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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