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Investing for Life, Not Just Wealth with Jimmy Lebenthal

What if the principles that make us better investors could also help us become better leaders, better decision-makers and live more fulfilling lives?

In this episode of the Business Elevation Show, Chris was joined by Jimmy Lebenthal, Chief Equity Strategist at Cerity Partners, regular CNBC contributor and author of How to Ride the Subway.

A former United States Navy submarine officer turned investment strategist, Jimmy has spent more than twenty-five years helping individuals and families navigate the financial markets with confidence, patience and perspective.

Drawing on his lifelong fascination with New York City’s subway system, Jimmy uses its stations, journeys and unexpected encounters as powerful metaphors for investing, leadership and life itself.

Together, Chris and Jimmy explored why long-term thinking almost always outperforms short-term reactions, how patience and curiosity create better outcomes, and why accepting unexpected invitations can sometimes change the course of our lives.

The conversation also explored the importance of purpose, relationships, family, financial wellbeing and using wealth as a means to create a positive impact rather than simply accumulate more.

At a time when markets, politics and technology are creating uncertainty, Jimmy shared practical wisdom for making better decisions, staying focused on what matters most and building lasting success.

Here are some insights from the interview you don’t want to miss:

1. The Subway = Life & Markets

Jimmy built his book’s philosophy around his childhood love of the New York subway. Every journey, connection, and unexpected detour holds a lesson about navigating financial markets and relationships. Embrace the ride, learn from every “station,” and don’t fear getting a little lost.

2. Time IN the Market Beats Timing the Market

Forget the day-trading hype. Jimmy delivered a reality check: success comes from staying invested in quality companies over DECADES—not trying to guess the next jump. Even if you bought at the peak before the ’08 crash and held on, your annualised return would be nearly 10%. Missing just 20 of the best days in 30 years? You’d lose HALF your gains.

3. It’s All About People

Whether on a submarine or Wall Street, Jimmy learned that mastering relationships is everything. The best stock picks or business strategies mean little if you can’t build trust, collaborate, and admit your mistakes. “People are everything.”

4. Learn from Experience (and Mistakes)

Wisdom = Experience + Errors. Jimmy shared stories of being humbled by mentors and missed calls. That humility is gold—especially for young professionals and investors. Seek feedback, admit when you’re wrong, and GROW.

5. Build Your Foundation, THEN Dream

Great portfolios rest on financially strong, well-managed companies with enduring business models—think Apple or Google. Want to make moonshot bets on quantum stocks or crypto? Fine…but only with surplus capital, after you’ve secured your base.

6. Bonds = Psychological Armour

Why invest in “boring” bonds if stocks return so much more? Sometimes it’s less about returns, more about keeping your cool. Bonds stabilise your emotions during market chaos, letting you stay invested for the long term.

7. Stay Curious & Be Open to Serendipity

Opportunities—from TV guest spots to Wharton admissions—came through unexpected connections for Jimmy. His advice? Accept every invitation. Stay open, keep learning, and leverage the magic of meeting people.

8. Read Both Sides, Always

In a world of influencers and clickbait finance “gurus”, Jimmy insists: voraciously read—especially opinions opposite yours. The real answers aren’t on TikTok; they’re in analysing facts from all perspectives and developing your OWN view.

9. Success = Money AND Meaning

Investing for life isn’t just about wealth—it’s about building a legacy of relationships, resilience, and purpose.

Good things happen when you’re least expecting them… sometimes an awful event can lead to a really good outcome.
– Jimmy Lebenthal

Join us for an engaging conversation about investing, leadership, and the timeless principles that help us navigate both financial markets and life with greater confidence, perspective and purpose.

You can listen to this Business Elevation Show interview with Jimmy Lebenthal & Chris Cooper here. Alternatively on Apple Podcasts, Spotify, Tunein, Amazon Music, iHeart Radio (latter US only).

More about Jimmy Lebenthal:

Jimmy Lebenthal is the author of How to Ride the Subway: Getting Around on Wall Street and in Life, as well as Cerity Partners’ chief market strategist and a partner in the New York office.

He has over twenty-ﬁve years of experience managing investment portfolios and is a regular contributor on CNBC.

Prior to joining Cerity Partners, Jimmy served as the chief executive ofﬁcer and chief investment officer of Lebenthal Asset Management, LLC, served as a ﬁnancial advisor for Goldman Sachs, and was a partner of investment ﬁrm Levy Harkins.

A former lieutenant and submarine officer in the United States Navy, he was awarded two Navy Commendation Medals and four Navy Achievement Medals. His education includes a BA from Princeton University and an MBA from Wharton School of Business. He is a Chartered Financial Analyst.

Jimmy Lebenthal grew up in New York City in the ’70s and ’80s, a hardscrabble time for Gotham. As a youth, the city’s extensive subway system drew his attention to a degree that can only be described as passionate. It was in those years that Jimmy ﬁrst started investing in public equities, which also became a lifelong passion.