Skippy and Doogles
Skippy and Doogles Talk Investing
For years, two of the world's greatest investing minds, Skippy and Doogles, have debated their investing philosophies. They started recording their phone calls to bring that stock market wisdom to the masses. Buckle up, because you never know where these conversations might go, and what kind of priceless investment knowledge will soon hit your mentals.
Author
Skippy and Doogles
Category
Podcast website
Latest episode
Jul 6, 2026
Where to listen?
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Episodes
I Left My Wallet in El Tokyo 16.01.2023 56:49
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 b...
Office Space is a Comedy, Not a Blueprint [2022 Episode Compilation] 09.01.2023 54:40
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...
Closing Out An Eggstraordinary Year 02.01.2023 54:18
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 pred...
Bow Knows This And Bow Knows That 26.12.2022 43:19
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. Join the Skippy and Doogles fan...
Deion Sanders Up In China 19.12.2022 52:17
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 decis...
The Pied Piper of New York City 12.12.2022 46:54
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 wi...
Little Caesars is Dead, Long Live Little Caesars 05.12.2022 48:02
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 histor...
You Gotta Spend Money to Spend Money 28.11.2022 1:00:53
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...
The SEC Doesn't Regulate Poop Emojis 21.11.2022 47:28
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. Join the Skippy and Doogles fan cl...
Angela Lansbury Would Be Disappointed 14.11.2022 54:17
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. Join the Skippy and D...
Welcome to the Janet Jackson Market 07.11.2022 53:17
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. Join t...
It's Cool to Be Kind w/ W. David Marx (author of Status and Culture) 31.10.2022 1:06:28
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. 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...
Sideways Markets From Wayside School 24.10.2022 56:49
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. Join the Skippy and Doogles fan club . You can also get more detail...
Wood You Mind Slowing Down? 17.10.2022 43:38
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,...
Can You Keep Up? FDR Make Me Lose My Breath 10.10.2022 51:04
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 hear...
Housing Be Beamin' While the Market's Screamin' Lehman 03.10.2022 46:21
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 for...
Weak Ties, Strongly Held 26.09.2022 45:56
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. Join the Skippy and Doo...
Peloton is the Jim Cramer of Companies 19.09.2022 35:33
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...
Interest Rates Are Up…But Not For Your Savings 12.09.2022 39:59
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. Join the Skippy and Doo...
It's Not Right, And It's Not OK 05.09.2022 53:54
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...
It’s APE’s World, We Just Live In It 29.08.2022 52:56
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. J...
Out of the Frying Pan, Into the Prison 22.08.2022 56:14
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 t...
Playing Hot Potato With Dynamite 15.08.2022 38:55
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. Join the Skippy and Doogles fan club . You can also get more details...
The Predictive Power of Trousers and Trainers 08.08.2022 42:39
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...
TINA and TASA in a TUSSLE 01.08.2022 44:31
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 p...
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