How to Know When It’s Time to Sell

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 

Kristie’s negotiation skills turned a good deal into a great one. 

Show Notes & Links

Connect with Kristie on LinkedIn

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.

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.