The Iced Coffee Hour

Kevin O'Leary, entrepreneur and investor known from Shark Tank and finance commentary. He talks portfolio strategy and index-only investing. He discusses AI's real economic impact and practical use cases. He covers real estate, collectibles like cards, and bold market and recession predictions for the near future.

Peter Schiff, economist and investor known for championing gold and Austrian economics. He debates Bitcoin versus gold, argues about monetary inflation and dollar risks. He recounts his Trump run tension, explains his move into foreign dividend and mining stocks, and outlines recommended allocations for precious metals and commodities.

Andrew Yang, entrepreneur and former presidential candidate known for advocating universal basic income, discusses AI's looming impact on work and policy. He highlights which careers face automation and which roles may remain safe. He explores how AI-driven wealth should be shared and outlines policy ideas to help displaced workers adapt.

Caleb Hammer, creator of the Financial Audit series and founder of DollarWise, is a blunt personal finance coach who calls out bad money habits. He tells wild Financial Audit stories, explains why micro purchases wreck finances, and argues behavior often beats income. He also discusses AI’s job impact, rebuilding DollarWise, business scaling, and dating-plus-money dynamics.

Shane Stoffer (Togi), YouTuber known for high‑stakes challenge videos and a supplement brand, opens up about risking it all and rebuilding. He recounts massive gambling losses, a risky coin flip that cost his Miami house, and the expensive logistics of producing large game shows. He also discusses addiction, finding faith, recovery, and the scramble to stabilize finances.

Logan Paul, entrepreneur and creator known for YouTube, Prime, and high-value Pokémon collectibles. He discusses selling a $16M Pikachu, the real costs behind a $4M wedding, and why he buys mansions, jets, and dinosaur fossils. Short, candid takes on discipline, money mindset, and building businesses while navigating public scrutiny.

Chris Camillo, investor and social arbitrage trader who spots cultural signals for investable ideas. He argues AI is accelerating into agentic systems, outlines rapid business use cases and tools worth paying for, and urges swift adoption this year to capture outsized opportunity. He also discusses AI’s effects on jobs, investing, and why he keeps taking big, high‑risk bets.

Kyle Forgeard, Canadian entrepreneur and entertainer behind NELK and Happy Dad hard seltzer. He discusses building merch into a business, launching and scaling Happy Dad, and balancing on-camera stunts with serious operations. He addresses team size, risky pranks and legal fallout, high-profile friendships, and big-picture plans for bigger pranks and new content directions.

Jason LeWien (JasonTheWeenie), streamer and content creator who rose from NFT and sneaker hustles to big-time streaming. He talks about money shifts, life at FaZe and the split, ambitious stunts like a $270K island stream, burnout and parasocial pressure, and wild offers from platforms and peers.

Hoovie (HooviesGarage) — YouTube car collector who buys, repairs, and documents cheap and exotic cars. He recounts buying a Bugatti and the tax and maintenance fallout. He talks about selling cars to cover bills, massive renovation and financial stress, burnout and a life reset. He outlines strategies to avoid depreciation, risky auction practices, and which classic cars might appreciate.