The Exchanges

Q Tell me, what do you know now that you wish you'd known at the start of GC, 22 years ago?

A It's a hundred percent about the founders. Not 99, it's a hundred percent. Forget about markets, forget about TAM, forget about even other co-investors. Myopically focus on your relationship with founders in choosing people who are going to build the next generation great businesses. The second thing, a very tactical thing, compounding your winners over a very long period of time, continuing to reinvest in your greatest businesses and your greatest founders produces the best outcomes. And the third is being super honest with your partners. Instead of promoting a company is doing well when it isn't, or having a situation where people get misinformation, always make sure that your partners have all the information they need to make the right decisions.

AI assessment note: “It's a hundred percent about the founders. Not 99, it's a hundred percent.”

Q to found it together. Before we go to GC there, you mentioned knowing Joel since you were five. This partnership is something that I heard from Hemon, from Adam, from Nico, from Quentin, and they all said about just how truly unique it is in anywhere in venture. I wanted to ask, what makes you guys such good partners? Like, what is the fabric that makes you so good together?

A One thing we did, which I think was a very good idea, is most people who start business with their friends, I think, can make a mistake. They say, let the business never get in the way of the friendship. We said the exact opposite. Let the friendship never get in the way of business. We are dear friends, but we are business partners. And our role in bringing these businesses to market, and in starting first few companies, and now General Catalyst was always, and we had to really focus on the business issues. Which means that if I'm doing something that's either pissing Joel off or wrong, he not only has the obligation, he immediately is going to come and say, hey, I think this, I think that. And there's no pretense that it's going to hurt our friendship. On the contrary, our friendship is going to be stronger because we have this integrity of real transparency. So that's a very important part of it. The second thing, which is harder at scale, it was easier when we were smaller, Sounds crazy. That's that Joe and I were classic divide and conquer. Very, very different skill set. So things that I like to do are very different in the business that Joe likes to do. And as a result, we don't overlap a lot. So we don't have conflict. On the contrary, we started the business by being able to divide up the opportunities and go execute. And since we trust each other, we don't have to sec…

AI assessment note: “Let the friendship never get in the way of business.”

Q How big was the first fund, and was it easy to raise?

A Yeah, we used our own money. Well, the first fund was probably seventy million dollars, and it wasn't even in GPLP, it was an LLC, because of course we were building a company, which is the only thing we thought we knew how to do. It was seventy million, most of it was from us, and then a handful of checks from some of our friends in Boston, who would become mentors to us, mostly investors, And other funds, because we had no investment experience, and we went to some of our friends and said, hey, will you help us? And they said, sure, can we put money in? So our first fund was all friends and family, but the majority of the money came from Joel and me.

AI assessment note: “first fund was probably seventy million dollars, and it wasn't even in GPLP”

Q When you had to go out to institutionals for the first time, how did that go?

A Well, there were a couple of fun ones. One was Joel and I left leaving an endowment, which was one of the Ivy endowments, and we were driving in my convertible Back to Boston from visiting this endowment. We were really excited because we got our first commitment from endowment, and I said, hey, that's a tremendous donation that they all made to us. And Joel looked at me and said, it's not a donation. They actually want their money back with a return. Because the only money that Joel and I had ever raised, knowing our backgrounds, was that we've built huge foundations around philanthropists our entire lives. So the only time I had ever asked anybody for money, our original business didn't require Investor money, and this was the first time, and my mentality was raising money to make the world a better place, not necessarily to build companies. But the response was quite mixed. One endowment that I sat down with, they asked this very important question. What's our investment experience? We said, none. And what's your tech experience? And we said, well, we built a tech-enabled business. That group turned around and said, I can't believe it. I will never get this 30 minutes back that you just took from me. Please leave. So I got back in the car and agreed that didn't go so well. But where we found a sweet spot was there was two people in particular that really believed in this ear…

AI assessment note: “But the response was quite mixed. One endowment that I sat down with”

Q with before. The interesting thing is I always ask, like, what's David's biggest strength? And the commonality amongst everyone's answers was incredible here. They said David is truly the best in the world when it comes to unique relationship building. When you reflect on that, What do you think you do that makes you so good at authentic, genuine relationship building with the companies and founders that you work with?

A So what you probably ask people, how good are David's financial skills? And they went, not so good. How good are his tech skills at evaluating product? Not so good. Is there anything that this guy does that's good? And they said, yeah, he gets along well with people, and he creates opportunities through relationships. So I think, Harry, we're all given some strengths, some weaknesses, and I'm a filmmaker, right? I mean, my background later is, you know, I'm a documentary filmmaker. I love the art of the story. So what I really want to try to understand when I meet founders is what's their journey going to be like? And most importantly, where can we be helpful in that journey? In that journey, it's going to be relationship driven. You and I mentioned before that, that your mom has MS, okay? And the first thing that I would talk to you about, if I met you, you were a founder, is I'd really try to understand Is your mom getting the healthcare? I would be biased. I'd say, is your mom in the UK? Which I know is good healthcare, but is there something in the United States that may be better? Now, I'm not doing that because I'm trying to gratiate myself to you. I'm doing it because I'm trying to develop a bond with you that's bigger than just making money. The second thing is, is that I realized that any one of us, including me, there's a limited amount that I can bring anybody, but I…

AI assessment note: “develop a bond with you that's bigger than just making money.”

Q And when you think about design objectives for the firm, did you always want to build a multi-stage, multi-geo global firm? What was the initial ideas, and how did that change over time?

A Well, people can't see because you and I are on video, but I'm laughing. Absolutely not. We had no plan. We had no strategy. We had no business model. All we knew is that we were going to take some of the money we just made selling our travel business, and we were going to hatch companies in Boston. The original slide that we had, which was just a photograph of a drive or board that we had, was very simple. Pick industries that were predominantly consumer because we knew nothing about enterprise or healthcare. But what we knew is, is that this is in the early 2000 that there were so many transformations that were going to happen around consumer that we had had experience building consumer business. So we just want to hatch the next generation of great consumer companies. So it wasn't just in other founders, which of course we wanted to do. It was the fact that we were going to hatch a bunch of our own companies. We're very clear not to call it an incubator. Because to us, an incubator is where you put sick babies, unfortunately, and it never really worked for us to call it an incubator, because an incubator also means throw a little money around and see what sticks. Our goal was from the start to be able to sit down with founders or our own team and hatch the next great generation of companies, and that's what we did at the beginning. And then what we realized is our ideas were…

AI assessment note: “Absolutely not. We had no plan. We had no strategy. We had no business model.”

Q to found it together. Before we go to GC there, you mentioned knowing Joel since you were five. This partnership is something that I heard from Hemon, from Adam, from Nico, from Quentin, and they all said about just how truly unique it is in anywhere in venture. I wanted to ask, what makes you guys such good partners? Like, what is the fabric that makes you so good together?

A One thing we did, which I think was a very good idea, is most people who start business with their friends, I think, can make a mistake. They say, let the business never get in the way of the friendship. We said the exact opposite. Let the friendship never get in the way of business. We are dear friends, but we are business partners. And our role in bringing these businesses to market, and in starting first few companies, and now General Catalyst was always, and we had to really focus on the business issues. Which means that if I'm doing something that's either pissing Joel off or wrong, he not only has the obligation, he immediately is going to come and say, hey, I think this, I think that. And there's no pretense that it's going to hurt our friendship. On the contrary, our friendship is going to be stronger because we have this integrity of real transparency. So that's a very important part of it. The second thing, which is harder at scale, it was easier when we were smaller, Sounds crazy. That's that Joe and I were classic divide and conquer. Very, very different skill set. So things that I like to do are very different in the business that Joe likes to do. And as a result, we don't overlap a lot. So we don't have conflict. On the contrary, we started the business by being able to divide up the opportunities and go execute. And since we trust each other, we don't have to sec…

AI assessment note: “Let the friendship never get in the way of business.”

Q they used to. I always ask, if you had a billboard on Times Square, What would you put on it? What does that company message say? Inspire me. Inspire everyone in New York. And I would say five percent can even give an answer, let alone a good answer. Would you agree with me? And I guess, how do you advise founders on the art of storytelling for that company?

A So the first thing I would say is forget about markets. Forget about TAM. Forget about CAC LTV. Forget about all the things you think traditional people are going to ask you. Paint a picture for me. What do you want to build? You asked me, what did I want to build the general catalyst with Joel? It would look like it is today. I just wanted to be on the journey with founders. That was good enough for Joel and me to get a mission straight that the two of us were going to go do. So I'm asking the same question of a founder. Forget about all the BS and all the buzzwords, and then what I'm going to do with you is I'm going to use that, and I'm going to build from that into the storytelling of what this business looks like. And if we do it together, which is going to be fantastic, then what we're going to have the ability to do is understand in our first or second or third meeting what the long-term vision looks like of the business. Who do we want to sell this product to? What's the product going to look like? I ask people a question. Who do you want around you on your team? If somebody says, well, I can do it all myself. I'm just going to hire a bunch of low-level people to help me. That's less inspiring to me, of course, than saying, hey, I need a co-founder that can do this or that, or I need people around me to do this. So I want people to To take the ingredients of the story a…

AI assessment note: “So instead of having an empirical discussion, we're having more of a creative discussion.”

Q And when you think about design objectives for the firm, did you always want to build a multi-stage, multi-geo global firm? What was the initial ideas, and how did that change over time?

A Well, people can't see because you and I are on video, but I'm laughing. Absolutely not. We had no plan. We had no strategy. We had no business model. All we knew is that we were going to take some of the money we just made selling our travel business, and we were going to hatch companies in Boston. The original slide that we had, which was just a photograph of a drive or board that we had, was very simple. Pick industries that were predominantly consumer because we knew nothing about enterprise or healthcare. But what we knew is, is that this is in the early 2000 that there were so many transformations that were going to happen around consumer that we had had experience building consumer business. So we just want to hatch the next generation of great consumer companies. So it wasn't just in other founders, which of course we wanted to do. It was the fact that we were going to hatch a bunch of our own companies. We're very clear not to call it an incubator. Because to us, an incubator is where you put sick babies, unfortunately, and it never really worked for us to call it an incubator, because an incubator also means throw a little money around and see what sticks. Our goal was from the start to be able to sit down with founders or our own team and hatch the next great generation of companies, and that's what we did at the beginning. And then what we realized is our ideas were…

AI assessment note: “Absolutely not. We had no plan. We had no strategy. We had no business model.”

Q with before. The interesting thing is I always ask, like, what's David's biggest strength? And the commonality amongst everyone's answers was incredible here. They said David is truly the best in the world when it comes to unique relationship building. When you reflect on that, What do you think you do that makes you so good at authentic, genuine relationship building with the companies and founders that you work with?

A So what you probably ask people, how good are David's financial skills? And they went, not so good. How good are his tech skills at evaluating product? Not so good. Is there anything that this guy does that's good? And they said, yeah, he gets along well with people, and he creates opportunities through relationships. So I think, Harry, we're all given some strengths, some weaknesses, and I'm a filmmaker, right? I mean, my background later is, you know, I'm a documentary filmmaker. I love the art of the story. So what I really want to try to understand when I meet founders is what's their journey going to be like? And most importantly, where can we be helpful in that journey? In that journey, it's going to be relationship driven. You and I mentioned before that, that your mom has MS, okay? And the first thing that I would talk to you about, if I met you, you were a founder, is I'd really try to understand Is your mom getting the healthcare? I would be biased. I'd say, is your mom in the UK? Which I know is good healthcare, but is there something in the United States that may be better? Now, I'm not doing that because I'm trying to gratiate myself to you. I'm doing it because I'm trying to develop a bond with you that's bigger than just making money. The second thing is, is that I realized that any one of us, including me, there's a limited amount that I can bring anybody, but I…

AI assessment note: “I'm doing it because I'm trying to develop a bond with you that's bigger”

Q When you had to go out to institutionals for the first time, how did that go?

A Well, there were a couple of fun ones. One was Joel and I left leaving an endowment, which was one of the Ivy endowments, and we were driving in my convertible Back to Boston from visiting this endowment. We were really excited because we got our first commitment from endowment, and I said, hey, that's a tremendous donation that they all made to us. And Joel looked at me and said, it's not a donation. They actually want their money back with a return. Because the only money that Joel and I had ever raised, knowing our backgrounds, was that we've built huge foundations around philanthropists our entire lives. So the only time I had ever asked anybody for money, our original business didn't require Investor money, and this was the first time, and my mentality was raising money to make the world a better place, not necessarily to build companies. But the response was quite mixed. One endowment that I sat down with, they asked this very important question. What's our investment experience? We said, none. And what's your tech experience? And we said, well, we built a tech-enabled business. That group turned around and said, I can't believe it. I will never get this 30 minutes back that you just took from me. Please leave. So I got back in the car and agreed that didn't go so well. But where we found a sweet spot was there was two people in particular that really believed in this ear…

AI assessment note: “the response was quite mixed. One endowment that I sat down with”

Q How big was the first fund, and was it easy to raise?

A Yeah, we used our own money. Well, the first fund was probably seventy million dollars, and it wasn't even in GPLP, it was an LLC, because of course we were building a company, which is the only thing we thought we knew how to do. It was seventy million, most of it was from us, and then a handful of checks from some of our friends in Boston, who would become mentors to us, mostly investors, And other funds, because we had no investment experience, and we went to some of our friends and said, hey, will you help us? And they said, sure, can we put money in? So our first fund was all friends and family, but the majority of the money came from Joel and me.

AI assessment note: “the first fund was probably seventy million dollars, and it wasn't even in GPLP”

Q When you've spoken about trust, you've mentioned your wife a couple of times. I'm really interested. You've had an incredible marriage, and you have an incredible partnership with your wife. What have been some of the biggest lessons to you, and I know this is a broad one, but of what makes a truly great marriage? As you said, you met when you were 17, or when she was 17.

A I think the key to marriages or partnerships, one is full transfer. You have to trust that everything that everybody tells you and everything they need to know is happening all the time, number one. Number two, I think the divide and conquer strategy in life is really an important one. Let's decide what you want to do. Let's decide what I want to do. You trust me to get this done. I trust you to get that done. And let's collaborate that way versus like everybody, because ego is the Biggest undoing of people, and if I feel like my ego is being compromised, you feel your ego is compromised, there is no solution to that. The third thing, we can marry people who are different. Joe and I have very little outside the office in common. I mean, we have multiple different interests, but the things we have in common bring us together. At home, it's the same way. They're deeply both filmmakers, but she runs our film business. Why? She's She's enormously competent. She's tremendously empathetic with filmmakers. She's so good at what she does. I trust her decisions. And as a result, we have this ability to create things that are really great because she's able to lead me and my thinking in a way that's fantastic. And if you permeates every part of our relationship, so, and she's very right brain, something that's really important.

AI assessment note: “I think the key to marriages or partnerships, one is full transfer.”

Q to have a connection with you, and I know that to do that I have to show more of myself than just, we're killing it, and yeah, life's great, thank you so much. But I often find this barrier of unwillingness to open up, which means I'm kind of just pushing against a brick wall sometimes. Do you ever feel this, and how do you approach it when you do?

A Part of developing a relationship with people is vulnerability. If you're self-confident, which you are, and you have the ability to deal with adversity, which you do, and you understand that the ups and downs make life fun and challenging at the same time, then your own vulnerability. So let's just say you're either one up or one down in most relationships. We try for parity, but you are not. So let's imagine, like, I probably four or five times a week, We'll meet people, kids, either friends of my kids, or kids of my friends, or just people in the GC network insight about what they should do next. The first thing I'm going to realize is it's a little bit overwhelming for them to talk about this, ok? They don't know me, and I've asked them to just share their inner secrets. What the hell do you want to do with your life? Who are you? So I don't do it that way. I often begin by saying, wow, this is really exciting. Can I tell you what life was like for me when I was 24? You know, I was a filmmaker trying to make documentary films, and it was like I couldn't make a living. I wasn't sure what I wanted to do, and I had a couple of ideas. And you can see, Harry, people's body language completely changed. They go from being uptight. Maybe this guy was a screw-up when he was younger, too, or he doesn't know what the heck was going on next. The reason why I'm doing this is, A, it's tr…

AI assessment note: “I often begin by saying, wow, this is really exciting. Can I tell you”

Q How do you think about enjoying an amazing relationship On the personal side, while also not losing an inch of performance on the professional and the work side, what does that look like to you?

A Wait, Well, you're using different definitions. You're putting activity and hours against process and outcome and success. I think being a well-rounded human, which includes having relationships with people, more empathetic, it makes you more creative. It makes you a fuller human being because you're not just Dealing with your own shit, you're now including other people in your life, which is very, very powerful. The second thing is, it's very important that you have a safe zone with people. Could be your girlfriend, could be your wife at some point, it could be just friends. You need people, and if you're alone, and you're alone at work, other than doing podcasts with me and others, but you don't have the benefit, your insecurities, your insights, your concerns about things with others, and I think because you don't have that at work, I think the interpersonal, I'm not a shrink, but I play one on TV, but I think having that relationship with your girlfriend is really important, maybe easily solvable, and they can't be done on your own. I think having a full life that includes fun, friends, sports, philanthropy, a loving relationship with somebody gives you a much better business person, an investor, and a much better mentor for founders. So I don't think you're less of a machine. I think you're more of a human being.

AI assessment note: “having a loving relationship with somebody gives you a much better business person”

Q When you've spoken about trust, you've mentioned your wife a couple of times. I'm really interested. You've had an incredible marriage, and you have an incredible partnership with your wife. What have been some of the biggest lessons to you, and I know this is a broad one, but of what makes a truly great marriage? As you said, you met when you were 17, or when she was 17.

A I think the key to marriages or partnerships, one is full transfer. You have to trust that everything that everybody tells you and everything they need to know is happening all the time, number one. Number two, I think the divide and conquer strategy in life is really an important one. Let's decide what you want to do. Let's decide what I want to do. You trust me to get this done. I trust you to get that done. And let's collaborate that way versus like everybody, because ego is the Biggest undoing of people, and if I feel like my ego is being compromised, you feel your ego is compromised, there is no solution to that. The third thing, we can marry people who are different. Joe and I have very little outside the office in common. I mean, we have multiple different interests, but the things we have in common bring us together. At home, it's the same way. They're deeply both filmmakers, but she runs our film business. Why? She's She's enormously competent. She's tremendously empathetic with filmmakers. She's so good at what she does. I trust her decisions. And as a result, we have this ability to create things that are really great because she's able to lead me and my thinking in a way that's fantastic. And if you permeates every part of our relationship, so, and she's very right brain, something that's really important.

AI assessment note: “I think the key to marriages or partnerships, one is full transfer.”

Q they used to. I always ask, if you had a billboard on Times Square, What would you put on it? What does that company message say? Inspire me. Inspire everyone in New York. And I would say five percent can even give an answer, let alone a good answer. Would you agree with me? And I guess, how do you advise founders on the art of storytelling for that company?

A So the first thing I would say is forget about markets. Forget about TAM. Forget about CAC LTV. Forget about all the things you think traditional people are going to ask you. Paint a picture for me. What do you want to build? You asked me, what did I want to build the general catalyst with Joel? It would look like it is today. I just wanted to be on the journey with founders. That was good enough for Joel and me to get a mission straight that the two of us were going to go do. So I'm asking the same question of a founder. Forget about all the BS and all the buzzwords, and then what I'm going to do with you is I'm going to use that, and I'm going to build from that into the storytelling of what this business looks like. And if we do it together, which is going to be fantastic, then what we're going to have the ability to do is understand in our first or second or third meeting what the long-term vision looks like of the business. Who do we want to sell this product to? What's the product going to look like? I ask people a question. Who do you want around you on your team? If somebody says, well, I can do it all myself. I'm just going to hire a bunch of low-level people to help me. That's less inspiring to me, of course, than saying, hey, I need a co-founder that can do this or that, or I need people around me to do this. So I want people to To take the ingredients of the story a…

AI assessment note: “I'm going to use that, and I'm going to build from that into the storytelling”

Q I mean, they did tell me about them. Not a cash to buy Adam. It's a 20 year journey with GC. Take me back. What was that founding aha moment for you with Joel? You decided you wanted to do venture post companies that you'd done with him before.

A What really happens is that Joel has been my best friend and my business partner. We met when we were five or six years old, and we've been just great friends ever since. And I have always loved the fact that I met my wife when she was 17. I was only a couple of years older. I met Joel when I was single digits. A lot of the relationships in my life have been very, very long term. But our road to venture capital is a quite unusual one. Joel and I built a business over the first eight or nine years of our business life and travel. And we built a whole bunch of travel businesses, and it was a fantastic start of business because the beauty of travel, which is the exact opposite of venture capital, is, is that travel people pay up front and then travel later. So you build this massive cash balance that allows you to build your business, and we built a business with several hundred million dollar business without ever having to raise venture capital. Now that's the public answer. The private answer, since you and I are talking privately, is that nobody was ever going to fund us. We had no experience, but in that building that Business. And in funding it through self-funding, and even still today, most VCs want to bet on something empirical, a track record, or something that they can point to that says, Harry, if they did this, then they could do that. And there was no way in the worl…

AI assessment note: “our road to venture capital is a quite unusual one”

Q How do you think about enjoying an amazing relationship On the personal side, while also not losing an inch of performance on the professional and the work side, what does that look like to you?

A Wait, Well, you're using different definitions. You're putting activity and hours against process and outcome and success. I think being a well-rounded human, which includes having relationships with people, more empathetic, it makes you more creative. It makes you a fuller human being because you're not just Dealing with your own shit, you're now including other people in your life, which is very, very powerful. The second thing is, it's very important that you have a safe zone with people. Could be your girlfriend, could be your wife at some point, it could be just friends. You need people, and if you're alone, and you're alone at work, other than doing podcasts with me and others, but you don't have the benefit, your insecurities, your insights, your concerns about things with others, and I think because you don't have that at work, I think the interpersonal, I'm not a shrink, but I play one on TV, but I think having that relationship with your girlfriend is really important, maybe easily solvable, and they can't be done on your own. I think having a full life that includes fun, friends, sports, philanthropy, a loving relationship with somebody gives you a much better business person, an investor, and a much better mentor for founders. So I don't think you're less of a machine. I think you're more of a human being.

AI assessment note: “gives you a much better business person, an investor, and a much better mentor for founders.”

Q That would be amazing. Listen, David, these episodes Those make me realize why I love what I do so much. You saw we kind of threw the schedule out the window, which is perfect. I'd love to ask, David, given your life in storytelling and filmmaking, what are storytelling and filmmaking, particular filmmaking, having common with venture capital?

A Great. It's about the arc of the story. How does one person tell a story that enables everybody around them to be inspired toward an outcome? So all of our films that we make hopefully are telling you a story about something that you really want to know. Icarus was the story of the Russian doping scandal, but it didn't start out that way. It started out as a film that a buddy of ours wanted to make about doping and biking. And when that didn't work out, it was just like venture capital. It was a pivot. We said, okay, that didn't work out. What's the next step? And he said, well, I want to go to Russia and find out how the Russians cheat. And we said, that's a fabulous film. And it ended up being a great film, win the Academy Award and all that. But for the director, Ryan Fogle, who's one of the best filmmakers in the world, it was like a venture capital outcome. It was down round that ended up being a multi-billion dollar outcome. The great hack, which is a story of Cambridge Analytica, that story helped break the scenario to the world about how bad some social media companies were rigging elections, abusing people's data, and that was a great story of truth to power. The dissident, the dissident's a story we made two years ago, which is how the Saudis killed Khashoggi, and out of that story came two things. Number one, Discovery about this product called Pegasus, which certain…

AI assessment note: “it was just like venture capital. It was a pivot.”

Q Tell me, what three traits would you most want your children to adopt?

A Well, number one, I think that I'd love To have them have a love of life and a generosity of spirit. Nina and I have hopefully built a family, and with Olivia and Julian, with power comes responsibility. To be able to give back and create a spirit of capacity to help other people, at the same time having a love of life and an empathy for people going forward. The second thing, the joy of seeing other people succeed and being a person of successes is a really, really fulfilling thing. I think if our kids had those, and then they were able to surround their lives with really wonderful people. In my daughter's case, I got great blessing in the cheek. Got married this summer to Streeter, who's a great, fabulous guy who I love dearly. Julian said it at their wedding, I finally got an older brother. And having my kids love the people in their lives and having that joy is extraordinary. But having them be part of other people's successes Is a month that lasts a lifetime.

AI assessment note: “Well, number one, I think that I'd love To have them have a love”

Q So let's go back to the beginning, then. When we have that decision to found GC on that beach in Hawaii, we have a blank canvas, and we can Design the fund and the principles in the way that we want to. When you think about the design objectives, what did you want to build back then? And how did the name General Catalyst come about?

A Well, the name General Catalyst is a fabulous friend of ours named Brian Beadall. And sitting around one day, we were trying to decide just as a friend, what were we? There were a lot of different names thrown around, but the name came up is that we're kind of a catalyst. We're kind of a catalyst in many different ways. We could have called the firm Catalyst. I mean, there is a catalyst. But what we wanted to be is we wanted to be catalysts, but in a way that was just around one thing, the journey of founders. So that's how we came up with the name. It wasn't a very creative way, but it seems to have sticked, and then obviously it's worked out well.

AI assessment note: “So that's how we came up with the name.”

Q So let's go back to the beginning, then. When we have that decision to found GC on that beach in Hawaii, we have a blank canvas, and we can Design the fund and the principles in the way that we want to. When you think about the design objectives, what did you want to build back then? And how did the name General Catalyst come about?

A Well, the name General Catalyst is a fabulous friend of ours named Brian Beadall. And sitting around one day, we were trying to decide just as a friend, what were we? There were a lot of different names thrown around, but the name came up is that we're kind of a catalyst. We're kind of a catalyst in many different ways. We could have called the firm Catalyst. I mean, there is a catalyst. But what we wanted to be is we wanted to be catalysts, but in a way that was just around one thing, the journey of founders. So that's how we came up with the name. It wasn't a very creative way, but it seems to have sticked, and then obviously it's worked out well.

AI assessment note: “Well, the name General Catalyst is a fabulous friend of ours named Brian Beadall.”

Q How does one give founder a permission to open their mindset to a new level of risk that maybe most others don't allow them permission? How do we let them see the uncapped upside and really allow them to expand their mental plasticity to it?

A Storytelling. Do it by analogy. You need to tell them, I've seen this before, and these are the things that work. It's not that complicated. It's hiring great people. Well, let's talk about a couple of things. The first thing you've got to evaluate is, is this person that's sitting in front of me Capable of the emotional, physical, and mental stress that it's going to take to build a business. Binary. If they're not that person, regardless of how good their idea is, they're not going to do it. Number one. Number two, are they going to attract talented people to work with them? Nobody has ever done this on their own. Are people going to want to work for them? Are they people that are going to gratiate themselves to others and inspire them through their leadership or their vision to want to work? We all know that. Great early stage companies are like cults. They all believe, they believe with a capital B. The third thing is, this sounds crazy, okay? In order to get a job, in order to get a date, in order to get into school, in order to get your first customer, in order to get people who want to work for you, all those skills require you to sell. Now, selling may not be dare to win, take the mountain selling, or commitment selling, but you've got to have founders that so believe In their company or so believe in their product that they can't believe that people would not agree wit…

AI assessment note: “Well, let's talk about a couple of things. The first thing you've got to evaluate”

Q I mean, they did tell me about them. Not a cash to buy Adam. It's a 20 year journey with GC. Take me back. What was that founding aha moment for you with Joel? You decided you wanted to do venture post companies that you'd done with him before.

A What really happens is that Joel has been my best friend and my business partner. We met when we were five or six years old, and we've been just great friends ever since. And I have always loved the fact that I met my wife when she was 17. I was only a couple of years older. I met Joel when I was single digits. A lot of the relationships in my life have been very, very long term. But our road to venture capital is a quite unusual one. Joel and I built a business over the first eight or nine years of our business life and travel. And we built a whole bunch of travel businesses, and it was a fantastic start of business because the beauty of travel, which is the exact opposite of venture capital, is, is that travel people pay up front and then travel later. So you build this massive cash balance that allows you to build your business, and we built a business with several hundred million dollar business without ever having to raise venture capital. Now that's the public answer. The private answer, since you and I are talking privately, is that nobody was ever going to fund us. We had no experience, but in that building that Business. And in funding it through self-funding, and even still today, most VCs want to bet on something empirical, a track record, or something that they can point to that says, Harry, if they did this, then they could do that. And there was no way in the worl…

AI assessment note: “where it all turned is one day after Joel and I sold our business”

Q How does one give founder a permission to open their mindset to a new level of risk that maybe most others don't allow them permission? How do we let them see the uncapped upside and really allow them to expand their mental plasticity to it?

A Storytelling. Do it by analogy. You need to tell them, I've seen this before, and these are the things that work. It's not that complicated. It's hiring great people. Well, let's talk about a couple of things. The first thing you've got to evaluate is, is this person that's sitting in front of me Capable of the emotional, physical, and mental stress that it's going to take to build a business. Binary. If they're not that person, regardless of how good their idea is, they're not going to do it. Number one. Number two, are they going to attract talented people to work with them? Nobody has ever done this on their own. Are people going to want to work for them? Are they people that are going to gratiate themselves to others and inspire them through their leadership or their vision to want to work? We all know that. Great early stage companies are like cults. They all believe, they believe with a capital B. The third thing is, this sounds crazy, okay? In order to get a job, in order to get a date, in order to get into school, in order to get your first customer, in order to get people who want to work for you, all those skills require you to sell. Now, selling may not be dare to win, take the mountain selling, or commitment selling, but you've got to have founders that so believe In their company or so believe in their product that they can't believe that people would not agree wit…

AI assessment note: “Well, let's talk about a couple of things. The first thing you've got to evaluate”

Q they fucked up on things that shouldn't be fucked up on. And I'm now kind of going back to this mindset of work with the 35, forty-year-olds who've done it, been there, made the mistakes on someone else's dime, and they're not gonna make them again. But then I kind of feel bad for that, and I'm like, really? How would you advise me with that kind of investment quandary?

A So I think that if you are going to be an investor in a company, whether you're a venture, Investor, or whether you are a, an angel. I think that we have to understand that with power comes responsibility, something we'll talk about later. And I think that if you are going to take the role of helping that founder, you need to help them candidly understand their strengths and what else they need, number one. Part of it is avoiding this issue that you have to be super well-rounded as a founder, and instead complementing or supplementing their team with co-founders or other people. If I'm a really strong product person, maybe I don't know how to sell, or vice versa. So instead of forcing that person to do things that they can't do, the second thing is what's the definition of success and failure? A very metaphysical rhetorical question, right? In our minds, a business that does not work out that most people would characterize as a failure is not a failure. It's a startup going. What I mean by that is we got to give people permission to go for it. And the biggest mistake and the biggest definition to us or me Of failure is not going for it. Not taking all of your intellectual and physical and mental resources and putting it and going for it. Forgiveness is a lot easier than permission. Push people around you hard to get the right answers. Push them to be curious. Push people to be …

AI assessment note: “instead complementing or supplementing their team with co-founders or other people.”

Q they fucked up on things that shouldn't be fucked up on. And I'm now kind of going back to this mindset of work with the 35, forty-year-olds who've done it, been there, made the mistakes on someone else's dime, and they're not gonna make them again. But then I kind of feel bad for that, and I'm like, really? How would you advise me with that kind of investment quandary?

A So I think that if you are going to be an investor in a company, whether you're a venture, Investor, or whether you are a, an angel. I think that we have to understand that with power comes responsibility, something we'll talk about later. And I think that if you are going to take the role of helping that founder, you need to help them candidly understand their strengths and what else they need, number one. Part of it is avoiding this issue that you have to be super well-rounded as a founder, and instead complementing or supplementing their team with co-founders or other people. If I'm a really strong product person, maybe I don't know how to sell, or vice versa. So instead of forcing that person to do things that they can't do, the second thing is what's the definition of success and failure? A very metaphysical rhetorical question, right? In our minds, a business that does not work out that most people would characterize as a failure is not a failure. It's a startup going. What I mean by that is we got to give people permission to go for it. And the biggest mistake and the biggest definition to us or me Of failure is not going for it. Not taking all of your intellectual and physical and mental resources and putting it and going for it. Forgiveness is a lot easier than permission. Push people around you hard to get the right answers. Push them to be curious. Push people to be …

AI assessment note: “if you are going to take the role of helping that founder, you need”

Q is, funny, I've been burned before and it's hurt me a lot. I don't really think I've probably got over it really since then, so I don't really trust many people. Point being to me, do you start from a relationship of full trust when you have new relationships? Do you start with no trust and it's there to be gained? And how do you evaluate trust in new relationships?

A Great question. I have certain things that I try to evaluate, and kind of as a message to people, and let me try these out on you, ok? These are kind of like what I consider just like my core things. What makes a purposeful, thoughtful life? And this will give you some insight on trust. The first thing, and again, I don't want to be gender specific on this, is Happy wife, happy life, whoever your spouse is. You've got to make sure that the people around you, in particular, the people that you love and love you, that's first and foremost. And one of the things I look for when I meet people early in relationships, do they have deep, sustaining, fulfilling friendships or relationships with family members? Somebody who's a loner and somebody that doesn't like to get along with people who has shitty relationships with their family, not as a rule, but it's pretty hard to imagine that they're going to be a great leader. And a great person to do it. The second thing, and this is very important one, Harry, is nobody's spared. Everybody runs into shit in their lives. Families, marriages, partnerships, companies. It reigns everywhere. When you realize that the issues that you're dealing with are not unique to David and Harry, but everybody else has those issues, you become less stigmatized, and it becomes easier for you to talk about the things that bother you or the things that are on yo…

AI assessment note: “These are kind of like what I consider just like my core things.”