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SPEAKER_04: All right, everybody. Welcome to another episode of This Week in Startups. It's our crossover episode with our friends at the Acquired Podcast. Ben Gilbert and David Rosenthal are with us. Again, they co-host Acquired.fm. Ben, of course, is the co-founder of Pioneer Square Labs, PSL Ventures, and David Rosenthal is an independent angel investor startup advisor. Boys, welcome back to the program.

SPEAKER_09: Thanks for having us. Thanks for having us. Thanks for having us. I've actually been, you've been browbeaten me so much over the past year. I have a small, small little angel fund. Now I'm following in your footsteps.

SPEAKER_14: Nicely done. Is this a rolling fund, may I ask?

SPEAKER_16: No, it's not. It's a traditional fund. I thought about the rolling fund. Wait, I think we discussed this last time. Decided to start small.

SPEAKER_04: Okay. What is the footprint of the fund? Is it trying to go for 10 or 20 or 5? What are you thinking? Micro?

SPEAKER_09: Micro. Micro. Very micro.

SPEAKER_04: So, so a couple of million bucks, a couple of million bucks. Yeah. Perfect. And so then you want to try to do 30 investments of 25, 50k, 100k, something in that range?

SPEAKER_21: Yeah, like, yeah, 100k ish, 50, and you got to hit 30 investments. Is that the portfolio concept?

SPEAKER_22: Yeah, 20 to 40. It's the plan.

SPEAKER_21: 20 to 40 at 100k.

SPEAKER_22: Do it in a year. No reserves. See how it goes.

SPEAKER_17: Got it. So this is, uh, like my first preschool, uh, you know, that toy series, My First Recorder.

SPEAKER_09: Yeah, that's exactly. We're calling it Kindergarten Ventures, actually.

SPEAKER_26: What are you calling it?

SPEAKER_09: The name is Kindergarten Ventures.

SPEAKER_21: Perfect. Uh, so this is going to be your test. Now, the problem with a such a small fund historically, uh, is that you, uh, David are not going to have a lot of fees to live off of. Even if you got 3% on $3 million, only 90k a year.

SPEAKER_29: Wow. So how are you going to survive, uh, in terms of fees? What are you thinking of fee structure?

SPEAKER_31: Well, that's why it's a good thing that I have the acquired podcast with Ben and, uh, my partner in this in Kindergarten, uh, Nat Manning is the COO of a company called Kettle.

SPEAKER_16: So he's full time founder. Perfect.

SPEAKER_33: And so, yeah, this is for our deal flow on the side.

SPEAKER_17: Love it. This is a great way to start off.

SPEAKER_04: You have other revenue sources. And as people know, uh, my first fund, I just did a 20% carry and no fees.

SPEAKER_31: We're not taking fees. It's a cause we didn't think it's right. Cause we're both full time on other things.

SPEAKER_04: And because like, what are we going to do anyway, but you should any legal fees or accounting or something you can put against it, but you're not taking management fees. Um, and that's, I did that on my first one as well. And that fund had calm and, uh, Robin hood in it. So haven't heard of them.

SPEAKER_38: Congratulations, by the way.

SPEAKER_44: I, I think that fund. Yeah, it's, it's, it'll be a day for you yesterday.

SPEAKER_04: You know, in a way, except I don't plan on selling Robinhood shares for a decade. Personally, I will distribute the shares at some point to our LPs, uh, when our lockups up, but

SPEAKER_46: I don't see a case for me wanting to sell those shares.

SPEAKER_47: When the company's only worth 30 billion, it's got 22 million active users. I don't know how you, y'all feel about it.

SPEAKER_49: So you're not like feeling a take the win, you know, lock it in.

SPEAKER_10: Heck no. I mean, think about the last double up. The last, the last two double ups in this game are so material.

SPEAKER_54: Oh, this is, we preach about this on acquired all the fricking time. This is the mistake that Sequoia learned with their Apple investment.

SPEAKER_57: They sold their Apple investment for $6 million total. They owned like 20% of the company.

SPEAKER_46: Makes no sense. You want to ride your winners, as we've been saying on the all in podcast a bunch,

SPEAKER_04: and it's time in market, not timing the market. I, I, I could see, I know this sounds crazy to folks. I could see some of this cohort that came out in the last, you know, group of, uh, Decacorns Coinbase, um, you know, cause I do think crypto is gonna be around for a while. I could see Coinbase, Airbnb, Uber, DoorDash.

SPEAKER_05: I could have seen Slack and certainly Robinhood. I could see all of those having a 10 to 20 X in them.

SPEAKER_62: Yeah. There's a great, well, this is perfect for the, the theme, the, the meat of the episode in a little bit that we'll get into.

SPEAKER_64: Yeah, it is actually, if you were to look at that cohort, Ben, I'll bring, oh, Ben, what do you think of David's plan? I think it's a great plan.

SPEAKER_03: I mean, why is it a good plan? What advice do you have for him?

SPEAKER_49: Well, there's so much opportunity just in the like acquired Slack alone from people pinging him and like pinging both of us and being like, Hey, I'm starting to start up. What do you think? I really liked the pod, um, that, you know, it's, it's a shame David hasn't had a firepower until now to take advantage of it. So I love the strategy. Uh, I also love, uh, I'm a, I'm a proud investor, uh, myself. That's right.

SPEAKER_70: And I asked David, 25, 50 in there, 25, 50.

SPEAKER_49: Maybe a little sub that I'm, I'm early on the journey, but, uh, I asked David,

SPEAKER_71: what commitments to make?

SPEAKER_49: What can you promise me? Like what's, you know, what, what kind of reporting are you gonna send me? And what's my portfolio structure gonna look like? And portfolio construction gonna look like? And you know, what, what stage are you playing at? And he just laughed at me and he was like, yeah, I mean, I'll let you know when there's returns. So I like the light lift that he's got going on.

SPEAKER_67: I, I like that as well. Now to be an LP in a fund.

SPEAKER_04: I do think there's two the, you know, putting aside returns, we, we're gonna be pretty sure David's gonna get good returns. He's got great deal flow. He's established in the industry. Anybody who is a startup that wants to get 25, 50 K would be, you know, wise to take his money. I think that's a no brainer, uh, or even a hundred, but you're gonna add a lot to it. But I do think thinking about when you're an LP in a fund, I'm in 20 funds or so, and I can't be in anymore, but I am thinking about being in this one. And the way that I would think about it is, uh, are you going to let us know about the

SPEAKER_63: deals in real time as you do them in one of these micro funds, David?

SPEAKER_08: Yeah. So the plan is, yes, we're still just getting up and running.

SPEAKER_09: I've been thinking about, uh, setting up a private channel in the acquired Slack for, and just putting all kindergarten folks in there, LPs, our founders.

SPEAKER_82: I'm in, if you do it, I'm do, if you're, I'm in for that. I'll put in 25.

SPEAKER_74: If you do, if you do that. Great.

SPEAKER_84: Only because- 25 paid to get access to the Slack channel.

SPEAKER_74: Well, I already have access to Slack channel. I'm a member of acquired FM, but I'm thinking if you do a deal and you're putting 25 in,

SPEAKER_04: maybe that's just, you know, good signal for me for a downstream syndicate investment.

SPEAKER_86: Great. Great, great. Downstream or current, right? It could be current.

SPEAKER_10: Yeah, sure. But, you know, uh, I'm going to assume some of those rounds might be closing up quickly and maybe I don't get into them, but, you know,

SPEAKER_09: Well, so that's what I was thinking is like, yeah, things are going on. We post about it in the cycle. Like, Hey, and then with the founders are in there and the RLPs are probably the largest group of LPs is, is GP's other venture firms. Uh, and then we've got other great folks in there.

SPEAKER_04: That was Mark Andreessen's plan. He was in our first fund. He was in my first fund and he came out of nowhere. And he's like, Oh, I heard you're raising a fund. I was like, would you hear that? He was like, ah, you know, I'm Mark Andreessen. And he's like, I'll put 50k in, and then, uh, uh, I kicked him out of the second fund or didn't invite him back because I invited him on the podcast. And he's like, uh, yeah, no, I'm not going to make it. And then his PR people were like, oh, well, you can have all these other people in the podcast.

SPEAKER_21: And I was like, no, Mark should come do a keynote at the event. And then Mark was like, do I have to be on your podcast and come to your events and do keynotes in order to be in business?

SPEAKER_04: But I just wrote back one word. Yes.

SPEAKER_93: You're like, dude, you should want to be on my podcast.

SPEAKER_04: Well, I was just like, you know what? You're being a jerk for no reason. And you're on everybody else's podcast. You know, you're on Panda, which is trashing you constantly.

SPEAKER_95: You know, like if you're on panda.com or whatever, like come on my podcast. Like it's, you know,

SPEAKER_04: that's where all the acrimony comes from with me and Mark.

SPEAKER_09: What is the origin of the twist name this week in startups?

SPEAKER_14: So I was on this week in tech with Leo Laporte. Yep. Because that's what I was wondering.

SPEAKER_21: I asked him, Hey, can I use the name to do this week in startups? Because I was only able to be on, you know, it was very hard to get a slot on this week in tech and I would be on one out of every four or five episodes.

SPEAKER_04: And I was trying to be on more because he's trying to pick my profile, but it was just like Kevin Rose was on and, you know, all these famous people were on at the time. And I was like, Hey, you know, I want to talk about startups more, because it was this week in tech was more about the new iPhone and whatever. And he was like, Yeah, go for it. And then I started doing other this weekends. And that kind of pissed him off a little bit. But we worked it out. We hashed it out.

SPEAKER_18: Nice. Because I was wondering, Ben and I were actually talking about this. Why?

SPEAKER_102: At this point. Shouldn't you just call this Jason Calagana show?

SPEAKER_04: 100%. Yeah, I mean, at some point. But I, you know, I kind of like my legacy of this weekend startups. But yeah, I'm doing it four days a week, five days a week. So it's kind of the Jason Calagana show. I guess. Yeah, I'll take that under advisement.

SPEAKER_49: And it's where I go to get my, you know, direct drip of Jason. Because when I'm listening to all in, you know, your boys are kind of trashing you a little bit. They're taking the mic. They're running with it. They talk too long. And then you try and talk. And someone's like, Oh, pass the ball, pass the ball. Why can't you learn to pass the ball? So it's nice to have the straight, the straight stuff.

SPEAKER_108: Thank you for that. It's, it's actually made it easier now that I'm doing four or five days a week on this show.

SPEAKER_74: You know, when I'm doing an interview with somebody, I don't need to interject as much

SPEAKER_04: because people got their fill of Jason from when I do the news up front. And then I do the interview on most episodes. And then on, then on all in, I'm just like, you know what, I'm just the point guard. I don't need to shoot. I'm just a pass first point guard. And if I get some reps in fine, but you know what, you're going to get enough of me from that.

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SPEAKER_04: So what other advice do you have for David, Ben, when he goes out on this road and tries to make these small bets?

SPEAKER_26: What should he do with his pro rata? Should he fight to get pro rata in deals? No. Should he do follow on?

SPEAKER_49: No, I don't think because look, I think getting pro rata in writing for a fund of that size seems a little bit silly to me. I think having like handshake agreements with the founders where you stay really close with them, you legitimately help the company during that round. And then you're there when the next round comes together for if it's an investment out of this

SPEAKER_117: fund or an SPV or whatever, like, it seems to make way more sense to me then especially for checks of this size.

SPEAKER_05: I am going to somewhat agree somewhat disagree.

SPEAKER_04: I agree that with the small checks, you're going to have a hard time in 2021. Getting pro rata for 2550 K check. Most of the time that's going to happen at what 250. In a seed round, you get pro rata 250 K, you'd be a major investor in a one or two. If you're lucky like yeah, but I only do deals when I have pro rata. That's my I would say 99 out of 100.

SPEAKER_31: Now we have it very much larger fund and your initial chances are much larger, right?

SPEAKER_04: Bigger check sizes.

SPEAKER_49: Yeah, yeah. And do you always actually get it? Like even if it's in the docs? Or does do people ask you to waive it at a future financing?

SPEAKER_04: I am of the I tell everybody up front, the founders, we plan on taking it forever. Um, and we plan on keeping our board seat forever if we own over five or 10% of the company.

SPEAKER_127: Um, and I mean, you're doing this at a way different scale.

SPEAKER_04: Um, you know what? I started at exactly your scale. So I would anticipate you would be doing it at my scale in five years. Um, then you should actually be preparing for that reality. Yeah. And so, you know, if you do get 50 K into the next, you know, Robin Hood, you I think asking for the pro rata in a nice way, if they will give you a side letter with it is well worth your time. I would ask every time.

SPEAKER_10: And if you get it one out of three, and the way I would signal it to in to the founders is,

SPEAKER_04: I just want to be able to place a bigger bet down the road with my syndicate and my LPs. And we will pop up an SPV. So do you have an SPV strategy for this yet? Yep. Yep. Yeah.

SPEAKER_123: Explain it.

SPEAKER_133: That's the whole strategy. Is to what? Oh, is that for for follow ons?

SPEAKER_13: When when it's a great follow on opportunity, and the founder wants us in that we do a SPV is not out of the fund funds too small.

SPEAKER_05: Perfect.

SPEAKER_04: So that is the model I pioneered. Uh, and you should totally work on because and where are you going to do those SPVs using

SPEAKER_13: a shore using AngelList AngelList they're managing the fund.

SPEAKER_04: Oh, they're managing the fund.

SPEAKER_110: What does that cost like 100 grand to set up the fund?

SPEAKER_31: Uh, no, no upfront cost. It's a 1% or I think it's 1% or either 20 or 25 K a year, whichever is smaller.

SPEAKER_64: Oh, that's a nice way to do it. Yeah. So 1% or 25 K, which in a $3 million fund would be basically the same thing.

SPEAKER_04: So for 10 years, 30 K a year would be 300,000 if the fund exists that long.

SPEAKER_140: If the fund exists that long.

SPEAKER_64: Other services are 100 K I think and 10, 10 K a year. So it winds up being about the same. Yep.

SPEAKER_142: So it was just, it was just easy. Do the SPVs come for free with that?

SPEAKER_09: Uh, I believe they do. Uh, if you're doing individual SPVs, I think AngelList is what?

SPEAKER_21: Like eight, 10 K and SPV, but basically 10 K and SPV and then 5 K in wiring fees. Uh, blue sky fees is, you know, the potential on top of that. So I do think it's very interesting the way you're constructing it. Using AngelList is a great way to do it. Um, yeah.

SPEAKER_127: Question for you. I would love to actually your advice on a specific piece of it.

SPEAKER_09: Um, so I'm thinking we're, we're gonna do a lot of seed and I've been doing most probably half of what I've been doing over the past year, year and a half as an angel has been seed. Um, but you know, we have, we have such great companies and folks on the pod and in the ecosystem. Uh, I've also been doing some A's B's C's, you know, just like small checks personally participating.

SPEAKER_13: Uh, I'm thinking we'll have some great opportunities for that, for the fund too. Do you, what do you do when you see stuff like that?

SPEAKER_04: Well, uh, we are doing increasingly series A's and series B's when we can get into them. Uh, and so we'll do a 50, uh, we'll do a, a new investment in a 50 to $200 million round. It has happened. Uh, that's not our bread and butter though. I think what I learned over my 10 year journey, which you're basically starting exactly where I started, um, which is you've got a podcast, you got the audience, you got the brand. Uh, what I quickly realized was the amount of work it takes to put in 25 or 50 K is the

SPEAKER_74: same amount of work as putting in 3 million. Yeah, and the amount of work you're gonna put into it over time is gonna be the same. So the quicker you can get to a larger dollar amount put in and to 10 to 20% ownership and

SPEAKER_26: the winners, the better you're gonna do. And when I went out with my second fund and my third fund to meet with the top, top, top, top, top, top LPs in the world, literally the top endowments. I got meetings with every single one in their office with the top person, right? Because I got a good brand and I was able to, you know, get those intros, et cetera.

SPEAKER_04: The thing they obsessed over was my ownership percentage of me being a solo GP. And I told them like, well, I'm gonna be a solo GP. So if you don't like that, what if you get hit by a car? I'm like, the fund wraps up. That's it. And, you know, a lot of people passed. Most people passed, obviously, and they couldn't get their head around the solo GP thing. And I was like, that's fine. I don't need you. What, what year was this? Uh, this would be 2016 to 2019 window.

SPEAKER_74: Yeah. Yeah.

SPEAKER_67: Um, I was just a weird beast. They couldn't understand. And then pioneer, I think is the right. Okay, sure. Yeah.

SPEAKER_04: You know, not for me to say, but you know, in a way, like if you were, yeah, of course, like for me, like, you know, it's not for me to say, but sure. Yeah.

SPEAKER_160: We'll say, we'll say.

SPEAKER_163: No, it never reminds me of the scene in, uh, get them to the Greek where they're like calling Russell Brad's character.

SPEAKER_95: Um, like, you know, it's like, he's like, yeah, you know, I sort of was going for with this African child music video and this theme album, like kind of a Jesus, like an electric

SPEAKER_74: Jesus. I mean, it's not for me to say I'm Jesus, but it's sort of, it basically compares

SPEAKER_163: up to Jesus with absolutely no self awareness. Um, yeah, as a rock star, it was pretty great.

SPEAKER_10: Um, but that was my big learning. And then they were like, what's your fault? All they wanted to know about was pro rata, follow on, etc.

SPEAKER_172: And I said, these are the large institutional LPs.

SPEAKER_10: And the reason they're asking that Ben is what?

SPEAKER_174: Why are they asking that question? Ben?

SPEAKER_49: Well, at the end of the day, this is not just a hit driven business. This is like a grand slam driven business. And so to the extent that you are in one of the few companies that will matter this decade on an enduring global scale, it's about owning as much of those companies as you possibly can.

SPEAKER_04: 100% correct. They believe they don't believe in spray and pray. They believe in hitting an outlier, the grand slam of grand slams and 10xing on that.

SPEAKER_10: So that's how they make money is when they get into an Uber WhatsApp or whatever,

SPEAKER_04: where they're in a fund that gets into one of those with a meaningful percentage that actually moves.

SPEAKER_13: And they're dealing with so much capital, you know, you're the Harvard endowment, you got 50 billion under management, like you need a lot to move the needle.

SPEAKER_04: Well, they they I think a lot of them are moving to a minimum of a $50 million check size for funds. That's like they're tiny. And I was doing a $44 million.

SPEAKER_178: I did a $44 million fund for a third fund.

SPEAKER_74: And then I realized, like, I don't really need them anymore. Because I can email my syndicate with a 300 members and have whatever 2030 $40 million fund popped up without doing any meetings. And then every time we do a syndicate deal, it does five times whatever the funds investment was.

SPEAKER_04: So we did 12 syndicate deals in June, we're on track to do 150 investments this year and put over 100 million to work. Even though I have a $44 million fund, I'm actually putting 100 million to work, which is sort of like being a GP with a $300.

SPEAKER_179: Now, are you leading in most things that you're doing? Most things now. Most things.

SPEAKER_180: Leading or leading co leading is probably the big thing.

SPEAKER_09: That's the that's the big question I have. We're gonna have to see how things evolve. You know, I've been I was an institutional VC for over a decade. All I did was lead. And it's been so nice not leading and following. And so the strategy here is follow. And we'll see how that goes.

SPEAKER_185: What you really want to do is hit one and then offer it to your L. Get a bigger allocation in all cases.

SPEAKER_21: So you find one you love you're putting 50k in. Ask them if they would be okay with you syndicating to your top LPs and friends. Another 250 and see what they say. I did that for calm and exactly those numbers. It was the first deal on Angelus from a syndicate was calm. And that was my first syndicate and I put 50k in. The syndicate came in for $328,000, $378,000, but 6% of calm 2 billion plus return.

SPEAKER_04: It's $120 billion position. It's the biggest return. Uh, we did a little pro rata. Um, but we actually were able to sell some in secondary twice along that journey to book some wins. So we still have 80% of our shares and it's the biggest return in the history of Angelus. Although because Angelus and I don't have a good relationship anymore. They never talk about that, I think, but I have the number one syndicate in the world, no longer an Angelus. And I have the number one return in the history of Angelus. No return comes anywhere close to calm.

SPEAKER_74: We're not saying you're Jesus, but not for me to say, but you should get on the SPV train

SPEAKER_04: immediately and say, if I could come up with, you know, 20 more people who put in 20k, would you be up for that? And just start that now because you're eventually going to get there and you're, and everybody's going to want you to put more money in.

SPEAKER_21: And, you know, Dave and Rosenthal is a brand. They're going to want you to have more on the cap table. Just give the founders what they want.

SPEAKER_04: Give your LPs what they want. And what happens if you have a common, you put 50k in from your fund. Great. It goes 400x. It becomes a $20 million position, whatever it is. Fantastic. But you could have put the other right 328,000 in and that goes 400x.

SPEAKER_21: And then you've got another 100 million behind it in returns. Marron, like that's what you're going for here.

SPEAKER_49: We had Ho Nam from Altos Ventures on for like a special episode of Acquired, what, two months ago, David? And Ho has this perspective where Altos is unique in this way. His comment is seed investing is the greatest discovery mechanism of all time. 100%. And they really, like, it's not a secret, but really their strategy is actually they're a growth investor, but they only growth invest in their own fund and their, their seed, you know, their fund, their early stage first check exists as a discovery mechanism to be able to better evaluate and better underwrite companies than the market could. So they know when to pile the huge dollars in the red information advantage way.

SPEAKER_74: 100%. You cannot trade on insider information in public markets. And that's all we trade on in private, correct?

SPEAKER_05: Yep. Like, literally, everything is insider trading in a private market.

SPEAKER_127: It's so, and you know, the funny thing about the Altos story, uh, and Ho and, and his partners

SPEAKER_09: is you would think like, it's so smart and it's what we do. And you would think the institutional LP community would love it. It took them decades to get the institutional LP

SPEAKER_31: community comfortable with what they're doing to your point, you know, Jason, about like,

SPEAKER_49: there, even if something makes sense and it's logical, if it's different than the way things are classically done, it's very difficult to get people on board because it's, it's new. It's, it's unproven. It might be better, but I do know the other thing works, maybe not perfectly, but it works. So I'm going to keep doing the other thing.

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SPEAKER_21: The more I watch what's happened, I realize, I came to this realization the other day, because I was like, I spent so much time on these big LPs. And they don't appreciate me. They don't understand what I'm doing. They don't appreciate me. And then I've, you know, at the time I had whatever 800 people in my syndicate, when I left Angel List, I wrote the book. Now it's at 8300. So it's 10x. And I'm doing 12 deals a month. I mean, I'm doing more deals.

SPEAKER_221: You're like a little tiger global over here.

SPEAKER_21: Well, you know, what happens is we, to exactly your point about Ho Nam at Altos, we have 65 of our 325 portfolio companies raising money right now. I literally had to take Emmy or Waterborne producer Jackie off of the accelerator. And I said, I know you want to do four more accelerator classes this year, do one, and then spend the rest of the time working with the 65 companies in our portfolio actively raising.

SPEAKER_04: Wow. 65. I mean, think about the scale of this, Ben. We would normally have a dozen companies. And you know what happens when your companies are raising,

SPEAKER_223: they need introductions.

SPEAKER_49: Oh yeah. That's actually the biggest choke point for a firm is that when companies are go, so, okay, let me take a step back. VCs can be valuable in lots of ways. The way in which they are the most valuable is helping you raise your next round in the best way possible from the best

SPEAKER_117: investors with the best terms in the shortest timeframe, or at least a timeframe that is reasonable to help the company go back to building.

SPEAKER_68: A hundred percent. Perfectly said.

SPEAKER_49: So when 65 of your companies are doing that concurrently, I don't know how you also do a podcast because oh my god, you are stretched thin.

SPEAKER_04: I mean, we literally had to say to everybody, tell us, you know, like fill out this form if

SPEAKER_74: you're raising essentially, and then I just had to put Jackie on it for 80% of our time to just,

SPEAKER_21: I told her every day, check in with 20 of the 65. Where's your fundraising at? So, you know, literally Monday, check in with 1520 Tuesday, check in with 1050. And let's keep this conversation going with them because some of them are going to fail. And then some of them want us to lead. And in some cases, we want to lead. So this is I think, David, the tip I'll give you is we require a monthly update in our side letter, which I'm not going to give any there was a profile written about me and maybe some of the controversial terms in my side letter, I'm not gonna give it any juice here,

SPEAKER_04: because it was so poorly written. But you guys read it, I'm sure. And there were a couple of controversial things there. One was that I require a monthly update, we require a monthly update, we've never sued a founder for not sending one. And we're happy to get for a year. What we do is we

SPEAKER_21: take the data, we put it into a spreadsheet, my team tells me, hey, J. Cal, these three companies doubled revenue in the last four months. What do you think? And I go to those companies and say, hey,

SPEAKER_04: would you like $1,000,000 out of $20 million valuation, we'll do a syndicate fund, we'll put

SPEAKER_21: in 150k? Well, you know, we syndicate 850. And we're done. Wow. And so that is the big tip is you have that information advantage given unsolicited offer. You know where I got that? Yeah, I've been

SPEAKER_230: thinking about this. I, I didn't realize that you're at this point, I steal that from. Well,

SPEAKER_04: Sequoia started. Yes, with WhatsApp. Yep. The unsolicited offer was the Sequoia innovation. So yeah, you know, three times. So here's the thing, I think what's that was three additional fundraisings, and nobody else was on the cap table, which means then Sequoia owned

SPEAKER_74: whatever percent 30%. I don't know, which means they wound up owning if that was 10%. Was that

SPEAKER_38: did they get 15% of Facebook? We kind of add Jim gets to our pool here? Yeah,

SPEAKER_49: I don't know. Yeah, that's pretty great. So here's the thing I've learned from like, I've been thinking about this particular issue. So I've watched a few great venture firms do it recently in in companies that we've been involved with at Pioneer Square Labs. And let's say, like, let's let's take a very negative view of it for a moment, you're like, wow, these guys are just trying to come in at a cheap price and buy up their ownership before there's a competitive market for this equity. They're not quite giving them the next valuation price. You know, this is sharky. However, what you're actually doing is, is pulling forward the time that they could raise and basically saying, if you don't want to do the work, whatever, great, you can take my term sheet, like I'm happy because I get my ownership, you're happy because you get more money in the door. On the other hand, the worst case quote unquote, worst case scenario is it gets shopped. And then suddenly there's a frenzy to fund this company that you're already a shareholder in.

SPEAKER_246: You win both ways. It's value created for you. It's value created for the company.

SPEAKER_04: It's a win win. When I gave these offers, I'll tell you the companies I gave them to Fitbot, Lead IQ, Neighborly. Who else was in our portfolio that I gave them to? Anyway, those were a handful of them. All of them said, of the four, the first four times I tried this, a grin, I did it with grin. Two of them said, Okay, I'll take the money. Yep.

SPEAKER_10: Immediately. The other two said, No, it's too low. One said it's too low. One said I don't want to

SPEAKER_04: raise money. The one that said it's too low. I said, Okay, great. Take it. Shop it. You have an

SPEAKER_108: internal offer and then come back to me. She did four meetings.

SPEAKER_127: Honestly, if you want to get a great external round done these days, like that's you got to do that. You got to be like, Hey, my insiders want more. I'm fighting them off.

SPEAKER_95: Exactly. So I did that. And it was only a million on 15. And the founder came back and said,

SPEAKER_74: You know what? I did four or five meetings. It was really annoying. And I don't want to change the governance of the company. And they were having a hard time getting to your number or slightly more than it. And you'll just do this. There's no paperwork. Nothing really has to change in the company. I'm like, Nope. Governance stays the same. We just give you a million dollars done. And

SPEAKER_04: then so three out of four took it. The fourth was fit bod. They really are like a Pegasus. They're kind of like calm, they don't raise money, they just make money and the cash balance keeps building. And then eventually I got them to take 2 million. And it was that evaluation that was four times more than my original offer. But they, you know, they forex revenue. So or 3x revenue and over some period of time. But that's the power move, I think, David, for you is to watch like a

SPEAKER_21: hawk and have that system where you can then jump in, ask for a pro rata. Even you could ask for super pro rata, which is a little bit polarizing. But you could say, Hey, can I put 50k in now and get 250

SPEAKER_26: in the next round or whatever? Now you have to have the ammunition for that, which you don't get.

SPEAKER_127: What's the way you manage the ammunition? Because you don't always I mean, at this point, you got a pretty good idea that your syndicates going to be there for when you call on it.

SPEAKER_04: It's critically important that you have a track record where you're sending some

SPEAKER_74: predictability. In the beginning, it was really difficult because I would tell founders will do 200 and 600 would come in or 100 would come in. Right. And I just told them, listen, after I did the first couple, I was like, I have no idea what's going to come in. If you want to do this.

SPEAKER_04: It's a process. It takes six weeks soup to nuts. And you know, that's obviously a liability now the amount of time it takes. So we've gotten that time down to three weeks or four weeks. But it's still a process. You have to write a deal memo, you have to circulate it. The good news now is we just did for a very high profile founder who gave me a million dollar allocation. We emailed the syndicate and said, This is super oversubscribed. Sequoia is in the deal. This other person's in the deal. As a favor, they gave me a million dollar allocation. We're going to allow I'm putting 250

SPEAKER_47: in from the fund 750 from the syndicate. It's going to be 150 people at 5000. We had $6 million in demand

SPEAKER_264: for that 750. I think it was easy to follow David until you're getting squeezed out by

SPEAKER_146: these ridiculous 600 of the 8300 members asked for an allocation in the first 48 hours.

SPEAKER_04: I've never seen anything like it. And many of them were asking for 75k 50k. And I just said, you can request whatever you want. But it's going to be 150 people at 5k each. So that's the level I've

SPEAKER_267: gotten to now where I'm basically hosting a lottery. Got it. That sounds stressful,

SPEAKER_102: though. See, this is the whole reason I kept this small. I mean, we could have raised 10 times the

SPEAKER_29: money. But I was like, I want I don't want that in my life. You do trust me, you want to be able to

SPEAKER_74: own 10% 15% of a unicorn. I've never I've only owned 5% of a unicorn, which was calm. I've to this

SPEAKER_04: date, I own five to 15% in many companies 20% many companies that broke the 100 million barrier. And I'm starting to watch those now. That becomes like a totally different ballgame because we own 15% of the company now that's worth 300. And I'm like, Oh, my God, that's $45 million position. You know, and the two biggest positions ever had were calm and Uber and those both broke 100 million. And I'm like, Wait a second, this company is not worth anywhere near calm or Uber's valuation. But we own so much of it 15% times 300. If they just get to a billion, I'm gonna have a $150 million position in this $1 billion company, it gets pretty exciting, you know. So there's two ways to win, you can hit, like, literally the sniper shot, which is what your fund is designed to do. Or, you know, you can get the shotgun or, you know, whatever, you can you can hit the 5% ownership, you got to get to 5% ownership

SPEAKER_185: and your winners, I think, to really move the ball forward. And you know, the winners. So why let other firms take it from you, David? I hear you. I hear you. And they want you they don't want these

SPEAKER_49: other firms. They want David. You could you could because they have you as a small owner on the cap table if you're throwing in, you know, 50k in a in a deal, but you're not like their board member. And the next time that they're going to go raise around and it's going to be a $10 million round, like, do they want to bring on some unknown? Or do they want you to step up and be the board member? I don't know if you're interested in that. But being a board member is a lot of work. David,

SPEAKER_63: David, how old are you, David? About to be 37. Okay. This is your prime earning window. 37 to 57.

SPEAKER_04: This is when you can make bang. Put your head down. Say yes to everything. That's a great founder.

SPEAKER_10: And do not worry about time or life work balance. Ben has no life. He's never had a life.

SPEAKER_287: He is. We put a lot of work into this podcast. You put a lot of work into your podcast.

SPEAKER_74: Well, no, I mean, here's the thing about your podcast. You know, when you have a top,

SPEAKER_21: you guys are top 10 tech podcasts consistently, when you're in the top 10 like that, and you have the deal flow we have, you can offer something to your founders now to, you know, it's not just a feeder

SPEAKER_04: system. That is the base level thinking of why everybody copied me as a blogger and as a,

SPEAKER_290: I'm not saying I'm Jesus or anything, but you know, when I climbed up, put me on the crucifix,

SPEAKER_04: you know, and they stabbed me and you know, whatever.

SPEAKER_291: I think, I think you know, you're not Jesus. You're, you're, you're, you're, you're Moses. You got the tablets. You're bringing us the tablets here.

SPEAKER_04: Right. But no, here's the thing. You, um, everybody thinks of it like a feeder system. That's like base level one thinking. And I understand that. What then you realize is, then you get to do the victory lap with your founders. And the fact that you get to include them on the pockets,

SPEAKER_223: have you had your investments on the podcast yet?

SPEAKER_295: Not yet, but we talk about them.

SPEAKER_223: Okay. So here's what you have to do.

SPEAKER_295: Because our format, you know, we do like the huge case studies.

Chamath Palihapitiya: I know that, but you can always do an extra one. You should just take two of your founders each,

SPEAKER_04: do a special episode, you have all four of them on, and you each ask them a couple questions, how the business is going, how you came to invest in the company. It's editorial gold,

SPEAKER_298: gold for the audience.

SPEAKER_09: We started doing with Paki and Mario. We are not going to say it wasn't inspired by all in not going to say it wasn't. Yeah. Uh, we do once a month we do, we call it the idea dinner where we all just get together. We talk our

SPEAKER_04: own. Perfect. It's great. It's great. And listen, there's a lot of people copying the, uh, the all in format now of just, you know, four bros for, you know, sisters or four brothers,

SPEAKER_148: whatever, just getting together and, and hashing it up. I think it's a great idea.

SPEAKER_304: Hey everybody. I thought I would bring Christina Cassioppo. I pronounced it correct. I'm hoping Christina got it. Yep. All right. You're the founder of Vanta. Uh, people have been hearing your ads on the pod for the last year, and I thought it'd be fun to have you on and you to explain why you created Vanta and what sock two is and why it's important people get it right.

SPEAKER_306: So let's start with what is sock two for people who are just realizing they have to become sock two

SPEAKER_308: compliant for sure. So sock two is at a tie level. It's sort of a customer asking you to prove your security. So if you've heard about one, it probably comes, you're probably a B2B company and you're, you're doing sales and somebody asks you, Hey, can I have your sock two report? Or, you know, Hey, can you go through security review? Or they usually don't phrase it like this, but Hey, I'm going to put a bunch of data in your product. And I want to know if you're actually going to be secure or leak it over the internet. So they ask you to get a sock two report.

SPEAKER_304: We know it's 20,000 to 50,000, maybe even a hundred thousand. You know, if you roll your own, you do it manually. What is the average Vanta customer spend?

SPEAKER_308: Yeah. So the average Vanta customer spends less. So kind of 10,000 on up from there, but then even in terms of the cost savings, it's a ton of time savings. So rather than kind of giving up an engineer or two for a year, which is just super painful, no matter how large your company is, it cuts it down to can be 20, 40 hours on the low end.

SPEAKER_306: All right. Fantastic. Well, thanks so much for coming on. And you've been very nice to our audience, giving them a thousand dollars off, which is a really significant and generous offer. Go to Vanta.com slash twist V-A-N-T-A.com slash twist to get a thousand dollars off your sock too. Thanks, Christina. Appreciate it. Thank you so much. It is interesting. So like on a meta level,

SPEAKER_49: just to talk about all in for a second, I've been trying to dissect it in terms of like why it's working so well. And obviously your personalities are fantastic. You all have inside and not SEC inside, but like, you know, inside your knowledge. Inside baseball. Inside baseball. Yeah. Inside baseball of a lot of really interesting

SPEAKER_320: dynamics going on. The poker story yesterday.

SPEAKER_49: But here's the thing that like you guys overcame, which is typically four voices is too many on a podcast, especially for male voices, because the audience typically gets confused. Each of you already had your own personas. So in creating this super group, it, it became something different. And in the format that you do, you've done it at such a fast pace where it's like, it's aggressive. It's like, it's moving at a quick clip. There's like, everyone's giving each other that like, you're absorbing knowledge that you can't get anywhere else because it's a very unique set of knowledge that you each possess. But you're having so much fun. Yeah, along the way that I think it's the number of people who could adopt that format successfully is very low. I think that's right. Here's the

SPEAKER_74: thing I always tell people because I was getting recruited during that Shark Tank era to be on a lot

SPEAKER_04: of the shows, like Planet of the Apps offered me to be on I declined on that one. I did a show with NBC, I did a pilot with the Weinstein company that didn't make it on air, thank God, that would have been really bad. And, you know, a lot of those shows I was going to do the really the big problem they had was credibility. If you didn't xy matrix on really, there's like three vectors, your credibility, your ability to entertain and speak publicly, and then your desire to do so. And if you take those three vectors, and you look at, you know, Chamath, he is highly credible, he's got that success. He's really good at speaking publicly. And he wants to do it, because he said to me the origin of all in was, hey, I want to do a podcast with you. And then you go to the next, the next, the next, you know, Sachs, great public speaker, very credible and wants to be on then you have Friedberg, who is very successful, kind of wants to be on but I had to push him a little bit. And then in terms of public speaking, I also had to push him a little bit and coach him to he brings a

SPEAKER_21: lot of magic to the pod. Absolutely. I mean, the episode we did without him this week, I was almost going to throw it away. I mean, it was good, but not great. I did my mind without him. And I think

SPEAKER_04: that any of the three of us on it's good, not great. But you're exactly right. Then you look at somebody like the Professor Cole takes, you know, he's not credible. He's not credible. He wants to be

SPEAKER_05: on TV. You know, and not a reluctant hero. And he can't speak any and he can entertain or speak,

SPEAKER_04: I guess it's cringe worthy entertainment, obviously, you know, pretty sexist and misogynistic and gross wrong. But no, but that's what I mean by credibility. So you a lot of the TV shows are like, we don't care that Prof G is wrong. He's taking his shirt off. He's entertaining. He talks about his ED, you know, but the thing I don't like about him is then him saying Sheryl Sandberg only has her job because she's a pretty face and that misogynistic kind of stuff, which I think is, you know, he's terrible at predictions, but you can be entertaining and terrible. Um, and that I think that's what I learned about media because all those TV shows would put people on who had no credibility, but really were loud voices. Um, and that was the problem, you know, they, they were putting on all these celebrities on planet of the apps.

SPEAKER_09: And so, so on the, on the tablets here, I gotta, that's, that's the last piece in the, in the tablet for me. Uh, yeah. How do you think about your J Cal portfolio allocation? You said, you know, like,

SPEAKER_31: you're, you're, you're still, you're also in the prime of your earning careers. You got your head down.

SPEAKER_65: 50. Uh, the media activities, the investing activities. Yeah. So the media I do, cause I love,

SPEAKER_04: um, and it literally is no effort for me to sit here and talk to you or to host all in. Obviously, that's like a, that's my superpower where it's also real business for you, right? Well, yeah, I mean, I think all, I think right now this week in startups is doing 3 million a year in revenue and sold out four days a week. And you'll be sold out five days a week soon. And we sell it out every year. So, you know, it's sold out for seven years in a row. And every year it sells out, we add more. So it's great. And it pays for the team. But for me, I just love doing it. You know, like this time with you guys, I'm writing down notes, and it will give me inspiration for things in my day job. And then in terms of investing, right now, my goal is to get to, to get the syndicate to, you know, over

SPEAKER_05: 10,000 members was always the goal, and to do 100 deals a year, and we already surpassed that. So now I'm setting a goal of 200 deals a year, and 20,000 members. And to be able to put 250 million to work a

SPEAKER_21: year, which I'm going to do it for 10 more years, we mean, I would put $2.5 billion to work with a syndicate as a solo GP. There's never been a solo GP who's put $2.5 billion to work. And so for people who are like, ah, he's the dumbest guy on the all in podcast, that is, that is, I'm afraid,

SPEAKER_68: correct. And actually, if you just competition, if you think about any venture firm per GP, if you divide total a under manager by five, by by number of GPs, yeah, probably on average five, has there ever been that much capital put together at that pace? Under one GP?

SPEAKER_345: No, I don't think so. I'm trying to think. Maybe Chamath would be actually the example of somebody who's putting that much to work. How many? How many GPs does the vision fund have?

SPEAKER_111: I don't know. That was a lot. A lot. Dozens, I would guess. A dozen, I guess,

SPEAKER_349: something. Who knows? The founders fund probably hits that. They probably have six partners at a

SPEAKER_22: given point in time. Yeah, five or six. And they're deploying a lot of capital. Yeah, so they have a

SPEAKER_10: billion $2 billion, six, probably 150 per fund per person, they raise a new fund every 24 months,

SPEAKER_74: 36 months. I think their funds are bigger than that. Okay, so let's say 200 million per partner, and you do five funds a decade. That's a billion dollars deployed per partner. I think that's possible,

SPEAKER_67: actually. Two and a half billion, but you know, whatever. I mean, I think I could sustain it and

SPEAKER_74: enjoy it. It just people have to get used to the fact that I am not the only person at the fund,

SPEAKER_04: which people are starting to get used to, like, so when I go on vacation this time, I literally told the people who are in the middle of raising, Jackie will manage the raise with you. And Heidi and

SPEAKER_111: whoever over the next whatever two weeks when I'm on vacation, and you know, I can jump in if you need me,

SPEAKER_49: but Oh, not now we're into an area that I'm extremely passionate about is leverage on time. So what are what are the areas where you're like, Oh, this is great. Like I can figure out a way to really scale this and get more leverage and have great people work with the company or work with the media. And what are the things where you're like, this actually is a core Jason activity that I cannot outsource?

SPEAKER_04: Um, this is a great question. I think when a founder is at a crossroads, um, where something is going really badly, like the company is imploding, or the company is getting bought, or they have a founder crisis with their co founder, that's when you got to call in the fixer, there's no substitute for me coming in, and you know, guiding them through that storm. So I would say you know, the storms, you know, a mini storm, no problem. But again, we're talking about serious, you know, the boats flipped, and you know, the passengers in the water, yeah, you're gonna need me to get on the helicopter, get out there and Coast Guard it, whatever. Um, the thing I've done

SPEAKER_21: in terms of leverage, which, you know, I think is something people, I discovered accidentally, was I

SPEAKER_26: started doing like an office hours type thing. And then I made it open to more and more people and

SPEAKER_04: then having a slack. So I do a thing where and I just got off it before this call, which is why I was 10 minutes late. Sorry. Um, I have had about 10 founders on two founders pitched me their three

SPEAKER_74: year model. So they said, here's our three year model. Here's what we're thinking, our three year plan. Yeah. So I realized because Doug Leone told me, you know, Jason, hope is not a plan, I would

SPEAKER_356: rather you have a plan for the company. And they just literally burned into my brain, like Doug Leone

SPEAKER_95: is like, super mensch. He speaks, you listen. Yeah, I mean, Doug Leone has my phone number, and he calls me sometime. And, you know, I see Doug Leone comes to my phone, I'd literally my heart rate goes whoop. And that doesn't happen with anybody anymore. And I, I know, but he's got a propensity to just call people on the phone and have a two minute conversation with you. And this has happened,

SPEAKER_31: you know, 20 times in my life. He more or less cold called the CEO of one of my angel investments on a Sunday a year ago. This is his power move. Like he just calls and he's like,

SPEAKER_95: He's from Sequoia. And you're like, Hi, Doug. You know, and sometimes it's something completely

SPEAKER_04: random. And sometimes it's something completely life changing where he's like, Oh, this LP would like to meet you. And would you be open to that? And I'm like, Yes, Mr. Leone. Anyway, when he told me that, then I started doing this with my companies. And, you know, if you are going through the three year plan, and eight other people are listening, nine other people are listening.

SPEAKER_21: And then you say, Hey, what are you what is the other nine founders thing? So those kind of group settings, where I am not the only person, but I'm leading the discussion socratically and asking the

SPEAKER_185: probing questions, man, is that a game changer for founders? And for me, you know, so that that's how

SPEAKER_382: I scaled myself. And I'm going to continue to do those kind of events. And then you know, if I'm doing

SPEAKER_21: four days a week, I told my team, give me the list of the highest revenue companies in our portfolio

SPEAKER_04: that haven't been on the podcast. And lead IQ fit bod, and grin, I just did dedicated episodes with

SPEAKER_21: those three companies in the last week or two. And I'm just going down the portfolio. And that's how I'm going to do it from now on when the companies hit 10 million, five to 10 million in revenue,

SPEAKER_04: I'm going to join the boards when they're under that amount, I'm gonna have the team, you know, be board observers, basically, on those. And so that's, that's, that's another honom. It's very

SPEAKER_49: similar to what he does, where he says, once you hit a $10 million run rate, even if you're one of my partners investments, now you have my attention. And now I start evaluating to figure out if we should be the

SPEAKER_305: growth investor in this company. Perfect. I mean, I think it makes total sense. There's like a,

SPEAKER_04: there's a clear benchmark of where to get to 17 managing partners and partners, not included masa and the CEO of SoftBank's investment team, according to our quick research vision fund has 10

SPEAKER_241: managing partners, not including masa. So that makes sense. So on a per partner basis,

SPEAKER_04: yeah, you would be deploying more. I think so. Yeah. I mean, also, I think the syndicate is turning into more of a platform than, you know, vis a vis Republic, you know, as opposed to a single person syndicate. So we did two deals this past year that were consensus deals. So we started this remote demo day, and I'm interested in your feedback on this, where we said, Hey, here's seven companies, which ones do you want to invest in when they broke 250 or 500? I think we just said, Hey, we'll do the diligence and we'll syndicate it. It's not necessarily Jason's deal. The syndicate voted collectively. So that's something

SPEAKER_21: I've got sloshing around in my brain is, Hey, if the syndicate wants to invest in this company and 100 members want to put in 10k each and it's a million dollars, who am I to stay in their way, we could just process it for them and take the carry do the diligence and manage the investment for them.

SPEAKER_49: So tell me more about what it means to for the syndicate to vote. Is it simple majority?

SPEAKER_211: Because remember, we're in a consensus driven industry.

SPEAKER_04: Well, if 100 people out of 8300 wanted to put skin in the game of 500k or more, it's such a small bet. And it's such a small amount per person, I think you could be pretty liberal promiscuous. I don't know what the word here is. You can be pretty aggressive. I think arrest is probably the best word. If it was 5 million, you really do want to have somebody who

SPEAKER_74: is the lead, right? So I think when you're making these 250 500k bats, and it's 100 people at $2500 or 5000. If you look at it like an experiment. Yep. It's almost like a Kickstarter, you know, kind of like a small bet. So the 25k bet. Can I give you some advice, Jason?

SPEAKER_49: Yeah, please. Like what I would do. So I think you need to. I think you need to knight some people within the syndicate to be smart money. To basically say you are signal creators. Because otherwise, I mean, you have literally written the book on how to become an angel investor. So you're going to attract every doctor and lawyer out there eventually. And so you got to make sure that some of them are going to be really good angel investors.

SPEAKER_396: And so it's starting to have the vast majority of them about them up. Yeah. Interesting. So

SPEAKER_74: you're your fun. I love this idea. By the way, deputizing people. I've also been thinking about the scout programs. Who's the guy who did the Indy VC thing that failed and he did the whole price. God, that's a good idea. It was a great idea. Bryce is I was a little critical of Bryce because with the indie idea, I was like, this is stupid. Like, why would you

SPEAKER_67: give founders back their money? Talk about putting a stake in the ground, the burning unicorn head. I loved it. I think it was good. I was like, this is dumb because

SPEAKER_04: you basically are going against the basic concept of venture capital, which is you're defined by your outliers. And you're saying you don't want outliers. I was like, thank you. I will send you all the people we say no to. And can you please send me the unicorns? He didn't appreciate it. And I

SPEAKER_169: invited him on the pod a couple times. He doesn't like me with good reason. I was super critical. But he

SPEAKER_21: did get something very right with a scout program, which was he opened it up to anybody. He had an incredibly diverse set. So he took Sequoia is like, you know, doing the management teams at the

SPEAKER_26: companies they invested in and you know, people in their orbit and he just said, Hey, I'm opening this wide open. And then he offered them a $5,000 cash payment if they made the investment

SPEAKER_05: as opposed to carry that could come down the road. And I was like, Oh, that's brilliant. That's brilliant. Just cash. So if you were some 25 year old,

SPEAKER_406: you're plugged in, you're relentless. That's a lot to you.

SPEAKER_49: It does create a signal though to get a deal across the line. Like it does create a strong

SPEAKER_90: incentive for you. No, but they just scout the deal. It's up to then Bryce or me or you or David

SPEAKER_74: to then shepherd the deal. They're just giving it to you. They're putting it on your plate saying, Huh? I found this company, you know, it's, it's going to be trading for free with, you know,

SPEAKER_04: for millennials and an app, you know, the end. And so I'm, I'm going to steal that idea from Bryce.

SPEAKER_31: I think that's actually, that's a really good idea. Cause it's asymmetric like to, to a fund, your $44 million fund, who gives you a 5k, whatever, that means. 5k great. Well, I was thinking of doing 5k. It means a lot.

SPEAKER_21: I was thinking of doing, let me see if you like this idea, 10k,

SPEAKER_05: zero carry 5k, 5% of our carry. So one of 20 points or zero cash and two points to carry 10%

SPEAKER_185: of our carry just for scouting it and filling out like a basic deal memo feels like, and then they

SPEAKER_04: wouldn't be officially scouts. I got to come up with another name for it, where they just are.

SPEAKER_414: They're, they're like, um, uh, talks about this, uh, they're your radar network.

SPEAKER_108: The radar network. They're just affiliates. Like they're just saying, Hey, here it is, but I'm not going to be on the board. I'm not going to shepherd the company. I don't even need

SPEAKER_26: to, you know, yeah, I don't even need to, um, be an official scout. So that's my fear is I don't

SPEAKER_21: want people running around. I had somebody who heard that we, cause we do, we do a carry Twitter bio becomes Jason Calacanis. Literally, that's what happened. Somebody literally did that. They said they were scouting for me and I was like, who told them is okay. And one person on my team was like, well, I told them we had a carry share, but I didn't tell them they were scout. Um, but they use

SPEAKER_231: scout like in a lower term and this person literally put their LinkedIn scout for Jason Calacanis. And then somebody's like, Oh, I met with your person. I was like, I was like, Hey, Jackie, Ashley, did this person work for us? They're like, no. I'm like, does anybody know anything about this? People started searching their emails and they're like, Oh, we found it.

SPEAKER_417: Our bed. Pretty crazy. When you think about it. All right. Well, we had a really great idea for

SPEAKER_74: this episode and it wasn't fund formation and innovating and venture capital, but here we are.

SPEAKER_04: Uh, and we were gonna do our Mount Rushmore of venture capital. I'm gonna call an audible here and say, let's do this for the next episode. Um, and we will pick our Mount Rushmore of venture capitalists and we should tee it up now. So let's tee this up for the next episode.

SPEAKER_420: Ooh, I like it.

SPEAKER_04: So we're gonna tee it up Mount Rushmore as a device means the top four of all time.

SPEAKER_74: You've seen this on sports shows where people say, here's my Mount Rushmore. It's LeBron,

SPEAKER_04: it's Jordan, blank and blank. And then you have this great vibrant debate. We're gonna do this for VCs.

SPEAKER_423: And we need to pick the criteria. Like, I think that's why it's going to separate into two episodes,

SPEAKER_49: because we could have a healthy debate here on like, just how would you decide who should go on Mount

SPEAKER_185: Rushmore? Yeah. But that's not the only lens. Is it Ben?

SPEAKER_49: No, you could also take the founder lens and say, if I could take a check from anyone, all other terms being equal, who was the greatest four people that I would want on my board?

SPEAKER_434: Right. So we can even say, is it today? Is it alive or dead? Ooh, right. Because you could say,

SPEAKER_21: Hey, listen, you have somebody like Don Valentine, uh, who founded Sequoia and did Oracle Cisco. I mean, kind of hard to even Atari. Yeah, I mean, how do you even, like, put Don Valentine in perspective here,

SPEAKER_04: you know, compared to Chamath or David Sachs. But you know, Don Valentine, rest in peace is not going

SPEAKER_10: to be able to be on your board today. So I guess you have to make some allotment here when you're doing your four of historical today and everything in between.

SPEAKER_414: I think we should I think we should say all of them in their prime.

SPEAKER_445: Okay, in their prime. Okay, I think that's a that's a nice way.

SPEAKER_49: So I'm starting a company in 1982. And, you know, that so if I'm taking Don Valentine, it's like the 80s Don Valentine.

SPEAKER_04: Got it. So if we're talking about Jordan, we're talking about Jordan is prime. We're not putting a 50 year old Jordan against a 36 year old LeBron.

SPEAKER_25: Yeah, no, no wizards here.

SPEAKER_74: Yeah, no wizards. Jordan, we're saying Jordan in the prime versus because some people are kind of retiring. And yeah, that makes total sense.

SPEAKER_448: So I think they I think they're actually three, though, potential

SPEAKER_09: vectors, vectors, and we should do I think we should decide on one of them. One is the LP perspective. Yeah, just straight up return driven. Yeah.

SPEAKER_13: One is the founder perspective that Ben said, which is who do who do? It's a competitive round. I could have anybody who am I choosing?

SPEAKER_49: Most helpful. And I do want to add one caveat to this. It's not the most founder friendly VC.

SPEAKER_227: It is the VC who will help me create the biggest win for everyone.

SPEAKER_04: Right, right, right, right. They're going to. Yes. So we're talking about 2007 Bill Gurley

SPEAKER_148: in his prime, you know, doing Uber and you know, every other incredible company did during that time.

SPEAKER_49: Got it. Right. Because otherwise, you could have someone who's just going to like roll over on every decision and be your, you know, have your proxy, which is like, that's, that's not really what we're getting at here. Right?

SPEAKER_09: Yep. Okay, so those are two. And then I think the third potential lens is your, you are starting a five person venture capital firm, you are one of the four,

SPEAKER_31: one of the five GPs who are the other four GPs you want.

SPEAKER_174: Wow, that's a powerful lens. So you're saying I'm building my own fund from scratch.

SPEAKER_457: Yep. That's kind of like building an all star team. Yeah.

SPEAKER_90: That's the best one, actually, because it takes everything into account. It takes the founder into account and it takes the LP. And I think you unlocked it, David. So this is basically,

SPEAKER_74: I'm starting a five person venture firm. I'm one, David's one, Ben's one, we're each starting a new

SPEAKER_04: venture firm, alpha, beta, delta, whatever. I don't know who wants to be the beta in this group, or the alpha. What are we starting like a sorority?

SPEAKER_274: Something I'm just coming up with generic names. Okay, we're starting Oak, Elm, and whatever, pick another tree. Gilbert and Rosenthal. What do you like?

SPEAKER_462: It actually sounds like a great law firm. That's a great law firm.

SPEAKER_464: It does, right? A bunch of immigrants, 1200 bucks an hour. We're gonna need a retainer here.

SPEAKER_05: But I like that. We each pick who we would want in our new venture firm to build around.

SPEAKER_49: I do like this one, because it does take the others into account. The question is, do we care how these characters interplay with each other? Like, can we pick some oil and water here?

SPEAKER_246: You have to think chemistry. You do have to think chemistry, how they work with you,

SPEAKER_74: how they work with each other? Are they gonna stab you in the back? Yeah, no, I mean, are you gonna have four alphas? Maybe they can't work together?

SPEAKER_10: It's definitely something to think about. You know, like, hey, listen, Keith Raboi is a heck of a VC.

SPEAKER_90: But what are you about to say? You're not putting Keith Raboi and Chamath in the same firm. I mean, what the happens if you have Raboi and Chamath in the same

SPEAKER_04: Monday morning meeting, and they're trying to decide on investing in a company, and Keith tells Chamath, he's an idiot, and Chamath tells Keith, he's an idiot. And these are two of the most successful guys. That's like having two. Oh, I would love that. That's like having Kobe, Kobe and LeBron, or Kobe and Jordan on the same team. There's only one

SPEAKER_456: basketball. Chaos agent. Oh, I love it. I'm a, you know, the Dungeons and Dragons, like when you're building your character. Yes. I'm chaotic good. Like, that's me. I'm chaotic evil. Yeah.

SPEAKER_122: Oh, great. So I would love chaos. This would be like putting Dennis Rodman

SPEAKER_90: in. And who was the guy who would say ball don't lie? Rasheed Wallace, Draymond Green, Rodman.

SPEAKER_261: Isn't Rodman already in there? And then who else is absolutely

SPEAKER_95: going to get a technical in the first five minutes of a game? Steven Jackson? Oh, no, Ron Artest went into the mouse.

SPEAKER_486: Oh, here's my team. Oh, yes. This is my team. Ron Artest, Rasheed Wallace, Draymond Green. And who did it? Dennis Rodman. Oh, my God. Me and those four guys in the NBA team. And you're the point guard.

SPEAKER_95: Literally, the four of them are absolutely getting technicals and getting two of them are kicked out of the game. We're playing three versus five. Oh, my Lord. But yeah, Steven Jackson is the only one who actually can, I think he's the only guy who

David Friedberg: actually beat up a fan in the history of the NBA. Our test choked a fan, I think. Wasn't that the coach? Oh, yeah. You're talking about Sprewell.

SPEAKER_493: Oh, that's Sprewell.

SPEAKER_95: That was Sprewell. Sprewell choked P.J. Carlissimo.

SPEAKER_493: P.J. Carlissimo, yeah.

SPEAKER_95: But from what I understand, P.J. Carlissimo said something.

SPEAKER_04: This is the inside story in the NBA that nobody knows. I don't know if this ever come out, but I know people in the NBA. Let's just say P.J. Carlissimo may have said something that was

SPEAKER_496: choke worthy to a player. Yeah, that'll do it.

SPEAKER_64: I don't know that that's true. But the people I know in the NBA said, you know,

SPEAKER_21: listen, I stay on Sprewell. I'm just leaving at that. I sim for Sprewell.

SPEAKER_16: Great. It was our test, right? You changed his name to Metta World Peace. Absolutely. That's right. Yeah.

SPEAKER_90: We're going to give him a tease.

SPEAKER_49: And maybe this will be good because then people can tell us, too, if they feel like we're forgetting people that they would want us to include in the discussion.

SPEAKER_74: All right. So here's what I think would be a good idea. We each do one pick today, but let's read down the list. Just a scratch list here. Just a starting list.

SPEAKER_04: Don Valentine, obvious. Ben, read the next one. John Doerr. That's a layup.

SPEAKER_502: Layup. Mike Moritz.

SPEAKER_47: That's an obvious one. Bill Gurley, obvious one. Peter Thiel. I mean, Facebook, Twilio, Palantir.

SPEAKER_506: We're going to go to the East Coast for this next one. Fred Wilson, representing New York City. I mean, come on. Twitter, Tumblr. Coinbase.

SPEAKER_384: Oh, neat.

SPEAKER_49: The question on this one is, are we talking Bond Capital or Kleiner Perkins, but Mary Meeker. And the question is, when was she in her prime?

SPEAKER_255: Well, you know, she was not an investor and was an analyst, but she was a great analyst.

SPEAKER_04: She's only been doing venture for a decade.

SPEAKER_396: I think we can say we could get her during her Morgan Stanley days as a VC.

SPEAKER_185: That would be a wild card because she eventually did move to VC, but if she had left in her prime, she was playing the wrong sport.

SPEAKER_178: You know, she should have been at a VC firm probably. But yeah.

SPEAKER_321: Yeah. Was she the lead analyst on Amazon for their IPO?

SPEAKER_518: I think that was girly.

SPEAKER_219: I think that was girly.

SPEAKER_518: So what what what what IPOs was she? I mean, probably everything.

SPEAKER_381: Probably Yahoo and all those kind of companies during that time. Blue Mountain Arts.

SPEAKER_306: Mountain Arts. Forgot about. Okay. So then you got Jeff Jordan from Andreessen Horowitz.

SPEAKER_49: So far, and David and I just finished our two part Andreessen Horowitz back to back five hour extravaganza on acquired. Are they 13 funds? Uh, I know they're 18.8 billion under management.

SPEAKER_13: I think in terms of the numbered early stage funds, they're on either seven or eight right now, but then they've got bio, they've got crypto, they've got growth. They've got the cultural leadership fund.

SPEAKER_49: But Jason, I noticed here, I don't see Andreessen or Horowitz on here. I just see Jeff Jordan on this list.

SPEAKER_531: Whatever. I got beef with Andreessen and Horowitz. They wouldn't come on the pod.

SPEAKER_95: They're PR people. Who's the woman who runs all their PR? Margaret. She's fantastic. Yeah. Oh God. Jeff though. Oh, we, we gotta, we gotta talk up Jeff.

SPEAKER_534: I can't stand her. I find her incredibly annoying. Jeff Joy. Jeff had.

SPEAKER_95: She's the one who jerked me around. They wanted me to have all the partners on and have, and I had to talk to her constantly. No offense.

SPEAKER_04: But, you know, listen, I'm Jason Calacanis. I'd only talk to the PR person. I got more countries in my LP and then you're putting me on your PR person to like, beg for scraps and try to convince them.

SPEAKER_64: And then they're like, she tried to horse trade with me a whole bunch. You know, have this person on the pod and then maybe we'll have him. And I was like, you know what? I'm out. I don't see. It does sound like. I'm beyond this. Like, I'm done with you guys. Like, and gals. It's enough. Like, I don't want to negotiate.

SPEAKER_21: Do you ever send them deals? Are you just done done? A hundred percent. I do the opposite. And I told that to them. Well, the other thing that happened was I, this is the thing that really pissed me off. There was, I was moderately pissed off about them jerking me around about coming to a conference or coming on the podcast.

SPEAKER_62: Oh, are you gonna talk about the Uber Series B?

SPEAKER_21: I think we should. I think we should do a diversion in a second. Let me just say that. That to me was like, just super annoying. And they were super annoying about it. And it was disrespectful. I felt to me, because I work really hard to put on these events. And they're free for founders. And you're showing up at everything else. And the second piece was then Margit or Margaret or whatever.

SPEAKER_04: Her name is like jerking me around and trying to horse trade with me to get their other partners and their terrible books that nobody reads that they buy 10,000 copies of to put on the, you know, list. And I was like, yeah, no, I'm out. But the thing that really got my goat was Mark was like, yes, that is company, send us companies. This is when they had their first fund second time. I send three companies, two of them. Mark gives the founders over, baits and switch the founders where Mark replied to the founders and said super nice things to the founders. The founders get excited. Those two founders flew in for meetings. Mark didn't show up for the meetings. Junior partners, whatever, show up. In both cases, they said the meeting was incredibly short. The founders, the partners were rude, were disinterested, and they felt like they had to take the meeting and couldn't end it fast enough. And that to me was, that was it. I was like, you know what, if I'm going to have this bad of an experience, my founders are going to have this bad of experience. And I told Mark, I'm taking every company. That's a unicorn. I'm bringing the ball down court. I'm sending it to Sequoia.

SPEAKER_546: To Benchmark. That'll really get them riled up.

SPEAKER_04: No, I did. And I was like, listen, Bill Gurley shows up for me on the podcast. Sarah Tavel comes on the podcast. Anybody I ask at Benchmark, Sequoia comes on the podcast. So they come to the events. My God, some of them even sponsored the events when I was getting started, I needed help. And then Andreessen Horowitz was just persnickety with me. And then they treated the founders badly. And then I was like, you know what, I don't need to have you in my fund. You said it directly to me, Mark, that I don't, you don't want to come to my events. And you don't want to have to be if you don't come to my events. Or show up for me on the podcast. Uh, then you can't be in my fund. Yes. I just decided right at that moment that I don't need to have this level of like, I mean, who's Mark Andreessen? Give me a break. You know, like, I'm sorry. Like, you're not that important. Ben Horowitz is not that important. You're not as successful as Sequoia or a benchmark. Your returns are much lower than theirs. So like, you're the 15th. I mean, in terms of capital under management, they're incredible. In terms of performance, they're far behind everybody else. Right. I mean, isn't that what you learned?

SPEAKER_548: Well, we did the math. No, they're they're second tier in their returns.

SPEAKER_09: They, uh, that was the knock on them for a long time. But they returned 11 billion dollars on Coinbase. And you can't really argue with that.

SPEAKER_355: The base case that we came up with, Dave, is it okay if I spoil it a little bit? Go for it.

SPEAKER_554: Yeah, spoiler. It gets more people to sign up.

SPEAKER_49: So they've raised almost 19 billion in funds. We really can only do analysis on the first like 8 billion raised because the rest is recent or bio or stuff that we weren't looking at.

SPEAKER_531: Yeah, you're in the bottom of the J curve. Yeah. Makes sense.

SPEAKER_49: So of like stuff they could be liquid on, we don't know if they've actually distributed, but on stuff they could, they've returned at least, and these are estimates, 25 billion from that eight, with the potential for like 10 to 20 more.

SPEAKER_10: Okay, so they'd be a 4x fund that puts them in the top 20% of funds. Yeah, top top tier.

SPEAKER_295: With a lot of as we were talking about earlier with just like a lot of dollars. Like this is just from the top 10.

SPEAKER_04: But I mean, if you're a 3x fund, that's fine. I mean, I returned on my first fund.

SPEAKER_49: And again, I'm saying they're absolute worst case scenario. These are the returns from their top 10 companies.

SPEAKER_04: I mean, it's still no Sequoia or Benchmark just on a IRR basis is what I would say. On IRR.

SPEAKER_49: Yeah.

SPEAKER_04: I mean, if you were an LP and you could put money into only one firm, Sequoia, Benchmark or Andreessen, you would do it in that order.

SPEAKER_423: It depends how much money I have to put to work. If it's a lot of money, I'm putting it to work in Sequoia. If it's a little money, I'm putting it to work in Benchmark.

SPEAKER_90: Okay, let's pick 10 million or 100 million. Okay, yeah.

SPEAKER_67: So you're debating Sequoia versus Benchmark, right? Benchmark is smaller. Sequoia is bigger. Do we care about multiples or do we care about cash? Okay, just let's play the LP game here for a second.

SPEAKER_108: We're all LPs. Here's your choices in their prime.

SPEAKER_68: Sequoia, Benchmark, Fred Wilson, Andreessen. Who's last? And we're assuming all of them are doing the same deal with me on carry.

SPEAKER_174: Same deal on carry in their prime.

SPEAKER_28: By Fred Wilson, do you mean USB as a fund?

SPEAKER_174: USB as a fund.

SPEAKER_185: Yes, you would pick it in the order of what? We're talking about Benchmark, Sequoia, Fred Wilson, Union Square, right? Or just Union Square and Andreessen Horowitz.

SPEAKER_143: Are we talking about today? Are we talking about in their prime?

SPEAKER_108: We all know who's last on that list for LPs. Dead last on that list is Andreessen Horowitz. We all know who's first. It's Sequoia.

SPEAKER_185: So then we're debating two and three, correct?

SPEAKER_31: The number of times on our Andreessen episode that we use the, um, if you're going to come at the king, you best not miss line about Sequoia.

SPEAKER_108: Yeah, they missed. But anyway, let's do it. Let's do it right now. You listen, you guys don't have to worry about your relationship with Andreessen, because you did your show already. In all honesty, who do you pick as your number one?

SPEAKER_567: In each of the firm's primes.

SPEAKER_21: In their primes.

SPEAKER_568: You can be an LP.

SPEAKER_49: Oh, all right. Well, here's the wild card is that, uh, there's a reasonable chance. I'd want to say Andreessen Horowitz today, because I think their prime is the next 15 years.

SPEAKER_04: Okay, fine. Let's take it as in the last decade. Who are you making your bet on?

SPEAKER_234: Like if web three is a thing.

SPEAKER_22: Yeah.

SPEAKER_67: If crypto is a thing, then they're going to be the best.

SPEAKER_22: They're they are best positioned.

SPEAKER_67: Yeah.

SPEAKER_04: Unfortunately, crypto is a total giant scam. And there's no actual use places out of NFT. So I think it's actually going to blow up in their lap. And it's going to work result in a ton of lawsuits. That's my best guess. I think they're all their crypto investments are going to be, you know, aside from Coinbase, which is a legit company operating. I think a lot of those projects are just never going to actually materialize. That's my, my gut. I think it's going to be, I think it's going to be like, what was the thing? What was the big, uh, investment that Khosla did?

SPEAKER_111: Uh, and he just got demolished. Ethanol.

SPEAKER_578: Oh, yeah, yeah, yeah, he did. All those ethanol funds or whatever, or, you know, at that time. Or the Kleiner green stuff.

SPEAKER_219: Well, who would be in that four? What would be your one, two, three, four?

SPEAKER_146: If you could be an LP. Well, let's just say it this way. If you'd be an LP and only two, what are you picking?

SPEAKER_109: I mean, the, the, whatever the 2007,

SPEAKER_49: eight, nine benchmark fund for sure. I mean, that in their prime, like that wasn't that fund at 12. X.

SPEAKER_581: You're going to go Sequoia and benchmark. I mean, that's basically it, I think. And Fred would be very close.

SPEAKER_582: I think the Sequoia funds with Airbnb and the like might have ended up being better. What's that? YouTube. What's that? Twitter.

SPEAKER_31: But, but yeah. Sequoia is definitely number one.

SPEAKER_586: All right, let's go down the rest of this list. Wait, wait, wait.

SPEAKER_49: I'm not trashing Andreessen. It's 25x gross. Benchmark's 2011 fund.

SPEAKER_74: Ooh. 25x cash on cash. And you're sitting here talking about Andreessen Horowitz's 3x, 4x best, worst case scenario.

SPEAKER_04: Like that's, that's the joke of all this is Andreessen Horowitz spends all this time doing marketing themselves and markets out there creating clubhouse groups and their own news site.

SPEAKER_173: And it's so funny, Jason, because before when David and I were like,

SPEAKER_49: what should we talk about on Jason's show today? I was thinking like, it'd be fun to kind of like equate what Jason is doing as like the pioneer to what Andreessen Horowitz is doing now.

SPEAKER_68: This combination, media empire, venture fund, investor. Listen, I'm not sour that they're copying me.

SPEAKER_04: I take it as flattery. What I do take offense to is that they didn't show up for me. And they treated my founders poorly.

SPEAKER_10: And then also, that is excusable. Yeah. And I also think they blocked me from clubhouse, which thank you for saving me money.

SPEAKER_508: But I really wanted to be in that deal at the time. Oh boy. And I think they were like, I think we talked about that on our first episode.

SPEAKER_90: They never invite me into any deals.

SPEAKER_04: They never show up for me and they treated my founders poorly. And then I look at Sequoia. I look at those other firms.

SPEAKER_10: All right. I regret never bringing up Andrews and Horowitz. Why did you trigger me?

SPEAKER_423: I'm so sorry. Let's keep going down the list.

SPEAKER_49: So after Jeff Jordan, we've got... Sequoia, China. Sequoia, China. You guys keep going. Monster.

SPEAKER_215: You guys read.

SPEAKER_49: Alfred Lin, Sequoia, early stage US.

SPEAKER_68: Back to back, two days back to back IPOs with Instacart and DoorDash.

SPEAKER_143: Airbnb and DoorDash. Yes.

SPEAKER_31: Yeah. It's like, I remember the Tom Amansky instructional videos on ESPN in the 90s. Back to back to back. National champions. It's crazy. Yeah. It's crazy. Then we got Bestie Chamath.

SPEAKER_16: Bestie C. Which, you know, his venture investments, you know, well, certainly good.

SPEAKER_09: I would argue, I think maybe you've got the inside info, info maybe, J. Cal.

SPEAKER_172: His non-venture investments even better. His call on Amazon, his call on Bitcoin, his call on Tesla.

SPEAKER_05: I think that's why he wanted to create a firm that was not limited to early stage venture. So yeah, Yammer, Slack, Box, Virgin Galactic, all good.

SPEAKER_21: All great. Yeah. All great. Uh, this idea of a crossover fund where he can just. Yeah. Put money into anything he thinks is going to go up. I think that's why, you know, when they talk about him blowing up social capital or rebooting it, I think it was very much like he was doing the traditional venture thing. And he's like, you know what? I think there's something that I would enjoy more. Yeah. Which is.

SPEAKER_136: This is a box that I don't want to fit myself into.

SPEAKER_21: I mean, do you guys think I could work at a big firm? Like, you think any of the big firms would like to have me as a partner? I mean, obviously.

SPEAKER_109: I mean, some wouldn't. It's too hard once you've done your own thing to do it. Correct. It's just, it doesn't work. All right. That's it. All right.

SPEAKER_423: So on Chamath, by the way, I do want to say, like, today is his prime. So like, if you're picking Chamath to be a part of your,

SPEAKER_227: your five-man firm, that's, that's today Chamath.

SPEAKER_345: Exactly. Aileen Lee, Cowboy Ventures. Great. Yep. Forerunner. Amazing.

SPEAKER_49: Yep. Vinod Khosla of obviously Khosla.

SPEAKER_345: I mean, I think he was the most successful venture investment ever

SPEAKER_110: with Juniper at one point in time.

SPEAKER_297: Yep. At Kleiner. He, he was, it was Vinod and John Doer at Kleiner.

SPEAKER_345: They were, they were just killing it. But that Juniper investment, Juniper Networks, from what I understand, was at the time, like a sick hit, like a crazy.

SPEAKER_49: Let's try and pull some data for next time on, on that one. Oh yeah. Obviously your boy, David Sachs, who, by the way, I also think would be today. Like, I think that's part of the magic also of all in is all of you are currently on your own rising stars. So it's not like you're pulling at anyone from, you know,

SPEAKER_625: David's angel portfolio pre-craft.

SPEAKER_49: Oh, unreal. It's unreal. Oh, it's unreal.

SPEAKER_90: Unreal. I mean, a lot of them were the series B's though, uh, in addition to angel. So keep that in mind.

SPEAKER_49: I mean, still, we just got done talking. We just got done talking about all that matters is getting into the binary companies of our decade.

SPEAKER_10: I agree. I agree. I'm just saying it's not a competition or whatever, but yeah. Yeah, no, he's done pretty, pretty amazing. Yeah.

SPEAKER_634: Keith, her boy, fellow PayPal mafia.

SPEAKER_49: Sounds like Jason obviously is putting in there, uh, along with Jamath and, uh, let's see, Annie Lamont. From Oak?

SPEAKER_637: I don't know her.

SPEAKER_87: She's lesser known, but.

SPEAKER_09: Uh, co, um, uh, co-managing director, co-founder of, of Oak, uh, HCEFT, which was Oak, but yeah, great, great healthcare and fintech investor.

SPEAKER_49: Chris Saka, who I think may have had the best multiple on a solo GP fund of all time with his investments in, in Twitter, a Twitter and Uber out of the same small fund.

SPEAKER_26: Yeah. I mean, that, that he had Twitter, Uber and Instagram in that fund. Ooh, insane. It was like a $3 million fund, right?

SPEAKER_04: It was an $8 million fund. I think he only deployed six or seven and I think it became worth a billion. So it was like a hundred X fund, which my first fund was a hundred X too. If you look at my scouts, $650,000 invested turned into 110 million. So it's so weird.

SPEAKER_648: I don't see the name Jason Calacanis on here.

SPEAKER_169: No, no, because it was small dollars, you know, like if it had been six million deployed, it would have hit that.

SPEAKER_649: For the record, we told Nick, we, we, we wanted J Cal on the list.

SPEAKER_04: No, I don't think I would be on this list right now. I'll be totally honest. I think it's, you know, my best days are ahead of me. All right.

SPEAKER_09: Well, we got last in the original list, sticking in the angel investment category, the OG, the original super angel, Ron Conway.

SPEAKER_74: I mean, I think that makes sense. I don't know the numbers from what I understand. He had such a small amount of Google.

SPEAKER_04: It actually wasn't material, but the Facebook was material. I think that's the, what, you know, you never know with this, you know, back channel, but it was like, I think he had 10,000 in Google or something.

SPEAKER_652: So depending on how long you held it, you know, it wasn't like a hundred K check in the angel round of Google.

SPEAKER_653: And then our, uh, two or two or one edition before.

SPEAKER_654: I had a Jim Breyer from Excel because I think like Peter Thiel gets a lot of glory from that

SPEAKER_49: Facebook investment. Excel had probably the single best venture investment of all time in there.

SPEAKER_05: I don't know what that resulted in today's dollars.

SPEAKER_04: I mean, that's the thing I'm thinking about with all these investments is I'm starting to think two decades now, uh, in all my investing 10,

SPEAKER_05: you know, six to 12 years as private companies, and then 10 to 20 years as public market companies is my current thinking of how to hold these.

SPEAKER_49: I mean, if you're going to end up with a Facebook, Amazon, Apple, Microsoft, Google caliber company, never sell. I mean, you just can't. Those companies are growing faster today than they have in the last decade.

SPEAKER_656: Absolutely.

SPEAKER_148: Breyer led Facebook's 12.7 million at a $98 million valuation.

SPEAKER_311: So 10% pretty wild. And it's worth a trillion now. What is Facebook?

SPEAKER_423: Yeah, I don't know. That's the thing I want to do some research on is what excels liquidation in from

SPEAKER_211: Facebook was, or at least their distribution. All right.

SPEAKER_10: I'm going to have lunch with Ho Nam.

SPEAKER_211: While you were talking about him, I just the best.

SPEAKER_500: Did this happen publicly on Twitter?

SPEAKER_26: No, I just literally DMed him on Twitter while you guys mentioned him. I was like, I don't know this guy. And I just wrote lunch question mark. And he was like, sure. This is why Jason's been so checked out this episode.

SPEAKER_117: He's just like been DMing the whole time.

SPEAKER_660: No, I'm not. I checked out. I'm engaged. Oh, what's this new theme music? Let's listen to your new thing. Oh, wait, wait, wait.

SPEAKER_71: We got one more though that we added during the episode. We got Jim Getz. How could we forget?

SPEAKER_173: Should we have young Spielberg and Mike Taylor play out this episode?

SPEAKER_04: We absolutely have to play. All right. Listen, thanks for coming on the show, boys. And we will do in two weeks, our venture investing, uh, Mount Rushmore, building a new firm. Us plus four, five person firm. Who do you put on it? Super group ventures. Super group ventures. When I'm back from my trip.

SPEAKER_169: Uh, here we go. Taking us out young Spielberg who got the truth. Bye-bye. Who got the truth?

SPEAKER_665: Is it you? Is it you? Is it you? Who got the truth now? Is it you? Is it you? Is it you?

SPEAKER_667: Sit me down. Say it straight. Another story. Everybody's talking. Nobody's listening. These days I feel lost, man. Lost in opinions. Everybody's fighting. Nobody's winning. Take me home. Cause I don't know what's going on in the world I'm living in. Everybody's break, break, breakin' up to dinner.

SPEAKER_668: Break, break, breakin' up. All this smoke I need to know.

SPEAKER_665: Is it you? Is it you? Is it you? Who we got? Is it you? Is it you?

SPEAKER_667: Is it you? Sit me down. Say it sh-

SPEAKER_669: I'm here for the cheek-talk. Uh-huh. They flip-flop like a seesaw. Uh-huh. Not free under these laws. Uh-huh. Now the world see what we saw. Uh-huh. People wonder what to do now. Uh-huh. It took a body cam to get the truth.

SPEAKER_668: Got so much to lose now. Break, break, breakin' up to dinner. All this smoke I need to know.

SPEAKER_665: Is it you? Is it you? Is it you? Who got the truth now? Uh-huh. Is it you? Is it you?

SPEAKER_667: Is it you?