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How far off are we from not needing any employees — ever?

I know this sounds a little out there, but maybe not. We're watching a dramatic shift happen, where more and more Founders are replacing all the people they used to hire with AI.

I don't love it. It's weird. I'm used to working with a team, and that has always been one of the best parts of my job: building startups. But for millions of Founders who are just starting out, who don't have the resources to hire an entire team, being able to do the things it used to take a team to do (without one) is awfully appealing!

This isn't an argument for why hiring people is "bad." It's not.

This is an exploration about how much longer we're going to need to hire anyone at all, and what that means...

A startup's work is never done — and that's a huge problem.

In reasonable parts of life, which startups clearly aren't, your workday starts and ends. You're told to do a job, you do it, and get paid on Friday. The correlation between your work, your progress, and your income is incredibly well understood.

But we don't have reasonable jobs, do we?

In our world, no matter how many times we cross a finish line, it's like we're instantly at the start of the next race, over and over and over. The moment we close a funding round, we're already out raising the next one. The moment we get a single paying customer, we need 100 more. Rinse, repeat.

How do you win a race that never ends?

The "Arrival Fallacy"

The problem starts when we actually believ...

Sometimes, the most important path for a startup has nothing to do with the startup.

As my fellow video gamers know, when you pursue something other than the main questline in a game, it's known as a "side quest." It's a tiny detour that you take to see if there are other riches to be found elsewhere.

In startups, those side quests may feel like a distraction, but in fact, they are often exactly what we need to keep our startups alive.

I'm a giant fan of side quests at startups, partially because my ADHD loves distractions and partially because I've found they pay really well.

The Myth of the Linear Path

The reason we get pushback on taking on side quests is that we seem to keep believing the myth that startups should follow a linear path.

Is it possible to recover from burnout?

Burnout doesn’t mean you’ve failed. It means you’ve slammed into the same wall every founder eventually hits.

The danger is mistaking your own exhaustion for your startup’s fate. Burnout feels permanent. It isn’t. Treat it like a setback, not a stop sign.

The real question isn’t if burnout will happen — it’s what you’ll do when it does. Some founders walk away too soon. Others find a second wind and do their best work on the other side.

We're So Connected — And Totally Lonely Despite endless digital tools, Founders are facing record levels of isolation, and only real human connection can fix it.

You Only Think You Work Hard There's a common misconception about 'working hard' within startups. Let's cha...

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...

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...

Most startup Founders never get rich — and it's 100% our own fault.

I'm not talking about not getting rich because our startup failed — that one is obvious. I'm talking about having a startup that actually worked and still not getting rich. And when I say "rich" I don't mean "Powerball Rich" I'm talking in most cases, making any money at all. As a whole, we tend to suck at making money for ourselves.

The reason for this is that the startup ethos is riddled with fallacies about how we should approach profit and wealth. We've constructed a narrative that glorifies sacrifice and risk while somehow completely overlooking common sense and profit.

Founders need a reality check. We need to remind ourselves that treading down the most dangerous pat...

Every Founder wishes they had more money, but we often don't realize what happens when we spend it.

There's this fascinating transition point that we go through as Founders where our problems start with income (because we always start with zero) and then quickly transition to debts (because someone always needs to be paid).

We put ourselves in this dangerous loop where instead of getting ahead on that next round of income, we actually dig ourselves deeper into a hole by adding exponentially more costs—and those costs aren't just financial.

We don't just grow income; we grow problems, and sometimes, way faster.

The Weight of Zeroes

When I was building my first startup with just a couple of college kids on payroll, I was terrified that I woul...

Some investors may be considered "angels" — but they are no saints!

That's why when it comes to getting "bailed out" by future investors, whether it be compensating us personally for money we've lost or helping to get our startup out of debt, we're entirely on our own. We've helped thousands of Founders raise capital, and invariably, many ask whether new investors would be willing to cover their previous losses or investments. The short answer is "absolutely not." But the longer answer may help you understand exactly why.

What Debts Are We Talking About?

The most common debts Founders ask about are personal debt they've created in financing the company or forgone compensation. The question often looks like, "I've put in $100,000 of my own m...

Most startups launch with $0 in funding, but no one ever really explains how the hell they do it. We keep saying, "They bootstrapped it," as if that explains anything other than "They didn't take on investors." What the heck does that even mean? What it is intended to mean is that we find creative ways to compensate people and buy things that don't involve using cash in the bank.

We can't possibly cover every use case of how startups find resources for $0, but let's take a look at the most popular categories that people run around looking for money for and see how we make it work.

Paying for People

Figuring out how to compensate people is where we're often stuck first. Most of us are familiar with paying folks with equity, but that's not th...