The credentials listed beneath my picture on the left are a quick synopsis of my resume. I’ve done a lot of different things and accomplished a lot. And those things are well and good, but, the truth is, those things don’t define me. You know what defines me? I grew up in a blue-collar family on the South Side of Chicago. When you hear about the South Side of Chicago, what do you think? Gangs, drug lords, murders, prostitution? It has those problems, to be sure. But in truth, the South Side gets a bad wrap. There are tons of good people there. I know.

But what is true is that the people there are tough. The best way I can describe the culture on the South Side is that its defining qualities are people drinking and fighting. And they’ve taken snark to a whole new level. Which means they make fun of people relentlessly and mercilessly. So, when you grow up in that world, you have to learn to let insults roll off your back like water. In my observation, people had one of two responses. Either they got [mentally] strong or they folded like a wilting flower. And if that weren’t enough, I had 3 older brothers who were just as relentless. So, I got hit with grief daily at home, at school and out in the neighborhood. However, as fate would have it, I was one of the people who became mentally tough.

Fast forward to my first job in finance out of college. I got hired at Ibbotson Associates in Chicago. It was founded by Roger Ibbotson who is a world-renowned Professor of Finance at Yale University. Unbeknownst to me, the first week on the job I discovered they held a monthly company-wide meeting called “Ibbotson U.” Being run by three PhD’s in Finance, it was a very academic place.

So, in these meetings, they packed the whole company (about 32 people) into a large conference room and these PhD’s would review some very high-level math I hadn’t seen before. I’ll never forget how inadequate I felt. I knew I had a gift in math, but what was this? As I looked around the room, I saw a lot of heads nodding in agreement. The whole room seemed to understand this stuff, but me. So, I did the only thing I knew how to do. Ask questions. What’s a singularity test? How does it work? Shouldn’t this equation produce an error term? Where is it? If we turn the error terms into a fresh time series, can we do something with it? And on and on. It quickly became apparent that I was the only one asking questions while everyone else seemed to get it.

I remember going back to my cubicle after that first meeting feeling very dejected. I realized this role was going to be a lot harder than I had thought. And where did all these people come from? What schools did they go to that the knew all this? WTH?

A month later, the next meeting comes along - and the same thing happens! Again, the meeting quickly devolved into a Q&A session between me and the professor. And yes, I was the only one who didn’t understand this stuff. WTH^2!!

Third month comes along and I attend my third Ibbotson U. meeting. Once again, SAME. THING. HAPPENS. Almost despondent, I slunk back to my cubical to ponder the day’s drubbing… but then something unexpected happened, and it changed my life. A woman from the meeting comes over to my cubicle. She said, “You asked a question in there and I didn’t really understand why you asked it, so I did understand his answer. Can you explain it to me?” So, I said, “Sure.” I stood up and we began talking about it. As I’m talking, I slowly see heads pop up from all the cubicles around us (like gophers on a golf course) and my colleagues began listening in to our conversation. Before I knew it, we had roughly a 45 minute conversation with about a half-dozen people. All these people who I had thought understood what was taught - actually didn’t.

In the coming months, this became the norm. We’d all go into the conference room for the Ibbotson U meeting and afterward, a large sub-group would gather around my cubicle. Only my audience in the meeting AFTER the meeting grew in size and duration. The professors would teach us all advanced concepts in finance - where I would ask tons of questions DURING the meetings - and then, in the meeting after the meeting, I would teach my peers what I just learned. I know it sounds crazy, but it’s true.

What I learned is that my colleagues were AFRAID to ask their questions, which of course blocked their growth. In contrast, my desire to succeed was greater than my fear of failure. But this was a lesson I learned growing up on the South Side in my formative years. Back then, I would be humiliated by people I knew 5 - 10 times a day. Hell, I’d get humiliated by my older brothers 3 times before breakfast. So, I never worried about public humiliation - at least not to the extent I would let it block my success. But for my colleagues at Ibbotson, it was just the opposite. Their fear of humiliation was greater than their desire to succeed. That people - anybody - would do that was completely anathema to me. But, I guess not everyone can be lucky enough to grow up on the South Side.

So, it was a huge life lesson. I wonder how many careers have been derailed because talented people have been thwarted by their own fears? Are you one of them? I know these things are easier said than done. So, if you like, we can arrange a side deal where I humiliate you every day like my brothers did. ;-) I’m kidding, of course. But there is a real point here. Confidence comes from know-how. And if fear is your issue, then know-how is the answer. Once you come to realize how different what I teach is, you’ll also come to understand it can change everything in your life. And this is what I’m after. Nothing would be more gratifying to me than to change people’s lives for the better.

I believe that there’s something about the human heart that you know truth when you hear it. And I’m all about it. So, you’re going to get heaping doses of it with me. Let yourself open up and respond to truth - whatever that means for your career - good or bad, up or down, left or right. If our paths are meant to cross, they will cross. But don’t short-circuit your future because of fear. Just like in sports, an athlete will miss 100% of the shots he doesn’t take. Get off the damn fence and jump in the game. And if this isn’t the life for you, that’s fine. I’ll be fine. But live a life worthy of your calling. I am. Are you?