How startup failure can help founders expel toxic traits

Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.

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How startup failure can help founders expel toxic traits

For entrepreneurs, self-improvement is the highest leverage way to maximize the output of their careers. Just as the qualities of the founders are the most important factor in early stage investing, improving as a founder and operator (and person) has compounding returns over the course of decades.

Building a startup is such an intense experience that it can magnify, surface, and force founders to confront some of their biggest flaws.

Founders who are successful may not be forced to reckon with some of their biggest personal flaws. Or worse, their success may reinforce that these flaws are actually a good thing.

In the early days of my first startup, early success gave positive reinforcement to some qualities that were ultimately problematic. My high conviction, blind confidence, and charisma helped me recruit early team members, get early investors, and get our early customers. I believed that through strongly held convictions and force of personality, I could build a successful startup.

The truth is that I was drunk on my own convictions and not intellectually honest. I was not open to disconfirming my own beliefs. When potential investors or partners offered thoughtful (and correct) critiques of what we were building, I was dismissive. When I sought feedback from investors, customers, and partners, I sought it from those who reinforced my own beliefs. My ego was at the controls, not my intellect.

This worked until it didn’t. Ultimately, if I had to offer a single explanation to why my first startup failed, it was my own toxic qualities.

In the wake of my failure, I was forced to reckon with this reality. Giving myself the space to examine my own personal flaws lead to the most important transition in my professional development: a transition from a charismatic, drunk-on-his-convictions 20-something founder, to a truth-seeking operator who applies conviction and charisma only when appropriate. The people I work with today would hardly recognize the 20-something founder I once was.

This is why I tell founders to give themselves time and space in the wake of failure to process what happened. Startup failure sucks – a lot. If it’s something you have to go through, you might as well extract as much value out of it as you can by using it as a lever for transformative self-improvement.

This is also one of the hidden benefits of starting a startup early in your career, while you’re still malleable. Even if the outcome is failure, you can get some of your “bad” qualities out, and provide room for the “good” qualities to start growing. The earlier you can expel the bad qualities, the more time in your career you’ll have to reap the rewards of the good qualities.

I think of an entrepreneurs’ first failed startup similarly to how Julian Shapiro writes about creativity and bad ideas in his post, the Creativity Faucet:

Visualize your creativity as a backed-up pipe of water. The first mile of piping is packed with wastewater. This wastewater must be emptied before the clear water arrives.

Because your pipe only has one faucet, there's no shortcut to achieving clarity other than first emptying the wastewater.

Let's apply this to creativity: At the beginning of a writing session, you must write out every bad idea that reflexively comes to mind. Instead of being self-critical and resisting these bad ideas, you must openly accept them.

Once the bad ideas are emptied, strong ideas begin to arrive.

Entrepreneurs have wastewater in the form of toxic traits that will hinder their success. An entrepreneur’s first failed startup is often just the expelling of that wastewater. Looking back, that’s what my first startup was for me.

Once that wastewater is emptied, entrepreneurs can build the rest of their careers with clear water.