Honestly? I think the next few years are going to be full of AI-generated everything: content, faces, voices, opinions, most of it trying very hard to convince you it's real. I'd rather build the version that's honest about what it is, has something actually worth saying, and doesn't take itself so seriously that it forgets to be interesting.
The Idea Started With Both of Us Being a Little Too Fascinated by AI
A few months ago, I was going down one of my usual AI rabbit holes reading about what these tools could actually do now versus six months ago, and my son Winston was doing the same thing, from his own angle. At some point the two of us landed on the same question: what would it actually look like to build an AI version of me? Not as a gimmick. As an experiment. We were both genuinely curious what was possible.
I floated the idea. Winston ran with it, and ran with it in directions I never would have thought of.
The Problem AI Dan Actually Solves
Here's the real issue that got me interested in the first place: I can't be everywhere. I can be at one deal, one meeting, one dinner with one investor, at a time. Meanwhile, the internet doesn't care about my schedule, it wants content constantly, from Monaco to Dubai to wherever the next interesting backdrop happens to be, on a timeline no single human can keep up with.
So the question became: what if we created something that could show up more places than I physically can?
Not a chatbot. Not a customer service bot answering FAQs. A version of me: same sunglasses, same dry take on money, same refusal to take any of this too seriously. Something that could exist in more places at once. That was the part I cared about but what Winston built turned into something bigger.
He's Not Trying to Fool Anyone
This is the part I actually care about getting right: AI Dan is not trying to pass as real. He looks like AI and he is supposed to. The moment you try to make an AI avatar look completely human, you have made something a little creepy and a lot dishonest. Nobody wants to find out later that the "real person" giving them advice wasn't real. So we didn't hide it, we leaned into it.
If AI Dan fools you for a second, that's a bug. If AI Dan makes you smile because you know exactly what he is and you're in on the joke anyway, that's the whole point.
What He's Built From
AI Dan isn't improvising. He's built on hours of me talking: real opinions, real phrases, the stuff I say often enough that apparently it's become a personality trait. "I'm an operator, not a fund manager." "Cash flow did this." If you've heard me talk about money for more than five minutes, then you have heard these lines. AI Dan just says them more often, in more places, without needing sleep.
you can read more about my philosophy here
Why the Purple Sunglasses Matter More Than You'd Think
The purple sunglasses aren't a costume, they are the whole signal. Sharp doesn't have to mean serious and smart doesn't have to mean stiff. If AI Dan showed up in a suit talking about EBITDA with no personality, nobody would remember him by Tuesday. The sunglasses are how you know, instantly, that this is still Clotine — still willing to be a little ridiculous while talking about something real.
What He's Not (And Why That Matters)
AI Dan doesn't give investment advice. He doesn't replace a conversation with me, or with anyone on the team, when it's time to talk about real numbers, real deals, real decisions. He is the front door, not the whole house. Think of him as the guy who gets your attention and tells you where to actually go, not the guy closing the deal.
Where It Went From There
Once Winston had the concept working, he didn't stop at Clotine content. AI Dan now has his own Instagram page including recurring characters, running bits, and adventures that have nothing to do with me, finance, or cash flow at all. Some of it is ironic, offbeat satire on whatever is happening in the world that week. A lot of it is just Winston being funny, using AI Dan as the vehicle.
I don't review most of it before it goes up. At this point Winston understands the character better than I do, and I'd rather let him run with it than turn it into something that needs my sign-off. If AI Dan says something ridiculous that has nothing to do with me or Clotine, that's not a slip. That's just Winston's sense of humor doing its thing.
Some of it you will love. Some of it you won't — and that's fine. I've never been the guy trying to make everyone laugh at the same joke. I'd rather make a few people laugh really hard than make everyone laugh a little.
The Real Reason
Honestly? I think the next few years are going to be full of AI-generated everything: content, faces, voices, opinions, most of it trying very hard to convince you it's real. I'd rather build the version that's honest about what it is, has something actually worth saying, and doesn't take itself so seriously that it forgets to be interesting.
But I also want to be clear about what AI Dan isn't. He is not a replacement for actually talking to me. If you want to know what I think about a deal, or you are deciding whether Clotine is right for you, that conversation still needs to happen with an actual person whether it’s me, or someone on our team. AI Dan can get your attention, but he can't do the part that matters, which is a real conversation about real money. To learn more about our side street philosphy and our team, click here.
That's kind of the whole philosophy behind Clotine, if I'm honest. We take money seriously. We just don't take ourselves too seriously while we are doing it. AI Dan is the second part. The actual investing — the deals, the returns, the conversations about what's right for you — that's always the first part, and that part is never going to be AI.
If a fund manager in a suit and an operator in purple sunglasses said the same thing about cash flow, I know which one I'd actually listen to.
That's AI Dan. That's also, credit where it's due, my son having a lot of fun and being genuinely brilliant at it.
Go Follow Him
If you want to see what Winston's actually building, go follow AI Dan (on instagram: @real_ai_dan. Some of it will make you laugh. Some of it will make you go "what did I just watch." Both reactions are correct.
