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From New York to Four Exits

How Eytan Wiener built, sold, and started again and why real success begins after the deal closes.

This week at EVOLVE, we had a different kind of conversation.
Not about growth. Not about metrics.
About what happens when you actually get what you were chasing.

We hosted Eytan Weiner, who’s done something few founders can say out loud four exits.
Four different chapters of building, scaling, and letting go.

And joining him were Stuart Thornton and Vinny O’Brien, both founders who’ve walked the same road, long nights, term sheets, and those silent mornings after the deal is signed.

What came out wasn’t theory.
It was truth.

Building to stay, not to sell

Eytan said something early on that set the tone for the whole hour:

It sounds simple.
But in a world obsessed with valuations, that’s almost rebellious.

He didn’t build with a buyer in mind.
He built with a problem in mind.
And that’s why buyers came.

His first company didn’t go viral, it worked.
Because he was solving something real.
And that’s what made all the difference.

Success, he said, isn’t about being ready to exit.
It’s about being worthy of being acquired.

Stuart’s version of the truth

Stuart Thornton sold his business too — eventually.
But he didn’t romanticize it.

He called the process “eight months of hell.”
Five failed negotiations.
One investor who made things harder than they had to be.
And a due diligence process that tested everything from his patience to his principles.

When silence hits

Eytan’s most powerful line wasn’t about money.
It was about what came after.

For a founder, that silence can be deafening.
The purpose that used to drive every day suddenly disappears.

No pitch decks. No fires to put out.
Just a void that money can’t fill.

That’s the part no one writes about the emotional hangover of success.
The loss of motion.
The loss of identity.

He said something that stayed with me:

Vision, ego, and self-awareness

When we asked about investing in founders, Eytan smiled:

That’s self-awareness the rarest trait in entrepreneurship.

He invests in founders who admit their blind spots.
Who don’t pretend to have it all figured out.

Vinny nodded. Stuart agreed.
Ego is easy to spot, and very hard to fix.

In every story they told, the turning point was never money it was humility.
The ability to ask for help, and the discipline to listen.Evolve for Senior Leaders

Lessons that linger

Here’s what the conversation really left behind:

• You can’t time an exit. You can only earn it.

• The best founders are problem solvers, not storytellers.

• Focus scales faster than diversification.

• Self-awareness is the new unfair advantage.

• Culture compounds. Always.

And maybe the most important one:
The real success begins after you sell.

Questions from the room

Our members never disappoint.
They asked what every founder secretly wants to know:

💬 “How prepared should you be for due diligence?”
Eytan laughed. “Prepared enough not to panic. But if you’re too prepared, you’re probably not growing fast enough.”

💬 “Do investors push for the wrong goals?”
“Some do. The best don’t. The good ones know value before valuation.”

💬 “Would you do it again?”
He paused. Smiled. “Already am.”

What makes founders like this special

Eytan, Stuart, and Vinny reminded us that business isn’t linear.
It’s human.

Behind every exit headline are months of doubt, exhaustion, and the quiet decision to keep showing up.

Their honesty was the real highlight no polished answers, no difficult terms, just lived experience.
They didn’t glorify success. They decoded it.

And in that, there was a kind of clarity that only comes from experience.

Closing thought

This was one of those EVOLVE sessions that felt more like a reflection than a talk.
Three founders, three different journeys, one shared truth — that the game doesn’t end when you sell.
It just changes shape.

Grateful to Eytan Weiner, Stuart Thornton, and Vinny O’Brien for taking us behind the headline.

And to our members, for asking the questions that made the hour unforgettable.

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