Paula Calimafde

The Heart of Law

Almost every evening at dinner, Paula Calimafde’s father would turn their dining room into a courtroom. A renowned litigator, he would “present” the case he was working on to his two daughters, and then ask them specific questions as if they were the judge or jury.  “I recall he was working on a mine explosion case, where the mining company had wanted to increase its productivity, causing the machines to overheat. The workers had been told to override the safety feature,” she remembers today. “He would ask us if we thought it was reasonable for a worker to turn off the safety switch even though there was a red sign over it that warned the user not to switch it off unless the entire machine was off.  Dad figured if he could explain a complex case to us, or see how we reacted to a set of facts, he would probably do okay with a jury.”

A decade later, Paula began law school at Catholic University in Washington, D.C., and realized she had already been taught most of the material. “I found myself thinking, ‘I know all of this already because my father spent fifteen years teaching it to me, and I didn’t even realize it at the time,” she recalls. “It gave me such an advantage. I understood so much and was able to enjoy law school rather than struggle through it. It really made me grateful to have grown up that way.”

Paula has since become a tax attorney and is now a Principal at Paley Rothman, the largest firm of estate planning attorneys in Montgomery County. Paley Rothman is a full service, primarily business-oriented law firm with tremendous capacity in commercial litigation, employment law, employee benefits, project development, real estate and tax.  She currently chairs the firm’s Retirement Plans, Employee Benefits, and Government Relations practice groups, and is a senior member of the Estate Planning, Tax, and Nonprofit groups. She has been nationally recognized on the “Best Lawyers of America” list, “SuperLawyers,” is a charter member of the American College of Employee Benefits Counsel, and is a member of the American College of Tax Counsel and the American College of Trust and Estate Counsel.  Being a member of all three Colleges places her in a very select group of attorneys in the country.  She also serves as the Chair of the Small Business Council of America and is the President and General Counsel of the Small Business Legislative Council. She spends a portion of her time lobbying, but focuses more on education through position papers and testifying before the Ways and Means, Finance and Small Business Committees on Capitol Hill.

Paula began working at Paley Rothman almost immediately after graduating from law school when it was still a small firm of only five people. It was founded about forty years ago by Steve Paley and Mark Rothman, who met at the Justice Department. They decided to start their own firm together, and since Montgomery County did not yet have any tax lawyers, they selected a location in Chevy Chase to open shop.

Today, the firm has 37 attorneys, all of whom work collaboratively in a collegial company culture. “I feel extremely proud to be a part of the Paley Rothman team, where I have been able to play an instrumental role in helping our clients accumulate wealth and keep that wealth in a tax-advantageous way,” she explains. “We help our clients maintain their wealth as much as possible during their lifetime, and at the time of their death, we preserve as much of that wealth as possible for their family or for other beneficiaries or charities they so desire.”

In many ways, Paula seems to have been born for her career, as her parents immersed her in law and politics from an early age. She grew up in Old Greenwich, Connecticut, where she and her younger sister experienced a happy, carefree childhood. Her father was an intellectual property litigation attorney who instilled in his daughters an understanding that there was nothing they couldn’t accomplish. “He always encouraged me to take risks,” she recalls. “He would constantly urge me to go as far as I could and never to let fear stop me. I think he recognized my ambition early on and wanted to nurture it as much as possible.”

Fortunately, Paula did not need much encouragement when it came to academics. As a child, she loved going to school and made excellent grades. Her mother, who stayed at home, was fiercely political, serving as town representative and being active in the League of Women Voters. Her parents’ influence inspired Paula to dream big—at age three, she would often tell adults that she wanted to be the President of the United States one day. “My mother was a very strict, strong woman, and she taught me that no one can intimidate me,” she recalls.

The encouragement she received from her parents was reinforced by the people she met growing up. Her father represented a major Japanese electric company, so the family traveled to Japan and met the heads of the corporation when Paula was a teenager. “We were exposed to many people who were highly successful at an earlier age than most,” she says. “Being in that environment with those kinds of people to look up to was very defining.”

Paula attended Swarthmore College for her undergraduate education, where she majored in political science. She decided to enroll at Catholic University for law school.  “I’ve always loved D.C.,” she recalls. “I thought it offered everything. Of course, politics was in the back of my mind, as I wanted to play within that arena as well.”

During high school, Paula spent a summer in New York City working at her father’s law firm. She enjoyed the experience, but decided early on that neither New York City nor intellectual property law was for her.  This led her to Washington, D.C., where, at Catholic University, she had a professor who had just come out of working for the IRS with an impressive background in tax and corporate reorganizations. However, he had little experience teaching law students, so he approached the class at a much higher level than he probably should have. “A lot of people in class had no idea what he was talking about, but I really enjoyed it,” she recalls. “I realized this was the area of law for me.  I really like the intellectual kind of competition, but in a clean way where no one is getting hurt.”

When she graduated in 1976, Paula began working with Steve Paley at Paley Rothman. She remembers her first assignment was a reorganization of a privately owned business. “I had friends working on Wall Street who were doing corporate minutes for several years, whereas we had paralegals to do that for us,” she recalls. “The fact that I chose to work at a small firm allowed me to jumpstart my career and do complex and interesting work early on.”

In 1986, Paula was selected as one of twelve commissioners for the White House Conference on Small Business, where she chaired the section dealing with social security, retirement plans, and health care. It was her first opportunity to work with the Small Business Administration, and in particular, the Chief Counsel at the Office of Advocacy, which assists small businesses on the Hill and with regulatory matters.  She found she had a natural ease for talking with people and understanding the politics around the issues. “I had never given a speech in front of two thousand people before,” she says. “The first time I did that, I felt like I had cotton in my mouth, but eventually I grew very comfortable giving speeches. I’m fortunate to have the skills necessary to work with disparate groups of people and find viable compromises.”

Most recently, Paula has accepted the position of President and General Counsel of the Small Business Legislative Council, a large non-profit trade association that represents a variety of small business trade associations on Capitol Hill. “They represent an extremely diverse population, including associations representing those in construction, florists, petroleum distributors, electrical contractors, transportation infrastructure, printing, and so on,” she says. “You have all these CEOs sitting around the table, discussing their issues and trying to agree upon an agenda that everyone feels comfortable with. It’s a very powerful, permanent coalition of trade associations.” She also serves as the Chair of the Small Business Council of America, which gives a voice to successful and stable small businesses throughout the country. The SBCA focuses exclusively on complex tax, employee benefits and health care issues that impact its members.

The Small Business Council of America has a business and legal advisory board comprised of professionals from around the country who specialize in and work with privately owned businesses, which can consist of small businesses or large family-owned companies.  When an agenda is agreed upon, it meets with members of Congress and their staff to discuss its proposals. “If we are successful, we’re able to turn an idea into a law to make life easier for small business.  Often, we work to simplify the law and reduce administrative or unnecessary burdens,” Paula explains. When the Small Business Council of America is not proposing new laws, it defends existing ones on the Hill that assist privately owned businesses, like those pertaining to retirement plans. “It’s very easy to explain why I chose to join and represent the SBCA. I am able to work to make the law better for small or privately-owned businesses, and we see results,” she explains. “It’s very rewarding to look at a tax code section and realize that you helped bring it into being. It’s a positive experience.”

Paula’s new position with the Small Business Legislative Council seems to be a perfect fit, considering her technical expertise in small and privately owned business taxation as well as corporate structure, qualified retirement plans, estate planning, and executive compensation. “I actually work in these fields, so when I go to Capitol Hill to speak to members or to testify, I’m not relying on a script that someone else has written,” she explains. “When you actually do what you are talking about on the Hill, people sort of wake up and pay attention a bit more because they know they’re talking to someone who’s in the trenches. They know that what I’m telling them is from my experience, so it’s going to be relevant.”

Since taking on her new role as President of the Small Business Legislative Council, Paula has had the opportunity to refine her leadership style towards a more collaborative effort. “My alma mater, Swarthmore College, is a Quaker school, and it taught me to work on an issue until a consensus has been reached by everyone involved,” she explains. “That’s the style of leadership I prefer. In the lobbying world, I’ve learned that today’s friends will be tomorrow’s enemies and then, at some point, friends again. Whatever you say will eventually get around to that person, so I try to sit down with people when a problem arises and deal with the issues right away. It’s so much more appropriate to deal with issues head on and up front.”

Paula’s husband, Alan Mark, is also a Principal at Paley Rothman, focusing on finance, project development, and biotech. They met when a fellow Paley Rothman partner set them up on a blind date years before Alan joined the firm, and the two immediately hit it off. “He’s only a few years older than me, but he’s been a great mentor for me,” she says. “He is a phenomenal lawyer and has been known to close deals that seem to present insurmountable issues. We decided early on that we would only talk about law at home if something in our legal life was really important. We knew if we didn’t do that we would end up only talking about the law and our jobs. We didn’t want a relationship entirely dominated by the law. We enjoy each other’s success, but our practices seldom overlap, even though we work in the same firm.” When she and Alan are not in the office, they put family first, often traveling with their children and doting on their grandchildren.

As she shifts her gaze forward, the future looks bright, having spent a lifetime working toward her passions and building upon the foundation her parents instilled in her. “I can imagine most people would think sitting around all day doing taxes would be boring, but I don’t see it that way,” she says. “I’ve been fortunate to have very interesting clients. They are intellectually exciting and passionate, writing books and discovering new cures, so it’s a really exciting way to practice law. You begin to care for your clients as friends or family, so caring about their best interest occurs naturally because for me, family has always come first.” Indeed, having enjoyed a life where family, law, and lawmaking are sown together seamlessly, Paula’s success comes from the heart as much as it comes from intellect and experience, lending it a rare and genuine nuance that is not soon forgotten.

Paula Calimafde

Gordon J Bernhardt


President and founder of Bernhardt Wealth Management and author of Profiles in Success: Inspiration from Executive Leaders in the Washington D.C. Area. Gordon provides financial planning and wealth management services to affluent individuals, families and business owners throughout the Washington, DC area. Since establishing his firm in 1994, he and his team have been focused on providing high quality service and independent financial advice to help clients make informed decisions about their money.

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