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Our Founder careers aren't defined by the size of our positive outcomes, they are defined by whether we've had one at all.

Therefore, if our outcomes are so important to us, shouldn't we first start with optimizing for the most likely outcome that will be meaningful to us? Is our idea more likely to become a $3 million business earning $1 million in profit or a $100 million business that could go IPO?

We need to start our journey, which implies an insane amount of tough decisions, aligning our path with outcomes that will not only be meaningful but those that we have the highest probability to achieve.

Optimizing for a Billion Dollars is Silly

To be fair, the "It has to be a billion dollars" is a mantra directly driven from the VC community...

It's really hard to convince people that money isn't the most important metric of a startup's success. Especially if those people happen to be investors, in which case, it actually is the most important metric.

But what we're talking about, as always, is what's important to Founders, and by extension to the people that work within that startup.

The broken part of the startup narrative has become this — "If it's growing fast and making money, it's successful, no matter what other costs are incurred."

I'd like to just go crazy for a moment and offer a new narrative — "If it's making everyone's lives geometrically better, then it's successful, and hopefully that means it's making money."

Focus on Making Lives Better? What?!

I know, I know. W...

When I’m listening to Naveen Jain describing his plan to create big business on the moon, it’s hard for me to grasp that he was once a poor child in India.

Today, Naveen is a billionaire and a very successful entrepreneur. His own recipe for success is, among other things, not knowing much and not being very good at anything. To me, that sounds like the opposite of what business life normally requires, yet Naveen isn’t joking, and his track record proves that he is not wrong either. After all, the young boy that grew up in poverty in India is today changing the world as we know it and has Sir Richard Branson and Google founder Larry Page as two of his good personal friends.

Jonathan: Naveen, I find it so inspiring that you have used entrepr...

Long after our startup is done, no matter what the outcome, our Founder reputations will live on.

And for many of us, that could actually present a real problem.

Unlike our resumes, which present essentially one dimension of our lives (our job performance), our Founder Reputation is built on how our performance affects so many people — employees, investors, customers, the media, and even our personal relationships.

Founder Reputations are Easy to Tarnish

From the get-go, we have two huge obstacles working against creating a great reputation.

First, we're about to build an organization that will likely (statistically) fail. It's sort of hard to build a winning reputation on the back of a potential failure that could result in the loss of job...

Decoupling startup stress from our "regular life" is one of the biggest challenges we deal with as Founders. Running a startup isn't like working at a job. The startup is a part of who we are, so our stress feels like it's imprinted into our very DNA.

Yet, at the same time, if we can't decouple our startup stress and our home lives, we risk destroying both. What we need is an actual strategy for freeing up our minds so that we can actually enjoy both sides of our lives.

Isolate and Attack the Problem

As Founders, we are awesome at attacking problems all day long at our startups. So why is it that we never isolate the problem of our "take-home stress" and attack it with the same intensity?

The first step is to isolate the problem as an actua...

As a Founder, no matter what I've ever accomplished I've never been OK with where I am. It's weird, too, because I started out with so little that accomplishing anything was a huge win. And yet, I find that my anxiety exists in nearly ever Founder I meet.

It almost seems like the very drive and ambition that makes us great Founders also makes it very difficult for us to just kick back and enjoy the status quo. It's as if we're Kevin Arnold constantly reaching for the car door handle of accomplishment while our asshole older brother Wayne keeps hitting the gas pedal when we try.

"Why wasn't my last accomplishment enough?”

When we had nothing but a dumb idea and a dream, the idea that this could turn into our day job was a massive milestone. ...

As Founders, we spend an inordinate amount of time setting and pursuing goals, yet the ones that truly matter — the ones that affect us personally — are often amorphous. If we're spending every waking moment working toward a goal, it stands to reason that our goals should have an insane amount of fidelity.

Where Does it all Start?

I remember my early years as an entrepreneur. I had a lot of ideas about what success meant for me and for the company that I was building. But, it wasn't until I had spent several years working on my business that I finally realized why felt unsatisfied.

I didn't have a clear definition of success.

This is a problem that plagues many entrepreneurs who want to build something great, but don't know how to define su...

Fresh from graduating at the bottom of my class in high school, I packed my $800 orange Datsun and moved to some weird place I'd never heard of before called "Ohio" to go to college. Back then the Internet didn't exist as we now know it, so when you left the state (unless you called someone on their home line) — you no longer existed.

I went ghost for almost 4 years — no trips home, no holidays — nothing. I lost touch with most of my friends and family. But while they were wondering what prison I was incarcerated at, I was busy building one of the first Internet companies.

The company did well, and when I returned, I was a millionaire. Little did I know that from that point on none of my relationships would ever be the same. Here are the ha...

Recessions breed incredible opportunities for startups, if only us Founders knew where to look and how to leverage them.

At its core, a recession distracts everyone all at once, meaning only a select few will have the fortitude and foresight to find advantages. What we need to do during these times is step back and look at the overall picture to understand not just what's happening to us, but what's also happening to everyone else.

This is where the opportunity begins.

Our Competition is Totally Distracted

It's really hard for anyone to stay focused on growth when the walls are closing in around us. That's why most of our competition will be circling the wagons and staying completely fixated on internal struggles and survival. This is a gol...

Breaking up with investors at the end of a failed startup journey is basically every Founder's worst nightmare. It's that awful conversation we did everything in our power to avoid. We rehearsed it over and over while starting at the ceiling at 3 AM. And yet, here we are.

How we break up with investors is as important as how we built the relationship to begin with. That's because in the startup world, building long standing relationships among key players, including investors, is all about treating those folks with respect at every step of the journey — even the shitty ending part.

We need to own the outcome

This is no time to point fingers. It was our job to create a successful startup; it didn't work out — we have to own that. This is th...