How to Handle a Seller

Buying a small business is a lot like dating someone fresh out of a long-term relationship. They swear they’re ready to move on, but suddenly, they’re crying over old photos and asking if you’ll still let them come over and check on the dog.

The psychology of a seller is a fragile, fascinating thing. You’d think selling a business is a clean break—a handshake, a wire transfer, and a celebratory drink. But in reality? It’s a slow-motion breakup filled with second-guessing, paranoia, and the occasional existential crisis.

So, how do you get through it without losing your patience, your mind, or the deal?

1. Accept That You’re Their Therapist Now

They’re not just selling a business; they’re selling themselves—their late nights, their wins, their mistakes. They probably built this thing from scratch, which means their self-worth is tangled up in revenue reports and customer reviews.

So, don’t be surprised when they start acting irrationally. One minute, they’re eager to sell. The next, they’re clinging to their desk like a toddler at daycare drop-off. Your job? Nod, validate their feelings, and gently remind them that they were the one who listed the business in the first place.

2. Keep Your Ego in Check

You might be thinking, “I’m rescuing them. I’m paying them actual money to retire in Boca and stop answering customer emails at 2 a.m. What’s the problem?”

The problem is, they don’t see it that way. They see you as the new step-parent to their beloved child. And like any reluctant co-parenting arrangement, they’re skeptical. They’re looking for a sign that you “get it,” that you won’t ruin everything they built.

The solution? Humility. Yes, you have big plans, but if you start pointing out all the ways they could have done things better, they’ll either ghost you or jack up the price just to make you suffer.

3. Pretend You Love Everything (For Now)

Think of it as house-hunting. You don’t walk into an open house and loudly complain about the wallpaper unless you want the seller to suddenly “reconsider” the price. The same logic applies here.

Even if the branding is 15 years out of date and their operations manual is a collection of handwritten Post-it Notes, play it cool. Praise their hard work, acknowledge their effort, and slowly introduce the idea of “building on their legacy” rather than burning it all to the ground.

4. They’ll Try to Back Out. Don’t Panic.

Sellers get cold feet. This is as inevitable as bad coffee at a conference. The moment they realize this is real, they’ll start coming up with reasons why they shouldn’t sell:

• “I think I’ll just pass it on to my nephew.” (The nephew does not want it.)

• “Maybe I’ll just scale back and run it part-time.” (They have never worked part-time a day in their life.)

• “I had a dream last night that I should keep it.” (This is not a valid financial strategy.)

At this point, you need to stay calm and not overreact. A panicked buyer gives them all the power. Instead, reassure them. Keep them moving forward. Get them back into a place of confidence by asking about their next chapter. Are they excited about spending more time with grandkids? Traveling? Starting something new? Anchor them in that vision, and they’ll remember why they wanted to sell in the first place.

5. Close Fast (Before They Change Their Mind Again)

A slow deal is a dead deal. The longer the process drags out, the more time they have to overthink it. So, get your financing locked in, keep communication smooth, and don’t introduce unnecessary complications.

At the final moment, when the contract is in front of them, expect one last wave of nerves. It might be a pricing tweak. It might be a sudden need for “just one more week to think.” Be patient—but firm. Keep them moving toward the exit like a bouncer at last call.

Final Thought: Sell Them on Selling

In the end, buying a business isn’t just a financial transaction—it’s an emotional one. The best buyers aren’t just good at spreadsheets and legal negotiations. They’re good at managing human psychology.

So, be patient. Be empathetic. And for the love of all things profitable, don’t roll your eyes when they start reminiscing about “the early days.” Because if you play it right, they’ll walk away feeling like they made the best decision of their life—and you’ll walk away with a deal that actually closes.