July 2025

So… You Wanna Sell Your Business But Keep a Slice of the Pie?

Let me tell you a little secret most people don’t talk about: selling your business doesn’t always mean walking away with a big fat check and heading to Cabo.

Sometimes, you’ve gotta play the long game.

That was me not too long ago. After 14 years of blood, sweat, bad coffee, and even worse client emails, I finally decided to sell my digital marketing agency. But the market wasn’t exactly raining down all-cash offers. Not unless I wanted to sell to some sketchy PE firm that would gut everything I built like a fish.

Instead, I sold the business with owner financing.

Yeah, it sounded complicated to me too at first. But stick with me—I’ll walk you through exactly how it worked, what I wish I knew sooner, and why it might actually be the smartest exit strategy you’ve never considered.

What Is Owner Financing in a Business Sale?

Before we get into the juicy details, let’s make sure we’re all on the same page. I spoke to Cliff Smith, the CEO at Business Broker News blog and this is that he said, “Owner financing is like being the bank for the person buying your business. Instead of them paying you everything upfront, they give you a down payment, and then you receive the rest in regular payments over time.”

Imagine selling your house, but instead of the buyer getting a mortgage, you become their mortgage lender. Only this time, it’s not a house—it’s your business baby.

Why I Went the Owner Financing Route

Let me rewind to the first real offer I got.

This guy, let’s call him “Greg,” came through a referral. Super enthusiastic, had that ex-startup bro energy (you know the type). He loved my business, saw potential, and was almost ready to buy. One tiny hiccup—he couldn’t get traditional financing.

Banks weren’t feeling him. SBA loan fell through. I was about to walk away, but then he hit me with: “Would you consider financing it yourself?”

At first, I thought… absolutely not. I’m not in the business of being a bank.

But after a couple of sleepless nights and a phone call with my accountant (shoutout to Lisa, the real MVP), I realized: this could actually be a win-win.

• I’d still get a decent chunk of cash up front

• I could earn interest on the payments (hello, passive income!)

• And I’d spread the tax hit out over time instead of taking it all in one brutal lump

It started sounding less like a risk and more like… a strategy.

Breaking Down the Business Deal (Without the Boring Legalese)

Here’s what we agreed on:

• Sale price: $480,000

• Down payment: $120,000 (paid at closing)

• Financed amount: $360,000

• Terms: 6% interest over 5 years, paid monthly

• Collateral: The business itself + a personal guarantee from Greg

We brought in a lawyer to write up a promissory note, outlined what would happen if he defaulted, and set up a schedule with auto-pay so I wouldn’t be chasing him down every 30 days like a glorified bill collector.

I won’t lie—signing the paperwork felt like sending your kid off to college. You hope they’ll thrive, but there’s still that tiny pit in your stomach wondering if they’ll burn the place down by Thanksgiving.

But this was all made a little bit easier because we spent time before purchasing to find the best business broker we could by reading this article on FOX4KC.

The First Year: Watching from the Sidelines

The first few months were… weird.

I wasn’t in the trenches anymore, but I still had this emotional investment. I’d randomly check the company Instagram. I even caught myself typing out an email to the new team with “suggestions” before deleting it like a sane person.

But Greg held it down.

Payments came in on time. He made some solid changes. Revenue dipped for a bit, but then bounced back. I realized I could relax a little. Maybe even trust the process.

If you’re thinking of going this route, here’s something I didn’t expect: the emotional rollercoaster. Letting go isn’t just about logistics—it’s about identity. You’re not just transferring ownership; you’re redefining your purpose.

That’s deep. And yeah, maybe I got a little too into journaling during that time. Don’t judge.

What I Wish I Knew Beforehand

Okay, let’s get practical. If you’re considering selling your business with owner financing, here’s what I learned the hard way:

1. Vet the buyer like you’re hiring a CEO
   Owner financing works only if the buyer is capable and trustworthy. Check their background. Talk to references. Ask hard questions.

2. Don’t skip the legal stuff
   Have a legit lawyer draft everything. Promissory note, security agreements, default clauses—the whole nine yards. Trust me, DIY contracts from Google templates will come back to haunt you.

3. Set up automatic payments
   Seriously. Don’t rely on anyone’s “I’ll remember” optimism. Put it on rails.

4. Stay emotionally detached (as much as you can)
   It’s easy to Monday-morning quarterback the buyer’s decisions. But once you sell, you’re not the boss anymore. Unless you like ulcers, let go.

5. Understand the tax implications
   Depending on your structure, you might qualify for the installment sale method, which can be way better than paying everything in year one. CPA guidance is essential here.

Would I Do It Again?

Honestly? Yeah. In a heartbeat.

Selling with owner financing wasn’t just a financial move—it was a chance to be part of a transition that actually felt… human. No corporate vultures, no ridiculous earn-outs, no soul-crushing 2-year “consulting” periods where you’re still running the show under a new logo.

I got paid. I got peace. And I got to see my business grow without me micromanaging the life out of it.

There’s something beautiful about that.

Key Takeaways: Selling with Owner Financing

• 💰 You don’t need an all-cash buyer to exit your business profitably

• 🧠 Vet your buyer like they’re marrying your daughter

• 📜 Legal structure is everything—don’t wing it

• 🧘‍♂️ Let go of control (and your ego)

• 💡 Tax perks can be real if structured right

Final Thought:

Owner financing isn’t for everyone. But if you’re sitting on a great business, and the right buyer comes along without the full cash… don’t automatically shut the door.

Sometimes the best exits aren’t about getting out fast—they’re about handing off the torch in a way that feels right.

Besides, what’s a little passive income between former owners? 😉

Let me know if you’ve ever gone this route—or are thinking about it. Always happy to swap stories and lessons over virtual coffee ☕️.

So, picture this: I’m sitting in my backyard with a half-cold cup of coffee, staring at a legal pad filled with doodles, numbers, and notes that only made sense to me at the time. I’d just told my accountant, “Yeah, I’m thinking about selling the business,” and he looked at me like I’d just declared I was going to live off the grid and raise alpacas.

That’s when I knew—I was really doing this.

Selling a business, especially one you’ve put your blood, sweat, and vacation days into, isn’t a simple Craigslist transaction. It’s more like navigating a jungle with a dull machete and no bug spray. I learned a lot, made a few wrong turns, and hopefully, by the time you finish reading this, you’ll avoid the traps I fell into.

Here are 10 common mistakes to avoid when selling your business, straight from someone who had to learn them the hard way.

1. Waiting Too Long to Prepare

You ever try to clean your whole house because a friend texted, “be there in 10”? Yeah, prepping to sell your business last-minute feels exactly like that—chaotic and slightly sweaty.

I waited until I knew I wanted to sell before getting my books in order, fixing operations, or even documenting my processes. Big mistake. Ideally, you want to start prepping at least 1–2 years before you actually list it. That gives you time to improve margins, clean up your financials, and build value that buyers will actually pay for.

2. Overvaluing Your Business

This one stings. I had a number in my head—let’s call it “The Dream Number.” It was based on emotion, ego, and a vague memory of what my cousin’s buddy got for his car wash chain. I ignored what the market would actually bear.

Don’t do what I did. Work with a valuation expert, like the ones on Business Broker News. A solid, data-backed valuation sets realistic expectations and prevents awkward “That’s adorable, but no thanks” conversations with buyers.

3. Hiding the Messy Stuff

There was a point where I thought I could “tweak” some of the less-attractive parts of the business during due diligence. You know, smooth over that one bad year, gloss over the employee turnover…

Buyers aren’t dumb. They will find everything. And if they feel like you’re hiding things? Trust goes out the window, deal dies on the vine.

Transparency builds credibility. It’s better to say, “Here’s a hiccup and how we’re fixing it,” than to get caught covering it up.

4. Trying to Do Everything Yourself

Look, I get it—your business is your baby. You don’t want anyone else feeding it, let alone selling it.

But unless you’ve sold a dozen businesses before, trust me on this: you need pros. I tried to juggle it all—marketing the sale, negotiating with buyers, running the day-to-day—and almost lost my mind (and a couple deals).

A good business broker, CPA, and attorney are worth their weight in gold. Let them do their thing while you focus on keeping the business healthy.

5. Not Vetting Buyers Properly

Oh man… the time-wasters. The “tire kickers.” The guy who scheduled four meetings and ghosted like he was auditioning for a dating app horror story.

Qualify your buyers early. Ask for proof of funds. Understand their intentions. If someone’s just curious or trying to “learn the ropes” on your dime, politely show them the exit.

6. Failing to Keep the Business Running Smoothly

This one’s easy to overlook. You’re emotionally checked out, you’re dreaming of retirement or launching your next gig—but if your numbers start slipping while you’re trying to sell? Buyers notice.

I had a slow quarter right when I started listing. It hurt the price and gave buyers the upper hand in negotiations. Keep grinding. Pretend you’re not selling and keep your team motivated, even if your head’s halfway on a beach already.

7. Overlooking Tax Implications

Here’s a fun surprise: just because someone hands you a big check doesn’t mean you get to keep all of it. 🤡

I didn’t fully understand how asset sales vs. stock sales would affect my bottom line—or how capital gains taxes would hit me like a truck. A good tax advisor can help you structure the deal to minimize what you owe Uncle Sam. Don’t wait until the ink’s dry to find that out.

8. Letting Emotions Get in the Way

I had to stop myself—more than once—from saying things like, “Well, if you don’t love this company like I do, maybe you’re not the right buyer.” 😅

It’s business. Buyers look at numbers, trends, and upside—not the time you slept in the office during your first product launch. Leave your heart in the background and keep negotiations professional.

9. Neglecting Confidentiality

Selling your business isn’t something you want on the office grapevine.

I let it slip to a vendor, and within a week, I had clients asking, “So… you selling?” That can freak out employees, suppliers, and customers. Use NDAs. Keep it tight. Control the narrative until the deal is solid.

10. Not Thinking About Life After the Sale

This part gets real. After the deal closed, I had a weird emotional crash. I’d spent years waking up with a purpose, and suddenly I was staring at my phone wondering if I should start a hobby or buy a kayak.

What’s next? Whether it’s a new venture, early retirement, or mentoring other entrepreneurs—plan for it. Otherwise, the “What now?” blues hit hard.

Final Thoughts: Learn From My Missteps (So You Don’t Repeat Them)

Selling your business can be one of the most rewarding experiences—financially and personally—but only if you do it right. I didn’t, at first. But the more I slowed down, brought in help, and got honest about the process, the better things turned out.

And hey, if you’re reading this with a cold coffee in your hand and a scribbled-up legal pad like I was, you’re already on the right track.

You got this.

Now go make a clean, smart exit—and maybe, just maybe, treat yourself to that kayak. 🚣‍♂️

P.S. Got a funny or painful business-selling moment of your own? Shoot me a message. Misery (and spreadsheets) loves company.