100+ Episodes: What I Have Learned Building MoonshotOS

Listen on: Apple Podcasts - Spotify - YouTube

To celebrate more than a hundred episodes, I handed over the microphone. Pete Moore, head of school at Oak Hill School, reached out with an idea: flip the format and let him interview me.

We covered my career supporting independent schools, the companies I started at the dawn of the internet, why I named the company MoonshotOS, and the calls I made to heads of school in the fall of 2023 that told me the pressure on the business model wasn't something I was imagining.

Pete also asked me to reflect on more than a hundred episodes of the podcast. I have recorded more than four hundred episodes across four different shows, and a good part of how I program this one is selfish. I don't have the answer, so I find someone who has done that well and ask them about it. That is why I understand the intricacies of the school business model far better than I did when I started this show. The rest of the conversation gets into where a school should start when everything feels overwhelming.

My thanks to Pete for his questions. Reflection is a practice I keep, and I am always grateful for another occasion to do it, particularly when someone else is choosing the questions.

5 Top Takeaways

• The pressure on the business model is real, and discovery calls confirmed it. Calling heads of school in the fall of 2023 turned a hunch into evidence. Hiring, enrollment, birth rates, and discounting kept surfacing in the same conversations.

• The independent school business model is challenged, not broken. We talked about that in the conversation, because the word matters. Broken suggests the thing needs replacing and invites panic at the board table. Challenged points to specific pressures a leadership team can identify and work on.

• What the market says it wants shifts, so validate before you build. Ask the same questions of everyone you talk to, because patterns only show up when the questions are consistent.

• Getting to root cause beats reacting to the symptom. Enrollment declines build quietly over years. Pulling one lever against the number you can see usually buys very little.

• Consistency is what makes a podcast work, not production value. Four hundred episodes across four shows, and the ones that lasted were the ones where the topic still held my interest three years in.