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Afford Anything · October 2, 2026 · 1h 9m

AI, Debt, and a Social Security Shortfall. Should Your Money Plans Change? With Rob Berger

Many retirees fear running out of money more than they fear dying. With AI reshaping the economy, $1 trillion in interest payments, and Social Security facing a shortfall, it's natural to worry. Rob Berger, former securities lawyer and founder of Dough Roller, discusses how to navigate today's high stock prices, when to trim concentrated positions, and how to create a retirement floor with guaranteed income. He also emphasizes that daily spending habits often matter more than investing expertise.

This summary was generated from show notes and public descriptions, not from a full transcript review. Details may contain inaccuracies.

Preview

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Evaluating High Stock Prices
Rob Berger explains how to assess whether today's high stock valuations warrant adjusting your asset allocation or retirement timeline.
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When to Trim a Concentrated Stock Position
Berger discusses the trade-offs of trimming a stock that has grown to dominate your portfolio, weighing concentration risk against tax consequences.

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