Jenny Harrington - Dividend Investing, Risk Management, and Building Reliable Income Streams

In this episode, hosts Michael Mauboussin and Tano Santos speak with Jenny Harrington, CEO of Gilman Hill Asset Management, about her approach to dividend-focused investing. Jenny shares her journey from early internships to portfolio management and explains how her strategy targets steady income through high-quality dividend-paying companies. The discussion examines risk management through cash flow, valuation discipline, and behavioral considerations that influence investor outcomes. Jenny also outlines her screening process, portfolio construction, and how she evaluates dividend sustainability. The conversation touches on lessons from market cycles, the role of communication in investing, and how technological changes may shape future opportunities and risks and much more! Key Topics: ● Introduction to dividend investing and its role in total returns (0:00) ● Jenny Harrington's early career and path into portfolio management (3:05) ● Lessons from internships and exposure to market professionals (3:10) ● Experience at Goldman Sachs and insights from the dot-com bubble (10:03) ● Transition to Neuberger Berman and developing an income strategy (15:01) ● Philosophy of portfolio management and client-focused outcomes (16:45) ● Structure of the dividend income strategy and screening process (20:58) ● Differences between dividend income and dividend growth investing (27:30) ● Portfolio construction, position sizing, and diversification approach (36:25) ● Case study: Clorox investment thesis and valuation framework (40:03) ● Case study: Best Buy and identifying value through free cash flow (46:06) ● Impact of Columbia Business School on investment philosophy (49:48) ● Importance of communication and behavioral discipline in investing (54:47) ● Views on AI, job disruption, and future market implications (57:02) ● Book recommendations and information sources (59:06) ● And much more! Mentioned in this Episode: ● Gilman Hill Asset Management ● Goldman Sachs ● Neuberger Berman ● Columbia Business School ● CNBC ● Van Leeuwen Ice Cream ● Best Buy ● Clorox ● Kimberly-Clark ● IBM ● Hewlett Packard ● PayPal ● Poor Charlie's Almanack by Charles T. Munger ● Pioneering Portfolio Management by David Swensen ● Elon Musk by Walter Isaacson Thanks for Listening! Be sure to

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Jenny Harrington - Dividend Investing, Risk Management, and Building Reliable Income Streams is an episode from Value Investing with Legends by Columbia Business School.

This episode is 01:01:51 long.

This episode was published on Apr 17, 2026.

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