Q:  How do I overcome impostor syndrome as a startup founder?

Maybe you never do.

When Michael Cannon-Brookes, co-CEO of $60B+ Atlassian, came to SaaStr Annual, he shared that he still hasn’t gotten over it:


When I spoke with Todd McKinnon CEO of Okta he said he still felt vulnerable all the way to $30m-$40m ARR. And that it still hurts folks to think Okta isn’t “cool enough” or “big enough” … even though it’s now a $30B+ company!

Jeff Lawson, CEO of Twilio, shared he was never really included when he was CTO of Stubhub … because he wasn’t 100% committed. A different but related point:

Maybe if you don’t have some of it, it’s hard to stand on the shoulders of other giants. They seem so … perfect and giant.

But they weren’t back then. Even after their IPO, maybe.

And a fun related post here: What the SaaStr Conference Taught Me About Imposter Syndrome

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