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

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur  we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing McKeel Hagerty.

McKeel Hagerty is the Chief Executive Officer and driving force behind
Hagerty, the world’s largest membership, insurance and automotive media organization for car lovers. Under his leadership, Hagerty has grown from a local insurance agency to a global market leader with more than $500 million in annual revenues. He is the former international board chairman for YPO – the world’s largest organization of chief executives – and 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: I always worked, even when I was very, very young. I mowed lawns to save up money to buy 600 apple trees that I planted behind our family’s house in Traverse City, Michigan. When the trees matured, I sold Ida Reds and Golden Delicious apples at the local farm market. The trick to selling produce at that market was to get a good stall. And to get a good stall from management, you had to drive something cool, so I borrowed a cool, old 1933 Ford pickup truck that my dad had restored, and it did the trick. I got a great stall and sold a fair number of apples. I didn’t get rich, but I learned a lot about being an entrepreneur, especially the value of location, location, location and the power of pricing.

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 was in a philosophy class reading Plato’s “Republic.” My goal at the time was to become a philosophy professor. Something in the text got me thinking about the family business back home. My parents owned an insurance agency insuring classic wooden boats, and I helped out during the summers. I loved philosophy and still do, but the entrepreneur in me won out. So, my pregnant wife and I moved back to Michigan with an idea to refocus the business from selling insurance to selling “community.” That was 1995. A few years later, I became CEO, and the rest is history. Today, we’re a global market leader protecting more than 2 million collector cars and boats. But we’re really more of an automotive lifestyle brand built around the idea that cars are fun. We’re weaving together the passion and love for automobiles with digital community, data and content, which is a lot more fun than insurance.

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

McKeel Hagerty: I’ve always been entrepreneurial but a group called YPO (Young Presidents Organization) really  super-charged my learning about business and leadership. YPO is the world’s largest organization of CEOs whose companies have a combined revenue in excess of $9 trillion. It’s an incredible learning experience that creates these virtuous relationships between knowledgeable people and people willing to learn. When I joined in 2000, I was a bit embarrassed because I didn’t have a business background, never took a finance class or any of that. I needed to get better faster, and YPO really unlocked this whole world of CEOs out there who were willing to share deeply about their experiences. Everybody in any walk of life needs unique guides, mentors and coaches. I’m a big believer in that, and I’m very grateful for all of the people in YPO who helped me, and I was proud to serve as the organization’s international board chairman in 2016-2017.

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: My mom and dad were my initial inspirations. My dad was the consummate salesman, very charismatic, and it was hard not to be amazed by how he charmed people. When they started Hagerty together, he was clearly in sales and had the subject matter expertise around insurance and cars, but she ran the operation. She set up accounting, hired people and kept everything running. After that, it was the people in YPO who inspired me. I’m also a big believer in finding inspiration throughout your life, whether it’s from reading and studying or finding other people to help guide and inspire you. I think that’s super important.

What do you think makes your company stand out? Can you share a story?

McKeel Hagerty: Our purpose and our people. We realized that if we wanted to grow, we had to be really centered around a purpose. A few years ago, I had a technologist in the autonomous vehicle world say to me, “Sorry, but I’m going to put you out of business.” And I said, “Henry Ford didn’t make horses go extinct 120 years ago, he just took them out of the daily transportation routine.” What did I know at this moment that this guy didn’t know? That there’s passion underneath pastimes like cars and horses, but I needed a purpose around it. And that purpose is preserving and expanding car culture. Yes, the future is autonomous vehicles, but there are an awful lot of people who love cars and driving, and our mission is to support and sustain that passion.

To do that, of course, we need to make a business that’s successful enough to do so. As a result, we can’t just be an advertiser or a sponsor; we have to be a part of the automotive community. That’s why we invest very heavily in media. Hagerty Drivers Club magazine, for example, is one of the largest automotive magazines of any kind in the world, with more than 600,000 subscribers. We actually are very bullish on publishing magazines, and we’ll be launching a new magazine each year in the next 4 or 5 years in the automotive space. Even during COVID-19, we’re acquiring car events, because we know when it’s safe there will be car events where people will want to see and show cars and race them, all the things people do.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

McKeel Hagerty: Curiosity is critical. I’ve met many, many leaders from all walks of life, all around the world, and those who stand out are always curious and passionate about learning. Soul, I think, is important as well. I don’t mean soul in the spiritual sense, though that’s important, too. I mean in the sense of emotional intelligence, kindness and appreciating beauty and other human beings. A third trait that is critical is self-discipline – that daily willingness to get up and do stuff that you may not like doing.

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 wouldn’t call it advice, but we’ve been told as a company, multiple times, that we’re just not going to be able to do something, and yet we’re able to do it, anyway.

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: I don’t believe in the phrase “work-life balance.” It’s all just life. Some parts of your life you get a paycheck for and some of it you pay for. What that means is sometimes your home life takes precedence over your work life, and vice versa. We tell people, “If you have to go to a PTO meeting or a play, go. Your child is important.” Over time, you develop a lot of mutual trust.

Also, as things like religious participation and social participation dwindle, more people are finding meaning in their work than they would have in the past. Leaders in businesses need to recognize that we fill a pretty important part in people’s lives and we’re either adding to their life quality or diminishing it. At Hagerty, we’ve chosen from the beginning to add to it. We built the whole business around learning opportunities to help people grow. Nobody is a finished product.  To help, we’ve developed Hagerty U, an internal education curriculum that offers 60-70 classes on everything from improving your business and interpersonal skills to a class where anyone in the company can get their hands dirty by helping in the restoration of a classic car.

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

McKeel Hagerty: The biggest lesson I learned from YPO is that trust begins with a willingness to be vulnerable – the willingness to show others that you’re a human being and you’re on a path alongside them. I hate the term “boss.” Whenever somebody refers to me that way, I say, “No, I get to work with you, we just have different responsibilities.” The second piece is you have to constantly create an environment where other people feel safe enough to be vulnerable and share things that they’re struggling with. Ultimately, you want to build a culture of trust and credibility where people are willing to do a lot when the company is struggling, not just when it’s rocking and rolling. And that starts with vulnerability.

Can you help articulate why doing that is essential today?

McKeel Hagerty: Life and business has changed. In a previous generation, leaders would say they just want to be respected. Well, you know, to be respected, you have to be respectable. The burden of respect is on you. You have to show up every day. To earn trust, leaders today need to have their act together.

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: They think about culture way too late. When a young entrepreneur asks me, “When should I start thinking about my company’s culture,” my answer is “The best day was yesterday and the second-best day is today.” Culture is that important.

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: Even though I run a larger company, one of the reasons I’m so fascinated by the venture capital world is that you get to see some of the most on-point, unlocked entrepreneurial spirit where a small team with scant funding and an idea could become the next Instagram. If you want to see somebody work 100 hours a week, go to one of those environments and you’ll see not just somebody working hard, you’ll see incredible insights, creativity and invention happening. It’s that excitement, the growth, the thrill of seeing something really small become viable, and the viable becoming bigger, and the bigger becoming truly successful that creates the highs. On the other side, the highs and lows of being in a quote ‘regular job’ are, unfortunately, culture related. The lows typically come from poor leadership or poor culture, if not from the performance of the company. If your biggest high is bonus day or the Christmas party, then you may want to look elsewhere. In the end, it’s hard to actually replicate this spirit as your business gets bigger and bigger. But leaders will find ways to tap into that spirit.

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: I don’t map success on a chart, like some in the business world. Business success for me is akin to peeling an onion. It’s found in those ‘aha!’ moments. I love finding something that’s been hidden there all along even after 20 years in the business. That’s really exciting and I have that happen to me several times a year. You find something that was always been there, right from the beginning, about a topic you thought you understood and are supposed to be the expert on. I find those ‘aha!’ moments to be bigger highs than balance sheet success.

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

McKeel Hagerty: There have been years where I felt like I had to travel all the time and it turned out to not be the case. I don’t care how much money you’re making, sometimes you find yourself stuck in an airport and you just kind of feel like a schmuck, waiting to get home to what really matters. One of the things I’m so excited about for myself – and for everybody and Hagerty – is that this pandemic has unlocked a world where maybe we don’t have to go everywhere all the time.

Based on your experience can you tell us what you did to bounce back?

McKeel Hagerty: To be honest, sometimes the recovery is about who you surround yourself with. Your family, your friends, your team. I’ve often needed other people to tell me, ‘Hey, stop traveling’ or ‘You’ve developed a bad habit.’ They’ve helped me realize that I can do an awful lot by being home, being rested and being able to think clearly. You know, maybe it’s OK to have people come visit me now and then?

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

McKeel Hagerty: A high level of physical fitness: I played sports growing up and in college. The only time I let myself go was in my late 20s and early 30s. I thought because I was married and traveling all the time for work that I had an excuse not to work out. I made a dramatic life choice that fitness is the foundation for all the energy that flows through your life. I became an avid cyclist and age group endurance athlete. Now I work out 6 days a week guided by a trainer. My fitness includes stretching, yoga, meditation and cold therapy. We are a wellspring of energy. Our job is the dig it out of our body and put it to work in our lives.

Great self-discipline: Self-discipline is about your whole life. It’s about doing stuff when you don’t want to but also about controlling your dopamine addictions. I learned in seminary that fasting is about more than food, it’s about telling yourself that you are in charge. This rubs off on people and has far-reaching positive impact.

Know when to work hard or rest: Achieving high performance requires one to understand that human performance is maximized when work and rest is in balance. Sometimes the answer to a problem is not going from 80 hours per week to 90 hours per week. Sometimes the answer is to go home and go to bed.

Be patient even if it doesn’t feel right: When bad things happen, we often try to fix them before we understand the full breadth of their impact. If something bad isn’t going to immediately kill you, sometimes the best thing is to let the event fully unfold so you can understand it better. Then you fix it at the core after it’s fully understood. Otherwise, your quick fix is just a patch on a larger problem.

Remember to celebrate the wins: Don’t just send someone flowers. Make it meaningful, name the people responsible in front of their peers, stay out late, go and party. Your team will remember your gratitude and pay it forward.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

McKeel Hagerty: I define resilience as bouncing back. That’s an essential quality for any entrepreneur. Resilient people learn from criticism and feedback rather than shrink from it. They view setbacks as opportunities. They make choices and deal with consequences. They have a drive to improve every day. And they have the courage to try something new and take a different path.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

McKeel Hagerty: When I was 13, I took on two very big projects: to start that apple orchard from the ground up and to restore a rusted-out old Porsche so that I could drive it in high school. At the time, I was just taking things one step at a time. There were points during each endeavor where the easy thing would’ve been to stop and turn back. However, the only way to get to the objective was to keep going…sometimes with dirt in my fingernails and rust in my eyes.

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

McKeel Hagerty: Yes, I hope so. I believe the job of top leaders is not just to show vision and create a culture of execution, it’s also about setting a positive mood. Challenges are all around us and sometimes we simply have to cheer people up! This starts with being aware of – and regulating – our own emotions but then extends to how we deal with others.

I grew up playing guitar in rock bands and have performed countless times on stage. And while my rock star ambitions are long in the past, along with my mediocre guitar skills, I know that leadership is essentially a performance. We wake up, we gather ourselves, workout and then get ready to perform every day.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

McKeel Hagerty: Everybody is looking to be a part of something. Whether that’s a new hire or a potential member. When you are mission-driven and you fuel that with an energetic and empathetic approach people will join you for all of the right reasons. They’ll join because of your purpose – why you exist – not because of what products and services you happen to offer.

Ok. Super. We are nearly done. 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.” I used this quote countless times in my YPO leadership journey. It’s tough work leading other CEO’s when you have no authority over them. So, you have to remind people of their purpose for gathering in an organization. This quote was on my mind when we created our purpose of saving driving as well.

How can our readers further follow you online?

McKeel Hagerty: I am also very active on LinkedIn. I encourage people to follow and interact with me there.

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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