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The Moment It Got Real

Let me set the scene.
Laptop open. Buyer on Zoom. My lawyer on mute (but very much giving me side-eyes on a second monitor). I was sweating through a decent shirt, pretending like I’d done this a hundred times.

Spoiler: I hadn’t.

But by the end of that call? I had the makings of a deal that felt like a win-win, not a win-meh. So if you’re selling your business and don’t want to get bulldozed, here’s what actually worked for me.

Step One: Know Your Walk-Away Point Before the Talk Even Starts

This sounds obvious until you’re offered a number that almost works. Then it’s tempting to just… bend.

I made a “non-negotiables” list. It included:

• Minimum sale price

• Payment structure (no 90% deferred nonsense)

• Timeline (no 18-month maybe-we-close limbo)

• Level of post-sale involvement (spoiler: very little)

That list was my anchor. Without it, I might’ve folded like a cheap tent the moment someone threw around phrases like “earn-out potential.”

Step Two: Price Is Only One Piece of the Puzzle

Here’s the trap: you get fixated on the dollar amount. But terms matter just as much—sometimes more.

One buyer offered me $500K all cash. The other? $600K… but over 24 months, tied to revenue benchmarks I had zero control over.

Guess what? I took the $600K.

Why? Because I negotiated:

• A 50% upfront payment

• Clear milestones that couldn’t be manipulated

• Legal protections if the business tanked post-sale

It took three weeks of back-and-forth, some creative structuring, and a few deep sighs—but I walked away with more and slept at night.

Step Three: The Power of “Let Me Think About That”

The biggest lie we tell ourselves is, “I need to respond now.”

No, you don’t. I once sat on a counteroffer for 48 hours, even though my gut reaction was “yes.” I wanted to say yes so badly.

Instead, I paused. I walked my dog. I drank absurd amounts of green tea. I even called a friend who once sold a SaaS company and made him break down his entire deal over tacos.

Only after that pause did I come back and say, “Here’s what would make this work for me.”

That phrase—not “no,” not “yes,” but “here’s what would make this work”—was magic.

Step Four: Don’ Be the Only One Without a Lawyer

Listen, I love reading contracts about as much as I love stepping on Legos barefoot.

But my attorney? She lived for that stuff.

She found:

• A clause that would’ve made me liable for future vendor debts

• An earn-out term that gave the buyer veto power on marketing spend

• A “non-compete radius” that included the entire internet (seriously?)

Having a professional in your corner is not just smart—it’s survival.

If you’re balking at legal fees, remember: one bad clause could cost you more than your entire asking price.

Step Five: The Final “Gut Check” Before You Sign

Here’s the moment no one talks about.

It’s 11 p.m. The contract’s on your screen. Your finger is hovering over “DocuSign.”

And you hesitate.

Not because the deal is bad, but because… it’s real now.

Before I signed, I re-read one paragraph. Just one.

The one that said I’d be officially out—ownership transferred, identity detached.

And I asked myself: Will Future Me thank me for this?

When the answer was yes—even through the nerves—I clicked.

Bonus Tip: Keep It Friendly, But Keep Receipts

I liked my buyer. Genuinely. We cracked jokes. Shared stories. Even had a beer after closing.

But don’t mistake chemistry for trust.

Every conversation? Followed up by email. Every verbal agreement? Documented.

Not because I expected things to go wrong, but because business is business. You owe it to yourself to protect the legacy you built.

Final Thought: You Can Win Without Being a Shark

I didn’t threaten. I didn’t bluff. I didn’t lowball or hardball or any of the other “ball” tactics people love to tweet about.

I just:
✅ Knew what I needed
✅ Stayed calm under pressure
✅ Negotiated for value, not just vanity
✅ Got good help (and actually listened to it)

And I sold my business on my terms.

That’s not just a good deal—it’s a great ending.

So… You’re Thinking of Selling Your Business?

First off, congrats. Seriously, getting to a point where you can even consider selling your business means you’ve built something worth buying. That alone puts you in rare air—like nosebleed-section-at-a-private-jet-auction rare.

Now, if you’re anything like I was (think: highly caffeinated, slightly panicked, staring at spreadsheets at 3 a.m. wondering what EBITDA really means), the idea of selling your business probably feels a little like walking a tightrope over a pit of flaming contracts and tax code.

But don’t worry—I’ve been there. Actually, I lived there for six exhausting, exhilarating months. I’ll walk you through what I wish someone had told me before I dove in face-first.

Step One: Get Real About Why You’re Selling

You need to ask yourself a brutally honest question—and no, it’s not “how much money can I get?”

It’s: Why now?

In my case, burnout had crept in like a raccoon through a cracked basement window. I was still “in it” mentally, but the thrill was gone. I wasn’t pushing new ideas, just pushing paper.

Whether it’s burnout, a better opportunity, or you just want to spend more time fly-fishing in Montana (respect), be crystal clear with yourself—and eventually your buyers—about why you’re ready to part ways. It sets the tone for everything else.

Step Two: Know What You’re Selling (Hint: It’s Not Just Profits)

Here’s a hard pill I had to swallow: your business isn’t just a pile of revenue and some office furniture. It’s systems, people, processes, brand, customer loyalty… and a story.

Buyers don’t just want your numbers—they want to know your business is a machine that runs without you needing to crank the gears every morning.

So, before I even thought about listing, I documented the living daylights out of everything: SOPs, workflows, client onboarding, the works. Yes, it was a colossal pain. Yes, it paid off big time when a serious buyer said, “Wow, this looks turnkey.”

Pro tip? If you are the business (hello, solo consultants ), start grooming someone now to handle client work, or at least build repeatable packages that can survive without you playing Captain Everything.

Step Three: Valuation Is Part Math, Part Witchcraft

This part? Oh boy. I felt like a contestant on Shark Tank every time I tried to figure out what my company was worth. There are formulas (SDE, EBITDA multiples, market comps), sure. But let’s be honest—value is also about perception.

I had one buyer offer 3x my earnings and another offer 1.5x—for the same business. The difference? One saw a future without me. The other saw a job opening they didn’t want to fill.

Here’s what worked for me:

• Hired a professional valuator (worth every penny)

• Talked to brokers even if I didn’t plan to use one

• Created a killer info packet that made my business look irresistible (think: business Tinder profile, but with more spreadsheets)

Step Four: List Smart, Negotiate Smarter

Okay, here’s the part that separated the wheat from the tire-kickers. I listed through a niche marketplace, but also tapped my network hard—LinkedIn posts, quiet word-of-mouth, even a few “I might be looking for a change” chats over overpriced oat milk lattes.

Then came the calls.

Some were laughably unqualified (“Can I pay with crypto?”), and others were dangerously slick (like, Wolf of Wall Street slick).

Eventually, I landed on two legit buyers. One was all-cash, the other offered a higher price… with seller financing.

I wanted to scream into a pillow.

In the end, I chose the second deal—but only after hiring a contract lawyer who made sure I wouldn’t be left holding the bag if payments went south.

Step Five: Due Diligence Is Basically an FBI Investigation

If you’ve ever applied for a mortgage, imagine that—but on steroids and laced with legal jargon.

Buyers will dig through your books, your systems, even your Google reviews. It’s not personal—it’s just smart business.

My advice?

• Keep immaculate records (seriously, QuickBooks is your best friend)

• Be honest about any skeletons in the closet (they will find them)

• Don’t try to hide that one angry client who left you a 1-star review in 2018 (I tried. It backfired.)

I made a checklist, treated it like my business’s annual physical, and actually pre-sent due diligence docs to look proactive. One buyer said it made me “look like a seller who knew what he was doing.” I just didn’t want to get ghosted.

Step Six: After the Sale… Who Are You?

This is where it gets weird. The moment the wire hit my account, I expected to feel triumphant. Instead, I felt… lost?

You spend years tying your identity to this thing. Then one day, poof—it’s not yours anymore.

For the record, I did eventually celebrate (two weeks in Spain, a little too much sangria). But more importantly, I planned for life after the business. Whether it’s starting something new, mentoring founders, or just chilling, give yourself space to figure out who you are without the company hoodie.

Final Thoughts: You’re Not Just Selling a Business—You’re Selling Years of Your Life

Look, this process isn’t for the faint of heart. It will test your patience, your ego, your sanity. But done right, it can be one of the most empowering exits of your life.

Just remember:
✅ Know your why
✅ Prep like a pro
✅ Get the right price and the right terms
✅ Guard your peace like a golden goose

And don’t forget to take a breath. You built something valuable. Now go sell it like you mean it.

Ready for a Successful Exit?
Stick around—I’ll be sharing the exact info packet I used (redacted, of course) in my next post. Trust me, it’ll save you weeks of stress.