International Society of Primerus Law Firms

Harvard Law alum opts for life with a more measured pace

Ryan Billings

By Brian Cox

Attorney Ryan Billings describes his six years working at a white-shoe law firm in New York as “crazy, wonderful, amazing, terrible, and caffeinated.”

Says Billings: “I basically worked and slept and did very little of the latter.”

With the expectation of billing more than 3,000 hours a year, Billings was a 24/7 captive of his job, regularly employing the showers and beds that were available at the firm.

“It was all-consuming, which was great and awful at the same time,” he says. “But I wouldn’t trade the experience for anything.”

Billings accepted a position at the prestigious law firm for the same reason he had chosen to attend Harvard Law School: He welcomed the intellectual challenge that came with being and competing among some of the country’s best legal minds.

He learned a tremendous amount about corporate law during his time at the firm, Billings says, but when he considered his future there, he saw too many partners with multiple failed marriages who never saw their kids and spent their entire life working. In short, it wasn’t a lifestyle price Billings was willing to pay.

“As much as you love it, you either have to fully commit to that career and accept all the consequences or you’ve got to get off that track,” says Billings.

He chose to get off the track and leave behind the bright lights of the big city to return to the greener environs of his home state of Wisconsin, from where more than a dozen years earlier as a brainy and eager college-bound student he had been only too enthusiastic to depart.

“When I’m in the state of Wisconsin, I am happier,” he says. “I don’t know how to describe it. It’s green. I like the people. I like the culture. I love the Packers. I don’t mind the winters. It’s my home.”

Billings is now chair of the Business Litigation department at Kohner, Mann & Kailas, S.C. in Milwaukee, just an hour south from the small city of Sheboygan where he grew up.

Ryan Billings and his wife Megan pose with the University of Wisconsin football mascot Bucky. Billings is a football fan with a special loyalty for the Greenbay Packers.

Sheboygan is located on the shores of Lake Michigan, and Billings characterizes it as a place “smaller than a closet” where everyone waves and is nice to each other. He has come to appreciate those qualities more and more over the years, standing in sharp contrast to the aggressive and in-your-face culture he regularly encountered in New York.

His father, Robert, sold insurance in the Sheboygan area, and his mother, Jean, was a zoning officer. Billings, the third of four sons, was a soccer player, a Boy Scout, as well as a saxophonist in the high school band.

He made up his mind to be a lawyer at the age of 14 when someone close to him got into serious criminal trouble and as a result of poor legal representation suffered severe consequences.

“I thought I’m going to be a good lawyer, I’m going to be someone who’s there for people who really need help and someone to stand up for them,” he says.

In addition, he says the law is a “constellation of things I’m good at: Thinking on my feet, extemporaneous speaking, logic, argument, rhetoric. All those things came naturally and were fun for me.”

A standout student who exceled at debate and forensics in high school, Billings says his academic aspirations were presaged in a photograph of him around the age of 6 where he is sporting a Harvard t-shirt. He had his aim on Harvard for as long as he can remember. As it turned out, his first stop was Princeton, where he studied philosophy, before he attained his goal of becoming a Harvard Law grad.

By the time Billings began law school, he had a strong sense that he wanted to be a business litigator. During the summer after college, pursuing his longtime commitment to defend people in need of good legal representation, he worked for the Public Defender Service in Washington, D.C. But three domestic abuse cases in a row made it clear to him that he didn’t have the stomach for criminal law.

“The hard-working lawyers at PDS do critically important work that makes a real difference, but criminal law wasn’t for me,” he says.

His law school experience was indelibly colored his first week at Harvard when the World Trade Center and the Pentagon were attacked on 9/11. The national tragedy rocked the core of the campus and fundamentally shaped Billings’ first year.

Ryan Billings met his wife Megan while she was a law librarian. The couple have now been married 7 years.
“The professors, the students, everybody was just shaken,” recalls Billings. “A lot of my classmates had family or friends who worked in the Twin Towers. It was devastating.”

It also was in his first year that Billings encountered a professor who profoundly influenced his understanding of law more than any other and was “the best legal mind I’ve ever seen.”

Gerald Frug was the Louis D. Brandeis Professor of Law at Harvard and taught contracts. He impressed Billings with the revelation that the meaning of any contract can be changed by including a “mental comma” in the right place.

“I think I learned everything important about law that first semester from my contract professor,” says Billings, who served as Notes Editor for the Harvard Law Review. “If you know contracts, you know law.”

When a battle-tested Billings returned to Wisconsin at the end of 2010 following his six years in New York, he joined a law firm where the difference in environment was “night and day.”

“I learned how important a law firm’s culture is to your level of happiness. How people relate to and treat one another makes all the difference in whether you end the day exhausted but happy or exhausted and miserable,” says Billings.

It was soon after his return that Billings met his future wife, Megan, who was a law librarian at the time and is now a historical fantasy novelist writing under the guise of M.K. Wiseman. The pair have been married for seven years.

When the law firm he was at merged with another firm three years later, Billings came to Kohner, Mann & Kailas. Known familiarly as KMK, the firm started as a collection firm for business-to-business debt in 1937 and is currently celebrating its 85th anniversary. Since its founding, the firm has further developed a business and financial services practice as well as a business litigation specialty.

“I think as a firm, we take different areas of focus, different skill sets and different practice areas and mesh them well,” says Billings. “The firm creates a synergy that is fun to be part of.”

Billings credits the successful synergy in part to the firm leadership’s willingness to learn what individuals are good at and to discover what drives them and makes them tick.

As head of the business litigation department at the age of 44, Billings is representative of the firm’s commitment to empowering younger attorneys.

“We have younger generations being actively encouraged to step up and take leadership roles,” says Billings. “The firm has made a very concerted effort to get younger lawyers involved, which I think has been a really smart policy and good for the vitality of the firm.”

During the COVID pandemic, the firm went remote in March 2020 and didn’t lose a step. The litigation department remains remote and Billings says his “productivity has been off the chart.” The department, too, has thrived.

“My people have been working their tails off. The numbers show it. We’re having our best year ever,” says Billings.

When Billings looks out at the legal landscape, he regrets what he sees as the unfortunate deterioration of collegiality in the profession.

“It seems to me the practice of law has gotten nastier and that it’s continuing to get nastier,” he says. “There’s an expectation from clients that they want you to be in the other side’s face.”

At the same time, he recognizes a concerted effort on the part of judges to promote and encourage collegiality and cooperation. He also sees a new generation of lawyers emerging who understand that serving their clients well often means efficiently working issues out with the other side.

“I think there’s a good trend from younger lawyers who have grown up to believe in a different model – that cooperation doesn’t mean weakness, doesn’t mean ineffective, non-zealous representation,” says Billings. “If you can work with the other side, you can save your client a ton of money and it’s not going to affect your representation negatively.”

Attorney Ryan Billings and his wife Megan are ice fishing enthusiasts. Megan proudly shows off a catch while ice fishing.

This penchant for collegiality is a central component in Billings’ involvement with Primerus™, which began when he attended an event in 2015.

“I love Primerus™,” he says. “Part of it is, they are good people to spend time with. As a lawyer you want be around smart, fun, good lawyers and I find them at Primerus™.”

Equally important, of course, is that Primerus™ has been instrumental to his practice. The organization has been a great driver of growth for the firm and has improved the quality and reach of its representation.

“I litigate all over the place and the way I do that is with Primerus™,” he explains. “I can market myself as an international law firm because we have lawyers all over the world. I can tell clients with confidence that I can be your quarterback for any litigation anywhere in the world because I know that anywhere I look I can call up a Primerus™ firm – probably someone I know and that I’m friends with – and they will get excellent representation. I’ve never been let down by Primerus™.”

Looking toward the future, Billings is turning his focus on mentoring the next generation of lawyers. As he grows his practice, he wants associates who are prepared to step up and accept a transition of responsibility and leadership. He works to instill in younger lawyers a sponge-like approach to learning. It’s an approach that has served Billings well.

“I try to learn from everyone I interact with,” he says. “If someone does something I think is good, I will shamelessly steal it and adopt it. I like to think I can learn something from everybody.”

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