For a very long time, I felt like my startup was a direct reflection of my worth as a person.

When my startup was doing well, I felt on top of the world (this was rare). But when my startup was struggling, which was 99% of the time, I felt it was a direct reflection of my own incompetence as a human, and I felt like hell. And so by way of that, I usually felt shitty.

It wasn't until I started exiting startups (good and bad exits) that my startups were just a moment in time. While they were a reflection of my output, they weren't a reflection of me. It took a few decades to figure that out, so let's see if I can help you do it in the next few paragraphs instead.

Our Startup is the Work We Perform — it's Output

I'm a Dad, a carpenter, a crea...

When I (Jonathan) read the book Exponential Organizations 3 years ago, a whole new world opened up for me. Up until then, I didn’t know Salim Ismail that well—just like a lot of other people, I guess.

Today, Salim Ismail is one of the hottest names in the business world. He has spent the last 7 years building Singularity University as its founding executive director and current global ambassador. Prior to that, Ismail was the vice president at Yahoo, where he built and ran Brickhouse, the company’s internal incubator. His last company, Ångströ, a news aggregation startup, was sold to Google in 2010.

Salim Ismail has founded and/or operated seven early-stage companies, including PubSub Concepts, which laid some of the foundation for the real...

Sometimes having to burn it all down is the best medicine our startup can take.

It sure doesn't feel that way at the time. When we're sitting across from an income statement that's been decimated and thinking of having to go back to our team, investors, and partners to tell them some truly horrible news, the last thing we're thinking is "Hey this might be great!"

But for those of you that have never been through it, I'm here to tell you, it may in fact be the best thing that ever happened to our startups.

That's because a Hard Reset gives us the one opportunity to go back and reset all of our decisions that we've made, teeing us up to build a far more efficient and capable startup going forward. It sucks — like I said — but it also has som...

I never expected to be an entrepreneur. My first business, the mobile user interface (UI) company The Astonishing Tribe (TAT), was set up by six friends who wanted to work with something we loved and learn from our own mistakes rather than from others’. I am not even sure that it actually felt like a startup. TAT became a completely unexpected giant success both personally and financially (the business was bought by Blackberry for $150 million).

When I started my second business, I wanted more than financial success; it had to mean something to me. I believe that an entrepreneur’s true purpose is to try, learn, and experiment rather than follow more conventional ways of achieving success. Therefore, there is more room for failure, which is ...

There we are, once again, sitting at yet another Founder get-together while everyone tells us how great their startups are doing. Oh shit, that woman just said that they raised a massive round of funding. That guy just said he just surpassed 100 employees. The other person (I'm losing count) just claimed they are growing 50% per month.

"WTF? I thought I was doing great and now listening to everyone else I feel like a total loser."

And there it is. The age-old startup-sizing "competition" where we indeliberately one-up each other with how amazing our startups are doing. In the process, we all make each other feel miserable about ourselves.

What's that? You don't do that at get-togethers? Well, if you're like most, you're doing it anyway in s...

It's ridiculous to think that anyone will ever be as committed to a startup as the Founder.

And yet, we're constantly beating ourselves up trying to find just the right combination of great hires, strong incentives, and attractive growth to convert all of this raw talent into the committed, startup-building machine that we've become.

But it's 3 a.m. and we're sitting in bed staring at the ceiling completely engrossed in nothing but the future of this startup. Why isn't everyone else? Is there some sort of magic formula that would convince the rest of the staff to also be sitting in bed staring at the ceiling? (In this scenario we're assuming we'd want people to do that...)

It's time we realize, as Founders, that expecting the same level of ...

"I want to put $50 million in the bank by the time I'm so I can retire early and never have to work again!"

Ah, the common refrain and justification of every startup dreamer, from the Founder across to the earliest employee. If only we could put that magic pot of gold into our coffers, then we could do what we really want to do.

Except it begs the questions:

1. How much of what we really want to do can we already be doing?
2. Do we really not want to work or do we really just want to feel safe?
3. What the eff are we going to do at (whatever age) with nothing to do all day?

Time and time again when I query Founders, beyond the surface level stuff, about how hard they have thought through this lifetime goal that they are sacrificing everything for...

How could we possibly be "right" as Founders when literally everything we are doing is unknown?

Think about it — we're building a startup that has never existed with a product that's being invented run by a team that's never worked together delivering to a customer who has never heard of us. Oh, and did I mention as Founders we've probably never done this before?

What about that formula drives certainty?

Separating Mistakes from Failure

Let me start by saying this — there is no possible way, NO possible way, that as a Founder we could possibly make the right decision over and over. In fact, the only way TO make the right decision is going to be to make tons of mistakes until we figure out which decision is correct.

We need to learn that whe...

Most of us Founders have never raised capital, so when we dig in for the first time, we're mostly guessing at how the game is played. And friends — it is indeed a game. The problem with this game is that as Founders, the odds are stacked way against us.

We actually make matters worse when we don't understand the rules, and instead revert back to our base instincts, which range from carpet bombing the investor with follow-ups to trying to translate "I think it's interesting" into 50 potential meanings, like a 16-year-old after their first date.

What we need is to be able to read the signals for what they are, and when we do, take our foot off the pedal if the signal says "stop" and jam the pedal when the signal is "yes."

Anything that's not ...

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...