44 minutes | Aug 6th 2019

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

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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 HIGHLIGHTSSahil’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/**Get more goodies here:http://MobileUserAcquisitionShow.comhttp://RocketShipHQ.comhttp://RocketShipHQ.com/blog
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