186. December 2025 Mailbag

31/12/2025 51 min

Listen "186. December 2025 Mailbag"

Episode Synopsis

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 Engagement03:09 First Listener Question: Balancing Financial Results and Industry Knowledge06:50 Using AI Tools for Investment Research08:27 Real-World Examples and Industry Research11:04 Brookfield Corporation: Legal Issues and Investment Risks14:50 MTY Foods: Cash Flow and Investment Potential22:28 Rebalancing Portfolios: Strategies and Considerations26:10 Risk Management in Asset Allocation26:54 Personal Investment Stories and Lessons28:21 Strategies for 401k, Roth, and Brokerage Accounts37:29 Handling Inheritance and Tax Implications45:26 Investing in Cannabis Stocks50:54 Conclusion and Viewer EngagementCompanies mentioned: AEO, AMZN, BN, CAVA, CMG, CRWD, CTRE, DRI, EAT, EPR, GOOGL, LOB, MCD, MELI, MO, MTY, NFLX, NUE, STLD, TAP, TSM, YUM*****************************************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