E440: What Steve Jobs Taught Me About Great Founders

What did Steve Jobs understand about building great companies that most founders miss? Steven Rosenblatt is Co-Founder and General Partner at Oceans, a seed-stage venture firm based in New York City. Drawing on more than two decades as an operator and investor, including his time at Apple and Foursquare, Steven shares what he learned working directly with Steve Jobs, how he separates ambitious founders from delusional ones, what drew Oceans to Etched, and why AI is creating a technology cycle unlike anything he has seen before.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Founders and ambitious are deep in detail. You can hear what they're saying. You can see what they're thinking about. They take you along their journey. They're very deep in terms of their thinking and they can articulate clearly what the company looks like today and where they want to take it. They may be wrong. It's very clear. Delusional is long on smoke and mirrors. You kind of look and you kind of say, they're light on details and substance, but pretty damn good on storytelling and there's a lot of smoke and mirrors.

• 0:30David Weisburd?

  You got to see firsthand Steve Jobs, got to work with him. What did you observe from working with Steve Jobs?

• 0:38Speaker 00

  What I saw from Steve was this incredible ability to go like so deep into the weeds on things. His ability to look at everything from like pixels and colors to then this incredible vision of what he wanted to do is just so unique. And it's very rare to find a human who's able to get so into the weeds and in such detail on so many things, but yet have such a grand vision.

• 1:06David Weisburd?

  So Stephen, you've spent over 20 years building companies, investing. What do great technology companies have in common?

• 1:15Speaker 00

  Starts with the people. I think first and foremost, it is without question, the companies that are able to attract the best talent, where the founders really appreciate and understand that in order to build a world-class organization and culture, you need world-class people and you need people better and great at specific things. And without question, the number one universal thing through all the different periods is people and talent.

• 1:46David Weisburd?

  Everybody wants to have great talent in their company, but how does one go about building a culture and a process of building great talent?

• 1:53Speaker 00

  It starts with the founder. I mean, you need money. So I think like, if you don't have capital, it's hard to pay people and you have equity. But it starts with someone who's, you know, I think smart people, they want to do big things. They don't want to do boring things. And so I think, you know, when I see a founder who's building something that truly is different, unique, game-changing, it's going to attract different type of people, right? Cause it's just a magnet. If there's this company that's being built and there's 15 of those companies, the best people, best talent may not see it as a challenge. So it's got to be a challenge. It's got to be something that you feel like you're helping and part of building.

• 2:36Speaker 00

  And I think the onus also is on the founder to make everyone feel like they're part of building it. It's not just the founder's company, it's everyone's company.

• 2:45David Weisburd?

  Have you been involved in one of these companies in your career?

• 2:48Speaker 00

  Yeah, I think I've been involved in several of them in different forms and fashion. When I was at Quattro Wireless in 2008, during the kind of early days of mobile, the founders, Andy Ishwar Lars, they were just incredible and super complimentary in terms of skill sets. And to join a mobile company when my wife was six months pregnant, right as the financial crisis was hitting, that's kind of crazy. But I did it because I loved them. I loved the culture. I loved the people. They were inspiring and they were about to build, I know now it's easy to be like, oh, it's mobile, that was obvious. In 2007, eight, it was far from obvious.

• 3:31Speaker 00

  I can't tell you how many people told me I was nuts for going to a company that was going to try and build something for a device that was like this small, when there was really a keyboard and Apple was just rolling out their first phone. But again, I jumped on because I just felt like they were so inspiring and they were incredible people.

• 3:50David Weisburd?

  As investor, how do you go about telling between ambition and delusion when it comes to top founders?

• 3:57Speaker 00

  Well, I think it's the difference between success and failure. Founders and ambitious are deep in detail. They have a, you can hear what they're saying. You can see what they're thinking about. You can, they take you along their journey. They're very deep in terms of their thinking and they can articulate clearly what the company looks like today and where they want to take it. They may be wrong, but it's very clear. Delusional is long on smoke and mirrors. You kind of look and you kind of say, they're light on details and substance, but pretty damn good on storytelling and there's a lot of smoke and mirrors. And I think that's also, you know, typically leads to the difference between success and failure.

• 4:41David Weisburd?

  We're talking about before we started recording that founders today have become so good at storytelling, so good at building narratives. As investor, how do you go about figuring out whether there's something there behind a founder's vision?

• 4:55Speaker 00

  Well, I think it's, it also starts with like, why are they building the company that they're building and what is the insight or what is the reason? What is it that they have? What is, you know, what's kind of deep in their veins, why they have to go build this? And again, are they building it because it's, they feel like it's a gold rush and they're building it because like, this is the time to make money? Or are they building it because it's something they have to do? Because you can tell how much they've done prior to building this company to get this company off the ground. You can hear it, you can see it, you can think, you can hear life experiences or things they've done prior work-wise, or they've already started grinding away and building. And it's just, it's so deep in their veins, I kind of, it's like in their, their heart

• 5:38Speaker 00

  and DNA, whereas others, you hear them and they like, I was like employee 3,000 at so-and-so company and I'm, and because of that, I'm so like magical and I'm going to go start this thing. But there's no substance there. There's no real concrete details there. And, and that's what we really try and unpack and look for, because you're right, there's a lot of great storytellers out there, but you got to sift through the BS.

• 6:02David Weisburd?

  There's an underrated rule from Ashton Kutcher, who alongside being an actor, is actually a really great angel investor. He was in Airbnb earlier and a bunch of $10 billion companies. And he, he frames it in that if you for one second feel compelled to quit whatever you're doing and work for that founder, that is the standard that it takes for him to actually invest. So it's not just vision in terms of, hey, here's what I'm going to do, or here's how I'm going to execute on it. It's literally a talent magnet drawing you to his or her vision to quit whatever it is that you're doing and focus on that dream.

• 6:41Speaker 00

  Well, first of all, Ashton Kutcher was an investor in Foursquare, my old company as well.

• 6:45David Weisburd?

  Another one.

• 6:45Speaker 00

  He didn't quit and come work for us, but he was around the office a bunch of times. But yeah, like, listen, I think that's it. I think there's something about amazing talent and amazing founders. And listen, it's not the only thing. There's a lot of people that are, you know, you're drawn to work for, who wind up not succeeding. But I think that is part of the secret sauce, which is whether it's, would I as an investor go quit and go, you know, if they hired, give me an assistant job, I'd go work for this, this person. Sure, I think that's part of it. But again, I think there's a lot of different, you know, dimensions that you look for, that may be one of them. But you know, their, their knowledge of what they're doing and their insight. The other thing too, I mean, if you think about a lot of great companies, they were pivots.

• 7:30Speaker 00

  And I do think there are certain founders that may be great at one thing, they have their blinders on, but they may not be able to then pivot. They may get so stuck in what they're building. And I do think there's something too about a founder who's able to process information and see what has changed to then take, you know, either their company a certain way or possibly completely change their idea.

• 7:57David Weisburd?

  That distinction between ambition and delusion.

• 7:59Speaker 00

  Yeah.

• 8:01David Weisburd?

  Speaking of exceptional people, you got to see firsthand Steve Jobs, got to work with him. What did you observe from working with Steve Jobs?

• 8:10Speaker 00

  It was a fascinating experience. And I think maybe kind of to take you a step back in terms of how that happened. So going back to the mobile company, we were building this company, Quattro Wireless. And 2009 was kind of the beginning of, you know, the App Store had just started taking off and mobile was just started taking off. You know, went from kind of BlackBerry to now the iPhone, obviously, and then the App Store. And there was a fierce competition between iOS and Android. And what Steve saw, that frankly, I didn't really process until I worked there, until he acquired our company, was that in order to sell these phones, he needed the developer. He wanted the best developers in the world to build apps because those who had the best

• 8:53Speaker 00

  apps were going to be the ones that, the phones that people wanted. So I got to work with him because he ultimately decided to buy our company, Quattro Wireless, which we can get into that story as well. But what I saw from Steve was this, this incredible ability to go like so deep into the weeds on things. So when we were launching iAd, which is the business we ultimately launched at Apple, his ability to like, look at everything that like, from like pixels and colors to then this incredible vision of what he wanted to do is just so unique. And it's very rare to find a human who's able to get so deep, so into the weeds and

• 9:37Speaker 00

  in such detail on so many things, but yet have such a grand vision. And, and I saw that pretty, pretty clearly with Steve.

• 9:44David Weisburd?

  This episode is presented by Juniper Square, the operations partner for private markets.

• 9:51David Weisburd?

  Kind of ties in to what we were talking about, what you look for in founders, which is this almost paradoxical grand vision with this meticulous planning and meticulous execution.

• 10:01Speaker 00

  I think I learned that, you know, and again, it's very, I don't want to, you know, I never benched for it because it's hard, there's only one Steve Jobs and then I think, you know, I don't know if there'll ever be another Steve Jobs. But there are that, you know, that was one of the key things I take away and I really like, it helped look for when I'm looking at founders to see what that kind of cocktail looks like.

• 10:21David Weisburd?

  Take me inside the room when you first met Steve Jobs and you spent three hours with him. What did you observe about him?

• 10:27Speaker 00

  So it started, I mean, so this was fascinating. So I was 33 years old, okay? And I was, they were basically getting close to the finish line to acquire a company for 300 million, around 300 million dollars. Company had only been around for three years. That was a lot of money in 2009. A 300 million exit didn't come along very often. That was big. And I was flying out to Cupertino with Andy Miller, who was a co-founder of Quattro Wireless, who was my boss, who had already spent some time with Steve. But Steve wanted to meet me because I was head of sales and if we were going to launch this new business for Apple, he wanted to meet me. So I was pretty nervous, you know, meeting with Steve Jobs. I'm pretty young.

• 11:10Speaker 00

  I walk into One IL, which is One Infinite Loop, which is the main, at the time, they didn't have the spaceship. It was the main office, that was where Steve's executive office was. And I walk in and they greet us and next thing I know, I'm in the elevator with Bruce Sewell, who's general counsel, and he says, congratulations. And I said, uh, okay, I think this means that they are going to acquire us. But I'm like, oh shit, this means that I can really screw up a 300 million dollar exit. And so I'm with Andy, we go up there and so one end, I'm like a little bit like monkey off the back, but I'm like, okay, now the only thing that can happen is I can ruin this deal.

• 11:55Speaker 00

  So I walk into, Andy and I, we get seated, we're in the executive conference room, that's Steve's executive conference room, his assistant sits us down. And next thing I know, you've got Tim Cook walking in, Eddie Q walking in, Scott Forstall walking in. And we're just sitting there talking, waiting like 20 to 30 minutes for Steve to come into the room. And it's a lot of small talk with them. And I was warned ahead of time, because Steve had just come back from being out, he had just come back, he had pancreatic cancer, he had just come back from his treatments, it was like really his first like weeks back at Apple. But I remember, you know, getting in the room, sitting in the room with the exec team, and then the questions came.

• 12:35Speaker 00

  And then it was, when you sat with Steve, first of all, it was just a barrage of questions. Like, it was just coming at you, but then there were these long awkward pauses. So imagine if you and I are doing this interview right now, you're asking me questions and we sit here, you start looking in the sky like this, like this, like this, for like a minute and a half with these most awkward pauses. And I'm sitting here being like, is he going to ask me a question? Is he not? Should I respond? What do you do? There were these most interesting pauses, I'd never experienced that before. And I've met with a lot of successful people.

• 13:11David Weisburd?

  Reminds me a little bit of Peter Thiel. Peter Thiel is famous for these long awkward pauses.

• 13:15Speaker 00

  Yeah, so I mean, I've never been with Peter. So it was with these long awkward pauses and then he just started asking, and they're these crazy, deep, thoughtful questions.

• 13:25David Weisburd?

  Like what?

• 13:26Speaker 00

  So what it was clear to me, what he really was trying to figure out was not the product that we had at Quattro Wireless, he could care less about that. It was, is this a team that I can trust? Because we at Apple don't know this business. We don't know how to sell ads and monetize and all the infrastructure to sell ads, to for developers, because we want developers to make money. So what he really was testing is, are these people that are going to teach us? Can we learn from them? Can they teach us an industry? He would ask us, what advertisers want? What do they love about you? How do they work? How do they operate?

• 14:08Speaker 00

  Now, he knew, listen, Apple was, he was, you know, notorious for being an incredible creative genius and a great advertiser himself. So he knew what advertisers wanted from a certain perspective. But it was a lot of depth, it was a lot of seeing how we'd fit in culturally. Because again, at the time, Apple only acquired at most 10 companies. So they, the biggest company they'd bought before us was P A Semi, a semiconductor company. So it was really about feeling whether we were going to be people who they can trust, culturally fit in, how we hired, what we looked for in talent, how we built, but how the customers that we were going to help bring in, could we teach Apple how to build a huge business here that would be different than anything else that existed?

• 14:52Speaker 00

  And that, there were three hours of questions to really assess that. Thankfully, we passed the test.

• 14:57David Weisburd?

  What did that teach you about how to acquire companies?

• 15:00Speaker 00

  Again, when I think about Apple, they were really not good at acquiring companies back then. It was not part of their DNA and muscle. And frankly, when they acquired us, there were a lot of things we had to teach them. Apple at the time had one P and L. Fascinating for a company that had all these, still at the time, had, you know, a number of different products. One P and L, one ultimate decision maker, Steve Jobs. I don't think that's how Apple exists today. I don't think, I think it's changed. But it was so unique. And then they were buying, and then our company, we were the only, um, division within Apple that truly was its own P and L. Everyone at Apple were, you know, and again, they were a hardware company and software company.

• 15:42Speaker 00

  And here they are, buying this company where they couldn't believe, you know, what certain people were making on the team, or why were people compensated or not engineers were getting this much equity? And we had to teach them a lot about, at the time, that when you're acquiring a company and it may not fit exactly how your existing company works, how do you ensure that they fit in to build a successful product? Fast forward, you know, Apple's, what we built for them, which was iAd, which is now Apple Ads, which is a multi, multi-billion dollars business under services. And I know that Quattro Code was still up and running up until, like, I know a couple of years ago.

• 16:25Speaker 00

  So I think it's, it's about, you know, most acquisitions don't do well. There's this kind of, you know, organ resistance usually, one way or another. I think what was fascinating for us is that Andy Miller, who was my boss, reported to Steve the entire time. When I was there, they didn't just take us and then put us under some obscure group. We got access to everything we needed at Apple. We had the best resources, the best people, because ultimately, Steve presented us at WWDC and we were one of the tent pole items in 2000, I think it was 10, uh, 10 or 11, yeah, 10 WWDC. So having his support at the top was really important.

• 17:09Speaker 00

  I think a lot of acquisitions fail because you get acquired and then they kind of put you in some obscure areas under someone who doesn't even know why the company bought you. And then, you know, you get organ rejection between the founders and that culture and the company.

• 17:21David Weisburd?

  What do you think Steve Jobs understood about company building that most founders fundamentally do not?

• 17:28Speaker 00

  I'd say a couple of things. Number one, Steve surrounded himself with complimentary personalities. There wasn't an, if you had more than one Steve Jobs in the room, it would have never worked, personality wise.

• 17:44David Weisburd?

  Why?

• 17:45Speaker 00

  When you think about Tim, because it's just too much friction. Steve is, he was such a hard-charging, intense person. When you look at Tim Cook, balanced out Steve, really kind, really comforting, operational rigor. Eddie Q, the dealmaker, the person who played a good cop to Steve's bad cop doing deals. I think what Steve, and I think a lot of the, what I've seen, incredible founders know what to do. I think Mark Zuckerberg did this with Sheryl, is they understand their personality. They understand that if there's too much of their extreme, that the company can't operate. If you had too much of that intensity, too much of that drive, too much of that, Steve kind of, you'd just drive people into the ground.

• 18:30Speaker 00

  And I think Steve knew how to surround himself with, and I think great founders do this, they surround themselves with complimentary talent and their personality flaws. And so I would say that's, that's certainly one of it. I think one thing. The other thing is this attention to detail, right? I think what made Apple so unique is, again, there can only be one Apple, and I think there's, it's very rare for other companies to try to emulate this to be successful. But you would focus on building, you know, your iPad or my watch, there's like a team that's like, just like focusing on like the numbers, right? Like, all they do is focus on the numbers, right? Or the, you know, this, the dial, right?

• 19:14Speaker 00

  Like, very specific teams doing very specific things that they obsess about the details. Now, it is really hard for most cultures to succeed doing that. But I, what I took away and what I learned is, you're better off doing a few things incredible than doing a lot of things mediocre. And that was something that I think Apple, and what I witnessed and saw, that culturally ingrained in how they did things. They didn't do a lot, but the things they did, everyone did something very specialized, which was pretty, pretty fascinating.

• 19:46David Weisburd?

  This addition through subtraction, what's an example of that?

• 19:49Speaker 00

  Like, when we were launching, uh, iAd, right, at the time. So iAd was this new platform, at the time, there were all these, you know, all mobile was a bunch of crap. There's all these banner ads, and there were small little banner ads, and you could barely read them. And Steve, to his credit, said, no, we're not going to just do, you know, have a little banner ad. We want, we want the things on any iOS device, we want them to be beautiful. We want them to be TV-like experiences. Again, back then, there wasn't a lot of video and there wasn't a lot of these incredible, like, mobile experiences. So when we were launching iAd and going out to the market and getting brands to participate...

• 20:31Speaker 00

  Literally every week for six to eight weeks, we had these launch partners that were going to go out. They were presenting at WWDC. And every week, those brands had to come back to Disney. It was Unilever. It was Nissan. And it was Citibank. And their creative teams had to literally ship their creatives that they were working on, that Steve would look at himself and review and give feedback on and send back. I mean, he was right. This is like, Apple just launched iPad. And it was the hottest company in the world. And it'd just gotten like totally its mojo, it was flying. And he's reviewing ads for a relatively small business.

• 21:15Speaker 00

  And I think like, it's that level of focus. And then the people that were working with us were like, literally focused on making sure like very specific stuff within the iAds that we're launching, were showcasing all of the benefits of the operating system, right? What made the native operating system features and function? So that was the experience that I had. But I know there are teams, I was exposed to teams, literally that were just working on like very particular things, the dial to hand on a clock on the watch, you know, like very, very specific and tedious things. And yeah, I mean, that's, again, I don't think it works at most companies,

• 21:56Speaker 00

  but I do think that obsession of detail, the great companies, the great founders, really obsessed about making sure their products are the best at the end of the day.

• 22:08David Weisburd?

  And he instilled that into the entire organization?

• 22:11Speaker 00

  Yeah, for sure.

• 22:12David Weisburd?

  How?

• 22:14Speaker 00

  Well, he challenged you. I mean, if you came to a meeting, we would have these meetings. And then, you know, when we were launching, we were preparing to launch this business, iAd. And Andy Miller, Andy would meet with Steve every week. And you better be prepared, like literally know, like be prepared and think about any possible question he could ask about the product, about the creative, about why we're doing certain things, why that brand is, you know, why we decided to take that brand on. And I was like Andy's therapist, because he would call me after these meetings. And he'd be like, Stephen, you want the good news or the bad news? Right?

• 22:57Speaker 00

  And like, or Stephen, today, oh my God, this was the best. Like, I didn't get yelled at today. And he was actually really happy and impressed with what we did. I will take that as a huge win. We're doing something right. So, oh my God, he called me a bozo. He yelled at me for something. And like, we have to go, go back to the customer and ask for, you know, tell them to change it up, or tell them we're not going to show that ad, even though we told them we were going to show it. So it forces, it almost like forced you to think about things from every angle and be prepared, because when you sat with that, you know, I didn't, I didn't sit weekly, but Andy did. And I'd come back and kind of hear it and take the brunt of it, which is, if you weren't

• 23:39Speaker 00

  prepared for that meeting, you would get destroyed. So you better have every single thing. So when you were sitting with the exec team, you better, you know your business. You gotta know your business. You gotta know everything about your business. And again, those are some of the lessons I've learned and taken away kind of going forward.

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• 26:05David Weisburd?

  That's why I question, some people say, well, Steve Jobs was this great CEO and founder. He was also an asshole. And he didn't have to be an asshole, that was more a bug. I question that, because a lot of these cultures of excellence, they rely on this constant policing. And people that have not been taken to their absolute limits, like they do in military training, like SEAL training, they're just not set up to hold themselves to the same level of excellence, then if they have somebody over their neck, breathing on them, yelling at them, and instituting this.

• 26:37Speaker 00

  David, we, he bought our company in, just end of December, 2009. We had no idea what they were ultimately, what their plan was. I had, I don't know, 200 something people at the company they acquired. And, you know, a good chunk of them were working on selling ad sales for this previous product. I got kind of sequestered into what we were going to be launching. I couldn't even tell my team. I had all these people working on the old product. No one knew what the heck I was going out doing. I had, it was kept quiet. The only thing we were told, or, you know, it was brought in, is that he wanted, I think

• 27:18Speaker 00

  we had two or three weeks where we had to tell Apple everything we wanted, because there was code freeze at the iOS level. So all our requests, like in three weeks, again, for a product that wasn't even live, that we didn't even know what we're building, code freeze. And then we were told, I was told for WWDC in June, Steve wants to announce to the world that we, we had this new product called iAd, and that we're going to make developers millions of dollars. Again, it went back to how did developers make money? Commerce or advertising? And he wanted anyone who was building on iOS to make the most money. Because if they made the most money, they were going to keep building and they wouldn't go to Android.

• 28:00Speaker 00

  And he was paranoid that, at the time, Google was selling most of the ads in mobile. And he was really worried that Google would pull out of the ad, pull out, and it would leave a massive void for the amount of capital. So I was told, we want to go make millions of dollars, and we wanted to go announce it. And essentially, between code freeze and like, we didn't even, we didn't have a product. I had like, we had vaporware, we had a deck. And we had to go sell millions of dollars worth of ads. Now, millions of dollars started out with Stephen. We want million dollar ad buys for our developers, because I want to go announce that we bring in tens of millions. So what started as a million when we first went out, I got Citi, we got Unilever, we

• 28:45Speaker 00

  got these same brands that I just said, and some of them agreed, we're in. A million dollars in mobile was off the charts. That broke records. Like Facebook in 2010 was not selling million dollar deals.

• 28:58David Weisburd?

  It was still a very early platform.

• 28:59Speaker 00

  Still a very early platform, especially in mobile. So I was like, million dollar deals? I mean, you're, we were, he bought a company doing $20 million in revenue, right? Or 22 million. Okay, we'll do it. We go out, we get people to buy it. And I never will, never forget when Andy called me after one of the meetings and said, Stephen, I want to tell you the good and bad news. The good news is Steve really loved that, he likes the brands, he's really happy that we got brands. But, but then he proceeded to say, I never told you we were going to do, we wanted million dollar deals, we want $10 million deals. I almost like, I almost literally like, lost my mind. I'm like, Andy, it's not going to happen. Like, how are we going to do $10 million deals with a product that doesn't exist on

• 29:44Speaker 00

  a marketing deck, when as it is, all the, like, the ad agencies were like yelling at us for even asking for a million dollars? Fast forward, we did four $10 million deals. We did $60 million in six weeks. I got an invite, and I think it was me, Andy, and maybe Ishwar, the other co-founder, and Jay, the head of engineering. We got an invite to WWDC. Assistant called and said, Steve would like you, Steve would like you guys to come, really happy with what we did. We did $60 million of revenue in six weeks on a product that wasn't even live, it existed. So to your point, listen, I think that type of founder is able to will you and help you find things that you didn't even know you could do.

• 30:29Speaker 00

  I honestly didn't think, I knew we could do them, I knew I was pretty good at the selling thing. I knew I was pretty good at building a business. I didn't think in mobile, into, in the financial crisis, you know, in this chaos, that we could, you know, post or post, where mobile was still early, that we could find that type of capital. And we did.

• 30:47David Weisburd?

  I want to get back in a minute on how you closed those deals, because I think that's a story in and of itself. But at that point, you were in your early 30s, you were really taken to the brink. Did that cascade later on in your career? Did that help develop you, or was that just this traumatic experience that you had to get through?

• 31:05Speaker 00

  Yes and yes. What it did was give me this incredible amount of confidence to be able to sit in the room with anybody, any executive, any founder.

• 31:17Speaker 00

  Doesn't matter whether they were billionaires, whether they built whatever company, I knew I could be in a room with them and I felt really good about that.

• 31:26Speaker 00

  I think it also made me, when I wound up deciding to go to Foursquare, I think it made me a better leader. It made me realize what I learned a lot about being a leader and a manager and building and running companies. But I also learned some of the things that I didn't love about Apple as a culture that I wanted to instill. But I also think, I spent two years literally on a plane back and forth from New York to Cupertino because Apple wanted a New York showcase and they wanted me to open up Apple's first business office in New York at the time. And, but I realized that life's short and I needed to do things that I loved and that I was inspired in. It kind of inspired me to want to go back and build again, really.

• 32:10Speaker 00

  And I knew that my best work wasn't necessarily sitting at a big company like Apple and building a product there. My best work was taking all the learnings and helping build something else, inspiring me to build something else. In fact, it really was a part of the impetus to eventually start Oceans, but I thought in 2012, before Foursquare, that I wanted to start a venture firm because of that because I felt like, okay, now I can, it helped round things out for me that I felt like I could now really give back to founders in ways that was really valuable to them.

• 32:47David Weisburd?

  This reminds me so much of SpaceX and the SpaceX culture. In SpaceX, you have these three groups of people. You have these lifers that are there for 20 plus years. They just can't find a bigger mission. So they want to make humans multi-planetary and they just can't find anything as interesting of that. And then you have these people that stay there five to 10 years and then you have people that burn out in six months. They just can't take the culture. SpaceX has this responsible engineer culture, which means if you're an engineer and the part's not available, you should be on a plane as engineer, tracking down this part. And some people just can't take it. But what's interesting about SpaceX specifically is that even the people that burn out, that

• 33:27David Weisburd?

  last five, six months there, they still, years later, look back at that experience as the most valuable work experience they had. Is that something that you saw at Apple in terms of that intensity? If you run a business, you probably start your morning with way too many tabs open. You're checking revenue, ad performance, email, inventory, spreadsheets. And before you've made a single decision, you've already spent your morning just figuring out what happened yesterday. That's what I like about Perplexity Computer. Instead of jumping between every dashboard yourself, Perplexity Computer could connect to the tools you already use and build a command center for your business. It could pull together things like revenue, ad spend, margins, inventory, and email performance, then show you what changed, where you might be losing money, and what you should look at next.

• 34:11David Weisburd?

  But what makes Perplexity Computer really interesting is that it could actually work on projects. It could help rewrite an email flow, build an ad campaign, or draft outbound outreach. And unlike most AI tools, you're not locked in into one model. Perplexity Computer orchestrates leading AI models behind the scenes and automatically chooses the right one for each step. For a limited time only, you could try Perplexity Computer for free. Head to pplx.ai/invest. That's pplx.ai/invest to try Perplexity Computer today. Most AI tools are still answering questions while Perplexity Computer is completing full projects. Support for today's episode comes from Square, the all-in-one way for business owners to take payments, book appointments, manage staff, and keep everything running in one place.

• 34:55David Weisburd?

  Whether you're selling lattes, cutting hair, running a boutique, or managing a service business, Square helps you run your business without running yourself into the ground. I was actually thinking about this the other day when I stopped by a local cafe here. They use Square and everything just works. Checkout is fast, receipts are instant, and sometimes I even get loyalty rewards automatically. There's something about businesses that use Square. They just feel more put together. The experience is smoother for them and it's smoother for me as a customer. Square makes it easy to sell wherever your customers are, in-store, online, on your phone, or even at pop-ups, and everything stays synced in real-time. You could track sales, manage inventory, book appointments, and see reports instantly, whether you're in your shop or on the go. And when you make a sale, you don't have to wait days to get paid.

• 35:39David Weisburd?

  Square gives you fast access to your earnings through Square Checking. They also have built-in tools like loyalty and marketing so your best customers keep coming back. And right now, you could get up to $200 off Square hardware when you sign up at square.com/go/HowIInvest. That's S-Q-U-A-R-E.com/go/HowIInvest. With Square, you get all the tools to run your business with none of the contracts or complexity. Run your business smarter with Square. Get started today. Support for today's episode comes from Square, the all-in-one way for business owners to take payments, book appointments, manage staff, and keep everything running in one place. Whether you're selling lattes, cutting hair, running a boutique, or managing a service business, Square helps you run your business without running yourself into the ground.

• 36:22David Weisburd?

  I was actually thinking about this the other day when I stopped by a local cafe here. They use Square and everything just works. Checkout is fast, receipts are instant, and sometimes I even get loyalty rewards automatically. There's something about businesses that use Square. They just feel more put together. The experience is smoother for them and it's smoother for me as a customer. Square makes it easy to sell wherever your customers are, in-store, online, on your phone, or even at pop-ups, and everything stays synced in real-time. You could track sales, manage inventory, book appointments, and see reports instantly, whether you're in your shop or on the go. And when you make a sale, you don't have to wait days to get paid. Square gives you fast access to your earnings through Square Checking. They also have built-in tools like loyalty and marketing so your best customers keep coming back.

• 37:05David Weisburd?

  And right now, you could get up to $200 off Square hardware when you sign up at square.com/go/HowIInvest. That's S-Q-U-A-R-E.com/go/HowIInvest. With Square, you get all the tools to run your business with none of the contracts or complexity. Run your business smarter with Square. Get started today.

• 37:26Speaker 00

  Yeah, it was, it was both. I think to your point, I think it was very polarizing for me personally. On one end, listen, it was, it was to be able to work, to sit with Steve Jobs as icon before he passed away while I was there in 2011, to be at Apple at a time where their reinvention was just this, you know, they were the hottest company. iPad, iPhone, everything was going, was just incredible. To do it under Steve, I still have these like Kodak moments, these, these Polaroid moments of, of so many of those, of what happened there. At the same time, it was mentally exhausting. I went from running a startup, which was really hard in the financial crisis where,

• 38:11Speaker 00

  you know, you didn't know if you were going to survive or not, where you were told, you know, Sequoia had come out with that paper, which was, you know, everyone needs to batten down the hatches and hunker down. And for us to come out on the other side of that was so exhilarating, so rewarding. But then to go to, you know, a big company like Apple, and I just love building things, I love growing things, I love inspiring my team, and you wind up at big companies, you know, you deal with big company stuff, you deal with a lot of internal politics, you deal with things that different types of personalities are attractive to a bigger company like Apple. So it really was, for me, both this incredible experience that I'll never forget and so

• 38:54Speaker 00

  many learnings, but it was emotionally draining. And I had two young, you know, kids at the time and little ones. So between that and flying back and forth and the pressure, that had also, you know, kind of gotten to me as well.

• 39:12David Weisburd?

  I want to move on to Etched in a Bit, which is one of these other singular companies of the current generation. But before then, I wanted to really tie the knot on how being around Steve Jobs helped you close these $10 million deals. How did that practically affect?

• 39:29Speaker 00

  Listen, I think you, it gives you this incredible amount of confidence when you know that you have the resources of people and the talent behind you that I'm not just selling vaporware. I am selling a deck. The product isn't live yet, but I know that the thing I'm, the thing that I'm asking people to trust us on, to give us $10 million on, I know deep down that it's going to positively impact their careers too. I know that it's going to change their lives. I know ultimately that if they can be the first brand and they were the brand manager,

• 40:09Speaker 00

  the media buyer, that actually executed one of the great, first great mobile ads, and they did it like the first on Apple's platform, that that would help them in their story. So I knew that it wasn't BS. I knew that it would have an impact on them. And so it was easier to sell that. I also knew I had a lot of resources who were helping us design and build and prototype to support these brands and what they were about to launch. And I knew that the PR exposure for those that were able to, you know, that were in, at the Worldwide Developer, you know, conference and Steve was presenting them on stage when

• 40:50Speaker 00

  they did live presentations and everyone looked at it and viewed it and it wasn't competing with so much noise that we have today, that it would be incredible for those companies. I wasn't quite sure, you know, how we were going to deliver the media value because the product hadn't launched and we didn't have enough, I didn't know if we'd have enough impressions, I didn't know, but I knew deep down inside that Apple would do the right thing and we would do the right thing for our customers. So I think that helped and made it valuable. But I remember the agencies, I remember David Cohen at Universal McCann, who was, you know, now runs the IAB, which is the biggest internet ad trade group.

• 41:30Speaker 00

  I remember him literally being like, almost like, get the heck out of my office. Like, you guys are like absurd with this ask. And then, you know, I'd be like, okay, the agencies really don't like us. But I'd sit with the brand manager, Rob Candelino at Unilever, who was launching Dove Men, or Mark at Citibank, and I knew that they saw something as to why they had to be part of this and that it was going to be incredibly helpful to them, their brands, their careers. Even though there were a lot of challenges and last minute, literally had to call Rob Candelino at Unilever and tell him last minute Steve decided to pull his ad, which was a really, really, like, one of the most difficult business conversations of my life because

• 42:14Speaker 00

  this guy had his agencies and teamwork working 24/7 over holidays for like three months.

• 42:21Speaker 00

  With the belief and the CEO of Unilever thinking that Dove Men was going to launch at WWDC. And two days before Steve and his people called us and said, sorry, we don't have time, we got to cut it out. That was the one brand they decided to cut out. So, you know, it was-

• 42:38David Weisburd?

  How did that conversation go?

• 42:39Speaker 00

  Oh, it was awful. Like awful. I mean, I thought like, and the funny thing is, I'm now like, pretty good, like, we're really good friends, Rob and I, and like, he's had a wonderful career. And honestly, I thought I was gonna, like, I was like, we're both gonna cry. Like, because I know the blood, sweat and tears he put into this, and I had to call him and be like, yeah, you're the brand that they ripped out two days before. And he was about to fly out, and I was like, Rob, listen, I'd still love to have you. You should come out, your team should come out, you've put all this work in, it's still great. And he was like, no, I can't come. And I was just like, oh, devastating. Like, that was one of the hardest business calls I've ever had to make.

• 43:20David Weisburd?

  Did that experience in itself harden you?

• 43:22Speaker 00

  Oh, yeah. Completely, because it's like, what are you gonna do? Like, I mean, I think deep down, he knew, like, it was, this was way above my pay grade, this was coming down from Steve, and there's nothing I could do to save this, as much as I wanted to and tried. And, uh, yeah, I think, again, it like, all part of like, listen, business is business. Sometimes it's not personal, and you got to make some really hard decisions, you got to make hard calls, you have to have hard conversations. And I think all part of, you know, the learning journey for me.

• 43:56David Weisburd?

  It's this paradox, I've had these things that I feared for years, and then they came through, literally sometimes my worst nightmares, and just confronting them, even though they were brutal to deal with and difficult. And a lot of these things aren't just one phone call, sometimes they're weeks or months of suffering. But at the end of it, you're still alive, and you didn't die. And that's just, gives you so much confidence, the ability, knowing that you could surpass these worst nightmares, it's just so powerful.

• 44:26Speaker 00

  I think it really helps. And unless you go through it, it's impossible to, you don't, there's no other, you can't read it in a textbook and learn it, you just have to go through it.

• 44:36David Weisburd?

  Tell me when you first met the founders of Etched, what did you see in them?

• 44:41Speaker 00

  So, my co-founder and business partner, Josh Ron, he calls me, I think it was on a Christmas Eve, he goes, Stephen, I met them, I met the guys. You got to meet them. I'm like, what guys? Josh, it's Christmas Eve, what are you talking about? He's like, I met these founders at Etched, you have to meet them. So, tell me about them. Well, they're building a semiconductor company to take on Nvidia for inference, and they're Harvard dropouts, and they're, whatever, 20 something years old. I said, Josh, we don't do hardware, we don't, uh, you know, oh, and they've already, you know, they've already raised, and, you know, they're kind of on their Series A. I said, Josh, we don't do Series A, we don't do hardware, what are you talking about? He's like, Stephen, just trust me, you have to meet them.

• 45:26Speaker 00

  They remind me of when I first met, literally was in the room with Mark Zuckerberg in 2007, and him interviewing, trust me. He's my business partner, I trust him. I said, great, so let's go. So, we set up a lunch, and we had lunch in Nomad at, I think it was La Pacora Bianca. And there, we sit down, and I'm literally blown away. Why am I blown away? Because the level of depth that they were able to go into the company they were building, and why they were building. Their fearlessness. I mean, they're building a semiconductor company, rack and chip, full stack, and this

• 46:08Speaker 00

  was three years ago, so I think it was 23, 20, you know, something like that, 20, yeah, 23, I think, when we first met them. Nvidia is the hottest company in the world, on its way, and you just hear this level of why, post LLM, how inference, I mean, they saw inference, they saw exactly how everything was going to go from post-training to inference, and that's where what was going to take on most of the compute. And you'd hear them articulate it in such a crisp way. So, you had fearlessness, this inability of like, yeah, we're gonna build this, we're gonna go build this, this company, this is why they're, we are so short on commute, like, compute. They just had this vision, and they saw exactly where things have gone. Back then, it was crazy, you were like, you guys are a little bit, you know, but you heard it, you saw it.

• 46:53Speaker 00

  They, I think great founders too, are not, like, the level, they're able to sell you in ways, but they're not salespeople. And they weren't selling, but they were selling. Like, they just inspired you, and you went along with the journey, and you walked out of there being like, oh, my God, yeah, this, these guys are incredible. And I saw this complimentary between Gavin and Rob. Gavin was this like mathematician, this real kind of like wizard genius, Rob had this uncanny, almost like, he was in a 20 something year old dropout, but it was almost as if he had 25 years of business experience, the way he spoke and articulated things.

• 47:33Speaker 00

  And I walked out of there being like, wow, those, those are, they're super complimentary, they're fearless, and the level of details in terms of, and how big their vision in is, you just walked out inspired.

• 47:46David Weisburd?

  Stylistically, they might have been different, but did you see some semblance between Gavin, Rob, and Steve Jobs? Or was it just completely different type of founder?

• 47:57Speaker 00

  I saw like, almost like, the two of them, not individually, but collectively, had like, pieces of, of what made Apple, Apple, and like, this just incredible vision and fearlessness, of like, we're gonna do this. The thing, though, that I have seen, and I've watched Etched build, and they do, the way they present, the way they present their product, their marketing, their design, the way they unveil their evolution to their investors, I've seen a lot of Apple, and I got off, I remember, like, one of the presentations early on, I got off, I'm like, wow, these guys are doing like, they remind me so much of how Apple unveiled product, simplicity,

• 48:41Speaker 00

  design. You don't see that in like semiconductor companies, and I think their level of detail, their level of, um, design, their level of aesthetic, was, as they've built, it reminds me more and more of, of some of that Apple DNA. But their brilliance, I think, the thing in common is this brilliance, this intelligence, this work, this, this level of work ethic, and this fearlessness, I think, is, is very evident in Etched, and I think why they've been able to achieve what they've been able to achieve in such a short period of time. And the future for them is just, you know, is incredible.

• 49:23David Weisburd?

  You started your career in 1999, and had the dot com boom, then lived through the global financial crisis, and mobile, today you have the AI platform. Does AI dramatically change what you look for in founders, or is it still the same old signs of excellence?

• 49:44Speaker 00

  I say this all the time, because we get asked a lot, like, what do you invest in? And I think in LPs have a really difficult time, understanding things that aren't black and white and fit in boxes. But if you're not investing in people as an early-stage investor, I'm not sure you're really going, you're an early-stage investor. And the one thing, through all these cycles and all these changes, that is tried and true, is there's something about the DNA of the founder that I still, like, without question is what makes or breaks these companies. And I think there's a couple of different things. One is, a lot of these founders are generally unemployable.

• 50:29Speaker 00

  Either there's no freaking way they would, any company would hire them, because they just don't fit into that company, or there's such a tremendous fear of working at a corporation, that these founders, like, that's the thing that, like, freaks them out the most. I think there is this reality distortion field, kind of Steve Jobs-esque, where-

• 50:56Speaker 00

  They kind of will their way to something. And I do see a lot of that. And then, again, there's this level of detail and vision that drives them. And that's what we look for. So that hasn't changed. And their ability to articulate what they're building and why they're building. And, and again, having that, like, in the veins type of passion. Now, then they have to be able to, you know, it has to make sense what they're doing. That's one thing that doesn't change with all these cycles. Lot of other things do change.

• 51:28David Weisburd?

  What changes?

• 51:30Speaker 00

  If you go back to kind of, you know, the internet days, capital was scarce. Right? It was like, you were actually, you know, you didn't have companies with these crazy balance sheets. It was scarcity and scarcity drove success. It was do more with less. That was part of the moat, which is

• 51:50David Weisburd?

  Scrappiness.

• 51:51Speaker 00

  Scrappiness. Can you build and get far with little? As time went on, you know, mobile, I think, then you started to see a mobile revolution. Started to, you started to see companies now disrupt a little bit of the old legacy companies. Right? I think Yahoo, which had such a big kind of internet portal days. You saw kind of that between mobile and social media, Facebook and the mobile revolution chip away at what used to be Yahoo. Now it's not doing very, doing very well, but it's a very different company than it was back in the day. So I'd say you chip away at these companies. But again, like mobile, the transformation, it took a while, right? Like, there still wasn't, there was a lot more capital. But it's, things took longer.

• 52:33Speaker 00

  I think the biggest thing that I see today, that's very different than the past. One is velocity. Things are happening at such an incredible speed that it's hard to keep up.

• 52:47David Weisburd?

  We had a company in our portfolio, zero to 18 months, 100 million revenue, La Cora.

• 52:52Speaker 00

  Yeah. And that, and that would have never happened back. Like, that's like unheard of, right? And so, you know, the question someone'd ask is, okay, is that sustainable? How much of that churn? But it doesn't matter. Like, the speed is, the velocity is something we've never seen before. I'd say the other thing that we're seeing now is that every technology company is up for grabs. I really believe, every software company. So for the last 15, 20 years, the SaaS companies that built, they had pretty entrenched moats. Right? Like, very specific moats. They had their customers. It was hard, as we all know, it's hard for big companies to change and to move things and change vendors and all that. I think a third of the S and P market cap is up for grabs right now. Like, I think everything's being reinvented.

• 53:37Speaker 00

  And so it creates this cocktail of chaos. And again, is another reason why they, why I think velocity, it just changing everything. Because everything's being reinvented now with AI from the ground up. And that's something that I think we haven't seen. The other thing, the last thing I'd say is capital. Right? The amount of capital did not, like, we have, did not exist in the last transformation. So there's an enormous amount of capital. That's fuel. Capital's fuel. I think I look at it very simple. Is there going to be companies that are bigger than we've ever seen before? But man, the companies that blow up are going to blow up in ways we've never seen before. And it's coming at some point on both sides of the kind of equation.

• 54:21David Weisburd?

  It's going to make WeWork look small.

• 54:23Speaker 00

  Oh, WeWork will look like, you know, oh, yeah. Oh, yeah, that company.

• 54:27David Weisburd?

  47 billion.

• 54:28Speaker 00

  Ah, nothing. Right? I mean, it will, the magnitude, I'm talking, you know, billions will implode on some of these companies. But the flip side is trillion dollar companies will create, be created, and there'll be multiple of them. And that was something that was impossible 15, 20 years ago.

• 54:45David Weisburd?

  Does today's AI boom look more like the dot com boom or the mobile transformation?

• 54:51Speaker 00

  It's got its own DNA. It's got its own personality. You know, it's like, I think the dot com boom, the reality is that you didn't have balance sheet. All the, everything was funded. It was VC funded and it was funded on hype and vaporware. And a lot of what was put in the ground, a lot of like just broadband in general that was built. Capacity, we over, we built over capacity. Right? So you just didn't have balance sheets. Today, you have fortress balance sheets. You have these companies that are generating so much cash. So that's why I think it's a very different profile. Mobile, you had a different form factor being created. We went from the desktop web to these small devices. And so everyone had to learn what that meant.

• 55:34Speaker 00

  Today, yet, we're not seeing different, like, the form factors are the form factors. Right now, there will probably be new form factors without question. Obviously, Meta's trying to do it with glasses and now the PIN. We'll see what happens. But I think the form factors people are comfortable with. And now it's just because you don't, engineers used to be the constraint. It's no longer the constraint. Everything's being built so much quicker. So I think AI has its own personality characteristics, its own uniqueness. And one of the things I think I test myself on, I think, you know, it's easy to say that, oh, it's going to look like the past and valuations are crazy and everything's, there's going to be a crash.

• 56:16Speaker 00

  And, and, you know, these companies aren't sustainable. And I see people on Twitter talk about, well, it's got to get back to basic unit economics. No one knows what the hell they're talking about. We don't know. I really think this is like, this has its own personality. I do think the world has changed dramatically. There's certain characteristics where history repeats itself, sure. But I don't think anyone has a freaking clue. And anyone who tells you they have a clue is full of shit. This moment in time is a revolution that we have not seen. Things are changing in a way we have not seen. There will be characteristics, but I think AI has its own personality, its own DNA. And this is, you know, it's, it's a brand new period of change, which is exciting for all of us who love change and growth.

• 56:59David Weisburd?

  So another way, we know that we're in some inning of the AI boom and the AI bubble. Why? Because we have human beings investing, at least for now. So at some point, it will get above its valuation, whether it's 10 billion to 100 billion to a trillion to 10 trillion. At some point, we will overcorrect because human beings are memetic. They see their neighbor investing at 100 billion, selling for a trillion. They want to now invest at a trillion and exit for 10 trillion. What we don't know, and what I agree with you, I think nobody knows, is what inning are we? Are we in the third inning? Are we in the eighth inning? Maybe we're in the first inning and nobody seems to have a good handle on it.

• 57:41Speaker 00

  Well, listen, I would say we're early, right? I think we're still early no matter what. What we, the thing we don't know is how much government can, how much governments across the globe actually constrain what were the growth. Because AI, I mean, listen, it's a hot potato. It's the one thing both parties agree on. I think it's the one thing probably the US and China probably are sort of agreeing on in terms of talking about. And so the growth potential and what that becomes, I would say we're in the early innings. Could all this be capped? Could there, put a lid on it? Could, could governments come in and say, we gotta like really slow this down and stunt the growth? Or stop this? It's possible, in which case we're farther along than we think. I don't know the answer.

• 58:26Speaker 00

  I don't think any of us know the answer. But this, unlike all these other cycles, the governments really never jumped in. Right? Like, you didn't really have to worry and, you know, I mean, yes, they did in certain regulations and rules, of course, and privacy issues and all that. Governments weren't going to come in and stop the growth. We don't know how the world's going to behave, knowing the potential that AI can do on a geopolitical level.

• 58:51David Weisburd?

  If you go back to 1999, you know, first joined, first startup here in New York City, and you could give yourself one timeless piece of advice that you could take through these 27 years, what would that be?

• 59:05Speaker 00

  I don't have a crystal ball, but I think the piece of advice is surround yourself with the best people. Be in the best communities. Be in front, be with the best people. Be where, be where talent is. Always be learning. I think that that was lucky. Listen, I was at Foursquare, Foursquare's ultimate exit, which happened last week, was, turned out to be not what we all hoped. But the learnings and the friendships and all the things I'm seeing from all the X Foursquare people were incredible. It was an amazing talent pool. It was an amazing group of people. A lot of those have gone on and are very instrumental now in all the next generation AI companies. I was around great people. The exit was terrible.

• 59:47Speaker 00

  I would also say there's a ton of learning there, which I try and implore on founders, which is all these valuation steps up. Be careful what you wish for, because all these paper gains are nothing and you can really lose and ruin your company, which we could talk about. But the general thing, though, is be in the right rooms, be in front of people. Don't care about titles. Don't care about anything. Just be, surround yourself, because the real learning happens in the trenches. It happens while you're doing the work.

• 1:00:17David Weisburd?

  Reminds me of the PayPal mafia. They had this, I believe it was 1.6 billion roughly. But that wasn't a thing. 1.6 billion back then, I think it's 2008. Massive, massive exit. But they've gone on to now start Elon Musk and Tesla, Peter Thiel and PayPal and Palantir, Joe Lonsdale and APC and all these unbelievable companies. And that's really the legacy of PayPal. It's not even the product. It's not even being early to a technological innovation. It's the people.

• 1:00:53Speaker 00

  Always the people. I was really humbled last week. I wrote a post about kind of like a postmortem on Foursquare that I published. And the amount of people commented who could be really angry and pissed that their shares are worthless or company. But it was completely the opposite. It was that experience catapulted me. That experience, your leadership and management style was so incredible that it helped me get to here. And these are people now that are, again, they're at, you know, I get asked all the time, how do you keep your network fresh? It's like, it's called, we've hired thousands of people. And those people at one point were 22 when we hired them. And now they're running something. They're at OpenAI.

• 1:01:37David Weisburd?

  That's downstream of being around the best people. They also get older and graduate.

• 1:01:41Speaker 00

  100%. Absolutely. And so I think it's, you know, the most rewarding thing isn't necessarily what, you know, the outcome. But I think what people take away is the learning and the experience. And I think that's one of the things when I look at New York, the impact that Foursquare had on New York, New York tech, how it inspired other founders to build, how we had this incredible community. And I think, you know, always, always in New York and this underdog mentality, right? Versus the West Coast. And I think that just creates this, again, this kind of like,

• 1:02:20Speaker 00

  this cauldron of incredible people and DNA and intelligence and energy that led to so many great careers from that, even though the ultimate outcome was not a good one.

• 1:02:36David Weisburd?

  I used to get asked once a month in different cities, different people from government, from universities, how could we create a Silicon Valley here and X city across the world? How is New York able to achieve what so many cities across the world?

• 1:02:52Speaker 00

  Well, I would laugh because I'd watch all the people during COVID be like, yeah, Miami is going to be the next thing. Or, you know, come to Miami. I'm like, okay, the only people going to Miami are billionaires and people, you know, crypto crazies and tax avoiders. I'm like, you know how long it takes to build an ecosystem? I saw the same thing in Austin, right? Same thing. It takes a lot, you know, to get density of talent takes, in New York, it took 20 years, right? I think it really started, like, when I think about New York's evolution, it started when Google brought engineers here in 2003, right? And Google opened up its first New York office. And they brought a lot of engineers. And yeah, listen, Foursquare sold to, you know, or Dennis started Crowley, the co-founder of Foursquare,

• 1:03:36Speaker 00

  had started Dodgeball, which sold to Google. And then when he started Foursquare, it took some engineers from Google to start Dodgeball. So the beginnings really started with Google kind of poured real engineering fuel onto the New York fire. And then Facebook, when Facebook opened, my partner Josh opened Facebook in 2007, they started to bring engineers here. So you had like Google and Facebook opened their second biggest engineering offices here in New York that brought talent. And then once you start getting the exits, that led to like the Tumblrs and Foursquare starting. And then people saw that. And then you started to see more and more VCs open up shop here because it used to be the East Coast was all Boston, right?

• 1:04:19Speaker 00

  I mean, there was like, you count on one hand the New York VCs. And then you started to see more New York VCs. But the talent, and then like the Mongo DBs of the world started. And Kevin Ryan's been incredible, you know, reason for the success of New York because, you know, between DoubleClick and Mongo.

• 1:04:34David Weisburd?

  And that was, the DoubleClick acquisitions seemed to be a really change in the.

• 1:04:38Speaker 00

  Pivotal, right? Because Google bought them. But it took 20 years. I mean, I started in New York in 99. There were a few of us crazies who said, we didn't want to move out to the Valley. We think New York's going to be here. We're going to stay here. And most of New York early on was in digital media, ad tech, more tech. But then it evolved over time. But it took a long time. And the thing that is so rewarding for me personally now is when I go into these rooms, we're going to the primary summit last week and seeing, you know, 2,000 people in that room. I knew it was going to happen. It's New York. New York's, you know, epicenter of so many industries. But it took a lot longer than I thought it would to get New York to be that way.

• 1:05:20Speaker 00

  So I think all these cities that try and do, it's never, it's just you need, you need talent density. And talent density takes a long time to get en masse. And it requires companies to move people. It requires exits because people need to have money so they're willing to take the risks and start their companies. It's just really hard. And I think that's why New York, that's why Miami's kind of become, I mean, I love Miami. It's a great place to live and visit. And there's some brilliant people down there that are great founders, but it's tiny. And you have people like Brian Distelberger, who started Windmill, come back from Miami to New York to build here. Any city or anyone who, you know, goes out there, it takes a long time. And you just have to have patience.

• 1:06:05David Weisburd?

  Yeah, New York reminds me of this fire. You had to have all these necessary components. You needed to have the engineering. You needed to have the exits. Point to these two exits because everyone would say, New York, you're not going to build something great. You have to go to Silicon Valley to build something big for the truly ambitious people. And then you, the final straw was, the final piece of the equation was really the funders coming in and putting, making it fundable once you had the engineers and the founder talent.

• 1:06:31Speaker 00

  It's funny, I had, one of our investors in doing diligence was a little hesitant to do, or they were like, they kept hearing from all the Valley, like, everything's in the Valley, not New York. So I had them talk to Ben Harowitz. And Ben Harowitz, I remember talking to him. He goes, Stephen, where do you think our second biggest office for Andreessen Horowitz is? It's in New York. We have hundreds of people in New York. He said, if we didn't believe in New York, we wouldn't have anyone in New York. And so I, again, I think like the Valley PR machine does a really great job trying to convince people that like there's the Valley and nothing else. We believe it wholeheartedly in the Valley. But to say that New York can't build a trillion dollar company,

• 1:07:15Speaker 00

  there will be, without question, multiple trillion dollar companies in the next 10 years that are, that start from New York, without a doubt. I'm highly confident of that. I couldn't say that 15, 20 years ago.

• 1:07:30David Weisburd?

  Well, Stephen, this has been an absolute masterclass. Thanks so much for stopping by.

• 1:07:34Speaker 00

  Appreciate the time, always fun.

• 1:07:36David Weisburd?

  If you enjoyed that conversation with Stephen, you're going to love the conversation right here.