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
- 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
My AngelList dashboard:
I started my rolling fund in August of 2020. The first three quarters of my rolling fund:
- 2020 Q3, 2.125 TVPI, 83% IRR
- 2020 Q4, 2.55 TVPI, 155% IRR
- 2021 Q1, 2 TVPI, 152% 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 (closer to $100K)
- Writing 100 checks a year
- Fees: standard 2% / 20% (+ .15% AL fees)
- 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, and Nick Kokonas.
There are currently 4/99 spots available in the core rolling fund. If you’re interested in investing, please click here to read the fine print and apply. The minimum is $25K.
If you’re a Qualified Purchaser, meaning $5m in “investments” which includes any vested startup stock you own, you can use this link which lowers the minimum to $1K (thanks to an SEC rule).