Lessons from McKeel Hagerty, CEO of Hagerty
I’m pleased to introduce to the website McKeel Hagerty, who is the CEO of Hagerty, an automotive enthusiast and insurance brand focusing on classic vintage cars, and the former International Chairman of YPO, a global leadership group that enabled him to travel the world interviewing notables like the late former U.N. Secretary General Kofi Annan, President of Rwanda Paul Kagame, Prime Minister of Singapore Lee Hsien, and Prime Minister of Canada Justin Trudeau.
McKeel, however, didn’t start out as a businessman and even when joining and expanding his family’s business didn’t set specific financial metrics but rather sought to create something of value. His entrepreneurial mindset and unique educational background, which he shared with me, have allowed him to carve a creative, and dare I say exciting niche in the world of insurance. Having worn a Hagerty jacket around before, I can say first-hand how he has built a community of classic car enthusiasts who want to connect with people equally as passionate. I sometimes have to avoid wearing it since people quickly find out my lack of knowledge about their prized car.
In the interview, McKeel shares interesting lessons not only from his life in business, but from his time in seminary school, and insights from world leaders. Our conversation was thought-provoking and showcases the many ways in which creativity and the creative process can take form.
Here are a few highlights, which I encourage you to read in full below:
Lesson 1: Always have something to say
“This idea of always being ready to have something to say, just got drilled into my mind during that period. When you’re a leader, you do not walk into a room without something to say. I don’t walk into a dinner now without somebody expecting me to say, ‘Hey, would you give a toast’. I never walked into a YPO anything without somebody saying, ‘Well, what do you think McKeel’”
McKeel takes with him a lesson from seminary school to always come prepared in case someone asks a question of you. As he clarified to me, this doesn’t mean butting in to say something at every moment, but to do the homework and know who you’re talking to and what you’re talking about. It could even be as small as saying a toast at dinner, but being thoughtful about communication is one of the cornerstones of his leadership style.
How I’ve thought about applying this lesson: When I’m having these conversations, knowing when to bring up the research vs. letting someone speak is an art form I’m still refining. But beyond looking at just who the person is and what they’ve done, I spend time looking at what’s going on that’s interesting in their field. I look at what they’ve said in prior interviews and think if there’s some new insight I can pull that can make it useful to not only readers but to the person sharing these thoughts out loud for the first time.
Potential exercise for you: If there’s a creative project you’re working on, consider logging your hours, including the time absorbing pieces of the broader conversation your work. By doing this, you’ll develop a deeper understanding of your own process and be able to talk more cogently about it to others.
Lesson 2: It’s better to seek creating value than winning the competition
“When you create value that way, or you create something new or do something differently than anybody has, It’s just a heck of a lot more fun.”
McKeel, like many of us, is by nature a competitive person who likes to win. But his business began to improve when he viewed it as an opportunity to create something of value for his customers, his employees, his family, and himself. Indeed, focusing on the end goal of what he wanted to create helped him be more innovative and thus win the competition too, but it was centered on a more balanced attitude.
How I’ve thought about applying this lesson: Thankfully I am not writing with the thought that it will be a business, so I’m less worried about competition to begin with. Even so, I am still competing for attention of readers. In turn, I think about what value I can create for someone who stumbles upon these interviews. These excerpts with exercises are by design something that I hope creates value to someone who wants to formalize some of their creative practices, and that to me has centered my purpose.
Potential exercise for you: In my last discussion with Abra Berens, I encouraged everyone to think about what they might owe to people who helped them along the way. In a similar way, I’d encourage you to take some time to journal the answers to the question, “What is the value you want to create for viewers/readers/engagers of your work?” Hokey or overly businesslike that it may be, I often try to come up with a “mission statement” for my projects to revisit when I get stuck.
Lesson 3: Lead yourself first
“You have to be able to demonstrate to the people around you that you can lead yourself effectively. You have to have a higher than average level of self-awareness”
This was a bit lost on me when I first heard McKeel said it but now as I’ve written up the interview it’s something that I’ve loved. It’s about the fact that if you are building something, make sure you are building yourself up along with it. Continue to study, take care of your physical and mental health, and build a community that will both support and challenge you to grow before you can inspire the same in others.
How I’ve thought about applying this lesson: If I want to build a community like McKeel has done for Hagerty, I have to think about what I want to emulate as a creator first. What discipline is required of me, what are my central motivators, and how am I dedicating time to this work relative the other important parts of myself are questions I have to answer first.
Potential exercise for you: What do you want to get done within the next few weeks? What are all the steps that would go into it, even the minutia (i.e., writing an email or learning more about a topic)? Write down each step and the timeline, and then try to assign “due-dates” which reflect a reasonable cadence that balances other obligations. It may be that your original timeline is too short – that’s okay and even a great thing to realize so you don’t get disappointed with unrealistic targets.
Full Interview Transcript:
Jack: Let’s start off with a bit about your background, as I remember when I was thinking of what to study my dad used to say you can really study anything and end up in business, and you’ve been a great example of this.
McKeel: As a very quick biography I was born and raised in Traverse City, I grew up here. I went to college in California where I went to study business and I ended up studying English Literature and Philosophy. I fell in love with academia and attempted to get become a Rhodes Scholar. I was a Rhodes Scholar finalist. I did not get it all the way and I because I just fell in love with traveling like I think you have and going to Europe and culture and story and meeting people who have just more cosmopolitan backgrounds. I really wanted to go back to Oxford and was close but instead I then went to a Russian Orthodox seminary. I was not raised that way. I went to St. Vladimir's Russian Orthodox Theological Seminary in New York, spent a couple of fantastic years there and got my master's in that and that's, that's a big part of my story. Hopefully we can unpack a little bit and then I wanted to get my PhD. I knew probably not in theology. So, philosophy was really my love. I went to Boston College and pursued my PhD, which I did not finish so I'm one of those that spent a couple years and then it was the siren call of a family life. I got married there and my wife was pregnant and then the family business was that was beckoning, and I had worked along the family business all that period of time, before coming back a couple years later to join YPO and then my whole world changed.
But back to the beginning if I may.The weird combination of it is, you know, I grew up in that entrepreneurial family, so my dad had this general insurance agency in Traverse City, my mom, who when I was very young, was kind of a housewife, but then joined him in the business and they work very closely together. And they later in 1984 really started Hagerty, the business that I run today out of the basement of our house and it was because they were always entrepreneurial.
I and my two older sisters, Kim and Tammy always kind of worked a little bit on the side things summer work, you know, like you go file stuff in the office when you're really young and then you maybe start selling things. I had an insurance license at 16. But for me, I always viewed myself as an entrepreneur and I wanted to figure out how to make my own money because what I really wanted to be was James Bond, and you know, I knew if you want to be James Bond, unless you're going to go kill people, you got to make money. For me that meant starting a business, not just having a job. The only thing I could think of then was like a passive income kind of business, and back then I planted an apple orchard when I was 12 or 13 years old to help put myself through college. My whole idea was to try to help my parents who were starting this new business and very mindful of money. I wanted to help since I knew I was going to go to college and it's probably gonna be expensive, so I planted this apple orchard and I also always had all sorts of other like side businesses, I painted cars, I did lawn care, anything I could do to in addition to school and sports and everything, even playing music. I was guitarist at the time I loved jazz, later I loved rock ‘n roll.
This entrepreneurial bent was I was underneath it, but I really felt that I was I was called more to a life of mind, a life of learning, a life of culture. And that's why when I pivoted from studying business, being a businessperson, to study English Literature and Philosophy and Pepperdine as I felt like I was deepening myself. It was about making myself more valuable to the world, being able to think more deeply, being able to articulate my thoughts with greater clarity rather than just moving and running around all the time. When you study philosophy, in the end, what you're trying to do is think about how you live life. It's not about do I really give, you know, a crap about Plato or Aristotle or Immanuel Kant? It's about life and really the big question how we ought to live.
Maybe the most interesting part of my background that people businesspeople ask me all the time is about this seminary time, was I really serious about studying to be a priest? I would say, honestly, to you, I was kind of lukewarm on it. I never really expected to be a priest. I was just really, really impressed by Russia, Russian culture and Russian intellectual culture. And the thought of being able to go live in New York for $6,000 a year and get a master's was pretty amazing. I went and I fell in love with it. It was like this really contemplative place people from all over the world came to this thing because it was a center of Orthodox theological thought. You didn't have to travel the world when the dorm was filled with 90 men from all over every imaginable culture that I could learn from and learn about how they lived.
I had this big unlock moment and that is for people studying to go become religious leaders, especially in a formal religious environment, if all you did was erased the religious language you realize these people are just leaders, they're being trained to go lead a community. They're going out to tell a story about a brand. They get people to believe in it. They have to replicate that message every day of the year around the clock, wherever they go, and they have to be able to translate that into different cultures. I found the leadership aspects of seminary really fascinating.
I did in fact, dabble with the thought of becoming a priest, and of course all the bishops honestly wanted to ordain me because I think they thought it would do a good job of it. I'm glad I resisted that. It still served me incredibly well. I believe the best CEOs are the best storytellers. And that's what I studied.
Jack: Going back quickly to the English literature. Did you have any sort of specialization within that or any types of books that you really remember from that time? Y
McKeel: I probably took, believe it or not more classes in medieval English literature than that. It wasn't really that I was so into it but there were a couple of really good professors there. If you wanted the best teaching, you went where the best teachers were. Then I kind of fell in love more with the not contemporary but 20th century English poetry, particularly English more than American poetry.
And when I didn't get the Rhodes Scholarship, I thought very deeply about going to Cambridge, and studying 20th century poetry, especially American poetry through the war, English poetry through the wars, World War One and World War Two, because this was real. It’s really fascinating time because you're talking about very modern contemporary minds, you know, people with lives and wanting to do things and the world was just kind of coming apart. They were trying to figure out how to articulate how these wars were shredding the world. Similarly, with philosophy, even though I probably ended up in the end studying a lot more ancient philosophy I was much more interested in existentialism. And, you know, there isn't a lot of philosophy done anymore, because I think philosophical thought shifted over to other fields, which if I were to do it today, I would do behavioral economics, instead of philosophy or I would do neuroscience. I think a lot of better questions are being asked by the fields of neuroscience and behavioral economics than philosophy today, but when you get to more contemporary philosophy, like call it Soren Kierkegaard who I wrote my master's thesis on in seminary.
It’s fine to look at ancient thinking, but I consider myself a thoroughly modern person. It was more interesting to study for contemporary stuff.
Jack: So, you wrote your thesis on philosophical topics while also studying theology? Was the program more flexible on studying things of that nature?
McKeel: Oh, they thought I was nuts. I thought I was nuts. I just had to find a thesis advisor who had studied philosophy who was willing to let me take this on. What I will just tell you the topic of m my thesis, a very funny phrase that Soren Kierkegaard is known for translated in English and it's called the teleological suspension of the ethical and what that was, is Kierkegaard wrote all these books autonomously, so you it’s hard to figure out exactly where his thought starts and ends relative to the characters who are speaking in the books. But there's this image of running all the way through of Abraham being willing to sacrifice his son, Isaac, which is the biblical story, because God told him to kill his son. Because he was willing to draws the knife and is willing to kill him, that's how he's proven to be the person of faith. And by the way, it was the Abrahamic faith that launched all three great religions of the West. And it was all that very idea that you're willing to make this great sacrifice, because supposedly God told you in the burning bush and all this sort of thing, and what Soren Kierkegaard talks about, and it's very much I mean, I think it's a very contemporary thing when you think about the challenges of terrorism or anti-vaxxers. They believe that God told them they shouldn't get a vaccine, so it’s this belief that when God tells you to do something, even if it's unethical, it's okay. That’s the teleological suspension of the ethical, that ethics gets thrown out the window, somehow when you're connected to these types of stories.
My master's thesis was about that subject, which I thought was kind of contemporary and you get to talk about stuff that they cared about as well. If you want to just like lose anybody's attention in a bar, use the phrase, teleological suspension of the ethical.
Jack: Well, most master’s thesis titles can lose anyone’s attention. I’d love to hear more about the storytelling aspect of the program. How has that influenced how you look at things?
Hagerty: First and foremost, this is a practical thing. I think the leaders I always admired tended to be pretty good communicators. They tended to be able to frame their thoughts and articulate their thoughts and make arguments in a compelling way. I don’t mean in a debate class way but in a really compelling way. Full of imagery, full of metaphor, full of story arcs. Like I said, I played guitar, so I was not afraid to get up on a stage and make a fool of myself. Ironically, in seminary, they had this evil practice. It was evil because that there are two major services all year long, and they happen every single day except for Sunday. You had a morning service, Matins, which means when the bells are ringing, and then you'd have Vespers which is evening service, right before dinner. They were in Latin. It was madness but I loved it because I trained myself early on to be a very early morning riser. I did my best thinking in the morning. By eight o'clock at night my mind is just garbage. I started usually four in the morning. By seven, I was done, I had my day of work done when everybody was kind of waking up and Matins was at 7:15 so I’d show up and it was beautiful. If you've ever been in an Orthodox Church, the smell of incense is extraordinary. The icons, the chanting, it's just this very lovely way to start the day.
The service had a couple of components that were always the same. There was an epistle reading from one of the Epistles in the Bible and Gospel reading and then there was a sermon, which usually was about five to seven minutes long. What would happen is the priest or whoever was serving and we have lots and lots of priests everywhere, so whoever was serving when it was time for the sermon, they'd come out and look around, see who is there and say, you're giving the sermon this morning, and it was part of your grade. You’re sitting there terrified that you're going to be picked and by the way, you were graded on how well your sermon connected to both the Epistle reading and the Gospel reading, which means you either read it in advance or you're listening really carefully. This idea of always being ready to have something to say, just got drilled into my mind during that period of time. When you're a leader, you do not walk into a room without something to say. I don't walk into a dinner now without somebody expecting me to say, “Hey, would you give a toast”. I never walked into a YPO anything without somebody saying, “Well, what do you think McKeel?”
That discipline taught me to pre-think and then to practice the skills of communicating verbally. You also have to be a good written communicator; you have to be able to write effectively and elucidate your thoughts. But this idea of being able to speak on the spot was really drilled into me during that period of time. Later even in my career when I was doing television, and then I did a bunch of live television where all this crazy stuff would happen and you're like, “Okay, well now what, and the cameras are on you so you know, the only person that's going to look like a fool is you if you have nothing to say.” It’s been a fun practice and I practice almost every day.
Jack: Now that you don’t have Matins, are you still waking up at four?
McKeel: I’m a big believer in owning the morning. My wife and I, we stretch together because it's before we work out. We get the candle going, it's in front of a Buddha now instead of an icon, and then we meditate together so we have a formal meditation practice and it's short 10 to 15 minutes every morning. Then we go workout, and you know, try not to look at our devices until after. If I were to ever write a book of daily rituals, I’d say own the morning and never give that up. On a Saturday, I give myself the ability to sleep until 6:30. That’s my catch-up time.
Jack: You mentioned earlier you wanted to generate passive income. How did you expand into classic cars, and what sparked your interest there?
McKeel: The core business idea under the business that my parents started was it was a niche business in wooden boat insurance, which didn't exist at the time they literally invented it. The whole premise was that people who own these types of things, care for them more than they would something else. This idea of personal care and valuing an object uniquely as if it’s more valuable even beyond its economic value. If you’re in the business of insurance, where you sell for risk, what that value does is it makes the economics perform fundamentally differently. If you really care about something, you'll probably take better care of it, you'll have less risk, you can charge less, you make more money. That was the core thing. In fact, if you're talking to my 86 year old mother today, she'd say, the business works because people take good care of their toys. That's it. That's the core underlying psychology of it. We expanded into the car business from the boat business in the early 90s. My sisters and I were now involved. And I moved back in 1995.I didn’t think I’d stay in Traverse City, I thought it was like a stop and I go back and restart my doctoral studies. I ended up falling in love with it because I realized business is fun. Business is philosophical, businesses is thoughtful, there was a way that I could really shape this. I liked our customers. I liked being able to make a little bit of money. I mean, that was good too.
But it really wasn't until YPO when I joined in 2000. I’ll never forget that day and that winter when your Dad came up to visit me and I was in one meeting and I didn't know that people were sort of watching me in this meeting and your dad drove up and met with me at Arts Tavern in Glen Arbor and convinced me that I should join and also join the forum.
I fell in love with them because I knew they were people like your dad. I met people that I liked and I wanted to be like and that they were not just about making money, they were about creating a whole life of value: business, personal, and family. It was really a big unlock and then when I really got into YPO I went way beyond the normal ask of just being a member to get into leadership and ultimately what led me to be global Chairman.
I started traveling around the world at all these events and I realized, here's this group of leaders that also have this idea that it's great to make a business. it's great to make money, but if you really change the lives of your employees and create opportunity for them rather than just making money that’s what’s special. I don't want to make why people are sound like they're saints because they're not all saints. But it was a style of leadership that I really liked. And as I met more of them, every time I'd see something cool, I just started plugging it into the business. I can literally go back each year and say, I went to this conference or I met that guy and then I came back, and I plugged it into the business and you know what we have today is so many orders of magnitude bigger than I ever expected. It was all because of finding people who had this approach to life and business.
Jack: As you just said, it's so much larger than you originally could have imagined. I wonder when you did go back in 1995, What was your initial kind of definition of success?
McKeel: For me, it's always been about this process of discovery. If I could go back to then and talk to that 9095 leader and say like don't waste your time on setting too many financial goals. I spent years being very competitive. If I’m competing just to compete than creating something new and how unlocking value I found it uninteresting. It’s a bit because of my background and personality. I mean I love to win and I'm a very competitive person, but it brings out a lot of ugly emotions when all you're thinking about is how you can beat somebody or take something away from them rather than I'm just going to create something so good that people want everything that I've got. When you create value that way, or you create something new or do something differently than anybody has, It's just a heck of a lot more fun. It brings energy to your teams. It's more fun personally, you don't wake up and have angry competitive vibe
Jack: You’ve talked about creating for business and how communities shaped you but I’ve always found how the Hagerty customer community is so strong that whenever I wear a Haggerty sweatshirt people come up and ask about classic cars. Was that something you all intentionally tried to cultivate?
McKeel: I knew insurance is about the least sexy thing that you could ever go out and spend your life trying to sell. If you really want to like not have friends tell them that you're an insurance guy. There's some great friendly insurance people but it is so tough to make insurance interesting. People just kind of view it as if you're a big bank. I went to a YPO branded conference at Nike out in Portland. They had all the top brass from Nike there and we spent like four days in the Nike Innovation Center. First thing they did was roll this sizzle reel of all the big Nike athletes. There was Michael Jordan and Tiger Woods and Lance Armstrong and Andre Agassi, and you’re in this big theater and you're just like, okay, I'm running my little business in Michigan, don't I wish I had Michael Jordan working for me. I mean, it was just intimidating. Then the CEO about two hours later talking about something else made something click for me and they showed another video. It was this high school basketball game and this kid draining three pointers and the crowd going nuts on a grainy, bad video. The CEO said, Look, I don't care whether there was a Nike logo in there. I don't care whether there was a Nike sponsored athlete in there. That game is about what Nike is all about. We're about the spirit of sport. Again it’s about getting out of the competitive mindset and thinking about what you want to create. You can actually pull just as much spirit that Tiger Woods pulls out of anything by just being at the right high school game.
I realized I had to shift my whole brand strategy to not being anything having to do with insurance and making it all about the love of the automobile. It's all about cars and the love and the passion that people have. As I said earlier, people take good care of their toys and that I can't invent. But I can tap into it if I stop acting like an insurance person. It was this whole pivot to tie more into the underlying humaneness of what people wanted, rather than what I thought I was trying to sell them.
I think that's probably one of the biggest unlocks of my life is go for the human story. And in fact, anybody who works closely with me about when we're creating a new product or when I leading YPO and we had an issue somewhere, we’d go back to, what's the human story? What's the underlying human drive that we're trying to tap into? How do we connect to that on a profound level? You can get people to do anything if you understand what their underlying motivations are.
Jack: I love the idea of tying back to the small games and the human issues.
McKeel: Which speaking of I know you had wanted to ask about Kofi Annan so maybe we could go there.
Jack: Absolutely
McKeel: My time with Kofi was for the Global Leadership Conference of YPO in Dubai that year. I was on the board of the event. I just got elected chairman. One of my jobs for the previous year and a half was to plan this event. It was really complex. Everybody wanted to go to Dubai. One of our challenges is we were trying to get the Israel chapter into Dubai, which today easy, but then it was hard. We worked with Sheikh Mohammed and his chief of staff and a bunch of people for a year to try to get them in. It just got harder and harder and then the Israeli chapter wasn’t happy. Then all this ugliness came out from all over the world. I was getting hate mail from, you know, members in LA, like how dare you mistreat our member. I'm like, Look, I'm a volunteer here. I'm just trying to do good. In the end we got 12 of the 40 in. We had Kofi Annan as one of our mainstage speakers and as incoming chairman, I got 30 private minutes with him. I went back there and I spent this time and in person, he was incredibly warm, and had that beautiful voice.
I finally said, well, since I have a Secretary General, I've got this complex problem I'm trying to solve this week, how would you think about it? It was a fake shadow of Arab-Israeli conflict, which was one of the biggest issue that he faced when he was Secretary General. I remember at first he said, Oh, very difficult, very difficult. Then he said, Well, tell me a little bit more about YPO. And I said, Well, YPO is organized locally in a chapter and then you have these small group forums and then you kind of have this regional structure and then their countries and then we have the global organization. And I said, I'm leading the global organization. He said, big global organizations like the UN, or like YPO, or even just big governments, they're really good at solving certain sorts of problems, especially like keeping people from getting into war with each other. That's really where the top-level abstracted organizations around the world do a good job. They tend to kind of solve for that. But what they can do is fairly limited. I remember him saying and I looked at my notes on this, he said, it won't create happiness. It won't create contentedness and it won't actually create a lot. Those big organizations won't create a lot of value locally. They may create coordination of the local units, but they won't create a lot of real value at the local level. So he said, probably a lot of what you're facing is that down at the local level are chapters that aren't very happy. They're not as happy as you think they are. If you want to make this better, you have to do more work at the local level. He said, when people asked me about Africa, and he was from Ghana, right, his people asked, how are we going to solve Africa's problems? And he said, town by town.
You just got to go in there and you go to work town by town. You're in Africa right now so you know you've got to help create value at the local level.
Later one of the best interviews I ever had in YPO was when I interviewed President Paul Kagame, the president of Rwanda. He ran the country on trying to eliminate just low level corruption, just like down to the clerk in the post office. How do you convince them that asking for a bribe for somebody to just mail a letter is not acceptable culturally anymore? The message from Kofi Annan was large global organizations are great at certain things and they're not great at others. So understand where your problems are. Where's that human need? I found that very powerful, and I've taken it with me ever since.
Jack: From your time in YPO, were there any other lessons that stuck with you, as a chairman or member?
McKeel: President Kagami was so interesting. I think the parallels between him in some ways like by temperament and Mandela are, I think, very fair, though, in Africa, the biggest fear about Kagami is that he's been in office too long. Anytime somebody is in office longer than 20 years, and he's been there for 30 so it just raises red flag. But I think for him, it's been more about stability than corruption. Of course, I'm not on the ground. I know a bunch of members from Rwanda, but I was very impressed by how thoughtful he was to realize that he needed to de-escalate the violence so differently. He came back to the country of his birth and sort of seized it from the bad guys who had, by the way, killed a million people with machetes in like 60 days. It was awful. I said the country must have been on fire. I remembered he looked at me and he says, literally, it was on fire. They burned everything down when they left. There wasn’t even a paperclip in the old administrative buildings. They ripped the copper wire out of the walls.
He said the biggest problem that he had was he had a list of 800 things that needed to be done and all everybody wanted was retribution against the bad guys. He had to develop a style of communication and allow for people to get together to both collectively mourn and do community work. So he did two things I thought were fascinating. One is anytime somebody came to him with this, saying you're so wonderful, you took the country back, now how can I go kill this dude that killed my brother? He would say first of all you will be heard. That was his first phrase. He said, I am listening, and you will be heard. But I have other priorities that I must attend to right now. That was first and foremost. I think it’s such an interesting thing to say when people are freaking out and it’s not something you can solve right now. The second big thing was that he moved the trials to community trials because they realized, if they put everybody who had committed genocide on formal trial, it would take 50 years to complete, that was the rough calculation. Everybody would be dead before the trials. So they decided to do these kinds of communal trials where it would bring the villagers together to put these people on trial. Then they pretty much eliminated prison time. They realized the only way that's going to work is we're going to all have to live together again. They decided not to use an external view of what a legal system should be. They used the local one to solve a local problem that was never going to be solved.
The final one that I thought was fascinating is they do a community service day, one day a month, and the whole country does it and what they do is he said, I don't know if you've ever been to Africa, but a lot of these cities are dirty and messy and there's garbage everywhere. He said so one morning of every month we all go out into the streets and we pick up garbage because we all want to keep our place tidy. The president is this very proper man. I imagine he probably makes his bed every morning and he's a pretty buttoned up, gentlemen, pretty quiet. He said what we do is we all pick up garbage for two hours, and then we come together as a community. We go through local issues where people get to voice concerns or things that they want to say then they have lunch and they go back to work. So the lessons for me are you will be heard, it’s okay to use a local practice to solve something people find really complex, and finally it’s important to create rituals of healing.
This idea of creating ritual appealing that even the president goes out and he picks up garbage with everyone, and just showing that willingness to lead. Another one that I found was fascinating is I spent quite a bit of time with Prime Minister Lee of Singapore and in my travels I believe there are three countries that were the most interesting in the way that they position themselves Rwanda as I've just talked about, Singapore which is extraordinary, and then the UAE, which is really a different type of animal in the Middle East.
But what was interesting about Prime Minister Lee when I asked him some questions, we started with what is it you're trying to do here? He said, I want to be the home for business in Asia. That was his phrase. Then he said, my father created this country from nothing. Our biggest problem was there were three cultures coming together the Malaysians, the Indians and the Chinese all living in this city state. All of them would bring their good and bad stuff from wherever their home countries are. He said, we're tiny, and we’ve got a billion people in India on one side, a billion of Chinese on the other side, and they all have the stuff that they love to shove on to their neighbors. We decided that’s not how we're going to run this. We're going to be the home for business in Asia, and that requires a few things. One, it's got to be safe. It's got to be incredibly safe, so that people you know, like the Hagerty’s and Lancaster's would want to send their beloved son over there and without freaking out about whether you're safe or not. The second thing is you have to have good education systems. If those people bring their families over, there's a good place for the kids to go to school and you have to have a good judicial system. Then banking systems so that it's safe for people to put money in the bank and sue each other if there's something goes wrong. You have legal recourse which by the way, what's the biggest problem in China right? Now all our YPO friends are trying to do business there. They know that they're operating on pretty thin ice. There’s this idea again that there's a whole country that operates on a pretty simple set of ideas, they’re storytelling, you know, creating the rituals that make people feel safe, make people feel like they're healing, and making people feel like they're creating value.
Jack: Those are great, great stories. Thank you for sharing. As the YPO Chairman, you were a volunteer and you enjoyed doing this, but you were also doing this on top of running Hagerty. I know you also do a lot of blogging and interviews yourself. How do you think about balancing these things?
McKeel: Well, hopefully you get a sense that I consider them to be very intertwined. As I said, leaders have something to say. I knew that when I became YPO chairman, and even though I love to read about history, and I did a lot of things like over here on this bookshelf behind me there are the 50 or so books that I read in the six months leading up to taking over as YPO Chairman because I knew I'd be traveling around the world. I had to have to say. I needed to be able to have context. I had pretty good background on the religious side, so I felt like I wasn't going to like step in my soup on that.
But when it came to history and other things, I spent a lot of time just preparing I guess that's my general approach to life, which is when somebody asks you a big question, I have something to say. My feeling about business has been especially through COVID and even leading up to COVID is business leaders are being asked more and more to fill a bigger role in people's lives as giving context to the world, as well as just giving meaning to things. I'm not religious at this point in my life, but as you think about religious practice is waning, and you have people describing needing more, in terms of spirituality and just connection with each other. They often rely on their employers and they rely on authority figures around them to give context. This idea of storytelling or understanding human need very much is intertwined for me, and what I realized is that every time I could learn more in in this more global sense of YPO not just going to a chapter meeting helped me in my business.
You can only go as far as you can build a team. And you know, I get it, it'd be probably pretty easy with my background for people to just, you know, overemphasize my role in the success of Hagerty. One of the things that I quietly think about is how do I make this business less McKeel centric? Because I don't think it's healthy over time. I spend most of my time on scaling a team and trying to be clearer in the way I give direction, clearer in the way I evaluate performance. I really give people the freedom to go win and be the next creators rather than it just being about something I learned about and put into play.
I mean, look, I'm happiest when I'm, I'm learning something. If I can put it into practice even better. I don't just learn to learn anymore. That was probably the biggest pivot for me going from academia, which is about learning to learn, and how many books you've read, rather than how many ideas can I put into practice? Now I'm much more of an idea-gatherer. I don't care how many books I read on a subject. It's how many ideas I can glean from the right sources.
Jack: In closing, what are some of the best practices that you would share or words of encouragement for someone who is looking to start either their own business or a creative projects.
McKeel: I have a pretty strong belief in the idea leading yourself first, especially if you aspire to be a leader. You have to be able to demonstrate to the people around you that you can lead yourself effectively. You have to have a higher than average level of self-awareness. That’s not just who you are but how you manage your emotions, how you take care of yourself physically, how you maintain generally consistent in the way you behave, act, and make decisions. People often point to when they lose faith in a leader is about them acting erratic, it's not because oh my god, Steve Jobs walked in and a bolt of lightning struck and invented the next new product that is going to make us all billionaires. That's not how life works.
I think about the opposite of what good leadership looks like. The opposite is it's erratic, it's self-absorbed. It's people lacking self-awareness and not being able to help other people articulate their emotions. From there what leadership looks like is pretty obvious. I don't believe in work life balance. I don't think there is such a thing. I think you get life. And I think how you spent life with people you love and people you want to spend time with is just kind of interwoven with what your work will be regardless. So my view is choose wisely because as you age and I have less life in front of me probably than I had behind me, is, I know there's certain things I'm not going to do much anymore. I give myself those little breadcrumbs going forward about the things I'm going to like to do going forward. For example like playing guitar, I'm not a great guitarist, but what you can’t see here is on either side of my computer screen, it's amps and guitars. Between every Zoom meeting, I just turn them on I blast AC/DC out and it just really changes my mind. Then I can go back to work a little bit more effectively. So lead yourself and use the opposite of good behavior to guide what good behavior is.
Build some disciplines into your that are fun and relaxing. There's a reason I play guitar. It's not verbal. It's not about storytelling. It's just making sound. I love to cook. Churchill famously learned to paint as a release and when I met President Bush, he took a painting for the same reason Churchill did which was just a way to not have to talk to people, and to create something visual and beautiful.
