E222: Why 90% of Managers Fail Before Fund 3

6 Oct 2025 · 1 h 9 min · 28 chapters

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In short

Why most venture fund managers fail around fund 3, and what GPs should learn from LPs—especially the role of long-term durability, portfolio construction, and “trust” in GP–LP relationships.

Guest backgrounds

Conrad Shang is managing partner/co-founder of Ensemble VC. He previously ran a $4B venture portfolio at UTIMCO within an $81.5B endowment, and earlier invested in unicorns at Norwest Venture Partners and Bain Capital Ventures. He’s also an institutional LP and a two-time venture capitalist.

Key claims

Great company investing isn’t sufficient for great fund management; fund building requires long-horizon portfolio construction and partnership-building. Venture is power-law; you must stay in the game through cycles. LPs are overwhelmed, so communication needs a “threshold of importance.” The #1 driver of successful GP–LP partnerships is trust, built over time and via “trust by proxy” (warm introductions).

Notable examples

2019 robotics/3D-printing homes company Icon (pilot fund) and later defense-adjacent shift; investments in Saronic (Series A) and Manifest (ex-Palantir founders). UTIMCO-style examples include LP education via annual meetings (e.g., shipbuilding vs China) and mid-year letters.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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The Role of General Partners and Limited Partners

0:45 to 2:30

Discussion on the insights GPs should have about LPs and the differences in perspectives.

“When you're a GP, you're so focused on putting one foot in front of the other.”

Building Durable Venture Firms

2:30 to 4:25

Exploration of what it takes to build a successful fund and the importance of long-term thinking.

“I like that framing, which is the GP is a business And some businesses get stuck in the short term, a little myopic, serving the next customer, if you think about the portfolio company as a customer.”

Survival in Venture Capital

4:25 to 4:49

Conrad emphasizes that survival and long-term vision are crucial in the VC industry.

“I mean, it was right after the financial crisis.”

The Power Law in Venture

4:49 to 6:10

Conrad shares insights on the power law dynamics in venture capital and the importance of patience.

“you want to play long ball and you want to think about durability because you want to be around long enough to successfully kind of build that franchise.”

Timing and Market Readiness

6:10 to 7:58

Discussion on the challenges of timing in venture capital investments and the need for durability.

“not you know sitting on your hands during that time it's super frustrating because you're meeting companies, the rounds are getting done by, you know, you know, great investors.”

Investment Examples and Trends

7:58 to 10:40

Conrad shares specific investment examples and how trends have evolved over time.

“If you had invested early in Apple as a public company or Meta or Tesla, you would have these phenomenal returns.”

The Importance of Team Dynamics

10:40 to 12:15

Discussion about the significance of team construction and hiring decisions in startups.

“further seeing, you know, really talented people, you know, moving in to fill this great need, right?”

The Power of a Village

12:15 to 12:39

Conrad stresses that it takes a village to create successful outcomes in ventures.

“Well, it's a double entendre, I suppose.”

Importance of Team Dynamics in Early Stage Investments

14:00 to 15:30

Learn about the significance of team composition and dynamics when investing in early-stage companies.

“Some of it you can measure with data and others you get context for meeting the founders.”

Lessons from UTIMCO: Trust as a Key to Success

15:30 to 19:00

Discover the pivotal lessons learned about trust and partnership in venture capital from the speaker's time at UTIMCO.

“So we go back and I love the fact that you asked that question about the short-term and long-term trade-offs.”
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Establishing Trust with LPs

19:00 to 21:10

Explore how to establish trust with Limited Partners (LPs) and the importance of trust by proxy in building relationships.

“People always think about, you know, the LP world is so distinct, right?”

Building Educational Relationships with LPs

21:10 to 22:40

Understand the necessity of educating LPs on market trends and how this fosters better partnerships.

“And it's really this mentality of treating your LPs as a true partner.”

Maintaining Open Communication with LPs

22:40 to 26:10

Learn the strategies for effective communication with LPs and building a two-way street of information exchange.

“Our last annual meeting, you know, before Saronic became such, in many ways, like on people's radar, Dino Mavrucas, who's the CEO and one of the co-founders, came and spoke at our annual meeting, right?”

Personal Connections in Professional Relationships

26:10 to 28:00

Discover the importance of personal connections and empathy in managing relationships between GPs and LPs.

“they do that they do it in ways where they over communicate but they do it in a more scalable way Right.”

Building Personal Connections with LPs

28:00 to 29:56

Learn about the importance of personal relationships between fund managers and limited partners (LPs).

“Like it absolutely extends, you know, beyond just, you know, a board meeting or like, Hey, did you hire the VP of sales that I interviewed, you know, two weeks ago?”

Navigating Difficult Conversations

29:56 to 34:43

Understand how to address issues with LPs and the importance of clear communication during crises.

“But I think this is where the relationship alpha is, where the truth lies.”

Navigating Difficult Conversations

34:51 to 35:02

Understand how to address issues with LPs and the importance of clear communication during crises.

“With Square, you get all the tools to run your business with none of the contracts or complexity.”

Trust Building and Relationship Management

35:02 to 38:58

Explore strategies for building long-term trust and relationships with LPs.

“The reality of it is if you look at it, if you're a GP and you've invested over many, many companies across cycles, this has happened more than a few times in your broad portfolio.”

The Challenges of Fundraising and Communication

38:58 to 42:04

Examine the challenges faced by fund managers in maintaining communication with busy LPs.

“And then this, the second thing I'd say, and look, I, I was, I was guilty as this, uh, guilty of this when I was at UTEMCO as well.”

The Overwhelm of LPs

42:04 to 43:36

Learn about the overwhelming number of pitches LPs receive and how that affects fund managers.

“I think that's that's kind of like an like, I don't know, like one principle to to to think about.”

Institutionalizing Investment Processes

43:36 to 46:10

Explore the importance of institutional processes in managing large endowments.

“And what I mean by that is the way that you operate a$2 billion endowment versus a$60 or$70 billion endowment, intuitively has to be different.”

Key Traits of Successful Managers

46:10 to 48:44

Identify the characteristics that differentiate successful fund managers from the rest.

“And so making sure that there was a mechanism in place to you know, get everybody on the same page.”

Building Strong LP Relationships

48:44 to 50:56

Discover how top managers maintain effective relationships with their LPs.

“So I'd say that's kind of, you know, the outcome of it was, you know, knowing kind of where folks were spending time, how they kind of thought about the world.”

Continuous Improvement in Fund Management

50:56 to 53:14

Understand the significance of iterative improvement in venture fund management.

“I'm not again, it sounds like, like, you listen to this, like, oh, of course, like, but Conrad, like, you know, I'm a solo GP, right?”

Ensemble Fund Performance and Approach

53:14 to 55:56

Learn about the unique approach and performance of Ensemble's fund one.

“all venture performance or any asset class is relative.”

Initial Strategy and Team Dynamics

56:00 to 57:24

Learn how the initial investment strategy evolved and the role of a diverse team.

“of very, very specifically, you know, finding great teams, right, not just great founders, you know, early, right, through a bunch of different signal that we could measure and track.”

Data-Driven Decision Making in Venture Capital

57:24 to 1:01:50

Discover how data and technology transform the investment decision process.

“And the best reflection of that is from, you know, the founders, we're now a team of 12.”

Identifying Signals for Successful Investments

1:01:50 to 1:09:26

Explore the unique signals and frameworks used to identify promising investments.

“And so for us, you know, that means not just having a box checking exercise of, hey, we, you know, we use ChatGPT or we buy a bunch of data from so and so that anybody can do, right?”
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Transcript

Automatic transcript. May contain errors.

0:00Today, I chat with Conrad Shang, who is the managing partner and co-founder at Ensemble VC, bringing a rare perspective with experience as both an institutional limited partner and a two-time venture capitalist. At UTIMCO, he oversaw a$4 billion venture portfolio within the$81.5 billion endowment, guiding investments across diverse asset classes and regions. Previously, Conrad invested in multiple unicorns at Norwest Venture Partners and Bain Capital Ventures, earning recognition as a top fund investor. Surprisingly, the shift from tier one VC firms to Alligator is a rare shift. They have a unique vantage point.

0:42What do you think GPs should know about LPs that's not intuitive being in the GPC? When you're a GP, you're so focused on putting one foot in front of the other. And, you know, what I mean by that is you're singularly focused on, you know, investing in, you know, one company at a time. And so in some ways, like you, you don't have the context of seeing the forest, I think, from the trees. And, you know, that analogy kind of can mean a bunch of different things. I think, you know, one, I think one of the takeaways, you know, from being in that seat is, you know, being a great investor is, you know, necessary but not sufficient to being a great fund manager.

1:25Right. So you can, you know, you can have invested in great companies, but when you go and decide to sit on this journey of building a fund, starting a company, right, that happens to be a venture firm. you know you're you know you're trying to build something you know durable you're building a team you're obviously uh you know fundraising finding great lps that um that believe in your mission single investment can be a you know you know five to seven years but when you're building a fund you know it's a minimum of 12 years effectively 10 to 12 years so the time horizon is longer to be a great you know fund manager you have to do so much more right you have to think about about portfolio construction, right?

2:09Not just a single investment, but what that looks like in a collection of investments. And even before you're investing, right? You're thinking about how to build a great partnership, right? Not for year one or for year two, but for year five, six, you're 10, 12, right? For fun two, three, four, five. And so you're, you're actually doing a lot of, of like reflection, I think before you go out to go, you know, you know, start a fund, like you really have to believe that the world may not need another venture firm, but the world needs your, you know, you know, venture fund. I like that framing, which is the GP is a business And some businesses get stuck in the short term, a little myopic, serving the next customer, if you think about the portfolio company as a customer.

3:01And some businesses are focused on the long term, which is how do we build more franchises? How do we be more strategic with our time, our money and our resources? And obviously you need both. If you're just strategic, you're in the Ivy Towers, you're not really getting anything done. So for GPs that are so focused on just making the next investment, what would be your one main piece of advice? It's easy, I think, to give advice. I think it's very difficult to live this. So I don't think we're immune from trying to balance between short term and I think long term goals. I think your LPs can actually play an important role in that.

3:47right um you know given the other managers that they've invested in that may be um you know much you know further out the advice i give you know gps that are um thinking about this or struggling with it i think one you know you know lps are more than just um you know all money is more than just green right in that standpoint right i think your lps you know you know besides Besides, you know, helping you give you the capital to go back, you know, great teams. They're also there to provide this very council of, you know, how to think about short term and long term. And, you know, long term is really about durability.

4:24I've been in venture since 2000, 2009, when I was at Bank Capital Ventures, which was not, frankly, a great time to be in VC. Right. I mean, it was right after the financial crisis. You know, I was I was worried that I, you know, I was concerned that, hey, I may not even have a job. I mean, just candidly. Right. Right. And I think the lesson there is, you know, venture is some ways about survival. Right. And I don't mean it in like, you know, I mean it in a very serious way in that because venture is across multiple cycles, you want to play long ball and you want to think about durability because you want to be around long enough to successfully kind of build that franchise.

5:10And I think there's an interesting data point. I may get the specific numbers wrong, but I heard Josh Koppelman talk about, you know, I think he looked at the numbers. He looked at the average VC from 1980 to, you know, 2000. Right. Just kind of an arbitrary data point. I think it was like something like 83 or maybe it was like, you know, 80 plus percent or 90 plus percent of the profit dollars made for the average VC was made in three years. Right. And so if you weren't a VC during those three years, not surprisingly, it's like 97 to 2000. Right. Then, you know, there is no money to be made for you or for your LPs.

5:47And so that data point in itself suggests you want to be durable. right you want to you know be prudent and disciplined in terms of how you invest you know in that moment it's incredibly difficult think about 21 22 right which is a great example of that i think at the time you know we thought we were doing the right thing but it was difficult because i think it was almost 12 months that we didn't do a single deal um and and you know you're not you know sitting on your hands during that time it's super frustrating because you're meeting companies, the rounds are getting done by, you know, you know, great investors.

6:27You know, they're obviously overvalued, you know, 2020 hindsight. And even at the time, and so it's, it's really hard to look around and see all of your peers being super active. And then you just sitting on your hands and everybody's looking at you like you're the, you're the crazy one. Like, but if you have the mentality, I think of, Hey, I want to be in the business over 20 years. I want to build a successful franchise, not just a, you know, to build a firm, not a fund, then, you know, you kind of have to put your big boy and big girl pants on and sometimes kind of sit it out or be very thoughtful about, you know, when to deploy or how to deploy.

7:06It's a bit of a paradox in that all venture is driven by these extreme power laws. So there's two things you could do. You could be extremely lucky, which of course is just not a real strategy. Or you could be sit around and wait long enough for that power lot to hit. And I think that's this asymmetry that gets unlocked by staying in the game by having those shots on goal is one of the most underrated aspects. I was just speaking to Dan Ives from Wedbush, this famous public investor. And the analogy that he gave is, in order to be a great public investor in the tech space, you have to be kind of average most of the time to 80 to 300.

7:47And once in a while, you hit this Jeff Bezos like 1000x home run. There's actually there's power law like dynamics in the public markets, not just in the private markets. If you had invested early in Apple as a public company or Meta or Tesla, you would have these phenomenal returns. So I think there's this paradox in that in order to hit these extreme outcomes, you do have to stay in the game. The way that you stay in the game is doing the work and also things like the boring things, portfolio construction, sizing, and just being in the game is such an underrated aspect. And it goes from when you're starting your first fund, first two, everything's against you.

8:28You don't have the track record. You don't have the LP relationships. Institutional LPs aren't taking a look at you. And by fund three, everything's going for you. But those four or five years is where 90 % of managers at a minimum fail. 100%. And I think here's a good example of it. You always hear, you know, you can be too early. Like you can be on time. You can be late to a sector. You can be too early in a sector, right? So when I was at Norwest, you know, ARVR, right, was a big thing. And, you know, and like it didn't quite live up to expectations, right? Folks were, you know, I think largely too early, you know, for us, when we were investing out, you know, we did our first, you know, I would say pilot fund.

9:17We invested in a company called Icon. So this is 2019. And Icon, for those of you who may not be familiar with, is a robotics company that does 3D printing. So they 3D print homes, wrapped up a project with Lennar, the nation's largest home builder, building 100 homes. But they also, you know, build for the like the DOD. Right. So if you think you can build structures that are concrete and print them, you can obviously do this in a conflict zone, build walls that are bulletproof and so on and so on. And so we invested in 2019. Defense was was not really a thing. Right. Right. Certainly there might have been dual use.

10:01And in many ways, it was almost like a like a like a like a knock on a company. Right. Selling it to the U.S. government. And it was taboo. It was taboo. Right. I mean, people are locking themselves in buildings, if you remember through that experience. And then recognizing over time, you know, where I think really high quality people, right, people go with their feet where they were saw opportunities and saw need to go build businesses. you know, that allowed us to go make, I think, a super impactful investment in our current fund. We were, you know, in the series A of Saronic. And then that kind of, you know, ended up, you know, further, I think, educating us, further seeing, you know, really talented people, you know, moving in to fill this great need, right?

10:49And now it's like, you know, now it's like obvious, right? There's, you know, these defense tech companies, but, you know, we followed Saronic with chaos. You know, we invested in a purely software company earlier this year called Manifest, where the two founders were, you know, ex-Palantir. The durability aspect of it, kind of back to the original question, is, you know, you have to play long ball because you don't necessarily know when, you know, the exact right time is. Right. But there are certain proxies that you can do, which is, you know, seeing where high quality talent is flowing. Which founding teams are the biggest talent magnets?

11:22That's kind of our specialty with our data platform. But if you're playing long ball, then you can kind of make those bets. And you can kind of let the world kind of catch up in some ways to where you're investing, where these high quality founders are building companies. I think oftentimes you hear these factors like talent, market size, traction. All these are positive. And you obviously want all of them. But where would you stack rank the flow of talent as a leading indicator of success? Is that more important than the market size? Is that more important than the traction? How would you stack rank that?

12:05I think it can depend on the stage, but even I think across stages, like it's kind of an easy question for us because it's a little bit on the nose, but, you know, we call ourselves ensemble, right? For a reason. Well, it's a double entendre, I suppose. So it was about us building a great team, but the initial idea of, you know, calling ourselves ensemble was really, you know, recognizing that it's all about the team. And that's really important. And I'll make the distinction between, you know, it's all about the founder or founders versus it's all about the team, right? I think it's an important distinction.

12:39And some people kind of, you know, kind of, you know, put everything in one bucket. The reality of it is, is it takes a village to go create an outcome. And, you know, I had the good fortune of, you know, being a seed investor in, you know, Casper. I was, you know, an early investor in Udemy. And so kind of saw what it means to really require a village to go create the outcome. And that extends beyond just the founders. And so for us, the most important thing is the team. And so when we look at a potential investment or we're tracking a bunch of different companies, I think there's a lot of signal, not just in the founders and where they came from, but how they think about who is their first hire, right?

13:29So is it an engineer? Is it someone on the sales side, right? Is it go to market, right? Because that speaks volume to, it's a reflection about how they think, how they're going to build the company. And it's also a reflection of themselves, right? Of, you know, trying to find folks that are complimentary, right? Or the type of company that are building, you know, very product engineering focused versus very go to market focused. and it also speaks volume of like how do they find this person right is it someone that they had known you know for a long time right is it someone that they had worked with before or is it you know they put a job posting out i'm not saying one is really good you know that's a good or bad but i think that dynamic of who's your first hire you know who's your first sales hire who's who's your first product engineering how do you sequence that right what does that team look like?

14:18How are they complimentary? There's so much of a story that tells. Some of it you can measure with data and others you get context for meeting the founders. And so what we like to do before we invest is we actually like to go on site, not always, but in most cases, we like to go to their office. We like to go meet the founders and we like to go meet other folks on the team, right? Very organically. And that just, I think that just speaks volumes to, I think the true reflection of a company, and I'd say particularly at the early stage.

14:57Going back to your time at UTIMCO, at University of Texas Endowment, as I mentioned, you went from the GPC at Bain and Norwest, Bain Capital Ventures in Norwest, to UTEMCO. What were some of the lessons you learned right away, which is like, holy crap, this is why these LPs liked us, these LPs didn't like us. In other words, from the LP perspective, what is something that became immediately obvious that is not obvious to most GPs today? this is one that is a little bit counterintuitive right think about a sports team or something in some ways right like you want to find the best absolute people like in their position right so you know you look at shooting percentage or whatever it is right um and each individual person who's highly confident is going to make a great team right the reality of it i think on the it doesn't quite translate on i'd say on the venture side and what i mean by that is the single most important factor that I observed when I was in the seat at UTIMCO was trust as the number one factor for a successful partnership.

16:15So we go back and I love the fact that you asked that question about the short-term and long-term trade-offs. If your goal is to go build durability and success, like repeatable success, then trust is 100%. the most important factor. And what I mean by trust is, you know, I think it starts with the partnership, you know, who you decide to go in business with. In this case, it's, you know, you know, Colin West, who I've known since, you know, 2013, right? When we were both kind of junior VCs, you know, just having moved to the Bay Area, you know, Colin was a friend of mine. My other co-founder, Gopi, you know, Colin and Gopi had worked together, you know, for four or five years, you know, prior to us, you know, really formalizing, you know, what ensemble is, you know, today.

17:03And that trust factor, you know, again, starts with the partnership, you know, you're not going to be in the same room, you know, you're, you know, all the time, you're going to 100 % disagree on things, right. And the question is, how do you react to that in the moment? Right? Do you let your ego get in the way, draw a line in the sand, and then defend it to the death? right so you know great for your ego but bad for the firm right i've seen situations like that where you know and i argue kind of the bigger the bigger the organization the harder it is to go is to you know do what's right for the organization there's so many different personalities um but then that trust starts to extend to the folks that you hire right um and you know meaning you want to give them as much rope as you can and you kind of like let them earn that trust and you give them more and more rope.

17:57And then it also extends to your LPs, right? You know, how you communicate, what you share, right? And in even more cases, right, your LP is not going to be in the room. You know, they'll make the investment. You know, you can catch up with them in annual meetings, newsletters, you know, like even over text, right? But the reality of it is that that LP is entrusting you, with dollars that are eventually going to go fund scholarships, right? And they're not going to be in the same room. And how do they have that level of trust that's going to extend beyond the life of this fund and certainly into the next?

18:35This term trust is a term many LPs use. And many LPs like you who are at University of Texas will say it's even more important than returns. let's double click and define exactly what it means to have trust with your LP. I know it sounds extremely obvious, but what are some examples and more importantly, what are some trade-offs? So what is the skin in the game for GP to have a trusting relationship with their LPs? People always think about, you know, the LP world is so distinct, right? But I think having been in all these different seats, there's actually way more similarities of the relationship between, into a founder and a GP and an LP and a GP.

19:18I actually like, I think it's super consistent. And so an example of that is when you meet with the founder, how you got introduced to that founder, right? Or how the founder gets introduced to that VC. And I think it's the same, you know, when it comes to, you know, the beginning or the commencement of an LP relationship, right? Which is, I think in the ideal case, you're being introduced by other GPs, right? Maybe that P is our investor in. And that GP, you know, has you very well over, you know, not three months, but over, you know, ideally years. And, you know, they can speak to that credibility and that trust factor, right?

20:03So I kind of define this as like trust by proxy, right? Trust is something that you cannot, or very, very difficult in most cases to establish in any way outside of time, right? Or a number of interactions, right? And the way sometimes to shortcut that is what I call trust by proxy, right? So you have a mutual connection that has deep relationships with, you know, both other sides that can kind of bridge that, right? Not in a perfect way, but in a way that can help kind of, you know, build that relationship. So that's one, right? What's the nature of the commencement of that relationship? Ideally, you want something through trust by proxy through warm introduction because it sets off the relationship.

20:55It's not a transaction. What it does is it catalyzes it in a relationship building exercise. exercise. And I would really credit my experience at UTIMCO, but also one of our recent hires, Caroline, who joined us from Vista. And it's really this mentality of treating your LPs as a true partner. So again, I kind of mentioned this earlier, but Beyond Capital. And that's like everybody kind of says that, but what does that actually mean? What it means is that it's two-way street, right? For the LP, you know, they obviously want a financial return, but they're also looking to educate themselves on, you know, specific, you know, areas that you may be investing in, right?

21:43Like, by the way, they're not just running a venture portfolio, right? And even though I was running, you know, venture at UTIMCO, I was also doing, you know, technology investments with, you know, buyout managers, right? And so, like, Sometimes the GP is so narrowly focused on their world and then forgetting that the LP, venture is important in many ways, like the alpha driver in their portfolio. But they're managing a public portfolio. They're managing a private equity portfolio. And what you're doing, actually, if you're investing in defense or investing in AI, it's going to affect the other portions of the book.

22:25And so what we do, and I think a lot of the managers do, is, or certainly the best ones, will take a step back and help educate their LPs on, you know, certain areas that they may be interested in. Our last annual meeting, you know, before Saronic became such, in many ways, like on people's radar, Dino Mavrucas, who's the CEO and one of the co-founders, came and spoke at our annual meeting, right? And this was like 2024. And and so like it kind of helped educate, I think, folks on, you know, what does it mean to you know, what does it mean to think about shipbuilding in the U.S.? What is the the challenge that the U.S.

23:08has relative to China? Right. Which has the biggest over 200 times the capacity of the U.S. and shipbuilding. And then I'd say the street goes the other way when, you know, we're investing, you know, in like real examples, we're investing in a fintech company that was basically doing like cross-border payments. and we know one of our LPs actually you know a multi-family office based in Houston actually owned a lot of these different kind of businesses that would be affected by it and they made introduction to one of their you know like you know businesses that was not venture backed right and we were able to have a conversation with them to help us understand you know what are the implications of you know cross-border payments specifically between certain corridors?

23:59Like, what does that look like? How is their business performing? Because ultimately, you know, the venture-backed business, if it's successful, is going to kill that business, right? And so how do they think about, you know, that threat? And so again, it goes back to, you know, thinking about building a firm, you know, with durability, long ball, having a deep partnership with your LP. And what that means tactically is like, you know, This sounds crazy, but like talking to your LPs, right? Like making sure that there is active two-way communication. Sometimes it's one way in the sense that you are sending probably more information than they're reacting.

24:39But you have to over-communicate with your LPs. One of the reasons I was so excited about a conversation is because you had that two different tier one VC seats. You had the tier one LPC. You were the customer. You were the buyer. and you were in the room having these conversations. And I think one of the things that GPs, when they hear you want to trust a relationship, they think, sure, great in theory. But in reality, how does that look? If you think about it from this construct of a partnership, which I love the framing, I have my business partner, Curtis, we sit down. We not only talk about business once in a while, we'll talk about, we are both now married.

25:19We talk about our wives. We talk about our families. Tell me where your analogy ends and maybe tell me the nuance and what it means to build a trusted relationship. Yeah, that's a great question. I, you know, the first way to answer that, again, going back to the analogy of, well, what do you what is it? What is a founder GP relationship look like? Right. So all those questions that you asked, how would you answer that with your own founders? right and so if you take that lens I think one it's hard to treat everybody equally right like let's say everybody in your cap team if you're the founder right very very difficult to treat everybody this practically right yeah it doesn't work right but that doesn't mean that the founder does not communicate with even the you know 0.1 percent owner on the cap table right so how do they do that they do it in ways where they over communicate but they do it in a more scalable way Right.

26:16So they're constantly sending updates. Right. Maybe it's a monthly update or a quarterly update. Right. They're giving they're giving the opportunity for even their small folks in the cap table to be heard and to be seen. Right. And that analogy against extends to the LP side where you may have some folks that aren't on your LPAC, maybe individual investors, but they should still be in the loop and updated. And then more importantly, you should reach out to them if one of them has a connection that's quite valuable. Like LPs and then GP, all they want to do is be helpful. They don't want to be viewed as just money.

26:57And sometimes it's only five days out of the 365 days in a day where that LP can be helpful. But in those five days, it can be extremely valuable for the GP. right and so i think it's uh you know taking the initiative to you know reach out to your lps you keep them updated uh but also you know make sure that you're seeking you know their advice when you know that they have um you know a much better knowledge base right you know they're like in my tempco days like you're raising a continuation fund right or you're thinking about um uh you know getting intel on a specific lp maybe in europe that wants to come in and they may have context.

27:38Right. So I think it's leveraging their unique knowledge base, you know, to help you make better decisions. And then, you know, where does the analogy, you know, end? I actually do think it's really important to, you know, think about not just the professional nature of the relationship, but also personal one. Right. Again, I go back to the founder GP thing. Right. Like it absolutely extends, you know, beyond just, you know, a board meeting or like, Hey, did you hire the VP of sales that I interviewed, you know, two weeks ago? Right. It's, Hey, I know you're about to have a kid, you know, that's super exciting.

28:13Right. You know, you must be thinking about a bunch of different things, kind of how to, you know, how to balance that. Right. Hey, you know, I know you're going through, you know, you know, a family, you know, personal thing, right. Like, you know, just acknowledging you and saying, Hey, like, you know, it makes sense for, you know, spend time on that or something, right? Like we're all human, right? Like just like the struggles of a founder who's starting a company going from zero to one, it's the same for, you know, fund managers, right? Or, you know, having to let go of a partner or whatever it is.

28:44Not all your LPs are going to be equipped, right? To be that, that coach. But you'll know the, you know, the few that you have a very deep, you know, personal connection with where it's okay, I think to, I think to share some of this, Right. And you have to be thoughtful, like about, you know, what it makes sense to share. And so it's never like I'm going to share everything or I'm going to share nothing. Right. That's not the framework. Right. The framework is like there's something in between. And I think a lot of folks take the mentality of one or the other. Right. And it's it's probably somewhere in between.

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29:17And I would probably say it's probably a little bit more towards being open. Again, it's not to everybody who's an LP in your fund. Right. You know, I think it's to a handful of folks that they may not even be your biggest check, but ones that, you know, you have a relationship with that you can be open with. Because the reality of it is everybody's aligned. Right. So, you know, your LPs and your fund for, again, at least 12 years. Right. Whether or not they decide to come in, you know, the next fund or not, you have to earn that. But if they're in your fund, it's a marriage for 12 years minimum.

29:55These are the conversations not many people have, certainly not through podcasts. But I think this is where the relationship alpha is, where the truth lies. One of the most prevalent memes in asset allocation today is that LPs are choosing to back fewer managers and more lead behind fewer arrows, to use the Google analogy. So there's this pressure to cut managers. how do managers balance the desire to have a trusted, long-term, sustainable relationship with LPs, while also, you know, at the same time where in the market, LPs are looking to chop managers? And how do you thread that needle? What are some best practices?

30:40That's obviously, I think, top of mind for folks. There's no silver bullet on any of this. my perspective on this, and it's, you know, I kind of put my old UTEMCO hat on, but also, you know, the ensemble hat at the same time. And the way I would answer this is, it is what it is, right? Meaning like, if you have an issue, whether it's, you know, performance, or, you know, within the organization, like, it's happened, right? It's the reality of it. and it's not the fact that like something like this surface because that happens to every firm right it's it's it's really the question of how do you address it and then how do you communicate it um and i think like the you know i think the advice i would give myself and i give others is you know i think understanding the like one that i think the gravity of what it is right And so you obviously don't want to communicate every little thing to your LPs, not because you want to avoid being transparent, but too, you want them engaged on the things that are the most important.

31:53Right. And if they have, you know, if they're managing, you know, I think you Timco had, I think it was like 16 Corvette VC managers and then some other, you know, legacy ones. If everybody is like, you know, every time, you know, I stub my toe or something, right, and I'm communicating that, the LP doesn't know when to engage on the things that are more important. Right. So there is a threshold of importance. Right. And as an example, right, like, you know, there's probably a lot of even at a small firm that, you know, there can be turnover at at the junior level. Right. So, like, do I communicate that?

32:26Do I not? Right. You know, I don't I'm not sure that that meets kind of the threshold. Right. But if it's someone more senior, then obviously, like that affects, you know, economics. It affects, you know, maybe some strategy things. So that may be something to, you know, communicate, you know, with your LPs. And then tactically, what you may want to do, right, just like a founder manages his or her board, you may want to have this conversation, you know, one-on-one initially, right, with the LPs that you have a very good relationship with, right, that you have this level of trust, right, and see how they react.

33:03and then, you know, and then bring them into the circle of trust where they're already in the circle of trust. And as you need to communicate that with other folks, they can help facilitate that or certainly give you advice, right? Meaning, you know, it's a serious issue for the firm. And, you know, you think it's like, you know, the most important thing going on in your life and in the world globally, right? Because it's the first time you've come up with, you've run across this. The reality of is, you know, for the LPs that have been in the business a long time, They see this, this is actually a more common issue, right?

33:34And so they can actually give you counsel on, you know, how serious this actually is and, you know, what to do in this situation. Again, you think about a founder, right? Who, you know, is in a situation of like, hey, you know, I had this co-founder, right? Support for today's episode comes from Square. It's all in one way for business owners to take payments, book appointments, man staff, and keep everything running in one place. Whether you're selling lattes, cutting hair, running a boutique, or managing a service business, Square helps you run your business without running yourself into the ground.

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35:05I don't know what to do. This could kill the business. The reality of it is if you look at it, if you're a GP and you've invested over many, many companies across cycles, this has happened more than a few times in your broad portfolio. And so you can actually have the data and the, you know, case studies to suggest, hey, like this is kind of how you might want to manage this. Right. Just like GPs have a portfolio of founders, you know, the best LPs also have a portfolio of VCs that they can pull from and draw experiences from. I think that's probably like selectively, I think, seeking counsel with the folks that you trust very, very deeply.

35:49to summarize one is you don't want to be like the girl who cried wolf you don't have to send every every day and you're going to seem like you're not able to regulate your own emotions you want but you do want more transparency so probably the default human benchmark to of communication is probably lower than the ideal one so for some reason gps on average which are way below their kind of optimal level of communication. And also you want to make sure that your communication and the narrative that you're putting out, even if it's transparent, that you explain it in the right way. And you might want to test that on a couple of trusted circle before you kind of blast it out to 150 LPs.

36:33Yeah, absolutely. I go back to, you know, what are the best practices that you would give a founder on communication? Right. And, you know, it should be similar to how you communicate with your LPs. It really shouldn't be that different. Right. I mean, there's a little bit of nuance to it. But at the end of the day, you know, you want your founder to not text you on every little thing that, you know, is an issue that comes up in the business. You know, surface the ones that are relevant, you know, maybe on a quarterly basis. Right. With, you know, in this, you know, you'd like to have that discussion one on one prior to the board meeting.

37:11right if it really warrants it um and you also want a founder to have a plan of action right in advance you know not not not ask you hey what i do in this for this problem but say here's the problem this is my course of action um you know am i missing something right what is your feedback on the course of action that i'm planning to pursue one of these things that i've been thinking about is this concept of rooting things. So rooting investment thesis. So everybody might make the same buy decision to buy Bitcoin. But if I spent a year thinking about why, when it goes up and down, I'm not going to sell.

37:51So it's great if you bought Bitcoin at$100. If it goes up to$200 and then goes down to$140 and you sold, then you gave up the other$120 ,000, the other, you know the the thousand x and i think this rootedness is also applies to relationships and lps if you assume that on a long enough time horizon and i've literally talked to jonathan gray from blackstone cliff astinus from aqr about this very topic if cliff astinus and jonathan gray have had issues in their franchise i guarantee with enough time uh any gp on this planet will have those issues and the way that they they handled it also by over communicating meeting with lps But I would also add kind of the subtext of what they were saying is they built this trust also over time ahead of that.

38:37So if you think about it as the trust and the relationship as a tree trunk, you could strengthen the roots of that tree trunk through trust ahead of the crisis. Because just and no one wants to be transactionalized. And if you're only talking to your LPs when you need them or when there's a crisis, it's not going to feel good for them. And you're likely on that chopping block that we talked about. But if you build that relationship ahead of time, not only will they maybe not take capital from you, if there's a good market opportunity, the smart LPs, the very top, top quartile LPs might even double down on you and allow you to actually, you know, build, build, build your alpha and build your franchise during difficult times.

39:19it's easy to you know sometimes say these things this is very hard to do in practice right so it's not like oh there's like a there's an instruction manual you do this and you do this at this cadence i think it's just if you just think about it right as a priority for the firm um then you know it'll naturally kind of follow um you know some of the things that you do right it's an aspiration i guess in some ways right you kind of have to aspire to build partnerships with their LPs, even if some of those don't look like that today. Right. And then this, the second thing I'd say, and look, I, I was, I was guilty as this, uh, guilty of this when I was at UTEMCO as well.

39:57Right. Like, you know, I'm not, I'm not casting stones on, on, um, on anybody here. Um, but you may over communicate, you may do everything to try to establish a great relationship with your LP, but that LP may just not reciprocate. That's going to happen. right that's okay right um but i think like again if you're thinking about playing long ball and durability um you just kind of have to go the extra effort to recognize that hey they're you know they're managing a bunch of stuff not just your fund and not just venture and so you may be sending them all this you know all these different materials you know asking to catch up when you visit you know you know wherever they're based and they may not you know get back to you that's okay right I think making the effort you know making sure that you're thinking of them is in itself I think what it means to be a good you know a good partner right say all this stuff and I think some people's reaction is like I tried that right but I'm not getting any love back and that's happened to us also but every now and then you know you'll get a note and say hey you know like we you know one of the things that we pride ourselves on since we since we started was we will write a mid-year letter, right?

41:12Like, and it's, you know, the first one, it was, you know, it took like months to write it because we never wrote one of these before. It actually wasn't that it was like, okay, when I go back and read it. But we've made it, we've made the effort to write a mid-year letter every single year. And then, you know, what's the greatest feeling in the world is when someone that you reached out to multiple times doesn't respond. But on this latest one, you know, they say, hey, like, you know, great, great mid-year letter, right? Really enjoyed reading it. Right. And so like. It's it's you kind of have to you get credit for being active and being thoughtful and and being consistent.

41:51Right. You'll get feedback occasionally, probably not as much as you would like. But, you know, you should make sure that you're always acting like you're thinking of them. Right. I think that's that's kind of like an like, I don't know, like one principle to to to think about. So Rahul Mugdal, he's one of the greatest fundraisers alive, if not the greatest. He's raised$99 billion. And he tells a story on the podcast I did with him in that he talked to a$1.2 billion foundation. The CIO told him that just that past year, he got 934 voicemails, not calls, but voicemails from managers, not in his portfolio and not even talking to him about investing, about how he should invest.

42:39And this is just this very, I guess, visceral way of showing how busy LPs are, how overwhelmed they are. It truly is oftentimes not you. It's them, not you. Did you find you were at UTEMCO, which in many ways is today, I think it has 60, maybe 70 billion. It's endowment. It's one of, if not the most kind of coveted LPs in the world. Tell me about your lived experience as a LP at such a prominent endowment. So I joined, you know, right a little bit before the new CIO Britt Harris joined. Britt was actually in our office, I don't know, like a month ago. And he had come from TRS, which is the Teachers Retirement System of Texas.

43:32And so I think one of the things that I really give Britt a lot of credit is, I think, further institutionalizing what was already a great endowment. And what I mean by that is the way that you operate a$2 billion endowment versus a$60 or$70 billion endowment, intuitively has to be different. One of the exciting things about UTEMCO is that the size of the endowment grew very, very dramatically over the last 20, 30 years. Right. And there's a lot of history to it. But some of it being in Texas, this was money coming from the Permian Basin. Right. Like just some random historical context there. And so UTEMCO had this really amazing opportunity and task of not being short on cash and cash inflows, but making sure that it was being invested at scale, but in a very thoughtful and strategic way.

44:44And to do it, I'd say, relatively quickly. And as that endowment, I think, grew, I think the UTMCA board, I think, rightly recognized the need to really institutionalize and really helped evolve the endowment from smaller endowment to one that frankly rivals the size of a pension fund. I think UTMPCO is number one or number two, depending on how you measure it. But effectively, it's like the largest endowment in the world. And so when I was there, I was kind of thinking about what processes that we want to apply you know, across UTEMCO to bring, you know, an additional level of rigor, but also a way to invest more repeatedly and consistently.

45:38Right. And, you know, what that tends to mean is, like, I think formalizing, you know, the investment process, you know, how opportunities got surfaced. as the organization grew, making sure that everybody in different parts of the organization were informed on what was coming down the pipeline. Again, an endowment is not just venture. Not everybody who sits around the table is equally versed in what that means, how to invest. Not everybody's heard of Sequoia. And so making sure that there was a mechanism in place to you know, get everybody on the same page. And, you know, in some ways kind of standardize, you know, that process.

46:23You know, at the time, you know, you know, whenever you put new process in place, you know, and you're learning and you're figuring things out and doing something new, like there are moments where it's not that fun, right? But, you know, now that, you know, I, you know, I'm in the C.D. Ensemble, you know, founded the, you know, co-founded the firm, it's really important to put process in place, right? So you're not collecting a bunch of shiny objects for one thing, right? And then two, you can have repeatability in your performance, right? And the grandest scale is an endowment. Like the endowment is gonna live beyond me, beyond you, beyond my kids, everybody's kids for generations.

47:07That's the hope, right? And so the time horizon is almost infinite. And so we have to, you know, in order to fund, you know, my scholarship and then maybe my kids will go to UT on a full ride, too. You have to create like repeatability, you know, consistency. And that was kind of an important lesson that we applied to Ensemble. So, you know, we're, you know, I kind of bucket ourselves as an emerging manager. Right. But when we've put together Ensemble, we always had the mentality, again, of being aspirationally, like institutional, right? And so taking some of the lessons, you know, not from like, you know, True Ventures Fund 1, but from True Ventures Fund 5, right?

47:49And saying, well, you know, how do we look more like them? How do we avoid, you know, maybe some hard lessons? And so how do we make ourselves institutional? Vinod Khosa popularized a$0 million business versus a$0 billion business, how they function from day one. And you did see a simulation of dozens, if not hundreds of funds, venture funds at UTIMCO, including some of the best funds in the world. What were some practices that the very top GPs or the GPs that made it, let's just define it in the outcome, what did they do from the very beginning that was different from the ones that were even second or third quartile?

48:32The best managers were the ones that could give you a sense of, you know, what they were looking at, how they saw the world in a given moment. Right. So that goes back to like over communicating and transparency.

48:47So I'd say that's kind of, you know, the outcome of it was, you know, knowing kind of where folks were spending time, how they kind of thought about the world. You may not agree with it or, you know, you may have questions about it, but you had a sense of like who they were and like how they were thinking about things. I think the second thing that the best managers did was, you know, I think go out of their way to make sure that you knew what they were thinking, you know, meaning that they would travel, you know, countless managers would make the effort to travel, you know, down to Austin. Austin's a great place, right?

49:23But some of our managers were in Berlin or, you know, Tel Aviv, but they would make that trip be very proactive about, you know, certainly you can read it in a mid-year letter or an update, but more importantly, to build on that relationship, that personal relationship, and that takes effort. So I think the best managers did that. And then I think three, the best managers also made sure that the LP relationship was with the firm, in addition to maybe having a strong, you know, like a close relationship with a specific partner. And so when I would go and visit specific managers, I'd have the opportunity to go meet with like, you know, multiple folks on the team, right.

50:04I'd have exposure to the whole partnership. I'd meet with folks. And, you know, that way you can kind of, the LP has a sense of, you know, how is this, how are these, you know, how is this partnership functioning, right? Are folks on the same page? You know, how are they, you know, how are they complimentary? Not when you're diligencing them on whether or not to re-upping this fund or to invest in the fund, but, you know, how they're, you know, working together, you know, after you've committed to the fund, right, as they're deploying the fund. But those are just, I think, some of the ways that, you know, GPs, I think, have, you know, like thoughtfully, I think, worked with, you know, some of their LPs.

50:43It's downstream of this partnership mentality. If you have a true partner, you're not going to send them a letter and you're going to make an effort to actually meet with them. And again, like, this is a hard thing to do. I'm not again, it sounds like, like, you listen to this, like, oh, of course, like, but Conrad, like, you know, I'm a solo GP, right? Or Conrad, you know, there's only like three people on the team, right? Like, we had to experience all this also. And, you know, there's some times where we probably could, you know, communicated better, could have done things better. The reality of it is like, Like, again, this is aspirational, right?

51:21So you have to make this a priority and kind of work towards best in class, right? But if you're not thinking about it, then you're not like, you know, it's like you go to the gym, like, you know, and you're not working a specific muscle continuously. There's no expectation that, like, you're going to, you know, run faster when you go on the track or something, right? You kind of have to constantly cultivate this, even knowing that, you know, this isn't going to like excellence is not overnight. Right. It's this mentality. And we kind of we practice this ourselves. I think a lot of the credit goes to Gopi, who's my other co-founder, who's our head of data science, head of engineering, of taking this like mentality of building software.

52:05Right. Which is like V1 is not going to be like lights out. Right. V1 is probably going to be maybe pretty, pretty crappy. right? But we're going to constantly iterate. It's not a point in time. And this is kind of it. This is a constant iteration. And our aspiration is to get to like V infinite, where every version of it will continuously be better. I know for a fact, next week, we're going to be better. The product's going to be better than the week before. And next year, it's going to be like dramatically different. And so we have that mentality, not just in us building product for, you know, for ensemble, but ideally in how we're managing, like, you know, marketing, how we're managing, you know, managing relationships with their LPs, like we're nowhere, we know we're not the best.

52:51We're far from it, I think, in a lot of different ways. But we're constantly looking inward and saying, hey, like, what can we do better? And then having the expectation that a lot of the things we do aren't going to work, and they may fail. But that's not an excuse not to constantly try to, you know, try new things to push the boundaries and do better. If you think about it, all venture performance or any asset class is relative. If you think of this as relationship alpha, so you have your returns, you have your information alpha, you have this relationship alpha, a little bit goes a long way if your peer group is never flying to, maybe Austin's a little bit easier, but maybe it's North Dakota or Alaska and you're flying once a year, that goes a long way.

53:37So a little bit goes a long way as well. So let's talk about Ensemble, your fund. Mutual friend told me that you have a 12x mark on your fund one. First of all, is that true? And two is tell me about how you went about constructing fund one. Well, one, yes, like we're very proud of the performance in our fund one. It was our pilot fund. And, you know, we had the great fortune and maybe misfortune of like of, you know, having a very novel concept at the time when we raised the first fund in 2018, which was around this idea that you could bring a product engineering culture and mindset to a venture fund.

54:23Right. So, you know, obviously that means being data driven, but really having this very different approach of in order to get better. Right. We're going to go build software. We're going to go build product. Right. We're not going to throw more people at it. Like we're not going to we're not going to we want to grow exponentially or step function through software versus grow linearly through people. And so at the time, right, the use of software and data was not super obvious. And so it was a very difficult fund to raise, right? Kind of pass the hat. It was a very, it was also a small fund, but we had the opportunity to go incubate this actually within Kauffman Fellows to really experiment, test this out.

55:12And our sole objective in that phone one was to really prove that we could use data and use software and product in a way that could significantly change how a venture firm would function, and then in turn, deliver better performance than, you know, like, you know, the typical venture fund, right? So that was kind of the thesis, right? Could we radically, you know, implement more product engineering into a venture firm? You know, did we expect it to be, you know, like a 12x fund? and hopefully like, you know, you know, greater than that, which we think it can given some of our positions, it's it outperformed our kind of wildest imagination, right, of, you know, of very, very specifically, you know, finding great teams, right, not just great founders, you know, early, right, through a bunch of different signal that we could measure and track.

56:14and then also use that early advantage to translate into collaboration with other funds and then earning access. Right. And so that was the thesis that we proved. We had 12 investments. I think it was like five or six of the 12 ended up being ended up companies being valued over a billion. Right. So we had, you know, big Zoom in that portfolio as an example. We have Perot, which is a prominent indie in that portfolio. And so that was, I think, the initial proof of concept that allowed us to go think about, you know, the natural question after that is, well, how do you scale this strategy? Right.

56:56You can you scale this strategy? Right. When you're writing bigger checks, can you actually earn bigger access? Can you actually collaborate with other funds? Can you have this kind of repeat hit rate in the next fund? And so that thesis around using data and product and engineering has evolved significantly since our fund one. And the best reflection of that is from, you know, the founders, we're now a team of 12. Half of the folks on the team are data scientists and engineers. And then the other half are investors and like folks in operations. So people kind of say, oh, well, every fund is a data driven fund now.

57:46Like, I hope that's the case, right? Because I think that'll actually deliver better allocation of capital. So I want more and more folks to be data driven. But, you know, two, like there's a spectrum of what it means to be product engineering focused, you know, fund. And, you know, we've extended, I think, that software advantage into every aspect of the venture fund. So not just on the sourcing side, but also in the winning and value add side. We've built products to help our founders access customers, you know, find great people to hire and then, you know, other functions as well. Give me a very specific example of how data helps you make better investments.

58:27The simplest way to describe it is thinking about how venture has been done, you know, since the very beginning, right? And the evolution of that, and maybe the minimal evolution of that, which is historically, you know, when venture first started, you put your firm on Sandhill Road, right? And, you know, founders, you know, there weren't that many firms. And so, you know, founders would find out about X firm and go visit you. Right. Over time, that's evolved to, you know, more nodes. Right. In other cities and other places. And, you know, founders don't necessarily just come to specific firms, but you basically find opportunities based on folks in your immediate network.

59:11So maybe you used to work at Stripe or maybe you've been in venture for X number of years, had companies went public. And so you're backing the folks that are leaving those companies. Right. But it tends to be a very kind of finite network of folks and you really don't know where to hunt. And so you're you know, think of it almost like a random walk. You're top of funnel. You're meeting a bunch of folks. And, you know, very few of them end up translating into investments. And the headline of that, and I always found this really odd, is, you know, VCs would always say, hey, you know, hey, you know, and I was like, you, Tim, like, hey, Mr.

59:51LP, you know, I met 10 ,000 companies or 1 ,000 companies last year. Right. And I made one, you know, I made one or two investments. Right. Out of meeting a thousand companies. And you're like, you know, and they're like they're so proud because it demonstrates the rigor that they have. And, you know, how how high a bar that they have. The reality of it is that conversion is pretty bad. If you think of any other, you know, sales organization, right, you get fired, right? If you had to meet a thousand people and you signed up one customer or, you know, like a PE firm doesn't work like that, right?

1:00:28And so the question is, is, well, how do you actually change that funnel very dramatically, right? Because the reality of it is you don't want to be spending time aimlessly meeting folks, right? Even folks that get recommended to you, right? Because you still have that conversion rate. The reality of it is you want to redistribute your time, right? from the low value activities of first meetings to the high value activities of building the relationship, finding them early, and then positioning yourself to win what is, you know, very, very competitive, you know, deals. And so it's shifting kind of what that funnel looks like from, you know, a pyramid to maybe, you know, a diamond in terms of like time allocation.

1:01:08And so what we've done is build a platform internally, we call it Unity. We have offshoot products called Discovery. You know, we have a value add product called GTM 2.0. There's multiple products that we have internally. But within Unity, what we're trying to do is dramatically change, you know, where time is spent. Right. So if you can actually refocus all of your energy on a smaller set of opportunities that have a higher probability of generating a big outcome, not a guarantee, then you can fundamentally reallocate all of your time to diligencing these opportunities and also winning them. And so the question is like, well, what does that look like?

1:01:53And so for us, you know, that means not just having a box checking exercise of, hey, we, you know, we use ChatGPT or we buy a bunch of data from so and so that anybody can do, right? It means, you know, building things, you know, vertically integrating, right? So building our own product internally, right? Like we don't, you know, there's nowhere else to get kind of what we do, right? because we've actually built all the infrastructure internally, right? Not just, you know, the application layer. And that also means fundamentally building new process in the firm, right? So how we meet as a team and how we run our process looks very, very different than what I did at Norwest and also on Bain Capital.

1:02:40We run it like a software company, right? Every month we know what opportunities that we're going to be focused on. We're probably 70 % outbound as a result of that. And then I'd say the latest kind of evolution of the firm is we've actually changed how we've hired. Right. And so that's probably the biggest distinction between, you know, at least outside looking in of what it means to be a, you know, a data driven fund is that we fundamentally re-architected what the organization looks like. So not only is my co-founder, one of my co-founders, you know, head of data science, head of engineering, right?

1:03:16Gopi came from IBM Watson. But we've hired, our most recent hires have been, you know, two of which have been on the engineering side, right? And so half of us are on the engineering and data science side, right? It's not a box checking exercise to say, okay, hey, you know, we have the enterprise license for ChatGPT and we've hired a data scientist, right? Like we're good to go. like we're data driven and we're going to have the advantage, right? The reality of it is like, you're constantly iterating, you're constantly building new product. And, you know, the new product that we'll release at the end of the year, like we just thought about six months ago, right.

1:03:54Or even three months ago. And so we're constantly like, you know, innovating and building new things internally, you know, versus, you know, like waiting for ChatGPT to release, you know, ChatGPT 5 and, you know, or doing a deep research report or something, right? Like, great. Like anybody can go do that, right? It's fundamentally changing how your investment process is, your decision process, and then what your organization looks like. Give me some of your secret sauce. What is some data that you're looking at that narrows down your top of funnel dramatically that you look for investing at the early stage?

1:04:30People always ask that. I'll give you a couple of examples of it. It's not like a Harvard Business School study, right, which is, you know, you know, the person that's like, you know, left handed that went to Stanford that, you know, you know, came from, you know, an immigrant family is going to be like, you know, the amazing founder, right? Like, it's not formulaic like that. The reality of it is there's a bunch of different signal. Think of it as like stacking alphas, right? It's where each individual signal may not be that relevant, but the amalgamation of multiple signals actually drives meaningful alphas.

1:05:08That's like point one, just in terms of like philosophy. The second one I think is contextualization. And that's what, you know, LLMs and what AI has really helped accelerate for us. meaning, you know, if you're building a company that's in the consumer world versus building something in the healthcare world, selling to, you know, health systems, how you build that team will look dramatically different, right? You could, each team could be very, very high quality. You know, both founders could have, you know, come from, I don't know, like Stripe or something, right? But how you build that team out and what that team looks like, and maybe what your co-founders will look like will look dramatically different, right?

1:05:50And it's intuitive because you go to market motion for a consumer company is very different than a healthcare AI company selling into health systems, right? And so because we built the infrastructure, all of our data is not just a stacking of a bunch of different signals, but it's the contextualization and knowing and understanding what a company does, right? So saying, hey, this is a great team, but not a great team for a consumer company, right? Or, hey, this is actually a great team within healthcare, within the AI, and also relative to the stage, like you have to contextualize it. So that's kind of like, I offer that because it's an important framework, right?

1:06:33And then like on the specifics, like one example that you can actually track and measure that folks kind of use intuitively, and I mentioned this earlier, is like, did people on the team work together in the past? Right. And so like, you know, what will happen in the traditional sense is you'll meet a founder and then you'll maybe meet the head of engineering and be like, oh, like awesome. Like, oh, like no, no wonder there's great chemistry that they, you know, seem to work well as a team because, oh, they had worked together for four or five years, maybe not in the last job, but, you know, in a prior job at like Facebook or something.

1:07:09Right. So you're like, oh, that, that actually is great. That makes a lot sense, right? There's probably less team risk there. Because, you know, they've known each other, they worked each other, they kind of know, you know, the skeletons in their closets or something, right. But it's kind of it's like, you know, ex ante, right? After the fact of you meeting the founder, what we've done, and it's not the only thing we look at, and sometimes it's less important. But you know, when founders choose to come together to work together, or their first, second, third hires are folks that they had worked together in the past, there's a lot of interesting signal where A players tend to want to work together again because they have the context of knowing how people work in high-pressure environments when the company's growing really quickly, or they're handpicking the best within a certain group.

1:08:05We do a fair amount of A &D or defense investing under the broader umbrella of deep tech. And you see folks at Andrel kind of leave together in pockets. Andrel may not love that, but you're seeing someone who's leaving as a founder being very selective about the folks that they're bringing to the team. Right. Maybe an old colleague, not in the same group as this other group at Andrew. Like we've seen that, you know, across the board. The reality of it is like you can actually measure that. Right. The challenge is, is that a human just can't do that at scale. Right. But, you know, building a product, you can measure that one attribute, but you can also look at a thousand attributes and you can do that across, you know, 100 ,000 companies.

1:08:59And you could do that across, you know, 30, 40, 50 million people. Right. Because the beauty of software infrastructure is that it's infinitely customizable and it's infinitely scalable. Right. So we don't have to go hire and build a giant team. Right. Which is like people are linear. Right. Whereas software and, you know, and data, you know, can be exponential. And it's at the very least, it's a step function. And so that's kind of our framework of how we solve problems. Awesome. Well, this has been a fascinating conversation. I appreciate you jumping on and looking forward to continuing this conversation live.

1:09:38This is great. Thanks, David. Thanks for listening to my conversation. If you enjoyed this episode, please share with a friend. This helps us grow. Also provides the very best feedback when we review the episode's analytics. Thank you for your support.

From the publisher

Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors?

In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out.

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