S2E10 - Meet the Team: Will Bennett

Dru is joined by Will Bennett, a Partner in SDV’s West Coast office, to discuss his career, the firm’s evolution, and the shared mission underpinning SDV’s partnership with Fenchurch Law.

Will reflects on SDV’s remarkable growth, what initially drew him to insurance coverage work, how U.S. courts approach policy interpretation, and the procedural contrasts between U.S. and UK litigation—topics he recently explored in greater depth with Joanna Grant during their comparative webinar.

The conversation also covers Will’s recent travels to Scandinavia, his impressions of London, and the distinctive quirks of Lloyd’s drafting and bespoke policies. To round things off, Will offers a glimpse into life in Southern California, from surfing and hiking to playing the mandolin.

Transcript

Welcome And Quickfire Warm-Up

Dru 0:03

Hello and welcome to a special episode of the PolicyHolder Podcast. Today I'm delighted to be joined by Will Bennett, a partner in SDV's West Coast office. SDV, which stands for Sachs, Dawn Burger and Vita, is an American law firm with one mission to level the playing field for insurance policyholders. Like FenChurch Law, SDV has a singular focus on insurance coverage. For those that don't know, Fenchurch Law and SDV have a best friends relationship. This relationship was formalized in April 2025 and involves cross-jurisdiction assistance, information sharing, and a shared common mission. A very warm welcome, Will. Thanks for having me. Great to be here. So on the Policyholder Podcast, we always start with some quick fire questions. Question one Yosemite or Yellowstone?

Will 0:47

Oh. Um let's go Yellowstone. I think Montana's amazing.

Dru 0:51

Okay. You could have said anything because I haven't been to white. Washington State or Washington City?

Will 0:58

Oh my goodness, you're killing me. Washington, DC, meaning Washington City? Yeah. Yeah. Washington, D.C. is pretty incredible. There's some of the best museums in the world there. Yeah.

Dru 1:07

That's you went you went to college near that, didn't you? Near the castle. I did, yeah, about an hour south of there in a town called Fredericksburg. Okay. Well, apologies for butchering the name of your great capital. Summer or winter?

Will 1:18

I live in Southern California, so in Southern California, probably winter when it's nice. Yeah.

Travel Stories And London Memories

Dru 1:26

Summer can get quite hot. I can imagine. And are you an early bird or a night owl? Uh more of an early bird. Okay, great. Jeremiah's rubbed off on me over the years. Well, it's a it's a pleasure to meet you, and thank you for coming on the podcast. Uh, firstly, how has your trip been? You were recently in Scandinavia. Uh, what was that like? Yeah, I love uh Copenhagen. Great city.

Will 1:49

Yeah, how are the Vikings? The Vikings are great. I got a chance to see the Viking Ship Museum, which was really interesting. Um, and it's a great food city.

Dru 1:58

Yeah, I've heard that. I've heard the restaurants there are amazing.

Will 2:00

Yeah, it's I mean, not to not to go off on too much of a tangent, but I think with the the NOMA thing, them having the best restaurant in the world for a couple of years. Yes, then that kind of splitting up and all the chefs going out and doing their own thing, you kind of walk around the city and just find all these like really amazing, incredible concepts.

Dru 2:16

It's cool. No, well, I'm I'm I'm I'm very jealous. And um how how are you finding London? Have you have you been here before?

Will 2:22

This is my third time in London. Uh welcome back. I'm expecting something really newsworthy to happen because the first time I was here was when Princess Diana died, and the second time I was here was the the Meghan Markle wedding.

Dru 2:34

So gosh.

Will 2:35

Um you weren't here for the wedding, were you? Surprise surprise surprise. I was here for my uh my best friend from childhood's wedding, which was just outside the city on the same day.

Dru 2:44

Oh wow, so he got married in was he from America?

Will 2:46

Did he get married? Yeah, he married he married a British woman.

Dru 2:48

Oh, that makes a lot more sense.

Will 2:50

Why is he getting married in the somehow decided to pursue a career in medieval history? Uh so I think he teaches medieval history over here after going to maybe York, University of York or something like that.

Dru 3:02

Yeah, I know. Lovely, lovely town. It's um it's very, very different to New York, I'll tell you that for free. I imagine.

Will 3:08

A lot of similarities with London, though.

SDV–Fenchurch Partnership Origins

Dru 3:10

Yes. New York and London. Yes, that's very true. Um, Will, you are a born and bred SDV. I'm not sure what you call yourselves, apologies if that's wrong. Having been a summer associate at the firm. So I suppose my question is how has the firm grown and changed in your time there?

SDV’s Growth And National Footprint

Will 3:27

Yeah, it's uh it's interesting. It doesn't feel at all like the same firm, but it also feels entirely like the same firm. Um when I started, there were just over 10 lawyers. Um, you would see every single employee in the firm every day. We were all in one sort of loop on a single floor of a building. And uh, with the exception of Jeremiah, who had kind of a hermit office off a little offshoot, everybody else was on one continuous round track. Um, and then you know, Jeremiah and I went out to California, and that was just a couple of us for a little while, but that's absolutely exploded in growth. Florida's done the same, you know. I think these days there's probably 40% of the firm on any given day that that I don't really even know. Wow. And the the work has sort of mirrored that same transition. We've always had big clients, you know, like Jeremiah was talking about in his podcast, I making a lot of references to that. So you'll have to listen to that if you haven't already. Um we've had Turner construction forever. Uh, but then, you know, as people from Turner went to other big contractors, they took us with them and the the brokers associated with them and the and all of that as well. And so the the work has gone from I think probably more regional feeling, more New York City centric, to really truly national, litigating just all over the place all the time.

Dru 4:46

Yeah. Must it must be really exciting to feel like your career grows with the firm as well. As you were getting more senior, the firm's getting bigger, and it kind of took you with it in a way.

Will 4:55

In some ways, it's almost the easiest marketing platform you could possibly ask for coming into as a partner.

Dru 5:01

And so what what attracted you to the weird and wonderful world of insurance coverage disputes when you were back in the day?

Will 5:09

Yeah. So I think SDV is something like 50 lawyers, and I think 48 or 49 of them had no idea they wanted to be insurance coverage lawyers. Same thing happens over here. You fall into insurance companies. So I'm one of that 48 or 49. I was a philosophy major in college. Um, I always enjoyed that sort of complex problem solving. I think the stereotypical comment in the US is like you either go to law school to make money or to help people, and maybe you could add like or be a glorified trial lawyer to that list. None of those were true for me. I just wanted to solve complex legal problems, especially ones revolving around words. And obviously, you know, what's better for that than insurance coverage disputes? Uh and then, you know, on top of that, I really like the people I work with. So that made it really easy.

Why Coverage Law And Problem Solving

Dru 5:54

Yeah, well, no, what it's a great answer. It's funny, you mentioned trial lawyers, though. I'm I'm curious to ask you about the US court system. So am I right in thinking that you yourself do advocacy advocacy because there's no barristers and that there's also a jury for civil cases, for example, in insurance disputes? Because that is wild to me, because we we don't we have a very learned, highly specialized judge in the high court who understands insurance, and it's basically their decision. In the court of appeal, there you have three judges, and they're all even more sort of knowledgeable and experienced and specialized. And it's it's fascinating to me that you you're not necessarily seemingly arguing points of law, but you in them in the states that is, you might be arguing jury points because you're maybe appealing to the jury more than the actual judge if they decide. So this is the very long-winded way of saying how does that situation affect how you present a case. Okay, there's a lot to that. Um I just monologued for about 10 years. My apologies.

Juries, Judges, And Summary Judgment

Will 6:54

No, no, no. Uh really good point. And and yeah, you you I think maybe you're also alluding a little bit to the article that Joe and I just did um on the differences between the UK and the US systems. Aaron Powell It's not that we're turning issues of law into questions of fact. That's not what we do. The insurance cases tend to actually be way more legal questions driven, right? There are issues of what does this phrase mean, what does that phrase mean? And then there are often factual issues that kind of tie along to that, what caused this loss, that kind of thing. And those will be dealt with separately, even though the case is ultimately technically heading towards a right to a jury trial, yes. There are intervals along the way where the judge and the court as itself has the opportunity to rule on the legal issues. And and usually, probably upwards of 90% of the time, insurance coverage cases resolve prior to that jury trial.

Dru 7:56

Right. Okay, I didn't appreciate that.

Will 7:58

Yeah. So like the motion for summary judgment is sort of the main procedural step in the in the insurance coverage case. You get through, you know, you get through your initial pleadings, you get through discovery, reexchange information and do all that stuff. Then you file your motion for summary judgment, and it basically poses to the court, you know, all of the facts necessary to decide this key legal issue are not disputed. And as long as the judge agrees that it can decide that legal issue based on a certain number of undisputed facts, it'll resolve at least that aspect of the case. And sometimes that resolves the whole case. Often it resolves the whole case. Even where it doesn't technically resolve the whole case, I think it probably practically resolves the case 90% of the time. Because there's only, you know, it's it's kind of weird to go in front of a jury and only try like 10% of your truly of your case. Yeah. You know, the it's not the same world as like, did this person run the stop sign and cause this accident? You're trying the whole picture to the jury in that case. In the insurance case, it's like there's just this one little narrow fact that matters to this giant legal analysis that the jury will never see. Right. That being said, insurance companies have a terrible reputation in the United States amongst the jury pool public. Um so having that element of like, hey, insurer, when we go to court at the end of this, you're gonna be in front of a jury who hates you. Plus, having US bad faith law and things like that is kind of a nice tool to have a stick to beat the insurer with.

Dru 9:27

Yeah. Um that that's that makes a lot more sense to me now. That thank you, Will. Um, and you are a bit of a sage because you sort of predicted my next question about the article that you wrote with uh with Joanna Grant about the similarities and differences between the the UK and the states. So in that process, what did you find most interesting or surprising in in what on your journey of discovery, should we say, about the differences between the England and the States?

Bad Faith Pressure And Settlement

UK–US Interpretation Contrasts

Will 9:55

It's probably just the the backdrop by which the courts will approach the issues that we're dealing with as insurance coverage layers. Um there's all sorts of really specific procedural things that are different and interesting. You know, you guys don't have depositions, for example, where we put the witness in a room and talk to them for eight hours about whatever we want and force them to answer questions in the discovery process, which is brutal. And I love that you don't have it, it'd be nice. Um but more interesting, I think, from a you know, 35,000 feet, is that 11,000 meters, something like that, uh, perspective, is you know, the US court is extremely governed by the plain language of what that policy says. And only if we can't, if the court can't figure out from just the face of that document with no background knowledge on insurance, no knowledge of the intent of the parties, any of that, only if the court can't figure out what it means based just on that will it look at anything else. Maybe. Right? Then maybe the court will consider parallel evidence, extrinsic evidence, you know, what did the underwriter intend? What did the broker say? What did the insured expect? Or it might just say, if this is unclear, the policyholder wins. I like the sound of that. Quite a few states that say that. Yeah, some big states. You know, Florida basically does that. California would say, what did the insured reasonably expect at the time it bought the policy, right? And then if we can't figure that out, then the policyholder wins. The UK is obviously completely different from that. The UK has got all these concepts of business common sense and reasonable understanding based on the ordinary meaning. Ordinary meaning of the words of the policy. Yeah, but but but based on the information that that was reasonably available to them at the time of the transaction and things like that. Um, which is, you know, I think a big piece of the confusion over all the leg three stuff that our firms have both been very involved in. You know, you you put a phrase like that in front of a US court, you're gonna get a completely different outcome, probably, than if you put a phrase like that in front of a UK court. The the understanding that the court's gonna be able to have about the background of those words is gonna be completely different and it's gonna influence the outcome.

Dru 12:12

Yeah, that sounds wonderfully convoluted to guess. Two different two two different understandings of the of the same word in two jurisdictions. And will I notice that you posted on LinkedIn, I have been sort of internet stalking you in preparation for this podcast. Oh boy. Uh, that you shared your eagerness to give a talk in the old library of Lloyd's. Uh-huh. What so what do you think of when you hear Lloyd's of London?

Will 12:34

Truthfully, as a policy holder lawyer in the US, um the enemy. No, no, not at all, not at all. Um, I think, oh boy, I'm gonna have to spend some time with the words on this policy because um there's so much less uh consistency in how things are written, and I can see the the British backdrop in the drafting of the forms here. Um and in the US as a policy holder lawyer, with all those rules I just talked about, where we're talking about plain language with Lloyd's forms. Honestly, I'm often kind of searching for okay, where's the thing that's not super clearly written for the US court that I can point out as something that they can latch on to, especially because you know, a lot of times Lloyds will tend to issue these policies that have, you know, seven forms and one of them's the lead form, but six of them follow, and you know, 80% of the way follow, and 20% is different stuff, and all that just creates a complex web of like the US court's gonna struggle with that.

Dru 13:38

Yeah, no, and also I think as as um as Jeremiah Jeremiah and I spoke about, uh, the bespoke nature of a lot of the policies as well means because I understand that in the States it's kind of like here's your standard policy, whereas there's actually quite an interesting Wikipedia page, which is some of the weirdest things that Lloyd's has insured. And it's it gets pretty bananas. As in there's a very famous Australian cricketer, not that you guys have any idea what cricket is, but they he had a very famous sort of handlebar mustache, and that was insured. Not him, his mustache was insured for like a hundred thousand dollars or something. I think there's something because it was so iconic.

Will 14:16

I think there's something kind of iconic on there about Dolly Parton, but I'll let you look that up and see.

Lloyd’s Forms And Bespoke Policies

Dru 14:20

Yeah, no, okay. Moving swiftly on. Um Will, it's been it's been great to chat, but final questions more about more about you, I suppose. What's what white might we find you doing on the weekend? What are your sort of hobbies?

Will 14:36

Yeah, a lot of things. Um, I'm definitely gonna start my weekend with a class at my gym and then go to the farmer's market after that. That's pretty much what's very Californian of you. Every single week. Probably gonna play my mandolin. I might go surf potentially, might go surf with Jeremiah. Um, we've done that many times. Go for a hike, probably take the dog for a long walk.

Dru 14:56

California just sounds like the nicest place. It's pretty nice. Yeah, I've pretty much I've been I've I've been there and it's just the climate for an Englishman, it's so good.

Will 15:05

Even for an American for many ways, it's so consistently good.

Dru 15:08

Yeah, and also it's stunning. Northern California. Sorry, I don't want to, but I I do think that parts of Northern California, like around San Fran, uh amazing. But I think the thing is, I think I've been to LA, but I think, given that I'm from England, I think it was a bit too hot for me. And I also went out to Joshua Tree, which is amazing. That's hot, but that was really hot. And then I went up over up the state and I was felt a bit more bit more at home where it wasn't quite so warm. Well, that sounds like a lovely weekend. I won't tell you what I do because it's a lot less interesting. But well, thanks so much for coming on. It's been it's been great to meet you. This is the first time that we've actually met, but I'm hoping to see a lot more of you over the next couple of days before you uh head back stateside. I'm happy to be here, I'm enjoying it. Thanks very much.