Seller Sit-Down: What Founders Wish They Knew Before Selling

There is a common theme with the founders/sellers I’ve talked to after selling their company:

“I wish I had known how much of a journey it would be.”

Here’s what I’ve learned from those conversations and what I’d tell any founder/operator who’s considering a sale:

It’s emotional, exhausting, and full of moments no one prepares you for.

This post is a blend of what I’ve consistently heard from those who’ve gone through it, along with my own experience.

“The emotions swung more than I expected.”

In the final weeks before closing, founders swing between excitement, fear, doubt, hope, and concern, sometimes in the same day.

You feel proud of what you built, uncertain about what comes next, and a little scared to let go.

That emotional rollercoaster? It’s normal, and it means you care.

 “I didn’t realize how long—and exhausting—it [the process] would be.”

Selling your company becomes a second full-time job.

Due diligence is intense. The questions feel endless. All while you’re still running the business day to day.

Many sellers tell me how draining it was, not just the logistics, but the emotional weight of explaining what had become second nature to them.

“After closing, I realized how much I actually knew.”

This realization hits everyone post-close:

“Even after all that diligence… the buyer still barely understands the business.”

That’s when it becomes clear: what felt intuitive to you—customer nuances, team dynamics, internal rhythm is actually hard-earned institutional knowledge.

You built the playbook. Only after stepping away do you fully see its depth.

“I wish I had taken time to enjoy the process.”

You may only go through this once, maybe twice.

Yes, it’s hard but it’s also rare. Buyers are interested. You’re being courted for something you built.

If you spend the whole process stressing, you’ll miss the chance to actually appreciate it.

Take the win. You earned it.

One Piece of Advice

This isn’t just a transaction. It’s a transition.

Give yourself the space to feel it.

Stay grounded in what matters.

And recognize how far you’ve come.

If you do that, you’ll walk away proud of how it ended.

If you’re thinking about selling, I’m always happy to talk through what it really looks like before you get too far down the path.

#SaaS #ExitStrategy #SoftwareAcquisition #SearchFunds #JaanCapital