The Insightful Investor with ALEX SHAHIDI

Unique perspectives to navigate financial markets

The Insightful Investor is a weekly podcast hosted by Alex Shahidi, Co-CIO of a leading RIA. With over two decades of experience managing billions of dollars in client assets, Alex offers unique access to some of the world’s premier investors and business icons.

Market Insights

Industry leaders share their views on markets and the economy

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Investing Insights

Discover perspectives and frameworks you may not have considered and learn the flaws with conventional investment approaches

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Industry Insights

Learn about the inner workings of the financial industry, including the incentives, how advisors think and the challenges inherent in the business

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Featured Guests

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Recent Episodes

Featured Guests | Investing Insights | 05.26.2026

#124 - Robert Smith: Enterprise Software, AI, Agentic Execution

Robert is Founder, Chairman, and CEO of Vista Equity Partners, which manages $107 billion in assets as of year end 2025, and a TIME 100 honoree—TIME magazine’s annual list recognizing the world’s most influential leaders across business, technology, and society. He shares how enterprise software is evolving into agentic execution, why AI strengthens rather than replaces software, how “bringing the model to the data” reshapes economics, and why companies must continuously evolve their systems, culture, and decision making to stay relevant through periods of rapid change.

Investing Insights | 05.19.2026

#123 - Chris Davis: Stewardship, Patience, Value Investing

Chris is Chairman and Portfolio Manager at Davis Advisors, an independent, employee owned investment firm managing $30B as of March 2026, and serves on the board of Berkshire Hathaway. We discuss stewardship and patience as core advantages in value investing, how market cycles test conviction, and the enduring lessons as well as the limits of the Buffett and Munger framework.

Industry Insights | 05.12.2026

#122 - Doug Merritt: Cybersecurity Risk in the AI Era

Doug is Chairman, CEO, and President of Aviatrix, which helps companies safely connect and manage their cloud systems, and former CEO of Splunk, which helps organizations understand what is happening across their technology and security environments. We discuss how AI is changing cybersecurity risk, why cyber is a leadership and business issue, and Doug’s leadership philosophy for navigating complexity and change.

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