By Steve Walsh, Techstars Mentor-in-Residence and Founder of Hands On Angel LLC

This week I came across two photos of myself.

The first was taken in 2018, about a month before I left my corporate career.

Suit. Tie. Executive headshot.

At the time, I was leading a large organization. I had a great team, a successful career, and a path that looked pretty predictable from the outside.

The second photo was taken a month ago while my wife and I were walking around Florida.

T-shirt. Sunglasses. No schedule. No boardroom. No corporate title.

Just two people enjoying a beautiful day together.

When I put the photos side by side, I couldn't help but smile.

Not because one version is better than the other.

Because both versions of me were successful.

Just in different ways.

The guy in the first photo spent years building a career. He worked hard, learned how organizations operate, managed teams, handled pressure, and developed skills that I still use every day.

The guy in the second photo is benefiting from everything the first guy built.

The interesting part is that somewhere along the way, my definition of success changed.

When I was younger, success looked like promotions, responsibility, title, and compensation.

Today, success looks more like freedom.

Freedom to decide how I spend my time.

Freedom to choose who I work with.

Freedom to take a random trip with my wife.

Freedom to help founders because I want to, not because I have to.

And that's what got me thinking about founders.

I spend my days talking to people who are building companies. Many of them are raising capital, hiring teams, chasing growth, and trying to hit ambitious goals.

There's nothing wrong with that.

But every once in a while, I ask a question that catches people off guard:

What are you actually trying to build?

Most founders immediately start talking about revenue.

Or valuation.

Or headcount.

Or product.

But that's not what I'm asking.

I'm asking what kind of life they're trying to create.

Because building a company and building a life are not always the same thing.

A company is a vehicle.

The life is the destination.

The mistake I see founders make all the time is spending years obsessing over the vehicle while never defining the destination.

They know how much they want to raise.

They know how many customers they want.

They know what valuation they want.

But they haven't stopped long enough to ask themselves what success actually looks like when they get there.

More money?

More freedom?

More flexibility?

More impact?

More time with family?

A lot of founders assume those things automatically come with success.

Sometimes they do.

Sometimes they don't.

That's why I believe one of the most important questions a founder can ask isn't:

"How do I build a great company?"

It's:

"What kind of life am I trying to build?"

Because if you don't answer that question first, you may wake up one day and realize you built a company that owns you.

The older I get, the more I believe success is less about what you've built and more about whether you've built it intentionally.

The funny thing is that when I look at those two photos, I don't see a right answer and a wrong answer.

I see two chapters.

The first chapter built the foundation.

The second chapter is enjoying it.

And if you're building a company today, I would encourage you to ask yourself one simple question:

Am I building a company?

Or am I building a life?

Until next time — keep building.

Cheers, Steve

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