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

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

Author: John Warrillow March 7, 2025 Duration: 1:10:04

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 


For any entrepreneur, the idea of selling the company they've built is both a daunting prospect and a potential pinnacle of success. Built to Sell Radio, hosted by John Warrillow, steps into that complex space with a clear, practical focus. This isn't about abstract theory; it's a weekly conversation grounded in real experience. Every episode features a different founder who has recently navigated the sale of their business. The discussion goes straight to the heart of the matter: understanding the personal and strategic reasons behind the decision to sell. Listeners get an honest breakdown of what worked, from preparation and valuation to negotiation, and perhaps more importantly, the unforeseen pitfalls and mistakes made along the way. It’s that candid post-mortem, the lessons learned in the trenches of a transaction, that provides unparalleled value. By compiling these firsthand accounts, the podcast builds a comprehensive library of exit strategies and cautionary tales. Tuning in feels like gaining access to a private mastermind, where seasoned entrepreneurs share the unvarnished truth about cashing in their life's work. If you're contemplating your own eventual exit, this series offers the nuanced, peer-to-peer insights you need to think like a buyer, protect your interests, and ultimately, build a business that is truly desirable. Built to Sell Radio serves as an essential guide, transforming the opaque process of selling a business into a clearer, more manageable journey.
Author: Language: English Episodes: 100

Built to Sell Radio
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