Skippy and Doogles Talk Investing

Hosted by Skippy and Doogles

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Episodes

297

Latest episode

Oct 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.

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60 recent

October 19, 202642 min

The Long And Short Of It (CoreWeave, trolley problem)

Skippy & Doogles dig into Bernstein Research's attempt to prove that anyone can build a sneaker brand and the explosive growth of long-short investing strategies designed to minimize taxes. Then we tackle the CoreWeave saga, where $130 billion in promised revenue meets mountains of debt, soaring bond yields, and some very optimistic friends at Nvidia. The episode wraps with AI addressing the trolley problem and raising some uncomfortable questions about what human work will actually be worth in the future. 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 .

October 12, 202649 min

A Fool and His Money Are Having a Blast (Chinese manufacturing, SpaceX, Robinhood)

Skippy and Doogles tackle why a top-10% income apparently isn't enough anymore. Then, how Chinese automakers are crushing their European competition on manufacturing costs. Doogles doesn't like that kids could soon receive individual shares from corporate donors. The episode wraps with Elon Musk's latest spectrum purchase, which has telecom stocks sweating, and Robinhood's Hood Summit, bringing together investors celebrating massive stock market wins. 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 .

October 5, 202643 min

The Zuck Stops Here (Zuckerberg, student loans)

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. 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 .

September 28, 202644 min

America Is 75% Off

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 skippydoogles@gmail.com .

September 21, 202621 min

Don't Let Facts Ruin a Good Forecast (OpenAI, the Lakers)

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 skippydoogles@gmail.com .

September 14, 202644 min

The Check Is In the Mail (Trump dividend, Coast FI)

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 skippydoogles@gmail.com .

September 7, 202647 min

Debt It Like It's Hot (Robert Kiyosaki, Nvidia, Broadcom)

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 skippydoogles@gmail.com .

August 31, 202650 min

If You Can’t Beat the House, Maybe Buy the House (Inside FanDuel's Stock) [Investment Committee]

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 skippydoogles@gmail.com .

August 24, 202652 min

You Had Me at Pancake Robot (Travis Kalanick's journey to Atoms)

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 skippydoogles@gmail.com .

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 .