He Went From MLB Pitcher to Insurance Exec at a Top-3 Global Broker

0:05Mike O 'Connor, four years MLB, rock star living out of the DC area. Yeah. Two kids? Two kids, yeah. Beautiful family. Five and 12. Love it. So we interviewed you before, so I know that Richard likes the same questions. I'll ask a couple of them, then I want to jump into who you are as really... Let's start off with this. What is life about? Yeah, that's a good question. Let's go deep right at the beginning. Yeah, hit me hard. Yeah, I just found out I was going to do this earlier this afternoon, so it reminded me when I was a pitcher. I was a left-handed pitcher coming out of the bullpen. The phone just rings.

0:40You just raised your right hand, though. You got to just jump. I got the mic in my left hand. For me, life, you know, I think it's, you know, my why at this point in my life is my family. I mean, I got a 5 - and 12-year-old just trying to give them the best life that I can. I finished playing about 10 years ago, played 12 years professional baseball, and had to figure out another thing. And I got into the insurance business in 2016 and been in it ever since. I love it. Tell me about what family means to you a little bit more. Like what do you do? How do you spend time? Quality? Because most parents today don't spend quality time with their kids.

1:15I'm just being real. Yeah, I think a lot of my success was just due to my parents and how involved they were with my life. And I think them being my role model, I mean, you know, I could work around the clock with what I do, but I try to have boundaries with what I do as far as being at all my kids' events, sports, taking them outside after school and just trying to get them out doing things, not on iPads and playing video games all day. So, yeah, I think it's important to spend time with your kids. My dad always found time to play catch with me in the backyard. He would catch my bullpens even when I was in pro ball, even when he, you know, take baseballs off his shins.

1:58So I think, you know, I don't know. His example has been, you know, kind of how I try my parents, what they did for me is what I try to give to my kids. Amazing. What is the$1 million lesson that you could add value to this room about what made you the best in your sport? Yeah, I think baseball is a huge mental game. A lot of people would say it's, you know, the game of failure. I think, you know, everybody has ups and downs in their business, And it's just, you know, trying to get better each day, be a good person, be a good teammate. I think that's, you know, kind of how I try to live my life and why I've been able to have success outside of sports.

2:36What have you learned through business now, taking your sports background, mindset, belief system, attitude, perseverance, all of that into the business world? And how have you become successful in business now? Yeah, I mean, going back to baseball, I mean, I think, you know, there's no there was no shortcuts, right? I had to work hard all throughout. I mean, I was a good player in high school, was good enough to go play D1 at George Washington University as a walk on. You know, just worked hard while I was there, got bigger, stronger, was able to get drafted and went from a college walk on to a major league player just through, I think, just dedication and hard work.

3:16So, I mean, I think, you know, getting into the industry I'm in now, just trying to, you know, start at the bottom and learn everything I can and just try to get better each day. What is your goals in business now? Because obviously you achieved top of the world for sports. And now what's your goals in business? That's a good question. Yeah, I think I'm in a good spot with my company. I work with Gallagher. We're the third largest insurance broker in the world. We can do a lot of different things. You know, I work with current athletes on some of their insurance needs. I do property and casualty insurance.

3:49And then I work with mostly real estate and tech business owners. You know, a lot of what we're able to do, I think, you know, can be valuable if something goes wrong. I mean, hopefully they don't need it. But, you know, it's a service that people need. And I think we do a great job doing that. What's the most costly financial mistake or mistake you've ever made in your professional career? yeah i think when i was young just not being more involved in my finances and not knowing more about that i mean you have an opportunity in sports to make a lot of money in a short period of time at a young age and i think um you know nil wasn't a thing so college wasn't really preparing guys for that i mean i was a finance major and you know in college and a lot of the stuff we learned wasn't things that helped me with financial literacy so yeah i think guys now have there's a lot more out there but there is a lot more you know pitfalls things that guys run into as well but yeah i think if i would have been more involved in some of that stuff earlier and knew more um you know maybe things would be a little different give one piece of advice um that you would want to for kids for parents of kids that you've learned that could make them maybe a better parent sure yeah i've you know i've coached a lot of kids at one point i did a lot of that when I played.

5:09I think just finding what your kids like, right? I think a lot of times, you know, parents have their sports and things that they like and just, you know, allowing your kids to tell you what they're really passionate about and then, you know, allowing them to do that. I think that's huge. I think a lot of times people push their kids in directions that they wanted to go and not what the kids want to go. Thanks, bro. Appreciate you. Thank you. Give a round of applause. Thanks, Daniel.

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