Designing a Legacy
What Matters Beyond the Deal
Something more
The conference room was silent except for the ticking of the wall clock. Across from me sat a founder who had just sold the company he’d built over 28 years. He had walked away with a life-changing check. But instead of the exhilaration you’d expect, his voice was flat. “I thought I’d feel… something more,” he admitted.
This is the part no one warns you about.
Most owners focus on the deal: the selling price, the tax strategy, the legal mechanics. And yet, I watch sellers find themselves adrift once the transaction is over. The scoreboard says they won, but it feels like the game ended before they were ready to leave the field.
That’s because selling a business isn’t just a financial transaction; it’s a personal identity shift. And if you don’t design for what comes after, you risk building wealth without building meaning.
The sudden quiet
When you’ve spent years (or decades) driving growth, leading teams, and fighting fires, the sudden quiet of post-exit life can feel like stepping into a soundproof room. Many founders underestimate how much of their daily purpose and personal relevance comes from their business. Without a plan, some spiral into boredom, overcommit to ill-fitting projects, or even buy another business just to feel that pulse again.
Here’s what no one tells you: the highest value you can extract from your business exit has nothing to do with EBITDA multiples or market timing. It comes from consciously shaping what you want your life, influence, and impact to look like once you no longer own the company.
The most successful sellers I’ve spoken with do one thing differently: they design the legacy layer of the deal before they negotiate the price.
One founder exited a specialty manufacturing business in the Midwest. Instead of rushing into the next thing, he had spent the prior two years working with a personal board of advisors to define the legacy he wanted: mentoring first-time founders, investing in community infrastructure, and building a family foundation. When the deal closed, he didn’t just step away.
He stepped into something he had already built.
Contrast that with another owner who sold quickly in a hot market without planning. His valuation was strong, but the post-exit vacuum left him chasing random ventures. Within 18 months, he felt like a spectator in his own life.
And the counterintuitive truth: designing your legacy before the deal can actually increase the sale price.
Why?
Because a founder who is emotionally prepared and has a clear post-exit vision negotiates from a position of confidence. Buyers can feel it. You’re less reactive, less desperate to cling to familiar ground, and more open to deal structures that optimize long-term wealth.
The highest ROI in an exit often comes from decisions made outside the deal room.
Designing your legacy
Your legacy design doesn’t have to be grandiose. It could be writing the industry playbook you wish you had when starting out. It could be funding scholarships for employees’ kids. It could be as simple as crafting a transition that leaves your team stronger than when you started. The point is to choose before the market chooses for you.
The future you want post-exit won’t just materialize on its own. It’s built in the quiet hours before you sign the LOI. It’s reinforced in the boundaries you set during due diligence. And it’s made real in the commitments you honor once the wire hits.
If you treat your exit as an endpoint, you’ll experience it as a loss. If you design it as a launchpad, you’ll experience it as an inflection point. The difference is everything.
So ask yourself: If the deal closed tomorrow, would you be ready to live the next chapter? And not just financially—would you be ready emotionally?
I’ll leave you with this: Your company might be your greatest asset, but your legacy is your greatest currency. Spend it well.
David Hermann, CEO of hermanngroup and M&A Advisor/Broker at Sunbelt Business Brokers of Colorado
David Hermann is a transformative advisor and strategist who turns complex business challenges into extraordinary successes. Known for driving over $500 million in documented financial improvements for clients, David partners with C-suite leaders to unlock their full potential. With 60+ speaking engagements, numerous publications, and a spot in the top 1% of Consulting Voices and top 1% of the Social Selling Index on LinkedIn, he’s passionate about making strategy, change leadership, and operations insightful and accessible.