First 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 [email protected].

This 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 [email protected].

Skippy & 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 [email protected].

Skippy & Doogles dive into Mitt Romney’s surprising New York Times op-ed calling to raise taxes on the ultra-wealthy — including himself. We also unpack the growing backlash to legalized sports betting, the subtle shift in public opinion, and why gambling fatigue is setting in fast. Then it’s on to Gen Z and the rise of financial nihilism.

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 [email protected].

Skippy & Doogles unpack three wild stories from the world of money, markets, and mayhem:

• Listener mailbag: “You guys called it!” — Oracle’s crash, Broadcom’s wild ride, and the return of Cisco (25 years later)
• Affordability all day, every day: A new Brookings study reveals that 1 in 3 U.S. middle-class families can’t afford basic living costs
• College Sports Go Corporate: The University of Utah just sold a piece of its future to private equity

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 [email protected].

This week, Skippy & Doogles unpack Burry's latest market outlook, shady behavior in prediction markets, and the bizarre death (yes, death) of TiVo. Plus: Apple’s massive buybacks, Caitlin Clark’s WNBA salary quiz, and why MicroStrategy might be headed for disaster.

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 [email protected].

Skippy and Doogles dive into the viral debate around “the real poverty line” and trust us, it’s not $31,000… but it’s definitely not $140,000 either.

Then we turn to Ray Dalio’s latest bubble commentary, unpacking what “80% of the way into a bubble” really means—and why cash, leverage, and forced selling matter more than clickbait headlines.

Finally, we close with the heartwarming Wall Street Journal piece on Charlie Munger’s final years. From yelling across rooms with Buffett to adopting new teenage friends at age 99, Munger kept compounding wisdom until the very end.

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 [email protected].

Skippy & Doogles dive into operating margins across industries, break down a wild Morningstar strategy that involved buying 4,000 terrible stocks and made bank. And then debate whether Google just leapt past NVIDIA in the AI chip race.

In this episode:

• Operating margin quiz: Ports vs. Pizza vs. Car Rentals
• A 70% drawdown strategy that might actually work
• Google’s surprise AI + chip resurgence (is Gemini now the AI model?)
• Value investing is still dead…for now

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 [email protected].

Skippy & Doogles fire up the investing time machine and revisit Seth Klarman’s 20 lessons from the 2008 financial crisis — lessons that feel alarmingly relevant in today’s overheated market. From the dangers of financial innovation to the privilege of liquidity, they break down the timeless wisdom and apply it to 2025’s investor landscape.

Plus, listener mail sparks debates on:

• The rise of working-class investors — is it a bubble signal?
• What “affordability” really means in an age of all-time high incomes and prices
• Whether it's time to build a bachelorette party GoFundMe app

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 [email protected].

Skippy & Doogles dive into two wild valuation stories this week: OpenAI's trillion-dollar fantasy and Kenvue's decision to sell itself short. This is a clinic on how markets misprice both risk and hype.

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 [email protected].