Why I Left A Successful Law Practice to Become a Sports Handicapper

Aug 25, 2015


One of the most common questions I get from prospective clients and strangers alike is, “why did you leave the practice of law to become a professional sports handicapper.”  The underlying tone of the inquiry is one of surprise and bewilderment, which is not surprising as the thought of giving up a successful career to pursue the unknown is too difficult for many to understand.

Ironically, I am a risk-averse person by nature so I appreciate the confused, perplexed and suspicious reactions from people when they first learn of my professional background.  But, the appeal of entrepreneurship was too strong to ignore, and the passion I had for sports handicapping and sports analytics was too ingrained in who I had become.

For those who don’t know my background, I graduated from the University of Connecticut School of Law in 2000 and was hired by a private litigation firm shortly thereafter.  I moved from Hartford, Connecticut to Fairfield County and started what turned out to be a very fulfilling and successful law career.

My seven years of practice were certainly rewarding – helping clients in need and advancing the interests of justice were two upsides to being an attorney.  I forged relationships inside the courtroom that helped me become a better person, not just a better advocate.  I was also fortunate enough to practice alongside some of the best attorneys in the state, and I will always be grateful for their mentorship and friendship.

I had no intention of becoming a professional sports handicapper; I simply enjoyed analyzing the games and generating a return on investment on a recreational basis. Helping fellow sports bettors put a few extra bucks in their pockets was also fulfilling.

I had enjoyed success handicapping sports (and investing on my own advice) for many years prior to 2007.  That success allowed me to organically develop a significant following on various sports handicapping forums where I posted my sports picks for free.

However, balancing the demands of my full-time job as an attorney with my recreational enjoyment of sports handicapping became too onerous.  My girlfriend at the time (and now my wife of 7+ years) was extremely understanding, but she deserved more and I knew it. My sleep schedule became nearly non-existent and the stress of balancing everything in my life became untenable.

In short, a decision had to be made, and it had to be made immediately.  I had reached the proverbial fork in the road that required a decision that would define the next chapter of my life.  Leaving the law firm that took a chance on me fresh out of law school and ultimately cultivated my legal career was a difficult decision.

In fact, it was one of the most difficult decisions I have faced in my life.  But, the undeniable passion I had for both sports handicapping and sports analytics ruled the day.  The next chapter of my life was yet to be defined, and I was ready to begin writing that chapter without regret.

After discussing the options with my friends and family, I reached the conclusion that pursuing a professional career in sports handicapping was not only possible, but also doable.  And, so it began – the development of a business plan that included, among other things, state filings to create a legal entity (LLC), spending tens of thousands of dollars creating a website and making difficult financial decisions.

In June of 2007 I left the demanding billable-hour requirements behind and established my own sports investment firm – Oskeim Sports Consulting, LLC (hereinafter “Oskeim Sports”).  The goal was to provide sports bettors with a legitimate alternative to the countless handicapping sites that peddle false information, get-rich-quick schemes and, frankly, fraudulent sales tactics.

Oskeim Sports would present a new way of doing business in the handicapping industry, one in which was predicated upon honesty and integrity.  I created an industry-first Code of Conduct; I implemented industry-leading transparency by creating a pick archive where every sports pick is published shortly after each game starts; I promote a generous Rewards Program and Satisfaction Guarantee that cannot be found elsewhere in the pick-selling business; and I provide a fully-transparent Net Profit and Return on Investment section that emphasizes what matters most to a sports bettor – his or her bottom line.

When people learn about my career path and give me the “deer caught in headlights” look, I just smile knowing that my decision to establish Oskeim Sports was one of the best I had made in my life.