The Five-Month Deal: What a Smooth Sale Actually Looks Like

Five months. Start to finish.

That’s how long it took to close my most recent—and probably one of my smoothest—deals.

If you’ve ever sold a business, you know how rare that is. Deals usually drag. There’s always a surprise. A delay. A last-minute freak-out.

Not this one.

And while a bit of luck never hurts, I think there were a few clear reasons it worked out the way it did.

1. We did the hard work up front

Preparation is boring until it isn’t.

Most owners think the heavy lifting starts once the business hits the market, but in reality, the best deals are won long before that. Our CIM wasn’t just a sales documentm it was a full, thoughtful story of the business. It answered 90% of buyer questions before they had to ask.

That meant fewer interruptions and more confidence from day one. When buyers don’t have to chase down details, they spend more time imagining what owning the business would actually feel like.

2. The data room was ready before the LOI

This one might be the most underrated step in the entire process.

We had the data room built, organized, and verified before an LOI was even signed. Financials, contracts, employee agreements—everything. The result was zero downtime once due diligence began. The buyer’s team could dive in immediately, which kept the momentum going.

Momentum is oxygen in a deal. Lose it, and the whole thing starts to suffocate.

Most sellers wait until after an offer comes in to start collecting documents. That’s like packing your bags after your flight’s already boarding. If you can do the work early, you remove weeks of friction later.

3. The deal team trusted each other

Everyone talks about the importance of having the right advisors. What’s less talked about is the chemistry between them.

In this case, both lawyers had worked together before. They trusted each other, and I had a good relationship with both. So when small issues came up, as they always do, nobody reached for their sword. We solved them quickly, quietly, and without ego.

Deals fall apart when people dig in instead of working together. You can feel it in the tone of emails and calls. But when everyone in the room shares a mutual respect and a clear goal, it changes everything. Instead of defending turf, you’re solving problems.

That trust doesn’t happen by accident. It’s built through years of doing the right thing, being responsive, and surrounding yourself with people who share your values. When you finally have a deal worth protecting, you’ll be glad you did.

4. The price was fair, not inflated

It’s tempting to swing for the fences on price. Every owner wants to maximize value, and they should, but there’s a fine line between ambitious and unrealistic.

In this deal, we didn’t chase the highest theoretical number. We priced it at what the business was truly worth, supported by clean financials and clear rationale. Buyers saw the value right away, and the seller felt respected. That balance made negotiations smooth.

A “fair” price isn’t just about the math. It’s about tone. It signals seriousness and maturity. It says: this is a real opportunity, not a fishing expedition.

When you start too high, you invite skepticism. When you start fair, you build credibility. That credibility saves you time, energy, and goodwill later.

5. We chose the right buyer

Not just the one who offered the most money, the one who actually fit.

Cultural alignment doesn’t sound like a financial term, but it might be the single biggest predictor of whether a deal actually closes. The buyer in this case understood the business, respected the team, and shared the seller’s values. They weren’t looking to gut the company or reinvent the wheel. They wanted to carry the torch.

That shared philosophy made the handoff almost effortless. Post-close, both sides stayed in touch, and the transition was smooth because there was real trust.

You can’t fake that fit. When the personalities, motivations, and expectations line up, it’s almost like gravity takes over. The deal just moves.

The part you can’t control, and the part you can

There will always be things outside your control in M&A. Timing. Market conditions. Buyer financing. Random life events that pull people off course.

But here’s what I’ve learned: the more intention you put into the parts you can control, the more you expand your luck surface area. That’s what makes these rare five-month deals possible.

The irony is that a smooth process doesn’t feel flashy when you’re in it. It’s quiet. No drama. Everyone just keeps doing what they said they would do. The deal crosses the finish line almost without you noticing, and one day you realize it’s done.

That’s the reward for doing the hard work early. No fire drills. No sleepless nights waiting on missing documents or arguing over small stuff that should’ve been caught months before.

It’s not luck. It’s discipline.

Why this matters

When you’ve been around enough deals, you start to see patterns. The ones that go sideways almost always suffer from the same root issues: disorganization, misalignment, or ego.

The ones that go smoothly tend to have something else in common: people who take the process seriously long before it starts.

If you’re planning to sell, start building your “five-month deal” conditions now. Build relationships with professionals you trust. Clean up your books. Get your data room in order. Price honestly. Choose buyers carefully.

You can’t guarantee a perfect process. But you can give yourself a fighting chance at a calm, efficient one. And in this world, that’s as close to luck as it gets.