Staying invested: the cost of missing best days

Why do most investors fail at the exact moments when staying invested matters most—and how can options help fix that? In this episode, I talk with Hamilton Reiner, Managing Director at J.P. Morgan Asset Management and CIO of the U.S. Core Equity Team, about how options can be used not for speculation, but to create discipline, manage risk, and help investors stay invested through market volatility. Hamilton shares lessons from more than three decades managing equities and derivatives, explains why volatility is misunderstood, and breaks down how hedged strategies, rebalancing, and risk-based portfolio construction can dramatically improve long-term outcomes—without requiring heroic market timing.

Highlights:

• Why options are about precision, not leverage
• Hedging vs. income: the two primary institutional use cases for options
• How downside buffers help investors stay invested during drawdowns
• Why volatility is a feature of equities, not a flaw
• The biggest behavioral mistakes investors make in up and down markets
• Why missing the best days destroys long-term returns
• How rebalancing quietly outperforms market timing
• The role of options inside a modern 60/40 portfolio
• Why risk tolerance—not asset allocation—should come first
• Lessons from 2008, 2020, and decades of market cycles
• The underrated power of compounding and staying in the game

Guest Bio:

Hamilton Reiner, managing director, is CIO of the U.S. Core Equity Team, Head of U.S. Equity Derivatives for J.P. Morgan Equity Asset Management, and a portfolio manager. He has been managing U.S. equities and U.S. equity derivatives for over 30 years, at firms such as Barclays Capital, Lehman Brothers, and Deutsche Bank. He started his career at the options investing firm O’Connor and Associates, where he developed his passion for derivatives investing. Hamilton obtained a B.S.E. in Finance from the Wharton School of the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Hamilton Reiner:

LinkedIn: https://www.linkedin.com/in/hamilton-reiner-7033594b/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:32) Understanding Options: Strategies and Historical Use (4:20) Managing Stock Gains and Behavioral Biases in Investing (8:16) The Importance of Risk Tolerance and Market Timing (18:27) Decision-Making Challenges in Institutional Investment (22:17) Market Uncertainty and the Role of the VIX (24:14) Volatility, Investment Sizing, and Portfolio Integration (30:18) Market Cycles, Behavioral Biases, and Career Advice (38:23) Key Investment Lessons and the Power of Compounding (43:09) Closing remarks