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There's absolutely no way to go through the startup journey and not screw something up — OK, a ton of things. So why, as Founders, are we so bad about admitting our mistakes?

Unlike many other aspects of life, both personally and professionally, admitting we're wrong appears to have much more painful consequences to Founders because so many more people are involved. When I worked at a job and I messed up, the only people that were affected were my boss (who was unsurprised) and potentially my co-workers (who definitely didn't care). The consequences of my mistakes were tiny.

But now I have 200 people that rely on me. If I make a mistake, it affects all of them, and in some cases all the people that they are connected to as well. As Founders...

Being a Founder is a job that anyone can get and no one is qualified for.

My 9-year-old daughter became a Founder last year within 60 minutes of forming her own company online (she didn't even need my help). I'd argue she's about as qualified as most of the Founders I meet at Startups.com, and that's not a knock. It's to say that none of us are "qualified" to be a Founder, not because we're not smart enough, or capable enough, or experienced enough — it's because fundamentally it's impossible to be qualified for this job.

We Can't Be An Expert At Everything

The difference between a Founder leading a startup and a CEO leading an established business is that the Founder has to be there from the start when no one else is there. That means the...

Who cares how fast we can scale if we're not around long enough to do it?

That was our motto at Startups.com since Day One. While it's a ton of fun to think of grand growth strategies to take over the world, it kinda helps to be solvent enough as a company to see them through (at least that's what we've heard). What we've developed over the past decade are essentially two strategies for every major initiative — a "Downside Strategy" where we plan out the worst that could happen and an "Upside Strategy" which considers growth.

Most startups don't actually do this. Instead, we have basically a growth strategy and then in the back of our minds, we sort of formulate this "Oh Shit! Strategy" which loosely envisions what could happen if this does...

As Founders, so many of us have joined this marathon because we believed there was our own version of "happiness" on the other side of it. The problem for many Founders, once they've "made it" is that they don't realize that money was never going to buy more happiness. In fact, it wasn't the problem they were solving for, to begin with.

Think of it like getting a big, honking bruise. In this case, that bruise is a metaphor for debt. When you have a bruise, you're constantly worried about it — it's super painful. So we think about how great it will be when it goes away. And eventually, it heals (we have some money). But all we did was get rid of the pain, we don't actually become "more healthy" than we were before.

The same goes for debt. Wh...

If most early-stage Founders were being completely transparent with their staff, their company updates would probably look something like this:

"Hey everyone, good to see you all on Zoom. So my quick update is this — We don't know if we have enough runway to make it to our next funding round. Also, I'm getting a lot of personal emails from folks saying they don't see the vision anymore. And personally, I don't really think this was the right decision for me or my family. So.. who wants to lead with OKR updates?"

That's the kind of truth that exists for us as Founders every day, and yet we find ourselves "hiding" that truth from our staff on a daily basis. Does that make us horrible people? Do all Founders leave this kind of information out?...

I've failed numerous times and watched countless other Founders do the same. We kept ourselves awake nonstop worrying about the outcome of our failures. We took years off of our life and put ourselves in horrible places mentally and physically.

And you know what we learned in the end? It generally didn't matter.

That's right, our "fear of failure" was always 100x worse than how the failure itself played out. And so we took desperate measures to avoid failure, like clearing the last of our savings, running up debt, and going yet another year without pay. At some point, we became far more intent on "not failing" than succeeding.

What we need is a method for dissecting failure into actionable bits.

Failure needs to be Unpacked

If we think ab...

Most Founders get rich without ever exiting their business. Yes, you read that right. We don't have to build a rocket ship that takes on gobs of funding for an IPO in order to have everything we want.

We just need to keep making money (and not even that much!)

While to most people this may sound obvious, in the startup world we tend to forget how this simple fact works. We keep thinking in terms of this big liquidity event where we get handed a giant check like we just won the Powerball. We picture ringing the bell on NASDAQ wearing the only nice outfit we own shaking hands with bankers and smiling for the camera.

And in the end, we picture having enough money to just do whatever the eff we want.

The Stacking Effect

I spend a ridiculous amo...

A few years back I was driving through a windy street of Bel-Air with my wife, looking at houses. If you ever want to feel ridiculously poor, I encourage you to do the same.

During our home tour we drove up beside a house under construction that was so big, we thought it was a hotel. We just kept driving around the perimeter of the house, and it just kept going! Our realtor told us it was the future home of Elon Musk.

A younger version of me would have said "Someday I'm going to have that house!" and believed wholeheartedly that there were some future series of events that would lead to that outcome. It's the blessing and curse of being a Founder I think.

I turned to my wife and said "I can't have that — and that's OK." Let me explain why t...

There we are, once again, sitting at yet another Founder get-together while everyone tells us how great their startups are doing. Oh shit, that woman just said that they raised a massive round of funding. That guy just said he just surpassed 100 employees. The other person (I'm losing count) just claimed they are growing 50% per month.

"WTF? I thought I was doing great and now listening to everyone else I feel like a total loser."

And there it is. The age-old startup-sizing "competition" where we indeliberately one-up each other with how amazing our startups are doing. In the process, we all make each other feel miserable about ourselves.

What's that? You don't do that at get-togethers? Well, if you're like most, you're doing it anyway in s...

To grow or to profit, that is the question!

There we are, with a fistful of profit in our hands (finally!) and an endless list of places to spend it! Do we hire another engineer to get our product shipped faster? How about increasing our marketing budget to scale customer acquisition? Or, and let's just get crazy, do we finally pay ourselves?

Profit First, then Grow

I'm going to go out on a limb and spat in the face of startup lore, which suggests that the only way to succeed is to bet the farm and grow. Think of me as the owner of a casino (in this case, that casino is Startups.com) who gets to not only witness a handful of people bet it all and get rich, but 100x more bet it all and fail.

What we miss in our passion for greatness is that...