The "T-Bill & Chill" Era Is Ending. What Should Investors Do Next? | Michael Lebowitz

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Aug 12, 2025

Michael Lebowitz, co-portfolio manager at Real Investment Advice, dives into the end of the 'T-bill and Chill' era. He discusses the speculative nature of the current market, comparing it to the dot-com bubble and the rise of high-beta stocks. Lebowitz highlights the importance of active management, risk strategies, and diversification in navigating potential volatility. He also critiques the reliability of economic data and advocates for utilizing real-time insights to inform investment decisions, especially as the Fed considers rate cuts.

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INSIGHT

Speculative Rally Echoes Dot‑Com Behavior

The recent rally was led by high-beta, low-profitability, speculative names rather than the MAG7 winners from 2023–24.
This mirrors early dot-com era behavior where risk appetite shifted to the most speculative stocks for a period.

ADVICE

Prepare A Ready Roster Of Stocks

Assemble a roster of potential stocks to buy so you can act quickly when rotations occur.
Rotate actively instead of holding yesterday's winners into a changing market.

INSIGHT

Beta Extremes Led Then Reversed

Beta deciles showed high-beta stocks surged ~1111% from 1998–2000 while low-beta floundered.
That extreme outperformance reversed over the full cycle to 2003, favoring low-beta later.

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Trillions in investor capital has been locked up in the "T-bill and Chill" trade for several years now.But will the Fed expected to cut rates materially over the next year, that trade is coming to an end.Where should all that capital consider going next?Portfolio manager Michael Lebowitz and I dive into this key question in this video.

WORRIED ABOUT THE MARKET? SCHEDULE YOUR FREE PORTFOLIO REVIEW with Thoughtful Money's endorsed financial advisors at https://www.thoughtfulmoney.com#interestrates #federalreserve #bondyields

0:00 - Welcome and Introduction

2:09 - Discussion on Speculative Market Trends and Dot-Com Echoes

4:00 - Comparison to Meme Stocks and Cathie Wood-Type Tech Stocks

5:40 - Historical Context of 1998-2000 Dot-Com Boom

7:11 - Analysis of High-Beta vs. Low-Beta Stocks1

1:50 - Growth vs. Value Performance During Dot-Com Era1

4:22 - Speculative Mania and Risk Management Strategies

18:03 - Importance of Diversification and Active Management

19:41 - Growth vs. Value Index and Historical Trends

22:01 - Small-Cap vs. Large-Cap and Profitability Trends

25:06 - Recent Market Trends and High-Beta Outperformance

29:03 - Potential Triggers for High-Beta Stock Correction

33:12 - Economic Slowdown as a White Swan Risk

38:01 - Critique of BLS Data Reliability

43:31 - Need for Real-Time Data and Fed Reform

47:51 - Model-Based Fed Policy and Transparency

50:21 - Bond Market Dynamics and Yield Curve Strategy

56:26 - Positioning for Potential Fed Rate Cuts

58:39 - End of T-Bill and Chill Trade Considerations

1:02:17 - Closing Remarks and Call to Action

1:04:14 - Michael’s Advice on Separating Politics from Investing_____________________________________________ 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.IMPORTANT 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 © 2025 Thoughtful Money LLC. All rights reserved.