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

About this episode

Stephen Scoggins shares insights on preparing a business for sale and the importance of strategic planning for entrepreneurs.

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…

People in this episode

Host: Justin Donald

Guest: Stephen Scoggins

Topics covered

• business exit strategies
• entrepreneurship
• company valuation
• tax strategies
• leadership
• personal growth

Keywords

• selling a business
• entrepreneur
• valuation
• asset sales
• stock sales
• quality of earnings
• liquidity event

Mentioned in this episode

Organizations: Build podcast

More episodes of The Lifestyle Investor - Investing, Passive Income, Wealth

• 294: How Vertical Integration Scaled This Real Estate Firm to $5 Billion AUM with Kip Sowden & Doug McKnight · June 11, 2026 · 41 min
• Lens #02: Why Doing "All the Right Things" Keeps You Broke · June 8, 2026 · 7 min
• 293: The Invisible Riptide That Pulls Entrepreneurial Dads Away From Their Family with Jeff Zaugg · June 4, 2026 · 35 min
• Lens #01: 3 Shifts the Ultra-Wealthy Already Made (And You Haven't) · May 31, 2026 · 7 min
• 292: The Firefighter Who Walked Away From Early Retirement And Chose Entrepreneurship with Jesse Flocken · May 28, 2026 · 41 min
• 291: The Power of Scheduling Think Time to Unlock Peak Performance with Talor Zamir · May 21, 2026 · 46 min