For my son's belated eighth birthday present, we took the family to Universal Studios. Four day passes cost $600. Four Express passes cost $1,120. Express lets you skip the line once on every ride. I've never really upgraded. I wait in line. I wasn't planning to start. But that morning I snuck into the bathroom of our hotel room, away from the stuffed animals flying past my face. I went back and forth in my head for five minutes. In thirty years, what will matter is whether w

Every day at 4pm I opened the D.A.V.E. portal, copied a number, and pasted it into a very good-looking Google Doc. D.A.V.E. was our admin portal, named after the strongest monster in the game. Nothing fancy. Just the numbers that mattered, one day at a time: how much people paid and how many kept coming back. For the size of our team, it was bananas. Most of it could be entered whenever. Daily users couldn’t. At 4pm, midnight in London, the count rolled over. If I didn’t grab

Money Is Personal, Part 2 — San Quentin, September 5, 2026 At San Quentin, you leave your phone in the car in the guest parking lot, which for me is a trip back to 1995, "Biggie give me one more chance." The gravel pops under my Stan Smiths and I think to myself, it's Labor Day weekend. Why am I even here? I'm a financial advisor from Berkeley walking into a prison to talk about feelings with men whose average time served runs longer than my brand manager has been alive. Nobo

Yesterday my son Ezekiel was walking around in his underwear, complaining about having to wear pants to school. Mommy was making him. I didn't lose anything. Weird that somehow I felt like I did. What does loss feel like? For me it's not simply sadness. It's my chest. Short of breath. Hands a little clammy, heart beating a little faster. Oh. Like that Doechii song. What have I actually lost? Mostly, I think it's the chance to make future memories with whoever or whatever's go