#100 – From Aspiring Billionaire to Indie Hacker with Sahil Lavingia of Gumroad

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After leaving his post as employee #2 at Pinterest, a teenage Sahil Lavingia (@shl) raised millions in funding from high-profile Silicon Valley to build a unicorn startup that could change the world — Gumroad. Today he lives in tiny Provo, Utah, spends much of his time learning to write and oil paint, and runs Gumroad as an indie business with the goal of…

Transcript

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Sahil Lavingia

Notes

What Are Similarities And Differences Between The Life Of An Indie Hacker And An Aspiring Billionaire at 0:52 Transcript
How Is Sahil Lavigia's Company Focused Different Now Vs. During His Venture-funded Days at 5:54 Transcript
How Is Failure Treated In Silicon Valley at 10:37 Transcript
What Was Sahil Lavingia Doing In Provo, Utah at 13:22 Transcript
How Do You Explain Gumroad To Someone Outside Of Silicon Valley at 18:46 Transcript
How Do You Explain Gumroad To Investors In Silicon Valley at 19:32 Transcript
How Did Sahil Lavingia End Up Working At Pinterest at 22:01 Transcript
Why Did Sahil Lavingia Leave Pinterest Before His Stock Vested at 26:47 Transcript
What Gave Sahil The Confidence To Build Gumroad Over The Weekend at 35:04 Transcript
Startups Success Stories Are Few, But Every Founder Believes They Are Building The Next Facebook. Why at 39:55 Transcript
How Can You Maximize Luck at 45:21 Transcript
Why Did Gumroad Struggle To Raise Series B at 55:07 Transcript
How Did Sahil Get Gumroad To Grow at 59:34 Transcript
What Makes A Great Business at 1:06:23 Transcript
When Did Gumroad Hit A Turning Point at 1:07:57 Transcript
What Notable Creators Started On Gumroad at 1:14:23 Transcript
Should We Aim For Billion Dollars Companies After All at 1:15:06 Transcript
What Is The Value In Helping Small Creators Succeed at 1:18:52 Transcript
What Was It Like To Lay Off The Entire Gumroad Team at 1:24:12 Transcript
Is Life A Series Of Distractions From Existential Dread at 1:35:14 Transcript
Are Startups Scary at 1:40:35 Transcript
Is Sahil Happier Now That Gumroad Runs On His Terms at 1:44:36 Transcript

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