The Right Road

“And ye shall know the truth and the truth shall make you free.” So reads the line from the Gospel according to St. John, inscribed along the entryway of Central Intelligence Agency Headquarters building. It was because he believed in the statement so much that Sheldon Leggett’s father came to have a crisis of vision so deep.

As Deputy Director responsible for Soviet Intelligence, Sheldon’s father had been a Cold War warrior through and through. “I can remember him vividly explaining the domino theory of Communism to me and why he believed we had to be in the Vietnam War,” Sheldon says. “He believed the American Dream wasn’t about success or money, but about righteousness and principle. To him, we were a nation that did the right thing. We were a nation that took the right road even if it was the hard road.”

Under this banner, Sheldon’s father helped build the CIA as an apolitical entity, responsible for getting all the intelligence there was and objectively separating the important from the irrelevant. It was then up to politicians to figure out what to do with it. When Richard Nixon became President of the United States, however, all that changed, and the CIA was asked to find intelligence in support of a given political agenda. “Staunchly committed to truth and intelligence, my father was deeply upset by the mandate to pursue intelligence like evidence in a legal case to support a political outcome,” Sheldon explains. “After Nixon’s policy toward Cambodia and then the Cuban Missile Crisis, my father couldn’t be a part of it anymore. With his vision of the world shaken, he decided to leave the agency he loved. I was thirteen at the time.”

It wasn’t the easy road forward, but for a man with the kind of uncompromising vision his father had, it was the only road. It’s the kind of vision that now defines Sheldon’s idea of leadership—vision that inspires people to do things the right way, even if it means rejecting the easy way. Now the founder and President of EKKO Title, an independent full-service title and escrow company specializing in home mortgage loan and refinance closings, Sheldon spent his formative years shaping the vision that continues to lead him today. “I’m best at stepping back and seeing the big picture, which is good for the clients we serve and for EKKO itself as we all work toward optimal outcomes,” he explains. It’s a skill for seeing the macro view that has been shaped not by taking the easiest or conventional road, but instead the right road.

Founded in 2008, EKKO serves Northern Virginia, Washington, and Maryland. Focused exclusively on buyer and seller resales, they do one thing, and they do it with excellence. The company’s approach is unique in an industry that has changed dramatically over the past 25 years. Until 1992, banks, mortgage companies, and real estate companies were prohibited from owning an interest in a title company. But new laws removed this prohibition and allowed affiliated business arrangements to arise, so long as they did not overtly direct business between them. “This doesn’t work in practice,” Sheldon says. “Big companies wouldn’t own their own title companies if they couldn’t drive business to them. They’ve put incentives in place compelling agents to drive that business to their own affiliates.”

EKKO is the largest title company in the state not affiliated with a bank, real estate company, or mortgage company. He’s up against hybrid institutions that aim to funnel deals to their own title company affiliates. In order for a consumer to borrow money from a bank, for instance, that institution might require the borrower to buy title insurance as well. “If they can determine their own insurability, set their price, and require you to pay for it, that’s great business for them,” Sheldon points out. “It’s a huge conflict of interest. When real estate agents or loan officers come to us, they know that the value they’re getting from us surpasses whatever incentive their employing companies are offering to use their own title companies. In an industry where the delay of a week can make a big difference, we’re known for closing quickly and successfully.”

With the rise of buyer agency also starting in 1992, title companies like Sheldon’s have become an arbiter in the settlement business, helping to achieve agreement between a buyer and seller. To this end, EKKO has a symbiotic relationship with a seven-lawyer real estate law firm Sheldon launched, called Leggett, Simon, Freemyers & Lyon. As a neutral party, they specialize in deescalating conflict situations to close the deal. “We close contracts and settle differences between buyers and sellers, almost as an alternative to a speed resolution situation,” Sheldon explains.

EKKO is now a company of 52 employees spread across ten offices, all in Virginia. And while the future of the industry remains to be seen, Sheldon is confident that affiliated companies simply can’t compete with EKKO as long as service is in the mix. Bust most importantly, Sheldon offers vision. “Good leadership is good management, enrolling people in the vision you have and the direction you want to go,” he says. “I’ve worked in dictatorial office settings, and they always seem to fail. It’s important to initiate people to your vision, or to modify your vision if people you trust aren’t buying in.”

This leadership philosophy has been sharply honed through a lifetime of keen observance of how power is wielded on an individual, institutional, and global level. Sheldon was born in Washington and spent his earliest years in an apartment on P Street. The family later moved to a duplex near Military Road. His father, a hard worker hailing from humble beginnings, was a World War II hero who came home to attend Princeton on the GI bill. He finished two degrees in just under three years and then went to Harvard Law School, where he was recruited to join the Office of Strategic Services (OSS), the predecessor to the CIA. As he helped to build the CIA, the family moved to McLean, Virginia, which was little more than farmland at that time.

Sheldon grew up as the oldest son with two older sisters and a younger brother, which their mother stayed home to raise. “She was very kind, sweet, and tolerant,” he remembers. “She was the traditional 1950s housewife in every respect.” The children played in the woods all day and would take their guns out back for target practice. Their elementary school was within walking distance, and Sheldon played Little League, the only organized sport around.

At the time, Sheldon wasn’t completely aware that his father was an employee of the CIA. He often left for months at a time without notice, but when he was around, he was a confident, fun man. Sheldon noted a marked shift, however, when he left the CIA and grew somewhat detached for a time. In some ways, father and son went through a crisis of vision at the same time. “He launched a computer company with some friends, and to me, he was part of the establishment I was meant to rebel against,” Sheldon reflects. “I started acting out, skipping school, and getting into trouble. I’d get a couple good grades and then get F’s because I was convinced I already knew everything, so why pay attention in school?”

At sixteen, Sheldon couldn’t be tamed. He landed free concert tickets to the shows around town from a family friend, a rock-and-roll promoter who relied on Sheldon’s advice for discerning which bands could fill which venues. He hitchhiked to Canada and later got kicked out of school. When he cut off his high school education permanently midway through his junior year, his father gave him the option of paying rent or moving out. Sheldon stayed with friends until he got a job with Mobile Car Care, and at the age of seventeen, he decided that going to college would be far more interesting than trying to finish his high school degree. With that, he filled out an application to Northern Virginia Community College (NOVA) where he took two classes and earned A’s in both. “Supporting myself at an early age and figuring out how to make it all work gave me a lot of self confidence,” he recalls.

When he was 18, Sheldon got in his old car with his girlfriend and drove to a town west of Denver. “All the beautiful people were going to Colorado, so we decided to start a life there,” Sheldon recounts. “I got a job building houses and transferred my college credits to the University of Colorado, where I was able to take more classes without showing a high school transcript.”

Shortly afterward, Sheldon got a once-in-a-lifetime offer to work in Nicaragua, where some of the few remaining native tribes still lived largely untainted by the civilized world. He decided to transfer his credits back to NOVA to complete an Associates Degree, when he was finally confronted with his lack of a high school degree. “I confessed I had never made it past tenth grade and had never taken the SATs,” he recounts. “They took me to meet with the Dean and the Provost, and they tried to lay out a path for getting my GED that would have taken six months. I drew their attention to their application form, which said they required a high school diploma, a GED, or the equivalent. I said, ‘If getting A’s in  your courses and meeting all the requirements for a degree at this institution is not the equivalent of a high school diploma, that doesn’t speak well of the institution.’ With that, they agreed to let me graduate, and I was probably the first ever to use the ‘equivalent’ box.”

In Nicaragua, Sheldon realized his dream of working as an archaeologist, only to find that he didn’t like sifting dirt for hours in the jungle looking for shards of pottery while being intermittently shot at as the country underwent a coup. Before long, he made his way to El Salvador and then Guatemala before joining a cultural anthropology group and finally traveling to the Amazon to work with the Yawa Indians. “Working with people was far more interesting to me than archaeology,” he says.

When he returned to Virginia, Sheldon transferred to George Mason University to complete a dual degree in History and Anthropology with a minor in Religion. His academic performance was much improved, but he still marched to the beat of his own drum and wasn’t afraid to challenge authority. In fact, when he was barred by the Dean of the Business School from enrolling in a particular course because it was full, he marched over to the University President’s office. It just so happened that the President, George Johnson, was in the process of interviewing for a new driver, and Sheldon was allowed to enter the President’s office since everyone assumed he was the applicant. Sheldon told his story, and Dr. Johnson agreed to call over to admissions.

The next day, Sheldon was admitted into the class, and he returned to Dr. Johnson’s office to thank him. The President then conveyed to Sheldon that he needed a student liaison to ensure he was connected with the student perspective. He offered Sheldon the job, which later entailed participation on radio shows, in interviews, and on trips to the state legislature as the school’s student liaison. They cultivated a solid relationship, and when Sheldon conveyed his interest in going to law school after graduation, Dr. Johnson put him through a pre-admissions summer trial program to test his commitment. It took hard work, but the young man proved himself and was admitted into George Mason Law School. “I had no intention of practicing law; I just liked the study of law,” he explains. “I liked the analytical thought process and wanted a graduate humanities degree. I also noticed that most of the successful businessmen my father knew had law degrees.”

By that time, Sheldon had launched a modest catering business serving DC’s music venues, providing customized offerings for bands coming through the area. He sold it for $15,000 to put toward tuition and commenced his studies in 1988. He used the opportunity to learn more about one of his heroes, a brilliant graduate of Yale University and Harvard business school who also found time to become an accomplished jazz pianist and VP of the Pacific Stock Exchange at age 23. Ken Uston had left that all behind when he learned how to count cards, making a name for himself in Las Vegas and becoming one of the most famous blackjack players of all time. He was banned from all casinos in Nevada and New Jersey for unfounded allegations of cheating and sued them both, winning in New Jersey but losing in Nevada on the same case. While it was being reviewed in the Supreme Court, he died mysteriously in 1987. “Uston was this brilliant mathematician who didn’t care about money—he just loved the game,” Sheldon says.

Sheldon decided to write his Law and Economics thesis on the remarkable figure, and found himself in the school’s law library one evening. There, he ran into a second-year law student, Katie, who asked for his help finding some cases. “As it turned out, she was looking for the Uston cases, too,” he says. “Of the six million cases in print at the time, we were looking for the same six. But she was interested in Uston for a very different reason. He was her father.” The two started dating, and six years later, they were married. “Katie’s been an incredible life partner and mother,” he remarks. “She’s a brilliant lawyer, exceptionally independent, and an incredible overachiever.” Katie was President of the Alexandria Bar and is now president of the National Organization of Bar Counsels, as well as a professor at the American University Washington College of Law.

After interning for the Department of Justice, Sheldon graduated from law school in 1990 and soon found himself a homeowner with $75,000 in student loans to pay off. He decided to practice law to eliminate his debt, landing a job with the preeminent ethics defense attorney in Virginia, David Rosenfeld. “He wrote the book on legal ethics,” Sheldon remarks. “If you were a lawyer and got into trouble, you called him. It was a very interesting experience.”

Over the next several years, Sheldon did some divorce work and civil litigation, which wreaked havoc on quality of life both in terms of the hours required and the subject matter of the cases. “I decided I had had enough of cross-examining children about mistakes their parents had made, or seeing people get fifteen years of jail time for marijuana possession when they had three children at home,” he recounts. “You can’t help but take on a lot of emotional baggage when you’re doing that.”

Sheldon decided to move on and received offers from three different law firms. One of them, a title company, offered him substantially less than the other two, but made an insightful sales pitch. “They guy observed that I wasn’t a lawyer at heart,” Sheldon says. “He told me I might get ahead at first with the other firms, but I’d hate it and quit after three years. If I went with him, I’d end up running a business in the long run, which is what I really wanted.”

With that, Sheldon again turned away from the easy road in favor of the right road, embarking on a journey that toed the line between law and business. He wielded the law in measured, sustainable ways, drafting documents and learning the business without the stress of prosecuting. When that title company was sold, he got an offer from a big holding company. “It seemed like a very secure job, and since Katie and I had just had our first kid, job security was at the forefront of my mind. But then they started downsizing and laying off people. I realized that the only job security is no fear of losing your job, and the only time you don’t fear that is when you work for yourself. That was a defining moment in leading me to decide I wanted to have an equity interest in any place I worked after that.”

With this new resolution, Sheldon joined several partners in launching MBG Settlement Group in McLean. But his partners later made the decision to sell that company as well. Sheldon decided he wanted more control over the fate of the companies into which he invested so much time and energy, so he decided to launch EKKO.

By that time, the real estate and financial crisis were just beginning to explode—a risky business move by some counts, but brilliant in retrospect. “We didn’t have any overhead, and we had nowhere to go but up,” Sheldon says. “There were a lot of talented people laid off and looking for opportunity. We couldn’t get any financing, so we bought a lot of things second-hand, but even that turned out great, because we had no debt.”

Now, Sheldon has found the perfect fit for his strong independent streak in entrepreneurship and EKKO. Like his father, who he remembers as the most selfless person he ever met, Sheldon strives to leave the world a better place, serving on the board of the Potomac River Conservancy and supporting St. Jude’s and the SIDS Foundation. “I didn’t inherit a dime from my father because he borrowed $100,000 to buy an ambulance for our county fire department, replacing the old Chevy suburban they were using for emergency runs,” Sheldon remembers. “He did all of that in secret—we didn’t find out until he died. It’s incredible to me that he did that, and I’m so glad. The things that mean the most in life are never material—they’re people. They’re my parents and siblings, my wife, the wonderful son I lost eleven years ago, and the wonderful son I have now.”

In advising young people entering the workforce today, Sheldon echoes the advice his father gave him, rooted in the logic that people work harder when they’re pursuing something they’re passionate about. “Don’t go for a field of study or a job just because of the money,” he says. “College is a time to grow and expand your mind and life experiences. You’ll pay attention, learn more, and work harder if you’re doing something you genuinely care about. Don’t be afraid to do something you like doing, and don’t be afraid of failure. Job security is essentially a myth, so take risks and pursue something you like, because that’s what gets you ahead in the long run.”

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