Skippy and Doogles Talk Investing

SaaSpocalypse Now? AI, Block Layoffs & the Trust Premium

Mon, 02 Mar 2026 02:30:00 -0700

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]

Mon, 23 Feb 2026 02:30:00 -0700

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 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.

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Is Software Dead or Just On Sale?

Mon, 16 Feb 2026 02:30:00 -0700

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)

Mon, 09 Feb 2026 02:30:00 -0700

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.

Hi-Ho Silver, and Away

Mon, 02 Feb 2026 02:30:00 -0700

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

Mon, 26 Jan 2026 02:30:00 -0700

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

Mon, 19 Jan 2026 02:30:00 -0700

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

Mon, 12 Jan 2026 02:30:00 -0700

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.

CEO of Berkshire is a Job I'm Glad I Don't Have [2025 Greatest Hits]

Mon, 05 Jan 2026 02:30:00 -0700

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

Mon, 29 Dec 2025 02:30:00 -0700

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

Mon, 22 Dec 2025 02:30:00 -0700

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

Mon, 15 Dec 2025 02:30:00 -0700

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 just sold a piece of its future to private equity

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.

Michael Burry Speaks, Prediction Markets Explode, and Why TiVo Just Died

Mon, 08 Dec 2025 02:30:00 -0700

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

Mon, 01 Dec 2025 02:30:00 -0700

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.

Operating Margins, 4,000 Terrible Stocks & the Wild Google Comeback

Mon, 24 Nov 2025 02:30:00 -0700

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 (is Gemini now the AI model?)
Value investing is still dead…for now

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.

20 Lessons from 2008 That Still Matter (Especially Now)

Mon, 17 Nov 2025 02:30:00 -0700

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 prices
Whether it's time to build a bachelorette party GoFundMe app

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.

OpenAI is a Masterclass in Market Mispricing

Mon, 10 Nov 2025 02:30:00 -0700

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

Mon, 03 Nov 2025 02:30:00 -0700

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.

How the NFL Prints Money, and Why College Tuition Just Crashed

Mon, 20 Oct 2025 02:30:00 -0700

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.

AI Hype Circle, and ETFs Are the New Casino Chips

Mon, 13 Oct 2025 02:30:00 -0700

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

Mon, 06 Oct 2025 02:30:00 -0700

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.

Ponzi Nation — RadioShack Scams, First Brands Shenanigans & PE’s Retirement Heist

Mon, 29 Sep 2025 02:30:00 -0700

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.

Robinhood’s New Private Fund Is a Terrible Idea

Mon, 22 Sep 2025 02:30:00 -0700

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.

$300 Billion of Fake AI Money and the Oracle OpenAI Bubble

Mon, 15 Sep 2025 02:30:00 -0700

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 investors should use.

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.

House Rich, Cash Poor: Why Americans Are Tapping Their Homes for Survival

Mon, 08 Sep 2025 02:30:00 -0700

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 markets
Kawhi Leonard, carbon offsets, and a $300M NBA sponsorship scandal

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.

Deckers Outdoor: Stock Turnarounds, Sheep Lawsuits & $11B Moonshots (Part 2)

Mon, 01 Sep 2025 02:30:00 -0700

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 hardest when it's down
A buyback strategy that would make Buffett proud
What history suggests about Deckers' next big brand

If you like investing case studies, turnaround stories, or shoes that feel like clouds—you’re in the right place.

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.

Deckers Outdoor: From Surf Bums to a $30B Shoe Empire (Part 1)

Mon, 25 Aug 2025 02:30:00 -0700

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

Mon, 18 Aug 2025 02:30:00 -0700

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 trade
Record stock buybacks: smart capital allocation or corporate cop-out?
Why Apple could’ve bought 470 companies… but didn’t

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.

Michael Mauboussin, PE Ratios & The Art of Future Value

Mon, 11 Aug 2025 02:30:00 -0700

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 or questions to skippydoogles@gmail.com.

South Park, Skinny Shots & the Market Meltdown

Mon, 04 Aug 2025 02:30:00 -0700

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

Mon, 28 Jul 2025 02:30:00 -0700

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 the show at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

Passive Income Lies, BrewDog Drama, and Zip Code Economics

Mon, 21 Jul 2025 02:30:00 -0700

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 get more details about the show at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

Youth Sports Are a $40B Racket — And Other Ways We Misallocate Money

Mon, 14 Jul 2025 02:30:00 -0700

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

Mon, 07 Jul 2025 02:30:00 -0700

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

Mon, 30 Jun 2025 02:30:00 -0700

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 show at skippydoogles.com, show notes on our Substack, and send comments or questions to skippydoogles@gmail.com.

Stablecoins, Speculation, and When to Sell a 10X Investment

Mon, 23 Jun 2025 02:30:00 -0700

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

Mon, 09 Jun 2025 02:30:00 -0700

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 Google
Listener mail: when should startup founders hire a finance pro?

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.

[Replay] How the World’s Best Investors Stay Rich, Wise, and Sane | William Green Revisited

Mon, 02 Jun 2025 02:30:00 -0700

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 investors
Why avoiding "the death line" matters more than chasing alpha
How great investors think probabilistically and live better lives because of it

This isn’t just about markets—it’s about mastering decisions, uncertainty, and your own temperament. One of our all-time favorites.

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.

No Free Lunch — Tipping, Student Loans, and Complex Investing Truths

Mon, 26 May 2025 02:30:00 -0700

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 system
Why classic investing wisdom doesn’t work in 2025, and why you can’t just be rigid in your investing philosophy

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.

Leverage Looks Brilliant, Until It Blows Up

Mon, 19 May 2025 02:30:00 -0700

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 accounts
Why fees are the silent killer of long-term returns
Basic Capital’s pitch vs. reality

Want to build wealth without stepping on financial landmines? Tap play.

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.

Is Warren Buffett Actually the GOAT?

Mon, 12 May 2025 02:30:00 -0700

Skippy & Doogles dive deep into the Buffett legacy—breaking down Berkshire’s insane 5.5 million percent return, the psychology behind his frugality, and whether longevity alone makes him the greatest. Plus, some spicy comparisons to Michael Jordan, Zuck, and Cold Stone Creamery pricing.

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.

McRecession, Doritos, and a Side of Disappointment

Mon, 05 May 2025 02:30:00 -0700

Are $20 fast food meals the new norm? Skippy & Doogles dig into what’s behind declining sales at McDonald’s and Starbucks, why Taco Bell is thriving, and the absurd new definition of “value.” Then we tackle the broken job market for college grads, the rise of AI as the “third door,” and why short-term thinking is stifling investment in the future.

Plus:

🍟 Why your McValue meal costs more than Chili’s

🎓 What’s really killing entry-level jobs

📉 Is venture capital delusional—or just addicted to management fees?

🧠 Listener mail: What’s an investor to do when everything feels uncertain?

👉 Rate, review, and follow the pod so you don’t miss a beat. It helps a ton!

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.

Yes Risk, No Rari (Yale’s $6B Sale, Student Debt Trouble, and YOLO Traders Gone Wild)

Mon, 28 Apr 2025 02:30:00 -0700

Yale is selling $6 billion of private equity holdings — is this the canary in the economic coal mine? Student loan repayments are back, and the numbers are worse than you think. Plus: YOLO traders are back in force, betting big on Bitcoin and meme stocks with dreams of overnight riches.

👉 Rate, review, and follow the pod so you don’t miss a beat. It helps a ton!

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.

Who Owns America? Foreign Capital, China’s Strategy & the Private Equity Squeeze

Mon, 21 Apr 2025 02:30:00 -0700

Foreigners own net $30 trillion in U.S. assets—should we be worried? Skippy & Doogles go deep on America’s financial entanglements, who holds our debt, and why global capital might be looking for the exit. Then they unpack the China standoff, how trade narratives are twisting, and what private equity’s "perfect storm" means for markets. Banter included. Charts not required.

In this episode:

Who really owns U.S. debt—and why it's less scary than headlines suggest
The “De-Americanization” of global capital: trend or tantrum?
Why China’s calling itself a “safe haven” (and yes, we’re side-eying that too)
The private equity bubble: what happens when no one's buying?
Inflation, leverage, and Powell’s impossible job

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Compounding When the World’s on Fire

Mon, 14 Apr 2025 02:30:00 -0700

Markets are twitchy, tariffs are flying, and the Economic Policy Uncertainty Index just hit 900. So... what now? This week, Skippy and Doogles channel Charlie Munger, debate whether it’s time to dump Chinese stocks, and wrestle with how (and when) to deploy cash in a world that makes zero sense. Plus: Howard Marks drops another banger memo, the NASDAQ flirts with 24/7 trading, and we break down the real deal with ESOPs and employee ownership.

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I Tariff So Hard Economics Can’t Find Me (How Bad Math Crashed the Market)

Mon, 07 Apr 2025 02:30:00 -0700

This week, Skippy & Doogles go scorched earth on the most chaotic economic policy rollout in recent memory. Trump’s new “reciprocal” tariffs? We break down the math (spoiler: it’s nonsense), the market fallout, and why it’s got economists, investors, and even penguins running for the hills.

Expect:

🔥 A full takedown of the tariff formula that makes zero economic sense
📉 Analysis of the worst two-day market drop since 2020
🧠 Economics 101 lessons on trade deficits, reserve currencies, and global supply chains
🐧 Penguins in suits. Yes, really.

If you've ever wanted to laugh through a potential recession, this is the episode.

⏱️ Timestamps:

0:00 – Intro: Singing, banter, and setting the economic disaster stage

2:30 – Oral history of the week: Trump’s Rose Garden announcement & TSMC confusion

6:40 – Why the 34% “reciprocal” tariff rate is complete fiction

10:30 – Economics lesson: Why trade deficits are misunderstood

14:45 – The Target analogy: Reciprocal tariffs and breakfast burritos

18:30 – Meme review: Penguins, charts, and the internet doing its thing

22:00 – Market reaction: S&P, NASDAQ, and recession odds spike

27:00 – Why this is a terrible negotiation tactic

32:00 – Apple, Nike, and how everyday prices will surge

37:00 – The global fallout: IMF, JP Morgan, Reagan Caucus respond

42:00 – Final rant: Why this is the worst policy move in decades

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Burrito Bowls, Now With Zero Percent Down

Mon, 31 Mar 2025 02:30:00 -0700

This week, Skippy’s in the U.S., Doogles is in Paris, and the global economy is somewhere between a punchline and a panic. We kick things off with a deep dive into the new 25% auto tariffs—what they mean for carmakers and investors. Then we pivot to the bizarre: Trevor Milton, the man who rolled a fake truck down a hill, just got pardoned. What does that mean for financial regulation and investor trust?

Finally, we unpack the rise of Buy Now, Pay Later… for burritos. Is it just a viral stunt or a symptom of a fragile consumer economy? And in the premium segment, we go inside Stanley Druckenmiller’s latest macro bet on pharma.

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.

Preferred Shares of Chaos

Mon, 24 Mar 2025 02:30:00 -0700

The Celtics sold for $6.1B?! We break down why pro sports teams are selling out, debate March Madness chaos, and roast Michael Saylor’s “Preferred Shares of Chaos” — a crypto-powered yield product that smells like a Ponzi. Plus: Treasury’s 3-3-3 Plan, and why America can’t build anything anymore.

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Is America Really Going Bankrupt?

Mon, 17 Mar 2025 02:30:00 -0700

In this jam-packed episode, Skippy and Doogles tackle everything from Elon Musk’s bold economic takes to why CEOs are afraid to speak out right now. They dive deep into the complexities of modern monetary theory—complete with a bucket analogy that might just change how you see government debt. Plus, they break down the current state of consumer spending. It’s sharp investing insights with a side of laughs—because who said finance has to be boring?

👉 Stick around till the end for premium-only insights and find out which stocks they think could be winners.

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Rewriting the Economy: Trump’s GDP Plan, Market Crashes & a Shifting World

Mon, 10 Mar 2025 02:30:00 -0700

Is the government cooking the books? This week, Skippy & Doogles dive into Trump’s plan to strip government spending from GDP—what it means, why it’s happening, and whether it changes how we measure recessions. Plus, we break down 150 years of stock market crashes to uncover the biggest investing lessons, and we analyze the wild shifts happening in the global economy—from rising military spending to trade wars and the Fed’s next move. Oh, and did we mention the ‘Strategic Bitcoin Reserve’? Buckle up, this one’s a ride.

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Booz, Buffett, and Billionaires

Mon, 03 Mar 2025 02:30:00 -0700

Skippy looks at Booz Allen Hamilton’s wild government contract dependency and what happens when the political winds shift. Doogles breaks down Warren Buffett’s latest (and maybe last?) Berkshire Hathaway annual letter. Skippy highlights how the top 1% now account for 50% of U.S. consumer spending, and asks what that means for markets. The episode wraps with some listener mail about how politics and morality should or shouldn't play in investment decisions.

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Bill Ackman’s Berkshire Bootleg

Mon, 24 Feb 2025 02:30:00 -0700

Skippy and Doogles tackle listener mail about Berkshire Hathaway's huge cash pile. Skippy talks through the recent $1.5b hack on ETH. The episode wraps with a deep dive into Bill Ackman / Pershing Square building "the next Berkshire Hathaway" with an increased investment in Howard Hughes.

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Bargains Gettin More Bargainy

Mon, 17 Feb 2025 02:30:00 -0700

Doogles loves Dave Portnoy going off about how the crypto bros can't hodl. Skippy talks through how functional unemployment is much higher than what the aggregate government data shows. Then he gets fired up about Jamie Dimon's rant about remote work. The episode wraps with Pershing Square's latest annual investor presentation.

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What Have You Done For Me Bukelatley?

Mon, 10 Feb 2025 02:30:00 -0700

Doogles highlights that El Salvador is calling in quits on Bitcoin as the national currency. Then he questions whether it's the right time to diversify outside the US. Skippy looks at the poor consumer sentiment in China. The episode wraps with two interview summaries with professional investors — Graham Duncan and Mike Maples.

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The Stocks From Ipanema Go Walking

Mon, 03 Feb 2025 02:30:00 -0700

Skippy and Doogles answer listener mail on Cathie Wood's underperformance. Skippy tells Visa to stop performing so well so they don't get shut down. Doogles talks through career lessons from David A. Patterson. Skippy is enamored by Warren Buffett's cash pile and it's market crash predictions. The episode wraps with a discussion about Twilio and Brazilian equities.

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Let’s Play Hide and DeepSeek

Mon, 27 Jan 2025 02:30:00 -0700

Doogles is fascinated by the US/China AI race, and specifically DeepSeek. Skippy is not happy with how American's are treating their finances. The episode wraps with a conversation about David Einhorn's latest take on how the market today is fundamentally broken.

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The Conundrum of the Personal Burger Taxi

Mon, 20 Jan 2025 02:30:00 -0700

Skippy pulls a 180 and now thinks that the US buying Greenland has some merit. Doogles stresses the importance of spending an unreasonable amount of time to allow for greatness. Skippy dives deep into the science of alcohol. The episode wraps with a discussion on stress and burnout, and then the US dollar's overvaluation.

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Reading Between the Lines

Mon, 13 Jan 2025 02:30:00 -0700

Skippy and Doogles tackle the relationship between interest rates, the economy and stock valuations. Doogles walks through Charlie Bilello's latest chart recap. Skippy covers traffic congestion in NYC. The episode wraps discussing Howard Marks' latest memo Bubble Watch.

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Brought to You By the Year 2035 [2024 Episode Compilation]

Mon, 06 Jan 2025 02:30:00 -0700

Celebrating one more year in the past! Skippy and Doogles go through Cliff Asness' look back at the market from the lens of 2035. The rest of the episode highlights from 2024 episodes including: Li Liu's principles of value investing, an interview with Cliff Asness, and David Tepper's take on investing in China.

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Who is Buying This Hogwash?

Mon, 30 Dec 2024 02:30:00 -0700

Skippy is flabbergasted by a man who takes saving money to the extreme. Doogles says to watch the cognitive load people are putting on their processes. Skippy shakes his head at how Bench Accounting shuts down. Doogles gives a PSA on cryptocurrency scams. The episode wraps with Mag 7 P/E ratios gone wild and how to prepare for a lost decade in stocks from Barron's.

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First There Was the War, Then the Capitulation

Mon, 23 Dec 2024 02:30:00 -0700

Skippy highlights the financial incongruence of NFL quarterbacks. Doogles shakes his head at a Techcrunch piece on Databricks waiting to go public. Skippy talks through US vs European value creation. The episode wraps with a discussion on entropy and its connection to investing.

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Pop Goes the Bubble ‘Cause the Bubble Say Pop

Mon, 16 Dec 2024 02:30:00 -0700

Skippy quizzes Doogles on a variety of topics and Doogles fails all of them. Then they go into the depths of listener mail, first talking about whether macro conditions and business environment justifies currently high Buffett Indicator levels, and then exploring another argument in favor of Bitcoin.

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While Your Feet Are Stomping And the Coins Is Pumping

Mon, 09 Dec 2024 02:30:00 -0700

Doogles talks about the current mindset of the American worker. Skippy talks market valuations in the US and parlays that into a conversation about pump.fun and the creation of meme coins. The episode wraps with Michael Saylor pitching Microsoft on buying Bitcoin and Howard Marks' latest memo about asset allocation.

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Oh The Places Stocks'll Go

Mon, 02 Dec 2024 02:30:00 -0700

Skippy returns from his Asian conquests and discusses the value in looking at international stocks. They discuss how hard it is to find a 200 bagger...and how long it takes to get there. The episode wraps discussing the "real value of money".

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The Quest for Insufferable Geniuses w/ Josh Scott and Adam Burrows

Mon, 25 Nov 2024 02:30:00 -0700

Skippy is out searching for new companies to invest in within the great continent of Asia, so Doogles is handling this one solo...but with two special guests. Josh Scott is an entrepreneur and investor who has also led multi-billionaire dollar businesses at eBay. Adam Burrows leads an early stage venture capital firm, Range Ventures, and is a former operator himself. It's a great conversation about the current state of the investing landscape and what comes next.

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Doogles Jumps the Shark

Mon, 18 Nov 2024 02:30:00 -0700

Skippy apologies and congratulates Theo on his polymarket victory. Doogles quizzes Skippy on the best YTD stock market performances through October. Doogles talks whether or not the AI bubble is behind us or ahead of us, using a recent Bridgewater report. The episode wraps by throwing shade at Chamath and discussing America's two economies.

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Curmudgeonry McMuffinry

Mon, 04 Nov 2024 02:30:00 -0700

Skippy talks through Jason Zweig’s list of market grievances in his latest commentary in the Intelligent Investor. Some French dude is betting $30 million on a Trump election victory. Douglas is excited that for profit tutoring might be back in China. The Dwayne Wade statue is used as a field goal distraction. The episode wraps with tax advantaged accounts, Jeff Bezos stock selling and the ultimate McDonald’s quandary.

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Millennials Do Debt Better

Mon, 28 Oct 2024 02:30:00 -0700

It's the 200th episode, people! Doogles starts off talking about the finances of millennials vs. baby boomers in the US. Skippy raises Invest America's idea of giving everyone "baby stocks". Doogles compares food prices in the US to other countries. The episode wraps discussing education costs and the YTD best performing years for the S&P 500.

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Mr. Statman, Bring Me Some Risk

Mon, 21 Oct 2024 02:30:00 -0700

Doogles covers a recent Ben Carlson piece on the importance of the sequence of returns in investing. Skippy likes a breakdown by Professor Statman about the different types of risk we should all take into account — investment, career, and social. The episode wraps with a discussion about richer households driving consumer spending in the US, and Visa being such a well run company.

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Unicorns, 10 Years Hence w/Aileen Lee (Founder of Cowboy Ventures)

Mon, 14 Oct 2024 02:30:00 -0700

Skippy and Doogles sit down with the one and only Aileen Lee. Aileen is the founder of the venture firm Cowboy Ventures, and created the term "unicorn" for companies worth at least $1 billion and less than 10 years old. Awesome convo.

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Don't Let An Accounting Professor Run Your Company

Mon, 07 Oct 2024 02:30:00 -0700

KIcks off with listener mail about a Duke research report on human capital investments during Covid. Doogles walks through a Graham Duncan piece on the 5 levels of investment prowess. Skippy throws shade at banks for making so much money while not paying high interest rates. The episode wraps with CZ getting out of jail and starting a Giggly company.

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David Tepper Just Don’t Care

Mon, 30 Sep 2024 02:30:00 -0700

Skippy talks through the pros and cons of legalized sports gambling in the US. Doogles covers the recent Chinese stock rally and David Tepper's take on the whole thing. The episode wraps with OpenAI's proposed shift to a for profit company.

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Silly Yeltsin, Trix Are For Kids

Mon, 23 Sep 2024 02:30:00 -0700

Kicks off with listener mail about refinancing given the recent interest rate reduction. Doogles covers a post about universities being debt factories. Skippy is loving the anniversary of Boris Yeltsin's visit to a Texas grocery store. Doogles walks through Marty Zweig's rules of investing. The episode wraps with Nike getting a new CEO and Microstrategy's continuing Bitcoin escapades.

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Boyz II Men, ABC, BBD...Less Tax For Your Family

Mon, 16 Sep 2024 02:30:00 -0700

Doogles hops back on his air conditioning soap box. Skippy is enamored with the cash flow generation of Visa. Doogles talks about the privileged tax strategy that is Buy, Borrow, Die. The episode wraps with a conversation about Only Fans' economics.

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Rub a Dub Dub, Costco is Da Club

Mon, 09 Sep 2024 02:30:00 -0700

Lots of listener mail! First up, Skippy can't get over how bad a recent Economist article is, called Has Warren Buffett Lost His Touch? Doogles praises Costco and all its glory. Skippy is more than skeptical about the potential for a new(ish) app called dub to succeed in helping people to copy other investors' portfolios. The episode wraps by discussing Aswath Damodaran's take on aiming for 10 baggers, formerly dominant stocks and a conversation between Howard Marks and Morgan Housel.

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A Branded Tattoo, I’ll Always Have You

Mon, 02 Sep 2024 02:30:00 -0700

Doogles passionately expresses his hotels rewards preference. Skippy makes a quiz out of the hottest brands people get tattooed on their bodies. Douglas covers the economics of Roblox. The episode wraps with a chance encounter upon EBITDA Growth Systems and 9 thoughts on money from George Mack.

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Some Guy On Some Other Job is Mr. Market

Mon, 26 Aug 2024 02:30:00 -0700

This is a premium episode week where Skippy and Doogles talk about recent stock buys — to become a premium subscriber head over here.

For non-subscribers, Doogles highlights Howard Marks' recent memo "Mr. Market Miscalculates" and a great blog post about the importance of expertise...as evidenced by piano tuning.

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Confirmation Bias, And it Feels So Good

Mon, 19 Aug 2024 02:30:00 -0700

Doogles practices the art of confirmation bias in a paper by the Federal Reserve of San Francisco about Americans running low on cash and high on debt. Skippy does the same in a review of recent 13Fs, and big funds buying some of his picks. Doogles talks through the recent lack of distributions to investors for private equity funds. The episode wraps with ARKK continuing to lose so so so so much more money for investors than it brings in as fees.

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Warren’s Hoarding Cash and Putting Apple in the Trash

Mon, 12 Aug 2024 02:30:00 -0700

Berkshire Hathaway has a record cash pile and Doogles speculates on what he might do with it. Skippy yawns at the market drop, talks Yen carry trade and the finances of the US VP candidates. Doogles marvels at the Nvidia H100 hoarders. The episode wraps with the terms of Pitbull buying the stadium naming rights to Florida International University.

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Will the Real Andy Grove Please Stand Up?

Mon, 05 Aug 2024 02:30:00 -0700

Skippy is enamored by Uber's cumulative to date operating losses. Doogles goes through the history of the one and only George Foreman Grill. Skippy shines light on the effectiveness of investing alongside Wall Street Bets. The episode wraps with the many failures of Intel and the history of dominant stocks in the market.

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Pull Yourself Up By Your Pigtails

Mon, 29 Jul 2024 02:30:00 -0700

Skippy discusses the rise of Junior Bridgeman, NBA 6th man to $600m empire. Doogles walks through the results of OpenResearch's recent universal basic income (UBI) study. Skippy talks through the profiles of Bitcoin owners. There's some debate over the merits of the CAOS ETF. The episode wraps with a convo about Collab Fund's recent post "Fill the Bathtub."

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Wonk and Circumstance

Mon, 22 Jul 2024 02:30:00 -0700

Skippy puts the magic of compounding on full display. Doogles runs through a research paper on balancing your career risk with portfolio risk. Skippy looks at stock volatility and Hawaiian Electric. Doogles continues his rant on US debt. The episode wraps with a political Bitcoin conspiracy theory and the sad life of UK stocks.

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The Skippyonaire Next Door

Mon, 15 Jul 2024 02:30:00 -0700

Skippy is very happy about the large number of new companies being started in the US. Doogles touts the skills of Priscila Barbosa and her Uber/Lyft scam empire. Skippy creates a new financial moniker called...the Skippy. The episode wraps talking about the state of US national debt.

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NYC’s $700 Million Schurprise

Mon, 08 Jul 2024 02:30:00 -0700

Doogles talks through a piece on how no one really understands interest rates, but Skippy isn't buying it. Skippy covers New York City's traffic disaster and the $700 million fall out. Doogles hits on Sequoia's $600 billion AI question. The episode wraps with the reality gap media has with politics in the US.

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Walgreens’ Milkshake Brought No Investors to the Yard

Mon, 01 Jul 2024 02:30:00 -0700

Nepotism remains alive as Bronny James gets drafted by the Lakers. Skippy gets nostalgic about Nike stock. Doogles can't believe how bad of a business Walgreens has managed to become. The episode wraps talking about the "Daddy Model of Wealth" outlined by Paul Graham.

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Why’d You Have to Go And Make Things So Concentrated?

Mon, 24 Jun 2024 00:45:00 -0700

Skippy kicks off with current stock allocation rates for Americans, then moves to the wild premiums that Costco and Nvidia stocks have right now. Doogles hits on a Global Financial Data article covering stock market concentration rates over the last 200 years. The episode wraps with a Wall Street Journal piece on financial lessons from our parents, self-inflated fund returns, and Doogles' current take on Broadcom.

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[Replay] Your Consumerism is Killing Me

Mon, 17 Jun 2024 02:30:00 -0700

This is a replay but still relevant episode from late 2021.

Skippy gets confused as to why Starbucks is adopting the blockchain (and you should be too). Then Skippy and Doogles discuss 3 big breakups this week — General Electric, Toshiba, and Johnson & Johnson are all splitting up their companies. Doogles calls out all of us for perpetuating inflation by buying too much stuff unnecessarily, based on some great reads from Bridgewater Associates and The Atlantic. The episode wraps walking through how much the last few crashes have hurt the market (and the next one won't be better), and how confirmation bias is ruining the world — great piece written by KCP Group called "Racehorses and Psychopaths".

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My AI Juice Is Worth Your Squeeze

Mon, 10 Jun 2024 02:30:00 -0700

Jensanity has hit new heights with Jensen Huang signing body parts over in Taiwan. Walkthrough of how to make good money in side hustles. Skippy covers a WSJ piece on how AI losing its fizzle. The episode wraps with a convo about the state of leveraged finance and a no good, terrible, bad advertising campaign.

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Get Your 10 Year Old to the Ballot Box

Mon, 03 Jun 2024 02:30:00 -0700

Premium subscribers get a couple hot stock research recommendations to kick it off. Doogles tackles listener mail that covers the book The Fourth Turning. Skippy laughs some more at Google AI and Salesforces' inability to use its own product. The episode wraps discussing the results of a YouGov survey about people's favorite decades.

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Hi-ho, the Derry-o, the Fama In the Dell

Mon, 27 May 2024 02:30:00 -0700

Listener mail hits on the controversial topic of Fama and French's data set shifting. Skippy goes off about supposed ridiculousness coming from Google's AI results. The episode wraps with a thought experiment comparing the cost of living in an all inclusive resort vs. living in "Middle America."

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Google Has Gone Full Hooli

Mon, 20 May 2024 02:30:00 -0700

Kicks off with listener mail about the multi-level-marketing shenanigans of IM Academy. Skippy teases Doogles about a winning pitch on shorting Pool Corp. Skippy plays with ChatGPT 4-o as his new financial analyst. Doogles covers an op-ed on taxing billionaires. The episode wraps with a quick hit on the failure of Red Lobster.

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Chocolate’s Called Liquid Gold For a Reason

Mon, 13 May 2024 02:30:00 -0700

Skippy honors the legacy of Jim Simons' legendary returns. Doogles covers people's inaccurate view of fairness. Skippy won't stop ranting about tech companies' capital expenditures. Doogles gives highlights from a recent financial literacy survey. The episode wraps with Howard Marks on debt and Doogles' most recent stance on Twilio.

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Skippy & Doogles Go To NewBraska

Mon, 06 May 2024 02:30:00 -0700

Skippy and Doogles TAKE OVER (but not really) the Berkshire Hathaway annual shareholders meeting in Omaha. We give you the run down on the dilly as it were.

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Debt La Soul is Dead

Mon, 29 Apr 2024 02:30:00 -0700

Doogles gets nostalgic about the Domino's 30 minute delivery guarantee. Skippy spits wisdom about debt and money from the book Letters to My Son. Doogles continues the debt train talking about home mortgages and credit card charge offs. The episode wraps discussing how to comprehend compounding, and the state of Chinese real estate.

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Pretty Ricky’s What They Call Him

Mon, 22 Apr 2024 02:30:00 -0700

Skippy talks about how Americans throw away $68 million in change per year. He then gives out a research recommendation of an American utility. Doogles walks through a New York Times piece claiming that the boom and bust cycle is dead. Doogles finally finished the book Same as Ever and talks through the highlights. The episode wraps discussing the headache that is taxes in the US.

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Keep the Credit Where Credit’s Due

Mon, 15 Apr 2024 02:30:00 -0700

We kick off with a barrage of listener mail on women's basketball, retirement, and David Einhorn stock picks. Doogles brings us a recent Cliff Asness interview and parlays that into lessons from Jensen Huang of Nvidia. Skippy is saddened that Intel can't get out of its own way. The episode wraps with a sad case of someone selling their credit history for money and Peloton as the next great media company.

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Tap That Social Security, Baby

Mon, 08 Apr 2024 02:30:00 -0700

Skippy is surprised to learn that Nike stock is on a 50% drawdown...yet still not cheap. Doogles walks through a piece on winning by avoiding blunders. Skippy takes us to microcap nerd land through an interview with the author of the NoNameStocks blog. The episode wraps discussing fee based financial advisors and "volatility laundering".

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Absolutely Never Always Use Absolutes

Mon, 01 Apr 2024 02:30:00 -0700

Skippy and Doogles are amazed at DJT's ability to have no business and all the valuation. Skippy picks a fight over the investing book A Simple Path to Wealth. Doogles covers a tweet about joining Nvidia as a new grad in 2013. The episode wraps talking about Michael Saylor selling Microstrategy to buy bitcoin and an interview with Aswath Damodaran.

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[Replay] The Market Has the Mouth of a Saylor

Mon, 25 Mar 2024 02:30:00 -0700

This is a replay of episode 77 from 2022.

Doogles recaps an article from The Atlantic about ending the "millennial subsidy." Skippy discusses the importance of companies adjusting right now to make sure they can last. Doogles gets gleeful about the "crypto winter" and shines a special light on Michael Saylor's continual dangerous pumping of Bitcoin. Skippy brings up a recent interview with Stan Druckenmiller from the Sohn Conference (awesome interview!). The episode wraps with some top notch listener mail — how does Skippy think about companies with debt, and whether bear markets are getting shorter.

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Six of One and 4000 Billion of the Other

Mon, 18 Mar 2024 02:30:00 -0700

Doogles talks through the most wealth destroying funds of the past decade. Skippy highlights the top 10 highest rated investment books. Doogles continues doom and gloom with the current level of non-mortgage interest payments in the US. The episode wraps with the best and worst capital efficient industries and the state of the Indian options market.

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Norway Or the Highway

Mon, 11 Mar 2024 02:30:00 -0700

Skippy talks about how Norway's sovereign wealth fund is thinking about getting into private equity. Doogles covers UBS' most recent global yearbook. Skippy pits Nvidia against some blue chip all stars. The episode wraps with the worst performing fund of the last 20 years and accepted lying in politics.

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It's Coal, It's Got the Juice

Mon, 04 Mar 2024 02:30:00 -0700

Things kick things off with listener mail on an interview with David Einhorn from Greenlight Capital. Doogles declares that the time of loosey goosey returns are over in retail. Skippy goes back in time, comparing the railroad industry in 1900 to tech stocks today. The episode wraps with Li Lu's principles of value investing.

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I Like to Be In America! For a Small Fee in America!

Mon, 26 Feb 2024 02:30:00 -0700

Doogles celebrates that the Japanese stock market is back to all time highs. Skippy rains on the parade by comparing Japan in the late 80s to big tech in the US today. Skippy walks through the price of the American dream according to Investopedia. Doogles talks process improvement, iBond redemption and hard to pronounce company names. The episode wraps with insider trading by the husband of a BP employee.

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ETF Yields So Hiiiiiiiiigh, High Above Me

Mon, 19 Feb 2024 02:30:00 -0700

Doogles covers listener mail on how Dave Ramsey is losing the under 40 crowd. Then he follows Jason Zweig's advice to watch out for covered call ETFs with supposedly high distribution yields. Skippy recaps three bets: Nvidia valuation, Meta, and Kohl's. Doogles shuns an Airbnb arbitrage scheme. The episode wraps with how Americans are feeling alone, the Buzz ETF coming to roost, and Lyft earnings.

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Choke the Woke, End Up Broke

Mon, 12 Feb 2024 02:30:00 -0700

Doogles tries the find the bottom of the Chinese stock market. Skippy wonders if the current model for the NCAA is about to end. Loud budgeting might be a friendship saver. Doogles doesn't understand whey there is proposed investor ESG regulation. The episode wraps with a $25 million deep fake fraud scam in Hong Kong.

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Smart Money Bets on Liberty Biberty

Mon, 05 Feb 2024 02:30:00 -0700

New Goldman Sachs report continues to say bet on America. Baupost, Point72, Berkshire and more are making an arbitrage bet on Liberty SiriusXM. TikTok investors continues down the nonsense train, and we love it. Chamath shuts down plans to raise a VC fund. Skippy and Doogles cover each of their recent top book recommendations.

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Housing is a Lens Into Civilization w/ Conor Dougherty (author of Golden Gates)

Mon, 29 Jan 2024 02:30:00 -0700

Skippy and Doogles sit down with Conor Dougherty, New York Times reporter and author of Golden Gates: Fighting for Housing in America. We discuss the role of the city, land investments in Detroit, government acting as real estate investors and more.

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Celebrating That Rent-a-Center Culture

Mon, 22 Jan 2024 02:30:00 -0700

The S&P 500 returns to all time highs! Skippy points out that Chinese stocks aren't a cause for celebration and Alibaba fundamentals aren't matching its stock performance. Doogles highlights investment lessons from 2023 according to Morningstar. Skippy goes to Rent a Center to get some Jordan 5s. The episode wraps with a politically charged economic survey, commercial real estate remains a conundrum and listener mail.

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Dat Money Be Gone

Mon, 15 Jan 2024 02:30:00 -0700

Skippy and Doogles cover listener mail on a blogger turned investor named Eddy J Elfenbein. Doogles is interested in the concept of expiring money. Skippy pours one out for Nick Saban, who retired last week. The episode wraps discussing the "quant winter" and Cliff Asness, and a shout out to Howard Marks' latest memo.

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Running 5Ks Does Not An Investor Make [2023 Episode Compilation]

Mon, 08 Jan 2024 02:30:00 -0700

For "I Roll With Skippy & Doogles" annual premium membership subscribers, we cover last year's portfolio performance (+26% for Skippy, +31% for Doogles) and this year's stock picks.

For all our other valued listeners, we have a compilation of some your favorite hits from last year — Tim Ferriss asks Warren and Charlie a question, a CEO values his time way too highly, Jokic doesn't care about basketball, and life lessons. Enjoy!

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Bird Bird Bird, the Bird Ain’t the Word

Mon, 01 Jan 2024 02:30:00 -0700

Doogles gives a recap of ARKK's 2023 performance. Skippy hits on performance highlights of different assets during the year. Doogles talks about the Vail vs. Alterra US skiing duopoly. Skippy hates on wasteful spending at universities, focusing on Auburn. The episode wraps with the sad and epic tale of Bird scooters.

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When They Move, We Move, Just Like That

Mon, 25 Dec 2023 02:30:00 -0700

The episode kicks off with listener mail on UPenn wunderkind value investors and Congress continuing to trade on individual stocks. Doogles takes awe at the Magnificent 7 and their continued dominance. The episode wraps with China's crackdown on gaming and Advertise Now, Pay Later.

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Rich Elon, Poor Elon

Mon, 18 Dec 2023 02:30:00 -0700

Doogles kicks off with listener mail on a playful strategy of buying the dip on anti-wokism. He then covers a piece on Elon Musk's financial troubles. Skippy discusses the complexity of making sports stadiums into economic development areas. Doogles talks signs that it's not time for a recessions. The episode wraps with Gen Z's favorite fashion brands, doomsayers, and a layout of US companies' geographic and income targeting.

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All You Can Eat Debt Buffet

Mon, 11 Dec 2023 02:30:00 -0700

Doogles walks through the economics of all you can eat buffets. Skippy drops a few more Charlie Munger quotes and discusses the recent interview between him and the Collisons. Doogles is impressed with the results from the largest universal basic income experiment. The episode wraps talking about the current state of corporate debt.

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Feeling That Munger Hunger

Mon, 04 Dec 2023 02:30:00 -0700

RIP to Charlie Munger. Doogles gives a PSA on the DJ Envy real estate debacle, and paying attention to what celebrities are pitching. Skippy hits on how stocks crushed in November. Doogles talks correlation between when people come of age and their percentage equity allocation. The episode wraps with Mark Cuban's gangsta move on selling the Mavs.

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Junk Bonds Got the Yields to Make Your Booty Go Smack

Mon, 27 Nov 2023 02:30:00 -0700

It's Black Friday at retailers, and at the Skippy and Doogles podcast. Check out our premium deals. Nvidia releases blow your mind earnings (again). Skippy lays out some stock research recommendations. Doogles tells a story from Gretchen Morgensen's book The Plunderers about private equity. The episode wraps with a Morgan Housel piece called the Full Reset and a FINRA marketing proposal that likely won't work.

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I Do Not Like It Sam I Am

Mon, 20 Nov 2023 02:30:00 -0700

Skippy and Doogles try to find the logic of Sam Altman’s boot from OpenAI. Doogles enjoys a Kayla Scanlon piece on the perception of the economy. Skippy hits on a couple points from Morgan Housel’s latest book. Doogles talks inheritance and inequality. The episode wraps with a quiz on real estate, a nice take on Goldman Sachs and how much you should be taking out of your retirement each year.

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Just Stop, Dave Ramsey

Mon, 13 Nov 2023 02:30:00 -0700

Skippy declares that it's definitely time to stop listening to Dave Ramsey. He also is intrigued with a mining company that may have some hidden gems. Doogles doesn't like the incentive structure that's been given to startup companies. Skippy doesn't understand how Isiah Thomas didn't know he and MJ had beef. The episode wraps talking about zombie companies.

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Ye And His Adidas Do the Illest Things

Mon, 06 Nov 2023 02:30:00 -0700

Skippy calls the SBF trial boring. Doogles lays parallels between Adidas, Kanye West, and the stock market. A CEO is upset that his buybacks aren't increasing his stock price. Doogles highlights recent Charlie Munger interviews. The episode wraps with WeWork, investing and the economy, and Stanley Druckenmiller calling out Janet Yellen.

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Free Will(y)

Mon, 30 Oct 2023 02:30:00 -0700

Skippy rips Doogles on his Twilio position. Doogles covers a recent Wall Street Journal article about mini-millionaires. Skippy discusses the existence of free will according to Stanford professor Robert Sapolsky. Doogles continues his tirade on the state of the American consumer. The episode wraps with Twitter losing authenticity, life lessons and Jamie Dimon selling shares.

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Snitches Get Riches

Mon, 23 Oct 2023 02:30:00 -0700

Skippy covers Morgan Housel's latest — A Few Laws of Getting Rich. Doogles is a fan of Paul Graham's post on being Superlinear. Skippy is mind blown and angry at Howard Marks. The episode wraps with Microsoft news and the loss of home purchasing power.

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Slimmer Waistlines, Slimmer Returns

Mon, 16 Oct 2023 02:30:00 -0700

Doogles goes down a professorial rabbit hole about weight loss drugs — Ozempic, Wegovy and Mounjaro — and their impact on the stock market. Skippy gets YIMBY and NIMBY about IRS audits. The episode wraps with an overview of a Zelle pool purchase scam.

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Impendio Infinitus

Mon, 09 Oct 2023 02:30:00 -0700

Doogles continues his tirade on company spending after reading a Wall Street Journal piece on US consumers acting like there's no tomorrow. Skippy talks Amazon's (alleged) price raising algorithm. Doogles loves a recent Noah Smith post about not falling victim to viral charts. The episode wraps with a book report from Skippy on Michael Lewis' new book Going Infinite.

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For the Love of the Fat Bears

Mon, 02 Oct 2023 02:30:00 -0700

Skippy and Doogles answer listener mail about some individual stock listener mail. Doogles hits on the difference between inflation rate and price levels. Skippy sees consumer credit card debt continue to rise. Doogles covers a JP Morgan piece on keeping investments simple. Skippy closes the loop on Dave Ramsey's beating the S&P 500 claim. The episode wraps with why selling is hard.

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Government Does Itself No Favors

Mon, 25 Sep 2023 02:30:00 -0700

Skippy has a bone to pick with Dave Ramsey. Doogles walks through an awesome talk that Bill Gurley gave at the All In conference. Skippy is amazed and encouraged by how much Singapore pays its government officials. Doogles sees danger in American's distrust of data and the state of the economy. The episode wraps with a paper about historical inflation shocks.

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Would a Stock Without a Dividend Earn As Sweet?

Mon, 18 Sep 2023 02:30:00 -0700

Doogles takes guidance from Mr. Money Mustache on what to do with your money in this "high interest rate" environment. Skippy schools in the difference between price only and dividend-inclusive returns. Doogles pulls out some investing lessons learned from New Found Research. The episode wraps with Skippy laughing at startup projections (including Starlink's) and a tweet on the difference between lifestyles in the US and Spain.

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Indebted and Fretted

Mon, 11 Sep 2023 02:30:00 -0700

Doogles is bewildered by a New York Times piece on the impact of college degrees on the wealth premium. Skippy sees more evidence of sophisticated ETFs using leverage, and wonders if that's smart or a sign of the times. Doogles has a car-filled double whammy — cars are more expensive and more invasive. The episode wraps with more executive sales of Nvidia stock.

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Getting My Stock Tips At Auntie Anne’s

Mon, 04 Sep 2023 02:30:00 -0700

Skippy spits knowledge on Nike shoe margins. Doogles tackles listener mail about mean reversion. Skippy has quick hits on Tesla price cuts and Nvidia price gains. Doogles is in awe of Li Lu's guest lecture at Columbia Business School from 2006. The episode wraps with pretzel fraud, Nick Maguilli's redemption, consumer credit and a 'what if' on interest rates.

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SPAC’d In the Face With Reality

Mon, 28 Aug 2023 02:30:00 -0700

Chamath gets called out (again) for the poor performance of his SPAC empire. Doogles discusses a blog post about KPI psychosis. Skippy hits on market forces and the US minimum wage. Doogles wraps the episode with a controversial discussion on mean reversion.

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When I Rich, You Rich, We Rich

Mon, 21 Aug 2023 02:30:00 -0700

Skippy points out that people are reading Michael Burry's 13F all wrong. Doogles loves the question raised by Gary Marcus around what if Generative AI is a dud. Skippy hits on rich people that feel poor. The episode wraps with the misuse of autonomous vehicles and speculation on the future of the US economy.

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A Mighty Big Bite of the Apple

Mon, 14 Aug 2023 02:30:00 -0700

Doogles highlights an Axios piece on how America might be losing its hustle. Skippy questions Berkshire Hathaway holding such a large position in Apple. Doogles pushes back hard on Nick Maggiuilli's take on income as a predictor of wealth. Skippy gives an update on Investment GPT's performance. The episode wraps with some gems from a 2006 interview with Bill Miller and a take on high yield stock performance.

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Retire? I Don’t Even Know Her!

Mon, 07 Aug 2023 02:30:00 -0700

Doogles talks about Americans' retirement readiness (spoiler alert: they're not ready). Skippy recaps some points from the Bill Perkins book Die With Zero. The Yellow Trucking logo debate continues. Doogles hits on a recent David Einhorn interview about value investing and parlays that into an analysis on the accuracy of guru market predictions. The episode wraps with Ben Carlson's article on the lack of importance of one year returns and the demise of another shopping mall.

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Seeing the World Through Yellow Colored Glasses

Mon, 31 Jul 2023 02:30:00 -0700

Skippy drops knowledge about running a rental car business in Dubai. Yellow trucking is going bankrupt after 99 years. Doogles covers a Collab Fund piece on cyclicality. US car prices have shot up, a potential sign that a soft landing may not happen. Doogles talks Japanese demographics. The episode wraps talking about Mbappe's $1b offer from the Saudi Arabian football club and US higher education elite college admissions by income.

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We Will All Be Robots Soon

Mon, 24 Jul 2023 02:30:00 -0700

Doogles has fun with a post that highlights how we've been saying that robots are taking over the world for over 100 years. Skippy has a problem with Nick Maguilli's recent piece called The Problem With Valuation. Doogles dives into a San Francisco child education account program. Skippy hits on key points from a recent Invest Like the Best podcast episode with Jeremy Giffon. The episode wraps discussing the Fed Now program and a Curbed article about commercial real estate.

TayTay Day

Mon, 17 Jul 2023 02:30:00 -0700

This is a premium episode week, so our public episode is short. If you want to become a premium subscriber, head over and join the Skippy and Doogles fan club.

On the premium episode, Skippy and Doogles discuss recent investment news, and then tackle ways to increase yours savings rates and specific stocks that are hitting their radars — research recommendations!

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Gotta Lose Money to Make Money

Mon, 10 Jul 2023 02:30:00 -0700

Skippy says it's time to look into considering selling those I Bonds. Doogles dives into a research paper about cognitive bias in financial decision making. Skippy is fascinated by slot machine gamblers making money on YouTube. The Musk/Zuck battle continues through the launch of Threads. The episode wraps with a conversation about the impact of interest rates on different parts of the inflation battle.

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Things Are Going South

Mon, 03 Jul 2023 01:30:00 -0700

Famed Colorado restaurant Casa Bonita won't use tipping. Skippy hits on economic growth happening in the Southeast US. Doogles is loving a recent Collab Fund piece "A Few Questions". Skippy discusses Morningstar's survey on why people pick financial advisors. The episode wraps with Gen Z's views on retirement and saving the world by printing and distributing $2 trillion.

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The Billionaire Death Match

Mon, 26 Jun 2023 02:30:00 -0700

Elon Musk and Mark Zuckerberg have decided to fight in a cage match. Warren Buffett is amazing. TransDigm shows CEOs can sell stock and still be bullish. Doogles walks through a Morningstar piece on portfolio mistakes. Skippy covers the benefits of living abroad and self awareness. The episode wraps with a recent interview of Bill Ackman by Harry Stebbings.

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Nuggets of Wisdom

Mon, 19 Jun 2023 02:30:00 -0700

Nikola Jokic responds to the Nuggets winning the championship as only he would. Reddit under fire for charging for API usage. Skippy lays out clear IRS data on where it should focus its audits. Doogles takes issue with corporate profits. Americans see tipping getting out of control. The episode wraps with Nvidia leadership selling shares, Cathie Wood buying Meta, and the continued divergence of growth vs. value.

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When Puts Comes to Shove

Mon, 12 Jun 2023 02:30:00 -0700

Casa Bonita is back in Colorado! Apollo's CEO says there's no alpha in the market. Skippy's Dave Ramsey disappointments continue. Doogles doesn't like Vegas changing the gambling odds. Skippy celebrates Messi coming to the US. Doogles compares Brandon Marsh's controlled aggression in baseball to good investing practices. The episode wraps with Skippy's decision on betting against Nvidia, and a great post by Nick Maggiulli on being rich and desperate.

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All Hail the Salvatious Seven

Mon, 05 Jun 2023 02:30:00 -0700

Nvidia is even too expensive for Cathie Wood. Skippy highlights the historical performance of the top 10 market cap stocks before and after they join the top 10. Doogles is foolishly amazed at how little cash the US government has relative to billionaires' net worth. What does Dollar General's performance say about the state of the US economy. The episode episode wraps with a breakdown on the cost allocation for food delivery apps.

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From the Pub to Your Ear Buds

Mon, 29 May 2023 02:30:00 -0700

I know we said this was a week off, but Skippy couldn't hold back — even though he's galavanting about Europe. We have a short emergency pod, hitting on Nvidia's uncanny rally continuing, current performance concentration in the S&P 500, the ascent of South Korean food, and the negative correlation between investment experience and investment confidence.

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Scurry Burry Investing Up a Flurry

Mon, 22 May 2023 02:30:00 -0700

On a quest for ridiculous things, Skippy hits on Michael Burry's portfolio and Nvidia's current valuation. Doogles is still interested in Japanese stocks. Skippy shakes his head at people throwing their money at the ChatGPT Portfolio. Doogles is saddened by the state of financial literacy in the US, backed by a recent research paper. The episode wraps with an overview of GMO's latest piece, and a homage to Sam Zell.

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Mungermania LVIII

Mon, 15 May 2023 02:30:00 -0700

Skippy ponders what we choose to measure and what we don't — centered around the NFL teams' varying travel schedules. Then he discusses Stan Druckenmiller's recent USC doom and gloom speech. Doogles fanboys over parts of the Berkshire Hathaway annual meeting. Skippy hits Doogles-inspired hot buttons: Robinhood, Twilio, and Cathie Wood. The episode wraps with a quick take on Propublica's recent piece on 'We Buy Ugly Houses'.

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No Pain, No Premium

Mon, 08 May 2023 02:30:00 -0700

Doogles marvels at how AI is changing...meaning Allen Iverson to Artificial Intelligence. Skippy takes the Warren Buffett challenge. Doogles walks through a recent AQR report on international diversification. Skippy can't believe that UC schools students are fighting to live on camp sites with current lack of affordability. The episode wraps with people being more worried about bank safety now than in 2008, and Chegg's stock hit on ChatGPT fears.

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I Feel REITs In My Fingers, I Feel REITs In My Toes

Mon, 01 May 2023 02:30:00 -0700

Skippy explores how much more money it would take for millionaires to be happy. Doogles covers a research paper on global stock wealth creation over the last 30 years. Skippy hates earnings week. Commercial real estate is not looking so good (REITs, anyone?). The episode wraps with talking about how rampant fraud is out there, and an article by Jason Zweig on college classes picking stocks for the long term.

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One Way Ticket Out of Pity City

Mon, 24 Apr 2023 02:30:00 -0700

Another CEO video, another foot in mouth — this time by the CEO of MillerKnoll. Doogles is impressed with Taylor Swift's financial savvy. Skippy is upset about the Tesla price drops, and then hits on a Conference Board report on economic leading indicators. Doogles talks through a software developers take on the impact of ChatGPT. The episode wraps with someone's ridiculous valuation of their own time, and an Atlantic article on the Myth of the Broke Millennial.

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Turning Kohl's Into Diamonds

Mon, 17 Apr 2023 02:30:00 -0700

Skippy kicks things off with two deep thoughts style quotes. Doogles uses the recent Warren Buffett interview with CNBC to quiz Skippy. Then they go into a series of quick hits on Jim Simons, staying invested, labor participation, Kohl's, Cathie Wood and more! The episode wraps with Doogles spitting a hot, and likely wrong, take on inflation.

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No Work And All Play Makes Jack A Dull Boy

Mon, 10 Apr 2023 02:30:00 -0700

Tech workers are saying that the main thing they don't do is...work. Doogles walks through Jason Zweig's seven traits of great investors. Skippy continues to watch the real estate market head toward bad. Doogles mocks active manager performance. The episode wraps with Skippy's amazement at Alan Greenberg's commitment to saving money for Bear Sterns in the 1980s.

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Two Good Friends and a Microphone [Seafarer Investor Podcast Interview]

Mon, 03 Apr 2023 02:30:00 -0700

Seoshin, host of the Seafarer Investor Podcast, interview Skippy and Doogles about their investing styles, what books they recommend, and what it's like to do the pod. Appreciate you, Seoshin, and hope you all enjoy!

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Stay In Your Lane, Liam Neesons

Mon, 27 Mar 2023 05:45:00 -0700

Doogles is concerned that Americans fear for the worst. Skippy likes free markets, so questions the new Los Angeles "mansion tax." Doogles gets amped about executives trading the stocks of their competitors. Skippy reviews an article about the spending and investments of people with less than $1 million at retirement. The episode wraps with nonsense interest rate expectations and a fraud score created by some smart academics.

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Why Can't Banks Just Be Normal?

Mon, 20 Mar 2023 02:30:00 -0700

Skippy and Doogles tackle some great listener mail asking why banks are always at the center of crises, and are any banks doing it right? Then they eye a few potential opportunities in the market. The episode wraps with a debate on what they would do next week if they were Jerome Powell — to raise or not to raise.

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You Down Wit SVB? Yeah FDIC!

Mon, 13 Mar 2023 02:30:00 -0700

Doogles thinks the world has gone too far with the new "body doubling" trend of watching other people work online. Skippy highlights how dividend investing during inflationary periods has historically paid...well, dividends. Doogles loves Bill Ackman's Covid trio investing homeruns. Skippy covers a great post about debating whether housing should be viewed as an investment. Then, what the people really want — what the heck happened with Silicon Valley Bank?? The episode wraps with a quick hit on betting on the WWE.

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America’s Got 99% Problems And Housing Is One

Mon, 06 Mar 2023 02:30:00 -0700

Doogles nerds out on a Todd Combs interview from the 2022 Graham and Dodd breakfast, looking at how Warren Buffett, Charlie Munger and Todd Combs analyze companies. Skippy highlights the fact that housing in America is historically unaffordable. Doogles shows that most goods and services that people need are also historically unaffordable. The episode wraps with quick hits on InvestmentGPT, whether it's time to buy bonds and the nonsense that is WeWork.

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Fees, Sir, I Want Some More

Mon, 27 Feb 2023 02:30:00 -0700

Skippy is appalled at Edward Jones' investment fees. Doogles finds Tim Ferriss' question asking at the 2008 Berkshire Hathaway meeting adorable. Skippy falls out of his chair at the number of developers working on Bitcoin's core. Doogles highlights a Twitter thread about A16Z. The episode wraps with the Airbnb bubble, AQR's 2022 performance and listener mail about climate change and Coinbase.

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Munger Don’t Care About You Or Anything That You Do

Mon, 20 Feb 2023 02:30:00 -0700

Doogles uses Winnie the Pooh's new horror film to spark a debate about "iconic copyrights". Skippy honors Charlie Munger's most recent curmudgeonry. Doogles explores a recent New York Times piece exploring an off the wall Bing AI experience. The episode wraps talking about stock buybacks and the dominance of the NFL.

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Beware the Sharknado Recession

Mon, 13 Feb 2023 02:30:00 -0700

Skippy learns more about Adam Neumann's company Flow, and is not impressed. Doogles fears for the future of Affirm and buy now, pay later. Skippy is entertained by college football economics. Pessimism continues to rule humanity. The episode wraps with a conversation about having a healthy relationship with money, the AI battle between Google and Microsoft, and continued layoffs.

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Johnny Needs a Fast Car

Mon, 06 Feb 2023 02:30:00 -0700

Skippy asks whether executive compensation, and humans' need for more, has gone too far. Doogles highlights a post from Investment Talk that walks through value investor Seth Klarman's 20 lessons from the Great Financial Crisis of 2008. Skippy talks about the book The Wealthy Barber, which Doogles finally read. Doogles walks through Greenlight Capital's most recent investor letter. The episode wraps discussing how US consumers are hurting, the current take on Meta's stock, and a research report analyzing the correlation of perceived penis size to wanting to buy expensive sports cars.

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Simply the Best, Worse Than All the Rest

Mon, 30 Jan 2023 02:30:00 -0700

Skippy lays out who wins and loses in the rewards credit cards game. Doogles pleads for the Belfer family to stop investing. The Anti-Jim Cramer Twitter account is on fire these days. Doogles walks through a study of active fund managers, and their views on the active vs. passive debate. Skippy wraps the episode discussing Bill Gurley's recent guest appearance on the Tim Ferriss Show podcast.

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Fantastical Rates and Where to Find Them

Mon, 23 Jan 2023 02:30:00 -0700

Doogles agrees that tech needs to stop doing stupid stuff that lead to people being laid off. Skippy is scared for the real estate market. Bill Gurley puts out tweets telling startup employees that it's time to get to work. Skippy accidentally joins meme stock mania after Ryan Cohen buys Alibaba stock. Doogles gets nerdy, covering a research paper with stock charts usually not seen. The episode wraps with a quick hit on Schiller CAPE and smart ways to manage excess cash.

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I Left My Wallet in El Tokyo

Mon, 16 Jan 2023 02:30:00 -0700

Skippy exposes that Tesla may just be a car company, and the importance of understanding fat tails in financial markets. Doogles chronicles the lost decade in Japan. Skippy runs through the economics of public transportation. Doogles is awed by the profile of a young, spry Warren Buffett. The episode wraps with quick hits on Microsoft's potential investment in OpenAI and the constant oversharing by FTX's Sam Bankman-Fried.

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Office Space is a Comedy, Not a Blueprint [2022 Episode Compilation]

Mon, 09 Jan 2023 02:30:00 -0700

For "I Roll With Skippy & Doogles" premium subscribers, we do a 2022 portfolio review and talk through our purchases for 2023 (you can sign up here).

For all our other valued listeners, we touch on new topics like Skippy and Doogles guest star on the Seafarer Investor Podcast (Apple, Spotify), "rookie traders" leaving the market, Salesforce troubles and an embezzlement scheme based on the movie Office Space. And then we provide a compilation of some of the most popular clips from 2022. Enjoy!

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Closing Out An Eggstraordinary Year

Mon, 02 Jan 2023 02:30:00 -0700

Doogles is amazed at the rise in egg prices, and how the current avian flu gets no attention. Skippy points out how much people are spending on their cars. Doogles sees a coming back to Earth for SPACs and AMC's stock price. Skippy wonders how the fact that 10 year stock return predictions roughly matching treasury yields will impact investment. The episode wraps with a discussion on earnings predictions vs. stock return predictions and a couple pieces of listener mail.

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Bow Knows This And Bow Knows That

Mon, 26 Dec 2022 02:30:00 -0700

Skippy covers the importance of chance and the movie It's a Wonderful Life. Doogles is McLovin the fact that FTX execs are flipping like flapjacks. Santa Clauses are making bank...and maybe this is related to home sales declines. Doogles covers Cathie Wood for one last time (maybe...). The episode wraps with talk of gift cards, gift cars, and Dogecoin vs. Coinbase.

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Deion Sanders Up In China

Mon, 19 Dec 2022 02:30:00 -0700

Doogles wonders if the White House leak of the CPI report is real. Skippy can't believe that Cathie Wood thinks that Zoom growing by 10x is the worst case scenario. Doogles covers a recent post about imitation and counter-signaling. Skippy highlights a Michael Moubassian study on capital allocation by CEOs. The episode wraps discussing performance culture at companies, covid in China, UCLA's decision to leave the Pac 12 and the power of shared accounts for married couples.

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The Pied Piper of New York City

Mon, 12 Dec 2022 02:30:00 -0700

NYC is looking for a rat czar, and Skippy might be interested. Doogles covers Fred Wilson's take on real estate and public stocks. Skippy covers the growing US vs. international stock divide. Doogles gets academic, looking at a KCP blog post on right vs left brain thinking. Blackstone's real estate shenanigans continue. The episode wraps with a convo on inverted thinking, big banks being stingy with savings, and inflation is gonna take awhile.

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Little Caesars is Dead, Long Live Little Caesars

Mon, 05 Dec 2022 02:30:00 -0700

There's one week left in the 60% off premium sale!

Skippy drops knowledge on the top food joints in America. Doogles walks through an article on how some countries are able to grow out of poverty, while others can't. Skippy tests Doogles' knowledge on industry growth during and post Covid. Listener mail covers (literally) shorting GameStop and Jim Cramer's follies. The episode wraps with a historical take on the impact of inflation on stock market valuations.

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You Gotta Spend Money to Spend Money

Mon, 28 Nov 2022 02:30:00 -0700

It's Episode 100! To celebrate, for 2 weeks take 60% off premium subscriptions to the show — thank you for supporting!

Skippy rants about the "buy more to save more" ethos. Doogles covers Howard Marks' recent memo, What Really Matters. The UN says that India's population is now greater than China's (and China is fading quickly). Doogles runs through some graphs from a recent Animal Spirits podcast episode on the 10-year treasury, savings vs. debt, Netflix vs. Disney, and Bird Global stock. The episode wraps with a conversation about high yield convertible notes.

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The SEC Doesn't Regulate Poop Emojis

Mon, 21 Nov 2022 02:30:00 -0700

Doogles covers recent happenings in the South Korean bond market caused by a fiasco at Legoland. Skippy heads back to FTX coverage, including its assets/liabilities and bankruptcy filing. Speaking of fraud, Elizabeth Holmes gets sentenced. Doogles highlights Elon Musk's ultimatum and the Twitter exodus. The episode wraps with some soapbox dialogue on Cathie Wood.

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Angela Lansbury Would Be Disappointed

Mon, 14 Nov 2022 02:30:00 -0700

Elon Musk unleashed the blue check mark and the internet goes wild. The crypto exchange, FTX, shows its true colors...and they don't look good. Elon Musk sends his first email to Twitter employees, and no one is happy. Doogles gets up in arms about a blog post about stock based compensation. The episode wraps with Mattress Mack winning big, and WeWork continuing to be WeWork.

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Welcome to the Janet Jackson Market

Mon, 07 Nov 2022 02:30:00 -0700

Skippy learns that if you win the lottery, don't tell your family. Skippy and Doogles debate the Alibaba investment thesis. Doogles is way too excited about earnings season, starring Twilio and Meta. Consumer debt and CEO sentiment perpetuate negativity. The episode wraps with a discussion on the Freakonomics episode about personal finance gurus and the current state of worker productivity.

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It's Cool to Be Kind w/ W. David Marx (author of Status and Culture)

Mon, 31 Oct 2022 02:30:00 -0700

Skippy and Doogles chat with W. David Marx, author of Status and Culture. David discusses what creates status in society, the economics of status, the impact of status on culture, and more. It's a fun and interesting conversation about society.

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Sideways Markets From Wayside School

Mon, 24 Oct 2022 02:30:00 -0700

Skippy and Doogles cover some bear market history to give a sense for how long this thing could last. They review JP Morgan's most recent Guide to the Markets. Skippy highlights the relationship between mental health and toxic work. The episode wraps with a brief rant on Peloton's former CEO's margin calls and a review of Open AI.

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Wood You Mind Slowing Down?

Mon, 17 Oct 2022 02:30:00 -0700

Even Taco Bell can't escape this bout of inflation. Doogles can't comprehend how the Wall Street Journal let a recent stock diversification article go to print. Skippy calls out Cathie Wood's open letter to the Fed. Doogles highlights the indirect rebuttal to Cathie Wood by the investment research firm Strategas. The episode wraps with Mark Zuckerberg's failing persistence to be the face of Meta, and two pieces of listener mail.

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Can You Keep Up? FDR Make Me Lose My Breath

Mon, 10 Oct 2022 02:30:00 -0700

Ray Dalio steps down from Bridgewater Associates, going out on top. Skippy thinks the UN is out its lane by asking central banks to halt rate increases. GMO has an interesting report on the tie between currency value disparity and investment returns. Doogles quizzes Skippy on best and worst performing stocks year-to-date. The episode wraps with a fantastic piece of listener mail that hits the heart of difficult investor psychology.

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Housing Be Beamin' While the Market's Screamin' Lehman

Mon, 03 Oct 2022 02:30:00 -0700

Skippy and Doogles release a premium episode hitting on some of their recent buys (you can become premium here). Cathie Wood is back to spewing economic nonsense. Housing remains expensive. Doogles recaps a Mark Suster post on what VC will look like after the crash. Skippy hits on data showing that market sentiment is near all time lows. Doogles covers Howard Marks' recent memo and discusses forecasting. The episode wraps with Annie Duke's new book "Quit."

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Weak Ties, Strongly Held

Mon, 26 Sep 2022 02:30:00 -0700

Skippy covers a recent study by LinkedIn on the value of weak ties and criticism about the study from a New York Times piece. Doogles enjoyed points raised in a recent post called "What I Miss About Working at Stripe." They then hit on the current state of the market and how they're working through that psychology. The episode wraps with a reminder that stock analysts suck.

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Peloton is the Jim Cramer of Companies

Mon, 19 Sep 2022 02:30:00 -0700

Kyle Bass captures the market's state of affairs perfectly on Meb Faber's podcast. Skippy highlights that banks are now losing deposits. Doogles continues to fear how much debt consumers are getting into. Peloton can't make a good decision to save its company, and Patagonia makes a great decision to give away its company. Doogles shines on more Jason Zweig goodness as he writes about international stock bargains. The episode wraps with the inevitable pain that comes with the simultaneous rise in housing prices and interest rates.

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Interest Rates Are Up…But Not For Your Savings

Mon, 12 Sep 2022 02:30:00 -0700

Doogles raises up a report by GMO calling for the fall of the "Superbubble". Skippy discusses banks, interest rates, and why big banks aren't keeping up with the rise. Doogles loves Jason Zweig's take on whether pricing power stocks are the way to go right now — exploring the 1970s are a historical case study. The episode wraps discussing the asymmetric world of book sales.

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It's Not Right, And It's Not OK

Mon, 05 Sep 2022 02:30:00 -0700

AMC's executives stay savvy and keep cashing out. Doogles is into Morgan Housel's "Big Beliefs" and simplification. Skippy is not surprised that folks confuse the words of Jason Zweig with Benjamin Graham. Doogles compares the art of writing with investing through Herbert Liu's blog. Skippy highlights the generational divide around "quiet quitting". The episode wraps with a convo on the gender pay gap, revenue increases due only to price increases, 401K nonsense, and the rental to buyer price ratio.

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It’s APE’s World, We Just Live In It

Mon, 29 Aug 2022 02:30:00 -0700

Skippy learns that Kevin Durant is rich. The most creative listener mail to date throws shade at A16Z and Adam Neumann for the recent investment in Flow. Doogles walks through AMC's most recent fundraising jujitsu. Skippy debates Biden's student loan forgiveness executive order. The episode wraps discussing the recent auditing agreement between China and the US, and Mark Zuckerberg on Joe Rogan.

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Out of the Frying Pan, Into the Prison

Mon, 22 Aug 2022 02:30:00 -0700

Skippy is fascinated with car wash roll ups. Doogles wonders why Gen Z isn't saving, but is betting big on Bed Bath & Beyond. Skippy puts out a PSA on Dan Price. Doogles highlights Michaels Burry's recent move to sell all his stocks and buy into prison company Geo Group. The episode wraps with Doogles hitting on Klarna's layoffs back in May and Skippy firing off some hot takes on the highest tipping states, the comeback of international stocks, college football's NIL rules and scary worker productivity tech.

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Playing Hot Potato With Dynamite

Mon, 15 Aug 2022 02:30:00 -0700

Doogles confuses Skippy with an Indian man that sued Indian Railways for $0.25. They review the Inflation Reduction Act. Skippy kicks off a discussion on the low reading levels across America. Doogles wraps the episode continuing the "what's the next surprise" conversation looking at current levels of corporate and consumer debt.

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The Predictive Power of Trousers and Trainers

Mon, 08 Aug 2022 02:30:00 -0700

Doogles revisits the discussion around the Fed raising interest rates all at once. Skippy raises the price to sales ratio of the recent purchase of the Denver Broncos. Michael Saylor is out as CEO of Microstrategy. Dollar stores are back in the conversations, quickly becoming the de facto grocery store for folks. Doogles discusses separating signal from noise, using a recent Farnam Street post and tips from Richard Feynman. Skippy is marveled by the UK's ability to precisely predict recessions. The episode wraps with Doogles pontification on what the next market surprise will be.

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TINA and TASA in a TUSSLE

Mon, 01 Aug 2022 02:30:00 -0700

The episode kicks off with the White House hedging on the definition of a recession. Doogles covers a post by Morgan Housel about the power of pattern matching. There's a robust conversation about housing — first on the role that government can play in long term housing stability, and then the pain that mobile home park residents are facing. Skippy wraps the episode with developing nations being put into debt, an innovative way to fight global warming, and how Halloween won't be the same this year.

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The Value In Preparation w/ William Green

Mon, 25 Jul 2022 02:30:00 -0700

William Green (author of Richer, Wiser, Happier) joins the podcast for the second time. It's a great conversation where we discuss what he learned since the book was released, what it's like to transition to a podcast format, and reflections on being close to some of the world's greatest investors. It is valuable, enlightening and vulnerable discussion.

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Powell, Just Get On With It Already

Mon, 18 Jul 2022 02:30:00 -0700

Skippy quizzes Doogles on the most beer guzzling US states. Doogles reviews topics covered in the May 2022 Sequoia Capital deck "Adapting to Endure" on the state of things. Skippy rants about Acorns, and wonders what would happen if Powell just raised rates 3% all at once. Doogles highlights investing red flags covered in the Noahpinion piece "BS in Investing". The episode wraps with a list of countries most likely to default and a heap of listener mail on Peloton, Factfulness, Celsius and Stripe.

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Post Malone Saves the Metaverse

Mon, 11 Jul 2022 02:30:00 -0700

Post Malone gives Doogles more confidence in the metaverse. Skippy recaps the book "Nickel and Dimed" in a convo about news deserts and socioeconomics. Doogles isn't happy that the crypto crash looks like it's hurting black wealth. Millennials are doing just fine, but are scared about their financial futures. In a hopeful reprieve, some evidence that recent generations are doing better than their parents.

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Is Radio Shack the Next Berkshire Hathaway?

Mon, 04 Jul 2022 02:30:00 -0700

Skippy recaps stock performance for the first half of the year (spoiler alert: it's not good). Doogles is enamored with Radio Shack's tweets. Skippy wonders what's up with people not seeing the Kohl's arbitrage. Doogles hits on highlights from a recent paper on being susceptible to financial BS. Skippy raises the parallels between fame and investing, and then gives in to the fact that some crypto might be a ponzi scheme. The episode wraps with a conversation about Atlassian and Columbia pulling out of the US News college rankings.

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Dear Bitcoin, Do You Know How Hedges Work?

Mon, 27 Jun 2022 02:30:00 -0700

Doogles dives into some 2000-2003 stock charts to discuss bear market rallies. Skippy covers another youngmoney.co post on not giving financial advice. Doogles uses a recent Bloomberg piece to highlight the difference between venture capital funds and hedge funds, and how those funds have gotten more conflated as of late. The episode wraps with listener mail about the debt cycle.

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The Market Has the Mouth of a Saylor

Mon, 20 Jun 2022 02:30:00 -0700

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When Bees Are Fish, No Portfolio Is Safe

Mon, 13 Jun 2022 02:30:00 -0700

In California, bees are now legally considered fish...Doogles doesn't know exactly how, but he feels that this will somehow bring down the market. Listener mail brings a youngmoney.co post called The Inefficient Market Hypothesis and evidence that people are flocking to dollar stores. Skippy covers a post on how Americans are beginning to seriously spend their excess savings. Doogles isn't happy with people moving less and less, and the potential impact on economic mobility. Skippy wants everyone to know that inflation is a worldwide issue. The episode wraps with two rants — Doogles on Cathie Wood, and Skippy on Joe's Biden take on Exxon.

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Don't Slap Grandpa at Costco

Mon, 06 Jun 2022 02:30:00 -0700

Doogles recaps a post from The Hustle about people being irrational (especially at Costco) about free stuff. Skippy hits on a CFO survey explaining how folks are thinking about debt, share buy backs and dividends. Investors are flooding into bonds right now. The episode wraps discussing Tommy Hilfiger's recent real estate arbitrage.

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Blue Chips and Red Crackers

Mon, 30 May 2022 02:30:00 -0700

Doogles is excited about the optimism that Jason Zweig brings in a recent Wall Street Journal article, and then Skippy rains on his parade. Skippy recaps some analysis on a YOLO portfolio that bought money losers at the end of 1999. Doogles is upset about people calling TerraUSD a blue chip investment. Skippy is angry about the mismanagement of Peloton. The episode wraps discussing how SPACs are completely falling apart, and Michael Moritz's take on the tech rout.

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If Being Rich is Sexy, Getting Rich Sure Isn't

Mon, 23 May 2022 02:30:00 -0700

Doogles recaps a great New York Times piece on a who are the rich in America and what creates happiness. Skippy discusses that the biggest market cap companies falling is creating most of the downturn...and he investigates some potential arbitrage opportunities. Doogles pulls highlights from a recent post called "The Market is Wrong Bro" about how we psyche ourselves out when riding market waves. Skippy and Doogles debate the differences between buying stocks and buying companies. The episode wraps with a discussion on Melvin Capital shutting down and Skippy drops some year to date stats.

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Numbers Don't Matter in Canada

Mon, 16 May 2022 02:30:00 -0700

The markets continue to fall, setting records held for decades and/or centuries. Skippy and Doogles start with a classic value vs. growth debate on what makes a good buy in a market like this. Then debt continues to pop bubbles — Doogles talks Better.com CEO and his personal loan guarantees, Skippy talks Michael Saylor and Bitcoin, and Doogles rants about buy now pay later. Skippy discusses the reason price divergence in the Terra USD stablecoin (Doogles doesn't get it). The episode wraps with a history lesson on dip buying during the dot com crash, and a discussion on Coinbase's stock plummet and disclosure.

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Sticking Through Thick and Thin w/ Justin Carbonneau (Validea Capital Management)

Mon, 09 May 2022 02:30:00 -0700

We have a special guest this episode, Justin Carbonneau of Validea Capital Management and co-host of the Excess Returns podcast. Justin has over 20 years of investing experience and covers a range of topics — the history of Validea, taking emotion out of investing, what's cheap in the market right now, the future of the 60/40 stock/bond portfolio, his favorite investing strategies, Bitcoin, and more. A fun and wide ranging conversation.

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This Never Happens, Except All the Time

Mon, 02 May 2022 02:30:00 -0700

Doogles compares Kanye to Twitter. People need to stop buying stock exceptions, as evidenced by over $1 billion lost on options by retail investors during the pandemic. Nasdaq hits a 14 month low, and Skippy yawns. Doogles uses a Bill Gurley Twitter thread to discuss how influential the period is when someone starts investing to their perspective on valuations. Skippy highlights the decreased relative affordability of housing over the last 20 years. The episode wraps with a strategy found on Reddit to have risk-free gains on sports betting apps.

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Blame It On the P-p-p-p-p-password Sharing

Mon, 25 Apr 2022 02:30:00 -0700

Skippy kicks off discussing how a Harvard student wrote an article that isn't optimistic about her classmates ability to lead. Doogles is fascinated by the divergence between productivity growth and wage growth in the US. Netflix is crashing and Skippy still can't find value there. The episode wraps with a chat about investing time horizons and Biden's decreasing popularity in the midst of spending so much money.

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A Twitter By Any Other Price Would Smell More Sweet

Mon, 18 Apr 2022 02:30:00 -0700

First up, listener mail on Cathie Wood's permabull status, and some mortgage rates are now below treasuries. Doogles covers a recent Not Boring post called The Current Financial Thing, which transitions into a discussion on the current state of raising venture capital. Elon Musk tries to buy Twitter, and Skippy thinks it is one of the most fascinating situations as of late. The episode wraps with Skippy's surprise at how much money billionaires have saved due to the 2003 tax cut on dividends.

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Bill Gross' Extraordinary Playlist

Mon, 11 Apr 2022 02:30:00 -0700

Doogles covers a recent essay by Kenneth French and the 5 things he's learned about investing over the past decades. Skippy gets back on his soapbox about Series I Bonds (and for good reason), and dives into more info on Bill Gross, the "bond king". Doogles thinks that Elon Musk is going to eventually buy all of Twitter. Skippy is fascinated by how much Walmart is willing to pay its truck drivers. The episode wraps with a discussion on Robinhood's business model and what's happening with housing.

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Between a JPEG Rock and a Hard Place

Mon, 04 Apr 2022 02:30:00 -0700

Listener mail points to a story of a man selling his JPEG rock for one millionth of his intended price. Doogles gives an overview of a post called "What is Money"? Skippy covers the most popular equities traded today...most of which no one should be trading. The bond market has its worst quarter in over 40 years. The episode wraps with Doogles taunting Skippy over the billionaire tax being back on the table.

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America's Self-Induced Filibuster

Mon, 28 Mar 2022 02:30:00 -0700

Doogles goes over a recent post in Full Stack Economics about how America can't build infrastructure fast anymore. Skippy revives his favorite game, Rational or Irrational, and then parlays that into an overview of a Time article about Ethereum's founder. Doogles gives a slow clap for the quasi-reopening of the Russian stock market. Skippy wonders if rising mortgage rates will help to cool the housing market. The episode wraps talking about the cash crunch in the commodities market and a celebration of Amazon's 2001 letter to shareholders.

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One Large Popcorn, Light on the Gold Please

Mon, 21 Mar 2022 02:30:00 -0700

Doogles makes it back from Vegas, and is convinced people are betting mostly with debt. AMC buys a large stake in a gold and silver mining company (?!). Skippy stays bullish on Alibaba (BABA), and wonders whether the thesis applies to other beaten down stocks with 1 billion plus users. Doogles points out that El Salvador's bitcoin experiment is not going well. Skippy quizzes Doogles on the hottest cities for college graduates. All praise that interest rates are finally going up. The episode wraps with covering how home value increases from last year outpaced average wages in the US, and a professor reps baby bonds to combat inequality.

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I'll Give You $100K for That Nickel

Mon, 14 Mar 2022 03:30:00 -0700

Skippy starts off with catching falling knives and the continued cheapness of Alibaba (BABA). Doogles gives some background on the nickel crisis and what this might mean for further damage in the auto industry. Skippy yells at politicians, especially Bernie Sanders who wants to stop oil companies from making money. Doogles walks through a Morningstar article about women and investing — and how sexist the investing community is. Skippy recaps a Columbia University post about faulty data in US News and World Report. The recent Bed, Bath and Beyond stock resurgence confuses Doogles. Skippy summarizes why people quick their jobs, and then the episode wraps with some non-US stock highlights by Doogles.

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Your Cash is No Good Here

Mon, 07 Mar 2022 02:30:00 -0700

Skippy kicks off with some highlights from the NFL Combine and their fashion. Doogles pivots to the Russian stock market closure and the high percentage of investments Russians have (had?) in their own market. Some quick hits on China — 1) them asking Russia to wait on the Ukraine invasion until after the Olympics and 2) their annual economic plan. Skippy covers car dealerships and how they don't want to take cash deals anymore because it brings down profits. Doogles wishes he could've been equity brothers with Buffett, who just bought more Occidental Petroleum (OXY). Doogles triples down on his recent stay invested pleas, highlighting a recent JP Morgan piece stating the same. The episode wraps with a convo on equity insurance and black swans.

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Our Hearts Are With Ukraine

Mon, 28 Feb 2022 02:30:00 -0700

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After Doogles kicks off with a celebratory hooray about the US Women's National Soccer Team getting a taste of victory with well deserved backpay, Skippy and Doogles discuss Russia and Ukraine. The show focuses on the potential economic and investing impact (and specifically SWIFT) of what is happening to the Ukrainian people, but their hearts and minds are with the people themselves. They then discuss market reversals and Charlie Munger's recent Daily Journal meeting. Skippy continues the dollar store war discussions with Family Dollar's recent rat infestation issues. Doogles raises a recent piece on Peloton's irrational growth expectations, and the episode wraps with a few quit hit items from Skippy.

Inspector Gadget Hacks Bitcoin

Mon, 21 Feb 2022 02:30:00 -0700

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The episode kicks off with listener mail on the 'ultimate portfolio' (Skippy and Doogles disagree) and some inside scoop on European stocks trading for the cheap. Doogles raises a recent Bitcoin heist arrest of a terrible amateur rapper. Skippy brings up another example of the cheap stuff catching up to growth — Hilton vs. Zoom. Doogles discusses a tweet storm about how terrible individual investors usually are. Skippy celebrates that the Fed FINALLY bans stock trading for its governors. The episode wraps with a convo about US compensation of Olympic medal winners.

Tesla, the King!

Mon, 14 Feb 2022 02:30:00 -0700

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Things kick off with some hilarious listener mail — a recent tweet from Aaron Levie re Zuck. Doogles follows up on his VTI research from last week re staying invested. Skippy drops knowledge on the trucking industry. Doogles highlights some interesting research about guaranteed income and UBI. Skippy and Doogles share a nonsensical audio clip about only investing in America and then discuss European value. Skippy raises increased chatter about banning Congress from trading stocks. Doogles rains praise on financial and energy stocks returns year to date. Skippy wraps the episode with a discussion about the economics of Spotify.

Peeps Be Done Gone Crazy

Mon, 07 Feb 2022 02:30:00 -0700

You can get more details about the show at skippydoogles.com, show notes on our Substack, and please send comments or questions to skippydoogles@gmail.com.

This episode kicks off with two pieces of listener mail — one on the 35 year old Big Mac Index, which gauges currency valuations off of the relative cost of a Big Mac in different countries; and wild ride the market took this week as demonstrated by Snap's earnings swing. Doogles discusses how Kansas is trying to give away free land. Skippy relates that to how Woodside, CA is claiming that their land is a mountain lion habitat. Doogles does some analysis to engrain in folks the need to stay invested — losing even just a couple of the best performing days will take a big chunk out of your investments. Skippy discusses a recent book that he didn't enjoy (The Dao of Capital), though he does think the psychology around Black Swans rasied in the book is worth while. The episode wraps talking about the Wordle acquisition, and a couple value investing-related quotes.

I Can Has Sweden?

Mon, 31 Jan 2022 02:30:00 -0700

You can get more details about the show at skippydoogles.com, show notes on our Substack, and please send comments or questions to skippydoogles@gmail.com.

Skippy kicks things off with listener mail — Ford is having so much demand that they needed to cancel pre-orders, so watch out Tesla. Doogles taps Farnam Street for some wisdom on not setting ourselves up to fail, and relates that to reactive hedging in the market. Skippy marvels at the overabundance of parking spaces in the US relative to the number of cars. Doogles rides the abundance track and discusses frothy startup valuations, and how the US wants to be like Sweden per a decade-old study in Americans' perceptions of inequality. The convo wraps with a discussion on some portfolios that have historically done well during downturns.

Calm Down Chicken Little

Mon, 24 Jan 2022 02:30:00 -0700

Doogles kicks things off with some listener mail re Goldman Sachs' outlook on the markets. Skippy recaps the terrible performance of some previous high fliers (Peloton, Docusign, Moderna....etc) over the past week, and Doogles highlights that Nasdaq corrections are very very common. Skippy hits on some great quotes from Howard Marks in his book "The Most Important Thing". Doogles claims victory in calling the SPACtacular disaster that we're now all witnessing, and Skippy points out that GMO is also claiming victory in its permabear status of calling the market crash (for the past 5 years...). Doogles covers recent news on the Microsoft acquisition of Activision, and the Spice DAO overpaying for a rare copy of Dune. The episode wraps with Skippy finding an NFT loophole and touching on the most recent crypto crash.

I Feel Tippy, Oh So Tippy

Mon, 17 Jan 2022 02:30:00 -0700

Dollar Tree customers are feeling "sick to their stomachs" over the 25-50% inflation that's happening over there. Melania Trump is continuing to release NFTs, which Doogles describes as a bubble of a bubble of a bubble. Doogles scolds Americans, saying that we know better, and points to some media examples to take a closer look — a recent LA Times article, a Netflix movie, and a book. Skippy and Doogles talk the importance and dangers of anchoring around baselines. Skippy lays out the biggest causes of inflation...and Doogles rants about his fright over people running out of money. They then discuss the amount of leverage that workers have, Skippy hits on a Zynga arbitrage opportunity he's scouting, and they wrap discussing a Stanford Business School piece on the economics of taxi cab tipping.

Nonsense and Glory [Your 2021 Favorites]

Mon, 10 Jan 2022 02:30:00 -0700

Skippy and Doogles have a different kind of episode for you today. First up is a ~20 minute preview of a portfolio review pod, which is available to "I Roll With Skippy and Doogles" annual subscribers at skippydoogles.supercast.com. Next is a compilation of fan favorite clips from 2021 — it's got some Second Life, some Cathie Wood, some NIMBY, and, of course, Chamath. Lots of glory, and lots of nonsense. 2021 was a blast with you all, and excited for the rest of 2022!

Confusing Buffett, Bernie and Orville

Mon, 03 Jan 2022 02:30:00 -0700

Welcome to 2022! It's rebalancing time, bringing tears to Doogles' eyes. Next week, Skippy and Doogles are going deep for a special premium episode available at skippydoogles.supercast.com, covering past performing and what they're looking to buy. This episode kicks off with Doogles covering the Buffett vs. Bernie spat over union workers, and how they're looking more and more alike as time guys on. Next, Skippy recaps a book he read recently called Pop! about historical bubbles. Doogles wraps the episode with a peculiar finding that he made recently about his largest holding, Dexcom.

What a Difference a Year Makes

Mon, 27 Dec 2021 02:30:00 -0700

Welcome to episode 52 — one year of Skippy and Doogles! We start off with the show's special consultant popping by to give a holiday recap and some gift ideas. Then Doogles sadly revisits China Mobile, one year after its US delisting, as it prepares for its Shanghai listing. Skippy raises the recent Jack Dorsey vs. the VC world battle that's taking place over Web3, and Doogles uses that as a transition to a recent Tim O'Reilly piece called "Why it's too early to get excited about Web3." (<- hot take) Doogles gets angry about platforms taking away all his content over contract disputes, and they debate whether platform or content is king. Skippy and Doogles both express skepticism over a recent "talk your book" claim by crypto house Pantera Capital that crypto is the biggest asymmetric bet of this generation, and the last show of the year wraps with a discussion on why stocks based on storytelling are getting crushed right now.

Who Moved My Cream Cheese?

Mon, 20 Dec 2021 03:30:00 -0700

The episode kicks off with listener mail — first a quick hit on some other unexplainable rudeness from the Better.com CEO, and then continuing to pull the thread on Cathie Wood's YOLO trip to nonsense through ARK. Doogles takes us back to MicroStrategy's Bitcoin holdings now that they're trying to figure out how to get yield from it. Skippy highlights how many rich people are currently in Congress (hint, more than there should be). Doogles finds a loophole in the dessert game — Kraft is currently paying people to buy any dessert that isn't cheesecake to try and help their cream cheese shortage woes. They then hit on the results from the last Fed meeting of the year, and wrap with Scott McNealy's take on price to sales multiples and a recap of Barry Ritholtz's recent interview with Michael Mauboussin on the Masters in Business podcast.

Metaversially Controversial

Mon, 13 Dec 2021 02:30:00 -0700

A friend of a friend tells Doogles that Sex and the City is hurting Peloton's stock. Skippy and Doogles discuss a recent Invest Like the Best podcast interview with Philip Rosedale and Bill Gurley about Second Life and the metaverse. Doogles officially names 'Fragility' as his word of 2021 (look out Merriam-Webster), and he's excited for what this might mean for 2022. Skippy comments on how inflation continues to impact wages, with companies setting aside almost 4% for payroll increases next year. The active vs passive investing debate continues, now fueled by Peter Lynch's recent comments about how he thinks the move to passive is a mistake. The episode wraps with misleading claims that Bitcoin's creator, Satoshi, has officially been unmasked, and a lesson for everyone to be less of a jerk than the CEO of Better.com.

Some Turkey With a Side of "Audio Issues"

Mon, 06 Dec 2021 02:30:00 -0700

Skippy eats some crow — first he got the wrong call earlier this year on Jim Harbaugh not performing after a salary cut, and second he said not to invest in China and that's exactly where he's found himself. Sticking with China, the future of Variable Interest Entities (VIEs) looks bleak, and they discuss what this means for their recent Alibaba investments. Doogles gives a rundown of the economic disaster that is occurring in Turkey right now and how Turkey's president is pouring salt into their economic wounds. Then onto bubble talk, a recent episode of the All In Podcast has a great summary of how inflated everything is, as well as why it's important to make you own decisions and not just follow what all the pundits are saying. Doogles plays a clip of a recent pundit who claimed to have "audio issues" when asked a very simple question on CNBC. The episode wraps with an anecdote of a couple that followed bad advice on buying alternative assets in their IRA, which is costing them hundreds of thousands of dollars.

ARKK You Kidding Me Right Now?

Mon, 29 Nov 2021 02:30:00 -0700

Doogles pleads for Cathie Wood to calm down as she starts testing "ARK on Steroids". That transitions in a recent Morgan Housel post called "Experts From A World That No Longer Exists" which discusses holding onto past "expertise" can get you into trouble if you don't also adapt. Skippy dives into some recent reading about Solana, and its potential advantages over Bitcoin and Ethereum. In the latest evidence of the markets going buckwild, more money was put into US equities in 2021 than the last 19 years combined (and it's fueled by margin debt). Doogles circles back to a Zillow conversation, highlighting a recent blog post on stevenbuccini.com contrasting Zillow's investment philosophy in data vs. that of Affirm. And the episode wraps with more Doogles' nerdy reads recommendations.

Never Underestimate Florida Man

Mon, 22 Nov 2021 02:30:00 -0700

Crypto talk continues in the news — Skippy and Doogles talk Crypto.com buying the naming rights for the Staples Center, ConstitutionDAO's bid to buy a copy of the constitution, and Florida Man claiming to be Satoshi, the creator of Bitcoin. Then Skippy recaps parts of a recent podcast interview with Arnold Van Den Berg where he talks the commodities supercycle and the psychological fortitude of value investors. Skippy gives a decade by decade drawdown quiz, and Doogles gets a B+ on his responses. Doogles talks the bubble in the venture capital / startup space, highlighting a recent Fred Wilson blog post on avc.com called "Seed Rounds at $100mm Post Money." The episode wraps with Doogles giving Skippy two international knowledge quizzes (one on GDP and one on historical all-time returns for different countries), and Skippy going on a rant about Green Bay Packers "financing."

Your Consumerism is Killing Me

Mon, 15 Nov 2021 02:30:00 -0700

Tesla vs. the World

Mon, 08 Nov 2021 02:30:00 -0700

Skippy kicks off with some strong research advice about Series I government bonds, which are paying out 7.12% for this 6 months period. Then he rolls into a series of Tesla quizzes, highlighting how Tesla's valuation continues to be outrageous compared to the rest of the auto industry. Doogles transitions the convo to Zillow's stock, which has taken a 67% beat down since February of this year, recently thanks in part to it shutting down Zillow Offers (its iBuying product). People are leaving their jobs, and Skippy thinks that crypto gains are to blame — Doogles thinks this is a terrible idea. Then they cover Morgan Housel's recent post, "The Same Stories Again and Again," which is well written and covers how history repeats itself. Skippy wraps the episode with a rant about how much money college football wastes by hiring and rapidly firing its coaches.

Zuck is Officially Off His Rocker

Mon, 01 Nov 2021 02:30:00 -0700

The episode starts with Skippy and Doogles discussing different types of risks based on a great post this week in Of Dollars and Data called "Risking Fast and Slow". Then, the topic on everyone's mind - what is Zuck up to with the metaverse. Doogles reminisces about his Second Life days and asks the question "has Facebook lost its way?". Doogles then brings up a fantastic article in Time about Black Bitcoin, which covers how Bitcoin is being embraced by people of color in search of financial liberation. Skippy rants for awhile about taxing unrealized gains, and Doogles brings up other points of view. The episode wraps with an overview of a recent post about how much wealth the US stock market has created over the last century, and how much of the world's stock market capitalization sits in the US right now.

The DWAC SPAC is BACK

Mon, 25 Oct 2021 02:30:00 -0700

Skippy and Doogles launch a Substack at skippyanddoogles.substack.com. Doogles starts off the newsletter with a deeper dive on his investment methodology and Q3 portfolio returns. Skippy stretches as usual to defend value investing, this time claiming that value stocks are a hedge against inflation. Speaking of inflation hedges, the DWAC SPAC shot up by nearly 10x this week upon announcement that it's getting into the Donald Trump media game. On the topic of risky trades, Doogles dabbles in options this week, which Skippy is not a fan of. The conversation wraps by discussing the expectations gap between financial advisors and their clients, and a few key questions for long term investors.

NIMBY, NIMBY Everywhere

Mon, 18 Oct 2021 02:30:00 -0700

Skippy forgets to stay in his lane, and begins to spew "wisdom" about genetics. Then Doogles provides his usual dose of happiness by centering the conversation around mounting consumer debt as demonstrated by the Nintendo game Animal Crossing. Skippy pulls out some excellent listener mail, covering a recent New York Times article on the California housing crisis called "Where the Suburbs End" (great read), highlighting how people want to solve the housing crisis so long as it's NIMBY (Not In My BackYard). This leads to a conversation about shadow inflation that's raising prices by decreasing the quality of goods and services. Going back to California, Doogles hits on more listener mail about hedge funds profiting off of PG&E stock. The episode wraps with Doogles getting Skippy fired up through a January 2021 blog post called "Bitcoin is a Ponzi," and with an overview of a recent economics paper showing that increasing equity cash flows has an impact on prices.

Hips Don't Lie, But Bank Accounts Do

Mon, 11 Oct 2021 02:30:00 -0700

Who has two thumbs and is giving up almost $400k per game this year in the NBA? Kyrie Irving. The convo starts with the quizzical nature of that choice, and then moves on to the equal quizzical nature of how it's easier to invest in Non Fungible Tokens (NFTs) than startup companies. Speaking of NFTs, next Doogles brings up listener mail re a Vice article covering the recent Evolved Apes NFT scam where the NFT creators took over with over $2m from investors.

Next up — hiding money overseas. And, allegedly, that's exactly what Shakira is doing according to the Pandora Papers, a recent data leak investigated by the International Consortium of Investigative Journalists (ICJ). Skippy parlays that into a conversation about a 2021 PBS documentary on the Fed, where there's a claim that the Fed isn't after supporting the rich, they're after supporting the poor...which just so happens to make the rich richer. Doogles raises a couple more points of greed — Robinhood's COO trading on Material Non-Public Information and Ozy Media faking voices on conference calls to raise money.

The episode wraps with a stock that Doogles is thinking about to get into, his first potential new investment since Q1 of this year.

Nancy Pelosi, Queen of the Markets

Mon, 04 Oct 2021 02:30:00 -0700

Skippy and Doogles kick things off with some double-threaded listener mail — 1) a nod to a robust investing data website, Nasdaq Data Link; 2) TikTokers are looking to Congress for their hot picks. Nancy Pelosi has been deemed Queen of the Markets by this crew...

Speaking of politicians trading stocks, 2 Fed Governors are resigning because they got caught with their proverbial hands in the cookie jar (note, it's bad form to trade stocks while lifting up the market through your policy decisions). Morgan Stanley released a fun paper called "Turn and Face the Strange" which discussing the resistance to change in both sports and investing (highly recommend this one).

Next up, China continues to ruin the markets, this time through the massively indebted property developer Evergrande. While on the topic of real estate, rental prices are going sky high due to a supply/demand imbalance...and imbalances continue to be everywhere as captured by the JP Morgan paper, "Dude, Where's My Stuff?". The episode wraps with a return to dollar stores, as Dollar Tree's prices are going beyond $1 to account for rising prices.

A Future of Negative Interest Rates w/ James Mackintosh (Wall Street Journal)

Mon, 27 Sep 2021 02:30:00 -0700

Skippy and Doogles developed a recent fascination with a Wall Street Journal article called "Digital Currencies Pave Way for Deeply Negative Interest Rates," and brought on its author, James Mackintosh, to walk through it. The result is a nerdily fun conversation about central banks, digital currencies, interest rates, and market psychology.

Narratives Up, Facts Down

Mon, 20 Sep 2021 02:30:00 -0700

Skippy goes straight Limitless — he had a reading extravaganza these week and brought it to the pod. The episode kicks off with listener mail to give some thoughts on where to push long term cash. This leads to a reflection on the 22 year old prediction of Dow 36,000.

Then comes a barrage of quick hit topics: MicroStrategy & Bitcoin, the China crackdown continues, Walmart doesn’t actually accept Litecoin, states and pay transparency, the ESG investing compensation machine, how gas stations make money, what it will take to retire, Ray Dalio and Bitcoin, the Cyberkong NFT…was Second Life right?, Buy Now Pay Later (BNPL), shipping clogged up in Southern California, and teaching personal finance in schools via stock picking.

Last, a couple non-quick hits are how narratives impact valuations and the art of keeping things simple.

A Broken Market is Still Right Twice a Day

Mon, 13 Sep 2021 02:30:00 -0700

The episode kicks off talking about how the world keeps moving faster and faster, and what that means for tech and economics (a new book "Exponential" hits on this in more detail). To continue the book review, Skippy brings up the book "The Art of Nonconformity" and get a crack out of its list of 11 things to do if you want to be unremarkably average. They then discuss how the market has transformed from one of risk taking (which is always present in investing) to risk seeking. The episode wraps with chat about how lower and lower interest rates might be a negative macro indicator on American society, and the self-reinforcing nature of inequality when it comes to wealth.

Sorry, Jenna, Maybe This NFT Will Help

Mon, 06 Sep 2021 02:30:00 -0700

A man proposes with an NFT and, surprisingly, it doesn't go well. Skippy and Doogles get some listener mail that has Chamath Palihapitiya podcasting his way back into Skippy's psyche — this time through a criticism of investing in Alibaba. This takes the conversation back into China and all the continuing happenings over there (e.g., risks of VIEs, video game restrictions, corporate "donations"). Skippy calls out the Renaissance Technologies billionaires that got hit with a massive $7 billion tax bill, and then gives a shout out to a recent Lex Fridman podcast that did a great job of covering blockchain and Bitcoin. The episode wraps with a discussion of SEC Chairperson Gary Gensler putting banning payment for order flow "on the table."

Investing in the Fashion Metaverse

Mon, 30 Aug 2021 02:30:00 -0700

Skippy kicks off with all the excitement that's currently surrounding Alibaba's stock. Doogles turns off the excitement by talking about the audit industry. Skippy continues the ongoing conversation around wealth inequality through a recent report "From wealthy enclaves to asset deserts" put out by the Economic Innovation Group. Next up is the the rising debt in Japan, which is now nearly 2x Japanese GDP. The episode wraps with a discussion of Ted Weschler's $264 million Roth IRA, and Bobby Hundred's commitment to driving street fashion into the metaverse through NFTs.

Hedgehogs, Foxes, and Woods — Oh My!

Mon, 23 Aug 2021 02:30:00 -0700

ISAs continue to be a hot topic in listener mail! Someone writes in to call out Doogles and his declaration that ISAs are debt. Then the conversation flows to investors as hedgehogs or foxes, an important concept when looking at the money losing stories chronicled in a recent Institutional Investor article, “How Millennial Investors Lost Millions on Bill Ackman’s SPAC”. Doogles uses this opportunity to bring up Michael Burry's bet against Cathie Wood's ARK Innovation ETF. Skippy raises Alibaba as a hot new investment from some very respected value investors, and how part of its recent decline comes from Jack Ma's political missteps. And the episode wraps with Coinbase's recent announcement that it's buying $500 million in a variety of cryptocurrencies.

TINA Scouts Out Some Mobile Homes

Mon, 16 Aug 2021 02:30:00 -0700

Things start off with some listener mail, adding Income Share Agreements (ISAs) to the conversation about the hidden costs of some types of debt. Then Doogles celebrates continued evidence of bi-partisanship in the government with the passage of the infrastructure bill in the Senate, and the introduction of a new bill (FRESH START) that aims to make it easier to discharge student loan debt when declaring bankruptcy. The conversation moves on to discuss large investments by private equity firms in mobile home parks (in a never ending search for yield), and whether asset-based investment advisor fees are justified. The episode wraps with a chat about an investment paper on genetics and investment bias, and a solid Chris Dixon tweet storm on Webt 3.0 and take rates.

Buying is Easy, Selling is Harder

Mon, 09 Aug 2021 02:00:00 -0700

Doogles comes across an inverse ETF targeting ARK innovation — never did we think we'd see an inverse ETF targeting a specific fund manager, but here we are (should we get in?). Then Skippy runs through the list of the most valuable teams in the NFL, according to Forbes. Doogles digs into his Nerd Alert fishbowl to talk through a recent research paper called "Selling Fast and Buying Slow" from the National Bureau of Economic Research, which analyzes the buying and selling behavior of a large number of institutional investors. Then the episode wraps with an overview of "Go Big Then Stop," a recent blog post on Of Dollars and Data, and a discussion on the rise of buy now, pay later companies like Affirm, Klarna and Afterpay (getting bought by Square).

Credit Suisse And the 1000x Rounding Error

Mon, 02 Aug 2021 02:00:00 -0700

Doogles leads off by talking about how Martin Shkreli uses a rare Wu-Tang Clan album to pay back his debt to the government. Then Doogles looks at the ridiculous debacle that was Credit Suisse's enablement of the Archegos collapse. Skippy and Doogles take a trip through small town America by discussing a recent Granola Shotgun article "We'd Rather Have the Iceberg Than the Ship" — a good breakdown of how chasing the shiny and new is short term thinking. Skippy discloses his new CEO crush on Ravi Saligram, who runs Newell Brands and enacted a no jerks policy that has turned around the company's financials. The episode wraps with discussing how brokerages make money, and the pros and cons of college football realignment.

Nonprofit Stocks Are All the Rage

Mon, 26 Jul 2021 02:00:00 -0700

Skippy breaks out some data from the Bureau of Labor and Statistics that shows how Americans spend their money based on age. Then, he grabs some quotes from a recent conversation on Bitcoin between Cathie Wood, Jack Dorsey, and Elon Musk before taking an unintentional jab at Doogles' recent Chinese investment woes (RIP TAL Education Group?). Doogles gets Skippy's view on whether to hold or sell when an investment gets acquired, and then they wrap with a brief discussion on solar value deflation.

Don't Trust Teenagers With Your Bitcoin Money

Mon, 19 Jul 2021 02:30:00 -0700

The conversation around inflation continues! Skippy and Doogles discuss the state of inflation, and whether or not Bitcoin makes sense as a hedge. Then they highlight two South African teenagers who started a crypto investment firm, and allegedly ran away with the money. Sticking on the crypto train, they talk through Dogecoin co-founder Jackson Palmer's tweet rant against crypto. Next up, MSCI may be trying to create the Ultimate Market Portfolio, a portfolio representing all of the world's assets. The episode wraps by revisiting Skippy's current thoughts on Intel given their recent $30 billion bid to purchase GlobalFoundries.

Like a Bear in a China Shop

Mon, 12 Jul 2021 02:00:00 -0700

Things kick off with a quiz — what company got acquired last week that Doogles calls the "official indicator of a bubble"? Then they cover Biden's most recent executive (non)order that tries to indirectly tackle competition and consumer protection. Next, they dive into China, stemming from the recent failure of Didi's IPO. Skippy uses this to revisit the failures that are America's education and healthcare systems. The episode wraps with Doogles going off on a nerdy finance rant because of his disagreement with the definition of a bear market.

A Dollar, A Dollar, My Kingdom For a Dollar!

Mon, 05 Jul 2021 00:00:00 -0700

Skippy and Doogles start with a dive into the excitement that is dollar store economics! These companies are money makers, and have historically shown they can do well during a recession. Speaking of recessions, the conversation then moves to how renowned economist Nouriel Roubini (aka, Dr. Doom) is saying that this next recession is going to be huge. They then discuss current outsized US investor expectations (i.e., US investors are expecting 17.5% go forward annual returns...) and how Robinhood's recently released S-1 shows it's at least partially fueling this nonsense. They wrap with an investing checklist and some hits from a great recent interview of Marc Andreessen by Patrick O'Shaughnessy on his podcast, Invest Like the Best.

Delawarean Gumption Moves Markets

Mon, 28 Jun 2021 03:00:00 -0700

The Roth IRA was created to fuel the retirement savings of 1) middle class Americans, and 2) Peter Thiel. Things kickoff with a discussion of Peter Thiel's $5 billion Roth IRA, quite a site to be seen. Skippy and Doogles then play a little game called Rational/Irrational where they judge the rationality of things like bubble psychology, the recent crypto crash and 48" vertical leaps. Recent government actions are up next, first with some small but meaningful movement on the infrastructure bill, and next with bi-partisan early support for some anti-big tech measures — both of which could move markets. Doogles then gives a history lesson on cross-shareholding in Japan as he searches for international investment opportunities, and the show wraps with an overview of a recent Lending Tree survey on American's use of debt to invest (spoiler alert: Americans are into it!).

Give Me All Your Inflation, Give Me All Your Debt

Mon, 21 Jun 2021 07:00:00 -0700

Prices are going up, and Skippy takes notice. He and Doogles discuss inflation over the last 100 years and what that might mean for today. And with inflation, comes the desire to hedge — Michael Saylor isn't immune to this desire, but maybe his Bitcoin hedge has gone a bit too far. After they discuss "going Michael Saylor", Skippy and Doogles hit on a recent Chicago Booth Review study about how the savings of the 1% is fueling the debt of the bottom 90%. And while we might be at a household wealth record, the fact that we're also at a corporate debt record is a problem. The episode wraps with a chat re pay transparency in Colorado and how some companies are trying to avoid hiring there.

Bukele vs the Volcano

Mon, 14 Jun 2021 06:00:00 -0700

Skippy and Doogles tackle many cryptocurrency topics this week — Microstrategy continues to be Bitcoin crazy, 401ks are adding crypto options, El Salvador has made Bitcoin legal tender, and, yes, Bitcoin transactions are traceable. After the crypto whirlwind, they discuss the movement in Asia known as "lying flat" and the potential implications for the future. Then, as if real estate couldn't get crazier, BlackRock is buying all the homes in America. The episode wraps with a discussion on ProPublica's coverage of the tax (non)payments of the richest people in the US, and then a little quiz on the world's richest countries.

To Cow or Not to Cow, That is the Question

Mon, 07 Jun 2021 07:00:00 -0700

It's a rare treat to have a company issue stock while simultaneously telling you not to buy it, but AMC did just that. Skippy and Doogles also respond to some listener mail regarding the trends in stock buybacks vs cap ex investments. Then they sift through some data from Ben Carlson's article "200+ Years of Asset Class Returns" to discuss the returns themselves as well as the prowess (or lack thereof) of CEOs as asset allocators. They revisit and update the Covid-19 vaccine / lottery tests happening around the world. The conversation wraps with a discussion on cows as investment vehicles, and some evidence demonstrating that NFTs have not yet shown that they can make the average artist money.

Skippy Becomes a Lumberjack

Mon, 31 May 2021 07:00:00 -0700

Doogles kicks off this episode with an homage to the horrific events of the Tulsa Massacre of 100 years ago on 5/31/1921. It's important to recognize history and learn from it. Then the crew dives into more about the current state of the crazy real estate market, as well as the potential loop the US is getting into regarding consumption and business investment. Skippy provides the world with his investment hypothesis around timber and some thoughts on using smart contracts to make us all better investors. The episode wraps with listener mail on paying off one's mortgage and balancing momentum and value.

Investing Where You Have An Edge w/ Adam Burrows (Managing Partner, Range Ventures)

Mon, 24 May 2021 07:00:00 -0700

Skippy and Doogles sit down with Adam Burrows, the co-founder and Managing Partner at Range Ventures (an early stage venture capital VC firm). After highlighting the similarities between the Dogecoin of today, and the Garbage Pail Kids of the 1980s, Adam gives insight into the basics of venture capital. And this starts a fun and fascinating journey into several topics including the difference between investing and gambling, the disproportionate reward given to storytelling today, and how to think about investing after a financial windfall. The convo wraps with some speculation about whether any of the most valuable companies today will be the most valuable in the future.

Blissfully Wasteful Car Wrecks

Mon, 17 May 2021 07:00:00 -0700

Doogles gets straight doom and gloom out the gate by bringing up the recent fast decline of Taiwan's stock market (the TAIEX). Skippy brings some playful to the conversation through The Hustle's recent article "The Economics of Movie Product Placements" — did you know that The Fast & The Furious franchise crashed almost 1,500 cars over the first 7 films? (well, now you do). Doogles does his homework, researching the % of stocks that have beaten the market over 10-year increments in the last 100 years, and quizzes Skippy on the figures. Then they wrap with Elon Musk's Bitcoin schizophrenia and Ohio's vaccine incentivization via lottery.

Compounding Goodwill w/ William Green (author of Richer, Wiser, Happier)

Mon, 10 May 2021 07:00:00 -0700

What an episode this one is! Skippy and Doogles take a break from their usual 1:1 banter of glory to sit down with William Green, the author of Richer, Wiser, Happier. William has spent the last couple decades interviewing, and learning from, some of the greatest investors of the last century and his most recent book summarizes what he's gathered on not only how to get beaucoup returns, but also (and more importantly!) how to live a fulfilled life while doing it. As Borat says, this episode is "very excite" — you'll enjoy it.

All Your Debt Are Belong to Us

Mon, 03 May 2021 07:00:00 -0700

Skippy and Doogles kick off the episode by reminding the world that there's debt everywhere — the US is breaking all borrowing records and it's pretty scary. Yet, everything keeps going up and to the right, and Skippy highlights Jason Zweig's recent article "What Happens When Stocks Only Go Up?" that says we should be wary of this phenomenon. Speaking of high prices, Doogles keeps his commodities rant going, which prompts Skippy to (re)rant about value outperforming growth in the future. They wrap by waxing poetic about whether companies can possibly stay out of social/political commentary in the wake of Basecamp's announcement that they're doing just that.

Let's Talk About Tax, Baby

Mon, 26 Apr 2021 07:00:00 -0700

Inexplicably, Skippy discusses college town pizza tastes. Then...back to reality, Skippy and Doogles discuss their view on their investment performance relative to "average investors" and recap their investment strategies. To Skippy's dismay, Biden's recent tax proposal becomes the topic of the week, and Skippy parlays this into a discussion around a great book he's reading, "Richer, Wiser, Happier." They wrap with a contemplation about what the excess cash in the market really means.

The Profitability of Unprofitability

Mon, 19 Apr 2021 07:00:00 -0700

Skippy gives a world class overview of how value investing came to be, starting with the godfather, Benjamin Graham. A heated debate erupts over Tobias Carlisle's book, The Acquirer's Multiple, and more specifically whether corporate management excellence equals investment excellence. After tempers subside, they cover an update on SPAC regulation and the Coinbase IPO. The convo wraps with a discussion on China's continued push for a national digital currency.

Hot Takes From the Dimons and the Damons

Mon, 12 Apr 2021 07:00:00 -0700

Doogles and Skippy review Jamie Dimon's (JP Morgan CEO) 2020 annual shareholder letter and the relative declining importance of big banks. Skippy follows up on a self-run custom crypto index he's building. Doogles' insomnia leads him down a Matt Damon rabbit hole filled with water investments. They wrap with a discussion on JP Morgan's latest Guide to Markets and Janet Yellen's call for a global minimum corporate tax rate.

Biden's Comin' in Hot!

Mon, 05 Apr 2021 07:00:00 -0700

Skippy and Doogles kick things off with a quiz about biggest drops for some of the best performing stocks of the last 20 years. Then they hit on alternative investments to equities, highlighting the role of cost savings as well as income generating returns. They revisit Jim Clark and the importance of a narrative when it comes to investing and valuations. Doogles gives an high level overview of Biden's recent infrastructure plan, and then they wrap with a discussion of the Archegos Capital meltdown and all its related nonsense.

Can't Drive? Blame the Wind

Mon, 29 Mar 2021 07:00:00 -0700

Skippy continues his claim that Intel will be victorious, and Doogles won't hear it. They talk about the insane Net Asset Value premium that the Bitwise ETF is currently sporting. Then onto the Suez Canal, where some shoddy canal navigation techniques are currently holding up ~10% of global trade — this leads Doogles to predict that we need to look to space, not water, to drive the future of trade. Skippy shakes his head because Doogles continues to lose money in Chinese investments, and they wrap with musings on Robinhood and SoFi's recent moves to help retail investors invest alongside Wall Street funds in IPOs.

On the Path to a SPACtacular Disaster

Mon, 22 Mar 2021 07:00:00 -0700

Skippy hails from beyond his home in this episode taken from the open road of America! After Doogles stumbles to discover Skippy's mystery location, they discuss Brian Armstrong's (Coinbase CEO) charity GiveCrypto.org. which turns into a convo about fraud potential in the space. Doogles spins that into the current nonsensical status of the number of IPOs (and SPAC IPOs, specifically) that are happening in 2021. They then talk about governance, and how to best incentivize corporate governance to act in the investors' best interest, and wrap with commentary on Goldman Sachs' recent report Black Womenomics (yes, that's the real title...).

An Ode to Excel

Mon, 15 Mar 2021 07:00:00 -0700

Skippy and Doogles cover the recent $1.9T (yes, with a T) stimulus package and what this might mean for the economy and the markets. Then there's a slew of 'Jack' news — a much need 'Jack Ma Whereabouts' update, and some bad ideas discovered in Jack Dorsey's beard. They wrap with Doogles dropping lyrics on the magical phenomenon that is Microsoft Excel.

Who is talking about Ford Motor Company?

Mon, 08 Mar 2021 07:00:00 -0700

Doogles got a house! He uses this new found platform as a homeowner to walkthrough a "sexy" (his word, not Skippy's) Harvard paper on city network migration. Then Skippy rightfully shifts the conversation to the rotation that's happening in momentum funds towards more traditional value plays. They (re)announce the launch of BUZZ ETFs, now with 100% more Portnoy support, and then wrap with a convo on recent symbolic changes in wages and unemployment before Doogles embarrasses himself with a cockamamie thesis on how to bridge the inequality gap.

Redistribute the Bubble

Mon, 01 Mar 2021 07:00:00 -0700

Skippy and Doogles' sleuthing uncovers that there might be a slight bubble going on in the housing market. They give some reasons, and hypotheses, as to why yields are up and stocks are down...including why Cathie Wood might need to check her "YOLO trip to nonsense" portfolio. Then Skippy does justice to crypto/blockchain through some beautiful, yet obscure markets. And, to wrap it up, why did AT&T spin off DirectTV, and is the Coinbase IPO a good idea?

The Case of the Cryptic Crypto

Mon, 22 Feb 2021 07:00:00 -0700

Roaring Kitting makes his presence felt at the Congressional hearing, giving Skippy + Doogles some needed hilarity in their weeks. They're also happy this week because it's time for 13Fs, providing good fodder to cover, mock, and praise the investment choices of the professionals. Skippy also cons Doogles into "investing" in some crypto, and Doogles scoffs at MicroStrategy's nonsensical choice of bitcoin purchases.

HVAC is the New Black

Mon, 15 Feb 2021 07:00:00 -0700

Bitcoin rears its head once again, this time because Tesla decides to "invest" $1.5 billion in this crypto. Skippy and Doogles discuss the merits of this latest questionable move by Mr. Musk, and then move on to the less questionable wisdom dropped on a recent interview between Meb Faber and Jeremy Grantham — arguably the best interview we've heard as of late. Then Skippy and Doogles to debate how to hedge against a potential correction (dare we say crash?!?). Doogles is laying his hat in the commodities game...and betting on HVAC! Only time will tell if his cockamamie rationale pays off.

The episode wraps with a run through of the most dominant equities over the last 90 years — spoiler alert, most individual stock investments don't pan out....so we should study failure, and not just success.

Brady and Buffett Walk Into a Bar

Mon, 08 Feb 2021 07:00:00 -0700

Jeff Bezos goes out on top! Doogles and Skippy agree this is the way to go, and wonder if Tom Brady should take notice. Skippy talks smack, and calls Warren Buffett the Tom Brady of investing. Then things get heated as Skippy goes off his rocker about Chamath Palihapitiya's take on value investing on a recent episode of Invest Like the Best. The episode wraps with a discussion about inequality in the US and how we need to get more people to be able to participate in capital and investing.

GameStop Keeps Printing Tendies

Mon, 01 Feb 2021 07:00:00 -0700

What else is there to talk about beyond GameStop? Nothing is the answer. Doogles gives a GameStop history lesson and the two debate whether this is a sophisticated market move by retail investors, and whether it's good or bad for the market.

The Search for the Deep Cheap

Mon, 25 Jan 2021 07:00:00 -0700

The stock market stays frothy, and Skippy has a hard time finding undervalued profits. Skippy and Doogles discuss the best stock performance indicator so far in 2021, the (questionable) return of Jack Ma, and how market performance is governed by both psychology and fundamentals.

The Harbaugh Fire Sale

Mon, 18 Jan 2021 07:00:00 -0700

Skippy and Doogles dive deep into the Fish Bowl for this one. Skippy discovers that people are giving up their $millions of Bitcoin because they can't remember their passwords. Then Doogles realizes that he might be bringing investor Howard Marks to the dark side of momentum after Howard's latest investment memo second guesses value. Doogles introduces some new research he's done that says that while the stock market might be frothy, we're not quite at the top. The episode wraps with a bizarre move by the University of Michigan and their head football coach, Jim Harbaugh and debate about the price/value divide in the US higher education system.

Will the Real Jack Ma Please Stand Up?

Mon, 11 Jan 2021 07:00:00 -0700

Doogles gives an update on his China Mobile debacle and then schools Skippy on the history of the world's richest people according to Forbes. Digging into the Fish Bowl, some heated debate ensues about Elon Musk's status as a lottery ticket and Skippy and Doogles question the whereabouts of the Chinese billionaire, Jack Ma. To wrap it up, Doogles admits that he might finally start #adulting as he debates buying a house.

No one's ever gone wrong by buying a Chinese stock

Mon, 04 Jan 2021 07:00:00 -0700

Skippy breaks down how he picks his value stocks, and Doogles waxes poetic on momentum. Then they cover Robert Schiller's product marketing prowess around CAPE, Doogles' recent nonsensical stock picks, and why most professional investors lose to their benchmark.