Skippy and Doogles Talk Investing
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.
SaaSpocalypse Now? AI, Block Layoffs & the Trust Premium
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@gmail.com.
Pinterest: Hidden Gem or Just a Pretty Picture? [Investment Committee]
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 WorldAI-powered discoveryStock-based compensationand more...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.
Is Software Dead or Just On Sale?
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.
Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)
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...
Hi-Ho Silver, and Away
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.
Got it Goin On Like Kroenke Kong
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.
The 5-Minute Buffett Test
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.
Play Stupid Games, Win Stupid Economies
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...
CEO of Berkshire is a Job I'm Glad I Don't Have [2025 Greatest Hits]
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.
Jim Beam Shuts Down, Tax Apps Block Holidays, and the $700M Wedding Ring Repo
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.
Mitt Romney Says Tax the Rich? Plus Sports Betting Regret and Gen Z Financial Nihilism
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.
Private Equity Invades College Sports: Utah’s $100M Gamble and Affordability is Broken
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...
Michael Burry Speaks, Prediction Markets Explode, and Why TiVo Just Died
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.
The Real Poverty Line, Ray Dalio’s Bubble Math, and Charlie Munger’s Last Lessons
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 S...
Operating Margins, 4,000 Terrible Stocks & the Wild Google Comeback
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 o...
20 Lessons from 2008 That Still Matter (Especially Now)
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 fa...
OpenAI is a Masterclass in Market Mispricing
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.
A $20K Robot Butler and Why 57% of Americans Don’t Invest
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...
How the NFL Prints Money, and Why College Tuition Just Crashed
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 note...
AI Hype Circle, and ETFs Are the New Casino Chips
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.
Japan, Debt, and the Downside of Free Money
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 Su...
Ponzi Nation — RadioShack Scams, First Brands Shenanigans & PE’s Retirement Heist
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, an...
Robinhood’s New Private Fund Is a Terrible Idea
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 o...
$300 Billion of Fake AI Money and the Oracle OpenAI Bubble
Skippy trades value stocks for $180 flannels and Burning Man invites — which can only mean one thing: we’re officially in fantasy land. The AI hype train hit a new gear as OpenAI agreed to spend $300B (of money it doesn’t have) with Oracle (for compute that doesn’t exist). Naturally, Oracle stock popped $250B in market cap. We break down why this deal is built on hope and hype, and why it might be the clearest sign yet of an AI bubble. The episode wraps with listener mail that covers whether AI productivity is real, and what tools newer in...
House Rich, Cash Poor: Why Americans Are Tapping Their Homes for Survival
Skippy & Doogles dive into the uncomfortable truth behind America’s housing obsession. Why are homeowners tapping their equity at record rates — even if it means refinancing into higher interest rates? It’s House Rich, Cash Poor season, and we’re breaking down what it means for the economy and your portfolio.
Plus:
Is homeownership actually a path to wealth? (Spoiler: Not for most.)Howard Marks on investor psychology and overpriced marketsKawhi Leonard, carbon offsets, and a $300M NBA sponsorship scandalJoin the Skippy and Doogles fan club. You can also get more details about the show...
Deckers Outdoor: Stock Turnarounds, Sheep Lawsuits & $11B Moonshots (Part 2)
In Part 2 of our Deckers Outdoor (NYSE: DECK) breakdown, we dive into the company’s wild transformation from 2003 to 2024—highlighting how a near-death sandal brand evolved into a $30B powerhouse behind UGG and Hoka.
Inside:
The 10,000% stock return from 2004 to nowThe $1.1M Hoka acquisition that became an $11B rocketUGG’s rise via Oprah, scarcity, and sheep dramaWhy Deckers always fights hardest when it's downA buyback strategy that would make Buffett proudWhat history suggests about Deckers' next big brandIf you like investing case studies, turnaround stories, or shoes that feel like clouds—you’re in the rig...
Deckers Outdoor: From Surf Bums to a $30B Shoe Empire (Part 1)
How did a couple of California surfers turn a flip-flop side hustle into one of the best-performing stocks of the past 20 years? In this two-part special, Skippy & Doogles unpack the wild origin story of Deckers Outdoor—makers of Teva, UGG, Hoka, and more.
This is Part 1, covering 1973–2003: a journey of grit, sandals, lawsuits, and ugly boots that somehow took over the world.
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.
ETF Survivorship Bias, Intel Drama, and the $1.3 Trillion Buyback Binge
Skippy & Doogles break down the real story behind ETF performance. Then they dive into the wild Intel CEO saga — presidential shade, stock pops, and suspicious options trades. Finally, it's a deep-dive into the $1.3 trillion stock buyback frenzy: what's driving it, and should you care?
In this episode:
The hidden truth behind ETF returns (hint: they’re worse than you think)Intel’s geopolitical mess and the mysterious options tradeRecord stock buybacks: smart capital allocation or corporate cop-out?Why Apple could’ve bought 470 companies… but didn’tJoin the Skippy and Doogles fan club. You can also get...
Michael Mauboussin, PE Ratios & The Art of Future Value
What do Apple and a Southern California utility have in common? In 2013, they traded at the exact same PE ratio — and Michael Mauboussin’s framework explains why. Skippy & Doogles break down the steady-state vs. future value equation, revisit the Apple vs. Edison International case, and pull fresh insights from Mauboussin’s recent conversation with investing legend Seth Klarman. Packed with valuation wisdom, brain-breaking math, and practical takeaways for today’s 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...
South Park, Skinny Shots & the Market Meltdown
First up: South Park goes full send with a Trump satire episode that has Doogles wondering if Matt & Trey are the last ones still doing their jobs. Then it’s on to the Novo Nordisk crash, where "skinny shots" meet IP loopholes and shady online pharmacies Finally, the jobs report is in—and it's messy.
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.
Ferrari Status & the Passive Investing Bubble
Skippy & Doogles are back and revved up. This week, they dig into what Ferrari's "one car less than demand" strategy teaches us about discipline in investing — and why most companies (and investors) can’t help but chase growth at all costs. Then, the duo explores a new research paper warning that the passive investing boom might actually be setting us up for systemic risk. Finally, they tackle a sobering question: why are English-speaking countries so unhappy — and could housing policy be the hidden culprit?
Join the Skippy and Doogles fan club. You can also get more details about...
Passive Income Lies, BrewDog Drama, and Zip Code Economics
Skippy & Doogles rip apart the worst “passive income” ideas making the rounds on Twitter (spoiler: vending machines aren’t passive). Then it’s off to BrewDog, the startup turned unicorn turned investor cautionary tale — complete with shady dilution, broken promises, and a side of bad beer. We also dive into new research on how your zip code shapes your credit score (and why America might run on debt more than Dunkin’), and wrap with the value of unpacking in understanding what career you want and how you want to invest.
Join the Skippy and Doogles fan club. You can also...
Youth Sports Are a $40B Racket — And Other Ways We Misallocate Money
Skippy & Doogles take on the $40B youth sports industrial complex, the myth of "smart money," and why partying might actually be dead in America. From private equity buying baseball fields to billionaires going broke, this episode unpacks the psychology behind bad investments—financial and social. Plus, we dive into Victor Haghani's “The Missing Billionaires” and what most financial advice gets totally wrong.
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.
Trump Accounts Debunked, PE Myths, and Incentivized Stupidity
Skippy & Doogles dig into the fine print of the “Trump Accounts” and discover… it’s not what the headlines promised. Is it an investing tool or just legislative cosplay? Then they hit the gas on private equity performance myths and finish strong with a discussion on incentivized stupidity—from lawn chairs and balloons to CEOs pumping their own stock.
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.
Venture Returns Unpacked, AI’s Internet Disruption, And The Dangerous Success of Stablecoins
Skippy and Doogles are back in your mentals with a triple-header of investing greatness. First up, a stablecoin thought experiment gone dark—what if Circle succeeds too much? Then, Cloudflare’s CEO drops jaw-dropping data on how AI is nuking the internet’s original traffic model. Finally, we break down two blog posts on venture fund returns—including Y Combinator's staggering 6,000x win with Airbnb.
Plus: Amazon’s long shadow over local business and why Skippy might owe central banks an apology.
Join the Skippy and Doogles fan club. You can also get more details about the...
Stablecoins, Speculation, and When to Sell a 10X Investment
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.
Circle IPO Frenzy, Tip Tax Madness, and America’s Adulting Crisis
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 surprising math behind “no taxes on tips”Why basic life skills are trending on GoogleListener mail: when should startup founders hire a finance pro?Join the Skippy and Doogl...
[Replay] How the World’s Best Investors Stay Rich, Wise, and Sane | William Green Revisited
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...
No Free Lunch — Tipping, Student Loans, and Complex Investing Truths
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.
Leverage Looks Brilliant, Until It Blows Up
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. realityWant to build wealth wit...
