The Exchanges

Q Very tough to do. I totally agree. That's a challenge, because you're right, it does set a precedent. Can I ask, what do you advise managers who say, I've got a big check, but they do also want to buy part of the GP. How do you advise those managers where it's also a bit of a sale of the GP as part of it?

A Yeah. Um, it really depends on who that person is and what the timeline is. So like, let's say, um, you know, really well-respected and dominant foundation came to you, Harry in 2018 and said, we want to put you in business with a two hundred million dollar fund and we'll do 75 of it and we'll introduce it to everyone we know. If they take part of your carry as a GP, um, Right. Not the management company where, where the, the fee income goes through. Right. Um, and you could say, well, normally I was going to have, um, 20 points to carry, but now maybe I'll have 16, but to get the two hundred million dollar fund, that name and all the network, you could say, yeah, for one fund. Okay. Right. Now the problems could be the other hundred and twenty five million that come with the 75 may also want That same thing. And so you'd have to operationally tell them, Hey, we're just doing this for the, for our anchor. Right. And some other people may say, well, I don't like that or, or whatever. Um, I think the problem comes in is when that's in perpetuity. Right. Um, so, so again, I go back to my airplane analogy, which is to get off the ground, you may have to spend some, some, you know, the jet fuel is more expensive.

AI assessment note: “you could say, yeah, for one fund”

Q One of the best, one of the best by far. Um, I want to dive straight in today. I spoke to some, some, many mutual friends, um, which was great fun, and I want to start with the firm itself being Haystack, and Hunter Walk, obviously from Homebrew, he asked, how do you decide what each thumb size for Haystack will be? Let's start there.

A Well, remember, um, the, the first four, I was never able to reach the target of what We wanted to raise. So there were always underwhelming in that sense, or, or what's the opposite of not oversubscribed? Uh, you know, what's the opposite of oversubscribed? And so for the last two, they were, they were just marked at 50. And so to answer Hunter's question, I thought of 50 in the first, the first fifty million dollar fund is like enabling us to get to a 10% position and precede seed rounds. And then in COVID, I felt like a lot of LPs were going to support us regardless of what we were doing and fund five at that fifty million stake was working. So I just thought, let's not complicate things. Let's literally use the same documents, the same size. It's a rinse and repeat strategy. Um, and, and, you know, I clearly communicated that to everyone because the model was working. Um, and so I just took the path of least resistance there rather than introducing, um, More variability. We probably could have raised a lot more, but I just felt like, hey, it's an easier pitch to go back to people when they can't meet you and can't meet the portfolio. Um, our next funds, by the way, will, will modestly grow, but I still think, you know, for what we do, it's gotta be under a hundred million dollars.

AI assessment note: “I thought of 50 in the first, the first fifty million dollar fund is like enabling us to get to a 10%”

Q Very tough to do. I totally agree. That's a challenge, because you're right, it does set a precedent. Can I ask, what do you advise managers who say, I've got a big check, but they do also want to buy part of the GP. How do you advise those managers where it's also a bit of a sale of the GP as part of it?

A Yeah. Um, it really depends on who that person is and what the timeline is. So like, let's say, um, you know, really well-respected and dominant foundation came to you, Harry in 2018 and said, we want to put you in business with a two hundred million dollar fund and we'll do 75 of it and we'll introduce it to everyone we know. If they take part of your carry as a GP, um, Right. Not the management company where, where the, the fee income goes through. Right. Um, and you could say, well, normally I was going to have, um, 20 points to carry, but now maybe I'll have 16, but to get the two hundred million dollar fund, that name and all the network, you could say, yeah, for one fund. Okay. Right. Now the problems could be the other hundred and twenty five million that come with the 75 may also want That same thing. And so you'd have to operationally tell them, Hey, we're just doing this for the, for our anchor. Right. And some other people may say, well, I don't like that or, or whatever. Um, I think the problem comes in is when that's in perpetuity. Right. Um, so, so again, I go back to my airplane analogy, which is to get off the ground, you may have to spend some, some, you know, the jet fuel is more expensive.

AI assessment note: “it really depends on who that person is and what the timeline is.”

Q Tell me my friend, final one, what was the most recent publicly announced investment and why did you get so excited?

A I think, oh, in part security, which is a, a team that left signal sciences that was, you know, doing a new way of like, uh, collaboration across like security teams. And we like this idea of like collaboration. Um, but again, it was a bet on the people, right? And so they may take it in a different direction, but, um, we just thought the, they had a mastery of product. They weren't trying to raise too much money. Um, they were the entrepreneurs we'd like to work with, which is they use us for very specific advice and then they sort of move accordingly and they reference really well. So we're really excited about that category overall and just working with the impart team.

AI assessment note: “in part security, which is a, a team that left signal sciences”

Q One of the best, one of the best by far. Um, I want to dive straight in today. I spoke to some, some, many mutual friends, um, which was great fun, and I want to start with the firm itself being Haystack, and Hunter Walk, obviously from Homebrew, he asked, how do you decide what each thumb size for Haystack will be? Let's start there.

A Well, remember, um, the, the first four, I was never able to reach the target of what We wanted to raise. So there were always underwhelming in that sense, or, or what's the opposite of not oversubscribed? Uh, you know, what's the opposite of oversubscribed? And so for the last two, they were, they were just marked at 50. And so to answer Hunter's question, I thought of 50 in the first, the first fifty million dollar fund is like enabling us to get to a 10% position and precede seed rounds. And then in COVID, I felt like a lot of LPs were going to support us regardless of what we were doing and fund five at that fifty million stake was working. So I just thought, let's not complicate things. Let's literally use the same documents, the same size. It's a rinse and repeat strategy. Um, and, and, you know, I clearly communicated that to everyone because the model was working. Um, and so I just took the path of least resistance there rather than introducing, um, More variability. We probably could have raised a lot more, but I just felt like, hey, it's an easier pitch to go back to people when they can't meet you and can't meet the portfolio. Um, our next funds, by the way, will, will modestly grow, but I still think, you know, for what we do, it's gotta be under a hundred million dollars.

AI assessment note: “enabling us to get to a 10% position and precede seed rounds”

Q Was it an error of selection being picking or access being adverse selection? You just chose what you could get the ownership in.

A I think it's a mix in that fund, but I would say primarily, uh, I would say 20% adverse and 80% just like, um, poor selection. And, and then, you know, that really changed that really course corrected in the next two funds where I feel like Boom. It just hit, hit, hit, hit, hit again. Um, I remember an LP telling me a long, long time ago, like just when I was starting that typically they'll, they stay with good managers for five funds and they assume that three of them will be so, so maybe two to three X funds. One of them will be a complete turd and one of them will be spectacular. Um, and so I kind of knew going into that one that this was going to be a change in motion. This is 2017 to 2019. Um, And so that's a fund I look back on as like where mistakes were concentrated.

AI assessment note: “I would say 20% adverse and 80% just like, um, poor selection.”

Q Um, and that is why they listened to 20 VC. And that's why I have a job and get paid too much money. Fantastic. Thank you guys. Um, I do want to ask, uh, Samuel, I'm starting, um, Shaw endowment fund now. Um, and you're in charge. Um, how do you run the venture allocations for Shaw endowment?

A I, I'd probably do it the way you alluded to earlier, which is I would, if I were an LP, like not living in the Bay area or New York, I would probably go spend a month in each location, meaning like get an apartment or Airbnb for an entire month, hang out With lots of people after hours, name check lots of people and place money with the people that the network told me were the most interesting. Now that's for early, right? Um, and then I would, I would probably have, I would probably recruit somebody who has VC deal experience to help go do directs on top of it. Um, And to stay close to the winning graduating companies. Um, and then I would, I would probably try to get into using my network, like five to 10 franchises where I feel like, um, you know, you want to be part of their ecosystems.

AI assessment note: “recruit somebody who has VC deal experience to help go do directs”

Q I get it. It's still, it's still fun to hear. Um, tell me my friend, what's the biggest miss and how did it change your mindset?

A The biggest miss was open C where, um, you know, I had helped. I had known Nick tomato for a long time. Like Nicole and Anand, I helped him raise some of his fund and introduce him to tons of LPs because I thought Nick was doing a fabulous job. And, you know, anyone who's met Nick knows he's like, this isn't like a, he's opposite of a tourist in crypto. So he would send, you know, because we were so helpful, he would send all the deals he was doing to us. And he sent us OpenSea three times. Um, now I don't know if OpenSea will end up Who knows what it'll be. Right. But for a period of time, you know, I had spent time with Devin. I had looked at the numbers. I didn't understand. I just thought it was about gaming. We didn't talk about NFTs earlier. And it was just sitting right in front of me. Like, why is this working? I think, I think the last round I looked at was like a 28 post extension. Um, and because I didn't understand it, I just let it go rather than just looking at what was working.

AI assessment note: “The biggest miss was open C where, um, you know, I had helped.”

Q fund was like eight million. It was like your proof of concept fund. So I totally get you. Um, can I ask the big challenge that I hear from a lot of GPs is there's a lot of people around the hoop, but they're not quite getting in the hoop. How do you create urgency with LPs to get them to a conclusion? Do you have any tips on this?

A Um, I wouldn't say I'm, I'm great at this. So grain of salt. Um, I think like at a certain point in your career and as an adult, you have to just be willing to walk away and accept a no in different formats. And so one, one way we do it is we kind of just say, Hey, you know, Julie Smith LP, like we're expecting like, you know, Hey, if we don't hear from you, You know, past this day, we're just going to assume that's, that's not a fit for you. That's okay. You know, um, but it's not like waiting around the phone for someone to call. It's more like we're going to move in this direction. Um, most LPs have plenty of time to decide. And so you, you don't wait for a response. You just sort of move forward on your own timeline.

AI assessment note: “if we don't hear from you, You know, past this day, we're just going to assume”

Q I totally get you. A lot of people, kind of like a sales cycle, I guess, in enterprise sales, think that, you know, it might help to offer, you know, preferential terms in terms of carry or in terms of fees. Have you ever done that, and how do you advise managers on preferential terms for first close, second close?

A Yeah, I think I haven't done that, uh, ever. Um, and, and not a lot of people have suggested that. So, Um, it's not probably something I would advise people to do, um, only because it could set a weird precedent over time. That being said, I think to get off the ground, you know, sometimes people have to make deals. Um, and so what I would just say is like, think, think about it in the sense of like, um, how, how do you survive and thrive? So the first point is like, how do you survive and get off the ground? Is like, you probably need to do what it takes to get the plane off the runway. Um, and so like, I wouldn't sit here and say, do it this way, do it that way. It's just like, okay, if you don't take off and leave the runway, then we're not, we don't have anything to talk about. Once you're in the air and can stabilize, I would move away from preferential terms, you know? And so like, basically if you, if you're, if you're, if you're trying to offer preferential terms to get the jet off the runway and get some thrust, That's fine, but just don't have it be, um, successive in, in future funds. Like, gate it to that one fund.

AI assessment note: “I haven't done that, uh, ever... gated it to that one fund.”

Q Um, and that is why they listened to 20 VC. And that's why I have a job and get paid too much money. Fantastic. Thank you guys. Um, I do want to ask, uh, Samuel, I'm starting, um, Shaw endowment fund now. Um, and you're in charge. Um, how do you run the venture allocations for Shaw endowment?

A I, I'd probably do it the way you alluded to earlier, which is I would, if I were an LP, like not living in the Bay area or New York, I would probably go spend a month in each location, meaning like get an apartment or Airbnb for an entire month, hang out With lots of people after hours, name check lots of people and place money with the people that the network told me were the most interesting. Now that's for early, right? Um, and then I would, I would probably have, I would probably recruit somebody who has VC deal experience to help go do directs on top of it. Um, And to stay close to the winning graduating companies. Um, and then I would, I would probably try to get into using my network, like five to 10 franchises where I feel like, um, you know, you want to be part of their ecosystems.

AI assessment note: “place money with the people that the network told me were the most interesting”

Q Totally with you there, and relationships at the center of it all, I couldn't be more aligned. What advice would you give to a graduate entering the workforce today, Samuel?

A You know, I always give this advice, and it's, it's just what I wish I had done myself, and it's hopefully broad enough that it doesn't apply to tech or VC, but it's, To have a mindset of an investor. And what I don't mean, I don't necessarily mean you buy these stocks or you buy this real estate, but everything you do is an investment. The time that you spend learning Mandarin is an investment. The time you spend taking a cooking class with your friends isn't some kind of investment. And to really think about how you're spending your resources and time to either have fun, get better, learn something, buy a property with your friends, buy a piece of artwork, Just to have that mindset, I wish I could rewind the clock back and have that mindset.

AI assessment note: “To have a mindset of an investor.”

Q raise that you said there are fun three, two specific elements that intrigued me with regards to one of your posts, Was you said about the time in the race, and you said a very specific race date. How do you mentally think about the race date, potentially not getting to it, and your thoughts around why it's important to do that? Mike Maples actually told me the same thing.

A You know, I think only in retrospect, which I mentioned in the post, the three things that I committed to for myself turned out to be helpful, but I was doing that to just control my own brain and my own kind of mental health, if you will. And so I told people I was going to stick within a range. I wouldn't take a dollar more than the top end of that range. I, you know, I told people I was going to budget six months and I told people that like, it's okay to say no, I'm going to still have money to continue investing. And so that kind of gave me peace of like, okay, this is just what I'm going to allot to this and kind of let it go after that. And again, I got very, very lucky at the very tail end of it. So we could, we could really be having a very different conversation right now. But I kind of chose for myself that It was taking so much time and so much of, like, my mental RAM, if you will, that I couldn't afford to do more.

AI assessment note: “doing that to just control my own brain and my own kind of mental health”

Q For sure. Absolutely. I am interested in, in, in another element though, being the second picking decision and how the larger fund size changes that. How did the larger fund size change your approach to reserves?

A Again, we're laying the groundwork for podcast number three, Harry. I don't, I don't know. I think that what I can say as it relates to reserves is people will ask you, what have you reserved in the past? And so I showed them my philosophy around reserving, which I'll go into. In fund one, I didn't know what reserves were at all. So people would ask me as I was finishing the fund, oh, hey, what's your reserve policy? And I literally was like, I don't know what you're talking about. In fund two, What I did was I put a third of the fund across four companies, and I kind of bulked up just to show that I could write a bigger check and follow. And then in fund three, which I just finished, I did quite a bit of one-to-one following, and then I put 12% of the fund into just two companies. So that would be the first point I would make, is you have to show a history of showing the ability to scale check size properly. Now, you don't want to veer off Because people know if you go from two 50 to a million to five million, unless you're an incredible investor, if you veer off that strategy, you're probably going to get into trouble. The second point I will make is now looking forward, the LPs will say, well, what's your reserve policy? And here I have like a slightly controversial view, which is I think the majority of LPs have taken the history of how VCs, institutional VCs, A, B, and C r…

AI assessment note: “In fund two, What I did was I put a third of the fund across four companies”

Q And what were your concerns then? You know, it's a, it's a very, um, big and momentous challenge to start your own fund afresh as a first time fund manager. What were your concerns going into it?

A Well, I'll answer that in two ways. It wasn't a momentous challenge for me because I really had no other option. I just either could do that or do nothing. I think maybe someone starting out to do their own fund and who have an alternative may view it as a difficult thing. I, I really, from that mindset, which is important to understand, I didn't have another option of what to do. I think when you get into it, the concerns that come up are, You have to get some social proof, and then how do you ask people that you know for money, and then if you're raising a smaller fund, it's probably their personal money, which means that, oh, hey, you know, I'm, I might be Facebook friends with this person, or I might know their family, and then this could be part of one of their kids' college funds. I don't know.

AI assessment note: “the concerns that come up are, You have to get some social proof”

Q I totally get you. So if we think about the fifty million dollar funds, what's the average ownership in those funds?

A We've been able to get close to seven percent initial entry ownership in the last two funds. Um, and it's been going up. I would say it's like a slow march What I call it is like, we slowly creep up the cap table. Um, but one of the things I'm, I'm really proud of with Haystack is if you look at, if you look at the activity, um, of all the deals over, over 10 years, I would say there's like a tight clustering between eight and fifteen million dollars as the entry point and the rounds being, you know, three million dollars or less. So to your point, Harry, I think that is kind of like a sweet spot medium deal for like a good founding team. I think the problem comes in as like how much evidence is there on the three and 15. I think we went through this period where, um, a lot of entrepreneurs were getting credit for having done nothing yet and getting three and 15 to start. The problem is now the gap to get the ten million dollar check is so wide. So what's the right entry point at seed? And I would argue that's changing to like teams that already have a product in market where there's some de-risking there where you can bridge gap from the C to A.

AI assessment note: “close to seven percent initial entry ownership in the last two funds”

Q What do you think are the biggest mistakes that GPs make in fundraisers?

A Uh, you alluded to some, right, which is just talking to people when they're raising, um, not, not really like having a richer conversation about what they're trying to do and why, um, Again, like the decks or the presentation just show a lot of pontification or like a lot of things that don't really matter. Um, so I think people, um, most VCs or emerging managers especially are not good fundraisers because they don't, they don't really have a north star to where they're going and why. And it kind of makes sense because it takes a while to develop that. Um, but at the same time, it's not as inspiring for, Someone will let go of their dollars.

AI assessment note: “talking to people when they're raising, um, not, not really like having a richer conversation”

Q I totally get you. And so that's what you're running away from. What are you running towards my friend?

A I think, um, you know, someone that you and I have talked about is like someone, someone like Roger Ehrenberg, where, where you're, you can try to become the investor of record and an important company and an important partner to a founder early. And then you show up on the S one, you know, and people are surprised, I think. That's just a running towards is like a lot of us as investors, for the most part, we can't do what entrepreneurs do. We choose not to do what entrepreneurs do. And so, um, we have the best job in the world. And so to get a chance to be close to one, you know, to sort of steal a line from the Reagan speech and touch a face of God. Is an amazing opportunity, you know.

AI assessment note: “running towards is like a lot of us as investors”

Q those that haven't really worked have often been head of product at Twitter, head of product at Twitch, head of product at amazing company, the hottest of hot seed rounds with Andreessen, Sequoia, you name it. And they all just kind of moved really slowly. They were very competitive, five on 25 rounds, and none of them really went anywhere. Have you found the same with that profile of deal?

A We avoid a lot of those, to be honest, because one is, but by the way, the logic for doing them for these big funds is applicable, like it makes sense to me, but I think for a fund like ours, which is small and constrained We don't get to take those type of shots. Like we maybe say we do three or four of those if we have a relationship per fund, but we were not able to do that as a matter of just normal business. Um, I think what you're saying we can unpack a lot, which is, are those hot seed rounds necessarily indicators of entrepreneurial value creation? Probably not. Um, Are they best suited to like understand what's at the cutting edge of product development or infrastructure? Probably. Um, but I think it goes back to this, like more, more, um, more philosophical question, which is our talented people also entrepreneurial. And I, I don't believe that. I believe there's tons of talented people who are not entrepreneurial and there are a bunch of entrepreneurial people who don't have the requisite talent. And so, Really what we're trying to do in terms of the meaning, not we just all of us should be trying to do is trying to find that overlap of who has. The talent plus the entrepreneurial ability. Um, I'm sure you've seen in some of these rounds, Harry, where, where we've been a part of it too. There isn't because the rounds are so competitive and people are fawning over the…

AI assessment note: “We avoid a lot of those, to be honest”

Q Oh man, I love it. I always love it with you. Um, uh, quick fire on. So, okay, let's start. We've done this many times. What's the new favorite book and why? Any that you've read recently and loved?

A So it's an article, but it's about one of the famous game creators on the New Yorker, um, from Nintendo, and it talks about, um, how he grew up in the woods in Japan and, like, saw all these amazing natural, um, you know, things in the wild, and that ended up becoming, um, The, um, the landscape in which he painted on for his video games. And I thought that was really interesting because so much of like people playing on computers like us, or, you know, working online, we forget about that. And like so many people are gamers and I love gaming as well. Uh, more, more casual gaming, but it's just interesting that this guy's whole inspiration came from being outside.

AI assessment note: “So it's an article, but it's about one of the famous game creators”

Q What do you think are the biggest mistakes that GPs make in fundraisers?

A Uh, you alluded to some, right, which is just talking to people when they're raising, um, not, not really like having a richer conversation about what they're trying to do and why, um, Again, like the decks or the presentation just show a lot of pontification or like a lot of things that don't really matter. Um, so I think people, um, most VCs or emerging managers especially are not good fundraisers because they don't, they don't really have a north star to where they're going and why. And it kind of makes sense because it takes a while to develop that. Um, but at the same time, it's not as inspiring for, Someone will let go of their dollars.

AI assessment note: “just talking to people when they're raising, um, not, not really like having a richer conversation”

Q those that haven't really worked have often been head of product at Twitter, head of product at Twitch, head of product at amazing company, the hottest of hot seed rounds with Andreessen, Sequoia, you name it. And they all just kind of moved really slowly. They were very competitive, five on 25 rounds, and none of them really went anywhere. Have you found the same with that profile of deal?

A We avoid a lot of those, to be honest, because one is, but by the way, the logic for doing them for these big funds is applicable, like it makes sense to me, but I think for a fund like ours, which is small and constrained We don't get to take those type of shots. Like we maybe say we do three or four of those if we have a relationship per fund, but we were not able to do that as a matter of just normal business. Um, I think what you're saying we can unpack a lot, which is, are those hot seed rounds necessarily indicators of entrepreneurial value creation? Probably not. Um, Are they best suited to like understand what's at the cutting edge of product development or infrastructure? Probably. Um, but I think it goes back to this, like more, more, um, more philosophical question, which is our talented people also entrepreneurial. And I, I don't believe that. I believe there's tons of talented people who are not entrepreneurial and there are a bunch of entrepreneurial people who don't have the requisite talent. And so, Really what we're trying to do in terms of the meaning, not we just all of us should be trying to do is trying to find that overlap of who has. The talent plus the entrepreneurial ability. Um, I'm sure you've seen in some of these rounds, Harry, where, where we've been a part of it too. There isn't because the rounds are so competitive and people are fawning over the…

AI assessment note: “We avoid a lot of those, to be honest”

Q Was it an error of selection being picking or access being adverse selection? You just chose what you could get the ownership in.

A I think it's a mix in that fund, but I would say primarily, uh, I would say 20% adverse and 80% just like, um, poor selection. And, and then, you know, that really changed that really course corrected in the next two funds where I feel like Boom. It just hit, hit, hit, hit, hit again. Um, I remember an LP telling me a long, long time ago, like just when I was starting that typically they'll, they stay with good managers for five funds and they assume that three of them will be so, so maybe two to three X funds. One of them will be a complete turd and one of them will be spectacular. Um, and so I kind of knew going into that one that this was going to be a change in motion. This is 2017 to 2019. Um, And so that's a fund I look back on as like where mistakes were concentrated.

AI assessment note: “I would say 20% adverse and 80% just like, um, poor selection.”

Q Sorry. What do you, what do you take away from that though? That like, fuck, it doesn't matter.

A You know, luckily that happened because it was in January, they hosted a meeting in January and I had just started that campaign in January. So I felt like I got this omen early. Right. Whereas like, I was probably in my head thinking like, oh yeah, like I'll meet her on this trip, you know? And so it went kind of one 80 real quickly, um, where I was like, okay, this will be difficult. Um, so I felt like, I felt like it was kind of a gift, um, in terms of the timing. Uh, the bigger mistake is like thinking naively that, um, all LPs will like want to see Once they've committed to you, um, want to see you succeed and want to just be along for the ride. If you, if you, um, like stay true to what you said you're going to do. And, um, it's interesting because like, I've, I've had to like fire is the wrong word. I don't think of it that way, but like I've, I've blocked two LPs from investing in, in future funds. And I think both of the behavior in, in what they did and how they did it. I just felt like, Hey, I don't work like that. You know, and I think a lot of work. Yeah.

AI assessment note: “The bigger mistake is like thinking naively that, um, all LPs will like want”

Q And what were your concerns then? You know, it's a, it's a very, um, big and momentous challenge to start your own fund afresh as a first time fund manager. What were your concerns going into it?

A Well, I'll answer that in two ways. It wasn't a momentous challenge for me because I really had no other option. I just either could do that or do nothing. I think maybe someone starting out to do their own fund and who have an alternative may view it as a difficult thing. I, I really, from that mindset, which is important to understand, I didn't have another option of what to do. I think when you get into it, the concerns that come up are, You have to get some social proof, and then how do you ask people that you know for money, and then if you're raising a smaller fund, it's probably their personal money, which means that, oh, hey, you know, I'm, I might be Facebook friends with this person, or I might know their family, and then this could be part of one of their kids' college funds. I don't know.

AI assessment note: “the concerns that come up are, You have to get some social proof”

Q That's our game, right? Um, I would say to the founder, Samuel is amazing. I love Samuel, but look at these deals. He can be a passenger, and so let me lead it, and let's put him as the passenger. Would you worry that by being willing to do both, you put yourself in a position where you can be pushed to the passenger seat? By anyone you're competing against?

A Um, not really, because I, I kind of have a Zen approach about it, which is our job is to teach the founders how to interact with investors and raise capital over successive rounds. And part of that should be to choose the best partners for you, you know? And so I, I kind of learned this from a Brad Feld interview where, um, You know, I think I asked him or I can't remember what the situation was. I think it was like at a Connie event, uh, Connie Louis Louis. And he just said, like, I mentioned some deal that they did that they lost maybe the true. Um, and he was like, I thought it was great. He was like, I'm friends with everyone at true. And the entrepreneur is really happy. So we're, we're fine with that. And I'm also fine with that.

AI assessment note: “not really, because I, I kind of have a Zen approach about it”

Q What, as I'm just being devil's advocate here, let's pretend we're on a partnership together. What can we do? We want to continue being in this franchise. We're either in or out. If we're out, that's tough for the relationship, and so I, I get you, but I don't see what can be done to remedy it in a very buoyant environment.

A I agree. And it's easier to say that today than, you know, a year or two ago. Um, I think what I've heard from LPs is like some of them picked a few to go stay on the train and a number of them last year dropped off. So a number of endowments, foundations, fund to funds who were long time investors in like top tier funds that have gone really, really big have for a variety of reasons just said, Hey, we're great. Thank you for all the returns. Thank you for the partnership. It's time. To move earlier, you know, for us. And so I think that like, I'm not saying that LPs should have abandoned all those, but I think they probably stand on too many trains than they should have.

AI assessment note: “some of them picked a few to go stay on the train”

Q What, as I'm just being devil's advocate here, let's pretend we're on a partnership together. What can we do? We want to continue being in this franchise. We're either in or out. If we're out, that's tough for the relationship, and so I, I get you, but I don't see what can be done to remedy it in a very buoyant environment.

A I agree. And it's easier to say that today than, you know, a year or two ago. Um, I think what I've heard from LPs is like some of them picked a few to go stay on the train and a number of them last year dropped off. So a number of endowments, foundations, fund to funds who were long time investors in like top tier funds that have gone really, really big have for a variety of reasons just said, Hey, we're great. Thank you for all the returns. Thank you for the partnership. It's time. To move earlier, you know, for us. And so I think that like, I'm not saying that LPs should have abandoned all those, but I think they probably stand on too many trains than they should have.

AI assessment note: “some of them picked a few to go stay on the train and a number of them last year dropped off.”

Q Final one, Samuel, and I'm excited for this one. What's the most recent publicly announced investment, and why did you say yes and get so excited?

A I decided in fund four, Harry, we don't really announce the investments, and it's an interesting topic. What happened in the first three funds is, I think, partly because we were successful in finding good companies early, and there was a good rate of series A conversion, and the venture industry grew. I just started hearing from founders that we would put them on site, or we would write a blog post about them, Too early, and they would get bombarded with VC's email. So they would forward it to me and say, do you know this person? Should I take this meeting? And that can just be super distracting for the entrepreneur before they're ready. So it's a balance between the entrepreneurs building the relationships with the downstream capital, which is super important, versus ignoring all the noise of the inbound and the robo calls and the big data platforms that are just sending you emails through outreach to see if you'll bite. So we actually don't really announce them. And occasionally an entrepreneur will want to do that, but what I try to do is announce these rounds in smaller circles when the entrepreneur is ready to go meet these investors. So kind of a counter answer to your question, but I don't even know.

AI assessment note: “we don't really announce the investments, and it's an interesting topic.”

Q That's our game, right? Um, I would say to the founder, Samuel is amazing. I love Samuel, but look at these deals. He can be a passenger, and so let me lead it, and let's put him as the passenger. Would you worry that by being willing to do both, you put yourself in a position where you can be pushed to the passenger seat? By anyone you're competing against?

A Um, not really, because I, I kind of have a Zen approach about it, which is our job is to teach the founders how to interact with investors and raise capital over successive rounds. And part of that should be to choose the best partners for you, you know? And so I, I kind of learned this from a Brad Feld interview where, um, You know, I think I asked him or I can't remember what the situation was. I think it was like at a Connie event, uh, Connie Louis Louis. And he just said, like, I mentioned some deal that they did that they lost maybe the true. Um, and he was like, I thought it was great. He was like, I'm friends with everyone at true. And the entrepreneur is really happy. So we're, we're fine with that. And I'm also fine with that.

AI assessment note: “not really, because I, I kind of have a Zen approach about it”