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Replacing the Founder: One CEO on Cracking the Code and the Unwritten Rules episode artwork

Oct 6, 2026 27 min

Replacing the Founder: One CEO on Cracking the Code and the Unwritten Rules

from Exit Horizon: CEO Insights Hosted by Andrew Henry, Lenny Castiglione

Regardless of an executives’ experiences or expertise, it’s never easy to be a new CEO. When it comes to replacing a company’s founder, though, the process can be even more challenging. In our first episode of Exit Horizon: CEO Insights, JM Search’s Managing Partner Andrew Henry speaks to Lenny Castiglione, CEO of Ob Hospitalist Group. A multi-time CEO, Castiglione succeeded Ob Hospitalist Group’s founder in 2015. Now, with his array of succession experiences, he offers advice to fellow CEOs preparing to succeed company founders. In this episode, Lenny provides tips on: Hiring an executive coach Seeking advice from the company’s founder(s) Shifting his perspective on remote leaders Checking in with employees regularly Download JM Search's 2026 CEO Compensation & Insights Study - featuring insights from 350 CEOs & Presidents. Learn more about JM Search.

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In our first episode of Exit Horizon: CEO Insights, JM Search’s Managing Partner Andrew Henry speaks to Lenny Castiglione, CEO of Ob Hospitalist Group. A multi-time CEO, Castiglione succeeded Ob Hospitalist Group’s founder in 2015. Now, with his array of succession experiences, he offers advice to fellow CEOs preparing to succeed company founders.

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Replacing the Founder: One CEO on Cracking the Code and the Unwritten Rules

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