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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.
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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 tradeoffs of investing in illiquid markets, how to distinguish between stocks that are cheap for a reason versus simply ignored, and why smaller investors may actually have an edge in parts of the market institutions can’t touch.This is a thoughtful conversation about process, discipline, and doing the work others won’t — not chasing hype, but uncovering opportunity in the market’s blind spots.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.
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 send comments or questions to skippydoogles@gmail.com.
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. 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.
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 notes on our Substack, and send comments or questions to skippydoogles@gmail.com.
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.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.
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 at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.
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 to skippydoogles@gmail.com.
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.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.
Skippy & Doogles unpack three wild stories from the world of money, markets, and mayhem:Listener mailbag: “You guys called it!” — Oracle’s crash, Broadcom’s wild ride, and the return of Cisco (25 years later)Affordability all day, every day: A new Brookings study reveals that 1 in 3 U.S. middle-class families can’t afford basic living costsCollege Sports Go Corporate: The University of Utah just sold a piece of its future to private equityJoin 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.
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.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.
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.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.
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:Operating margin quiz: Ports vs. Pizza vs. Car RentalsA 70% drawdown strategy that might actually workGoogle’s surprise AI + chip resurgence (is Gemini now the AI model?)Value investing is still dead…for nowJoin 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.
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:The rise of working-class investors — is it a bubble signal?What “affordability” really means in an age of all-time high incomes and pricesWhether it's time to build a bachelorette party GoFundMe appJoin 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.
Skippy & Doogles dive into two wild valuation stories this week: OpenAI's trillion-dollar fantasy and Kenvue's decision to sell itself short. This is a clinic on how markets misprice both risk and hype.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.
Skippy & Doogles are back and asking the hard questions:Would you drop $20K on a humanoid robot to do your dishes... or spy on your family? We break down the new NEO robot, what it means for tech, labor, and your creepy futuristic dinner parties.Then we dig into a Philly Fed study revealing why 57% of Americans still don’t invest in the stock market—with stats that’ll surprise you. Finally, we tackle the explosion of gamified investing and prediction markets—and why everyone seems to be betting on everything.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.
Skippy & Doogles break down how the NFL became America’s most valuable ad agency — and why college tuition at one law school just dropped $13K overnight. We kick things off with a mystery quiz on sports league revenues, then dig into a Goldman Sachs report showing the full $260 trillion global portfolio. Jim Simons drops in (kinda) with a legendary gold trade, and we wrap with what the student loan cap just exposed about higher education pricing.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 sad, Skippy is confused, and together they try to untangle the absolute nonsense of modern markets. From OpenAI’s mystery valuation and AMD’s pop to the ETF industry's new wave of leveraged chaos, it’s all starting to look like a big, expensive game of Monopoly—with no banker.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.
Skippy & Doogles unpack what Japan’s economy can teach us about the long-term effects of debt, demographics, and currency devaluation. It's a trip from macroeconomics to your insurance premiums — with detours through Warren Buffett shade, Elon Musk’s movie takes, and listener shoutouts from Bulgaria to Big Ten country.And for premium listeners, we break down sectors that are relatively cheap in today's market and might be worth researching for your portfolio.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.
Skippy and Doogles wade into the deep end of financial nonsense — and it’s murkier than ever. From First Brands and their spark plug shell game to RadioShack’s straight-up Ponzi scheme, they dissect why scams are the market's current business model. Then it’s on to a comment about Oracle’s $300B AI pre-order, Jane Street’s billion-dollar options arbitrage in India, and why private equity firms are drooling over your retirement account.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 Robinhood’s latest move: launching a private fund for retail investors. Is it financial innovation—or a terrible idea wrapped in slick UX? The guys then break down how this mirrors the dot-com era, why closed-end funds can burn you, and what happens when private markets meet public hype. Plus: a GQG report claiming we’re in 1999, not 1995—and some top-tier listener mail that’ll make you think twice about compound interest.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.
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