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Stock Sharks: The Deep End

Welcome to Stock Sharks, where we break down the biggest stories in investing, the stock market, business, AI, real estate, and the economy. Every episode features market analysis, interviews with top investors, CEOs, entrepreneurs, and industry experts. Whether you’re a beginner or an experienced investor, you’ll get actionable insights, deep conversations, and practical strategies to help you build wealth and stay ahead of the markets.

Latest Episodes:

Kevin O’Leary: The Next Big Bet — AI’s Real Winners, Uranium, Bitcoin & the $11M Card Sep 18, 2026

Show notes

Kevin O'Leary — Mr. Wonderful — sits down across the table to reveal where his money is actually going next. It's not the AI stocks everyone's chasing.

Kevin breaks down the 5% rule that's protected his portfolio for decades — and the brutal dot-com margin call that taught it to him, losing $3-4 million an hour as Bear Stearns called every four hours. Then he gets into the trades: why the real AI winners are the companies producing electricity (including Google's $3 billion power deal in Finland), why he bought a 10% weighting in Canada the day the trade war started, and why uranium and the Nordics are his highest-conviction power plays for the next three years.

We also cover his IPO playbook, how he researches a stock in 20 minutes, buying private companies at 3.5x free cash flow, AI transforming medicine, Bitcoin and the tokenization debate, Q-Day — the quantum computing threat to crypto — stablecoins yielding over 3%, and the $11 million Mickey Mantle card he thinks trades like a Picasso in 20 years.

In this episode:

The 5% rule and surviving the dot-com crash
The power trade behind AI
The contrarian Canada bet
Uranium, nuclear SMRs, and the Nordics
Bitcoin, quantum computing, and stablecoins
The $11M Mickey Mantle card

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Nothing in this episode is financial advice.

Dan Niles: The AI Bubble, OpenAI vs Anthropic & When the Music Stops Jul 01, 2026

Show notes

Dan Niles of Niles Investment Management joins us for a wide-ranging conversation on where the market actually is right now. Dan called the June AI speed bump two days before chip stocks rolled over. Here he explains why he thinks we're 100% in a bubble, why he's still buying anyway, and where he sees the hardest-run stocks falling 30 to 50% before this AI cycle busts.

We cover the memory shortage almost nobody is pricing in, why today looks more like 1997 than 1999, and what happens the day good news stops moving stocks. Dan breaks down the AI arms race, OpenAI vs Anthropic and who actually wins, whether AI itself is getting commoditized as models get cheaper, plus a quick take on Elon Musk's companies.

Then we go macro: where interest rates settle with the Fed on hold, and the national debt now near double the level that once terrified investors. Dan has been through two busts before, the dot com collapse and the 2008 crisis with his fund housed inside Lehman the week it failed, and he walks through what breaks first when the music stops.

He also opens up on the story behind it all: the $50 Merrill Lynch account he opened in college, walking away from designing microprocessors at Digital Equipment for Wall Street, standing alone with zero buy ratings at the top of the dot com bubble, and why emotional control is the trait he says matters most in this business.

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