Angel investments
I've made over 30 angel investments. Most notable exits include Toast ($25B), Circle ($6.8B), Oqton ($180M) and Ticketbis ($165M). ClassPass reached unicorn status, and my early positions in Bitcoin and Ethereum have also done well.
| Year | Company | Description | Status |
|---|---|---|---|
| 2025 | ActivePieces | Open source workflow automation (Seed) | |
| 2024 | TechWolf | AI-powered skills intelligence (Series B) | |
| 2023 | NineID | Access management for industrial buildings (Seed) | |
| 2021 | Oqton | Manufacturing software (Series A) | Sold to 3D Systems for $180 million |
| Gist | Social shopping (Pre-seed) | Status unknown | |
| Orbit Fab | Spacecraft refueling (Seed) | ||
| 2020 | Mast Reforestation (originally called DroneSeed) | Drone reforestation | |
| 2019 | Cake | Open banking services | Sold to Levenue at a loss |
| 2018 | Circle | Crypto stablecoin issuer (Secondary) | IPOed at $6.8 billion valuation |
| Madison Reed | Home hair care | ||
| 2017 | NodeSource | Enterprise Node.js (Series B) | Sold to i2 Holdings |
| Cafe X | Robotic coffee shops | ||
| Rezi | Rental management (Seed) | Failed; shut down | |
| Moltin | Headless ecommerce (Seed) | Sold to Elastic Path | |
| Ethereum | Cryptocurrency | Hodl-mode | |
| 2016 | Madison Reed | Home hair care | |
| Bitmovin | Video infrastructure (Series A) | ||
| Reaction Commerce | Open source ecommerce | Sold to Mailchimp | |
| Soothe | On-demand massage (Series B) | ||
| NodeSource | Enterprise Node.js (Series A) | Sold to i2 Holdings | |
| Mautic | Open source marketing automation | Sold to Acquia | |
| Fitspot | On-demand fitness | Sold to Gympass | |
| 2015 | ClassPass | Fitness membership network | |
| FirstLine | On-demand doctor visits | Failed; shut down | |
| SketchDeck | On-demand design | ||
| Level | Custom framing | ||
| Drive | Online car sales | Failed; shut down | |
| LittleBird | Social influencer discovery | Sold to Sprinklr | |
| NodeSource | Enterprise Node.js (Seed) | Sold to i2 Holdings | |
| One Month | Online learning | ||
| OneSignal | Push notifications platform | ||
| Open Collective | Fiscal sponsorship for communities | ||
| RecargaPay | Mobile payments for Latin America | ||
| Seaters | Event seat management | ||
| Toast | Restaurant management (Convertible note) | IPOed at $25 billion valuation | |
| Zycada Networks | Edge computing platform | Sold to Palo Alto Networks | |
| Ticketbis | Event ticket marketplace | Sold to eBay for $165M | |
| Purse | Bitcoin e-commerce | Failed; shut down | |
| Signpost | CRM for local businesses | ||
| 2014 | Soothe | On-demand massage (Series A) | |
| Buffer | Social media scheduling | ||
| 2013 | Bitcoin | Cryptocurrency | Hodl-mode |