Now · June 2026
The bets I was making in June 2026.
An archived entry — what I was actually changing, chasing, and being changed by that month, kept exactly as it was written.
The bets
What I am changing this month.
The operating system is the moat, not the founder
Summer pulls everything toward The Cooling Company.. and the position I am taking is that a service business compounds through its team and its system, not through the person who started it. The deeper bet is that local ownership that reinvests beats private equity that extracts.. and that the gap between them is not sentiment, it is how the math reads over a decade.
Run the company on the tools, or do not sell them
We have started running gardenpatch on gardenpatch.. the same software we sell is now doing real work inside the company. The bet is that dogfooding is the only honest proof a tool exists.. if it cannot run the place that built it, it has no business being sold to anyone else.
The cost of AI is the people, not the model
I am watching executives race for the right answer with AI.. and the numbers are starting to argue back: data out of Microsoft suggests the technology can cost more than the people it was meant to replace. The question underneath the race is whether this is growth at all costs.. companies shedding the very people who built them, only to learn the bill was higher all along. The position I am taking is that adoption is a human-change problem.. the ones who win bring their people across, they do not buy their way past them.
Authentic at scale, or not at scale at all
I am building the systems that let me make and share the thinking behind the work.. the talks, the writing, the ideas underneath the companies. The bet this month is that none of it can come at the cost of sounding like a brand.. the moment a founder becomes a perfectly-packaged product, the trust that made the work matter quietly leaves the room.
The questions
What I am chasing.
How do you build from purpose without becoming a product?
When everything has to be packaged and presented perfectly, a part of me starts to feel like merchandise. I do not yet know where the honest line sits between sharing the work and performing a version of myself.
What does it actually cost to bring people into the AI era?
Not the technology.. the people. Every leader I talk to is solving for the right answer with AI. I am more interested in the question almost no one is pricing.. what it takes to carry a whole team across without leaving anyone behind.
Where did the social world go after 2020?
Something in the way we gather quietly broke that year, and I am not sure all of it came back. The question I keep returning to is whether real human connection can be rebuilt on purpose.. or whether it only ever arrives by accident.
Reading
- The Seven Meanings of Life.. Thomas Hylland Eriksen
- Sum: Forty Tales from the Afterlives.. David Eagleman
- Still deciding which of those two to open first this month
- The open feed on X.. learning in real time from the sharpest people thinking out loud
Thinking about
- What it costs to be known for your work rather than simply known
- How to meet people as a person and not a position
- Whether the version of me that existed before 2020 is gone or only gone quiet
- What bringing people along really costs when the technology moves faster than the trust
- How a talk can change a room instead of impressing it
- Whether building a life and building companies are the same discipline or opposite ones
This is the current month. See the live /now page.