The Mirror of Entrepreneurship: What PE Talent Reveals About Leadership

In this episode of the Leadership Quotient Podcast, Henry Myers, Co-Founder and Managing Director at High Water Search, shares why entrepreneurship is one of the clearest mirrors for leadership and what that reveals about talent in private equity today. Drawing on his path from finance into building a global PE-focused search firm, Henry explains how personal responsibility, self-awareness, and discernment shape effective leaders on both the investor and operator sides of the table. He unpacks why great recruiting is less about volume and pedigree and more about pattern recognition, timing, and deep alignment between a firm’s culture and an individual’s direction of travel. Henry and Lindsay explore the growing bifurcation between mega-funds and emerging managers, how incentives like carry structures shape behavior and collaboration, and why many investment professionals struggle when moving from large institutional platforms into more entrepreneurial environments. They also discuss the behavioral traits that increasingly differentiate successful PE leaders—empathy, adaptability, communication, and the ability to build trust with founders and management teams—and why reputations travel fast in a small ecosystem. The conversation closes with a look ahead at how private equity talent needs are shifting as value creation replaces multiple expansion, AI reshapes deal teams, and a new generation of leaders reassesses what kind of firms—and cultures—they actually want to build.