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The Pursuit of a Career in Law

April 20, 2021

In this episode…

The path to a career in law is a challenging yet rewarding one. Our guest on this episode of Engaging Experts is Jonathan Schwartz, who looks back most fondly on defining moments in his career and sheds light on how he has achieved success.

Jonathan reflects on the importance of influential mentors in his life, and the advice that they shared. Now, Jonathan is able to offer advice and mentorship through the form of thought leadership, which is a primary focus of his. Whether it’s publishing his writing, or hosting Goldberg Segalla’s Timely Notice podcast, Jonathan is looking to offer insight and help professionals in the industry.

On this episode, David Seeley interviews Jonathan, who is a partner at Goldberg Segalla, the vice-chair of the Insurance Law Committee at the Defense Research Institute and has the highest peer rating standard by Martindale Hubbell.

Episode Transcript:

Note: Transcript has been lightly edited for clarity. 

Host: David Seeley, Business Development Executive, Round Table Group

Guests: Jonathan L. Schwartz

Introduction: Welcome to Engaging Experts, the podcast that goes behind the scenes with influential attorneys. Our guests will describe their practice and expertise. Then, we will go deep on various topics related to effectively using expert witnesses.  

David Seeley: Hello, and welcome to another edition of Engaging Experts. This is David Seeley, Business Development Executive with Round Table Group and one of the hosts of this podcast series. We have a great guest for you today, Jonathan Schwartz. Jonathan is a partner at Goldberg Segalla and chair of the firm’s Cyber Risk Coverage Practice. Jonathan received a Bachelor of Arts degree from George Washington University, Elliott School of International Affairs, and his Juris Doctorate from the University of Illinois College of Law graduating magna cum laude. Jonathan was the former chair of the 2019 Insurance Roundtable and currently serves as the vice-chair of the Insurance Law Committee at the Defense Research Institute. In addition, Jonathan is a top-rated lawyer by Super Lawyers, he has the highest peer rating standard by Martindale Hubbell, AV preeminent, and he has been recognized as a best lawyer in America consecutively from 2018 to 2021. Jonathan, we are delighted to have you with us today. I’m looking forward to diving in, but first, let’s pause briefly for this sponsorship message. 

Announcer: This episode is brought to you by Round Table Group, the Expert on Experts®. We have been connecting attorneys with experts for over 25 years. Find out more at  

David Seeley: Welcome, Jonathan. Thank you for being our guest on this episode. 

Jonathan Schwartz: David, thank you so much for having me on the show. I appreciate the opportunity to engage with your listeners. 

David Seeley: You are most welcome. Jonathan, I must admit I have been so impressed reading your bio and learning about all your accomplishments. It has been a true pleasure getting to know a little bit more about you and your background. I would like to start right at the beginning if you don’t mind. At what age did you know you wanted to become an attorney?When did you realize that was something that you were looking for?Was there anyone or anything that led to that decision? 

Jonathan Schwartz: I think I have wanted to be an attorney my entire life. I come from a family that is primarily comprised of doctors and lawyers. I found out very quickly that medicine was not my true calling, so that left me with only one option.With that said, I look to my Aunt Esther, who is a very accomplished lawyer who happens to be in the same practice area that I am. It is only by happenstance that I ended up in that practice area.Nonetheless, I always looked up to her and she inspired me to pursue the practice of law. 

David Seeley: Can you tell us a little bit about the early days when you first started your career?What was that like, and how have things changed for you throughout your career? 

Jonathan Schwartz: Well, David, I think that to better understand the early days of my career, it is important to understand where I came from. When I was in law school, I found myself attracted to the specialty of intellectual property. I really concentrated in law school on making myself the best intellectual property law student I could be until I found that it was not the best fit for me. Then I pulled back a little bit and decided to find an opportunity that would allow me to reset and find what my true calling was. In doing so, I found myself at the Illinois Appellate Court right atter law school as an appellate court clerk. While I was there, I experience a number of different areas of the law, but really found that I was interested in appellate practice. Coming out of the Illinois Appellate Court I found myself looking for a job in in civil appeals and I connected with a firm, which ended up being my first firm, and they allowed me to do civil appeals as part of my practice.They also said we don’t quite have enough work for you to do appeals full time and would you mind also doing insurance coverage work? I said,” I am not entirely sure what that is, but if you pay me a salary, I will certainly do that for you.” That is what I did, and I found that while I really enjoyed appeals, insurance coverage is kind of a similar animal, but I think is one that I found even more exciting. I quickly transitioned to the world of insurance coverage and it is through that and my involvement with the Defense Research Institute (DRI) that I find myself where I am today. 

I started off in insurance coverage and then [continued] moving from one firm to the next and continuing to build my practice and find the right platform for me. I eventually ended up at Goldberg Segalla, helping them open up their Chicago office in 2014.How did this all change? How is practice today very different from when I started practice?I’m not entirely sure for me that it really is. Again, I found myself, as my career went on, specializing more and more in the field of insurance coverage. I would say the one big difference between when I first started versus now is technology, and, most importantly, I think the ability for people to work remotely. When I was first starting, we had laptops. We could bring them to and from, but I think it was the ubiquity of Wi-Fi, and the ability to have smart phones that allow us to communicate effectively with our firms when we are not in the office. That has been the largest and most significant change that I can point to from when I started in practice. 

David Seeley:  I am sure, [particularly] with the recent pandemic for the last year and a half, we have gone to an even more remote setting and [are] now able to work from home. When you look back on your career do you have any defining moments that you appreciate a little bit more now than you did? It was advice from a mentor, or life lessons you took from colleagues that you have worked with. 

Jonathan Schwartz: I think every one of my moves throughout my career has provided a defining moment, but I look back most fondly on some of the mentorships from some of the partners that I worked with over the years.The first one I would note is the person I worked for in my first firm, Jim Horseman. Jim was always kind enough to impart some very sage advice about the practice of law and the one that always stuck with me most was that you are now a professional and that means that you have toalways act like a professional. It is hard to take off the lawyer hat when you leave the office because you remain a private practicing lawyer. With that in mind, I think that the sound bite that he used was, “It is time to be a professional.  

As I went to the next firm, the person I worked with most closely, and I consider one of my mentors, always stressed the importance of reputation and building a reputation. It issimilar to the real estate motto, which is, location, location, location.  In his words, it was always, reputation, reputation, reputation.” That was something I took away as one of the other important life lessons. 

As I transitioned into an in-house experience, I worked with another attorney who was one of the most brilliant people I have ever worked with. He gave me the concept of precision. It is very important to be precise in everything that we do, and so he always was kind to lend a book or provide some guidance about how to become a little bit better. I think after my experience there, I always end up with certain legal resources at my fingertips. Even as I am working from home in this pandemic environment, I still bring home copies of some of the legal texts that I find most important, including the ones from Bryan Garner. When I found myself at Goldberg Segalla, the mentorship I have gotten from some of my partners has been invaluable.One of the ones that sticks out the most is the importance of perspective in the big picture and helping me to best understand how everything fits together. It is something along those lines that I have always treasured as I have grown in my practice.  

The final one that I will mention is not from one of my partners.When I was admitted to the Commonwealth of Massachusetts as a practicing lawyer midway through my career, I found out that one of the requirements for licensure was that you had to attend in person a new lawyer’s seminar. So, I found myself about 12plus years into my career sitting in a big classroom with a lot of lawyers who had never been in practice, a lot of fresh out of law school attorneys. At the end of the day, they brought in a judge to talk to us about the legal profession. It was a great talk. What I took from it most was an opportunity to talk to him afterwards. I had come off a situation where I had gotten into some loggerheads with opposing counsel. I could have handled the whole situation better and we got a little crosswise with the judge in that case. I talked to the Massachusetts judge, and we talked about what could I do to work through the situation. There are opportunities in every crisis to learn from it and to make things better. This judge was kind enough to encourage me to reach out to the judge who I had gotten crosswise with and to not only apologize but talk to him a little bit about what I could do better and gain some mentorship from him. I think that the lesson I learned from that judge is that judges, along with attorneys, are human.They have been in a similar position that you have, and just because you get yourself in a hot spot it does not mean that there is not an opportunity to learn from it.So, remember that judges are human is a very important lesson that I learned. 

David Seeley: That all sounds like you got some good advice, adhered to it, and put it into practice. I appreciate your perspective on that. It is something to look up to. You have been at this quite a while, and when you look at best practices and things you have learned from the people that you just talked about, is there a routine, that you found that gives you the best traction and results? I am sure it is a case by case or a matter-by-matter instance, but are there bigger principles? Perhaps you have found what works well for you and gives you great traction. 

Jonathan Schwartz: If there was an opportunity for routine in my practice, I think my practice would be a lot easier. I find myself every day continuously trying to figure out what the right answers are and usually the right answers are presented by questions in a whole host of different areas. So, even though I would say my practice is primarily comprised of insurance coverage, I still find myself daily being confronted with all kinds of different product lines, different types of carriers, different jurisdictions... There is always a new and interesting question as far as best practices go. It is all about precision. It is about making sure that you understand the question that is being asked, and to never be afraid to ask the question. Always dig in.Never settle for less than you can. There is the right answer and then there is a good enough answer and I do not ever want to be in the position where I am settling for good enough when the right answer is attainable. You will put in that extra effort as a professional to try to get to all the right answers that you can at the end of the day. Remember that you are providing guidance to your clients and trying your best to give the best guidance you can. In doing so you try to put yourself in their shoes and think about the pressures and the external forces that they are dealing with when giving your advice so that your advice is as helpful to them as possible.  

The final thing I would mention, as far as best practices, is to be responsive. Again, it is not important that you give an answer in the first 30 seconds of receiving an inquiry, email, a phone call, but it is important that you must be as responsive as you can, noting the time constraints, when the client asked you the question. It is most important that you give the client the right answer in as timely a way as possible. 

David Seeley: I am imagining that client can get anxious and wonder where you are on something, and I can certainly appreciate that. I would like to shift gears just a little bit here. One of the things we have not talked about yet is your impressive background. I did not highlight it in your introduction, but you are a regular host for our listeners of Goldberg Segalla’s Timely Notice podcast and also a prolific speaker and writer on recent developments affecting the insurance industry. Why don’t you tell us a little bit about how you became involved in those two endeavors? 

Jonathan Schwartz: Sure, absolutely, David. The writing aspect is something that I have been doing ever since law school.Even in law school, I entered some writing competitions because I had interesting ideas that I wanted to pursue, and it is important for the purpose of legal scholarship to get them on paper. Ever since I was in law school, even as a young associate, I was publishing regularly. I found it to be important to develop your legal acumen by studying areas that you might not be familiar with. If you ever want to be thought of as an elite thought leader in this space, you have toactually fulfill your end of the bargain by providing thought leadership. That is something I have always found to be important, and I am very thankful that I am at a firm that supports that leadership, as Goldberg Segalla does.Speaking has always been something I have been interested in as well. When I was in high school and college, one of my primary activities was policy debates, so I always found myself on my feet speaking, researching, and arguing interesting points.I find it a natural extension of my skills that I developed through policy debate and whatnot to enter the legal profession and then, from there, see the thought leadership that I developed turn into scholarship that I could not only pass on through the written word, but also by presenting at conferences, trade organizations, and other opportunities to speak to people who might not be able to read the other pieces that that I provide. 

The question about the podcast is an interesting one, David. I have been interested in podcasts for many years.I subscribe to probably too many podcasts. [I am always] listening to a podcast or another that interests me, and I found that a few years ago, as I was thinking about what I could do to continue to further my legal scholarship, I realized there really was not a podcast out there for the insurance industry with respect to claims, claim trends and other things related to what I do. I approached my firm and said, “This would be a good idea to try to put out this podcast, and they were supportive. I am very thankful for that. We started from the ground up, coming up with ideas, reaching out to everybody in my network, who would listen and asking them if they would come on the podcast.My partners have been very accessible, willing to throw their hat in the ring and speak to me about an area that they are interested in, or they are an expert in. I found that throughout the entire experience, we published well over 100 episodes. We are very proud of what we have created, and it is a great opportunity to provide yet another way that people can consume the content. There are a lot of people who write newsletters, and they are terrific, and I read a lot of them. There are people who write to Law 360. People who write for trade publications and trade magazines. But again, the one area I did not find a lot of opportunity for content consumption was podcasts. I know that I am always listening to them when I am on the go.People are traveling, at least they were before the pandemic, and so I thought it was a great opportunity to give them an app, to give them a way to consume some interesting trends and hot topics in the car, the train, or on the plane. 

David Seeley: I listened to many podcasts myself and I do those in the same situations whether it is in a car, on a run or something like that. It is such a great additional resource for us, and we appreciate you doing that. When you think about young people that are in law school or young people that come up and ask you, “I am considering being an attorney,” or, “I am interested in law school,” what is the best piece of advice that you would give to someone making that consideration? 

Jonathan Schwartz: My advice is as follows: the legal profession, especially private practice, is hard.It is not an easy profession. I would say there are easier ways to make a buck.For those of us who love the legal profession as much as we do, there are a few things that run through us that make us a special breed. I guess the question I would ask of either a new law student or someone who is considering applying to law school is what is about the legal profession that interests you? What is it about the practice of law that makes you think that it would be a good fit for you? Why do you want to be a lawyer? Those are the kinds of introspective questions that I think are important and you would be surprised how many times you get the answer, “I am not sure why, but I did not think my philosophy degree was going to pay the bills.” Or you might hear something like, “My parents are lawyers and I think I should do that too.” Those are interesting reasons but not the best reasons because you find a lot of people that went to law school either not using their legal degrees these days or [they] have used a legal degree but are doing so in a completely different area. That is great and, certainly, law school is not intended to make a private practitioner out of everybody, and that is not what we are looking for.I know that there are many ways you can use your law degree. [However] law school is expensive for the most part and [while] I had a great time in law school, it is a difficult three years.It is one of those gut-check moments. Is this really what I want to do before I jump in? There are many different attractions, and you want to make sure that you are in it for the right reasons. 

David Seeley: That is a great answer and I hear you loud and clear on the challenges that someone would have going into that profession.That is wise advice, and this has been a wonderful time that we have had today, Jonathan. I hear the passion in your voice as well, and that is awesome to hear. Thank you for being a guest on our show today, it has been our pleasure. Is there anything else that you want to add or say before we wrap it up? 

Jonathan Schwartz: David, I thank you very much for the opportunity to let me come on and tell a little bit about my story. It feels a little bit like this is your life and going back talking about some of the things that led me to where I am today, I am very proud of where my career path has taken me. Again, I appreciate the opportunity to share that with your listeners, especially those who are considering the practice of insurance coverage.Those who are thinking about going to law school and especially those who have been in it and are looking for inspiration. How can I develop some thought leadership in this space? Maybe listening to this will energize them to publish, speak or develop their podcasts. It has been a great opportunity to speak with you. I thank you for the opportunity. 

David Seeley: It has been our pleasure and thanks again, Jonathan. 

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After a quarter century helping litigators find the right expert witnesses, Round Table Group’s network contains some of the world’s greatest experts. On the Discussions at the Round Table podcast, we talk to some of them about what’s new in their field of study and their experience as expert witnesses.

The Pursuit of a Career in Law

Jonathan L. Schwartz

2021: Jonathan Schwartz is a partner at Goldberg Segalla and chair of the firm’s Cyber Risk Coverage Practice. Jonathan was the former chair of the 2019 Insurance Roundtable and currently serves as the vice-chair of the Insurance Law Committee at the Defense Research Institute. In addition, He is a top-rated lawyer by Super Lawyers, he has the highest peer rating standard by Martindale Hubbell, AV preeminent, and he has been recognized as a best lawyer in America consecutively from 2018 to 2021 Update: Partner - Insurance Coverage and Extracontractual Liability with Freeman Mathis & Gary, LLP (March 2022-Current)

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