Derek Coburn built a $3-4K monthly comic-book business as a teenager, then became a top financial advisor at MassMutual through relentless cold-calling. He spent decades chasing income and client numbers to prove doubters wrong, only realizing at 45 that he'd optimized for the wrong metrics and needed to rebuild around values instead.
Chapters
I found myself in a classroom full of kids chanting, "Who do we hate? We hate Derek." I found myself in and out of the principal's office with my parents, with the teachers, with the guidance counselors telling me that I wasn't going to be successful in life because I wasn't getting good grades. I mean, ironically, I was running a comic book business that was making like $3,000 to $4,000 a month in cash. I said one time, like, I think I'm making more money than everybody in this room except for maybe my father. So I don't understand why you don't think I'm going to be successful. But I heard that message And I heard it frequently. And then I had all the girls telling me that they didn't want to be my girlfriend or date me. And, and I thought back and I'm like, you know what? My life, I think, just became one big giant, like, you don't think I can do something? Watch me. And I just think that that was how I dealt with the trauma at the time. Instead of maybe going awry, going off the deep end, getting angry, doing like, who knows what, I just channeled it and I just said, I'm going to prove all these people wrong.
Yeah. Another mutual friend, Nathan Barry, recently said, uh, Entrepreneurship is a trauma response. And I think there's some, some truth to that really is you're, you're, what I'm hearing is you're going down this path really to, to prove to the world that you're worth something.
Yeah. And I did it and I, I have a lot of amazing people and a lot of amazing stuff in my life because of that. And I'm married to the love of my life. I've got incredible kids. I have more friends than most adults that I know. And I don't need to prove anybody wrong anymore. But yet I was finding myself and still do sometimes waking up a lot of days feeling like, who are we going to prove something to today? And in order to prove somebody wrong, you need an adversary, right? So it's like I'm like manufacturing drama or issues. So it's my body's like, let's do this again. Like, we're so good at like proving people wrong and look at all the amazing shit that we have to show for it in our life. So like, when are we going to do it again? And I'm like, I don't think that I knew what it felt like to have a calm central nervous system until I was 45 years old, maybe like 3, 4 years ago. And I'm really trying to lean into a place and I, I'm giving myself a lot of credit for what I've done over the last couple of years to where I can be not from a place of having to prove anything to anybody. Cause I don't feel like I need to anymore. I just think that like my body and my habits and my tendencies were driven by that for so long that it's hard just to shake them overnight.
Well, take me back to those Proving Energy days. What was your first taste of success? What was that like?
It was, it was the comic books, man. I was like young compared to all the other people that were doing that at the time. My mom loves telling the story about how she can't believe how she let me drive to Chicago and New York with these other comic book dealers at the time. And it was because I'd like just successfully and accurately convinced her that these guys were like complete dorks and they were just not going to get into any trouble and not cause any harm. I would buy up like 20, 30 copies of a comic book for like $2 locally. We would go to these big comic book shows and I would meet the artists. And because I was the 16-year-old or the 15-year-old kid, they would do more for me than they would do for the adults. You know, I would get 30 copies signed. I'd bring them back and sell them for $20 apiece. And so I, I do remember, even though I share that I was being told at a younger age that I wasn't going to be successful, I do remember feeling very confident that they were all wrong. That they were wrong, at least about that part, that I wasn't going to be successful by their metrics. But I knew that I was going to be successful in my own way.
And how did that translate to business? What was your first real business?
Well, my first real business, I'll say, was as an intern for a financial advisor at American Express Financial Advisors between my junior and senior year of college. And I was just really good at cold calling. That was like the main factor that was going to determine whether you were successful or not in that industry. It didn't matter if you were smart. Like, they didn't have certified financial planning degrees back then in 1998, 1997. They didn't have— you couldn't go to college and get a major in financial planning like you can now at some colleges. It was just like, how much rejection can you tolerate before you break? And I was making 500 phone calls a week for this financial advisor, and I was so good at it that they had me give a talk to the other financial advisors who, like, it was their job, it was their livelihood. They needed to make appointments and get new clients to pay their mortgage. And I was giving them a pep talk. I was a junior in college, right? They offered me a job. I was able to, to kind of like just take off like my senior year of college because I knew that I could just slip into this opportunity no matter where I ended up. But yeah, man, getting shot down by people during the day and getting shot down by girls at night when I was going out to all the bars and everything. And I just very quickly developed this wall, this like, the rejection doesn't bother me. I'm not taking personally.
Yeah, it's interesting to trace the arc from you're never going to be successful, all these people telling you, and you internalizing the story of watch me. Cold calling is sort of the ultimate way to do that.
Yeah, man.
Yeah.
I mean, it was— I mean, I knew once I started, I ended up starting my career with a different company, with MassMutual in 1998. And I just knew exactly how many dials I had to make in order to end up with a certain amount of revenue by the end of the year. Like I had that dialed in from a system standpoint. I set lofty goals, I hit them, and it served me really well. Until, until it didn't. But it served me really well for a long time. Yeah.
Let's talk about it served you well until you didn't, because that's, that's the arc that most successful high performers go through, right? This trauma response to, I'll prove the world, watch me. You're smiling and dialing. Been there myself. I know how hard that is. And, and you find the success that they told you you'd never have.
How did that feel? It felt good, man. I ended up becoming very good friends with a guy who played for the Baltimore Ravens at the time. And I was in Baltimore at this point in my career, and I was going out with the team like the year that they won the Super Bowl in 2000. And I was like going to the best parties, living it up, man. It was a lot of fun. I started working with some of them, but it ended up not sticking because I ended up also starting working with attorneys. And as I got better at cold calling and better meeting different types of people, you're meeting attorneys and they're ready to get your advice about how they should invest their money from day one. Whereas with the, a lot of the players, it was like a lot of energy had to go into convincing them why they shouldn't buy like their 6th car or why, you know, they should open up a brokerage account in the first place. And then I met Melanie, you know, eventually became my wife and I lost a lot of the non-financial perks that came with that lifestyle. And so I sort of like drifted away from it a little bit, but that felt really good. And I would say the reason I made the comment, it felt good until it didn't, is I think that goals ended up taking my business to a place that ended up causing me a lot of problems. I think I woke up one day and I had 300 clients and I only liked working with like 25% of them. And I was looking around at my peers. I was qualifying for all these big fancy trips. I was on cruise ships in the middle of the Mediterranean, going, bouncing from place to place. I was 10, 15 years younger than everybody else there, and they all had 2,000 clients and they all didn't like working with the majority of them. And, and I just had to, like, take a step back and say, you know, how did I end up with all these people that I don't like working with? And one of the reasons was, oh, it's because I set goals to have X number of clients by the end of the year, X number of new assets under management, X number of new insurance policies sold. And I think subconsciously every year in September and October, I said, these goals are within reach and I'm going to hit these goals. And I brought in people and I brought in certain clients that would help me check those boxes. And then I ended up 5 years later with a whole lot of people like that I didn't like working with and like we just didn't like jive all that effectively.
And when you were setting goals and systematically checking them off, what was the cost to you personally for kind of living this life that sounds like it was out of alignment with who you really are?
I am not sure that I have any regrets and I am preaching a ton of balance right now. And in the book that I just came out with, like really preaching that there's another way besides just opting into the money game that the majority of people are playing. And I think that almost all of the really great, wonderful things that I have in my life right now are directly correlated with me working 80 hours per week when I was in my 20s. And so maybe I could have had more balance then, but like, what else was I going to do with my time? I mean, I was just like, I didn't have the kids at that time. I didn't have the wife at that time. And so I'm not sure that, that I feel bad about it or that it was that because I got out of it. I, we could talk about how I, how I transitioned away from these people that I didn't necessarily want to continue working with, but it was all good, good learning, good lessons and good experience.
