Gumroad founder Sahil Lavingia is investing $5 million a year into early-stage technology startups

Gumroad founder Sahil Lavingia has teamed up with AngelList to launch his debut $5 million rolling funds to invest in early-stage entrepreneurs. He will be cutting $100,000 to $250,000 checks for startups and has a particular interest in B2B, SaaS, future of work, video and developer tools.

Talking to TechCrunch, Lavingia said that he didn’t even know he wanted to be a VC. The entrepreneur has made some angel investments in Lambda School, Figma, Haus, Clubhouse and HelloSign (later Dropbox acquired it). Eventually, though, he says angel investing got too expensive for him to do, so he stopped.

Post the Black Lives Matter Movement, he invested in four startups founded by Black entrepreneurs. Later, Lavingia worked with AngelList to create his fund and has capital commitments of $1.25 million per quarter in a $5 million per year fund. In a tweet, and on his website, he later announced that he will be cutting these checks.

Let the fun(d) begin! Starting today, I am investing $5 million a year into early-stage startups via $100K-250K checks. More info 👇🏽

Let me know if you have any questions!https://t.co/LInbiH1q6b

— Sahil Lavingia (@shl) August 5, 2020

About Sahil Lavingia

Lavingia was the second employee at Pinterest. He left it to start building Gumroad, a platform to help creators sell products to consumers. Then the company went through a gutting round of layoffs and restructuring in 2015. You can read about his story of the failure in a post titled “Failure to build a billion-dollar company.” Today, Gumroad is at $10 million ARR and is growing 100% year over year with a team of 10 people.

He recounts his failure as "growing too fast".

About the fund

On the website, Sahil says, "I’m looking for founders who have a deep understanding of the space they are in. They typically read a lot and haven't waited for permission to get started. They have hard skills if not degrees and don't have access to the traditional startup ecosystem."

He further added, "I am interested in products that are soon-to-be obvious but only recently possible. They solving a difficult, boring, complex problem with an easy-to-use, elegant solution. I’m particularly interested in b2b, SaaS, commerce, the future of work, video, and developer tools."

Who are the investors?

LPs in the find list will include:

• Naval Ravikant, founder of AngelList
• John Lilly, ex-CEO of Mozilla
• Minal Hasan, founder of K2 Global
• Saikat Chakrabati, ex-Chief of Staff for AOC
• Matt Mullenweg, creator of WordPress
• Arlan Hamilton, founder of Backstage Capital
• Tim Ferriss, author
• Greg Brockman, ex-CTO Stripe, CTO OpenAI
• Nick Kokonas, co-owner of The Alinea Group
• Paul McKellar, the founding team of Square

And finally Sahil himself. He will be putting 80% of his management fees back into the fund as LP capital.

How to contact him?

Formal approach: send a deck or memo to sahil@hey.com or he is casual enough to answer queries on Twitter @shl asking for help on something.