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Podcast Summary: The Twenty Minute VC (20VC) - Episode with Ryan Akkina
Episode Overview Title: 20VC: How MIT Selects Venture Managers to Invest in Guest: Ryan Akkina, Global Investment Team Member at MIT Investment Management Company (MITIMCo) Host: Harry Stebbings Air Date: [Specific Date Not Provided]
Key Themes
- The evolution of venture capital landscape
- MIT's investment strategies and criteria for evaluating fund managers
- The dynamics of direct investing versus traditional fund investment
- The challenges faced by LPs (Limited Partners) in today's market
Key Discussions
- From Engineer to LP with MIT
- Background of Ryan Akkina:
- Transitioned from engineering to management consulting before joining MIT.
- Emphasized the importance of understanding the LP world and the decision to work with an endowment like MIT.
- Career Insights:
- Turning down a VC opportunity early in his career due to concerns over track record and the competitive nature of venture capital.
- The Manager Evaluation Process for MIT
- Evaluating New Managers:
- Ryan discusses the criteria for selecting fund managers, emphasizing the importance of:
- Track record
- Ability to attract top-tier founders
- Relationship-building with entrepreneurs.
- Common Pitfalls:
- Reflects on past mistakes made in evaluating managers and how those experiences shaped his current evaluation process.
- How MIT Builds Their Portfolio
- Portfolio Construction:
- Describes MIT's diversified approach:
- Core relationships with larger investments ($50-150 million).
- Smaller investments in less mature funds ($10-20 million).
- High-risk opportunities with minimal initial checks ($1 million).
- Reasons for Not Reinvesting:
- Discusses the criteria that lead to not re-upping with certain managers.
- MIT: The Direct Investor
- Direct Investment Strategy:
- Ryan elaborates on the rationale behind direct investments versus fund investments.
- Highlights the conviction in investing directly in known companies like Coupang and Rippling.
- Approach to Underwriting:
- Emphasizes thorough due diligence and understanding the business model before making direct investments.
- LP Markets Today and Future Directions
- Current Landscape for LPs:
- Ryan discusses the challenges LPs face in today’s market, particularly regarding:
- Liquidity constraints.
- The competitive nature of fundraising.
- Advice for Emerging Managers:
- Stresses the importance of relationship-building and treating fundraising as an enterprise sales cycle.
Key Takeaways
- Evolution of the VC Landscape:
- The venture capital industry has become more competitive and commoditized, making it harder for LPs to secure profitable investments.
- Importance of Relationships:
- Building lasting relationships with fund managers and founders is crucial for success in venture investing.
- Risk Management:
- Ryan emphasizes the importance of assessing risk through careful evaluation of managers and understanding market dynamics.
- Navigating Direct Investments:
- Direct co-investing can offer significant advantages when executed with thorough diligence and a clear understanding of the company’s potential.
- Perspective on the Future:
- The landscape for LPs may remain challenging, yet there are opportunities to be found, especially for those willing to adapt and innovate.
Additional Remarks The episode provides deep insights into the workings of venture capital from an LP’s perspective, highlighting the complexities of investing in a rapidly changing environment. Ryan's experiences at MITIMCo serve as a valuable blueprint for navigating the venture capital landscape successfully.
For more insights, listeners are encouraged to visit the [Twenty Minute VC website](http://www.20vc.com) for additional resources and episodes.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00So today, at least in the US venture portfolio, we probably have maybe six to eight core relationships, 50 to 150 million per fund. And then after that, we have another bucket where the check sizes are typically 10 to 20 million per fund. And those are things where they may be less mature managers. And so that's why we're not writing this big of check. A third bucket we have now is things where basically we'll write a million dollar check because maybe it's extremely early and the person had no track record, not even an angel track record, let's say, or we're doing it to work with them to source COVID -19 in the future.
0:34This is 20VC with me Harry Stebeng's name very excited to welcome a very special guest today, a brilliant partner to me and 20VC and one of the leading LPs fund investors in the venture business, Ryan Aquina, member of the global investment team at the MIT Investment Management Company, which is responsible for managing MIT's endowment and pension plans. Ryan is invested in the lights of Sequoia, Cliner Perkins, Andrewsson, Greenos, and initialised to name a few. Ryan also leads many of MIT's direct co -investments, including most notably into Coupang and Ripling. But before we dive into the show's day, Hyve is the marketplace for private stock.
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3:37Remote opportunity is wherever you are. You have now arrived at your destination. Ryan, I am so excited for this. I love love that you're here. So thank you so much for joining me today. My pleasure. The tables return now. The tables return now. So this is going to be fun. The LP world is an interesting one. How did you make your way into the world of funding, investing and being an LP and come to bit on my tea. Well, it's definitely not a job that you think of as a kid or something in some way, right? I mean, I didn't even know the job existed probably until my early 20s. You know, Rich and I thought I'd be an engineer and I was lucky.
4:11I had this interesting job in high school where I worked at HP and then tell working on microchip design on this project called the itanium processor. And so I assumed when I went to college, I'd probably do doubly and, you know, be an engineer after that. But I went up at Stanford about four summers into my internship at HP and Intel. We're on this process, so I decided I didn't really like working as an individual contributor engineer in a cubicle somewhere and wanted to do something different. So I switched to something at Stanford called Management Science and Engineering. In retrospect, maybe what I should have concluded is I just didn't like working at big company.
4:44But anyway, I did that, and I was also part of a lot of entrepreneurship activity at Stanford, if you will. There was this club called Bases that helped organize the career fairs and and the speaker series and things like that. So I got to meet a lot of interesting VCs and entrepreneurs through that, got to work with some interesting firms as well. This was back before YC was so well known, for instance. And I remember one spring, I think, we helped organize a YC startup school events on the Stanford campus. So I got to see that from pretty early days. So, you know, actually when I was graduating, I thought, well, maybe I'd like to become a venture capitalist.
5:17And I also started a company with some friends, my senior year, that a few months in I decided it was unlikely to work out so I didn't stick with it. They actually went on with it for four or five years I think and went through YC and made a go of it. But anyway, I actually thought about becoming a venture capitalist school and I hadn't offered it a firm, but I ended up deciding, you know, I don't really have a right to win there, right? I had seen by that time that the returns were pretty concentrated in just the top people and not having been an entrepreneur or even a senior executive or something to check.
5:47I just thought, well, you know, is this really the best thing for me to start off at 22 and just carry someone's bag and probably not be very much value -ed. But then inexplicably, I decided to be a management consultant instead. So I did that for about a year. It was a good experience. I learned a lot, but about six months in, I could already tell. I didn't want to do that for the full two or three years that you typically do it as an analyst. And I remember that I'd been interested in investing from seeing venture capital. And obviously, I still didn't have a good reason to be in venture capital.
6:15I thought, what else can I do to learn about lots of different types of inventors? and where could I work for good costs as well. And so that's how I got the idea of working for an endowment or foundation and learned about this whole LP world. And it just happened that MIT had a job posting on their website. So I applied to that and through chance and luck basically wound up there in 2009. And that was 15 years ago. I've been there ever since. And so I'm saying you said about the right to any key to your voice that on the show the other day that the single most important question any manager has to answer is why do the single best founders in the world choose to work with you over and else?
6:48Yeah, and I always find it astonishing how few LPs are sent. 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 15 years there now at MIT the landscape 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? It's gotten a lot more difficult for a lot of reasons I think one is, I mean, if you just think of this strategy we used to have, and I think a lot of other large end diamonds had for some time It was basically sit back, see who the top five or six firms are focused on series a's in the US mainly You know, we had a good enough brand as MIT or other end diamonds 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 70s 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.
7:56There are for venture firms different sector specialists and so forth There's a lot more waterfront to cover first of all and secondly, it's a lot more competitive I mean, I think it's been said for a while that Ventress kind of a cottage industry or at least it was, but now, you know, it's probably every day there's an article in the Wall Street Journal or the FT about something in Ventraland or startups. It's become a very... I think, I think, Doug Lee, I need to put it well, which is that, you know, we've transitioned from a boutique cottage industry with high margins to a commoditized low margin business, unfortunately.
8:28Sadly. Right. Right. So we have to try and still find the places where we can make high margins, and that's become very difficult obviously. I don't think we ever go back to that boutique I'm margin business. I think we've forever privatized or hedge fundized. Our business has changed so seismically and there's not a going back. Just like hedge funds are the asset allocation industry that they are on. Productivity is do you agree with me or do you think we do get that to the more boutique industry? I agree with you. I think this is something that only goes one direction and of course there will be cycles like right now in things to you know having a bad the past few years, it's become a little less popular and there's a little less competition, but I think that is a secular trend.
9:08It's going to be an industry with more capital and more eyes on it. I don't mean to push back when you, but MIT is a great name, period. Can you really not get into great funds and be a little bit sit back? Oh, absolutely. I mean, there are several very impressive firms that we missed. And if we were to try and get in today, you know, you never know, but 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, if 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.
9:42But yeah, I mean, these firms, once they're discovered, and it happens early and earlier now, they rightfully prioritize their existing LPs and the people who back them from the beginning when they're thinking about who to give capacity to for future funds. And so you go earlier, now they add down the funnel. Peter the kind at SCS said on the show that now's the best time ever to be investing in emerging manages. I think he's right though, right? I mean, I think one of the hard things is seeing who's truly dedicated and who truly wants it badly, right? And during times like this, when it's much harder to raise capital, you see which new firms really want it badly and the ones who don't are disappearing, right?
10:20So I think that's one thing. And of course, look, at least for some period of time while we're in a downspirer there'll be a little bit less competition and valuations will be better as well. Which firms have you back just to provide some contacts for listeners? Yeah, well, as I said, we've been lucky that we've been in this game a long time as an institution, right? So we're lucky to be in a lot of the big names you would expect, you know, Sequoia, Cliner Perkins, and Dreson, et cetera. And then there's some newer things as well that we've done in the past 10 or 15 years, like say, green oaks or white combinator initialized.
10:48Those would give some flavor for some of the things we do. Great. Now it's super helpful in terms of contact setting. So I do want to kind of go through the stages that we kind of invest in funds and start with the pick and I'd love it if we can go as granular as possible. It's a crap question, so forgive me for it But when we think about the evaluation of new farm managers, what is it that we're honing in on and how do we think about Manager evaluation? The way I usually try to bucket it into different areas for evaluation is See pick when right we need people who can see the best deals then we want them to be able to pick the best ones to try and invest and then finally they need to actually be able to win allocation on sales right because there's lots of people who have great deal flow and who can pick the right stuff but the final boss I just 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 service how well do these GP service their founders and ensure that when they're in the next competitive deal that founder they just back to just going to be a positive reference for the next one.
11:50What do you think is the most important? I know that all needed to win. But actually, some less than others respectfully, I know many managers and we see it obviously in our reference data that actually have very poor NPS and founders don't like working with them. They actually continuously pick diamonds in their office. They don't actually even see that much. But they are great pickers. How do you think about really what's primary? 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?
12:23Although, of course, there are people who win, and you know, you hear crazy stories about, but I would say we tend to spend the most time thinking about the winning and servicing angle, which kind of feed on each other. Because I think, 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 focus our evaluation on those final two pieces, the winning in the picking. Or sorry, the winning in the servicing. In terms of actually, when we think about track record, many LPs kind of place it primary and we have Peter again at SCS on the Chavereers and he said it's like a fourth or fifth for me, like it's backward looking.
13:01How do you think about the primary nature of track record or not? It really depends on how mature the person's track record is, right? I mean, obviously, we're for looking at new fun. There is no track record to evaluate. Although I would say when we back a new fund, we do probably have a bias towards people who at least have some kind of angel track record. And so that can give us some hints to their taste and ability to do things. Of course, it's not everything. And someone may be in a dozen unicorns or something from last 10 years, but if they were only really small checks, that doesn't necessarily tell us about their ability to put a big check into something like that in the future.
13:38So we try to, I'd say the earlier someone is in their career, the more we have to focus on qualitative or subjective things. Like, I don't think it should be underestimated how important just likeability is. When a founder chooses someone to be on their cap table, they know it's going to be a partnership that's going to last for a very long time, right? And if they're choosing between say three GPs who are sort of equally credible and impressive, of, you know, there may be one GP who they just buy better with for whatever reason, right? And they pick that person. So that's actually, even though it sounds so simple, that's not an aspect of this to be underestimated.
14:12And a lot of the time we spend with GPs, I'm often asking myself, you know, what kind of founder would this particular person appeal to and why? And an interesting observation I heard about Sequoia once actually is that one of the things that made them so successful, there was this period where they had Mike Moritz and Jim and Gets and Doug Leone all kind of in their prime, all very impressive VCs in their own right. But interesting, they each have kind of a different flavor of entrepreneur that they would appeal to. So between having those three really impressive people who all kind of had different entrepreneurs, they would appeal to that, allowed Sequoia to cover a really broad swath.
14:49In terms of like, I think we learn a lot from mistakes, actually. When you think about picking mistakes that you've made in the past, what did you see or not see that with the benefit of hindsight you wish you had or you missed. It's funny. I mean, I can't point to that many things that are like the common things that go wrong. One thing is just I think sometimes we underestimate how badly people wanted it, right? Like it takes a long time to be successful at this game and I think it can be probably a slog for the first five to seven years. I think the feedback loop you have to get going is a VC is you need to have some wins that make you super credible to other people, right?
15:25And then that allows you to have better deal flow, have better winning ability, etc. And then you have that positive feedback loop. You know, some people may be very impressive and have an interesting thesis and work really hard and then for whatever reason after five to seven years they just they didn't get a lucky strike and it's harder for them to say well but at that point right because people pointed that person say well they've been doing this a long time and they haven't been successful yet maybe they're not that good right? But there's other people who do get lucky more quickly. They're lucky enough to get that feedback cycle going.
15:55So sometimes I think it's partly luck. But you know, what are other things that go wrong? I think sometimes people... Can I ask you the first three years of a firm post -backed one? What are the signs where you go, yes, I'm glad we're in there? Because the companies, I mean, respectfully, if it's in the first three years, they might have raised up round sure, but up round, you know, funny, common. There's not limited me access. What is it in the first three years of a fund investment way L .I? This one's good. Honestly, I would say in the first three years, you usually can't tell. It would be some time between three and five years where we start to see whether some of their companies really inflected.
16:28We don't necessarily care whether something is head and up around, although obviously that there's signal value there. If we see they've backed some companies that are really starting to get fundamental traction and have the potential to be iconic companies, that's the proof. That's what we have to wait and see. That's the only time we know more concretely that something's really working. I spoke to Neil native of 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? I think sometimes firms grow too big too quickly and that forces them out of whatever their sweet spot was.
17:03I think another issue is frankly if people have a spell of success, sometimes they become American 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, etc. That can happen sometimes in cars, someone who was otherwise on a good trajectory to go sour. Honestly, sometimes people just lose their motivation, once they've been successful enough. And that's a key thing we try to suss out 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?
17:36Yeah, no, I totally get you on the starting of the motivation side. in terms of following your managers, I obviously speak to a lot of LPs and they say, the hardest thing is, I'll rock star manager, I'm not going to name names, but name your great rock star managers, it's an incredible firm now, needs the firm, they've just scaled so much and now we don't really want to follow them, not because we don't like them, but because it's a $3 billion raise. Yeah, $2 billion raise. How do you think about that balance of supporting the manager who's done very well? Yeah. But also the opportunity course of that cash could be put to use much earlier and a higher multiple uninvested opportunities.
18:12Yeah, it's tough. I mean, our default is always to be loyal to the people who were already invested in, right? But I think it is a reality that in the LP business, we're always on this treadmill of every firm, no matter how great has a half life, right? No firm is going to be great forever. They'll eventually buy to generate generational transition or something if they even try. So, how do we evaluate when people are getting too big? We think about things like, okay, how many great GPs do they really have on the team? How much can each of those people put to work? How much historically have they put to work per year?
18:43Things like that, which try to give us some idea of what's reasonable. And of course, sometimes people, they just go a little bit too far and that's when we have to start scaling down. How do you tell a manager that you're not going to reinvest? That's a hard conversation to have. Yeah, I mean usually we try to know it well ahead of time and tell them relatively early and whatever their fundraising processes But there's no there's no way to sugar cut it right that's definitely you know one of the least fun aspects of this job I always ask like firing. It's like if that's surprise It's probably on the person firing so I probably yeah, I totally agree So he was a firm said kill it and scale green oaks I chatted to Neil before, as I mentioned, he said that you, in particular, an MIT put a flag in the ground for him and for Greenoes.
19:29First, which really made Greenoes in some ways achieve what they'd have done. Can you take me to that decision? Why are you back, Neil? Yeah, what you saw that others didn't. It's funny, that decision almost didn't happen, and I told, I didn't tell Neil this story until somewhat recently. But actually, when we first invested in Greenoes, 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 Greenhouse at that time was raising its first institutional fund and you know was not well known at that time.
20:01So definitely didn't fulfill that criterion. And I remember actually you know my boss Seth and I decided let's leave this and look at fun to or something. And the next but I slept on it and then the next day I decided to call my boss Seth back and say you know what I think we should at least make a small bet on this to start and we did, which is lucky we did because that's been one of our most successful 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 raises his fund, he'd done a bunch of individual deals, not with the fund, but sort of on a deal -by -deal basis, raising money for each thing.
20:37And we talked to a number of the founders that he worked with, like Bob from Kupong, for instance. We do thousands of reference calls, right? and so we're pretty attuned and calibrated to when something stands out. And the way founders talked about Neil was, it was really exceptional, relative to most calls we do. So that's to doubt, you know, he had an interesting thesis at that time too on e -commerce, which was part of why we backed him, although he evolved over time and is much broader now. But, you know, at the end of the day, it was a bet on him and Benny and a gut feeling, really. So many things to unpack there.
21:09First, to what extent do you understand strategy shift? When a manager says, We're doing e -commerce, we're doing SaaS, and then, see, a lot of it was not that. Yeah. To what extent is that? Okay, moving with the times versus now, that's not what we underwrite. Yeah. Ah, there's definitely a tension there, right? I mean, we want people to do what they say, but if they discover the original strategy is not likely to work, then obviously we want them to evolve, right? So I think it's about communicating that early if you are going to shift your strategy and doing it very purposely and being clear about why.
21:42You said they're about, you know, sleep on it and actually I wanted to put a small check in for us. How do you think about position sizing and building a portfolio book of funds that how many is enough, how many do you want to have? What is that all it like? So today at least in the US venture portfolio we probably have maybe six to eight core relationships we would refer to them as where we're writing checks of like 50 to 150 million per fund. So some of those big names you would think about right? And then after that we have another bucket where the check sizes are typically 10 to 20 million per fund.
22:16And those are things where they may be less mature managers. And so that's why we're not writing as big a check. Or it could be that, you know, it's just a fun with a very small size. And so we just can't scale it to 50 to 150 million. Because maybe it's only $100 million fun or something, right? And of course, there's often many other LPs around the table. And then the third bucket we have now is things where basically we'll write a million dollar check. because maybe it's extremely early and the person had no track record, not even an angel track record, record let's say, or we're doing it to work with them to source COVID -19.
22:49So in terms of the number of things, so as I said, there's maybe six to eight really big core things. In the middle bucket, there's probably about 20 managers today. And then in the third bucket, it's something we only started in the last couple of years. There's I think maybe three things in that so far. And we hope to put a lot more on that bucket in the future. Okay, how much do you put out a year in terms of venture funds? In terms of dollars, it varies a lot depending on where we're in this. Anything I can't ask you to. How does it vary? 21 versus 23? It peak, we probably put somewhere between one and one and a half billion out per year.
23:27But to give you an illustration of how much it can change, it peak, we probably were putting three billion out the door in one year, and now we're probably down to about a third of that, to maybe a billion dollars. One thing that changes the deployment pace for you is the deployment pace of managers. We saw temporal diversification become a myth in 2021 or supposedly so. To what extent is it okay for managers to compress deployment timelines as they did? I mean, we saw many do 12 month deployments. Yeah, I mean, I would say that's probably one of the things where we most wish people had been more disciplined, right?
24:01And when people... I think we got too much of a break if I'm honest, Ryan. Yeah. like LPs do not chastise venture investors more as they should for 12 months' appointments. Yeah, well it's the tension there right is the the top DCs have scarce capacity relative to you know their fun size relative to the universe of LPs who might like to invest there's a big mismatch that right and so I think LPs often feel reticent to criticize people too harshly right but I mean look we all know that that we were all disciplined for some period of time right it's not a secret and virtually everyone did it. I mean, if we were gonna say we're not gonna invest in people who were undisciplined in 21, we would have a very, very sinusoidal.
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24:43We could only invest in new people basically, right? So I think we have to try and make sure that at least people are being intellectually honest about making mistakes and being undisciplined and forthright about what they learned and we have to move on. Yeah, I mean, I did the analysis here that when we compare our entry price now of us is 18 months ago is 43 % lower. And the last nine companies we've done, that is held true. I'm glad that Temple Diversification does still exist. Yeah. Well, look, another thing I'd say is as someone who works on both public markets and private markets, in the public market, if a manager went all to cash in their portfolio, we wouldn't like that either.
25:20We would say they're trying to time the market, right? So similarly, I don't think you can criticize VCs for deploying money during a bubble period, right? Now, do I wish they deployed less? Sure. Oh, 100%. I don't know. You can ever sit out. 100%. You mentioned that kind of the public exposure and role you have. A lot of people always said about the denomination effect when publics were not performing. And it was leading obviously to a pullback on the private deployment side. How's that changed now with now's that actually doing well on public looking good? Yeah. Has it made less pressure on private deployment?
25:53It's certainly improved things for us. We're less liquidity constrained now than we were say, the bidding of last year. But the major issue still continues to be that there's all these big companies like Stripe, for instance, from the last cycle that have not had liquidity events yet. And so until some of those things get liquidity, we'll probably still be more constrained than we otherwise would be. Yeah. Is it challenging, also, given your role with MIT and actually having outflows to the, I presume, required in terms of scholarships and maintenance and everything involved, which is incredibly important, obviously.
26:26But a lot of LPs don't have mandated outflows that it 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? It certainly makes it a more tricky situation, but 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 put out. I would say the last two years are unusual because of this dual problem of one, we normally we assume all our managers are going to 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.
27:02So that was one thing. And then secondly, doubled in size. And doubled in size. And this crop of big companies has taken much longer to achieve liquidity than we expected. So I'd say there was sort of an unusual effect there in this cycle. But normally we know we have to pay out about 5 % of our assets per year to support our institution. That never really changes. We have a smoothing formula for that, but that's pretty consistent. So we generally know what we need to do. I think this is a very unusual period. How do you think about the liquidity challenge? We mentioned Stripe, so even there's many others that your data breaks as well.
27:37We have this whole generation of companies that's almost formed in your economy of like pre -IPO but should be IPO companies in many respects. How are we not sort of liquidity question? There's a lot of companies waiting. I mean, there's so much we can do strictly speaking, right? I mean, there are some cases where maybe, particularly if there was a co -investment, we could encourage a manager to sell some secondary or something. But there's not much we can do, right? We're waiting like everyone else for these things to IPO. 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 investors who have been there a long time and maybe obligated by their fund lives to get out.
28:15It's anyone's guess what's going to happen to the prices of these things when the lockup windows expire, right? Do you ever think about selling positions and managers? We often hear about managers getting out and getting liquidity. Do you ever think about actually selling positions and funds? Well, certainly think about it. We almost never do it because we're not willing to do it at a low price. The reason these secondary funds exist is obviously to get high IRRs themselves. Generally speaking, if we're selling a package of something to someone smart and they think they're going to make a 20 % plus IRR, that means that's what we should probably just hold these things.
28:49So luckily we've never been in a dire enough liquidity situation where we had to do that. I think we would only do that if we were really forced to. No, I totally agree. I mean we've seen 80 % discount on some. But look, if we can get a good price, certainly we'll think about. But that's virtually never the case. You said about the third bucket being sometimes people who can provide good directs, you mentioned coupang earlier. I know that you're very active in terms of direct investing. Why is that such an important part of strategy do you think? Well, I think there's a number of things we like about it.
29:20One is just, you know, if you could have another tool in your toolbox for making good investments, why not build that up, right? Secondly, I mean, I personally find it easier in a lot of cases to write a big check to a common best 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 know what's going to happen, right? And as we've, you know, talked about a little bit, even with people who have a really good track record, you can't fully predict how they're going to do with that next check, right? But if we have an opportunity to invest in something with that, we know is a great company today at a reasonable valuation and sometimes with a really great structure around it as well.
29:56I find it much easier to have that conviction that what do you mean by a great structure around it? Well, so for example, Neil might have mentioned the coupon case. The most of the money we invested in that was in this special structured note where we felt it had very protected downside, but managed to keep a lot of the upside as well. So it was very easy to have high -comic that situation for us at least. How do you protect the downside in that way? Well, basically, it was a note where it was the most senior thing in the capital structure. And of course, we had a view about the minimum future EV of that enterprise, right?
30:31And relative to that, it was very small. So it was just, it was very tough for us to envision a scenario where this thing got primed and we didn't at least get our money back. How do you think about the decision -making process in the underwriting process on the direct site, because I see a lot of actual kind of LPs make the mistake of not doing the work and not trusting the manager and just falling in the middle, where they kind of have someone half the time, kind of check out the company and it's just done poorly. They meet in the messy middle. How do you think about the underwriting process?
31:01We 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 interested in it, it was when we did a reference call on Neil with the company, and we're very impressed with bomb. And that was something Neil actually invested in before Greenox 1. And so we were kind of disappointed actually that we were investing in this new fund where it was not gonna 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.
31:29And sure enough, within a few years after that, Neil did see there being a potential opportunity to put the structure ground together and let us know. And we had enough time to go visit the company in South Korea and tore some of the warehouses and things like that get to know bomb 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 and China or Flipkarten India turn out to be interesting as well. So that was some of what turned us on to the opportunity and in that case we were able to spend quite a lot of time getting to know the company, getting to know the financials, getting to know the structure and really being thoughtful about it.
32:09Okay, so we know that we want to invest. How do we think again about portfolio allocations and sizing on a per position basis? It depends on our liquidity at any given time, but there's a huge range, honestly. So in the case of Coupon, that was 120 million coin investment for us. And we made, I think, a distribution price is 7 .8x or something like that. It's probably a little lower now that the stocks come down a bit, but that was a large outcome for us, obviously. Sometimes it's constrained by what we can get. There's another opportunity where we co -invested in snowflake before an IPO, 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 if we had the opportunity.
32:50But I'd say it's a wide range. Just something's earlier stage and less certain doesn't have as much structure. It may only be a 5 million dollar. I may be varying into completely dangerous territories here, but why not? At the incentive structure is financially right in endowments. What I mean by that is 120 million, 7, 8, that is a huge amount of carry if you're in a traditional fun structure. Do endowment funds have the financial incentive structure? Right. I mean honestly, I think the answer is no. 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.
33:25And I think also it helps that 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. What was the right way to do it? If you were to construct a family office, I give you blank canvas. How do I create an incentive structure that allows for people to be really motivated to take risk on manager evaluation?
34:02You know, we see this commonly between us, but a lot of the firms that exist today, we're not excited and I started about moving forward, but you definitely won't get far if I put a money in X -Felton. Bro, how do we move away from that and what's the right incentive structure? Well, it's tough. I'm with two minds on this, right? There are good reasons for endowments and foundations to have the incentive structure set 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 a free option on an institution's capital by giving them carry necessarily.
34:33So there's good reasons to do it the way it is done. But if I had to 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 and the investments the firm was making, either money they already had or a large portion of whatever their bonus might be. And I would probably We say yes, there has to be some kind of incentive structure, maybe over a suitable hurdle. Yeah. It can ask, on the direct investing again, in terms of pricing, matters a lot, the lost price sensitivity for a lot of managers.
35:07When you think about your lessons over 15 years, how do you reflect on your relationship to price when doing directs? And what are you looking for? Is it a three -axe? Is it a ten -axe? Is it a tough question, right? I mean, obviously we're all weighted a little bit to what we see happening in the public markets at any given time, right? And I think at one point during the peak of the bubble, we were weighted to much higher exit valuations than we should have been. We made mistakes like everyone else. I would give ourselves some credit for at the peak of the bubble. We said no to several co -investments where, you know, people with that we really respect and still respect.
35:40We're pounding the table to do these things and we said no. Do you worry that they won't come back to you if you don't do them? I've had this with quite a few RPPs when they say, we'll do it if you won't bring us the next one, Mike. If you need us to. And I'm always like, you don't have to do something you don't want to. Yeah, and that's fine, but you worry that if you don't, they won't come again. You know, it's always a concern, but look, I think you have to be, you have to be just spent at the end of the day and say no to things that are marginal uses of your capital. And could there be a few cases where we can be helpful with a smaller check for something that's right on the margin for us, but a big deal to that manager, sure.
36:14Occasionally, we might do that because we think overall it's NPV positive, right? But you know, I think another thing that keeps people coming back to us is we're probably one of the few LP certainly one of the few university endowments who can react to one of these things very quickly in big size. I mean, I talked about how in the case of coupon we had quite a bit of time to look at it, but there are other cases where, you know, with Neil for instance, there was a big article maybe last year about the deal he didn't replaying, right? And that came together over a weekend, right, during this bank collapse.
36:44Are you able to take me to that? I probably can't talk about in detail, but the point I'm making is that within a few hours on a Friday night, we made the decision to back that deal. I don't think there's many LPs who can do that. How do you decide it that way? I don't know if you can go into the decision that you can process, but that is an incredibly compressed timeline. I don't know any of the commercialized check in that timeframe. Well we didn't write the whole thing. I mean, honestly Neil probably had several other, you know, several of Neil's LPs are very good. I'm sure there were others that participate as well.
37:16In a situation like that, a lot of it is trust, right? I mean, we trust Niels' judgment, but also that was in another case where the structure was fantastic. We knew a lot about the company already. We had several other people. We know who had a really high opinion 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 because we knew about the company in the founder already. we had a lot of trusts already in Neil and his team. And thirdly, the structure was really fantastic. Can I ask, when do you think about the direct investing mistakes?
37:51You've had 15 years, I'm sure there's some. What have you learned from the ones that I haven't worked out? Yeah, the worst of that I've been involved in at least was an oil and gas investment. Can I ask what happened? Well, basically what happened was, so there was an oil cycle, right? And there was a manager we were invested in who was very good at doing this play basically where there was this thing they could do for a number of years where, as you know, right, shell technology has really improved and innovated a lot in the last 15 years. And there was a period where it was a relatively new thing to be doing horizontal exploration of certain oil plays.
38:25And so they found this interesting area where it had been vertically explored with vertical wells, but not horizontally explored, which could really increase the yield of oil you could get from the acreage, right? because it was vertically explored, they had a pretty good idea from looking at those wells where things would probably work and where they wouldn't. But, you know, the bigger buyers of these parcels of acreage typically wouldn't give you full credit. So what these guys would do is they would buy the stuff that hadn't been horizontally explored, like a large parcel. And then they'd do a few wells here in their horizontal wells to prove it out, and then they would flip it for a big MOI, right?
39:01Anyway, there was a period where there was a big oil decline, and they found it a new place basically thought would be good to do that. And it did work out initially, but then the problem was actually, it was so successful that it was very hard to flip this package because it got so big. Right, I mean, this thing was worth, I think, well over a billion dollars at peak. And at peak, it was probably like a five to seven X for us. And anyway, so the way they wanted to exit it was, they ultimately merged it with another small public company that had complimentary acreage. And then we just had this perfect storm of, you know, new CEO, we had an oil price decline after that.
39:37They drilled a few bad wells as well. The company they merged with had a fair amount of debt already. And so things just spiraled down, right? And so I don't, you could say look, what did you learn from that? You just, you know, everyone knows not to do commodity oriented things with high leverage and all these other potential problems. I, at least as it relates to venture capital, I think one of the things I learned from that is, I think we didn't appreciate how brittle these small -shale businesses can be, particularly if you're going to not just flip acreage, but actually try to fully produce it, because the decline rates on these walls are so high, even though on a well -basis they can have high IRRs, the decline rates are so high, if you're trying to really maximize production, you have to basically reinvest your whole balance sheet every year.
40:19And even if someone is really good at that, let's say they get it right 80 % of the time. Well, 0 .8 times 0 .8 times 0 .8 times 0 .8 times 0 .8, after five years you're starting this face pretty significant probabilities of the big loss. In some ways, I think that's what happened there. What does my takeaway? You have to be very careful with businesses where you have to reinvest the balance sheet every year. You have to continuously reinvest the customers. Other parallels, I sometimes notice, things like gaming or maybe you have a very high trend rate in the customers. My friend just bought a sports team with his private equity fund for several billion dollars.
40:53He said, the thing I didn't expect, it cost 500 million to keep this fucker running every year. Yeah. And you're like, that's, that's different. Yeah. So, you know, that's an example. That's not your confidence. Because I think that, you know, I suppose Doug will be only actually in the show about this. Like when you have a loss or none of us, but something that does not perform was expected, it can hit your confidence. And the winners of those that as he did is like, pick yourself up on me, go. It, of course, it hurt me a little. I mean, I think I was lucky that I had had some other successes I was involved in by then.
41:22And so it's not like, you know, that was the only thing I'd done and then it was a failure. And I mean, I'm amazing, actually, I think on that particular deal, we still recovered about a third of our capital or something like that. So it wasn't a zero, but, you know, you always, yeah, I mean, it has to, it impacts you a little bit, of course, but luckily things have been fine since then. Has your investing style changed over the years? Fifteen years of the long time has how you think, how you prioritize, what you prioritize changed. Well, for one thing, I personally spend a lot less time on the public markets than I I used to.
41:53I mean, actually, when I started at MIT, I was mostly doing public markets stuff, but I'd say in the last seven to 10 years, I've sort of switched to doing mostly private stuff. I just find it much easier for me and my personality to, 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, you know, the NASDAQ, right, as a public manager. That's incredibly difficult to do on a consistent basis. That's That's one thing that's changed for me. I think another thing is I think after seeing things play out over a couple cycles, I trust my judgment a little more.
42:27Right, I mean, there are things that happen during the peak of bubbles where you didn't think something would do nearly is, wow, maybe there's something you passed on, right, for good reasons, and then it doesn't credibly well, and you know, it's a rather confusing. But sure enough, these things eventually come down to earth. It's funny you ask that about to my mistakes, right? Because actually the biggest mistakes I think about are actually errors of a mission, of things that did really well. And probably the number one thing I think about right now is, you know, I mentioned we're investors in YC and when Sam left YC around then we also had an opportunity to invest in OpenAI and we didn't do it.
43:01So that's definitely an era of a mission that why I think about a lot. A couple things. I mean, one, it was a very unusual structure as people now know to, you know, it was unclear how they were going to achieve success technically at the time. So it was just, you know, we felt it was a very speculative bet at the time and, you know, I think that's the case where we probably said we should have said look we know Sam we know he's a special person this is a huge idea make a small bit. Can I ask you that they're about kind of speculative nature of that. How do you actually think from a portfolio and sorry for being broad but it's really that from a portfolio level like how much being public how much being private what cash looks like and the right level of risk profile to have across the actual whole portfolio.
43:40Yeah so ideally we want to be probably about half half public's private we typically carry anywhere from 5 % to 10 % in cash and short duration government securities. In terms of total risk, probably one of the main ways we think about it is we have a concept called drydown beta where essentially if the market is down 10%, we only want to be down and say not more than 7 .5%. So we try to keep it 0 .75 beta or less. Easing less manages coming back to market now. Absolutely. Are there fun slides to the expectations changing? Yeah, yeah, happily they are smaller. How do you think about deployment now?
44:19I think the medium take your life to present a very gloomy environment. I don't always agree with it. It's not actually what I'm saying necessarily. How do you think about deployment stands? Do you think LPs are close for business? People who are not closer business, I think people have to do things in smaller size or might not be able to do as many new things as they would otherwise like. But I think especially for the firms that have top reputations, I don't think they're having that much trouble raising money, right? I think they always have more LPs who want to invest than they have capacity.
44:49So I don't think the top firms are hurting in that regard. I mean, maybe if they try to raise too much, they'll get more pushback, the normal, more critique, which maybe is a good thing. I think it's a smaller managers or the emerging managers that are going to have a lot more trouble raising capital in this environment. What would you say is change about venture to say? Well, I would like it to be less competitive. I don't think that's going to happen. For managers who are contemplating raising today, what would be your biggest piece of advice? I think you have to treat the process like an enterprise sales cycle, right?
45:19Which means you think it is a numbers game. I always say line funnel. I actually say lines not dots, which is Marxist is the command which is interesting. You have to build relationships over time. If you think you're going to meet someone in a fundraiser and raise, you can do. Yeah. It's rare. Yeah, you know, another piece of advice I'd have on that is that it's good to build relationships where you don't necessarily want to force people to evaluate you too early. Particularly with large institutions, it can be the case that, you know, once they evaluate you once, they may not be willing to look at you again.
45:48If an LP is very picky and usually does very mature things, you know, you don't want a situation where you get them to evaluate you prematurely and then you're permanently ridden off. I mean, no one's ever permanently ridden off. That's a bit dramatic, but, you know, if you can, I think it's good to know who you're trying to raise from, what sort of their sweet spot, and try to keep them from doing that full evaluation until you're really at the right point to be evaluated by that person. I think a lot of managers also struggle when it comes to the account table construction of their funds and there's a lot of advice to run around about LP concentration.
46:20Don't let anyone have over 20%. There's a lot of different aspects. When you think about advising managers on how to construct the ideal LP base, what would you say? You probably don't want to exceed 10 to 20 % except in very unusual circumstances. Part of it is just what kind of business do you want to run, right? Obviously, if you have a large number of LPs, you shouldn't underestimate the time that it takes to manage those relationships, right? And if you're going to have, say, hundreds of LPs, you may need, you know, some people in your business who are dedicated to managing those relationships, right?
46:52Do 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. Yeah. 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 aisle? 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, managed to keep you updated and like, you know, what's going on and can get you access to that person when you occasionally need it.
47:29And of course, something we try to do as LPs is not be overly demanding in the time we take from people, right? 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. I was spoken obviously 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 last -hands? Well, it's, I mean, it's something we're wondering about as well. I mean, there was an area of great success for us for some period of time.
48:02We're doing a lot less there now. I mean, we're not going to categorically not do it at all yet, but we are reducing it and to the things that we keep doing, we're very careful about whether there are people that we think are going to keep from sensitive areas of investment, right? And obviously, also, we don't know how these regulations might change in the future. So that's another reason to keep it small. Final one before we do a quick five. When we think about firm building, generational transition is often the place where many people and many Alps are seeking to say that's where firms fall down.
48:35You said most people bought at least one generation. What do the best to ensure generational transition is done while in your purview and experience? Yeah, it's very hard. I think the reason it's hard is because it's unusual to have exceptional people and then it's very hard to find the next generation of exceptional people. right? It's hard to make lightning strike twice. And then of course the bigger your firm is in the more GPs you have in some ways it gets exponentially harder right? If I was lucky to have three really good people it's extremely difficult for me to have another cohort of three really good people come up next but you know the people that do it well you know I think one they're very thoughtful about it they're very thoughtful about mentorship and and making sure that the next generation of people has the right skills to be successful and I think also So they're thoughtful about how they share economics and they don't wait too long to do that.
49:26And I think one of the reasons a lot of firms sometimes lose some of their best people is because they know how to do that quick enough. One thing I do have to ask, and I promise them to be a quick firm, is you know, we've seen this generation of firms really scale up and really become capital accumulators, asset gatherers, some people say, do you want to be in those firms? And I think I want to speak to many companies that are like, I'll still get a three X. And I'm like, if you think you're gonna get a three X on a three or four billion dollar fund, either on being too negative, how do you feel about this?
49:56I mean, certainly the probability of hitting a three X is much less. So I think in some cases we can still justify it, but yeah, I mean if a firm gets too big and we're no longer confident that we can make exceptional returns, over time we're gonna have to scale out. Listen, are you ready for a quick far? Sure. So what few changes your mind on in the last 12 months? Probably hard tech. I wouldn't say I've completely changed my mind on it. Not to say I have a really hard set of you either way, but I think I used to be much more skeptical of them and I think the existence of things like Tesla and SpaceX and Enduro have forced me to reconsider some of my biases.
50:30So you are inherently more positive in hard -tech investing? I'm more positive now than I was in the past. Do you need to be a specialized firm to win? I don't think so. What do LPs do today that will look at in 10 years' time and think, wow, for the every different time. I mean, something I chuckle about a little is just how prosyclicable people are and, you know, two years ago, everyone wanted to do lots of late stage and solo capitalist and crypto. And then a year later, they all think it's dead and don't want to do that ever again. I think most of those things will come back. What won't come back?
51:03Hmm. That's a good question. Like, I don't think... I believe in crypto, but I don't think my NFTs will come. I mean, even there, I'm not... I don't want to be totally close minded, right? I mean, a lot of the thing, something I think I'm always humble about is a lot of the things that have turned out to be the best businesses or things that many people would have thought were totally crazy. So, you know, look, I don't use NFTs myself, but I don't want to completely close myself to the notion that something there could be successful. So what won't come back? You know, this reminds me of, I think it's a quote from the Ind recent folks.
51:37I think they say something like nowadays when an entrepreneur comes in and tells us a crazy idea We assume they're right. It's just that their timing might be off and I tend to follow that as well Yeah, they also say the sensual thing is a bad idea just a bad time. Yeah. What would you most like to change about the world of L Pete's hmm tough question. Yeah, I don't think I have a good take there. I'd have to think about it I would change box -ticking nature. Well, that's not gonna change At least not for the majority. But actually the best would definitely don't show it. Well, yeah, I think that you, I don't know about heritage and about Harvard, like, doesn't feel like a boss take.
52:12Well, look, I mean, that's what makes some of these groups special, right? They're able to get beyond that. What was the best age you had me ever been to? Tough questions, Harry. Honestly, most age gyms are kind of the same. Are they pretty born? I mean, they, you know, they're often, depending on the firm, they're often highly produced. I mean, it's always useful to get some time talking to people, right? But look, I think a lot of them are probably longer than they need to be. What's the best investment advice you've received? When things are going well, you're never as smart as you think you are, and when things are going poorly, you're never as dumb as you think you are, either.
52:45What advice do you give most often to other LPs? Well, I mean, honestly, we don't talk to other LPs that much. Now, I mean, we try... there are some, of course, right? But we try to say independently minded, right? and I think the more you talk to other LPs, the harder that it's to do. Which reminds you of a new knoughton that you would really like to be in? Probably Founders' fun. Why are you not in that? I mean, that's a case where when they got started, just, you know, no one from MIT spent much time with them, and I think now it's, you know, it's a point I just saw, like, it was too late. What makes Neil Mata so good?
53:15I think it's a combination of his ambition, his great judgment, and I think he's made it should be very likeable and useful to Founders. What's the hardest element of your job? other than time, everyone's the time. Well, I mean, the thing I dislike most, of course, is having to disappoint people, right? Because for every hundred meetings we take, right? I mean, we might only invest in one thing, basically. So that means disappointing a lot of people. And of course, it's even harder when it's someone that you work with potentially for many funds. Yeah. Why would you personally like to be in 10 years, Ron?
53:46When we have this in 2034, Christ. Uh, what was Ron then? You know, I'll probably be doing something similar at MIT or a family officer or something similar. Listen, Ron, I've loved this. I really appreciate it. I think not enough license is shown on this area of the industry. I so appreciate the transparency and thank you for being so good. My pleasure, guys. Thank you. I do just want to say a personal thank you to Ryan again. He's been an incredible partner to me with 20VC. He was fantastic on that episode. If you want to see the full video, you can check it out on YouTube by searching for 20VC, that's 2 -0 VC.
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From the publisher
Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company.
In Today's Episode with Ryan Akkina We Discuss:
1. From Engineer to LP with MIT:
- How did Ryan make his way into the world of fund investing as an LP with MIT?
- Why did he turn down the chance to be a VC early in his career?
- What does Ryan know now that he wishes he had known when he started at MIT?
2. The Manager Evaluation Process for MIT:
- What does Ryan look for most when investing in new managers?
- How important is track record when evaluating a new manager?
- What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process?
3. How MIT Builds Their Portfolio:
- How does MIT construct their portfolio from private to public to everything in between?
- What are the three different types of check sizes that MIT writes when investing in new managers?
- What are the most common reasons why MIT will not re-up with a manager?
- What are the single biggest reasons why great managers turn bad?
4. MIT: The Direct Investor:
- Why does MIT see so much opportunity in direct investing?
- How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process?
- How do MIT think about the right number of direct deals to make up their portfolio?
- How do they approach check sizing on a per-company direct investment?
- What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset?
5. LP Markets Today and Where We Go From Here:
- Are LPs open for business today? What type of firms will not struggle? Which will?
- How does Ryan view liquidity windows today? When will M&A and IPO markets open?
- What would Ryan most like to change about the world of LPs?
- Why does Ryan believe the LP incentive structure in terms of compensation is broken?




