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The Real Talk You Wish Someone Gave You Sooner

Let’s Be Honest—There’s No Magic Number

I’ll never forget the day I realized I had absolutely no idea what my business was worth. I was sipping lukewarm coffee in a paper cup that had definitely seen better days, flipping through a half-crumpled folder of P&L statements, and wondering, “Am I about to screw myself over?”

If you’ve ever asked yourself, “What’s a fair price to sell my business for?”—welcome to the club. It’s not just about spreadsheets and formulas (though there are plenty of those). It’s about timing, emotion, market appetite, and sometimes, just good old-fashioned gut feeling.

But let’s unpack it, step-by-step—without the fluff.

1. Start With Reality, Not Fantasy

When I first floated the idea of selling my business, I had some… strong feelings. You know the type: “I built this from scratch, worked weekends, sacrificed holidays—this thing is worth millions!”

Spoiler: that’s not how buyers think.

Buyers aren’t buying your blood, sweat, and tears—they’re buying cash flow, systems, and future potential. Cold, I know. But it helped me detach emotionally and think like a buyer.

Here’s what helped ground me:

• SDE or EBITDA Multiples: Most small-to-mid businesses sell for 2-5x SDE (Seller’s Discretionary Earnings) or EBITDA. If you’re a $400K/year SDE business, your selling price might range from $800K to $2M, depending on risk, industry, and growth potential.

• Industry Trends: Some industries are hotter than a summer sidewalk in flip-flops (tech, health services), while others cool faster than microwave pizza.

2. Dig Into the Numbers—but Tell a Story

You know how some people can cook a five-course meal using just whatever’s in the fridge? That’s how I approached prepping my books. My QuickBooks looked more like a mystery novel than a balance sheet.

But cleaning up my financials was like finally changing a lightbulb I’d ignored for years—it just made everything clearer.

Buyers want:

• Clean P&L statements (preferably 3+ years)

• Logical add-backs (don’t try to sneak in your dog grooming expenses)

• Forecasts they can actually believe

And here’s the kicker—numbers matter, but stories sell.

I crafted a narrative around how the business weathered COVID, pivoted fast, and built a loyal customer base. That gave buyers confidence that the systems weren’t just duct-taped together.

3. Market Conditions Matter (Even If You Don’t Like It)

I had a friend try to sell his ecommerce brand in early 2023. Let’s just say, it was not a seller’s market. Multiples had dipped, buyer funding dried up faster than my enthusiasm at tax time, and deals got stuck in due diligence limbo.

What I learned? Timing isn’t everything, but it’s… like, 70%.

If interest rates are high, buyers get picky. If your industry’s trending on TikTok, you’ll have a bidding war. If the economy’s looking uncertain? Expect offers to dip and deals to stretch out.

Pro tip: Don’t try to “wait for the perfect moment.” That’s like trying to time the stock market—it’s more art than science. Focus on being ready.

4. Intangibles Can Boost—or Kill—Your Valuation

I had an incredible brand. Strong reviews. Loyal email list. Smooth supply chain.

But my Achilles’ heel? Me. I was too involved. I was the bottleneck. I was doing sales calls, ops, and some support. That scared off buyers like I’d told them the building had termites.

So I spent six months “de-owner-izing” the business. Trained a VA. Delegated ops. Built a simple SOP. Like magic, the perceived value jumped.

Here’s a quick cheat sheet of intangibles that matter:

• Owner independence ✅

• Recurring revenue ✅

• Customer concentration ❌

• Strong brand presence ✅

• Team in place ✅

5. Ask Around—But Don’t Copy Everyone

Everyone and their mother will have an opinion about what your business is worth.

My CPA told me one thing, my business broker another, and my neighbor who flips NFTs said I should accept crypto and retire on an island.

In the end, I interviewed a couple of business brokers and got a third-party valuation. That gave me a realistic anchor before I started fielding offers. Remember, a “reasonable” price isn’t just about numbers—it’s what you are willing to accept and what the market’s willing to pay.

6. Your Reason for Selling Affects the Price (No One Tells You This)

Buyers aren’t dumb. If you’re selling because you’re burned out, great—they’ll ask for a discount. If you’re selling because you want to scale up into a new venture and have systems humming along? Suddenly, you have leverage.

When I made my exit, I framed it like this: “This business has untapped potential I no longer have the bandwidth to pursue, but it’s set up for a smart operator to double revenue within 18 months.” Boom. That’s value, not desperation.

So… What’s Reasonable Then?

Let’s boil it down:

A reasonable price to sell your business is…

✅ 2–5x your SDE or EBITDA
✅ What the market is paying in your industry
✅ What your business can support post-sale (no inflated nonsense)
✅ A number that makes sense for both sides
✅ Enough for you to walk away happy and not resentful

Final Thought: You’re Not Just Selling a Business. You’re Selling a Chapter of Your Life.

I won’t pretend it was easy. The last week before the deal closed, I barely slept. I questioned everything. Was I selling too low? Was I making a mistake?

But here’s what I’ve learned since:

• Peace of mind is worth something.

• A clean break feels better than dragging things out.

• And your next chapter? It deserves all the focus.

If you’re wondering what your business is worth, don’t just look at spreadsheets. Look at your story, your systems, and your sanity. That’s where the real value lives.

Got a question about pricing your business? I’m not a guru—I’m just a guy who’s been through it, and lived to tell the tale (with a few gray hairs and a much better accountant).

Would you sell your business if someone offered the “right price” tomorrow?

So let me take you back to a humid Tuesday morning — the kind where your shirt sticks to your back before you’ve had your first sip of coffee. I was staring at the same spreadsheet I’d been tweaking for days, half-hypnotized, half-horrified. And it hit me like a freight train in slow motion: It’s time to sell the company.

Yeah, that company. The one I built from scratch with a busted laptop, too much coffee, and enough trial-and-error to qualify as a psychological experiment. It was my baby, my burden, and, increasingly, my burnout.

What follows is not some soulless MBA checklist. This is the real-deal, gritted-teeth, reggae-on-repeat journey I took to let go of a business I loved — and do it without selling my soul or ending up in a fetal position on my office floor (okay, just once… but that’s a story for another time).

Step 1: Get Real With Yourself — Like, Brutally Real

Before I even talked to a broker or whispered a word to my team, I had to stare down the existential beast in the mirror.

Why was I selling? Burnout? Boredom? A desire to go live on a beach in Jamaica and write a philosophy book nobody asked for?

(Answer: All of the above.)

But here’s the truth — you’ve got to name your “why” or you’ll get knocked around in this process like a leaf in a hurricane. I journaled. I meditated. I even talked to my plants. You don’t need to go full Bob Marley-zen like I did, but take the time to figure it out. You’ll need that clarity when the emotional sucker punches start flying.

Step 2: Get Your House in Order (a.k.a. Clean Up Your Mess)

You ever try to sell your car with fast food wrappers still in the back seat? Yeah — don’t be that person with your business.

I started digging into my financials and found things I hadn’t looked at since the Obama administration. Subscription I forgot to cancel? Check. Vendor overcharging me for years? Double check. Some revenue “estimates” that were, let’s say, optimistically creative? Yeah… that too.

So I rolled up my sleeves, put on some dub, and did the work:

Cleaned up my books with my CPA.

Documented key systems and processes.

Put contracts, leases, and licenses in a neat little Dropbox folder.

And yep, finally canceled that $89/month software I hadn’t used since 2018.

If a buyer is going to look under the hood, don’t let them find a raccoon living in the engine, know what I mean?

Step 3: Find Your Tribe (Because Going Solo is for Suckers)

Next up? I brought in the pros. Look, I thought I could DIY this sale at first. I mean, I sold $500K worth of product last year — how hard could this be?

Spoiler alert: hard. Like “suddenly you’re on a Zoom call with a private equity guy who talks like a Bond villain” hard.

So I hired a business broker. A good one. (Sidenote: interview at least three and trust your gut — mine wore Birkenstocks to our first meeting and I weirdly respected it.)

The broker:

Helped me value the company realistically (not emotionally).

Created a killer info packet for buyers.

Acted as a buffer so I didn’t have to talk money like a used car salesman.

And perhaps most importantly — kept me from throwing in the towel when I got ghosted by that “serious” buyer from Boston.

Step 4: Keep It Hush-Hush (Until It’s Time)

Listen, loose lips sink ships — especially in the business world. I kept things very under wraps.

Only my lawyer, my accountant, and my broker knew in the beginning. Not even my top managers had a clue. I didn’t want rumors flying and morale tanking before I even had an offer.

When it was time to tell the team, I sat everyone down, face to face. I told them the truth: I was proud, I was tired, and I wanted them to be part of something bigger moving forward.

There were tears. There were hugs. And then… there was cake. Always bring cake.

Step 5: Negotiate Like a Rasta with a Rolex

Selling your company is not a garage sale. Don’t slap a price tag on it and hope for the best. This is a dance — and you’ve got to know your worth.

We had three serious offers. One lowballed. One overpromised and underdelivered. And one — the one we chose — came in slightly under our asking price but had the smoothest transition plan and the best vibes.

Yup. Vibes matter.

I negotiated hard, but fair. We tossed in an earn-out clause, a 90-day training period, and a champagne clause (okay, not really — but I did toast with champagne when we closed).

Step 6: Let Go — Gently, But Fully

The last week before the handoff, I stood in my empty office and ran my hand along the dent in the wall where I once threw a stapler during a particularly passionate sales call.

Letting go is weird. It’s like breaking up with someone you still love, but who you know you can’t build the future with.

But guess what?

It felt right.

Now? I’m sipping iced coffee on a porch somewhere warm, running a small advisory biz, and trying to figure out TikTok. (Don’t judge.)

Key Takeaways (a.k.a. The TL;DR for the Skimmers)

Get honest about why you’re selling — don’t just chase the money.

Clean up your books and documents so buyers don’t get scared off.

Hire a solid business broker — it’s like having a tour guide through a jungle.

Keep it quiet at first, then communicate with your team with heart.

Negotiate smart — don’t settle, but don’t get greedy either.

Let go fully — so you can move on to whatever’s next with peace.

Selling your company isn’t just a business decision. It’s a personal, emotional, spiritual odyssey, man. And if you do it right, it can be a beautiful chapter — not a tragic ending.

You don’t need to be rich or ruthless to pull it off.

You just need to be real.

Now go light some incense or pop a bottle. You earned it.

Peace, profits, and perspective ✌️
— A guy who lived it, loved it, and let it go