Is a Market Crash Coming? AI Bubbles, Bear Markets & Retirement Risk With Special Guest Jim Stack

The Dow is hovering near 50,000. AI stocks are dominating the market. And investors are feeling both confident and anxious at the same time.

It's the first Friends Talk Money episode of 2026, and we’re joined by expert market strategist Jim Stack, founder of InvestTech Research, to unpack what’s really happening beneath the surface of today’s stock market and what it means for investors nearing or in retirement.

Jim explains why extreme market valuations don’t cause bear markets, but dramatically increase the risk. He also breaks down why indexing may no longer feel as diversified as investors think, how the “K-shaped economy” is being driven by paper wealth, and why capital preservation matters more than chasing upside late in a bull market.

In this episode, we cover:

• Why today’s market feels eerily similar to past bubbles
• The real danger of AI stock mania (and what history tells us)
• How a 50% loss can delay retirement by years
• Jim Stack’s “Ulcer Index” and the true cost of bear markets
• Why Warren Buffett is sitting on hundreds of billions in cash
• Defensive portfolio strategies for investors 50+
• Index fund concentration risk most investors overlook
• Housing, interest rates, and what retirees should consider next

Jim has successfully helped investors navigate market downturns for over 40 years, including the 1987 crash, the dot-com bust, and the 2008 financial crisis. His message is clear: this isn’t about market timing, it’s about risk management.

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