The Exchanges

Q Can I be so bold and ask, was that the first real money that you made? I think when you first have your big hit, it does change a lot mindset-wise. Was that your first, and did it impact your mindset?

A Uh, yeah, it was my first. So I used that merger proceeds to pay down my student loans. So I was, I was student loan free in 2007. So call it, I was 35. Um, cause I've been with tell me now for, you know, eight years at that point. And, uh, it changed my mindset in so far as like, wow, this is possible, right? I was an immigrant from Egypt. My parents came here, you know, with nothing's crap, classic, great immigrant story for America. But it was sort of proof positive when you see that many zeros in your bank account, you're like, wow, this, this is actually the land of opportunity, and it really is. Um, so in that way, but, but I was sort of still someone who didn't spend the money, was afraid it would go away at any time. So my lifestyle didn't change, but, but my attitude, uh, did change.

AI assessment note: “Uh, yeah, it was my first.”

Q Yeah. Just listening to that. Um, uh, I, I do want to also, um, and Alfred asked this one. Okay. Moving on from the benchmark side, Dara today, what do you honestly think of Dara's management? How do you feel? Good? Bad? What are the thoughts?

A I mean, there's no, just let's start at a factual basis. The company's valuation Is lower today than it was when Dara took over. And even if you account for the macro environment, the Nasdaq's still up 50%, he's down 50%. So it just is. Then you're like, oh, what about ride sharing? Ride sharing is down. Well, what about e-commerce? Amazon up and Wix.com and Overstock are down. So Uber should have been the leader in this category and brought everyone up and showed them how to make an efficient business model. Um, there's been an enormous talent train. The company is loaded with debt right now. It's one of the only ride sharing the companies in the world with net debt. Um, is lost in food delivery to, um, DoorDash big. We went from a 60 point sort of gap to, you know, being the opposite. And that's a thirty billion dollar mistake if you think that, you know, Uber could have been DoorDash. So, um, you know, by all objective measures, it hasn't succeeded from a financial standpoint. So, you know, he's a nice guy. He cleaned up the company in terms of things that were sort of excess from a culture standpoint. He was a diplomat. He was able to get the company public, but in terms of hiring talent, innovating, and succeeding from a financial standpoint, you know, it's not, it hasn't happened. It's a, it's an F, you know.

AI assessment note: “by all objective measures, it hasn't succeeded from a financial standpoint”

Q Just insanely cool to hear. Um, I, I do want to flip though. Uh, what was the worst deal you've ever done? We've all made mistakes. What was the worst deal you've done? And what did you learn from that?

A The worst deal I've done? Well, you know, they have to be material to be bad, right? So I'm not going to tell you about the small, the small, we call them SLDs, small shitty deals. Um, uh, uh, so shitty little deals. Um, so I'm not going back to that because every company sort of does deals. They make mistakes. I'll talk about big one. I'd say that the deal that Was under my watch. I didn't like it at the time, but I, you know, it got done was, was Uber acquiring, um, auto, which was the autonomous car division that, uh, that gets started out of Google guys. It was, and I didn't like it for different reasons. It turned out to be a bad deal because of that ended up in that lawsuit with Google, but it was so complicated with multiple earnouts and who owned what entity. And I, as a lawyer, I come from a little bit start with start with simple and then complicate if you have to. And it was this complex kind of thing where it was a sort of a separate company. And I didn't like the ideas of, of other employees having different motivations at my company about what they were going to do. I want everyone to be motivated the same way. So I tussled with Travis on it. He won. We did that deal. Um, we got some great people that, that are now running Uber Freight. So there was like a great talent migration there. But it ended up in destroying our relationship with Google. So the cost to that…

AI assessment note: “the deal that Was under my watch... was Uber acquiring, um, auto”

Q I have to start with, um, actually one from Dave Clark, but Dave Clark highlighted the breadth of your experiences pre Really diving into being the OG that you are today. We have, uh, Harvard, Stanford, Goldman, lawyer, uh, Department of Defense, and he asked, which of these best contributed to your success today, do you think, on Reflection?

A I mean, you know, sort of none of them. The best one was the Bill Campbell thing. When I got to the Valley, um, Bill Campbell was associated with Kleiner Perkins, um, and Kleiner Perkins back in that day was the VC. They did Amazon, Google, um, John Doerr was, was the man. There was no one, what he touched turned to gold, and he was buddies with Bill Campbell, and he invested in Tell Me, that first company I was telling you about, and Bill took a liking to me, and I was 25, and he became my mentor, and he's the one who sort of propelled the future startups. He's the one who propelled, you know, working at the White House for Secretary Robert Gates. The education stuff didn't propel me for much of it, except meeting the guys, Hadi, Ali, David, Alfred. Um, so those are the two sort of influence, I'd say, that got me there.

AI assessment note: “I mean, you know, sort of none of them. The best one was the Bill Campbell thing.”

Q What do you think got them over the line on that deal?

A Besides the industrial logic, I really believe that it was mine and Jean Lou's relationship. Um, we spent a week, a week together in a dark hotel negotiating this, and she trusted me at that point. And then we flew to Macau and we flew to Macau because, um, we didn't, she was well known in China. She was a family of a politician. And if they saw her with some American and be like, oh, this is DD Uber merger happening. So we flew this hotel room in Macau for another four days with lawyers and the whole thing. And we really just pushed it through. She and I, we got our teams on board. We got our CEOs on board. We got our lawyers on board to count. And this is a cross border M and a China, us consumer. It was so complicated. And every day I made sure at the end of the day, say, Jean, how are we doing? Are we, How are you and me? Did I say anything that you didn't like, that you thought was wrong? Let's clear it out. Sort of like a marriage. Before you go to bed, you clear your air. We cleared our air every day, and then we closed the deal, and I remember going, she asked me to go to dinner the day after the deal closed, and she's like, I heard you were such a tough negotiator. I was like, I am tough, aren't I? She said, no, but you're fair. You told me what you were going to do, and you did it every single time. No matter what it was, no matter what clause, you said, I'm gonna get…

AI assessment note: “I really believe that it was mine and Jean Lou's relationship.”

Q Dave Clark asked me a question to ask you, and I thought it was, and he did a crying laughter emoji face, and I was like, well, that tells me that I should probably adapt it slightly. Are SPACs over, and what did you learn from yours?

A SPACs are over. Um, what I learned from mine is that I relearned a lesson that I am not a financial engineer. I'm a deal maker. And SPAC, the SPAC world is not deal making. It's financial engineering. It's moving money around from one part of the ecosystem to another. And trying to get the IPO out fast and about disclosures and what you're allowed to say in this situation versus not. It is just, and this is, I think, unfortunately, what Dara does at Uber, what a company like Verizon does, they're all, they're all financially engineered. They're not innovating. And so when there's a market collapse, all these financially engineered Frankenstein products, like a SPAC collapse, and, and that's what's happened. And It used to be a backwater financial product, and Chamath brought it to be mainstream, and I think it's just gonna retreat back to being a backwater financial product.

AI assessment note: “SPACs are over. Um, what I learned from mine is that I relearned a lesson”

Q Can I be so bold and ask, was that the first real money that you made? I think when you first have your big hit, it does change a lot mindset-wise. Was that your first, and did it impact your mindset?

A Uh, yeah, it was my first. So I used that merger proceeds to pay down my student loans. So I was, I was student loan free in 2007. So call it, I was 35. Um, cause I've been with tell me now for, you know, eight years at that point. And, uh, it changed my mindset in so far as like, wow, this is possible, right? I was an immigrant from Egypt. My parents came here, you know, with nothing's crap, classic, great immigrant story for America. But it was sort of proof positive when you see that many zeros in your bank account, you're like, wow, this, this is actually the land of opportunity, and it really is. Um, so in that way, but, but I was sort of still someone who didn't spend the money, was afraid it would go away at any time. So my lifestyle didn't change, but, but my attitude, uh, did change.

AI assessment note: “yeah, it was my first... it changed my mindset in so far as like, wow”

Q How do you do that? Is it small talk? Is it, oh, have you had a nice trip?

A It was, it's exactly not that. When people go, oh, how was your flight? Where'd you come in from? Where are you staying? The small talk stuff is fine, but it's, it's, it sort of betrays a little naivete, like that you care, or they care, because if there's, you're in a serious negotiation, no one cares about that. They just care about, like, what you're trying to do. Um, it was more about Trying to build some trust. And so one of the ways I built trust with Jean Lou would say, Hey, I'd be interested to hear your perspective. We were in this competitive battle here. Here's how I saw it. What did you see? Um, something that wasn't sort of central to negotiation, but try to establish a rapport about how both of us saw the same incident so differently. And she's like, Oh, we didn't, we didn't shut off all your phones or send spam text messages to drivers saying they weren't going to get paid. I was like, you didn't? Who did? And then we'd have a joke about like, well, who is trying to sabotage both of us? Um, and it was a little bit of that until, and it took me four days of going to that dark hotel room until she allowed me to bring one of my colleagues to at least take notes so that I wasn't over man here. It was that kind of rapport that started it. So rapport matters and knowledge of what their problems were matter. And Sufficient humility, but sufficient strength projection sh…

AI assessment note: “It was, it's exactly not that... It was more about Trying to build some trust.”

Q Just insanely cool to hear. Um, I, I do want to flip though. Uh, what was the worst deal you've ever done? We've all made mistakes. What was the worst deal you've done? And what did you learn from that?

A The worst deal I've done? Well, you know, they have to be material to be bad, right? So I'm not going to tell you about the small, the small, we call them SLDs, small shitty deals. Um, uh, uh, so shitty little deals. Um, so I'm not going back to that because every company sort of does deals. They make mistakes. I'll talk about big one. I'd say that the deal that Was under my watch. I didn't like it at the time, but I, you know, it got done was, was Uber acquiring, um, auto, which was the autonomous car division that, uh, that gets started out of Google guys. It was, and I didn't like it for different reasons. It turned out to be a bad deal because of that ended up in that lawsuit with Google, but it was so complicated with multiple earnouts and who owned what entity. And I, as a lawyer, I come from a little bit start with start with simple and then complicate if you have to. And it was this complex kind of thing where it was a sort of a separate company. And I didn't like the ideas of, of other employees having different motivations at my company about what they were going to do. I want everyone to be motivated the same way. So I tussled with Travis on it. He won. We did that deal. Um, we got some great people that, that are now running Uber Freight. So there was like a great talent migration there. But it ended up in destroying our relationship with Google. So the cost to that…

AI assessment note: “was Uber acquiring, um, auto, which was the autonomous car division”

Q to ask is, um, and again, I can't remember who it was. Um, but someone asked this, and I liked it. Here you go, Emil. Travis, and you, you are back running Uber. You said, um, you know, before about, you know, the lost opportunity in, uh, food. You spoke about Uber Freight. What are the opportunities that you would have jumped on? What would you not have jumped on?

A Yeah. I think we, instead of buying, um, Kareem in the Middle East, Postmates, Jump Bike, um, I think all of those will be a hundred percent write downs. Those are some of the worst acquisitions done in tech. Um, maybe Postmates may be the worst acquisition done tech in the last five years. So it's for a three billion dollar company that was like going to be a zero within three months. And we got nothing out of it. No market share gain, nothing. So there was just a bunch of. You just bad, I guess, sort of, and I think Dari was trying to repeat the Expedia thing, which is like, buy all these random things, like stitch them together, and like, that's a platform. It's kind of not how it works. Um, so I would have beaten door, we would have beaten DoorDash, guaranteed. We were ahead by 30 points when Travis Knight left, so letting that atrophy was not an option. Um, I think we would have had an Instacart competitor way earlier, and we would have been, if not ahead of Instacart by now, but neck and neck with them. In every continent, just not one continent like Instacart's in. So even if you think Instacart's a fifteen billion dollar business, I think we could have built a sixty billion dollar business globally on that, on top of Eats, which was another, another 60 to a hundred billion if we'd won DoorDash, and we were going to beat Deliveroo, and then the rides business where Uber,…

AI assessment note: “instead of buying, um, Kareem in the Middle East, Postmates, Jump Bike”

Q What do you think got them over the line on that deal?

A Besides the industrial logic, I really believe that it was mine and Jean Lou's relationship. Um, we spent a week, a week together in a dark hotel negotiating this, and she trusted me at that point. And then we flew to Macau and we flew to Macau because, um, we didn't, she was well known in China. She was a family of a politician. And if they saw her with some American and be like, oh, this is DD Uber merger happening. So we flew this hotel room in Macau for another four days with lawyers and the whole thing. And we really just pushed it through. She and I, we got our teams on board. We got our CEOs on board. We got our lawyers on board to count. And this is a cross border M and a China, us consumer. It was so complicated. And every day I made sure at the end of the day, say, Jean, how are we doing? Are we, How are you and me? Did I say anything that you didn't like, that you thought was wrong? Let's clear it out. Sort of like a marriage. Before you go to bed, you clear your air. We cleared our air every day, and then we closed the deal, and I remember going, she asked me to go to dinner the day after the deal closed, and she's like, I heard you were such a tough negotiator. I was like, I am tough, aren't I? She said, no, but you're fair. You told me what you were going to do, and you did it every single time. No matter what it was, no matter what clause, you said, I'm gonna get…

AI assessment note: “I really believe that it was mine and Jean Lou's relationship.”

Q the complete retrenchment away from them, for sure. Um, I do have to discuss two final elements before we do a quick fire. Number one is Alfred Lin told me about, you know, fatherhood. And what a prominent part of your life that is now, which is amazing to hear. How did becoming a father change how you think, both as an ambassador, as an operator, how did it change?

A Without being You know, sort of saccharine about it. Um, it, I'm, I just turned 50, so I have a two and a half year old daughter. Um, I will say that I don't, it is now, you know, I knew this intellectually, but now I feel it viscerally. I don't know how I could have done the work that I would wanted to do at Uber, 70 hours a week, and no one was telling me to do it. It wasn't like, you know, hustle culture, blah, blah, blah. This was Emil loving my job, right, at Uber, doing 70 hours a week. Traveling all over the world trying to build something important and had a successful marriage and a kid. I just don't know how it's possible. And I don't think it is. So, um, it changed me insofar as now I know why tech, whether I like it or not, is a young man's game, young man and woman's game in that there is a certain reason that you, you know, young people start startups. It's because they have the time and energy to do it, and the risk appetite that you have, don't have as much when you have other important things in your life like I do now.

AI assessment note: “it changed me insofar as now I know why tech, whether I like it”

Q Do you remember he used to sleep with his BlackBerry on his chest? I want to finish on the final one. What are the next five years hold for you, Emil? 20, 27. Where are we at?

A Yeah. So I, I think that I'm, I'm going to be, I need to be doing something important, um, and singularly focused again. So I'm looking for that starting now. The SPAC is done as of last month. Um, and now I am looking for the next Challenge I could spend five to 10 years on. Um, and that's taking a lot of forms. I'm talking a lot of people. Is it starting something? Is it buying something? Is it taking something private and running it? Um, all those things, but I need to be running something because, you know, if we're, I'm 50, if we're going to live to a hundred, I might, I may be on the back nine, but just what, you know, the 10th hole, not the 17th. So I got, I got a lot of time to go.

AI assessment note: “now I am looking for the next Challenge I could spend five to 10 years on”

Q How do you do that? Is it small talk? Is it, oh, have you had a nice trip?

A It was, it's exactly not that. When people go, oh, how was your flight? Where'd you come in from? Where are you staying? The small talk stuff is fine, but it's, it's, it sort of betrays a little naivete, like that you care, or they care, because if there's, you're in a serious negotiation, no one cares about that. They just care about, like, what you're trying to do. Um, it was more about Trying to build some trust. And so one of the ways I built trust with Jean Lou would say, Hey, I'd be interested to hear your perspective. We were in this competitive battle here. Here's how I saw it. What did you see? Um, something that wasn't sort of central to negotiation, but try to establish a rapport about how both of us saw the same incident so differently. And she's like, Oh, we didn't, we didn't shut off all your phones or send spam text messages to drivers saying they weren't going to get paid. I was like, you didn't? Who did? And then we'd have a joke about like, well, who is trying to sabotage both of us? Um, and it was a little bit of that until, and it took me four days of going to that dark hotel room until she allowed me to bring one of my colleagues to at least take notes so that I wasn't over man here. It was that kind of rapport that started it. So rapport matters and knowledge of what their problems were matter. And Sufficient humility, but sufficient strength projection sh…

AI assessment note: “It was, it's exactly not that. ... It was more about Trying to build some trust.”

Q we've mentioned M&A, we've mentioned fundraisings. We're in this very kind of weird new world where, and most of us actually haven't kind of seen a recession or, you know, downtown like this. So I want to ask you with your kind of OG status, How do you analyze fundraising and M&A in the current market today? And I'm just gonna put the general question there for you to take.

A Yeah, so I'm, I'm deep in the capital markets now with a lot of the companies I work with. I'm on the board of our advisor, and I said, guys and gals, last year was FOMO. You want to create FOMO with investors if you're trying to raise a round or merger partners. This year is JOMO. Joy of missing out. They are happy to miss out on whatever deadline you put on them for whatever round. They're happy to not take a look if you've got something in hand. So those, that whole strategy of FOMO and Creating pressure and dynamics is over. Don't try it. Stop. It may, it's got, you are going to be disfavored and people are going to say, thank God I didn't have to look at that company and say no. So the humility factor from entrepreneurs has to come back in terms of what's realistic and we're getting there. Um, because you're starting to see some of these rounds not happen or you're starting to see things creak a little bit. I think we're at the end of the beginning, though, not the end of the end. The next phase is structured rounds, down rounds, like true down rounds, um, and then sales were, unfortunately, companies sort of not making it, and I think that'll happen in Q one, you know, the phase two will happen in Q four, Q one, and then Q two to Q three will be phase three.

AI assessment note: “last year was FOMO... This year is JOMO. Joy of missing out.”

Q the complete retrenchment away from them, for sure. Um, I do have to discuss two final elements before we do a quick fire. Number one is Alfred Lin told me about, you know, fatherhood. And what a prominent part of your life that is now, which is amazing to hear. How did becoming a father change how you think, both as an ambassador, as an operator, how did it change?

A Without being You know, sort of saccharine about it. Um, it, I'm, I just turned 50, so I have a two and a half year old daughter. Um, I will say that I don't, it is now, you know, I knew this intellectually, but now I feel it viscerally. I don't know how I could have done the work that I would wanted to do at Uber, 70 hours a week, and no one was telling me to do it. It wasn't like, you know, hustle culture, blah, blah, blah. This was Emil loving my job, right, at Uber, doing 70 hours a week. Traveling all over the world trying to build something important and had a successful marriage and a kid. I just don't know how it's possible. And I don't think it is. So, um, it changed me insofar as now I know why tech, whether I like it or not, is a young man's game, young man and woman's game in that there is a certain reason that you, you know, young people start startups. It's because they have the time and energy to do it, and the risk appetite that you have, don't have as much when you have other important things in your life like I do now.

AI assessment note: “it changed me insofar as now I know why tech... is a young man's game”

Q My biggest mistakes have always been when I relied on someone else, even if they're amazing, never do that. Um, tell me what mistake have you made in hindsight you wish you hadn't made?

A You know, I, I wished one of the things that, you know, besides like wish we'd never had benchmark as an investor at Uber, I wished that one of the things that happened with these hyper growth companies is we should have turned the corner earlier. Cause what I described companies when they're startups as tribes, And as your tribe gets bigger, you start to intersect with other tribes and you better become a civilization or the tribes are going to be at war. So you build these companies. They're actually really civilizations. They're not tribes and you can't run them like tribes anymore. You have constituencies, you have politics, you have to have governance. You have to have clear, transparent rules that everyone can follow and Uber, Airbnb, let's all became those things. And it's hard to turn. And Reed Hoffman talks about the pirate first to whatever, Matrix that he's got, I have something similar. It's like, you got to turn from a tribe to a civilization. Had Uber done that a little earlier, I think we could have, you know, potentially avoided some of this chaos.

AI assessment note: “besides like wish we'd never had benchmark as an investor at Uber”

Q How did you get Travis over the line on the flip side? That seems like a tough thing to do as well.

A Um, it, Travis and I worked together so well, the two, the thing that we had lots of discussion about was M&A. Should we buy Lyft, should we not buy Lyft? Should we merge with Didi? Should we not buy Didi? Should we sell, buy Grab, all the different rod sharing companies around the world? I was always for it before he was for it. But the China thing was so unique, Harry. No, think about what consumer tech companies operate in China. Zero. There was, there's enterprise tech like Hewlett Packard and IBM and all those guys, but no one else had done that. And we didn't ask for permission. We just did it. We showed up in, you know, Hangzhou and in Hunan province, and we just launched Uber. So there was some amount of risk to that, that yeah, if you don't sell it, it might just not exist one day, given sort of the government roles. And we were spending A hundred million dollars a month competing there. Cause it's remember it's, this is the biggest market in the world. Um, 1.3 billion people, and we were going to win. And I just raised three and a half billion from the Saudis. And so we were going to win. So the combo of those things made the industrial. And then when I handed the deal on a platter, I was like, this is done. This doesn't, you know, let me start. This is finished. 45 days from beginning to end. He agreed. That's how I got him over there.

AI assessment note: “when I handed the deal on a platter... He agreed. That's how I got him”

Q Well, I mean, I mean, listen, I told you, this is like us having a chat with a bourbon. How do you weigh that? Because I'm, I sway between the two. Um, so how do you think about centrality of founder versus market versus product?

A Yeah. So I'm founder first and I do believe, and I will say, I will say this and I'll have this argument with anyone that a mediocre founder with a great idea and a big market Might win, but it's also not that fun to be along the ride with because if they're mediocre, so if you're going to work there right now, this is working versus investing right now. If you're going to work somewhere for me, who the founder is, and if it's your co-founder is the most important thing by far, most companies pivot anyway. So what market you started and might not be the market you end in, um, but product, you know, but, but the product, what are they trying to do? Is it A big enough idea, uh, period. So as an employee, it was, it was, uh, it was founder, and then it was product, and then it was market. As an investor, it's still founder for me, but then the market matters because the product, I don't know, the product's gonna, you know, it depends on how good the founder is. It depends on how competitive the market is, how much it evolves, how much money is going into it, the macro climate, all those things.

AI assessment note: “So I'm founder first and I do believe”

Q We're going to talk about the acquisition. I just have to ask them, listening to you, it was kind of, you know, so early in your career, you were so young at that point in, did you really feel the weight of expectation having raised so much money and really kind of bluntly being a lot less informed than you are obviously today?

A Yes, but that's how owners not renters feel, right? I was, I was, you know, when I started telling me I was still a couple of layers down in the org, It wasn't like I was, you know, out there, uh, as a co-founder who's 25. I was a business guy, and as you know, business guys are not top of the totem pole in Silicon Valley, right, in general. Um, so I had to work my way up, work my way up. But then, I think the way I did that is because I cared every day about that company, uh, and the people in it, and the mission. And when you care that much, no matter what position you are, you feel the weight. But that weight makes you better, right? It makes you stronger. You put weight on your shoulders, you walk around all day, your legs are going to get stronger, right? So, um, that weight was real because I'd recruited my friends. My cousin had interned there, Jared Hecht had interned there, Matt Window. A lot of the, you know, Silicon Valley, uh, you know, Illuminati, so to speak, had spawned from Tell Me, PayPal, Opsware, which was Ben, where Ben and Mark came from. All these companies were in and around the same time and employee pool, you know.

AI assessment note: “Yes, but that's how owners not renters feel, right?”

Q I'm, I'm going for it, but I'm too interested. I think I've heard other people say it was when Travis lost the support of the team that it, it made it impossible. Is that fair or not fair?

A I mean, Benford's a sophisticated organization. You can imagine them asking them at some, some subset of the team to tell, you know, The board that they weren't satisfied with the team. Um, and but, you know, there's a lot, you could imagine them hiring a PR person and a law firm and a strategy consultant and all the things that come with, with the scorched earth tactics they used, um, and that being the outcome people saw. But the reality is, yes, he's lots of support. But remember, and here's a critical fact. Travis agreed to take a leave of absence after his mom died. And after we had that board meeting, he said, I'm gone. I need to go take time to do, but not leadership family. And I, and, and everyone agreed on the board, unanimous board vote. 10 days later. Is when they cornered him in a hotel room in Chicago and gave him the, I'm going to smear you letter or you're going to quit without counsel in an hour letter. So anyone who says that it was the support of the team that caused that, he agreed to take a leave of evidence. He was in a hotel in Chicago interviewing a COO candidate to take the job so that he could have some time to go do what he needed to do. So just think about that when people, you know, bring up this.

AI assessment note: “anyone who says that it was the support of the team that caused that”

Q I do want to move to, uh, my world, which is obviously venture, where we sit on the sidelines and do very little, unlike, you know, uh, you know, operators like you. Um, you decided, and then you decided to go full-time investing with Cotu, um, Uh, and then you decided to go back to being an operator. What was the thinking behind that move back to being an operator?

A You know, the coach, you guys did me a great favor. They said, come in for six months and see if you look, you know, you like being an investor and we'll see if we like you. And there's some of the best in the business. Philippe Lafont, Thomas Lafont, Daniel Seft, Chris Fredrickson, when he was there, Dan Rose, you know, Matt Mazio, they're, they are pros and they have built an incredible franchise in China. In late stage, they're just, oh, they're, they're just very innovative, and I like them a lot, so I love doing the China stuff, so I said, okay, I could do the China stuff, I could do late stage stuff, and they're, I just, I am not built to oppose an entrepreneur in a negotiation. I know that sounds crazy, but I can't sit, I can't sit in the investor seat and not empathize with the entrepreneur I'm negotiating with, which is what you do when you're an investor. Um, I'm just, it's, it's a hard to, I'm, I can help the GoPiff guys go up against Masa, Tiger, who, you know, you name it. Me bearing down on Roth and Jared Hecht, and these guys, it's just not in my DNA.

AI assessment note: “I am not built to oppose an entrepreneur in a negotiation.”

Q Is it stuck, or is it sticking to your knitting? Do USV do the same? Um, I mean, Ribbit don't actually. They've scaled up a lot. Um, but there are, you know, Aleph in Israel who I rate a lot, um, Michael Eisenberg. Is it sticking to your knitting, or is it just being behind the times?

A I mean, Lyft stuck to their knitting, and they're about, they're getting crushed. Um, the word, they're not changing with the world. You got to play the game on the field, and the game on the field is different than it was, and I'll tell you what, Harry. There are going to be fewer tech acquisitions in this antitrust environment. Fewer, much fewer. So your outcomes for mid, middle companies like tell me are going to be farther, you know, fewer and farther between. So there are going to have to be that there were the, the returns coming from the big winners, the big win. And to win big, you've got to try to invest across multiple stages. And that's what Sequoia can do. That's what age can do. That's what rivet can do. That's what DST can do. And I think if you can't, You're just going to get, have to get lucky because there's going to be fewer and fewer mid-level winners to sort of bet, to return the portfolio. Uh, so you have to find the ones that are going to 10 exit.

AI assessment note: “Lyft stuck to their knitting, and they're about, they're getting crushed.”

Q Well, I mean, I mean, listen, I told you, this is like us having a chat with a bourbon. How do you weigh that? Because I'm, I sway between the two. Um, so how do you think about centrality of founder versus market versus product?

A Yeah. So I'm founder first and I do believe, and I will say, I will say this and I'll have this argument with anyone that a mediocre founder with a great idea and a big market Might win, but it's also not that fun to be along the ride with because if they're mediocre, so if you're going to work there right now, this is working versus investing right now. If you're going to work somewhere for me, who the founder is, and if it's your co-founder is the most important thing by far, most companies pivot anyway. So what market you started and might not be the market you end in, um, but product, you know, but, but the product, what are they trying to do? Is it A big enough idea, uh, period. So as an employee, it was, it was, uh, it was founder, and then it was product, and then it was market. As an investor, it's still founder for me, but then the market matters because the product, I don't know, the product's gonna, you know, it depends on how good the founder is. It depends on how competitive the market is, how much it evolves, how much money is going into it, the macro climate, all those things.

AI assessment note: “So I'm founder first and I do believe”

Q I'm, I'm going for it, but I'm too interested. I think I've heard other people say it was when Travis lost the support of the team that it, it made it impossible. Is that fair or not fair?

A I mean, Benford's a sophisticated organization. You can imagine them asking them at some, some subset of the team to tell, you know, The board that they weren't satisfied with the team. Um, and but, you know, there's a lot, you could imagine them hiring a PR person and a law firm and a strategy consultant and all the things that come with, with the scorched earth tactics they used, um, and that being the outcome people saw. But the reality is, yes, he's lots of support. But remember, and here's a critical fact. Travis agreed to take a leave of absence after his mom died. And after we had that board meeting, he said, I'm gone. I need to go take time to do, but not leadership family. And I, and, and everyone agreed on the board, unanimous board vote. 10 days later. Is when they cornered him in a hotel room in Chicago and gave him the, I'm going to smear you letter or you're going to quit without counsel in an hour letter. So anyone who says that it was the support of the team that caused that, he agreed to take a leave of evidence. He was in a hotel in Chicago interviewing a COO candidate to take the job so that he could have some time to go do what he needed to do. So just think about that when people, you know, bring up this.

AI assessment note: “anyone who says that it was the support of the team that caused that”

Q that, and I love the kind of, ah, what is mentality. Can I ask, you know, we, we mentioned kind of COE-II earlier. We've seen many firms come in, whether it's your altimeters, D-ones, durables, and then obviously SoftBank slightly before that, but like this explosion of capital. What does that mean for the founders? Is this a great thing? Is this a bad thing? How do you analyze that?

A For founders, it's more a good thing than a bad thing. That means that Um, there's more capital out there. So if your business model requires more capital, you can get it. And look, people are going to say, oh my God, it's loose capital, free money, blah, blah, blah. Companies like Uber, like Airbnb started in that era for a reason. It's because we could raise a lot of money and like try a bunch of stuff. And if money's too tight, maybe we wouldn't have gone into Uber Eats. We just would have like Lyft stayed in our lane. So there is some value, the loose money cycles, They actually have a purpose and, and they're an example of looser money policies, um, the D ones and tigers of the world. So having that is the overvaluing they created. Great. I don't know. It's not great for other investors who wanted to get in cheaper, I guess, but it's great for entrepreneurs. Um, you know, I do worry that because money of them are crossover funds, when their public market portfolio goes down, they get, you know, fearful of their private market portfolio. So they're not as consistent, but, You know, then you have bond capital, who I love consistent. They're not really in the public markets or in between, um, the late stage. Those kinds of companies have been great additions to the ecosystem that didn't exist 10 years ago.

AI assessment note: “For founders, it's more a good thing than a bad thing.”

Q We're going to talk about the acquisition. I just have to ask them, listening to you, it was kind of, you know, so early in your career, you were so young at that point in, did you really feel the weight of expectation having raised so much money and really kind of bluntly being a lot less informed than you are obviously today?

A Yes, but that's how owners not renters feel, right? I was, I was, you know, when I started telling me I was still a couple of layers down in the org, It wasn't like I was, you know, out there, uh, as a co-founder who's 25. I was a business guy, and as you know, business guys are not top of the totem pole in Silicon Valley, right, in general. Um, so I had to work my way up, work my way up. But then, I think the way I did that is because I cared every day about that company, uh, and the people in it, and the mission. And when you care that much, no matter what position you are, you feel the weight. But that weight makes you better, right? It makes you stronger. You put weight on your shoulders, you walk around all day, your legs are going to get stronger, right? So, um, that weight was real because I'd recruited my friends. My cousin had interned there, Jared Hecht had interned there, Matt Window. A lot of the, you know, Silicon Valley, uh, you know, Illuminati, so to speak, had spawned from Tell Me, PayPal, Opsware, which was Ben, where Ben and Mark came from. All these companies were in and around the same time and employee pool, you know.

AI assessment note: “Yes, but that's how owners not renters feel, right?”

Q Okay. Can I just ask a question on that? Do you let your, um, not opponent, but do you let the person on the other side of the table know the depth of information that you have, or do you want to keep it in wealth of reserve?

A The framework number two is the less information you give and the more you get the better. Um, and so none of this is sinister. It's just, If they haven't done the research, I'm not going to do it for them on me, but, but if I've done the research and it's just, this is Google stuff, right? I'm not, you know, this is nothing nefarious. This is just trying to put a picture around someone. If you had to write a chapter on Harry's life, I want to be able to write it before I get in the room with you. Um, and so whether I told you I wrote that or not, uh, you know, is my advantage to, to, to keep if I can do that. Um, and, and information is power and people don't, don't, Don't realize that enough, um, that the more you learn, the better you're going to be at these things, even about your own company.

AI assessment note: “the less information you give and the more you get the better”

Q I think it was Keith Raboy when I had him on the show. He said, pay to play rounds. I've never ever made my money back from this. Would you say the same, and how would you approach pay to play as an investor?

A I don't like pay to play either, man. I, I, I, you know, Lime had to do one a couple of years ago, um, the scooter company and Uber put in a hundred million dollars. And I told her, I was like, this is the, this is not a good idea. These pay to play things never work. It didn't work at bird. It didn't work at Lime. And it was somewhat specter specific. I just think. I've never seen them work, but I'm sure there are examples. If you do your homework, uh, Harry, like if we were negotiating and you study this, someone has made these work. I just haven't heard of them myself either. And I'd pay to play is different. That is a recap. That's stage three, you know, her, you know, category four hurricane, you know, a recap, right? Structure down round recap. Those are kind of different things in my mind in the spectrum.

AI assessment note: “I don't like pay to play either, man... These pay to play things never work.”

Q Are there any glaring misalignments that you see that you think more founders should be aware of?

A Totally. So, so, or when early stage investors Get to this point where there's just a lot of paper gains. We, there should be sort of term limits on board seats, like term limit out. If I get to, you know, a 10 X return and can get you some liquidity, then you can move on because the early board members who sit on late stage companies, it's fear based naturally there. There again, the, the, the, the natural incentives are Not to do what the company needs to do next to grow the next 10 X. And so that natural misalignment, it's not wrong. It just is, you know, it's just how it is. Um, those things could be, could be jiggered a bit. And so more, the thing we, I wish we did more of Uber is give more investors liquidity when they get scared. I would be like Venturex sell. Like, I'll find you someone to sell to sell, go get the second G six and the, you know, the whatever. The discovery property in Wyoming, and then leave me alone and let me build a business. Um, and I, I wish I'd done that. So early stage becoming late stages where there's a real disconnect still.

AI assessment note: “early stage investors Get to this point where there's just a lot of paper gains”