7 reasons an entrepreneur’s first “small” exit can be so meaningful

Selling a business, even a “small” sale of 6 or 7 figures, can be life-changing financially.

But ask any entrepreneur who’s been through a sale, and they’ll tell you it’s about so much more than the check.

Sometimes, what’s even more valuable than the money, is the education.

That was the case for me the first time I sold a business. It was a content agency, and I sold it to a media company that wanted to bring us in-house.

What I learned through that acquisition set me up for another “small” exit later, when I sold a content site. And it heavily impacted how I thought about growing all of my future businesses, too.

A first exit—even a modest one—reshapes how you think about building, owning, and valuing a business. 

It recalibrates your sense of what’s possible, what you’re worth, and what you actually want. That’s true regardless of how much you sold for, whether you walked away completely or stuck around for the transition.

Here’s what that first sale can teach you—and why the lessons are often worth more than the money.

1. It opens your eyes to what’s possible

Selling something you built from scratch for a substantial amount of money brings home the point that this is possible.

That you don’t have to work for someone else to make a good living, that you can do work you enjoy and build something meaningful and still support your family. That’s huge.

It’s also a big reminder that you can build a respected company while bootstrapping, and that raising millions of dollars, while hip, isn’t the only way to succeed.

2. It helps you realize what you’re worth

Once you make a good sum of money from something you built, your expectation of how much you should earn increases.

Some of this has to do with the financial freedom money provides, because it means you can take time to be thoughtful about how to bring in revenue the next time around. That’s a real privilege.

But once you know you can provide value that’s worth real money, you’re unlikely to go back to the land of undervaluing anything you sell, especially your time.

3. You learn about the process of an acquisition

The first time you go through the process of selling a business and transitioning everything to the new owner, there’s a lot to learn.

Basics like how an acquisition works. Business terms that might not have mattered to you before. Financial concepts you previously might not have needed to understand.

You also learn about the pain points, what can be hard, what you should watch out for.

As a result of going through this, you learn how to better set up a company for possible acquisition down the road. Once you’ve sold, you can look into the future and see how to organize your next business the optimal way from the beginning.

(Editor’s note: We have a module in The Exit Playbook that covers what to think about from an acquisition perspective when you first start a business.)

4. You look at the “rules” of selling with new perspective

If you educate yourself about acquisitions, you’ll find all sorts of guidelines about how much your company should be worth.

Most of the popular formulas are based on a combination of metrics, including EBITDA. You can even find guidelines for multiples your company might sell for.

While those guidelines can serve as helpful benchmarks, there’s also a case for simply throwing all of those calculations out the window.

Why? Because the only two metrics that truly matter in a sale are:

• How much you need to earn to make the sale worth it for you, and
• How much the buyer is willing to pay to make the acquisition worth it for them.

Yes, it’s really that simple.

I saw this play out when I sold one of my web properties in 2021.

If I’d followed traditional wisdom, a content site might have sold for maybe 5x EBITDA that year. But that content site hadn’t been highly profitable. It was always a side project, so I never relied on it for income, and that meant we could prioritize growth and systems over profit. Whenever we earned money, I put it back into growing the site or outsourcing operations so I didn’t have to do it myself, rather than pocketing the money.

So if you looked at this content site from a profit-formula standpoint, it wasn’t worth much. But when it came to negotiating a sale, that didn’t matter.

What mattered was what it was worth to me, and what it was worth to the potential buyer. 

For both of us, that number was way higher than any formula would suggest, because the site had a big readership, lots of SEO traffic (which mattered back in 2021), and a trusted reputation.

That experience proved that the guidelines around selling any company are just that: guidelines. Use them as a way to set reasonable expectations, but don’t let them limit what you achieve.

5. It emphasizes the importance of systems

If you’ve sold a business, you’ve probably managed to figure out how to get it to run without you or at least get most pieces to run without you.

This can be a hard concept to implement when you first set out to grow a company. But once you see systems and processes in action—and you see just how much more valuable this makes your company when it’s time to sell—you’ll never again grow a business without them.

This is one of the biggest things second-time founders do differently: they build the company so it doesn’t rely too much on them. Low founder dependency makes your company far more valuable.

6. It sets you up for a bigger exit next time—if you want it

The first time you grow and sell, you learn. Then next time you build a company, you can move more quickly, and in all likelihood, create something even better.

You won’t make the same mistakes twice. For your next venture, you’ll set it up the right way to begin with, and you’ll take the most efficient route to profitability.

Of course, you’ll probably face new challenges the second time around, especially because most entrepreneurs don’t want to build the same business twice.

You’ll want a new challenge, so you’ll do something slightly different or maybe even completely different. Hopefully it still leverages some of your skills, but you’ll face new obstacles you didn’t face the first time and feel like a beginner all over again.

7. You’ll move one step closer to figuring out what you want

While going bigger and faster with the next company is possible, it’s optional. And it might not be what you want.

For example, I’d love to sell another company someday. But I have no desire to work toward a massive exit. That’s just not me. I don’t want to run a huge company. I prefer to work with a small team, so I can have less stress and more fun.

My goal is to hit that sweet spot of work I love doing that provides high value for others and high income for my family.

Lucky for me, you don’t have to have a big exit to be successful! Lots of founders stack smaller exits throughout their career, or hold onto a successful company for years without ever pursuing an acquisition.

Each of these approaches are valid—it just depends on what’s right for you. And sometimes, experimenting with lots of different ways of building is the best way to figure that out.