Angel Investing
My Angel Investing Journey
I started angel investing because I wanted to put my money where my mouth was. After years of working at startups and advising founders, I figured the best way to learn was to actually write checks. This series documents that journey: the thesis I developed, the deals I made, and what I learned along the way.
Every investment review in this series is written with the same goal: to be honest about what I saw, what I thought, and what happened. Some of these companies have done well. Others haven’t. That’s the nature of early-stage investing, and pretending otherwise wouldn’t help anyone.
The Thesis
Introducing My Angel Investing Journey lays out how I think about angel investing: what I look for, what I avoid, and how I structure my approach. If you’re thinking about angel investing yourself, start here for the framework behind the individual decisions.
The Deals
Each investment review covers what the company does, why I invested, and my assessment at the time. They’re organized chronologically, which also happens to track how my thinking evolved as I got more deals under my belt.
2021-2022: Early Investments
The first batch of investments covered a wide range of sectors as I was still refining what I gravitated toward:
- Flexbase - fintech for construction and contracting businesses
- Homeroom - rethinking the student housing experience
- The Essential (formerly Move.co) - consumer products
- Semicab - logistics and freight optimization
- Alga Biosciences - biotech tackling methane emissions from livestock
- Beyond Aero - hydrogen-electric aviation
- Cambrium Bio - computational protein design
- Seer.ai - AI-driven analytics
- DeepSentinel - AI-powered home security
2023: Refining the Approach
By 2023, patterns in what I liked were becoming clearer, and the deals reflected that:
- Switchyards - community and workspace for early-stage founders
- Jericho Security - AI-driven cybersecurity training
- Scout Space Systems - space domain awareness and tracking