The 5 Deal-Killing Mistakes

Mistake 1: No Urgency = Dead Deal

Deals without deadlines die. Period.

You need a compelling event for the buyer to move. Without urgency, they'll "evaluate" you for 18 months while their priorities change and your deal becomes old news.

Set real deadlines: "We need to close by Q4 for tax reasons." "Our board meets in 6 weeks and I need a decision." "We have another interested party who needs an answer by Friday." "If you can't close within 3 months, we should stop talking."

Then stick to them. Kill deals that drag past your deadlines. If the deal is real, urgency won't kill it. It will increase the probability of closing.

Mistake 2: Not Being Ready to Walk Away

In every one of my exits, the deal only got serious when I threatened to kill it. Not as a negotiation tactic. I genuinely meant it.

Example: Their lawyers tried to increase escrow from 10% to 15% after I'd made it clear I wouldn't go above 10%. I said "absofuckinglutely not," then redlined it back to 8% and said now it's 8% or we're walking.

Suddenly they found a way to make 8% work. Once you put your foot down, things move. If you're not willing to walk away, you have no leverage.

Mistake 3: Acting Like the Deal Is Done Before It Actually Is

This is the classic "counting your chickens before they hatch" mistake, and it kills deals in two devastating ways.

First: Premature celebration and taking your foot off the gas. A deal is not done until the wires have cleared. Period. The moment you start thinking "this is going to happen" before it has actually happened, you open yourself up to overlooking things, not double-checking details, and not following up with the right people.

There are so many things that can go wrong between signing and closing that you should never let your guard down. Keep working as if the deal might fall through, because it might. Stay vigilant on every detail until the money hits your account.

Second: Telling too many people before the deal closes. When you start acting like the deal is done, you risk the buyer getting cold feet if they hear through the grapevine that you're already celebrating. Your team starts behaving differently, taking different actions, and those changes can have negative ramifications on the deal itself or even post-closing integration.

Keep your circle tight. Only tell people who absolutely need to know, and remind them that nothing is final until it's final.

Mistake 4: Letting Others Control Your Deal

It's easy to get lost in what everyone else wants. Your investors want maximum return. Your banker says buyers want this structure. Your employees want job security. Your lawyers and advisors say "you can't do that" or "this isn't market."

Here's why this kills deals: If you don't keep what you want at the forefront of your mind and beeline towards it, if you try to prioritize what everybody else wants instead, you're going to end up at a place where you're not excited about the deal anymore.

When that happens, one of two things will kill your deal: Either you'll kill it yourself because you're no longer excited about it, or your lack of excitement will drag the deal on and on until it dies from being dragged on too much.

Save yourself the time, the trouble, and the headache. Make sure you're getting what you want out of the deal.

It's your company and your deal. Everyone else works for you, not the other way around.

Tell them what you want done and make them figure out how. Examples: "We want 90% cash at close." "We want a 6-month escrow period." "I want to keep my entire leadership team for 2 years minimum." You're paying advisors $50K-$5M+ to execute your vision, not limit your options.

Don't let other people's agendas or limitations dictate the terms of your exit. This is your moment. Make the deal work for you.

Mistake 5: Not Anchoring Price First

All the negotiation advice says "let them make the first offer." That's bullshit.

In every deal I've done, we agreed on price before starting diligence. I always said the number first: "It has to be somewhere around X" or "We won't consider anything below Y multiple."

Anchoring works. You want them negotiating down from your number, not up from theirs.