Skippy and Doogles

Skippy and Doogles Talk Investing

Business EN ↓ 282 episodes

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

Business

Podcast website

skippydoogles.com

Latest episode

Jul 6, 2026

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Episodes

First There Was the War, Then the Capitulation 23.12.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show notes on...

Pop Goes the Bubble ‘Cause the Bubble Say Pop 16.12.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogl...

While Your Feet Are Stomping And the Coins Is Pumping 09.12.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the sho...

Oh The Places Stocks'll Go 02.12.2024

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". 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...

The Quest for Insufferable Geniuses w/ Josh Scott and Adam Burrows 25.11.2024

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 abou...

Doogles Jumps the Shark 18.11.2024

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. Join the Skippy and Doogles fan club . You can also get m...

Curmudgeonry McMuffinry 04.11.2024

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...

Millennials Do Debt Better 28.10.2024

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. Join the Skippy and Doogles fan club . You can als...

Mr. Statman, Bring Me Some Risk 21.10.2024

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. Join the Skippy...

Unicorns, 10 Years Hence w/Aileen Lee (Founder of Cowboy Ventures) 14.10.2024

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. 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 question...

Don't Let An Accounting Professor Run Your Company 07.10.2024

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. Join the Skippy and Doogles fan club . You can...

David Tepper Just Don’t Care 30.09.2024

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. 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 qu...

Silly Yeltsin, Trix Are For Kids 23.09.2024

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. Join the Ski...

Boyz II Men, ABC, BBD...Less Tax For Your Family 16.09.2024

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. 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 comme...

Rub a Dub Dub, Costco is Da Club 09.09.2024

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 bag...

A Branded Tattoo, I’ll Always Have You 02.09.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show at sk...

Some Guy On Some Other Job is Mr. Market 26.08.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show...

Confirmation Bias, And it Feels So Good 19.08.2024

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 m...

Warren’s Hoarding Cash and Putting Apple in the Trash 12.08.2024

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. Join the Skippy and Doogles fan club . You can als...

Will the Real Andy Grove Please Stand Up? 05.08.2024

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. Join the Skippy and Doogles fan club . You can also get more details about th...

Pull Yourself Up By Your Pigtails 29.07.2024

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." Join the Skippy and Doogles fan club . Y...

Wonk and Circumstance 22.07.2024

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. Join the Skippy and Doogles fan club . You can also get more details a...

The Skippyonaire Next Door 15.07.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show not...

NYC’s $700 Million Schurprise 08.07.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show at sk...

Walgreens’ Milkshake Brought No Investors to the Yard 01.07.2024

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. Join the Skippy and Doogles fan club . You can also get more details about the show at skippydoogles.com , show notes on our Substa...

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