Field Notes from 20 Years of NYC Startups

What if AI made you more present, not more addicted?

Dennis Crowley (Dodgeball, Foursquare) shares field-tested lessons from 20+ years building in NYC, plus the thesis behind Hopscotch Labs and Beebot: ambient, context-aware experiences designed to push you into the real world instead of into a feed. We also get tactical: notebooks, hiring, early-stage chaos, and the mindset that keeps founders in the game.

Watch or listen: Youtube, Apple, Spotify

Chapters

(00:00) Intro — A founder’s field notes from NYC

(03:05) Why writing things down changes your brain

(09:10) “You fall to the level of your systems”

(14:45) From Dodgeball → Foursquare → Hopscotch Labs

(19:35) BeeBot — proactive, wearable AI and why it’s hard

(27:15) Hiring for uncertainty: side projects, skill, and resilience

(34:30) NYC tech evolution — capital, talent, and density

(41:10) Burnout advice — rest, don’t quit

Connect with Keith or Dennis

Follow Dennis on LinkedIn: https://www.linkedin.com/in/dpstyles/

Follow Dennis on Substack: https://teendrama.substack.com/

Hopscotch Labs: https://hopscotchlabs.co/

BeeBot: https://dens.medium.com/say-hello-to-dj-beebot-592cdc1f1704

Follow Keith Cowing on LinkedIn: https://linkedin.com/in/keithcowing

Join the Executives Unplugged Inner Circle for free coaching via email: https://execs.tv

Subscribe to the show:

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Spotify: https://open.spotify.com/show/1Bw7KhjlUzFjMoFhdfNAKN

Apple Podcasts: https://podcasts.apple.com/us/podcast/executives-unplugged/id1769131263

Full Transcript

Dennis Crowley: People have always said why New York and not San Francisco? It's like, ' cause New York is just a much more interesting city than I, San Francisco, in my opinion. This is a greater diversity of people and careers and industry here.

And I've always said that of all the things going in New York, like tech is the seventh most important thing or the 10th most important thing.

And that's what's wonderful about it.

Dennis Crowley: This is Executives Unplugged. I'm Keith Cowing, your host and executive coach. My guest today is Dennis Crowley. Dennis is the founder of Dodgeball and Foursquare and now Hopscotch Labs. He has been building, scaling and selling companies. In New York City for 20 plus years, and he has amazing ideas about how to install systems as an entrepreneur to avoid burnout, how to build a world-class team and building a future of technology that is about improving communities and social interaction, not disintermediating them.

Let's jump in.

Keith Cowing: I wanna jump right in on a specific topic that I find fascinating, which is your field notes, notebooks. What notebook are you on and how does this fit into your life as an entrepreneur?

Dennis Crowley: All right. I got a book right here. This is, notebook number 119. I've got maybe one page left in my book. So it's, I gotta sit down at a coffee shop sometime next week and go through the process of, you know, I cross everything off when I'm doing well. Hold on. Lemme back up. Like, I care everywhere I go.

There's never a time where I don't have it. I'm constantly taking notes on like, stuff that I have to do and you know, like ideas for products or like things to do with the kids. But then also I kind of keep a list of like, advice to myself. You know, things I want to like, keep in mind for future projects.

You know, a lot of this stuff gets copied over from one notebook to the next, almost like a, like a, you know, 100 commandments that I carry around with me.

Keith Cowing: how do you know it's 119? Do you literally keep track of this?

Dennis Crowley: Yeah, it says book number 119, right in the front up here. And I have like a notebook, I'm sorry, I have two shoe boxes full of these books all just kind of lined up. And I thought that at some point maybe I would like take them and photograph them and make like a big, like, collage out of them.

But it seems like a lot of work.

Keith Cowing: I've heard from scientific research that the neurochemistry in your brain is connected to your hand in a way where literally if you physically write with a pen, it connects to your memory in a different way, and it sinks in more than if you take notes on your computer or just think about it.

Do you find that this is a way to reflect and capture ideas? Tell me about how it impacts your work.

Dennis Crowley: , I always use this brand like Field Notes brand, and they've got, I think, the statement on the website, which is like, I don't. Write it down to remember it later. I write it down to remember it now. And, and I, I agree with that, where it's like the act of writing it down just kind of commits it to memory in a, in a different way.

You know, I go back through this book, you know, like a couple times a day and I flip through the pages and I make sure that like, you know, almost everything gets crossed out. Everything turns into something, whether it's an email or something in like a, you know, a, a bug ticket, you know, in linear or something, or a calendar entry for like, I'm gonna take the kids to this thing. , One of my kids has got.

, Some A DH ADHD issues and it's like the ability to keep his brain focused on stuff. And I, through dealing with that, I've kind of realized I kinda have the same thing where like, we can be at a dinner and I'll have something that pops in my head and I, I can't focus on the conversation because I'm trying so hard to hold onto that thing.

And so I realized if I just write it down, it like frees my brain up. It's like, oh, that's captured. Okay. Go back to the conversation. You don't have to remember that now. It's okay if you forget it. 'cause it's written down. And so it just allows me to be more present. Like it's, it quiets my brain when it's too active.

Keith Cowing: I try to do the same in, in my own life where I have a lot of different projects and I'm not as physical world as the notebook I maybe need to take up. This habit, but I, I kind of think of college where I'd have a physics book and I'd work on physics, but then I, after the test, I'd close the physics book and I'd put it away and I'd work on math.

And physics didn't haunt me while I was working on math. But now I have so many little things in email and text and everything haunts me all the time. And I find a five have way to just close loose ends and just close the book mentally and sort of put it aside. Then I can actually focus on the thing in front of me, and this may be the skill of the next 10 years, is the ability to focus in a world that works against you.

Dennis Crowley: It's just like you need to have a, you need to have a system for something, like people like this is my system, like this works for me. It doesn't work for everyone, but like I feel like everyone needs to have some version of a system that works for them.

Keith Cowing: I like the saying you don't rise to the level of your goals, you fall to the level of your systems, and you have to

Dennis Crowley: Interesting. Okay.

Keith Cowing: that hold you up in place. And, um, thinking about the stuff that you've worked on, you're on your third. Iteration, at least of starting a company in New York City.

You had dodgeball that sold to Google, you had Foursquare. Now you're working on your latest project. How do you. Keep up the passion to do it three times. How do you give young entrepreneurs advice to play the long game and not burn out?

Dennis Crowley: , I feel like this the stuff I've always, you know, been working on it kind of follows that, that theme of like, software in cities. And I feel like as long as I've lived, like I started doing that when I lived in New York because the city was overwhelming and I was trying to design software to make it less overwhelming and it just continued working.

You know, kind of on that in, in that direction. And so, yeah, it's been a couple different projects. It's been a couple companies, but it's kinda the same thing. And, you know, that's almost like my hobby. Like that's the stuff that I think about when I walk around the city. It's like I notice things and I try to remember things and I try to way think of ways to make things more efficient.

And that's just like. I just, I like to do that and then I, I write a lot of this stuff down and sometimes you have this idea to make a product that solves a problem, and then sometimes, you know, you start working on that project and it turns into a product and then you start working on that product and it turns into a company and then you end up working on that company for a long time.

And that this has kind of been the, the thing that's happened over and over again. , I think the trick is trying to make it not feel like work, like certainly like building a company is work. Like we have a bunch of people, we have to manage them. There's like bills to be paid and investor memos to write and like that.

That's work. But like sitting down at a whiteboard and trying to sketch out like, okay, what do we think the future of this thing looks like? That doesn't feel like work to me, that feels like fun to me. And so, you know, I think it's, the trick is like just finding a thing that, like, it, you know, finding a version of the work that energizes you instead of draining your energy.

Keith Cowing: you've done this many times in New York. There are a few people, I can say, 20 years of entrepreneurship starting companies, and. Going through the whole realm, what's different for you this time? What's easier, what's harder? How do you approach this differently than the first company you started?

Dennis Crowley: this one we're working on now is, is pretty hard just because, uh, the thing we're doing is like a it's like a city guide for AirPods. Through the lens of a AI powered radio DJ that talks to you when you put your AirPods in. Like, first of all, that's like a mouthful.

It's a lot. There's nothing else that's like this, like it's interruptive AI that's like we have your headphones on, just sends you messages. Um, and so it's like there's nothing else like it, so there's nothing else to crib from, you know, you can't be like, oh, let's just, let's just steal that design pattern from that successful product over there like we are.

Like inventing the way that this stuff is supposed to work, which is both exciting, but also like, it's, it's like, it's challenging and it's, it's frustrating, like when we did dodgeball, like Dodgeball was very inspired by like, the marauders map in Harry Potter. And so it's like, oh, this is a thing.

Like we are inspired by that thing. Let's go make that thing. Yeah, there was a lot of stuff we had to figure out, and then we did Foursquare. It's like, well, let's kind of just do dodge ball, but we'll do it on the iPhone. And then we did all this other stuff on top of it. And in this. This is just like totally different.

'cause the tools are totally different and the, you know, the people that I'm working with are totally different and the skill sets of those people are totally different. You know, to, to have engineers that can also double as product people because they're, you know, augmenting their skills with AI.

And to have product people that can moonlight as engineers because they just do everything in cloud code. It's just like, it's a. It's a weird team of people that can do a lot of different things, which is just totally different than the way that we had built previous companies. And it's like, it's very exciting, but then it's also like, it's just hard to, it's overwhelming.

It's hard to kind of keep up with it.

Keith Cowing: Talk to me a little bit about the juxtaposition between, you're always on the cutting edge of it was mobile and then it was GPS and it was location and it was, now it's ai and on the flip side you have an old notebook that looks like it's from 1980 and you write with a pen. Like how do you combine these two things in your head and does that give you a break from all of the screens?

I also think it's interesting that. Your product is not screen based. It is ai and it's leveraging things, but it's not about staring at a screen and touching and tapping really. And so how do you think about the newest of technology, but maybe some, very not new modes of interacting with things like speaking to somebody.

Dennis Crowley: Yeah, I could, I could write like a whole manifesto about this, you know, like there was, we, we built Foursquare we, we built the company vision imagining that like people were gonna use their phones less and less as contextual where computing became the norm. And so we, we had built all this infrastructure that was meant to.

Help usher in this like world of contextual work computing. Like we were looking at things like Google Glass and you know, like a long time ago, like we were building Snap, snap to place technology, the ability for your phone to like check in without you even having to use your phone or press the button.

Like it was really hard stuff back, like, you know, just like 10 years ago. Around that time was the rise of like Snap and Instagram where these companies were like, no, no, no, no, no. We want you to use your phone all the time. And like, here we are being like, no, no, no. The goal was to check in as quickly as possible, put your phone away, and then hang out with your friends.

And so there was this divergent vision for where the future was like, oh, I guess like what the future was supposed to be. And that's, that's the version that that won. Oh no, we're gonna just be glued to our phones all the time. We are gonna engineer software so that you do not wanna put your phone down.

And that was just always the antithesis of what we wanted to do, right? Like the last stuff that we worked on at Foursquare was like, let's make apps that you don't even have to use. Right? Like a version of Foursquare that you never, that works without even touching it. And that's, that's what we started messing around with some of the AirPod stuff.

And so after I left Foursquare and I worked on a couple different things, like, you know, I have a soccer startup called Street fc and I've got this, I run a soccer team called, uh, um, Kingston Stockade in, in the Hudson Valley. And, you know, analog projects like people out in the real world doing stuff facilitated by software.

But then, you know, when I, I kind of got drawn back into like, let's build another thing for cities, but it's like, let's, let's make a thing that you don't have to use. Like there's, there's no feed, there's nothing to look at. There's nothing to it know. It's, it's like a imagine like a TikTok style algorithm that gives you stuff that you're endlessly interested in.

But that stuff is in the real world. And the more you walk around, the more it tries to convince you to walk more and see more. You know, like make the stickiness happen in the real world as opposed to make it happen on the screen. And it's like that, that is not the way that the world is going, right?

Like we're getting to the point where everyone wants you to put the headsets on and dis disappear from reality. But that's not the version of the world that we want to live in. And so I'm trying to make the thing that. Allows us to live in the version of the world that we wanna live in.

Keith Cowing: There. There's two threads in there that I think are fascinating. One is contextually aware, and then the other one is, what I hear is basically ambient. It's behind the scenes and it helps you do things in a better way, but it's not the front and center purpose and it, so I spent a bunch of time in healthcare tech and ambient is a.

Topic there where you can just have it record the conversation with the physician and the patient, not so that you spend more time with the computer, so you spend less so you can actually talk to your patient and do your work and have everything else just go, bill Medicaid, take care of that for me, et cetera.

And it seemed, I feel like part of that is coming through here and then the contextually aware is. Really relevant right now with ai, where AI is super powerful, but only if you give it the right context. And getting context is a very tricky problem. And so talk to me a little bit more about those two themes, that ambient nature of it, to use technology to be less in your face, but to help you enjoy life and then that contextually aware, how do you work on that problem?

Dennis Crowley: that's the stuff that's tough, right? Like in order to make stuff that feels personalizing contextually work, it has to know you. And the only way to get these systems to really know you is that you train it on data that, that you've produced, or that you've written, or that you've liked, right?

You know, any of these algorithmic systems that are serving up stuff that you like, like they're. They're learning your preferences by observing your behavior. And so we, we need to have a, a piece of that. And then there's the other thing of like understanding people's context in, in the real world, like where are you moving?

Is this like how quickly are you on a bike or are you walking? Are you in the subway or in your car? Are you in a, in a city, in a suburb? Are you in a familiar neighborhood and unfamiliar neighborhood? Are you with friends or strangers? Like, are you in between meetings? Do you have time? Right? Those are things that we're all.

We're trying to understand all those signals and we, we can understand about half of them, right? The way that, you know, the project we're working on now, it's called Bebot, and you know, as you move through the city, it detects changes in neighborhoods and it's like, oh, you're never in this neighborhood.

I recognize that you crossed over in the boundary. Let me see if I can find something interesting that's happening nearby or to, you know, nearby and like within the next, like, you know, 18 hours that might be of interest to you based on all the things that we know about you. You know, like I, I was just at my kid's school for like a parent teacher thing and I walked out, I put my headphones in and it's like, Hey, , just so you know, there's like a, , 30th anniversary of Pac-Man exhibit that opened up on 52nd Street.

If you wanna go check it out sometime this weekend. And I was like that's pretty good. Like it knows, I like video games. It knows I like vintage stuff. It combines them, it finds this event on the internet about this Pacman thing that's opening. It sends a one sentence push notification. Now did I get that at exactly the right time?

I'm like, no. I left my kids school. I'm running back here to jump on this on podcast with you. Like maybe that's not the best time to hear it, but it's probably better that I heard the message than not hearing the message. And it was like at least relevant to my. You know, to, to my interest and my context in the sense that like, it's happening this weekend and it's happening in this city.

And so like we're kind of slowly getting better at this. I always tell the team, like, the product gets like, you know, 5% better every week and you just keep compounding that over time. Eventually kinda have a thing that, that works pretty well.

Keith Cowing: And talking about solving these hard. Technical problems, design problems, product problems. You are a product person, a designer at heart, at least from the outside. It seems you really care about designing solutions for these problems. How do you think about hiring on your team? When should A CEO hire a chief product officer?

Dennis Crowley: Yeah, it's, um, a great piece of advice I got a while ago was like, you know, CEO is a job, but like. You, there's different types of ceo. You either the sales CEO or you're the bd, CEO or you're the, engineering CTO, you're the product CTO. And so I've always thought that I was more of the product type of c of CEO. So I can be like, all right, I can fill in for the head of product for most things. And I did that for a long time at Foursquare before we eventually hired. People to run it. With the project that we're working on now, just because like the tools are so different, uh, we hired a lead product person almost immediately just because I met this woman who was a.

Just like very, very skilled, like really into the product and had worked in stuff in adjacent spaces and was very fluent in like, AI tools and, and technology. And it's like, you just know not only do you know stuff that I don't, but you know how to work in a way that I don't know how to work.

Um, you know, given that, like, I think there's. A whole crop of, younger folks that are just, AI tools first, where I feel like I have to work to kind of make the AI tools native to my workflow. It's like just, organic for some of these folks. Um, so that was, that's different.

And it's been wonderful because I feel like from the beginning I kind of have like a, a counterpart to, to bounce ideas off of. And I think that's, that's really a big part of it, you know, like. You know, to really simplify it, it's really hard to sit like at a whiteboard and just draw the same thing over and over by yourself and get some insight.

You really need to do it in front of an audience of two or three people. I ideally like your co-founders, your team, and you're like, this is how I think about the world, like. What do you guys think of this? And then they come up and they draw their own things and you erase it and you draw it again.

Like we, for the first, um, you know, like, like six months that we were working on this project with a small team of like four or five people, we would do this exercise of like, we like drawing the company and every Monday we would like draw the product, the whole thing on the whiteboard. And every week when you would, you do the same exercise, but it would be like 10% different.

From week to week, and it's like, well, this week we drew this part and we left out the part that we drew last week. And it's like, it just was the, the constant evolution of the thing. And then you realize the parts that weren't changing week over week were the things that we really needed to build.

And you can't do that by yourself. Like you have to have other people in the room. And they don't necessarily need to be like the head of product, but they have to be people that. Like some of them have to be technical, some of them have to be design focused. Some of them have to be product people.

Some of them have to, have empathy towards, you know, UX and what people do out in the real world. Building a team that has diverse opinions and then constantly having the same conversation over and over again with the team has been very helpful for us.

Keith Cowing: People can get obsessed with frameworks and spreadsheets and rankings and very analytical stuff. What you're saying is you draw it a bunch of times and it evolves and maybe there were 10 things, but there's four that always come up. So hey, those are the four that we're starting with 'cause it's clearly the core of the story.

Dennis Crowley: yeah. And the teams can use, you know, use whatever tools you want. Like we've jumped from, like, from tr, from Trello to Asana, to, we're using linear now. You know, it's like, I don't care what tools you use, like just migrate from one thing to the next. Just find a system that works. It's like the notebook, right?

This is a system that works for managing my brain. Like the company has found a system for managing, you know, the way that we work, kind of like a little bit in the office, a little bit outside the office. It just, you know, you just gotta find a thing that works and then just double down on it.

Keith Cowing: You mentioned skill when you talked about bringing on your head of product, you didn't say experience, and I'm interested in your view on experience versus skill when you're bringing on a product person and how you value each and how you test for each.

Dennis Crowley: The experience is important, important in the sense that, like, have you built something before? Have you built something from scratch? Like, do you have the, the empathy for how hard it is to go from zero to one and then to have you lived through the experience of like.

You made something that didn't work and you had to change it and that didn't work and you changed it again, and maybe it worked and maybe it didn't. And I think that's important. You know, in terms like we're not at the point yet where I'm hiring for the experience of, I've managed a big team in a big company.

Like if anything that feels like it's a. It's a skillset that we don't really want at the moment. You know, I feel like we're more like, I've been more biased towards, um, trying to bring people together that have worked at smaller companies on smaller teams, and they're just kind of live through the uncertain early days of something because those people are less likely to get.

Frazzled with the uncertainty, right? Because, you know, there is that, that notion of like, is this gonna work? I don't know. We got 18 months worth of runway. We'll figure it out. Like, what do you mean 18 months? It's like, hey, this is just a startup. Like you get, you know, you raise some money, you have a window to figure something out.

You figure it out or you don't. And some people are really comfortable operating in that environment and some people. Or not, and you know, it, same thing with the environment of, um, okay, you have a job description, but the job description is kind of like, make sure that all the stuff gets done right.

And but that's not my job. Like that's, you know, you, you can't really bring people like that on in an early startup days. It's just, you know, it's everyone's gotta work on a little bit of everything. we're kind of inventing what we think the future of proactive AI is supposed to look like in these wearables. And like, you have to be comfortable with that.

Like, we're gonna try a whole bunch of stuff in a lab US is not gonna work. And like, maybe there is no answer. Maybe there's no way to make it work right now. And you kinda have to be like, comfortable with that uncertainty and up for the. For the, the journey of it. You know, a a friend of mine said something like a week not too long ago where it's like, you know, when you lay out your company vision, which we just did for the first time, like a couple weeks ago, like I articulated, like, here's the vision and here's the, the vision and the mission.

And it's like, okay, we are a team and we are on a quest together. Like a role playing game like Dungeons and Dragons style quest to complete that, that vision, you know, and it's like a. It when you think of it through the lens of like, you've assembled this party that has to go and solve this quest.

It's just it's a it's a different thing that like, we just come to work and we work on this project. It's no, no. We exist to solve this thing that may be unsolvable, but we're gonna try our best to solve it. And that's, it's just a different framing, but it's a framing that I really like.

Keith Cowing: What are the biggest mistakes you think CEOs make when hiring in the early stage?

Dennis Crowley: , Putting too much weight on the fact that like, someone worked on this successful project at Facebook three years ago, you know, like, oh my gosh, this person did this thing. It's like, yeah, but like. As part of a team of, 20 people that was, you know, working on infrastructure that's 15 years old and bulletproof, supported by a team of 50,000.

You know, like I, I remember very distinctly when we hired like when we were scaling up Foursquare, and we hired our first couple, our first couple people, we hired them out of Google and they came and worked at Foursquare and they had never worked on non Google infrastructure before. And they're like, oh, you don't have.

You don't have anything here. There's no tools. I'm like, yeah, nothing. You gotta build all of it from scratch. And it was just like, it was just eye-opening. And so you kind of, you know, people that have been in big companies for a long time, they get really comfortable with those environments and tools and that, that's fine.

It's great. But like, in, in these things that start from scratch, you just don't, you don't have a lot of those luxuries. You have to get people that are okay with that. And I, it's also like. You know, we, we certainly have we we're working with people that worked at big companies for a while, which is great because they come with the experience of, we're working with a guy that's been a Twitter for a bunch of years, and Twitter was a hard place to work.

Like Twitter had lots of different leadership changes, lots of different mission and vision changes. Lots of changes and like, philosophy and what are we doing and what's important and what's not. And it's like, you know, for someone to have to live through that experience. Maybe it's not a startup.

'cause Twitter's huge, but like you, you are in the chaos and you understand the chaos. Right. And so I think, you know, just having lived through an environment like that is, is a thing to, to seek out and not discriminate against.

Keith Cowing: Interesting. I've lived through some of that chaos myself as a product person on the team at Twitter in earlier days. When you think about, I think it's very interesting of taking somebody from a big company and bringing them to a startup environment where. I've seen more often than not coming from a Microsoft, a Facebook, a Google that somebody's super skilled and really great, but they get in the early environment and for one reason or another it just doesn't work.

And I'm curious what your take is on how to test for. Will it work when they make this transition? 'cause there's some people that really will do well. They're just bottled up in a big company and they don't fit there, and they would do great in an early stage, but it's very hard to know in advance. Is it worth the risk for both sides to roll the dice?

Do you just look for people that have early stage experience or is it like Twitter is saying you don't have early stage, but you have uncertainty and chaos and so therefore, maybe you can make it through here. Or you have something else in your life where you've dealt with uncertainty and chaos.

Dennis Crowley: Yeah, I mean, I think it's, you look for people's side projects, you know, like what, what does you do on the side? Like everyone's got a side hustle, like, what is it? And sometimes it's like, oh, I'm been working on this project. I, it's an app. I never really launched it. I've been working on it. It's a game, whatever.

And it's like, well, let me see it. Like, oh, it sucks. I just like, let me, let me see what it is. You know? And I think it's those people that have these passions that, like you continue to kind of crank on it a little bit outside of, outside of your day job. And a lot of times it, it's, it's like, you know, it's an app, it's a game, it's something technical and it show, you can see someone's thought process through that.

We work out of like a you know, a venture studio called Betaworks. There's a lot of people there that are just like going from project to project. Like we're, we are in an environment where we are exposed to a lot of people that spend their time working on a lot of things concurrently.

As opposed to like, oh, I'm just one person that's been at Google for 15 years. Like, I don't know a ton of those people, like the people that I hang out with regularly, like they're all working on five different things, and we just, like, I feel comfortable working with those people and like we, we are, we have access to that pool of people that does those types of things.

And so those are the types of people that we gravitate towards hiring. Like, like if this thing works and we get, and it turns into like, oh wow, this is a real company. We gotta scale up. We got 20, 30, 40 people. Like, then you start to go dig into these bigger companies and bring out these people that really know how to like build and manage and operate and and, you know, and deal with these teams.

But I think in the moment that we're in, it's about who, like who are the missing Lego pieces that we need to get this thing to the, the point that it works.

Keith Cowing: And you mentioned Betaworks, high density environment of entrepreneurial, interesting, exciting, passionate people that gets to the New York City ecosystem. What's changed in the New York Tech world from 20 years ago when you were doing this and how does it look now to build a company? I.

Dennis Crowley: Yeah, it's, we think about this stuff a lot 'cause there's like this 30th anniversary of New York Tech thing coming up, and so there's this big party. The big gala going on. So I've, I've got, it's funny, there's a lot of conversations about like the old days I think the two big things that have changed is number one, if you go all the way back, there was people that thought that the internet was just gonna be like a fad and it wasn't like a real.

Business and like, certainly like there was like the 1.0 and then the big crash and then the 2.0 and it was like a 2.0 where all the, all the people that were really passionate about the idea of the internet really started to build meaningful stuff. 'cause they were, they were not the ones that were just like, you know, working in it because it was a hot thing to do.

It was like they were really passionate about the space. The other thing is, when we were trying to fundraise for for Foursquare, back in the early days, it was just not a lot of venture in, in New York. It was a couple funds, like, you know, uni square ventures and you know, a handful, a handful of others.

But just, there wasn't like, you would go to Boston, you'd go to Philadelphia, you'd have to go down to out to San Francisco to meet with most of them. And then

Keith Cowing: For the first meeting too, this was, there was no zoom meeting for the first

Dennis Crowley: Oh,

Keith Cowing: had a 20 minute coffee, it was in person.

Dennis Crowley: yeah. And like this, I think this is one of Foursquare's claim to fame to be honest, is that like we were so hot in those early days that funds that missed out on the deal.

Like we probably talked to 'em, but they just missed out on it. Like they ended up putting people in New York where it's like, we can't miss out on these deals anymore. And I mean, it was us and it was Tumblr. And it was Etsy. There was like three, three of us in the early days. And then, you know, you started to see like, .

First rounds got like one person in New York now, like they rented one desk, like Spark Capital's. Got someone in New York and then you started to see more funds kind of putting a presence in New York. So they were part of the ecosystem and that made it easier for New York companies to raise money, and then of course, what I think is one of the biggest contributors is, Google, New York built the biggest engineering organization that maybe New York has ever seen. And I remember people thinking like, these guys are crazy if they think they're gonna build an engineering organization in New York.

I was part of that cohort that moved into the, the Google plex, right? What at, at that time. And we were thinking they are never gonna fill this space. And of course, like they filled that space and like five other buildings since. But all those, like a lot of those people got recruited out to other startups and it was a real superpower.

For the early cohort of New York Tech companies to be able to reach into Google, New York and Don not just pull out an employee, but to pull out like five of them. Five people that had worked together like that all knew how to hire based on the Google system, all knew how to work together based on the Google system.

They were trained Google PMs or trained Google engineers and like that was like a gift to be able to hire. Like a dozen of those people out and have them all working together on a different project that wasn't related to Google. And it was a huge accelerator, I think, for the New York Tech scene.

Keith Cowing: One of my theories on that too is on the talent side where you need founders to. Start things and you need builders to build things. I think we had some of that back then. The director tier is how you scale things and I don't think there was any director tier talent in New York that really understood tech and how to build.

And on the west coast you could just go hire somebody from Dropbox or Facebook or whatever. And on the east coast it was super hard and now there's this huge bench of director talent where when it's working and you need to scale the org and the company, you can bring in amazing people that know how to build, but also know how to scale.

And that just wasn't there before.

Dennis Crowley: yeah, and also on the sales and BD side. And that's like, I remember this was something we struggled with in like 20 13 or something. And I remember this being a knock against New York Tech at that moment in time where it's like in the valley is still still better because like you can hire that, you know that BD executive from such and such and they come with the squad, like they come with the team.

Like you're not just hiring one person. Of course, you hire one person at a time, but then that person recruits all of their people. And now I think that infrastructure exists. But like, you know, like it started first with engineering and then maybe with product, then with design, and then with sales, and then with bd.

But like now New York has all that stuff.

Keith Cowing: When you went from the early days to scaling at Foursquare, how did you deal with that as a leader, as a CEO that. Has to transform from, black magic and adrenaline to, Hey, we're operating a real company here.

Dennis Crowley: We were thankful to have good experienced board members at the time. That was probably the, like the big superpower we had is that by having, folks from Union Square and folks from Spark and folks from Andresen Horowitz yes, they're very talented investors and board members, but they, because they're very talented, they're also on the boards of all these other companies.

And so, we would have these problems, like whether it could be, you know, technical issues, BD strategy, you know, personnel issues, and. You could bring 'em up to the board and they would say, I can't tell you what the answer is, but I can tell you how Twitter dealt with this, how Pinterest dealt with this, how Facebook dealt with this, and how, you know, this other company's dealing with it.

And so here's the menu of options. And then you'd look and be like, oh, well, why don't we do a little bit of what Twitter did and a little bit of what Etsy did, and then that's our solution. Having quality board members means they probably sit on other boards, or they're part of funds that are involved in other boards.

So they, they have access to all the answers and they don't like, again, they don't give you the answers, but they give you the menu of options to choose from. And sometimes that's the best thing you can get out of it.

Keith Cowing: What are you excited about for the next 10 years of New York Tech?

Dennis Crowley: People have always said why New York and not San Francisco? It's 'cause New York is just a much more interesting city than I, San Francisco, in my opinion. This is a greater diversity of people and, and careers and industry here.

And I've always said that of all the things going in New York, like tech is the seventh most important thing or the 10th most important thing.

Half the people you meet don't give a shit about the tech thing you're working on.

And that's what's wonderful about it. You got all these people that are here for a reason to like do their thing and prove their thing in this city that just has this endless amount of stimulation and has all this overlap of all this talent.

And then you've got this like huge democratization of you can just type a paragraph into Claude code about what you want and kind of almost get something out of it. You give those tools to people in an environment where there's just like a huge density of, of like talent and culture and interest.

Passion and good stuff will come out of it, especially when all you got, all these people that are uh, newly have the ability to make these things without having to spin up a huge engineering team or really understand engineering.

Keith Cowing: Where can fe people find your new project?

Dennis Crowley: Oh, um, let's see. The company is called Hopscotch, right? So it's hopscotchlabs.co, not.com, dot co. Um, you can also go to the app store. It's on iOS. You can search for Beebot, for AirPods. And then I am pretty easy to find on the internet too. I'm on threads and it's kind of still doing the Twitter thing.

So I'm just at Dens.

Keith Cowing: And are you hiring?

Dennis Crowley: Selectively, we have room to hire, I gotta find a designer. I gotta find someone that can help with growth. If we met a really amazing uh, AI engineer, right? Some, you engineering background, but like really into. Massaging prompts and organizing data based off of that we would probably opportunistically hire that person.

The answer is yes. The answer was no. But now that I'm talking about it, yeah, the answer is yes. Yeah.

Keith Cowing: so if you're world class designer, AI engineer, show your work, show your portfolio. Dennis can take a look.

Dennis Crowley: And if you like working on weird stuff, right? Weird stuff that like, maybe it works, maybe it doesn't, no one else is doing this stuff. Maybe there's a reason nobody else is doing it, but that's, we think that's the fun thing.

. Can I have one last thing just 'cause I had my wife bring this from the other room. You were asking about burnout I felt the moment of should I be working on another thing in this space before? Again, it's I've done this, am I doing the same thing and blah, blah, blah.

And I just really hit this this point where I was like, I just don't, I just dunno if I can do it again. And I was on the high line in New York and I walked by this guy that was selling, um, like postcards. And I, I found this one. And I looked at it and I was like, okay, that's it. That's the answer.

If you get tired, learn to rest, not to quit. .

It like spoke to me and yeah, I bought it and I hang it in my room now. And that's kind of like the, the mantra where it's like, don't. Don't quit 'cause you're burned out. Just like take a break, feel yourself up again. Get back to work, go back to the thing that you're good at, go back to the thing you're passionate at.

And that's kind of been my, my North Star for a bit and I figured that was just worth sharing right at the end of this thing.

Keith Cowing: Awesome. I'm glad you got your rest. Look forward to you lighting it up again, Dennis.

Thank you.

Dennis Crowley: Thanks for having me on. This was super fun. Appreciate it.

Keith Cowing: That was fun. I look forward to the next decade of New York Tech. If you know an entrepreneur, especially in New York City, share this episode with them. Dennis has some great insights and inspiration and motivation, and if you enjoyed it, then go ahead and give us a positive review on your favorite platform.

And if you'd like to chat, reach out to me directly. You can find me at https://kc.coach or send me a note on LinkedIn. Until next time, enjoy the ride.