Selling a Business is Hard

Perspectives

Selling a business can be a little messy and a little stressful, no matter the size. At Trailhead, we've sat in the shoes of buyers and sellers and know firsthand what the experience is really like.

Selling a business is really hard.

It can be complicated, emotional, and a little uncertain at every step along the way. Having personally sat on all three sides of the table: - buying, selling, and brokering - each is a little different.

Buying a business was all excitement and new beginnings for me. I was leaving a job and supremely confident this was the right next step.

Selling was all anxiety. It should have been exciting, but I was so concentrated on making sure nothing derailed the sale that I didn’t stop to enjoy the last few months of ownership, the employees, and getting to drive really big trucks every once in a while (I owned a waste hauling business).

Sitting in the middle as an intermediary is all drive. It’s still exciting, it’s still stressful, but we’re laser-focused on getting our client the best deal we can while making sure the deal closes. We all have the same goal: the buyer wants to buy, the seller wants to sell, and we want to see both parties close, but it's easy for the parties with the most at stake to lose sight of that in the heat of the moment. And by the way, when the deal closes, and the money is wired, and everyone takes a deep breath because we can relax? It isn’t over - now the fun really begins and an adversarial relationship here doesn't benefit anyone.

What does this all mean? It means we’ve chosen to partner with business owners during what will be a stressful and uncertain few months.

The lender will change their underwriting standards a week before closing.

The seller will decide to just shut down because selling is not worth the trouble.

The deal will die multiple deaths before being resurrected. Always.

But when the wire hits and the deal closes, it’s worth it. The business owner gets to step back from the company she’s grown and poured her heart into, and a new leader gets to pick up and grow where she left off. Employees stay employed, customers stay happy, and we get to do it all over again.

March 2, 2024