Skippy and Doogles Talk Investing

What's a Little Tax Lie Between Friends?

13 Apr 2026

Contributed by Lukas

We kick off with CNBC’s all-time “upside/downside” moment (it's honestly embarrassing). Then Skippy talks through tax myths and the Social Secur...

Private Credit is Hotel California For Your Money

06 Apr 2026

Contributed by Lukas

We kick things off in the cognitive dark forest, where sharing your ideas might ...

What Are We Doing?!

30 Mar 2026

Contributed by Lukas

Doogles is wondering what the heck is going on. Markets feel disconnected, AI spendin...

Betting on Missiles is Not Investing

23 Mar 2026

Contributed by Lukas

Doogles breaks down the story of prediction markets influencing real-world reporting. Then Skippy covers what Americans think is gambling vs. investin...

You Too Can Be a Sucker

16 Mar 2026

Contributed by Lukas

Skippy introduces Tommy the Car Guy, a YouTube negotiator who charges $1,000 to call dealerships and beat them down on price. Then we break down what ...

SaaSpocalypse Now? AI, Block Layoffs & the Trust Premium

02 Mar 2026

Contributed by Lukas

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....

Pinterest: Hidden Gem or Just a Pretty Picture? [Investment Committee]

23 Feb 2026

Contributed by Lukas

Is Pinterest stock (PINS) a hidden gem… or just a really good looking business with a monetization problem? In our first-ever Investment Committee e...

Is Software Dead or Just On Sale?

16 Feb 2026

Contributed by Lukas

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 "Som...

Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)

09 Feb 2026

Contributed by Lukas

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 whe...

Hi-Ho Silver, and Away

02 Feb 2026

Contributed by Lukas

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 ...

Got it Goin On Like Kroenke Kong

26 Jan 2026

Contributed by Lukas

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). Doogl...

The 5-Minute Buffett Test

19 Jan 2026

Contributed by Lukas

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 a...

Play Stupid Games, Win Stupid Economies

12 Jan 2026

Contributed by Lukas

First up, Venezuela. Once the richest country in South America, now economically uninvestable. We unpack how oil wealth turned into a curse, what "Dut...

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

05 Jan 2026

Contributed by Lukas

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 por...

Jim Beam Shuts Down, Tax Apps Block Holidays, and the $700M Wedding Ring Repo

29 Dec 2025

Contributed by Lukas

Skippy & Doogles wrap up 2025 (and year five of the pod!) with a rapid-fire round of wild investing stories, billionaire blowups, bourbon shutdown...

Mitt Romney Says Tax the Rich? Plus Sports Betting Regret and Gen Z Financial Nihilism

22 Dec 2025

Contributed by Lukas

Skippy & Doogles dive into Mitt Romney’s surprising New York Times op-ed calling to raise taxes on the ultra-wealthy — including himself. We a...

Private Equity Invades College Sports: Utah’s $100M Gamble and Affordability is Broken

15 Dec 2025

Contributed by Lukas

Skippy & Doogles unpack three wild stories from the world of money, markets, and mayhem:Listener mailbag: “You guys called it!” — Oracle’s...

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

08 Dec 2025

Contributed by Lukas

This week, Skippy & Doogles unpack Burry's latest market outlook, shady behavior in prediction markets, and the bizarre death (yes, death) of TiVo...

The Real Poverty Line, Ray Dalio’s Bubble Math, and Charlie Munger’s Last Lessons

01 Dec 2025

Contributed by Lukas

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 $140,00...

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

24 Nov 2025

Contributed by Lukas

Skippy & Doogles dive into operating margins across industries, break down a wild Morningstar strategy that involved buying 4,000 terrible stocks ...

20 Lessons from 2008 That Still Matter (Especially Now)

17 Nov 2025

Contributed by Lukas

Skippy & Doogles fire up the investing time machine and revisit Seth Klarman’s 20 lessons from the 2008 financial crisis — lessons that feel a...

OpenAI is a Masterclass in Market Mispricing

10 Nov 2025

Contributed by Lukas

Skippy & Doogles dive into two wild valuation stories this week: OpenAI's trillion-dollar fantasy and Kenvue's decision to sell itself short. This...

A $20K Robot Butler and Why 57% of Americans Don’t Invest

03 Nov 2025

Contributed by Lukas

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 bre...

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

20 Oct 2025

Contributed by Lukas

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...

AI Hype Circle, and ETFs Are the New Casino Chips

13 Oct 2025

Contributed by Lukas

Doogles is sad, Skippy is confused, and together they try to untangle the absolute nonsense of modern markets. From OpenAI’s mystery valuation and A...

Japan, Debt, and the Downside of Free Money

06 Oct 2025

Contributed by Lukas

Skippy & Doogles unpack what Japan’s economy can teach us about the long-term effects of debt, demographics, and currency devaluation. It's a tr...

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

29 Sep 2025

Contributed by Lukas

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...

Robinhood’s New Private Fund Is a Terrible Idea

22 Sep 2025

Contributed by Lukas

Skippy & Doogles dive deep into Robinhood’s latest move: launching a private fund for retail investors. Is it financial innovation—or a terrib...

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

15 Sep 2025

Contributed by Lukas

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 hyp...

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

08 Sep 2025

Contributed by Lukas

Skippy & Doogles dive into the uncomfortable truth behind America’s housing obsession. Why are homeowners tapping their equity at record rates —...

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

01 Sep 2025

Contributed by Lukas

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-...

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

25 Aug 2025

Contributed by Lukas

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 spec...

ETF Survivorship Bias, Intel Drama, and the $1.3 Trillion Buyback Binge

18 Aug 2025

Contributed by Lukas

Skippy & Doogles break down the real story behind ETF performance. Then they dive into the wild Intel CEO saga — presidential shade, stock pops,...

Michael Mauboussin, PE Ratios & The Art of Future Value

11 Aug 2025

Contributed by Lukas

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 framewo...

South Park, Skinny Shots & the Market Meltdown

04 Aug 2025

Contributed by Lukas

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...

Ferrari Status & the Passive Investing Bubble

28 Jul 2025

Contributed by Lukas

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 i...

Passive Income Lies, BrewDog Drama, and Zip Code Economics

21 Jul 2025

Contributed by Lukas

Skippy & Doogles rip apart the worst “passive income” ideas making the rounds on Twitter (spoiler: vending machines aren’t passive). Then it...

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

14 Jul 2025

Contributed by Lukas

Skippy & Doogles take on the $40B youth sports industrial complex, the myth of "smart money," and why partying might actually be dead in America. ...

Trump Accounts Debunked, PE Myths, and Incentivized Stupidity

07 Jul 2025

Contributed by Lukas

Skippy & Doogles dig into the fine print of the “Trump Accounts” and discover… it’s not what the headlines promised. Is it an investing to...

Venture Returns Unpacked, AI’s Internet Disruption, And The Dangerous Success of Stablecoins

30 Jun 2025

Contributed by Lukas

Skippy and Doogles are back in your mentals with a triple-header of investing greatness. First up, a stablecoin thought experiment gone dark—what i...

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

23 Jun 2025

Contributed by Lukas

This week, Skippy & Doogles break down the real risks (and hype) around stablecoins — why they’re booming, what regulators just did, and why m...

Circle IPO Frenzy, Tip Tax Madness, and America’s Adulting Crisis

09 Jun 2025

Contributed by Lukas

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...

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

02 Jun 2025

Contributed by Lukas

This week, we're rewinding to one of our most loved convos ever—with Richer, Wiser, Happier author William Green.William spent 25+ years interviewin...

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

26 May 2025

Contributed by Lukas

This week, Skippy & Doogles tackle the uncomfortable truth behind the phrase “there’s no free lunch.”They break down:Why tipping culture is ...

Leverage Looks Brilliant, Until It Blows Up

19 May 2025

Contributed by Lukas

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)—...

Is Warren Buffett Actually the GOAT?

12 May 2025

Contributed by Lukas

Skippy & Doogles dive deep into the Buffett legacy—breaking down Berkshire’s insane 5.5 million percent return, the psychology behind his frug...

McRecession, Doritos, and a Side of Disappointment

05 May 2025

Contributed by Lukas

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 th...

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

28 Apr 2025

Contributed by Lukas

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 num...

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

21 Apr 2025

Contributed by Lukas

Foreigners own net $30 trillion in U.S. assets—should we be worried? Skippy & Doogles go deep on America’s financial entanglements, who holds ...

Compounding When the World’s on Fire

14 Apr 2025

Contributed by Lukas

Markets are twitchy, tariffs are flying, and the Economic Policy Uncertainty Index just hit 900. So... what now? This week, Skippy and Doogles channel...

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

07 Apr 2025

Contributed by Lukas

This week, Skippy & Doogles go scorched earth on the most chaotic economic policy rollout in recent memory. Trump’s new “reciprocal” tariffs...

Burrito Bowls, Now With Zero Percent Down

31 Mar 2025

Contributed by Lukas

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...

Preferred Shares of Chaos

24 Mar 2025

Contributed by Lukas

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...

Is America Really Going Bankrupt?

17 Mar 2025

Contributed by Lukas

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....

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

10 Mar 2025

Contributed by Lukas

Is the government cooking the books? This week, Skippy & Doogles dive into Trump’s plan to strip government spending from GDP—what it means, w...

Booz, Buffett, and Billionaires

03 Mar 2025

Contributed by Lukas

Skippy looks at Booz Allen Hamilton’s wild government contract dependency and what happens when the political winds shift. Doogles breaks down Warr...

Bill Ackman’s Berkshire Bootleg

24 Feb 2025

Contributed by Lukas

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 wr...

Bargains Gettin More Bargainy

17 Feb 2025

Contributed by Lukas

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 ...

What Have You Done For Me Bukelatley?

10 Feb 2025

Contributed by Lukas

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 diversi...

The Stocks From Ipanema Go Walking

03 Feb 2025

Contributed by Lukas

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. ...

Let’s Play Hide and DeepSeek

27 Jan 2025

Contributed by Lukas

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 e...

The Conundrum of the Personal Burger Taxi

20 Jan 2025

Contributed by Lukas

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 ...

Reading Between the Lines

13 Jan 2025

Contributed by Lukas

Skippy and Doogles tackle the relationship between interest rates, the economy and stock valuations. Doogles walks through Charlie Bilello's latest c...

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

06 Jan 2025

Contributed by Lukas

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 ep...

Who is Buying This Hogwash?

30 Dec 2024

Contributed by Lukas

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 processe...

First There Was the War, Then the Capitulation

23 Dec 2024

Contributed by Lukas

Skippy highlights the financial incongruence of NFL quarterbacks. Doogles shakes his head at a Techcrunch piece on Databricks waiting to go public. ...

Pop Goes the Bubble ‘Cause the Bubble Say Pop

16 Dec 2024

Contributed by Lukas

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 wheth...

While Your Feet Are Stomping And the Coins Is Pumping

09 Dec 2024

Contributed by Lukas

Doogles talks about the current mindset of the American worker. Skippy talks market valuations in the US and parlays that into a conversation about p...

Oh The Places Stocks'll Go

02 Dec 2024

Contributed by Lukas

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....

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

25 Nov 2024

Contributed by Lukas

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...

Doogles Jumps the Shark

18 Nov 2024

Contributed by Lukas

Skippy apologies and congratulates Theo on his polymarket victory. Doogles quizzes Skippy on the best YTD stock market performances through October. ...

Curmudgeonry McMuffinry

04 Nov 2024

Contributed by Lukas

Skippy talks through Jason Zweig’s list of market grievances in his latest commentary in the Intelligent Investor. Some French dude is betting ...

Millennials Do Debt Better

28 Oct 2024

Contributed by Lukas

It's the 200th episode, people! Doogles starts off talking about the finances of millennials vs. baby boomers in the US. Skippy raises Invest Americ...

Mr. Statman, Bring Me Some Risk

21 Oct 2024

Contributed by Lukas

Doogles covers a recent Ben Carlson piece on the importance of the sequence of returns in investing. Skippy likes a breakdown by Professor Statman ab...

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

14 Oct 2024

Contributed by Lukas

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 "unicor...

Don't Let An Accounting Professor Run Your Company

07 Oct 2024

Contributed by Lukas

KIcks off with listener mail about a Duke research report on human capital investments during Covid. Doogles walks through a Graham Duncan piece on t...

David Tepper Just Don’t Care

30 Sep 2024

Contributed by Lukas

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 ...

Silly Yeltsin, Trix Are For Kids

23 Sep 2024

Contributed by Lukas

Kicks off with listener mail about refinancing given the recent interest rate reduction. Doogles covers a post about universities being debt factorie...

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

16 Sep 2024

Contributed by Lukas

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...

Rub a Dub Dub, Costco is Da Club

09 Sep 2024

Contributed by Lukas

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 prai...

A Branded Tattoo, I’ll Always Have You

02 Sep 2024

Contributed by Lukas

Doogles passionately expresses his hotels rewards preference. Skippy makes a quiz out of the hottest brands people get tattooed on their bodies.&...

Some Guy On Some Other Job is Mr. Market

26 Aug 2024

Contributed by Lukas

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-subscri...

Confirmation Bias, And it Feels So Good

19 Aug 2024

Contributed by Lukas

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...

Warren’s Hoarding Cash and Putting Apple in the Trash

12 Aug 2024

Contributed by Lukas

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 ...

Will the Real Andy Grove Please Stand Up?

05 Aug 2024

Contributed by Lukas

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 ...

Pull Yourself Up By Your Pigtails

29 Jul 2024

Contributed by Lukas

Skippy discusses the rise of Junior Bridgeman, NBA 6th man to $600m empire. Doogles walks through the results of OpenResearch's recent universal basi...

Wonk and Circumstance

22 Jul 2024

Contributed by Lukas

Skippy puts the magic of compounding on full display. Doogles runs through a research paper on balancing your career risk with portfolio risk. Skipp...

The Skippyonaire Next Door

15 Jul 2024

Contributed by Lukas

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 ...

NYC’s $700 Million Schurprise

08 Jul 2024

Contributed by Lukas

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 disa...

Walgreens’ Milkshake Brought No Investors to the Yard

01 Jul 2024

Contributed by Lukas

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 busine...

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

24 Jun 2024

Contributed by Lukas

Skippy kicks off with current stock allocation rates for Americans, then moves to the wild premiums that Costco and Nvidia stocks have right now. Doo...

[Replay] Your Consumerism is Killing Me

17 Jun 2024

Contributed by Lukas

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)...

My AI Juice Is Worth Your Squeeze

10 Jun 2024

Contributed by Lukas

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 cov...

Get Your 10 Year Old to the Ballot Box

03 Jun 2024

Contributed by Lukas

Premium subscribers get a couple hot stock research recommendations to kick it off. Doogles tackles listener mail that covers the book The Fourth Tur...

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

27 May 2024

Contributed by Lukas

Listener mail hits on the controversial topic of Fama and French's data set shifting. Skippy goes off about supposed ridiculousness coming from Googl...

Google Has Gone Full Hooli

20 May 2024

Contributed by Lukas

Kicks off with listener mail about the multi-level-marketing shenanigans of IM Academy. Skippy teases Doogles about a winning pitch on shorting Pool ...

Chocolate’s Called Liquid Gold For a Reason

13 May 2024

Contributed by Lukas

Skippy honors the legacy of Jim Simons' legendary returns. Doogles covers people's inaccurate view of fairness. Skippy won't stop ranting about tech...

Skippy & Doogles Go To NewBraska

06 May 2024

Contributed by Lukas

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 i...

Debt La Soul is Dead

29 Apr 2024

Contributed by Lukas

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. Do...

Pretty Ricky’s What They Call Him

22 Apr 2024

Contributed by Lukas

Skippy talks about how Americans throw away $68 million in change per year. He then gives out a research recommendation of an American utility. Doog...