3 Mistakes We Made Selling Our Businesses (So You Don’t Have To)

After successfully building and selling two businesses—including an award-winning bar—we thought we had everything figured out. But looking back, there are three things we wish we’d done differently. These weren’t small oversights. These were costly lessons that could’ve saved us thousands, reduced stress, and put us in a better position for what came next.

Whether you’re thinking about selling now or building with that goal in mind, here are three big mistakes we made—and what we’d do instead.

1. We Should’ve Used a Broker from Day One

We didn’t start with a broker. We thought we could handle it ourselves, keep more money in our pocket, and control the deal.

We were wrong.

A good broker doesn’t just list your business—they know how to value it, market it, and protect your interests throughout the process. They have buyers you don’t have access to and know how to create demand and urgency.

By the time we brought one in, we were already knee-deep in a stressful process and missing leverage. If we had started with a broker, we would have sold faster and for more.

Lesson: Don’t cheap out on professionals who do this every day. You built something valuable—treat the sale like it.

2. We Should’ve Considered Self-Financing

We took the entire payment upfront. It felt good—until tax season hit.

Depending on how your deal is structured, the IRS can take a huge bite out of your sale. We didn’t realize how much smoother (and smarter) self-financing could be from a tax perspective.

Yes, it means taking payments over time. But in many cases, that setup can reduce your tax burden significantly—and provide ongoing monthly income.

Lesson: Talk to a tax professional before you sell. You might not need all the cash upfront, and the government definitely doesn’t need more of it than necessary.

3. We Didn’t Charge Enough

We underestimated the value of what we built.

When you’re in the day-to-day grind, it’s easy to miss the big picture: the brand equity, loyal customer base, systems, reputation, and future potential. We priced based on what felt fair—not what the business was actually worth to someone else.

It wasn’t until after the sale that we realized we left money on the table. The new owner was set up to win big. That should’ve been reflected in the price.

Lesson: Your business is likely worth more than you think—especially if it runs without you, generates consistent revenue, and has room to grow. Price it accordingly.

Final Thoughts

Selling a business is more than just a transaction—it’s the exit from years of sweat, risk, and hustle. Make it count.

Don’t repeat our mistakes. Get professional help. Think about taxes early. And above all, know your worth.

If you ever want to talk about your exit strategy—or just want someone who's been there to bounce ideas off—we're happy to share what we’ve learned.

Because success isn’t just about building the business. It’s about exiting smart, too.