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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...

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...

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's the least we need as Founders to be happy?

For as much time as we invest in building our startups to achieve our goals, we spend shockingly little time in identifying what those goals actually mean. The danger in not defining our minimum viable happiness goals is that we wind up hoping to "find happiness" but never really defining how to get there.

And that's a pretty big problem when we're in the early stages of building a startup when very little helps fill our "happiness meter."

It's easy to make big, lofty, far away goals, but frankly, that's pretty useless right now. What we need to do is identify the shortest term, minimum goals that will make us happy so that we do everything in our power to get there as quickly as possible.

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 most expensive time to raise capital is when we're most vulnerable.

This paradox is the heart and soul of where we get leveraged as Founders, particularly when we're giving up valuable equity. What we need to do in those vulnerable moments is step back and ask ourselves "Is this the best possible time to take on dilution or can we find a way forward that costs us less later?"

If we've never built a startup before, we may not even realize how important this question is. For those of us that have, we're hyper-aware of how badly we get beat up in our previous startup by not being more mindful of protecting ourselves when we were most vulnerable.

Our goal then should be identifying our moments of vulnerability and crafting a more viable pat...