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?
Podcasts in the app Replaio Radio Coming soonPodcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts
Episodes
Buying is Easy, Selling is Harder 09.08.2021 44:37
Doogles comes across an inverse ETF targeting ARK innovation — never did we think we'd see an inverse ETF targeting a specific fund manager, but here we are (should we get in?). Then Skippy runs through the list of the most valuable teams in the NFL, according to Forbes. Doogles digs into his Nerd Alert fishbowl to talk through a recent research paper called "Selling Fast and Buying Slow" from the...
Credit Suisse And the 1000x Rounding Error 02.08.2021 44:59
Doogles leads off by talking about how Martin Shkreli uses a rare Wu-Tang Clan album to pay back his debt to the government. Then Doogles looks at the ridiculous debacle that was Credit Suisse's enablement of the Archegos collapse. Skippy and Doogles take a trip through small town America by discussing a recent Granola Shotgun article "We'd Rather Have the Iceberg Than the Ship" — a good breakdown...
Nonprofit Stocks Are All the Rage 26.07.2021 45:35
Skippy breaks out some data from the Bureau of Labor and Statistics that shows how Americans spend their money based on age. Then, he grabs some quotes from a recent conversation on Bitcoin between Cathie Wood, Jack Dorsey, and Elon Musk before taking an unintentional jab at Doogles' recent Chinese investment woes (RIP TAL Education Group?). Doogles gets Skippy's view on whether to hold or sell wh...
Don't Trust Teenagers With Your Bitcoin Money 19.07.2021 47:57
The conversation around inflation continues! Skippy and Doogles discuss the state of inflation, and whether or not Bitcoin makes sense as a hedge. Then they highlight two South African teenagers who started a crypto investment firm, and allegedly ran away with the money. Sticking on the crypto train, they talk through Dogecoin co-founder Jackson Palmer's tweet rant against crypto. Next up, MSCI ma...
Like a Bear in a China Shop 12.07.2021 52:22
Things kick off with a quiz — what company got acquired last week that Doogles calls the "official indicator of a bubble"? Then they cover Biden's most recent executive (non)order that tries to indirectly tackle competition and consumer protection. Next, they dive into China, stemming from the recent failure of Didi's IPO. Skippy uses this to revisit the failures that are America's education and h...
A Dollar, A Dollar, My Kingdom For a Dollar! 05.07.2021 48:47
Skippy and Doogles start with a dive into the excitement that is dollar store economics! These companies are money makers, and have historically shown they can do well during a recession. Speaking of recessions, the conversation then moves to how renowned economist Nouriel Roubini (aka, Dr. Doom) is saying that this next recession is going to be huge. They then discuss current outsized US investor...
Delawarean Gumption Moves Markets 28.06.2021 55:02
The Roth IRA was created to fuel the retirement savings of 1) middle class Americans, and 2) Peter Thiel. Things kickoff with a discussion of Peter Thiel's $5 billion Roth IRA, quite a site to be seen. Skippy and Doogles then play a little game called Rational/Irrational where they judge the rationality of things like bubble psychology, the recent crypto crash and 48" vertical leaps. Recent govern...
Give Me All Your Inflation, Give Me All Your Debt 21.06.2021 46:03
Prices are going up, and Skippy takes notice. He and Doogles discuss inflation over the last 100 years and what that might mean for today. And with inflation, comes the desire to hedge — Michael Saylor isn't immune to this desire, but maybe his Bitcoin hedge has gone a bit too far. After they discuss "going Michael Saylor", Skippy and Doogles hit on a recent Chicago Booth Review study about how th...
Bukele vs the Volcano 14.06.2021 57:04
Skippy and Doogles tackle many cryptocurrency topics this week — Microstrategy continues to be Bitcoin crazy, 401ks are adding crypto options, El Salvador has made Bitcoin legal tender, and, yes, Bitcoin transactions are traceable. After the crypto whirlwind, they discuss the movement in Asia known as "lying flat" and the potential implications for the future. Then, as if real estate couldn't get...
To Cow or Not to Cow, That is the Question 07.06.2021 50:04
It's a rare treat to have a company issue stock while simultaneously telling you not to buy it, but AMC did just that. Skippy and Doogles also respond to some listener mail regarding the trends in stock buybacks vs cap ex investments. Then they sift through some data from Ben Carlson's article "200+ Years of Asset Class Returns" to discuss the returns themselves as well as the prowess (or lack the...
Skippy Becomes a Lumberjack 31.05.2021 46:52
Doogles kicks off this episode with an homage to the horrific events of the Tulsa Massacre of 100 years ago on 5/31/1921. It's important to recognize history and learn from it. Then the crew dives into more about the current state of the crazy real estate market, as well as the potential loop the US is getting into regarding consumption and business investment. Skippy provides the world with his i...
Investing Where You Have An Edge w/ Adam Burrows (Managing Partner, Range Ventures) 24.05.2021 44:14
Skippy and Doogles sit down with Adam Burrows, the co-founder and Managing Partner at Range Ventures (an early stage venture capital VC firm). After highlighting the similarities between the Dogecoin of today, and the Garbage Pail Kids of the 1980s, Adam gives insight into the basics of venture capital. And this starts a fun and fascinating journey into several topics including the difference betw...
Blissfully Wasteful Car Wrecks 17.05.2021 44:54
Doogles gets straight doom and gloom out the gate by bringing up the recent fast decline of Taiwan's stock market (the TAIEX). Skippy brings some playful to the conversation through The Hustle's recent article "The Economics of Movie Product Placements" — did you know that The Fast & The Furious franchise crashed almost 1,500 cars over the first 7 films? (well, now you do). Doogles does his ho...
Compounding Goodwill w/ William Green (author of Richer, Wiser, Happier) 10.05.2021 1:32:01
What an episode this one is! Skippy and Doogles take a break from their usual 1:1 banter of glory to sit down with William Green, the author of Richer, Wiser, Happier. William has spent the last couple decades interviewing, and learning from, some of the greatest investors of the last century and his most recent book summarizes what he's gathered on not only how to get beaucoup returns, but also (...
All Your Debt Are Belong to Us 03.05.2021 40:28
Skippy and Doogles kick off the episode by reminding the world that there's debt everywhere — the US is breaking all borrowing records and it's pretty scary. Yet, everything keeps going up and to the right, and Skippy highlights Jason Zweig's recent article "What Happens When Stocks Only Go Up?" that says we should be wary of this phenomenon. Speaking of high prices, Doogles keeps his commodities...
Let's Talk About Tax, Baby 26.04.2021 46:11
Inexplicably, Skippy discusses college town pizza tastes. Then...back to reality, Skippy and Doogles discuss their view on their investment performance relative to "average investors" and recap their investment strategies. To Skippy's dismay, Biden's recent tax proposal becomes the topic of the week, and Skippy parlays this into a discussion around a great book he's reading, "Richer, Wiser, Happie...
The Profitability of Unprofitability 19.04.2021 49:32
Skippy gives a world class overview of how value investing came to be, starting with the godfather, Benjamin Graham. A heated debate erupts over Tobias Carlisle's book, The Acquirer's Multiple, and more specifically whether corporate management excellence equals investment excellence. After tempers subside, they cover an update on SPAC regulation and the Coinbase IPO. The convo wraps with a discus...
Hot Takes From the Dimons and the Damons 12.04.2021 47:24
Doogles and Skippy review Jamie Dimon's (JP Morgan CEO) 2020 annual shareholder letter and the relative declining importance of big banks. Skippy follows up on a self-run custom crypto index he's building. Doogles' insomnia leads him down a Matt Damon rabbit hole filled with water investments. They wrap with a discussion on JP Morgan's latest Guide to Markets and Janet Yellen's call for a global m...
Biden's Comin' in Hot! 05.04.2021 46:06
Skippy and Doogles kick things off with a quiz about biggest drops for some of the best performing stocks of the last 20 years. Then they hit on alternative investments to equities, highlighting the role of cost savings as well as income generating returns. They revisit Jim Clark and the importance of a narrative when it comes to investing and valuations. Doogles gives an high level overview of Bi...
Can't Drive? Blame the Wind 29.03.2021 49:40
Skippy continues his claim that Intel will be victorious, and Doogles won't hear it. They talk about the insane Net Asset Value premium that the Bitwise ETF is currently sporting. Then onto the Suez Canal, where some shoddy canal navigation techniques are currently holding up ~10% of global trade — this leads Doogles to predict that we need to look to space, not water, to drive the future of trade...
On the Path to a SPACtacular Disaster 22.03.2021 44:11
Skippy hails from beyond his home in this episode taken from the open road of America! After Doogles stumbles to discover Skippy's mystery location, they discuss Brian Armstrong's (Coinbase CEO) charity GiveCrypto.org. which turns into a convo about fraud potential in the space. Doogles spins that into the current nonsensical status of the number of IPOs (and SPAC IPOs, specifically) that are happ...
An Ode to Excel 15.03.2021 50:20
Skippy and Doogles cover the recent $1.9T (yes, with a T) stimulus package and what this might mean for the economy and the markets. Then there's a slew of 'Jack' news — a much need 'Jack Ma Whereabouts' update, and some bad ideas discovered in Jack Dorsey's beard. They wrap with Doogles dropping lyrics on the magical phenomenon that is Microsoft Excel.
Who is talking about Ford Motor Company? 08.03.2021 46:35
Doogles got a house! He uses this new found platform as a homeowner to walkthrough a "sexy" (his word, not Skippy's) Harvard paper on city network migration. Then Skippy rightfully shifts the conversation to the rotation that's happening in momentum funds towards more traditional value plays. They (re)announce the launch of BUZZ ETFs, now with 100% more Portnoy support, and then wrap with a convo...
Redistribute the Bubble 01.03.2021 46:50
Skippy and Doogles' sleuthing uncovers that there might be a slight bubble going on in the housing market. They give some reasons, and hypotheses, as to why yields are up and stocks are down...including why Cathie Wood might need to check her "YOLO trip to nonsense" portfolio. Then Skippy does justice to crypto/blockchain through some beautiful, yet obscure markets. And, to wrap it up, why did AT&...
The Case of the Cryptic Crypto 22.02.2021 48:57
Roaring Kitting makes his presence felt at the Congressional hearing, giving Skippy + Doogles some needed hilarity in their weeks. They're also happy this week because it's time for 13Fs, providing good fodder to cover, mock, and praise the investment choices of the professionals. Skippy also cons Doogles into "investing" in some crypto, and Doogles scoffs at MicroStrategy's nonsensical choice of...
Similar podcasts
Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.