May 29, 2025

Steve Whitteberry: Navigating Business Ownership Transitions: Strategies for Success and Legacy Building

27 minutes

🧠 What’s Your Business Really Worth — and Are You Ready to Let Go?
Most business owners think they’ll know when it’s time to transition — but are they prepared for what it really takes to exit without regret?
In this episode of Legacy Leaders, guest host James Moore sits down with Steve Whitteberry, M&A advisor and founder of Invictus MA, who specializes in helping privately held businesses navigate ownership transitions. Together, they explore the often-overlooked realities of exit planning, sharing valuable insights and practical tips for business owners nearing retirement or preparing for succession. Steve draws from decades of experience in finance, M&A, and corporate leadership to discuss valuation gaps, emotional readiness, and why exit planning isn’t just about a number — it’s about legacy. This episode is a must-listen for entrepreneurs, business owners, and advisors looking to lead their company into its next chapter with purpose and clarity.

🔑 Key Takeaways:

💵 Valuation Reality Check: Most owners overestimate their business’s worth based on personal financial goals — not market realities.

🧰 Opinion of Value vs. Full Appraisal: Steve explains a cost-effective way to understand what your business could actually sell for in the next 18 months.

🧠 Transition is Emotional: Owners struggle with identity and letting go — and many don’t think beyond “golfing” into their next purpose.

🏗 The Stronger the Team, the Smoother the Exit: If your business can’t run without you, it’s not ready to sell.

📊 Start Sooner Than You Think: Planning now — even if you’re years from retiring — means a better, more profitable outcome later.

"Most business owners determine value based on what they need to retire — not what the business is actually worth."

"If you can leave your business for six months and it runs without you, that’s a business ready for transition."

"Planning a transition isn’t an expense — it’s an investment that can return 10x or more."

💬 Quotes from Steve Whitteberry:

🔗 Conclusion:
Exit planning doesn’t start when you're ready to leave — it starts when you’re ready to think differently about your business. To connect with Steve, visit invictusma.com or email him directly at [email protected].
🎁 BONUS: Mention this podcast to receive a complimentary copy of How to Transition from Your Business Without Regret or the Beating the Boomer Bust report!

Learn more about your ad choices. Visit megaphone.fm/adchoices

...more

View all episodes

By Stan Miller & Katie Beth Hand

22 ratings