Two Exits from One Business: Opportunity, Risk, and the Second Bite

Legacy Beyond Wealth with Rob Shelton · Sep 10, 2026 · 13m

Selling a business doesn’t always mean walking away with one check and closing the chapter. Rob explains how some owners are taking cash up front, staying involved, and keeping the possibility of another payday later. The opportunity can be significant, but so can the risk when that second exit depends on factors outside your control.

Here’s what we discuss in this episode:

🏢 Larger Buyer: Scale may increase value

🩺 Case Study: Medical practice structures earnout

🤝 Buyer Protection: Future results reduce risk

💵 Seller Benefits: Gain liquidity and flexibility

⚠️ Earnout Risk: Future payments…