First Fridays 35. October 2026

In this October 2026 Mailbag, Jason and Jeff tackle listener questions on portfolio management, sector consolidation, and the psychology of holding laggards while the broader market sits near all-time highs. They evaluate whether Zeta Global's business intelligence tools pose a threat to TJX Companies' off-price retail moat, debate how to narrow down starter positions across housing and renewable energy stocks like Meritage Homes, Enphase, and First Solar, and dissect what to do when former long-term winners like MercadoLibre, Netflix, and Axon go through painful drawdowns. Plus, Jeff breaks down how doubling down on Texas Instruments at the bottom of the semiconductor cycle turned a 30% loser into a market-beating position.

In this episode, Jason and Jeff tackle the often-misunderstood world of fixed income to answer a critical question: Should you still own bonds? The hosts break down exactly why bond funds were decimated in 2022, the mechanics of the inverse correlation between interest rates and bond prices, and the vital difference between holding bond funds versus holding individual bonds to maturity. Finally, they explore why the current 5% yield environment makes fixed income a compelling wealth-preservation tool for investors looking to lock in their gains from the AI stock boom.

In this completely unscripted episode, Jason and Jeff tackle the broad economic vibes surrounding the market’s resilience despite mounting geopolitical and macroeconomic uncertainty. The duo debates whether the normalization of sports betting and prediction markets is quietly threatening the culture of long-term stock investing. Plus, they unpack the complicated psychology of adding to massive winners, analyzing why Jason is considering a starter position in Broadcom despite its stretched valuation, and evaluating whether QuantumScape’s latest manufacturing pivots are a sign of commercial maturity or a yellow flag for a cult stock.

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.

Jason and Jeff pull back the curtain on their Savvy Trader portfolio to examine the core mechanics of long-term portfolio construction. Using real-world examples from their own holdings, the hosts debate the discipline required to let a multi-bagger winner run versus the psychological battle of confronting a 70% drawdown. They tackle the dangerous allure of the sunk-cost fallacy, evaluate whether high-growth portfolios actually benefit from defensive "ballast" stocks, and break down how position sizing can keep single-stock blowups from derailing your long-term compounding.