184. Bill Brewster: From "Junk" to Quality

Bill Brewster, host of The Business Brew, joins us for a candid conversation about the mental toll of stock picking and his evolution from "cigar butt" value investing to quality compounders. We dive deep into his sharp criticism of Disney CEO Bob Iger, debate whether Berkshire Hathaway is facing a "conglomerate discount" after its recent management shakeup, and discuss why sometimes the best investing strategy is simply admitting you might be the "dumbest person in the room."00:24 Introducing the Guest: Bill Brewster00:50 Bill's Investment Philosophy04:05 Frameworks vs. Rules in Investing06:59 Evolving as an Investor11:01 David Gardner's Influence18:18 Goals vs. Incentives in Investing24:03 Building a Robust Investing Framework24:27 Traits of Quality Enterprises26:18 Economic Moats and Management Insights27:45 Disney's Leadership and Strategic Shifts32:58 Berkshire Hathaway's Future LeadershipCompanies mentioned: BN, BRK.B, CLPT, COST, DIS, FAST, GIS, JPM, MCD, MELI, NFLX, OLN, OXY, PM, SHOP, WBD, WMT*****************************************Check out The Business Brew: https://www.thebusinessbrew.com/*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

It's time to grade our 2025 predictions (spoiler: we were mostly wrong) and make some reckless new calls for 2026. We debate whether Oracle or Alphabet will be the next mega-cap winner, if Tesla's full self-driving ambitions will crash the stock, and why Strategy might be the single most dangerous stock to own next year. Plus, we ask the big question: Will the market finally crash in 2026, or is the AI bubble just getting started?00:16 Reckless Predictions and Accountability00:34 Catching Up After the Holidays01:42 Reviewing Last Year's Predictions06:03 Stock Picks for 202511:10 Stocks to Avoid in 202520:46 Reflecting on Housing Market Predictions24:30 S&P 500 Prediction Review25:16 New Predictions for 202626:35 Oracle's Market Potential27:29 Alphabet's AI Advantage28:43 ASML and GE Aerospace Predictions31:55 Kinsale Capital and Stock Picks34:29 Stocks to Avoid in 202640:31 Reckless Predictions for 2026Companies mentioned: AAPL, ASML, BRK.B, DFH, ENPH, GE, GOOGL, GRBK, INTC, KNSL, LLY, LEN, MELI, META, MSFT, MSTR, MTH, NVDA, ORCL, PHM, PLTR, TREX, TSLA, WMT*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jason and Jeff discuss why the best time to analyze a company might be weeks after they report, and share their personal strategies for this quieter period. 03:00 Why You Should Wait a Month Before Analyzing Earnings 06:00 Early Investing Mistakes 12:00 Panic-Buying and the CrowdStrike Example 15:00 How Incentives (and "Being First") Skew Financial Media 20:00 Annual Reports & The Rexford Industrial Deep Dive 24:00 The Value of Community: Canadian Solar 26:00 Spreadsheets and "Quiet Time" Research 29:00 Timing Buys Around Earnings Dates35:00 Improvements: Investing Journal? (Airbnb)Companies mentioned: ABNB, CRWD, CSIQ, REXR, TTD*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

In this month’s mailbag, Jason and Jeff tackle the "Book Value" bear thesis for Lemonade and discuss when the company might finally reach profitability. They also address a listener's dilemma about what to do with a losing position in PayPal, debating the sunk cost fallacy and the company’s turnaround prospects. Finally, the hosts weigh in on whether Cava or Chipotle is the better buy right now and explain how to choose between Brookfield Corporation and Brookfield Renewable.01:13 Mailbag: Answering Your Questions03:01 First Question: Lemonade's Book Value Bear Thesis16:25 Second Question: Adding to a Losing Position23:40 Pandemic Impact on Digital Growth23:48 PayPal's Strategic Shift24:22 Dividend Announcement and Future Outlook25:15 Investment Decisions and Opportunity Cost25:59 PayPal's IPO Journey and Current Challenges26:46 Investor Caution and Decision-Making28:23 Market Confusion and Analytical Challenges31:58 Chipotle vs. Kava: Investment Insights32:13 Fast Casual Dining Industry Analysis41:16 Brookfield Renewable vs. Brookfield CorporationCompanies mentioned: BAM, BEP, BN, CAVA, CMG, DRI, ETSY, LMND, PINS, PYPL, SBUX, SOFI*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jason and Jeff challenge their own investing biases and debate whether they’re wrong about holding three specific stocks: Ryman Hospitality Properties (RHP), Texas Instruments (TXN), and Dream Finders Homes (DFH).00:42 Today's Topic: Questioning Your Investment Thesis02:26 Listener Engagement and Support04:21 Stock Spotlight: Ryman Hospitality Properties09:36 Analyzing Ryman's Performance and Strategy22:29 Stock Spotlight: Texas Instruments23:22 The Importance of Analog Semiconductors24:34 Texas Instruments' Business Strategy25:59 Challenges and Opportunities in the Analog Chip Market27:40 Evaluating Texas Instruments' Stock Performance32:53 Home Builders: A Sector Analysis33:48 Dream Finders Homes: A Deep Dive35:14 Investment Strategies and Portfolio ManagementCompanies mentioned: AMD, DFH, GRBK, HLT, MAR, MTH, NVDA, NVR, O, RHP, TXN*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jason and Jeff are joined by John Rotonti for a conversation on the current state of the market and the AI bubble. John explains his "iron fist" investing philosophy and why the worst thing you can do is let go of a true compounding machine too early.01:38 John's Career Update04:21 Investment Philosophy and Challenges11:55 Market Insights and AI Discussion16:57 Infrastructure and Technological Shifts28:59 Tariffs and Economic Impact30:36 Legacy Companies in AI Infrastructure32:15 Cyclical Nature of Markets and Inflation33:29 Interest Rates and Economic Policies36:07 Pricing Power and Consumer Behavior43:56 AI Adoption and Market Potential48:36 Investment Strategies and Market History54:54 Conclusion and Final ThoughtsCompanies mentioned: APH, BIP, BN, CMG, INTC, NVDA*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

In the November livestream, we started with a market "vibe check" on the recent AI stock sell-off, debated the "AI bubble", floated a hot take on Apple's "wait and license" strategy, and answered live questions from viewers. We also announced the Q3 portfolio contest winner.01:58 Market Vibes and Stock Performance10:29 AI Revolution and Market Speculations25:41 Brookfield Asset Management and Sentinel One Insights34:13 Exploring the Cybersecurity Landscape34:58 The Impact of Cybersecurity Outages37:42 SanDisk and the AI Boom41:43 Investing Unscripted Portfolio Contest45:58 Reflections on Stock Picks and Market Trends56:17 Political Implications on the Stock Market59:44 Closing Remarks and Future PlansCompanies mentioned: AAPL, AMZN, BAM, BN, CRWD, GOOGL, META, S, SNDK, TSLA*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jason and Jeff chat about the "circular" AI deals, whether AI stocks are just hype, and what it would actually take for this bubble to keep inflating. In this episode, we ask:Are AI stocks dangerously overvalued? What are these "circular deals" between companies like Nvidia, AMD, and OpenAI? Is this AI rally just like the dot-com bubble? Will AI lead to massive job losses, or will it just change what our jobs look like? Where will all the energy come from to power AI? (And what does this mean for nuclear power?) How we're thinking about investing and building a resilient portfolio right now.00:23 Exploring the AI Bubble00:56 Pitching the Premium Plan03:38 Market Crash Expectations06:33 AI's Impact on the Market15:55 Energy and AI: A Symbiotic Relationship22:41 The Future of Jobs in an AI-Driven World26:16 AI's Impact on Employment and Economy27:08 Amazon's AI Evolution with Alexa28:05 AI's Role in Business and Education33:34 AI's Influence on Market and Investments37:10 Future of Top Companies and AI42:06 Investment Strategies Amid AI UncertaintyCompanies mentioned: ADBE, AMD, AMZN, ASML, LMND, NOK, NOW, NVDA, TSM*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jason and Jeff answer listener questions about Pinterest stock, the nature of individual stock-picking, their financial goals, favorite podcasts, and Halloween candies on this episode of Investing Unscripted.01:14 Analyzing Pinterest as an Investment03:24 The Challenges of Monetizing Pinterest10:10 Listener Question: Are Stock Pickers Narcissists?23:09 Determining Financial Goals24:33 Understanding Retirement Income Needs25:16 The 4% Rule Explained26:56 Building Healthy Financial Habits27:51 Personal Investment Strategies29:50 Reflecting on Long-Term Investment Returns30:40 Fun Questions: Podcasts and Halloween Candy34:24 Investing in Candy CompaniesCompanies mentioned: HSY, MDLZ, NSRGY, PINS*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jason and Jeff discuss the concept of moats in investing, exploring their validity, limitations, and real-life applicability across various industries, including technology, retail, and pharmaceuticals.01:25 Debating the Existence of Moats04:01 Intangible Asset Moats: Apple and Nike15:12 Pharmaceutical Moats and Patent Protection16:42 Cost Advantages and Efficient Scale24:13 Amazon's Distribution Network Moat24:44 The Amazon Shopping Experience26:05 Amazon's Cost Advantage and Business Model28:18 Switching Costs and Market Stickiness29:12 Shopify's Role in E-commerce31:15 The Risk of Complacency in Companies with High Switching Costs36:59 Network Effects in Business43:55 The Importance of Competitive AdvantagesCompanies mentioned: AAPL, ADBE, AMZN, KO, MA, NKE, ON, SHOP, TSM, UA, V*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: [email protected]: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted******************************************Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest