Ep 484 How to Know When It’s Time to Sell


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Mar 06 2025 70 mins   35

Kristie Shifflette built a 13-location Orangetheory Fitness empire from scratch—bootstrapping a capital-hungry business, personally guaranteeing leases, and taking on risk most founders wouldn’t touch. In the end, it paid off for Kristie and in this episode, you’ll discover how to:

  • Bootstrap a capital-intensive business without giving up control

  • Reduce your risk when taking on an investor

  • Attract entrepreneurial employees who will care as much as you do

  • Think about the $10 million milestone (and why it matters to private equity)

  • Know when to take some chips off the table—and when to double down

  • Ace management presentations with an acquirer

  • Play hard to get (even when you want to sell)

  • Get an acquirer to bump up their offer

  • Max out an earn-out payment—even if you don’t quite hit your targets

  • Spot an acquisition offer that’s likely to be re-traded