May 6, 2020

Leading Hearts as Well as Minds, with McKeel Hagerty

Episode 78:

McKeel Hagerty began playing with cars as a boy and hasn’t stopped since, turning his parents’ local insurance agency into an automotive lifestyle brand known internationally for its passion and commitment to the car and driving community.

Since 1997, he has been the CEO of Hagerty, the world’s largest provider of specialty insurance and hobby support to the enthusiast vehicle market. During his tenure, the company also has evolved into a leading automotive media company and the hub of the biggest car club in America, Hagerty Driver’s Club, with more than a million members.

From the beginning, McKeel has felt a responsibility to support organizations and initiatives that help ensure that classic vehicles and the driving lifestyle continue to thrive well into the future. The company’s youth programs have helped thousands of young drivers learn the nearly lost art of driving a manual transmission, and through a new partnership with Skip Barber Driving Academy, thousands more are upgrading their driving skills so they feel more confident and in control on the road. The company also supports the Historic Vehicle Association, which works on behalf of its nearly 600,000 members to protect and celebrate the automobile as a significant part of our culture, and the RPM Foundation, which provides restoration and preservation training programs for the next generation of automotive, motorcycle and marine craftsmen. Most recently, the company has doubled-down on its belief that cars are meant to be driven by acquiring, which is used by millions of motorsports fans to find and register for motorsports events from track days and road rallies to vintage races and motocross.

McKeel is the recent former Chairman of the Board for YPO, the premier global leadership organization with more than 27,000 chief executives in more than 130 countries. During his term, he traveled the world talking about leadership and success with world leaders and innovators, including Hillary Clinton, Justin Trudeau, London Mayor Sadiq Khan, author and philosopher Yuval Harari, and many others. Many of the lessons learned from those discussions are shared in McKeel’s upcoming first book, “Boundless: A Guide to a Flourishing Life in a Disoriented Age,” which will be published by ForbesBooks.

What you’ll learn about in this episode:

  • How Hagerty is benefiting through the crisis by having built their culture on the idea of being a growth mindset company
  • What it means to dig the well before you’re thirsty
  • Why McKeel’s first focus when everything first started with the coronavirus was just to get his team breathing
  • Why McKeel likes to go deep with his people, reintroduce them to themselves, and allow them to be human
  • The importance of realizing that you are not just leading people through the reality of the crisis but you’re also leading them through their fears and anxiety
  • How significant it is to embrace the fact that you are not just leading minds, you are leading hearts as well
  • How trust is built by showing vulnerability as a leader
  • What leadership lessons McKeel has learned in turning Hagerty from a small local insurance agency into a global market leader and automotive lifestyle brand
  • How Hagerty has been helping employees cope with working from home and the pressures of the coronavirus crisis

Additional resources:

  • Website:
  • Twitter: @Hagerty
  • LinkedIn:
  • Website: Good Bowl is a premium fast-casual Vietnamese eatery that offers a fresh, healthy and unique dining experience while providing their guests an opportunity to easily contribute to their communities. The Good Bowl donates $1 to charity for every bowl sold. Guests will have the opportunity to select from three charities that include a local, national and global non- profit organization.

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