Investing Unscripted

186. December 2025 Mailbag


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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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Investing UnscriptedBy Jason Hall and Jeff Santoro

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