Sahil Lavingia is the founder and CEO of Gumroad.
Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few. In Today’s Episode You Will Learn: 1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset? 2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing? 3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms? 4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table? 5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this? Items Mentioned In Today’s Show: Sahil’s Fave Book: How to Win Friends and Influence People As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Sahil Lavingia (@shl), founder and CEO of Gumroad, joins Erik on this episode.They discuss:- The story of starting Gumroad, raising money, and getting featured in the media.- Going from a twenty person company to a five person company to a single-person company.- The advice he would give to a younger version of himself if he was starting over again.- The creator economy and which types of content do well.- How to think about raising capital.- Time as a status symbol, the merits of cities, and what it means to “play poker with an open hand.”Thanks for listening — if you like what you hear, please review us on your favorite podcast platform. Check us out on the web at villageglobal.vc or get in touch with us on Twitter @villageglobal.
Sahil Lavingia is the founder and CEO of Gumroad, a web platform where creators can sell products directly to consumers with quick, simple links. Sahil was the second-ever employee at Pinterest before starting Gumroad with the goal of making it a billion-dollar company. Gumroad got off to an explosive start, but it eventually imploded. Sahil managed to keep the company afloat and made it independent, healthy, and profitable. Although Gumroad isn’t the billion-dollar company Sahil originally imagined it would be, it has created tremendous value for creators who’ve generated nearly $190 million from selling their creations on the website. You can say hello to Sahil on Twitter and read his viral article on his failure to build a billion-dollar company at this link. Sahil and I discuss: Why he dropped out of college only after a semester What it was like to be the second-ever employee at Pinterest The critical difference between one-way and two-way decisions Why Silicon Valley is far less risky than people assume How he ended up with $8 million in his bank account as a 19-year-old founder of Gumroad Why Gumroad eventually imploded after an explosive start What it was like for Sahil to navigate this public failure and what advice he would have given himself How Sahil finally turned the company around Why he believes his definition of success as building a billion-dollar company was flawed from the very beginning Why you should start a company if you’re thinking about it.
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Creator Details

Location
Portland, Oregon, United States of America
Episode Count
3
Podcast Count
3
Total Airtime
2 hours, 24 minutes
PCID
Podchaser Creator ID logo 202729