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I'm an incredible failure. Or at least, I try to be.

Over the past 30+ years of building startups, my greatest superpower has been my willingness and ability to embrace failure. If we don't understand how important failure is in the startup game, we have almost no chance of ever succeeding.

That's because we're in the game of failure. Not all out failure, like we're going out of our way to tank our startups (although that's kind of the default condition, sadly).

We're in the business of taking massive chances on unproven markets and products. There's zero chance that we're just going to get it right miraculously without running into a massive number of failures along the way.

But that's fine — so long as we get freakishly good at how to fai...

The business of predicting the future is going out of business.

AI is making a mess of everything. No matter how good (or bad) you were at forecasting what’s next, you could always rely on a few basic assumptions.

You knew that you’d be hiring certain types of people. You knew where you’d be finding customers. You knew that if you built a product, it would be around long enough to sell it.

Now? WTF.

The Sands Are Shifting Too Fast

Now, if I build a product, I have no idea if I can pull traffic from Google, because I don’t even know if people will be using Google to search anymore (I don’t). When I go to build that product, I don’t know who I’m going to hire because AI now does the stuff I used to hire people for.

Even if I get the damn thin...

What happens when we trade productivity for humanity?

We didn’t mean to do this. We didn’t wake up one day and decide that connection was optional. We chased speed. We chased leverage. We chased tools that promised fewer interruptions and more output. And they delivered. Quietly, efficiently, relentlessly.

Somewhere along the way, we stopped noticing what disappeared. Conversations became messages. Presence became availability. Thinking out loud became thinking alone. We didn’t lose our teams. We optimized them out of our daily lives. And now an already lonely job feels emptier than it ever has.

The Sprint Toward Efficiency

Ever since COVID, the startup world has not just adopted remote work. We embraced it at full speed. Slack replaced hal...

AI is about to make the concept of a traditional job obsolete.

That's great news, because it means they are going to get replaced by Founders building startups.

Welcome to the next generation of employer — You.

While everyone else is scrambling to wonder what's going to happen to so many jobs lost (and it's a real issue), we're thinking about what happens next. Does everyone just "lose their job" and stop working? Of course not. We create new ones.

The only difference this time is that those new jobs will largely be created by the next generation of Founders who need to rely on themselves for employment, not a corporation. And that makes things awfully interesting.

The Death of "Big Employment"

Within the next 5 to 10 years, the concept of ...

If you're a Founder for long enough, the question isn't whether you'll get burnt out - it's if you'll understand how to recover.

In order for us to do what we do, which is create something from absolutely nothing, we have to have a superhuman amount of energy and focus. Yet what we do daily saps that energy, and at some point, it's very difficult to get it back.

So when we're completely fried, and vacations and breaks are no longer doing anything for us, how do we get that spark back?

In Case You Missed It

Startups Don’t Go Bankrupt — Founders Do Startups don’t truly go bankrupt until their Founders go bankrupt. The problem is that Founders are often so focused on their startup’s finances that they overlook their own ability to stay afloat ...

Firefighters run into a burning building with the optimism that they'll get out. Founders run into a burning building and decide they are going to stay there for the next decade.

So how do we maintain our optimism when we know this thing's going to be burning down everywhere for a long time?

One of the many traits that define good Founders is our ability to sustainably live in a world that actually doesn't exist. While we're bleeding cash, turning over staff, and struggling just to get a product out the door, we still see the final, successful product just over the horizon.

How is being completely delusional our greatest tool for success?

In Case You Missed It

Am I Lying or Just Being Optimistic? Will our strong conviction that what we’re b...

I used to be popular... now I'm just productive.

For a long time, I used to think that the more I built my personal brand, the more successful my startup would become. I spent countless hours at networking events, speaking gigs, and 5 nights per week doing dinners to expand my network. At the time, I was awfully popular.

Then one day, during my millionth speaking event, one of my investors pulled me aside. He said, very bluntly, "WTF are you doing here? I invested in your startup, and all I see is you showing up at every networking event doing speeches. Why aren't you back in your office building a company?"

He was right. While I was busy building my personal brand, what I wasn't doing was building my startup. Yes, more people knew about my...

What if getting bigger makes us a worse company?

It's become the fundamental startup dogma that if you want to be a real startup, you have to scale as fast as possible and become as big as possible.

Bigger team. Bigger revenue. Bigger everything.

What if the very things that make this company special right now, our culture, our energy, our freedom, get destroyed by growth? What if the freedom we fought so hard for turns into investor stress, board expectations, and straight-up self-loathing?

There's a point where the concept of growth masks the destruction of what made us great to begin with.

In Case You Missed It

We Get Paid For Finishes, Not Starts As Founders, it's important for us to remember that nothing matters until the end goal is r...

“Just Be Yourself” is wonderful Founder advice 6% of the time

In startups, authenticity is valuable, but unfiltered honesty can be nuclear. The idea of being our authentic selves sounds great, but it assumes that what comes out of our mouths doesn’t carry serious consequences. When we are responsible for people, money, and reputation, being ourselves without a filter can destroy everything we have built.

This isn't a knock on who we are as people. It is a reminder that no matter who we are, we have a responsibility to apply a filter, and the less we understand that responsibility, the more it will cost us.

In Case You Missed It

Can I Hire Someone to Run My Startup for Me? Passing the reins sounds easy until you realize some parts of a start...

As a startup Founder, I've got a very long list of issues with myself, and that's just fine.

Want to hear my list?

• I'm obsessive. I can't stop working even when I hate what I'm doing.
• I'm hell-bent on control even though I know what I do offers next to none.
• I ignore successes and play failures on an infinite loop.
• I have zero attention span; I've already forgotten the opening line of this article.

Sound familiar? Maybe awful? It used to be for me. But at some point, I stopped trying so hard to "fix" me and started asking myself, "What is it about my fucked-up-ness that I can harness for good?"

What if there isn't a fix but instead a whole new world that opens up when we embrace how messed up we are?

The False Prophet of Fix

Hundreds of t...