The Exchanges

Q It is very, very kind of you. I'm still scratching my head wondering how it actually worked, but I'm thrilled that it did. I do have to ask, and I love context, so like, what was your entry point into the world of tech? We look at this glittering career that you've had. What was the entry point?

A I mean, honestly, it was being on the sidelines in Silicon Valley. You know, I'd come out after business school. It was right around the year, 2000. So.com one dot O and all of my friends were getting written up in the New York times out of Harvard and they were starting these startups. You know, I grew up in Western Pennsylvania. I didn't know, you know, my parent, my dad worked at a steel company. My mom was a teacher. Like I just didn't have the exposure to it. And so I go out West and I was like, well, I'm going to at least just Watch the tech companies. So I went to an investment bank where we were taking growth companies public. And it was from that vantage point that it built my pattern recognition because we had separated research and banking. And so I was going out and meeting with company after company after company and figuring out like, which of these is going to go IPO one day? Like, how do I determine this? And a lot of it was, you know, just starting to understand business models, leadership Profiles, like which company was going to make it. And that was really the entry point was just this high, you know, sample really. I mean, you know, sometimes you go to a company and you see that single company here. I had looked at hundreds of companies. I don't know if it had gotten into the thousands, but certainly many, many companies would meet with CEOs every single da…

AI assessment note: “I went to an investment bank where we were taking growth companies public.”

Q I, you teed me up so nicely there. What are the decisions that only a CEO can make?

A I'll give examples. I mean, right now, you know, we're looking at our brand. And if you think about, so we've got a lot of different software brands underneath Corral. So we've got parallels. So like running windows on a Mac or our remote application start, we've got all these sub brands. I've got Winzip. I've got, and so this idea of what do we call ourselves? What is the narrative of Our organization. I don't think anybody else in the organization can do that work. I have to craft the mission of where we are, the purpose of why we are here, how we call ourselves. Now I can have help on like writing elements of it, but it's really my decision to guide that next three, four, five, six, 10 years of this company. And how do I go do that? It's crafting where the narrative comes. The other key things that only a CEO can do is put the CEO team in place too. Like When I left OpenTable and I was looking at president jobs, I was like, well, it's just a two variable equation. I have to like, like the people and the company. Whereas here, I just had to like the company because I've got to put the team in place to go make that company successful. And so I think it's really about getting the right people in the organization to lead and drive. And the third thing, so like I would say brand mission, you know, kind of purpose of the company, the people of the company. And then really the thir…

AI assessment note: “I would say brand mission, you know, kind of purpose of the company, the people”

Q element of, like, only CEOs can make that decision being board engagement, board interaction. You have this incredible purview, obviously, Running the board that you do today, but then also sitting on Kimberly Clark, Affirm, among others you have done before. So the question that I have is, how has sitting on other boards, as you have done, impacted how you think about great leadership of your own board today?

A Everything. I will say, so the very first board meeting I ever attended, I came back and my next presentation to my own board changed radically. I realized these people show up You know, five times a year, or maybe a lot more often in some VC board that they just simply don't have the context. In fact, somebody gave me this advice early on. They said, don't underestimate how little your board retains. And I was like, oh my God. Right. So like you realize like, you know, they're coming in, they're having to reshift their own context. They're having to understand the problem that's in front of them. I was way, not too in the weeds, but I just, I presumed too much context that the board had. And what I really needed was the board who give, I like to say, the provocation. It is, you're there to stimulate thought and idea around something by virtue of my diverse set of experiences. I'm going to stimulate that with the team around me and say, Oh, have you thought about this? Have you thought about that? So I both have radically changed how I present to my board and how I communicate. And then I understand sort of the limitations between what it means to be on a board and where, what it means to be an operator. And you don't want those lines to cross because then it gets not as effective.

AI assessment note: “I both have radically changed how I present to my board and how I communicate.”

Q when I was going through, you know, your journey, which is too Special that I couldn't not dive on, honestly. One was like Walt Disney. Like one of the most foundational companies definitely in the last, I mean, 50 years. So I have to ask, when you look back at your time there, how did your close to four years there impact how you think about leadership and management today?

A You know, Disney really was foundational, as you say. I mean, first of all, I got up close with Bob Iger, and anybody who has the chance or opportunity to learn from him, he's written a great book. I think it's called What a Ride. But he had this Incredible ability to one day, like, conduct high-end diplomacy for Disneyland Shanghai, and then the next day, debate the finer points of The Sims with me, and I was like, how is this possible? Like, how can he go from here to there? And so this ability to kind of deep dive on a topic and come back up, and just the breadth of awareness, context-setting skill set that that takes. I also, you know, carry with me, like, just some funny things. Like, in the Zoom world, like, Disney paid attention to your, like, Executive hygiene. And so like, did you start a meeting on time? Did you end a meeting on time? How did you conduct the meeting? And so there was a little bit of pomp in there, but I think there was the craft of leadership was considered. And so I think that's where I got a lot of the early lessons about how to think through. And I would say, you know, my time at Disney was during a really transitional and transformational point in its history. You know, it had been this tech leader, honestly, when you think about the early days of animation and And then modern media had sort of lost its way, and Netflix was coming around, and they…

AI assessment note: “I think that's where I got a lot of the early lessons”

Q It is very, very kind of you. I'm still scratching my head wondering how it actually worked, but I'm thrilled that it did. I do have to ask, and I love context, so like, what was your entry point into the world of tech? We look at this glittering career that you've had. What was the entry point?

A I mean, honestly, it was being on the sidelines in Silicon Valley. You know, I'd come out after business school. It was right around the year, 2000. So.com one dot O and all of my friends were getting written up in the New York times out of Harvard and they were starting these startups. You know, I grew up in Western Pennsylvania. I didn't know, you know, my parent, my dad worked at a steel company. My mom was a teacher. Like I just didn't have the exposure to it. And so I go out West and I was like, well, I'm going to at least just Watch the tech companies. So I went to an investment bank where we were taking growth companies public. And it was from that vantage point that it built my pattern recognition because we had separated research and banking. And so I was going out and meeting with company after company after company and figuring out like, which of these is going to go IPO one day? Like, how do I determine this? And a lot of it was, you know, just starting to understand business models, leadership Profiles, like which company was going to make it. And that was really the entry point was just this high, you know, sample really. I mean, you know, sometimes you go to a company and you see that single company here. I had looked at hundreds of companies. I don't know if it had gotten into the thousands, but certainly many, many companies would meet with CEOs every single da…

AI assessment note: “I went to an investment bank where we were taking growth companies public.”

Q think about the next scale, you as the leader have to scale with every evolution of the company. How do you think about that? How do you advise also founders? I get so many founders say, I don't know if I can do it. Like, I've never done it before. How do you think about yourself scaling and what you advise founders and In terms of scaling with the company.

A Yeah, it's a really interesting problem, and I, I've spent a lot of time thinking about it, because I've been at such wildly divergent-scaled companies, and what I've observed is this kind of exponential path of breakage. Companies tend to break at 50 people, because it's like, you used to be able to just get everybody in the room, and like shout at them, or put them in a Slack channel, and tell them what to do, and you knew every single person, and you could direct everything that they did. And then the next break point is about a 150 people, but curiously also Dunbar's number, so You know, you can only hold that number of relationships in your head. And that's, I would say the biggest break point that I see most companies hit. It means like, and this was exactly what happened to me at Playdom. Like we hit one 50 and like pretty, you know, all the software that's helped companies grow, but like we didn't have an HRIS. It was like in somebody's like spreadsheet on Excel or we had never written a policy about anything. And so all of a sudden you have these people and you're like, oh my God, how do you communicate to them? How do you get them aware of So one 50 is a breakpoint. I see 502,010 thousand. So it's just like exponential curve because essentially what happens is when you get more people, the decision trees kind of fan out and how you used to make decisions needs to chan…

AI assessment note: “what happens is when you get more people, the decision trees kind of fan out”

Q when I was going through, you know, your journey, which is too Special that I couldn't not dive on, honestly. One was like Walt Disney. Like one of the most foundational companies definitely in the last, I mean, 50 years. So I have to ask, when you look back at your time there, how did your close to four years there impact how you think about leadership and management today?

A You know, Disney really was foundational, as you say. I mean, first of all, I got up close with Bob Iger, and anybody who has the chance or opportunity to learn from him, he's written a great book. I think it's called What a Ride. But he had this Incredible ability to one day, like, conduct high-end diplomacy for Disneyland Shanghai, and then the next day, debate the finer points of The Sims with me, and I was like, how is this possible? Like, how can he go from here to there? And so this ability to kind of deep dive on a topic and come back up, and just the breadth of awareness, context-setting skill set that that takes. I also, you know, carry with me, like, just some funny things. Like, in the Zoom world, like, Disney paid attention to your, like, Executive hygiene. And so like, did you start a meeting on time? Did you end a meeting on time? How did you conduct the meeting? And so there was a little bit of pomp in there, but I think there was the craft of leadership was considered. And so I think that's where I got a lot of the early lessons about how to think through. And I would say, you know, my time at Disney was during a really transitional and transformational point in its history. You know, it had been this tech leader, honestly, when you think about the early days of animation and And then modern media had sort of lost its way, and Netflix was coming around, and they…

AI assessment note: “that's where I got a lot of the early lessons about how to think through”

Q Okay. Given the limits of their knowledge retention, how does that change how you engage with them and extract the most value from them? Is it coming with very strategic, direct questions? How does it change?

A Yeah, I think the key thing is, so a board's going to ask, like, say they ask 10 things, but they don't have data on all those things, and so my job is to go back to the board and say, look, I've looked at each of these questions you've asked. I prioritize them relative to their impact on the business, and these four things you guys were asking about, honestly, it's like, these are one percent movers, so they're not really going to change, you know, so it's really about assessing magnitude of how big could that idea be, Inside my organization, there's no way the board's going to know or be able to size those opportunities. So it's my job to go, Hey, we've sized these. We've now prioritized them. And these two things we talked about, I think are critical and foundational for the center and future of our company. These eight things, honestly, they're going to be a distraction. And usually the board's like, great. I mean, every now and then you get a board member who has a pet peeve, About something. And that's an interesting one to handle, and maybe I've been that to other people. I hope I haven't, but I, I like to hope that I'm just trying to understand better, but that, that can happen occasionally where that, that line does get blurred.

AI assessment note: “my job is to go back to the board and say, look, I've looked”

Q Okay, so what's the favorite book and why?

A I love so many books. The one that I read that I was really just eye-opened was Cast by Isabel Wilkerson. And it reflects essentially, you know, race relations in America, but also India and other parts of the world. They go through Nazi Germany. And to me, I look at Cast as just a great limiter of humanity. You know, I think it's like, we are not taking advantage of every human being's right to contribute. And I just open my eyes on so much There's structural, sclerotic, frankly, ways that we do things, and I think about it in the microcosm of my own company, and it's like, how are we limiting our ability to, to kind of lean in? So for me, it was just this really eye-opening and groundbreaking from that dimension, and I think everybody should read it.

AI assessment note: “The one that I read that I was really just eye-opened was Cast by Isabel Wilkerson.”

Q Gosh, you should be an inspirational speaker. I feel like so pumped after hearing that we're going to be better on the next side. This is fantastic. Can I ask, what does being stuck look like? For people to think like, am I stuck? Is it like, lack of passion and being dampened? What is stuck?

A You know, for me anyway, it was showing up, I was like, kind of afraid to go in the office, but I was fearful. Like, I didn't know the environment that I was in. It was uncertain. I didn't know if I was going to like, lose my job the next day. I didn't know if I was I think I lost the truth of myself. Like I didn't feel like myself. I didn't feel like the best version of myself. I didn't feel like coming in every day. Like, yeah, we're going to crush it today. I felt smaller and I felt I wasn't showing up with all of my lights lit almost. Like, I just was like, ah, I'm going to just come in and do my best and hope to not piss somebody off. And inevitably, because of that, you're operating at like 60% capacity, right? Like essentially what was happening when I prefrontal Frontal cortex had shut down, and I was, like, in the lizard brain, my amygdala back here, and we all know you lose, like, 40, 50 IQ points when you do that, so I was literally dumber and a worse worker, right, like, when you show up to work that way, and I think that's why, like, I'm so obsessed about, you know, creating very inclusive environments, because you're just 10 times the worker if you can show up and do the job versus worrying about, like, oh my god, is my boss gonna yell at me today? Oh my god, like, I think Google has studied this, where the number one Factor in high performing teams is psychologic…

AI assessment note: “for me anyway, it was showing up, I was like, kind of afraid”

Q ask, you mentioned being a thousand miles an hour, kind of, all the time. I love that, and I feel it plenty when I interview you. It's why it's such a great interview. Do you ever sit back and appreciate what you've done, what you've achieved, if it was a great quarter? Do you take the time to be like, actually, we did well. I'm going to enjoy this moment.

A I've actually had to learn to do that, because naturally, you know, my time equals zero is always, like, Three months before it hits everybody else, so I have to recognize, like, they're just seeing this for the first time. You've already been processing it, so now, like, you know, like, we just did our quarterly town hall this morning, and we had great results, like, really, truly fantastic, and now I'm, like, thinking, I'm, like, did I really stop, and I feel like I did, but I think it's important to acknowledge and to celebrate the wins along the way. I have become an AA yoga student, and I think the act of, like, forcing myself to slow down, to kind of, like, Take monkey mind. Like, when you're standing on your head, you really do have to just focus about what you're doing right in that moment, and I found it so therapeutic, because people who are like, you know, like, I'm constantly, like, I'm moving a lot, and they just, like, literally invert, and it's a sign and signal to my body, like, slow down, take a minute, and it's in those moments that I think you have this element of refresh and creativity kind of well That you refill because you got to go at it the next day. I mean, operating is a full body contact sport. I like to say, and so you're in it and on it all the time. And so you better take care of yourself in order to be able to give back to that organization. And …

AI assessment note: “I've actually had to learn to do that”

Q the importance of market timing. A mentor told me the other day, Harry, where you're going to get undone is you have to understand the corners you can cut versus the corners you can't cut. It's a good point, and I've thought about it pretty constantly through the last few days. How do you think about that question, especially in leadership and how you do things and new initiatives today?

A I am a corner cutter by nature, I'd say. In fact, I've surrounded myself with, like, iDotters and T-Crossers. So that they keep me safe sometimes. I mean, I think a lot of leadership too is just self-awareness. Like what is my temperament? What do I like to do? And I am thousand miles an hour and I am, you know, I'm hopping, like I'll dive into product and then I'll go into like, you know, our infrastructure technology and then I'll go into marketing and then I'll be over here in finance. And so I'm everywhere. And by definition of that, you know, I don't know if I'm fully jack of all trades, master of none, but I'm hopefully a master of a few of them. But I know that I, I want people around me who are going to be I'm obsessed about the detail. And so I think it's about finding that complimentary skill set for yourself such that you can decide, okay, like these are details that maybe I can't cause. And they're going to come up to you and say, hey, time out. We got to really focus on this because if you don't fix this, this is going to be a problem. And I love people who do that because, you know, I can kind of get moving and somebody who pushes me and says like, you got to pay attention here and it's going to be real. And I think, you know, one of my favorite reference points Questions to ask is who would make a great number two for this person? And what that reference question…

AI assessment note: “I am a corner cutter by nature, I'd say. In fact, I've surrounded myself”

Q Gosh, you should be an inspirational speaker. I feel like so pumped after hearing that we're going to be better on the next side. This is fantastic. Can I ask, what does being stuck look like? For people to think like, am I stuck? Is it like, lack of passion and being dampened? What is stuck?

A You know, for me anyway, it was showing up, I was like, kind of afraid to go in the office, but I was fearful. Like, I didn't know the environment that I was in. It was uncertain. I didn't know if I was going to like, lose my job the next day. I didn't know if I was I think I lost the truth of myself. Like I didn't feel like myself. I didn't feel like the best version of myself. I didn't feel like coming in every day. Like, yeah, we're going to crush it today. I felt smaller and I felt I wasn't showing up with all of my lights lit almost. Like, I just was like, ah, I'm going to just come in and do my best and hope to not piss somebody off. And inevitably, because of that, you're operating at like 60% capacity, right? Like essentially what was happening when I prefrontal Frontal cortex had shut down, and I was, like, in the lizard brain, my amygdala back here, and we all know you lose, like, 40, 50 IQ points when you do that, so I was literally dumber and a worse worker, right, like, when you show up to work that way, and I think that's why, like, I'm so obsessed about, you know, creating very inclusive environments, because you're just 10 times the worker if you can show up and do the job versus worrying about, like, oh my god, is my boss gonna yell at me today? Oh my god, like, I think Google has studied this, where the number one Factor in high performing teams is psychologic…

AI assessment note: “for me anyway, it was showing up, I was like, kind of afraid”

Q think about the next scale, you as the leader have to scale with every evolution of the company. How do you think about that? How do you advise also founders? I get so many founders say, I don't know if I can do it. Like, I've never done it before. How do you think about yourself scaling and what you advise founders and In terms of scaling with the company.

A Yeah, it's a really interesting problem, and I, I've spent a lot of time thinking about it, because I've been at such wildly divergent-scaled companies, and what I've observed is this kind of exponential path of breakage. Companies tend to break at 50 people, because it's like, you used to be able to just get everybody in the room, and like shout at them, or put them in a Slack channel, and tell them what to do, and you knew every single person, and you could direct everything that they did. And then the next break point is about a 150 people, but curiously also Dunbar's number, so You know, you can only hold that number of relationships in your head. And that's, I would say the biggest break point that I see most companies hit. It means like, and this was exactly what happened to me at Playdom. Like we hit one 50 and like pretty, you know, all the software that's helped companies grow, but like we didn't have an HRIS. It was like in somebody's like spreadsheet on Excel or we had never written a policy about anything. And so all of a sudden you have these people and you're like, oh my God, how do you communicate to them? How do you get them aware of So one 50 is a breakpoint. I see 502,010 thousand. So it's just like exponential curve because essentially what happens is when you get more people, the decision trees kind of fan out and how you used to make decisions needs to chan…

AI assessment note: “what I've observed is this kind of exponential path of breakage.”

Q you handle, like, what I think is the most challenging element, which is when you're not in the room and the decision's being made, how do you ensure that they're as ambitious as they should be, and not just go for the safe option because they don't want to get fired if it doesn't go right? How do you inspire people to be their best and not worry about downside?

A Yeah, and I will say I, I hit that head on when I was at OpenTable, because if you look at the history of OpenTable, it just worked, and it's not fair to just say that, but it is the power of a network effect Two-sided marketplace business. Essentially we had supply, we had to pan. It was a scaled two-sided marketplace. And the beauty of those is they do just sort of work. However, it works until it doesn't meaning like if you don't evolve the product, if you don't step into the future, eventually you will get overtaken. And so when I got into the company, we were at a point at which the software that we had inside the restaurant was an old Microsoft on-prem distributed database, like not in the cloud. And we needed to move into the cloud and we needed to move fast and we needed to take advantage of all that that would have to offer. But you have now this company where everything just sort of worked. And so there's this like learned helplessness of like, well, if I do something, it works. If I don't do something, it works. So I'm just maybe not going to do as much, or I'm afraid to do as much. And so I did kind of hit my head against the wall, I would say for like the first year. Cause I was like, why can't they just, why are they ambitious? Why are they trying? Why aren't they going? I had hired a chief people officer and he said, well, you know, he's like, can I give you some…

AI assessment note: “I hit that head on when I was at OpenTable”

Q How do you handle that? Because every founder, I'm sure, has a VC mostly with a pet peeve, and they just keep on drilling. What is the right way to approach that?

A In my view, like, if you feel like it is a, it is just not the right path, it's just to bring them in. And say, like, all right, let's go deep. Let's spend an hour on this. You and me, let's just go deep, and let's understand. We might also just be talking past each other, because on the one hand, I'm a big believer in, there's usually a kernel of truth, even if I disagree with you, like, I'm staunch disagreement with you on 99%. There's, like, that one percent that I have to say, how can that be true? So I just try to flip it and say, like, even if I don't want to do it, I don't think it, like, how can it be true? And then I usually, I Do a curiosity session where we just like, let's go deep. Let's understand. And maybe I'm missing something. I think being defensive and saying like, I know it all day, how dare you? Like, that's obviously not going to be great. And it's certainly not a place of curiosity either. Like, I think you want to lean in and be like, well, let me understand this better. Like, why are you obsessed about it? Give me your data. Maybe they have data you've not seen around the market externality. That's really important back to the prior part of the conversation. So I think all of that's really important. To lean in with curiosity, and then to not let it repeat, though. I think it's kind of like a stuck state, back to that other part, is if you just let them…

AI assessment note: “just to bring them in. And say, like, all right, let's go deep.”

Q the importance of market timing. A mentor told me the other day, Harry, where you're going to get undone is you have to understand the corners you can cut versus the corners you can't cut. It's a good point, and I've thought about it pretty constantly through the last few days. How do you think about that question, especially in leadership and how you do things and new initiatives today?

A I am a corner cutter by nature, I'd say. In fact, I've surrounded myself with, like, iDotters and T-Crossers. So that they keep me safe sometimes. I mean, I think a lot of leadership too is just self-awareness. Like what is my temperament? What do I like to do? And I am thousand miles an hour and I am, you know, I'm hopping, like I'll dive into product and then I'll go into like, you know, our infrastructure technology and then I'll go into marketing and then I'll be over here in finance. And so I'm everywhere. And by definition of that, you know, I don't know if I'm fully jack of all trades, master of none, but I'm hopefully a master of a few of them. But I know that I, I want people around me who are going to be I'm obsessed about the detail. And so I think it's about finding that complimentary skill set for yourself such that you can decide, okay, like these are details that maybe I can't cause. And they're going to come up to you and say, hey, time out. We got to really focus on this because if you don't fix this, this is going to be a problem. And I love people who do that because, you know, I can kind of get moving and somebody who pushes me and says like, you got to pay attention here and it's going to be real. And I think, you know, one of my favorite reference points Questions to ask is who would make a great number two for this person? And what that reference question…

AI assessment note: “I am a corner cutter by nature, I'd say. In fact, I've surrounded myself”

Q Can I ask a weird one? My hip is not too personal, but it's like, how do you rebuild? As you said, it is a full body contact sport. It's brutal sometimes, and you just get beaten, and you're just like, I'm done. How do you rebuild when that happens?

A It's a good question. I played sports in high school and college, and I think the act of losing and getting back up, like falling down, and like just that, that simple process of like falling down, like I'm down, oh, no, that hurt, that I'm down, I'm gonna just, but I, but you've gotten up so many times. You just know, Like, it's just part of the process. Like you build it into the muscle memory almost where, you know, just like, this is what it feels like. Okay. I'm down. All right, here we go. Let's go get, the only time that I really didn't work for me was I was in a situation where I felt like I had never not been able to make it work in my life. Like I've always been malleable enough that, like I said, like I showed up on wall street, like you want me to be like a swearing dude? Like that's who I am. Like I'm showing up. And so I've always just modulated my behavior for the environment that I was in until I got into a situation where I couldn't. And I will tell you that I got stuck for a period of time because I'd always been able to figure it out. And so what I realized was that I had to rewrite my own narrative. And I think for me, it was, you can always make it work dot, dot, dot with good people. Like, but if there's like really bad people involved or what, you know, like you're not necessarily going to make it work. And so for me, basically prevented myself from the f…

AI assessment note: “what I realized was that I had to rewrite my own narrative.”

Q Can I ask a weird one? My hip is not too personal, but it's like, how do you rebuild? As you said, it is a full body contact sport. It's brutal sometimes, and you just get beaten, and you're just like, I'm done. How do you rebuild when that happens?

A It's a good question. I played sports in high school and college, and I think the act of losing and getting back up, like falling down, and like just that, that simple process of like falling down, like I'm down, oh, no, that hurt, that I'm down, I'm gonna just, but I, but you've gotten up so many times. You just know, Like, it's just part of the process. Like you build it into the muscle memory almost where, you know, just like, this is what it feels like. Okay. I'm down. All right, here we go. Let's go get, the only time that I really didn't work for me was I was in a situation where I felt like I had never not been able to make it work in my life. Like I've always been malleable enough that, like I said, like I showed up on wall street, like you want me to be like a swearing dude? Like that's who I am. Like I'm showing up. And so I've always just modulated my behavior for the environment that I was in until I got into a situation where I couldn't. And I will tell you that I got stuck for a period of time because I'd always been able to figure it out. And so what I realized was that I had to rewrite my own narrative. And I think for me, it was, you can always make it work dot, dot, dot with good people. Like, but if there's like really bad people involved or what, you know, like you're not necessarily going to make it work. And so for me, basically prevented myself from the f…

AI assessment note: “You just know, Like, it's just part of the process. Like you build it into the muscle memory”

Q you handle, like, what I think is the most challenging element, which is when you're not in the room and the decision's being made, how do you ensure that they're as ambitious as they should be, and not just go for the safe option because they don't want to get fired if it doesn't go right? How do you inspire people to be their best and not worry about downside?

A Yeah, and I will say I, I hit that head on when I was at OpenTable, because if you look at the history of OpenTable, it just worked, and it's not fair to just say that, but it is the power of a network effect Two-sided marketplace business. Essentially we had supply, we had to pan. It was a scaled two-sided marketplace. And the beauty of those is they do just sort of work. However, it works until it doesn't meaning like if you don't evolve the product, if you don't step into the future, eventually you will get overtaken. And so when I got into the company, we were at a point at which the software that we had inside the restaurant was an old Microsoft on-prem distributed database, like not in the cloud. And we needed to move into the cloud and we needed to move fast and we needed to take advantage of all that that would have to offer. But you have now this company where everything just sort of worked. And so there's this like learned helplessness of like, well, if I do something, it works. If I don't do something, it works. So I'm just maybe not going to do as much, or I'm afraid to do as much. And so I did kind of hit my head against the wall, I would say for like the first year. Cause I was like, why can't they just, why are they ambitious? Why are they trying? Why aren't they going? I had hired a chief people officer and he said, well, you know, he's like, can I give you some…

AI assessment note: “five of your company values are essentially move faster. It was like progress over perfection.”

Q You said about the CEO team there. I have to dig in on that. The hardest one for me, and I'm asking the easiest of questions today, my word, but it's like, how do you know when a stretch exec or a stretch VP is a stretch too far, and how long do you give them?

A It is the really hard thing. Question, because I think, you know, I'm a big believer in driving the personality, but I also think if I wasn't a CEO, I would either be hopefully a standup comedian on my good days, but, uh, I would be a psychologist. Like I need to understand. What are you really good at doing? You know, what do you love to do? What does the company need you to do? And oftentimes where this all gets out of balance is I'm asking somebody to do something they either aren't very good at, and we're all spiky in different dimensions. So understanding where is this person really awesome? Where are they? Maybe not. Or they like, they hate doing that thing. Like they're just not into it. And their, their attitude is like, I don't want to do this thing. In fact, we promoted a guy today. And one of the questions I asked the manager, I said, how ambitious is he? And he was like, oh, he's very ambitious. I was like, great. I was like, because his desire to do these things is going to be higher. He's going to want to lean in. He's going to want to try these things. And so I think you have to kind of ask those questions and say, like, are all those pieces in alignment? Like, cause it could be that like what you're, and this is, by the way, this evidences a lot in these scale problems. So the person who was amazing with From zero to 50 often can't take the next leap. Some peopl…

AI assessment note: “oftentimes where this all gets out of balance is I'm asking somebody to do”

Q Final one for you. If we sat down in five years time, and everything has gone to plan, as we said, I wish you had known it would go to plan. Where would we be then?

A Well, for me and my company, I mean, I think it's, we're kind of an underdog story. You know, I think we have old software here and there, and we're rewriting the future, and we're rebuilding it from the inside out, and so I think it's people, I hope, look at me and go, huh, how on earth did she do that? I never would have thought she could have taken that set of assets, and it became that thing, and you know, I look at people like Lisa Su at AMD, and what She started with and where she is right now, and it's just like, nobody would have looked at that at that time and thought that that could have happened, so a story like that would be just remarkable.

AI assessment note: “a story like that would be just remarkable”

Q is absolutely conversations like this, which is why I love this so much, not touching the schedule, but I'm so interested. You said there about, like, give this street away for free. When you have a new initiative, a new plan like that, how long do you give it as a test? Like, how long is enough enough before you go, cut it, guys, this is not working, all girls?

A Yeah, I think it is the most important question. First of all, you know, I always ask, what is the unscalable thing we need to do to get to scale? And so you do a lot of unscalable things. And so like, at some point you just start being stupid, right? Like, you know, you keep turning the crank and you're, and I think that's, what's embedded in that is, is this fight for product market fit. And I think when you're in a bigger company, you have product market fit over here, but if you're not looking at the adjacencies and trying to understand the tangential product market fit, if you will, and I think it is an iterative process. And I think it gets back to point of view. It's like, How strong is your hypothesis? How much do you believe that this product does in fact need to exist? And therefore it's just one more tweak. And so it's really an element of, you know, and I'm a big believer in data, right? Like, you know, I would trust all else, bring data. Like it was my time at Playdom where, you know, we were more of a data company truly than a gaming company, I would say. But there are times where your belief in what that end product state needs to be and your belief in what that customer experience needs and could be is what I think often propels and you see entrepreneurs do this all the time where they're like at it and at it and at it. There are also externalities, I guess, lik…

AI assessment note: “How strong is your hypothesis? How much do you believe that this product does in fact need to exist?”

Q to keep spinning and which 40 to let drop. Execs are either plate adders or plate removers. Plate adders have to go. So, love that one. It's practically on my wall. But if we think about, like, fundamentally, when we look at plate removers, we want them in our team. When you think back to the best in your career, what are the clearest signs someone is a plate remover?

A Well, first of all, I tried in my early career to be the plate remover. And so it comes from like, you know, I wasn't always the CEO. I wasn't always the one in charge. I mean, I literally forgot this story, but like it goes literally back to my earliest earliest days where I literally would remove the physical plates. I was a bus girl. I remember one of my first jobs and my job was not to remove like the place that people had finished eating on, but I was like, oh, that needs to go. I need to get back to the kitchen and I need to run. And so there's job that needed to be done. I saw what needed to be done, and I was leaning in and figuring out where it needed to go, and I just went and did things, and so I would tell my boss, like, hey, I thought about this, and I realized that you need to be doing this, so I'm gonna go take care of this, and I solved this, and they would be like, great, you know, it was almost like, oh my god, like, you thought about that, and then you took care of it, or, you know, and it's not like you were going rogue or doing something crazy, it was, these things are not, like, obvious, but it was also, like, not adding drama. Into a situation either where, you know, you just felt like, God, like you could mix it up in there. So I started out by being, I think a plate remover myself. I think when I look at executives, it is that person, you know, I think …

AI assessment note: “I saw what needed to be done... and I just went and did things”

Q You said about the CEO team there. I have to dig in on that. The hardest one for me, and I'm asking the easiest of questions today, my word, but it's like, how do you know when a stretch exec or a stretch VP is a stretch too far, and how long do you give them?

A It is the really hard thing. Question, because I think, you know, I'm a big believer in driving the personality, but I also think if I wasn't a CEO, I would either be hopefully a standup comedian on my good days, but, uh, I would be a psychologist. Like I need to understand. What are you really good at doing? You know, what do you love to do? What does the company need you to do? And oftentimes where this all gets out of balance is I'm asking somebody to do something they either aren't very good at, and we're all spiky in different dimensions. So understanding where is this person really awesome? Where are they? Maybe not. Or they like, they hate doing that thing. Like they're just not into it. And their, their attitude is like, I don't want to do this thing. In fact, we promoted a guy today. And one of the questions I asked the manager, I said, how ambitious is he? And he was like, oh, he's very ambitious. I was like, great. I was like, because his desire to do these things is going to be higher. He's going to want to lean in. He's going to want to try these things. And so I think you have to kind of ask those questions and say, like, are all those pieces in alignment? Like, cause it could be that like what you're, and this is, by the way, this evidences a lot in these scale problems. So the person who was amazing with From zero to 50 often can't take the next leap. Some peopl…

AI assessment note: “It is the really hard thing. Question, because I think, you know”

Q is absolutely conversations like this, which is why I love this so much, not touching the schedule, but I'm so interested. You said there about, like, give this street away for free. When you have a new initiative, a new plan like that, how long do you give it as a test? Like, how long is enough enough before you go, cut it, guys, this is not working, all girls?

A Yeah, I think it is the most important question. First of all, you know, I always ask, what is the unscalable thing we need to do to get to scale? And so you do a lot of unscalable things. And so like, at some point you just start being stupid, right? Like, you know, you keep turning the crank and you're, and I think that's, what's embedded in that is, is this fight for product market fit. And I think when you're in a bigger company, you have product market fit over here, but if you're not looking at the adjacencies and trying to understand the tangential product market fit, if you will, and I think it is an iterative process. And I think it gets back to point of view. It's like, How strong is your hypothesis? How much do you believe that this product does in fact need to exist? And therefore it's just one more tweak. And so it's really an element of, you know, and I'm a big believer in data, right? Like, you know, I would trust all else, bring data. Like it was my time at Playdom where, you know, we were more of a data company truly than a gaming company, I would say. But there are times where your belief in what that end product state needs to be and your belief in what that customer experience needs and could be is what I think often propels and you see entrepreneurs do this all the time where they're like at it and at it and at it. There are also externalities, I guess, lik…

AI assessment note: “I think it is the most important question. First of all, you know, I always ask”