Skippy and Doogles Talk Investing

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...

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 costs College Sports Go Corporate: The University of Utah...

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 o...

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 Jour...

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 Rentals A 70% drawdown strategy that might actually work Google’s surprise AI + chip resurgence...

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 wor...

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@g...

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,...

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...

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.co...

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...

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...

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 list...

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...

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 Mar...

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 now The $1.1M Hoka acquisition that became an $11B rocket UGG’s rise via Oprah, scarcity, and sheep drama Why Deckers always fights harde...

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...

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 geopolitica...

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 va...

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 skippy...

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...

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 o...

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 get...

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...

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 Airbn...