Common Mistakes Sellers Make + What the Right Advisor Should Help You See

Most founders obsess over valuation and then get surprised when post-sale life feels off.

The truth? The real mistake happens earlier: not understanding the buyer, the deal dynamic, or what really matters in the long run.

Here are the common pitfalls and how to avoid them:

Mistake #1: Not Truly Understanding the Buyer

The biggest mistake sellers make is stepping into a transaction without really understanding who they’re selling to.

That includes understanding the buyer's:

• Motivation

• Decision making style

• Long-term vision

• Track record under pressure

This isn’t just a PE issue. It can happen with strategics and search funds too. 

If a seller doesn’t understand where the buyer is going or how decisions will get made it’s much harder to feel confident or supportive after the transaction.

Valuation is important but it’s only about 65% of the equation. The other 35%?

That’s qualitative.

Mistake #2: Trying to Sell the Whole Story Instead of the Real Strength

Sellers often present their business as a platform that “can do everything.”

The reality is: great companies are sticky because they do a few things exceptionally well and THAT's what makes customers stay.

When I evaluate a company, I’m not just asking what’s possible. I’m asking:

• What is this company best in the world at?

• Why do customers stay?

That’s the thread I want to pull. That’s what will carry into the future.

Mistake #3: Viewing Negotiation as a Win-Lose Game

I wish more sellers heard this at the beginning of a process:

“You’re not negotiating against someone. You’re solving a problem with someone.”

Good advisors help you step back and ask:

• What actually matters to me?

• What does the buyer need to feel confident?

• How do we get to a place where we both sleep at night?

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Selling can feel personal. You’ve built something meaningful, and when buyers ask hard questions, it can feel like they’re second-guessing your work.

But if a buyer didn’t appreciate what you’ve built, they wouldn’t be interested.

They’re not poking holes. They’re trying to understand the business they’ll soon be responsible for.

What I Wish Every Advisor Would Say at the First Meeting

“Let’s look at the whole picture, including what your life looks like after the deal. Let’s understand who this buyer is, not just what they’re offering. Let’s work together to make this process one that reflects the quality of what you’ve built.”

That kind of framing leads to better outcomes, not because the deal is perfect, but because it’s aligned.

If you’re thinking about selling (or already in conversations) take the time to ask deeper questions, about yourself, about the buyer, and about the future.

#SaaS #Software #SearchFunds #ExitPlanning #JaanCapital