Skippy and Doogles dig into who’s actually making money in the AI value chain and what happens when the profitable parts depend on someone else continuing to lose money. Then they take on the great venture capital benchmark debate: if SPY and QQQ can beat most funds with lower fees and full liquidity, what exactly are you paying for? Finally, they look at the rise of daily stock trading among young men, the Robinhood generation, and why investing shouldn’t feel like a trip to the casino.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

Skippy and Doogles unpack the spectacular unraveling of Situational Awareness, a hedge fund that reportedly went from roughly $30 billion to $8 billion in a matter of weeks. Then the conversation turns to Larry Ellison and Oracle’s enormous AI infrastructure gamble.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

This week, Skippy and Doogles dig into the downside of blindly following billionaires, the economics behind Florida’s Brightline rail system, and the surprisingly complicated battle between Uber and Waymo. They also explore why AI may be less of a civilization-ending superpower and more of a very capable, occasionally unreliable intern.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

We discuss how AI better work out because it is everywhere (obviously)...stocks, bonds, and VC. Then we turn our attention to a viral essay arguing that millennials and Gen Z are poorer, lonelier, and generally doomed (we disagree).

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

Seed valuations have officially gone off the rails. Skippy and Doogles break down why brand-new startups are raising massive rounds at eye-popping prices. Then, they head to Costco, where a longtime cashier has become a millionaire the old-fashioned way: by showing up, saving consistently, and letting compounding do the heavy lifting. Finally, they dig into Fundsmith’s surprising portfolio overhaul, the pressure of investor outflows, and what happens when a value investor capitulates to market forces.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

Doogles covers Polymarket’s alleged influencer ad mess, including fake bets and fake wins. Then they crack open SoftBank’s shareholder deck, featuring golden eggs, goose value, and possibly the most bizarre visual explanation of alpha ever presented to investors. Skippy then hates on Scott Galloway’s viral money comments. The episode wraps with a detour into life lessons from watching European Soccer and a few stock research recommendations for premium subscribers only.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

This is a quick-hit episode that connects World Cup Taco Bell tourism, inheritance drama, remote work rage, Syracuse’s enrollment problem, Dave Ramsey’s questionable credit card math, and why everyone feels broke while the stock market keeps minting billionaires.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

We break down the math behind a $400K college decision, comparing Ivy League prestige, flagship state schools, trade school, and the emotional pull of “dream school” thinking. Along the way, we hit SpaceX IPO mania, wild price-to-sales ratios, US soccer propaganda, and NBA Finals drama.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

Skippy and Doogles dig into Benedict Evans’ latest AI deck that covers eye-popping AI valuations, data center capex, and whether LLMs become commodities. Then, Micron goes nowhere but up, Americans are falling behind on credit card bills, and a new Journal of Finance paper asks whether investors are actually risk-averse, or just trapped by tiny frictions and bad defaults.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].

This week, Skippy and Doogles chat about the SpaceX IPO and ask if your TAM is basically “the entire digital economy plus maybe Mars,” do fundamentals still matter? Then they turn to a viral MasterCard sell decision as a case study in how not to handle underperformance, before wrapping with Chris Hohn’s concentrated portfolio of toll booths, rails, ratings agencies, and other monopolies.

Join the premium Skippy and Doogles fan club. You can also get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to [email protected].