggins, entrepreneur, author, and host who built multiple companies including a nine-figure business and completed a 2023 exit. He talks about preparing a company 3–5 years before sale, structuring management buyouts and seller financing, quality-of-earnings diligence, F-reorgs versus asset sales, and building leadership, SOPs, and incentives so a business can scale beyond its founder.

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ANECDOTE

Why Stephen Decided To Exit After 25 Years

Stephen sold after 25 years because he realized he wasn't the right leader to scale to $150M and wanted new purpose.
He merged with two operators, set a 5-year roadmap, provided cash and seller financing, and exited December 29, 2023.

INSIGHT

AI Integration Can Multiply Valuations

Incorporating technology or AI can dramatically expand multiples because it positions the business as a platform.
Stephen expected 8–20x multiples depending on AI integration and recurring EBITDA of $10–12M.

ADVICE

Use Seller Finance And Rollover Equity To Bridge Buyers

Use seller financing and minority rollover equity to align incentives when strategic buyers or management lack full cash.
Stephen sold 20% as a minority stake, provided seller financing, and remained board chair to mentor the new team.

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It’s crazy when you think about it, but less than 1% of entrepreneurs ever sell their companies. Even fewer do it intentionally, strategically, and on their terms. If you’re building a business without preparing for a future exit, you may be leaving millions on the table or worse, creating a company that can’t function without you.

Stephen Scoggins knows this firsthand. He is a speaker, author, and host of the Build podcast who created multiple companies — including one that grew to nine figures in annual revenue and successfully exited in 2023. But his story isn’t just about a financial win. It’s about faith, leadership, identity, and learning how to structure a business so it can scale beyond you and create meaning and purpose in your life.

You’ll hear what Stephen believes most entrepreneurs get wrong about selling their business, and the tax strategies he’s now implementing after a massive liquidity event. We also dive deep into his journey from sleeping in his car to building companies that employ hundreds — and how faith shaped every turning point along the way.

In this episode, you’ll learn:

✅ Why most entrepreneurs wait too long to prepare their business for sale and what Stephen recommends for runway time prior to an exit.

✅ How quality of earnings can dramatically impact your final valuation and why buyers use it to justify lowering your multiple.

✅ The difference between asset sales versus stock sales and why an F reorganization can have a dramatic impact on value.

Show Notes: LifestyleInvestor.com/28 1

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