Skippy and Doogles Talk Investing

Hosted by Skippy and Doogles

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Episodes

288

Latest episode

Aug 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

August 17, 202648 min

I'm Not Profit, You're Profit

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 skippydoogles@gmail.com .

August 10, 202640 min

Reread My Returns Until You Understand

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 skippydoogles@gmail.com .

August 3, 202645 min

Leopold and the Terrible, Horrible, No Good, Very Leveraged Month

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 skippydoogles@gmail.com .

July 27, 202643 min

No Train, No Gain

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. 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 .

July 20, 202636 min

AI Better Work Out

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). 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 .

July 13, 202640 min

You Reap What You Seed

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 skippydoogles@gmail.com .

July 6, 202638 min

All Eggs, No Goose

Doogles 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 .

June 22, 202640 min

The Joneses Are Everywhere

This 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 .

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 .