McKeel Hagerty of Hagerty: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Maud DeVito
McKeel Hagerty of Hagerty: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

McKeel Hagerty is the Chief Executive Officer and driving force behind Hagerty, the world’s largest membership, insurance, and automotive media organization for car enthusiasts.

Under his leadership, Hagerty has evolved from a local insurance agency into a global market leader with over $500 million in annual revenues.

He has also served as the former international board chairman for YPO – the world’s largest organization of chief executives – and as a general partner of Grand Ventures, a Grand Rapids, Michigan-based venture capital firm focused on providing emerging companies with early-stage capital and strategic support.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

McKeel Hagerty: Absolutely. Entrepreneurship has been a part of my DNA since childhood. It began with a venture planting 600 apple trees in Traverse City, Michigan, where I sold the fruit at local markets.

Transitioning into the insurance realm, I drew from my family’s background in insuring classic wooden boats. This journey ultimately evolved our business focus from insurance sales to nurturing a vibrant community centered around classic cars and boats.

“Entrepreneurship has been a part of my DNA since childhood. It began with a venture planting 600 apple trees in Traverse City, Michigan, where I sold the fruit at local markets.”
McKeel Hagerty

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

McKeel Hagerty: My biggest “aha moment” came during my doctoral studies when I realized the potential to refocus our family business from selling insurance to selling “community.”

This shift in perspective, coupled with a deep passion for automobiles, paved the way for the evolution of Hagerty into an automotive lifestyle brand.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on?

McKeel Hagerty: I’ve always had entrepreneurial tendencies, but my involvement with YPO (Young Presidents Organization) significantly accelerated my learning about business and leadership. YPO provided a platform for me to learn from experienced CEOs and cultivate essential entrepreneurial skills.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

McKeel Hagerty
“We are dedicated to preserving and expanding car culture, and this mission permeates everything we do, from insurance services to media offerings.”

McKeel Hagerty: My parents were my initial inspirations. My father’s salesmanship and my mother’s operational acumen laid the foundation for our family business. Additionally, my involvement with YPO introduced me to a network of inspiring individuals who played a crucial role in shaping my entrepreneurial journey.

What do you think makes your company stand out?

McKeel Hagerty: Our company’s purpose and people are what truly set us apart. We are dedicated to preserving and expanding car culture, and this mission permeates everything we do, from insurance services to media offerings.

Our commitment to this purpose has fueled our growth and positioned us as a leading automotive lifestyle brand.

You are a successful business leader. Which three character traits do you think were most instrumental to your success?

McKeel Hagerty: Curiosity, soul, and self-discipline have been pivotal to my journey. Curiosity fuels ongoing learning and innovation, while the soul cultivates emotional intelligence and empathy.

Self-discipline instills consistency and resilience, essential traits in navigating challenges and seizing opportunities.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

McKeel Hagerty: I’ve learned that it’s essential to trust your instincts and not be swayed by naysayers. Throughout my journey, there have been instances where I ignored my intuition and followed conventional wisdom, only to regret it later.

“Building trust and credibility requires authenticity, vulnerability, and a commitment to transparency.”

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

McKeel Hagerty: Cultivating a supportive work culture begins with prioritizing employee well-being and fostering open communication.

Encouraging work-life integration, providing opportunities for growth and development, and recognizing employee contributions are essential for maintaining a healthy and resilient workforce.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

McKeel Hagerty: Building trust and credibility requires authenticity, vulnerability, and a commitment to transparency. By demonstrating integrity, empathy, and a genuine concern for stakeholders, leaders can establish themselves as trusted authorities within their industry.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

McKeel Hagerty: One common mistake is neglecting to prioritize company culture from the outset.

Establishing a strong cultural foundation early on is crucial for fostering employee engagement and driving long-term success.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

McKeel Hagerty
“Maintaining a positive attitude during difficult situations is essential for resilience and problem-solving.”

McKeel Hagerty: Entrepreneurship is inherently unpredictable and involves taking risks that often result in both triumphs and setbacks.

Unlike traditional employment, where roles and responsibilities are typically predefined, entrepreneurs must navigate a constantly evolving landscape characterized by uncertainty and volatility.

While this dynamic can lead to exhilarating highs, it also exposes entrepreneurs to significant stress and pressure, contributing to the emotional rollercoaster of entrepreneurship.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

McKeel Hagerty: One of the most exhilarating moments in my entrepreneurial journey was realizing the impact of our company’s purpose in uniting enthusiasts and fostering a sense of community.

Witnessing the passion and enthusiasm of our members at automotive events and gatherings reaffirmed the significance of our mission and fueled my excitement for the future of our brand.

What Are Your “five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”?

McKeel Hagerty:

1. A high level of physical fitness: Physical fitness is essential for maintaining energy and resilience in the face of adversity. By prioritizing my health and well-being, I’ve been able to sustain high performance and navigate the emotional ups and downs of entrepreneurship effectively.

2. Great self-discipline: Self-discipline is crucial for maintaining focus and productivity, especially during challenging times. Through consistent habits and routines, I’ve cultivated the discipline needed to persevere and overcome obstacles in my entrepreneurial journey.

3. Know when to work hard or rest: Achieving work-life balance is essential for preventing burnout and maintaining overall well-being. By recognizing the importance of rest and relaxation, I’ve been able to recharge and approach challenges with renewed energy and perspective.

4. Be patient even if it doesn’t feel right: Patience is key in entrepreneurship, as success often requires time and persistence. By embracing patience and trusting the process, I’ve learned to weather uncertainties and setbacks with resilience and determination.

5. Remember to celebrate the wins: Celebrating achievements and milestones is crucial for maintaining morale and motivation. By acknowledging and appreciating progress, I’ve cultivated a positive and supportive work culture that fuels continued success and growth.

How Would You Define Resilience? What Do You Believe Are The Characteristics Or Traits Of Resilient People?

McKeel Hagerty: Resilience is the ability to adapt and bounce back from adversity, challenges, and setbacks. Resilient people demonstrate perseverance, optimism, and a growth mindset.

They view obstacles as opportunities for learning and growth and possess the emotional strength and flexibility to overcome adversity.

Did You Have Any Experiences Growing Up That Have Contributed To Building Your Resilience? Would You Mind Sharing A Story?

McKeel Hagerty: Growing up, I undertook several ambitious projects, such as starting an apple orchard and restoring a vintage Porsche.

These experiences taught me the value of perseverance, determination, and resilience in the face of challenges and setbacks.

By embracing adversity and learning from failures, I developed the resilience needed to succeed in entrepreneurship.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

McKeel Hagerty: Maintaining a positive attitude during difficult situations is essential for resilience and problem-solving.

I’ve found that focusing on solutions rather than dwelling on problems, seeking support from others, and practicing gratitude helps me maintain a positive outlook during challenging times.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team?

McKeel Hagerty: A leader’s positive attitude sets the tone for organizational culture and morale. By fostering optimism, enthusiasm, and resilience, leaders inspire confidence and motivation in their team members. This positivity not only enhances employee satisfaction and engagement but also cultivates trust and loyalty among clients and stakeholders.

McKeel Hagerty

What Is Your Favorite Inspirational Quote That Motivates You To Pursue Greatness? Can You Share A Story About How It Was Relevant To You In Your Own Life?

McKeel Hagerty: Antoine de Saint-Exupery said, “If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea.”

This quote resonates with me as it emphasizes the importance of purpose and vision in driving meaningful and transformative outcomes. By inspiring others to embrace a shared vision and pursue their passions, leaders can catalyze innovation and create lasting impact.

This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!

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