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

Episode Date: November 26, 2025

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.

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

covering Europe, 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 just started this new gig in the hedge fence space. And here were these two crazy guys that told me that they were going to invest in technology companies between the coast. And this maybe tells you a little something about who I am. 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. 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 4, Fund 5, 5, on 6, once it's already consensus. But you saw something while they were in their Fund 1. What exactly did you see that made you want to drop everything and join Drive? 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. 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, was it? And by the way, I've never done an easy fundraise. So lesson learned there. It never gets easy. It never gets easy. Why is that? Because you're always going kind of towards larger funds. And why does it never get easy? It never gets easy because there's always, there are always new factors because in venture, unlike say event 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 bear market, it's hard because coffers are dry. And in a bull market, it's hard because LPs

heads 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, venture firms, I think, have a really high retention rate because they're very small partnerships. But LP's strategic initiatives shift so much over a three-year period that someone who you were really close with in Fund 2 may have a completely different set of priorities when you go out with Fund 3. And yes, it's on you to stay close to that and manage that evolution as it goes. But 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 fundraisers 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 existing network. What's the difference between networking and honing the existing network? Tell me about that. With an existing network, you have a set of really close relationships that you would leverage

to 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. 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 network 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 neither, 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 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 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 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 factors that we could see coming, like the lack of liquidity in L.P.'s coffers, but there's other things that you didn't see coming where the administration is trying to hamstring endowment 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 an 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 had only focused on my existing relationships in the endowment space, I wouldn't be able to close the 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 on the 200 pensions and the 50 RIAs and the 20 private wealth platforms and making sure that. that 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.

How do you balance relationships with the numbers game aspect of fundraising? It's such a great question because this is the kind of thing I think about when I'm playing 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 sales eat. I haven't run into a roadblock with it yet. The most important thing that I do is, even though it's transactional, it doesn't mean it's not fought 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 growth equity managers because that's what's lacking 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 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 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. And so if I can only put, 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, I build fidelity with both of them. And that philosophy on how to build CNIFI in the way that I'd like it to be built. I think that 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 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. It'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 it's going to be a platform shifting type of check and capital partner. 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 in 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 a fundraising for their firm or they're the founding GP, the fundraising, it's one thing that they do. And the second thing is paradoxically, once you're in this club, they give just the best service ever. So they give the seven-star hotel treatment to each one of those people and become non-transactional. So in many ways, they're very, very calculated in the front, who gets into the VIP, 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 doesn't matter because what matters is that we're going to make sure that you're having 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 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 fundraiser. I just have a very different philosophy on that. I don't, I don't have a ton of particularly close relationships, and I'm not looking for those. 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 after the ones that are the most attractive. That might be, I might be misconstruing part of what you're saying, but to me, I would never, for example, build a relationship with the GP 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 really deliver 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 digging 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 fundraise. Then I'm going to market map the pension world, see whose dollars match up best to

the fundraise, right? If you're raising a $500 million vehicle, I want to be in front of as many $50 million checkwriters 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 outsource CIOs, whatever that might be. And that mix, that market mat is frozen in time. 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, 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 managers against each other. I don't think that serves anyone. And I also want to make sure that, you know, there are multiple potential points of interests in a specific LP market segment. So some pensions might be really interested in early stage health care.

Others might be interested in late stage cyber security. Some way may like a thematic approach. Others may want diverse, 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 this exercise 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.

I also do multiple fundraisers a year for different managers. I wouldn't be in business if I was waiting for LPs to, 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, it's a big decision because you can't. 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 is so low, which is something I annoyingly always come back to. When you're talking about GPs, you're talking about for the GPs that you invest in or just other GPs. But when we first started Sine Finet, it always had to be because, you know,

I was starting it on my own, like in my garage. It's a nice garage. Ha, ha. Now it is. I'm sad as the garage, I think. 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 learned from really, really smart GPs and portfolio managers during my life, I want to build a product because product scales and services are harder to scale. And so I thought. got, 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? 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-C deck, right? the first version of your mission isn't what you bring to market because when we were launching this, it was 2022 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 a first close. I've done enough fundraising that in the first six months, you need to be well into a first close to have a successful fundraise. And so it becomes a self-fulfilling prophecy

about directions. Yeah. Yeah. And so I was like, there is no product market fit. 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 can I tell for you today? And that's your entry into this VIP world. And then you manage the relationship once they're inside the VIP.

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 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 a 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 are in part or entirely in charge of, completing, i.e. completing a fundraise, that we do that successfully in the least amount of time.

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 make it sure we understand their needs so that I'm not going to go knock on someone's door with the 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 and where, you know, the LPs priorities correspond to what the GPs are offering. 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 just, 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 LBFRA. 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. You have to focus on your immediate fund. But you want to 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, that 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 think, well, you're going to track me. Oh, you know, that's a way to 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 LPEC's this GP. If they're not a fit, they add value to my life. Therefore, I will add them again, this neuroassociative conditioning between seeing a specific person and having a positive experience. 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 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

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 um but in order to really square yourself into the tracking 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 they are active in venture and they are deploying capital. That goes to the behavior. How do you know that somebody's going to

invest? They're investing currently. 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? Yeah. 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. 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. Yeah, it's funny because now I've had several decades of raising capital, whether startups, venture funds, and almost without an exception, the people that get triggered by this question are the ones that 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, you get extremely triggered by that question. It's a very important question. And so that's why I'm like, man, you know, when you talk about these star fundraisers,

having these really deep relationships and, you know, going to the U.S. Open 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. No problem, according to the calendar, but you will be so, like, you become so inefficient. And I think because people are so over-scheduled, 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 dreams. So I think that's, to your point, part of YLPs 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. I'm not going to waste any more time. But there's an amazing, there are three amazing pre-seed management. 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? When you want more for your business, start with Northwest Registered Agent, the company that helps you build your complete business identity from the ground up. Northwest gives you access to thousands of free guides, tools, and legal forms to help you launch, grow, and protect your business all in one place. Your business identity isn't just your name or logo.

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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, I'm not going to be able to guilt that person and to continue 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. I wonder what that's like rooted in. Why why people almost take an apologetic 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 scenes 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 makes me want to do more work.

So I become a more efficient machine. And I think that that is true. That is very like true in terms of how I want to build every relationship and grow the network. A better way to frame it than maybe transactional is this kind of reservoir. So you have a reservoir and you build goodwill. Because 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. But 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. that's a really interesting way of looking at it so so so now to to to bring that by the wheels by the way my heels 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 my my wife always invoked my my wife always invokes my master's degree in psychology from Harvard I always feel almost guilty 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 develop 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 in to drive Fund 1 that deployed half, half of their capital

in Fund 1. So extremely early and you helped build that franchise. You obviously had a prolific career also at TPG. Let's say a fund comes to Sine Fini today and to you, Yasmin. And let's say they're an attractive fun. Let's say they check all the boxes. How do you go about, tell me the step-by-steps on how you go about helping them raise a fun. I'm actually, I onboarded one this week, really exciting spin-out. And so it's a, it's a great thing to frame up as I'm truly in the middle of it. The people who are a great fit, because again,

And again, you know, the marriage between me and the GPs is also a very big one. We're not cheap. And 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, wanted to do a close in January. Wanted to do a $500 million raise? We want to be done in March. And I'm like, woo, spicy. Love it. And other times, by the way, I join managers when

they're between fundraisers 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 want great, I've built great relationships to it because I think that through 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 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 And 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 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 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, either become successful or it doesn't. There is a manager that I would love to work with 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 from them,

but because I chase managers and I get shot down 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 hunter, not a farmer, just like they say in that. It's the Ashton Kucher, investing principle. Ashton Kuchar, surprisingly, to a lot of people

is a great seed investor. He's one of our clients. Okay. Ashton has this thought experiment, which is when he makes a C 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 the GP or to the founder. And he could have 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 say more amazing things about Ashton as an investor.

I find him truly inspiring. And a Midwesterner as well. And a Midwestner. 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. It's almost like shameful. 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. 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. Oh, yeah. I mean, last weekend, I was trying to think of 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 um areas of competence get

get sharper other new areas of incompetence start forming because you're upleveling 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 the only three half years of our own existence. And so I was playing around this weekend with this program just so that, you know, what does the LLM think the story is versus 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 flussing around, but, you know, I'm not, it's what I want to do. It's not because that's like my KPI 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. 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 on during the week. Totally. I don't have people weekend shame me anymore.

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 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 clearly love your managers. And I think about it, to your point, like I think about that every week. And then someone once told me something that I always fall back on.

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 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. 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. And that quote is something that I fall back on when I start thinking, oh, I'm just going to join one of my managers. So honestly, I don't know which one I'd pick. My unsolicited advice to you would be to weaponize your people pleasing. What does that mean? I have 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 pleasing, how do I be the best people pleaser in the space? And 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. Well, 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 that. 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 her. world. 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, Howard, 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 Wayne owns less than 10 percent.

of NVIDI, I believe. So to become a billionaire, to become a decadillionaire, you have to please the entire market, 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. 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 you put it in a very eloquent way is 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 short, like, direct juxtaposition to the idea of people gleezing. There's a famous essay by Paul Graham, which is why nice founders can become successful. to answer your question, you can 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 natural resources and monopolies, you have to be ruthless. I just listen to founders, founders on John Rockefeller, Founders podcast. 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 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 rootfulness is not something that you need to succeed in the privates and the alternatives markets. You certainly see different types of personality succeed, but you have seen nice and very effective people.

Michael Reese, for example, is a great example that he's built as behemoth 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 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 frame certain asset classes as interesting and how do you become passion? For example, hard tech, building the next rockets, the next, you know, neural links, all these things. It's hard actually not to be excited about it. 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? I don't. I gravitate towards the most, more spiked.

see 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, okay, 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 public companies out there.

We'll see how many $200 billion 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 some of my managers do are pre-IPO round. but they are very much still in like the 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, alternative asset class, the delta between bad, good, and great is the biggest spread from any other market segment.

And the median is not worth it. Put it back in the S&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-bide approach to venture. Indexing venture does not forget you the return profile that you take the long-term your liquidity risk for. 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'm not trying to single out. mid-market buy-up. 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. Some of them are interesting, obvious, and some of them are hard interesting. Some of them are really interesting, but they haven't shaped it up, package 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. If you did have to get excited about a bio fund, let's say that you were going to hire somebody with experience there and you were going after that space. What would be the source of kind of passion? Where 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. 100% of people. And what does that mean? 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.

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, 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 going to do that because I'm dying to put all my managers under one roof. 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, their data. But what's not data is people, 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 isn't a player and the GP is an A player, and we've worked 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. It doesn't matter how good they are. They can't work together. Dysfunctional teams or not highly synced teams are the standard. And highly functional, cohesive teams are the accession. 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. And it's because of the people and their dynamic, 100%. Well, yeah, it's mean, we only covered, I think, two of the questions I wanted to ask. So we're going to 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. David, it was so lovely to speak with you. And I really love that you infuse, 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. And it's unexpected and I really love it. Thank you. Well, that's quite challenging to do. So I'm very flattered. And

thanks to Jasmine so much. And look forward to sing down. in. Absolutely. 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 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.