Dipping toes in angel investing.

I’m ending the year by pushing a handful of drafts that have something useful but that I’ll probably never finish. I’ve dubbed this draft week, and this is one of them!

As I get a bit deeper into my career, I’ve gotten a bit more focused on exploring the professional side-projects folks take on. In the past few years, I’ve spent time getting a sense for book writing, conference speaking, and podcast speaking. Some of those I’ve enjoyed (book writing), others I’m not planning to do much more of (conference speaking), and over the past year I’ve been exploring angel investing a bit more.

I started by reading what’s out there, including Angel Investing: Start to Finish (Wallin, Baltaxe), Angel: How to Invest in Technology Startups (Calacanis), and Fool’s Gold?: The Truth Behind Angel Investing in America (Shane). I also started a Twitter thread asking about what motivated folks to angel invest, and there were a bunch of great comments, especially those by Cristina Cordova, Joshua Schachter, and Mayank Verma. The cited motivations fell cleanly into those listed in Fool’s Gold?:

1. To make money
2. To get involved with private companies
3. To learn new things
4. As a hobby job
5. To find a job
6. To help the community
7. Because a friend has a business

The two that I’m personally interested in are (3) learning new things and (6) helping the community. In particular, my professional hobbies like writing center on the idea of nudging the industry towards what I believe is a more effective and inclusive version of itself, and my underlying question is whether angel investing is a more useful pursuit towards that end than writing another book or publishing more blog posts.

Working with my wife, we put together a budget for angel investing in 2021 and 2022, which I’m excited to use to answer that question. That budget is roughly enough for four investments each year. For 2021, I’ve made a particular emphasis on investing into different sorts of companies and opportunities (pre-seed, seed, a small fund, etc).

Over the course of the year, we did make the planned four investments, writing $25,000 checks, and the learning has begun! From these early learnings, we’ll refine our investment hypothesis a bit as we go into 2022. I’m still not quite sure what the refinements will be, but a few ideas: more focused on areas I understand (infrastructure engineering, etc), early stage but about to hire (I think my experience is most useful here), and founders less centralized in Silicon Valley (these folks have relatively less access to investment, and helpful to learn about the recent hypothesis that much of the next round of innovation will be away from current innovation centers).

My best bet is that I’ll really enjoy exploring angel investing as a hobby for a few years and then refocus my increasingly narrow time allocated to professional hobbies back to writing, but excited to see if I change my mind along the way.