Skippy and Doogles Talk Investing

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 Soc...

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. Join the premium Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show notes on our Sub...

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. Join the premium Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com...

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. Join the premium Skippy a...

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. Join the...

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...

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 protei...

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. Join the premium Skippy and Doogles fan club . You can also get more details about t...

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. Join the premium Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show notes on o...

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. Join the premium Skippy and Doogles fan club . You can also get more deta...

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 privat...

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&n...

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 ep...

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...

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 migh...

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? 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@...

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: ARPU vs. Meta (and why that gap matters) The 9x monetization problem between the U.S. and Rest of World AI-powered discovery Stock-based compensation and more... At ~$18 per share and down big...

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." 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 .

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...

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. 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 se...

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. Join the premium Skippy and Doogles fan club ....

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. Join the premium Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show note...

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...

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! Join the premium Skippy and Doogles fan club . You can also get more details about the show a...

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. 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 t...