How Things Dont Grow; Reflections on Failing To Be a Billionaire - with Sahil Lavingia (CEO at Gumroad) - a podcast by Shamanth Rao

My guest today is Sahil Lavingia, and this is an incredibly powerful, honest & inspiring episode. Sahil is today the founder & CEO of Gumroad, a platform that helps creators get paid for the work they do. What is significantly more impressive though is Sahil’s journey to where he is today. Sahil was in many ways a prodigy as a teenager, working on apps & websites - and making $100k by age 15. He joined the University of Southern California, only to drop out after a semester to join the then fledgling platform Pinterest to build their iOS app as employee #2. Within a year, he left Pinterest - before his shares vested - to found the company that he hoped would be his magnum opus, what he announced on Twitter as a ‘billion dollar company idea’ before he launched it. This was Gumroad - and for a while he seemed to be a man who, at age 19, could do no wrong. Until things started to go wrong. Growth began to stall. Sahil and his team put their soul into the business - and they couldn’t do what it took to hit the targets they need to hit to make it a venture-scaleable business. In what was a wrenching time, he had to lay off three fourths of his company - and find his own path forward. This is Sahil’s story - about how things don’t always grow, and how sometimes that’s ok - but only if you make your peace with it.


KEY HIGHLIGHTS

• Sahil’s early work in design and development as a teenager that led him to make his first $100,000 and become financially independent.
• The path that led Sahil to be described as the most interesting teenager in Silicon Valley and the #2 employee at Pinterest, less than two years after he started learning to code. 
• Why Sahil left Pinterest less than a year after joining, before his stocks vested  and what about Gumroad inspired him to keep working on it.
• Why Sahil decided to go deep on Gumroad rather than seek out his next new project. How writing and painting helped him cultivate the patience that let him do this.
• Sahil’s cold email strategy of acquiring his first few customers – and why it was effective for him.
• Why Sahil was obsessed with becoming a billionaire from early on.
• How Sahil coped with the fact that Gumroad would never become a venture-bankable billion dollar company.
• How Sahil thought about ‘front loading his retirement’ why ‘diversifying his identity’ was crucial.
• What inspired Sahil to write the Medium piece about his journey.
• The reframing of impact that was crucial to Sahil’s coping with the change in circumstances for his business.
• The difference in lifestyle in Provo, Utah, compared to San Francisco.

Check out the full transcript and show notes here:
https://howthingsgrow.co/how-things-dont-grow-reflections-on-not-being-a-billionaire-with-sahil-lavingiaceo-at-gumroad/

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