Sahil Lavingia is the CEO and Founder of Gumroad, a platform to help creators create more through simple e-commerce and audience tools. He is also known for insightful and refreshing points of view on Twitter and Medium. To round it out, he’s also a designer, painter in addition to being a technology CEO and writer. Sahil and I have had similar paths in creation, from tech to design to art, as well as being a founder that has seen almost everything.

From being employee #2 at Pinterest to starting his own company, to coverage in just about every magazine, every investor in Silicon Valley wanted to be a part of what he was building to layoffs, then more layoffs, to then being the only person running his company, bordering on depression for a long stretch of time, and now back to a tight-knit team and a business that will bring in over $5m in revenue this year, profitable and actually growing faster than ever.

In addition to the experience he’s had, he’s begun to articulate what it has been like as a creator, and his tweets and essays on the topic, up there with Justin Kan, Eric Ries and a handful of other guests have given people some of the most realistic glimpses of what it’s truly like, and I can’t wait for you to hear this behemoth of an episode.

#149: Assumptive Leap of Fear