Richard Feynman kept a dozen problems in his head at all times. Not to solve them. To carry them. Whenever he encountered a new idea or technique, he tested it against each problem. Most of the time, nothing happened. Occasionally, something clicked.
I've borrowed the practice. These are the problems I think about most. Some are professional, some are personal, and the boundaries between the two are thinner than I'd like to admit.
What moves a market is the thing that happened six months before the search. I keep circling this question because I've seen it play out twice now (at Apptegy and across the Fox Den portfolio) and I'm still drawing the map.
The inputs look the same: food, wine, interesting people, a good question to start. But the outputs vary wildly. I think this is a design problem more than a luck problem, and I haven't solved it yet.
And as a host, I'm still trying to figure out what it looks like for me to connect even while I'm facilitating connections.
I spend most of my working hours trying to reconcile them, finding the brand moves that create measurable pipeline within 18 months while building something durable enough that the next owner inherits momentum, not a machine that needs constant feeding.
I see founders who are on their fifth company, but I rarely see lifelong operators make the jump. That's interesting to me. I see it in myself. There's an itch I want to scratch, and I haven't found the right version of it yet.
Superintendents face a perception problem (the public thinks schools are failing) and a culture problem (teachers feel undervalued), and most treat them as separate challenges. They're not.
The superintendent who figures out how to tell a story that's honest enough to build trust externally and specific enough to build pride internally changes a community. I've seen glimpses. I haven't seen a repeatable playbook.
The deeper question is about identity, whether you see yourself as someone who trains or someone who tries to fit training in. Those are different people with different outcomes, and the transition between them is harder than any program.
You can't manufacture serendipity, but you can engineer a higher probability of it: by showing up, staying curious, saying yes to things that don't obviously fit.
The question I keep returning to is where the line is. When does openness become lack of focus? When does saying yes to everything mean you've stopped choosing?
I'm thinking about how to build an investment approach that takes advantage of proximity and pattern recognition without drifting into overconfidence or distraction from my actual job.
But when I look at other portfolio companies (logistics, healthcare), the same approach doesn't translate directly. I'm trying to figure out whether the principle is universal and the tactics need to change, or whether some markets respond better to capture than creation.
But awareness is tricky to cultivate in a child. Push too hard and you create anxiety. Don't push at all and you get entitlement. I don't have this figured out, and anyone who says they do is selling something.
The best product doesn't always win. The most trusted, most familiar, most socially safe choice does (or the one that's most intriguing and someone can't forget).
I think about this when I'm building campaigns, but I also think about it when I'm deciding which book to read or which person to call back first.
I moved here in 2016 and have built everything since from here. The question I carry is whether the advantages of a quiet place compound the way the advantages of a loud one do. I think the answer is yes, but I'm still testing it.
These aren't rhetorical. I collect notes, quotes, books, and conversations against each one. If you're thinking about any of these problems, or if you think I'm asking the wrong version of the right question, I'd like to hear from you. Pick a time to talk.