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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.

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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 ...

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.

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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...

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...

Entry-level workers are no longer U.S. college grads—in fact, some aren't even human anymore.

The world of entry-level talent has completely changed in the past decade, particularly for startups. Not too long ago, startups raided colleges with an implicit understanding that among college grads, you could find someone who was smart (the college part), willing to work hard (lots of free time), and relatively cheap (first job).

I know this well because I was exactly that—young, relatively smart, insanely hungry, and freakishly cheap to hire. Since then, I've been trying to find my 19-year-old clone every single day of my Founder life. What has changed, though, is that the most fertile hunting grounds for those folks are no longer U.S. colleges...

Our most broken assumption in Year 1 is that anyone will stick around for Year 2.

Spoiler Alert: They won't, and the cost of giving away a ton of equity and responsibility to people who won't be around for long is incredibly expensive.

I see this play out all the time, especially with First Time Founders who naively think that everyone who promised to help launch their startup in Year One will actually stick around to do it. It’s easy to make that mistake — when everyone’s talking a big game and acting just as excited as we are to build something amazing, we can’t help but believe them.

But all of a sudden, people stop showing up. That Co-Founder CTO whom we thought was going to build the whole product for "free" goes MIA. That mentor who ...

At what point do we find out if all of our startup sacrifice was worth it?

The prevailing theory is that as Founders, we can justify our sacrifices of time, money, and emotional energy for the bounty of riches we'll enjoy on the other side. It's almost hard-coded into all of us the moment we take the plunge to start something.

But what happens when we're on the other side and we're forced to come to terms with whether or not those sacrifices were justified? Can we truly replace what was lost in getting here with what was gained through our efforts? What if we straight up made a bad bet?

Let me tell you a personal story about my journey as a Founder over 30 (very long) years of building startups and my assessment of a mountain of sacrifice o...

The startup world is in a "Silent Recession" that no one is talking about, and it's a real problem.

Most of the Founders I speak to in private say the same thing — their business isn't going well. It's a combination of a weird economy, a Nuclear Winter in startup funding, and sky-high interest rates. Economists can tell us that the stock market is at an all-time high, unemployment is down, and inflation means people are spending too quickly. Yet if you talk to enough Founders honestly, they will tell a very different story.

If you're at a point where you're trying to understand why things aren't quite going as well as they should, let me shed some light on things my friends. We're in a Silent Recession among startups, where secretly they ar...