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Sahil Lavingia Reflecting On My Failure To Build A Billion Dollar Company Gumroad And Beyond.

Sahil Lavingia is the founder and CEO of Gumroad, a web platform where creators can sell products directly to consumers. He started the company while working at Pinterest in San Francisco, raised venture capital and ascended to the elites, but eventually, changed his trajectory, fired everyone and relocated to a small town in Utah. Why this was the right path for Sahil, and why venture capital is not a fit for everyone, it's all in this episode.

Updated on October 16
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Key Smash Notes In This Episode

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Sahil started by learning design and code for the web, with a simple goal to make enough money to buy some games. Soon thereafter, he took a free online course from Stanford on developing for the iPhone, doing it while he was still a high-school student. He then started to experiment, making more apps. Eventually, Sahil went to college at USC, and only lasted for four months before he dropped out and joined Pinterest to work on their iPhone app full time.

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Although much like in any early startup is was not yet clear where the product would be, Sahil says it was clear they had a great team, and that was an indication of potential success, and what made Pinterest a great team to join.

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One Friday night, Sahil designed a set of icons he'd designed. He wanted a tool to sell this digital file on the internet for $1, but no mechanism to do it was available.

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If you work on something that you are passionate about, you will end up finding other people who are passionate about their work, and if your interest (or needs) overlap, you will meet one another.

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Yes. Living in Palo Alto ten years ago, Sahil felt like he had missed the boat. But, fast-forward to now, having worked his way up, he was able to meet some of the known people in Silicon Valley, and new entrepreneurs have come up, forming new social circles. It's possible to do this anywhere, so long as there's a community willing to work hard.

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Gumroad was the first project Sahil created which not only got 50 visitors from Hacker News on the day it was launched, but was also the only project of his that was helping people to earn a living, by helping them sell creative work on the internet.

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