The Exchanges

Q My friend, you teed me up there. What's one or two of those misses which really comes to mind?

A I mean, I have so many, so, I mean, some of the seminal ones, I would say, were where I truly knew the person, and I knew they are a genius, and so these are, like, the stupidest misses. So at my first startup, LinkExchange, we had this brilliant contractor who was younger than us, so I was 25, Max Lefton was 22, and when we sold our company, he left to start PayPal. We all knew Max was, like, just a whole next-level brilliance. I mean, when he walked into the office, people would Speak in hushed tones. Oh my gosh, it's Max Lefgen. And the original PayPal idea, actually, I think it was called Confinity or some other weird name. It was almost a joke. It was this app for Palm Pilots to zap money using infrared. It almost felt like an episode of Silicon Valley. Like, that's not a business. Come on, who's going to be zapping money via infrared from one Palm Pilot device to the other? In hindsight, though, investing in PayPal was not about the original business idea. It was about investing in Max Lefgen. That was one miss, and same time frame, one of my smartest friends from Harvard, Craig Silverstein, was probably the top guy in our CS program. He and my brother and I were probably always vying for which of us is the best coder in the Harvard class of 94 in computer science, and it was probably Craig. After, I think in 1999, he was leaving his Stanford PhD program to join a new sta…

AI assessment note: “That was one miss, and same time frame, one of my smartest friends”

Q better wait and for the someone amazing and hire someone decent. And a lot of people responded saying, that's quite a luxury actually, Harry. And we just need to put bums on seats and get People in their positions, and good is actually better than perfect. Do you agree with that, and is there a stage of company where you don't need the best, and good is better than perfect?

A I agree with your original tweet. There have been painful periods. It takes pain. It takes sacrifice. It means you have to pull more all-nighters. It means your smaller team needs to work harder until you find the right people, and so, of course, there's a point at which you might need to make a compromise, but I've always found that if you're interviewing someone, and you're like, ah, They're not quite right. You'll soon find they were actually terrible. You know, if flaws reveal themselves within the first hour or two, there's bigger issues there, and I would sooner hold out for someone that you feel like this person is perfect. I would also agree that this is a luxury. At some point, you might have to say, we can't do this anymore. We are, you know, we need more sleep. We need somebody. But certainly with, I'm thinking back to early days of Dropbox, they specifically faced this. It was like six people for the longest time. You know, my brother and I as advisors Kept pressuring them. Don't just hire anybody. Keep your hiring bar as high as possible. You know, hire superstars. And it was harder. It took more than a year to convince Aditya Agarwal to join as a head of engineering, for example. It wasn't without sacrifice, but I would say worth it.

AI assessment note: “I agree with your original tweet. There have been painful periods.”

Q the only ones at the table. You kind of did that. So I guess my question is, did you not follow the advice that we give so many, which is like, appear like you have leverage and have a position of power and strength. Like, when I listen to that, I'm like, it could have created FOMO for him, where he did bid up. How do you think about that?

A I would agree that you should bring leverage and strength to a deal, and this applies not just to selling your company. Obviously, it applies to fundraising. If you're raising your next You should be strong, but there's a big difference between being strong and being misleading. One thing I learned and I've passed on to the other founders is you can show strength without implying anything that's not true, especially if you're negotiating with somebody who has more experience. If you overplay your hand, they will know it. In my case, I don't know how many deals I had done at that point, but certainly not as many as Steve Jobs. And most founders have not gone through as many fundraisings as the VC has, obviously, right? As a VC, we see whatever. Multiple deals a week, and so you can tell when somebody's overplaying their hand. Now, to be strong without misleading, all you need to do is to say, I won't accept that. You don't need to say why. You don't need to make implications for, I have a better offer or I don't. If you simply say, we won't do it for less than X, that's strength. You can say that. Don't manufacture false information or false implications as to what else. If I had said to Steve merely, we wouldn't take a deal less than one 50, that would have been just as strong without Having the implication of something untrue. The other element I'd say, though, is humility, wh…

AI assessment note: “there's a big difference between being strong and being misleading.”

Q better wait and for the someone amazing and hire someone decent. And a lot of people responded saying, that's quite a luxury actually, Harry. And we just need to put bums on seats and get People in their positions, and good is actually better than perfect. Do you agree with that, and is there a stage of company where you don't need the best, and good is better than perfect?

A I agree with your original tweet. There have been painful periods. It takes pain. It takes sacrifice. It means you have to pull more all-nighters. It means your smaller team needs to work harder until you find the right people, and so, of course, there's a point at which you might need to make a compromise, but I've always found that if you're interviewing someone, and you're like, ah, They're not quite right. You'll soon find they were actually terrible. You know, if flaws reveal themselves within the first hour or two, there's bigger issues there, and I would sooner hold out for someone that you feel like this person is perfect. I would also agree that this is a luxury. At some point, you might have to say, we can't do this anymore. We are, you know, we need more sleep. We need somebody. But certainly with, I'm thinking back to early days of Dropbox, they specifically faced this. It was like six people for the longest time. You know, my brother and I as advisors Kept pressuring them. Don't just hire anybody. Keep your hiring bar as high as possible. You know, hire superstars. And it was harder. It took more than a year to convince Aditya Agarwal to join as a head of engineering, for example. It wasn't without sacrifice, but I would say worth it.

AI assessment note: “I agree with your original tweet. There have been painful periods.”

Q you mentioned Alfred, and I want to go back to LinkExchange, and I want to start with our first story of the day, and I decided to say chronologically here, I thought it would probably be a little bit easier, but when we think about This story with Alfred, Link Exchange, 1995. What happened? How did you lose a hundred and twenty-five million dollar deal by being too honest, Ali?

A Yeah, so this is a story that I just tweeted about last month after almost 20 years. I was 25. It's very interesting because the time frame we're talking about was exactly the time that I was realizing as a 25 year old that betting on startups is all about betting on people. And I had told myself, I want to develop this super skill. And so as a head of biz dev for our company, I was trying to find other startups, not just based on their technology, but trying to evaluate their people, finding other startups for us to partner with. I found this incredible startup with just truly what felt like magic, this company ViaWeb, whose CEO, Paul Graham, I could tell from within the first conversation was brilliant, and his other folks were also brilliant, and I really wanted to partner with them. And then at the same time, Yahoo wanted to So we were trying to acquire via web and we'd reached sort of a handshake, rough handshake agreement. Like we had, you know, it wasn't a solid agreement, but we had reached an understanding. Yeah, we could do this. And then we received a term sheet from Yahoo for them to acquire my company. It was a hundred and twenty five million dollar acquisition, which was enough to make me, you know, as a 25 year old, very wealthy. It's much more money than I had ever expected in my life, but more importantly to make many of our employees very wealthy. So we accept…

AI assessment note: “we received a term sheet from Yahoo for them to acquire my company”

Q the only ones at the table. You kind of did that. So I guess my question is, did you not follow the advice that we give so many, which is like, appear like you have leverage and have a position of power and strength. Like, when I listen to that, I'm like, it could have created FOMO for him, where he did bid up. How do you think about that?

A I would agree that you should bring leverage and strength to a deal, and this applies not just to selling your company. Obviously, it applies to fundraising. If you're raising your next You should be strong, but there's a big difference between being strong and being misleading. One thing I learned and I've passed on to the other founders is you can show strength without implying anything that's not true, especially if you're negotiating with somebody who has more experience. If you overplay your hand, they will know it. In my case, I don't know how many deals I had done at that point, but certainly not as many as Steve Jobs. And most founders have not gone through as many fundraisings as the VC has, obviously, right? As a VC, we see whatever. Multiple deals a week, and so you can tell when somebody's overplaying their hand. Now, to be strong without misleading, all you need to do is to say, I won't accept that. You don't need to say why. You don't need to make implications for, I have a better offer or I don't. If you simply say, we won't do it for less than X, that's strength. You can say that. Don't manufacture false information or false implications as to what else. If I had said to Steve merely, we wouldn't take a deal less than one 50, that would have been just as strong without Having the implication of something untrue. The other element I'd say, though, is humility, wh…

AI assessment note: “there's a big difference between being strong and being misleading.”

Q My friend, you teed me up there. What's one or two of those misses which really comes to mind?

A I mean, I have so many, so, I mean, some of the seminal ones, I would say, were where I truly knew the person, and I knew they are a genius, and so these are, like, the stupidest misses. So at my first startup, LinkExchange, we had this brilliant contractor who was younger than us, so I was 25, Max Lefton was 22, and when we sold our company, he left to start PayPal. We all knew Max was, like, just a whole next-level brilliance. I mean, when he walked into the office, people would Speak in hushed tones. Oh my gosh, it's Max Lefgen. And the original PayPal idea, actually, I think it was called Confinity or some other weird name. It was almost a joke. It was this app for Palm Pilots to zap money using infrared. It almost felt like an episode of Silicon Valley. Like, that's not a business. Come on, who's going to be zapping money via infrared from one Palm Pilot device to the other? In hindsight, though, investing in PayPal was not about the original business idea. It was about investing in Max Lefgen. That was one miss, and same time frame, one of my smartest friends from Harvard, Craig Silverstein, was probably the top guy in our CS program. He and my brother and I were probably always vying for which of us is the best coder in the Harvard class of 94 in computer science, and it was probably Craig. After, I think in 1999, he was leaving his Stanford PhD program to join a new sta…

AI assessment note: “That was one miss, and same time frame, one of my smartest friends”

Q provide them with candidates for roles, and really lean on VCs for hiring. I'm like, bluntly, the best founders hire themselves. The Collison's fucking killed it on hiring. You know, many of the great founders who've done the same. It almost frustrates me. Like, how do you feel about that? And like, I know Neo obviously, oh, Great at hiring, but like, do you really think the other VCs are?

A It's an interesting question to post to me, so I would say it is my fucking job, so I am happy to be leaned on for that, but I would agree at the same time, most VCs are not good at that, and regardless, I don't want anyone, including myself, to be a crutch. I think of it more as a augment, teaching founders best practices, you know, so that they become independently strong at it, and, you know, the best companies, you know, pick up Build their own muscles, need less and less help over time. Any investor or mentor or advisor is going to have some sort of, you know, exponential decay in how helpful they can be because hopefully the founders and their executive team over time become greater than we are. And I would say for me as an investor, as a mentor, the true joy of being a mentor and investor is to see somebody younger than yourself grow to be stronger than you and bigger than you and more successful than you. And I've had the Extreme pleasure and privilege of having seen that multiple times with, you know, many companies like some of the ones I just mentioned.

AI assessment note: “I would agree at the same time, most VCs are not good at that”

Q I do want to finish for a quick fire though. On a third and final story, you mentioned the greats of Google there. Switching tasks to different greats, but Jimmy Iovine, Bono, Fucking love Bono, but take me to this story. What happened there, and how did it go down?

A Yeah, so first of all, I also love Bono. Truly one of the most wonderful humans, I think, in history. He was the hero of the story, and that he came and sort of helped save me from. Essentially, I bungled negotiation with one of the most powerful people in the music industry, which was, my startup was in the music industry, and one part that I'm proud of with this story is that I've always been on the side of Creators. Whether it's, my first company was about helping small businesses. The second company I like was about helping musicians. In some ways, I would say, and what I do at Neo today is helping founders. In this negotiation, Jimmy Iovine, you know, the music industry was very much with its back against the wall in 2007, 2008 era, and they were like a wounded tiger lashing out at anyone. Not only was it outright war between the music industry and the tech companies, but also there was a Cold War going on between the music industry and their own bands, because bands who had signed record contracts decades ago were jockeying to figure out in the new internet era who owns the digital rights, and so U-Two was one of Jimmy's largest bands, presumably partners, but they were also actually kind of in a war as to who has the rights to their digital presence. We were on the side of helping the band, and as a result, we became the first Front in this war. YouTube posted a amazing …

AI assessment note: “Essentially, I bungled negotiation with one of the most powerful people in the music industry”

Q You said you thought about it a lot. You know, I think one thing that plagues investors is FOMO. How do you think about FOMO and regret as an investor today? I'm intrigued.

A So it's interesting. Yeah. FOMO is, it can really be a misleading thing, right? It can be both a reason to make good decisions or a reason to make mistakes. I have generally tried as much as I can to, as an investor to try to find my own compass, to try not to focus on who else is doing what and what if I miss out. And rather in terms of whether it's a good investment, find my own reasons. And also in terms of convincing them to take our money, try to win based on our merits. I should start by saying I'm extremely confident about what NIO brings to the table. When we invest in a company, we don't just invest capital. We help build the company, and by that I mean we help build their engineering team, which is the engine that creates everything, and for most of our successful portfolio companies, we sourced something like half their early engineers. In some cases, more than half. Because I have that confidence, I don't tend to get as worried about losing deals, and if there's, I certainly do lose deals, but I often feel like, you know what, if they didn't see the value in what we offer, maybe it's not that big a loss to us either. Maybe they don't actually need that help. It could often mean they don't realize how hard hiring is, and if somebody hasn't reached that realization yet, they might not actually be as strong a founder, and when they do, we might get a second bite at the…

AI assessment note: “try to find my own compass, to try not to focus on who else is doing what”

Q when you take money from an investor, that is a responsibility, just like it is for me when I raise money from LPs. For you to then go and raise money for a separate fund on the side to spend time investing someone else's money, having taken my money invested in your company, I have a problem with that. How do you feel about founders raising funds on the side?

A I mean, I think I agree with you for a few reasons. First of all, I can barely do one thing well, let alone do multiple things well. I'm deeply skeptical of somebody who is a CEO of a startup being able to also run anything else. Now there are obviously some very inspiring exceptions. Elon Musk is, you know, simultaneously running multiple companies or Jack Dorsey, but not counting these superhumans, the generally I would say do one thing really well. And if you're the CEO of a company, don't also start a fund. So on both sides, right? Like to be a VC is hard. Hard work. And lastly, I would say if you are a great angel investor as a founder, you can probably make more money just in angel investing. Why would you want to dilute your possibilities by taking on other money? I would agree with you. I don't think it makes sense. I think founders angel investing is really great. One aspect of it that I do like is that I've always thought of it as a life cycle that today's founders are tomorrow's investors. I think it's nice to help everyone realize that, you know, investors aren't Some kind of evil species or different species. They are just a different life stage of the same species. You know, we all believe we're all in the same game of building amazing companies. We're just, you know, playing different roles in the ecosystem.

AI assessment note: “I think I agree with you for a few reasons.”

Q Can I ask, you mentioned Dropbox there. You had an incredible experience with Dropbox as an investor, as an advisor, really with the front row seat. What were some of the big takeaways, and how did it impact your mindset, do you think, Ali?

A Well, you know, I'd say the common arc From my own first startup and what I was saying about Alfred and through various angel investments to Dropbox has to do with people. I remember actually the first founder that I mentored after selling my own company was my twin brother, Hadi. This is 20 years ago. He was starting his first startup, and he said, what are the three top pieces of advice that I would give him as a young founder? And Hadi always liked things in threes. So I thought about it, and I said, number one, hire the best people. Number two, hire the best people. Number three, hire the best And when we were investors in Dropbox, well, Hadi gave the same advice to young Mark Zuckerberg at Facebook that we were early advisors to, but also gave the same advice to Drew and Dropbox. I'd say pretty much every time we met with them, what we spoke about were people, whether hiring or coaching them through firing their first person. Beyond that, we started giving an annual talk at Dropbox on the importance of hiring, on techniques for recruiting, just as we'd given Facebook this advice, gave them the advice of building an intern program on Hiring younger people than themselves. Dropbox did a lot of innovation in terms of their intern program. For example, they had a parents weekend where they would invite the parents of the interns to come just so that they would feel comfortable…

AI assessment note: “pretty much every time we met with them, what we spoke about were people”

Q you mentioned Alfred, and I want to go back to LinkExchange, and I want to start with our first story of the day, and I decided to say chronologically here, I thought it would probably be a little bit easier, but when we think about This story with Alfred, Link Exchange, 1995. What happened? How did you lose a hundred and twenty-five million dollar deal by being too honest, Ali?

A Yeah, so this is a story that I just tweeted about last month after almost 20 years. I was 25. It's very interesting because the time frame we're talking about was exactly the time that I was realizing as a 25 year old that betting on startups is all about betting on people. And I had told myself, I want to develop this super skill. And so as a head of biz dev for our company, I was trying to find other startups, not just based on their technology, but trying to evaluate their people, finding other startups for us to partner with. I found this incredible startup with just truly what felt like magic, this company ViaWeb, whose CEO, Paul Graham, I could tell from within the first conversation was brilliant, and his other folks were also brilliant, and I really wanted to partner with them. And then at the same time, Yahoo wanted to So we were trying to acquire via web and we'd reached sort of a handshake, rough handshake agreement. Like we had, you know, it wasn't a solid agreement, but we had reached an understanding. Yeah, we could do this. And then we received a term sheet from Yahoo for them to acquire my company. It was a hundred and twenty five million dollar acquisition, which was enough to make me, you know, as a 25 year old, very wealthy. It's much more money than I had ever expected in my life, but more importantly to make many of our employees very wealthy. So we accept…

AI assessment note: “on the eve of the acquisition, I had drinks with Jerry Yang”

Q You said you thought about it a lot. You know, I think one thing that plagues investors is FOMO. How do you think about FOMO and regret as an investor today? I'm intrigued.

A So it's interesting. Yeah. FOMO is, it can really be a misleading thing, right? It can be both a reason to make good decisions or a reason to make mistakes. I have generally tried as much as I can to, as an investor to try to find my own compass, to try not to focus on who else is doing what and what if I miss out. And rather in terms of whether it's a good investment, find my own reasons. And also in terms of convincing them to take our money, try to win based on our merits. I should start by saying I'm extremely confident about what NIO brings to the table. When we invest in a company, we don't just invest capital. We help build the company, and by that I mean we help build their engineering team, which is the engine that creates everything, and for most of our successful portfolio companies, we sourced something like half their early engineers. In some cases, more than half. Because I have that confidence, I don't tend to get as worried about losing deals, and if there's, I certainly do lose deals, but I often feel like, you know what, if they didn't see the value in what we offer, maybe it's not that big a loss to us either. Maybe they don't actually need that help. It could often mean they don't realize how hard hiring is, and if somebody hasn't reached that realization yet, they might not actually be as strong a founder, and when they do, we might get a second bite at the…

AI assessment note: “find my own compass, to try not to focus on who else is doing what”

Q when you take money from an investor, that is a responsibility, just like it is for me when I raise money from LPs. For you to then go and raise money for a separate fund on the side to spend time investing someone else's money, having taken my money invested in your company, I have a problem with that. How do you feel about founders raising funds on the side?

A I mean, I think I agree with you for a few reasons. First of all, I can barely do one thing well, let alone do multiple things well. I'm deeply skeptical of somebody who is a CEO of a startup being able to also run anything else. Now there are obviously some very inspiring exceptions. Elon Musk is, you know, simultaneously running multiple companies or Jack Dorsey, but not counting these superhumans, the generally I would say do one thing really well. And if you're the CEO of a company, don't also start a fund. So on both sides, right? Like to be a VC is hard. Hard work. And lastly, I would say if you are a great angel investor as a founder, you can probably make more money just in angel investing. Why would you want to dilute your possibilities by taking on other money? I would agree with you. I don't think it makes sense. I think founders angel investing is really great. One aspect of it that I do like is that I've always thought of it as a life cycle that today's founders are tomorrow's investors. I think it's nice to help everyone realize that, you know, investors aren't Some kind of evil species or different species. They are just a different life stage of the same species. You know, we all believe we're all in the same game of building amazing companies. We're just, you know, playing different roles in the ecosystem.

AI assessment note: “if you're the CEO of a company, don't also start a fund.”

Q What would you have done differently? And is there a takeaway for founders that other than maybe don't have a margarita?

A I would agree. Do not drink when you're having major business discussions. It's interesting because I've asked myself, some level I would have done the same. Like, I think that the exuberance I had Seeing something wonderful and talking about it. I never want to become such a cynic that I suppress that, but I think what I would perhaps say the common theme of all of my mistakes I'd say in business are impatience. In hindsight, I could have waited, you know, three or four days and then tell Jerry what I really thought after our deal was closed. And by the way, it might not have made a difference. The accounting thing might've been the real reason, but I think one of the things as a younger, both as a founder and probably as an investor has been one of my flaws is So that's perhaps one learning, but I would say that the other learning that I was hundred percent right on was the evaluating of these people. These people truly were geniuses, and obviously with what Paul and Gang have accomplished since, if anything, I would say it was Yahoo's loss not to keep them longer.

AI assessment note: “In hindsight, I could have waited, you know, three or four days”

Q provide them with candidates for roles, and really lean on VCs for hiring. I'm like, bluntly, the best founders hire themselves. The Collison's fucking killed it on hiring. You know, many of the great founders who've done the same. It almost frustrates me. Like, how do you feel about that? And like, I know Neo obviously, oh, Great at hiring, but like, do you really think the other VCs are?

A It's an interesting question to post to me, so I would say it is my fucking job, so I am happy to be leaned on for that, but I would agree at the same time, most VCs are not good at that, and regardless, I don't want anyone, including myself, to be a crutch. I think of it more as a augment, teaching founders best practices, you know, so that they become independently strong at it, and, you know, the best companies, you know, pick up Build their own muscles, need less and less help over time. Any investor or mentor or advisor is going to have some sort of, you know, exponential decay in how helpful they can be because hopefully the founders and their executive team over time become greater than we are. And I would say for me as an investor, as a mentor, the true joy of being a mentor and investor is to see somebody younger than yourself grow to be stronger than you and bigger than you and more successful than you. And I've had the Extreme pleasure and privilege of having seen that multiple times with, you know, many companies like some of the ones I just mentioned.

AI assessment note: “I would agree at the same time, most VCs are not good at that”

Q What would you have done differently? And is there a takeaway for founders that other than maybe don't have a margarita?

A I would agree. Do not drink when you're having major business discussions. It's interesting because I've asked myself, some level I would have done the same. Like, I think that the exuberance I had Seeing something wonderful and talking about it. I never want to become such a cynic that I suppress that, but I think what I would perhaps say the common theme of all of my mistakes I'd say in business are impatience. In hindsight, I could have waited, you know, three or four days and then tell Jerry what I really thought after our deal was closed. And by the way, it might not have made a difference. The accounting thing might've been the real reason, but I think one of the things as a younger, both as a founder and probably as an investor has been one of my flaws is So that's perhaps one learning, but I would say that the other learning that I was hundred percent right on was the evaluating of these people. These people truly were geniuses, and obviously with what Paul and Gang have accomplished since, if anything, I would say it was Yahoo's loss not to keep them longer.

AI assessment note: “In hindsight, I could have waited, you know, three or four days”

Q I would love to start here with a little bit of storytelling, though, in the way that, you know, bluntly, it was a different route into venture. So tell me, how did you make your move from operating into the world of venture and most recently come to found Neo?

A Yeah, so Neo is a, I call it a mentorship community. It's a diverse mentorship community. Community and VC fund. Our mission is to identify America's most promising CF students and help them become tomorrow's tech leaders. I'd say I started Neo because I wish existed when I was a college student, and it's also what I wish existed when I was a young founder. When I was 24, the most important lesson I learned as a founder was the importance of people. I realized that the people we hired made the difference between success and failure, and the first five or 10 are most important because they hire the next 50 to a hundred. And in particular, I also learned the importance of betting on young people. It's funny you mentioned Alfred, because at my first startup, Alfred was a part-time accountant. He was a friend of ours from college. In the first year or so, I was kind of anti-Alfred. The other co-founders knew him better, and they're like, this guy's brilliant. And I was like, why are we having somebody who is a PhD student at Stanford at the time, part-time? My co-founders were suggesting we should make him our CFO. And I was like, what are you talking about? He's our age. We should have somebody older with more experience. Experience as our CFO, why would we bet on somebody so young who's never done that before? And so for about a year, Alfred reported to me and I was trying to fin…

AI assessment note: “I started Neo because I wish existed when I was a college student”

Q Can I ask, you mentioned Dropbox there. You had an incredible experience with Dropbox as an investor, as an advisor, really with the front row seat. What were some of the big takeaways, and how did it impact your mindset, do you think, Ali?

A Well, you know, I'd say the common arc From my own first startup and what I was saying about Alfred and through various angel investments to Dropbox has to do with people. I remember actually the first founder that I mentored after selling my own company was my twin brother, Hadi. This is 20 years ago. He was starting his first startup, and he said, what are the three top pieces of advice that I would give him as a young founder? And Hadi always liked things in threes. So I thought about it, and I said, number one, hire the best people. Number two, hire the best people. Number three, hire the best And when we were investors in Dropbox, well, Hadi gave the same advice to young Mark Zuckerberg at Facebook that we were early advisors to, but also gave the same advice to Drew and Dropbox. I'd say pretty much every time we met with them, what we spoke about were people, whether hiring or coaching them through firing their first person. Beyond that, we started giving an annual talk at Dropbox on the importance of hiring, on techniques for recruiting, just as we'd given Facebook this advice, gave them the advice of building an intern program on Hiring younger people than themselves. Dropbox did a lot of innovation in terms of their intern program. For example, they had a parents weekend where they would invite the parents of the interns to come just so that they would feel comfortable…

AI assessment note: “the common arc From my own first startup... to Dropbox has to do with people.”

Q I would love to start here with a little bit of storytelling, though, in the way that, you know, bluntly, it was a different route into venture. So tell me, how did you make your move from operating into the world of venture and most recently come to found Neo?

A Yeah, so Neo is a, I call it a mentorship community. It's a diverse mentorship community. Community and VC fund. Our mission is to identify America's most promising CF students and help them become tomorrow's tech leaders. I'd say I started Neo because I wish existed when I was a college student, and it's also what I wish existed when I was a young founder. When I was 24, the most important lesson I learned as a founder was the importance of people. I realized that the people we hired made the difference between success and failure, and the first five or 10 are most important because they hire the next 50 to a hundred. And in particular, I also learned the importance of betting on young people. It's funny you mentioned Alfred, because at my first startup, Alfred was a part-time accountant. He was a friend of ours from college. In the first year or so, I was kind of anti-Alfred. The other co-founders knew him better, and they're like, this guy's brilliant. And I was like, why are we having somebody who is a PhD student at Stanford at the time, part-time? My co-founders were suggesting we should make him our CFO. And I was like, what are you talking about? He's our age. We should have somebody older with more experience. Experience as our CFO, why would we bet on somebody so young who's never done that before? And so for about a year, Alfred reported to me and I was trying to fin…

AI assessment note: “I started Neo because I wish existed when I was a college student”

Q I do want to finish for a quick fire though. On a third and final story, you mentioned the greats of Google there. Switching tasks to different greats, but Jimmy Iovine, Bono, Fucking love Bono, but take me to this story. What happened there, and how did it go down?

A Yeah, so first of all, I also love Bono. Truly one of the most wonderful humans, I think, in history. He was the hero of the story, and that he came and sort of helped save me from. Essentially, I bungled negotiation with one of the most powerful people in the music industry, which was, my startup was in the music industry, and one part that I'm proud of with this story is that I've always been on the side of Creators. Whether it's, my first company was about helping small businesses. The second company I like was about helping musicians. In some ways, I would say, and what I do at Neo today is helping founders. In this negotiation, Jimmy Iovine, you know, the music industry was very much with its back against the wall in 2007, 2008 era, and they were like a wounded tiger lashing out at anyone. Not only was it outright war between the music industry and the tech companies, but also there was a Cold War going on between the music industry and their own bands, because bands who had signed record contracts decades ago were jockeying to figure out in the new internet era who owns the digital rights, and so U-Two was one of Jimmy's largest bands, presumably partners, but they were also actually kind of in a war as to who has the rights to their digital presence. We were on the side of helping the band, and as a result, we became the first Front in this war. YouTube posted a amazing …

AI assessment note: “Essentially, I bungled negotiation with one of the most powerful people in the music industry”

Q sell you so well, Ali, on the vision. I could sell the shit out of you, yeah? And I could be very shallow in terms of what's behind the scenes. My point being, you know, especially in an engineering-first world where they're less charismatic, most often, bluntly, and less salesy, How do you think about talent detection when it's not as obvious as I think it used to be, actually?

A I'll say one of the things that for me was a truly formative point in my career was when I was a twenty-four-year-old founder, we were struggling with how to evaluate candidates, and in particular candidates older than ourselves. We were trying to hire a VP of sales and a VP of engineering, and we were 24, and we'd get a candidate who was 34, and their resume just looked intimidating. We'd have five candidates, and they all looked Great. We had really, you know, we just weren't sophisticated about how do you tell whether someone's better than someone else. And our lead investor was Sequoia and Mike Moritz was on our board and would come multiple times a week to our office and join us in these interviews. So I'd interview the candidate and Tony would interview the candidate and then Mike would interview the candidate. And then we would debrief afterwards. And I learned so much from Mike. He would eviscerate these candidates where I'd be like, yeah, they seemed good. And he'd be like, absolutely not. And I realized there was a Skill that I didn't possess.

AI assessment note: “I realized there was a Skill that I didn't possess.”

Q sell you so well, Ali, on the vision. I could sell the shit out of you, yeah? And I could be very shallow in terms of what's behind the scenes. My point being, you know, especially in an engineering-first world where they're less charismatic, most often, bluntly, and less salesy, How do you think about talent detection when it's not as obvious as I think it used to be, actually?

A I'll say one of the things that for me was a truly formative point in my career was when I was a twenty-four-year-old founder, we were struggling with how to evaluate candidates, and in particular candidates older than ourselves. We were trying to hire a VP of sales and a VP of engineering, and we were 24, and we'd get a candidate who was 34, and their resume just looked intimidating. We'd have five candidates, and they all looked Great. We had really, you know, we just weren't sophisticated about how do you tell whether someone's better than someone else. And our lead investor was Sequoia and Mike Moritz was on our board and would come multiple times a week to our office and join us in these interviews. So I'd interview the candidate and Tony would interview the candidate and then Mike would interview the candidate. And then we would debrief afterwards. And I learned so much from Mike. He would eviscerate these candidates where I'd be like, yeah, they seemed good. And he'd be like, absolutely not. And I realized there was a Skill that I didn't possess.

AI assessment note: “I realized there was a Skill that I didn't possess.”