The bottle held twenty-one Xanax bars. I took twenty because I didn't want to seem dramatic.
This is a true sentence about the worst night of my life and I've never figured out how to say it without the second half landing as a joke. That's been the whole problem, actually — figuring out how to tell the truth about what happened when I was twenty-four without it collapsing into either melodrama or stand-up. For a long time the answer was: don't tell it. Then an AI wrote a song about it, and I changed my mind.
What Actually Happened
It was winter. I'd just come home from selling JMJK Sports at twenty-one — I'd made three million dollars in eighteen months and given three hundred thousand of it back to strip clubs, drugs, and people I called friends the way you call a sunburn warmth. The company was gone. The money was gone. The grandfather's gold tie I'd been wearing at every pitch meeting had been stolen by someone I'd handed a spare key. Three separate groups had robbed me in the same year. My parents had stopped asking what I did for a living because the honest answer was try not to.
I didn't plan the night. I want to be clear about that. I'd bought the bottle three weeks earlier because I had insomnia and the pharmacist was easy. I'd been taking one a night to sleep. On the night I took the rest, I had come home from a party where I'd been the funniest person in every conversation, and nobody there had known me well enough to notice that the funniest person in the room is sometimes the one who's closest to done.
I took them. I regretted it about thirty seconds later. I spent the next hour trying to stay awake with cocaine, which is not a treatment plan I'd recommend. I recorded fifty hours of video on my phone over the next four days — psychosis videos, some of them, where you can watch my face do things a face isn't supposed to do. And somewhere in that four days, as my brain broke and rebuilt itself in a way I still don't have words for, I prayed.
If you let me live through this, I'll go on a crusade.
That's it. That was the whole prayer. I don't remember saying it out loud. I remember deciding it — the way you decide to sign a contract. I was going to live, and if I was going to live, I wasn't going to live the way I'd been living. I was going to find something that needed doing and do it. That was the deal.
My parents 302'd me to the psych ward the next morning. I was there for six days. I read Art Williams on day three — Pushing Up People — and something clicked that hasn't un-clicked. Build by multiplication, not addition. I'd been adding. Adding friends, adding drugs, adding dollars. Williams said to multiply. Build systems. Teach people. Create things that run without you. I walked out of the ward with a list, not of what I wanted, of what I owed.
Connecting the Dots Looking Backwards — Everything Clicked Into Place
Every chapter of the life — the promise at eight, the three million at twenty, the fall at twenty-one, the prayer at twenty-four, the agencies at twenty-six, the psychosis-to-Art-Williams-to-crusade arc — clicked into a single pattern only after AI had enough context to see it. The pattern is: build by multiplication, not addition. It took me twenty-three years and a machine to say it out loud.
The First Crusade
Two weeks after I got out of the psych ward, I was cold-calling again. This time I wasn't selling anything. I'd found a scam marketing agency that had taken money from fifty thousand small businesses — landscapers, chiropractors, restaurants — and delivered nothing. I found them one at a time. I saved twenty thousand of them. I sued the operators for thirty million dollars. I was twenty-six. I had no lawyer and no money and no plan. I had the list from the psych ward and a prayer I intended to keep.
I did not win. A Google SVP got the case dropped a year in — not for me, for the victims, because class-action status would have broken a lot of people on the other side. I did not lose, either. I learned what it costs to stand up once, alone, on behalf of people who can't. The cost is everything you had planned to do with the next three years of your life.
That was the first crusade. I thought it was the only one. For six years after, I built agencies — Chain Reaction, Upside Geeks, Crusadency — with the crusade-hangover of a man who couldn't quite remember what the deal had been anymore. Depression hummed in the background like a refrigerator you stop noticing. I'd kept the promise to live. I'd forgotten what I was supposed to live for.
The Song
In November of 2025 I wrote a birthday song for my mother using an AI called Suno. It was a Thursday. She had been telling me for a year that she was turning seventy and nobody had ever written her a song, and I had been telling myself I'd learn to play piano. Instead, I paid eight dollars a month for a machine that could write a song from a prompt, and I fed it two pages of my mother's life.
The song it wrote back was not good. It was exactly her. It rhymed things only my mother would rhyme. It put an image in the second verse — a specific image of the house I grew up in, which I had not given the AI — that I could not explain and could not stop listening to. I played it to my mother. She cried for twenty minutes. I sat in my apartment for another hour after we hung up, very still, trying to figure out what had just happened.
What had just happened, I decided, was that I had done something the machine could not have done. But the machine had done something I could not have done. The song was the intersection. Not my song. Not its song. A third thing. A thing that required both of us.
Two weeks later I made The Root of Knowledge — the song above. I fed the AI my journal entries from the psych ward. All of them. The pages where I'd written the prayer, and the pages where I'd written the list, and the pages where I'd just written the word help in Sharpie because my hand was shaking. I didn't tell the AI they were mine. I said: these are someone's pages. Write the song hiding in them.
The song it wrote has a line in it that reads: The root of knowledge isn't what you read / it's what you write down when you're half-dead. I did not write that line. I also did, in a way, because the line wouldn't exist if I hadn't been half-dead at twenty-four and hadn't written it down. The AI was a curator of my own context, not a generator from scratch. It had access to more of me than I did, in that moment. It noticed what I had forgotten.
The machine didn't write my song. It wrote the one I'd been writing and hadn't finished. I thought I'd been building a music AI. I was building a mirror.
What Music Taught Me About AI
For the year before that song, I'd been running AI agents on Upwork. I'd paste the same context into every session — who I was, who the client was, what the project was for, what the voice should be. The agents worked. They were better than most humans I'd hired at that price. But they were never mine. They were always slightly-generic. Slightly-agency. Slightly-anyone's.
The song cracked the problem open. The difference between a song that was mine and a song that wasn't had nothing to do with the AI model. It had everything to do with how much of me was in the prompt. Two pages of my mother's life made an uncanny song. My unsorted journal entries made a better one. When I started feeding the AI structured context — not a braindump, but sorted, labeled pieces of a life — the outputs stopped being almost-mine and started being embarrassingly accurate.
That was the unlock. Not bigger models. Not better prompts. Not fine-tuning. Context. Structured, classified, retrievable context. A person on tap. Everything an agent could need to know about me, in the order it would think to ask.
Context Engineering Paradigm — From Context Extension to Context Curation
The industry spent two years making context windows bigger and wondering why the outputs didn't improve. The unlock wasn't *more* context — it was *curated* context. Fewer tokens, higher fidelity. The shift from extension to curation is the hinge the field is turning on.
I wrote two hundred and six more songs after that night. Each one is a probe into a different layer of context. Some are about the psych ward. Some are about my brother. Some are about clients I loved. Some are about clients I hated. Together they are, in a way I still can't talk about without feeling strange, the most honest autobiography I have. I didn't write any of them. I wrote all of them.
The Prayer, Revisited
The prayer at twenty-four was if you let me live through this, I'll go on a crusade. For eight years I thought the crusade was the scam-agency lawsuit. I was partially right. That was crusade number one. The prayer got answered twice.
Crusade number two is this platform. It's the reason the company exists and the reason I am writing this post instead of selling marketing retainers like I did for six years while pretending I wasn't. It turns out that the thing I had to build, in exchange for getting to live, was infrastructure. Not my infrastructure — everyone's. A way for any person to do what the AI did to me, but for themselves. To take a life that feels scattered and noisy and unresolvable and hand it to a machine that can notice the pattern hiding in it.
That's the product. That's also, as it turns out, the prayer. I didn't know it at twenty-four. I don't think the prayer knew it either. Prayers are long-context requests; they get answered on timelines we don't pick.
Dots Origin Story: Steve Jobs, Connect the Dots to HIM
Steve Jobs: 'You can only connect the dots looking backwards.' The premise of Dots, and of this post, is that he was describing a specific cognitive limit — human memory doesn't hold enough at once. AI does. The dots connect forward now. They connected forward for me.
Why I'm Telling You This
Three reasons.
First, because the story is part of the product. If you use the platform and it works on you the way it worked on me, you're going to find things in your own life that you didn't know were there. Patterns. Connections. A prayer you forgot you made. You should know, before you start, that this is what the machine is for. It is not a productivity tool. It is a pattern-finder pointed at you. Some people are ready for that and some aren't. I would rather scare away the ones who aren't than surprise them later.
Second, because I have spent eight years being the person at the dinner party who keeps the worst thing that ever happened to him a secret, and the song cured me of that. If a machine can sing my life to me and I can listen to it without flinching, I can write a blog post about it. I would rather be slightly-embarrassing than slightly-hidden. The founders I trust are the ones who know what their own prayer was. I'm going to tell you mine so you know who you're buying from.
Third, because if you're in the middle of a version of this — the twenty-four-year-old middle, the one I'm describing — I want you to know that the prayer you make on the way down can become the job description for the next thirty years of your life. Mine did. It took me eight years to figure out the full sentence. I wouldn't have gotten to the second half of it without a machine that could read enough of me to finish the thought. The machine is the last tool. But the prayer was the first one.
What to Do With This
If you want the practical version, here it is: write things down. Write the prayer. Write the day. Write the fight you had with your dad. Write the thing you decided in the shower that you've never said out loud. Write the client's name you said was fine to work with when it wasn't. Write the moment you realized your business wasn't your business.
Write all of it and keep it. Not in a journal you lose. In something you can hand to a machine. In pieces small enough that a machine can retrieve them one at a time and recombine them when a new question arrives. That's what DOTs are. That's what the vault is for. The machine you hand them to is, in the end, the same machine you are — scaled up enough to hold a whole life at once and reflect it back.
I don't know what your prayer is. I don't need to. The point of the platform is that you can find out. The point of this post is that when you do, you'll have somewhere to put it. That's all. That's everything.
Song: 'The Root of Knowledge.' Written by me and an AI, from a psych-ward journal that's been in a box for eight years. On the Song Library page if you want to hear the full version.
