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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...

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 ...

Competition tends to be a distraction that's 100 feet taller than the reality.

As startup Founders, we've all had that moment when we thought our very existence was going to end because some competitor made some announcement that would crush us. We worry constantly that we're going to "lose to our competition" when in fact who we really lose to is our customer, and by way of that, our own product.

We need to rethink how competition really affects us, or in many cases, sorta doesn't.

It's Not "Winner Take All"

We have this mentality that one company, whether it's ours or our competitors, will "dominate" the market and take all of the market share. We will be insane and penniless wondering how we ever succumbed to that evil genius and their ...

A war cannot be won on two fronts — especially if you're a startup Founder.

When I talk to Founders, I often ask them, "OK, so things are tough at work — what are they like at home?" and it surprises them. First, it surprises them because it's a very personal question. Then, it surprises them because they realize why I'm asking.

I ask because I care about them as a person, and I know if they are fighting a war at work (aren't we all?) the only way to make it much worse is to go home to an equal or greater fight.

Our support at home is our greatest strength or Achilles Heel depending on what we have going on — and boy, do we all have a lot going on when it comes to our home life.

Two Battles, One Health Bar

I think of everything like a video...

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...

Founder success is almost never what we picture it to be.

When we think of wildly successful Founders our minds easily jump to billionaires like Branson, Blakely, and Musk, balancing a life of magazine cover story photoshoots with keynote presentations and TV interviews. Our most "successful" Founders often have this air of glamour around their success.

But as it happens, Founder "success" feels way less glamorous. In fact, the most exciting success milestones are often so mundane when they occur that we don't even realize they happened. But this success is a culmination not of a single event, but a series of tiny events that we later look back and realize was when our success was truly defined.

We Always Make Payroll

For most of our journ...

The difference between lying and optimism is often told in the outcome.

As Founders, we spend an inordinate amount of time telling stories about how the future of our startups MIGHT turn out. Often, those stories balance the line between being optimistic gestures of hope and a sordid tale of deceit.

When we tell our customers we'll be able to deliver a product we don't have the personnel to deliver (yet), are we lying? When we stand anxiously in front of investors boasting that we'll become a billion-dollar unicorn, are we misleading them? And when we recruit someone to leave their high-paying job to work for an idea we've barely proven, are we betraying their trust?

This is the moral dilemma we face as Founders every day while we convince ...

Startup culture has gone from glorifying victory to glorifying effort.

"Hustle Porn" has become more and more popular, particularly on social media, where would-be champions of entrepreneurship proclaim their insane personal sacrifices to the Gods of Startups. We're constantly wooed with tales of Founders putting in insane hours, risking it all, and coming away with the spoils of success to show for it.

How much of this is really a celebration of hard work and is how much is just the equivalent of giving ourselves a Participation Award for effort?

"I just put in 100 hours this week!"

Let's start by debunking the myth that working 100 hours in a week is somehow a victory to be lauded — it's not. The intention is that we're SO dedicated to ou...

Sometimes our startup IS our social life.

When we put it like that, it almost sounds kind of sad. We're told by others (heretics!) that we need a life inside and outside of our startup. We're supposed to have families, loved ones, and friends who we create amazing experiences with that have absolutely nothing to do with work. And of course, that's important.

But our startups aren't just about work — they are also a very important part of our social fabric whether we want to believe they are or not. In fact, if we were to sell our startup and have nothing to do with it, many of us would miss the very real social connection we took for granted.

As Founders, we get to enjoy a very special kind of opportunity to build and expand our social live...