Skippy and Doogles Talk Investing

Hosted by Skippy and Doogles

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Episodes

280

Latest episode

Jun 2026

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About the show

For years, two of the world's greatest investing minds, Skippy and Doogles, have debated their investing philosophies. They started recording their phone calls to bring that stock market wisdom to the masses. Buckle up, because you never know where these conversations might go, and what kind of priceless investment knowledge will soon hit your mentals.

Listen to episodes

60 recent

June 15, 202637 min

A Degree Too Far

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 skippydoogles@gmail.com.

June 1, 202640 min

Anthropic Thunder

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 skippydoogles@gmail.com.

May 25, 202638 min

Houston, We Have a TAM Problem

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 skippydoogles@gmail.com.

May 18, 202640 min

A Dog’s Life Economy

Skippy and Doogles dig into the weird state of today’s market: IPOs are rarer, companies are older, profitability is harder to find, and a lot of the action has disappeared into private markets. Using Jay Ritter’s IPO data as a jumping off point, they compare today’s IPO landscape to the dot-com era and ask whether the public market data is missing the real story. Bubbly valuations, massive market concentration, shaky consumer sentiment, private credit concerns, happy hour economics, and the newly coined “Dog’s Life Economy,” where everyone keeps running full speed until something breaks.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 skippydoogles@gmail.com.

May 11, 202629 min

Our Losers Lose Better

Skippy and Doogles dig into the fine art of losing money with confidence. First is GameStop’s bid for eBay. Then we turn to Kalshi, where the PR team tried to debunk some analysis from the Wall Street Journal by claiming their losers aren't as losering as other losers. The episode wraps with a breakdown of Price’s Law, why a tiny number of winners drive most outcomes, and the Anheuser-Busch protein claim.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 skippydoogles@gmail.com.

May 4, 202645 min

Slow and Steady Wins the Balance Sheet

Skippy and Doogles ask a dangerously un-American question: what would it take to build a company that lasts 500 or even 1,000 years? We dig into ancient Japanese businesses, and then jump into Richard Hamming’s famous talk on doing great work, covering ambition, independent thinking, hard problems, and resilience.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 skippydoogles@gmail.com.

April 27, 202648 min

Chamath is Still Dancing When the Music Stops

We kick things off poking fun at a classic Chamath clip. Then we dig into whether Tim Cook is actually one of the greatest CEOs ever. We break down why over-saving might be ruining your “rich life.” We wrap with a discussion on Polymarket and AngelList's new USVC fund.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 skippydoogles@gmail.com.

April 20, 202647 min

The Future of Investing is Lies

We break down a wild idea from Jack Dorsey: what if companies don’t need hierarchy anymore? Then we explore if AI is trained to create plausible narratives, not truth, what happens when those narratives scale across markets? We wrap with the Investment Excitement Ratio, the classic tale of chasing the story vs. fundamentals.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 skippydoogles@gmail.com.

April 13, 202641 min

What's a Little Tax Lie Between Friends?

We kick off with CNBC’s all-time “upside/downside” moment (it's honestly embarrassing). Then Skippy talks through tax myths and the Social Security reality nobody wants to admit. That's followed up with sports talk, including Wisconsin funding football like it’s a hedge fund, and the NBA’s most important proposal: beer prices based on wins and losses. The episode wraps with a deep dive into private credit and the “factory model” of investing, where more money usually doesn’t mean better returns.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 skippydoogles@gmail.com.

April 6, 202645 min

Private Credit is Hotel California For Your Money

We kick things off in the cognitive dark forest, where sharing your ideas might just get you out-executed by Big Tech. Then we pivot to a growing problem in private credit: everyone wants their money back, but not everyone’s getting it. We wrap things up with SpaceX potentially going public at a $2 trillion valuation and Buffett's contradictory nature.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 skippydoogles@gmail.com.