Yesterday, I was talking to my AI Chief of staff, Tiro, about what to do with this newsletter, and it was boring me to death.
I had told it (him? who knows?) I was getting tired of writing about AI for small-business owners. I’ve been doing that for just over a year and the problem is that what I’m working on now is so deep into the technical implementation that SMB owners aren’t interested. Do you want to hear about blind adversarial review in your CI/CD pipeline? I didn’t think so either.
At the same time, I’m not interested in writing the 1000th, “Here’s how to build an AI Chief of Staff,” blog. The reality is that the more involved I get in building these systems, the further I get from what most owners want to know.
So I told Tiro I wanted to return to something that had interested me long before any of this: building a business that can operate without you, and then figuring out what to do with the independence you've earned.
It came back with a sensible plan. Delegation. Better decisions. Taking a vacation without the business falling apart.
I could imagine every article and knew that I’d rather stick a fork in my eye than write any of them.
"That's all so boring," I told it.
Then I had an idea. What if I gave it access to the stuff I pay attention to every day? I told Tiro to look at my newsletter subscriptions in Gmail to get an idea of what actually interested me.
This is the stuff I read by choice. There were newsletters, podcasts, and blogs on economics and investing, politics and human behavior, technology, history and book reviews. Marginal Revolution alongside Stratechery, Robin Hanson alongside Pitchfork Papers. Wine and cocktails made an appearance too.
The conversation improved immediately. After some back and forth, Tiro summarized:
“My interpretation is that your interests run toward understanding the forces shaping your life, seeing through conventional explanations, and finding room to act on your own judgment. Business ownership is one way into that. So are money, technology, politics, history, and culture.
That changes my advice. A sequence about delegation, decision rights, and taking a two-week vacation would squeeze your interests into the same narrow service relationship you’re getting tired of: every week, produce another useful lesson for an owner.
You could instead write a publication people follow because they want to see what you make of things. Your experience owning businesses gives that writing substance. It doesn’t have to dictate every subject.”
Mic drop. That’s me. Thanks, Tiro.
Let’s see where it leads.