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The Road Less Traveled By: The Book that Helped Sahil Lavingia Raise $1M in Seed Funding for Gumroad

Sahil Lavingia was a freshman in college when he met Ben Silbermann, the founder of Pinterest, for coffee. They talked ideas after a USC football game and that same semester, Lavingia made the decision to drop out and join the…
by Caitlin Schiller | Aug 23 2015

Sahil Lavingia was a freshman in college when he met Ben Silbermann, the founder of Pinterest, for coffee. They talked ideas after a USC football game and that same semester, Lavingia made the decision to drop out and join the tiny Pinterest team.

Soon, Lavingia would design and build the iOS app for Pinterest, the pinboard-style digital organizer beloved by cooks, crafters, the fashion savvy, and pretty much anybody who ever liked something on the internet. It was a bold move for a college freshman, and it was only the first. The second started with a pencil.

“I always do that, get into something and see how far I can go.” ― Richard Feynman

No 2: Pencil

Late one night in April of 2011, Lavingia was toiling over the design for a pencil icon that had to look realistic. When he finished, his first thought was “I wish I had this four hours ago.” That’s when he realized that more people must be having similar night-before-a-deadline experiences—ones in which a well-made supplement to your own work could really save the day, or at least a measure of sanity.

This, he thought, might be an idea worth pursuing. Considering he already followed other designers on Pinterest and Twitter, Lavingia even had a market for it.

The dream began to form: a place for designers, writers, artists, and coders to offer their wares, one that would
integrate with the social networks he already used and be as simple as He designed and built the first version over a weekend and people loved it.

An idea sticky as gum

In 2011, Sahil left Pinterest to found Gumroad, a payment company that lets makers of every variety sell their work directly to their followers on Twitter and Pinterest.



When he made the decision to follow the pencil and listen to his gut—which was clamoring to design products again—he wasn’t sure how things would turn out. Happily, making strong moves to pursue a goal he believed in couldn’t have gone better.

In that first year and at only 18 years old, Lavingia raised seed funding of $1.1 million. He curried 7 million in Series A funding only a year later.
Today, Gumroad users offer thousands of products and even offer around 2,000 feature films for rent. It was also recently voted one of the 50 Most Innovative Companies by Fast Company.

The success Gumroad is seeing today took some grit, it took a gamble, and it also took a great book.

Surely you are joking Mr Feynman

Lavingia’s pick for The Spark is Surely You’re Joking Mr. Feynman, a collection of essays and commentary by Nobel Prize-winning physicist Richard P. Feynman.

Feynman was a genius of physics, but perhaps before anything, he was an enthusiastic liver of life whose adventures included but were not limited to: painting a naked female toreador, cracking the uncrackable safes guarding the most deeply held nuclear secrets, accompanying a ballet on his bongo drums, and investigating the explosion of the Challenger space shuttle.

Painting ladies and playing drums might seem a little out there for founders’ inspiration fodder, but these capers are very applicable to Lavingia’s life and how Gumroad is growing.

“The book teaches you to enjoy life,” he says. “Do the things you want to do. Make sure you are aligned with a goal that benefits the people around you, and you are going to work harder, be more fun to work with, and produce better work.”

Speaking of work, one of the ways in which Lavingia sees Gumroad making an impact is by allowing people to earn livings in new and different ways, without needing to be employed full-time. It’s clearing the way for more people to take novel, left-of-center paths—which also happens to be a reason for which he loves Feynman’s book.

Working on the road

It teaches you a love for life outside of the traditional path. This is good accidental prep, because we’re moving toward a more non-linear world,” he says.

Learn what the rest of the world is like. The variety is worthwhile.

Lavingia’s trajectory so far makes a great case for a scraping linearity. he developed apps in high school, went to college, then dropped to head to Pinterest. Now, he’s founded a company that will allow more people around the world to pursue lives that don’t look like their parents’. The non-linear path he was inspired to blaze by Feynmann’s book is going somewhere.

Buy the book on Amazon here, or check out more books on living a life uncommon on Blinkist.

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