Insightful Investor

Alex Shahidi is a Co-Chief Investment Officer who has spent more than two decades managing billions in client assets, and his podcast Insightful Investor reflects that hands-on experience. The show's stated mission is to surface counterintuitive, misunderstood, or underappreciated investment ideas — the kind of insights that get lost when financial media gravitates toward the same consensus narratives every week. The guest caliber is consistently high. Recent episodes have featured leaders from Boston Partners (managing $125 billion), Franklin Templeton ($1.6 trillion in assets), and Vanguard, alongside former executives from entertainment companies like 20th Century Fox and Paramount who discuss the intersection of media, technology, and capital flows. The conversations tend to focus on themes that span multiple asset classes: private credit evolution, longevity science and its impact on retirement planning, gold as portfolio insurance, and how AI is reshaping quantitative investing. With 110 episodes and a perfect 5.0-star rating (albeit from a smaller review base of 19), the show is newer and less well-known than some of the giants on this list. But that relative obscurity works in its favor — Alex is not chasing audience share with hot takes. The fireside-chat format gives guests room to develop ideas fully, and Alex's background means he can push back with informed follow-ups when a claim needs scrutiny. Episodes run about 45 to 60 minutes and publish weekly. Insightful Investor is a strong pick for experienced investors looking for ideas and perspectives that are not already priced into the market consensus. Alex has been named to Forbes and Barron's lists of top advisors, and his two published investment books inform the show's analytical approach.