Thoughtful Money with Adam Taggart
Thoughtful Money with Adam Taggart

Ready For A Bear Market? Most Investors Aren't | Ted Oakley

September 24, 2026

AI Summary

5 min read

Ready For A Bear Market? Most Investors Aren't

Ted Oakley, founder and managing partner of Oxbow Advisors, has been managing money through market cycles for decades. In this conversation with Adam Taggart, he describes a market that looks healthy on the surface but is far more fragile than most investors realize. The S&P 500 and NASDAQ sit near all-time highs, yet Oakley points out that the average sector is down about 18-19% from its high. The headline indexes are being carried by a single story: artificial intelligence.

The AI Concentration Problem

Oakley sees the current market as a "one trick pony" where everything is tied to AI. Pull AI out of the economy, he says, and those strong GDP numbers would look very different. The top ten companies now make up roughly 41-42% of the S&P 500 index. Oakley warns that investors who think they are diversified by owning an index fund may be in for a surprise: "If you own the index, you're not very diversified. You might think you are, but you're really not."

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What you'll learn

  • 1 (01:00) **Bear Markets Are Inconceivable to Today's Investors** - Oakley opens by contrasting the frequency of bear markets in the 70s/80s (every few years) with the current generation's lack of experience, noting the Fed can't bail everyone out this time.
  • 2 (03:16) **The Economy Is a "One-Trick Pony" Tied to AI** - Oakley explains that strong GDP numbers are misleading because the entire economy is riding on AI, and pulling that out would make growth look much worse.
  • 3 (04:48) **Under the Hood, Most Sectors Are Already Down 18-19%** - Oakley reveals that despite the headline indices being near highs, 11 of the S&P 500's sectors are down significantly, creating a misleading picture of market health.
  • 4 (06:18) **Finding Value Outside the AI Hype** - Oakley describes running constant screens for high-quality, low-valuation companies with good cash flow, finding them primarily in energy and materials, not AI.
  • 5 (08:25) **The AI Bubble is Worse Than the Dot-Com Era** - Oakley explains that unlike the late 90s, where only telecom and tech were bubbly, every sector today is trying to tie itself to AI, making a potential bust far more widespread.
  • 6 (13:04) **The AI Bust Could Be as Bad as the Dot-Com Crash** - Oakley draws a direct parallel to the late 90s, arguing that while AI will eventually be productive, the current valuations on the top companies are unsustainable and a correction will be comparable in scale.
  • 7 (17:09) **A Generation of Investors and Advisors Has Never Seen a Real Bear Market** - Oakley warns that both retail investors and professional money managers lack the experience to handle a classic, multi-year bear market, leading to panic selling at the worst possible time.

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Guests on this episode

Ted Oakley Adam Taggart

Show Notes

TALK TO TED & HIS TEAM at Oxbow Advisors FOR FREE by filling out the short form at https://www.thoughtfulmoney.com/oxbowHigh-net worth financial advisor Ted Oakley is concerned about how so many investors AND financial professionals are unprepared to deal with the next bear market when it arrives.We are very overdue for one. And yet, most investors act as if the current bull market is going to last forever, taking on far more risk in their portfolios than circumstances merit.For a deep discussion on today's market risk with an advisor who has successfully navigated more bear markets than most people alive, watch this video.#bearmarket #corporateearnings #marketcorrection _____________________________________________ Thoughtful Money LLC is a Registered Investment Advisor Promoter.We produce educational content geared for the individual investor. It’s important to note that this content is NOT investment advice, individual or otherwise, nor should be construed as such.We recommend that most investors, especially if inexperienced, should consider benefiting from the direction and guidance of a qualified financial advisor registered with the U.S. Securities and Exchange Commission (SEC) or state securities regulators who can develop & implement a personalized financial plan based on a customer’s unique goals, needs & risk tolerance.All the details on Thoughtful Money's relationship with the financial advisors it endorses, many of whom regularly appear on this program, can be found in the following documents. We highly recommend you review these documents as they cover the terms that will apply should you choose to work with one of these firms at any time after watching this video.Thoughtful Money Disclosure Document: https://thoughtfulmoney.com/disclosureThoughtful Money Agreement: https://thoughtfulmoney.com/agreementIMPORTANT NOTE: There are risks associated with investing in securities.Investing in stocks, bonds, exchange traded funds, mutual funds, money market funds, and other types of securities involve risk of loss. Loss of principal is possible. Some high risk investments may use leverage, which will accentuate gains & losses. Foreign investing involves special risks, including a greater volatility and political, economic and currency risks and differences in accounting methods.A security’s or a firm’s past investment performance is not a guarantee or predictor of future investment performance.Thoughtful Money and the Thoughtful Money logo are trademarks of Thoughtful Money LLC.Copyright © 2026 Thoughtful Money LLC. All rights reserved.

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