Business Leaders Podcast: One More Turn
“What happens after I sell and the wire hits?”
You might not have even thought to ask that question—until you were providing wire instructions.
Then it hits you: you’d prepared for the transaction perfectly… and your life after it not so much.
Here’s what nobody tells you:
The good news? You received a large wire.
The bad news? No monthly paycheck. No company benefits. No calendar. No team. No identity tied to what you built. And according to Exit Planning Institute research, 75% of founders experience seller’s regret in their first year.
Conversations with owners who already sold ($5M-$100M exits) and are now 1-36 months into “the rest of their life.” Not the highlight reel. Their actual experience.
The identity void when your title disappearsMarriage renegotiation when you’re suddenly homeHow the first Monday with nothing on the calendar actually feelsThe investment mistakes made in the first 90 daysThe blind spot in traditional exit planning that left them unprepared
If you’re 1-3 years from your own exit, this is your reconnaissance. If you’ve already sold and thought you were the only one struggling—you’re not. These founders said yes to the interview to share their hard-earned wisdom and insights.
Hosted by Bob Roark, CEPA | 200+ episodes with business owners | Exit planning specialist and business owner.
This podcast provides general educational information and is not personalized financial advice. For advice specific to your situation, consult a qualified professional.
© 2026 Bob Roark · more info
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