David R. Gray Jr.

The founder of The Law Offices of David R. Gray, Jr., Ltd., and an active investor in the Chicago real estate market, David R. Gray is an attorney and a member in good standing with the Chicago Bar Association and the Illinois State Bar Association. Despite frequently representing clients as both plaintiff and defendant in trial and appellate court through his private practice, Mr. Gray also represents Wheeler Financial, Inc., as its General Counsel. Specializing in all facets of real estate, including taxation, litigation and appeals, Mr. Gray’s expertise in this specific area of the law is well known and greatly respected throughout the region.

The former chairman of the Chicago Bar Association’s Real Estate Taxation Committee, Mr. Gray put his expertise to good use by serving as the co-author for two chapters of the Illinois Institute of Continuing Legal Education Real Estate Taxation Handbook. A graduate of Valparaiso University School of Law who also holds an undergraduate degree in philosophy from the College of Charleston, Mr. Gray is frequently sought after for speaking engagements and has long been a contributor to a variety of programs made possible through the Chicago Bar Association, including its CLE programs.

Where did the idea for The Law Offices of David R. Gray, Jr., Ltd., come from?

My father practiced law in Chicago for over 50 years, so I knew very early on that I wanted to pursue a legal career and that I would like to do so by going into private practice.

What does your typical day look like and how do you make it productive?

While every day and every client is entirely unique, most days start with county tax court in the morning followed by an afternoon spent in the office to work on my caseload or to handle closings. As for remaining highly productive day after day, there is no better motivation than the thought of returning home to my wife and son once my workday has come to a close.

How do you bring ideas to life?

I like to think of myself as a man of action, so I make every effort to immediately bring an idea to life rather than waiting for it to take shape in my mind or trying to talk it out over a lengthy period of time. I like to be diligent and prefer to get right to work on making things happen.

What’s one trend that really excites you?

In terms of real estate investing, I feel like there is a burgeoning trend that could make private lending a potentially game-changing option.

What is one habit of yours that makes you more productive as an entrepreneur?

As much as I like to take immediate action, I also understand the value of collaboration. This balance has been critical to my continued success and productivity in every one of my professional endeavors.

What was the worst job you ever had and what did you learn from it?

There have actually been quite a few over the years. I worked as a dishwasher and waited tables in a restaurant, and I was also involved in sales for a period of time. These experiences enabled me to have a better sense of how people often have their own way of doing things and require a leader who understands how to get the most out of them despite the differences in their approach.

If you were to start again, what would you do differently?

Every mistake I have made has played a role in shaping who I am today, so I wouldn’t change a thing even if I could.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

A lot of people look to me for my expertise in real estate law, but that does not mean there is nothing more for me to learn on the subject. I am always looking for ways to expand my knowledge and understanding of all subjects, and I feel this has been a central component of my professional success.

What is one strategy that has helped you grow your business? Please explain how.

I stay very active in the field and try to contribute to enhancing the knowledge base of those in the community. By doing this, I feel that the community is enriched by the information I provide and subsequently become more aware of the fact that my firm understands the nuances and subtleties regarding this area of the law.

What is one failure you had as an entrepreneur, and how did you overcome it?

Just like any other entrepreneur, I have made a lot of mistakes along the way. The key is to learn how to “fail forward,” as this will ensure that something positive comes out of any mistake that is made.

What is one business idea that you’re willing to give away to our readers?

I believe in taking copious notes throughout every meeting, and while I actually enjoy this, many of my peers do not. I feel that a note-taking service targeted to legal professionals would be an excellent idea.

What is the best $100 you recently spent? What and why?

I took my son to see the Bulls play the Warriors at the United Center. We had great seats and had a wonderful time together even though the Bulls weren’t able to get the win.

What software and web services do you use? What do you love about them?

I tend to rely on hand-written notes, but my office staff has set up a program that makes transferring my notes to a digital file incredibly easy.

What is the one book that you recommend our community should read and why?

Flourish: A Visionary New Understanding of Happiness and Well-Being,” by Martin Seligman. The premise of the book is that a meaningful professional life stems from succeeding in the face of difficult circumstances and not in the accumulation of wealth. This is why entrepreneurial pursuits are often the most rewarding endeavors.

What people have influenced your thinking and might be of interest to others?

My father, an attorney who practiced law for over 50 years, has been a major influence on my life. Martin Seligman, the author of the aforementioned book, has also had an influence on the way I approach my professional work.


David Gray on LinkedIn: