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Founders won't change people's personalities, we can only manage them. And that's where we fail over and over.

How often do we get frustrated by someone in our organization that we just wish we could change? They lack motivation, discipline, or they just don't play well with others. In our Founder minds, we just need this one inspirational heart-to-heart talk, or some Karate Kid montage, where they come out the other end a changed and improved human.

We have a hard time believing we can't "manage" our way into the outcome we're looking for, but what we're actually missing is that there are certain aspects of humans that go beyond what we can manage in the first place. And our lack of recognition of this boundary creates a colossal waste of ...

The worst time to get tired in a race is at the end.

Now, imagine we've just run a marathon (it's called a startup) and at the very end of that marathon is the finish line (it's called an exit), but we're too tired to make it across. Can you imagine a worse time to be out of energy than the moment where we're just about to win the race?

Yet many Founders, by the time we get to our most important milestone (the sale), just have nothing left. So we capitulate. We agree to silly terms, or unrealistic expectations, not because we think it's a good deal, but because we just want to be done with any deal. We're incredibly vulnerable, and that's incredibly dangerous.

"But I Just Want to be Done With it!"

Look, I get it. By the time we're teeing up...

The one thing everyone remembers about a relationship is how it ended.

As Founders, if we're around long enough, we're going to see the end of a boatload of relationships, and as such if we're not keenly aware of how important it is that we end those relationships gracefully, we're going to end up with a whole lotta angry exes.

There's really no way around this. Unlike our lives as an employee, where it was just us and our boss, when we are the boss, we're at the center of so many important relationships. Whether it's investors, staff, customers, partners, even the media — all of those relationships have a cost, and when they end, those costs actually multiply.

Later on in life, we learn how important it is to have "good breakups" because w...

The moment we sell our startup — the party is over.

Sure, we'll throw an actual party to thank everyone for taking the ride with us. We're going to issue well-crafted statements internally and externally about how this new partner is what we've been waiting all long for, regardless of whether it actually was.

But once those momentary celebrations subside, we're going to look around at what's left like a frat house after an all-night rager and think "Well damn, now what?" We worked so hard to get to this point, we often have no idea what would happen to the startup once it reached that penultimate moment. But, we're about to find out.

Waking Up Next to a Stranger

By the time we've signed the deal and watched that big wire land in our account...

The best way for Founders to gain power is to create it for themselves.

When I was a kid, I spent my whole existence feeling powerless, like all of my needs and dreams were tied to someone else's rules. I dreaded that feeling, but at every turn the reinforcement of the power dynamic was there, whether it was from my parents, my teachers, or Leeno who owned the pizza place that I worked at when I was 14. They had the power, they had the say. All I could do was make the best of their rules.

And if my adolescence taught me anything, it's that I absolutely hate being told what to do.

While I was a happy kid, I was miserable at my station in life. I thought I'd be the unwilling pawn in someone else's game, always working just smart enough to ma...

I don't remember going to college. I know I went, but I don't remember anything about my college experience, because unlike everyone else, I was too busy working on my startup.

I remember rollerblading (1990s!) across the quad to class on a beautifully sunny day and watching a bunch of my friends playing volleyball and having an amazing time. I wanted to play so badly, but I didn't. I had to get through class so I could skate back to the office for an all-night coding session on a new client project.

This isn't a story about how that effort paid off (it did), this is a story of how badly I regret never having played that day. It's a story of how so many of my life experiences were mortgaged for the sake of building my startup, and how looki...

Show me a startup that was once hot and I'll show you a Founder that got totally distracted by their own bullshit. As Founders, we're in the business of making dreams come true — particularly our own — so when everyone around is telling us how amazing we are, it's really hard to wake ourselves up and realize none of it is real.

Once hot startups all had a moment when everyone was praising what they did. The reason they are "once-hot startups" is that in the very moment they needed to be the most focused, they went off track believing their own press. It's a challenge that as Founders, if we understand, we can put ourselves in a position to avoid altogether.

When We're Up, We're Blind

When things are going well, we assume we've finally "made...

At a recent Founder Group meeting, one of the Founders asked the rest of the group if they regretted selling. All of them had past exits, ranging from a few hundred million to over a billion dollars.

With so much money at stake, and in each case billions of dollars "left on the table" post-exit, not one Founder had a single regret. It had nothing to do with what they cashed out for, it had everything to do with what they were willing to "let go".

We all share the same concern that if we sell too early we're going to look back on what became a trillion-dollar company and cry about all that we left behind. But there are actually a lot of ways to not only help hedge that financial concern, but also come to terms emotionally with walking away.

Offices are a relic that we keep using to justify work.

Think about it like this — if offices had never existed, and a bunch of us were building a startup, do you think anyone would agree with this proposal:

"Let's find a spot that's inconvenient to get to, separates us from our lives, requires us to work in the least comfortable setting, and leaves us doing essentially the same thing we did at home."

"Oh, also, let's pay a fortune for it."

Whoever made that insane proposal would probably get booted off the management team! And yet, here we are, clinging to that relic of a working environment like it's a badge of honor.

"But We Need Them to Build Culture"

Culture is incredibly important, but let's not hard code the concept of "having cultur...

What if our current startup success can't be repeated?

As Founders, we're ridiculous optimists, and for all of our "vision" we're pretty damned short-sighted. In our minds, if things are going this good now, it stands to reason that they will go even better in the future. It has to, right? We'll be better connected, more experienced, and way more prepared than we were for our current startups!

But that's not how startups work. The startup game isn't chess, where the conditions are similar and we're just more experienced. It's more like blackjack, where we know a little bit more, but the variability changes on every hand.

Don't Know What You Got, Til It's Gone

(If you sang this last headline in a Cinderella power-ballad, you are my people). ...