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
Gotta Lose Money to Make Money 10.07.2023 35:11
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 b...
Things Are Going South 03.07.2023 48:51
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. Join the Skippy and Doogle...
The Billionaire Death Match 26.06.2023 45:36
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. Join the Skippy and Doogles fan club . Y...
Nuggets of Wisdom 19.06.2023 1:00:42
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 gr...
When Puts Comes to Shove 12.06.2023 47:43
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 gre...
All Hail the Salvatious Seven 05.06.2023 41:17
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...
From the Pub to Your Ear Buds 29.05.2023 23:04
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. Join the Skippy and Doogles fan club ....
Scurry Burry Investing Up a Flurry 22.05.2023 43:50
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...
Mungermania LVIII 15.05.2023 54:40
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 pie...
No Pain, No Premium 08.05.2023 52:49
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 tha...
I Feel REITs In My Fingers, I Feel REITs In My Toes 01.05.2023 37:10
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...
One Way Ticket Out of Pity City 24.04.2023 50:10
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...
Turning Kohl's Into Diamonds 17.04.2023 43:20
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. Join the Skippy and Doogles fan club . You can also get...
No Work And All Play Makes Jack A Dull Boy 10.04.2023 38:39
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. Join the Skippy and Doogles fan clu...
Two Good Friends and a Microphone [Seafarer Investor Podcast Interview] 03.04.2023 1:19:00
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! 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 skippydoogl...
Stay In Your Lane, Liam Neesons 27.03.2023 44:39
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 cre...
Why Can't Banks Just Be Normal? 20.03.2023 51:10
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. Join the Skippy and Doogles fan club . You can also get more details about the show...
You Down Wit SVB? Yeah FDIC! 13.03.2023 56:15
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 r...
America’s Got 99% Problems And Housing Is One 06.03.2023 42:57
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, whethe...
Fees, Sir, I Want Some More 27.02.2023 52:09
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. Join...
Munger Don’t Care About You Or Anything That You Do 20.02.2023 47:11
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. Join the Skippy and Doogles fan club . You can also get more details about the sh...
Beware the Sharknado Recession 13.02.2023 47:44
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. Join the Skippy a...
Johnny Needs a Fast Car 06.02.2023 53:59
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 wra...
Simply the Best, Worse Than All the Rest 30.01.2023 40:00
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. Join...
Fantastical Rates and Where to Find Them 23.01.2023 51:06
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 wr...
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