Dear SaaStr: did you ever have a situation where you were talking to a person but that person turned out to be a billionaire?

I’ve done OK, but I’ll never be a tech billionaire.

However, I’ve met and worked with many (as crazy as that sounds to say “many”) in my start-up and SaaStr journey.

A few observations of B2B SaaS Billionaires:

  • They have imposter syndrome, too. I loved this session with Mike Cannon Brookes of Atlassian at SaaStr Annual 2019 when we talked all about it. Even as CEO of a $25b Cloud company you can’t help but still look up at Microsoft, Apple, Amazon, etc. So if you are feeling a bit of imposter syndrome yourself, know you are in good company!

  • They are confident but mostly, humble. There are definitely some exceptions, but most SaaS billionaire or close-to-it CEOs I’ve met are extremely confident in the sense they know their business and markets cold. But it’s SaaS. They still have to win new customers every month, every quarter. In that sense, it never really gets easier. Just easier to predict. So I think that, and the risk of new entrants in the space eventually disrupting them, also keeps them humble. Stewart Butterfield is confident and humble. Eric Yuan is confident and humble. Etc. etc.

  • They are deeply passionate about what they do, and about the long-term journey. It is impossible not to be infected by the enthusiasm of someone like Jeff Lawson of Twilio.

  • They are going very, very long. It was seen as odd, back in the day, when Jeff Bezos bet so long on Amazon. But the best B2B leaders are all going very long now. We’ll all learned recurring revenue truly compounds. That you can go from $100m ARR to $1b in ARR if you have happy customers and a top-tier product. And then beyond $1b in ARR

So finally, to answer the specific question, if you meet a SaaS billionaire, you’d know they were a special leader. But I really don’t think you’d know they were a billionaire per se. They are a lot like other great CEOs. Just even more … present.

Last billionaire story, not SaaS. I met Jeff Bezos just once, really not that long ago. I wasn’t sure what to say. I just said, “I’m a very long-time, super-happy customer.” He gave me a big, real smile. I think delighting the customer, for those of us who are really going long and committed, that never gets old.

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