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Watch a founder negotiate with an investor and you'll see something close to ruthless. Every percentage point gets argued. The valuation gets stress-tested. The term sheet gets a lawyer. The pro-rata rights get a fight. By the time the wire hits, every share that just left the founder's pocket has been priced, justified, and earned a receipt in actual cash.

Now watch the same founder grant equity to a co-founder, an early employee, or an advisor.

They give it away like Halloween candy.

50% to a stranger they met at a hackathon. 2% to an early employee with a six-month vesting cliff and no performance gates. 0.25% to an advisor who once sent a useful email and never showed up again. The math, when you actually do it, is brutal — and it's the...

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...

Every Founder lies about why they are building a startup.

It's not because they are deceptive; I find Founders to be the most vulnerable and honest people I've ever met. It's because they aren't honest with themselves about why they are really building their startups.

When you ask a Founder why they are building, they are inevitably going to give you a stock answer like "I want to change the world!" or "I want to build a huge company!" and, of course, that sounds flowery and wonderful.

But that's not the real answer. The real answer is why are we building anything at all? What is the core purpose within us that drives us so hard to run through walls, empty our bank accounts, and set fire to our personal lives? It's not because we couldn't w...

Keeping control of a startup has nothing to do with owning the majority of it.

You can own 90% of your startup and still have to answer to someone else.

We hear this all of the time from Founders when raising money "I want to make sure I don't dilute too much of my company to investors because I want to maintain control of it."

Ah, the illusion of control.

In our minds, it means that we have enough ownership interest that no one can tell us what to do. We believe we can raise capital and take on outside investors without also having to be driven by them.

As it turns out, we can lose control of our startups in a lot of ways that have nothing to do with owning a majority share.

What is Control, Really?

Let's first define what controlling a co...

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...

Our happiness is directly proportional to our expectations. So what if we completely botch our expectations for how well our startup should do?

In over 30 years of helping Founders and most certainly in my own journey, I have never, ever heard a Founder give me a set of expectations that seemed perfectly reasonable.

For some reason, we all sprint into this abyss with the most insane expectations of how our startups are supposed to perform with almost zero grounding in either reality or reason.

While that may sound optimistic and exciting, it's also a giant recipe for failure and disappointment. Not because we're not awesome, but because what we assumed success would look like doesn't even remotely resemble reality.

The Snowflake Myth

Of cou...

What actually happens when the Founder runs out of gas and just can't keep going?

Does the startup just... stop?

In a world where we're all facing some level of burnout, we also have to consider what would happen to our startups if we just stopped contributing.

I've coached nearly a thousand Founders and CEOs through this "outta gas" problem, as well as myself, and I can tell you without question — it's never as bad as it sounds!

Burnout is Inevitable

Look, we all get burnt out eventually.

It doesn't matter what kind of superstar athlete you are in your startup, there's only so much of this pace we can endure before we run out of gas. This shit is hard.

The late nights, the nonstop worrying, the constant "if we can just make it past this mi...

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.

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...