The Unlikely Journey From Practicing Law to Selling Sports Picks

Dec 6, 2017

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As high school graduation approached, my desire to be a teacher remained steadfast.  The profession provided a unique opportunity to give back what so many of my teachers gave me – a foundation to succeed in the real world.  I had always been good with numbers so teaching math seemed to be logical destination after graduating from college.

At some point during my sophomore year in college, my passion for politics merged with a growing interest in the law.  My coursework started to revolve around political science and pre-law classes.  As my senior year approached, I had made the decision to attend law school.

At the time, it just made sense since politics and the legal profession seemed one-in-the-same in many respects.  With my choices of where to attend narrowed to Wake Forest University and the University of Connecticut School of Law, I decided to return to my home state of Connecticut.

I graduated from the University of Connecticut School of Law and embarked on what would become a successful seven-year career at a private litigation firm in Fairfield County.  It was at this point that my interest in sports handicapping took off.  I started reading every book on sports betting that I could get my hands on.

My evenings and weekends were quickly consumed by my growing passion for sports handicapping.   The prospect of generating a significant return on investment by betting on sports also peeked my interest.

After spending a good part of two years studying the concepts surrounding sports investing, I made the decision to join a public sports handicapping website called Statfox in 2005.  The site largely consisted of a forum of amateur sports handicappers like myself sharing betting advice and offering free sports picks.

In addition to reading every conceivable book on statistics, analytics and probability, I also studied some of the more successful professional handicappers in the industry.  I analyzed their work product in an effort to reverse-engineer their methodology. I started developing my own math models and statistical databases.

I primarily focused on enhancing my understanding of three important aspects of sports handicapping – fundamental, situational and technical analysis.  Other members of Statfox started noticing the success I was having with my sports picks and my following started to grow by the day.

The challenge was balancing my professional job as an attorney with my growing passion for sports handicapping.  There came a point in late 2006 in which I began entertaining the idea of becoming a professional sports handicapper.

With the unwavering support of my girlfriend (and now wife) and family, I put together a business plan to determine whether a sports handicapping business was feasible.

Could I support a family by selling sports picks?  Was I willing to leave my law practice to pursue a new career in the sports picks industry?  Was there room in the industry for another sports picks service?

These were all questions that needed to be answered and the business plan wasn’t a crystal ball with answers to these and other issues.  On the flight home from my parent’s house in Hilton Head Island, South Carolina on January 2, 2007, I made the decision to leave the practice of law and start Oskeim Sports Consulting, LLC.

After hiring a web design firm and filing the requisite paperwork to legally form a limited liability company, I launched Oskeim Sports in June of 2007.  Fast-forward ten years to June, 2017 and Oskeim Sports continues to flourish in the sports picks industry.

From receiving 32 awards from independent sports monitors to generating an unprecedented return on investment, my journey from behind an office desk to the front lines of selling sports picks has been a rewarding one.  To this day, I’ll never forget the look on the partner’s face when I told him I was leaving the law practice to start my own sports picks service.

His doubt and subsequent ridicule still drives me today.  I learned quickly the importance of using negativity as fuel to grow my business.  When a stranger asks if I am a bookie, I simply shake my head and smile.

In upcoming blog articles, I will write about my experiences from the day I established Oskeim Sports to current day.  From the fraud perpetrated by competitors to the stresses imposed on my family, you will get an inside look at what it’s like to own and operate a sports picks service. To get a great glimpse about my overall experience and this industry as a whole, view the video below.

Sports Handicappersv2 from Jeffrey Keim on Vimeo.