What would it take for you to sell your business?

Carmina Santamaria
Feb 9
4 min read

The conversation most business owners are avoiding

Most business owners who start a business think: “I’m going to nourish and grow this baby and we’re going to grow old together”.. I know I did! With almost each one of my businesses, no joke! I fell in love with the idea, I pushed as hard as I could to take each one of them off the ground.

I remember once, a respected mentor of mine asked me: “what would it take for you to sell your business?”

I said: “No way! I’m not selling it, this is mine and I want to keep it!”

And then he started throwing numbers at me..

I go: “No, nope, no..” and then the number became so significant (9 digit number) that I started to think about it... “OK, maybe, I would consider it at that range.”

It turns out, I too had a number for my baby. Internally, it almost felt disgusting, but I did have a number.

It wouldn’t be until years later that I would come to experience an exit.

Unless you’re a serial entrepreneur who’s built multiple companies, most business owners don’t think about an exit strategy. You might think - like old me- that you want to keep the business, maybe transfer it within the family.

Now here is a hard truth: Most kids don’t want your business. 🙁 - don’t hate the messenger, I’m only sharing hard data here.

Right now, there are 5.5 million family businesses in America. These aren’t just mom-and-pop shops - they employ a massive chunk of the U.S. workforce. And guess what? The next generation would rather you sell and hand them the cash than take over the day-to-day operations. 😱

This isn’t about lazy millennials or Gen Z kids who “don’t want to work.” This is about a fundamental shift in what people want from their careers and lives.

Most family business owners don’t realize: While you’re waking up at 5 AM to open the shop like you’ve done for 27 years, your kids are watching you miss their soccer games, skip vacations, and stress about payroll every other week. They saw the sacrifice and tears. They just don’t want to make it themselves.

However rare these days, I do know a couple of business women who are working on the family business transfer from different ends: one of them is transferring the business and another one is receiving the business and taking the reigns. In my opinion, that’s awesome, they get the chance to build on the legacy that cost decades of building versus starting from scratch.

The Numbers Don’t Lie

Bloomberg estimates that $18 trillion - yes, with a T - in small-business value is about to change hands in the coming decades. That’s entire industries, communities, and legacies up for grabs.

And here’s the kicker: Most of these business owners have zero succession plan. They’re approaching retirement assuming their kids will “figure it out” or “eventually come around to the idea.”

Spoiler alert: They won’t.

What This Means for You

If you’re counting on your kids to take over, it’s time for an honest conversation. Not the “someday you’ll run this place” conversation you’ve been having since they were twelve. A real one.

Ask them: “Do you actually want this business, or are you just afraid to disappoint me?”

The answer might sting. But it’s better to know now than to wake up five years from retirement with no plan and a kid who’s been dreading this conversation as much as you have.

There are options besides the traditional sale

You know who’s paying attention to this massive wealth transfer? Private equity firms. They’re consolidating entire sectors, stepping in when families don’t have a plan and heirs don’t want the business.

Is that a bad thing? Not necessarily. For many owners, PE offers a real exit with real money - and in some cases, you can stay involved if you want to. It’s rather common for PE firms to ask the business owner to stick around for a transition period - a couple of years- and then you can get to walk away. It’s not the boogeyman. It’s an option.

But here’s the catch: unless you have an exit strategy, selling is really hard. Stats show that only 1 in 11 businesses listed for sale actually get sold. Don’t take my word for it—research it yourself. I said hard not impossible!

So What Do You Do?

If you’re still here and didn’t just close this article, here’s what I want you to sit with: