General partner

I am the founder and CEO of Gumroad, a service that helps creators get paid for their work—over $500 million to date. We raised money from Kleiner Perkins, First Round, Naval Ravikant, Chris Sacca, and others. I wrote about that journey here (1M reads). I also have 250K followers on Twitter.

I got my start in Silicon Valley as employee #2 at Pinterest, and since then have angel invested in about 100 startups including Figma, Notion, Vercel, HelloSign, and Mercury.

Track record

• HelloSign, 2011 Seed, sold to Dropbox for $230M in 2019 (18x)
• Movable Ink, 2011 Seed, raised $50M Series D in 2022 (205x)
• 3 others that didn't work out, all in: 50x in 11 years, 40% IRR

I was focused on Gumroad from 2012-2016–no angel investments.

• Lambda School, 2017 Seed, raised $74M Series C in 2020 (20x est., 112% IRR)
• Squad, 2019 Seed, acquired by Twitter
• Makerpad, 2019 Seed, acquired by Zapier
• Brave Care, 2019 Seed, raised Series A at 4x valuation
• Circle, 2020 Seed, up 33x
• Clubhouse, 2020 Series A, has since raised from A16Z at 40x valuation
• Notion, 2020 Series B