Your brain loves the “safe” choice, and the market punishes it more often than you think. We grab a hypothetical time machine and make the kinds of decisions that feel obvious in the moment then reveal what really happened when history played out. From the 2000 NFL draft (Courtney Brown vs a “skinny fat” quarterback named Tom Brady) to the 1984 NBA draft (Sam Bowie vs Michael Jordan), we watch rational logic turn into legendary regret.

Then we jump to investing and replay 2007, when BlackBerry looked unbeatable and Apple’s keyboard-less iPhone got laughed at. We also dig into two stories that aren’t about missing the winner at all, but about getting fooled by something that was never real: Theranos and Nikola. It’s a blunt reminder that hype, glossy press, and a good demo video are not the same as working technology or a durable business.

The emotional gut punch is Amazon. We follow a $5,000 investment through brutal drops including a 94% crash, another major decline, and the 2008 financial crisis then compare what happens if you sell versus hold. That sets up the core takeaway for long term investing: picking the right company is hard, but holding through volatility is the real filter. We end with the data on why only a small slice of stocks drives most market gains, why even pros struggle to beat the market, and why a simple index fund can be the cheat code for passive investing and wealth building. If this hit home, subscribe, share it with a friend who stock picks, and leave a review with the biggest investing lesson you’ve learned.

A $3 Laboo Boo from Goodwill sounds like a silly flex until it turns into the cleanest investing lesson we know: the same thing people overpay for at peak hype often shows up later at a steep discount. That’s exactly how we think about IPO investing, especially when everyone starts yelling that SpaceX, OpenAI, and Anthropic are about to go public and “regular people” can finally get in.

We walk through what an initial public offering actually is, why it feels like an important purchase opportunity, and why that feeling can be dangerous. By the time a company reaches the public market, venture capitalists, hedge funds, and insiders have often been in for years at far better prices. We also unpack the famous first-day “IPO pop” and the uncomfortable truth behind it: even if the average pop exists, high-speed traders and institutional access mean retail investors often buy after the jump, not before it.

Then we get concrete. We talk Rivian’s meteoric run and brutal fall, GoPro’s hype cycle, and what those stories teach about valuation, expectations, and paying today for profits that may or may not ever arrive. We also share why broad index funds and long-term investing often beat chasing the hottest IPOs, plus our simple rule for handling the next blockbuster listing: wait at least a year, let the hype cool, and judge the business on real numbers.

If you’ve ever felt FOMO on an IPO, hit play, then subscribe, share the episode with a friend who loves “can’t miss” stocks, and leave a review. What’s the most hyped investment you’ve ever regretted buying?

We almost invested in a cartoon moose. Instead we learned the secret rich people don't want you to know - and it involves rabbits doing what rabbits do.

In this video we break down:

• Why your money needs to be multiplying like rabbits RIGHT NOW
• The $500/month habit that turns into $57 million
• The 3 funds that do all the work for you
• The fee trap that steals 25 cents of every dollar you make

If you're 17 and nobody has taught you this yet, this video is for you. If you're older and still don't know this, no judgment. Watch anyway.

$1,000 invested in Apple in 2007 = $200,000 today. You're welcome.

Subscribe to Triple The Money. We're 17 and we might know more than your financial advisor.

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