
Insightful Investor
The Insightful Investor is a weekly podcast hosted by Alex Shahidi, Co-CIO of one of the nation’s leading RIAs. In a conversational, “fireside chat” format, Alex interacts with some of the world’s premier investors and business icons to share market insights rarely found elsewhere. While many investors echo common sentiments, our “insights” include concepts that we believe are counterintuitive, widely misunderstood, or underappreciated. With over two decades of experience managing billions of dollars in client assets, Alex offers unique access to some of the industry’s top thinkers. He has authored two investment books and contributed to leading journals, and he consistently ranks among the elite financial advisors by Forbes and Barron’s. As an independent and innovative voice, Alex offers a fresh take on investing. We invite you to tune in and would love to hear your feedback.
https://insightfulinvestor.org/
Latest episodes

38 snips
Apr 22, 2025 • 1h 18min
#67 - Soo Chuen Tan: Long-Term Equity Investing
Soo Chuen is the founder of Discerene Group, a $2.5 billion investment manager (as of 12/31/24) specializing in fundamental, contrarian, long-term value investing in global equities. He shares insights into his unique investment approach, which emphasizes patience, structural moats, and significant margins of safety.

Apr 15, 2025 • 59min
#66 - Jason Illian: Leadership, Legacy, Principles
Jason Illian, co-founder of Highmount Capital, shares his insights on leadership and legacy through a lens of integrity and curiosity. He emphasizes redefining success to focus on significance rather than just profits. Illian discusses innovative investment strategies that prioritize relationship-building, explores the impact of technology on various industries, and highlights his $100 million investment in Dude Perfect. He also contrasts building a legacy with constructing an empire, advocating for humility and empowerment in entrepreneurship.

4 snips
Apr 8, 2025 • 57min
#65 - Julian Brigden: Macro and Market Outlook
Julian Brigden, Co-Founder of Macro Intelligence 2 Partners, shares his insights on global macroeconomic trends, focusing on the U.S. dollar and stocks. He discusses the historical influences shaping economic power and the effects of AI on productivity and national debt. Brigden also delves into the Mar-a Accord and its implications for trade dynamics. Geopolitical tensions, particularly between the U.S. and China, are explored, along with strategies for diversification and navigating market risks in an evolving economic landscape.

Apr 1, 2025 • 1h 2min
#64 - Katie Koch: Effective Leadership
In this discussion, Katie Koch, CEO and President of TCW, shares her impressive career journey from Goldman Sachs to leading a global asset management firm. She delves into the essence of empathetic leadership and the balance between ambition and authenticity. Katie discusses the transformative impact of AI on investment strategies and the importance of adaptability in a shifting economic landscape. She also highlights the delicate navigation required amid rising market volatility, emphasizing the complexities and inherent risks in investing.

13 snips
Mar 25, 2025 • 1h 3min
#63 - Paul Podolsky: Art and Science in Investing
In this conversation, Paul Podolsky, Founder and CIO of Kate Capital and former portfolio strategist at Bridgewater Associates, shares his wealth of knowledge in investing. He explores the fusion of art and science in investment strategies, discussing the complexities of market volatility and the necessity for personalized approaches. Paul critiques conventional wisdom, particularly the risks tied to relying on the S&P 500, and delves into the critical roles of gold and Bitcoin as diversifiers. He highlights the importance of adapting strategies amidst geopolitical uncertainties.

79 snips
Mar 18, 2025 • 1h 10min
#62 - Jeffrey Gundlach: Big Picture Outlook
Jeffrey Gundlach, the founder and CEO of DoubleLine Capital, shares his expert insights on the shifting economic landscape. He discusses the impact of rising interest rates and inflation on investment strategies. Gundlach emphasizes the need for portfolio diversification amid increasing national debt. He critiques current fiscal policies, arguing for reform to better serve future generations. The conversation also touches on the emotional aspects of investing and the risks associated with market trends, including the dominance of major stocks.

6 snips
Mar 11, 2025 • 1h 10min
#61 - Jonathan Ruffer: Financial History, Market Cycles, Outlook
Jonathan is the Co-Founder and Chairman of Ruffer, a London-based investment firm focused on absolute returns. Jonathan shares his unique insights on financial market history, long-term cycles, and his market outlook, drawing on nearly five decades of experience.

Mar 4, 2025 • 55min
#60 - Josh Kanter: Legacy Building, Family Owner’s Manual
In this engaging discussion, Josh Kanter, Founder and CEO of Leaf Planner, combines nearly 25 years of family office expertise with personal anecdotes. He dives into the importance of creating a family owner’s manual, emphasizing how clear communication is crucial for multigenerational wealth management. Josh also highlights the challenges wealthy families face, including navigating family dynamics and ensuring continuity. With insights on customizing privacy in wealth management, he offers practical advice on building sustainable legacies that prioritize values over mere financial capital.

Feb 25, 2025 • 1h 10min
#59 - Bob Prince: Portfolio Engineering, Psychology of Investing
Bob Prince, Co-CIO of Bridgewater Associates, shares nearly forty years of expertise in hedge fund management. He discusses the intricate art of portfolio engineering, emphasizing the necessity for diversification and strategic assessment in today's fluctuating markets. Bob highlights the psychological aspects of investing, urging investors to embrace humility and continuous learning. He also addresses the impact of global economic shifts and stresses the importance of adapting strategies to manage risks effectively. Get ready for invaluable insights that blend psychology with practical investment approaches!

Feb 18, 2025 • 55min
#58 - Richard Orlando: Wealth Psychology & Legacy
Richard is the founder of Legacy Capitals and author of Legacy and Love Your Clients. He explores the human side of wealth and delves into family dynamics, generational challenges, and strategies for preserving legacies.
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