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

September 10, 2026

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 aren’t guaranteed

📈 Equity Ownership: Private shares aren’t cash

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.


Go inside the episode:

0:00 – Intro

2:30 – Medical Practice Example

4:35 – Buyer Strategy

5:29 – Specialty Risks

6:12 – Financial Risks

7:28 – Future Payments / Second Payday

8:20 – Larger Company Equity

9:41 – Worth the Risk?

10:45 – Case Study Lessons

11:55 – Main Takeaways


Helpful Resources:


Phone: 801-717-9237

Schedule your no-cost discovery meeting: https://www.axiowm.com/what-we-do

Get your copy of Rob’s books: https://www.axiowm.com/book

Let us speak at your next event: https://www.axiowm.com/speaking

Check us out on YouTube: https://www.youtube.com/channel/UCtidWpldZGUBLmr24oWy87Q


Subscribe & Follow The Show On Your Favorite Apps:
YouTube
Spotify
Apple Podcasts
Amazon Music
iHeart Radio
Podchaser

DISCOVER MORE...

ai scams
By Rob Shelton • October 29, 2026
Scams are getting more sophisticated, and even people who consider themselves careful can be caught at the wrong moment.
using your wealth
By Rob Shelton • October 22, 2026
Rob offers insight into how gratitude, generosity, and a clearer sense of purpose can shape the way families think about what their money is ultimately for.
protecting wealth
By Rob Shelton • October 15, 2026
Rob dives deep into why successful families should look beyond market risk and think about the other events that could disrupt the life their wealth is meant to support.
Show More