The Thin Slice

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. Nobody's paying me. Isn't that the number one rule in business, don't work for free?

The answer I use by default, by habit, is that it lights me up. Same answer I gave about teaching high school math. I didn't teach math to help kids. I taught it because it was fun. True, but let's be real, still not quite an actual answer. So it bothered me the same way it bothers me when the numbers are off by a tenth of a decimal point.

Here's the better one, and it took me a while to figure out. This is a real creative outlet. It's not a side effect. It's the drug.

Which sounds absurd. A workshop about money is not where anyone goes looking for art. But teaching math is art, and it's not the lesson plan that's the magic. Students are not robots. You cannot run a good classroom without reading it and picking up on the energy. The art is live. Reading who was engaged, and who was bored, and who was about to say the thing that would open it up for everybody.

I write the worksheets at my desk. That part is craft, and there's art in it. I think a lot about the order of the questions and wanting to have an arc. I have to decide what word replaces freedom on a wheel I'm handing to men serving life. But the actual composition happens in the room, in real time, and none of it is on paper.

The structure is this: the men pair off. One man answers, and his partner asks the questions and writes down what he says. They go all the way through, then they switch. I stay out of it. That's a deliberate choice and it's the closest thing to a signature I have. I'm not the one holding the pen. In fact, I leave a Lamy pen in the room every time I go. The room isn't oriented toward me. And the answers come out different because of it — you say something to another man across a table that you would not say to a Jewish guy from Berkeley in a Money Is Weird ball cap.

Intentionally, two questions run back to back. What does money mean to you right now. And then: when you think about money today, what's the first feeling that shows up.

A man tells you money means security, and then says the first thing he feels is anxiety.

Another says stability, security, opportunity. Then hunger.

A third says a tool to live my life the way I want, then freedom and frustration, and adds: this is a fear.

One writes that money means freedom to participate in society. First feeling: powerless.

Eight of twelve ran that way, and never the other direction. Not once did a man define money as something grim and then report feeling fine. Money never over-delivered.

The second question works because of how fast it is. Ask someone what money means and you get a dissertation about who they are. Ask us how we feel and the truth arrives seconds later, and we don't notice the dissonance.

We define money by a future we don't have yet and feel it through a past we didn't choose. The present is the thin slice in between.

That's what we were looking for here today. That's the art. Finding and making room for that slice.

The other half of the art is what I have to keep out. Put a room of well-read incarcerated men in front of the subject of money and there is a wide-open door marked the global capitalist system. That's what I loved about graduate school. Everything is under the umbrella of capitalism. But that's not what we're doing here.

One man wrote that he doesn't like capitalism, rich getting richer, poor getting poorer, and he isn't wrong, and it is the single fastest way to lose the afternoon. Because that conversation is about a system, and there is nothing to do at the end but sit around and agree that it's systemic. I steer around it. Not because it's untrue. Because it isn't the canvas I set up for the men to paint.

At the end I asked what's one thing about money you'd like to understand better. How to make it. How to invest it and grow it. How to make it efficiently instead of working harder. Over and over, in different handwriting.

They told me exactly what they wanted, and I'm the expert wealthy folks pay to do this for them. And a good part of the answer is closed to them. Compounding is a long-term machine and there's no runway. Very little capital. No access to E-TRADE. I can't hand a Roth IRA at 22 to anyone in that room.

But that's the reversal, and it's the part of this I don't get anywhere else. They're telling me what they want to learn. In a building where every other hour of the day is scheduled for them by somebody else, they're handing me the curriculum. Sometimes paying clients have a hard time with that. They've been trained to ask me what they should want, or what they should do.

And closed isn't the same as gone. What's open was already in the room when I got there. One man runs a 40/60 split, spending forty and saving sixty percent, on almost nothing. Except the designer glasses, which I get. They all confessed to overspending on Ramen. The store is open once a month, so by week two or three there's a secondary market. A few of them pool what they have and talk through options together. One wrote that what's changed is that he now trusts his ability to create and manage money, and that it's growing in spite of being in prison.

What I keep coming back to, though, is everything money stood for that has no financial answer at all. Being unable to provide anything real for your children is not a budgeting problem. Being someone's dependent when you were the one who provided is not a cash flow issue. There is no magic potion. I read those sheets when I got home and understood that some of what these men handed me, just like my clients, is not mine to solve, and that I was going to carry it anyway.

So if the practical thing people assume I'm best at is mostly unavailable to these guys, what am I actually doing? The same thing I do with my clients. I'm helping them tell their story. Not the one about the numbers, the one underneath it that the numbers often stand in for.

We're making something. With twelve men who aren't supposed to make stuff. Maybe that's restorative, maybe it's not. But it's art.

At the start of the day everyone was tasked with writing the early money story from our first session in one sentence. Mine was: I wanted to be seen.

During the session, two men, working separately from the same prompt, described money as if it walked in and sat down across from you — as a guy in Pendleton.

One of them named Lev.

I came in to show them a world they don't see. I left having been shown something about mine.

I wanted to be seen. So I don't think I get to complain about being seen.

Though for the record, the shirt is custom from Al's Attire in North Beach. Now that's a whole other story.