James Regas

There is no way I could bring ideas to the forefront unless I had conceived or had laid out a written plan. Not only did it give me a chance to create goals and timelines to reach these goals, but it gave me a sense of what exactly I needed to do and how I would go about doing it.


Equipped with an extensive range of legal expertise, James A. Regas has made a name for himself over the course of a 60-year career as a prominent Chicago attorney. Having founded Regas, Frezados, and Dallas LLP, he aims to be the voice for individuals unable to fight for their own rights. With an abundance of resources and a firm of qualified professionals, James A. Regas has received recognition by the organized bar.

However, despite his legal success, James has also pursued various philanthropic endeavors, dedicating his career to improving the lives of Chicago residents in more ways than one. James Regas was a recipient of the Brotherhood Award from the Chicago Conference of Brotherhood for his efforts with the Hyde Park Community Hospital. Initially operating a private care facility under the name of the Illinois Central Railroad Hospital, the building was transformed into a not for profit community hospital that caters to minority populations in the surrounding area.

James is also an active member of the Chicago Greek Community and is an acting president of both the National and United Hellenic American Congress and Hellenic Bar Association. James Regas has proven himself indispensable in preserving and integrating Greek heritage into America and has taken on a multitude of projects including organizing the renovation of the Greek Delta neighborhood of Chicago. For his exemplary work for the Greek community, Mr. Regas has been awarded many accolades, including the very prestigious Urbs in Horto Award from the city of Chicago.

James A. Regas also worked extensively with the Western Policy Center, a Washington-based think tank, as its chairman. Eventually merging with the Woodrow Wilson International Center for Scholars, the Western Policy Center focused on crafting a forum for discussion regarding American policy in the Mediterranean and Balkan regions. Among his other titles and achievements, Mr. Regas also worked as the Chairman of the Board of the Western Springs National Bank and served proudly in a number of civic and religious organizations. Mr. Regas also received the Ellis Island Medal of Honor for his community endeavors. Despite his extensive volunteer endeavors, James A. Regas remains a dedicated husband and father and continues to cultivate positivity and support in his community.

Where did the idea for your law firm come from?

It wasn’t so much an idea as it was a passion for helping others who do not have a voice. Whether it was my work in Regas, Frezados & Dallas LLP or my many charitable endeavors, my goal was to be a voice for disadvantaged people and to help them in any way I could.

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

Before I retired, my typical day started by organizing my tasks by their importance and when they had to be completed. I would then go down the list until I was finished for the day. The paralegals at my firm were very helpful and worked to alleviate the heavy workload. We had clients that ranged from small business owners to corporate titans and the workload reflected our heavy caseloads.

How do you bring ideas to life?

I do a lot of planning and research and then execute the ideas. Before my retirement, I juggled several projects and new ideas at once. There is no way I could bring them to the forefront unless I had conceived or had laid out a written plan. Not only did it give me a chance to create goals and timelines to reach these goals, but it gave me a sense of what exactly I needed to do and how I would go about doing it.

What’s one trend that excites you?

I had run into a few attorneys that I once collaborated with, and they were telling me about Machine Learning. It’s essentially cut research time in half. It also helps us to create better cost estimates for each client. Not only does this trend save attorneys a lot of time, but it also makes them far more efficient. I am all about efficiency in everything I do.

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

Trying to maximize efficiency in everything I do has proven to be very effective. Remaining organized and adhering to a specific schedule is an excellent way of creating a routine. Self-discipline is essential and although results may vary depending on the individual, there are many ways to be productive.

What advice would you give your younger self?

I’d say to try and take more time for myself, rather than working so many hours each day. Before I retired from my law firm and from the various organizations I was a part of, I was working well over 60 hours per week. After a while, work like this burns a person out. While I don’t regret the hard work that I put into my many projects, it’s always important to strike a good balance between one’s work life and personal life.

Tell us something that’s true that almost nobody agrees with you on?

Deciding to undertake my work with the Hyde Park Community Hospital definitely had people thinking I was in over my head. I had a vision of what I wanted to do going into the project and I didn’t let anything deter me. When you surround yourself with hard-working, intelligent individuals, anything is possible.

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

I’ve done a lot of different things that have helped me over the years in terms of making my business ventures healthy and prosperous. There is a saying about how dreamers dream, but successful people execute those dreams and make them a reality. I am always validating my ideas and testing out ways I can make these ideas feasible for the masses. I put a lot of research into whatever I do so I can find the best method of making my ideas a reality.

What is one strategy that has helped you grow your business?

I had built quite a positive reputation for myself amongst the community with my various civic and religious endeavours, so people already knew they could trust me and my business. Word travels fast, too, so our successes in the courtroom became well-known in and around Chicago.

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

All professions and/or businesses have setbacks. The key is to use these experiences as learning opportunities and to grow from them. There were always times when setbacks would cause brief moments of discouragement, but I always just kept going.

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

The best business idea that I can give to readers is to find something they are passionate about and work on that. You don’t want to undertake something that you don’t believe in because it really can make you less effective in the long run. However, when someone makes a profession out of something they enjoy, it doesn’t even feel like work most of the time.

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

I recently purchased several volumes of a series that chronicles the lives of history’s greatest leaders and thinkers. There’s a profound amount of wisdom that can be gained from reading about the lives of others, particularly individuals operating on a national or international scale.

What is one piece of software or a web service that helps you be productive? How do you use it?

There are a few pieces of software that I liked using when I practiced law. Of course, you had Microsoft Office Suite, which allowed us to write many various contracts and documents for our extensive client base. But another one we used frequently is Abacus Law, a case management system. This software was quite helpful in making sure that everything we needed to do was done promptly.

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

I am going to go with the classic ‘How to Win Friends And Influence People’, by Dan Carnegie. It was published in 1936 and is still popular almost a hundred years later. It teaches you how to take your ideas and express them in such a way that you eventually earn money from them. It helps with leadership skills and how to attract enthusiasm among individuals from the ground floor all the way to your company’s CEO and investors. So, if there is any book that your community should take a look at, this would be my top choice.

What is your favorite quote?

My favorite quote is something I live by every day, and it’s helped me tremendously. The quote is from Epicurus and goes “Being happy in your relationships does not develop courage. You gain it by facing challenging times and life-changing adversity.”Meaning without challenges in your life, you cannot develop the courage to overcome them.

Key learnings:

● Do a lot of planning and researching before attempting to execute your ideas.
● Maximize efficiency in your life to accomplish your goals.
● Facing challenges in life builds character and can shape you into a better, more courageous individual.