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I've failed numerous times and watched countless other Founders do the same. We kept ourselves awake nonstop worrying about the outcome of our failures. We took years off of our life and put ourselves in horrible places mentally and physically.

And you know what we learned in the end? It generally didn't matter.

That's right, our "fear of failure" was always 100x worse than how the failure itself played out. And so we took desperate measures to avoid failure, like clearing the last of our savings, running up debt, and going yet another year without pay. At some point, we became far more intent on "not failing" than succeeding.

What we need is a method for dissecting failure into actionable bits.

Failure needs to be Unpacked

If we think ab...

Most Founders get rich without ever exiting their business. Yes, you read that right. We don't have to build a rocket ship that takes on gobs of funding for an IPO in order to have everything we want.

We just need to keep making money (and not even that much!)

While to most people this may sound obvious, in the startup world we tend to forget how this simple fact works. We keep thinking in terms of this big liquidity event where we get handed a giant check like we just won the Powerball. We picture ringing the bell on NASDAQ wearing the only nice outfit we own shaking hands with bankers and smiling for the camera.

And in the end, we picture having enough money to just do whatever the eff we want.

The Stacking Effect

I spend a ridiculous amo...

A few years back I was driving through a windy street of Bel-Air with my wife, looking at houses. If you ever want to feel ridiculously poor, I encourage you to do the same.

During our home tour we drove up beside a house under construction that was so big, we thought it was a hotel. We just kept driving around the perimeter of the house, and it just kept going! Our realtor told us it was the future home of Elon Musk.

A younger version of me would have said "Someday I'm going to have that house!" and believed wholeheartedly that there were some future series of events that would lead to that outcome. It's the blessing and curse of being a Founder I think.

I turned to my wife and said "I can't have that — and that's OK." Let me explain why t...

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...

To grow or to profit, that is the question!

There we are, with a fistful of profit in our hands (finally!) and an endless list of places to spend it! Do we hire another engineer to get our product shipped faster? How about increasing our marketing budget to scale customer acquisition? Or, and let's just get crazy, do we finally pay ourselves?

Profit First, then Grow

I'm going to go out on a limb and spat in the face of startup lore, which suggests that the only way to succeed is to bet the farm and grow. Think of me as the owner of a casino (in this case, that casino is Startups.com) who gets to not only witness a handful of people bet it all and get rich, but 100x more bet it all and fail.

What we miss in our passion for greatness is that...

Every startup dies a few deaths before it lives forever.

But that's not what they tell us in the startup Founder brochure. Instead, we make up this fairy tale that our startup must be a great idea that instantly takes off, leaving customers and investors standing in line to hand us their cash. We keep making great decisions while we struggle to stay on top of our meteoric rise. Our days are jam-packed between photo shoots for magazine covers, headlining major conferences, and giving powerful speeches at company retreats.

Sound familiar?

No, of course it doesn't. Because that's not how any of this shit goes. The real version of a startup involves failing incessantly, sometimes to the brink of shutting down, until we rise back up and finally ...

When we sell our startup, it's not the simple financial transactions we all think it is. While we zero in the wealth event and the "freedom," we rarely take stock of the significant cost that comes with it.

Our startups aren't just about an income stream — it's not just a job. It's a part of us, something we created from scratch and worked tirelessly to bring into this world (I'm really trying to avoid a child-birthing analogy, out of respect to any woman who's delivered an actual child!).

When we think about selling, we need to think about all of the things that are going to be taken away, not just the dollars and freedoms that will be added. We often find that our startups provide a much deeper reward than what just having a job implies ...

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...

As Founders, when we give away equity determines how much we're going to lose.

That's because the equity game, and our job of holding on to it for dear life, is really about vulnerability. The more vulnerable we are, the more we give away. The stronger our position is, the more we retain. It's really that simple, and yet, especially if this is our first startup, it's hard to realize when we're giving up too much too early.

There are really three moments in time where we have to really consider our timing and our approach — when we add co-founders, hiring early employees, and when we take on seed capital. What we often don't realize is that there is a lot of strategy to when and how we pull these triggers, while a lack of strategy has massiv...

There's no paycheck in starting companies. It's the finishing part that matters.

I say this because many of us simply love the thrill and idea of starting another startup. There's always this thought — "Boy, if I could just launch this one idea that I can't stop thinking about (while forgoing my existing startup), it'll be amazing!"

Here's where the logic in that breaks down over, and over, and over.

It's Gonna Cost us 7-10 Years to be Right or Wrong

Every single time we start something anew, we reset the clock on how long it will take to make it successful. No matter how good we are, the maturation rate of a company will almost always take 7-10 years — if we're actually successful with it. That's the successful timeline, not the un-success...