I Asked 5 AIs to Make Me Money (One Dominated) - Ep. #317
The Koerner Office - Business Ideas and Deep Dives with Chris Koerner
July 14, 2026
⸻ Ride the AI tidal wave together. ━ ━ I sat down with Brandon Doyle to break down his experiment giving Claude, ChatGPT, Gemini, Grok, and Perplexity $1,000 each to invest in the stock market.
Speakers Brandon Doyle, Chris Koerner
TopicsEntrepreneurshipBusiness
Brandon Doyle (0:00)
Claude's more than doubled my money already. So, pretty sweet. I decided to give five different models real money. Claude, Chachiputti, Gemini, Grok, and Perplexity. Let me just see how smart they actually are. I told them, it's a competition against the other four, and they have to win, or I'm gonna cancel my subscription with them.
If they lose, I'm canceling. And I said, there's only gonna be one winner.
Chris Koerner (0:24)
You've like 30x'd on Claude.
Brandon Doyle (0:26)
Claude's killing it. So everybody just needs to try to catch up to Claude on here. Yeah, it's been interesting, especially to watch Gemini as it started losing my money and then basically became a gambler.
Chris Koerner (0:41)
So the reason you flew here to Texas today is to tell us how you used AI to make you money passively, correct?
Brandon Doyle (0:48)
Correct.
Chris Koerner (0:49)
So tell us what your what your thinking was when you started this experiment.
Brandon Doyle (0:54)
Yeah, so I started like six months ago or maybe a little less using the different AI models to manage my money. Everybody started talking about how smart Claude was and obviously ChatGPT and all the others. So I figured, okay, well, let me just see how smart they actually are. So I decided to give five different models, $1,000 of real money, and which I know is not nothing, but I wanted it to be basically enough to where I didn't want to do it like 50 bucks, because then I was thinking, well, maybe I would just neglect it or whatever. So I gave them each $1,000 of real money.
And the ones I gave was Claude, ChatGPT, Gemini, Grok and Perplexity.
Chris Koerner (1:37)
Okay. A thousand each.
Brandon Doyle (1:39)
A thousand each. So 5,000 bucks I put in.
Chris Koerner (1:41)
And I think the amount of money is important because there needed to be stakes.
Brandon Doyle (1:44)
Yeah.
Chris Koerner (1:45)
If it's 20 bucks, 50 bucks, then you're not going to take it seriously.
Brandon Doyle (1:48)
Yeah. So 5,000 bucks.
And I know that perplexity, in case the commenters and viewers want to know this, so perplexity basically uses the other models to make its decisions as it sees fit.
Chris Koerner (2:00)
So it's the model to end all models.
Brandon Doyle (2:02)
Yeah.
Chris Koerner (2:03)
But that doesn't necessarily make it better.
Brandon Doyle (2:05)
Yeah, not necessarily. And so I thought those would be the best five to choose.
Rock, I definitely wanted to include because of its connection to X and the Twitter firehose of information.
Chris Koerner (2:19)
So you're thinking like maybe more social mentions will equate to a better return.
Brandon Doyle (2:23)
That's what I...
Chris Koerner (2:23)
Buying a certain stock.
Brandon Doyle (2:24)
Yeah, that's what I had assumed basically. Gemini obviously is owned by Google, so they've got all that connection there with Google searches and whatever else. And then Chachi Buti and Claude are similar in how they're made and built and stuff.
So yeah, so I gave them each $1,000. And yeah, this is in late 2025 is when it started. And what I did was I told them, so I told them that they can be as risky as possible, and it's okay if I lose all my money. And I had to actually work that prompt in pretty hard because at the start, they kept only giving me theoretical recommendations.
Chris Koerner (3:02)
It's worried about liability.
Brandon Doyle (3:03)
Yeah.
Chris Koerner (3:03)
It's trying to hedge.
Brandon Doyle (3:04)
Yeah.
Chris Koerner (3:04)
It doesn't want to be responsible for you losing money.
Brandon Doyle (3:07)
Yeah. So that was my first obstacle is basically getting them all to agree to give me... I said, I want... I'm going to give you real money and I want real recommendations.
Grok, they were fine with it right away, which is kind of funny because that's like the most liberal, the most loose. Yeah. Yeah. Yeah. Yeah. So, Boris, like Chachipati and Claude were very apprehensive to basically allow that, I guess you could say.
Chris Koerner (3:32)
Now, before you continue, let me ask you like, why was that important to you? To prompt it like you can lose my money. What...
Brandon Doyle (3:38)
Yeah. I just...
If you sign up for Robinhood or whatever, and then they'll ask you questions when you first sign up and it's like, do you have experience in the stock market? What is your time horizon with your investments? Do you need the money right now? So, I think just by nature, these investing platforms also, like they want to cover their tracks in regards to liability, and so I just wanted to get through that with the AI models too.
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