Skippy and Doogles Talk Investing

This week, Skippy & Doogles break down the real risks (and hype) around stablecoins — why they’re booming, what regulators just did, and why most “innovations” here just rebuild the same old financial system. Plus: how to think clearly when your investment 10X’s overnight (and why that’s often a red flag). Join the Skippy and Doogles fan club . You can also get more details about the show at s...

This week, we break down the Circle IPO frenzy — is this stablecoin stock the next big thing or pure speculation? 🚀 Then we dive into the new tip tax law and why it’s creating unexpected winners and losers. Finally, we explore America’s adulting crisis: why are so many young adults Googling “how to use a mop”? 🤯 Topics covered: Circle Internet Group (CRCL) IPO: is the hype justified? The surpris...

This week, we're rewinding to one of our most loved convos ever—with Richer, Wiser, Happier author William Green . William spent 25+ years interviewing the greatest investors alive—Buffett, Munger, Howard Marks, Joel Greenblatt—and distills their wisdom into a blueprint for life, not just investing. In this deep dive, we talk about: The habits of resilient investors Why avoiding "the death line" m...

This week, Skippy & Doogles tackle the uncomfortable truth behind the phrase “there’s no free lunch.” They break down: Why tipping culture is what it is (and who really pays) The student loan forgiveness debate—and what it says about the system Why classic investing wisdom doesn’t work in 2025, and why you can’t just be rigid in your investing philosophy Join the Skippy and Doogles fan club ....

This week, Skippy and Doogles dig into one of the worst retirement product we’ve ever seen: Basic Capital. It promises 5x leverage on your 401(k)—what could go wrong? We break down the math, the sales pitch, and why this kind of financial “innovation” can trap you in a debt spiral. Plus, we talk hidden fees from trusted advisors, and why “just 1%” could cost you 25–30% of your future wealth. In th...

Skippy & Doogles dive deep into the Buffett legacy—breaking down Berkshire’s insane 5.5 million percent return, the psychology behind his frugality, and whether longevity alone makes him the greatest. Plus, some spicy comparisons to Michael Jordan, Zuck, and Cold Stone Creamery pricing. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , s...

Are $20 fast food meals the new norm? Skippy & Doogles dig into what’s behind declining sales at McDonald’s and Starbucks, why Taco Bell is thriving, and the absurd new definition of “value.” Then we tackle the broken job market for college grads, the rise of AI as the “third door,” and why short-term thinking is stifling investment in the future. Plus: 🍟 Why your McValue meal costs more than...

Yale is selling $6 billion of private equity holdings — is this the canary in the economic coal mine? Student loan repayments are back, and the numbers are worse than you think. Plus: YOLO traders are back in force, betting big on Bitcoin and meme stocks with dreams of overnight riches. 👉 Rate, review, and follow the pod so you don’t miss a beat. It helps a ton! Join the Skippy and Doogles fan cl...

Foreigners own net $30 trillion in U.S. assets—should we be worried? Skippy & Doogles go deep on America’s financial entanglements, who holds our debt, and why global capital might be looking for the exit. Then they unpack the China standoff, how trade narratives are twisting, and what private equity’s "perfect storm" means for markets. Banter included. Charts not required. In this episode: Wh...

Markets are twitchy, tariffs are flying, and the Economic Policy Uncertainty Index just hit 900. So... what now? This week, Skippy and Doogles channel Charlie Munger, debate whether it’s time to dump Chinese stocks, and wrestle with how (and when) to deploy cash in a world that makes zero sense. Plus: Howard Marks drops another banger memo, the NASDAQ flirts with 24/7 trading, and we break down th...

This week, Skippy & Doogles go scorched earth on the most chaotic economic policy rollout in recent memory. Trump’s new “reciprocal” tariffs? We break down the math (spoiler: it’s nonsense), the market fallout, and why it’s got economists, investors, and even penguins running for the hills. Expect: 🔥 A full takedown of the tariff formula that makes zero economic sense 📉 Analysis of the worst...

This week, Skippy’s in the U.S., Doogles is in Paris, and the global economy is somewhere between a punchline and a panic. We kick things off with a deep dive into the new 25% auto tariffs—what they mean for carmakers and investors. Then we pivot to the bizarre: Trevor Milton, the man who rolled a fake truck down a hill, just got pardoned . What does that mean for financial regulation and investor...

The Celtics sold for $6.1B?! We break down why pro sports teams are selling out, debate March Madness chaos, and roast Michael Saylor’s “Preferred Shares of Chaos” — a crypto-powered yield product that smells like a Ponzi. Plus: Treasury’s 3-3-3 Plan, and why America can’t build anything anymore. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.c...

In this jam-packed episode, Skippy and Doogles tackle everything from Elon Musk’s bold economic takes to why CEOs are afraid to speak out right now. They dive deep into the complexities of modern monetary theory—complete with a bucket analogy that might just change how you see government debt. Plus, they break down the current state of consumer spending. It’s sharp investing insights with a side o...

Is the government cooking the books? This week, Skippy & Doogles dive into Trump’s plan to strip government spending from GDP—what it means, why it’s happening, and whether it changes how we measure recessions. Plus, we break down 150 years of stock market crashes to uncover the biggest investing lessons, and we analyze the wild shifts happening in the global economy—from rising military spend...

Skippy looks at Booz Allen Hamilton’s wild government contract dependency and what happens when the political winds shift. Doogles breaks down Warren Buffett’s latest (and maybe last?) Berkshire Hathaway annual letter. Skippy highlights how the top 1% now account for 50% of U.S. consumer spending, and asks what that means for markets. The episode wraps with some listener mail about how politics an...

Skippy and Doogles tackle listener mail about Berkshire Hathaway's huge cash pile. Skippy talks through the recent $1.5b hack on ETH. The episode wraps with a deep dive into Bill Ackman / Pershing Square building "the next Berkshire Hathaway" with an increased investment in Howard Hughes. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , sho...

Doogles loves Dave Portnoy going off about how the crypto bros can't hodl. Skippy talks through how functional unemployment is much higher than what the aggregate government data shows. Then he gets fired up about Jamie Dimon's rant about remote work. The episode wraps with Pershing Square's latest annual investor presentation. Join the Skippy and Doogles fan club . You can also get more details a...

Doogles highlights that El Salvador is calling in quits on Bitcoin as the national currency. Then he questions whether it's the right time to diversify outside the US. Skippy looks at the poor consumer sentiment in China. The episode wraps with two interview summaries with professional investors — Graham Duncan and Mike Maples. Join the Skippy and Doogles fan club . You can also get more details a...

Skippy and Doogles answer listener mail on Cathie Wood's underperformance. Skippy tells Visa to stop performing so well so they don't get shut down. Doogles talks through career lessons from David A. Patterson. Skippy is enamored by Warren Buffett's cash pile and it's market crash predictions. The episode wraps with a discussion about Twilio and Brazilian equities. Join the Skippy and Doogles fan...

Doogles is fascinated by the US/China AI race, and specifically DeepSeek. Skippy is not happy with how American's are treating their finances. The episode wraps with a conversation about David Einhorn's latest take on how the market today is fundamentally broken. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show notes on our Substack ,...

Skippy pulls a 180 and now thinks that the US buying Greenland has some merit. Doogles stresses the importance of spending an unreasonable amount of time to allow for greatness. Skippy dives deep into the science of alcohol. The episode wraps with a discussion on stress and burnout, and then the US dollar's overvaluation. Join the Skippy and Doogles fan club . You can also get more details about t...

Skippy and Doogles tackle the relationship between interest rates, the economy and stock valuations. Doogles walks through Charlie Bilello's latest chart recap. Skippy covers traffic congestion in NYC. The episode wraps discussing Howard Marks' latest memo Bubble Watch. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show notes on our Subs...

Celebrating one more year in the past! Skippy and Doogles go through Cliff Asness' look back at the market from the lens of 2035. The rest of the episode highlights from 2024 episodes including: Li Liu's principles of value investing, an interview with Cliff Asness, and David Tepper's take on investing in China. Join the Skippy and Doogles fan club . You can also get more details about the show at...

Skippy is flabbergasted by a man who takes saving money to the extreme. Doogles says to watch the cognitive load people are putting on their processes. Skippy shakes his head at how Bench Accounting shuts down. Doogles gives a PSA on cryptocurrency scams. The episode wraps with Mag 7 P/E ratios gone wild and how to prepare for a lost decade in stocks from Barron's. Join the Skippy and Doogles fan...