The one thing you can’t teach an entrepreneur

Startup founders are like sponges.

You basically can’t be an entrepreneur if you aren’t relentlessly curious about people, technology, business and culture — constantly remixing those ingredients in your head to find new and better ways of doing things.

Because they’re so intellectually agile, founders can learn almost anything if exposed to the right vectors, whether it’s high-performing peers, experienced mentors, academic environments or direct trial-and-error.

But there’s one thing that can’t be taught — and I know because I keep hoping to be proven wrong about it and making the same mistake over and over.

My work as a startup investor isn’t focused on companies, but on founders: helping extraordinarily smart and creative people reach their full potential as creators, builders and leaders. Whenever I meet someone with the intellectual and emotional capacity to be a founder, I want to do whatever I can to help them realize that goal.

But there is an awkward truth about successful founders — awkward because it can manifest in decidedly ugly and antisocial ways. At the deepest levels of their psyche, often hidden even from themselves, they have a hunger that they can’t control.

This hunger goes by many names — ambition, competitive drive, the will to win — and it’s hard to talk about because it is formed around a hard kernel of insecurity and shame. 

For every successful founder I know the story is the same: somewhere along the way someone important to them told them they weren’t good enough and would never amount to anything. The anger and self-doubt embedded in them by that searing experience becomes a nuclear core fueling their relentless drive for the rest of their lives, long after they have proven the doubters wrong.

Founders who learn to bank and control this fire are among the most productive and effective people in the world. Those who fail to master it self-destruct as their hunger for domination leaks into their personal relationships and poisons their capacity for empathy.

But no matter how brilliant a founding team is, if one member of that team doesn’t carry this uncomfortable burden, that startup’s odds of success go from low to infintesimally small. 

It can’t be taught — in fact it would be wrong to try, because it would require inflicting deliberate emotional damage on another human being. Though risky, it can be added, by bringing in additional founders or early hires who carry necesary the emotional scars. But if it’s not baked into the culture at the most fundamental level, no amount of investor, mentor or board support can infuse a startup with the unstoppable force needed to overcome the indifference, hostility and scorn that the world piles on anyone who dares to try something new.

Founders aren’t born but made, first by the hurt the world gives them and then by their lifelong fight to forge that hurt into something beautiful and strong.


  1. myBestHelper

    This is an interesting observation and I knew I had seen it somewhere before… Just saw where – Peter Sims / Bill George from Stanford have a leadership book “True North” where they talk about this in a more generalised way: “Many leaders experience what you describe as a “crucible,” or challenging period in life that deeply tests them and transforms their understanding of leadership.” (comment by Alexandra T Greenhill, CEO myBestHelper)

  2. Raub Dakwale

    This choked me up and made me re-live some moments in my life. Thanks for writing it, hope all’s well!

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