INTERVIEW | Make Money by Thinking Long-Term and Avoiding the Market Timing Trap with Jim Lebenthal episode artwork

EPISODE · Jun 16, 2026 · 30 MIN

INTERVIEW | Make Money by Thinking Long-Term and Avoiding the Market Timing Trap with Jim Lebenthal

from Travis Makes Money · host Travis Chappell

Jim Lebenthal, Chief Market Strategist at Cerity Partners, joins Travis to share lessons from more than 25 years of managing investment portfolios and advising clients through every type of market environment. A former U.S. Navy submarine officer and regular CNBC contributor, Jim brings a unique perspective on investing, discipline, risk management, and human behavior. Drawing from his new book, How to Ride the Subway, he explains why successful investing often comes down to patience, trust, and resisting the urge to outsmart the market. On this episode we talk about: How Jim’s early experiences investing shaped his career in wealth management Lessons learned from serving as a nuclear submarine officer in the U.S. Navy Why trust, empathy, and communication are essential in financial advising The dangers of market timing, day trading, and speculative investing Current market conditions, inflation concerns, and the future of major AI-driven IPOs Top 3 Takeaways Long-term investing consistently outperforms attempts to time the market, and missing just a handful of the market’s best days can dramatically reduce returns. Successful financial advisors build trust through empathy, honesty, and consistent communication—not just investment performance. Speculation and gambling often masquerade as investing, but true wealth creation comes from patience, discipline, and owning quality assets over time. Notable Quotes "Trust is the currency of the financial advisory world." "The best days in the market almost always happen right next to the worst days." "Trading rapidly is a good way to lose money." Connect with Jim Lebenthal: Book: How to Ride the Subway: Getting Around on Wall Street and in Life CNBC: Regular contributor on CNBC's Halftime Report Company: Cerity Partners LinkedIN: https://www.linkedin.com/in/james-lebenthal-2793685/ A Word from Our Sponsors: Today's episode is brought to you by our incredible sponsors. Their support allows us to continue bringing you conversations with top investors, entrepreneurs, and thought leaders. Be sure to check out the links below and support the brands that help make the Travis Makes Money Podcast possible. - Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! - To learn more about Mode Mobile and its investor community, go to https://invest.modemobile.com/travismakesmoney -Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.Capture leads, nurture them, and close more deals—all from one powerful platform.Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices

Jim Lebenthal, Chief Market Strategist at Cerity Partners, joins Travis to share lessons from more than 25 years of managing investment portfolios and advising clients through every type of market environment. A former U.S. Navy submarine officer and regular CNBC contributor, Jim brings a unique perspective on investing, discipline, risk management, and human behavior. Drawing from his new book, How to Ride the Subway, he explains why successful investing often comes down to patience, trust, and resisting the urge to outsmart the market. On this episode we talk about: How Jim’s early experiences investing shaped his career in wealth management Lessons learned from serving as a nuclear submarine officer in the U.S. Navy Why trust, empathy, and communication are essential in financial advising The dangers of market timing, day trading, and speculative investing Current market conditions, inflation concerns, and the future of major AI-driven IPOs Top 3 Takeaways Long-term investing consistently outperforms attempts to time the market, and missing just a handful of the market’s best days can dramatically reduce returns. Successful financial advisors build trust through empathy, honesty, and consistent communication—not just investment performance. Speculation and gambling often masquerade as investing, but true wealth creation comes from patience, discipline, and owning quality assets over time. Notable Quotes "Trust is the currency of the financial advisory world." "The best days in the market almost always happen right next to the worst days." "Trading rapidly is a good way to lose money." Connect with Jim Lebenthal: Book: How to Ride the Subway: Getting Around on Wall Street and in Life CNBC: Regular contributor on CNBC's Halftime Report Company: Cerity Partners LinkedIN: https://www.linkedin.com/in/james-lebenthal-2793685/ A Word from Our Sponsors: Today's episode is brought to you by our incredible sponsors. Their support allows us to continue bringing you conversations with top investors, entrepreneurs, and thought leaders. Be sure to check out the links below and support the brands that help make the Travis Makes Money Podcast possible. - Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! - To learn more about Mode Mobile and its investor community, go to https://invest.modemobile.com/travismakesmoney -Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.Capture leads, nurture them, and close more deals—all from one powerful platform.Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices

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INTERVIEW | Make Money by Thinking Long-Term and Avoiding the Market Timing Trap with Jim Lebenthal

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This episode is 30 minutes long.

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This episode was published on June 16, 2026.

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Jim Lebenthal, Chief Market Strategist at Cerity Partners, joins Travis to share lessons from more than 25 years of managing investment portfolios and advising clients through every type of market environment. A former U.S. Navy submarine officer...

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