Skippy and Doogles wade into the deep end of financial nonsense — and it’s murkier than ever. From First Brands and their spark plug shell game to RadioShack’s straight-up Ponzi scheme, they dissect why scams are the market's current business model. Then it’s on to a comment about Oracle’s $300B AI pre-order, Jane Street’s billion-dollar options arbitrage in India, and why private equity firms are drooling over your retirement account.

Join the 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 dive deep into Robinhood’s latest move: launching a private fund for retail investors. Is it financial innovation—or a terrible idea wrapped in slick UX? The guys then break down how this mirrors the dot-com era, why closed-end funds can burn you, and what happens when private markets meet public hype. Plus: a GQG report claiming we’re in 1999, not 1995—and some top-tier listener mail that’ll make you think twice about compound interest.

Join the 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 trades value stocks for $180 flannels and Burning Man invites — which can only mean one thing: we’re officially in fantasy land. The AI hype train hit a new gear as OpenAI agreed to spend $300B (of money it doesn’t have) with Oracle (for compute that doesn’t exist). Naturally, Oracle stock popped $250B in market cap. We break down why this deal is built on hope and hype, and why it might be the clearest sign yet of an AI bubble. The episode wraps with listener mail that covers whether AI productivity is real, and what tools newer investors should use.

Join the 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 dive into the uncomfortable truth behind America’s housing obsession. Why are homeowners tapping their equity at record rates — even if it means refinancing into higher interest rates? It’s House Rich, Cash Poor season, and we’re breaking down what it means for the economy and your portfolio.

Plus:

• Is homeownership actually a path to wealth? (Spoiler: Not for most.)
• Howard Marks on investor psychology and overpriced markets
• Kawhi Leonard, carbon offsets, and a $300M NBA sponsorship scandal

Join the 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].

In Part 2 of our Deckers Outdoor (NYSE: DECK) breakdown, we dive into the company’s wild transformation from 2003 to 2024—highlighting how a near-death sandal brand evolved into a $30B powerhouse behind UGG and Hoka.

Inside:

• The 10,000% stock return from 2004 to now
• The $1.1M Hoka acquisition that became an $11B rocket
• UGG’s rise via Oprah, scarcity, and sheep drama
• Why Deckers always fights hardest when it's down
• A buyback strategy that would make Buffett proud
• What history suggests about Deckers' next big brand

If you like investing case studies, turnaround stories, or shoes that feel like clouds—you’re in the right place.

Join the 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].

How did a couple of California surfers turn a flip-flop side hustle into one of the best-performing stocks of the past 20 years? In this two-part special, Skippy & Doogles unpack the wild origin story of Deckers Outdoor—makers of Teva, UGG, Hoka, and more.

This is Part 1, covering 1973–2003: a journey of grit, sandals, lawsuits, and ugly boots that somehow took over the world.

Join the 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 break down the real story behind ETF performance. Then they dive into the wild Intel CEO saga — presidential shade, stock pops, and suspicious options trades. Finally, it's a deep-dive into the $1.3 trillion stock buyback frenzy: what's driving it, and should you care?

In this episode:

• The hidden truth behind ETF returns (hint: they’re worse than you think)
• Intel’s geopolitical mess and the mysterious options trade
• Record stock buybacks: smart capital allocation or corporate cop-out?
• Why Apple could’ve bought 470 companies… but didn’t

Join the 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].

What do Apple and a Southern California utility have in common? In 2013, they traded at the exact same PE ratio — and Michael Mauboussin’s framework explains why. Skippy & Doogles break down the steady-state vs. future value equation, revisit the Apple vs. Edison International case, and pull fresh insights from Mauboussin’s recent conversation with investing legend Seth Klarman. Packed with valuation wisdom, brain-breaking math, and practical takeaways for today’s market.

Join the 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].

First up: South Park goes full send with a Trump satire episode that has Doogles wondering if Matt & Trey are the last ones still doing their jobs. Then it’s on to the Novo Nordisk crash, where "skinny shots" meet IP loopholes and shady online pharmacies Finally, the jobs report is in—and it's messy.

Join the 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 are back and revved up. This week, they dig into what Ferrari's "one car less than demand" strategy teaches us about discipline in investing — and why most companies (and investors) can’t help but chase growth at all costs. Then, the duo explores a new research paper warning that the passive investing boom might actually be setting us up for systemic risk. Finally, they tackle a sobering question: why are English-speaking countries so unhappy — and could housing policy be the hidden culprit?

Join the 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].