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 skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

This week, we break down the Circle IPO frenzy — is this stablecoin stock the next big thing or pure speculation?

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 investorsWhy avoiding "the death line" matters more than chasing alphaHow great investors think probabilistically and live better lives because of itThis isn't just about markets—it's about mastering decisions, uncertainty, and your own temperament. One of our all-time favorites.Join the 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.

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 systemWhy classic investing wisdom doesn't work in 2025, and why you can't just be rigid in your investing philosophyJoin the 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.

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 this episode:The case against leveraged retirement accountsWhy fees are the silent killer of long-term returnsBasic Capital's pitch vs. reality Want to build wealth without stepping on financial landmines? Tap play.Join the 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.

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, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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:

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.

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:Who really owns U.S. debt—and why it's less scary than headlines suggestThe “De-Americanization” of global capital: trend or tantrum?Why China's calling itself a “safe haven” (and yes, we're side-eying that too)The private equity bubble: what happens when no one's buying?Inflation, leverage, and Powell's impossible jobJoin the 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.

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 the real deal with ESOPs and employee ownership.Join the 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.

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:

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 trust?Finally, we unpack the rise of Buy Now, Pay Later… for burritos. Is it just a viral stunt or a symptom of a fragile consumer economy? And in the premium segment, we go inside Stanley Druckenmiller's latest macro bet on pharma.Join the 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.

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.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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 of laughs—because who said finance has to be boring?

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 spending to trade wars and the Fed's next move. Oh, and did we mention the ‘Strategic Bitcoin Reserve'? Buckle up, this one's a ride.Join the 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.

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 and morality should or shouldn't play in investment decisions.Join the 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.

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, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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 about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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 about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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 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.

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, and send comments or questions to skippydoogles@gmail.com.

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 the show at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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 Substack, and send comments or questions to skippydoogles@gmail.com.

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 skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

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 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.

Skippy highlights the financial incongruence of NFL quarterbacks. Doogles shakes his head at a Techcrunch piece on Databricks waiting to go public. Skippy talks through US vs European value creation. The episode wraps with a discussion on entropy and its connection to investing.Join the 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.

Skippy quizzes Doogles on a variety of topics and Doogles fails all of them. Then they go into the depths of listener mail, first talking about whether macro conditions and business environment justifies currently high Buffett Indicator levels, and then exploring another argument in favor of Bitcoin.Join the 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.

Doogles talks about the current mindset of the American worker. Skippy talks market valuations in the US and parlays that into a conversation about pump.fun and the creation of meme coins. The episode wraps with Michael Saylor pitching Microsoft on buying Bitcoin and Howard Marks' latest memo about asset allocation.Join the 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.

Skippy returns from his Asian conquests and discusses the value in looking at international stocks. They discuss how hard it is to find a 200 bagger...and how long it takes to get there. The episode wraps discussing the "real value of money".Join the 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.

Skippy is out searching for new companies to invest in within the great continent of Asia, so Doogles is handling this one solo...but with two special guests. Josh Scott is an entrepreneur and investor who has also led multi-billionaire dollar businesses at eBay. Adam Burrows leads an early stage venture capital firm, Range Ventures, and is a former operator himself. It's a great conversation about the current state of the investing landscape and what comes next.Join the 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.

Skippy apologies and congratulates Theo on his polymarket victory. Doogles quizzes Skippy on the best YTD stock market performances through October. Doogles talks whether or not the AI bubble is behind us or ahead of us, using a recent Bridgewater report. The episode wraps by throwing shade at Chamath and discussing America's two economies.Join the 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.

Skippy talks through Jason Zweig's list of market grievances in his latest commentary in the Intelligent Investor. Some French dude is betting $30 million on a Trump election victory. Douglas is excited that for profit tutoring might be back in China. The Dwayne Wade statue is used as a field goal distraction. The episode wraps with tax advantaged accounts, Jeff Bezos stock selling and the ultimate McDonald's quandary.Join the 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.

It's the 200th episode, people! Doogles starts off talking about the finances of millennials vs. baby boomers in the US. Skippy raises Invest America's idea of giving everyone "baby stocks". Doogles compares food prices in the US to other countries. The episode wraps discussing education costs and the YTD best performing years for the S&P 500.Join the 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.

Doogles covers a recent Ben Carlson piece on the importance of the sequence of returns in investing. Skippy likes a breakdown by Professor Statman about the different types of risk we should all take into account — investment, career, and social. The episode wraps with a discussion about richer households driving consumer spending in the US, and Visa being such a well run company.Join the 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.

Skippy and Doogles sit down with the one and only Aileen Lee. Aileen is the founder of the venture firm Cowboy Ventures, and created the term "unicorn" for companies worth at least $1 billion and less than 10 years old. Awesome convo.Join the 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.

KIcks off with listener mail about a Duke research report on human capital investments during Covid. Doogles walks through a Graham Duncan piece on the 5 levels of investment prowess. Skippy throws shade at banks for making so much money while not paying high interest rates. The episode wraps with CZ getting out of jail and starting a Giggly company.Join the 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.

Skippy talks through the pros and cons of legalized sports gambling in the US. Doogles covers the recent Chinese stock rally and David Tepper's take on the whole thing. The episode wraps with OpenAI's proposed shift to a for profit company.Join the 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.

Kicks off with listener mail about refinancing given the recent interest rate reduction. Doogles covers a post about universities being debt factories. Skippy is loving the anniversary of Boris Yeltsin's visit to a Texas grocery store. Doogles walks through Marty Zweig's rules of investing. The episode wraps with Nike getting a new CEO and Microstrategy's continuing Bitcoin escapades.Join the 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.

Doogles hops back on his air conditioning soap box. Skippy is enamored with the cash flow generation of Visa. Doogles talks about the privileged tax strategy that is Buy, Borrow, Die. The episode wraps with a conversation about Only Fans' economics.Join the 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.

Lots of listener mail! First up, Skippy can't get over how bad a recent Economist article is, called Has Warren Buffett Lost His Touch? Doogles praises Costco and all its glory. Skippy is more than skeptical about the potential for a new(ish) app called dub to succeed in helping people to copy other investors' portfolios. The episode wraps by discussing Aswath Damodaran's take on aiming for 10 baggers, formerly dominant stocks and a conversation between Howard Marks and Morgan Housel.Join the 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.

Doogles passionately expresses his hotels rewards preference. Skippy makes a quiz out of the hottest brands people get tattooed on their bodies. Douglas covers the economics of Roblox. The episode wraps with a chance encounter upon EBITDA Growth Systems and 9 thoughts on money from George Mack.Join the 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.

This is a premium episode week where Skippy and Doogles talk about recent stock buys — to become a premium subscriber head over here.For non-subscribers, Doogles highlights Howard Marks' recent memo "Mr. Market Miscalculates" and a great blog post about the importance of expertise...as evidenced by piano tuning.Join the 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.

Doogles practices the art of confirmation bias in a paper by the Federal Reserve of San Francisco about Americans running low on cash and high on debt. Skippy does the same in a review of recent 13Fs, and big funds buying some of his picks. Doogles talks through the recent lack of distributions to investors for private equity funds. The episode wraps with ARKK continuing to lose so so so so much more money for investors than it brings in as fees.Join the 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.

Berkshire Hathaway has a record cash pile and Doogles speculates on what he might do with it. Skippy yawns at the market drop, talks Yen carry trade and the finances of the US VP candidates. Doogles marvels at the Nvidia H100 hoarders. The episode wraps with the terms of Pitbull buying the stadium naming rights to Florida International University. Join the 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.

Skippy is enamored by Uber's cumulative to date operating losses. Doogles goes through the history of the one and only George Foreman Grill. Skippy shines light on the effectiveness of investing alongside Wall Street Bets. The episode wraps with the many failures of Intel and the history of dominant stocks in the market.Join the 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.

Skippy discusses the rise of Junior Bridgeman, NBA 6th man to $600m empire. Doogles walks through the results of OpenResearch's recent universal basic income (UBI) study. Skippy talks through the profiles of Bitcoin owners. There's some debate over the merits of the CAOS ETF. The episode wraps with a convo about Collab Fund's recent post "Fill the Bathtub."Join the 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.

Skippy puts the magic of compounding on full display. Doogles runs through a research paper on balancing your career risk with portfolio risk. Skippy looks at stock volatility and Hawaiian Electric. Doogles continues his rant on US debt. The episode wraps with a political Bitcoin conspiracy theory and the sad life of UK stocks.Join the 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.

Skippy is very happy about the large number of new companies being started in the US. Doogles touts the skills of Priscila Barbosa and her Uber/Lyft scam empire. Skippy creates a new financial moniker called...the Skippy. The episode wraps talking about the state of US national debt.Join the 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.

Doogles talks through a piece on how no one really understands interest rates, but Skippy isn't buying it. Skippy covers New York City's traffic disaster and the $700 million fall out. Doogles hits on Sequoia's $600 billion AI question. The episode wraps with the reality gap media has with politics in the US.Join the 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.

Nepotism remains alive as Bronny James gets drafted by the Lakers. Skippy gets nostalgic about Nike stock. Doogles can't believe how bad of a business Walgreens has managed to become. The episode wraps talking about the "Daddy Model of Wealth" outlined by Paul Graham.Join the 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.

Skippy kicks off with current stock allocation rates for Americans, then moves to the wild premiums that Costco and Nvidia stocks have right now. Doogles hits on a Global Financial Data article covering stock market concentration rates over the last 200 years. The episode wraps with a Wall Street Journal piece on financial lessons from our parents, self-inflated fund returns, and Doogles' current take on Broadcom.Join the 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.