Mastering the Deal: Earn-outs, Equity Rolls & Seller Notes—Risk or Reward?

Most owners want 100% cash at closing. Most acquirers want the opposite—they try to hold back as much as possible and tie it to future results. That tug-of-war defines the negotiation. 

In this week’s episode of Built to Sell Radio, you discover how to turn common transition structures from potential pitfalls into opportunities for upside. 

You’ll learn how to: 

• See when an earn-out is a raw deal—and when it’s a smart bet. 

• Weigh the upside of rolling equity against the loss of control. 

• Decide if seller financing is strategic leverage or unnecessary risk. 

• Decode why acquirers push these structures and how to push back. 

• Spot situations where the second bite of the apple can be worth more than the first. 

• Learn from real stories—like Rob Walling and Adam Coffey—about when these deals worked and when they didn’t. 

• Protect your downside while still leaving room for upside. 

Listen now to hear how experienced founders have navigated these three transition types—and what you can learn for your own exit. 

Show Notes & Links

The 4 Types of Acquirers

Adam Coffey’s episode

Rob Walling’s episode 

Steve Dvitikos episode

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About Our Guest

Inside the Mind of an Acquirer

Steve Divitkos — Acquisition entrepreneur and search-fund investor; Founder of Mineola Search Partners and former CEO of Microdea, where he doubled revenue and quadrupled equity value before exiting.

Adam Coffey — PE operator turned best-selling author of The Private Equity Playbook, The Exit Strategy Playbook, and Empire Builder; spent 21 years as a PE-backed CEO completing 50+ acquisitions and multiple billion-dollar exits.

Rob Walling — Serial entrepreneur and investor; co-founded TinySeed and MicroConf, founded Drip (acquired), and hosts Startups for the Rest of Us—a go-to voice for bootstrapped SaaS founders.