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
Our Losers Lose Better
May 1100:29:46Tap to summarizeSkippy 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.
Transcribe →Slow and Steady Wins the Balance Sheet
May 400:45:33Tap to summarizeSkippy 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.
Transcribe →Chamath is Still Dancing When the Music Stops
Apr 2700:48:43Tap to summarizeWe 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.
Transcribe →The Future of Investing is Lies
Apr 2000:47:26Tap to summarizeWe 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.
Transcribe →What's a Little Tax Lie Between Friends?
Apr 1300:41:01Tap to summarizeWe 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.
Transcribe →Private Credit is Hotel California For Your Money
Apr 600:45:50Tap to summarizeWe 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.
Transcribe →What Are We Doing?!
Mar 3000:46:48Tap to summarizeDoogles is wondering what the heck is going on. Markets feel disconnected, AI spending is getting absurd, and some of the biggest companies in the world are making moves that are either genius or complete chaos. OpenAI is guaranteeing 17.5% returns. Meta’s massive AI spending spree continues. Skippy rants on sports, private equity, and why everything feels optimized for profit and not fans. The episode wraps with thoughts on Tim Ferriss’ “self-help trap.”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 →Betting on Missiles is Not Investing
Mar 2300:43:00Tap to summarizeDoogles breaks down the story of prediction markets influencing real-world reporting. Then Skippy covers what Americans think is gambling vs. investing. Next, would you rather bet on a $500B AI data center… or own Coca-Cola, a railroad, and a cash machine like PayPal? The episode wraps with a Morningstar piece on what the real long term winners on AI might be, and a few names that keep popping up on Skippy's radar.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 Too Can Be a Sucker
Mar 1600:33:28Tap to summarizeSkippy introduces Tommy the Car Guy, a YouTube negotiator who charges $1,000 to call dealerships and beat them down on price. Then we break down what might be the worst acquisition saga in corporate history in Time Warner Discovery. Skippy looks at a fascinating study on grocery stores and home prices — Trader Joe’s and Sprouts appear to predict booming neighborhoods… while Target and Walmart might signal the opposite. To wrap, we dive into a The Atlantic experiment: a journalist is given $10,000 to gamble so he can write about America’s sports betting boom.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 →SaaSpocalypse Now? AI, Block Layoffs & the Trust Premium
Mar 200:39:38Tap to summarizeIs SaaS dead — or just getting repriced? We break down the viral “SaaS apocalypse” thesis, the 2028 AI doom scenario, and Block’s 40% layoffs. Are AI agents about to replace CRMs, workflows, and entire jobs?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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