E250: The GP Fundraising Playbook: From First Meeting to Final Close

What does it really take to raise a venture fund—and why does fundraising never get easier, even at Fund 5 or Fund 6? In this episode, I talk with Yasmine Lacaillade, Founder of Sinefine and one of the most respected capital formation leaders in venture. Yasmine shares her journey from TPG Axon in London to joining Drive Capital at Fund I—years before it became consensus. We discuss why fundraising is always difficult, how LP sentiment shifts every 2–3 years, and why top fundraisers treat the process like enterprise sales rather than relationship maintenance. Yasmine breaks down her market mapping framework, why the top of the funnel must always stay wide, how to qualify LPs quickly, and why “adding value first” is her core operating principle. She also explains how she evaluates new managers, how to identify true LP demand today, and why people, culture, and team cohesion matter more than anything else in venture.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  Tell me the story about how you moved from London to Columbus, Ohio.

• 0:03Speaker 01

  It was definitely the last place I ever thought I would be prior to moving to Ohio. I moved here for personal reasons. My ex-husband had a family business that was headquartered here. And I had just joined TPG Axon in London, which was an amazing opportunity for me to work with. A big spin out from Goldman Sachs on the hedge fund side, who was building a really big hedge fund platform under Dave Wonderman's broader TPG platform. And I was supposed to go execute everything in Europe. And then life happened. And I'm a family-first person. So we moved to Columbus and I worked remotely for TPG Axon covering Europe,

• 0:45Speaker 01

  which was a crazy way to live your life, honestly. I was on one of those old-school Citrix dial-ups. This was before remote work was well thought through. When I got to Columbus, I serendipitously was introduced at a cocktail party to two Sequoia partners who were, at the same time as us arriving here, were lifting out of Sequoia to bring venture to America. And I'd just started this new gig in the hedge fund space. And here were these two crazy guys that told me that they were going to invest in technology companies between the coasts. And this maybe tells you a little something about who I am.

• 1:27Speaker 01

  But it was one of those opportunities that, once I heard it, I couldn't unhear it. And I basically called them up and said, I'll take out the garbage for you. I'll do whatever you want, but I do know how to fundraise. And so I could be in charge of your investor relations. And that is the start of my Columbus journey, which has been, quite frankly, the most exciting decade and a half of my life.

• 1:53David Weisburd?

  It's interesting because a lot of times when people hear narratives about Sequoia or Drive, they're hearing it at a later vintage, so Fund IV, Fund V, Fund VI, once it's already consensus. But you saw something. While they were in their fund one, what exactly did you see that made you want to drop everything and join Drive?

• 2:13Speaker 01

  This is the story of my life. It is contrarian and exciting, and I am super drawn to incredibly smart people. I always want to be the dumbest person in every room. And when I met them, those two things were true. With the advent of cloud infrastructure, great companies can be built anywhere. And Silicon Valley was already getting frothy in 2012. The idea of huge TAMs existing outside of Silicon Valley logically made so much sense. When you think about the GDP of the middle of America, it was at the time the fifth largest GDP in the world.

• 2:57Speaker 01

  And that was an opportunity that seemed super obvious to me. But to your point, it wasn't as obvious to the LP community. And the LP community, I think when they, we started, the thought was very much one, I mean, they're very humble. But of course, you think, oh, every Sequoia LP is going to want to do a Sequoia spin out. That doesn't end up being the case because there was so much new for the LPs to have to chew on and defend in front of their own ICs that, you know, what we thought would be a really easy fundraise wasn't.

• 3:39Speaker 01

  And by the way, I've never done an easy fundraise, so lesson learned there.

• 3:43David Weisburd?

  It never gets easy, Fund5.

• 3:45Speaker 01

  It never gets easy.

• 3:46David Weisburd?

  Why is that? Is that because you're always going kind of towards larger fund sizes? And why does it never get easy?

• 3:54Speaker 01

  It never gets easy because there's always...

• 3:58Speaker 01

  There are always new factors because in venture, unlike say, event in in a hedge fund space where you have these open end structures which are constantly, which have their own issues, right? Because there's a constant liquidity. So you you're constantly really close to the market, but you're constantly also at risk of losing it. So that's a different beast. But in the venture world, you really are only in market every two and a half years. And so much changes in the world in two and a half years. At a macro level, sentiment changes or liquidity profiles change. And it's as hard in a in a bear market, it's hard because coffers are dry. And in a bull market, it's hard because LPs heads

• 4:42Speaker 01

  are exploding because everyone is trying to raise money so quickly. And I just don't think they have the bandwidth to address it all. And so it's always really hard to manage that sentiment. And then at the micro level,

• 4:56Speaker 01

  venture firms, I think, have a really high retention rate because they're very small partnerships. But LPs strategic initiatives shift so much over a three year period that someone who you were really close with in Fund Two may have a completely different set of priorities when you go out with Fund Three. And yes, it's on you to to stay close to that and manage that evolution as it goes. But just, just the natural evolution of every business means that the priorities year one and the priorities year three are going to shift. And so I think the most important element of fundraising is understanding that that dynamic and understanding how much things shift and knowing that no two fundraises

• 5:38Speaker 01

  will be the same because of those sentiments. And that means that every fundraise, you need to have the ability to not only manage the people that are already bought in and will continue to buy in, but to manage the churn and know that like the skill set that you as the fundraiser need to have is the skill set of networking, not honing the just honing the existing network.

• 6:01David Weisburd?

  What's the difference between networking and honing the existing network? Tell me about that.

• 6:05Speaker 01

  With an existing network, you have a set of really close relationships that you would leverage to

• 6:13Speaker 01

  Get money through the door. When you're constantly networking, it's more of an enterprise sales model where you need to have a really big top of funnel at all times. Because what is going to convert is not the same raise over rates. So in my opinion, that's the only way to be long term successful. First and foremost, because personal relationships don't turn into transactions. That's just not the way the world works anymore. Also, you know, even if I was a very well networked person and, you know, had everyone that allocated on speed dial, realistically, you could maybe, if you're really good and really social, which I am neither,

• 6:57Speaker 01

  have 50 great relationships. And then you have to bank that those, a good portion of those 50 relationships are going to convert. Because at any scale, whether you're a $50, a $50 million fund or $5 billion fund or $15 billion fund, you're going to have at least 50 relationships in there. And so to me, the math doesn't work on that because the conversion rate is too low in any one fundraise. And so my approach to fundraising has always been one of make sure that if your conversion rate is under 5%, that your top of funnel, you know, nets out to whatever the number is that you that you want to convert, that you have the right amount in top of the funnel, you know, if you're not,

• 7:41Speaker 01

  if you're not in touch with over 700 accounts, you're not going to be able to close on your fundraise, no matter what size. And so to me, that is networking where you're constantly building out new nodes, new networks, because things shift. Today, I would say that, you know, there's, there's factors that that we could see coming, like the lack of liquidity in LPs coffers. But there's other things that you didn't see coming where the administration is trying to hamstring endowment.

• 8:15Speaker 01

  Capital, right? And so if they don't know how much of the long-term assets are they're going to need to feed the annual working capital lines, then they don't know how much money they're going to be able to pull into their long-term pool. So all the endowment relationships that I've built over the last decades, some of those might be effect might transact in the next fundraise, but a lot of them couldn't due to factors that I had, I, they have nothing to do with. So if I'd only focused on my existing relationships in the endowment space, I wouldn't be able to close a fundraise. But if I had spent my time making sure that I'm along with the 100 endowments that are out there, I'm focusing

• 8:55Speaker 01

  on the 200 pensions and the 50 RIAs and the 20 private wealth platforms and making sure that those, uh, uh, those decision makers are also aware of what we do and how we do it, then I've got a much better shot at being successful.

• 9:12David Weisburd?

  How do you balance relationships with the numbers game aspect of fundraising?

• 9:17Speaker 01

  It's such a great question because this is the kind of thing I think about when I'm laying in bed or in the shower. You know, how do I build this business where I am building a high degree of trust with my GPs and creating a high degree of trust with the LPs, therefore being transactional with neither, but understanding that the true nature of this is in a way transactional, is in a way enterprise salesy. I haven't run into a roadblock with it yet.

• 9:54Speaker 01

  The most important thing that I do is even though it's transactional, it doesn't mean it's not thought through. So if I have a conversation with an LP and they tell me that what they're looking for in their book over the next 12 months is to fill out.

• 10:17Speaker 01

  Growth equity managers, because that's what's lacking in their, in their current portfolio. I'm not going to go send them a seed manager. And so I think that making sure that while my volume might be high and, and the, the conversations are quite broad, that they are not empty and that when an LP gives me intel on what they're doing, that I respect that first and foremost. And that to me creates a win-win because I think the, the greatest thing you can do is give back people their time. And that sounds so trite, but I think it's the only thing that we're all short of.

• 10:58Speaker 01

  And so if I can only, if I, if I make sure that I only put qualified leads in front of my GPs and conversely, that I'm only showing LPs a segment of the market that they're interested in,

• 11:11Speaker 01

  I build fidelity with both of them. And that philosophy on how to build CNA FNAE in the way that I'd like it to be built.

• 11:23David Weisburd?

  There's a couple of truisms I've picked off from some of the greatest fundraisers like Rahul McDowell, who's raised 99 billion. And there's a couple of paradoxes to how the top fundraisers work. So one is they'll spend an inordinate amount of time with individuals. So they kind of pick their shots very early. His example, I think it took him 15 years to get a check from University of Texas. He's kept on delivering value. That model, however, although Rahul might not admit it and other people might not admit it, it only works if the underlying capital pool is large. And if that underlying check is going to be sizable and is going to be a platform shifting type of check and capital partner.

• 12:06David Weisburd?

  What a lot of the top fundraisers do is they're extremely selective at the onset. One way to frame that is there's no such thing as a small LP or a small relationship. Every LP even and especially sometimes when they make a hundred or $250,000 check, sometimes those are the most difficult to manage and most time consuming and energy consuming relationship. Making the bets on the right LPs on the front end, I found to be something that almost every top fundraiser, whether they're literally fundraising for their firm or they're the founding GP of fundraising. One thing that they do. And the second thing is paradoxically, once you're in this, this club, they give just the best service ever. So they give the seven star hotel treatment to each one of those people

• 12:48David Weisburd?

  and become non transactional. So in many ways, they're very, very calculated in the front. Who gets into the VIP? And then, and then once you're in, then you get the full service. You never have to pay. You know, you could invest 10 years down the road, five years down the road. It doesn't matter because what matters is that we're going to make sure that you're having a great experience throughout the entire process. And at some point, to your point, you're going to want to do a growth equity fund. It's inevitable that, that at some point, there's going to be a match between what you're doing, what that LP is doing. And you just have to be around the hoop at that point. So there's this kind of paradox I've seen the best fundraisers.

• 13:22Speaker 01

  I just have a very different philosophy on that.

• 13:26Speaker 01

  I don't. I don't have a ton of particularly close relationships and I'm not looking for those.

• 13:38Speaker 01

  I am, however, really focused on market mapping. I learned a lot of that from working with really brilliant GPs. Right? If you're going after a certain market, make sure you know every player in the market. Who are the biggest players in the market? What are they doing? And then go out, go after the ones that are the most attractive. That might be, I, I, I might be misconstruing part of what you're saying, but to me, I would never, for example, build a relationship with the GP.

• 14:13Speaker 01

  In the hopes that in the next 15 years, something might hit. First and foremost, or sorry, I meant LP, not GP. First and foremost, because LPs have, get so bombarded, so bombarded. I feel bad every time I send them an email, and it's a lot. You know, I try to be really deliberate about when I send them something. I try to make sure it's something that, you know, as our attention spans gets shorter, is bite sized by nature up top, and then they can hear dig in deeper through further literature, the call, whatever it may be. But to me, it's much more important to say, like, say we're market segmenting. We think pensions are going to be really important in this coming fundraiser.

• 14:55Speaker 01

  Then I'm going to market map the pension world, see whose dollars match up best to the fundraiser, right? If you're raising a $500 million vehicle, I want to be in front of as many $50 million check writers as possible, because that's the best return on time versus $5 million investors. If you're raising a $50 million fund, you should be. And so it sort of scales to, I would say, you know, anyone who could be up to 10% of the fund. That's, I think, your ideal customer profile. And then I go after those that are active, either directly via their consultants, their outsourced CIOs, whatever that might be. And that mix, that market map, is frozen in time.

• 15:40Speaker 01

  So as much as I would love to, when I add in a new, when I take on a new client, go back to my market map and rinse and repeat the same process, the reality is going to be very, the names will likely still be very similar, because pension funds don't pop up every decade, century. But their priorities will shift, and what they're interested will shift. And I also make sure that, by the way, my GPs don't overlap in strategy and style, so that I have a menu of things that are different. Because I don't, A, want to be selling competitive, competitive managers against each other. I don't think that serves anyone. And I also want to make sure that, you know,

• 16:20Speaker 01

  There are multiple potential points of interest in a specific LP market segment. So some pensions might be really interested in early-stage healthcare. Others might be interested in late-stage cybersecurity. Some may like a thematic approach. Others may want diverse mandates, whatever it may be. In that sense, like the tagging, the interest tagging of your LP base is super important because it allows you to do these exercises quite quickly. But it is, I think, really different from saying, I'm going to build relationships with these 20 VIPs and then something will hit. I don't find it effective.

• 17:04Speaker 01

  I also do multiple fundraises a year for different managers. I wouldn't be in business if I was waiting for LPs for the match to be made. Because, by the way, this is like a marriage, right? When you invest in a venture fund, you are invested for the next 12 years. It is a big decision, no matter, you know, how close or how far away you sit, like whether you're the family member whose assets are going into it or a fiduciary who is responsible for someone else's assets. It's a big decision because you can't reverse it very easily. And so I think the matches are really hard to make. And so you need to have a ton of shots on that because the probability of them converting

• 17:47Speaker 01

  is so low, which is something I annoyingly always come back to.

• 17:50David Weisburd?

  When you're talking about GPs, you're talking about for the GPs that you invest in or just other GPs?

• 17:55Speaker 01

  But when we first started CNA FinA, it always had to be because, you know, I was starting it on my own, like in my garage.

• 18:05David Weisburd?

  It's a nice garage.

• 18:06Speaker 01

  Ha, ha, now it is.

• 18:07David Weisburd?

  I'm sad as the garage right now.

• 18:10Speaker 01

  Yeah, you should see my garage. And it was always, it always had to be an extension of my skill set, which was around investor relations and capital formation. But I am very aware that this is a services business. And again, having learnt from really, really smart GPs and portfolio managers in my life, I want to build a product because product scales and services are harder to scale. And so I thought, okay, I'm going to go out and find really interesting managers to work with. Help them institutionalize their LP base. And in that process, also invest alongside of them. So why wouldn't I build a fund of funds that invests in managers?

• 18:52Speaker 01

  So we also put our own capital to work with these managers and a number of others that we think are really interesting. And so that was Plan A, and it was kind of like my pre-seed deck, right? The first version of your mission isn't what you bring to market because when we were launching this, it was 2022, 2020 into 2023. There's a really brutal market and I will never blame the market for anything. This is, I'm taking full accountability. I, we, the team that have put together to do this, could not get a fund of fund off the ground. So when it was clear within the first six months of being in market, that we weren't going to be able to get to a first close.

• 19:35Speaker 01

  I've done enough fundraising that by in the first six months, you need to be well into a first close to have a successful fundraise. And so we should-

• 19:43David Weisburd?

  It becomes a self fulfilling prophecy in both directions.

• 19:46Speaker 01

  Yeah, yeah. And so I was like, there is no product market fit.

• 19:49David Weisburd?

  So to contrast your style, maybe from a Rahul's is he is focusing on the individual and you are focusing on what the LP needs today. So you are delivering the product, solving the number one or top three pain points of the LP today. And once that LP invests into a fund that you're partnered with, then they're going to be there for the long term relationship. You don't have to worry about how do you build a relationship with an existing LP? That's much easier than building a relationship with a prospective LP. So you're focusing on what problem guys help free today. And that's your entry into this VIP world. And then you manage the relationship once they're inside the VIP.

• 20:27Speaker 01

  Yeah, but I would say that my true VIPs are my GPs. So, you know, we work closely with three, four managers at a time, no more at this point, right? We want to, we want to build out the business and probably double that. But we need, we need, I need to clone myself in a certain respect in order to do that. And we're really going out and making sure that both the GP and the LP's time is protected in the sense that we want to make sure that when we go to market with a product, when a GP goes to market with a product, which we're in part or entirely in charge of completing, i.e. completing a fundraise, that we do that successfully in the least amount of time.

• 21:09Speaker 01

  And because we have so many conversations with the LP community, we already know who we should go out to with that particular product because of the market mapping, market mapping work we did, because we're out in the market talking to the LPs and making sure we understand their needs, so that I'm not going to go knock on someone's door with a product they don't need, because by the way, that also damages my relationship with that LP. I want LPs to know that I will only reach out to them with things that might be of interest. The VIP list of LPs is different for each manager, so I'd have four different VIP lists, right? And there could be some overlap, but for the most part, there isn't. And so I've got like four different blocks of, I guess, VIP LPs that correspond to each manager

• 21:52Speaker 01

  and where, you know, the LP's priorities correspond to what the, what the GPs are offering.

• 21:58David Weisburd?

  And this is where I think a lot of GPs get it wrong, which is the most difficult thing to do is to get the first meeting with an LP and decision maker. The second most difficult thing is to get the second meeting with the LP decision maker. And the third is the third meeting. And I say that in jest, but a lot of people don't realize how important that first meeting is in getting that second meeting. And how many, that pipeline from first to second meeting might be 10%, it might be lower depending on the different dynamics. What does it mean to deliver on that first meeting? It means, A, being a good listener, not transactionalizing them, figuring out what they need. Forget about what you need, which is obviously money from the LP, but figuring out, A, if they're even a fit. If not, how could you salvage the rest of the meeting and perhaps build a relationship over time? We talked about this, that you could only build so many relationships.

• 22:43David Weisburd?

  You have to focus on, on your immediate fund. But you want to be, make sure that that LP goes out of that meeting saying, wow, that was awesome. Maybe not a fit, but we're going to be tracking them because LPs also have two buckets. Well, they have three buckets. One is we're never going to meet with them, although they'll never say that again. Two is we're going to track them. And three, this is something that we might invest in this vintage. People oftentimes thinks, well, you're going to track me. Oh, you know, that's a way of blowing me off. That's actually a pretty small bucket of LPs or GPs that LPs track. You want to get in that bucket at the worst case. And the way to do that is to deliver on that first meeting. And if you take that down to the most basic neurobiological levels, you want to create self reinforcing behaviors that says LP sees this GP. If they're not a fit, they add value to my life. Therefore,

• 23:27David Weisburd?

  I will add them again. This neurosociative conditioning between seeing a specific person and having a positive experience.

• 23:33Speaker 01

  Such a good point. I make a lot of efforts of knowing a lot of GPs, even though we don't work with a lot of GPs. And it is exactly for that reason. And my managers are actually all very good at understanding that first order issue or concept where if I, if you're able to deliver some sort of value, you stay front of mind, or I wouldn't, that's a transactional way of putting it. You start building a level of trust. I think that's what it like comes down to. And

• 24:14Speaker 01

  when in a first meeting, you're going to, you're going to either fall into the tracking bucket, or we're not going to take the second meeting, right? Those are your two not, not perfect options. Like, perfect option is we're going to go do the work on this.

• 24:28Speaker 01

  But in order to really square yourself into the tracking and, and I'm going to keep you on our list camp, it's exactly that. And you can do that if you know enough GPs. You're obviously talking to people who are active in the venture market. And by the way, there are cases where, you know, new entities pop up all the time. And I'm going to make sure that before I put any entity in front of one of my GPs, that I know that

• 24:53Speaker 01

  They are active in venture and they are deploying capital.

• 24:55David Weisburd?

  That goes to the behavior. How do you know that somebody is going to invest? They're investing currently.

• 24:59Speaker 01

  Correct.

• 25:00David Weisburd?

  Everybody says they're open for business, but how many investments have you made in the last six months? It's the same question that startups ask GPs. Okay, you're active. How many have you invested? How many SaaS companies? How many consumer companies?

• 25:10Speaker 01

  Yeah. And, and I found that I find that LPs over the last decade have become much more transparent about that. I think people used to be, and maybe this is me also being younger in my career and less bold about asking the most important question, which is exactly that.

• 25:28Speaker 01

  Like, what have you done in the past six months and what are you looking to do the next 12? That's what it's about.

• 25:32David Weisburd?

  Yeah, it's, it's funny because, and now I've had several decades of, of raising capital, whether startups, venture, funds. And almost without an exception, the people that get triggered by this question are the ones who are not trying to be transparent. And the people that want, that have a scarcity of time and are looking to truly deploy capital, love that question because it's a way of saying, how do I not waste your time? The people that are just trying to waste your time get extremely triggered by that question. It's a very important question.

• 26:01Speaker 01

  And so that's why I'm like, man, you know, when you talk about these, these star fundraisers having these really deep relationships and, you know, going to the US Open and, and doing all these things, I'm like, you know what? I feel like that's most people's last thing they want to do when they're done with a super long week of work and they have been doing back to back Zooms and they still need to write five menos and they, you know, haven't had the time to do anything. And I think that in a Zoom first world, the world has gotten too efficient. Things have to happen too quickly, in my opinion. No one has time to breathe. You could be on, you could do 10 Zooms a day.

• 26:40Speaker 01

  No problem, according to the calendar, but you will be so, like, you become so inefficient. And I think because people are so overscheduled, more than ever, being a little more transactional and saying, right out of the gates, let's make sure that us being in a conversation right now is a good use of both of our times. I think is everyone's dream. So I think that's, to your point, part of why LPs are opening up more because they're like, okay, I only do one new manager a year and right now we're looking for pre-seed. Great.

• 27:16Speaker 01

  I'm not going to waste any more time, but there's an amazing, there are three amazing pre-seed managers operating in these three spaces. Here are their names, here are their details. And I've asked them if they're willing to share the decks. And if yes, here they are. If you would like me to put you in touch with any of them, happy to do so. Something like that, that is super useful, right?

• 27:36David Weisburd?

  I have a rather radical psychological idea. And that's that every relationship outside of family is essentially transactional. And the only time it comes up is when it becomes uneven. When both parties, when either one party is not benefiting from the relationship or both parties are not. So it's upon everybody's imperative to make sure that they're always adding value to the relationship. And the best relationships are the ones that are non-zero sum. Transactional and zero sum are not the same thing. In fact, in order to have a great relationship that's transactional, it must be by definition non-zero sum, where both parties are better off. But I do believe maybe a cynical view, and maybe it's not a popular view. But I do believe taking that mindset and going into any relationship and saying, I need to add value every single time.

• 28:18David Weisburd?

  I'm not going to be able to guilt that person into continuing to meet with me or doing whatever you need them to do. It's my impetus and it's on me to bring the value into the relationship so that they want to add. The other person does not owe me anything. I owe it to them to be valuable in the relationship.

• 28:31Speaker 01

  I wonder what that's like rooted in, like, why, why people almost take an apologetic

• 28:40Speaker 01

  like approach to that? Because you know what? The way that you say it so eloquently, I'm like learning something from you right now. As you were saying that, I'm like, forget maybe the word transactional, because it kind of has a negative connotation to it, which it shouldn't. But maybe it's about efficiency and even efficiency is seems like there's no, there's no heart in it, right? First of all, I derive, we're all self-interest of humans. So I derive joy from knowing I have added value to someone else's day. That actually increases my endorphins and wants, makes me want to do more work. So I become a more efficient machine. And I think that that is true.

• 29:23Speaker 01

  That is very like true in terms of how I want to build every relationship and grow the network.

• 29:32David Weisburd?

  A better way to frame it than maybe transactional is this kind of reservoir. So you have a reservoir and you build goodwill. Cause I think when people think transactional, they think, well, Yasmin, I've known you for seven years. I asked you for a favor, you said, no, you know, I'm blocking you. They presume that it's like one by one, but there's this reservoir of goodwill. And if I've had seven years of great relationship with Yasmin, maybe the relationship could take seven years of bad years, seven years of famine, seven years of feast. At some point though, year eight, maybe year 10, I'm not going to want to engage in that relationship further. And maybe that doesn't rub people the right way. But if you look at observed behavior, that's exactly what essentially every human being is evolutionary wired to do.

• 30:13Speaker 01

  That's a really interesting way of looking at it.

• 30:19David Weisburd?

  So, so, so now to, to, to bring that back.

• 30:22Speaker 01

  My wheels, by the way, my wheels are like, I'm like, can I marinate on that for a bit? Can we pause for like 10 minutes and then like let my brain explode a little bit?

• 30:30David Weisburd?

  My, my wife always invoked my, my wife always invokes my master's degree in psychology from Harvard. I always feel almost guilty to, to mention it. But you know, this, I had two years to basically develop some of these theories and it was in the middle of my career. So I was able to, I had a pragmatic frame to it versus just a purely educational way to look at it. This is where I developed some of these theories, but neither here nor there. I want to go back. So you went in and full credit goes to you. You went into drive, fund one that deployed half, half of their capital in fund one. So extremely early and you helped build that franchise. You obviously had a prolific career, also had TPG. Let's say a fund comes to CNA FNA today and to you Yasmin. And let's say they're an attractive fund. Let's say they check all the boxes.

• 31:15David Weisburd?

  How do you go about, tell me the step by steps on how you go about helping them raise a fund?

• 31:23Speaker 01

  I'm actually, I on boarded one this week. Really exciting spin out. And so it's a, it's, it's a great thing to frame up as I'm truly in the middle of it.

• 31:39Speaker 01

  The people who are a great fit, because again, you know, the marriage between me and the GPs is also a very big one. We're not cheap.

• 31:51Speaker 01

  And

• 31:54Speaker 01

  I was thinking about this a lot recently because the managers have to trust me quickly. They have to believe that I am really good at my job, but they don't really have the luxury of watching me do my work for six months. A lot of times I get a call because they're like, want to do a close in Jan- or first close in January, want to do a $500 million raise, we want to be done in March. And I'm like, woo, spicy, love it.

• 32:25Speaker 01

  And other times, by the way, I join managers when they're between fundraises and we have the luxury of time of building up a new pipeline. But that's usually not in reality when people are saying, I want help. And so they have to learn to trust me really quickly. And so the most important thing when we just, when GPs decide to or want to consider working with us is references from the other GPs that we've worked with, from my time at Drive, LPs as much as GPs. So yes, I am transactional, but that doesn't mean I don't have great, I've built great relationships to it because I think that through

• 33:09Speaker 01

  being efficient or transactional and creating value for the people that you are interacting with professionally, you create a great relationship, you know? I may not be going sailing with them on the Cape. I don't know why, where that came from, I've never done that. But we have a very effective and efficient relationship that benefits both sides. And so I think, you know, Those references are super important. And then I usually, you know, I start to our point, maybe all of this, maybe everything I do in life comes down to this core principle. I try to add value before I'm asking them to sign with me. Right? Whether it is making some valuable introductions, whether it's reshaping their deck, whether it's

• 33:53Speaker 01

  putting the skeleton of a data room together and just telling them what they need to do in the next day, week, month, in order to get where they are, putting together a framework of the types of LPs they have to go after. You have to show that you understand what they're trying to accomplish. So I usually do that. And then, you know, it either becomes successful or it doesn't. There is a manager that I would love to work with that set that recently told me, we don't know if we need, we don't know if we need the help. Does that mean that I shut them off? No. When I meet someone who would be a great match for them, I always send them their way because, not because I'm playing the long game and eventually I want something back

• 34:36Speaker 01

  from them, but because I chase managers and I get shut out too. But I want to work with people that like, that usually people that like I want to go work with versus it's like, I want to be a hundred and not a farmer, just like they say in the.

• 34:53David Weisburd?

  It's the Ashton Kutcher investing principle. Ashton Kutcher, surprisingly to a lot of people, is a great seed investor and.

• 34:59Speaker 01

  He's one of our, our client.

• 35:02David Weisburd?

  Okay. Ashton has this thought experiment, which is when he makes a seed investment, if he for one second wants to quit whatever he's doing and go join the founder, that's that one second of cognitive dissonance, that's when he knows he invests. It's not this like, oh, I think he's going to be good at recruiting, or I think he's going to be good at fundraising. It's like, take my money, take my time. It's this like almost impulsive desire where you're drawn to, to the GP or to the founder.

• 35:26Speaker 01

  And he couldn't be more right. And by the way, he is a prolific thinker. He's an out of the box thinker. He has an incredibly product oriented mind. He's a fantastic advisor, leader. I couldn't see, I couldn't say more amazing things about Ashton as an investor I find and truly inspiring.

• 35:46David Weisburd?

  And a Midwesterner as well.

• 35:47Speaker 01

  And a Midwesterner. And he's so right in that every manager I work for, there's one day a week where I just want to go work for them full time. And it's so funny that you say that because I never say that out loud. But that is 100% how it goes.

• 36:06David Weisburd?

  It's almost like shameful.

• 36:07Speaker 01

  Yeah, I'm like, I'm too obsessed with my managers. I truly am kind of embarrassed about it. But I think that's the way it should be.

• 36:14David Weisburd?

  The opposite is also true, which is if you see it as a J O B, a job, or something you have to do, it's also a signal.

• 36:21Speaker 01

  Oh, yeah. I mean, last weekend, I was trying to think of,

• 36:25Speaker 01

  how do I, how do I reshape the narrative around this fund? That I don't know, that I don't know yet, right? Because I, and I always think about that. I hate becoming a record. And I think that every fundraise, a fund evolves. Areas of competence get, get sharper. Other new areas of incompetence start forming because you're up leveling. And then there's other pieces that you have to build that you haven't built yet. And likewise, I think your narrative, year one and year 15 are radically different. Not because you're not being honest, but because there is an evolution to the story. Just like there's been an incredible evolution to my own story in my, the only three and a half years of our own existence.

• 37:10Speaker 01

  And so I was playing around this weekend with this program just so that, you know, what does the L L M think the story is versus what I, how I tell the story? And what can I learn from a new perspective that could help me shape a narrative into something more interesting? And I'm doing this on a 4 P M. On a Sunday. Because I'm at home just fluffing around, but you know, I'm not, it's what I want to do. It's not because that's like my K P I for the week. It's because every minute of my life, I am honestly thinking about how to make these managers successful. And how can I contribute to their success?

• 37:51David Weisburd?

  The way that I put it is, is I get to do whatever I want on the weekend because I work all week long. And that includes working more and nobody is going to shame me for working more because I earned it through working during the week.

• 38:02Speaker 01

  Totally.

• 38:03David Weisburd?

  I don't have people weekend shame me anymore.

• 38:05Speaker 01

  Agreed. And every other weekend I don't have my kids, which gives me more bandwidth. I carry a ton of mom guilt. And when I do, when my, when my kiddos are around, I need to. You know, I, I, I take a different approach and sometimes it'll be late in the evenings on a Saturday night. I would say I have a pretty non-existent social life, but that's okay because I don't really care for one. This is what I want to be my life's work right now. I get asked the question all the time, why don't you go in-house full-time? You love, you clearly love your managers. And I think about it, to your point, like, I think about that every week.

• 38:45Speaker 01

  And then someone once told me something that I always fall back on.

• 38:53Speaker 01

  And that's, I don't know what it says about me, you're the psychology master, not me. It said, you have to start building your own dreams or you'll be busy your entire life building someone else's. And that distinction for me is what keeps me on my own track. Because I am a people pleaser by nature. And if I, if I don't set the boundary, I will spend my entire life pouring everything that is of me into someone else's stuff because I want them to be successful. That is what fills me up.

• 39:32Speaker 01

  And then I have, and it's a much harder exercise for me to really put boundaries around it and say, the most important success is my own. And even as I say that, I still have to build the muscle that that doesn't make me super selfish. That makes me in charge of my own destiny more than I ever before, but it is a hard one. Um, and, and that quote is something that I fall back on when I start thinking, oh, I'm just gonna join one of my managers, though honestly, I don't know which one I'd pick.

• 40:06David Weisburd?

  My unsolicited advice to you would be to weaponize your people pleasing. What does that mean? I've weaponized it with this podcast. I love making people look good and I just, I've become extremely good at it and I deliver this product and I build these relationships at scale and I keep up with relationships with all the people I listen to a podcast. Instead of fighting my people pleasing, instead of focusing on how do I not be a people pleaser? How do I be the best people pleaser in the space? And we're, right now, we're the number two LPGP podcast and, you know, if we continue, we'll be the number one. And instead of going against my programming, against my DNA, I've weaponized and gone through it and embraced it.

• 40:41Speaker 01

  Wow. That's the best advice I could get and to take it full circle on what we started talking about. You know, if you think about adding value, right? The question you're really asking on a phone call is, how do I make this person successful? That's people pleasing. People pleasing just sounds bad. But really, the question, how do I make this person successful? Is a really fulfilling one. It is a central weave inside of like the fabric of our world.

• 41:12David Weisburd?

  If you think about, I go back, I won't use Elon because he's politically, people, people agree or disagree. But some of the greatest people pleasers, how I would look at it is Bill Gates. He made, I think at some point, 4,000 millionaires. This was in the 90s when a million dollars and he pleased 4,000 people. You could argue whether that was his operating principle or whether he cared about that. But the greatest people pleasers is the ones that create the most amount of value where it goes into the ecosystem. I think Jensen Wang owns less than 10% of Nvidia, I believe. So to become a billionaire, to become a decade billionaire, you have to please the entire market, both, both internal and external parties in order to achieve that. So people pleasing, when you take away the shame out of it, could be an extremely like potent economic force.

• 41:57Speaker 01

  I hadn't thought about it that way because honestly, I've always thought that to be a true world-class leader, you need an element of ruthlessness. And I've always wondered, do I have that ruthlessness in me or not? And maybe that's not the mark. Maybe I'm thinking about it the wrong way because the way he put it in a very eloquent way is

• 42:18Speaker 01

  a much more tangible way of seeing it. And also positive versus, you know, ruthless. Ruthless doesn't have to be negative, but there's this undertone of self-serving, which is in direct juxtaposition to the idea of people pleasing.

• 42:36David Weisburd?

  There's a famous essay by Paul Graham, which is why nice founders can become successful. To answer your question, you could say, well, you don't have to be ruthless. You know, you could create a bunch of bumper stickers, but I think it's contingent on the industry. I think in certain zero sum, if you're in gangs, if you're a natural resources monopoly, you have to be ruthless. I just listened to founders, founders on John Rockefeller founders podcast.

• 43:01David Weisburd?

  And he was just absolutely ruthless, absolutely zero sum. Some would say conniving, and it's still impressive to read about how he did it, even if you don't want to embrace those aspects of his personalities. But in certain aspects, like creating funds and certain non-zero sum, I think, in fact, the opposite, I think your your reputation catches up to you. And I think that reputation of delivering value is what matters. I think the niceties are not important. And a lot of times, frankly, those niceties are just fakeness. And it's masquerading as not providing value and just like being in the room. But I think ruthfulness is not something that you need to succeed in the privates and like alternatives markets. You certainly see different types of personalities succeed, but you have seen nice and very effective people. Michael Reese, for example, is a great example of that.

• 43:46David Weisburd?

  He's built this behemoth with with Dahl and Blue Owl. And one of the most nice and long term thinkers. Obviously, we talked about Rahul, arguably the greatest private fundraiser in the world. He has that that style. Now, it doesn't mean it's the only style on the planet that works. I'm curious, one thing that I've had trouble, so now you could be my psychologist, is how do you how do you frame certain asset classes as interesting and how do you become passionate? For example, heart tech, building the next rockets, the next, you know, neural links, all these things. It's hard actually not to be excited about it. And it's hard to fumble that narrative. How do you build a narrative around lower middle market private equity or growth equity in SaaS companies?

• 44:31Speaker 01

  I don't.

• 44:35Speaker 01

  I I gravitate towards the most more spicy, early stage, risky stuff because I like it. Because it is exciting. Venture math is really important. And that really is about around portfolio construction and making sure that you're taking enough ownership and it's right size to your fund size. So you can create fund returners inside of it. When I do the math on managers I want to work with, I look at their portfolio. I look at the companies that are interesting. I look at how much they own. And then I say, OK, what do these companies need to be worth to be fund returning? Outcomes. And if that number is 200 billion, I'm out. That number is 2 billion. I meant there are plenty of 2 billion dollar public companies out there.

• 45:21Speaker 01

  But we'll see how many 200 billion dollar companies end up materializing in the next couple of years. There's. You know, a lot of noise out there right now. But I don't actually today do anything in the buyout sphere. The only thing that that some of my managers do are pre-IPO rounds. Uh, but they are very much still in like the they're they're all venture or venture growth names. The thing I'd know to be true on the venture asset class is unlike any other asset class, alternatives asset class, the delta between that good and great is the biggest spread from any other market segment. And there and and the median is not worth it.

• 46:06Speaker 01

  Put it back in the S and P because it's not they're not good risk adjusted returns. So I don't actually believe in people that are taking a super diverse buy approach to venture. Indexing venture does not forget you the return profile that you take the long term liquidity risk for.

• 46:21Speaker 01

  Because finding great is such a challenge, such a puzzle, such a quest, such a search. I think it's really interesting and I think different parts of the market. And I I'm not trying to single out mid-market buyout. But if that delta is really small between that good and great, and you're pretty much like you know your return band and there's a formula to it. It is a lot of math and financial arbitrage. It's not that I feel like what you end up selling is more of a commodity. The cool thing about venture is being able to find a manager that's really interesting.

• 47:04Speaker 01

  Some of them are interesting, obvious, an obvious interesting. And some of them are hard interesting. Some of them are really interesting, but they haven't shaped it up, packaged it up in the right way. Or they're really interesting, but there's a blip in what they've done in the past that we need to now work into. Why is that not going to happen again in the future? Things like that. They're just such incredible journeys and it's so much fun to be a part of telling those stories.

• 47:33David Weisburd?

  If you did have to get excited about a bio fund, let's say that you were gonna hire somebody with experience there and you were going after that space, what would be the source of kind of passion? What are the sources of passion? Obviously, one is what they invest in. So they might not be investing in SpaceX. But what are other things that get you excited about a manager? Maybe their culture, their team building?

• 47:53Speaker 01

  100% the people.

• 47:54David Weisburd?

  And what does that mean?

• 47:55Speaker 01

  There's only one commonality between every manager I work with. And it's the first thing I said is they inspire me. Good people.

• 48:04Speaker 01

  Really trustworthy people. They might be difficult. Most great managers are difficult. And I say difficult in the sense that your EQ has to be high to work with a big, a large number of venture managers because they're very eccentric. Like, they're very unique. And they have no, like, they could all be in the same room and have a phenomenal dinner conversation. And by the way, I'm gonna do that because dying to put all my managers under one roof.

• 48:34Speaker 01

  But they're all very, they have these, they're all eccentric in a way. And I want to be drawn to that eccentricity. And I want to know that I can work with it in a really constructive way. And when I can feel that click, which is usually in the first or the second conversation, I know it'll be a good engagement. Because numbers are numbers and, you know, what you invest in is what it is. And there's certain parts of the story that you cannot, like, they're data. But what's not data is people who work really well together, the sum of the parts is greater. If you don't work well together, and I've seen this inside of the firms that I've worked with, like, if the IR person is an A player and the GP is an A player, and we've worked

• 49:19Speaker 01

  with firms that have internal teams too, but those A, or they're both A players, but they're cut from a very different cloth, they live on different planets, doesn't matter how good they are, they can't work together.

• 49:30David Weisburd?

  Dysfunctional teams or not highly sync teams are the standard and highly functional, cohesive teams are the exception. Which is why I used to wonder why LPs are so obsessed about team cohesion, how long the GPs have worked with each other. But it's because on average, the average fund will not make it to the third vintage, will not make it to the fourth vintage.

• 49:49Speaker 01

  And it's because of the people and their dynamic, 100%.

• 49:54David Weisburd?

  Well, Yasmin, we only covered, I think, two of the questions I wanted to ask. So we're gonna have to do this again. But it's been an honor and a privilege to have you here. And I'm from the Midwest, so looking forward to meeting in Columbus or New York City very soon. And thanks so much for sharing your wisdom.

• 50:09Speaker 01

  David, it was so lovely to speak with you. And I really love that you infuse.

• 50:15Speaker 01

  You speak to really interesting people all day long. And so I really appreciate when you can create, use your tribal knowledge and impart it on people. So it's not just like I'm speaking to you. It's like you're, you've actually, you've, you've made, you've made my mind swirl around several times in this podcast and that's so fun and engaging. I really loved it and appreciate it. And it's something that I'm going to be marinating on.

• 50:45Speaker 01

  And it's unexpected and I really love it. Thank you.

• 50:47David Weisburd?

  Well, that's quite challenging to do. So I'm very flattered and thanks Yasmin so much and look forward to seeing you soon.

• 50:54Speaker 01

  Absolutely.

• 50:54David Weisburd?

  That's it for today's episode of How I Invest. If this conversation gave you new insights or ideas, do me a quick favor. Share with one person in your network who'd find it valuable or leave a short review wherever you listen. This helps more investors discover the show and keeps us bringing you these conversations week after week. Thank you for your continued support.