Skippy and Doogles dig into the economics behind a proposed $5,000 government “dividend” and ask the obvious question: where exactly is $1.2 trillion supposed to come from? From there, they head straight into AI doomsday territory, including warnings of superintelligence, extinction risk, and whether quitting Anthropic is really the best way to save humanity.

They also break down the suddenly popular Coast FI retirement formula, debate whether it’s useful financial planning or just basic math with better branding, and wrap with perhaps the most important policy innovation of our time: White House arcade games.

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Skippy & Doogles dig into the Rich Dad, Poor Dad approach to leverage, why $1.2 billion in debt may not mean what the headline wants you to think, and where smart investing ends and financial gymnastics begin. Then we turn to AI stocks, PEG ratios, Nvidia, Broadcom, Micron, and the big question of whether these companies are actually cheap, or are investors correctly betting that today’s insane growth can’t last forever?

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We put Flutter Entertainment (ticker: FLUT), the parent company of FanDuel, through the Skippy & Doogles Investment Committee. We dig into its dominant position in sports betting, its playbook for conquering new markets, the regulatory headaches that come with operating around the world, and whether its growing scale could become a serious competitive moat.

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Skippy & Doogles go from Costco-fueled gambling and Darth Vader at city council to questionable sports-team valuations, Nike’s multiple compression, and whether elite colleges have decided failing is simply too impolite. The episode wraps with a meaty discussion of David Sinra's recent interview with Travis Kalanick.

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Skippy & Doogles dig into the venture capital mindset that profitability can signal a lack of ambition. Then they dive into the tangled web of insurance assets, private credit, and sports franchise ownership. The episode wraps with a discussion around the importance of understanding what you're doing.

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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.

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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.

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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.

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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).

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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].