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...

early inheritance
By Rob Shelton September 17, 2026
A successful legacy may ultimately be measured less by what you leave behind and more by what you prepare others to do with it.
lifestyle creep
By Rob Shelton September 3, 2026
A bigger house, better vacations, private school, or a second home may all be affordable, but what happens when yesterday’s luxuries quietly become today’s obligations?
business investor
By Rob Shelton August 27, 2026
Bringing in a new investor can feel like a major win, but the order of operations matters more than many business owners realize.
Show More