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

Industry Insights | Investing Insights | 03.10.2026

#113 - Young Lee & Asheesh Gupta: Audax AI Value Creation

Young is Co President at Audax Private Equity, and Asheesh is a Managing Director overseeing the firm’s Strategic Resources Group and Portfolio Support team at Audax, a leading middle market PE platform managing $19.5 billion (as of year end 2025). We discuss how Audax is intentionally embedding data and AI into its operating model and portfolio companies to systematically enhance decision making, scale its Buy & Build strategy, and drive durable value creation.

Investing Insights | Market Insights | 03.03.2026

#112 - Carl Kaufman: Public Credit Risk Discipline

Carl is Co President and Co CEO of Osterweis Capital Management, a boutique investment firm founded in 1983 with approximately $8 billion in AUM (as of 12/31/25). We discuss public credit through an absolute return lens, with an emphasis on downside risk management, cycle awareness, and where markets may be mispricing risk.

Investing Insights | 02.24.2026

#111 - Jack Sommers: Culture, Principles, Focus, Always

Jack is the Co Founder and Executive Chair of Income Research + Management (IR+M), a specialist fixed income firm managing approximately $131B (as of 12/31/25). We cover his father son origin, first principles discipline, and how focus and culture power a client first edge—plus independence, balance, succession, and where their portfolio construction diverges.

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