Mergers and Acquisitions: Lessons from the Trenches

People think selling a business means you finally made it. Years of hustle paying off in a sweet deal that sets you up for life. That's the dream version. Real life looks a lot different.

The process gets messy. 

Many deals fall apart, and some that close turn into headaches. 

Founders who thought they built gold mines find out buyers see dirt. Others who think they won the negotiation end up with the short end of the stick.

Here's what it really looks like.

The Deal Starts Way Before Anyone Says "Let's Talk"

Most owners wait too long to prepare for a sale. They think they can fix operations, clean up finances, and polish everything after deciding to sell. This is why so many deals crash during due diligence. Buyers want a company that's already strong, ready to grow, and not dependent on the owner. The right time to start preparing? Years before you even think about exiting.

Owners who run their businesses like they could sell tomorrow, whether they plan to or not, build real value. That means having systems on paper, a leadership team that can take over, and revenue you can count on. A buyer won't pay for what your business might become. They pay for what it is today, and they discount what is may provide in the future.

Buyers Want a System, Not Another Job

A business where the owner makes all the big calls won't attract buyers. The more you handle day to day, the less your company is worth. The best exits happen when you're already not needed.

A company with a solid team, written processes, and a wide range of customers simply commands more money. Buyers want something that keeps running smoothly whether you stick around or not.

The more your business needs you, the harder it is to sell. 

Sometimes it becomes impossible.

The Right Buyer Often Surprises You

Most owners think they'll sell to a competitor or bigger player in their field. Those deals happen, but they're not always your best bet.

Private equity groups, your management team buying you out, or individual investors often offer better opportunities. Some buyers aren't even in your industry but see strategic value in what you've built. These buyers will typically pay you much more than transactional buyers.

Owners who fixate on one type of buyer limit their options. The best deal rarely comes from the first place you look.

Terms Matter Way More Than Price

An owner hears a big number and gets excited. That's almost never what ends up in your pocket.

An offer of ten million dollars means little without understanding how the deal works. Earn outs, seller financing, tax bills, and employment agreements all affect what you actually take home.

A smaller offer with better terms may very well put more money in your pocket. Money now beats promises later, and owners who skip the fine print always regret it.

The Emotional Impact Hits Hard

Selling isn't just a money move. 

It's a huge identity shift.

Many owners don't realize how different life feels after the exit. For years, your purpose and identity was tied to the business. When that vanishes, it can leave you feeling lost.

The smoothest transitions happen when you have something to move toward, not just something to walk away from. Maybe a new venture, an advisory role, or a passion project that's been waiting in the wings.

The money matters, but your personal journey matters just as much. Owners who don't plan for life after business often struggle more than expected.

Build for Value, Not Just Cash Flow

A business set up to maximize this year's income isn't the same as one built to sell.

Many owners run companies to pull out maximum profit right now or reduce their tax bill. Buyers look for something that can grow, scale, and keep generating returns long after you're gone.

The best time to think about selling is years before you want to exit…and definitely before you want to burn it to the ground.  

Build something that works without you in the picture. 

Create systems that run independently. 

Treat every year like a buyer is watching.

And remember, a great exit isn't about picking the perfect time to sell. It's about building something that's always ready for its next chapter at all times.