Podcast
Skippy and Doogles Talk Investing
Hosted by Skippy and Doogles · EN
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.
41episodes
Episodes
Newest firstAll episodes
Leopold and the Terrible, Horrible, No Good, Very Leveraged Month
4d ago00:45:09Tap to summarizeSkippy 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 skippydoogles@gmail.com.
Transcribe →No Train, No Gain
2w ago00:43:49Tap to summarizeThis 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 skippydoogles@gmail.com.
Transcribe →AI Better Work Out
3w ago00:36:16Tap to summarizeWe 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 skippydoogles@gmail.com.
Transcribe →You Reap What You Seed
4w ago00:40:25Tap to summarizeSeed 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 skippydoogles@gmail.com.
Transcribe →All Eggs, No Goose
Jul 600:38:52Tap to summarizeDoogles 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 skippydoogles@gmail.com.
Transcribe →The Joneses Are Everywhere
Jun 2200:40:15Tap to summarizeThis 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 skippydoogles@gmail.com.
Transcribe →A Degree Too Far
Jun 1500:37:39Tap to summarizeWe 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.
Transcribe →Anthropic Thunder
Jun 100:40:55Tap to summarizeSkippy 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.
Transcribe →Houston, We Have a TAM Problem
May 2500:38:45Tap to summarizeThis 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.
Transcribe →A Dog’s Life Economy
May 1800:40:19Tap to summarizeSkippy 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.
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