Spoiler alert: It wasn’t all yachts and champagne. But it wasn’t all sharks and spreadsheets either. Somewhere in between, I learned a few things, bruised my ego (twice), and walked away with a deal that changed my life.
If you’ve ever sat in your office at 2 a.m., sipping a flat LaCroix, staring at a profit-and-loss sheet like it’s hieroglyphics, and wondered, “Is it time to sell?” — this one’s for you.
The Moment I Knew It Was Time to Sell
I didn’t wake up one day and yell, “That’s it, I’m selling to private equity!” Nope. It was more like a slow burn.
The business had grown beyond what I could (or frankly, wanted to) manage. We were doing 8-figures, had 47 employees, and Slack was pinging me more than my teenage daughter. Every decision felt like playing chess underwater.
The tipping point? A six-hour argument over an enterprise software migration that cost us $142,000 and my last shred of sanity. That night, I looked at myself in the mirror, beard scruff and all, and said: “This business needs a new daddy.”
Why Private Equity? Why Not Just Sell to a Competitor?
Great question. I flirted with the idea of selling to a competitor. Had a few coffees. Some Zooms. One guy even pitched me from his yacht (bro… we get it).
But every convo felt like they were buying me, not just the business. They wanted me chained to the company for another 5 years. Nah, I didn’t build this thing to stay on as middle management.
Private equity firms, on the other hand, had structure. Teams. Processes. They weren’t buying me—they were buying the system I’d built. That was the dream. They wanted scale, not babysitting.
The Dance: Getting Courted by Private Equity
When word got out that I was “considering strategic options” (PE code for I might be selling, hit me up), the inbox filled up faster than a TikTok trend.
Most of them came with fancy decks and slick jargon. “We unlock synergies.” “We enhance enterprise value.” Bro. Just tell me if you’re gonna gut my team or not.
Eventually, I landed on a group out of Chicago. Sharp suits, but they didn’t talk down to me. They saw the value in my customer base, loved our margins, and didn’t flinch when I dropped my number. We’re talking real grown-up energy.
Due Diligence: A Fancy Way of Saying “Let’s Turn You Inside Out”
Once we agreed on a rough valuation and LOI (that’s Letter of Intent, aka the pre-nup before the marriage), it got real.
They asked for everything. Bank statements, tax returns, contracts from 5 years ago that even I forgot we had. One guy literally asked for our “historical churn by cohort.” I had to Google it.
I won’t lie—due diligence felt like a root canal while running a marathon. But here’s the thing: if your books are clean, and your ops are tight, you’ll get through it. Barefoot and bruised, maybe. But through it.
The Exit: What I Walked Away With (And What I Didn’t)
The deal closed 92 days after signing the LOI. I sold 85% of the business for a mid-8-figure valuation. Kept a little skin in the game because hey, why not ride the wave one more time?
The money hit my account on a Tuesday. I took a breath that felt like I’d been holding it since 2017.
But here’s what they don’t tell you: the day after the wire clears, you still wake up at 6 a.m. Your mind still races. You don’t instantly become Zen because your bank app has extra commas.
I had to relearn how to not be the boss. It was weird. Kinda like watching your kid get adopted by a really rich family. You’re happy, proud, a little jealous… and kinda sad.
Would I Do It Again?
100%. But I’d do it smarter.
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I’d get a better M&A advisor from day one. Mine was good. But I needed great.
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I’d prep the business like I was selling a house. Fix the leaky faucets, paint the walls, organize the drawers. Translation? SOPs, clean financials, scalable team.
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I’d be more honest with myself earlier. I held on longer than I should’ve. Not because I loved it… but because I was scared of what came next.
Final Thoughts: Should You Sell to Private Equity?
If your business is humming, but your soul is fried… if you’ve taken it as far as you can, but it still has room to grow… and if you’re cool letting someone else drive while you sip margaritas (or build your next empire)—then yeah. It might be time.
Just know this: it’s not just about the money. It’s about knowing when to let go. It’s about trusting that what you built is strong enough to live beyond you.
Oh, and make sure your lawyer actually reads the fine print. Trust me on that one 😅
Selling to private equity doesn’t mean selling out. It means knowing your worth, cashing the check, and walking away with your head high.
Just don’t forget to enjoy the ride. Even the bumpy parts.
Because one day, you’ll look back and realize… that crazy little business? It changed everything.