Episode transcript:
Note: This transcript is generated from a recorded conversation and may contain errors or omissions. It has been edited for clarity but may not fully capture the original intent or context. For accurate interpretation, please refer to the original audio.
JOHN QUINN: This is John Quinn, and this is Law, disrupted, and today we’re talking to Jen Prosek of the eponymous firm Prosek. Prosek is a, I’m gonna say communications firm, although actually I don’t think that does justice to Jen and what she does. I think what she does, to my mind, she’s the best there is.
But for those in our audience, there may be some who knows Jen, that aren’t familiar with you or your firm. Maybe we could start out with you just giving a just short thumbnail sketch of what Prosek is, what it is that you do?
JENNIFER PROSEK: Sure. Thank you for that lovely compliment. Prosek is likely the largest firm globally that focuses on marketing, communications and reputation management, primarily for financial institutions and investors, although we work in healthcare, technology and other sectors too.
But, finance has always been our claim to fame.
JOHN QUINN: So, I mean, I know you don’t really, uh, there are no peers for Prosek in my experience, but if people, you must get asked sometimes who, who are your principal competitors? Who would you say, just so people have some kind of understanding of your place in the marketplace?
Maybe it’s probably different. Probably different for different verticals.
JENNIFER PROSEK: Yeah. It depends what door you come in. You know, if you want a rebrand versus a crisis, you kind of have different kinds of competition. But I would say in general, in the communications world, it’s the Brunswick, Teneo, FGS, Joele Frank kind of crew that we see.
Most certainly John, when we’re dealing with special situations or lawsuits, that’s the crew that we’re seeing the most. Right.
JOHN QUINN: And, of course where we, our paths cross, tends to be in litigation related matters. We all know, the court of public opinion is a thing just like it’s the court and the court trials play out, litigations try out in the public sphere. That’s the truism. Now we all know that, and you’ve done a lot of that kind of work. Maybe just that might be a good place to begin, to give us your thoughts or approaches to assignments where, you know, you’re working with a client and you’re working with some lawyers, and what’s a very public dispute?
JENNIFER PROSEK: So I think in general, I’ll just run down a few of the things that come to mind. First is alignment. You know, the lawyers and the communicators have to be in lockstep. They have to have a strategy that they agree on. It’s not really good if the lawyers think one thing and the PR people think another, but that’s really important.
I think having a discipline strategy, you know, I think there’s a lot of temptation and a 24/7 news cycle where everything’s happening so fast to operate at that level of speed. But sometimes you have to like really slow down, talk about your strategy and be disciplined versus just speedy. I think there is a tendency to wanna do something versus not do something in today’s world.
My partner Andy always says, you know, don’t break into jail. You know, limiting.
JOHN QUINN: I like that.
JENNIFER PROSEK: Unnecessary talking. Right. Many of our clients do break into jail by saying too much, you know, understanding the rules of the road with the media, when to fight back, when not to fight back, when to be silent, when not to be silent, when to say no comment, when not to say no comment.
Everything you do publicly will create, a perception, and those perceptions go on forever. And you know better than I do. You can win a case and lose your reputation. Those two things don’t always go together. For sure. So remembering that reputations take a long time to heal. Just being very strategic, preparing for the obvious moments that matter.
We’re gonna file something that’s a trigger, we’re gonna do something that’s a trigger. So knowing the moments that matter, and then really, I think in today’s world, more than yesterday’s world, back to that, reputations last a very long time. What large language models say about you, understanding how they work, how they’re influenced, how they’re, how your reputation is fixed in that world is more important than ever because I don’t know, if I didn’t know John Quinn and I was walking to a meeting, I’d be asking my premium chat.
JOHN QUINN: I mean, that’s interesting. I’d actually never thought of that. Can you, change or influence the output of a large language model on one of your clients? And if so, how do you, how do you do that?
JENNIFER PROSEK: Now, listen, everyone in the business is trying to figure out how do the, how does the algorithm work? How does the algorithm work versus Google?
There are firms that make millions and billions, this is all they do, but in general, I always say an offense is a good defense when it comes to a large language model or Google. So for instance, if you’re not feeding the machine positive, relevant, momentous news about you, the machine is sucking up whatever’s out there.
So you can have some control by having a positive content program, right? You can also understand what large language models, how they rank, what they picked. Now, third party media is always ranked really high just like it is on Google. So that really matters.
JOHN QUINN: And we’re, yeah, we’re not talking about search engine optimization here.
We’re talking about the output from LLMs.
JENNIFER PROSEK: Yes. But you know, they work a little bit the same. Where they work differently, when you go to your LLM, you’re asking a very specific question and the machine’s trying to answer that very specific question, so it’s gonna pull the content that answers that very specific question.
You don’t do that as much with Google, right? If I said, where did John Quinn go to school and did he get A’s, that’s a very specific question. It’s gonna pull from wherever it can pull from. So I would say content matters a little more with large, so it might pull from your LinkedIn. It might pull from third party media, it might pull from a letter you wrote somewhere publicly.
So I think it’s a more dynamic universe.
JOHN QUINN: Yeah.
JENNIFER PROSEK: But in general, the only way to fix bad things, right, is to flood the zone with good things and suppress those bad things over time.
JOHN QUINN: That’s, I’ve never had this with anyone before that’s given communications campaign or strategy or episode, something that you were involved in.
It could be a litigation or it could be something else, rebranding or reputation management, where you think, and you probably can’t mention names, don’t wanna mention names, which you thought was a big success, where you really thought you were able to make a difference. Can you give us an example, just giving us a flavor of what you do and what the outcome would be?
JENNIFER PROSEK: I’m gonna pick something relatively safe because it’s relatively public. And I, you know, when I think over my career, what are some of the most interesting cases? This is not a litigation, but I think it’s relevant. So, years ago, maybe 17 years ago we met a firm called Bridgewater.
They were not very public. They were very under the radar screen. And what was happening was they had a very specific culture and not everyone agreed with that culture. It’s very controversial and it started to become public. They’re controversial culture…
JOHN QUINN: Just so people know, Ray Dalio, who was the founder and longtime, CEO and chairman and CIO of Bridgewater at which, at one time, had 160 billion under management, was the largest hedge fund in the hedge and had a very unique culture where, you know, they videotaped meetings. Yeah, yeah. People graded each other in real time. Scored their contributions in meetings, what they said, meetings were reviewed, the tapes were reviewed.
Everybody had a so-called baseball card. Every, you know, you were always being ranked by your colleagues on, you know, various metrics, are you, how good are you, your expression, are you empathetic? Are you whatever? And everybody had a baseball card that you were ranked. And then a culture he called Radical Transparency.
JENNIFER PROSEK: That’s right. Radical.
JOHN QUINN: I’m very familiar with this. And he’s written a book called Principles and actually that’s, we’ve done work with Ray who’s a fascinating individual. But yes, this was a highly controversial culture.
JENNIFER PROSEK: Yeah. Yes. So radical truth and transparency, so, this was at a time where if you were running a hedge fund or a private equity firm or investment bank, you were not public about anything.
You were under the radar. That’s just the way it worked. And, we met Ray and his colleagues and he said, what do you think we should do about this? And we said, we think you should go on the front foot with your culture story because it’s so unique and so fascinating and it leads to the best investment returns in the world.
Let’s not forget that, least at the moment. And we think the world will be fascinating and you should take control of your own narrative. Why would you let others write potentially negative stories when you could tell the story of why this culture is so unique? Maybe not for everyone, but very effective.
So Ray took that on board and went out and started to tell his culture story his way. And you just, you just said it. The world became fascinated. This is why you know about it. So fascinated. You know, we took Ray on stages, we you know, had interviews, we did it. The world became fascinated and it led to a bestselling book called The Principles.
And he’s written many books since then and I think we could all agree he’s one of the most interesting thought leaders in the world. We still work with Ray. But I tell that story because at the time, the bravery, it took that client to actually get on the front foot.
JOHN QUINN: Well, he did, he did kind of take to the stage.
He did. He’s pretty much on a stage somewhere it seems like every week of the year.
JENNIFER PROSEK: Well, guess what he learned? He liked it and he is good at it. And by the way, for a lot of founders who become thought leaders, it leads to kind of a second act, which is, you know, look at David Rubenstein, right?
What a second act. You know, he’s a TV host now.
JOHN QUINN: Many people think he’s just a TV host or a podcaster. What else? You know, they dunno.
JENNIFER PROSEK: Right.
JOHN QUINN: Right.
JENNIFER PROSEK: So the point of that story is like sometimes getting on the front foot, taking control, still telling your pro story publicly in the right way.
But listen, in a high-stakes litigation, this is, these are all the chess moves that the, you know, a John Quinn and a Jen Prosek are making along the way to try to take control of that narrative and put it forth in the most effective way.
JOHN QUINN: Right. So I’m gonna ask you a question. I would’ve my own answer to this.
I’m not interested in hearing your own answer. What do you regard as your superpower? I have a view about what, from my perspective and our experience together, what your superpower is. What do you think is your superpower
JENNIFER PROSEK: The firm, or?
JOHN QUINN: Let’s do both.
JENNIFER PROSEK: Okay. Well, my superpower, I suppose, is I love getting to know founders and business owners and CEOs. I’m personally fascinated and I love introducing them to each other because I believe that one, a new connection can change the course of your life, your kids’ life, your business trajectory. So, as you know, I’m a convener. That’s my number one superpower and I do it.
Yes, because it’s commercially beneficial to me and my clients, but I also do it ’cause I love it. I do it for free.
JOHN QUINN: Yeah so interesting because I was gonna say, your superpower is you’re a connector.
JENNIFER PROSEK: There you go.
JOHN QUINN: Which is what you said.
JENNIFER PROSEK: Yes.
JOHN QUINN: You have an amazing ability to do that. And I think it is, you’re obviously, you have a lot of interests.
You’re curious, so you can talk to people and you’re good at drawing people out. Jen convenes dinners and other events and gets people who, some know each other and some don’t know each other, around the table for a meal and has the ability to spark conversations. And she begins these with an icebreaker.
Like remember one was something about birth order, where were you?
JENNIFER PROSEK: Yeah.
JOHN QUINN: And what, what is your order in your family? Which I also, I’ve always thought that’s very important. So you got people sharing things like that. Another one was at one time was, grade your popularity in high school on a scale of one to five, and then how did that change in college?
Right. And you know, they seemingly, maybe you might say kind of silly little things and they’re not business oriented, but it works, people talk. By the way, I did a dinner in Dubai and I used the popularity in high school.
JENNIFER PROSEK: Oh good. That makes me happy. Yeah, no, I love introducing people to each other.
I feel like the most valuable thing in life is your network and I’ve learned that in business and finance, people are afraid of humanity. But if you use it the right way, the exact right way, not a silly way or not irrelevant way, it does break down everything down to wow, we’re just a bunch of people.
And I think if you could do that early in an event, you just get a much richer conversation. I mean, we spent 90% of the time talking about politics and geopolitics and issues and business, whatever. But starting with something personal really just gives you a sense of the other humans in the room.
And you know, I always want everyone to follow up with each other and do business and make great things happen. So it makes it a little easier.
JOHN QUINN: I mean, when you get a real conversation going over a dinner among people, there’s something magical that happens.
JENNIFER PROSEK: Oh, so great. Nothing makes me happier.
JOHN QUINN: I love it, yeah.
So I did this dinner in Dubai and I don’t know, I mean, obviously it had a lot to do with the people who were there but we had a relatively, I would say high level conversation, yeah, about AI and Frontier AI and things like our large language models at dead ends, should we be going in a different direction rather than, yeah, the brute force prediction. A technology of an LLM, should we go into a different direction where it’s really symbolic? Concepts where you assigned on graphs, trees about related concepts, and so you’re connecting concepts, not predicting what the next letter or word would be and it was really an interesting conversation.
Everybody was chipping in and, and it was…
JENNIFER PROSEK: That’s great.
JOHN QUINN: It was, A I think useful for everybody there, but, and B, interesting and everybody learnt something and really fun.
JENNIFER PROSEK: I think. Listen. People like you and me have zero time. So when people make time for something and then walk out and say, that was really valuable, that just makes me so happy.
Yeah because you know, it is valuable to get in a room with 20 amazing human beings. So to have something to say there, there’s nothing like it in life. But getting that right, there’s a certain formula to it.
JOHN QUINN: Yeah. How did you get in this line of work? I mean, I assume, where were you, you weren’t always doing this kind of work or what’s your background and how did you get into this?
JENNIFER PROSEK: No, I have a funny background. I was an English major in college, didn’t know what I wanted to do, so I interned about a million times. I did an internship in law market research, a million of them. And then I end up in this weird little internship in a fashion PR firm. And, I was pretty sure I didn’t love the fashion part, but it was very obvious to me the communications part was something I might have been, I might be born to do. So I figured that out early. My parents were teachers and they were very upset that I went to school for English literature ’cause they thought, you know, I’m never gonna get a job. So I made sure I had like a zillion internships and communications before I graduated, but I graduated into a pretty bad recession.
I didn’t get a job in a big firm and a training program, and I ended up meeting one guy who had an idea to start a business. And I didn’t wanna work for him. I didn’t wanna start up. Everything about it was wrong. The clients were oh, the worst. That was the start of this.
JOHN QUINN: And that was how long ago?
JENNIFER PROSEK: I don’t wanna say. Okay. Alright. So a long time ago, 1992.
JOHN QUINN: Okay.
JENNIFER PROSEK: Yeah.
JOHN QUINN: Well that was, you started when you were 12 years old, I assume.
JENNIFER PROSEK: That’s right.
JOHN QUINN: So what would you say is a lesson you’ve learned about communication? Something important that most people don’t really appreciate.
JENNIFER PROSEK: Oh boy, there’s so many.
I have my entrepreneurship lessons and my communications lessons. And I think the entrepreneurship ones are more interesting, but in communications, listen, I think, I hate the word ’cause everyone uses it, but authenticity, when the day, I think, not being AI, there’s an exercise we have here called nailing the narrative.
If you ask me, you know, I have 500 employees, most of them are better than me in something, I’m still the best at nailing the narrative. And what that means is I can walk into the most boring company or what other people think is boring, differentiate and figure out what is the unique selling proposition and the unique story this company needs to tell to get on the map.I just know it when I see it.
JOHN QUINN: Is that like one sentence or one phrase or one word or paragraph?
JENNIFER PROSEK: Like usually it could be a paragraph. It could be one line. It depends. We can shrink it or expand it, but nailing the narrative to me is the most priceless thing we do because if I can give you the language that gets other people excited to buy from you, or work for you, or invest in you, I’ve changed the trajectory of your business, right?
So nailing the narrative is the first thing you need to do, like before you start squawking to the world, like what are you squawking about and is it interesting and differentiated? We are in the noisiest world ever. So what makes you interesting and unique? I mean, one of the things I loved about the first day we met, you handed me a baseball hat and it said, most feared on it.
And I looked you up and it said you are voted the most feared law firm in the world every year. And I have to say, that’s a very clear, and to me, compelling reason to hire you or be afraid of you. But like, it just, it says what you do and it says you do it the best. And I loved it.
And you know, I also loved it because it wasn’t boring. No. You know. We work with financial institutions, big technology companies, whatever. You’re sort of trained to be boring. I don’t like boring. I want a little sizzle, a mistake. So I think a narrative should have something to it. Radical truth and transparency, right?
JOHN QUINN: Right.
JENNIFER PROSEK: The narrative around the culture. Think about how effective that is.
JOHN QUINN: One communications person said to me that if your campaign doesn’t make you a little bit nervous. Effective.
JENNIFER PROSEK: Yes.
JOHN QUINN: You think that’s true?
JENNIFER PROSEK: I wanna be nervous, but I wanna be excited. I wanna be, I wanna sit on the edge of my seat a little and say, tell me more.
JOHN QUINN: Right?
JENNIFER PROSEK: Right. The fear. Most feared law firm in the world, I have about a zillion questions for you. How did you build it? Why? Why are they afraid of you? Like, why are you so scared? I wanna know. I think it works. Radical truth and transparency. What the heck does that mean? I don’t have that culture. And then you say, yeah, then you unpack all the stories behind it.
You’re like, oh my God, of course I wanna, this sounds wacky to me.
JOHN QUINN: You know, this is not you. You talk about people in the finance world, you know, being the way they are.
JENNIFER PROSEK: Yeah.
JOHN QUINN: They don’t wanna be out there. They’re not gonna wear hats that say you know, most feared or whatever the banking equivalent of that is saying, most feared isn’t even for all the partners in our firm.
JENNIFER PROSEK: No, I know, I’ve heard, I’ve heard your own partners say they don’t like it.
JOHN QUINN: I know. Yeah. Some of my partners would, wouldn’t be caught dead wearing one of those hats.
JENNIFER PROSEK: Guess what? My daughter, who’s 18 stole my hat from me.
JOHN QUINN: As you know, it’s on my business card and I know a lot of my partners cringe over that.
What’s your advice to them? Speaking to my partners who cringe.
JENNIFER PROSEK: My advice is differentiated is priceless. And I think that in law firm circles, OMG, the most undifferentiated space in the world. I like it versus not like it. I’m sure there’s a couple instances where it doesn’t really work, but you know what?
Here’s the deal. Yeah. You can’t be everything to everyone all the time. So there’s gonna be somebody, yeah. I always say like, listen, I’m not for everyone, but I know who I’m for, you know, we decided long time, we call our culture and army of entrepreneurs. We’re very, we always say we have grit, hustle, and humanity.
Guess what? That’s not for every client, but you know what? 90% of them wanna work with us, because of that vibe.
JOHN QUINN: So I have to follow up you, you know, I had asked you about what you learned about commun, important lessons about communications that most people don’t know, and you had an aside, well actually I have ones on being an entrepreneur, which are even better.
I have to ask you about one of those. Okay. What is it about being an entrepreneur that you’ve learned that most people don’t know? It’s important.
JENNIFER PROSEK: So remember I was an entrepreneur when I was 22 by accident. I didn’t know what I didn’t know, but, what I learned pretty quickly was the two most powerful words in business are just ask.
JOHN QUINN: Yeah.
JENNIFER PROSEK: People are afraid to ask. I got so good at asking because I was young and I had to ask. And what ended up happening and then I went to business school later and the most powerful class that took a business school, of course, was negotiations. And you realize like, wow, you can negotiate anything, ask for anything.
So, and it has to be, you can’t be gross. You have to be, if there’s an art of the ask, right time, right place, right? Everything. But people are afraid to ask. I always say, ask me how many entry level students or entry level kids here at EC ask me for 15 minutes of my time. Zero.
JOHN QUINN: Mm-hmm.
JENNIFER PROSEK: They’re afraid to ask.
Yeah. Why aren’t they asking? That’s crazy. You don’t want a relationship with me? Like, yeah, so they’re not not asking because they don’t want it, they’re asking ’cause they’re afraid or they think it’s not the right thing or whatever. So it’s this form of risk taking. So I learned very early you should ask and there’s very little downside to not asking.
So that’s one thing I learned early to solve, not dwell. If you put all your energy into solving problems and zero of your energy into dwelling on things that happen to you, you’re gonna be just fine. You’re gonna put all your energy in the right direction. So that’s another one. I have a million of these though.
I can go on.
JOHN QUINN: You ever think about writing a book?
JENNIFER PROSEK: I have written two.
JOHN QUINN: Oh, I should know that.
JENNIFER PROSEK: No, you shouldn’t.
JOHN QUINN: Well, no, I mean, you haven’t given me copies. I don’t think you’ve ever referenced them. You’re hiding your light under a barrel there, Jen.
JENNIFER PROSEK: Well, they’re both kind of old because I decided I don’t really like being an author, but we could talk about that. My first book was called an Army of Entrepreneurs. It was about how I built Prosek. By building an entrepreneur army of entrepreneurs, because I was an early 20 something. How do you build a firm when you don’t know anyone and you don’t know anything?
You get older people who are smarter than you to build the business for you. So that was my first book in the army of entrepreneurs, and that worked so well when I had my daughter a zillion years ago. I got really fascinated by if I could make adults more entrepreneurial, could I make my child more entrepreneurial?
So that was about how to sort of bake an entrepreneurial child. And I wrote that with a child psychologist, which was sort of interesting.
JOHN QUINN: How old is your daughter?
JENNIFER PROSEK: She’s 18, she just got into college. So we don’t know if she’s entrepreneurial yet.
JOHN QUINN: Yeah, I have five daughters.
JENNIFER PROSEK: Oh my goodness.
JOHN QUINN: Yeah. One’s an academic. She has a PhD in Ottoman History.
JENNIFER PROSEK: Oh, wow.
JOHN QUINN: The next one is a lawyer term psychotherapist.
JENNIFER PROSEK: Okay. Well that kind of works.
JOHN QUINN: The next one’s a venture capitalist.
JENNIFER PROSEK: Wow.
JOHN QUINN: The next one’s a fertility doctor.
JENNIFER PROSEK: That’s what I wanna do with my next life.
JOHN QUINN: And the last one does what I do. She’s a litigator.
JENNIFER PROSEK: Oh my god. What an amazing, successful brood you have.
JOHN QUINN: Yeah. So what’s something, I mean, you must have clients sometimes who come to you and they have unrealistic expectations about what even you can do.
JENNIFER PROSEK: All the time.
JOHN QUINN: Tell us a little bit about that.
What is unrealistic for clients to expect a firm like yours to be able to do>
JENNIFER PROSEK: Like there’s the offensive defense side of our business. So let’s talk about defense, which is usually crisis communications’ unrealistic client. You can kill that story, can’t you? Why can’t you kill that story?
If there’s a legitimate, truthful story that is gonna be written about you or your firm, you can, I can shape it and I can take it maybe from a level 10 down to a level four, but I’m not gonna be able to kill it. Killing stories is pretty hard. So I think for some reason there’s often a belief that firms like ours go around killing stories.
I mean, we kill them when we’re not, they’re not truthful. Like if a journalist is going up the wrong route, we can convince them you’re gonna be embarrassed by writing a story ’cause it’s totally inaccurate, then we can kill a story. But if it isn’t, we’re not gonna kill a story. So that’s a frustration on the defense side.
On the offense side, the unrealistic client thinks they are sitting on the most magical company or invention in the world. And guess what? It’s not.
JOHN QUINN: Oh.
JENNIFER PROSEK: So we can make it. Listen, we are masters at making the boring un-boring, but it doesn’t mean you’re gonna be on the cover of a publication. So we always found in the startup world in Silicon Valley, there was always that, that breeds a certain type of person who thinks they’re gonna be on the cover of something for a not so exciting thing.
JOHN QUINN: Jen, I could talk to you all day. You’re such an interesting interlocutor. I love talking to you. At least in the podcast world, all good things have to come to an end.
JENNIFER PROSEK: Yes, absolutely.
JOHN QUINN: And yeah, I’m sure you’ve got some things to do. So, thanks for being with us.
JENNIFER PROSEK: Thank you for having me.
JOHN QUINN: This is John Quinn. We’ve been speaking with Jen Prosek of the Prosek Firm. This has been Law, disrupted.
Thank you for listening to Law, disrupted with me, John Quinn. If you enjoyed the show, please subscribe and leave a rating and review on your chosen podcast app to stay up to date with the latest episodes. You can sign up for email alerts at our website. Law-disrupted fm or follow me on X at JB Q Law or at Quinn Emanuel.
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Published: Jan 14 2026






