Money Expert: This Wealth Setup Only Happens Once…And It JUST Happened Again! | Chris Camillo artwork

Money Expert: This Wealth Setup Only Happens Once…And It JUST Happened Again! | Chris Camillo

The Iced Coffee Hour

May 24, 2026

HIMS: Get personalized and affordable care for Hair Loss, ED, Weight Loss, and more at https://Hims.com/ICEDAirbnb: Find a co-host at https://airbnb.com/hostGusto: Try Gusto for FREE for 3 months at https://gusto.com/ICEDShopify: Sign up for a $1 per month trial period at https://shopify.
Speakers: Chris Camillo, Jack Selby, Graham Stephan
**SPEAKER_1** (0:00)
Insurance isn't one size fits all, and shopping for it shouldn't feel like squeezing into something that just doesn't fit. That's why drivers have enjoyed Progressive's Name Your Price tool for years. With the Name Your Price tool, you tell them what you want to pay, and they show you options that fit your budget. Enough hunting for discounts, trying to calculate rates, and tinkering with coverages. Maybe you're picking out your very first policy, or maybe you're just looking for something that works better for you and your family. Either way, they make it simple to see your options. No guesswork, no surprises.
Ready to see how easy and fun shopping for car insurance can be? Visit progressive.com and give the Name Your Price tool a try. Take the stress out of shopping and find coverage that fits your life on your terms.
Progressive Casualty Insurance Company and Affiliates. Price and coverage match limited by state law.

**Chris Camillo** (0:52)
I've been waiting for this trade for over a decade, and there's eight figures between the three.

**Jack Selby** (0:58)
Eight figures?

**Chris Camillo** (0:59)
In one day, I was up 5.5 million.

**Graham Stephan** (1:01)
But how did you know when the rest of the market wasn't picking it up?

**Chris Camillo** (1:07)
I think investors are making some of the most irrational, emotionally driven decisions that I've ever seen in my life. We're trying to define the AI moment with what we know, and that's the wrong way to look at it.
What is going to be created over the next 20 years? What new industries will pop up? I can't even imagine.

**Graham Stephan** (1:27)
How should the average person invest in 2026?

**Chris Camillo** (1:30)
This is the last easy trade of the AI super cycle. Economies will change.
Everything we know about business, about assets, all of that is going to radically change, and the moment is now to place your bets and be part of that, or be left out of that.

**Graham Stephan** (1:54)
Chris Camillo, thank you for coming on The Iced Coffee Hour.

**Chris Camillo** (1:57)
Happy to be back.

**Graham Stephan** (1:58)
What's interesting is that you were right about Amazon in our last podcast. It's since been up about 30-40 percent. You were right about Bloom Energy. You called it around $60. It hit $300.
You doubled down on Robinhood at $38. I'm really curious, how much money do you make from those trades?

**Chris Camillo** (2:19)
There were probably three of the biggest trades in my life.
There's eight figures between the three, and it's been the best few months that I've had in 18 years. It's been big.

**Jack Selby** (2:33)
Eight figures?

**Chris Camillo** (2:34)
Oh, yeah. Definitely eight figures off the three trades. I think Amazon was an eight figure trade alone.
Last time I was on, I told you I was doing this. I've been waiting for this trade for years. I've been waiting for this trade for over a decade. I always say having a prepared mind is one of the most important things an investor can do, because it's usually during the years when there aren't any high conviction trades like that, that you have to prepare yourself to make the move when one comes around. So I've been waiting for it.

**Graham Stephan** (3:04)
But how did you know when the rest of the market wasn't picking it up?

**Chris Camillo** (3:10)
I think the one thing that I'm really good at, is independent thinking and not getting sucked in to market noise and other people's opinions. So when I develop a high conviction thesis like I did with Bloom, with Robinhood, especially with Amazon, I'll generally spend anywhere between 50 and 80 hours doing deep dive due diligence. So my thesis is baked. I've seen the counter argument. I know what the other side of that argument looks like, and I obviously don't agree with people that are on the other side. Then when the market made their big move against Amazon, which was we don't believe that the 200 billion is a good idea, I thought that was patently wrong. So I was like, if that's the reason why they're going to take Amazon down, is because they're spending 200 billion due to an opportunity that Amazon sees right in front of their face, I will take the other side of that bet. And Amazon has a really long history of making prudent decisions when it comes to capex. Now, I think a lot of investors these days, I don't know if they don't remember 15 years ago or 20 years ago, right?
I don't quite understand what's happening with institutional and retail Wall Street. I think investors are making some of the most irrational, emotionally driven decisions that I've ever seen in my life. And I think they're half-baked.

119 more minutes of transcript below

Feed this to your agent

Try it now — copy, paste, done:

curl -H "x-api-key: pt_demo" \
  https://spoken.md/transcripts/1000651996090

Works with Claude, ChatGPT, Cursor, and any agent that makes HTTP calls.

From $0.10 per transcript. No subscription. Credits never expire.

Using your own key:

curl -H "x-api-key: YOUR_KEY" \
  https://spoken.md/transcripts/1000769378025