Early-stage entrepreneurship is messy

Really great conversation between Gumroad CEO, Sahil Lavingia (in which I’m a tiny, microscopic investor) and Jason Calacanis (1:08:47 to1:09:25).

This part of the conversation resonated with me due to my own experience, but it was reassuring hearing it from Jason who has investments in more than 200 startups, including Uber, Thumbtack, and Calm.

“You invest in somebody they're 19-20 years old, like Mark Zuckerberg was or was like, that's kind of how it works, it's really messy. And then, sometimes it works out brilliantly. And then, there's a spectrum in between of every permutation, but if you're looking for perfection, do not, do not work with humans… and certainly not entrepreneurs and startups, early-stage startups.

“There is no perfection here, if perfection is your goal for the love of God get out a chessboard and spend 10 hours a day, just grinding it out on a chessboard because you will get to a 2,000 rating.”

This common experience does not excuse poor behavior, but a bit of seasonal chaos comes with any startup.