The Exchanges

Q tools. So my question to you is, how do you think about MVP in terms of how recent lean startups kind of promoted it obviously hugely, and it spawned the movement that is the lean startup. And now we have more of a pushback against the lean startup and MVPs and move fast and break things. Where do you sit on the move fast and break things, lean startup methodology?

A In general, I'm very pro, which is to say, and here's why. I think one of the mistakes that I see many founders make is they have a preconception about the world. And they're unwilling to test whether or not it's true. They're just so sure it's accurate that they kind of plow ahead. Oh, I know I'm right about thing X, Y, Z. I don't actually need to talk to anyone to verify it. Whereas for me, I think like, even if you're sure you should probably still double check if, in other words, if I'm positive, if I'm a hundred percent sure about something that makes me nervous because nothing in the world is that cut or dry. So it makes me think, oh, is this actually a blind spot for me that I have not really had a chance to diligent. And so I love the idea of when possible running lightweight experiments to verify that your assumptions are actually correct. And for our company, one of the things that was really, really fun about it is on day one, we signed up our first three customers because I just called them up and I said, Hey, who's doing your bookkeeping today? Oh, you know, we can actually do it better. You should sign up with pilot. And the way that we provided the services, I just did their books and QuickBooks online, just like any other bookkeeper would. So the actual shape of our business allowed us to actually get into the market immediately and Because of kind of how we had…

AI assessment note: “In general, I'm very pro, which is to say, and here's why.”

Q No, I totally get you. Can I ask, what are the right questions to ask when assessing the potential fit of an acquirer that will really give you that indication of whether it's the right company for you over another acquisition offer?

A It's not that dissimilar from a hiring process. I mean, the questions that we asked when we explored the Previously was, look, is this going to be a good home and a good outcome for our team? And actually that was number one for me, which is the team has taken a bet on us and the team is trusting us to do right by them. And I think for me, that was the strongest obligation I felt. Then question two is, is there alignment between what we were trying to do and what the acquirer would like to do? Is this an acquisition where the product or the company or the technology are going to live on in some way, or is this an acquisition that is purely for the talent? And I think being very sober and honest with yourself Why is the acquirer interested? And are the reasons that the acquirer interested consistent with the reasons that I'm excited about this? In other words, if you had a product and you're like, I can't wait to continue building this product at the acquirer, and the acquirer actually just doesn't want to build the product at all. Instead, they want your engineers. That's probably not going to be a relationship that you're going to be that happy with.

AI assessment note: “is this going to be a good home and a good outcome for our team?”

Q I'm the excited one, but I want to kick off today with a little on you, so tell me, how did you make your way into the world of startups? There have been three now, and then what was that aha moment with Pilot?

A Yeah, so it's a long story that actually begins all the way back in undergrad, so my co-founder is Jeff Jessica and I were all at MIT together undergrad. And to make it even nerdier, not only were we at MIT, we were in the computer club at MIT. That's how we all first met. So we first met socially. Exactly. We first met socially. We're taking classes together. As we graduated, you know, we got together. We said, we really want to do a company. And so we started a company based on Jeff's master's thesis. It was called Case Gleiss. We had technology that could update systems while they were running. And we actually bootstrapped that company. We did it for about three years and Then Oracle acquired it, and we were in Boston this whole time. And so that was our first real startup experience. And I think after having that under our belt, after our time at Oracle, we were there for a year and a day, we were really, really itching to get back into it. So as soon as we left Oracle, we got the band back together. We said, okay, we want to do another company. We started a company called Zulip, which was a group chat tool for businesses, kind of like a Slack-like product at the time. I think Slack was making a mobile game at the time, at a time when people were quite skeptical of the space. We operated that company for about two years. Dropbox acquired it. We all moved to San Francisco to…

AI assessment note: “it's a long story that actually begins all the way back in undergrad”

Q on the theme of people, though, themselves, because, you know, I always look, especially when assessing opportunities for founder market fit, if I can say that terrible coinage without blushing. But you've said to me before that passion is overrated in starting companies. So it kind of goes counter to that. What did you mean by that? And does it reduce the importance of founder market fit, do you think?

A Yeah, that's a good question. And I think my perspective on this is a little bit subtle, which is to say, if you had asked me five years ago, Wasim, are you passionate about bookkeeping? I'm positive I would have, first of all, I probably would have laughed. And then I probably would have said, no, absolutely not. And so I think one of the things that's interesting, or at least in our experience, and for all of our companies, for the first one, it was these reboot list software updates. For the second one, it was group chat at work. And for this company, it's bookkeeping for startups and small businesses. If you'd asked me before any of those companies, how excited are you to spend a bunch of time with Linux system administrators really getting into the weeds on how they install software updates? That's not something I would have identified for you a long time ago as, oh, that's an area I'm passionate about. I think for me, what I'm really passionate about, or where I really find joy in, is talking to folks, understanding the problem they have, explaining to them what we're up to, and then hearing them say, oh, wow, that's really, really interesting to me. That's really going to solve a big pain point I have. And so what I really need to say is I think many founders, especially first time founders kind of have this approach. It's like, well, I'm not that excited about HR softwa…

AI assessment note: “where I really find joy in, is talking to folks, understanding the problem”

Q No, I totally get you. Can I ask, what are the right questions to ask when assessing the potential fit of an acquirer that will really give you that indication of whether it's the right company for you over another acquisition offer?

A It's not that dissimilar from a hiring process. I mean, the questions that we asked when we explored the Previously was, look, is this going to be a good home and a good outcome for our team? And actually that was number one for me, which is the team has taken a bet on us and the team is trusting us to do right by them. And I think for me, that was the strongest obligation I felt. Then question two is, is there alignment between what we were trying to do and what the acquirer would like to do? Is this an acquisition where the product or the company or the technology are going to live on in some way, or is this an acquisition that is purely for the talent? And I think being very sober and honest with yourself Why is the acquirer interested? And are the reasons that the acquirer interested consistent with the reasons that I'm excited about this? In other words, if you had a product and you're like, I can't wait to continue building this product at the acquirer, and the acquirer actually just doesn't want to build the product at all. Instead, they want your engineers. That's probably not going to be a relationship that you're going to be that happy with.

AI assessment note: “is there alignment between what we were trying to do and what the acquirer would like to do?”

Q to ask you, cause that makes me think about bootstrap days almost. And I know that one of the companies that you did the first was bootstraps and then obviously the latter two were VC backed. So it's an interesting one. And you said before that VC is potentially overrated. So it naturally is a VC. This terribly pains me to hear what seems. So what needs your thinking here?

A Sure. What I would really say is something a little bit less provocative, which is look, VC is not right for every business. And I think We all do the industry a disservice when we overly fetishize it. In other words, I think there are companies that need venture capital and want to be venture backed and will operate at venture scale. And for those companies, VC is not overrated at all. In fact, it's required. But I think there are many companies in the world that have the potential to be terrific companies that will yield terrific outcomes for their founders that don't require venture capital. And in particular, and I don't think this should be the goal, but if your goal is wealth creation, I think it's much easier to make A hundred percent of the ten million dollar company than one percent of the billion dollar company. And so I think we sort of do ourselves a disservice where we say, well, VC is the only way. And we talk about lifestyle businesses very dismissively. I think if you're thoughtful about kind of what you actually want and what your objectives are with your company, it is not obvious that it per se requires venture capital.

AI assessment note: “VC is not right for every business. And I think We all do the industry a disservice”

Q Can I ask, do you have a favorite interview question? It's one of my nerdy favorite questions to ask.

A I don't. I mean, I think the thing increasingly that I, and this kind of harkens back to Mathilde's thing a little bit, where the thing I feel most passionately about is on the interviewing process is just there being rigor in the process itself. In other words, before you bring in someone for an interview, ideally you've written the role requirement. You know what the role is that you're trying to hire. You know what the skills that you need are. And you've built an interview day that actually tests for those skills. So if they say, oh, I need a front end engineer who knows react and knows how to use Git, but also like, can you SQL or whatever? Like let's build an interview day that actually probes on those things that are requirements. The best interview gives you a signal as to where the candidate spikes. A mediocre interview will let you say no for candidates that are bad, but don't really let you like good candidates really shine. And so I think being very, very rigorous about building the process, I think is much, much more important than I have this one gotcha question, or I have this one question that I think really teases out a lot about the candidate.

AI assessment note: “I don't.”

Q with respect to that. I guess my question is then subsequently, if you do choose to go down the venture route, as you have done with Pilot, and you have some of the best and best This is that you can get behind you. How do you think about investor selection? It's a massive choice that lasts for 10 years. How do you think about that crucial investor selection moment?

A I think about two things, and this sounds trite, and I think when people told us this, I didn't really believe them, but in retrospect, like they were very much on the money about it, which is you are signing up for a long-term partnership and relationship. And so if you're viewing it from a transactional perspective about, well, let me just optimize for the absolute best terms. I think you're being a bit short-sighted because you're going to spend so much time with your board member over the course of this company. Like I text with our board member all the time. He and I probably talk literally every week, and we're going to do that for the next 10 years, I assume. And as a consequence, if you don't feel like that person has conviction in your business, if you don't feel like you trust them, if you don't feel like they have your back, I think it would be a mistake to work with them.

AI assessment note: “you are signing up for a long-term partnership and relationship”

Q Can I also, in terms of the final element, we said about kind of the team there and scaling teams. I've spoken to, as I said, investors and team members before, and they said about this amazing culture that you have internally. And so what do you deliberately do to create this atmosphere? And maybe what advice would you give For scaling founders who want to create the same atmosphere?

A You know, I think for me, it has been about how do we create a place actually where we ourselves are very, very excited to work. And for me, that was about being surrounded by really smart, really talented, kind people who are amazing at what they do, who will challenge us to do our best work. And then falling out from there, I think is, of course, your biggest lever on this is hiring. And I think this is sort of well-trodden advice land. But I think one of the things that's very important is Making sure that you keep the hiring bar high. In other words, if you debrief on a candidate, and your conclusion is, oh, I don't know, maybe, like, they might be able to do a good job here. Like, that should be a no. Like, you should only bring on board people that you're very, very excited about, because what is your culture, if not the sum of the people at the company? So I think being very, very thoughtful about really designing and running good, rigorous interview processes, selecting for folks who are smart and driven and intellectually honest and kind, and then I think, importantly, building a culture that recognizes that the best people don't necessarily look or act or sound or come from the same backgrounds or experiences that you did, and trying to very, very mindfully and thoughtfully create a place where, look, we want to get the best people here. And to get the best people her…

AI assessment note: “keep the hiring bar high. In other words, if you debrief on a candidate”

Q I absolutely love hearing that story. I didn't know about that at all, but, uh, totally with you there. What's your superpower in company building? That one was from Shrav.

A Yeah. Sort of my initial answer would have been something like, well, I've done a lot of different things. Like I've done a little bit of sales. I've done a little marketing. I've done a little bit of engineering and Et cetera, et cetera. But I think bubbling out kind of one level higher, I would say it's just like empathy. In other words, again, my job now is not doing things. My job now is attracting and retaining the best people to do those things better than I can do. And so I think just like being human and understanding that you are also a person and you have goals and dreams and desires. And like, let's figure out how to scratch those itches while also having you contribute here at Pilot.

AI assessment note: “I would say it's just like empathy.”

Q Can I ask, when you actually kind of dive into the nitty-gritty, maybe more granular, how did the experiences with the prior two impact your operating mindset today with Pilot?

A Definitely. So I think the first company was very, very much about honestly, really just learning how to run a company one-on-one. When we first started K splice back in 2008, and we were all right out of school, my questions were really like, what is a CRM? How do I sell a thing? How do we even make a company? How do you make job offers to people? How do you hire people? How do you fire people? How do you coach? There's just like some very foundational. This is what a high performing team looks like. And I think there was just a lot of really learning on the streets of, Hey, we just have to figure out how to make this happen. So I think the first company was really about forcing us to learn these foundational things about how to run a startup. And then observing the experience at Oracle, observing the experience at Dropbox, our own experience, kind of giving it another shot at Zulip, I think really helped us refine our own, I don't want to say philosophy, but basically our own approach about how to best run companies.

AI assessment note: “the first company was really about forcing us to learn these foundational things”

Q the team and the tech, and when I spoke to many of your investors, as we chatted about before the show, they all said to me about especially the kind of founding relationship that you have with your co-founders. Obviously, it's been three companies now. What have been your biggest learnings on what it takes to have such a successful founding relationship, as you have done with Jeff and Jessica?

A Yeah, it's a good question, and it's a tough one, because for us, it really grew out of something organic, meaning I've known Jeff and Jessica for now 15 years, and we've worked together professionally for the past decade, and so I think the things that have really built up over that time are a strong degree of mutual trust and respect, and then also real clarity about expectations. In other words, I know what I'm gonna get when I work with Jeff and Jessica, and they know what they are gonna get when they work with me, and in fact, I can probably, with 95% accuracy, predict for you Jeff or Jessica's reaction to any given topic, and they can do the same. So I think at this point, the reason it lets us be so high-performing is that one of the biggest risk factors to any company really is founder drama, founder relationships, tensions there. For me, I just know that that has been really de-risked. And how did that happen? Well, I mean, it's the result, I think, of a lot of blood, sweat, and tears. It's we were thrust into these challenging, difficult situations, and we found a way to make it work.

AI assessment note: “a strong degree of mutual trust and respect, and then also real clarity about expectations”

Q It's interesting you said this, because Mathilde called in at front, said something similar in the way that she said, this grand mission and huge passion, actually, organizational discipline is far more important. I'm intrigued. How do you think about organizational discipline with regards to this kind of comparison with passion?

A Here's sort of how I think about it. I think there are some companies that people are not well-suited for. Like to your point about founder market fit, there has to be something there. In other words, if I hate legal work, I should probably not be starting a company that does the work of law firms. Or if the actual topic area itself is not one that I'm disinterested in, but perhaps like I'm actively opposed to spending time on or doesn't really jive with my own skill sets, I think that's going to be a problem. But I think Matilde is right where I think companies succeed by, to some extent, really just like putting one foot in front of the other in a really smart, thoughtful street. Strategic way, which has much more to do with how the company's organized, what the company's principles are, kind of the actual, almost tactical rather than strategic aspects of the business.

AI assessment note: “I think Matilde is right where I think companies succeed by, to some extent”

Q Can I ask, do you have a favorite interview question? It's one of my nerdy favorite questions to ask.

A I don't. I mean, I think the thing increasingly that I, and this kind of harkens back to Mathilde's thing a little bit, where the thing I feel most passionately about is on the interviewing process is just there being rigor in the process itself. In other words, before you bring in someone for an interview, ideally you've written the role requirement. You know what the role is that you're trying to hire. You know what the skills that you need are. And you've built an interview day that actually tests for those skills. So if they say, oh, I need a front end engineer who knows react and knows how to use Git, but also like, can you SQL or whatever? Like let's build an interview day that actually probes on those things that are requirements. The best interview gives you a signal as to where the candidate spikes. A mediocre interview will let you say no for candidates that are bad, but don't really let you like good candidates really shine. And so I think being very, very rigorous about building the process, I think is much, much more important than I have this one gotcha question, or I have this one question that I think really teases out a lot about the candidate.

AI assessment note: “I don't.”

Q to ask you, cause that makes me think about bootstrap days almost. And I know that one of the companies that you did the first was bootstraps and then obviously the latter two were VC backed. So it's an interesting one. And you said before that VC is potentially overrated. So it naturally is a VC. This terribly pains me to hear what seems. So what needs your thinking here?

A Sure. What I would really say is something a little bit less provocative, which is look, VC is not right for every business. And I think We all do the industry a disservice when we overly fetishize it. In other words, I think there are companies that need venture capital and want to be venture backed and will operate at venture scale. And for those companies, VC is not overrated at all. In fact, it's required. But I think there are many companies in the world that have the potential to be terrific companies that will yield terrific outcomes for their founders that don't require venture capital. And in particular, and I don't think this should be the goal, but if your goal is wealth creation, I think it's much easier to make A hundred percent of the ten million dollar company than one percent of the billion dollar company. And so I think we sort of do ourselves a disservice where we say, well, VC is the only way. And we talk about lifestyle businesses very dismissively. I think if you're thoughtful about kind of what you actually want and what your objectives are with your company, it is not obvious that it per se requires venture capital.

AI assessment note: “VC is not right for every business. And I think We all do the industry a disservice”

Q and moving fast. I do want to talk about scale. So that's a perfect segue. One of the things that comes with scale that we have chatted about before and again, I asked for contrarian statements and you more than delivered. So I'm sure there's nuance to this, but you said before, never sell your company. So why do you say this, and what were your big lessons on exits?

A Sure, and it's a little bit hypocritical advice in that we have sold two companies prior to this. But I think the thing that is an easy mistake for first time founders to make in navigating an M&A process is it's sort of like the VC thing where you're overly focused on the terms or the number and you're not really thinking hard enough about life post deal. Because the deal for either a financing or for an acquisition is just the beginning. It's the beginning of a much larger relationship you're going to have with the company. And so I think many founders say, well, I'm just going to take the bigger number. As opposed to saying, well, what is the place that I actually want to work? What will my role be there? Am I excited to stick around there for a while? Do I think I can really contribute? And very economically, even if you have a deal, and that deal vests over a certain time period, and company A and company B, like company A has the better offer, but you think you're less likely to stick around at company A. Company B, even with the lower offer, may be the one that puts more dollars in your pocket, or may be the one that you actually enjoy spending time at more, which I think you'll find being at the acquirer You know, the money doesn't make the day-to-day better or worse. The day-to-day is what the day-to-day is, and I think people fail to really optimize heavily for how ex…

AI assessment note: “easy mistake for first time founders to make in navigating an M&A process”

Q Can I also, in terms of the final element, we said about kind of the team there and scaling teams. I've spoken to, as I said, investors and team members before, and they said about this amazing culture that you have internally. And so what do you deliberately do to create this atmosphere? And maybe what advice would you give For scaling founders who want to create the same atmosphere?

A You know, I think for me, it has been about how do we create a place actually where we ourselves are very, very excited to work. And for me, that was about being surrounded by really smart, really talented, kind people who are amazing at what they do, who will challenge us to do our best work. And then falling out from there, I think is, of course, your biggest lever on this is hiring. And I think this is sort of well-trodden advice land. But I think one of the things that's very important is Making sure that you keep the hiring bar high. In other words, if you debrief on a candidate, and your conclusion is, oh, I don't know, maybe, like, they might be able to do a good job here. Like, that should be a no. Like, you should only bring on board people that you're very, very excited about, because what is your culture, if not the sum of the people at the company? So I think being very, very thoughtful about really designing and running good, rigorous interview processes, selecting for folks who are smart and driven and intellectually honest and kind, and then I think, importantly, building a culture that recognizes that the best people don't necessarily look or act or sound or come from the same backgrounds or experiences that you did, and trying to very, very mindfully and thoughtfully create a place where, look, we want to get the best people here. And to get the best people her…

AI assessment note: “your biggest lever on this is hiring... Making sure that you keep the hiring bar high”

Q I absolutely love hearing that story. I didn't know about that at all, but, uh, totally with you there. What's your superpower in company building? That one was from Shrav.

A Yeah. Sort of my initial answer would have been something like, well, I've done a lot of different things. Like I've done a little bit of sales. I've done a little marketing. I've done a little bit of engineering and Et cetera, et cetera. But I think bubbling out kind of one level higher, I would say it's just like empathy. In other words, again, my job now is not doing things. My job now is attracting and retaining the best people to do those things better than I can do. And so I think just like being human and understanding that you are also a person and you have goals and dreams and desires. And like, let's figure out how to scratch those itches while also having you contribute here at Pilot.

AI assessment note: “bubbling out kind of one level higher, I would say it's just like empathy.”

Q I'm the excited one, but I want to kick off today with a little on you, so tell me, how did you make your way into the world of startups? There have been three now, and then what was that aha moment with Pilot?

A Yeah, so it's a long story that actually begins all the way back in undergrad, so my co-founder is Jeff Jessica and I were all at MIT together undergrad. And to make it even nerdier, not only were we at MIT, we were in the computer club at MIT. That's how we all first met. So we first met socially. Exactly. We first met socially. We're taking classes together. As we graduated, you know, we got together. We said, we really want to do a company. And so we started a company based on Jeff's master's thesis. It was called Case Gleiss. We had technology that could update systems while they were running. And we actually bootstrapped that company. We did it for about three years and Then Oracle acquired it, and we were in Boston this whole time. And so that was our first real startup experience. And I think after having that under our belt, after our time at Oracle, we were there for a year and a day, we were really, really itching to get back into it. So as soon as we left Oracle, we got the band back together. We said, okay, we want to do another company. We started a company called Zulip, which was a group chat tool for businesses, kind of like a Slack-like product at the time. I think Slack was making a mobile game at the time, at a time when people were quite skeptical of the space. We operated that company for about two years. Dropbox acquired it. We all moved to San Francisco to…

AI assessment note: “that was our first real startup experience”

Q on the theme of people, though, themselves, because, you know, I always look, especially when assessing opportunities for founder market fit, if I can say that terrible coinage without blushing. But you've said to me before that passion is overrated in starting companies. So it kind of goes counter to that. What did you mean by that? And does it reduce the importance of founder market fit, do you think?

A Yeah, that's a good question. And I think my perspective on this is a little bit subtle, which is to say, if you had asked me five years ago, Wasim, are you passionate about bookkeeping? I'm positive I would have, first of all, I probably would have laughed. And then I probably would have said, no, absolutely not. And so I think one of the things that's interesting, or at least in our experience, and for all of our companies, for the first one, it was these reboot list software updates. For the second one, it was group chat at work. And for this company, it's bookkeeping for startups and small businesses. If you'd asked me before any of those companies, how excited are you to spend a bunch of time with Linux system administrators really getting into the weeds on how they install software updates? That's not something I would have identified for you a long time ago as, oh, that's an area I'm passionate about. I think for me, what I'm really passionate about, or where I really find joy in, is talking to folks, understanding the problem they have, explaining to them what we're up to, and then hearing them say, oh, wow, that's really, really interesting to me. That's really going to solve a big pain point I have. And so what I really need to say is I think many founders, especially first time founders kind of have this approach. It's like, well, I'm not that excited about HR softwa…

AI assessment note: “half of the joy is the joy of building it, of the craft”

Q Totally. No, I do agree with you on that. I do want to finish, though, with my favorite, which is, what do the next five years hold for you and for Pilot, and just how big could it get? Is this changing the way we think about bookkeeping entirely?

A Yeah, I'm really, really excited about this company because I think the opportunity is so large, which is for every company, and you must do this all the time, for every company I ask, Look, how big is the market? And how much pain is there here? Is it a nice to have or a need to have? And for us, we say, look, well, how big is the market? Who needs bookkeeping? Literally every company needs bookkeeping. And then how badly do they need it? It's basically legally required. It's not an optional thing. You have to do the books for your company. And so when you multiply out those things, you actually landed this quite, quite huge market. I think the back of the envelope math on this is something like sixty billion dollars a year or I spent every year on SMB bookkeeping and accounting in the US alone. So it feels to me like the opportunity is so large, and it can definitely support a large, iconic, enduring public company. And I'm very, very excited to be on that path to take this company there. So five years from now, I will definitely be still here at Pilot, just continuing to grow the business.

AI assessment note: “So five years from now, I will definitely be still here at Pilot”

Q and moving fast. I do want to talk about scale. So that's a perfect segue. One of the things that comes with scale that we have chatted about before and again, I asked for contrarian statements and you more than delivered. So I'm sure there's nuance to this, but you said before, never sell your company. So why do you say this, and what were your big lessons on exits?

A Sure, and it's a little bit hypocritical advice in that we have sold two companies prior to this. But I think the thing that is an easy mistake for first time founders to make in navigating an M&A process is it's sort of like the VC thing where you're overly focused on the terms or the number and you're not really thinking hard enough about life post deal. Because the deal for either a financing or for an acquisition is just the beginning. It's the beginning of a much larger relationship you're going to have with the company. And so I think many founders say, well, I'm just going to take the bigger number. As opposed to saying, well, what is the place that I actually want to work? What will my role be there? Am I excited to stick around there for a while? Do I think I can really contribute? And very economically, even if you have a deal, and that deal vests over a certain time period, and company A and company B, like company A has the better offer, but you think you're less likely to stick around at company A. Company B, even with the lower offer, may be the one that puts more dollars in your pocket, or may be the one that you actually enjoy spending time at more, which I think you'll find being at the acquirer You know, the money doesn't make the day-to-day better or worse. The day-to-day is what the day-to-day is, and I think people fail to really optimize heavily for how ex…

AI assessment note: “people fail to really optimize heavily for how excited am I to be at the acquiring company”

Q Can I ask, when you actually kind of dive into the nitty-gritty, maybe more granular, how did the experiences with the prior two impact your operating mindset today with Pilot?

A Definitely. So I think the first company was very, very much about honestly, really just learning how to run a company one-on-one. When we first started K splice back in 2008, and we were all right out of school, my questions were really like, what is a CRM? How do I sell a thing? How do we even make a company? How do you make job offers to people? How do you hire people? How do you fire people? How do you coach? There's just like some very foundational. This is what a high performing team looks like. And I think there was just a lot of really learning on the streets of, Hey, we just have to figure out how to make this happen. So I think the first company was really about forcing us to learn these foundational things about how to run a startup. And then observing the experience at Oracle, observing the experience at Dropbox, our own experience, kind of giving it another shot at Zulip, I think really helped us refine our own, I don't want to say philosophy, but basically our own approach about how to best run companies.

AI assessment note: “helped us refine our own, I don't want to say philosophy”

Q again, I always use the show for my own personal advice. So apologies for this. But if resiliency is the key when assessing the strength of a founder, which Often it's stated that it is. How do you assess resilience? Again, this could be in candidates who are adding to the team, but how do you think about assessing resilience within people when either hiring them or investing in them?

A Yeah, it's hard because you can look at their track record, you can talk to their references, and those things will give you a fairly comprehensive picture, but that's all backwards looking. It's impossible to know kind of how it will look going forward. And so I think there's, of course, you sort of have to do your research, you have to do your diligence on it. But at the end of the day, I think there's just a, in my exercise, To take a bet on this person, knowing that some bets work and some bets don't. And I think when it comes to hiring, the critical thing there is when it's not working or if it's not working, not being afraid to have that hard conversation to acknowledge that and to do the right thing to fix it.

AI assessment note: “look at their track record, you can talk to their references”

Q It's interesting you said this, because Mathilde called in at front, said something similar in the way that she said, this grand mission and huge passion, actually, organizational discipline is far more important. I'm intrigued. How do you think about organizational discipline with regards to this kind of comparison with passion?

A Here's sort of how I think about it. I think there are some companies that people are not well-suited for. Like to your point about founder market fit, there has to be something there. In other words, if I hate legal work, I should probably not be starting a company that does the work of law firms. Or if the actual topic area itself is not one that I'm disinterested in, but perhaps like I'm actively opposed to spending time on or doesn't really jive with my own skill sets, I think that's going to be a problem. But I think Matilde is right where I think companies succeed by, to some extent, really just like putting one foot in front of the other in a really smart, thoughtful street. Strategic way, which has much more to do with how the company's organized, what the company's principles are, kind of the actual, almost tactical rather than strategic aspects of the business.

AI assessment note: “I think Matilde is right where I think companies succeed by, to some extent”