Oct 14, 2026 · 31 min · 10 segments
Every day, roughly 10,000 baby boomer business owners hit retirement age, and most of them have no exit plan. The conventional wisdom says they have two choices: sell or shut it down. Richard Shaull…
Can you go into those first chapters and kinda explain a bit more? And I wonder, too, before you do that, it, you know, it, it does seem like in this new culture, it's almost like the number of times you sell is almost like...
But I know a lot of people who talk about selling, and to your point, they're not happy with the outcome, or financially it wasn't a big win.
Like, a lot of businesses only trade for, like, three times seller discretionary earnings.
So it's like three years of income, and you take the taxes out, all the fees out of that It's only like a year and a half.
So what do you do after that year and a half? And a lot of people don't talk about that, that you're basically just back to getting a job if-
And, and, and I think this is where, again, that, that narrative that the scoreboard is how many exits you've had, it really serves two groups primarily.
You just have to recognize that they're playing a very specific game, and you have to decide if you wanna be part of that game.
And of course, if you're a VC-backed company and you're scaling to the moon, that's just kind of the road.
But for the vast majority of business owners in the US, they didn't actually really start their business to sell.
If they reflect on it, some of them started it because they wanted to have freedom.
And so I just think it's important for owners to really think through what do they actually want, what's the real outcome that they're aiming for, not one that's given to them by some external investor.
Can you go into those first chapters and kinda explain a bit more? And I wonder, too, before you do that, it, you know, it, it does seem like in this new culture, it's almost like the number of times you sell is almost like...
But I know a lot of people who talk about selling, and to your point, they're not happy with the outcome, or financially it wasn't a big win.
Like, a lot of businesses only trade for, like, three times seller discretionary earnings.
So it's like three years of income, and you take the taxes out, all the fees out of that It's only like a year and a half.
So what do you do after that year and a half? And a lot of people don't talk about that, that you're basically just back to getting a job if-
And, and, and I think this is where, again, that, that narrative that the scoreboard is how many exits you've had, it really serves two groups primarily.
You just have to recognize that they're playing a very specific game, and you have to decide if you wanna be part of that game.
And of course, if you're a VC-backed company and you're scaling to the moon, that's just kind of the road.
But for the vast majority of business owners in the US, they didn't actually really start their business to sell.
If they reflect on it, some of them started it because they wanted to have freedom.
And so I just think it's important for owners to really think through what do they actually want, what's the real outcome that they're aiming for, not one that's given to them by some external investor.
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