Why are all hugely successful entrepreneurs jerks as a person?

They aren’t. At least not in B2B / SaaS.

Although sometimes, they were a little bit arrogant or jerky on the way to being successful.

I’ve interviewed and talked backstage with the CEOs and founders of Atlassian, Slack, Box, Twilio, Intercom, Blackline, Coupa, Sendgrid, Veeva, Trello, New Relic, Mulesoft, Appdynamics, Domo, Qualtrics, Asana, Zendesk, Zuora, Zoom and scores of others that have IPO’d and/or gone on to huge successes.

None are jerks. At least — not by this point. By the time they hit say $100m in ARR they are all humble, thoughtful, appreciative, gracious, and in their own different ways, charming. Quietly confident by this point, yes — they can see the future pretty well by $100m in ARR or more — and often protective of their time, but that’s about as far as it goes on the arrogant scale.

In fact, they all make you feel special in the few minutes you do get with them. I don’t know how they do it, but they all have this super power.

You can get to $15m-$20m in ARR just charging up the hill, sometimes. Arrogance combined with some ignorance may even help a bit in this transition phase.

But I don’t think you can get to $50m+ in SaaS without learning how to truly lead a heterogenous group of individuals. How to get customers, prospects and employees to see the merits of your vision. And importantly, as time goes on — how to respect their vision as well and their contributions.

This is what makes the CEOs and founders a bit more humble.

Often, though, I see a bit of hubris crop in around $10m-$20m ARR or so in the fastest-growing SaaS companies. They think they’ve sort of figured it out. They are finally breaking out. VCs are banging down the door. Everyone finally wants to work for them. They sometimes feel like a bit of a genius at this stage.

And then by the next stage … say $30m-$50m ARR … they realize they haven’t figured it out at all. It’s time for their team to figure it out. And for them to help build and guide the team to get there. I think that de-jerks anyone that was even a bit of a jerk at $10m-$20m ARR.

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Published on June 5, 2018

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