David R. Gray, Jr. is the owner and founder of The Law Offices of David R. Gray, Jr., Ltd., a firm primarily focused on tax collection, enforcement litigation, civil litigation and a wide variety of legal issues relating to matters of real estate. In addition to the caseload he is tasked with handling through his own firm, Mr. Gray also serves as the General Counsel to Wheeler Financial, Inc., an investment company based out of Chicago, Illinois. With expansive and varied experience in trial and appellate court, Mr. Gray has represented clients involved in court proceedings as both the plaintiff and the defendant, and he has further represented clients in real estate transactional matters as well.
Mr. Gray is an active investor in the Chicago real estate market, utilizing his vast knowledge of the subtleties of real estate law to ensure a successful property investment portfolio. In fact, Mr. Gray’s expertise in real estate law is so widely respected that he was sought out to co-author several chapters of the Illinois Institute of Continuing Legal Education Real Estate Taxation Handbook, contributing his expertise to a chapter on tax bills and payments along with an additional chapter covering tax deed and indemnity fund proceedings.
Holding an undergraduate degree in philosophy from the College of Charleston and a law degree from Valparaiso University School of Law, Mr. Gray formerly served as the chairman of the Chicago Bar Association’s Real Estate Taxation Committee and remains a member of both the Chicago Bar Association and the Illinois State Bar Association.
How did you get started? What inspired you to start this business?
My father enjoyed a lengthy and successful career as an attorney, so I was already deeply interested in a career in the legal field. After studying philosophy at the College of Charleston, my interest in law became even deeper and reinforced my desire to pursue a career as a lawyer and to eventually start my own private practice.
How do you make money?
Mainly through my work at The Law Offices of David R. Gray, Jr. Ltd., but I also serve as the General Counsel to Wheeler Financial and maintain a healthy interest in real estate investing.
How long did it take for you to become profitable?
It took a bit longer than I had initially hoped, but I made sure to have a contingency plan in place in case profitability was not achieved within the timeframe I had originally planned.
When you were starting out, was there ever a time you doubted it would work? If so, how did you handle that?
My father had a long career in law and was an experienced real estate investor, so whenever I had any doubts I could easily seek his advice and restore my sense of self-confidence.
How did you get your first customer?
My first client actually sought me out after seeing the firm’s services advertised locally.
What is one marketing strategy (other than referrals) that you’re using that works really well to generate new business?
I stay involved in real estate investing and serve in a variety of roles related to real estate law, so people in the area are quite familiar with my work and are aware of my expertise in this particular area of legal practice.
What is the toughest decision you’ve had to make in the last few months?
As a practicing attorney, there are very few days when I am not faced with a tough decision. I simply make sure to approach each decision from a pragmatic point of view and ensure that I collaborate with others to arrive at the best course of action.
What do you think it is that makes you successful?
I truly enjoy what I do, and for that I am extremely grateful.
What has been your most satisfying moment in business?
I experience a tremendous sense of joy whenever I am able to achieve a favorable outcome for any client I am representing.
What does the future hold for your business? What are you most excited about?
There is a lot of room for growth for the law firm and for my real estate investments, so there is a lot to look forward to in the future.
Who has been your greatest influence in terms of your professional endeavors?
I am quite fortunate to have studied under many great attorneys and educators over the years, but no one has had a greater impact on my career than my father, who practiced law in Chicago for over 50 years.