How I invest
Angel Investing
I write $1–10K checks into early-stage companies, mostly AI infrastructure, developer tools, and robotics. The goal: back people building the picks-and-shovels for the next wave of AI applications, not the applications themselves.
Thesis
Three rough buckets I look at:
- AI infrastructure: the layers that let teams ship AI without gluing together a dozen brittle services: inference, evals, observability, orchestration, security. Where I spend most of my day-job and podcast time, so where I have the strongest read on what's real.
- Developer tools: anything that meaningfully changes how engineers build, ship, or operate software. I've spent the last six years inside two developer-tooling companies and a podcast about developer experience; this is the space I have opinions about.
- Adjacent bets: robotics, fintech infrastructure, and the occasional consumer AI play when the founder is exceptional and the wedge is defensible.
I lean toward people I've gotten to know, through Chain of Thought guests, prior operator overlap, or doing the work alongside them in their early product. I prefer to be useful (intros, GTM advice, content distribution) over passive.
Active portfolio
-
The world's publishing platform.
-
AI customer service for e-commerce.
-
Consumer AI assistant.
-
AI game-creation platform.
-
Deepfake and document-authenticity detection.
-
Execution authority for API integrations.
-
B2B stablecoin payments and online banking.
-
Industrial robotics and haptics.
-
Lab-automation robotics.
-
DTC custom orthotics via AI scanning.
-
AI marketing platform.
-
Non-alcoholic craft beer.
-
Ultralight backpacking apparel.
-
Diversified YC batch fund.
Checks by year
15 checks since 2022, counting positions that have since shut down or exited. The list above is current holdings only; 2026 is year-to-date.
Advisory
A check is a vote of confidence; an advisor role is a standing one, months of hands-on work alongside a team, not just a wire. Two so far:
- Swytchcode (opens in new tab) 2025–present
Execution authority for API integrations.
- Ridwell (opens in new tab) 2019–2020
Doorstep pickup for hard-to-recycle household waste.
What I'm useful for
- Developer GTM: I've run developer marketing and ecosystems at three developer-tooling companies. I can tell you what works, what burns money, and which motions don't survive contact with a real audience.
- Content distribution: Chain of Thought, LinkedIn, Substack, useful for credibility narratives and reaching technical buyers.
- Intros: Access to my network of podcast guests, fellow angels, and dev-tool operators, built over years of conferences and ecosystem work. Disproportionately strong in inference, evals, observability, and developer productivity.
Pitching me
Best path: warm intro through someone we both know. If that's not available, message me on LinkedIn with a one-paragraph what-you-do + what-you-need. I'm slow to first reply but I read everything.
Disclosures: positions and/or advisory roles in companies listed above. I do not provide investment advice; nothing on this page is a recommendation. Portfolio is a snapshot. Not necessarily complete, not necessarily current.