Hiring Guru: David R. Gray Jr. Multi-tasking Investments

A Chicago based lawyer, real estate investor and General Counsel to Wheeler Financial, a private investment company, David R. Gray Jr. founded his legal practice to focus primarily on legal matters concerning real estate, real estate taxation and civil litigation. Much of his work is representing investors like Wheeler Financial and servicing their investment portfolios. What makes this interesting is how David took something many would call boring or mundane and diversified to keep his own interest alive.


What is nature of the investments you manage?

"Real estate tax lien certificates purchased at county tax sales. These investments are complex but typically beneficial to all parties involved."

"County tax sales ensure local governments are able to efficiently collect their delinquent tax revenue and investors have an opportunity to obtain attractive risk adjusted returns. For the property owner, a tax lien sold to a private party is typically a much better option than any available loan and State law provides ample time to repay the amount owed."

What is it that keeps your interest in this industry?

"I enjoy the work because it's a combination of law, finance and real estate. I have spent the last 15 or so years working in this industry and have met countless numbers of people, from all walks of life. I take great pride in the numerous times I have been able to relate to people and take the time to work a deal out where the delinquent taxpayer can remain in their home while the investor maximizes its returns. These type of win-win resolutions are common for me but often overlooked by critics of the industry."

How/where can someone invest in tax sales?

"Every state has different laws concerning tax liens, but these kinds of sales -- county tax sales or otherwise -- occur with relative frequency and are announced by local government well in advance. Potential investors should exercise caution in seeking to purchase tax liens, just as they would with any other investment. After obtaining a tax lien it is crucial the investor have proper portfolio servicing and management. Tax liens require active and specialized asset management which is something I have specialized in over some 15 years."

How important is it to keep personally connected to the process of procuring new talent/personnel for your team?

"Extremely. An appropriate hiring process is the backbone of strategic planning for any organization and the process should be tailored to the job. For example, a hiring process for a legal position will involve different details than a process for a financial position because different skills and knowledge are required. We go to great lengths for our investors and clients, so it is absolutely necessary to ensure we put together the best possible group of professionals."

What are your thoughts about hiring and employment?

"Obviously I need to spend time with the candidate and I will involve others as well to get different perspectives. I look for candidates with a positive attitude, motivation, people skills and personal responsibility. Due to the unique nature of my work, I invest a great deal of time training a new hire. It is therefore vital to ensure I am bringing in the right person."

"I have learned a great deal about leadership over the years. One thing I've learned is the health of a team starts with the health of its leader. If the leader demonstrates strong character and values, he will attract people who have similar qualities. The best leaders lead by example and influence others to be their best."

Best interview question you have asked?

"Probably, "why do you want to work here?" Finding the true motivation of the candidate is critical. I want people on my team who are motivated to help others and develop themselves, not ones who have self-serving agendas. If the candidate is currently employed, I will ask why they want to leave."

Any hilarious, or conversely, horrifying interview stories?

"Not that I wish to share. (Writer's note: Attorneys never answer this question!) Generally, candidates and new hires are on their best behavior at first. It's only after a few months of employment when their true colors come out. This is why a longer process is necessary and why I seek to attract those with strong character and ambition. I look for people who want to improve themselves day after day. Once an employee has been trained and has settled in, my role is to encourage and support them in their purpose."

What has driven you in building personal success?

"Success? How do you define success? I don't define it in terms of money or power like others do. Success to me is about achieving goals, improving every day and finding satisfaction and happiness in life. Success is about positively influencing the people we interact with. This is a lifelong process. I take my career very seriously and work very hard. Many people, from my clients, business partners, employees and family depend on me to be at the top of my game. For me to do that, I need great people with great attitudes on my team. I have always been very generous in sharing my specialized knowledge with the legal community. Perhaps someday I would like to slow my practice down and teach; but not today."