Pod Insights How I Invest with David Weisburd E358: The Woman Behind the World's Top GP Brands | Jen Prosek About this episode What if the biggest edge in investing isn’t capital or strategy—but how clearly the world understands you?
In this episode, I sit down with Jennifer Prosek, Founder and Managing Partner of Prosek Partners, to discuss how branding, narrative, and communication have become core drivers of success in financial services. Jennifer explains why firms went from ignoring marketing to depending on it, how “efficiency and preference” directly impact fundraising and deal flow, and why owned media and the “digital blink” now shape first impressions. We also explore how founders should think about storytelling, differentiation, and building long-term trust in an increasingly competitive capital landscape.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 David Weisburd? Jen, you are the Prosek in Prosek, the famous marketing communications firm primarily focused on financial services. You started that way back in 1995. Maybe we fast forward to 2008. Why did the industry have such a tailwind in 2008 following the global financial crisis?
0:17 Speaker 01 I am a startup entrepreneur. In some ways, I have a boring resume because I basically started my business. And this is what I've been doing for a long time. But when I started the business, financial services firms were very much under the radar screen. And that sort of style of the day was keep your head down, don't engage. It was like no engagement with stakeholders zone. And there was zero appreciation for brand. And there was really no front footed proactive marketing or communications, especially in institutional finance. If you were a consumer finance company, of course, there was some marketing. And I had the zany idea that one day that might change. And so for the first few years of the business, I was selling something no one wanted to buy. But the financial crisis came and every financial services firm had a black eye.
1:00 Speaker 01 Famously, the Goldman's of the world had the worst problems. And they went to the market and they said, okay, defense doesn't work. We need offense. We need to fix our brand. We need to be proactive. We need to be front footed with reputation management with marketing. Who does that? And there we were, sitting there. So that was when the business took off.
1:16 David Weisburd? When you say firms weren't focused on branding, I can't help but think about the correlation with just private equity and venture capital firms in the 1990s. So I had Professor Steve Kaplan, famous University of Chicago professor. And he said that he's been teaching private equity since the 90s. And in the 90s, private equity managers would come into class and he would ask them, how do you differentiate? Like, how do you look at your competition? They would say, oh, we don't do that.
1:36 Speaker 01 Yes.
1:37 David Weisburd? As if it was like a dumb question. And then in the 2000s, I started doing now. And now you have these hyper competitive niches and differentiation. So I wonder whether branding went from something that, why would we spend money to that, to a painkiller? You need to have branding.
1:50 Speaker 01 100%. So I'm in the like, you know, glory days of my firm because literally I have to convince no one now in financial services that brand matters. No one. So it really went from one place to the other. And I graduated Columbia Business School. And when I went to business school, People looked at me like I had 10 heads. They're like, what do you do? Why do you do that? And aren't you going to be a banker or consultant? I mean, it was just completely bizarre that I could be there doing what I did. And I spent a lot of time trying to even convince the professors and the curriculum makers, like, you really should care about, especially like, reputation management, like, even at least have some appreciation for crisis communications or crisis management. No interest whatsoever. And that has changed so much.
2:30 David Weisburd? Has it dramatically changed again in the last couple of years?
2:34 Speaker 01 Well, just the velocity. Even five or eight years ago, I would say, you know, 50% of the firms were really serious about brand. Now, I would say 100% of the firms. So it happened fast, but there are a few reasons, right? So COVID was one of them, actually. So if you were a dealmaker or fundraiser and you were sitting behind the screen and you were like, how am I going to do a deal or raise money like this? You, for the first time, went to places like LinkedIn, desperate to connect with people. COVID threw a lot of people into the idea of marketing and doing things differently. Like, could I reach them through digital or audio or some other means? So that was a little bit helpful. But really, it's more the competitive nature. And then, da, da, da, the last three to four years, this, what we call reaching for retail, this interest in the wealth channel by institutional finance has meant you really have to have a brand.
3:18 Speaker 01 Because now, if you don't have a brand, the financial advisor doesn't know to sell your product, and the high net worth person doesn't know to ask for your product. So that is why you've really seen, like, I think the marketing and comms space around those firms going for the wealth channel is really interesting. So, you know, you saw Carlyle go into an F1 partnership last year. Why? That's not just because Harvey Schwartz might like F1. That's because they're reaching for retail, right? They're trying to get brand awareness with the financial advisors and the high net worth individuals.
3:50 David Weisburd? If you take a step back and you look at the LP market, because essentially, who's the customer of these GPs and these general partners? Most of the institutional capital, the pension funds, foundations, endowments, they've deployed most of their capital in their core, call it their core managers. They're 15 to 25 per asset class.
4:06 Speaker 01 Yep.
4:07 David Weisburd? And they have some room at the edges, but they're not a huge source of new capital. Now you have sovereign wealth who's coming on board, obviously huge checks, but there's only so many sovereign wealth funds in the world. And the second net new capital is the RIA slash the retail.
4:21 Speaker 01 Yes.
4:21 David Weisburd? And if you're a manager that wants to grow, you have no choice, but you have to focus on that.
4:25 Speaker 01 That's exactly right. And that requires brand and marketing. Yes.
4:30 David Weisburd? And that's why you have Blackstone doing these somewhat cringey.
4:34 Speaker 01 Oh, yeah. John Gray's running videos. Yeah.
4:36 David Weisburd? I meant more the holiday videos.
4:37 Speaker 01 Okay. I think the holiday video, my view, is probably also a talent play. But I think the running videos and the constant amplification of kind of in a more retail way is clearly they figured out like, we could reach the retail audience and it doesn't cost a lot of money LinkedIn to do and it's working. The great thing about LinkedIn is you have a lot of data at your fingertip to know, is it working, is it not? Who am I reaching? Who is clicking? Who's converting? So I think they've figured out a relatively inexpensive way to market to the retail channel. And they were first and they were experimental and people like to cringe, but they're still looking at it.
5:11 David Weisburd? The latest stat that I heard is 95% of retail capital today is going into five firms, the Blackstones, Apollos, KKR's of the world.
5:20 David Weisburd? You have some of these clients, but you also have a lot of clients that are not the five biggest firms in the world. How can they play the marketing game in an offensive way? And where's the alpha for smaller firms?
5:30 Speaker 01 The smaller firms have to decide, like, what are we the best at? You have to kind of be so specialized or so good at what you do that it's like picking a boutique that does that versus a supermarket that does everything. Whether you're Blackstone or whether you're the smaller manager, it comes down first to what we call nailing the narrative. What's your story? Why are you unique? What's the unique selling proposition? Why should I buy you? So you start with nailing the narrative and then you execute through the channels that make sense. So I do think smaller or midsize managers can win. The problem with the retail channel is it's very expensive to market to because it's just a much bigger universe. So those smaller managers have to decide. Do I really have the wherewithal to do this?
6:13 Speaker 01 Because whether it's going to be armies of distribution people internally or big consumer marketing spends, you're going to have to do something to go and make that a reality.
6:23 David Weisburd? Expert calls have always been one of the most powerful ways to build conviction. But today, investors are asked to cover more companies, move faster, and do it with leaner teams. With AlphaSense AI-led expert calls, their TGS call service team sources experts based on your research criteria and lets the AI interviewer get to work. The magic is in the AI interviewer, purpose-built and knowledgeable-based information to conduct high-quality, context-rich conversations on your behalf, acting as a trusted extension of your team. Then they take it one step further. Your call transcripts flow natively into your AlphaSense experience and become queryable, searchable, and comparable. So your primary insights plug directly into earnings prep, digital work streams, and pitch books with zero tool switching.
7:07 David Weisburd? And with AlphaSense expert call services, the AI-led expert calls are just one option because we know the importance of a hybrid expert research approach. AI for coverage and efficiency. Humans for complexity and conviction. It's the institutional edge that scales research without scaling headcount. For hedge funds, that means validating thesis assumptions across dozens of experts before earnings instead of a handful. For private equity, it means faster pre-IOI scans and deeper commercial diligence. For investment banks and asset managers, that means pulling real operator perspectives straight into models and sector positioning without disconnected tools or manual handoffs. All of it lives inside the AlphaSense platform, trusted by 75% of the world's top hedge funds alongside filings, broker research, news,
7:52 David Weisburd? and more than 240,000 expert call transcripts, turning raw conversations into comparable, auditable insight. Take advantage of AlphaSense AI-led expert calls now. The first to see wins, the rest follow. Learn more at alphascense.com/HowIInvest. At the risk of asking an extremely dumb question.
8:11 Speaker 01 No. Nothing's dumb.
8:13 David Weisburd? Retail.
8:13 Speaker 01 Remember, nothing's a bad question.
8:14 David Weisburd? You have a firm that goes out to, quote unquote, retail.
8:17 Speaker 01 Yes.
8:18 David Weisburd? How does retail buy? Is it through their RIAs? Is it through the large platforms? Is it inbound? What's the common practice in how funds convert retail interest into AUM?
8:30 Speaker 01 Yeah, there's a number of ways. Either you get on a platform like a Morgan Stanley, a UBS, et cetera, it's Merrill Lynch, right? One of the big wirehouse platforms. You get your product on the platform and that's hard. That's a big win, but guess what? That's only step one. Then every Merrill Lynch FA across the, you know, country has to know you exist and pull it off a platform. So even if you arrive and you're successful and you're like, wow, I'm on the UBS platform. You got to figure out how their FAs are going to want to want your product, right? So there's still a lot of marketing that has to be done. And again, you could reach those UBS FAs all over the country through, you know, events, through LinkedIn, through media, through paid advertising. And then there's a lot of elbow grease, like let's go see the high net worth group of Merrill Lynch in, I don't
9:14 Speaker 01 know, Palm Beach, Florida. Where are we going to go? So it's a big effort. And then there's the independent channel, you know, the independent, the RIAs. And same kind of marketing you have to do there, but they're obviously a squirlier bunch, you know, to capture all of them. And of course, you've probably talked to like a case or an I capital. There are these marketplaces, these technology platforms that have popped up to try to offer the product in a centralized marketplace to so. But again, it's a lot more work than marketing to institutions.
9:46 David Weisburd? Maybe we could double click there. So it's hard enough to get on the Morgan Stanley platform, UBS, but that's not enough. How does one activate the FAs? And is there a way to activate the underlying investors as well? Or is the best practice really going after the FAs?
10:00 Speaker 01 90% of the firms that are reaching for retail are targeting the FAs first because it's much easier to target the FAs than it is to go out to.
10:09 David Weisburd? It's more scalable.
10:10 Speaker 01 Yeah. High net worth individuals, that's like a harder thing to do. And I would say that a lot of the marketing that goes on still has a lot of professional development and education to it. So Blackstone University is teaching FAs about alternatives, right? So there's still a lot of education going on. So the marketing is both education and also like. Brand lift amplification of the brand, right? And then there's a lot of, like I said, event marketing going on. So we work with CASES platform. They have a conference every year that is like the Milken Conference for financial advisors for RIAs. So they all come together and the content is all focused on the democratization of alternatives and how to sell alternatives to your clients and what you should sell to your clients and what you shouldn't sell to your clients, et cetera. So it's fascinating.
10:53 Speaker 01 If you go to the CASES conference, you'll get Robert Smith at Vista talking to the FAs about Vista versus talking to LPs about Vista. So it's very similar, but it's different because the retail channel is different.
11:06 David Weisburd? Last time we chatted, you said that brand helps managers with efficiency and preference. What did you mean by that?
11:11 Speaker 01 We're working for a pretty tough crowd, right? The founders of private markets firms are rigorous people and they only spend money if they're going to make money. So a lot of people think about marketing and public relations as like, oh, we're out there just trying to raise our profile. My view, if we're not hitting the bottom line, forget it. We're not lasting with our clients.
11:27 David Weisburd? Too expensive for that.
11:28 Speaker 01 Too expensive. We're not going to last. We want to be partners forever. So how do we do that? So we do that when our work hits the bottom line. And how do you hit the bottom line? If I can create efficiency and preference, I hit the bottom line. So efficiency, right? You're going to go out and fundraise. The LPs don't know who you are. They don't know your story. They don't know what you stand for. They don't know your products. When you have that meeting, you're having the first meeting and you're spending about 90% of it educating. Say you could have that meeting and they know who you are. They don't need education. They like what you do. They're down with it and they just want to get down to business. Now you're everything's second meeting or maybe the third. That's efficiency. That's priceless. So we can create a lot of efficiency and then we can create preference. Like say that same LP already has in their mind that of all the firms in your category,
12:11 Speaker 01 you're probably the best. That's preference, right? So we have a rubric we call talent, deals and capital. If we can create efficiency and preference across talent, deals and capital, we are bottom line. So if we can help you raise money more efficiently and effectively, win. If we can help you source deals better, win. And if we could have the best talent coming to you versus you looking for them, win. So we try to wrap our strategies around those things. That's the simplistic way to think about it.
12:40 David Weisburd? A lot of managers, for whatever reason, don't see themselves as businesses or as products themselves, but of course, they're in a marketplace. And one of the biggest misconceptions is that a first meeting is a first meeting, that regardless how you get to that first meeting, all else being equal, it's equal, but all else is never equal.
12:55 Speaker 01 Yes.
12:55 David Weisburd? If you could get introduced by an existing LP, by existing GP, if they've been listening to five of your podcasts, not only does that help you get the meeting, yes, it helps with that for sure, but it also dramatically reduces the sales lifestyle.
13:07 Speaker 01 And I have to say, of all of the communications mediums, I think podcasts are the most effective in creating the second or third meeting. Because if an LP or a recruit or a portfolio company CEO you want to do business with has listened to you for 45 minutes, your story, your strategy, your personality, and they have any sort of preference, you're just way ahead of the game. So I do think podcasts are an exceptionally great place. I tell all my GPs, you know, as long as you're effective at communicating and you can hold a whole 45 minutes, it's going to be an asset you can use for a long time. It's not a one-time appearance. It's an asset.
13:47 David Weisburd? My co-founder of my business here, Curtis, is sitting down, but I started the podcast with Eric Thornburg. So the co-founder of the podcast, Eric Thornburg, he now runs a media for Andreessen Horowitz. And one of their, Marc Andreessen and Ben Horowitz' thesis on that is the media part of the business needs to be either driven or underwritten by the founders. It has to start at the founders or it cannot succeed. So another way, if you put it through not the founders and you have to dress it down with PR and basically sanitize it, it's not going to be effective. What are your thoughts on that?
14:15 Speaker 01 Listen, there's nothing like a founder taking hold of their own story. It's always the most effective. I mean, everyone wants to hear from the founder. The founder sets the tone. And I always say, especially in the GP land, you want to understand the firm, you want to understand the founder. Having said that, everyone wants their firm to live on for hundreds and hundreds of years. So it's incredibly important that your management team, your second tier of management gets good at this and you can prove to the world, there's a bench of talent here that can survive me. I'm, you know, it's like, great, you want to talk to me, but like, this company can live on. So I do think, yes, that's true, but we spend a lot of time trying to make sure that we show the market more than the founder, if that makes sense.
14:57 David Weisburd? I know you're not necessarily actively coaching yourself, but if you had to coach a GP and the trade off between being sincere and not hitting any kind of like regulatory or PR processes, how would you coach somebody on a podcast that has a fund? What are some best practices and what are things to avoid?
15:13 Speaker 01 Well, you certainly have to avoid stepping on a regulatory mine because if you end up there, it's not going to have been worth doing the podcast. But you have to understand that we are all competing on differentiation and memorability. So if you have nothing to say that is interesting, if you want to water down your message so much that it's like everyone else's, don't even bother. Right? When these things are effective is that the audience got some value. So like you want to come to these things with a great story and insights. You know, hopefully someone who listens to this podcast says, oh, efficiency and preference, that totally makes sense to me. Now I understand why we would do this. Right? So you want to be giving the audience the gift of something, the gift of knowledge or an insight or something. My advice would be what is the goal of doing the podcast? First of all, what do you want to achieve?
15:56 Speaker 01 If the answer is, I want LPs to really understand my strategy, you better spend some time on your strategy on the podcast. Right? But you also have to understand what makes a good podcast and what gives a gift to the audience and what achieves your goal as the host. You don't want the podcaster to walk out and be like, that was boring or I got nothing or it was a total commercial. Like you can't do that either. So it's this balance between, you know, what is your goal and are you delivering against your personal goal? But are you also delivering on the host's goal and the goal of the audience? Right? You want to deliver.
16:25 David Weisburd? You need to have a point of view and I think people forget that podcasts are opt in and you're competing against, I'm competing against Joe Rogan.
16:31 Speaker 01 That's right.
16:31 David Weisburd? Against the top podcasters in the world. So the moment that people think that you're selling or not taking a point of view.
16:37 Speaker 01 Yes.
16:37 David Weisburd? Or have no unique opinion, they're just going to fast forward. Even if I as the host want people to listen, it doesn't matter.
16:43 Speaker 01 I also say, because I do a ton of moderating on stage. The backfire of performing badly is huge. You remember the crap moderator, the guy onstage who said nothing and wasted your time. You remember that. So it's like, don't even dare do it. It can be a brand backfire, in my view.
17:03 David Weisburd? For a GP that has a finite budget, maybe not a small budget, but not a large budget, like the large. One thing that I've learned from talking to hundreds of investors, founders, and business leaders is that planning for the future isn't just about growing assets. It's also about protecting the people who matter most. Life comes with a lot of important milestones. Maybe you're buying a home, starting a family, planning for college, or simply thinking more intentionally about your financial future. As those responsibilities grow, it's worth making sure you protect those you love. Not sure what kind of life insurance you may need? Concerned about how much it may cost? Think life insurance is too complicated? Your local State Farm agent can help answer those questions. They can help you explore your options for life insurance and choose coverage that you can adjust as your family's needs change over time. Financial protection for your loved ones when it matters most.
17:48 David Weisburd? Learn more about life insurance at statefarm.com. Like a good neighbor, State Farm is there. One thing that I've learned from talking to hundreds of investors, founders, and business leaders is that planning for the future isn't just about growing assets. It's also about protecting the people who matter most. Life comes with a lot of important milestones. Maybe you're buying a home, starting a family, planning for college, or simply thinking more intentionally about your financial future. As those responsibilities grow, it's worth making sure you protect those you love. Not sure what kind of life insurance you may need? Concerned about how much it may cost? Think life insurance is too complicated? Your local State Farm agent can help answer those questions. They can help you explore your options for life insurance and choose coverage that you can adjust as your family's needs change over time. Financial protection for your loved ones when it matters most.
18:32 David Weisburd? Learn more about life insurance at statefarm.com. Like a good neighbor, State Farm is there. One thing that I've learned from talking to hundreds of investors, founders, and business leaders is that planning for the future isn't just about growing assets. It's also about protecting the people who matter most. Life comes with a lot of important milestones. Maybe you're buying a home, starting a family, planning for college, or simply thinking more intentionally about your financial future. As those responsibilities grow, it's worth making sure. You protect those you love. Not sure what kind of life insurance you may need? Concerned about how much it may cost? Think life insurance is too complicated? Your local State Farm agent can help answer those questions. They can help you explore your options for life insurance and choose coverage that you can adjust as your family's needs change over time. Financial protection for your loved ones when it matters most.
19:16 David Weisburd? Learn more about life insurance at statefarm.com. Like a good neighbor, State Farm is there.
19:20 Speaker 01 Every budget is finite.
19:22 David Weisburd? What are the lowest hanging fruit? If a GP comes to you and says, I'm ready. I'm sold, Jen, on I need to do media. I need to be offensive. What's the lowest hanging fruit that he or she could implement from day one?
19:32 Speaker 01 So I would say, first of all, it's all custom. Meaning what is that GP trying to achieve? Is it deal sourcing? Or is it fundraising? Or is it talent finding? Or is it something else? So first we have to figure out like, what are the most important things to achieve? And then that strategy would be built against that. And then the tactical plan. Having said that, I'll answer your question. Somebody asked me the other day, if I was a relative startup and really didn't have much budget, what would you recommend I do? Well, first of all, this nailing the narrative thing. It all starts with like, do you have a message that resonates? Make sure you do spend time on your messaging and your story and your narrative. Cause without that, what we're talking about is this empty story or all the same, or just forget it. You're wasting your time. So you gotta start there. The great news about today's world is in addition to the media that we read,
20:16 Speaker 01 the earned media, as we call it, there's a lot of owned media. Your website, your LinkedIn, your newsletter, whatever. There's such an opportunity to own your own media channel. And I would say to look at that, like I write a newsletter called Leadership in Volatile Times on my LinkedIn. It is probably in the top three most valuable things I do because I get tons of engagement with the right people. It doesn't cost me much. I do it myself. I post it myself. So the low hanging fruit is really where you don't have to obviously pay anyone else to do it. And you could reach the audience you want and you could build your own channel. I think that's really cool. And, and I can't say enough about LinkedIn because every LP you want, every recruit you want, every. You know, CEO of a portfolio company you want to do business with is going to be
20:59 Speaker 01 out there. You can't skip LinkedIn. If you have something to say and you're a little less risk averse, getting to know the media that covers your particular world can be very fruitful because you can build a relationship with those folks and they start calling you for your opinion and you start appearing. And then we call this the third party endorsement. If you're reading the Wall Street Journal and they're quoting you versus 10 other folks, there's just sort of this implied, that guy must be kind of smart, as long as you're saying smart things. But that's also a little bit risky. I think a little bit of media, a little bit of speaking, a little bit of LinkedIn. But I will say this, I believe the most important thing in life right now is what I call the digital blink. If you remember Malcolm Gladwell's book, The Blink, like, it'll take very few seconds for me to size you up and you size me up. Well, before I came in here, if I didn't know your
21:44 Speaker 01 podcast, I'd be asking ChatGPT, what's the reputation of this podcast? Is it a top podcast? What is so and so like? Who's been on it? And in two seconds, I get the digital blink. Like, this is what I believe, right? So how is what I'm doing influencing how LLMs are, what LLMs are saying about me and my company? And this is like the, I think, the most important new world of what we're doing is how does the content we're putting out, how is it sized up and how is it served up? Large language models, et cetera. And you'd be surprised, this is my best advice for someone with a limited budget, you don't have to do a lot. If you did one quality thing a quarter that influenced your digital blink, you'd be great. You'd be great. Because it's really not about quantity, it's about
22:26 Speaker 01 quality. But you want to have, the reason I say one thing a quarter, you want to have some sort of repetition. So you're building this content machine. So what if, God forbid, along this journey, there was something bad? Like, you had bad performance and the media wrote about it. And that's now being sucked up by the LLMs, the bad news. If you don't have any other good news happening, if you haven't built this muscle of content around it, there's no context, there's nothing else, it's only the bad stuff. So I always say to clients, offense is a good defense. If you have a positive offense engine of your milestones, your news, your thoughts, your this, that will help you when the chips are down. And ultimately speaking, most people who run businesses are going to hit a speed bump, hopefully a small one, along the way.
23:09 David Weisburd? So many great things to unpack there.
23:12 David Weisburd? Said another way, offense, the best defense is a great offense is not having a strategy is a strategy. The strategy to be passive. I remember there's this whole industry of reputation management on Google. And the way that would work is if you had something bad on the first page of Google, they would put in a bunch of things and then the first page would go to the second page. And that's how you kind of do it. Same thing in LLM world.
23:29 Speaker 01 Yeah.
23:30 David Weisburd? If you don't have anything about you and God forbid you have something negative that happened, that's going to dominate.
23:33 Speaker 01 That's exactly right.
23:34 David Weisburd? The LLM prompt.
23:35 Speaker 01 The difference with the LLMs, which is super interesting is you're right. Google ranks basically by credibility. So if you have a negative story in New York Times, good luck pushing that to page two, three, four. It takes forever because it's so highly ranked in terms of Google's credibility score. In LLM world, we're asking questions. Like I'm asking a specific question, like where did you go to school? Or who are you married to? Or what are your preferences? Or what's your reputation? So it's sucking up content in a little bit of a different way. That's what's so fascinating about LLM world and online reputation management is it's a little bit different than the Google world. Now, it still also ranks content by credibility scoring. That still matters, but it's way more dynamic than Google.
24:17 David Weisburd? I want to go back to something they said. You said a lot of interesting things in a row.
24:20 Speaker 01 Oh, good.
24:20 David Weisburd? So we need to unpack. One is the way that would categorize it is before you do media, what are you saying? Because all media is, is an amplifier.
24:30 Speaker 01 That's right.
24:31 David Weisburd? So if you don't have something smart to say, you could, just as a thought experiment, send it to a billion people.
24:36 Speaker 01 Right.
24:36 David Weisburd? And now you're going to be known as an idiot.
24:38 Speaker 01 Yes. Right.
24:39 David Weisburd? Fame and brand and getting out there is not always a positive thing. And there's plenty of examples which.
24:44 Speaker 01 A lot.
24:45 David Weisburd? Both in finance and outside of finance. So first is what is your messaging? And upstream of messaging is actually strategy. What is your right to win?
24:52 Speaker 01 Right.
24:53 David Weisburd? So there's a whole question of how do you explain your right to win? But first you must have a great right to win. It's easier to explain something good than it is to, to improve your strategy. Secondly, and we might disagree here, but I used to have a newsletter and started a podcast and I actually got probably a thousand subscribers in a couple of months on the newsletter. And the reason I stopped, it's not because I have anything against newsletters. I didn't, my heart wasn't in it. I didn't love it and I knew that all media more or less is about compounding your advantage. And if I wasn't going to do it for 10 years, I should quit in two months.
25:22 Speaker 01 Yep.
25:23 David Weisburd? A lot of people don't want to quit and don't want to pick, pick their, their tool. So I look at media a lot and. What is your best tool out there? For me, it's podcasting. For other people, it's newsletters. I know people that love writing and waking up every day and they look forward to it. And I'm like, there's no way in hell I'm going to beat Jen in writing because she loves it. I don't.
25:39 Speaker 01 What I tell my daughter about like finding, you know, your career. You could pick something that people say is going to be the most successful or the most money making. But the guy in the crazy niche you've never heard of, who's passionate and loves it and wakes up every day to kill it. He's going to be the most successful guy in that weird little thing. And he's going to kick ass over the mediocre banker. In my whole career, people looked at me like I had 10 heads. It's like in finance, they're like, you're getting your MBA in finance and you're doing that weird, what is that? Communications thing, but I knew I could be a mediocre banker. I could be a killer financial communications person. And so I stuck with that and it worked out. So I think you're right. You have to do what you are, you're, you're sort of naturally built to do. And then it's much more successful.
26:21 David Weisburd? One test to that, a lot of people ask me, I want to start a podcast. And the test to that is would you continue doing it if no one's listening?
26:29 Speaker 01 That's right.
26:29 David Weisburd? If no one's reading, because nobody will listen, nobody will read for so damn long.
26:33 Speaker 01 Yes.
26:33 David Weisburd? That if you are not intrinsically interested in that medium, you will fail.
26:36 Speaker 01 Totally. So for example, not that you asked me this, but if you did, Jen, how did you build this company in your twenties to a company? That's number one in the private markets. And I would say I, a lot of things, I basically ate my own cooking, but I figured out like something of value that other people need that I love to do. It's to your point about you love your podcast, something that like, you wouldn't even have to pay me to do it. I like it so much and that is convening. I get a kick out of introducing people to each other and knowing something magical came out of my introduction. Right? So I believe in network value. I believe that the right introduction can change the course of your career, your business's trajectory. So I started doing small salon dinners with founders where I didn't introduce them to each other. I'd moderate the table and make them all look like a million bucks.
27:21 Speaker 01 But when they left the room, they all knew quite a bit about each other. So that if they wanted to follow up and do a deal or hire each other's kids or whatever, they'd do it. I'd never know what they did, but whatever. These dinners became so magical that, and I never sold myself because like, who wants to come to a dinner where I'm selling Prosek? Who cares? I was basically gifting this network and it became such a gift to other people that people would call me up and be like, Jen, it's so amazing that you keep inviting me to these unbelievable dinners where I meet all these people who become friends and people I do business with. I'd love to do something with you. And that would be like, okay, let's do something together. And I think when you do something you love, and I love that and I continue to love it. It's my passion. I love it. It makes me so happy. People tell me all the time, like these two female CEOs that met at one of my dinners,
28:06 Speaker 01 they hired each other's sons because one wanted to be in sports and one wanted to be in finance. And I'm like, that's amazing. You know, so that stuff just drives me. You've just got to find the thing that doesn't feel like work that you love. And podcasts is like that for you.
28:17 David Weisburd? You've weaponized your people pleasing.
28:18 Speaker 01 Yeah, exactly.
28:20 David Weisburd? I'm like, okay, I'm a people pleaser. I can't do anything about it. I could go back to my childhood and through a time machine, or I could just embrace it and productize it and play to that strength. You also said, one other piece of advice that I have for people, and this is a cultural norm that we have in our companies, is do shitty first versions. Because all first versions are shitty. And the way that I apply that and people ask me, hey, I want to go on a podcast. I'm like, find the smallest podcast in the world. Go there. Seven people will listen to it. It's going to go poorly and you're going to learn. Do like five to 10 of those. Because you're always going to be paralyzed to go on these large podcast platforms and embarrass yourself. Because guess what? There's a non-zero chance you will embarrass yourself if it's your first podcast. You're going to listen back and you're going to be like, oh, I can't believe I sound like that. I look like that. But just start somewhere is another thing and it goes with any medium as well.
29:03 Speaker 01 I tell people that all the time about, you know, taking the stage. You wouldn't for the first time go up in front of 10,000 people in the most high profile thing, right? Like you have to put in your reps. I do it all the time. I still freak out about it every time I do it like. But I know what's going to happen. I know how I feel. I know when I'm resonating like, because I've put in my 10,000 hours. But I agree, most people can't be brilliant the first time. So you have to put in your reps.
29:30 David Weisburd? So you went from 1995 to hustling and bustling to your first couple of clients. When you grew during the global financial crisis, today you are the number one firm. I don't even know who the number two is, no offense to anyone else in the industry. You guys just dominate so much. What's next for Prosek?
29:47 Speaker 01 I thought there was a limitation maybe to like the size of the finance world. Like I'm going to run out of financial companies, whatever. But finance takes you everywhere, right? When you represent the best investors in the world, they're investing in healthcare and technology and this stuff. So you can basically go anywhere. So we have a lot of really cool options. I would say like our healthcare business has really taken off. For example, I would say our crisis communications business, which is a very hard business to break into because there were really amazing players there before I was born. Our crisis special sits book growth doubles every year for a lot of reasons. But what's really next for Prosek to me is figuring out this network value piece. We are two degrees of every great investor in the world. And I'm intrigued by what does that mean? What's the next place to go with that? Do we do a little bit of fundraising?
30:32 Speaker 01 Do we have a broker dealer? So we're kind of like right now trying to play around with what that looks like. I always say I'm so lucky. I have a front row seat to these crazy, incredible, amazing investors. And I learned from them and I kind of copy the things that they do. So we've also started a little venture portfolio. We have a GP stakes business where we take stakes in other firms, try to grow them. So there's a lot of stuff cooking. We are an extremely entrepreneurial place because that's what drives me. I love the craft, but I really love business building even more. So all of those things are on the list.
31:03 David Weisburd? And you're a super connector. You were introduced to me by one super connector, Ron Biscardi. You're also close with Rahul McDowell, who's a good friend of mine, also a super connector.
31:12 Speaker 01 Yeah.
31:12 David Weisburd? And I'm a growing super connector. I'm trying to learn to be better. What are some rules for growing your network and becoming a super connector?
31:19 Speaker 01 It comes back to giving gifts and the law of reciprocity. So even when I was in my twenties, I figured out.
31:28 Speaker 01 I remember this woman went from being the head of communications at Morgan Stanley to the head of communications at AIG, I think it was. And I'm thinking, just psychoanalyzing, when you go from investment banking to insurance, what happens? You don't know the industry so well, right? And you probably don't have the best network in the industry. So I called her and I said, you just got this great job. Congratulations. How would you like to meet the head of communications at Prudential? You know, a peer. And she's like, oh, my God, that would be amazing. I mean, and I'm like, OK, I'll set it up. So I'd set up a lunch and I'd introduce the two people and I'd go to lunch. And now we were all friends because I gave something of value and never asked for anything in return. Like, I just gift and sort of wait to see if the phone would ring, right?
32:09 Speaker 01 So I think it's trying to figure out, as a connector, the best connectors have figured out what the other person needs. Like, who do they need to meet? Why do they need to meet them? And then the best ones don't have a lot of selfish motives, right? When I connect people, I literally am like, it'd be great to get something back, but if it never happens, I don't care. Like, I really just enjoy that I did something for someone, right? And that's the best recipe because, you know, who wants to be sold to, right? No one wants to be sold to. When you're authentically interested in the other person, how they tick, what they need. I've had many people that become clients literally call me and be like, you've done so much for me, it's almost uncomfortable. Now I get to do something for you. So, back to my daughter, I always teach my daughter, like, don't ask for something from someone unless you've done something first.
32:53 Speaker 01 Not in every case, but that's generally my rule.
32:56 David Weisburd? Do you, do you know Adam Grant?
32:58 Speaker 01 Yeah.
32:58 David Weisburd? Is he a personal friend?
32:59 Speaker 01 No, but I admire him.
33:03 David Weisburd? And he wrote this famous book, Give and Take, where, I'm getting the numbers wrong, but I think something like 20% of people are givers, 20% are takers, and the vast majority of people are these reciprocators.
33:15 Speaker 01 Yes.
33:15 David Weisburd? And this is actually wired in evolutionary psychology. So evolutionary, millions of years ago, if you did not reciprocate, you would get ostracized from society, which basically meant death.
33:25 Speaker 01 Interesting.
33:25 David Weisburd? So this isn't necessarily people being good or bad people. People could weave in morality into, but this is in our DNA. So to your point, if you truly give and not like fake give or say, hey, I know this person, but you don't know them, or you make an introduction where one person's like really annoyed with a meeting, there's a lot of variations of things that look like giving that's actually taking. But if you're truly giving, call it 60% of the population will be compelled to give to you, and they'll feel this extreme drive to give because In years past, if you wouldn't reciprocate, you'd be kicked out of the tribe.
33:53 Speaker 01 I did not know that. That's very interesting. I do know somebody, this is interesting. I was desperate for like a speaker at a meeting like a million years ago, like an offsite meeting. And I had this guy named Kevin Carroll. He's still out there, but now he, he actually makes games for a living and they've been very popular games. But he was like a life coach or something. And he came and he did this exercise and he made people stand up and said, okay, you know, person A and person B, person A, close your fist. Person B, you need to convince person A to open their fist. And then, you know, you did it and half the people opened their fist and half didn't. All right. And then they turned it around. Person B, you got to convince person A to open their fist. Now, the point was the law of reciprocity, that the people who opened their fist, when they went around the other
34:35 Speaker 01 way, the other person opened the fist. And when the people that clenched their fist the whole time, the other time, 99% of the time was a clenched fist. And when you think about this in like the email world, if I send a shitty email to you, you kind of send a shitty one back. If I send a smiley emoji, you've got to send that vibe right back. And that's kind of what he taught me. It's a little bit of the Adam Grant thing. But I think that's just basically human.
34:58 David Weisburd? If you go back to 1995, you could give yourself one piece of timeless advice that would have helped you build Prosek even bigger than it is today. What would that be?
35:07 Speaker 01 It would probably be to not, you know, I bootstrap my business. I never had debt, but I never had an investor. So I was worried about spending. I would have invested in talent in a more aggressive way earlier in the game. When you start, you kind of like, you know, you want to spend less, you want to do like, in my world, in every world, talent is everything. And you, investing in the right talent early just accelerates your success. So I probably would have done that a little earlier. I would have also done for myself what I tell my clients to do. I didn't do a lot of branding and marketing for our firm in the beginning, just didn't have the time, didn't have the whatever. And when I got around to doing what we do for our clients for ourselves, I was like, oh, this stuff really does work.
35:51 David Weisburd? You've grown this large firm. How do you spend your time? So you have 100% of time in a week. Where are you spending your time?
35:58 Speaker 01 It's a great question.
35:59 David Weisburd? What would you like that time allocation to be?
36:00 Speaker 01 Because talent still is the number one indicator of our success. I spend a lot of time with talent, whether it's the talent we have or it's a talent I'm trying to have. That's, I don't know what percentage that's a piece of it. Clients, I mean, I care about my clients. I still have, I don't know, 35 clients I'm really quite engaged with.
36:22 Speaker 01 I do do a lot of convening and moderating. It's just my thing, just like the podcast is your thing. I love it. I spend a lot of time there. Operating the business, I love operating business, spend a lot of time there. And then, listen, once you get to the top, I always say if you have a 51% good day, you're beating the system because you are the chief problem solver. You are. So I spend a lot of times.
36:42 David Weisburd? As Elon says, all the problems go up to the CEO.
36:43 Speaker 01 That's right. And if you're not a brave, I always say if you don't prune the garden, the weeds take over. I am the gardener.
36:50 David Weisburd? What does that mean?
36:50 Speaker 01 I'm the chief nudge officer and I'm the gardener. Chief nudge officer means like I am the driver. I am, people are shocked at my firm. Like, how did you know that? How did you know to push me right now? Like, I'm like, I know.
37:02 David Weisburd? The answer is always push.
37:03 Speaker 01 Yes, the answer is always pushed. The answer is always push and faster. And the chief gardener just basically means you don't walk by the weeds, you pull them. I don't ignore mistakes or problems. I dive into them and fix them now. I believe in fast problem solving. So I spend a lot of times there. But I think problem solving, even in the worst day, can kind of oddly electrifies me. I like hairy problems.
37:28 David Weisburd? Is that something that you learned to rewire your brain? Or have you always liked solving problems?
37:31 Speaker 01 I think I've always liked it. I would also say, not to psychoanalyze myself too much, but I had some really hard things happen in life really early, I realize. And when you have really hard things that are solved early, when you show up to the workplace, you're like, oh, my God, this isn't that hard. So I feel like comparatively speaking, I've always had this like. That's not so bad. It's gotta be really bad to get me fluffed up about it.
37:54 David Weisburd? So I grew up, my family came here with $600. We're refugees from Russia. And I went to private school on scholarship and I had this eighth grade party, eighth grade at my place. And I remember we had hot dog buns and hamburger buns and we ran out of hot dog buns. So we only had hamburger buns and my classmates wouldn't eat the hot dog and the hamburger buns. And at that point, I realized, holy crap, if this is how fragile everybody is, biggest problem in life, I'm gonna run circles around these guys.
38:19 Speaker 01 When you have a gritty, early life, even if it's painful, it's kind of a gift. Because there's so many, to your point, fragile, not resourceful, thin-skinned people. So to some degree, I think having a little bit of trauma early ends up being good for your work life.
38:37 David Weisburd? Well, Jen, you're truly a legend. Your firm has been a great partner to us, dozens and dozens of guests. So thanks so much for the partnership.
38:44 Speaker 01 Thanks for having me. Loved it.
Previous E357: CalSTRS CIO: Where Do You Invest $390 Billion Today? Next E359: What Charlie Munger Taught Me About Venture Capital Page updated October 30, 2026 · transcript and summary are machine-generated