The Exchanges

Q I would love to kick off it with some context. You know, we look at the incredible behemoth that is Slack Day, but it all has to start somewhere. So how did you make your way into the world of startups, and how did you come to found Slack?

A I'm not even sure where to start there. I mean, I guess one lucky break was... Starting college when I did, which is 1992, so I got exposed to the internet really early, kind of before the web became a thing, which meant that I could become a web developer back when there was very, very few of them in the world. In 98, I got my first dot-com job, which I quit in the very beginning of 2000. I actually quit in, like, kind of mid-late February 2000, so just before the crash, and convinced one of my co-workers to start a, um, to take his, like, side project from Which was a website called gradfinder.com, which is a competitor to classmates, and this is many years before Facebook, so it was so many people we used to organize high school reunions. I convinced him to, let's make that a company, and we raised a tiny bit of money, and it got acquired. A couple years later, started another company called Ludicorp to build a web-based, massively multiplayer game called Game NeverEnding. That didn't work, but we made Flickr instead. Flickr got bought by Yahoo, spent three years at Yahoo, and then most of that original Flickr team got back together to start Another company called TinySpec to build a web-based massively multiplayer game that didn't work, and then we ended up with Slack.

AI assessment note: “most of that original Flickr team got back together to start... ended up with Slack”

Q Can I ask, do you have like a leadership position? Coach, a mentor, an advisor. When you have these core leadership questions, you go to them, and they are your sounding board for these momentous decisions, be it around whatever the big kind of strategic question could be for you as the leader.

A Not any one person, and there's a kind of an array of people. So I have some people whose leadership style I admire, or, you know, decision-making I admire. John Dono, who's now the CEO of Nike, is one of those. But I've never had any kind of full-time mentor, and the people that have made the biggest difference are A woman named Chris Cordell, who was until literally yesterday my chief of staff, and now has started her own consulting business, has been great. She's been at Slack for five and a half years or something like that, so supported me through a lot of change. And I've been very lucky in that I get along with and have a lot of respect for our board members, and they've been incredibly helpful as well. Different board members at different times, but they've always been people that I can come to with big questions and get good advice.

AI assessment note: “Not any one person, and there's a kind of an array of people.”

Q I would love to kick off it with some context. You know, we look at the incredible behemoth that is Slack Day, but it all has to start somewhere. So how did you make your way into the world of startups, and how did you come to found Slack?

A I'm not even sure where to start there. I mean, I guess one lucky break was... Starting college when I did, which is 1992, so I got exposed to the internet really early, kind of before the web became a thing, which meant that I could become a web developer back when there was very, very few of them in the world. In 98, I got my first dot-com job, which I quit in the very beginning of 2000. I actually quit in, like, kind of mid-late February 2000, so just before the crash, and convinced one of my co-workers to start a, um, to take his, like, side project from Which was a website called gradfinder.com, which is a competitor to classmates, and this is many years before Facebook, so it was so many people we used to organize high school reunions. I convinced him to, let's make that a company, and we raised a tiny bit of money, and it got acquired. A couple years later, started another company called Ludicorp to build a web-based, massively multiplayer game called Game NeverEnding. That didn't work, but we made Flickr instead. Flickr got bought by Yahoo, spent three years at Yahoo, and then most of that original Flickr team got back together to start Another company called TinySpec to build a web-based massively multiplayer game that didn't work, and then we ended up with Slack.

AI assessment note: “most of that original Flickr team got back together... and then we ended up with Slack.”

Q Totally get you there. Can I ask, it makes me think of like, and I totally agree with you in terms of make it inevitable, but it also does rely on like market timing. How do you think about your own patience, and do you get frustrated in terms of speed of market adoption and market timing?

A Well, I would say no, just because the, I feel like I've been so lucky throughout my whole life with the, with the timing and things have worked out well. Now, You know, you said the speed of adoption. It's not a hundred percent dependent on us, but one thing I think we've never done especially well is answer the questions. What is Slack? Why is it important? How is it different? We've had various answers, and you know, some are better than others, but the cleaner and more powerful of an answer we have for that or those questions, the faster it'll get adopted. So it's not something that just, um, is happening in the external world, and we're Passers by observing it. It's something that we actively cause, and so if we're impatient, we should be impatient with ourselves.

AI assessment note: “Well, I would say no, just because the, I feel like I've been so lucky”

Q like, company vision, Yeah. It's hard to imagine slack would be what it is today when you started tiny spec. And I always find vision can be quite constraining because it can actually kind of, um, restrain the upside because you never quite expect it to go as well as it can. How do you think about kind of vision as a constraint and how important do you weight vision?

A It's pretty open as a term. And I think that there's, you know, we say our vision is a world where organizational agility is easy to achieve regardless of the organization, the size. So that's very, Very nonspecific. Like, it, it doesn't, um, tie us to, to much, and in that sense, it's more of, like, a, a statement of aspiration, I guess, rather than ambition. Speaking of Andreessen Horowitz, so, you know, we, we raised money, uh, for the game. We had five or six million dollars left when we decided to shut it down and work on Slack, and we prepared this presentation for their partner meeting to go and say what we were going to do, and to be clear, we already had the money, and they wanted us to keep going. Like, no VC would want a third of their money back when they could Kind of play the lottery one more time, but we went down there and our big ambition, like we believe that if we captured all of the addressable market, we would have a hundred million dollars a year in revenue and thereby be a billion dollar company. And it's funny looking back at that now, because I don't remember exactly how long it took us, but certainly less than two years to get to a hundred million dollars in ARR. So we had no idea how big it would be. So in the case where vision is talking more about the values or Or aspirations, uh, in the, in a broad general sense, I think it's probably a good thing.…

AI assessment note: “A vision of a very specific outcome, like a state of the world, I think is probably less valuable.”

Q Can I ask, do you have like a leadership position? Coach, a mentor, an advisor. When you have these core leadership questions, you go to them, and they are your sounding board for these momentous decisions, be it around whatever the big kind of strategic question could be for you as the leader.

A Not any one person, and there's a kind of an array of people. So I have some people whose leadership style I admire, or, you know, decision-making I admire. John Dono, who's now the CEO of Nike, is one of those. But I've never had any kind of full-time mentor, and the people that have made the biggest difference are A woman named Chris Cordell, who was until literally yesterday my chief of staff, and now has started her own consulting business, has been great. She's been at Slack for five and a half years or something like that, so supported me through a lot of change. And I've been very lucky in that I get along with and have a lot of respect for our board members, and they've been incredibly helpful as well. Different board members at different times, but they've always been people that I can come to with big questions and get good advice.

AI assessment note: “Not any one person, and there's a kind of an array of people.”

Q out. Final question before the quickfire. And it's like, talk about a big decision you made. The direct listing is probably one of the biggest. Like, where, and this was from a founder who, um, chose a similar decision to you, and, and he asked the question to you, why do you stand on the SPAC versus direct listing versus IPO debate, and how do you often find yourself advising?

A I haven't done a lot of advising. I mean, I've given, related my experience, and given some of my opinions, but I think it's so dependent on circumstance that there's really no general rule. There's certainly no general rule today about whether Direct listing is better than a traditional IPO, or a SPAC is better than either of them. Partly because pre-SPAC, the real decision, I think, came down to, do you want to raise more money right now? And if you don't, then a direct listing is better than, um, than an IPO. SPACs, you can raise money. I mean, I think that you more or less have to, but to the extent that people think about it as kind of a hack to get around the regulatory process, while there's a lot of kind of There's a lot of detail, and there's a lot of paperwork, and there's a lot of things that maybe aren't a great use of time in the normal regulatory process. There's also an enormous amount of value there, and I think that we started three years or so before, maybe four years before we went public, for what we called public company readiness. In fact, PCR was like an acronym inside the company to refer to that, and the kind of discipline and the governance mechanisms and the controls you put in place are incredibly valuable. The actual mechanism by which you come to be listed, I think is much less important.

AI assessment note: “The actual mechanism by which you come to be listed, I think is much less important.”

Q Totally get you there. Can I ask, it makes me think of like, and I totally agree with you in terms of make it inevitable, but it also does rely on like market timing. How do you think about your own patience, and do you get frustrated in terms of speed of market adoption and market timing?

A Well, I would say no, just because the, I feel like I've been so lucky throughout my whole life with the, with the timing and things have worked out well. Now, You know, you said the speed of adoption. It's not a hundred percent dependent on us, but one thing I think we've never done especially well is answer the questions. What is Slack? Why is it important? How is it different? We've had various answers, and you know, some are better than others, but the cleaner and more powerful of an answer we have for that or those questions, the faster it'll get adopted. So it's not something that just, um, is happening in the external world, and we're Passers by observing it. It's something that we actively cause, and so if we're impatient, we should be impatient with ourselves.

AI assessment note: “if we're impatient, we should be impatient with ourselves.”

Q Josh Trishnan before the show, and he said even when everything was going as well as it was with Slack and is with Slack, Stuart would always start the board meeting with everything that wasn't going well, which is unusual for most of our founders. So talk to me about this. Why did you choose this slant, and why did you feel that was the right way to do it?

A I think that's just my natural disposition, and I felt kind of vindicated to a certain extent when I finally read that, uh, Charlie Munger essay. Gosh, now I can't remember what it's called. The Psychology of Human... It's definitely not psychology of human confusion, but it's something like that, and apparently at Berkshire Hathaway, they had a sign over the, one of the conference rooms, or maybe, uh, Warren Buffett's office, or something like that, that said, tell us the bad news first, it is only the good news that can wait, and part of that is creating a culture where people are open about the problems, so the not falling prey to the, what Charlie calls the Persian messenger syndrome, so that Kill the messenger thing, because you have to understand what's going well and what's not going well, and if people feel like they can't bring up problems, that's very difficult. But for me, it's always just been, those are the things we need to work on. The things that are going well are good. You know, there might be opportunities for them to, for us to do even more well, but if there's an opportunity for us to do more well, then that's a problem. And it's not a style that works for everyone. You know, for me, listing all the challenges or the problems or things that aren't going well is Is an expression of optimism, because I believe that we can do something about them, and for cert…

AI assessment note: “I think that's just my natural disposition”

Q Can I ask you, a lot of entrepreneurs struggle in terms of tying their identity to their company, and I guess when you have such a monumental success like Slack is today, how do you think about kind of your identity being tied to Slack, and how do you manage that relationship of the two, identity and company?

A Yeah, it's very difficult, to be honest, and so it's hard not to take it personally when things aren't going well, and Unfortunately, on the flip side, when things are going well, while I may feel good about myself, it hardly feels like it's something intrinsic to me. So there's a lot of luck, and there's a lot of timing, and there's a lot of just, you know, good things that can happen. It does make it difficult in thinking about, you know, the future. I don't mean necessarily me leaving Slack, but how to devolve power, and how to delegate, and how to set up the company to For the scale that we're at now, it's a little over 2500 employees and a billion dollar run rate for, for billing, so it's, you know, it's a pretty big company, and it can't just be tied to me forever. Probably haven't put enough effort into instilling or building a culture that's powerful enough that it has a lot of momentum. On the other hand, part of that is just because everything's happened so fast. You know, it's, in one sense, gosh, six and a half years is a long time, but in another sense, going from, oh, I mean, it's an immense amount of change.

AI assessment note: “it's very difficult, to be honest, and so it's hard not to take it personally”

Q Josh Trishnan before the show, and he said even when everything was going as well as it was with Slack and is with Slack, Stuart would always start the board meeting with everything that wasn't going well, which is unusual for most of our founders. So talk to me about this. Why did you choose this slant, and why did you feel that was the right way to do it?

A I think that's just my natural disposition, and I felt kind of vindicated to a certain extent when I finally read that, uh, Charlie Munger essay. Gosh, now I can't remember what it's called. The Psychology of Human... It's definitely not psychology of human confusion, but it's something like that, and apparently at Berkshire Hathaway, they had a sign over the, one of the conference rooms, or maybe, uh, Warren Buffett's office, or something like that, that said, tell us the bad news first, it is only the good news that can wait, and part of that is creating a culture where people are open about the problems, so the not falling prey to the, what Charlie calls the Persian messenger syndrome, so that Kill the messenger thing, because you have to understand what's going well and what's not going well, and if people feel like they can't bring up problems, that's very difficult. But for me, it's always just been, those are the things we need to work on. The things that are going well are good. You know, there might be opportunities for them to, for us to do even more well, but if there's an opportunity for us to do more well, then that's a problem. And it's not a style that works for everyone. You know, for me, listing all the challenges or the problems or things that aren't going well is Is an expression of optimism, because I believe that we can do something about them, and for cert…

AI assessment note: “listing all the challenges or the problems... is an expression of optimism”

Q is, like, when you think about very strategic decisions that could be expansions into new country, it could The expansions into alternative product adjacencies, like reversible versus irreversible decisions. How do you think about those, where continuous iteration may not really be such an option, and actually it's, hey, are we fundamentally going to enter a new market? Yes or no. And there's a lot more binariness to the outcome.

A Yeah, I mean, so that's a great question, and they're definitely very different things, and the parlance that's caught on in Slack, and I think probably elsewhere is borrowed from Jeff Bezos in the one-way doors and two-way doors, so... A lot of times, deep into a discussion about something, someone will say, well, that's a two-way door, meaning we can just stop debating this at some point. We can try it, and if it doesn't work, we can revert. Most of the tough ones, uh, as you point out, are not that way. They're really, um, one way. Nevertheless, I still like to find some reason that trumps all of the other reasons, and, and hang on to that. Like, so, I mean that, Distinct from a process of coming up with a giant list of pros and cons, and then kind of trying to assign values to them, and summing them up, and seeing which side has more points. There's almost always, to me, one reason that's fundamental, and it can still be wrong, so it's not that you can proceed with certainty on those, but in the absence of some fundamental reason for something, the challenges that inevitably arise just generate their own problems of pros and cons, and indecision, and hesitation. Said early on that being an entrepreneur can be a lot like doing parkour, and obviously not physically, because I'm, I would not be a good parkour participant. But what I mean is, you have to keep moving. You have t…

AI assessment note: “I still like to find some reason that trumps all of the other reasons”

Q out. Final question before the quickfire. And it's like, talk about a big decision you made. The direct listing is probably one of the biggest. Like, where, and this was from a founder who, um, chose a similar decision to you, and, and he asked the question to you, why do you stand on the SPAC versus direct listing versus IPO debate, and how do you often find yourself advising?

A I haven't done a lot of advising. I mean, I've given, related my experience, and given some of my opinions, but I think it's so dependent on circumstance that there's really no general rule. There's certainly no general rule today about whether Direct listing is better than a traditional IPO, or a SPAC is better than either of them. Partly because pre-SPAC, the real decision, I think, came down to, do you want to raise more money right now? And if you don't, then a direct listing is better than, um, than an IPO. SPACs, you can raise money. I mean, I think that you more or less have to, but to the extent that people think about it as kind of a hack to get around the regulatory process, while there's a lot of kind of There's a lot of detail, and there's a lot of paperwork, and there's a lot of things that maybe aren't a great use of time in the normal regulatory process. There's also an enormous amount of value there, and I think that we started three years or so before, maybe four years before we went public, for what we called public company readiness. In fact, PCR was like an acronym inside the company to refer to that, and the kind of discipline and the governance mechanisms and the controls you put in place are incredibly valuable. The actual mechanism by which you come to be listed, I think is much less important.

AI assessment note: “it's so dependent on circumstance that there's really no general rule.”

Q is, like, when you think about very strategic decisions that could be expansions into new country, it could The expansions into alternative product adjacencies, like reversible versus irreversible decisions. How do you think about those, where continuous iteration may not really be such an option, and actually it's, hey, are we fundamentally going to enter a new market? Yes or no. And there's a lot more binariness to the outcome.

A Yeah, I mean, so that's a great question, and they're definitely very different things, and the parlance that's caught on in Slack, and I think probably elsewhere is borrowed from Jeff Bezos in the one-way doors and two-way doors, so... A lot of times, deep into a discussion about something, someone will say, well, that's a two-way door, meaning we can just stop debating this at some point. We can try it, and if it doesn't work, we can revert. Most of the tough ones, uh, as you point out, are not that way. They're really, um, one way. Nevertheless, I still like to find some reason that trumps all of the other reasons, and, and hang on to that. Like, so, I mean that, Distinct from a process of coming up with a giant list of pros and cons, and then kind of trying to assign values to them, and summing them up, and seeing which side has more points. There's almost always, to me, one reason that's fundamental, and it can still be wrong, so it's not that you can proceed with certainty on those, but in the absence of some fundamental reason for something, the challenges that inevitably arise just generate their own problems of pros and cons, and indecision, and hesitation. Said early on that being an entrepreneur can be a lot like doing parkour, and obviously not physically, because I'm, I would not be a good parkour participant. But what I mean is, you have to keep moving. You have t…

AI assessment note: “I still like to find some reason that trumps all of the other reasons”

Q like, company vision, Yeah. It's hard to imagine slack would be what it is today when you started tiny spec. And I always find vision can be quite constraining because it can actually kind of, um, restrain the upside because you never quite expect it to go as well as it can. How do you think about kind of vision as a constraint and how important do you weight vision?

A It's pretty open as a term. And I think that there's, you know, we say our vision is a world where organizational agility is easy to achieve regardless of the organization, the size. So that's very, Very nonspecific. Like, it, it doesn't, um, tie us to, to much, and in that sense, it's more of, like, a, a statement of aspiration, I guess, rather than ambition. Speaking of Andreessen Horowitz, so, you know, we, we raised money, uh, for the game. We had five or six million dollars left when we decided to shut it down and work on Slack, and we prepared this presentation for their partner meeting to go and say what we were going to do, and to be clear, we already had the money, and they wanted us to keep going. Like, no VC would want a third of their money back when they could Kind of play the lottery one more time, but we went down there and our big ambition, like we believe that if we captured all of the addressable market, we would have a hundred million dollars a year in revenue and thereby be a billion dollar company. And it's funny looking back at that now, because I don't remember exactly how long it took us, but certainly less than two years to get to a hundred million dollars in ARR. So we had no idea how big it would be. So in the case where vision is talking more about the values or Or aspirations, uh, in the, in a broad general sense, I think it's probably a good thing.…

AI assessment note: “A vision of a very specific outcome, like a state of the world, I think is probably less valuable.”

Q like, you know, do you find then that you seed the thoughts to let them then come to the conclusion on their own first? And I guess the secondary question is, like, how does one also keep an open enough mindset that although the conclusion in your head is said is what you want, actually someone could bring a more optimal conclusion? Like, how do you think about those things?

A Yeah. You know, maybe, actually, this is the one area where I have learned something, you made me think of it, is being very explicit about the things that I either don't have an opinion on, or don't have a strong opinion on, or I'm sure about, or I just, you know, have no expertise and, and, um, nothing to contribute. So, you know, there's things where I have some kind of intuition or opinion, but I don't have any belief in it. You know, really early in, in our history, how to approach enterprise sales. I'd never done it before. I didn't really You didn't have any direct experience of the challenges and, and the kind of objections that people have to overcome or the process, and so that part is very easy for me to say I don't understand. I often have pretty strong opinions around the technical implementation of something, so the, like, the architectural decisions that we're making, not because I care so much about how they're implemented today for what we're trying to accomplish today, but for the implications that they carry for the future, because I Anyone who has been successful with any kind of software project, either in, like, the software industry, meaning enterprise, or consumer apps, or any kind of technology, knows that at some point, more than half of the effort just goes into paying off old technical or design debt, and if you can avoid that, then it's great, but I…

AI assessment note: “I don't leave a lot of space for people to come back with better answers”

Q Can I ask you, a lot of entrepreneurs struggle in terms of tying their identity to their company, and I guess when you have such a monumental success like Slack is today, how do you think about kind of your identity being tied to Slack, and how do you manage that relationship of the two, identity and company?

A Yeah, it's very difficult, to be honest, and so it's hard not to take it personally when things aren't going well, and Unfortunately, on the flip side, when things are going well, while I may feel good about myself, it hardly feels like it's something intrinsic to me. So there's a lot of luck, and there's a lot of timing, and there's a lot of just, you know, good things that can happen. It does make it difficult in thinking about, you know, the future. I don't mean necessarily me leaving Slack, but how to devolve power, and how to delegate, and how to set up the company to For the scale that we're at now, it's a little over 2500 employees and a billion dollar run rate for, for billing, so it's, you know, it's a pretty big company, and it can't just be tied to me forever. Probably haven't put enough effort into instilling or building a culture that's powerful enough that it has a lot of momentum. On the other hand, part of that is just because everything's happened so fast. You know, it's, in one sense, gosh, six and a half years is a long time, but in another sense, going from, oh, I mean, it's an immense amount of change.

AI assessment note: “it's hard not to take it personally when things aren't going well”

Q like, you know, do you find then that you seed the thoughts to let them then come to the conclusion on their own first? And I guess the secondary question is, like, how does one also keep an open enough mindset that although the conclusion in your head is said is what you want, actually someone could bring a more optimal conclusion? Like, how do you think about those things?

A Yeah. You know, maybe, actually, this is the one area where I have learned something, you made me think of it, is being very explicit about the things that I either don't have an opinion on, or don't have a strong opinion on, or I'm sure about, or I just, you know, have no expertise and, and, um, nothing to contribute. So, you know, there's things where I have some kind of intuition or opinion, but I don't have any belief in it. You know, really early in, in our history, how to approach enterprise sales. I'd never done it before. I didn't really You didn't have any direct experience of the challenges and, and the kind of objections that people have to overcome or the process, and so that part is very easy for me to say I don't understand. I often have pretty strong opinions around the technical implementation of something, so the, like, the architectural decisions that we're making, not because I care so much about how they're implemented today for what we're trying to accomplish today, but for the implications that they carry for the future, because I Anyone who has been successful with any kind of software project, either in, like, the software industry, meaning enterprise, or consumer apps, or any kind of technology, knows that at some point, more than half of the effort just goes into paying off old technical or design debt, and if you can avoid that, then it's great, but I…

AI assessment note: “being very explicit about the things that I either don't have an opinion on”

Q Can I ask, it's, it's a very composed and Strategic and rational mindset. Have you always had it as a mindset? And I guess, like, how have you seen your leadership mindset evolve over time, given the experience that you've had now?

A Yeah, they're almost separate modes of thinking and separate tasks. So when I said I feel very high degree of conviction or a lot of confidence about a certain domain of decisions, I studied logic. I did a lot of logic as an undergrad. I mean, like, actual logic that has funny symbols in your thesis project is to do proofs of Various theses and stuff like that. That's really ingrained, and I tried to explain this to people as the way that you approach Minesweeper, And now we're getting to a world where fewer and fewer people are familiar with Minesweeper, the classic Windows game, but for those of people who vaguely remember it or don't know it, it's not really that great of a game. You're presented with a grid. There are all the squares are covered. When you click, you uncover them, and if you click on a bomb, you lose, but if you don't click on a bomb, it uncovers all of the adjacent squares that aren't bombs. And puts a number on each square that says how many bombs are adjacent to it, and from that, it's very easy to deduce, unfortunately not in every case, which is the flaw of the game, but it's very easy to deduce which ones must be a bomb, and therefore which ones cannot be a bomb, and you can really, you know, either identify, if you're doing things correctly, the decisions that where it's just luck, and the decisions where you can, you can have a lot of confidence. Lea…

AI assessment note: “I studied logic. I did a lot of logic as an undergrad.”

Q I think it's an incredibly strategic answer. I do have to ask you, like, how did you think about it with the early acquisitions of your, you know, Flickers, and then also over time with Slack?

A Well, money alone does definitely not make you happy. I know some people who have a lot of money and are fairly miserable. It definitely makes things easier, though, so while it Doesn't magically make you happy. It creates the conditions where a lot of stress has gone from your life. If you're having to choose between diapers and food every week, then you're in a much different position with respect to the degree of stress in your life and the challenges you face. So I said in some interview, I don't even remember where now it was, but there's kind of three levels of wealth, and one is I don't have to worry about my debts, and the second one is I don't care what anything costs in a restaurant, because I very clearly remember, like, choosing between two dishes, and one was Two dollars more than the other, and I decided I couldn't splurge on the more expensive thing. And then the third one is you don't care what vacations cost. And after that, I think it's probably all about the same. And people who have a lot of money want more money, not because they're going to do something with it. Generally, they're going to give it away, but because it's how you keep score. It's kind of like Ben Horowitz from Entries in Horowitz. One of our investors was explaining salespeople to me back when we first started having to hire salespeople and And they're very driven by the money, not because t…

AI assessment note: “Well, money alone does definitely not make you happy.”

Q like, you know, for me, like my company is so much a part of me that when I go on holiday and I don't have that kind of company element and company activity, I'm actually thoroughly lost and quite unhappy. Like, how would you advise me with that entanglement so much of self and company? That when you don't have it, even for a brief period, you're quite fundamentally lost.

A That's a good question. I mean, to be honest, I don't, um, experience that, but I think it's probably just a kind of cognitive or emotional disposition. I'm constantly worried about the things outside of the company when I'm focused on the company and constantly worried about the company when I'm focused on anything outside. So that's probably an unhealthy genetic inheritance of a Jewish mother and got a little bit of the Jewish mother worrying genes. Yeah, I guess, you know, maybe it's just a function of age or priorities. The hard part for me is imagining if it was totally gone, then how would I feel? With a group of CEOs, um, and among them was, uh, Ryan Smith from Qualtrics, and he just bought the Utah Jazz, and I was teasing him a little bit, you know, like, you're a little, like, young to be a professional sports team owner. To be clear, I'm very happy for him. He's loved the jazz his whole life. I mean, it's a, you know, it's a family-run business, and it's going to be Huge and all that stuff, but it is, it is funny that there's, um, like a class of occupation that is professional football team owner, because it's people who have retired from companies where they had a lot of prestige, and they had a lot of power and wealth, and they're not ready to just be that who they are as a person without any of that, and therefore they, and this is my armchair psychoanalysis, so w…

AI assessment note: “to be honest, I don't, um, experience that, but I think it's probably”

Q I think it's an incredibly strategic answer. I do have to ask you, like, how did you think about it with the early acquisitions of your, you know, Flickers, and then also over time with Slack?

A Well, money alone does definitely not make you happy. I know some people who have a lot of money and are fairly miserable. It definitely makes things easier, though, so while it Doesn't magically make you happy. It creates the conditions where a lot of stress has gone from your life. If you're having to choose between diapers and food every week, then you're in a much different position with respect to the degree of stress in your life and the challenges you face. So I said in some interview, I don't even remember where now it was, but there's kind of three levels of wealth, and one is I don't have to worry about my debts, and the second one is I don't care what anything costs in a restaurant, because I very clearly remember, like, choosing between two dishes, and one was Two dollars more than the other, and I decided I couldn't splurge on the more expensive thing. And then the third one is you don't care what vacations cost. And after that, I think it's probably all about the same. And people who have a lot of money want more money, not because they're going to do something with it. Generally, they're going to give it away, but because it's how you keep score. It's kind of like Ben Horowitz from Entries in Horowitz. One of our investors was explaining salespeople to me back when we first started having to hire salespeople and And they're very driven by the money, not because t…

AI assessment note: “Well, money alone does definitely not make you happy.”

Q Can I ask, it's, it's a very composed and Strategic and rational mindset. Have you always had it as a mindset? And I guess, like, how have you seen your leadership mindset evolve over time, given the experience that you've had now?

A Yeah, they're almost separate modes of thinking and separate tasks. So when I said I feel very high degree of conviction or a lot of confidence about a certain domain of decisions, I studied logic. I did a lot of logic as an undergrad. I mean, like, actual logic that has funny symbols in your thesis project is to do proofs of Various theses and stuff like that. That's really ingrained, and I tried to explain this to people as the way that you approach Minesweeper, And now we're getting to a world where fewer and fewer people are familiar with Minesweeper, the classic Windows game, but for those of people who vaguely remember it or don't know it, it's not really that great of a game. You're presented with a grid. There are all the squares are covered. When you click, you uncover them, and if you click on a bomb, you lose, but if you don't click on a bomb, it uncovers all of the adjacent squares that aren't bombs. And puts a number on each square that says how many bombs are adjacent to it, and from that, it's very easy to deduce, unfortunately not in every case, which is the flaw of the game, but it's very easy to deduce which ones must be a bomb, and therefore which ones cannot be a bomb, and you can really, you know, either identify, if you're doing things correctly, the decisions that where it's just luck, and the decisions where you can, you can have a lot of confidence. Lea…

AI assessment note: “Leadership? Totally different. I mean, like, really, no one or very few people follow”

Q like, you know, for me, like my company is so much a part of me that when I go on holiday and I don't have that kind of company element and company activity, I'm actually thoroughly lost and quite unhappy. Like, how would you advise me with that entanglement so much of self and company? That when you don't have it, even for a brief period, you're quite fundamentally lost.

A That's a good question. I mean, to be honest, I don't, um, experience that, but I think it's probably just a kind of cognitive or emotional disposition. I'm constantly worried about the things outside of the company when I'm focused on the company and constantly worried about the company when I'm focused on anything outside. So that's probably an unhealthy genetic inheritance of a Jewish mother and got a little bit of the Jewish mother worrying genes. Yeah, I guess, you know, maybe it's just a function of age or priorities. The hard part for me is imagining if it was totally gone, then how would I feel? With a group of CEOs, um, and among them was, uh, Ryan Smith from Qualtrics, and he just bought the Utah Jazz, and I was teasing him a little bit, you know, like, you're a little, like, young to be a professional sports team owner. To be clear, I'm very happy for him. He's loved the jazz his whole life. I mean, it's a, you know, it's a family-run business, and it's going to be Huge and all that stuff, but it is, it is funny that there's, um, like a class of occupation that is professional football team owner, because it's people who have retired from companies where they had a lot of prestige, and they had a lot of power and wealth, and they're not ready to just be that who they are as a person without any of that, and therefore they, and this is my armchair psychoanalysis, so w…

AI assessment note: “to be honest, I don't, um, experience that”