Lawyer-Alumni profile: Rob Shepherd (PoliSci/History ‘07, Quinnipiac Law ‘10)

This is the latest entry in our new series of profiles of lawyer-alumni, in which I ask attorneys to respond to questions about their career paths.  If you’re an alum who’d like to be profiled, please just send me an email.  You don’t have to still be practicing law!  In fact, it would be very helpful for prospective law students to hear not just from happy and successful attorneys, but also from those who have left practice, who are not as satisfied as they thought they would be, or who work in a law-related field without a law degree.  For more contacts with our lawyer-alumni, join the UMass Amherst Lawyer-Alumni and Pre-Law Network.

Rob Shepherd
Tax Associate
McGladrey LLP

What’s your current position and primary practice field(s)?
I am a tax associate at a large accounting firm in Stamford, Connecticut. At my current position I primarily work in the taxation area of high-net worth individuals. This means I generally try to cater to the tax needs of multimillionaires and even a few billionaires. Generally the focus is on estate and financial planning which often also brings in other areas of taxation ranging from corporate and partnership tax to non-profit and international issues.

How did you get here – what led you to this field and practice setting?
I wanted to be an attorney since the age of nine. Initially I was fascinated by the theoretical concepts of our governmental systems; namely their ability to delicately balance order and liberty. Unlicensed liberty obviously leads to chaos as it the ultimately permits the strongest to oppress the weakest and deprive them of the ability to actually exercise their own liberty. Conversely, however, the government should not focus too heavily on order or it will subsume liberty. Absent liberty, individuals will not advance society culturally, economically or technologically. So I saw the government, particularly in the democratic-republican system in place in the United States, as performing a pivotal role in trying to balance these two somewhat conflicting interests. I also believe that attorneys play an incredibly important part in this process as they are—as litigators, planners, jurists or legislators—intimately involved in maintaining this balancing process.

Unsurprisingly I decided to major in Political Science to further develop my interest in this role of the attorney while maintaining an eye toward law school. Courses like Constitutional History and Comparative Law with Professor Daniel Gordon and courses taught by Professor Jeffrey Sedgwick only further fueled my interest. I ultimately applied to a few law schools and attended the Quinnipiac University School of Law. At Quinnipiac I became conflicted between my interests in constitutional law, which directly focuses on maintenance of the balance between individual liberty and societal order, and contract law. My interest in contract law extended from my view that while ultimately subject to governmental made law, contractual agreements in a way were their own ordering system through which individuals attempted to retain maximized liberty. In entering into a contract, individuals give up some liberty—namely to do acts in violation of the contractual agreement—to obtain the benefit of a stable and orderly relationship between the other party to the contract in hopes of obtaining a—generally economic—benefit.

In pondering whether to focus more heavily on contract or constitutional law I realized that both are heavily guided by the acts and needs of businesses. To better understand this and, to hopefully provide better services to my future clients, I enrolled in Quinnipiac’s dual JD-MBA program. Going into my second year of law school I was required to take a basic Federal Income Tax course. Although I feared the class would bore me terribly, I actually found myself enamored with the subject as it uniquely combines both private and public ordering systems with a focus on the needs of businesses. It also helped that Quinnipiac, albeit small, has a particularly strong tax program. I became particularly interested in estate and gift taxation as it seems among the most politically driven areas of tax law as it is constantly changing and hence producing chaotic situations for clients attempting to plan. For instance, in 2010 the Federal estate tax rate was 0% and for 2013 it may raise as high as 55%!


Describe a typical day/week – what are the kinds of tasks you engage in on a regular basis?
Every day is completely different, which I love. However, this also means that I don’t really have a typical day or week. My work consists of a unique mixture of research, tax dispute resolution, tax planning and tax compliance. My research tasks range anywhere from something as small as finding something in the instructions to a particular tax form to researching complex information about estate planning tools. My tax dispute resolution primarily comes through correspondences with the Internal Revenue Service and State Departments of Revenue about audits or assessments with which the particular client disagrees. These can range anywhere in difficulty from notifying the IRS that it made an obvious error in calculation in assessing the client’s tax return to trying to resolve cases where a client’s identity was stolen and a fraudulent return filed on their behalf. Tax planning tasks primarily take the form of estate planning which often combines both research and compliance skills but goes further. Essentially I take a client’s circumstances and goals and work through research and calculations to determine the best way to reach those goals, generally passing assets to loved ones without incurring massive taxation. Compliance is mostly filling out tax returns. 

How many hours/week do you work? How’s that work/life balance thing working out for you?
Working in public accounting has an incredibly varied schedule. The hours used during our “busy season” stand in stark contrast from the hours the rest of the year. During the non-busy times of the year—about 6 months during the year—I usually get to work at about 8:30 am (after a 60-90 minute commute on the train and a 20 minute walk to work) and try to leave promptly at 5 pm so I can catch the last train until 7:30 pm (which gets me home at 9ish). Occasionally I am stuck at the office until 7:30 or even later (around 9). I generally don’t work weekends.

For the other 6 months, our “busy season,” I put in significantly more hours including on the weekends. The average weekday workday is about 8 am to 9 pm (plus the commute each way). On the weekends, employees are allowed to pick our own hours provided our work gets done so I generally work about 11 am to 11 pm on Saturdays. In theory, employees are entitled to at least one day off but I generally work Sundays as well. I think the longest I have ever been in the office during a busy season day was 8 am to 2am the next morning. A 18 hour workday may sound shocking (and to most people I am sure it is) but given the hours I put into law school, I really don’t find it to be a big deal.

Despite the tough hours though I do get very good paid time off; if you add together vacation time, sick time, holidays and bonus days off I could take from 5-6 weeks off during the year.

What do you like most about what you do?
I like how the type of work, particularly in planning, touches on many different areas and require you to use multiple different parts of your brain. While most jobs, particularly for attorneys, are reading and writing heavy some others are more numbers focused. Mine interestingly combines both and requires a thorough understanding of tax laws. All of this, of course requires constant learning which I love.

Where did you go to law school? What’s your favorite memory from law school?
I went to the Quinnipiac University School of Law. My favorite memory is when I found out I was going to have my journal article—What Roosevelt Thought: A Roughrider’s Guide to the USTEA, 23 Quinn. Prob. Law Jour. 311 (2010)— published. The excitement of being published, particularly in a legal journal, is unparalleled.

What did you major in at UMass? How has it been helpful to you in your law career?
I was a Political Science and History dual major. I also obtained a Certificate in International Relations from the Five College Consortium. I use the knowledge obtained from my studies from time to time but not very often. My political science background provides me insight into the workings of government and public policy which often provide context to existing and proposed tax laws and regulation. History also plays into this as well. Finally, although certainly used to a far lesser extent, a thorough knowledge of how nations relate to one another provides added context to tax treaties which are studied in doing international tax work.

What’s your favorite UMass memory?
Being in the greatest marching band in the world and getting to know its legendary leader, George N. Parks, very well.

Did you take time off before, during or after college? If so, what did you do?
No, I went straight through. I know many people feel like they gained a lot from working between undergraduate and law school. While I cannot personally attest to that I personally believe I did not miss out on much going straight from undergrad.

What non-law experiences have ended up being surprisingly useful to you in your legal career?
Not to be repetitive, however, the opportunity of being in the UMass Minuteman Marching Band has proven incredibly helpful to me. I learned more from my time in the band than perhaps any other experience. The band taught me leadership, communication, and organizational skills that I don’t believe I could have learned elsewhere but I use in my life on a daily basis. Beyond that, Mr. Parks instilled in his band members the importance of also making the most of every opportunity and treating people with the utmost of decency and respect. Additionally, the band further developed the importance of hard work and determination which served me significantly throughout law school.

Any choices along your career path that you particularly regret or are especially grateful for?
I am particularly grateful for my decision to take a significant number of writing courses at UMass. Although I tested out of the freshman writing requirement, I ended up taking three junior level writing courses, a course for my political science major and two history courses with significant writing components. The writing skills I learned in these courses, particularly the history courses, greatly aided me in law school and in my positions after graduating. Most individuals are poor writers. This is particularly true with my generation which is over reliant on spelling and grammar checking technology and too familiar with “text-messaging lingo.” To have an advantage in such a critical field provides significant opportunities and I highly recommend to anyone considering a professional career to take as many writing courses as possible.

If you couldn’t be a lawyer any more, what would you do? (Or: what’s your second career going to be?)
I would be a professor.  I would love the opportunity to teach as it would let me share my knowledge with students while also working on various research projects and publications. Additionally, like my current job, a professor must constantly learn and be abreast of changes in their field.

How do you respond when someone asks your advice about whether to go to law school?
That it really depends. There is already a significant over-saturation of attorneys in the market and diminishing opportunities to do well in the field. Regardless, too many people are going into the law with the expectation that they will eventually make a ton of money. I think that is a flawed view to take of legal education. As bad as the economy as a whole is right now, it is even worse for the legal field in particular. Far too many people think a JD instantly means a lot of money. It is for some attorneys, particularly those who go to a school like Harvard or Yale, but for the vast majority of attorneys it is not or at the very least is not true for a very long time. So for my basic response I generally pose a question: “If you could hypothetically go to law school for free but only if you agreed to make $0 from using your law degree during the rest of your life, would you still go?” If the answer is yes—likely because they want that intellectual challenge and to better understand the world—then by all means that person should go. If there is any hesitation or the answer is no, then they should very seriously think about whether they should go. The point is not that attorneys never make money but rather that I don’t believe it is proper in the current environment of legal employment for money to be a significant consideration in choosing whether to go to law school.

If you could have dinner with any lawyer, real or fictional, living or dead, who would it be and why?
James Madison, the father of the US Constitution, so I could ask him his thoughts on the development of constitutional precedent since implementation of the document.