Investing Billions - E440: What Steve Jobs Taught Me About Great Founders

Episode Date: October 9, 2026

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.

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 stuff. smoke and mirrors. You got to see firsthand Steve Jobs, got to work with him. What did you observe from working with Steve John? 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 I have such a grand vision. So, Stephen, you've spent over 20 years building companies and investing. What do great technology companies have in common?

It 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. 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? 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? Because it's just a magnet. If there's a 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 in part of building. 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. Have you been involved in one of these companies in your career? Yeah, I think I've been involved in several of them in different forms in 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 complementary 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 love them. I love the culture. I love 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. 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. As investor, how do you go about telling between ambition and dilution when it comes to top founders? 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. 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? Well, I think 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, they're building it because they feel like it's a gold rush. And they're building it because like this is the time to make money. 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 workwise or they've already started grinding away and building and it's just, it's so deep in their veins. It's like in their heart 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 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've got to sift through the BS. There's an underrated rule from Ashton Coucher, who alongside being an actor, is actually a really great angel ambassador. He was in Airbnb earlier and a bunch of $10 billion companies. And 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. Well, first of all, Ashton Coucher was an investor in Foursquare-Maiwal company as well. another one he didn't quit and come work for us but he was around the office a bunch of times but yeah like listen i 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 what i as an investor go quit and go you know if they hired me an assistant job i'd go

work for this person. Sure, I think that's part of it. But again, I think there's a lot of different dimensions that you look for. That may be one of them. But, you know, 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. 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. That distinction between ambition,

delusion. Yeah. 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? It was a fast. It was a fast, 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, Quatra 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 Frank 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 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, Quatcha Wireless, which we can get into that story as well. But what I saw from Steve was 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 in such detail on so many things, but yet have such a grand vision. And. And, And I saw that pretty clearly with Steve. This episode is presented by Juniper Square, the operations partner for private markets. 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.

I think I learned that, you know, and again, it's very, I don't want to, you know, I never benched board because it's hard. There's only one Steve Jobs. And 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. Take me inside the room when you first met Steve Jobs and you spent three hours with him. What did you observe about him? 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. The 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 Cooper Tino with Andy Miller, who was a co-founder of Quachar 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. young. 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, 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 so I walk into Andy and I we get seated we're in the executive conference room that Steve's executive conference room his assistant sits us down and Nick 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 exact team. And then, then the questions came. 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 pause. I'd never experienced that before.

And I've met with a lot of successful people. It reminds me a little bit of Peter Thiel. Peter Thiel is famous for these long, awkward pauses. Yeah. So I mean, I've never been with Peter. So it was, it was these long awkward pauses and then he just started asking. And they did these crazy, deep, thoughtful questions. Like what? So what it was clear to me, what he really was trying to figure out was not the product that we had at Quacha 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 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? 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. There's a lot of seeing how we'd fit in culturally. Because again, at the time, Apple only acquired at most 10 companies. So the biggest company they'd bought before us was PA 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?

And there were three hours of questions to really assess that. Thankfully, we passed the test. What did that teach you about how to acquire companies? 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&L. Fascinating for a company.

I had all these still at the time, had, you know, number of different products. One P&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 division within Apple that truly was its own P&L. Everyone at Apple were, you know, and again, they were a hardware company and software company. 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, we're 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 dollar business under services. And I know. the Quatro Code was still up and running up until, like, I know a couple of years ago. So I think it's, it's about, you know, most of the 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 poll items in 2000, I think it was 10, 10 or 11, yeah, 10 WWDC. So having his support at the top was really important. 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 cult. in the company.

What do you think Steve Jobs understood about company building that most founders fundamentally do not? I'd say a couple of things. Number one, Steve surrounded himself with complementary personalities. There wasn't an, if you had more than one Steve Jobs in the room, it would have never worked personality-wise. Why? When you think about, 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 what I've seen, incredible founders know what to do. I think Mark Zuckerberg did this with Cheryl, is they understand their personality. They understand in 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. And I think Steve knew how to surround himself with, and I think great founders do this, they surround themselves with complementary talent and their personality flaws. And so I would say that's certainly one of it.

I think one thing. The other thing is, attention to detail, right? I think what made Apple so unique is, again, there can only be one Apple. And I think 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? 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 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, it 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 fascinating. This edition through subtraction.

What's an example of that? Like when we were launching, 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 was all these banner ads and there were small little banner ads and you can 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 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, 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 writing, you know, this is like, Avila just launched iPad and, you know, it was the hottest company, you know, in the world and it just gotten like totally its mojo, was flying. And he's reviewing ads for a relatively small business. And I think like it's that level of focus. And then the people that were working with us were like literally focus on making sure like very specific stuff within the I ads that we're launching. We're showcasing all of the benefits of the operating system, right? What made, you know, the native operating system features and function.

So, you know, 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 that dial the 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, but I do think that obsession of detail, the great companies, the great founders, really obsess about making sure their products are the best at the end of the day. And he instilled that into the entire organization. Yeah, for sure. How? Well, he changed. challenge 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 I had. 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? And like, or Stephen, uh, 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 prepared for that meeting, you would get destroyed. So you better have every single thing. So when you were sitting with the exact team, you better, you know your business. You've got to know your business.

You got to know everything about your business. And again, those are some of the lessons I've learned and taken away kind of going forward. One thing I've learned from talking to hundreds of investors is that great investment firms aren't built on investment returns alone. The firms under are great at the things most people don't see. Their operations, their relationship with LPs, and the quality of information they use to make decisions. And here's what AI has changed. Every firm now has access to the very same models, so the intelligence isn't the edge anymore. The edge is what you could feed it.

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And with Alpha Sense, you know exactly what that is. The edge goes to whoever can trust their information and prove it. See it for yourself. Start your free trial at Alpha-sense.com slash how I invest. That's Alpha-sense.com slash how I invest. That's why I question some people say, well, Steve Jobs was this great CEO and founder. It 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 were just not set up to hold themselves the same level of excellence. Then if they have somebody over their neck, breathing on them, yelling at them, and instituting this.

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, I had all these people working on the old. product, no one knew what the heck I was going out doing. I had to, it was kept quiet. The only thing we were told or, you know, it was brought in is that he wanted, I think 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 once he announced to the world that 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. 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 City. We got Unilever. We 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. It was still a very early platform. Still very early platform, especially in mobile. So I was like, million dollar deals. I mean, you're coming. We were, he bought a company doing 20 million dollars in revenue, right, or 22 million. Okay, we'll do it. We go out. We get people to buy it. And I never will forget when Andy called me after one of the meetings and said, Stephen, I, I want to tell you the

good and bad news. The good news is Steve really love 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 want a million deals. We want 10 million dollar 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 dollar deals with a product that doesn't exist on 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 dollars deals. We did $60 million in six weeks. I got an invite and everything was me, Andy, and and maybe each other other co-founder and Jay, the head of engineering. We got an invite to to WWDC. As assistant calls, 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 and a product that wasn't even live it existed. So to your point, listen, I think that type of founders able to will you and help you find things that you didn't even know you could do.

I honestly didn't think. I knew we could do it. I knew where 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. I want to get back in a minute on how you close those deals because I think that's a story in and itself. But at that point, you were in your early 30s. You were really taken to the brink. Did that cascade

later on your career? Did that help develop you? Or was that? that's just this traumatic experience I had to get through? 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. 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. 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 realized 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 short and, and, I needed to do things that I loved and that I was inspired. And it kind of inspired me to want to go back and build again, really. 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 part of the impetus to eventually start oceans. But I thought in 2002, 12 before Forest Square 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 me. 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 at 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 burnout that last five, six months there, they still, years later, look back at that experience

as the most valuable work experience they had. Was that something that you saw at Apple in terms of that intensity? Yeah, it was both. I think to your point, I think it was very polarizing for me personally. On one end, listen, it was to be able to work to sit with Steve Jobs' 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 Polaroid moments 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, 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, it was so exhilarating, so rewarding. But then to go to, you know, 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. 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 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. 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? 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. 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, the media buyer, that actually executed one of the first great mobile ads. 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 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 is, you know, now runs the IAB,

which is the biggest internet ad trade group. 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 a brand manager, Rob Candolino 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 in 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 this guy had his agencies and teamworking 24-7 over holidays for like three months with the belief and the CEO of Unilever thinking that Doveen 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. How'd that conversation go? 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 going to, like, I was like, we're both going to 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 it. 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 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. The data experience in itself hardened you? Oh, yeah. Completely because it's like, what are you

going to 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, yeah, I think, again, it, like, all part of, like, listen, business is business. Sometimes it's not personal and you've got to make some really hard decisions. You've got to make hard calls. You have to have hard conversations. And I think all part of, you know, the learning journey for me. 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 confront hunting 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 just gives you so much confidence. The ability, knowing that you could surpass these worst nightmares, it's just so powerful. 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 in a textbook and learn it.

You just have to go through it. Tell me when you first met the founders of Etched. What did you see in them? So my co-founder and business partner, Josh Ron, he calls me, I think it was on a Christmas Eve. He goes, Steve, and I met them. I met the guys. I met the guys. I met the guys.

Josh, it's Christmas Eve. What are you talking about? He's like, I met these founders at Etch, you have to meet them. So tell me about them. Well, they're building a semiconductor company to take on Nvidia for inference and their Harvard dropouts and they're whatever, 20-something years old. I said, Josh, we don't do hardware. We don't, you know, oh, and they've already, you know,

they've already raised and, you know, they're kind of on their Series A. It's 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. 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 them. I said, great. So let's go. So we set up a lunch and we had lunch a nomad at, I think it was La Pekora 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 was three years ago so i think it was 23 20 you know something like that 28 20 yeah 23 i think when we first met them invity is the hottest company in the world on its way and you just hear this level of why post l lm 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

a crisp way. So you had fearlessness, this inability of like, yeah, we're going to build this. We're going to go build 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. 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,

these guys were 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. And I walked out of there being like, wow, 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. Stylistically, they might have been different. But did you see some semblance between Gavin Robb and Steve Jobs? Or was it just completely different type of founder? 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 going to do this the thing though that i've seen and and i've watched

etch 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 present things 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, design. You don't see that in like semiconductor companies. And I think their level of detail, their level of design, their level of aesthetic was, as they've built, it reminds me more and more of some of that apple DNA. But their brilliance, I think the thing in common is this brilliance, this intelligence, this work, this level of work ethic and this fearlessness, I think is

very evident in Aston. I think why they've been able to achieve what they've been able achieve in such a short period of time. And the future for them is just, you know, is incredible. Start your career in 1999 and the high-down the dot-com boom and live 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 X-E? 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 are in 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 different things. One is a lot of these founders are generally,

generally unemployable. 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 is, you know, ask, where they kind of will their way to something. And I do see a lot of that. And then, 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 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. A lot of other things do change. What changes? 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 can you get scrappiness? Scrappiness.

Can you build and get far with little? As time went on, you know, mobile, I think then you started to see the mobile revolution. 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 Facebook and the mobile revolution chip away at what used to be. And Yahoo is now 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. 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. We had a company in our portfolio, zero to 18 months, 100 million revenue, Lagora. Yeah. And that would have never happened back. That's like unheard of, right? And so, you know, the question someone to ask is, okay, is that sustainable?

How much of that turn? 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 modes, right? Like very specific modes. 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&P market cap is up for grabs right now. Like I think everything's being reinvented. And so it creates this cocktail of chaos. And again, is another reason why I think velocity is 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 like we have did not exist in the last transformation. So there's an enormous amount of capital. That's fuel. Capital is fuel. 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.

It's going to make we work look small. Oh, the we work will look like, you know, oh, yeah. Oh, yeah, that company? 47 billion. Yeah, 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 be created and there'll be multiple of them.

And that was something that was impossible 15, 20 years ago. Does today's AI boom look more like the dot-com boom or the mobile transformation? It's got its own DNA. This kid'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 Hypen 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 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 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. 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, Matt is 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 really going to be a crash. 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 a brand new period of change, which is exciting for all of us who love change and growth. So another way, we know that we're in some ending 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 $10 trillion, at some point we will overcorrect because human beings are memetic. They see their neighbor investing out $100 billion, selling for a trillion. They want to now invest out a trillion and exit for $10 trillion. What we don't know, and what I agree with you, I think nobody knows is what ending 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 out.

Well, listen, I would say we're early, right? I think we're still early no matter what. The thing we don't know is 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 U.S. 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, were in the early innings. Could all this be cap?

Could they put a lid on it? Could governments come in and say, we got to 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. 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.

But 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. 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? 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 with the best people, be where, be where talented 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. 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 can 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. It reminds me of the PayPal Mafia. They had this, I think, I believe, it was $1.6 billion, roughly. But that wasn't the thing. 1.6 billion back then, I think it's 2008. It's massive, massive exit.

But they've gone on to now start Elon Musk and Tesla, Peter Thiel and PayPal and Palantir, Joe Lonsdale and 8VC and all these unbelievable companies. And that's really a legacy of PayPal. It's not even the product. It's not even being early to a technological innovation. It's the people. Always the people.

I was really humble last week. I wrote a post about kind of like a post-mortem on Four Square that I published. And, you know, the amount of people commented who could be like really angry and pissed that their shares were worthless or company. But it was completely the opposite. It was that experience catapult. upholed me. That experience, your leadership and management style was so incredible that it helped me get to hear. 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 for,

you know, and those people at one point were 22 when we hired them and now they're running something. They're at Open AI. That's downstream of being around the best people. They also get older and graduate. 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 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. 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 was New York able to achieve what so many cities across the world? Well, I would laugh because I'd watch all the people during COVID be like, yeah, Miami's 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. Listen, 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, you know, listen, Force Square sold to, you know, or Dennis started Crowley, the co-founder of Foursquare had started Dodgeball, which sold to Google. And then when he started Foursquare, took some engineers from Google to start Dodgeball. the beginnings really started with Google kind of poured real engineering fuel into 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 open 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 tumblers 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? I mean, there was like you count on one hand in New York VCs. And then you started to see more New York VCs. But the talent.

And then like the Mongo D.Bs of the world started. And Kevin Ryan's been an incredible, you know, reason for the success of New York because, you know, between double click and Mongo. And that was the double click acquisitions seemed to be a really change in the 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 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 or 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. So I think all these cities that try and do it, 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 Distalberger who started windmill come back from Miami to New York to build here. Any city or anyone who goes out there, it takes a long time. And you just have to patience. 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, build something big for the truly ambitious people. And then the final straw was the final piece of the equation was really the funders coming in and making it fundable once you have the engineers and the founder talent. It's funny. I had one of our investors in doing diligence was a little hesitant to do. where they were like, it 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 Harwitz, I remember talking to him. He goes, Stephen, what do you think our second biggest office for Angeason Harwitz 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, 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, there will be, without question, multiple trillion dollar companies in the next 10 years that start from New York, without a doubt. I'm highly confident of that. I couldn't say that 15, 20 years ago. Well, Stephen, this has been an absolute masterclass.

Thanks so much for stopping by. Appreciate the time. Always fun. If you enjoy that conversation with Stephen, you're going to love the conversation right here.