Carroll Hauptle

Righting the Boat

When Carroll Hauptle was asked to come to Berlin in 1977 to work on the production of Samuel Beckett’s one-act play, Krapp’s Last Tape, he was only 22 years old. There, he worked for Beckett himself, the Nobel Prize-winning playwright who had ushered in the breakthrough to modern drama. “I had no debt, no house, no car,” Carroll remembers today. “We did sixteen cities in thirty days, four performances apiece. We also later played the German international art festivals alongside troupes from Poland, Russia, Italy, Singapore—all over the world.”

Krapp’s Last Tape is a play that examines  remorse and frustration over the passage of time. As the 68-year-old protagonist listens to recordings of his former self, the audience witnesses a fragmentation of identity and a sense that life trends toward something unbearable. The arc of Carroll’s own life, however, bends with a different meaning, melding the pieces of his former experiences into a path paved smooth by his proclivity for fighting against entrenched injustices.

In his work as the founder of The Law Offices of Carroll Hauptle, the law has become an art form like the play productions of his youth. “With law, I do what I do because it presents an opportunity to use analytical, out-of-the-box thinking to create solutions for people and businesses,” he says today. “I see them as works of art. And in the very best cases, they give me the opportunity to “right the boat” and correct some of the world’s injustices.”

Launched in 1993, the firm’s bread and butter is estate planning, but it also takes on business formation and operations work for foreign clients looking to establish or expand their presence in the U.S. Its expertise spans transactions, real estate, copyright, trademark, human resources, and software licensing. “I occasionally litigate, but only if I know I’m going to win, and only if it has some aspect of righting the boat,” says Carroll. “We often use Rule 11 to seek sanctions against attorneys who bring frivolous lawsuits. I’ll never forget a case in 2002, when I was up against one of the biggest law firms in the U.S. and won a six-figure award for my client using that rule. I hope that the work I do makes people think twice about pursuing cases like that.”

Carroll’s heart, however, remains with estate planning, and the opportunities it affords to provide trusted counsel and advice to clients. Given his ability to see contrary positions, he has no problem navigating challenging dynamics to advocate for the best interests of all parties involved, whether working on the architecture of an estate’s setup, securing the future of a special needs child, or creating the best conditions for peace between siblings that don’t get along. “I get to step a little outside the basic lawyer role and give advice my clients might not be able to see otherwise, which can be the most valuable advice of all,” he says. “Even outside of estate planning, my strategy and inclinations run contrary to how most lawyers operate—often because, in my opinion, they’re focused on the wrong things. They tend to advise people not to take any risks. When other lawyers are telling a client why they can’t do something, I’m the one telling them they can if they are careful, and here’s how.”

These inclinations are reminiscent of his father, who remained extraordinarily compassionate and empathetic toward victims of societal injustice despite the outlooks of many of his acquaintances. His mother, as well, was recruited to be a CIA agent at a young age, and had a strong sense of principles and ethics. Carroll came of age amidst the Vietnam War era, which gave way to what many believed would be a new America—an opportunity to give people a better shot at life. “That era was all about righting the boat, and it helped to shape my worldview,” he says.

Carroll was born in Wilmington, Delaware, the second of four children in a Roman Catholic family. His mother’s family had arrived in America in the 1700s and had been given land near Chestertown by Leonard Calvert, the first governor of Maryland. She was Phi Beta Kappa at the University of Delaware, where she met Carroll’s father, a Delaware football player and coach who had served as a bomber pilot in the waning days of World War II. He graduated with a degree in engineering, and when they married, he took a sales job with a plastics company called Hercules, and then with DuPont.

Due to the nature of his father’s work, the family moved frequently throughout Carroll’s childhood, to the extent that he attended eight different elementary schools. He can still recall the wonderful stone house his mother found for them in Vero Beach, Florida, with Spanish marble floors and two miles of private beach.

The family returned to Delaware for a brief stint and then moved to Hingham, Massachusetts, where they found stability and community over the next three years. “It was a beautiful town—an ideal New England hamlet with wonderful neighbors, great schools, and free swimming and sailing lessons,” he remembers. “It was a way of life that stood in stark contrast to the move that came next, to Mundelein, Illinois.”

Mundelein was a town of lakes, woods and dairy farms north of Chicago—a place where women routinely ran errands with curlers in their hair, and where people would park a car in the middle of a frozen-over lake to take bets on when the ice would melt enough for it to fall in. “It was a big change for us, especially for my socialite mother who loved to entertain, but we came to make lifelong friends and enjoy living in the country,” says Carroll.

He was entering seventh grade at the time of the move, and he’ll never forget his first day of public school in Mundelein. During recess, the kids were playing soccer in the yard using a makeshift utility ball, large and rubbery. A 16-year-old boy much larger than Carroll came barreling at the ball, but Carroll saw he had a shot at it too. “I was hell bent for leather, wanting to show the kids I could do my stuff,” Carroll recalls. “Our feet hit the ball at the same time, but thanks to the law of dynamics, my velocity beat his mass, and he flew up in the air. The experience taught me that the odds aren’t always what you think they are.”

Carroll forged a close connection with a teacher who was eager to teach Latin, sticking around for extra lessons once the school day was over. He also had the opportunity to observe how one’s surroundings influence cultural and intellectual development. Carroll’s own development was supplemented by the close relationships he developed with adults, and his incessant eagerness to learn. His mother taught him French at the age of eight, while Mrs. DuPont would invite him to read Moby Dick over tea with her while summering on Block Island. “That was who I was,” he says.

Carroll landed a full-ride scholarship to the Portsmouth Abbey preparatory school in Rhode Island, where he would study the classics from Benedictine monks alongside some of the wealthiest families in the country. And while other kids showed up for their first day of school in limousines and nice cars, Carroll had taken a bus from the airport and walked the last three miles with his possessions in his grandfather’s steamer trunk. Despite his socioeconomic disadvantage, Carroll saw that he could hold his own, both academically and athletically. He took up gymnastics and became captain of the team. Throughout his time at Portsmouth, he was at or near the top of his class academically, even taking on student teaching in his senior year.

Carroll and his mother had targeted Portsmouth Abbey as a portal to the Ivy League, and Carroll’s hard work paid off when he was accepted to Yale, again on scholarship. He continued his concentration on languages and decided to major in English literature. He studied hard, fell in with the music crowd, and developed close friendships over games of bridge. They moved off-campus for his junior and senior year, and Carroll managed to finish his classes a semester early, earning him a few months of freedom.

With that time, he continued his work study as head usher at the Yale Repertory Theater, where he saw performances by the likes of Meryl Streep, Henry Winkler, and Christopher Lloyd. Carroll had realized a love of theatre earlier in his college career, which solidified when Patrick McGee, the actor for whom Krapp’s Last Tape was written, came to campus to do a reading of the play. Carroll had interviewed McGee, going on to  videotape a performance of the play with himself playing Krapp. “I was twenty years old playing a 65 year old man,” Carroll laughs. “It was probably horrible, but it gives you an idea of how aggressive I was about this theater business. That summer, I worked summer stock in New Hampshire, where a crew of us built an entire stage and performed show after show.”

When he graduated from college, Carroll decided to forego the well-beaten paths toward law, medicine, and finance, instead opting to pursue theatre. He returned to the Chicago area and took a job with the San Quentin Drama Workshop, a theater company formed inside the prison and made famous by Martin Esslin in his introduction to the Theater of the Absurd. The Workshop was captained by Rick Cluchey, who had been paroled after a dozen years behind bars on December 12, 1966 by then-governor of California, Pat Brown. Upon his release, Rick had gone to New York and formed a new troupe which performed Rick’s own play called The Cage, a piece about the damage that imprisonment can do. The Workshop produced the play at the Arena Stage Theater in DC, then for both Houses of Congress, and then took it to Europe, also performing Samuel Beckett’s Endgame. After hearing praise for the Workshop’s staging of Endgame, Beckett asked to meet Rick and invited him to assist in directing a production of Waiting for Godot at the Schiller Theater in Berlin—the first production of Godot to be directed by Beckett himself.

When Carroll first met Rick, he had just returned to Chicago from Berlin with production notes and stage directions for Godot. The Workshop mounted the show at the local American Indian Center, to very good critical reviews. With his good friend and life-long mentor John Jenkins, Carroll found federal grant money to launch a Native American theater company, called Echo Hawk Theater. Rick was then asked to return to Berlin, where he received a grant from the German government to stage Krapp’s Last Tape at the Akademie der Kunste. “Beckett had agreed to direct him, and Rick asked if I wanted to come over and help,” Carroll recalls. “Who wouldn’t? So my friend Bud Thorpe and I got on a plane, hitch-hiked around the capitals of Europe, showed up in Berlin, and started doing plays with Rick and Sam Beckett.”

During that time, Carroll was directly responsible for making sure the show went well on several runs and on tour, including operating the lights, sound, and on-stage machinery. And during that work, Europe had changed him. “When I came back to the States, my mother told me I looked like a well-dressed hippie,” he laughs. “I said yes, but I’m having fun.” He relocated to Minneapolis, where he took a stage management position with the Minneapolis Children’s Theater and independently mounted two small Beckett plays, Not I and Theater II, which were very well received in the press.

Now 28 years old, Carroll decided to go to New York and see what was next. There, he got a “day job” as a paralegal doing patent litigation, his second stint at legal work. It went so well that he decided to go to law school, enrolling at American University. In his third year of school, he worked in the public interest clinic representing Vietnam veterans seeking service connected disability claims or hoping to upgrade their discharges. Carroll won four out of his six Vietnam veteran cases—an unheard-of track record for a student.

Carroll finished law school in 1987 and was promptly hired by a firm called Landis, Cohen, Rauh and Zelenko. Among his first assignments in that capacity was to work on the Supreme Court brief seeking reparations for Japanese Americans who had been arrested and imprisoned during World War II. A critical footnote citing a report from the general in charge of the West Coast military—the only report on the subject of Japanese American loyalty—had confirmed the utmost allegiance of that demographic. But someone had erased that footnote from the Supreme Court brief. In a classic “righting the boat” scenario, Carroll and his team were dead-set on bringing justice. Although the case was lost on jurisdictional issues, Japanese-American Senator Inouye was later able to secure reparations for the families of those who had been imprisoned.

Two years later, Carroll followed Mike Rauh, his mentor, to a law firm that turned out to be very poorly managed. “It wasn’t my world, so I got out,” Carroll says. “I went home and called some people, and before I knew it I had started a law firm.” Carroll sent out postcards to all his contacts letting them know he was launching his own practice. In the first month, he made $64. The next month, he earned twice as much. By the third month, his income had climbed to $700. Then he got word that a Yale classmate was putting together a television company and needed to start a Delaware corporation and fund it with half a million dollars.

Carroll agreed to take on the work, traveling to New York to meet with fellow Yalie John Gavin, and to discuss how the company would air European sports to South American countries. For three years, Carroll served as VP and General Counsel on the project, building up contracts to get the venture off the ground. It ultimately faltered, but it was also exhilarating. “These were smart, fun people, embarked on a wonderful enterprise,” he says. “I regret none of it.” The turn of events allowed Carroll to return to the practice of law, taking on an assortment of litigation, business formation, and telecommunications work. An especially notable case was the wife of Frank Darling, who sought justice for an attack that killed her husband and another, wounding two others, outside the CIA compound at Langley. Carroll was successful in convincing the Justice Department to fund a reward for the capture of the killer at a hotel in Pakistan. “My work is never about just sitting at a desk,” he remarks. “I’m always out and about, seeing if there is some way to do what others see as impossible.”

Through the years, Carroll has had the joy of a successful marriage raising two wonderful children. While they were in elementary school, he got involved teaching a course in Sherlock Holmes and Arthur Conan Doyle to a fourth grade class. This reignited his love of the classroom, leading him to earn a master’s degree in Languages and Literature and teach writing and rhetoric. He has now connected with an independent startup private school. “They needed someone who could teach, do legal, raise money, and help run the school,” he reports. “That’s me to a ‘T.’ I look forward to supporting their mission, teaching children not through lecture, but instead through theatre and the arts, in an active multi-age classroom.”

When advising young people about their career paths in the working world today, Carroll emphasizes the value of flexibility in a constantly evolving world. “Don’t imagine that you’ll have just one career,” he says. “The world shifts quickly enough that if you aren’t completely satisfied with how things are going, you can simply change direction. When I realized that practicing law had led me to lose my sense of humor, I took to teaching writing in college classrooms, which allowed me to regain it. I honestly believe that the world of global communication and business is only just now opening up, and this will help us all get along.”

Beyond that, Carroll borrows from Chögyam Trungpa Rinpoche, a great Buddhist thinker who advises that whenever you go to meet someone significant in your life, bring them something, even if it’s just a kind word or a compliment. “The idea is to be generous with people you care about,” says Carroll. Most recently, when going to meet an old friend, he took her the gift of an old poster from the 1977 Krapp’s Last Tape production, with a drawing scrawled in Beckett’s own hand on the back. Carroll had found it amidst his old journals—the equivalent of the voices from Krapp’s past selves that cause so much strife in the play. Carroll’s own voice from the past is one of meaningful remembrance, allowing him to connect more deeply with the people in his life today.

“Beckett loved to spend days walking through cities, visiting museums to encounter paintings, searching for meaning in art, finding ideas for his work,” Carroll says. “In studying his work, and in living my own experiences, I’ve found that we can all stand up in our lives – to right the boat so the sailing is smoother for all.”

Carroll Hauptle

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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