Ep. 009: Sahil Lavingia

Polymathic Audio by 2PM Inc.

Sahil Lavingia built Gumroad in a weekend. At 19, the eCommerce entrepreneur was on top of the world. Within a few months, he raised $1 million from a who's who of investors: Naval, Max Levchin, Accel, and First Round. Soon after, Lavingia raised capital from Kleiner Perkins Caufield & Byers. In total, he raised $8.1 million. In a now-famous essay on his journey from venture-backed founder to boot strapped entrepreneur, he shares a bit about his journey. There was a rise, the fall, and a continued return.

The idea behind Gumroad was simple: Creators and others should be able to sell their products directly to their audiences with quick, simple links. No need for a storefront.

I built Gumroad the weekend I thought up the idea, and launched it early Monday morning on Hacker News. The reaction exceeded my grandest aspirations. Over 52,000 people checked it out on the first day.

Later that year, I left my job as the second employee at Pinterest — before I vested any of my stock — to turn Gumroad into what I thought would become my life’s work. [1]

Lavingia languished in the spotlight until growth stalled.

We grew the team. We stayed focused on our product. The monthly numbers started to climb. And then, at some point, they didn’t.

Gumroad has become a stalwart in the creator economy because of Lavingia's next steps. From nearly shuttering to a profitable, lifestyle business: Gumroad has fueled millions in monthly commerce for content creators. It's spawned competition from platforms like Patreon, Memberful, and now Substack. But I wouldn't count the founder out. Lavingia is playing a long game, he's growing on cash flow, and he has a specific vision for the creative future. In fact, he's planning an active role in it.

Known for his insightful tweets and quick wit, Lavingia is now raising a fund to continue acting on his intuitions. From funding underrepresented minorities to new proponents of internet-born creativity, the Creator Economy is just beginning. He's taken it upon himself to make it more accessible. For Sahil Lavingia and Gumroad, they're well positioned to profit from it.

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