Podcast
Skippy and Doogles Talk Investing
Hosted by Skippy and Doogles · EN
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.
42episodes
Episodes
Newest firstAll episodes
SaaSpocalypse Now? AI, Block Layoffs & the Trust Premium
Mar 200:39:38Tap to summarizeIs SaaS dead — or just getting repriced? We break down the viral “SaaS apocalypse” thesis, the 2028 AI doom scenario, and Block’s 40% layoffs. Are AI agents about to replace CRMs, workflows, and entire jobs?Join the premium 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.
Transcribe →Pinterest: Hidden Gem or Just a Pretty Picture? [Investment Committee]
Feb 2300:47:50Tap to summarizeIs Pinterest stock (PINS) a hidden gem… or just a really good looking business with a monetization problem? In our first-ever Investment Committee episode, we take a deep dive into Pinterest.We break down:ARPU vs. Meta (and why that gap matters)The 9x monetization problem between the U.S. and Rest of WorldAI-powered discoveryStock-based compensationand more...At ~$18 per share and down big from highs, is this a turnaround story, an acquisition target, or a value trap? As always: do your own research. We’re here to sharpen thinking, but the decision is yours.Join the premium 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.
Transcribe →Is Software Dead or Just On Sale?
Feb 1600:43:14Tap to summarizeSoftware stocks are getting hammered. Adobe at 7 year lows, Salesforce crushed. We discuss why and then cover our takes on the recent viral piece "Something Big is Happening."Join the premium 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.
Transcribe →Finding Value Where No One Is Looking w/Lee Roach (author of The Value Road Substack)
Feb 900:42:34Tap to summarizeIn this episode, we’re joined by deep value investor Lee Roach, author of The Value Road Substack, to explore what it really means to find value where no one else is looking.Lee shares his unconventional path from working overnight shifts in a manufacturing plant to becoming a full-time investor and writer. We dive into his approach to deep value investing, with a focus on micro-cap and nano-cap stocks, why “cheap” isn’t enough without a catalyst, and how patience and psychology play a critical role when prices move against you.We also discuss the tradeoffs of investing in illiquid markets, how to distinguish between stocks that are cheap for a reason versus simply ignored, and why smaller investors may actually have an edge in parts of the market institutions can’t touch.This is a thoughtful conversation about process, discipline, and doing the work others won’t — not chasing hype, but uncovering opportunity in the market’s blind spots.Join the premium 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.
Transcribe →Hi-Ho Silver, and Away
Feb 200:31:28Tap to summarizeSkippy & Doogles break down the epic silver smackdown, one of the wildest commodity crashes in nearly a century. Also, a quiz on the most popular dating profile words by state (spoiler: Missouri is… a zoo). Then OpenAI’s funding drama continues.Join the premium 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.
Transcribe →Got it Goin On Like Kroenke Kong
Jan 2600:38:26Tap to summarizeFrom Walmart parking lots to $5B stadiums, Stan Kroenke’s is winning. Skippy goes off on Nike’s scarcity games (just give the man a jacket). Doogles drops tariff truth bombs courtesy of Germany's Kiel Institute. And the Acquired Podcast’s 10-year recap sparks a convo on scarcity, podcasting as compounding, and whether we’ve been doing this all wrong.Join the premium 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.
Transcribe →The 5-Minute Buffett Test
Jan 1900:38:26Tap to summarizeWarren Buffett says it only takes 5 minutes to know if a company’s worth buying. Skippy & Doogles unpack what he really means.Plus: US workers are getting a smaller slice of the pie — lowest since 1947, and Elon Musk says don’t save for retirement. Cool. Cool cool cool.Join the premium 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.
Transcribe →Play Stupid Games, Win Stupid Economies
Jan 1200:40:25Tap to summarizeFirst up, Venezuela. Once the richest country in South America, now economically uninvestable. We unpack how oil wealth turned into a curse, what "Dutch Disease" really means, and how Norway played the game better. Then it's onto growth investing. What actually makes a great growth stock? We break down a killer piece by James Gaultry, the Costco vs. LVMH debate, and why high ROIC plus reinvestment opportunities are rarer than you think. Finally, we dive into Pablo Torre’s podcast episode on scoring — and the existential trap of chasing the wrong metrics in life, money, and college rankings.Join the premium 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.
Transcribe →CEO of Berkshire is a Job I'm Glad I Don't Have [2025 Greatest Hits]
Jan 501:10:52Tap to summarizeThis is a very special episode very year! For "I Roll With Skippy & Doogles" premium subscribers, this is where we do our 2025 performance and portfolio review. And for all other listeners (we appreciate you too!) you get a greatest hits compilation from our most listened to episodes from 2025. Enjoy!Join the premium 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.
Transcribe →Jim Beam Shuts Down, Tax Apps Block Holidays, and the $700M Wedding Ring Repo
Dec 2900:47:16Tap to summarizeSkippy & Doogles wrap up 2025 (and year five of the pod!) with a rapid-fire round of wild investing stories, billionaire blowups, bourbon shutdowns, and ultra-wealthy tax dodging that’s so ridiculous it ruins Christmas.Join the premium 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.
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