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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...

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...

What if the time comes when we trade our sacrifice for a payout and we find it wasn't what we had hoped?

Years ago I was sitting at dinner with my wife discussing the final details of closing on our new home in Bel Air, California. My wife, being the smarter of us, was lamenting the cost, and said that it was a big undertaking for our family, and she was second guessing whether we should do it.

I told her that was a big problem for me, but not because of the house. I said "I've been working every waking moment, non-stop for nearly 30 years. Every life event I skipped, every holiday I didn't celebrate, every experience I'll never get back was a promise I made to myself. That promise was that one day, it would enable me to do something extrao...

Congratulations — you just sold your company! Time to sit back and see the decimal places on your bank account sprint to the right!

Now you've got the means to do whatever you want with your newfound wealth. You've worked so hard to get here — what could possibly go wrong?

Everything. Everything can go wrong. And for many Founders it really does.

Whenever a Founder I know has a wealth event, the first thing I do is get in front of them and give them a very specific speech. I've been giving this speech for over 30 years, and I'd like to share it with you today.

I've lovingly titled the speech "Congrats, now don't fuck it up!"

You Only Need to Win Once

The problem with gamblers like us is that we love to win. So the idea of not winning again...