If you ask a business owner what percentage of their net worth is tied up in their business, most will say somewhere between 70–80%. Starting a business takes time, effort, and sacrifice, so it’s no surprise that founders often pour everything they have into making it work.

What’s striking about that stat is this: Only 17% of businesses are actually prepared to sell or end up completing a transaction.

And of those that do sell, 70% of owners report feeling unhappy after the deal closes, often because they weren’t fully prepared for what comes next, financially or emotionally.

Selling a business is hard.

That’s where the Business Transitions Summit comes in. This one-day conference gives business owners the knowledge and connections they need to plan for a successful exit. I first attended last year and am excited to see it continuing and expanding to more cities.

This year’s summit featured a wide range of speakers, including entrepreneurs, former owners, wealth managers, investors, and more. Topics covered everything from shifting from doubt to decisive action, to building massive value in your business, understanding and minimizing tax consequences, navigating M&A, and beyond.

Here are three key takeaways I had from this year’s conference:

Dissect Your Fear

Jeff Schiefelbein, a successful entrepreneur and founder of Undivided Life , spoke about fear including how it shows up in our lives, and how to move through it with courage and clarity. His message: fear is inevitable, but it doesn’t have to control us.

This is especially relevant to business owners facing transition. Fear is often the hidden reason exit planning gets delayed or avoided altogether. Whether it’s fear of losing purpose, fear of financial uncertainty, or fear that the business can’t survive without you — it’s real, and it’s common.

But here’s the catch: if fear goes unexamined, it becomes a barrier to smart decision-making.

A few key takeaways from his talk:

• We all feel fear.
• Fear isn’t going away.
• The worst case scenario almost never happens (but if it does, you can handle it).
• Fear is often rooted in the false belief that you’re not equipped to face what’s ahead (but you are).

Jeff shared moments in his life where fear could’ve stopped him:

• Letting go of CARPOOL at Texas A&M, the impactful nonprofit he founded at Texas A&M that over the years has given ~300,000 safe rides home.
• Quitting a corporate job in Texas in his early 20s to move to New York City and pursue disco dancing — a decision that raised more than a few eyebrows. Imagine breaking this news toyour parents?
• Starting and scaling businesses, each with its own risks and unknowns.
• On a personal level, navigating the complexities of fatherhood and the unexpected challenges that come with it.

So what do you do with fear? Jeff offered a simple approach: discern and decide.

Visualize the situation. Ask yourself, “Who am I in this moment?” Write out pros and cons. Let go of the illusion of a perfect past. If you catch yourself thinking, “I wish I had never…” — pause and reframe: you did.

Later in the day I heard Walt Bettinger say, “I’ve given up all hope for a better past.”

No regrets. Now paddle like hell.

Talk things out. Try silent meditation. Embrace the fear. Feel it and take action anyway. Even in fear, stay calm. And know the fight is worthy.

Planning is Critical

Tom Bronson, CEO of the Business Transitions Summit, posed a key question to business owners throughout the event: Are you the sun?

In other words, does everything in your business revolve around you or around a clear mission, shared values, and a strong team? Can your business run without you?

To help owners assess this, Tom encouraged owners to self-assess through a few questions:

• Do you take most sales calls yourself?
• Do you approve nearly every major decision?
• Does your team depend on you daily?
• Have you documented most of your key processes?
• Have you taken a real vacation in the past year?

If you answered yes to the first few and no to the last ones, your business probably isn’t set up to sell at the valuation you’re hoping for. And more importantly, it may not be positioned to thrive without you.

That’s why long-term planning is critical.

Focus on Your People

Walt Bettinger, former CEO of Charles Schwab and now Co-Chair, shared a simple but important reminder: Your people matter more than anything else.

After college, Walt Bettinger started his career as a pension auctioneer (sounds fun, right?). Not exactly glamorous, but it gave him a front-row seat to how the retirement industry worked. Before long, he decided to strike out on his own. At just 22, he founded The Hampton Company, a retirement plan provider he named because, as he put it, “it sounded old” and he figured that might help build trust.

The company would eventually be acquired by Charles Schwab, but his story isn’t just about business success. It’s about grit, humility, and staying grounded in your values.

• For nine months, he cold-called companies with no response.
• Eventually, someone at a large company gave him a shot and decided to hire him.
• After landing his first major client, he discovered a small rounding error in a retirement report.

He faced a choice: stay quiet or speak up. What would you do?

He chose to own the mistake. The client’s response stuck with him. She told him, “Mistakes are normal. How you recover is important.”

That mindset shaped his leadership style from then on. While building Hampton, Walt created a culture rooted in trust, respect, and empowerment:

• Employees voted on bonus allocations.
• He implemented pay transparency across the company.
• When evaluating future executives, he looked for two things: humility and emotional intelligence.

He also shared a story from one of his business classes in college:

At the end of a final exam, the last question read: “What’s the name of the person who cleans your classroom every day?” Walt didn’t know. He’d seen her many times but never asked. Walt, a studious student who was accomplishment driven and prided himself in his grades, earned a B in the class.

Her name was Dotty.

That moment stuck with him. It taught him that everyone matters — on your team, in your company, in the room. Everyone has a story and the potential to contribute.

Walt also emphasized the importance of personal priorities. As a single dad, he once declined the CEO position at Charles Schwab because he didn’t want to move his kids from Ohio to San Francisco. He later accepted the role when the timing aligned with his family’s needs.

His message was clear:

• You can’t have everything at once.
• But you can decide what matters most and stay true to it.

Work-life balance may be challenging, but living in alignment with your values is always possible.

Final Thoughts

This year’s Business Transitions Summit was full of practical advice and personal insight, but what stood out most was the human element and the stories behind it all. Whether it’s managing fear, preparing for succession, or investing in people, transitioning a business isn’t just a financial decision — it’s a personal one.

If you’re a business owner, founder, or advisor, I’d highly recommend attending in the future. The conversations are real, the people are thoughtful, and the lessons stay with you.

#ExitPlanning #Entrepreneurship #BusinessTransition #PrivateEquity #LegacyPlanning