I’ve supported ~40 companies as an angel investor and trusted advisor.
If you want to submit a pitch, I built a GPT to help me evaluate opportunities:
Howard Marks, one of the all time great investors, has stated there are only three ways to be successful at investing:
- Be better at massaging current data
- Be better at making qualitative judgments
- Be better at figuring out what the future holds
I try to focus on #2. To me, angel investing starts with the person. I underwrite each opportunity from the bottom up, looking for characteristics I’ve observed across the formidable founders I’ve worked with and studied from. A few of these traits:
- Fast iteration and learning cycles
- Growth mindset increases their slope
- Adept at navigating the maze
- Embraces unknown on their own path
- History of outlier accomplishments
- Seeks excellence
- Agency for company & situation
- Tenacity & resiliency under duress
While I’m not sector-focused, it’s rare for me to invest in consumer products, media, or non-technical teams. I lean into areas and themes aligned with my background, network, and interests:
- Enterprise SaaS, Dev Tools, and Infrastructure
- Fintech and Private Markets
- Commerce Enablement
- Future of Health
Intangible LLC: I often co-invest with Kevin Weatherman via Intangible LLC (Kevin and I have invested in 20+ companies together since 2018).
I also love supporting emerging managers. During my time at On Deck I built a large network of GPs and resources. I’m happy to help with GTM and/or deck reviews.
More On My Investing
Crypto, D2C, consumer social, life sciences, medical devices, media, and gambling
My first angel check was in 2017 into Electric AI. A few of my first-check investments include: Levels, Warp.dev, Kinta AI (exit), Crtsl and Ghst. Series A investments include: PayJoy, OneSignal, Motion and Banner. LP investments include: Notation Capital, Orange DAO/Fund, On Deck Runway Fund I & II, Inuka Capital and Incisive VC.
I will let you know on our first call whether I’m interested, or not. While I have been the first yes several times, it’s unusual, and I prefer to invest in rounds with some additional investor legibility (note: it’s my job to help you get it!). As an angel, I write small checks (<$25,000), but strive to add outsized value.
There are four primary ways I help founders (outside of being a trusted advisor and being happy to take your call — anytime):
- Introductions & Network: I open my network to founders in my portfolio (using Cabal)
- Help Building Momentum: At On Deck we taught founders that fundraising is a muscle: you become better with practice and process (good technique and a game plan). I often spend time with founders working through their approach, including: company narrative, deck/memo, angel introductions and investor CRM.
- Actioning the Cap Table: I’ve coached multiple founders on getting maximum value from the cap table. I have a specific approach I teach and use.
- Tactical Insight/Experience: During my time as an operator/founder I built systems and experience in operations, management, growth and GTM. I’m happy to roll-up my sleeves for a working session, or to discuss playbooks and best practices.