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
The Value In Preparation w/ William Green 25.07.2022 1:21:05
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. Join the Skippy and Doogles fan club . You...
Powell, Just Get On With It Already 18.07.2022 59:57
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 cou...
Post Malone Saves the Metaverse 11.07.2022 48:18
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...
Is Radio Shack the Next Berkshire Hathaway? 04.07.2022 47:39
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...
Dear Bitcoin, Do You Know How Hedges Work? 27.06.2022 49:22
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. Join the Skippy a...
The Market Has the Mouth of a Saylor 20.06.2022 1:09:24
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 (awes...
When Bees Are Fish, No Portfolio Is Safe 13.06.2022 42:00
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 w...
Don't Slap Grandpa at Costco 06.06.2022 46:31
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. Join the Skippy and Doogles fan club . You can also get more deta...
Blue Chips and Red Crackers 30.05.2022 55:46
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 c...
If Being Rich is Sexy, Getting Rich Sure Isn't 23.05.2022 50:15
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....
Numbers Don't Matter in Canada 16.05.2022 58:00
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 re...
Sticking Through Thick and Thin w/ Justin Carbonneau (Validea Capital Management) 09.05.2022 42:58
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 mo...
This Never Happens, Except All the Time 02.05.2022 49:31
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 rela...
Blame It On the P-p-p-p-p-password Sharing 25.04.2022 48:32
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 spendin...
A Twitter By Any Other Price Would Smell More Sweet 18.04.2022 45:51
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...
Bill Gross' Extraordinary Playlist 11.04.2022 57:43
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....
Between a JPEG Rock and a Hard Place 04.04.2022 51:31
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...
America's Self-Induced Filibuster 28.03.2022 42:59
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 hou...
One Large Popcorn, Light on the Gold Please 21.03.2022 48:48
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...
I'll Give You $100K for That Nickel 14.03.2022 55:10
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 sex...
Your Cash is No Good Here 07.03.2022 37:38
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...
Our Hearts Are With Ukraine 28.02.2022 54:44
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 . 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 f...
Inspector Gadget Hacks Bitcoin 21.02.2022 39:26
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 . 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 arr...
Tesla, the King! 14.02.2022 48:33
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 . 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 trucki...
Peeps Be Done Gone Crazy 07.02.2022 49:41
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 demonst...
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