Kennedys Alumni Network podcast

The Windy City and beyond: lessons on the market with John LaBarbera and Matt Walsh

In conversation with Anna Weiss, Global Relationship Development Director at Kennedys

From opening a new office to switching sides at a global broker, John LaBarbera and alumnus Matt Walsh share practical takeaways for navigating clients, courts and carriers.

Chicago is a small market with a big presence. In this episode, Kennedys Partner John LaBarbera and alumnus Matt Walsh (now Managing Director at Aon) revisit the early days of building Chicago; what changes when you move to the broker side, and the forces shaping US risk and claims today. From nuclear verdicts to evolving exclusions. Their common thread: relationships and reputation travel further than any single case win.

Takeaways:

  • Treat every difficult conversation as reputation management.
  • Tie legal advice to business impact.
  • Anticipate exclusionary wording shifts around emerging risks.
  • For multijurisdictional programmes, align courtroom realities with corporate risk appetite early.
  • Invest in your triad: client–carrier–broker

Anna Weiss
[00.00.00]
Everyone who's been part of Kennedys, whether you're with us now or have moved on, has helped shape the firm into what it is today. Whether your time here was brief or spanned many years, you remain an important part of our story. I'm Anna Weiss, global relationship development director at Kennedys, and this is the Kennedys Alumni Network podcast. Today we're heading to the Windy City, known for bold voices and persuasive talk, to hear about the early days in Chicago and beyond, transitioning to the broker side, to what keeps us up at night and not just eating deep dish pizza. But regardless of how many years you've been practicing, there are always new lessons to learn. I'm joined by John LaBarbera, a fellow Kennedys partner, and alumnus, Matt Walsh, now managing director at Aon. Thank you, John and Matt, for joining us today to swap stories, share a few tips and traps, and talk about what makes a Chicago market tick and what those lessons can teach us about navigating client relationships anywhere in the world. Welcome to the podcast. So, John, tell us a little bit about where you started, where you're now and your shared history with Matt. 

John LaBarbera
[00.01.16]
That's a broad question, Anna, but I started before practicing law, working in the insurance industry. I had positions in underwriting and claims, and then in the early 2000, I had a second career and became a lawyer. So I've been practicing since 2001, and I work primarily in the insurance and reinsurance space in Chicago. I also split my time in Texas and throughout the world, essentially, and my relationship with Matt goes back to 2010, where we met and worked together as partners at another law firm. And Matt had the lucky circumstance of being in an office next to mine. So I'm sure he's got lots of stories about me based on that and that alone. But Matt and I have known each other for 15 years. We've worked together, we're friends and really happy he's here today on the podcast with us. 

Anna
[00.02.55]
Great. Thanks, John. And I think that's a great segway into hearing your view Matt on, you know, how it was to be neighbors with John and what you two achieved together. I know you have some amazing accomplishments that you did setting up the Chicago office. Love to hear a little bit from you, Matt, on that. 

Matt Walsh
[00.03:13]
Yeah. So yeah, as John said, we met in 2010. We had another law firm. I was at that law firm for years before John joined, and it was a when John joined, it was a godsend. Not only did I gain a friend, but I gained a working partner that I valued very much. And we were there for three years. And then I guess it was in August or September of 2013, when I'll call it Kennedys’ predecessor, Carroll McNulty & Kull. This is more John's doing reached out and we decided to start the Chicago office of Carroll McNulty & Kull. And that happened to be the same day that Carroll McNulty & Kull also started their Philadelphia office. So he went from just new Jersey to now new Jersey and Philly and Chicago. So there was ten of us who started that office again, six from our firm and four from another firm. And it was a very hectic but exciting time, and I was there until 2022, I believe, when I left and joined Aon as their head of casualty claims. So here we are, and John and I have remained friends throughout. 

Anna
[00.04.30]
That's fantastic. So a little known fact, is I actually lived in Chicago during that time when we did not have a Kennedys Chicago office, and I think I was probably the first person to register some kind of tax status there, which was kind of funny. So it's really exciting to see the growth of the Chicago office and all across the US. And I know, John, you're also in Austin a lot and you travel globally a lot, which is fantastic. But let's take a moment to go back to Chicago, and let's talk a little bit about the personality of the Chicago insurance market. If you can share, you know, a little bit of history about why Chicago is quite a hub for insurance and how it has evolved during the time you've been practicing. John, would you like to take that? 

John
[00.05.18]
Yeah, certainly, Anna. And that's a that's a great question. Illinois and Chicago itself has long been a hub for the insurance industry. It is the headquarters of some of the largest insurers in the world and internationally. It is also the headquarters in the US for a number of years. So it's a great marketplace. And in addition to the insurers, you have the two biggest brokers in two of the biggest buildings in the world, right here in Chicago. So I think it's been a blessing to have access to those resources, those clients, those kind of relationships. And it also has allowed for growth. I mean, the legal practice in Chicago is, it's a big city, but the insurance litigation or insurance advisory practices is really small. It's a handful of people. And so I've been able to develop great relationships with folks that have carried on throughout the years, including Matt and Martha and a number of our colleagues who were in the Chicago office and went off to do other interesting things, either in the insurance world or servicing the insurance world. 

Anna
[00.06.34]
Yeah, it's great to see, you know, the journeys that our alumni have taken, all the different avenues and angles that they have gone. And, Matt, perhaps now's a good time for you to tell us a little bit about your role at Aon, how the transition was. And you're one of the brokers in the big buildings that I always saw downtown. And I know that we have a lot of in the skyline of large brokers and insurers. So could you tell us a little bit about that transition and life, you know, now for you? 

Matt
[00.07.03]
Yeah,  it's been a great transition. And again. You know, just the background. I wasn't looking for it. It just so happened that one of my best friends was at Aon, and they needed somebody to run their national casualty claims. And the transition from a work standpoint was easy in one sense, considering I'd been, you know, I didn't have to get clients anymore. I don't have to bill. And that was great. But from a from a work standpoint, there wasn't much of a transition at all. Because what I'm doing at Aon, really two things our coverage, advocacy for our clients. Although now I'm not on the insurer side, I'm on the policyholder side, but it's really no different. It's reviewing coverage issues and figuring out, you know, who's right, who's wrong. And the other part of my work is really looking at drafting policy wording and all the stuff that I just mentioned. The coverage issues and the drafting and policy wording is stuff that I did as a lawyer. So it was a pretty easy transition. I am not a broker, so I didn't have to learn, you know, I didn't have to learn a new skill set because that that's not me. So what? The transition was easy and it's been wonderful. And frankly, I still work a lot with Kennedys sometimes on the other side, but also referring stuff to Kennedys when it's not, you know, an insurance type matter. But it's so it's been a great transition. 

Anna
[00.08.30]
That's fantastic. And I think you've touched on an interesting point there, which is your role covers sort of the origination, the drafting, the commercial aspect to insurance as well as occasionally then as it moves into the claims side. And I think Kennedys was historically known more for the claims and the defense type of work that we did. But over the years, I certainly know my practice and the practice of many of us at the firm has evolved. So it's really wonderful to hear that you are using, you know, Kennedys now in your role, including on the non-sort of contentious aspects to insurance. And so we've really evolved a lot in that sense. And you touched on a point which was, you know, you're not a broker. You're looking at it from the eyes of the lawyer. Can you share with us a little bit about, you know, the stakeholders that you now have? And you know, how your clients have you like, has shifted since you've been on a different in a different role looking at things you're no longer in private practice. You're no longer looking at, say, your insurer or reinsurer client, but your client base is probably a little different. And how you navigated through some of that change. I would love to hear a little bit about that. 

Matt 
[00.09.45]
My client base because I'm the, the national lead is all big markets, you know, whatever you think is a fortune 500 type of company, that's my client now. But frankly, when there's advocacy needed for me in terms of a claim, the people that I'm advocating with not for, but with are the same insurers that I worked with when I was at Kennedys. So that side of the equation hasn't changed at all. It's just I'm just I just happened to switch from one side of the V to the other side of the V, kind of. So it's really, I mean, Kennedys, when we were doing coverage work for our insurers, we were doing coverage cases against the same types of clients or firms or mega corporations that I'm now working with. So it was it's kind of like, you know, I get the best of both worlds, seeing how these major insurance companies work and now seeing how these major, you know, companies work. So it's very interesting in that sense. 

Anna 
[00.10:48]
That's great to hear. And, John, I mean, your practice has evolved a lot as well over the years. I think that for Kennedys through Kennedys and I know we've handled some files, some cases together, and we get all sorts of curveballs these days. What do you see as what's coming along? How has your practice evolved? How do you see that the industry is moving? 

John 
[00.11.10]
Yes Anna, so I started out as a young lawyer working. Exclusively in disputes, but disputes of all natures defense, products, liability defense, professional liability. I did some insurance coverage work over the years. It is now evolved to being more reinsurance focused, both on the transaction side, contract word and contract drafting and advice in that area. So very similar to Matt, in that regard, but also in disputes. And my practice in the last decade has evolved to include more regulatory and transaction advice, with companies primarily looking to enter US markets and helping them with licensing and corporate formations and guiding them through those processes. So it's been a great evolution, but I always consider my role the same. I'm an advocate, of course, for my client and my client's positions, but I'm also there to give them advice as well. So even in contentious disputes, my goal is not fundamentally different than Matt's goal, which is to provide my clients with the best advice that we can give them. And then also being a zealous advocate for them when we're in in the dispute room, be it an arbitration or a litigation proceeding. 

Matt
[00.12.33]
And sometimes, Anna and John, and John, you know this well, and so do you, Anna. Sometimes the advice that you're giving on either side, whether you're giving it to the insurer or giving it to the client, isn't necessarily something they want to hear, but it's very important to you have the advocacy piece, but you also have the advice piece saying like, well, you know, you're wrong or something like that, but that's you got to keep that in mind when you're doing the kind of work we do. 

Anna 
[00.13.01]
Absolutely. John, do you want to say something about that? 

John
[00.13.05]
It's critically important. And it goes to our relationship with our clients. They have to have trust that you're giving them the right advice. And that is demonstrated by explaining why their course of conduct might not be the right course or why the position they're wanting to take might not be the best position, not only in a particular in a particular case, but from a business perspective. So being able to have a good relationship with clients that you can have those candid discussions is of the utmost importance. 

Matt
[00.13.40]
I'll add one more thing to that, Anna. And what I've learned more so being at the broker than I did while being a lawyer for insurers is that you have to understand that this these are really partnerships. I mean, the client, the insurer and the broker, it's real. It begins as a partnership and especially with insurers that are ongoing. Writing ongoing business with these clients. It's not only from a you know, you don't only look at it from a claims perspective and you know who's right, who's wrong, but you've got to look at it from a business perspective, saying, you know, maybe we can take one on the chin here. Because of the strong business partnership we have, not only with between the client and the insurer, but also with Aon, because, you know, remember, Aon's the one who's driving a lot of who gets the business and who doesn't. So the partnership thing has really resonated with me once I got to Aon and how important the partnership stuff is, because I didn't see that as much as just being a lawyer and an advocate for the insurance company when all it was trying to win that claim. The partnership thing didn't come into play as much, but it certainly resonates now when I'm at Aon. 

John
[00.14.53]
I think you all recognize that. And that's why I'm not surprised you're successful is because you've always taken a holistic approach to dealing with client problems, and not just myopically focusing on the case in front of you, but the implications and the ramifications that go beyond that. And really not only giving excellent legal advice, but excellent business advice at the same time. 

Anna
[00.15.19]
Yeah, definitely the case. I think that is the same across the globe. And the world is becoming smaller and smaller. And I think the relationships that we build is really what helps business move. And these things get handled, you know, gracefully, especially if it is a difficult topic or you're giving someone some advice they really don't want to hear. But, you know, if you built that rapport and you have that partnership, as you say, Matt, it's that trust that you come to say, well, okay, on this occasion, okay, I'll just have to suck it up and move on. So, you know, that's one of the reasons why I think an alumni network and the opportunity to connect with people in the market that have touched with Kennedys or its successors or predecessors, you know, CMK’s alumni, you know, it's so great for us to maintain contacts and build our networks. And then the goal is eventually, you know, to make new connections with the other connections that come along, in the passage of meeting up with other alumni. So, yeah, the market is small and we are there to all help each other. 

And ultimately, insurance does help make the world go around in so many ways. I think for the outside, that may sound like a very funny comment to make, and certainly a lot of people don't really understand all the nuances of insurance. But insurance really does help, you know, make things move and resolve a lot of issues. And so doing it in partnership with each other is definitely something that helps and also makes our life a lot, much, a lot better, a lot easier. Right? But there must have been a time in each of your roles where you've had a difficult situation or you've thought, oh, I wish I had done that differently, or how could I do that better? Or maybe you were just really good at keeping your cool in those kind of conversations where you are delivering news that they may not like. Do you have any stories you can share, or any examples of something where you can say, oh, I wish I'd done this differently, or I learned to do this over time, and this is now my go to and how I approach these types of things. Or is that a very difficult question to ask? 

John
[00.17.21]
I don’t think you have enough time in your podcast, because I can always find something I could do better or differently. I think it's hard of part of being a lawyer and providing legal services to clients is always understanding that there is room for improvement. No one person is so good at their craft that they can't learn something or do something. One of the most enjoyable aspects of my job now is working with young lawyers, because they bring energy and enthusiasm. Everything's new to them and it's an excellent environment to practice in. In terms of things I've learned with clients. Oh, yeah, I've had clients explained to me, you know, you gave us this bit of information. Next time try to do it this way. Right. And you got to take those things to heart. Everyone who knows me will tell you I'm extraordinarily defensive, though, so it may not appear that I take those things to heart. And by nature, you know, we're in a combative business at the end of the day. So one thing is to have a tough skin. But the other thing is you really need to listen to your clients. It's the most important thing. The marketplace is small, and your reputation takes years to earn and can be destroyed in seconds, and you may never get it back again. So really, trying to be as levelheaded, as reasonable, and certainly open to other people's thoughts and ideas is of the utmost importance in having any hope of being a success, as an attorney or as a business person who is responsible for providing services to others. 

Anna
[00.19.17]
I think that's very sound advice, John. Totally agree. Matt, anything you want to add on onto that? Like from your experience, I know you both open and ran an office. It's not just about the technical. There's the people aspect that you touched on John, and anything to share there?

Matt
[00.19.33]
I think John pretty much clocked it pretty well. And it's really a learning curve. I mean, there are lots of things I did as a young lawyer that, you know, I wouldn't do now. I mean, I can't give you any examples, but it's just a learning curve. And frankly, you know, my demeanor has always been relatively calm, which I think helps me. But yeah, there's lots of things I would I would do differently. If I look back at myself, you know, 30 years ago when I started out, or maybe even more than that. Yeah, there are things like I didn't know and I maybe I didn't do it right. But I've learned that over the years and I still do things today after being a lawyer for 35 years now that maybe, you know, maybe I'd like to change. Not as much as I used to, but yeah, it's just it's a learning curve. That's all it is. 

John
[00.20:20]
And even outside of the practice. When we opened that office in Chicago, it was pretty entrepreneurial in a sense. We're working on a boxes. We just moved into space that was, you know, not renovated. Renovations were happening down the hall for space we'd eventually take over. You know, you have to get used to a new, you know, a brand new office. There were a group of us who had worked together for  a long time, but we had other people joining us and other people outside of Chicago that we were getting to know, getting to work with. So it was really it was an exciting time. I think it's because people like Matt and Martha and Ben Bloom, who retired recently from Kennedys, you know, that was a great core group of people. Even Daisy Khambatta, who was in 
Chicago, who heads up our Austin office now, it was a great group. The good thing about it was we were all friends working together, kind of feeling our way through the dark protect particularly, you know, those first few days. 

Matt
[00.21.24]
Yeah. And frankly, I mean, John knew Chris pretty well back then, but I, I go back with Chris Carroll, back to his days at McElroy Deutsch, so I knew Chris and Meg and Gary way before we joined. In fact, they tried to hire me back in 1995. Oh, wow. And I'm like, I'm not moving to New Jersey, but so the transition was easier, I think, for folks like John and I, John, who knew Chris from a couple of cases working on, and me, who, who knew the, the, the Kennedys folks from way back so that that made the transition easier instead of having to get to know everybody in New Jersey, I knew all the, you know, a lot of the principals already. So that made it easier. 

Anna
[00.22.06]
Yeah. Well, congratulations. I think it is a great success story, and I love that you all started as friends and you still are all friends, regardless of all the different paths you've all taken. And you said something there, Matt, I'm not moving to New Jersey and a Chicago is home for you. So let's talk back a little bit more about Chicago. So I'm going to ask you some kind of fun questions. Now for those that don't know Chicago so well, I mean, what's it famous for? Let's think… pizza. So let's start with that. Let's go for a deep dish or a thin crust. Matt, are you a deep dish guy or something else? 

Matt
[00.22.40]
Well I'll call. I do love deep dish, but I'll qualify that as saying Chicago's got its own style of thin crust, which isn't like anywhere else. It's called tavern style or cracker style pizza, and it's very thin. It's usually well done. It's not like the slices you're getting in Philly or New York or anything like that, cut in squares. That's probably my favorite pizza. So I'm putting the I'm putting the third entry into your question. I say tavern style pizza is my favorite. 

Anna
[00.23:08]
Excellent. And you, John, which one would you go for? 

John
[00.23.11]
I agree with Matt, I, I prefer the tavern style and I consider that the Chicago style of pizza 

Anna
[00.23:19]
Awesome. And are we Cubs or White Sox or which team do we support? Or none of the above?

Matt
[00.23.26]
No, it's only the Cubs and people that support the White Sox like John. They don't really belong in the city. You know, it's the country. 

John
[00.23.33]
I'm a White Sox fan. I grew up south of the Eisenhower Expressway. So that's where I get my bonafides from. And I recognize after many years that people have the right to support the Chicago Cubs. 

Matt
[00.23.49]
I'll say this. And I'm not one of those Cubs fans that hates the Sox. I wish them well. There's an old saying in Chicago from White Sox fans. It says, who are your two favorite teams? And the answer is the Go-Go White Sox and whoever plays the Cubs. 

Anna
[00.24.11]
There is something really special about going to Wrigley Field, though. I love that experience of going to watch a game. It's really fun. 

Matt
[00.24.19]
Wrigley Field is a beautiful park, I'll give you that. 

Anna
[00.24.22]
It is beautiful. So yeah, let's talk a little more on Chicago then. So you're both has spent a lot of time with your career in Chicago, but I know that the roles you both have now take you further afield. So outside of Chicago, is there a favorite city that you go for work or that you have particular dynamic in the market that you like to go to? I mean, for work, what would you each say? Matt, I'll start with you. 

Matt
[00.24.47]
Well, I would like, since I'm national, I'm all over the place, but I mean the primary places I visit a lot because of the insurance industry are New York, London and Bermuda. And I got to say of those three. I like Bermuda the best just because it's Bermuda. 

Anna
[00.25.05]
Interesting. Good choice. And you, John?

John
[00.25.09]
Oh I have to say Austin, but, I think New York or London, just from a business perspective, though, do a lot of my work in Kentucky, New Jersey, Pennsylvania, California. So we get all over. 

Matt
[00.25.26]
And, you know, like we said at the beginning of this about Chicago, how it's a huge insurance industry, it's also a huge litigation industry for coverage cases. 

John
[00.25.35]
But a lot of my litigation work has been in the south, the southwest and the East Coast. So it gets around. But, you know, Chicago, the Circuit Court of Cook County is the busiest court system in the world. There's always opportunities for litigation in Chicago, and having a familial familiarity with it is very helpful for clients, because it's overwhelming to a lot of lawyers who just come to Chicago for the first time. I personally grew up there. So I'm very comfortable in that biosphere, if you will. But it's very different than other places like New York or New Jersey, that that have different practices and different procedures. 

Anna
[00.26.25]
Yeah, and I think Kennedys now has offices all across the US, which is great. And your opening of the Chicago office was kind of the beginning of a huge amount of growth in the US beyond the new Jersey, New York offices. And I think the fact that we have lawyers in those offices that are qualified in different jurisdictions, like yourselves, helps us to understand and give our clients, you know, that more diversified advice, or certainly for me, for example, as an English qualified lawyer, when I'm speaking to people in the London Market, I understand what their concerns are. And so when they see things that are different elsewhere, I can help sort of highlight and say, this is where we need a lawyer from this jurisdiction or that jurisdiction. And it's really great that we now have that global presence to be able to do that. 

But there are quite a few areas in the world right now where it's a common issue across all jurisdictions. And I'd like to spend a couple of minutes, if we can, about what is it you think that is keeping up our clients at night? Right now are the issues that we're going to encounter coming down the line, you know, in the next couple of years that you think would be worth sharing a few thoughts on right now? 

Matt 
[00.27.37]
Well, I can tell you from my perspective and from a claims perspective. You know, the thing that's keeping clients up at night are the verdicts, the what you call nuclear or thermonuclear verdicts. Because it not only affects, you know, it affects their bottom line, it affects what they're from, terms of what they got to pay and claims. Because there's, you know, with my clients there's huge sur is huge deductibles, but also the premium dollars they got to spend to get insurance these days. That's what's keeping them up. You know coverage issues come and go and you deal with those one on one. Yeah, that's the main thing. The other thing is. Because of, you know, what I call emerging issues and everything. You know, we're seeing, you know, insurers come up with different types of exclusions all the time. So trying to navigate those keeps clients up as well. Probably not as much as, you know, the what's coming out of their bottom line from the nuclear and thermonuclear verdicts. But those are really the two things, I think, that keep our clients up. 

Anna 
[00.28.45]
Yeah, that's very interesting. And John, what would you say that you see coming? 

John
[00.28.49]
I think on the insurer and reinsurer side, it's the exact same the exact same things, the litigious nature of the United States and the uncertainty as to jury, the jury system and the results that that can ensue from there. They struggle with that, particularly companies outside of the United States. Even people who worked for the United States for their entire career don't quite have an appreciation for the volatility. And I think volatility is if I had to pick a word. That's what keeps people up at night. Um, yeah. Volatility and uncertainty. 

Anna
[00.29.30]
Yeah. And I think actually I mean volatility certainly in the US and as you touched on the jury aspects, but actually globally there's a lot of volatility right now which it must be a major concern for insurers and for clients. You know, for the corporates who are trying to plan their next five years of business and whatnot and not knowing exactly which direction things are going to go, it's very tough. Are there any emerging themes, litigation trends or regulatory shifts that you see particular to Chicago or beyond that are going to impact? I mean, beyond the topics that we talked about, anything particular regarding maybe regulatory? John, I know that you mentioned earlier, we've seen more insurers register and want to sell insurance across the United States from the global perspective. Are you seeing that there is an upward trend to that, to registrations, or are you encountering more sort of red tape and challenges in terms of getting things done? 

John
[00.30.31]
No, from a regulatory standpoint, I see a lot of activity with clients wanting to enter the US markets and the regulators throughout the country are excited at the prospect. Many jurisdictions like Oklahoma, Rhode Island, Connecticut, South Carolina, very, very interested in working with the regulated community. So I think there's great opportunities along with that is managing risks as well, because the topic we just ended with, once you start doing business in the United States, that's what you have to contend with. So it's the people I'm working with generally have an appreciation of that and their comfort in the space that they're looking at. 

Anna
[00.31.22]
Yeah, I can imagine. And Matt, anything to add in that particular?

Matt
[00.31.27]
Well, from a claims perspective, you're always going to have, you know, plaintiffs coming up with, you know, new liability theories, new products. And, you know, everybody knows about PFAS, the rubber chemical, which hasn't really hit yet from a buy perspective, but certainly has an environmental perspective. But you're also seeing things like the biometric information privacy acts. That's really started all the way. But frankly, the biggest concern now are probably companies that have large auto fleets, because auto is really driving a lot of these nuclear type verdicts. And, you know, stuff like third party hauling is a big issue that's coming down the pike. Now, when you're when a company hires a third party to haul their goods and you know how they can be protected from that liability, which players attorneys are trying to, you know, pierce that now. So those are a couple of things that I'm seeing a lot of. 

Anna
[00.32.22]
How do you see that the legal market's going to change then? And what do you think is something that you personally will do to keep learning and adapting with the changes that we see coming along? 

Matt
[00.32.33]
Well, I don't from a personal perspective, I don't know. But for me, industry perspective and I'm part of this like entity that's trying to reduce the volatility in the legal market. So the insurers, clients and brokers have gotten together to try to, you know, reverse the course of the volatility, the nuclear verdicts, the advertising, third party funding is a huge thing. We're finally coming together as a group hiring lobbyists and trying to reverse course a little bit to the extent we can. We're way behind the very well-coordinated plan of Spa, but that's something I think is a very important point is that insurers, clients, brokers have to work together to try to push back on third party funding. Attorney advertising, nuclear verdicts, runaway judges, stuff like that. And I think that's occurring as we speak. I'm not promising how successful will be, but that's something that I see that in the future that would really help. 

Anna
[00.33.36]
Good that it's really good to hear that. I think that's very valuable. And certainly it's our responsibility wherever we can I think in the sector, in industry, we're in to try and help affect those changes and not forced by numbers and success together is always greater than our individual efforts. John, anything you would like to add on that in terms of how you see that you'll keep up to speed with, you know, all these changes and how we can facilitate anything, at least from our perspective?

John
[00.34.05]
Well, in my view, it's technology. Technological advancements are changing everything. If I go back to the very beginning of my professional career. I didn't have a computer on my desk. If I wanted to send a letter, I hand wrote it, put it in the bin, it went down to typing. It came back up to me, I read it, I edited it, went back, it came down. Those days today are gone and everything is instantaneous communication. I not only have a computer on my desk, I have one in my pocket that I can make telephone calls with too. And I think the use of technology is just going to further accelerate and change the way the world operates, which will change the way my client's industry operates, and it'll change the way I operate. So really just trying to stay on top of that and being able to adapt to that ever evolving environment. 

Anna
[00.35.02]
Totally agree with that. I think that we cannot avoid the fact that it's coming. It's been here for a while and it's not going anywhere. Right. So it's only a matter of staying ahead of the speed at which it's moving, which is the challenge, I think, because it's taking a life of its own. And so keeping up to speed is key. And in terms of the Alumni Network and what we're building at Kennedys, what are you both most excited for out of that network? I mean, the fact that we're here and we're sharing fantastic stories of the past, also considerations of the present, looking forward to the future. From my perspective, it's been really interesting to hear your perspectives, but there must be something as well that you reach happy to share about what the network will hopefully provide to you and what you're excited for coming up in the next few months. 

Matt
[00.35.52]
I mean, from my perspective. Honestly, it's just getting to see people that I was friends with that I haven't connected with in a while. And, you know, a lot of these folks are at insurance companies who I deal with. So knowing someone there who I worked with before, you know, if I have an issue with that particular insurance company, it's a little bit easier for me to connect, you know, if they're the right person to connect with and talk things in a very straightforward manner. So that's really I think that's a great benefit for the Alumni Network. And frankly, you know, like I said earlier, I've, I have referred several things to Kennedys on an insurance wave just because, you know, I relished my time there. And I think there's great lawyers there and I wouldn't refer something to someone I didn't think was a good lawyer for the client I had. 

Anna
[00.36.45]
That's great. And just for the record, I did not ask Matt to say that. I really appreciate that! That's very good. But I think that is, you know, that is the goal is really to get everybody together, to reconnect, to make more connections. And as we've said, this is a people industry. It's all about those relationships and the trust that we build. So finding other people from Kennedys, even those that you didn't know already and meeting the team as it is now in Chicago, that's something I'm really excited for when we come and do the alumni events. I think it's going to be great for a new people to meet each other and share their common, you know, shared journeys, but also independent and separate ones that we can all learn from that, which is great. How about you, John? 

John
[00.37.29]
What I think is great about the alumni organization is just having an outlet to keep relationships going. We're all busy. Everyone has really busy careers, but it's a group of really bright, intelligent people, many of whom I'm friends with, and it's a great opportunity to just keep in touch with people and not necessarily hoping to get business from someone, but maybe bounce ideas off of a lot of what we do. Day to day is not run of the mill. Typically, we get hired because we're dealing with a topic or an issue that no one has dealt with before. So getting other perspectives, getting the broker's perspective, getting a policyholders perspective. It is invaluable in allowing me to provide advice to my clients and to keep a network of people because you never know where anyone's going to end up. I mean, people who knew me in 1996 would not anticipate what happened today. And so, yeah, it this is an industry built on relationships. It's built on partnerships, as Matt said, and just finding a good outlet for fostering those things. I think really you can't measure the value of something like that. 

Anna
[00.38.52]
Fantastic. Thank you. And I know we've handled some really interesting curveballs before, so you're absolutely right. Those are the fun ones we love to see. Don't we? I was smiling while you were commenting on that. So one last question for each of you, and I'd love to ask this question because I never know what answer I'm going to get. But if I was to ask you one word to describe Kennedys, what would that one word be? 

John
[00.39.19]
I think the word that best describes Kennedys to me is collaboration and global. I have to pick two words because I'm a lawyer. I can always say in two words what others can say in one. 

Matt
[00.39.32]
Yeah. You know, what came to mind at first is growing. Growing. I mean, let's look at that from where we were in 2013 to where you are in 2025. It's just. Yeah, it's been amazing. 

Anna
[00.39.46]
Well Matt always we because once an alumni, always an alumni I think so yeah you can have it as growing. I love that. I think those are both great words. Well the three words are all fantastic words. 

And thank you, Matt and John. That has been a fantastic conversation. I loved hearing how those early experiences shaped not just your relationships, but your whole careers. It's a reminder that every market has its own rhythm, but how each market can also be quite similar, and the better that you get at learning from experiences with clients and in whichever room and place you are, wherever you are in the world, the more that you can grow and develop and there were always able to learn something new. If you'd like to stay connected, join our upcoming alumni events in Chicago, New York, and Miami. Or register for the Kennedys Alumni Network to hear more stories, insights, and opportunities. Please do check out our website. Thanks for listening and thanks again to John and Matt for sharing their lessons from the market. 

Highlights from the conversation

Building something from the ground up

Timecode: 00:03:13

“When John joined, it was a godsend. Not only did I gain a friend, but I gained a working partner that I valued very much. We were there for three years. And then… we decided to start the Chicago office… there were ten of us who started that office again, six from our firm and four from another firm. It was a very hectic but exciting time”

Matt Walsh

Advice clients don’t want to hear

Timecode: 00:13:40

“Sometimes the advice that you're giving on either side, whether you're giving it to the insurer or giving it to the client, isn't necessarily something they want to hear, but it's very important… you have the advocacy piece, but you also have the advice piece”

Matt Walsh

“They have to have trust that you're giving them the right advice. And that is demonstrated by explaining why their course of conduct might not be the right course… not only in a particular case, but from a business perspective.”

John LaBarbera

Reputation travels further than any single win

Timecode: 00:17:21

“The marketplace is small, and your reputation takes years to earn and can be destroyed in seconds, and you may never get it back again. So really, trying to be as level-headed, as reasonable, and certainly open to other people's thoughts and ideas is of the utmost importance.”

John LaBarbera

What’s keeping clients up at night

Timecode: 00:27:37

“The thing that's keeping clients up at night are the verdicts, the what you call nuclear or thermonuclear verdicts… it affects what they've got to pay and claims… the premium dollars they’ve got to spend to get insurance these days.”

Matt Walsh

“They struggle with that, particularly companies outside of the United States… volatility is, if I had to pick a word, that's what keeps people up at night.”

John LaBarbera