It’s clear that Jason Freeman loves being a lawyer. He loves the courtroom. He loves the strategy and the challenges. And he really loves representing an underdog. But ask him about his passions outside the law and soon Freeman is talking about his deep appreciation for music and the piano. It also doesn’t take long before he brings that discussion—and passion—back to the practice of law. Music and law, it seems, have more in common than meets the eye—or ear.
“In a way, I guess I started my legal career through the lens of music. I actually wrote my law school personal statement about my journey on the piano. Believe it or not, I only applied to one law school, so I guess it worked.
“I actually began playing the piano in college, and just became obsessed – spending hours every day. I taught myself and was completely absorbed with it.”
Freeman entered college as an athlete playing baseball. “So much of my life to that point had been focused on baseball. But I eventually realized that I’d really taken it about as far as I could. When I gave up baseball, piano somehow became my new obsession. I just picked it up and literally couldn’t put it down.”
“I have this personality where I just go all-in.”
“Music,” Freeman says “provides a window into deeper connections. There’s clearly an emotional, subconscious element at play, but there’s also an underlying set of rules and principles that guide what’s going on. “In a lot of ways that interplay provides a useful model for approaching problems and understanding how and why different arguments resonate. When you break music down, when you really connect with how it flows and how it fits together, you discover there’s an art and a science there. When you get into that analytical side of music and start to think about it conceptually, you find that there’s a hidden language underneath that’s both logical and artistic at the same time.”
The same holds for practicing law. “I’m a trial lawyer. That’s really all I ever aspired to be. As a lawyer, your job is to persuade decision-makers, to tell your client’s story in an impactful way. That requires a willingness to really understand people – to look beyond this idealized conception of the law, of a blind lady justice, to see that there’s something deeper going on. Like it or not, judges and juries are guided by emotion and reason. They’re human. And the law is ultimately a human thing. As a trial lawyer, I think you ignore that at your peril. You know, I don’t think you can truly understand the jury system – and, I would say, the law – until you appreciate that.”
Much of his practice focuses on tax law and white-collar litigation. In those areas in particular, attorneys are often navigating uncharted territory in the law.
“That’s where it’s most fun. In the process, we’re often dealing with dense statutes, dissecting their meaning and searching for support for our story or interpretation. You have to break it down, parse sentences, and really take a philosophical approach to language and its meaning. The ability to command written language, to tell a compelling story – it’s one of the most important aspects of our role. And it’s amazing when you can infuse emotion and color into black-and-white words and just emphatically express your view of an issue in a compelling way. It works a lot like music does.”
ACCOUNTING AND LAW
Freeman is the founding member of Freeman Law, PLLC. He’s also a CPA. The combination has served him well in his career. Next year, he will serve as the youngest chairman in the history of the Texas Society of CPAs, a role that he is very excited about. He is also the current president of the North Texas Chapter of the American Academy of Attorney-CPAs.
Freeman never had aspirations to be a CPA or an accountant, but he was intrigued by several accounting courses in college. “A lot of times I look back and recognize that I am not the prototypical CPA – or tax attorney for that matter. I wanted to be a trial lawyer. I’m creative and try to approach everything from a novel perspective. But my CPA background has been instrumental in my practice. I use it every day and it gives me a perspective that has often been the difference in finding that winning angle in a financial dispute. While I sometimes look back and wonder how I ended up taking that route, it’s turned out to be one of the best professional decisions I’ve ever made.”
Freeman graduated with a joint Bachelor of Business Administration and Master’s degree in Accounting from the University of Texas at Austin. He earned his Juris Doctor with high honors from the University of Texas School of Law.
He says there was no “Aha” moment that led him to a career in law. It was something that he knew he wanted to do from a very young age. There were no lawyers in his family. “I grew up in a very small, rural town. Believe it or not, the first house we lived in was condemned and a church let us live there rent free – so it was a pretty humble start.”
His father was a pharmacist and rancher, as was his grandfather. “They were entrepreneurs, created small businesses that grew from very little. That had a lot of influence, I think, on my taking the risk of starting something myself.”
His younger brother became a well-respected neurologist. “He and I have always loved to talk about neuroscience and the human psyche – how it works and what makes people tick. I think that mindset has been helpful in terms of thinking about how to influence a jury or a judge. I had absolutely zero interest in medicine. I just knew that I would be a lawyer.”
His family has had a significant influence on his career and philosophy – particularly his father. “My dad was killed about 10 years ago in a tractor accident on our ranch in the hill country. I remember that morning I got a call from my mother saying they found him under the tractor. He was in his early 50s and his death came out of nowhere. Events like that really shape your life.”
As the oldest of his brothers, he delivered the eulogy, a process he found therapeutic. “It made me really think about what he stood for and how he had shaped me. The theme of that eulogy was a principle that he had told me hundreds of times – ‘Whatever we are given, we leave better than we found it.’ I think that left me feeling a responsibility to maintain and grow that ideal.”
Freeman’s firm has seen incredible growth in the nearly five years since he founded it. “I have committed everything I have to building something really special with this firm. Though it started out as just me, in the end, I want this thing to be something much, much bigger than me. I tell everyone who joins our team that we are committed to building the best law firm in the world in our areas of practice. It’s important to set goals high – really high. And we have to have their buy-in or they just won’t be a good fit, and I make sure everyone knows this from the beginning and is committed to the level of work that it takes to achieve a goal like that.”
Freeman deliberately wanted to create a boutique and focused firm. He foresaw changes coming in the legal market and a shift that was putting a lot of pressure on the middle market in particular. He felt that the model he was creating would provide a competitive edge and was the best niche to deliver truly exceptional legal representation. He says his management philosophy involves fostering a creative and diverse team of talented people, putting them in positions to succeed and letting them do the job.
“I let people grow into their capabilities and to test out what those capabilities are. That’s frankly the opportunity that I was given as a young lawyer, and it made practicing law very fulfilling.”
DRESSED FOR SUCCESS
Freeman says, “Believe it or not, tax law, of all things, can provide for some pretty interesting litigation opportunities. I’ve actually tried criminal tax cases to a jury down in the U.S. Virgin Islands and had appeals and oral argument with the Third Circuit Court of Appeals when it travels to St. Croix. You could find some worse locales I suppose. Every case and every client is so important. But one sticks out to me in particular.”
Mii’s Bridal and Tuxedo served customers in the Garland area for decades. The small company was owned and operated by an elderly couple from Thailand. One day agents from the IRS arrived and confiscated the firm’s entire inventory of wedding gowns and dresses, sewing machines, and other equipment to settle the company’s alleged debt. The inventory was sold at auction that same day for pennies on the dollar.
The couple was never accused of committing a federal crime. In fact, Freeman says the alleged tax debt, which was just over $30,000, wasn’t even correct in the first place.
Freeman says the case exemplifies the reason he became an attorney. “Here was this elderly couple. They spoke broken English. They didn’t have any money. They were, well, destitute and had literally lost everything. Imagine, your life’s savings and livelihood being seized by 20-plus armed government agents and sold off within four hours.”
“I’ve seen a lot of crazy things with the IRS, but this particular situation was about as bad as it gets.”
Although his firm was in its early stages, he took the case on—acutely aware that it was something of a financial risk with limited financial upside. His firm was up against a powerful, and well-resourced opponent – the Department of Justice. “You just have to love that kind of challenge.” In this case of David vs. Goliath, there was a happy ending to the story.
He adds, “Regardless of the odds, the case was fun and just so incredibly important to me. I viewed the case as precisely the reason I became an attorney, and I felt lucky they somehow found me. I never had any motivation to work for the government – I don’t think I could ever see it. I was always interested in protecting the little guy and kind of relish having the odds against me. I remember thinking that this case just seemed so important to me, or righting the wrong just seemed so important, that I felt like if I could just win this one case, I’d be happy with my career, whatever happened after that. Cases like that really are why you go to law school and become an attorney.” And cases like Mii’s played a part in Freeman’s recognition as one of the leading tax controversy attorneys in the nation.
LEARNING BY TEACHING
Freeman serves on the law school faculty at SMU’s Dedman School of Law, where he teaches a course in federal income taxation. “Teaching has shaped my trial and advocacy skills — perhaps more than any other training,” Freeman says.
He says there is no better way to become an expert than to prepare to teach that complex material to bright students who ask good, insightful questions that test you and that’s especially true in a complex legal arena like tax law. The interplay with students hones his analytical skills.
“I love the classroom part. I love the interactive part. I love not knowing what’s coming next from them and working through and explaining complex topics. And I enjoy working with the students. Thinking critically about how to teach effectively and how to convey concepts really forces you into the minds of the listener – to think about things like whether you are assuming knowledge that isn’t there and learning how to truly connect. So much of what we do as lawyers is teaching. So the last eight years or so of teaching at SMU have had a huge impact on my approach as an advocate.”
Freeman says there is a common denominator among most of the things that lead to being a successful lawyer and that is the ability to connect, to have empathy, to genuinely care. He believes authenticity is 99 percent of the job when it comes to influence – whether it’s being a leader or trying to sway a jury. “And as simple as that sounds, it’s really not. We work in a profession that often creates feelings of imposter syndrome, it comes with a lot of forces that lead you to question yourself and to feel like you need to be something that you’re not. One of the most significant insights I’ve had is that people – whoever they are – can genuinely connect with other people of all types and viewpoints. If people see you as authentic, chances are much greater that they’ll listen and consider what you have to say. A lot of the technical advocacy skills that we constantly work on as lawyers are skills at the margin – they’re important, but they only do so much good if you don’t have authenticity.”
Freeman still plays the piano. He and his wife, Laura, a Realtor, have three kids: Gia, Chloe and Beckett. The family attends church at Hope Fellowship and is very involved in their community. Freeman says he has tried to pass along his appreciation for music to his children. The kids often join him at the piano and with a number of musical instruments.
“We have a lot of instruments. They bang on everything,” he says.
After family, it is still the law that rewards, enlivens and fascinates his life. “I love the diversity. I love the learning aspect of it. The single most enjoyable thing has to be making a difference for clients, literally changing someone’s life for the better. It’s such an honor to have the opportunity to practice law and to represent my clients. It’s something I’ll do until the day I die.”