Paul Donovan: “Be passionate about what you do”

Be passionate about what you do. People may wonder how I can be passionate about tax law. My father always told me that since you must do something every day, you might as well do it with passion. If you do, the day goes by faster, you will have more satisfaction with your work, and […]

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Be passionate about what you do. People may wonder how I can be passionate about tax law. My father always told me that since you must do something every day, you might as well do it with passion. If you do, the day goes by faster, you will have more satisfaction with your work, and you will be more successful. He was right.


The legal field is known to be extremely competitive. Lawyers are often smart, ambitious, and highly educated. That being said, what does it take to stand out and become a “Top Lawyer” in your specific field of law? In this interview series called “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law”, we are talking to top lawyers who share what it takes to excel and stand out in your industry.

As a part of this interview series, I had the pleasure of interviewing Paul Donovan.

Paul Donovan has been a lawyer and CPA for over 25 years. He worked with the “Big Four” for many years, structuring multi-national real estate transactions for Fortune 500 companies and wealthy investors. Paul recently moved his practice to South Florida, and there he advises clients on domestic and international real estate development and investment tax matters.


Thank you so much for joining us in this interview series. Before we dig in, our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law? Did you want to be an attorney “when you grew up”?

Practicing law runs in my family. It started when my grandfather decided to forego a boxing career to start a family and work in the Suffolk County District Attorney’s office in Boston. After work, my grandfather would bring home court transcripts for my father to read. My Dad fell in love with the law, and after serving his country in World War II, he practiced law in Boston for over 50 years.

In high school, my father asked me what I wanted to do for a career, and I told him I wanted to follow in his footsteps and practice law. He advised me to specialize if I wanted to practice law. Because I was good at math, we decided I should specialize in tax law. I studied finance and accounting in college, became a CPA, and then went to law school. Early in my career, I developed a passion for real estate and have focused on that industry throughout my career.

Can you tell us a bit about the nature of your practice and what you focus on?

Most of my practice is transactional. I assist real estate development and investment clients and structure and execute their deals in a tax-efficient manner.

You are a successful attorney. Which three character traits do you think were most instrumental to your success? What unique qualities do you have that others may not? Can you please share a story or example for each?

One quality that separates me from other tax attorneys is that I am a CPA and a lawyer. Most lawyers enter the profession because they don’t like math. However, to be a top tax lawyer, you must have the “bi-lingual” ability to speak numbers and words. I’ve always had good math and accounting skills. Also, tax lawyers share the stage with tax accountants. The relationship between the two professions can be contentious, similar to the relationship between architects and builders. Being both a lawyer and a CPA allows me to communicate more easily with both. It also gives me “visibility” on how my tax planning should be executed and reported to tax authorities.

Another trait is that I am a tenacious researcher, and I’m always willing to out-hustle the other side by digging deeper into the facts and the law of an issue.

Lastly, clients have told me that my people skills stand out in a field of law that is notoriously filled with some dry personalities. Clients prefer to hire attorneys they know, trust, and like. It is easier to get to know a client and gain their trust if you have good people skills. Clients are human and want to know that you are human too.

Do you think you have had luck in your success? Can you explain what you mean?

To me, luck is being prepared for when opportunity knocks. Opportunity is everywhere in every business, and if you’re not ready to take advantage of that opportunity, you will miss it. My first big opportunity came when I represented a developer of a new townhouse development in downtown Boston. The entitlement process was contentious with the city. However, we were able to secure all the necessary permits and financing. Before that, I spent several years studying the real estate industry and the tax issues involved therein. When the opportunity came knocking, I was ready to open the door.

Do you think where you went to school has any bearing on your success? How important is it for a lawyer to go to a top-tier school?

Where you go to law school has little influence on whether you will be a good lawyer. However, there is no question that where you go to law school will significantly influence the number and type of opportunities available to you as a lawyer. Top-tier law schools are tribal echo chambers. Their graduates protect their own and generally only offer opportunities to other graduates from top-tier law schools.

If you didn’t attend a top-tier school the best way to combat this bias is through success. The more success you have in practice, the less critical your diploma becomes.

Based on the lessons you have learned from your experience, if you could go back in time and speak to your twenty-year-old self, what would you say? Would you do anything differently?

If I could talk to my 20-year-old self, I would tell him to start networking immediately. It is never too early to start building your brand, and you will never have a bigger audience with whom to do that than when you are in school.

This is not easy work. What is your primary motivation and drive behind the work that you do?

My clients and my family are my primary motivation. Both depend on me to do my job well.

What are some of the most interesting or exciting projects you are working on now?

I am currently advising a client on structuring a US-based real estate investment and development company. I am also advising a client on forming an “Opportunity Zone” for low-income housing.

Where do you go from here? Where do you aim to be in the next chapter of your career?

From here, I hope to build out a small boutique firm that will embrace new technology, enabling us to work for anyone in the world from anywhere in the world.

Without sharing anything confidential, can you please share your most successful “war story”? Can you share the funniest?

My most successful war story has nothing to do with tax law. I accepted a pro bono criminal matter involving a juvenile convicted of first-degree murder and sentenced to prison for life without the possibility of parole even though he killed nobody. There was intense media coverage of the case, and I was a tax attorney involved in a high-profile criminal case with no previous criminal experience. Nonetheless, we appealed his conviction based on recent Supreme court rulings and secured his release. My client spent over twenty years in prison for a murder he did not commit and was one of the first juvenile prisoners released applying the new Supreme Court rulings. The case has been the subject of several local and national television documentaries, newspaper articles and may also become the subject of a book. To say it was the most gratifying moment of my career would be an understatement.

The funniest story came from the same case. I went to visit my client in prison. As I entered the facility, I had to walk by the yard where several inmates gathered. As I walked by, I endured several rounds of whistles and catcalls. I started laughing and looked over at the inmates, and they were laughing as well. It was a moment of levity in an otherwise serious matter.

Ok, fantastic. Let’s now shift to discussing some advice for aspiring lawyers. Do you work remotely? Onsite? Or Hybrid? What do you think will be the future of how law offices operate? What do you prefer? Can you please explain what you mean?

I use a hybrid method. I have a system that allows me to be in an office any day I choose or to work remotely. Thus, I use support staff who work remotely as well.

The “law office” concept will be forever transformed as more attorneys choose to work remotely. Recently, one of the “Big Four” accounting firms announced that it will give all 55,000 employees the option to work remotely. The “Big Four” hire more tax attorneys than any other law firm in the world. This announcement will have a ripple effect across the entire professional service industry.

How has the legal world changed since COVID? How do you think it might change in the near future? Can you explain what you mean?

The legal profession is notoriously slow to adapt to technology. However, the legal world has changed dramatically since the beginning of covid, and the changes are here to stay. In litigation, depositions, hearings, exchange of discovery materials are all conducted online now. Courts conduct civil and criminal trials online more frequently, and judges can clear their dockets much more quickly.

Because it is easier for lawyers to work remotely, the cross-jurisdictional practice of law has become prevalent. Soon you will see more states enter into reciprocal admission agreements to accommodate the online cross-jurisdictional practice of law.

We often hear about the importance of networking and getting referrals. Is this still true today? Has the nature of networking changed or has its importance changed? Can you explain what you mean?

Tax law is still a referral business. Many companies offer law firm advertising services. Most of these services cater to high volume practices such as personal injury law. However, tax law is a very specialized field. People don’t feel comfortable hiring a tax attorney from a cold call.

Based on your experience, how can attorneys effectively leverage social media to build their practice?

For tax lawyers, social media can be helpful to demonstrate your knowledge and status in the field. I like to use Twitter to keep existing clients current on tax law developments and show my expertise to potential new clients.

Excellent. Here is the main question of our interview. What are your “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law?” Please share a story or an example for each.

  1. Be passionate about what you do. People may wonder how I can be passionate about tax law. My father always told me that since you must do something every day, you might as well do it with passion. If you do, the day goes by faster, you will have more satisfaction with your work, and you will be more successful. He was right.
  2. Work hard. It may seem axiomatic, but to be a successful lawyer, you must resign yourself to working hard and persevering through a daily minefield of problems, each of which can derail a client matter. There are no shortcuts.
  3. Do your own research. My father advised me never to rely on someone else’s research and be skeptical of “expert” opinions. Experts often become lazy and rely on their reputations. This advice has helped me tremendously throughout my career, and I have often taken tax positions contrary to the experts favorable to my clients that were proven correct.
  4. Love your family. To be successful in any profession, you need motivation. Nothing motivates me more than my family, and practicing law is the conduit through which I provide for them.
  5. Play golf on Sundays. Practicing law is hard and practicing tax law is exponentially hard. It would help if you tried to take a break from it at least once a week. For my father and me, that break was Sunday morning golf. (He won all the time.)

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might see this. 🙂

There are many such as Justice Anthony Kennedy, Larry Bird, or any one of the living presidents. However, if I had to pick one, it would be Jamie Dimon. To me, he understands the world’s interconnectivity better than anyone and has a vision for where the world is heading legally, socially, politically, and financially.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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