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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
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