In the final episode of 2025, Jason and Jeff empty the mailbag to answer listener questions about managing sudden wealth, tax strategies, and portfolio management. They debate the pros and cons of rebalancing versus letting your winners run (featuring a look at Jason’s highly concentrated Roth IRA) and discuss how to handle a financial windfall like an inheritance. The hosts also break down the risks of complex conglomerates like Brookfield, analyze whether MTY Food Group is a value play or a value trap, and give their unfiltered take on whether recent political news finally makes Cannabis stocks investable.
00:23 Listener Mailbag and Community Engagement
03:09 First Listener Question: Balancing Financial Results and Industry Knowledge
06:50 Using AI Tools for Investment Research
08:27 Real-World Examples and Industry Research
11:04 Brookfield Corporation: Legal Issues and Investment Risks
14:50 MTY Foods: Cash Flow and Investment Potential
22:28 Rebalancing Portfolios: Strategies and Considerations
26:10 Risk Management in Asset Allocation
26:54 Personal Investment Stories and Lessons
28:21 Strategies for 401k, Roth, and Brokerage Accounts
37:29 Handling Inheritance and Tax Implications
45:26 Investing in Cannabis Stocks
50:54 Conclusion and Viewer Engagement
Companies mentioned: AEO, AMZN, BN, CAVA, CMG, CRWD, CTRE, DRI, EAT, EPR, GOOGL, LOB, MCD, MELI, MO, MTY, NFLX, NUE, STLD, TAP, TSM, YUM
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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
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In this holiday special, Jason and Jeff wrap up 2025 by reviewing the year's biggest stories—from the AI boom to inflation and trade wars. They discuss whether the AI narrative is showing any cracks and debate which sectors might dominate in 2026, with Jason making a case for homebuilders and Jeff eyeing the energy sector. The hosts also reveal the simplified rules for the 2026 Investing Unscripted Portfolio Contest, inviting listeners to submit their "buy and hold" picks for charity. Finally, they share their "YOLO" picks and confess what they got wrong in 2025.
01:25 Upcoming Contest Announcement
02:00 2025 Year in Review
05:47 AI Dominance and Market Trends
13:08 Stock Picks for 2026
18:19 Sector Predictions for 2026
23:25 AI and Renewable Energy: The China Factor
24:53 Reflecting on 2025: Biggest Misjudgments
27:39 Lemonade's Unexpected Success
30:48 Top Performing Stocks of 2025: Predictions for 2026
34:47 Robinhood's Race Against Time
37:30 2026 Stock Contest: Rules and Guidelines
44:29 Wrapping Up: Final Thoughts and Holiday Wishes
Companies mentioned: GOOGL, ENPH, LMND, MU, NEM, NVDA, PLTR, HOOD, STX, SNPS, WBD, WDC
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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
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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 Brewster
00:50 Bill's Investment Philosophy
04:05 Frameworks vs. Rules in Investing
06:59 Evolving as an Investor
11:01 David Gardner's Influence
18:18 Goals vs. Incentives in Investing
24:03 Building a Robust Investing Framework
24:27 Traits of Quality Enterprises
26:18 Economic Moats and Management Insights
27:45 Disney's Leadership and Strategic Shifts
32:58 Berkshire Hathaway's Future Leadership
Companies mentioned: BN, BRK.B, CLPT, COST, DIS, FAST, GIS, JPM, MCD, MELI, NFLX, OLN, OXY, PM, SHOP, WBD, WMT
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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
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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 Accountability
00:34 Catching Up After the Holidays
01:42 Reviewing Last Year's Predictions
06:03 Stock Picks for 2025
11:10 Stocks to Avoid in 2025
20:46 Reflecting on Housing Market Predictions
24:30 S&P 500 Prediction Review
25:16 New Predictions for 2026
26:35 Oracle's Market Potential
27:29 Alphabet's AI Advantage
28:43 ASML and GE Aerospace Predictions
31:55 Kinsale Capital and Stock Picks
34:29 Stocks to Avoid in 2026
40:31 Reckless Predictions for 2026
Companies 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
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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
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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 Dates
35:00 Improvements: Investing Journal? (Airbnb)
Companies mentioned: ABNB, CRWD, CSIQ, REXR, TTD
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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
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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 Questions
03:01 First Question: Lemonade's Book Value Bear Thesis
16:25 Second Question: Adding to a Losing Position
23:40 Pandemic Impact on Digital Growth
23:48 PayPal's Strategic Shift
24:22 Dividend Announcement and Future Outlook
25:15 Investment Decisions and Opportunity Cost
25:59 PayPal's IPO Journey and Current Challenges
26:46 Investor Caution and Decision-Making
28:23 Market Confusion and Analytical Challenges
31:58 Chipotle vs. Kava: Investment Insights
32:13 Fast Casual Dining Industry Analysis
41:16 Brookfield Renewable vs. Brookfield Corporation
Companies mentioned: BAM, BEP, BN, CAVA, CMG, DRI, ETSY, LMND, PINS, PYPL, SBUX, SOFI
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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
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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 Thesis
02:26 Listener Engagement and Support
04:21 Stock Spotlight: Ryman Hospitality Properties
09:36 Analyzing Ryman's Performance and Strategy
22:29 Stock Spotlight: Texas Instruments
23:22 The Importance of Analog Semiconductors
24:34 Texas Instruments' Business Strategy
25:59 Challenges and Opportunities in the Analog Chip Market
27:40 Evaluating Texas Instruments' Stock Performance
32:53 Home Builders: A Sector Analysis
33:48 Dream Finders Homes: A Deep Dive
35:14 Investment Strategies and Portfolio Management
Companies mentioned: AMD, DFH, GRBK, HLT, MAR, MTH, NVDA, NVR, O, RHP, TXN
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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
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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 Update
04:21 Investment Philosophy and Challenges
11:55 Market Insights and AI Discussion
16:57 Infrastructure and Technological Shifts
28:59 Tariffs and Economic Impact
30:36 Legacy Companies in AI Infrastructure
32:15 Cyclical Nature of Markets and Inflation
33:29 Interest Rates and Economic Policies
36:07 Pricing Power and Consumer Behavior
43:56 AI Adoption and Market Potential
48:36 Investment Strategies and Market History
54:54 Conclusion and Final Thoughts
Companies mentioned: APH, BIP, BN, CMG, INTC, NVDA
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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
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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 Performance
10:29 AI Revolution and Market Speculations
25:41 Brookfield Asset Management and Sentinel One Insights
34:13 Exploring the Cybersecurity Landscape
34:58 The Impact of Cybersecurity Outages
37:42 SanDisk and the AI Boom
41:43 Investing Unscripted Portfolio Contest
45:58 Reflections on Stock Picks and Market Trends
56:17 Political Implications on the Stock Market
59:44 Closing Remarks and Future Plans
Companies mentioned: AAPL, AMZN, BAM, BN, CRWD, GOOGL, META, S, SNDK, TSLA
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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
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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 Bubble
00:56 Pitching the Premium Plan
03:38 Market Crash Expectations
06:33 AI's Impact on the Market
15:55 Energy and AI: A Symbiotic Relationship
22:41 The Future of Jobs in an AI-Driven World
26:16 AI's Impact on Employment and Economy
27:08 Amazon's AI Evolution with Alexa
28:05 AI's Role in Business and Education
33:34 AI's Influence on Market and Investments
37:10 Future of Top Companies and AI
42:06 Investment Strategies Amid AI Uncertainty
Companies mentioned: ADBE, AMD, AMZN, ASML, LMND, NOK, NOW, NVDA, TSM
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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
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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 Investment
03:24 The Challenges of Monetizing Pinterest
10:10 Listener Question: Are Stock Pickers Narcissists?
23:09 Determining Financial Goals
24:33 Understanding Retirement Income Needs
25:16 The 4% Rule Explained
26:56 Building Healthy Financial Habits
27:51 Personal Investment Strategies
29:50 Reflecting on Long-Term Investment Returns
30:40 Fun Questions: Podcasts and Halloween Candy
34:24 Investing in Candy Companies
Companies mentioned: HSY, MDLZ, NSRGY, PINS
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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
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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 Moats
04:01 Intangible Asset Moats: Apple and Nike
15:12 Pharmaceutical Moats and Patent Protection
16:42 Cost Advantages and Efficient Scale
24:13 Amazon's Distribution Network Moat
24:44 The Amazon Shopping Experience
26:05 Amazon's Cost Advantage and Business Model
28:18 Switching Costs and Market Stickiness
29:12 Shopify's Role in E-commerce
31:15 The Risk of Complacency in Companies with High Switching Costs
36:59 Network Effects in Business
43:55 The Importance of Competitive Advantages
Companies mentioned: AAPL, ADBE, AMZN, KO, MA, NKE, ON, SHOP, TSM, UA, V
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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
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Jason and Jeff are joined by financial planning expert Robert Brokamp to discuss key concepts in retirement planning for individuals at every stage of their career, covering topics such as 401(k)s, Roth IRAs, pensions, and the importance of cash and bonds in both accumulation and retirement phases.
00:48 Introducing the Guest: Robert Brokamp
01:31 Previous Episodes and Listener Feedback
02:32 Retirement Planning for New Adults
04:51 Maximizing Employer Match Contributions
09:25 Roth vs. Traditional 401(k)
13:21 Pensions and Retirement Income
21:46 Retirement Lifestyle and Planning
25:56 Emergency Funds and Cash Management
27:14 Living in Uncertainty: The Need for a Backup Plan
27:47 Retirement Savings: Stocks vs. Cash
28:02 The Importance of Cash in Volatile Markets
29:46 Approaching Retirement: Adjusting Your Portfolio
30:55 Building a Cash Cushion and Transitioning to Bonds
33:02 Understanding Bonds: Funds vs. Individual Bonds
36:01 The Impact of Interest Rates on Bonds
44:51 Holding Stocks in Retirement
49:21 Required Minimum Distributions and Tax Strategies
50:51 Finding Joy in Work and Retirement
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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
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Jason and Jeff discuss the potential for an upcoming market crash in 2026, reflecting on last year's predictions, and explore the impacts of AI investment, interest rates, inflation, and tariffs on the market, providing insights on how to adjust investment strategies in uncertain times.
01:55 Reflecting on Last Year's Market Crash Predictions
06:09 The AI Boom and Market Speculation
14:37 Interest Rates and Economic Concerns
24:06 Economic Stability and Employment
24:23 Impact of AI on Entry-Level Jobs
24:55 Government Shutdown and Unemployment
25:43 Inflation and Tariffs
30:27 Investment Strategies and Market Predictions
30:52 Savvy Trader Portfolio Insights
32:28 Long-Term vs Short-Term Investment Goals
37:37 Practical Uses of AI in Investing
40:06 Preparing for Market Crashes
Companies mentioned: CRWV, MSFT NVDA
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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
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In the October livestream, Jeff and Jason discuss the challenges of trimming stocks amid rapid gains, the temptation of big winners, QuantumScape's potential, and managing personal investment decisions to maximize long-term gains.
04:32 Market Trends and Economic Uncertainty
08:40 Stock Talk: QuantumScape and Investment Strategies
29:13 Ducati's Quantum Leap
29:36 Corning Partnership Boosts Stock
30:26 Investor Concerns and Market Reactions
31:53 Speculative Investments and Market Sentiment
35:06 Strategies for Managing High-Performing Stocks
38:07 Balancing Portfolio and Trimming Positions
Companies mentioned: MELI, NVDA, QS, SHOP, SOFI, WINA
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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
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Jason and Jeff randomly analyze each other's stock portfolios, presenting spontaneous bear cases and discussing whether they would buy shares today.
00:35 Explaining the Random Stock Challenge
04:08 First Stock Analysis: LGI Homes
11:59 Second Stock Analysis: Roku
18:21 Third Stock Analysis: QXO
25:27 Fourth Stock Analysis: Airbnb
35:48 Simon Property Group: Malls Aren't Dead Yet
42:28 Procore: Modernizing the Construction Industry
52:26 Reflecting on Investment Strategies
Companies mentioned: ABNB, LGIH, ROKU, SPG, QXO
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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
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Jason and Jeff respond to listener questions on stock-based compensation, restaurant industry investments, and recent market dynamics related to the Trade Desk, while sharing their insights on various investing strategies and market trends.
00:37 Listener Questions and Engagement
02:58 Quarterly Earnings Debate
17:32 YouTube Comments and Trade Desk Discussion
23:27 Market Sentiment and Trade Desk Analysis
23:48 Ad Tech Industry Dynamics
26:08 Stock Valuation and Future Prospects
30:25 Stock-Based Compensation Discussion
38:44 Investing in Restaurant Stocks
47:45 Spam Comment of the Month
Companies mentioned: AMZN, ASAN, CAVA, CFLT, CMG, CPNG, CRWD, MCD, MELI, MSFT, SBUX, SE, TTD, XYZ
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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
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Jason and Jeff interview David Gardner, co-founder of The Motley Fool, to talk about his new book 'Rule Breaker Investing,' investing philosophies, and a friendly stock-picking competition.
00:48 Welcoming David Gardner
01:27 David's Early Investing Journey
03:24 The Rule Breaker Philosophy
08:52 The Importance of Holding
19:30 Valuation and Intangibles
33:16 Misunderstandings of Rule Breaker Investing
37:23 Reflecting on Stock Picks and Surprises
37:48 The Humility in Investing
38:27 Lessons from Stock Picking
41:42 The Value of Direct Stock Buying
43:11 Fun with Stock Picking Games
43:55 Introducing the Smattering Six
46:06 Stock Picking Contest
01:04:06 The Importance of Long-Term Investing
Companies mentioned: AMZN, AX, CPNG, MELI, NVDA, PCOR, TBBB, TMDX, WRBY
Check out David’s new book: https://www.rulebreakerinvesting.com/
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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
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Jason and Jeff discuss stocks that are performing well and those struggling in their portfolios, evaluate the companies' performances, and share their thoughts on portfolio management and future investment strategies.
02:33 Discussing the Mailbag and Listener Engagement
04:09 Starting the Stock Discussion: Mercado Libre
05:54 Deep Dive into Mercado Libre's Performance
18:31 Exploring Lemonade and Upstart
27:03 Navigating Investment Conviction and Price Anchoring
29:07 Evaluating Lemonade's Growth Strategy
32:05 Understanding Upstart's Market Position
35:55 Moderna: A Long-Term Bet on mRNA Technology
42:38 Live Oak Bank: A Small Business Lender's Journey
49:27 Wrapping Up and Final Thoughts
Companies mentioned: AX, LMND, MELI, LOB, MRNA, SHOP, UPST
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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
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Jason and Jeff discuss cryptocurrencies, delve into financial strategies like options trading, and take questions from the audience about market trends, the housing market, and more.
00:32 3D Printing and Future Technologies
03:07 AI and Investment Predictions
06:46 Market Vibes and S&P 500 Discussion
15:13 Investment Strategies and Options Trading
20:43 Economic Outlook and Rate Cuts
32:21 Crypto and AI Speculation
32:57 Potential AI Market Risks
33:57 Electricity Generation Concerns
34:16 Gradual Slowdown in AI Spending
34:57 Crypto Bubble Indicators
36:23 Housing Market Stability
36:43 Sopranos and New Jersey
38:10 Housing Market Fundamentals
46:14 QuantumScape Investment Discussion
51:09 Office Real Estate and Labor Market
53:05 Pandemic Stocks and Market Perception
53:39 Zoom's Future and Investor Sentiment
Companies mentioned: LMND, QS, ROKU, TBBB, TFSL, UPS, ZM
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