Dear SaaStr: As a CEO, Who is The Most Talented Founder You Have Ever Met?

A few of the most talented I’ve ever met.  Ok, let me qualify this by saying earlier in my career.  As part of SaaStr, I meet so many incredible founders from HubSpot to Monday to Slack and more that I can’t count those, for the most part.   So I’m excluded the CEOs and founders, for the most part, that I’ve met though SaaStr itself as there are too many great ones.

But here are a few that stood out so much, that I truly learned something profound from them:

#1. Peter Gassner, CEO of Veeva.

This was an eye-opener to me. Peter was part of an amazing batch of CEOs that Emergence Capital invested in, including me. The batch included tons of Unicorns: Yammer, Intacct, etc. But Peter was the best of the best. That fund (Emergence II) is one of the best venture funds of all time. It was just when SaaS was taking off, but before everyone could see it.

How was Peter the best? He could see the future. Not just of Veeva even at say $2m in ARR when we met, but even of my own little start-up. That clarity into the future of my own company — not 100% accuracy, but clarity — stunned me. And the ability to share it with me in a way I could process and understand. (Elon Musk, for all his quirks, has a similar superpower).

Today, Veeva is worth $15 billion. The CEO that could see the future the best — and figure out how to get there — did the best. Even in a class of unicorns.

A great SaaStr Annual session with Peter here:

#2. Therese Tucker, CEO of Blackline was perhaps our most inspirational / popular speaker yet.

Watch her session from Annual 2017, and if you aren’t inspired, you are doing it wrong:

#3.  Rene Lacerte, CEO of Bill, was perhaps the most committed SaaS CEO I’ve ever met.

Rene made a 20+ year commitment to the space from Day 1.  I’ve almost never seen this truly before.  Therese was just as commited a CEO, but tilted and evolved to what worked.  Rene was the most committed to the space and vision from Day 1 and stayed true from the ’90s through today.


And a bonus, non-SaaS founder (and one admittedly with a lot of negatives and baggage:)

4. Travis Kalanick, ex-CEO of Uber. Travis is obviously a very controversial entrepreneur now, and I in no way endorse the sexism and cultural issues at Uber during his time there.

But pre-Uber, I met Travis at a lunch with a colleague. He was still working at a struggling startup in downtown San Mateo, which I think ultimately sold for just $10m and maybe was down to 2 employees at that point. His prior start-up also made no money. This was well before Uber was even a glimmer.

But at lunch, in perhaps 2004, we sat down and he explained the future again. This time, it was the future of video on the internet. I had never seen the future explained that clearly before. This was back when video barely worked on the ‘web at 320×240 for short bursts in creaky Flash.

So now, that’s what I look for:  An amazing CEO that can see the future, and ideally, has a handful of customers already.

So far, I’ve done OK as an investor. When I met CEOs of $10B Talkdesk at $1m in ARR (Tiago Paiva), $3B Algolia at $150k in ARR (Nicolas Dessaigne), $2.5B Salesloft at $10k in MRR, Logikcull at $300k in ARR, and many others … they could see the future. I saw the exact same when I met the CEOs of Intercom, Gusto and others very early. Add the ability to see the future to incredible drive and a great team … and you can’t be stopped. You just can’t.

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