How I Invest with David Weisburd - E358: The Woman Behind the World's Top GP Brands | Jen Prosek
Episode Date: April 29, 2026What 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
Discussion (0)
Jen, you are the ProSec and ProSec, 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?
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 the sort of style of the day was keep your head down, don't engage.
It was like no engagement with stakeholder 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.
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. When you say firms weren't focused on branding,
I can't help us 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.
Yes. As if it was like a dumb question. And then in the 2000s, I started doing now. 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 pain killer? You need to have
branding. 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 a 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, like, even at least have some appreciation for crisis communications
or crisis management, no interest whatsoever.
And that has changed so much.
Has it dramatically changed again the last couple of years?
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 different.
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, 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.
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 comm 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.
If you take a step back and you look at the LP market, because essentially, 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 and their
call it their core managers. They're 15 to 25 per asset class. 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. Yes. And if you're a manager that wants
to grow, you have no choice, but you have to focus on that.
That's exactly right. And that requires brand and marketing. Yes.
And that's why you have Blackstone doing these somewhat cringy.
Oh, yeah. John Gray's running videos. Yeah. I meant more of the holiday video.
Oh, okay. I think the holiday video, my view, is probably also a talent play. But I think the running
videos and the constant, you know, 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 are still looking at it.
The latest stat that I heard is 95% of retail capital today is going into five firms, the Blackstone's
Apollo's KKRs of the world. 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 an offensive way?
And where's the alpha for smaller firms? 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 mid-sized 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?
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.
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of asking an extremely dumb question. No, nothing's a dumb. Remember nothing's a bad question. You have a firm
that goes out to quote unquote retail. Yes. How does retail buy? Is it through their RIAs? Is it
through the large platforms? Is it inbound? What's the common practice and how funds convert retail
interest into AUM? There's a number of ways. Either you get on a platform like a Morgan Stanley,
a UBS, etc., it's Merrill Lynch, right? One of the big wirehouse platforms, 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
FAA across the 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
a lot of elbow grease. Like, let's go see the high net worth group of Merrill Lynch in, I don't 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 squirrelier 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. 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? 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...
It's more scalable.
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 Case platform.
They have a conference every year that is like the milking 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.
If you go to the case 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.
Last time we chatted, you said that brand helps managers with efficiency and preference.
What did you mean by that?
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.
Too expensive for that.
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 can 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, 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 then. And
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.
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.
Yes.
If you could get introduced by an existing LP, but if they've been listening to five of your podcast,
not only does that help you get the meeting, yes, it helps with that for sure,
but it also dramatically reduces the sales life cycle.
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 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.
My co-founder of my business here, Curtis is sitting down, but I started the podcast with Eric Tornberg.
So the co-founder of the podcast, Eric Torrenberg, he now runs media for Andreessen Horowitz.
And one of their Mark Anderson and Ben Horowitz thesis on that is the media part of the podcast.
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 do you
thoughts on that?
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.
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.
That makes sense.
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 crises,
how would you coach somebody on a podcast that has a fund? What are some best practices and what are things to avoid?
Well, you certainly have to avoid stepping on a regulatory mind 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,
like everyone else's, don't even bother, right? When these things are effective is that the audience
got some value. So 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? 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 was a total commercial.
Like, you can't do that either.
So this is 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.
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.
That's right.
Against the top podcasters in the world.
So the moment that people think that you're selling or not taking a point of view or have no unique opinion, they're just going to fast forward.
Even if I as the host want people to listen, doesn't matter.
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 on stage who said nothing and wasted your time.
You remember that.
So it's like, don't even dare doing it.
It can be a brand backfire in my view.
For a GP that has a finite budget,
maybe not a small budget, but not a large budget,
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Support for today's episode comes from Square.
The all-in-one way for business owners to take payments,
book appointments, man and staff,
and keep everything running in one place.
Whether you're selling lattes, cutting hair,
running a boutique,
or managing a service business,
Square helps you run your business without running yourself into the ground.
I was actually thinking about this the other day
when I stopped by a local cafe here.
They use Square,
and everything just works.
Check out is fast, receipts are instant,
and sometimes I even get loyalty rewards automatically.
There's something about businesses that use
Square, they just feel more put together.
The experience is smoother for them, and it's smoother for me as a customer.
Square makes it easy to sell wherever your customers are, in store, online, on your phone,
or even at pop-ups, and everything stays synced in real-time.
You could track sales, manage inventory, book appointments, and see reports instantly
whether you're in your shop or on the go.
And when you make a sell, you don't have to wait days to get paid.
It gives you fast access to your earnings through Square checking.
They also have built-in tools like loyalty and marketing.
Your best customers keep coming back.
Right now, you can get up to $200 off Square hardware when you sign up at square.com
slash go slash how I invest.
That's SQ-U-A-R-E.com slash go slash how I invest.
With Square, you get all the tools to run your business with none of the contracts or complexity.
Run your business smarter with Square.
Get started today.
Support for today's episode comes from Square.
The all-in-one way for business owners to take payments, book appointments,
man and staff, and keep everything running in one place.
Whether you're selling lattes, cutting hair, running.
a boutique or managing a service business, Square helps you run your business without running yourself
into the ground. It's actually thinking about this the other day when I stopped by a local cafe
here. They use Square and everything just works. Check out as fast, receipts are instant, and sometimes
I even get loyalty rewards automatically. There's something about businesses that use Square. They
just feel more put together. The experience is smoother for them and it's smoother for me as a customer.
Square makes it easy to sell wherever your customers are, in store, online, on your phone, or even at
and everything stays synced in real time.
You could track sales, manage inventory, book appointments,
and see reports instantly whether you're in your shop or on the go.
And when you make a sell, you don't have to wait days to get paid.
It gives you fast access to your earnings through Square checking.
They also have built in tools like loyalty and marketing.
Your best customers keep coming back.
And right now, you can get up to $200 off Square hardware
when you sign up at Square.com slash go slash how I invest.
That's SQ-U-A-R-E.com
slash go slash how I invest. With Square, you get all the tools to run your business with none of the
contracts or complexity. Run your business smarter with Square. Get started today. Every budget is finite.
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? 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 funding 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. Because 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 got to start there.
The great news about today's world is in addition to the media that we read, 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 and 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 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 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.
in, 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
podcast, I'd be asking chat, GPT, 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, etc. And you'd be surprised, this is my best advice for some with the 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 quality. But you want to have the reason I say one thing a quarter.
or 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,
you're 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.
So many great things to unpack there. Said another way, offense, the best defense is a great
offense is not having a strategy as 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 done. Same thing in the LLM world. If you don't have anything
about you, and God forbid you have something negative that happened, that's going to dominate
the LLM prompt. 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.
I want to go back to something you said.
You said a lot of interesting things in a row.
Good.
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.
That's right.
So if you don't have something smart to say, you could just as a thought experiment,
send it to a billion people.
Right.
And now you're going to be known as an idiot.
Yes.
Right.
Fame and brand and getting out there is not always a positive thing.
Right.
There's plenty of examples, which help.
A lot.
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?
Right.
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 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
months on a 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. Yeah. A lot of people don't want to quit and don't want to pick
pick 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 everything.
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. What I tell my daughter about like finding your career, you could
pick something that people say is going to be the most successful or the most moneymaking.
But the guy in the crazy niche you 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'd 10 heads
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 sort of naturally built to do. And then it's much more successful.
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, if no one's reading?
Because nobody will listen, nobody will read for so damn long that if you are not intrinsically interested in that medium, you will fail.
Totally.
So, for example, not that you asked me this, but if you did, Jen, how did you build this company in your 20s to a company that's number one in the private markets?
And I would say 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'd,
I didn't introduce them to each other.
I'd moderate the table.
I make them all look like a million bucks.
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 ProSec?
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
these unbelievable dinners where I meet all these people who become friends and people I do business
with, I 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, 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. So that stuff just drives me.
You just got to find the thing that doesn't feel like work that you love.
And podcast is like that for you.
You've weaponized your people pleasing.
Yeah, exactly.
I'm like, okay, I'm a people pleaser.
I can't do anything about it.
I could go back to my childhood to a time machine,
or I could just embrace it and productize it and play 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.
build, go there. Seven people will listen to it. It's going to go poorly and you're going to learn. Do like five to ten 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 nonzero 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. 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. So you went from
1995 to hustling and bustling to your first couple 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
pro-sec. 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 or whatever. But finance takes you everywhere, right?
When you represent the best investors in the world, they're investing in health care 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 health care 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 doubles every year for a lot of reasons.
But what's really next for ProSec 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? 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 learn 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.
And you're a super connector.
You were introduced to me by one super connector around Descartes.
You're also close with Rahul McDowell, who's a good friend of mine.
I love those guys.
Yeah.
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?
It comes back to giving gifts and the law of reciprocity.
So even when I was in my 20s, I figured out, 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, okay, 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?
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.
Not in every case, but that's generally my rule.
Do you know Adam Grant?
Yeah.
I see a personal friend.
No, but I admire him.
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.
Yes.
And this is actually why are an evolutionary psychology.
So evolutionary millions of years ago, if you did not reciprocate, you would get ostracized from society, which basically meant death.
So this isn't necessarily people being good or bad people, people could weave in morality into it.
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 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 drive. 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 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 of them.
All right, and then they turned it around.
Person B, you've 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 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 kind of 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.
If you go back to 1995,
you could give yourself one piece of timeless advice
that would have helped you build ProSec
even bigger than it is today.
What would that be?
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.
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?
it's a great question.
What would you like that time allocation to be?
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.
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 spent a lot of time there. Operating the business. I love operating business. Spent 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 spent a lot of times. All the problems go up to the CEO. 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. What does that mean? I'm the chief nudge officer and I'm the gardener. Chief Nogooj officer means like I am the driver. 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.
The answer is always push.
Yes, the answer's always pushed.
The answer's always pushed and faster.
And the Chief Gardner 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 spent 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.
Is that something that you learned to rewire your brain, or have you always liked solving problems?
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 got to be really bad to get me, you know, fluffed up about it.
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 talk 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 going to run circles around these guys.
When you have a gritty early life, even if it's paid.
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.
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 a partnership.
Thanks for having me.
Loved it.
