I announced yesterday that we’re back in Boston, and that I’m doing something new. At the end of my day, my primary activities are pretty similar.

  • I’m looking at a couple spaces for startups and starting to work on things (more on that soon).
  • I’m still advising and angel investing (email me!)
  • I’m planning to write a lot more now.

One silver lining about the events at Dark this summer was the timing. As some people know, I did my first year at Harvard Business School six years ago. The length of time you’re allowed to be gone after the first year is... five years.

When it became clear I wouldn’t be continuing at Dark, I re-enrolled myself. It’s three months this fall (now-December) and then late January - May. The obvious question here is “why bother?”

First, fodder is important for new ideas. When I’m working on something new, I need to see other ideas. Here, I default to seeing 2-3 businesses a day and hearing people analyze them. HBS is full of students, faculty, and community members who want to talk about each others’ ideas.

Second, HBS is intellectually fascinating. The content is good but it’s also pedagogically cool to see how new courses are introduced and taught.

This is particularly true now. HBS is built around a model of putting a lot of extroverts in one room. COVID has challenged that assumption. It was interesting to watch Nokia try (and fail) to adjust to iOS and Android, and similarly I am enjoying this process.

For better or for worse, what HBS teaches does have an impact on the broader world. Even just in the five years, I’d argue the tone in the room has changed. Diversity and inclusion rarely came up five years ago, today it comes up in nearly every conversation about teams and people. It feels genuine and gives me some hope.

Third, there are some classes I wanted to take. There were a couple I still wanted to get a stronger foundation for, but having spent most of my educational career on very tangible skills (hello engineering, design, and finance), and some stuff I just wanted do for fun. I’m so excited to finally take a class that involves reading books and analyzing what their protagonists do.

The last time around, I was very insecure about being at HBS. I felt like everyone in tech kept going “this thing is useless” and I had a lot of qualms about if I’d still be able to achieve my goals. It turned out well last time, and I still feel that insecurity. I considered not telling anyone, and yelling “surprise!” after graduation. Instead I’d rather be honest about it. I’m happy to have this support structure for launching the next thing.