Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
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Answered raw tape
D 5 · C 5 · P 5 · Cm 5 5.00
Q You said about the top three programs there. Uh, I do have to ask what you made of Sam Altman's, uh, post, uh, where he said about, well, I see obviously taking entrepreneurs who, uh, they wouldn't take them if they'd been to other incubators or accelerators. What did you make of that? You must've read that and thought, huh, that's interesting, Sam.
A Hmm. Yeah. Well, I, I did read that and actually I responded in a blog post with what I thought. I don't, I don't think Sam said that exactly. I think what he said was people who've gone through a prior accelerator program probably have a higher bar for their performance, um, and that YC will have some higher level of expectation if they've, quote, been accelerated, unquote, before. I think I generally agree with the underlying premise that Sam was trying to make. It was more his conclusion and recommendations afterwards that I disagreed with pretty vehemently. I think his Response generally was, if you don't get into YC, just hang out and wait and keep trying, and eventually you might get into YC, and that's better than doing any other accelerator program. He didn't exactly say that either, but I think that was his implied statement. I think that's kind of laughable and actually probably really poor advice for entrepreneurs. Um, usually I think Sam and YC in general is an amazing program, and they offer lots of benefits and advice. In this particular case, I think they were being a little bit more Uh, selfishly directed about their advice to entrepreneurs.
AI assessment note: “It was more his conclusion and recommendations afterwards that I disagreed with pretty vehemently.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Were they hot rounds? Obviously, fantastic companies. Now, you imagine there'd be incredibly competitive rounds. Were they hot rounds in the early days?
A Um, no, no. SlideShare and Mashree certainly were not, like, super competitive rounds, um, although, you know, strong team and capable founders. Mint.com, I guess, was probably a little bit competitive, um, Certainly by the time the A round happened, I put about 25 K into the A round, but I'd already been, you know, helping the company here and there a little bit. So, you know, maybe Mint.com was kind of the hot round, but, but certainly, you know, when I invested, when we invested in Lyft out of FB Fund, I guess it was called Zimride at the time, and when we invested in Credit Karma and Twilio, um, they were not really that competitive rounds, even though, you know, the founders were compelling most of the time. They were, you know, that particular time of Time, 2008, nine, 10 was actually a pretty tough period of time for people to raise capital.
AI assessment note: “SlideShare and Mashree certainly were not, like, super competitive rounds”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q I'm intrigued to hear how you ensure that you can invest the amount that you want to in follow on rounds. Uh, obviously they're very competitive. Sometimes you can get pushed out by the larger players. How do you ensure that you get into those rounds?
A Well, we can't. We don't always know that we're going to get into those rounds. A lot of the time we have to, you know, work hard to have a good relationship with the founder. You know, sometimes we can, you know, get that relationship contractually by, you know, signing the investment agreement, asking for Follow on investment rights. Uh, we usually do that so that we can invest in at least one follow on round. Um, with our accelerator companies, we have a kind of fixed structure that we invest into and we ask for a 500 K, uh, option to invest in the follow on round where we don't exceed 20% of the round. So, you know, typically if someone's raising a series a that might be, you know, two, three, five million dollars, we would like to be able to invest up to 500 K, but we're not usually the lead in that scenario. But most of the times, you know, most of the times we get some ability to follow on, uh, but you're correct. We don't always. And again, that's why we have a very large portfolio strategies. We want, you know, to get that to happen in at least enough scenarios where we can deploy follow on capital into our winners.
AI assessment note: “Well, we can't. We don't always know that we're going to get into those rounds.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Do you have a problem with entrepreneurs who've been to other accelerators before?
A No, and in fact, I was going to mention, you know, we've been investors through our seed investment program in a bunch of YC companies, over a hundred. I think we're actually one of the top three or four investors in YC companies over the years. Um, and same thing with Techstars. I think we've done at least 40 or 50 of the Techstars companies as well. So, we don't, we do compete at one level, but we also Invest in their, in their companies. I would say, you know, probably a third of our overall portfolio has gone through our own, uh, program. So maybe 500 out of the 1500 companies, uh, probably another 500 went through some other program. So whether that's YC or Techstars or AngelPad or SeedCamp or whatever, we've invested in plenty of other companies that have gone through both major, you know, globally recognized programs here in the U.S. as well as other programs, uh, around the world. Uh, and actually frequently for us, we find companies that Come from other programs around the world that may do those programs before they come to the U.S. and do ours or YC or someone else.
AI assessment note: “No, and in fact, I was going to mention, you know, we've been investors”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And in terms of the ownership state that you take in these companies, when you have such large portfolios, what does that look like? Does it allow you with the increased fund size? You know, it's not a 300 K fund now with 500. It's a much bigger fund. Does that small ownership still carry over to big venture returns?
A Well, I think it does work for us. Uh, the typical ownership that we hold in most of our seed round investments is probably between one to five percent. Maybe a little bit higher in some of the international geographies where valuations are lower. For Accelerator, it might start at around five to seven percent, depending on when we invested. Um, but most of those investments are probably never going to be higher than 10%, and in a lot of cases, they might be, you know, only around five percent or smaller. But the point that I was making with Michael is that ownership really isn't the math that we use to kind of think about how we invest. Uh, we really think more in terms of number of investments and the likely probability distribution of finding large outcomes. And then potentially we think about, you know, reserving capital for following on and our winners, but still our second check, you know, investments are probably not going to be as, uh, great an outcome as our first check. You know, so when we think about investment, we really think about, you know, about two percent of our portfolio doing 50 X or better, and hopefully about five percent of our portfolio doing 20 X or better. Uh, and then we might have another 10 to 20% that gets us some positive return. So that's probably going to give us a base criteria, a base outline of maybe two to three X in performance. And if we'…
AI assessment note: “typical ownership that we hold in most of our seed round investments is probably between one to five percent”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q to the investment strategy, does your investment approach require unicorn exits to have a good return? Uh, we saw the tweet storm last week between you and Michael at Sundana. So I'm sorry for starting that one. I feel a bit of a, I don't think you're sorry one bit. No, not at all, actually, but let's go with the, does it require unicorn assets to have a good return?
A Uh, well, it certainly helps. Uh, I don't think it's required necessarily. So in my angel investment portfolio, I made about 13 investments. Uh, I did some advisory work for a few other companies, but let's say it's maybe 15 companies. There were no unicorns in that group of companies, but I had three What we would call centaurs or a hundred million plus, uh, sort of exits, um, on a relative basis, all of those companies were probably between a 10 to 20 X return on investment. And so, you know, three out of 13 or three out of 15 is probably a hit rate that's maybe higher than I would normally expect, but let's say that's somewhere around, you know, maybe a 20% sort of hit rate on winners. You know, so I, I basically made about a million dollars, maybe a little bit more than that on 300,000. And so a three X Return or slightly more than a three X return. The investment period return period maybe was around seven or eight years. Uh, I don't know if that's typical, but in that case, you know, I made a decent return, at least measured on the IRR basis. That's probably around a 20% return plus or minus, but I didn't have any unicorn. Now when we invest, we do expect to find unicorns, but we do a lot larger portfolio size. Um, our expectations are that we'll find those You know, unicorns, or at least, let's say, 50 to a hundred X return profile companies, probably not more than two p…
AI assessment note: “it certainly helps. Uh, I don't think it's required necessarily.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q You said about the top three programs there. Uh, I do have to ask what you made of Sam Altman's, uh, post, uh, where he said about, well, I see obviously taking entrepreneurs who, uh, they wouldn't take them if they'd been to other incubators or accelerators. What did you make of that? You must've read that and thought, huh, that's interesting, Sam.
A Hmm. Yeah. Well, I, I did read that and actually I responded in a blog post with what I thought. I don't, I don't think Sam said that exactly. I think what he said was people who've gone through a prior accelerator program probably have a higher bar for their performance, um, and that YC will have some higher level of expectation if they've, quote, been accelerated, unquote, before. I think I generally agree with the underlying premise that Sam was trying to make. It was more his conclusion and recommendations afterwards that I disagreed with pretty vehemently. I think his Response generally was, if you don't get into YC, just hang out and wait and keep trying, and eventually you might get into YC, and that's better than doing any other accelerator program. He didn't exactly say that either, but I think that was his implied statement. I think that's kind of laughable and actually probably really poor advice for entrepreneurs. Um, usually I think Sam and YC in general is an amazing program, and they offer lots of benefits and advice. In this particular case, I think they were being a little bit more Uh, selfishly directed about their advice to entrepreneurs.
AI assessment note: “I think that's kind of laughable and actually probably really poor advice for entrepreneurs.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And final question before we dive into Quickfire, I want to ask about, we mentioned the PayPal team earlier, often named PayPal Mafia, one of the most amazing teams ever assembled, uh, clearly. But did you guys have any idea at the time what an extraordinary group that you were? And what was it like working with these guys in the beginning?
A Well, I hesitate to put myself in that group because I have not created a billion dollar company, at least not yet. Um, well, maybe we'll see. I think, you know, I had the really good fortune to work a little bit of time with some of those folks. Um, initially when I started at PayPal, Dave Sachs was my boss who went on to run Yammer, which got acquired by Microsoft for about a billion bucks. I got the chance to work pretty closely with, uh, Steve Chen and Chad Hurley and Jaud Karim, who are all the founders of YouTube. They were really great people. I, you know, didn't Realized they were going to create the world's largest video platform, but they were great to work with.
AI assessment note: “didn't Realized they were going to create the world's largest video platform, but they were”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Were they hot rounds? Obviously, fantastic companies. Now, you imagine there'd be incredibly competitive rounds. Were they hot rounds in the early days?
A Um, no, no. SlideShare and Mashree certainly were not, like, super competitive rounds, um, although, you know, strong team and capable founders. Mint.com, I guess, was probably a little bit competitive, um, Certainly by the time the A round happened, I put about 25 K into the A round, but I'd already been, you know, helping the company here and there a little bit. So, you know, maybe Mint.com was kind of the hot round, but, but certainly, you know, when I invested, when we invested in Lyft out of FB Fund, I guess it was called Zimride at the time, and when we invested in Credit Karma and Twilio, um, they were not really that competitive rounds, even though, you know, the founders were compelling most of the time. They were, you know, that particular time of Time, 2008, nine, 10 was actually a pretty tough period of time for people to raise capital.
AI assessment note: “SlideShare and Mashree certainly were not, like, super competitive rounds”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And in terms of the ownership state that you take in these companies, when you have such large portfolios, what does that look like? Does it allow you with the increased fund size? You know, it's not a 300 K fund now with 500. It's a much bigger fund. Does that small ownership still carry over to big venture returns?
A Well, I think it does work for us. Uh, the typical ownership that we hold in most of our seed round investments is probably between one to five percent. Maybe a little bit higher in some of the international geographies where valuations are lower. For Accelerator, it might start at around five to seven percent, depending on when we invested. Um, but most of those investments are probably never going to be higher than 10%, and in a lot of cases, they might be, you know, only around five percent or smaller. But the point that I was making with Michael is that ownership really isn't the math that we use to kind of think about how we invest. Uh, we really think more in terms of number of investments and the likely probability distribution of finding large outcomes. And then potentially we think about, you know, reserving capital for following on and our winners, but still our second check, you know, investments are probably not going to be as, uh, great an outcome as our first check. You know, so when we think about investment, we really think about, you know, about two percent of our portfolio doing 50 X or better, and hopefully about five percent of our portfolio doing 20 X or better. Uh, and then we might have another 10 to 20% that gets us some positive return. So that's probably going to give us a base criteria, a base outline of maybe two to three X in performance. And if we'…
AI assessment note: “typical ownership that we hold in most of our seed round investments is probably between one to five percent”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q to the investment strategy, does your investment approach require unicorn exits to have a good return? Uh, we saw the tweet storm last week between you and Michael at Sundana. So I'm sorry for starting that one. I feel a bit of a, I don't think you're sorry one bit. No, not at all, actually, but let's go with the, does it require unicorn assets to have a good return?
A Uh, well, it certainly helps. Uh, I don't think it's required necessarily. So in my angel investment portfolio, I made about 13 investments. Uh, I did some advisory work for a few other companies, but let's say it's maybe 15 companies. There were no unicorns in that group of companies, but I had three What we would call centaurs or a hundred million plus, uh, sort of exits, um, on a relative basis, all of those companies were probably between a 10 to 20 X return on investment. And so, you know, three out of 13 or three out of 15 is probably a hit rate that's maybe higher than I would normally expect, but let's say that's somewhere around, you know, maybe a 20% sort of hit rate on winners. You know, so I, I basically made about a million dollars, maybe a little bit more than that on 300,000. And so a three X Return or slightly more than a three X return. The investment period return period maybe was around seven or eight years. Uh, I don't know if that's typical, but in that case, you know, I made a decent return, at least measured on the IRR basis. That's probably around a 20% return plus or minus, but I didn't have any unicorn. Now when we invest, we do expect to find unicorns, but we do a lot larger portfolio size. Um, our expectations are that we'll find those You know, unicorns, or at least, let's say, 50 to a hundred X return profile companies, probably not more than two p…
AI assessment note: “well, it certainly helps. Uh, I don't think it's required necessarily.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q I'm intrigued to hear how you ensure that you can invest the amount that you want to in follow on rounds. Uh, obviously they're very competitive. Sometimes you can get pushed out by the larger players. How do you ensure that you get into those rounds?
A Well, we can't. We don't always know that we're going to get into those rounds. A lot of the time we have to, you know, work hard to have a good relationship with the founder. You know, sometimes we can, you know, get that relationship contractually by, you know, signing the investment agreement, asking for Follow on investment rights. Uh, we usually do that so that we can invest in at least one follow on round. Um, with our accelerator companies, we have a kind of fixed structure that we invest into and we ask for a 500 K, uh, option to invest in the follow on round where we don't exceed 20% of the round. So, you know, typically if someone's raising a series a that might be, you know, two, three, five million dollars, we would like to be able to invest up to 500 K, but we're not usually the lead in that scenario. But most of the times, you know, most of the times we get some ability to follow on, uh, but you're correct. We don't always. And again, that's why we have a very large portfolio strategies. We want, you know, to get that to happen in at least enough scenarios where we can deploy follow on capital into our winners.
AI assessment note: “Well, we can't. We don't always know that we're going to get into those rounds.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Do you have a problem with entrepreneurs who've been to other accelerators before?
A No, and in fact, I was going to mention, you know, we've been investors through our seed investment program in a bunch of YC companies, over a hundred. I think we're actually one of the top three or four investors in YC companies over the years. Um, and same thing with Techstars. I think we've done at least 40 or 50 of the Techstars companies as well. So, we don't, we do compete at one level, but we also Invest in their, in their companies. I would say, you know, probably a third of our overall portfolio has gone through our own, uh, program. So maybe 500 out of the 1500 companies, uh, probably another 500 went through some other program. So whether that's YC or Techstars or AngelPad or SeedCamp or whatever, we've invested in plenty of other companies that have gone through both major, you know, globally recognized programs here in the U.S. as well as other programs, uh, around the world. Uh, and actually frequently for us, we find companies that Come from other programs around the world that may do those programs before they come to the U.S. and do ours or YC or someone else.
AI assessment note: “No, and in fact, I was going to mention, you know, we've been investors”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q You mentioned the accelerator there. Obviously, 500 startups, big accelerator program. I was chatting to a VC friend of mine the other day, and he stated that accelerators have big issues with adverse selection With regards to the best entrepreneurs not going through them. Does that pervade into your thoughts much?
A I think that's kind of bullshit. I mean, that really depends a lot on the program. When things were first getting started with accelerators, maybe that's the case, and I think if you, if you have very, very accomplished entrepreneurs, perhaps those who've already had exits before, or have raised venture capital before, you know, I think they have the option to certainly raise directly from BCs, but, um, I don't think you see that criticism, at least of the more established accelerator programs. There's, there's some people who say, Hey, I don't need that. I've already got a network. I've already got the resources I need for help with customer acquisition and distribution or with other areas. But I think you've also seen very successful companies come back and do an accelerator program or founders who've had, you know, exits come back and do an accelerator program a second time. And I certainly think for first time entrepreneurs, the network is really, really important. So, you know, people who get into either, you know, 500 or Y Combinator or Techstars or another top program, You know, probably the network and the alumni and the connections and the help is worth, you know, the relatively small amount of dilution, uh, and usually that's, you know, made better through the valuation increase or bump that you're likely to get, uh, if not, you know, all the other connections. I mean…
AI assessment note: “I think that's kind of bullshit. I mean, that really depends a lot on the program.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q You mentioned the accelerator there. Obviously, 500 startups, big accelerator program. I was chatting to a VC friend of mine the other day, and he stated that accelerators have big issues with adverse selection With regards to the best entrepreneurs not going through them. Does that pervade into your thoughts much?
A I think that's kind of bullshit. I mean, that really depends a lot on the program. When things were first getting started with accelerators, maybe that's the case, and I think if you, if you have very, very accomplished entrepreneurs, perhaps those who've already had exits before, or have raised venture capital before, you know, I think they have the option to certainly raise directly from BCs, but, um, I don't think you see that criticism, at least of the more established accelerator programs. There's, there's some people who say, Hey, I don't need that. I've already got a network. I've already got the resources I need for help with customer acquisition and distribution or with other areas. But I think you've also seen very successful companies come back and do an accelerator program or founders who've had, you know, exits come back and do an accelerator program a second time. And I certainly think for first time entrepreneurs, the network is really, really important. So, you know, people who get into either, you know, 500 or Y Combinator or Techstars or another top program, You know, probably the network and the alumni and the connections and the help is worth, you know, the relatively small amount of dilution, uh, and usually that's, you know, made better through the valuation increase or bump that you're likely to get, uh, if not, you know, all the other connections. I mean…
AI assessment note: “I think that's kind of bullshit. I mean, that really depends a lot on the program.”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q Um, when you, when you do follow on, how do you avoid the common problem of a structure like yours of the negative signaling that can occur in the wider market? Do you think about that?
A Uh, we think about it a little bit, and it does, again, matter, but I think people tend to overthink this. I think that the signaling issue, whether it happens for us or even other downstream investors, you know, well, first of all, I would say signaling is an issue when the lead investor in a prior round doesn't follow on in the next round substantially enough, and that's more likely the case for an institutional lead investor who's playing a seed or series A role where they're on the board or they were the biggest investor in the previous round. That's Really not a typical role for us to play. Um, you could argue that maybe coming out of our accelerator, we might have that situation, but that's not quite the same, and we're usually not the lead investor in seed or series A rounds, but it does happen. My perspective on this is typically that if the founder or other investors are more worried about my investment decision than the baseline performance of the company, there's already likely some kind of problem there. You know, I would I have to say that the most important thing in making a decision to invest in the company is the company's performance. If the founders are worried about, you know, whether I'm going to follow on or not, or the next round investors are worried about whether I'm going to follow on or not, it's probably because there's not strong metrics or performan…
AI assessment note: “That's Really not a typical role for us to play.”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q Um, when you, when you do follow on, how do you avoid the common problem of a structure like yours of the negative signaling that can occur in the wider market? Do you think about that?
A Uh, we think about it a little bit, and it does, again, matter, but I think people tend to overthink this. I think that the signaling issue, whether it happens for us or even other downstream investors, you know, well, first of all, I would say signaling is an issue when the lead investor in a prior round doesn't follow on in the next round substantially enough, and that's more likely the case for an institutional lead investor who's playing a seed or series A role where they're on the board or they were the biggest investor in the previous round. That's Really not a typical role for us to play. Um, you could argue that maybe coming out of our accelerator, we might have that situation, but that's not quite the same, and we're usually not the lead investor in seed or series A rounds, but it does happen. My perspective on this is typically that if the founder or other investors are more worried about my investment decision than the baseline performance of the company, there's already likely some kind of problem there. You know, I would I have to say that the most important thing in making a decision to invest in the company is the company's performance. If the founders are worried about, you know, whether I'm going to follow on or not, or the next round investors are worried about whether I'm going to follow on or not, it's probably because there's not strong metrics or performan…
AI assessment note: “we're usually not the lead investor in seed or series A rounds”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q How do you think you grew working with people like this?
A Well, I think, you know, getting to work with and, um, probably watch the progress of a lot of those folks. I think Peter and Max and Reid Hoffman and a bunch of others, it obviously had lots and lots of success, but the lessons that we probably learned at PayPal were probably learned in the trenches with a lot of other people on the team. Um, and those were, you know, how to build product and how to do marketing, um, kind of how to deal with tough situations when, you know, maybe fraudsters are trying to steal money from you or other large companies like eBay or Visa card associations are competing with you. And I think, you know, there was just a lot of really thoughtful and smart people there that, you know, we had to move quickly. Otherwise, you know, we'd get our asses kicked. One of the things I do think is interesting that people don't always Understand is, you know, PayPal maybe didn't have as a very easy road when it was getting started. If you compare maybe a couple of companies like, you know, Microsoft or Yahoo or Google, those three probably all discovered their business models relatively early and then really had dominating performances. If you look at a few others, maybe like Amazon or Facebook and PayPal, they had really strong growth, but they had some challenges in really getting the business model worked out or a lot of, you know, tougher situations. And I th…
AI assessment note: “the lessons that we probably learned at PayPal were probably learned in the trenches”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q question. I crowdsource some questions here. A special interview crowds or some questions. So one from Matt Lerner, uh, distro dojo, 500, London office. Uh, and he asks you, you've backed the likes of mint, twilio, send grid lift. What were you thinking when you saw those deals? Uh, did you know how they'd turn out in any sense over others? Uh, and were they hot as themselves as rounds?
A I guess the three that I invested in while I was still kind of, uh, Doing amateur angel investing. Mashery, uh, SlideShare, and Mint. I think with both SlideShare and Mashery, I don't think either of them looked like a slam dunk win. I guess with Mint.com, there was, you know, probably an expectation that this could be a really big story, and Aaron Patzer, who was the founder and CEO, was a pretty impressive founder. Even, even the first time that I met him, he was, you know, had a product that was pretty compelling and was a very, you know, confident entrepreneur. So, I don't, I don't know. I mean, I still feel like, Most of the time, when we, when I invest in companies, or when we, 500, invest in companies, it's very, very early, and it's hard to predict what's going to happen in the future.
AI assessment note: “with Mint.com, there was, you know, probably an expectation that this could be a really big story”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q When you don't get into them, why do you think that is? Do you think that's the big boys pushing you out? Do you think that's founders? What are the reasons you think and how do you look to rectify them going forward? I know you're not going to be happy with that.
A Uh, yeah, that's definitely happened. Um, sometimes it's larger investors who want to take as much of the next round as they possibly can. Sometimes, uh, we don't always have those rights contractually. Um, sometimes we may not always have capital available or we may choose not to put in money in those rounds, but more often than not, it's usually because there's demand for the round and it's oversubscribed and, you know, the participants in the round are trying to jockey for their position. I think that doesn't happen as much as, you know, maybe people might be concerned about. It does happen. The funny thing is sometimes it happens in rounds that are hot that don't end up really being that valuable, and a lot of times it doesn't happen in rounds where it's not that hot, but later it becomes valuable. So I don't really think that there's as much correlation with, hey, this seed round or this A round is really hot, and later that becomes Uber. You know, that does happen every once in a while, but I would say if I look back on a lot of the deals that ended up becoming really big for us, you know, Twilio and Credit Karma in particular, and maybe a few others, they weren't hot when we invested, or weren't that, they weren't so hot when we invested that we couldn't get into the round, or we couldn't get into a follow-on round. So yes, it happens, but I don't know that that's a huge…
AI assessment note: “sometimes it's larger investors who want to take as much of the next round”
Answered raw tape
D 5 · C 3 · P 5 · Cm 3 4.10
Q And then your favorite blog or newsletter, what are the must reads for you?
A Uh, there's a bunch that I like out there. I definitely, you know, uh, good friends with Mark Suster read his stuff all the time. He's probably one of the more thoughtful people out there. Brad Feld and Fred Wilson have, uh, been sort of mentors and, you know, are small investors in our fund, and they've kind of been, you know, huge influences, I think. Uh, Brad certainly has written tremendous amounts online, uh, way in the past. Naval doesn't write quite as much as he used to, and, you know, really Nivi and Naval did a lot of work with Venture Hacks that I thought was very helpful, but that was probably more like five to 10 years ago before they did AngelList. There's a lot of other, you know, great folks out there. I, I think, you know, One thing is maybe not to worship other blogs too much and think about writing yourself. I think there's a lot of folks who probably, you know, could start their own blogs and, you know, get a voice heard. I think it's really important to not just lean on, you know, everybody else doing that work, but even for younger folks who are getting into the industry to write down their thoughts. Charles Hudson, I think has actually done a great job.
AI assessment note: “Mark Suster read his stuff all the time”
Answered raw tape
D 4 · C 4 · P 4 · Cm 4 4.00
Q question. I crowdsource some questions here. A special interview crowds or some questions. So one from Matt Lerner, uh, distro dojo, 500, London office. Uh, and he asks you, you've backed the likes of mint, twilio, send grid lift. What were you thinking when you saw those deals? Uh, did you know how they'd turn out in any sense over others? Uh, and were they hot as themselves as rounds?
A I guess the three that I invested in while I was still kind of, uh, Doing amateur angel investing. Mashery, uh, SlideShare, and Mint. I think with both SlideShare and Mashery, I don't think either of them looked like a slam dunk win. I guess with Mint.com, there was, you know, probably an expectation that this could be a really big story, and Aaron Patzer, who was the founder and CEO, was a pretty impressive founder. Even, even the first time that I met him, he was, you know, had a product that was pretty compelling and was a very, you know, confident entrepreneur. So, I don't, I don't know. I mean, I still feel like, Most of the time, when we, when I invest in companies, or when we, 500, invest in companies, it's very, very early, and it's hard to predict what's going to happen in the future.
AI assessment note: “it's very, very early, and it's hard to predict what's going to happen”