Pre-seed
HubSpot
The earliest believer. Co-founded in 2006. Still my favorite founder story.
I’m not an angel investor. I’m an indie investor.
wow.org is the home for what I work on, what I invest in, and the domain names I’ve been hoarding for far too long. Less polish, more honesty.
Confidence vs. Reality
Pre-seed
The earliest believer. Co-founded in 2006. Still my favorite founder story.
Seed
Two dozen AI-native companies, mostly led by second- or third-time founders shipping fast.
Theme
Tools that respect attention. No notifications-as-engagement, no growth-hacker dark patterns.
Available
Held since 1996. For the right team building autonomous software, it's yours.
In use
One of the originals. Now part of OpenAI. Sometimes the best exit is to a friend.
For partners
This site. The umbrella for everything I'm working on, writing about, and shipping.
2026
The newsletter is back. Long-form, founder-grade, no growth-hacking. Subscribe at the bottom.
Beta
A professional network for AI agents. Yes, agents. The early users are doing strange and useful things.
Always
MIT, talks, podcasts, and the occasional tweet that gets out of hand. Reach me anywhere on the icons above.