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Just because it's our startup doesn't mean we still have upside in it.

Anyone who's taken on a single round of capital and has suffered the painful dilution that comes with has had the first taste of "reduced upside." We accept it though, like taking awful medicine because we know it'll make things better in the end. But at some point that medicine stops working.

At some point, we look around and realize that our startup no longer provides the kind of upside for us we thought it would. It was easy to overlook when we could see us "making billions" but now reality has set in and we realize we just have a really stressful job that pays us way below market.

Call it What it is

First off, we have to call it what it is — a shitty deal. Is it a sh...

Retirement is a beautiful lie we Founders tell ourselves.

We fantasize about one day selling our startup, retiring, and living this gifted life that makes all of our sacrifices worthwhile. We see this perfect existence that was only constrained by the shackles of our work and the drudgery that was our startup.

Yet it turns out while it may be a fantasy for us, many enterprising Founders before us have actually playtested this fantasy for real. As it happens, nearly all of us develop some version of the same fantasy and later on come to the same (much more sober) reality.

It turns out, it's really easy to tell ourselves what we're going to do when we retire, but actually doing any of that stuff is harder than building the startup it took to ...

The worst advice Founders get consistently comes from their hometown.

I call these the "local yocals" and every hometown has them. They are well-meaning advisors who try to guide a Founder through the startup stages but instead fill their head with irrelevant, outdated, and in many cases straight-up bad advice.

Every single time I talk to a Founder that's been clearly led astray, I ask where they got that advice. And in almost every case, it's from someone that simply isn't relevant to the startup ecosystem. It's their well-meaning uncle who made a boatload of money in commercial real estate, or a local angel investor who has no idea who YCombinator is, or the "startup guru" who had the one exit in town but has never left the state.

From a ...

Sometimes the biggest financial startup success comes one paycheck at a time.

In our startup ecosystem, we've become infatuated with the concept that in order to be a successful startup we've got to have some massive IPO or sale. We sometimes forget that 99% of startups actually don't have that outcome and those people are buying Ferraris just the same.

The way most startups get rich isn't by that fairy tale exit (those are awesome BTW!) but by chipping away at growth and financial outcome over a longer period of time that gets them to the same outcome.

Digging a Hole vs. Building a Ladder

Imagine we've got two different paths toward creating our financial success. We're all pretty familiar with the first one, which is "digging a hole" beca...

Faking it as a startup is pretty much what being a startup is all about.

As first-time Founders, we just don't realize that it's the norm. Instead, we worry ourselves about not being a big enough company, not having a full staff, or not having a proven product.

Well, guess what? If we're just starting out, we fake everything!

Our Fake Website

"But wait, won't people find out that all we have right now is a cheap landing page that my cousin created and just a couple of products available?"

Yes, and they generally won't care. When is the last time you deliberated on the corporate structure of a company before making a purchase? Probably never. Most customers assume there is some level of functionality and deliverability in our product becaus...

Founders don't get the luxury of sharing openly — at least not without consequences.

Unfortunately, we learn this lesson the hard way, from acting and sharing like we used to do as an employee, only to find out that Founders don't get the same "safe space" we once enjoyed as employees.

Our startups are now a complex web of relationships, responsibilities and again, consequences that we need to understand and respect every time we're about to open our mouths about, well, anything.

It Wasn't Like This Before

When we were in our last job as an employee, we didn't really understand consequences the way we do now. If we got really pissed about something a co-worker did, we could hop on a Slack chat or if we were really clueless about this stuff,...

I have a confession — I am in a very unhealthy relationship... with my work.

Here's the thing — I absolutely love my job. I get to sit around and bullshit with Founders all day. This is my dream job, by design. We're normally conditioned to believe that our jobs are some sort of liability that we should try to escape from whenever possible. We want to retire so we don't have to work anymore. I think of not doing my job as Michael Jordan would have thought about no longer playing basketball — it's not how I'm built.

But over time this obsession has created some brutally bad habits that have become a massive liability later in life. Fortunately, I know there are many other Founders dealing with the same issues (because I talk to them all the ...

Being a startup shouldn't be a goal, it should be a milestone we're doing everything to get beyond.

As it happens, a "startup" is just the formative years of our existence. And while the term itself is rife with excitement, it really masks our true ambition which is to become a plain ol' "company" without the "startup" in front of it.

It's perfectly fine for us to revel in our startup years, but in the back of our minds, as Founders, we should be thinking "How quickly can I stop being a startup?" and work our tails off to drop that title as soon as possible.

Startups are Sexy - at First

To be fair, being labeled a "startup" is sexy as hell at first. We're associated with wildly important terms like "growth," "opportunity," and "big outcomes...

Why are we still paying people in units of time?

It's been about 100 years since the Industrial Revolution and yet nearly everyone on the planet still gets paid like a dock worker, where units of time equal measurable production.

That made sense when nearly everyone had an output that could be tracked by time, but in our current economy, why do we still think every job should be performed for exactly 40 hours within a 9 to 5 schedule?

We're at a point where we can no longer justify a one size fits all type of output metric. It's time we burn down the old institution of work hours and build a new mechanism that actually applies to what employers are paying for, and what employees actually do.

Let's Pay for Outcomes

As Founders what we care...

What happens to funded startups that can't raise any more funding?

We enter the funding "No Man's Land" where startups go to linger and eventually die a very long, unceremonious death. No one talks about it — certainly not the Founders who are left with the breathing corpse that was their once-hot startup. Certainly not the investors who have written off their investment long before anyone else.

Yet everyone knows we're digesting in the Sarlacc pit for a thousand years without any idea what to do about it.

Having been in this fiery wasteland more times than I care to admit, I learned that at some point Founders have pretty much three options to escape, and "we'll just hold out for funding" isn't one of them.

Buy it Back

Let's start with per...