AI Investing: Are We Repeating the Dot-Com Bubble and 2008 Mistakes?
Feb 04, 2026Artificial intelligence is everywhere right now. From headlines about soaring tech stocks to conversations about how AI will change the world, the excitement is unmistakable. But for those planning retirement, this enthusiasm can feel unsettlingly familiar.
In a recent episode of Leibel On Fire, retirement planner Leibel Sternbach and host Freddie Bell explored how today’s AI surge echoes past market cycles—specifically the dot-com boom of the late 1990s and the financial crisis of 2008. While the technology may be new, the investor emotions driving the market are anything but.
During the dot-com era, investors believed that eyeballs mattered more than revenue. Companies achieved massive valuations without clear paths to profitability, all based on expectations of future growth. Eventually, reality caught up. Markets didn’t crash overnight, but over several painful years, many portfolios lost more than half their value. For retirees, that kind of drawdown can be devastating.
What makes today different—and potentially more dangerous—is the level of concentration. A small number of companies dominate the AI infrastructure space, from chips to data centers to large language models. Current valuations assume decades of uninterrupted growth, similar to what companies like Google achieved over 25 years. But history shows that technology rarely stays dominant that long without disruption.
For retirees and pre-retirees, the biggest challenge isn’t predicting whether AI is a bubble. As Leibel explains, bubbles are only identified after they pop. The real issue is risk management. If markets decline 40%–50%, someone still working has time to recover. Someone already retired does not.
That’s why protecting downside risk matters just as much as participating in upside growth. Retirement portfolios need balance. There must be money positioned for growth, but also money structured to preserve income, stability, and lifestyle—even if markets take years to recover.
Leibel shares a powerful example from Mark Cuban, who sold his company to Yahoo at the height of the dot-com boom. Rather than assume prices would keep rising, Cuban protected his downside. When Yahoo stock collapsed and never recovered, that decision preserved his wealth while others were wiped out.
The lesson is clear: smart investors don’t rely on optimism alone. They plan for uncertainty.
At Yields4U, Leibel’s 3-2-1 Retirement Plan is built around this reality. It focuses on three buckets, two investment strategies, and one coordinated plan designed to help retirees stay invested without exposing their entire future to market hype or fear-driven decisions.
AI may reshape industries, but it shouldn’t dictate your retirement security. The goal isn’t to rush in or run away—it’s to act with balance, discipline, and intention.
If you’re approaching retirement and wondering how today’s market excitement fits into your long-term plan, now is the time for a thoughtful conversation.
Schedule a consultation with Leibel Sternbach and his team to review your strategy and protect the retirement you’ve worked so hard to build:
https://www.yields4u.com/pages/book
Have Questions? Get the answers you need.
