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I’ve reinvented myself so many times I don’t even remember what version 1.0 looked like.

At various points, I’ve been a commercial actor, a web developer, a carpenter, an author, and an entrepreneur. Some of those roles overlapped, some I left behind entirely. Reinvention isn’t just something I’ve done — it's coded into my DNA.

And as Founders, it's in all of our DNA to fundamentally re-invent ourselves. So why do we feel so stuck in the roles we hold today? Why does shifting paths feel so risky, so disloyal to the identity we've built — when our entire existence is built on questioning assumptions?

What would it take for us to wake up tomorrow and say, “Screw it, I’m doing something completely different”?

We Get Easily Stuck

In most career...

Being a Founder has always been a lonely experience. So how is it that with a million ways to connect to each other, we've never been more lonely?

In the past couple of years when I sit down with Founders in person, I always ask how well they are maintaining their personal relationships. In the past few years, I've noticed a significant downward trend where more Founders are finding themselves more isolated from the world around them.

Being a Founder was always isolating, but this trend really concerns me.

We used to live in a world where we were surrounded by co-workers by day, out with friends and loved ones at night, and having conversations on the phone with those we couldn't connect with in person.

Since then, we've begun to build a ...

How do we become confident Founders when none of us have ever done this before?

As a startup CEO for over 30 years, I can tell you I have the confidence now, but when I was starting at 19... not even close. I was so out of my depth I was terrified to even tell people I was a CEO for fear they would laugh at me. And they often did.

Back then, I thought confidence was something certain people were just born with — like being tall or having good skin. Growing up, there were always those kids who seemed like they had it figured out. I assumed they had something I didn’t.

Years later I'd come to know those same supposedly confident people very well, and I'd learn a valuable lesson — no one is just "naturally confident." It all comes from experie...

What if college simply doesn't make sense for aspiring Founders — are we ready to sacrifice this sacred cow?

Last week I was having lunch with a very successful old friend who made over $100 million in his career. He wanted me to sit down and advise his 18-year-old son who had just graduated high school. The first thing he said was, "He's decided to skip college and go straight to starting his own company."

This is the first time I've heard a parent say that out loud, but I'm starting to think it certainly won't be the last.

My immediate gut reaction was going to be some defense of college, even though I dropped out as fast as I could to start my first company. But no matter how many points I sped through in my mind, I couldn't come up with...

What if our startup is only failing because we refuse to let it evolve?

There’s a moment in every Founder’s journey when nothing feels like it’s working. The product isn’t catching on. The sales aren’t converting. The market isn’t responding. And the creeping voice starts to whisper: “Maybe this just isn’t going to work.”

But what if it’s not the startup that’s failing — it's us?

What if we're the ones who are holding on too tightly to the original product or vision that we're preventing our startup from evolving into what it's meant to be?

The Myth of the Perfect Plan

Most of us fall in love with an idea before we’ve ever tested it. That’s how this whole thing starts. We get a flash of inspiration, we build the deck, and we convince oursel...

A year ago, on a random Tuesday afternoon, I was driving home from an appointment and called an old friend — someone I’ve known for years, a high-level exec with big responsibilities and serious sales goals.

I asked him what he was up to. He said, “I’m floating in my pool.” I laughed. I thought he was joking. It was 2pm... on a Tuesday! People like him (people like us) don’t do that.

So I asked him why. He paused, like he’d never really been asked that question before, and simply said, “It makes me happy.” That was it. No explanation, no excuse. Just a basic truth. And in that moment, it hit me: the fact that I didn’t know that answer was my problem, not his.

In Case You Missed It

We Need a Strict Definition of Personal Success Every moment...

In my early 20's I had my first taste of success, and like any idiot who has a couple of extra dollars (and typically happens to be a guy) I spent a bunch of money on a fancy sports car. It felt like a trophy for having accomplished something great. I couldn't wait to share it with my friends.

It... did not go well.

I had an old friend from Middle School in town the weekend that I bought it, and when I unveiled this shiny new toy, here's what I got: "Yeah, well, it must be nice." This may not shock you, but he was not happy about the situation. He resented it, and he resented my success. At the time I was truly shocked, but now having been down this road for a while, I'm well aware of why.

As Founders we often believe that our success will ...

What happens when the company we built no longer needs the version of us who built it?

At some point, I walked into a building as the CEO of a company with over 600 employees. I looked around and realized our HR department had more headcount than our whole company used to be, which made sense because we were managing $10 million a month in payroll.

Our focus had moved toward doubling headcount — again. We were recruiting top execs from Fortune 500 companies to help us plan an IPO. These were the same people who would have never even looked at my resume a few years earlier!

I was 26 years old at the time, and it was becoming evident to everyone, especially me, that this company had clearly outgrown me. It was time for me to go — but what do ...

Wil’s Personal Note: “Founders, I want you to give yourself 100x more credit than you probably are for doing what you’ve already done. If we lose perspective of our progress, we’ve already lost. We need that perspective to fuel our next big win.”

When I was living in Beverly Hills, I felt like a total loser. This isn't some lame setup to a humble brag, I'm telling you I never saw this coming and it pissed me off.

As a kid growing up without much, I never thought in a million years I'd be living in Beverly Hills, so my expectations heading into life were very low. But every morning when I would wake up, I would look across this sun-drenched canyon and see the most amazing houses you would ever see — literally billionaire homes.

Do you know...

What if we had a passion that consumed us more than our startup?

Being a Founder means thinking about your startup constantly. It’s not just work—it’s identity. And over time, it quietly starts to absorb more and more of our energy, attention, and sense of self.

For most people with “normal” jobs, the solution to burnout is taking a break—a vacation, a long weekend, a few nights offline. That works because their jobs stop when they walk away. But for Founders, our jobs never really stop. Our minds don’t clock out at 5pm. Even when we’re technically away, our brains keep running the simulation—funding, hiring, product, growth.

We can’t pretend like we can just flip the switch and shut it off. But what we can do is create a counterforce—somet...