225. September 2026 Mailbag

In this September 2026 Mailbag, Jason and Jeff tackle listener questions on when it makes sense to "average up" on massive winners, analyzing David Gardner’s contrarian approach to building a Rule Breaker portfolio. The hosts then explore the specific valuation and counter-cyclical margin arguments behind Jason's recent purchase of The TJX Companies, and debate the psychology of co-managing spousal IRAs. To close the episode, the duo reviews listener submissions for a "5 Stocks for 10 Years" portfolio, ultimately drafting their own hypothetical decades-long portfolios from the audience's picks. 02:03 Patreon Shoutout 03:07 Rapid Fire Housekeeping 04:15 Mailbag Begins 04:58 Double Down Winners 16:50 TJX Valuation Debate 24:42 ResMed Growth Outlook 28:20 When to Take Profits 29:56 When Valuation Matters 31:50 Couples Managing IRAs 34:49 Risk Across Net Worth 38:18 Spreadsheets And Aggregation 43:06 Five Stocks For 10 Years 44:19 Discord Picks Breakdown 48:23 Picking Five From The List Companies mentioned: AER, AMZN, ASML, AXON, BAM, BN, BRK.B, COST, CVX, ISRG, LLY, LMND, MA, MEDP, META, RBRK, RMD, SBUX, TBBB, TJX, TSM Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com ***************************************** To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted ***************************************** Join our Patreon Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription! Learn more about your ad choices. Visit megaphone.fm/adchoices