Reflections on a Successful Business Sale: Insights from Cannon

What does it really take to sell a business without regret? In this anniversary conversation, Cannon Carr shares his experience of leading his firm through a major transition—what went as expected, what surprises hit hardest, and how preparation years in advance made all the difference.

From the importance of clean books and solid processes, to setting non-negotiables, to navigating the emotional toll of the deal, Cannon gives a candid look behind the curtain of mergers and acquisitions. He also unpacks his Three R’s Framework—Reward, Reinvest, and Repurpose—and why values are just as important as valuation.

Whether you’re a business owner considering your own exit or simply curious about how big deals come together, this episode delivers insight, vulnerability, and practical takeaways you won’t hear anywhere else.

What You’ll Learn in This Episode:

• Why two-thirds of business sales end in regret—and how to avoid that outcome.

• The foundational work every owner should do 2–3 years before a sale.

• The role of non-negotiables in deal negotiations.

• The emotional toll of selling—and how to stay grounded through it.

• Why shared values with a buyer are just as important as valuation.

• The importance of diversified wealth before a transaction.

• How Cannon’s Three R’s framework shaped his decisions.

• The personal and family impact of going through a business sale.

• How Vistage peer groups, EOS, and trusted advisors played into the process.

• Final advice Cannon gives to business owners considering a future exit.

Resources & Links Mentioned:

• Cannon Carr’s website & resources: cannon-carr.com

• EP Wealth Advisors: epwealth.com

• Vistage: vistage.com