Episodes

INDUSTRY INSIGHTS | MARKET INSIGHTS | 10.27.2026

#146 - Jim Carey: Durable Financial Services Businesses

Jim Carey, Co-CEO of Stone Point Capital, discusses building one of the leading financial services-focused investment firms, which manages $80B in assets (as of July 31, 2026). He shares lessons from three decades of investing, including how to identify durable businesses, navigate complexity, avoid common behavioral pitfalls, and think about the opportunities and limits of AI in investing.

INDUSTRY INSIGHTS | 10.20.2026

#145 - Jennifer Prosek: The Business of Reputation

Jen Prosek is the Founder and CEO of Prosek Partners, a leading strategic communications and marketing firm that has advised many of the world's largest asset managers, private equity firms, hedge funds, and financial institutions. We discuss what exceptional founders understand about reputation, how brand creates competitive advantage, the future of communications in an AI-driven world, and why trust remains one of the most valuable assets a business can build.

FEATURED GUESTS | INVESTING INSIGHTS | INDUSTRY INSIGHTS | 09.01.2026

#138 - David Booth: Evidence Over Noise

David is Chairman and Co-Founder of Dimensional Fund Advisors, a global asset manager with $1.1 trillion in AUM (as of 6/30/26) and one of the pioneering voices in evidence-based investing. He shares lessons from more than five decades in the industry, covering how markets work, why uncertainty creates opportunity, the importance of judging decisions rather than outcomes, and how investors can tune out noise to build lasting wealth.

INDUSTRY INSIGHTS | INVESTING INSIGHTS | 08.11.2026

#135 - Luke Sarsfield: Finding Alpha in Private Markets

Luke, CEO and Chairman of Ridgepost Capital, oversees $43B in AUM (as of 3/31/26) and previously spent over two decades at Goldman Sachs, including as Global Co-Head of Asset Management. He shares how private markets have evolved, where durable alpha still exists—particularly in the middle market—and what truly separates top investors from the rest.

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.

INVESTING INSIGHTS | MARKET INSIGHTS | INDUSTRY INSIGHTS | 04.14.2026

#118 - Jon Hirtle: The True OCIO Playbook

Jon is Executive Chairman and Co-Founder of Hirtle Callaghan, a pioneering OCIO firm overseeing approximately $26 billion in assets as of the end of 2025 for families and institutions. Our conversation explores how structure, philosophy, execution, and culture inform long term portfolio construction, along with views on risk, manager selection, private markets, and industry change.

INDUSTRY INSIGHTS | 03.24.2026

#115 - Dr. Szymanski: Building Healthspan with Medicine 3.0

We take a brief detour from our usual investment focused conversations to welcome Dr. Jared Szymanski, a leading physician in preventative and precision medicine. Dr. Szymanski explains how Medicine 3.0 reframes risk, extends healthspan, and helps people stay ahead of the “big four” diseases long before symptoms appear—offering insights that echo the long term, forward looking mindset central to disciplined investing.

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.