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.
1. Where does demand come from before someone knows they need something?
Most marketing captures demand that already exists. Somebody searches, you show up. That works until it doesn't, because in most markets the vast majority of your buyers aren't shopping.
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.
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.
2. What makes a dinner party with strangers actually work?
I used to host dinner parties regularly. Some nights the table catches fire and people exchange numbers in the driveway. Other nights the conversation stays polite and forgettable.
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.
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.
3. How do you build a brand that compounds?
Private equity gives you three to five years. Brand compounds over ten. Those two timelines fight each other constantly.
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 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.
4. How can operators become founders, especially when they've always been an operator?
This question lives rent-free in my brain. There are seasons when it dominates my thinking.
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.
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.
5. What can school district leaders do to change public perception and improve staff culture at the same time?
I spent eight years in K-12 marketing and communications, and this was the undercurrent of everything.
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.
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.
6. How do you stay physically strong when your schedule and energy belong to other people?
Four kids, a demanding job, a body that doesn't recover the way it did at 25. The advice is the same everywhere: wake up earlier, meal prep, find your non-negotiable hour. I've done all of that. It works until it doesn't.
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.
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.
7. What's the relationship between serendipity and strategy?
I keep saying serendipity is underrated as a strategy, and I believe it. But I also know that's an incomplete thought.
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?
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?
8. What should a personal investment strategy look like for someone who sees deal flow but isn't a professional investor?
I sit close enough to deals and portfolio companies to have opinions about markets, operators, and timing. But having opinions and having a disciplined strategy are different things.
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.
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.
9. Why does demand creation work in some verticals and not others? (Or does it always work and we just measure it wrong?)
At Apptegy, a print magazine and a podcast drove more pipeline over five years than any paid campaign. That's a demand creation story.
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 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.
10. How do you raise kids who are self-aware without making them self-conscious?
The most important part of my life. I want my kids to be aware, creative, and thankful. I've found that's a better filter than smart, successful, or accomplished.
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.
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.
11. What makes someone choose your thing when they weren't looking for anything?
This is the demand creation question, but zoomed out past marketing. Rory Sutherland would call it psycho-logic: the idea that human decisions are governed less by logic than by perception, context, and the path of least resistance.
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.
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.
12. Can you build a meaningful professional body of work from a place like Little Rock?
New York has density. San Francisco has capital. Austin has momentum. Little Rock has space: to think, to build without performance pressure, to stay close to the kind of communities that most industries overlook.
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.
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.