An Unfiltered Conversation with David Tisch, Founder of BoxGroup

We could. I just self-deprecated.

My best talent. I don't, I don't, I have a shrink. And I've chosen at this point in my life to not self-assess. And I feel like in work, what I do every day is, is yesterday is just less important than tomorrow. And you're only as good in venture as your next investment. And that isn't to say the choices that you've made historically don't matter. And it isn't to say that you can't learn from them. But there's like a relevancy to the job and the relevancy is about today and tomorrow. And so I think over time, you're either you grow into or you learn is like, you have to like continue to stay relevant and almost operate with one foot in front of the other versus this like big, broad step back thesis. So what are my talents? I don't know. Like I'm trying to be a good parent. I feel like that's where I'd like to find talent.

Three of them. I like them differently every day. And they like you, you're told like you, you spread your love equally. I think over a course of like time, that's probably true. But on a minute to minute basis, there really is ebb and flow of like favorites and, and I'll put 10, 8 and 6. And they're awesome. And I think like what a privilege it is to, to be able to bring little people into the world and like live your life through their eyes. And so I think from a like human standpoint, that's great. And I think at work, what I think hopefully Box Group is able to do is, is build a team of talented people. And so when I look at talent in a work setting, I think a lot of that is around people. And I think that is both from a who works here and who we grow this business with together. There's a lot of continuity at our organization, which I feel incredibly fortunate about. And then on the founder side, it's, you know, the, the job is, is an amazing job. You meet people at a point when they have a dream and you get the opportunity to be part of watching someone's dream come true. And someone has an idea, someone has a passion, someone has a energy to go create something from nothing and we're fortunate enough to be able to see that happen. And the, the joy in this job comes from people that you're able to, to be part of their journey. And I think that's a extraordinary thing.

Yeah, we'll have to, you have to, I mean, that would be weird if I did it. The story behind my first investment is a company called Boxee. So Box Group's named after Boxee. Roku, which is around today, Boxee was a Roku competitor. The idea was cable was evil, which proved out right. And we should all get rid of cable, which proved out right. And so they built a box, Boxee, that you could plug into your TV and gradually begin siphoning off a cable from pre-streaming, pre-Netflix. So I met Avner and Gidan. They had worked at Big Tech and they started things before and they were just amazing. They had this passion for sort of freeing people from this, this monopoly. And I invested $25,000. It was an angel investment. I didn't want to write my name on the cap table for some reason. So I created an LLC called a Box Group because box for Boxee and the box was like a cool nightclub in the city at the time and felt like, I don't know, it made sense and group felt bigger than me. And so I never thought that was going to be, that's also a lifelong name that mattered. And so that's where Box Group came from and invested in Boxee. They had an amazing journey. They raised their next round from Fred Wilson, which is like, as a student of venture is like ultimate goal as someone in New York, Fred's the best. And so my first deal was sort of followed on by USV and Fred Wilson. They ended up in front of Congress talking about the cable monopoly and they ended up selling the company to Samsung. And so that was the first one.

All right. What are we talking about? What was little David doing? Well, yeah. So I think timing is so important and so hard to appreciate, right? There's like the context of what the world looked like. If you go on today, what's beautiful about ChatGPT is, if you go on and you ask like, describe the generation sort of from 1978 to 1983. And there's a name for it. It's called the Xennials. And why it's interesting is we're this sort of micro five-year generation that experienced the development of technology in real time. And so we started off on dial-up internet. We watched the deployment, the development of the web. We watched cell phones and the switch from analog to digital. Like I remember the invention of almost everything and the foundation of like what modern technology is in real time. And I think that that sets a foundation for life that's so different from people who grew up with all of these things in their life. In third grade, I used the computer. In fourth grade, I owned an Apple II GS. I started off on the internet at 2400 baud. And then we developed into high-speed internet and then eventually Wi-Fi. And so I was exposed to tech early on through the Oregon Trail. It's also called the Oregon Trail Generation, which is a game. And we floppy actual floppy disks, fake floppy disks, and then CD-ROM. Like every one of these old antiquated texts, there's like a list going viral on Twitter of how many of these 40 things have you done. And I'm all 40. And I think that is like old people in general. And then this micro generation. I'm not old yet. I'm pretty old. But I think this micro generation just experienced the development of the world that today is taken for granted in real time. And I think that that really impacted my childhood. I was a computer nerd and like an internet nerd before those things were real. I grew up on AOL chat rooms meeting strangers that you didn't know anything about. There was no identity. We were doing both totally clean and happy things and totally nefarious things. At the same time and ebbing and flowing in between. And then you watched the internet get created. My father worked on Wall Street and he had an early Bloomberg terminal, a laptop. And so one of my first experiences on the internet is going on his Bloomberg to look up sports stats and sports information. And I always felt like I had this information advantage because of this Bloomberg terminal on fantasy sports. So I played fantasy sports when I was a kid. I lived a suburban childhood outside of New York and I have a brother who's seven years younger. I have a four year old, a three and a half year old younger brother. We just such different childhood because the internet was around when he was in middle school and high school. And the internet wasn't when I was.

He runs a startup. It's a health care company. It's called Atria. It's awesome.

We invested at Box Group. I just think when you look at, again, timing. Timing matters. Seven years is a dramatic difference in what the world is like. And sometimes that's political. Sometimes that's innovation based. Sometimes it's societal. These moments of time are hard to capture retroactively. In college, I was a history major and my obsession was studying today in a historical context. How do you experience the present in the lens of history? And I actually think in terms of venture investing, thinking about the future in a historical context is really important because you're trying to say where are we going? And it's very hard to say where we're going if you don't know where we've been.

He's three and a half years younger. Also in tech right now. He's not in tech. He's not in tech.

They're still waiting for us to get jobs. But I think again, that's generational, right? If you come from a family where everybody's supposed to be doctors and lawyers, you come from a family where everybody's a professor and you're doing something different, it's very hard to understand and appreciate these things. And so I think what's amazing about our industry is it's filled with rebels. And I think today it's a little bit more acceptable and a little bit more known. And there's more information about it. But at the end of the day, there's a rebellious nature to starting a company. I am going to do something that nobody else has ever done, or I'm going to do something that someone else has done way better than they have. And so you're fighting a challenger fight. And I think on the venture side, you're not doing that. You're not a founder. And I think there's a clear delineation between VCs and founders. But you are fortunate to join that rebellious journey that the founders are going on. And so I think when I think about my job in context of trying to explain it to others, because when you're later stage in venture, you're doing finance. When you're early stage venture, you're backing dreams. And I don't try to explain my job to other people. I don't think it's that interesting until you meet the people that we're investing in. And that's interesting. But when you're talking to people at a party or at a family event and trying to explain it, you're like, what are you guys? Like, here's some dumb idea I backed. And then six years later, you're like, look at that dumb idea. That thing worked. But what's not dumb are the people. The people are the glue here, but trying to teach people outside of this about the people that you're backing is very hard to do.

No, I didn't have a plan. I think, again, timeline-wise, 2003, I graduated college. The internet had went up and all the way down. In New York, there's not a tech scene. So the idea of finding a way into technology just wasn't a career path or a viable option. Law school felt like a nice punt of making a decision for three years. I thought it was a good foundation to learn how to make decisions in process. And then when you get there, you realize it's a vocational school to be a lawyer, which makes sense. And I don't want to be a lawyer. But I finished law school and found my way into tech. I think when you look back on people's stories, a lot of the time, they're not linear. They're random. There's jumps. There's risk. There's timing. There's opportunities that are hard to contextualize retroactively. But in the moment, they are just living in that decision-making experiences. And so mine was, I didn't want to be a lawyer, spent a year in real estate finance. Didn't like that. TechCrunch had started. I was reading about startups at Ruby on Rails. And I was like, I have to figure out how to jump. And I jumped. Started a company with a friend from college. He wasn't ready. I wasn't ready. We had no idea what we were doing. We were going to the early days of tech meetup. We were meeting engineers who were working at big companies and learned through trying. Ended up joining a big company that was not an exciting company. I learned a lot of bad lessons from that experience. It was two years. But I met a ton of fascinating people. We were 2007 through 2009 able to hire people in an economy that nobody was hiring. And I think that was fortunate. And so I met a ton of the people that fast forward a decade were early foundations of what today is the modern New York tech scene. Because these people were sort of circling around and looking for jobs, starting companies, leaving companies. And so that experience there was foundational to what I do today. And so 2009 dove head first after I left there dove head first into being an investor and starting what we do today.

I worked at a big information services company. It was a company, again, timing. There's a service called 411. Used to call 411 when you needed a phone number or an address. And you paid a lot of money to do that. And they were the B2B service provider behind the 411 service that was offered on a variety of phones. And so they had this big call center organization, a big database. And I ran the internet division, which was taking a lot of the data assets and trying to modernize them into technology products. So it's sort of built a skunkworks team inside this organization. And I think working inside a big companies and trying to innovate is always friction filled. And I think doing it in a time when a change of technology was complicated. The iPhone hadn't, I think the iPhone had just been invented. The App Store was coming. Twitter, I was like one of the early users of Twitter. And then it gave up my account because I forgot my password. But somebody one day looked and it was very early. So I was like a startup junkie working inside this big company trying to innovate from within. And I just think that's a really hard thing to do when there's not a top down buy-in on what actually innovation inside the company looks like. And so you were building here and fighting friction there. And I think that that was a lot of the lessons. And a lot of lessons were people driven. Just like how do you work in big organizations? I learned very quickly I'm not a good employee. I'm a bad employee.

Everything. I'm not an employee. And so I learned that the hard way. You learn lessons when you're young, know it all and trying to tell, experience people what to do. And I think we're not going to listen to you. And good lessons learned.

So I left there and I got fortunate. I'd made about seven or eight angel investments. And one of them was in Boxee. The third investment I made is in a company called ID.me. We started as TroopSwap. It pivoted. It's like the most amazing story. Blake Hall is this amazing entrepreneur. It's such a precious lesson to get when you invest in a company in 2009. We're now in 2025, 16 years later. And ID.me feels like overnight success 16 years later and still early in their journey. And so it allows you to understand the timelines in this business. And Blake is still as hungry and ambitious as he's ever been and 16 years in. And has now gotten out and told his story. And I think it's like a unique startup that's still under the radar and still growing. So that's a third investment. And I went up to a conference in Boston to learn how to be an angel investor. That's what the conference was about. It's called the Angel Boot Camp.

I met people. I don't know that I learned. I think you learn back then again, it was a nascent industry. And so if you looked around that room, in that room were these very eventual like luminary investors. Some had built things and started investing. Some were just starting, but I met an amazing group of people, including the founder of Techstars, ended up talking to him and figuring out why they weren't in New York at the time. And then got fortunate enough to partner up with him and help launch and run the program here in New York. As I did that, I realized I was signing up to be an investor. And so that was when I started to take Box Group more seriously. So started and ran Techstars here in New York and simultaneously sort of escalated our investing in Box Group. And I was doing both of those things simultaneously for about three years together, at which point shifted over to Box Group full time.

So the first sort of nine years of Box Group are personal capital. So it was myself, my dad, and my two brothers as a piece. We were prescient enough to invest out of a fund structure. So I actually look back and can say like our first fund or second fund or third fund, which are all privately backed. And then our fourth fund, we raise money from outside helpers.

Box Group one is 2007, but it's really 2010 through 13. So it's while I was at Techstars and then a year after Techstars. And my partner, Adam, left Techstars with me to do Box Group full time in 2012. And so Adam was here from the very beginning. Box Group two, again, private fund 2013 through 15 expanded our team in 2015 out on Nimi and Greg, who are still here 11 years later. Greg left for a minute, but we don't punish him for that. Came back. So amongst the four of us, there's a ton of continuity. Adina joined before we had raised outside capital. Clare had interned here before we were raising outside capital. And so amongst the six people that are here for a long time, everybody's here before we took on outside capital, which is a really cool narrative. And so we've watched and experienced together the evolution of what we've done.

Yeah, good stuff, not at work.

I've always been a collector. And I think that there's such a parallel in collecting and investing to me. It's seeing appreciation of assets. And I think it started in my life and it's really my connection to the Internet. And there's so many people on the Internet who started here with baseball cards. It's sports cards.

Very much. Unfortunate. Gary's a good friend. It's interesting. So Techstars and Gary, it comes together. I invited Gary to come speak at my first Techstars recruiting event. And so Gary got on stage. He's on stage, cursing at everybody.

I'm like, this guy's nuts. Still is. Gary and I started doing baseball cards in the same era. And baseball cards are the first Internet P2P commerce. So it started on the AOL message boards. AOL had on their message boards a like post around reputation. Like this person's good. This person's not good. And then one day slowly you started to see these links show up on the AOL message boards for a new startup called eBay. And the whole collectibles industry switched from the message boards over to eBay almost overnight. And the day eBay went public, a majority of the items on eBay were baseball cards and the others were TY Beanie Babies. Beanie Babies were amazing collectible. And you learn, I think, from really investing in things and watching them appreciate what growth looks like. And so cards were awesome because cards versus Beanie Babies are like an isolated collectible built on rarity. Cards have this real life performance to it, which I think is more parallel to a startup in many ways of like you invest in a rookie and you're betting on what their performance in real life can be. And sometimes it works and sometimes it does it. And so you have like hype and then it doesn't work. You have hype and it works. You have hype, it works and doesn't work and then goes back up. And so you see the careers of athletes and performance happen and it aligns to the value of their cards. And I think when you look at startups, it's not actually parallel, but there's a lot of lessons to be had. And so collecting has always been something I've been interested in. The toys and bear bricks or what these are called. I didn't know what to put on my shelves when I was a borderline grown up. Like you can't put sports memorabilia because it's weird. I didn't like have pictures or books because I didn't really like pictures are weird because it's like pictures of me. It doesn't make sense. And then books just not my thing to fill shelves with. So here came the toy.

There was a store in New York called Kid Robot and they sold these things called lab bits, which are like smoking pig rabbit things that were weird. They just looked weird and cool. They were like, I want one of these.

And so I did. The bear bricks were the collectible amongst a sea of collectibles in that there were more of them. They did partnerships. So Disney Grateful Dead. They've done partnerships with all this different IP and they different sizes, different materials, and they became sort of the focus of the collection over time. And I turned out all the other stuff.

My son's into it. He's not like, it hasn't clicked fully yet, but we'll get there. My daughters don't care about them like cool Disney cards and they're like, why? I'm like, oh, sorry. But I get them bears. They like half tolerate them.

I just don't think you need to create analogies to everything, right? Like everything is actually different and trying to compare things is like convenient, not necessary. I think there are lessons. I think there are extractions, but I think that's how life works is you can experience a ton of things. And if the next thing you do is not exactly the thing you did in the past, trying to over relate them doesn't make sense. Instead, trying to extract the lessons from something and say, okay, what are the takeaways that I can take and then reapply? That's more interesting. And so with art, you can find parallels, but you can also find holes in that comparison. So, do I own art? Yeah, because it looks cool on the wall. I don't like own art because that's what startups look like. I probably should if I was good at art, but I don't do that.

No one knows, right? That's the magic of adulthood. No one knows anything. And you get there, you're like, oh, that person also doesn't know anything. And you're just making it up. And then you're telling the story later of like, I knew. That's why like kids are fascinating because they ask a question. I'm like, I am about to make up some nonsense. I'm going to say it in a factual way. You're going to listen. It's hopeful in that what I'm telling you is like good advice. Like you can understand it. You give them guidance. You like help them experience things. But I think that like the idea of confidence and conviction are really complicated. And having conviction in yourself, having confidence in yourself is great. And I think it's a really important way to operate. But I think is a lot of really smart people say you have incredibly strong beliefs that are lightly held. And I think that life is sort of about that. You can believe in something. You can go all in at something. And then the second that the facts change or you're experience easy to think about something else, it's important to sort of pull back and iterate or move. And I just think you should apply that throughout life. The cost of change and the cost of stickiness is really expensive. Right. Don't stay in something that isn't giving you the most important return. And return isn't money. Return is is broad. Whatever it is, whatever it is to you, return to be satisfaction. It could be money. It could be friendship. It could be stability. There's a lot of factors that go into it to what matters to an individual. And I think one of the interesting things about startup investing is we spend a lot of time here asking why are you doing this? What what is this about? Is this about a mission? Is this about a passion? Is this about an interest? Is this about money? Is this about changing the world? All of those things are good answers. We just want to know what your why is and why are you starting a company? Why this one? Why do it with the people you're doing it with? Why are you taking this strategy? Why does the product look like this? The why is how you understand people. It's how you understand a lot of the world. And I think that those are the lessons that you can take and apply to so many things.

I don't take anything that ever happened in my life for granted. I appreciate opportunity. I was born into an incredibly fortunate situation and family. And I take none of that for granted. But if I look at the foundation of that upbringing into what I do today, there is no direct parallel. Like nobody said you should go into tech. My grandfather, who is an amazing entrepreneur and started a company, didn't believe in the internet. He told me it was the dumbest thing in the world. And I'm like, oh, you were totally wrong. And my father still doesn't believe in the style investing that I do. He is a value investor in the public markets. And so he wants to understand like, what is something worth today and not view things in sort of a long term appreciation. And so you can't always connect the dots. And I think that like you take risk. Sometimes they work. Sometimes they don't. Then you take those lessons and keep reapplying it. Like we invest in a company today at Box Group. And I will find out if that company works somewhere between three to 15 years. And three years will be a short term data point. And then, but in that story, which then you tell on podcasts and you listen to or you watch on videos, there's a human. And inside of that story is a human with a dream. And that person who starts the company and it never works, that story never gets told. They go out for a year. They fail. That person highly likely has not failed that many times in their life, if ever. So you're now taking somebody who's incredibly smart, ambitious, risk taking. They start a company. They have an idea. They go about it and they fail. That is going to impact them psychologically. It's going to pack them emotionally, physically in all aspects of their life. Sometimes the way that they handle that story is to say like, fuck it. I'm just going to try again. And sometimes it's deeply internalized and they need to like rebuild to start again. And in the podcast, the video world, the emotional side of startups doesn't get told. And I think when you're living in this world, that's the part that I think is the most interesting is that we get to experience through investing in people, the human side of this business. When somebody exits their company for $100 million, which in startup world, isn't that much. In real life, is an insane amount of money. That person makes life changing money and life changing for every person is a different number. And it's all like in some context. And I think to watch somebody that you met when they were 18 or 22 or 30, and they have this life changing moment, it means something. And it's amazing to see. Their life's changed. And when they fail, their life has changed. And everything in between. And then you are fortunate enough to be part of these N of 1 stories. And these N of 1 stories are you meet a founder and they have an idea and they start the idea and it works. And it doesn't always work like this. It rarely works like this, but it works. And they've now built a company that's worth a billion dollars or five or 30 billion dollars or a bigger. That's this N of 1 story and watching that impact is just astonishing and a true privilege.