Ep 34. Exit Regret is Real: Here’s How to Avoid It with Brian Dukes
Many founders dream of a big exit, but what happens when it doesn't feel like a win?
In this episode, Brian Dukes, entrepreneur and co-founder of ExitWise, the identity crisis so many founders face after selling their business, and why most aren't ready for what comes next.
He shares how taking time off, redefining success, and setting clear boundaries helped him reset and build again, this time, on his own terms.
We talk about identity loss, founder ego, post-exit regret, why empathy matters so much in M&A and how to avoid the post-exit regret no one prepares you for.
If you're building to sell, or already thinking about what comes after, this conversation will help you prepare beyond just the numbers.
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Brian Dukes began his career in Big 5 Consulting, later earning an MBA from the University of Michigan. Rather than follow a traditional corporate path, he joined a Ford Motor Company startup, and a few years later co-founded a digital marketing agency that became a leader in the automotive space. Through building and exiting that business, he gained firsthand experience with the emotional and strategic complexities of M&A.
In 2022, Brian co-founded ExitWise, an M&A advisory platform that helps entrepreneurs navigate exits with clarity, empathy, and the support he once wished he had. Today, he helps fellow founders plan and execute successful exits, and design a life they won’t want to exit from.
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00:00 – Welcome and intro to Brian Dukes
01:45 – Brian’s “very traditional path” that took a sharp entrepreneurial turn
03:15 – Why the entrepreneurial journey feels more like family than competition
05:00 – The moment Brian left his job (while expecting a baby!) to start his business
08:15 – Why he thought he was “done” after the exit… and what happened 30 days later
10:45 – The surprising reason he co-founded Exit Wise
14:30 – Boundaries vs. balance: a better way to build a business and a life
18:45 – What the first 30 days post-exit really looked like
24:00 – The mindset shift that helped him design a better business (and life)
28:15 – The unexpected grief of exiting, and how Exit Wise supports founders through it