Skippy and Doogles Talk Investing

Skippy and Doogles tackle student loans, trillion-dollar TAMs, and the seemingly unkillable Mark Zuckerberg. We dig into the guy who may have missed out on $1 billion of NVIDIA stock. Then we hit on a new proposal tying federal student loan eligibility to graduate earnings. The episode wraps with how Meta/Facebook has been declared dead again and again, and why Zuckerberg may be better positioned for the AI race than people think.

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Skippy & Doogles dig into the bizarre two-speed stock market, where household names like Nike, Campbell’s, Clorox, PayPal, and Kraft Heinz have been crushed while a handful of mega-cap tech stocks keep the S&P 500 looking just fine. They also unpack Berkshire Hathaway’s absurd cash pile, why it now rivals the reserves of entire countries, what falling foreign demand for U.S. Treasuries could mean for interest rates, and whether AI spending is creating real long-term value or just a very expensive game of musical chairs.

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 walk through forecasts that are really just the numbers required to tell the story investors need to hear. We dig into OpenAI’s staggering cash needs, whether AI regulation could create a moat for the industry’s biggest players, and why projecting anything five years out in AI may be an exercise in creative writing. Then we cover the Lakers’ new owners' very ambitious assumptions about what fans will be willing to pay.

Plus, premium subscribers stick around for Inside the Trade.

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 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.

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 & 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?

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 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.

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 & 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.

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 & 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.

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 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].