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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...

*"Fear and uncertainty are at an all time high right now among Founders, but this what we are built for. In the most uncertain times we build our greatest dreams. We plow forward when everyone else runs away. Stand strong, friends, we're gonna get through this together."

— Wil Schroter*

There’s a funny thing about building a startup: if it doesn’t scare the hell out of you, you’re probably not building it right.

Founders like to dream big, talk big, and pitch big. But behind every pitch deck and inspirational LinkedIn post is a cold, shaky hand wondering if this is the moment everything falls apart. That’s not weakness — that’s the real cost of greatness.

Even small outcomes can require big risks, and those don't come with a safety net. The...

Guessing is Not a Successful Sales Strategy. Create an ideal customer profile instead.

Think your product is “for everyone”? That’s cute. It’s also a ticket to early stage startup hell.

One of the top reasons startups fail (42%!) is building something nobody actually needs. Translation: they never clearly defined who their real customer was. In startup post-mortems you’ll hear the haunting refrain: “no market need.”

An Ideal Customer Profile (ICP) is the antidote to that fate. It’s the crystal-clear picture of who truly needs what you’re selling. An ICP helps in qualifying leads effectively, ensuring your sales and marketing teams focus on the target audience.

Without it, you’re basically playing darts blindfolded and hoping for a bullseye...

What's the difference between a startup that's growing and just getting fat? Startups are synonymous with growth, so much so that we treat growth and the prospect of "getting bigger" as exclusively good. If we're growing, we must be winning, and therefore "growth is good."

But what happens when that growth turns from muscle to big, sloppy fat? All of a sudden, growth isn't good anymore. In fact, it's just kinda gross. Well, that's exactly what happens at startups, and it's not just when we hit thousands of people post-IPO. It can happen when we hit 20 people, and we're no longer the lean startup we were meant to be.

As Founders we need to be hyper-conscious about every bit of growth and whether it's actually making us more healthy overall.

We need to get back to building the startup that inspired us to begin with — we need to get back to our "Why."

Part of the Founder journey, really for all of us, starts with this amazing inspirational period of hopes and dreams, where we have this idea that we just can't wait to bring into the world. At that moment, all rationale and reason give way to exuberance and optimism — we become completely and utterly intoxicated with what's possible — and it's incredible!

At that very moment, we are filled to the brim with our "Why." Our "Why" is the entire purpose of building our startup. It's different for all of us, but it typically is a combination of personal goals, product vision, and desire to put a little dent in the universe. If you talk ...

No matter how much success we create with our startups, it almost never "cures" our need for validation. If anything, it often makes it worse.

It usually starts with this feeling that we need to prove the world wrong, and when we do, we'll have the last laugh (which is just code for "I need personal validation"). The relationship between building a startup and getting "revenge on something" is particularly strong with Founders because the very nature of what we do is so damn combative!

Haters and doubters are as much a part of our startup DNA as investors and customers. We've all had someone who thought we'd never pull this off, who questioned our ability and idea. Whether we admit it publicly or not, we all want to show them how incredibly...

As Founders, we're so worried about losing control of our startups to investors that we completely overlook how we secretly lose control to everyone else.

The fact is, most Founders don't lose control of their startups to investors; they lose control of their startups to their own organizations, whether or not they even have investors. We do it willingly, in the name of progress, and we celebrate those milestones the entire time, all the while being totally unaware of how we've let things slip.

It's not until years later when we realize we can't make key decisions independently, we can no longer shape the product vision how we'd like, or we simply can't get anything done anymore, that we realize we've lost control through our own doing.

In...