The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Ryan Akkina argument clarity score 4.3/5 from 39 exchanges on raw tape · average scores: directness 4.6 · coherence 4.7 · precision 4 · compression 3.8 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay, so we know then we want to invest. How do we think again about portfolio allocations and sizing on a per position basis?

A It depends on our liquidity at any given time, but there's a huge range, honestly. So in, you know, in the case of Coupang, that was a hundred twenty million co-investment for us. We made, I think, a distribution price is seven to eight X or something like that. It's probably a little lower now, uh, that the stocks come down a bit, but You know, that was a large outcome for us, obviously. You know, sometimes it's constrained by what we can get. I mean, there's another opportunity where we co-invested in Snowflake, uh, before it IPO'd, and in that case, we were only able to get a few million bucks allocation, even though, given what we knew about the company, we would have invested a lot more, uh, if we had the opportunity. Uh, but, you know, I'd say it's, it's a wide range. If something's earlier stage and less certain, doesn't have as much structure, uh, it may only be a five million dollar check.

AI assessment note: “It depends on our liquidity at any given time, but there's a huge range”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q also given, you know, your role with MIT and like actually having outflows that are, I presume required in terms of scholarships and maintenance and everything involved, which is incredibly important, obviously. But A lot of LPs don't have mandated outflows that have to be made. Is that difficult? Because you kind of have to project forward into unknown times, and you don't know what you're going to need when.

A It certainly makes it a more tricky situation, but, you know, we, we have a lot of ways of modeling this, right? And for the most part, we're able to be pretty consistent in the check sizes we, we put out. I would say the last two years are unusual because of this dual problem of One, we normally assume all our managers are gonna raise every two to three years, and there was a period where basically everybody deployed a fund in one year and then raised again right away. So that was one thing, and then secondly- And doubled in size. And doubled in size, and, and this crop of, uh, you know, big companies has taken much longer to achieve liquidity than we expected. So I'd say there was some, there was sort of an unusual effect there in this cycle. But, but, you know, normally we know we have to pay out about five percent, um, Of our assets per year to support our institution. That never really changes. Uh, we have a smoothing formula for that, but, uh, you know, we, that's, that's pretty consistent. So we generally know what we, we need to do. It's just, I think this is a very unusual period.

AI assessment note: “It certainly makes it a more tricky situation, but, you know, we, we have”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Okay, so we know then we want to invest. How do we think again about portfolio allocations and sizing on a per position basis?

A It depends on our liquidity at any given time, but there's a huge range, honestly. So in, you know, in the case of Coupang, that was a hundred twenty million co-investment for us. We made, I think, a distribution price is seven to eight X or something like that. It's probably a little lower now, uh, that the stocks come down a bit, but You know, that was a large outcome for us, obviously. You know, sometimes it's constrained by what we can get. I mean, there's another opportunity where we co-invested in Snowflake, uh, before it IPO'd, and in that case, we were only able to get a few million bucks allocation, even though, given what we knew about the company, we would have invested a lot more, uh, if we had the opportunity. Uh, but, you know, I'd say it's, it's a wide range. If something's earlier stage and less certain, doesn't have as much structure, uh, it may only be a five million dollar check.

AI assessment note: “It depends on our liquidity at any given time, but there's a huge range”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q want to kind of Go through the stages that we kind of invest through in funds, and start with the pick, and I'd love it if we can go as granular as possible. It's, it's a crap question, so forgive me for it, but when we think about the evaluation of new fund managers, what is it that we're honing in on, and how do we think about manager evaluation?

A So I think the, the way I usually try to Kind of bucketed into different areas for evaluation is, um, and I think I've heard other people say this before too. It's certainly not original to me. It's see, pick, win, right? We need people who can see the best deals or at least a very large volume of deals, right? Hopefully the best deals are inside that set. Uh, then we want them to be able to pick the best ones to try and invest in. And then finally they need to actually be able to win allocation of those deals, right? Because there's lots of people who have great deal flow and who can pick the right stuff. But the final boss, so to speak, is, okay, can you get that entrepreneur to pick your term sheet over someone else who's really impressive? And then finally, I'd add, uh, service. How, how well do these GPs service their founders and, and ensure that when they're in the next competitive deal, uh, that founder they just backed is going to be a positive reference for the next one.

AI assessment note: “way I usually try to Kind of bucketed into different areas for evaluation is”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q mean, that is the question in my mind in many respects. Before we get into that and how you think about kind of picking and selecting managers, you know, you mentioned the 15 years there now at MIT. The landscape's changed a lot in that time. Is it harder than ever before today? And how do you think about comparing then and now in terms of investing in venture funds?

A It's gotten a lot more difficult for a lot of reasons. I think one is, I mean, if you just think of the strategy we used to have, and I think a lot of other large endowments had, For, for some time, it was basically sit back, see who the top five or six firms are focused on series A's in, in the US mainly. And, um, you know, we had a good enough, uh, brand as MIT or other endowments and foundations to wait till these things were pretty proven. Not to mention we've been investing in these things a long time. I mean, MIT has been investing in venture firms since I think at least the seventies, perhaps even earlier. Uh, so we could be a little bit lazy, and sit and wait, and then get into whatever the top firms were, and there wasn't a huge number of them, right? And today, I think the ecosystem is hugely more complex, right, in terms of stage, in terms of geography, in terms of all sorts of, you know, different business models there are for venture firms, different, uh, sector specialists, and so forth. So it's just, there's a lot more waterfront to cover, first of all. And secondly, It's a lot more competitive, um, right? I mean, I think it's been said for a while that venture is kind of a cottage industry, or at least it was, but now, uh, you know, it's, it's probably every day there's an article in the Wall Street Journal or the FT about something in venture land or startups. …

AI assessment note: “It's gotten a lot more difficult for a lot of reasons.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q also given, you know, your role with MIT and like actually having outflows that are, I presume required in terms of scholarships and maintenance and everything involved, which is incredibly important, obviously. But A lot of LPs don't have mandated outflows that have to be made. Is that difficult? Because you kind of have to project forward into unknown times, and you don't know what you're going to need when.

A It certainly makes it a more tricky situation, but, you know, we, we have a lot of ways of modeling this, right? And for the most part, we're able to be pretty consistent in the check sizes we, we put out. I would say the last two years are unusual because of this dual problem of One, we normally assume all our managers are gonna raise every two to three years, and there was a period where basically everybody deployed a fund in one year and then raised again right away. So that was one thing, and then secondly- And doubled in size. And doubled in size, and, and this crop of, uh, you know, big companies has taken much longer to achieve liquidity than we expected. So I'd say there was some, there was sort of an unusual effect there in this cycle. But, but, you know, normally we know we have to pay out about five percent, um, Of our assets per year to support our institution. That never really changes. Uh, we have a smoothing formula for that, but, uh, you know, we, that's, that's pretty consistent. So we generally know what we, we need to do. It's just, I think this is a very unusual period.

AI assessment note: “It certainly makes it a more tricky situation, but, you know, we, we have a lot of ways of modeling this”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I, I totally agree with you in terms of that timeline. I spoke to Neil Mato before the show, and he said, ask him specifically for the funds which are firing, which are working really well. What are the reasons that they go sideways?

A Well, one thing is, uh, I think sometimes firms grow too big too quickly, right? And that forces them out of whatever their sweet spot was. I think another issue is, you know, frankly, if people have a, uh, spell of success, uh, sometimes they become arrogant, right? And sometimes they lose their intellectual honesty and their humility, and they start to make worse decisions and treat people worse and not work as hard, et cetera. Um, that, that can happen sometimes and cause someone who was otherwise on a good trajectory to, To go sour. Yeah. There's a lot of things that can go wrong. Another thing I'd point to is, um, honestly, sometimes people just lose their, their motivation, right? Once they've been successful enough. And that's a key thing we try to suss out, right? When we get to know people, what is it that drives them and how long is this really going to keep them competing at the top of their game for?

AI assessment note: “Well, one thing is, uh, I think sometimes firms grow too big too quickly”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said about the third bucket being, you know, Sometimes people who can provide good directs. You mentioned Coupang earlier. Um, I know that you're very active in terms of direct investing. Why is that such an important part of strategy, do you think?

A I think, I think there's a number of things we like about it. One is just, um, you know, if you can have another tool in your toolbox for making good investments, why not, uh, build that up, right? Uh, secondly, I, I mean, I personally find it easier in a lot of cases to write a big check to a co-invest than to a blind pool fund, right? Because no matter your conviction in someone, When you're writing them a blank check, you know, we don't, we don't know what's gonna happen, right? And as we've, you know, talked about a little bit, even with people who have a really good track record, uh, you know, you can't, you can't fully predict how they're gonna do with that next check, right? But if we have an opportunity to invest in something that we know is a great company today at a reasonable valuation, uh, and sometimes with a really great structure around it as well, it's, I find it much easier to have high conviction in that.

AI assessment note: “if you can have another tool in your toolbox for making good investments, why not”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I don't mean to push back on you, but MIT is a great name, period. Can you really not get into great funds and be a little bit sit back?

A Oh, absolutely. I mean, there are several, uh, very impressive firms that we missed. Uh, and if we were to try and get in today, you know, you never know, but in, in, I think in many cases, maybe we would be able to get in, but the check size we would be able to get would be relatively small. Small enough that we would question whether it was worth doing, but maybe that's something we should think about. There might be cases where we would be willing to do something even with a really small check just for the relationship. But yeah, I mean, these firms, uh, once they're discovered and it happens early and earlier now, You know, they, they rightfully prioritize their existing LPs and the people who back them, uh, from the beginning when they're thinking about who to give capacity to for future funds.

AI assessment note: “there are several, uh, very impressive firms that we missed.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q How do we answer the liquidity question? I'm sure you get it from Seth and from other people, but What's the answer? There's a lot of companies waiting.

A I mean, there's not much we can do, strictly speaking, right? I mean, there's some cases where maybe, uh, particularly if there was a co-investment, we could encourage a manager to sell some secondary or something. But, you know, there's, there's not much we can do, right? We're, we're waiting like everyone else for these things to, to IPO. And, and I think another thing we're concerned about, of course, is with a lot of these companies, so much of the cap table is owned by, uh, investors who have been there a long time and maybe obligated by their fund lives to get out. Uh, it's anyone's guess what's gonna happen to the prices of these things when the lockup windows expire, right?

AI assessment note: “there's not much we can do, strictly speaking, right?”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Do you mind that? I find IR teams respectfully, and there's nothing against them, but they just create a layer that removes from the human relationship with the GP. I think it also impedes your ability to get good directs, because you lose that messaging with Neil, or messaging with whoever that is. Are you turned off by IR?

A It just depends on how it's done, right? I mean, I think there are some people who do a really good job at it, and, you know, they manage to thread that needle of protecting the time of the GPs who you want focused on their main job, right, which is investing, but still, you know, manage to keep you updated, and like, you know, what's going on, and can get you access to that person, uh, when you occasionally need it. And, and of course, something we try to do as LPs is not be overly demanding in, The, the time we take from people, right? Uh, you know, we're always very conscientious of the fact that we want most of these people to be spending most of their time out on the field, right? Chasing the best deals and not, you know, with us or other LPs.

AI assessment note: “It just depends on how it's done, right?”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q mean, that is the question in my mind in many respects. Before we get into that and how you think about kind of picking and selecting managers, you know, you mentioned the 15 years there now at MIT. The landscape's changed a lot in that time. Is it harder than ever before today? And how do you think about comparing then and now in terms of investing in venture funds?

A It's gotten a lot more difficult for a lot of reasons. I think one is, I mean, if you just think of the strategy we used to have, and I think a lot of other large endowments had, For, for some time, it was basically sit back, see who the top five or six firms are focused on series A's in, in the US mainly. And, um, you know, we had a good enough, uh, brand as MIT or other endowments and foundations to wait till these things were pretty proven. Not to mention we've been investing in these things a long time. I mean, MIT has been investing in venture firms since I think at least the seventies, perhaps even earlier. Uh, so we could be a little bit lazy, and sit and wait, and then get into whatever the top firms were, and there wasn't a huge number of them, right? And today, I think the ecosystem is hugely more complex, right, in terms of stage, in terms of geography, in terms of all sorts of, you know, different business models there are for venture firms, different, uh, sector specialists, and so forth. So it's just, there's a lot more waterfront to cover, first of all. And secondly, It's a lot more competitive, um, right? I mean, I think it's been said for a while that venture is kind of a cottage industry, or at least it was, but now, uh, you know, it's, it's probably every day there's an article in the Wall Street Journal or the FT about something in venture land or startups. …

AI assessment note: “It's gotten a lot more difficult for a lot of reasons.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q How do you decide in that way? I don't know if you can go into the decision making process, but that is an incredibly compressed timeline. I don't, I don't know any that can write that size check in that timeframe.

A Well, we didn't write the whole thing, to be clear. I mean, honestly, Neil probably had several other, uh, You know, several of Neil's LPs are very good. I'm sure there were others that participate as well. Um, you know, in, in a situation like that, a lot of it is, is trust, right? I mean, we trust Neil's judgment, but also that was another case where the structure was fantastic. You know, we knew a lot about the company already. Uh, we had several other people we know who had a really high opinion of, uh, of Parker. So I think we had a prepared mind for it as well. So it was a combination of, we had a prepared mind for Because we knew about the company and the founder already. We had a lot of trust already in Neil and his team. And thirdly, the structure was really fantastic.

AI assessment note: “it was a combination of, we had a prepared mind”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I don't mean to push back on you, but MIT is a great name, period. Can you really not get into great funds and be a little bit sit back?

A Oh, absolutely. I mean, there are several, uh, very impressive firms that we missed. Uh, and if we were to try and get in today, you know, you never know, but in, in, I think in many cases, maybe we would be able to get in, but the check size we would be able to get would be relatively small. Small enough that we would question whether it was worth doing, but maybe that's something we should think about. There might be cases where we would be willing to do something even with a really small check just for the relationship. But yeah, I mean, these firms, uh, once they're discovered and it happens early and earlier now, You know, they, they rightfully prioritize their existing LPs and the people who back them, uh, from the beginning when they're thinking about who to give capacity to for future funds.

AI assessment note: “there are several, uh, very impressive firms that we missed.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q want to kind of Go through the stages that we kind of invest through in funds, and start with the pick, and I'd love it if we can go as granular as possible. It's, it's a crap question, so forgive me for it, but when we think about the evaluation of new fund managers, what is it that we're honing in on, and how do we think about manager evaluation?

A So I think the, the way I usually try to Kind of bucketed into different areas for evaluation is, um, and I think I've heard other people say this before too. It's certainly not original to me. It's see, pick, win, right? We need people who can see the best deals or at least a very large volume of deals, right? Hopefully the best deals are inside that set. Uh, then we want them to be able to pick the best ones to try and invest in. And then finally they need to actually be able to win allocation of those deals, right? Because there's lots of people who have great deal flow and who can pick the right stuff. But the final boss, so to speak, is, okay, can you get that entrepreneur to pick your term sheet over someone else who's really impressive? And then finally, I'd add, uh, service. How, how well do these GPs service their founders and, and ensure that when they're in the next competitive deal, uh, that founder they just backed is going to be a positive reference for the next one.

AI assessment note: “bucketed into different areas for evaluation is... see, pick, win”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I, I totally agree with you in terms of that timeline. I spoke to Neil Mato before the show, and he said, ask him specifically for the funds which are firing, which are working really well. What are the reasons that they go sideways?

A Well, one thing is, uh, I think sometimes firms grow too big too quickly, right? And that forces them out of whatever their sweet spot was. I think another issue is, you know, frankly, if people have a, uh, spell of success, uh, sometimes they become arrogant, right? And sometimes they lose their intellectual honesty and their humility, and they start to make worse decisions and treat people worse and not work as hard, et cetera. Um, that, that can happen sometimes and cause someone who was otherwise on a good trajectory to, To go sour. Yeah. There's a lot of things that can go wrong. Another thing I'd point to is, um, honestly, sometimes people just lose their, their motivation, right? Once they've been successful enough. And that's a key thing we try to suss out, right? When we get to know people, what is it that drives them and how long is this really going to keep them competing at the top of their game for?

AI assessment note: “one thing is, uh, I think sometimes firms grow too big too quickly”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q How do we answer the liquidity question? I'm sure you get it from Seth and from other people, but What's the answer? There's a lot of companies waiting.

A I mean, there's not much we can do, strictly speaking, right? I mean, there's some cases where maybe, uh, particularly if there was a co-investment, we could encourage a manager to sell some secondary or something. But, you know, there's, there's not much we can do, right? We're, we're waiting like everyone else for these things to, to IPO. And, and I think another thing we're concerned about, of course, is with a lot of these companies, so much of the cap table is owned by, uh, investors who have been there a long time and maybe obligated by their fund lives to get out. Uh, it's anyone's guess what's gonna happen to the prices of these things when the lockup windows expire, right?

AI assessment note: “there's not much we can do, strictly speaking, right?”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said about the third bucket being, you know, Sometimes people who can provide good directs. You mentioned Coupang earlier. Um, I know that you're very active in terms of direct investing. Why is that such an important part of strategy, do you think?

A I think, I think there's a number of things we like about it. One is just, um, you know, if you can have another tool in your toolbox for making good investments, why not, uh, build that up, right? Uh, secondly, I, I mean, I personally find it easier in a lot of cases to write a big check to a co-invest than to a blind pool fund, right? Because no matter your conviction in someone, When you're writing them a blank check, you know, we don't, we don't know what's gonna happen, right? And as we've, you know, talked about a little bit, even with people who have a really good track record, uh, you know, you can't, you can't fully predict how they're gonna do with that next check, right? But if we have an opportunity to invest in something that we know is a great company today at a reasonable valuation, uh, and sometimes with a really great structure around it as well, it's, I find it much easier to have high conviction in that.

AI assessment note: “easier in a lot of cases to write a big check to a co-invest”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q I may be veering into completely dangerous territories here, but Why not? Um, are the incentive structures financially right in endowments? When I, what I mean by that is a 120,000,007, eight X. That is a huge amount of carry if you're in a traditional fund structure. Do endowment funds have the financial incentive structure right?

A I mean, honestly, I think the answer is no. Like, uh, I think we're able to do what we do because I have to give credit to our CIO, Seth. He's created a culture where People care about doing these things and want to do these things, and I think also it helps that, um, because we had a period of success, I think we had, you know, we built up enough credibility in our own situation to feel comfortable taking some of these risks, right? But yeah, I mean, the traditional endowment or foundation, I think part of the reason they're not good at this stuff is they don't have an incentive to be right, and people, when they don't have an incentive to take risks, they're not going to want to stick their necks out.

AI assessment note: “I mean, honestly, I think the answer is no.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q How do we move away from that? And what's the right incentive structure?

A Well, it's, it's tough. I'm on, I'm of two minds on this, right? Because I think the, the reason, there are good reasons for endowments and foundations to have the incentive structures that they have, because something that the governance is typically concerned with is they want to make sure things don't go awry, right? And they don't want to give people, you know, a free option on an institution's capital, right? By giving them carry necessarily. So, you know, there's good reasons to do it the way it is done, but I, you know, if I think, if I had a blank sheet of paper, if I were running a family office, let's say, I would probably do something where, one, people would be required to invest a lot of their own money in the investments the firm was making. Um, you know, either money they already had or a large portion of whatever their bonus might be. Um, and I would probably say yes, there has to be some kind of incentive structure, maybe over a, a suitable hurdle.

AI assessment note: “if I had a blank sheet of paper... people would be required to invest a lot”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Do you mind that? I find IR teams respectfully, and there's nothing against them, but they just create a layer that removes from the human relationship with the GP. I think it also impedes your ability to get good directs, because you lose that messaging with Neil, or messaging with whoever that is. Are you turned off by IR?

A It just depends on how it's done, right? I mean, I think there are some people who do a really good job at it, and, you know, they manage to thread that needle of protecting the time of the GPs who you want focused on their main job, right, which is investing, but still, you know, manage to keep you updated, and like, you know, what's going on, and can get you access to that person, uh, when you occasionally need it. And, and of course, something we try to do as LPs is not be overly demanding in, The, the time we take from people, right? Uh, you know, we're always very conscientious of the fact that we want most of these people to be spending most of their time out on the field, right? Chasing the best deals and not, you know, with us or other LPs.

AI assessment note: “It just depends on how it's done, right?”

Answered raw tape D 5 · C 5 · P 4 · Cm 3 4.45

Q How do you decide in that way? I don't know if you can go into the decision making process, but that is an incredibly compressed timeline. I don't, I don't know any that can write that size check in that timeframe.

A Well, we didn't write the whole thing, to be clear. I mean, honestly, Neil probably had several other, uh, You know, several of Neil's LPs are very good. I'm sure there were others that participate as well. Um, you know, in, in a situation like that, a lot of it is, is trust, right? I mean, we trust Neil's judgment, but also that was another case where the structure was fantastic. You know, we knew a lot about the company already. Uh, we had several other people we know who had a really high opinion of, uh, of Parker. So I think we had a prepared mind for it as well. So it was a combination of, we had a prepared mind for Because we knew about the company and the founder already. We had a lot of trust already in Neil and his team. And thirdly, the structure was really fantastic.

AI assessment note: “It was a combination of, we had a prepared mind”

Answered raw tape D 4 · C 5 · P 4 · Cm 4 4.30

Q But they are great pickers. You have, how do you think about really what's primary?

A I mean, I think if you're a great picker, And you're not really that well liked. It can work. I mean, it depends on how competitive your space is, right? So I think in seed, that's probably more doable than in series A, for instance, right? Um, although of course there, there are people who win and, you know, you hear crazy stories about, um, I, but I would say we tend to spend the most time thinking about the, the winning and servicing angle, which kind of feed on each other. Because I, I think, you know, look, there's at least several hundred people in the industry at any given time, GPs I'm talking about, who have good deal flow and good picking abilities. The competitive aspect forces us to, to focus our evaluation on those final two pieces, the winning and the picking, or sorry, the winning and the servicing.

AI assessment note: “we tend to spend the most time thinking about the, the winning and servicing angle”

Answered raw tape D 4 · C 5 · P 4 · Cm 4 4.30

Q How do we move away from that? And what's the right incentive structure?

A Well, it's, it's tough. I'm on, I'm of two minds on this, right? Because I think the, the reason, there are good reasons for endowments and foundations to have the incentive structures that they have, because something that the governance is typically concerned with is they want to make sure things don't go awry, right? And they don't want to give people, you know, a free option on an institution's capital, right? By giving them carry necessarily. So, you know, there's good reasons to do it the way it is done, but I, you know, if I think, if I had a blank sheet of paper, if I were running a family office, let's say, I would probably do something where, one, people would be required to invest a lot of their own money in the investments the firm was making. Um, you know, either money they already had or a large portion of whatever their bonus might be. Um, and I would probably say yes, there has to be some kind of incentive structure, maybe over a, a suitable hurdle.

AI assessment note: “if I had a blank sheet of paper, if I were running a family office”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q Has your investing style changed over the years? 15 years is a long time. Has how you think, how you prioritize, what you prioritize changed?

A Well, for one thing, I, I personally spend a lot less time on the public markets than I used to. Um, I mean, actually, when I started MIT, I was mostly doing public market stuff, but I'd say in the last seven to 10 years, I've sort of switched to doing mostly private stuff. Uh, I, I just find it much easier for me and my personality to, uh, I think generate alpha on the private side. I mean, the public side is always becoming more competitive. You think, if you think venture is competitive, try making alpha versus, uh, you know, the NASDAQ, right, as a public manager. That's, Incredibly difficult to do on a consistent basis. That's one thing that's changed for me. I think another thing is, um, I think after seeing things play out over a couple cycles, I trust my judgment a little more, right? I mean, there are things that happened during the peak of bubbles where, uh, you know, you didn't think something would do nearly as well. Maybe there's something you passed on, right? For good reasons, and then it does incredibly well, and, you know, it's a rather confusing, but, but sure enough, these things eventually come down to earth. Well, it's funny you ask that in, about some of my mistakes, right? Because actually the biggest mistakes I, are actually errors of omission, of things that did really well. And probably the number one thing I think about right now is, uh, you know, I m…

AI assessment note: “I've sort of switched to doing mostly private stuff.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q But they are great pickers. You have, how do you think about really what's primary?

A I mean, I think if you're a great picker, And you're not really that well liked. It can work. I mean, it depends on how competitive your space is, right? So I think in seed, that's probably more doable than in series A, for instance, right? Um, although of course there, there are people who win and, you know, you hear crazy stories about, um, I, but I would say we tend to spend the most time thinking about the, the winning and servicing angle, which kind of feed on each other. Because I, I think, you know, look, there's at least several hundred people in the industry at any given time, GPs I'm talking about, who have good deal flow and good picking abilities. The competitive aspect forces us to, to focus our evaluation on those final two pieces, the winning and the picking, or sorry, the winning and the servicing.

AI assessment note: “we tend to spend the most time thinking about the, the winning and servicing angle”

Answered raw tape D 4 · C 5 · P 4 · Cm 4 4.30

Q How do you think about the underwriting process?

A Well, ideally we, we do like to get to know these businesses. And so ideally we like to get to know them well ahead of time. And in the case of coupon, for instance, you know, when we first got, uh, interested in it, it was when we did a reference call on Neil with the company and we're very impressed with Uh, bomb. And that was a, that was something Neil actually invested in before Green Oaks won. Uh, and so we were kind of, uh, you know, disappointed actually that we were investing in this new fund where it was not going to have that exposure. Right. And so we told him if there's ever an opportunity for us to invest alongside you in this company in the future, let us know. Uh, and, you know, and sure enough, within a few years after that, Neil did see there being a potential opportunity to put the structured round together and let us know. And, You know, we had enough time to go visit, uh, the company in South Korea and tour some of the warehouses and things like that, get to know BOM a little bit better. I'd also say, I think we had a prepared mind because by that time, obviously we'd seen Amazon work in the US, right? We'd seen some other things in other countries like say JD in China or Flipkart in India turn out to be interesting as well. Uh, so that was some of what turned us on to the opportunity. And, and in that case, we were able to spend quite a lot of time getting …

AI assessment note: “ideally we like to get to know them well ahead of time”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q Yeah, no, I, I get you completely. Can I ask, I, I've spoken obviously to, to many over the last few months and a lot of them regret activity in China. How do you think about China today moving forward? Any lessons?

A Well, it's, I mean, it's something we're wondering about as well. Uh, I mean, it was an area of great success for us for some period of time. You know, we're definitely, I think like many others, we're, we're doing a lot less there now. Uh, I mean, we're not gonna categorically not do it at all yet. Um, but we are reducing it, and to the things that we keep doing, we're, you know, we're, we're very careful about whether they're people that we think are gonna Keep from, uh, sensitive areas of investment, right? And, and obviously also we don't know how these regulations might change in the future. So, uh, that's another reason to keep it small.

AI assessment note: “we're doing a lot less there now. Uh, I mean, we're not gonna categorically”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q Has your investing style changed over the years? 15 years is a long time. Has how you think, how you prioritize, what you prioritize changed?

A Well, for one thing, I, I personally spend a lot less time on the public markets than I used to. Um, I mean, actually, when I started MIT, I was mostly doing public market stuff, but I'd say in the last seven to 10 years, I've sort of switched to doing mostly private stuff. Uh, I, I just find it much easier for me and my personality to, uh, I think generate alpha on the private side. I mean, the public side is always becoming more competitive. You think, if you think venture is competitive, try making alpha versus, uh, you know, the NASDAQ, right, as a public manager. That's, Incredibly difficult to do on a consistent basis. That's one thing that's changed for me. I think another thing is, um, I think after seeing things play out over a couple cycles, I trust my judgment a little more, right? I mean, there are things that happened during the peak of bubbles where, uh, you know, you didn't think something would do nearly as well. Maybe there's something you passed on, right? For good reasons, and then it does incredibly well, and, you know, it's a rather confusing, but, but sure enough, these things eventually come down to earth. Well, it's funny you ask that in, about some of my mistakes, right? Because actually the biggest mistakes I, are actually errors of omission, of things that did really well. And probably the number one thing I think about right now is, uh, you know, I m…

AI assessment note: “in the last seven to 10 years, I've sort of switched to doing mostly private stuff.”

Answered raw tape D 3 · C 5 · P 5 · Cm 4 4.25

Q What you saw that others didn't? Just help me understand it.

A Yeah, well, it's, it's funny, uh, that decision almost didn't happen, and I, I told, I didn't tell Neil this story until somewhat recently, um, But actually, uh, when we first invested in Green Oaks, it was back during the period where we were a bit more conservative in the VCs. Would, we would back, and as a general rule, we didn't want to back anyone who didn't already have a great brand. And of course, Green Oaks at that time was raising its first institutional fund, uh, and, you know, was not well known at that time. So it definitely didn't fulfill that criterion. Um, and I remember actually, you know, my boss, Seth, and I decided, you know, let's, let's leave this and look at fund two or something. Um, and the next, but I slept on it, and then the next day I, I decided to call my boss, Seth, back and say, you know, I think we should at least make a small bet on this to start, and we did, and which is, it's lucky we did, because that's been one of our most successful, uh, relationships of the last 10 years. But, you know, to answer your question, what did we see in him? I think one thing that stood out even then was, before he raised his fund, he'd done a bunch of Uh, individual deals, not with the fund, but sort of on a, uh, you know, a deal by deal basis raising money for each thing. And we talked to a number of the founders that he worked with, uh, like bomb from coupon …

AI assessment note: “to answer your question, what did we see in him? I think one thing”

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