Skippy and Doogles Talk Investing

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?

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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.

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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.

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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.

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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.

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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.

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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.

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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).

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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.

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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.

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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.

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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.

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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.

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This week, Skippy and Doogles chat about the SpaceX IPO and ask if your TAM is basically “the entire digital economy plus maybe Mars,” do fundamentals still matter? Then they turn to a viral MasterCard sell decision as a case study in how not to handle underperformance, before wrapping with Chris Hohn’s concentrated portfolio of toll booths, rails, ratings agencies, and other monopolies.

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Skippy and Doogles dig into the weird state of today’s market: IPOs are rarer, companies are older, profitability is harder to find, and a lot of the action has disappeared into private markets. Using Jay Ritter’s IPO data as a jumping off point, they compare today’s IPO landscape to the dot-com era and ask whether the public market data is missing the real story. Bubbly valuations, massive market concentration, shaky consumer sentiment, private credit concerns, happy hour economics, and the newly coined “Dog’s Life Economy,” where everyone keeps running full speed until something breaks.

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Skippy 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.

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Skippy 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.

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We 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.

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We 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.

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We 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.

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We 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.

Doogles 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.”

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Doogles 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.

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Skippy 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.

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Is 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?

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Is Pinterest stock (PINS) a hidden gem… or just a really good looking business with a monetization problem? In our first-ever Investment Committee episode, we take a deep dive into Pinterest.

We break down:

At ~$18 per share and down big from highs, is this a turnaround story, an acquisition target, or a value trap? As always: do your own research. We’re here to sharpen thinking, but the decision is yours.

Software stocks are getting hammered. Adobe at 7 year lows, Salesforce crushed. We discuss why and then cover our takes on the recent viral piece "Something Big is Happening."

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In this episode, we’re joined by deep value investor Lee Roach, author of The Value Road Substack, to explore what it really means to find value where no one else is looking.

Lee shares his unconventional path from working overnight shifts in a manufacturing plant to becoming a full-time investor and writer. We dive into his approach to deep value investing, with a focus on micro-cap and nano-cap stocks, why “cheap” isn’t enough without a catalyst, and how patience and psychology play a critical role when prices move against you.

We also discuss the trad...

Skippy & Doogles break down the epic silver smackdown, one of the wildest commodity crashes in nearly a century. Also, a quiz on the most popular dating profile words by state (spoiler: Missouri is… a zoo). Then OpenAI’s funding drama continues.

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From Walmart parking lots to $5B stadiums, Stan Kroenke’s is winning. Skippy goes off on Nike’s scarcity games (just give the man a jacket). Doogles drops tariff truth bombs courtesy of Germany's Kiel Institute. And the Acquired Podcast’s 10-year recap sparks a convo on scarcity, podcasting as compounding, and whether we’ve been doing this all wrong.

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Warren Buffett says it only takes 5 minutes to know if a company’s worth buying. Skippy & Doogles unpack what he really means.

Plus: US workers are getting a smaller slice of the pie — lowest since 1947, and Elon Musk says don’t save for retirement. Cool. Cool cool cool.

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First up, Venezuela. Once the richest country in South America, now economically uninvestable. We unpack how oil wealth turned into a curse, what "Dutch Disease" really means, and how Norway played the game better. Then it's onto growth investing. What actually makes a great growth stock? We break down a killer piece by James Gaultry, the Costco vs. LVMH debate, and why high ROIC plus reinvestment opportunities are rarer than you think. Finally, we dive into Pablo Torre’s podcast episode on scoring — and the existential trap of chasing the wrong metrics in life, money, and college rankings.

Jo...

This is a very special episode very year! For "I Roll With Skippy & Doogles" premium subscribers, this is where we do our 2025 performance and portfolio review. And for all other listeners (we appreciate you too!) you get a greatest hits compilation from our most listened to episodes from 2025. Enjoy!

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Skippy & Doogles wrap up 2025 (and year five of the pod!) with a rapid-fire round of wild investing stories, billionaire blowups, bourbon shutdowns, and ultra-wealthy tax dodging that’s so ridiculous it ruins Christmas.

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Skippy & Doogles dive into Mitt Romney’s surprising New York Times op-ed calling to raise taxes on the ultra-wealthy — including himself. We also unpack the growing backlash to legalized sports betting, the subtle shift in public opinion, and why gambling fatigue is setting in fast. Then it’s on to Gen Z and the rise of financial nihilism.

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Skippy & Doogles unpack three wild stories from the world of money, markets, and mayhem:

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This week, Skippy & Doogles unpack Burry's latest market outlook, shady behavior in prediction markets, and the bizarre death (yes, death) of TiVo. Plus: Apple’s massive buybacks, Caitlin Clark’s WNBA salary quiz, and why MicroStrategy might be headed for disaster.

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Skippy and Doogles dive into the viral debate around “the real poverty line” and trust us, it’s not $31,000… but it’s definitely not $140,000 either.

Then we turn to Ray Dalio’s latest bubble commentary, unpacking what “80% of the way into a bubble” really means—and why cash, leverage, and forced selling matter more than clickbait headlines.

Finally, we close with the heartwarming Wall Street Journal piece on Charlie Munger’s final years. From yelling across rooms with Buffett to adopting new teenage friends at age 99, Munger kept compounding wisdom until the very end.

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Skippy & Doogles dive into operating margins across industries, break down a wild Morningstar strategy that involved buying 4,000 terrible stocks and made bank. And then debate whether Google just leapt past NVIDIA in the AI chip race.

In this episode:

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Skippy & Doogles fire up the investing time machine and revisit Seth Klarman’s 20 lessons from the 2008 financial crisis — lessons that feel alarmingly relevant in today’s overheated market. From the dangers of financial innovation to the privilege of liquidity, they break down the timeless wisdom and apply it to 2025’s investor landscape.

Plus, listener mail sparks debates on:

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