The Exchanges

Q have to ask, and this is going back slightly more than I normally would, but I'm too intrigued. I've done my research, and you came from a fascinating background, being a large Irish family growing up on the East Coast. I have to ask, how do you think your early and maybe more formative years shaped your thinking and philosophy as an innovator, and then as kind of a manager?

A Yeah, I mean, a couple things come to mind. So I'm number six of seven kids, so we had a family of nine in a small house with I think we had one bathroom and three bedrooms, so we're pretty crammed in there, and I think being in small area with a bunch of people, you become really tuned to who's angry today, who's crying today, what's the dynamic in the house, and just being programmed that way for the first 18 years of my life, as I became an entrepreneur and building and leading teams, it's not so much I'm thinking about who's crying today, and hopefully that doesn't happen too often, but I'm just very tuned to how people are getting along and working, and I think you'd be a successful entrepreneur, and this has been said many times by a lot of people, but I believe that the most important thing you can do is build the culture and the team and the interactions, so to me, some of that programming started when I was young, and then on the entrepreneurship standpoint, my dad was a pipe fitter, didn't go to college, but he's very scrappy, self-taught, multiple trades, And one of the things I used to do with him on the weekends would go to garage sales or yard sales, and we would buy things like used air conditioners and fix them up and then sell them. We might buy one for 20 dollars and we sold it for a hundred dollars. I don't remember what the prices were, but watching my dad l…

AI assessment note: “that taught me a little bit about entrepreneurship”

Q Absolutely. Priority versus reactive. It's one of the big lessons Fred is teaching me. I would love to ask, you mentioned, obviously, that kind of calendar optimizations. How do you think about email? I'm sure your inbox is immensely full continuously. How do you look to manage and productivize email?

A Yeah, so I get about 400 emails a day that are not spam, and I have three main inboxes. I have dozens of email addresses, but they come in one of three places. So Lola is the one I'm checking during the day, and my email is paul at lola.com, so your listeners should feel free to email me if they have a question about travel or anything else. And then I have my personal email, which is a Gmail account that, like, friends and family have, I have a third inbox, which is for everything else. So like my email for Amazon and Netflix and any company I do business with is on my e-commerce email. I almost never check that one unless I'm looking back to get something. As far as my personal and my work email, I am a big believer in OneTouch. So I really don't like email applications that allow you to defer an email to look at later because that means you've looked at it twice. And what I do, so Fred emails me and says, Hey, who's the copper that built those desks for you? It's only going to take me 30 seconds to haul someone out of my contacts and share contact with Fred now. It's the same 30 seconds it would take now as it would take if I defer it and do it tomorrow. So why not just do it now? So the quick ones I try to do quickly, and there's really, there's four things I do with an email. I mean, I'm really into alliteration, so I like that these all begin with the letter D in this cas…

AI assessment note: “As far as my personal and my work email, I am a big believer in OneTouch.”

Q the world of venture, from Mike at Sequoia, to Joel at GC, to GV, IVP. I mean, the list really does go on, Paul. But an area where, again, the network said you're truly talented. So for me as a VC nerd, my first question has to be, having worked with so many VCs, and so many of the best, what have you found really encapsulates the very special VCs?

A I'm trying to think of the best that I've worked with. So I think, you know, Mike and Sequoia and Joel General Cattle is certainly two of the best. And first of all, I look at them both as incredibly bright. They're able to succinctly sum up and find ways to state back to an entrepreneur. An entrepreneur might have some of a grand vision. And both of those guys are really skilled at finding ways to position something really simply. So really good synthesis and articulation of really simple vision, which at the beginning of a journey is really important to help you focus. And then the other thing I like about, when I think about the different PCs I've worked with, that I've enjoyed working with, like Harry Nellis is at Excel London. He's been exceptional. I've worked with him since the beginning days at Kayak, and I've been lucky enough to have him back me at Lola as well. He's just really astute with sort of running a board meeting and getting a team working together, doing the research between the meetings, being really encouraging, driving you to do more, raising the bar all the time, I think is really good. Finding other companies that have done better than you in certain ways that you can learn from. So it's all about that coaching and pushing and being a cheerleader, but also pushing someone ahead. And I think the best VCs are good at that.

AI assessment note: “really good synthesis and articulation of really simple vision”

Q Can I ask, when you as the founder maybe disagree with the direction that a board is suggesting, How do you eloquently and graciously reject it, so to speak, and pursue your own direction? Is there a right way to do it?

A Yeah, I mean, there's a right way to do it in person, and then also as a follow-up, and a lot of times in person, what I'll say is, that just doesn't sound right to me, and I'll try to explain why it doesn't sound right, so I'll argue back to them, and I, I try not to be argumentative, but I want to be honest and direct, and so if a board is trying to get me to do something which I think is defocused, I'll say, I think that's a really great idea, but I don't think we can think about that until we get X, Y, and Z done. So just try to keep focus on what are the top three priorities. It's something that good board members have helped me with because as someone who wants me known as an idea generator, I can suffer from adding too many things onto the agenda, but I think in that people have coached me with that, I've tried to use those skills back with my board to say, we can't leave a board meeting with 50 action items. You know, we have to, to really effective, you have Think about what are the two or three really, really most important things, and then make sure you crush those between board meetings. So in my minutes back to the board that I write out by hand, sort of pen on paper during the board meeting, then I transcribe them into a Google document and email them out usually the same day. I don't write down everything the board says, and maybe this is bad. I write down the th…

AI assessment note: “I'll say, I think that's a really great idea, but I don't think”

Q have to ask, and this is going back slightly more than I normally would, but I'm too intrigued. I've done my research, and you came from a fascinating background, being a large Irish family growing up on the East Coast. I have to ask, how do you think your early and maybe more formative years shaped your thinking and philosophy as an innovator, and then as kind of a manager?

A Yeah, I mean, a couple things come to mind. So I'm number six of seven kids, so we had a family of nine in a small house with I think we had one bathroom and three bedrooms, so we're pretty crammed in there, and I think being in small area with a bunch of people, you become really tuned to who's angry today, who's crying today, what's the dynamic in the house, and just being programmed that way for the first 18 years of my life, as I became an entrepreneur and building and leading teams, it's not so much I'm thinking about who's crying today, and hopefully that doesn't happen too often, but I'm just very tuned to how people are getting along and working, and I think you'd be a successful entrepreneur, and this has been said many times by a lot of people, but I believe that the most important thing you can do is build the culture and the team and the interactions, so to me, some of that programming started when I was young, and then on the entrepreneurship standpoint, my dad was a pipe fitter, didn't go to college, but he's very scrappy, self-taught, multiple trades, And one of the things I used to do with him on the weekends would go to garage sales or yard sales, and we would buy things like used air conditioners and fix them up and then sell them. We might buy one for 20 dollars and we sold it for a hundred dollars. I don't remember what the prices were, but watching my dad l…

AI assessment note: “just being programmed that way for the first 18 years of my life”

Q Can I ask, we mentioned kind of falsehoods around big rounds and IPOs. How did you feel when Kayak IPO'd?

A I mean, it was fun. It was a defining event for the company. A lot of people made a bunch of money, which is exciting. My assistant made a bunch of money. The engineers made money. It was great, but it didn't change things one day to the next day for our customers, so For us, we had more cash in the bank, and we could invest more in marketing, try to accelerate top-line growth, but other than that, the same thing we focused on before the IPO, we focused on afterwards, which is, how do we service these customers better? How do we approve these products? I will say, at Kayak, I was the CTO. My co-founder, Steve, was a CEO, and he had to deal with all the stuff about being public, so I didn't have to deal with the finance part of the house, which I'm really Glad about it. I focused on the product and on customer support, which I really love doing. And that didn't change day to day.

AI assessment note: “I mean, it was fun. It was a defining event for the company.”

Q Absolutely. Priority versus reactive. It's one of the big lessons Fred is teaching me. I would love to ask, you mentioned, obviously, that kind of calendar optimizations. How do you think about email? I'm sure your inbox is immensely full continuously. How do you look to manage and productivize email?

A Yeah, so I get about 400 emails a day that are not spam, and I have three main inboxes. I have dozens of email addresses, but they come in one of three places. So Lola is the one I'm checking during the day, and my email is paul at lola.com, so your listeners should feel free to email me if they have a question about travel or anything else. And then I have my personal email, which is a Gmail account that, like, friends and family have, I have a third inbox, which is for everything else. So like my email for Amazon and Netflix and any company I do business with is on my e-commerce email. I almost never check that one unless I'm looking back to get something. As far as my personal and my work email, I am a big believer in OneTouch. So I really don't like email applications that allow you to defer an email to look at later because that means you've looked at it twice. And what I do, so Fred emails me and says, Hey, who's the copper that built those desks for you? It's only going to take me 30 seconds to haul someone out of my contacts and share contact with Fred now. It's the same 30 seconds it would take now as it would take if I defer it and do it tomorrow. So why not just do it now? So the quick ones I try to do quickly, and there's really, there's four things I do with an email. I mean, I'm really into alliteration, so I like that these all begin with the letter D in this cas…

AI assessment note: “I get about 400 emails a day that are not spam, and I have three main inboxes.”

Q Can I ask, what do you think makes the best hiring ability? What do you think makes those best people at hiring so good?

A I think it's a couple of things. I mean, one is you need to be a storyteller and get people excited in the vision. And the second one is you need to have some humility and excitement for other people. So they don't see you as a banker on the other side of the desk who's going to say yes or no, but they see you as a collaborator and someone who's like really, really excited to work with you and someone who I try to leave people with the impression about if there's a guy I convinced To come in and meet me for a job interview, either at my company or at a Starbucks, let's say near where he currently works. I want him to leave that meeting thinking that I woke up today just to meet with him, that he was the person I was most excited to talk with. I think having that connection allows people to visualize, yeah, what would it be like to work with this person? So it's always just about making that connection, sort of selling a vision, and then letting people see how they can fit into it and how they might work with you.

AI assessment note: “one is you need to be a storyteller and get people excited in the vision”

Q Can I ask, we mentioned kind of falsehoods around big rounds and IPOs. How did you feel when Kayak IPO'd?

A I mean, it was fun. It was a defining event for the company. A lot of people made a bunch of money, which is exciting. My assistant made a bunch of money. The engineers made money. It was great, but it didn't change things one day to the next day for our customers, so For us, we had more cash in the bank, and we could invest more in marketing, try to accelerate top-line growth, but other than that, the same thing we focused on before the IPO, we focused on afterwards, which is, how do we service these customers better? How do we approve these products? I will say, at Kayak, I was the CTO. My co-founder, Steve, was a CEO, and he had to deal with all the stuff about being public, so I didn't have to deal with the finance part of the house, which I'm really Glad about it. I focused on the product and on customer support, which I really love doing. And that didn't change day to day.

AI assessment note: “I mean, it was fun. It was a defining event for the company.”

Q I mean, I think having the ability to hire someone who's better or smarter than you requires, in some cases, maybe incredibly measured ego and kind of, as you said, humility. How do you think about kind of ego and that element in today's startup world?

A There's a term I use called arrogant humility. What I mean by that is you want people that have been successful, for sure, and they don't have to have done what you need them to do right now. I think success translates. If you've had someone who's very successful in one part of their life, a lot of times that means they've Skills which drive success, which can drive in another part of their life, and you want people that, you know, they're aware they've been successful, so they have some confidence. If people have confidence, confidence is attractive, and it will cause other people to follow them, but you want people who not only have, like, confidence in their skills, but who have curiosity, and who want to learn skills from other people, so it's that combination of, I have confidence, like, I know the things I'm really good at, but I also know I can find people who have skills that I don't have, and I want to meet those people and hang out with those people.

AI assessment note: “There's a term I use called arrogant humility.”

Q Yeah, absolutely. I mean, I guess on the flip side, the super interesting part you said there about kind of some of the board members you've had, what have been your big learnings on kind of really driving effectiveness on the board management level?

A Well, certainly you want a high functioning board where the board itself gets along with each other. I've had situations where a board member is really talented on their own, but they're annoying in a board meeting. So I've had to coach board members about how I want them to operate in my board meeting. So for example, I'm not going to name names, but I have one board member who is absolutely brilliant, but would come up with an idea during the board meeting and really want to make sure that his idea was heard. So he would say the idea over and over and over again. So he'd repeat it once, then again, five minutes later, again, an hour later, and It was irritating and distracting to the meeting that he kept pushing his agenda so much, and so at one board meeting, I did something which is a little bit harsh, which is when he had an idea that I could tell this is one of these things he's going to push, I wrote it up on the whiteboard, and like two or three word summary, and then five minutes later, when he pitched it again, I said, yeah, yeah, I already wrote that one down, basically saying, dude, there's no reason. We don't need to waste time on this. I got it, and there's little things that you try to coach your team, and although you want to learn from your boards, You need to coach your board a little bit too, and part of that is about having clarity about what things your boa…

AI assessment note: “I've had to coach board members about how I want them to operate”

Q Well, don't worry. Fred will tell you I'm similarly terrible at process, but I mean, in the book, it does discuss your multiple scribblings of startup ideas in the middle of the night. And the interesting element for me is with so many ideas, how do you determine the good from the great and the ones that you really delve in and focus on versus those that you maybe don't?

A Yeah. The thing that I look for is, you know, it's common wisdom that ideas are cheap. What matters is execution. And so what I do with my ideas is it's not Not that unusual. I think yesterday I got up at 3:30 a.m. and wrote a SPAC or something, and it's not that unusual to come up with an idea, and then you pitch it, and then it just falls flat, and no one wants to buy in on it. So what I like to do to validate the idea is I write up a SPAC or a design, and then I pitch it, and I might be pitching it to a family member, a friend, a colleague, and it's only when I get one person excited do I say, okay, maybe there's something here, and then I pitch it to more and more people, and before I build Code. It's about, can I get a bunch of people excited about this idea? And in particular, can I get people to help me work on this idea? And a lot of times I will have side projects aside from my day job. Like I work pretty hard at my day job, but a lot of times on nights and weekends, I'll work on something on the side. And I generally only pursue those if I can sign, find someone to take them forward. So that to me is the easiest way of validating. Does this idea hunt?

AI assessment note: “So what I like to do to validate the idea is I write up a”

Q Can I ask, what do you think makes the best hiring ability? What do you think makes those best people at hiring so good?

A I think it's a couple of things. I mean, one is you need to be a storyteller and get people excited in the vision. And the second one is you need to have some humility and excitement for other people. So they don't see you as a banker on the other side of the desk who's going to say yes or no, but they see you as a collaborator and someone who's like really, really excited to work with you and someone who I try to leave people with the impression about if there's a guy I convinced To come in and meet me for a job interview, either at my company or at a Starbucks, let's say near where he currently works. I want him to leave that meeting thinking that I woke up today just to meet with him, that he was the person I was most excited to talk with. I think having that connection allows people to visualize, yeah, what would it be like to work with this person? So it's always just about making that connection, sort of selling a vision, and then letting people see how they can fit into it and how they might work with you.

AI assessment note: “one is you need to be a storyteller and get people excited in the vision”

Q We spoke about kind of some of the best there in Bill Clinton for Charisma, and you've angel invested in many companies, you've worked with many different founders. I'm intrigued. Where do you see many tech founders going wrong, maybe, in their hiring approach today?

A Well, I think either the tech founder lacks humility, and they're arrogant, and they only hire people that would be subservient to them, so they don't hire people that are daring enough, and they're going to challenge them and push them. That's how one Failure, I see. And again, this is a little bit cliche, but to be the best at recruiting, you literally want to hire people that are smarter than you and stronger than you. And a lot of entrepreneurs lack the confidence for hiring people stronger than you. And it's something that I've never really worried about. Like, when I meet someone who's amazing, I had breakfast this morning with the head coach of Harvard University basketball team. And okay, so I don't have a need to hire a basketball coach, but the guy was amazing. I'm just thinking, like, I want to hang out with this guy. Like, I want to find some Project to work on together. To me, it's not finding someone who will report to you that you can boss them around. It's finding someone that is electrifying and exciting, and then you can learn from and have skills that you don't have. And then just saying, I'm going to find a way to work with this person. So I would just say my advice to entrepreneurs, just aim really, really high. Find people that inspire you and then find a way to come up with a shared vision where they can help you build something that you couldn't do on yo…

AI assessment note: “tech founder lacks humility, and they're arrogant, and they only hire people that would be subservient”

Q Yeah, absolutely. I mean, I guess on the flip side, the super interesting part you said there about kind of some of the board members you've had, what have been your big learnings on kind of really driving effectiveness on the board management level?

A Well, certainly you want a high functioning board where the board itself gets along with each other. I've had situations where a board member is really talented on their own, but they're annoying in a board meeting. So I've had to coach board members about how I want them to operate in my board meeting. So for example, I'm not going to name names, but I have one board member who is absolutely brilliant, but would come up with an idea during the board meeting and really want to make sure that his idea was heard. So he would say the idea over and over and over again. So he'd repeat it once, then again, five minutes later, again, an hour later, and It was irritating and distracting to the meeting that he kept pushing his agenda so much, and so at one board meeting, I did something which is a little bit harsh, which is when he had an idea that I could tell this is one of these things he's going to push, I wrote it up on the whiteboard, and like two or three word summary, and then five minutes later, when he pitched it again, I said, yeah, yeah, I already wrote that one down, basically saying, dude, there's no reason. We don't need to waste time on this. I got it, and there's little things that you try to coach your team, and although you want to learn from your boards, You need to coach your board a little bit too, and part of that is about having clarity about what things your boa…

AI assessment note: “You need to coach your board a little bit too”

Q We spoke about kind of some of the best there in Bill Clinton for Charisma, and you've angel invested in many companies, you've worked with many different founders. I'm intrigued. Where do you see many tech founders going wrong, maybe, in their hiring approach today?

A Well, I think either the tech founder lacks humility, and they're arrogant, and they only hire people that would be subservient to them, so they don't hire people that are daring enough, and they're going to challenge them and push them. That's how one Failure, I see. And again, this is a little bit cliche, but to be the best at recruiting, you literally want to hire people that are smarter than you and stronger than you. And a lot of entrepreneurs lack the confidence for hiring people stronger than you. And it's something that I've never really worried about. Like, when I meet someone who's amazing, I had breakfast this morning with the head coach of Harvard University basketball team. And okay, so I don't have a need to hire a basketball coach, but the guy was amazing. I'm just thinking, like, I want to hang out with this guy. Like, I want to find some Project to work on together. To me, it's not finding someone who will report to you that you can boss them around. It's finding someone that is electrifying and exciting, and then you can learn from and have skills that you don't have. And then just saying, I'm going to find a way to work with this person. So I would just say my advice to entrepreneurs, just aim really, really high. Find people that inspire you and then find a way to come up with a shared vision where they can help you build something that you couldn't do on yo…

AI assessment note: “tech founder lacks humility, and they're arrogant, and they only hire people that would be subservient”

Q Can I ask, when you as the founder maybe disagree with the direction that a board is suggesting, How do you eloquently and graciously reject it, so to speak, and pursue your own direction? Is there a right way to do it?

A Yeah, I mean, there's a right way to do it in person, and then also as a follow-up, and a lot of times in person, what I'll say is, that just doesn't sound right to me, and I'll try to explain why it doesn't sound right, so I'll argue back to them, and I, I try not to be argumentative, but I want to be honest and direct, and so if a board is trying to get me to do something which I think is defocused, I'll say, I think that's a really great idea, but I don't think we can think about that until we get X, Y, and Z done. So just try to keep focus on what are the top three priorities. It's something that good board members have helped me with because as someone who wants me known as an idea generator, I can suffer from adding too many things onto the agenda, but I think in that people have coached me with that, I've tried to use those skills back with my board to say, we can't leave a board meeting with 50 action items. You know, we have to, to really effective, you have Think about what are the two or three really, really most important things, and then make sure you crush those between board meetings. So in my minutes back to the board that I write out by hand, sort of pen on paper during the board meeting, then I transcribe them into a Google document and email them out usually the same day. I don't write down everything the board says, and maybe this is bad. I write down the th…

AI assessment note: “I'll say, I think that's a really great idea, but I don't think”

Q Can I ask, have you found it a interesting slash tough transition moving from CTO to CEO with Lola?

A Yeah, I've gone back and forth a few times. So Lola's my fifth company. I think at the core, I mean, I'm an engineer by training. My best skill, if I had to put me functionally on an org chart, I would say would be product manager. Which is sort of the role I played at Kayak as a CTO. We didn't really have any product managers. We had some designers. If you look at where I spend my time on a day-to-day basis, it's, you know, trying to get the team excited, leading the team, hiring and all that. But then once you get the team excited, like, what are they excited about? What are they working on? And to me, it's design of the product and evolution of the product. And evolution of the product happens from customer support. What's working? What's not working? It happens from sales. What's work? What's not working? What are the prospects like? What don't they like? And that's the fun part of the job for me. And some of the other parts of being a CEO, frankly, I'm not great at and I don't love doing. So luckily I have some amazing people around me who are really good at the stuff that I'm terrible at.

AI assessment note: “some of the other parts of being a CEO, frankly, I'm not great at”

Q Kind of speaking about the ability to really make those strong connections, do you think this is a skill that you can learn over time, or do you think it's something that's natural, God-given, so to speak?

A No, I definitely, I mean, there are some people who are more gifted than others. I'm just trying to think of, like, the most charismatic people I've ever met. I met Bill Clinton once. Actually, I ran into him at a bar in Haiti, which is pretty funny, and the guy is just ridiculous charisma, where I think anyone around him wants to connect with him and work with him and all that, but It's also trainable, for sure. I mean, you think about the extreme case where a child is autistic and can't make eye contact. There's pretty good academic research and progress about how you can take a kid who's even autistic and teach them some techniques about how to connect with people a little bit, and so if you can teach a kid suffering from autism about that, just think about what you can do to teach people who don't have a disorder like that, but how they can better connect with people, and there are a lot of techniques, and it's everything from, I remember You know, many years ago, I hate the title of this book, but I love the book when I read it, which is how to win friends and influence people.

AI assessment note: “there are some people who are more gifted than others... but It's also trainable”

Q No, absolutely. I mean, you mentioned the idea there of inspiring other people to get excited about the project. I spoke to other mutual friends who said that Paul's the best founder I've ever seen in the world of hiring. So starting with that, how do you approach the realm of hiring from a macro perspective? Let's start with that.

A Yeah, it's something I'm just always, always, always focused on, and I don't know what caused me to focus on it so much, but literally on the way to this interview, so I'm set up in my home office right now, and I had a breakfast meeting this morning, and so I just sat in the back of an Uber and On the way from my breakfast meeting back home so I can make, take this interview. And during my Uber ride, I'm going back and forth on my phone, and someone reached out to me, believe it or not, on TaskRabbit, and there's a woman who did a task to me like a year ago, and I vaguely remember, I never met her in person, but being really, really impressed with her organizational and writing and all that, and she reached out to me on TaskRabbit this morning, commenting on something she had read about me, and I immediately thought about I forgot about this woman. Yeah, she was an amazing writer. It's just something I should, else I should hire her for. And I just pinged her back and said, you know, what are you working on these days? And it's just, I'm always trying to find, if I find someone who's amazing, that's talent, I like matching them. And even if I can't match them to something like at my day job, Lola, can I introduce them to a friend of mine who maybe is looking for a writer or whatever? I just love the matchmaking process.

AI assessment note: “It's something I'm just always, always, always focused on”

Q No, absolutely. I mean, you mentioned the idea there of inspiring other people to get excited about the project. I spoke to other mutual friends who said that Paul's the best founder I've ever seen in the world of hiring. So starting with that, how do you approach the realm of hiring from a macro perspective? Let's start with that.

A Yeah, it's something I'm just always, always, always focused on, and I don't know what caused me to focus on it so much, but literally on the way to this interview, so I'm set up in my home office right now, and I had a breakfast meeting this morning, and so I just sat in the back of an Uber and On the way from my breakfast meeting back home so I can make, take this interview. And during my Uber ride, I'm going back and forth on my phone, and someone reached out to me, believe it or not, on TaskRabbit, and there's a woman who did a task to me like a year ago, and I vaguely remember, I never met her in person, but being really, really impressed with her organizational and writing and all that, and she reached out to me on TaskRabbit this morning, commenting on something she had read about me, and I immediately thought about I forgot about this woman. Yeah, she was an amazing writer. It's just something I should, else I should hire her for. And I just pinged her back and said, you know, what are you working on these days? And it's just, I'm always trying to find, if I find someone who's amazing, that's talent, I like matching them. And even if I can't match them to something like at my day job, Lola, can I introduce them to a friend of mine who maybe is looking for a writer or whatever? I just love the matchmaking process.

AI assessment note: “it's something I'm just always, always, always focused on... I just love the matchmaking process.”

Q Can I ask, have you found it a interesting slash tough transition moving from CTO to CEO with Lola?

A Yeah, I've gone back and forth a few times. So Lola's my fifth company. I think at the core, I mean, I'm an engineer by training. My best skill, if I had to put me functionally on an org chart, I would say would be product manager. Which is sort of the role I played at Kayak as a CTO. We didn't really have any product managers. We had some designers. If you look at where I spend my time on a day-to-day basis, it's, you know, trying to get the team excited, leading the team, hiring and all that. But then once you get the team excited, like, what are they excited about? What are they working on? And to me, it's design of the product and evolution of the product. And evolution of the product happens from customer support. What's working? What's not working? It happens from sales. What's work? What's not working? What are the prospects like? What don't they like? And that's the fun part of the job for me. And some of the other parts of being a CEO, frankly, I'm not great at and I don't love doing. So luckily I have some amazing people around me who are really good at the stuff that I'm terrible at.

AI assessment note: “some of the other parts of being a CEO, frankly, I'm not great at”

Q But I'd love to finish then on the next five years for you and for Lola, what's the exciting roadmap ahead?

A I mean, this is going to sound funny, and I don't know if my investors would like this answer, but I want to create the place that's the most exciting place of people's career. And I want my team to become more successful this year than they were last year. I want people to grow in their skills. I want them to love their job, and I want them to help me bring more people, exciting people into the company. And when I, as an investor, when I think about investing in a company, I'll go visit them, I'll visit their office, and you can feel the energy, whether it's there or not. You know the team sort of has the mojo. And creating this electrifying environment where people are very brilliant, but passionate. They love working together. That's the magic. And that's step one of all the other stuff you have to do as an entrepreneur. So when I think about what I want to do today or this year or next five years, it's create those electrifying teams.

AI assessment note: “when I think about what I want to do... next five years, it's create those electrifying teams”

Q Can I ask, has that process changed for you over time when you look back to your very early days starting out compared to maybe now? How has that process changed?

A I mean, early in my career, it was obviously programming related. I would try to find things that both were Allowed people to do something more efficiently, but also was differentiated from competitors, so I was really into doing unique solutions or novel solutions. Yeah, that started early on in my programming career, and I guess I'm probably more of a creative person than a process person. Like, I'm terrible at process, which is bad, but on the flip side, I've been pretty lucky to, um, be able to participate in teams where this is like a lot, a lot of idea generation, and it's the most fun part of entrepreneurship for me is tackling a problem and saying, can we come up with a new way to solve this?

AI assessment note: “I'm probably more of a creative person than a process person. Like, I'm terrible”

Q Can I ask, has that process changed for you over time when you look back to your very early days starting out compared to maybe now? How has that process changed?

A I mean, early in my career, it was obviously programming related. I would try to find things that both were Allowed people to do something more efficiently, but also was differentiated from competitors, so I was really into doing unique solutions or novel solutions. Yeah, that started early on in my programming career, and I guess I'm probably more of a creative person than a process person. Like, I'm terrible at process, which is bad, but on the flip side, I've been pretty lucky to, um, be able to participate in teams where this is like a lot, a lot of idea generation, and it's the most fun part of entrepreneurship for me is tackling a problem and saying, can we come up with a new way to solve this?

AI assessment note: “I guess I'm probably more of a creative person than a process person.”