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When is our ego an asset and when is it our greatest enemy?

The startup world is loaded with big egos, and if we're being honest, it kind of needs to be. We operate in one of the most insecure environments there is, where everyone is creating something out of nothing and hoping that next week they can simply make payroll. Without a little overconfidence, that's not an easy path to follow.

But that same overconfidence, when it's just pure ego, can also be our downfall. There's a point where we're no longer just confident, we're actually starting to lose our self-awareness altogether, and that's a dangerous spot. Many Founders don't even see it happening.

We Treat Assumptions like Facts

Early in our startups, we're forced to make a lot of big...

The way to get rid of Founder Impostor Syndrome is to just be a wildly successful Founder... right?

Actually no — and it surprisingly gets worse over time.

Founder Impostor Syndrome is what we feel when we think we're not truly qualified or capable of being a successful startup Founder. We second guess all of our decisions and outcomes because we have an endless stream of more successful Founders to compare ourselves to.

What we fail to realize is that no matter what we achieve, we never lose the feeling of being "less than qualified" we simply convert it to something else where we feel just as insecure.

Here's how it tends to happen.

We all Start as Freshman

Launching our startup is like showing up on the first day of High School as a do...

Startups are an excellent way to make money — for everyone else.

We all love hearing the story about that super-successful Founder who made a billion dollars growing their startup. Those legends fuel the myth that we "rank and file" Founders must also be swimming in our Scrooge McDuck vaults of cash.

Yet, I speak to thousands of Founders and if there's one common thread when it comes to money — it's that most of them are beyond broke!

So how is it that we can spend so much time building a wealth engine that doesn't actually provide any wealth for us? Where is all that money going anyway?

"Back of the Line, Pal!"

The problem starts with us. When we launch our startup, we're wildly resource-constrained, so we start off by sacrificing our own ...

No one will ever create more guilt over startup failure than the Founder.

Startup Founders have an insane ability to manufacture epic amounts of guilt over their own failures. It's almost like we do some magical alchemy that takes every pound of failure or criticism and turns it into a metric ton of guilt.

But should we really feel this guilty over failing at our startups?

There are two answers here. The first is — everyone does it. But that is of very little help. The second answer is just "no." Failing at a startup is painful but should not be a source of guilt. Guilt comes from our misunderstanding of what actually just happened.

Startups Typically Fail

For those that are unaware, most startups fail. Most Founders are doing this for the...

Startup Founders love the idea of full transparency when it works for them.

At first glance, it's hard to argue against the idea of "full transparency" in our startups. Who wouldn't want the inside information about what's really happening at a startup? Doesn't that make everyone feel more informed, safe, and supportive?

But try running a startup for long enough, and you'll quickly start to see that the concept of full transparency only works when things are good. The reality of running a startup quickly devolves into lots of shitty situations where going "full transparency" is more likely to sink our startups than improve them.

We Want Transparency When it's Positive

Startups often love the idea of full transparency in the early days when ...

For as much as we startup Founders love to innovate business models, we sure have done a lousy job of innovating on the employment model. Our salary lines tend to be our single largest expense in a company, and yet the biggest innovation we've had to date has been moving to a remote work system.

We've agreed that we don't need offices or "40-hour work weeks" anymore, so why haven't we agreed that we don't need the "full-time salaries" that came with them?

(Gasp!)

Yeah, I said it. Yeah, I'm about to be exponentially less popular. And, well, I wasn't that popular before, so… But seriously, why haven't we reconsidered compensation in an era where everything has become fractionalized?

Full-Time is Dead

Very few people actually work full-time an...

We need to treat every successful startup like it's our last — because statistically speaking, it probably will be.

In the startup biz, there are tons of second and third acts (I'm on my 9th) but there are very few that are ever equally successful. That's a problem for us as Founders, because we can easily lose sight of how important a single success is, and waste the opportunity thinking there will simply be another.

What if there isn't? What if this startup success, in whatever form it has right now, is the last successful startup we'll ever build? Shouldn't we treat it like gold versus assuming this is "one of many"? What happens if we get this wrong?

The Odds are Stacked Against Us

The first thing we need to understand is that the odds ...

Every good startup dies a thousand deaths before it ever lives.

We don't like to believe that because it sounds awful. Who would get excited about doing anything that sounded like it was going to die a bunch of times? Yet death — in the form of setbacks, restarts, and in some cases implosions — is kind of what we do for a living as Founders.

Pretending like we're going to get through this whole thing unscathed is like picking up a video game on the hardest setting and thinking we're going to beat the entire game without ever losing a life. It just doesn't work that way.

So just like our blinking Super Mario coming back to life for the 1,000th time, we've got to learn how to play through the whole game while pretty much expecting to lose a f...

The only thing harder than making a ton of money is giving it away to family.

On paper, it sounds easy. We've finally got some dough and now we can hand it out like Robinhood to all the people in need. What could feel better than helping our family with a little extra cash?

That's until we find out what a giant tangled mess of problems it tends to create. What we are thinking about is how helpful we can be, but what we're not thinking about — and where most Founders live in regret — is what a can of worms we open from here on out.

It. Never. Ends.

The problem with giving away money once is that once we open those floodgates, they are nearly impossible to close. All it takes is a single act of kindness to send those gates crashing open.

Here...

Venture-funded startups grow way beyond their means because they have to.

Time and time again we get asked by (typically bootstrapped) Founders about why in the hell venture-funded startups love that so-called "fake growth."

You've seen this before, when a new startup raises gobs of venture capital, hires hundreds of new people, burns through tens of millions of dollars (or more!), and then later on has to crash and burn the whole thing because it never actually made any money.

From the outside, it seems insane. What Founders don't realize is that this whole "fake growth strategy" isn't just some bizarre misstep - it's an actual playbook. We look at stories like WeWork and ask "How could anyone let that happen?" Well, it turns out, there's...