McKeel Hagerty is the CEO of Hagerty. Hagerty is an American automotive lifestyle and membership company and the world’s largest provider of specialty insurance for classic vehicles. He is the former Chair of Young President’s Organization (YPO). YPO is a global leadership community of extraordinary chief executives — more than 30,000 members from 142 countries. McKeel is also a Co-Founder and General Partner at Grand Rapids, Michigan-based venture capital firm Grand Ventures.

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The Learning Leader Show

  • Arete is a concept in ancient Greek thought that, in its most basic sense, refers to “excellence” of any kind. This meaning was related to the idea of the fulfillment of purpose or function, the act of living up to one’s full potential. 
  • In his early twenties, Mckeel planned to be a Russian Orthodox priest. He earned his master’s degree in theology from Saint Vladimir’s Orthodox Seminary in Yonkers, New York.
  • Why McKeel tracks everything:
    • “I noticed that people who accomplished a lot kept track of their life.” He tracks: sleep, exercise, diet, goals, and more
      • Think, “What am I trying to do?”
    • “We are in the golden age of habit formation.”
    • “The best leaders are constantly looking for better ways to do things.”
    • “Intrinsic motivation is imperative for happiness.”
    • “I’m inspired by what I see in others.” — The spirit of the craftsman
  • In 1999, Hagerty had 35 employees… They now have 1,600.
  • The lightning bolt moment – McKeel went to a YPO branding conference at Nike. And learned about how Nike viewed branding.
    • “Nike is the spirit of the sport.” — Think more like a club than a company.
    • McKeel created a membership organization and media brand as part of his business.
  • Leadership “Must-Haves”
    • Growth mindset – you are not a finished product
    • “I don’t believe in work-life balance. You get life.”
    • Curiosity in the interview process
    • They need to understand what they will need to learn along the way
  • The power of YPO:
    • 30,000 members
    • It’s operational leaders doing work with people
    • It’s a wholistic view of life
    • The Learning Leader Show is tightly in line with YPO
    • In 2016, McKeel was elected Chairman
  • Keys to a great YPO group:
    • Holistic leaders (business, personal, family)
    • Egos checked at the door
    • Vulnerability and generosity are the keys to breakthrough leaders
  • McKeel has interviewed some of the world’s most notable leaders (Hillary Clinton, Sheikh Mohamed of Dubai, Paul Kagame, Prime Minister Lee of Singapore)
  • His writing practice:
    • General Eisenhower would sit alone and write out his thoughts… Ask yourself, “What’s the narrative here?”
    • Write summaries of what you learn from books, podcasts, videos, articles…
  • Apply to be part of my Leadership Circle


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