How to Know When It’s Time to Sell
- Kyle Winder
- Mar 10
- 2 min read
Kristie Shifflette built a 13-location empire. Learn when to sell, attract investors, and maximize your exit strategy.
About this Episode
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. 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
Kristie’s negotiation skills turned a good deal into a great one.
About Our Guest
Kristie Shifflette
Kristie Shifflette is a seasoned entrepreneur and fitness industry leader who built a 13-location Orangetheory Fitness empire from the ground up. With a keen eye for business growth and a fearless approach to risk, she successfully navigated the challenges of scaling a capital-intensive franchise while maintaining control. Known for her strategic mindset and sharp negotiation skills, Kristie has mastered the art of building, leading, and ultimately selling a thriving business on her terms.
Definitions
Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.
Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.
Letter of Intent (LOI): This document outlines the basic terms and conditions of a deal before a formal agreement is drawn up. It serves as a mutual commitment between the buyer and the seller to move forward with the transaction on the agreed-upon terms.
Re-Trading: This occurs when a buyer attempts to renegotiate the purchase price of a deal after initially agreeing to one. It is often seen unfavorably as it occurs after due diligence, seemingly exploiting newly discovered information.
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