I was 25 when I was first approached with the idea of running an excess and surplus lines insurance brokerage firm. Regrettably, I declined. I just didn’t think I was ready. My MBA was about a semester and a half away from completion. My son wasn’t born; American International Group (AIG) was on the brink of collapse, Lehman had just been told to essentially “get lost” by the federal government, Fannie Mae was in need of government attention and I was also 45 days away from closing on my mortgage—which, of course, was backed by Fannie Mae.
One might agree that the timing just was not right.
I remember a few days after I declined the offer. I kept thinking about business executives that I’ve long admired, like Don Thompson, president of McDonalds, Rob Johnson, former president of BET, E. Stanley O’Neil, CEO of Merrill Lynch (until he arguably led it into a tailspin), Ken Chenault, CEO of American Express, Ronald Williams, CEO of Aetna, Ursula Burns, CEO of Xerox and of course Sean “Jay-Z” Carter, CEO of Def Jam Recordings and Roc-A-Fella. I began to think about them more and more, and ask myself if they ever turned down what seemed to feel like a once-in-a-lifetime opportunity. I beat myself up pretty badly. I could not get out of the way of my own mind—I felt in my heart that I had made the right decision by letting the opportunity go, but I couldn’t let go.
I’ve never been 6’5”, and I’ve also never been able to place six words in a sentence that rhyme and tell a story at the same time. Nevertheless, saying “no” that morning in my mind was equivalent to letting my NBA contract go, or watching my record deal sail away. But, truth be told—I couldn’t disappoint my son. I didn’t want to accept a position that would limit my ability to be there for him in any way that he needed me to be. Waiting and preparing for the “ideal” opportunity seemed hopeless, so instead, I created the ideal opportunity.
For the next 12 months, I committed myself to finishing my MBA, I committed myself to becoming a better broker, and to setting aside time for Carter. It paid off. A private equity firm called and asked if I could be willing to act as president and CEO of a brokerage firm of my own creation—this time, I said yes.
Within a few days of my affirmative response, I was flying all over the country, meeting presidents of other insurance companies, garnering their support and advice. I remember vividly sitting in the office of one president in Scottsdale, Arizona. He said, “Earl, this has got to be one of the best days of your life.” Part of me was ashamed that it was not, but I felt the need to embellish. “Yes, it’s an incredible experience,” I said.
“I’ve waited quite some time for this—I’m really grateful to be here and as president of Hybrid Insurance Group, I will do everything I can to make sure I don’t disappoint you.”
He didn’t say it, but his eyes did—“How long did you rehearse that one in the mirror, Earl?” When he asked me the question about happiness it was as if I forgot how to speak—or better yet, how to think. The birth of my son was a happy experience, but that was almost a category unto its own. Simply saying I was “happy” would not do that experience justice. When he asked me if this was one of the happiest experiences that I had, I was embarrassed to say that it wasn’t. Most grateful moment, absolutely, but happiest: no.
Racing my father as a child was one of the happiest moments of my life. The garage was almost finished. The foundation was poured, the walls were up, and the only thing left to do was put on the roof. At the age of six, it seemed like an eternity before the garage would ever be finished. Each day, I would follow my father out the door and sit next to his job site.
It’s crazy, because of all the memories that I have, this is the only good one I have of my father—at least, that I can remember.
This particular morning, I asked my father to race me around the garage and he agreed. I made a decision that I was going to win. I wasn’t sure how, but I knew this morning would be different. We lined up; I tried to get my foot ahead of his, but he quickly corrected me. He had white Reebok classics on, the top of his sneakers had gray stains from where the cement dripped. He had blue jeans on with a white T-shirt that had a hole under the right arm. He didn’t have a belt on, which I’m sure drove my mother crazy. Of course I had on my Reebok classics, but the writing on my sneakers was blue; his was white. I had every intention of winning the race that morning.
“On your mark, get set, go!” My father quickly got ahead of me. At the first turn he slipped, and then we were into the backyard. If I could get ahead of him around the shed, I knew I could win. We passed the shed and I could hear him laughing behind me. I kept running uninterrupted, made the final turn and, with a few yards left, I made it—I won. This moment in time was without a doubt one of the happiest moments of my life. I am not sure if he knew then or ever how much that morning meant to me, but it meant virtually everything to me for a number of years. I made a decision to win and I actually won.
So much of what it took for me to start Hybrid Insurance Group, formulate a team of energetic free-thinkers, and generate approximately twelve million of premium in its first year was learned by losing to my father in these silly foot races except for that morning. Each and every day, I make a decision to operate one of the most ethically-sound, innovative insurance brokerage firms in the country.
The races around the garage with my father never happened again. I don’t remember seeing the classic Reeboks after that day. I knew where mine were, but I don’t remember seeing his. My mother’s love for my father changed, as did her facial expressions when he was around. He didn’t make her smile anymore—I wasn’t sure why, at the age of six but I knew their love changed. Their body language said it all—it was over. Soon thereafter, my father was on a plane back to his native island of St. Croix, and I would not see him again for some eight years—and then, a year after that, when we buried him.
I was 14 when my father passed away. At the time, I found it somewhat ironic that my father went back to St. Croix, considering the fact that my parents met at Oakwood College in Alabama. My mother, a native of Kingston, Jamaica, moved here to further her nursing education and my father was at Oakwood College as a result of the GI Bill.
When I share the story of my race with my father, many find it odd that I shed more tears upon finding out that Johnnie Cochran passed away from a brain tumor than I did when I learned of my father’s death. It took me many years to rectify the inconsistencies in my mind that made sorrowful events seem more tragic if they involved iconic figures in my upbringing. I don’t know what my sentiment surrounding the passing of these individuals say about me as a black male, a fatherless child, a brother, a son, a nephew, an uncle and a father, but I understand what it says about where I came from and where I am going.
When I think about the exemplary men around me growing up, there were very few. I learned about a man loving a woman by watching the Huxstables on The Cosby Show. The first black male lawyer I ever saw was on The Fresh Prince of Bel-Air. I grew up in a world where the men that I admired were men that I never met. Meanwhile, I had a father who only taught me how to find comfort in pain, and sadly, I don’t believe it was his intent to teach me that lesson. I remember wishing that my father was like Rob Johnson—of course, I had no idea what he was like as a parent, or if he even was a parent, but I felt more connected to him than I was to my own father.
I never want my son to ever feel that way.
At 27 years old, as the father of Carter Esteban O’Garro and as the president and CEO of Hybrid Insurance Group, I have learned a considerable amount about winning, quite a bit about losing and a little about keeping score. I have learned that the greatest victories I have experienced came when winning wasn’t the focus, but excellence was. I learned that losing only made me better at winning, and I learned that keeping score allows me to stay ahead of my losses. Sean “Jay-Z” Carter, Don Thompson, Rob Johnson, Johnnie Cochran, and E. Stanley O’Neil made me realize that I could play.
As a black boy raised by a single mother, knowing you “can” has the ability to be so powerful. Making a decision to win is something to which I’ve committed myself daily for as long as I can remember. It’s easy to develop excuses for why something can’t happen. I’m sure my mother could have developed a million excuses as to why she didn’t want to be a great mother, but she made the choice on a daily basis to commit herself to being who she was to me.
Twenty-one years later - one child, one less parent, four siblings, and one less grandparent - I realized something beautiful about life. I realized that the comfort that we find in pain is equally as important as the love that we find in one another, regardless of how temporal it may seem. The lessons that I learned by racing my father are what allow me to forgive him for not being a good father, especially when I needed him most.
The lessons that I learned by reading about how Rob Johnson created BET and eventually sold portions of his firm, or how Ursula Burns turned around Xerox, or listening to Sean Carter talk about the formation of Roc-A-Fella as he sits down with Warren Buffet inspire me to never forget the power of my thoughts and passions. Like these great business leaders, I too aspire to go beyond myself and be someone that another generation can use as a mirror, and an inspiration for their leadership and ambitions.
One might agree that the timing just was not right.
I remember a few days after I declined the offer. I kept thinking about business executives that I’ve long admired, like Don Thompson, president of McDonalds, Rob Johnson, former president of BET, E. Stanley O’Neil, CEO of Merrill Lynch (until he arguably led it into a tailspin), Ken Chenault, CEO of American Express, Ronald Williams, CEO of Aetna, Ursula Burns, CEO of Xerox and of course Sean “Jay-Z” Carter, CEO of Def Jam Recordings and Roc-A-Fella. I began to think about them more and more, and ask myself if they ever turned down what seemed to feel like a once-in-a-lifetime opportunity. I beat myself up pretty badly. I could not get out of the way of my own mind—I felt in my heart that I had made the right decision by letting the opportunity go, but I couldn’t let go.
I’ve never been 6’5”, and I’ve also never been able to place six words in a sentence that rhyme and tell a story at the same time. Nevertheless, saying “no” that morning in my mind was equivalent to letting my NBA contract go, or watching my record deal sail away. But, truth be told—I couldn’t disappoint my son. I didn’t want to accept a position that would limit my ability to be there for him in any way that he needed me to be. Waiting and preparing for the “ideal” opportunity seemed hopeless, so instead, I created the ideal opportunity.
For the next 12 months, I committed myself to finishing my MBA, I committed myself to becoming a better broker, and to setting aside time for Carter. It paid off. A private equity firm called and asked if I could be willing to act as president and CEO of a brokerage firm of my own creation—this time, I said yes.
Within a few days of my affirmative response, I was flying all over the country, meeting presidents of other insurance companies, garnering their support and advice. I remember vividly sitting in the office of one president in Scottsdale, Arizona. He said, “Earl, this has got to be one of the best days of your life.” Part of me was ashamed that it was not, but I felt the need to embellish. “Yes, it’s an incredible experience,” I said.
“I’ve waited quite some time for this—I’m really grateful to be here and as president of Hybrid Insurance Group, I will do everything I can to make sure I don’t disappoint you.”
He didn’t say it, but his eyes did—“How long did you rehearse that one in the mirror, Earl?” When he asked me the question about happiness it was as if I forgot how to speak—or better yet, how to think. The birth of my son was a happy experience, but that was almost a category unto its own. Simply saying I was “happy” would not do that experience justice. When he asked me if this was one of the happiest experiences that I had, I was embarrassed to say that it wasn’t. Most grateful moment, absolutely, but happiest: no.
Racing my father as a child was one of the happiest moments of my life. The garage was almost finished. The foundation was poured, the walls were up, and the only thing left to do was put on the roof. At the age of six, it seemed like an eternity before the garage would ever be finished. Each day, I would follow my father out the door and sit next to his job site.
It’s crazy, because of all the memories that I have, this is the only good one I have of my father—at least, that I can remember.
This particular morning, I asked my father to race me around the garage and he agreed. I made a decision that I was going to win. I wasn’t sure how, but I knew this morning would be different. We lined up; I tried to get my foot ahead of his, but he quickly corrected me. He had white Reebok classics on, the top of his sneakers had gray stains from where the cement dripped. He had blue jeans on with a white T-shirt that had a hole under the right arm. He didn’t have a belt on, which I’m sure drove my mother crazy. Of course I had on my Reebok classics, but the writing on my sneakers was blue; his was white. I had every intention of winning the race that morning.
“On your mark, get set, go!” My father quickly got ahead of me. At the first turn he slipped, and then we were into the backyard. If I could get ahead of him around the shed, I knew I could win. We passed the shed and I could hear him laughing behind me. I kept running uninterrupted, made the final turn and, with a few yards left, I made it—I won. This moment in time was without a doubt one of the happiest moments of my life. I am not sure if he knew then or ever how much that morning meant to me, but it meant virtually everything to me for a number of years. I made a decision to win and I actually won.
So much of what it took for me to start Hybrid Insurance Group, formulate a team of energetic free-thinkers, and generate approximately twelve million of premium in its first year was learned by losing to my father in these silly foot races except for that morning. Each and every day, I make a decision to operate one of the most ethically-sound, innovative insurance brokerage firms in the country.
The races around the garage with my father never happened again. I don’t remember seeing the classic Reeboks after that day. I knew where mine were, but I don’t remember seeing his. My mother’s love for my father changed, as did her facial expressions when he was around. He didn’t make her smile anymore—I wasn’t sure why, at the age of six but I knew their love changed. Their body language said it all—it was over. Soon thereafter, my father was on a plane back to his native island of St. Croix, and I would not see him again for some eight years—and then, a year after that, when we buried him.
I was 14 when my father passed away. At the time, I found it somewhat ironic that my father went back to St. Croix, considering the fact that my parents met at Oakwood College in Alabama. My mother, a native of Kingston, Jamaica, moved here to further her nursing education and my father was at Oakwood College as a result of the GI Bill.
When I share the story of my race with my father, many find it odd that I shed more tears upon finding out that Johnnie Cochran passed away from a brain tumor than I did when I learned of my father’s death. It took me many years to rectify the inconsistencies in my mind that made sorrowful events seem more tragic if they involved iconic figures in my upbringing. I don’t know what my sentiment surrounding the passing of these individuals say about me as a black male, a fatherless child, a brother, a son, a nephew, an uncle and a father, but I understand what it says about where I came from and where I am going.
When I think about the exemplary men around me growing up, there were very few. I learned about a man loving a woman by watching the Huxstables on The Cosby Show. The first black male lawyer I ever saw was on The Fresh Prince of Bel-Air. I grew up in a world where the men that I admired were men that I never met. Meanwhile, I had a father who only taught me how to find comfort in pain, and sadly, I don’t believe it was his intent to teach me that lesson. I remember wishing that my father was like Rob Johnson—of course, I had no idea what he was like as a parent, or if he even was a parent, but I felt more connected to him than I was to my own father.
I never want my son to ever feel that way.
At 27 years old, as the father of Carter Esteban O’Garro and as the president and CEO of Hybrid Insurance Group, I have learned a considerable amount about winning, quite a bit about losing and a little about keeping score. I have learned that the greatest victories I have experienced came when winning wasn’t the focus, but excellence was. I learned that losing only made me better at winning, and I learned that keeping score allows me to stay ahead of my losses. Sean “Jay-Z” Carter, Don Thompson, Rob Johnson, Johnnie Cochran, and E. Stanley O’Neil made me realize that I could play.
As a black boy raised by a single mother, knowing you “can” has the ability to be so powerful. Making a decision to win is something to which I’ve committed myself daily for as long as I can remember. It’s easy to develop excuses for why something can’t happen. I’m sure my mother could have developed a million excuses as to why she didn’t want to be a great mother, but she made the choice on a daily basis to commit herself to being who she was to me.
Twenty-one years later - one child, one less parent, four siblings, and one less grandparent - I realized something beautiful about life. I realized that the comfort that we find in pain is equally as important as the love that we find in one another, regardless of how temporal it may seem. The lessons that I learned by racing my father are what allow me to forgive him for not being a good father, especially when I needed him most.
The lessons that I learned by reading about how Rob Johnson created BET and eventually sold portions of his firm, or how Ursula Burns turned around Xerox, or listening to Sean Carter talk about the formation of Roc-A-Fella as he sits down with Warren Buffet inspire me to never forget the power of my thoughts and passions. Like these great business leaders, I too aspire to go beyond myself and be someone that another generation can use as a mirror, and an inspiration for their leadership and ambitions.