Selling Your Business? It’s Homework or Heartache

Selling your business might seem like a big, exciting step. But behind the celebrations and the champagne, there’s a less glamorous truth: every company sale is a crossroads, and one wrong move could lead to a wave of 'seller’s remorse.'

Homework might not be glamorous, but it’s essential before any deal. If you’re not prepared to do that, you’re set for heartache. Trust me, I’ve been there.

I once led a services business that got scooped up by a big software company. It seemed perfect on paper – they got new capabilities, we got a premium check. But within weeks, it became clear they only had eyes for a fraction of what we did. The rest? Left dangling in limbo, morale tanked, and top talent started walking. I soon followed. 

Not long after, I built another business, SHARE Creative, and this time, I knew the drill. Fast-forward to 2020, when SAMY Alliance came knocking – with a deal that hit the sweet spot: no drama, no hard lessons, just a dream integration. 

So two very different experiences. But experiences that taught me what it takes to sell your business; what to look for in an acquirer and what to do after the deal happens. Here are some of those lessons…

Align Your DNA, Not Just Your Deal

First, scrap the idea that any buyer will do. The magic lies in alignment – not just strategic fit. You’re looking for an operational and cultural match. You need to ask the hard questions: Do they share your values? How’s their track record with other acquisitions? What value have those deals created? And don’t just take their word for it – talk to the leaders of companies they’ve acquired. If they sidestep these conversations, that’s your cue to reconsider.

Your Team’s Welfare – A Non-Negotiable

Your people are your legacy. So you need to safeguard their future. Ask how the buyer plans to integrate your team and protect their growth. Look for terms that shield the core team and ensure they won’t end up as collateral damage in a half-baked integration plan. They were after all, the reason you’ve got to the enviable position of being attractive enough to be bought.

Clarity is Key – Look for Vision, Not Vague Ambitions

Too many execs can’t articulate a clear vision post-acquisition. If a buyer can’t give you a crisp, no-BS rundown of their goals and how your company fits in, run. Fast. The best buyers have a clear, inspiring plan for your combined future and can communicate it with ease. Anything less, and red flags should be raised. 

Integration is More Than a Buzzword – Demand Proof

True collaboration can’t be faked. Get behind the scenes, see how the buyer’s teams work across regions, functions, and hierarchies. Is it an actual integration, or just lip service? And while you’re at it, request a look under the tech hood. Ask your CTO to take a fine-tooth comb to their IP, tech, and platforms. And get the whole team involved in that process. If they’re reluctant to share, then again alarm bells should be ringing.

Timing Isn’t Everything – It’s the Only Thing

The timing of your sale matters. Sure, you want a strong EBITDA, but don’t wait for the peak only to face a deflated post-sale slump. Strike when you’re on the rise but with room left to grow, ensuring a smoother ride during the earn-out phase.

What’s in It for You? Spell It Out

Lastly, let’s talk about you. Selling a business is not like the end of a film - with you riding off into the sunset. You’re moving from the driver’s seat to a new role within a larger machine. Will you still get to build, create, and shape? Will it scratch that entrepreneurial itch, or will you find yourself tethered to corporate red tape? Be blunt: understand exactly what you’re signing up for.

After all, you still want something to get out of bed for after you sign on that dotted line.