Why did you choose to go into Venture Capital and what would you recommend to any young person who aspires to work in VC one day?

My path into venture was somewhat accidental.

But the reason was simple: I Wasn’t Done. I wanted to do more, but after co-founding two reasonably successful venture-backed start-ups … I couldn’t do a third start-up. Not a traditional one. It just all took everything out of me.

Being a founder CEO is the best job in the world. But it is so, so, so hard. And two as a co-founder (plus two start-ups as an exec team member before that) was as many tours of duties as I could take.

I had to hang it up.

But, I still had the passion, and the commitment.

So I’ve been lucky to help build SaaStr into a pretty interesting global community that helps thousands of founders worldwide, and sort of, a $6m+ “businesses” today (that’s our operating budget — we don’t make any profits though).

And to have the opportunity to invest in a handful of the most promising founders I just happen to meet from that community.

Doing both together is pretty rewarding. Kind of, sort of, like Startup #3.

So what’s my recommendation to folks that aspire to VC?:

  • First, understand it isn’t nearly as glamorous as it looks.
  • Second, understood it’s a tiny and super nichey segment of money management.
  • Third, understand it’s hyper-competitive, especially in the Bay Area. Why would you win? Ask yourself that honestly.
  • And Fourth, understand great Founder CEO > VC. If you can be an epic founder, do that over VC. At least, do that first. Why be on the sidelines, in a tiny firm, when you could be changing the world?


  • As a job … if you are patient, and can wait a long time to make real money … it’s interesting. And you can get pretty good at it.

Just don’t over glamorize it.

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Published on July 4, 2016

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