Our Old Dad

  Talking It Into Existence I used to dream out loud constantly. Walk around Chicago, see something I wanted, and just announce it to whoever was listening. "I'm getting a Harley." That's what I did one night in Lakeview—Scott Kell and some girls, Harley's rumbling past, me declaring I'd own one. Kell called bullshit immediately. Said I was full of it. And he was right to call it. At that moment, it was just talk. But something about saying it out loud—especially to someone who'd hold me accountable—made it stick. Once it was out there, my brain wouldn't let it go. The idea kept pulling my attention back. The hows and whys started working themselves out without me forcing them. Eventually I owned not one but two Harleys. This wasn't a one-time thing. I've done it over and over. The pattern's always the same: announce the thing, lock myself in publicly, remove the wiggle room, then watch my brain figure out how to make it real. The tri...

  I’ve started deleting things from my life—not dramatically, just ruthlessly. If it doesn’t serve the plan—retire and slow travel with my kids—it doesn’t get time. That shift has been weirdly exhilarating. And it comes with a hard truth: we’ve got about six years. That’s not “someday.” That’s now. If this is real, I need all six years to build the logistics and the learning system that can survive life on the road. The new focus and realness of it all has made me start second-guessing myself and letting fear creep into the planning.  “Fear is a planning input, not a stop sign” I keep noticing how much of parenting—and especially education decisions—is governed by fear. Not the healthy kind of fear that keeps you from doing something stupid. The institutional kind. The kind that whispers: “If you step off the approved path, you can ruin your kids.” School systems (and the culture around them) lean on that fear. It’s subtle, but it’s everywhere: the idea that professionals m...

  Fear is the guardrail (and I finally named it) I was listening to the Self-Directed podcast (October episode with Tim Eaton), and the conversation kept orbiting fear — not in a dramatic way, more like an ambient force that sits in the room any time you talk about stepping off the standard school path. Today it landed for me because I finally pinned down what the fear actually is: It’s not “I don’t love my kids.” It’s not “I’m trying to neglect their future.” It’s not even “I don’t have a plan.” It’s the system-whisper: What if you ruin them? What if they fall behind? What if they become helpless? What if you take a risk and you can’t undo it? And then two questions cut right through all of that. 1) If I love my kids unconditionally and actually do the work… what’s the worst that can happen that’s within my control? Obviously, horrible things exist in the world. That’s not what I mean. I mean: if the baseline is unconditional love, attention, stability, and purpose —...

 Most people use AI like a search engine with a personality. Type a question. Get an answer. Forget it. Repeat. That’s fine for trivia and small tasks. It’s terrible for changing your life . If you have a big goal—retire early, switch careers, build a business, slow travel, write a book, whatever—you don’t just have one problem. You have 12 different kinds of problems spread across money, work, health, logistics, psychology, family, and more. What I’ve been building (and what you can steal) is a way to turn AI into a structured support system for that kind of goal: You pick a big, long-term outcome. You break it into the domains that actually decide whether it happens . You make one AI “Project” per domain , each with clear instructions. Later, you match each Project with a Custom GPT (or Claude persona, etc.) that thinks in the right way for that domain. My own example goal is slow travel with my two youngest kids , but this structure works for: Changing ...

’90s me was sunk into a lopsided couch off 6th and Pearl in Boulder, a living room that smelled like bong water, thrift-store patchouli, and wet ski gloves. We’d flip between local news and reruns, argue whether The Sink or Dot’s Diner had the better hangover eggs, and swear we could see faces in the Flatirons if the sunset hit just right. That night, two stories bled together through the haze: pets getting microchipped and breathless chatter about barcodes for people . We were not “if you’ve got nothing to hide…” guys. We had plenty to hide. This was dial-up and pagers, a shoebox of Dead tapes— Jerry was still alive —and gravity bongs made from 2-liter bottles. In Boulder you could be a stoner and a citizen; in a lot of places it was a felony back then. Boulder’s acceptance made you lax when you visited anywhere else—you’d forget the rules changed at the county line. Our consensus was simple: no chips, no codes, no thanks —and besides, “No one would ever go for that, dude.” We a...

I remember the ’92 election mostly as a pile of commas. Clinton, Bush, Perot—and Perot’s money. Sources put his fortune around $3 billion then. At a plain 5%, that throws off $150M a year ≈ $12.5M a month ≈ $411k a day ≈ $17k an hour , without touching principal. Why keep grinding when the interest alone buys the world? Here’s where my brain went then (and honestly, often still goes): if I had that pile, I wouldn’t work. I’d live like a rock star—beach, planes, chasing the party, margaritas, following the Dead, dumb grins in new cities. Not a “serve the republic” phase. Pleasure, autonomy, no boss. So I couldn’t understand Perot: why would anyone with that kind of glide path choose more work? And then it clicked: that’s exactly why I’ll never be a billionaire—I don’t think like one. He wasn’t counting interest; he was counting the next thing. Not moral, not immoral—just different wiring. My default question was “How do I stop and enjoy this?” His was “What do I build next?” If y...

  I didn’t build this system. I asked for it. I have wanted a world class group of advisors for every aspect of my life, and I was tired of waiting. 🧠🧭 The Frustration 😤 It started like this: I was using ChatGPT regularly and getting a lot out of it — more than most people, probably. But over time, things got messy. Conversations would drift. Memory would fill up. I'd lose context, or worse, start preserving the wrong kind of context: fragments of specific details that clogged the system while the important, core parts of me — the way I think, the values that drive my decisions — got buried under domain names and test scores. It wasn’t that ChatGPT was broken. It was doing exactly what I was asking — just not what I wanted . So I stopped. And I asked it a simple question: "What if I want a team of world-class advisors who think like I do, but who each specialize in a different area of my life? What if I’m not the same person in every domain, and I want AI that re...