Tuesday, June 12th, 2007...1:25 am
From Here To There
In my last post I wrote about my company, Sportsvite.com. In this post I want to write about my career and discuss how I got here and where I want to go. I’ve taken a more unconventional path than many of my classmates and peers. There have been times where I’ve probably confused you with some of my career decisions. I know that because I’ve often confused myself. Yet somehow I feel like I’m perfectly on track.
I’m not sure where to start this story but I’ll begin with the summer before my freshman year of college. I somehow simultaneously and freakishly developed a serious interest in both reading books and the stock market. I liked to read all kinds of books but I naturally gravitated towards Wall Street classics such as Liar’s Poker, Monkey Business, Bonfire of the Vanities (I realize it is fiction) and Barbarians at the Gate. At the same time I opened an Ameritrade account and “invested” my hard earned money trading option contracts. As I read about tycoon’s ruthlessly making billions, I was losing hundreds and was soon broke. It left a bad taste and I have never really been able to rationalize the market to myself.
Still, I had the itch to learn more about finance and I hustled to get an internship at Neuberger Berman after my freshman year. I worked there for two uneventful summers and began to wonder if finance was all it was cracked up to be. At the same time I started diving into Ayn Rand, Kurt Vonnegut and Jack Kerouac and began asking myself those larger than life, unanswerable questions that people who think too much tend to do (hint: working in finance is not the answer).
I entered the Michigan Business School and it turned out to be one of the most fascinating and educational experiences in my life. The b-school is basically a factory that churns out bankers, consultants and accountants. Intelligence is admirable but ferocious determination and a relentless work ethic are essential characteristics needed for success in the ultra competitive environment. I’m still not exactly sure what motivated these kids and where they came from (they certainly weren’t living at 701.south.forrest) but I certainly wasn’t able to compete at their level. So I decided to compete on my own level.
As my classmates prepared for their prestigious summer internships I planned a trip to Australia and then spent a summer bumming around in LA. Despite the weird looks from classmates and “underachiever” label I was pretty sure that spending my summer at the Great Barrier Reef was way better than having my very own pager on Wall Street. I ended up having a great summer and soon realized that I only had to listen to myself and I would be all right.
I tried to make the most out of the business school. I took most interesting classes, focused on Computer Information Systems, participated in extracurricular activities (not just for the food either), worked with professors on independent studies and attended lectures and workshops. I wasn’t all that concerned with homework and grades and barely maintained an acceptable B-school GPA.
So when it was time to interview on campus I wasn’t all that excited and couldn’t really distinguish myself. The results were disasterous and I must have struck out on at least 12-15 interviews. I felt like Doug Mientkiewicz playing in New York. I’m not good at fake enthusiasm and telling an accountant/recruiter that I was born to be a number crunching android wasn’t exactly my specialty. I realized this at the time but there was a hell of a lot of pressure to do what everybody else was doing. My ultimate example of indifference came when I had the inside track on a private equity (the term was just beginning to get hot) position at a major bank in NYC but was too lazy to leave school and fly to NYC because I didn’t want to miss the weekend in Ann Arbor.
During this time I happened to create my very own college basketball fan site called Littyhoops. I am and have always been a fanatical and obsessed college basketball fan. Since I wasn’t doing school work or preparing for interviews senior year I had an awful lot of free time and a good portion of that time went towards watching college basketball. I decided that I wanted my voice to be heard by my peers and a website seems like an interesting way to do that. I built everything myself and spent countless hours designing, coding, writing and marketing the site. Right away I received recognition from my friends. I remember going on a trip to Wisconsin and kids I didn’t know were following my picks on Littyhoops. I wasn’t sure what this all meant and definitely wasn’t making any money from it but I spent more and more of my time working on Littyhoops. I figured that if this was something I loved to do in my free time, why not try and make it my full-time job. So I started to look for internet jobs in sports.
It took awhile but the summer after I graduated I was offered a job to be a web editor at the Official College Sports Network. I was offered the job over the phone after speaking about my experience with Littyhoops. The job paid like crap and was on the other side of the country in Carlsbad, CA. But heck, if I really wanted to do something I love then I had to live with the consequence of having to move to San Diego and live on the beach.
I spent 16 months in San Diego and this is where my b-school education paid off. I was by far the most motivated and driven person in the office. Within months I moved from my lame and thankless editorial position to a business development job created for me where I ran the college sports auction program. After OCSN was acquired by CSTV, I was the first person to transfer to the CSTV office in New York City.
I was confident I was destined for greatness at CSTV. Working on the internet side of a high profile college sports start-up was the perfect job for me. Perfect. I was lucky enough to work on amazing projects such as March Madness on Demand. I created the firsts mainstream college fantasy football game, had direct interaction with top executives and was promoted to a Director position within months. Unfortunately, it wasn’t for me. While I appreciated and valued the learning experience I wasn’t enjoying myself and couldn’t see a future for myself there. It threw me for a loop. Here I had the perfect job and I was unsatisfied. Once I realized that CSTV was no longer the answer, I knew I had to move on to my next experience.
After taking time off to travel (best experience of my life) I spent a summer trying to uncover, evaluate and secure opportunities and find a place where I could feel comfortable, control my own destiny, and have the freedom to operate on my own terms. Eventually, I found all those things at  Media and Sportsvite and once again I’m in love with my job.
There is no guarantee that Sportsvite will be successful. Amazingly, that doesn’t worry me. When it comes to my career, I’m somehow blessed with an extreme confidence in myself and my ability to define and then reach my own success. I’m not sure why I feel this way but I do and it allows me to take risks, work on my own terms and create my own ethical, business and career goals. Right now, that seems to be more important to me than my financial security. I’m pretty sure that will change as I go through life and have more responsibilities and people who depend on me but I guess that’s why it’s great to be young.
I don’t think I’m a lifelong serial entrepreneur. While I find the start-up world fascinating I also find it tiresome as hell and realize there are easier ways to make it big. I’m not sure I’m married to the digital media industry for the long haul. It’s a great place to be for a young thinker but I’ve witnessed older executives who work in a constant state of fear and are asked to predict the unpredictable and it doesn’t seem all that glorious. I’m not sure I want to stay in the sports world. Obviously, it allows me to better relate to my work (what can be better than saying it is my job to make it easier for people of the world to play sports or watch the epic USC – Notre Dame game from the field!) Unfortunately though, I don’t always experience the innovation and originality in sports that I crave.
I guess I’m trying to say I really have no idea what I am going to do next, or in five years or how I am going to make my mark. Luckily, I’m not the least bit concerned. I might just have a few rays of that PB sunshine still in me after all.