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)
- 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
- Jam, 2020 Pre-seed, raised from USV at 8x
- Vercel, 2020 Series B, has since raised at 3x valuation
- Baseten, 2019 Seed, has since raised at 6x valuation
- Figma, 2020 Series D, has since raised at 5x valuation
I started my rolling fund in August of 2020. The first three quarters of my rolling fund:
- 2020 Q3, 3.17x, 93% IRR
- 2020 Q4, 3.11x, 113% IRR
- 2021 Q1, 2 TVPI, 74% IRR
Markups by firms like A16Z, Tiger Global, Coatue, and Founders Fund.
I am interested in products that are:
- soon-to-be obvious but only recently possible
- solving a difficult, boring, complex problem with an easy-to-use, elegant solution
I’ll look at anything, but especially B2B SaaS, future of work, consumer social, and developer tools.
I will look for founders who:
- have a deep understanding of the space they are in – they typically read a lot
- haven't waited for permission to get started – they have hard skills if not degrees
- don't have access to the traditional startup ecosystem – they may be younger, URM, etc
Put simply: product-focused tinkerers.
I have access to high-quality companies from around the world, because:
- I have a fast-growing audience–my large Twitter audience and now a Penguin Random House-published book–of founders who respect me because I operate a successful business and write about the good parts and the bad parts.
- I have a strong network from living and working in Silicon Valley and tweeting from afar.
Founders want me on their cap table, because:
- I am a founder. Founders want to raise money from founders, because we have experience.
- I am a designer and engineer, but often most importantly a user:
- I have an engaged audience that can move the needle for them, in an organic way:
Examples of my success getting into deals:
- Invested in HelloSign as an 18-year old kid with no track record, after attending YC’s Demo Day by cold emailing Paul Graham. (Anyone can do this, few do.)
- This tweet got 200K impressions, led to 200 emails from URM founders, and 4 checks wired:
My primary focus will be helping founders think through their product, offering design and marketing feedback as they head toward their next financial milestone, often a Series A.
- Earliest-stage startups (and tokens)
- Check size range: $100K-$250K
- Writing 50+ checks a year
- Fees: standard 2% / 20% (+ .15% AL fees), 30% after 3x
- Minimum: $12.5K per quarter
LPs include Naval Ravikant, Arlan Hamilton, Matt Mullenweg, Elad Gil, Tim Ferriss, John Lilly, Minal Hasan, Josh Kopelman, Marc Andreessen, Tiger Global, and Nick Kokonas.
There are currently no spots available in my core rolling fund.
You can sign up to be notified about the rare deal-by-deal via my syndicate.
If you’re a Qualified Purchaser, meaning $5m in “investments” which includes any vested startup stock–I’m talking to you, founders!–you can use this link which lowers the minimum to $1K a quarter (thanks to an SEC rule).