Second in Command: The Chief Behind the Chief with Cameron Herold

Ep. 608 - FAN FAVORITE | YPO President and COO Sean Magennis - Lead With a Servant's Heart

September 22, 2026·45 min
Episode Description from the Publisher

Ep. 608 - FAN FAVORITE | YPO President and COO Sean Magennis - Lead With a Servant's HeartWhat does it take to lead an organization of 27,600 CEOs across 135 countries while still leading with a servant's heart?In this Fan Favorite episode, Cameron Herold sits down with Sean Magennis, former International Chairman of the Entrepreneurs' Organization (EO) and former President and COO of YPO, now EVP at Scouting America, to revisit one of the show's most insightful conversations on peer leadership.Sean's path is rare: he bootstrapped his own business from South Africa to Canada with no debt and no laptop, then spent over two decades immersed in confidential peer groups before helping run one of the largest CEO communities in the world.They get into how YPO's confidential "Forum" model teaches CEOs to speak from experience rather than give advice, why businesses evolve through life stages the same way people do, and the exact habits that keep his partnership with YPO's CEO in sync.Listen now.Sponsored by:Redirect Health offers healthcare benefits that finally make health insurance optional: a 24-hour online primary care and RX membership that protects your business by guiding employees before problems happen. Learn more: redirectcoo.comTimestamped Highlights00:00 YPO and the Mastermind Landscape for Entrepreneurs02:10 Sean Magennis: From EO Forum Committee to YPO07:15 The Volunteer Addiction: 23 Years of Peer Group Leadership10:05 Inside YPO Today: 27,600 Members and $9 Trillion in Member Sales13:40 The Forum: YPO's Confidential Peer Group Model for CEOs16:20 How YPO Teaches Vulnerability and Builds Trust Among CEOs19:00 Forum in Business: Bringing Peer Principles to the Workplace27:00 How Businesses Evolve Through Lifecycle Stages Like Humans36:20 Sean's Key COO Skills: Ego Management, Coaching, and Coordination43:00 The CEO-COO Partnership and Sean's Biggest LessonAbout the GuestSean Magennis is EVP at Scouting America. At the time of this recording, he was President and COO of YPO, the global community of chief executives, where he led alongside a 27-year YPO member CEO and a board of 17 CEOs overseeing 27,600 members in 135 countries. He began his career in South Africa before moving to Canada in 1990, where he bootstrapped an organizational development and executive search business across Canada, the US, and Mexico, and served as past International Chairman of the Entrepreneurs' Organization (EO).Mentioned ResourcesEntrepreneurs' Organization (EO)Dow LimitedCollege Pro PaintersFortune's Best Places to Work listImportant LinksConnect with Cameron: Website | LinkedInExplore the COO Alliance – The World's Leading Community for Seconds in CommandGet Cameron's book: Second in Command, Unleash the Power of Your COO BookClaim your FREE copy: Second in Command: Unleash the Power of Your COO BookTake his course: Invest

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