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.
- HelloSign, 2011 Seed, sold to Dropbox for $230M in 2019 (18x, 44% IRR)
- Movable Ink, 2011 Seed, raised $30M Series C in 2020 (48x, 54% IRR)
- 3 others that didn't work out, all in: 15x in 10 years
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