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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). ...

Caution — This is a topic people feel very strongly about. My goal here is to open up a conversation to help Founders and their staff to find common ground to build from.

Over the past year, there have been heated reactions to companies like Coinbase and Basecamp instituting strict policies to remove discussions about "societal issues" from workplace forums. This has subsequently spawned some really passionate discussions among Founders about where they stood on the issue.

The workplace is changing rapidly, as well as the voices within it, yet many Founders aren't entirely clear as to what is "normalized" in workplace culture and what is taking things too far one way or the other. We're all going to need to think through these issues very c...

The idea of bringing on a "Superstar Advisor" is usually a total sham.

This isn't because the advisors themselves are a sham (they may be), but more so because our expectations of what these superstar advisors can do are way out of line.

The cost to this notion is giving away valuable equity or creating lob-sided revenue deals without really thinking through what these folks can realistically contribute. It's so easy for Advisors to make bold claims about what's possible, but like the rest of us, it's incredibly hard to back them up consistently.

But again, this normally isn't the fault of the advisors — it's our fault. We lull ourselves into expectations of these heroes that are totally unrealistic, and in many cases, not even what these ...