73: Sahil Lavingia, Founder and CEO of Gumroad

Square One: Conversations with the Best in Business

This week it was awesome to dive deep into startups with Sahil Lavingia, Founder and CEO of Gumroad. Sahil’s seen it all in Silicon Valley - he was employee #2 at Pinterest, started Gumroad with a traditional venture backed structure, pivoted the business to be venture free and now has a rolling fund he operates in his spare time investing $7M a year in startups. We talked a lot about the differences in running a venture backed company vs. a company that lives and breathes off the balance sheet. We chatted about the difference in psychology of running these types of businesses and how clarity of thought comes through when you get out of the echo chamber.

Sahil has worked to remove friction and increase democratization in nearly everything he’s done - a lot of this principle is what underscores Gumroad. He’s taken this same perspective to investing. Some of my favorite insights from this conversation include: (1) how to leverage community and audience, (2) why everyone should invest in early stage companies, (3) the trope of the world’s venture capital being perfectly allocated and (4) how democratization and access will continue to lift humanity out of its early J curve.