20VC: A Masterclass in Leadership and Scaling Companies: The Decisions only the CEO Can Make, The Secret To Talent Acquisition and Retention and How To Find The Unscalable Things that are Fundamental To Scale with Christa Quarles, CEO @ Corel Corporation

Christa Quarles is the CEO @ Corel Corporation, building software solutions that simplify the task journey for knowledge workers. Prior to Corel, Christa spent close to 4 years as CEO @ Opendoor, driving a chapter of transformational change for the company. Before Opendoor, Christa was Chief Business Officer @ NextDoor, and finally pre-NextDoor, Christa spent 4 years at The Walt Disney Company where she led Disney Interactive to profitability as Senior Vice President, Interactive Games. If that was not enough, Christa is also on the board of Affirm and Kimberly Clark. In Today’s Episode with Christa Quarles You Will Learn: 1.) How Christa made her way into the world of startups having spent close to 10 years in investment banking? What were the biggest takeaways from her time at Walt Disney? How did her 3 years as CEO @ Opentable impact how she approaches leadership today? 2.) Company Breakpoints: What are the different breakpoints in the scaling of companies? When did this start to happen at Opendoor? How does decision-making need to change with scale? How can leaders ensure teams feel safe to be the most ambitious they can be? In what ways can leaders create environments of safety for them to be their best selves? 3.) The Role of the CEO: What decisions can only the CEO make? How can leaders determine when a C-Suite hire is a stretch too far? How has Christa's board membership on other boards changed how she runs her board today? Given a board's limited information, how can leaders extract the most out of them? 4.) "Operating is a Full Contact Sport": When has Christa found operating and leading the hardest? When faced with hard times, how does she push through them? How does Christa advise leaders on the challenges of their own scaling process? Where do many make mistakes in their own scaling? What is a "stuck state" and why is it the worst state to be in? 5.) Team Building and Trust: How does Christa approach trust today? Does she start from a position of being fully trusting or not trusting and there to be gained? What is Christa's favourite interview question to ask? In what way does Christa believe truly special candidates represent their passions in interviews? Item’s Mentioned In Today’s Episode with Christa Quarles Christa’s Favourite Book: Caste, The International Bestseller

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back. This is 20 VC with me, Harry Stebbings. And today, we're joined by one of the best operators in the valley today in my mind. So diving straight in, I'm so thrilled to welcome Krista Quarles, CEO at Coral Corporation, building software solutions that simplify the task journey for knowledge workers. Prior to Coral, Krista spent close to four years as CEO at OpenTable, driving a chapter of transformational change for the company. Before Krista was Chief Business Officer at Nextdoor. And finally, pre-Nextdoor, Krista spent close to four years at the Walt Disney Company, where she led Disney Interactive to profitability as Senior Vice President of Interactive Games. If that wasn't enough, Krista's also on the board of a firm and Kimberly Clark today. I'd also want to say a huge thank you to Jeremy Liu at Lightspeed, both for the intro and for some amazing questions and suggestions today.

• 0:44Harry Stebbings?

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• 1:26Harry Stebbings?

  Join companies like Stream, Hasura, Benapos, and unlock more sales with SecureFrame. And 20 VC listeners get 10% off at SecureFrame.com/20VC. I'm finding I've always been a big history fan, and so I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the very first venture fund in Silicon Valley, Cooley's formed more venture capital funds than any other law firm in the world, with 50-plus years working with VCs. They help VCs form and manage funds, make investments, and handle the myriad of issues that arise throughout a fund's lifetime. So to learn more about the number one most active law firm representing VC-backed companies going public, head over to Cooley.com and also check out CooleyGo.com. But that's enough from me, so now I'm so excited to hand over to Krista Quares,

• 2:10Harry Stebbings?

  CEO at Coral Corporation.

• 2:18Speaker 01

  You have now arrived at your destination.

• 2:21Harry Stebbings?

  Chris, it is such a joy to have you on the show today. I've been so looking forward to this one. I heard so much from Jeremy and from Max before the show, but thank you so much for joining me today.

• 2:29Speaker 02

  I'm so excited to be here and congrats on six years of this and two VC funds later. So it's awesome to be on the show.

• 2:37Harry Stebbings?

  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?

• 2:49Speaker 02

  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 dot 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'd 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.

• 3:27Speaker 02

  Because we had separated research and banking. 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 day. And it was my job to figure out winners and losers. And I think that was the interesting part. I think where veered off was like, I was super tired of just sitting on the sidelines, armchair quarterbacking, as we say in America.

• 4:12Speaker 02

  And I was like, I want to go play the game. And so the only way to do it here is to just go to a startup. And so I went to a small gaming company called Play-Doh and we were second to Zynga and we were really launching this whole games as a service. This concept, so we had cloud, we had social, we had new business model, we had everything that you could possibly figure out as new. And that was really the entry point. I dove in, I gave away a giant bonus that I was gonna get in my old banking world to go join this company. Cause I like, I was like, screw it, I'm just gonna go. And I didn't get paid my bonus. That year I left in December and I was gonna get paid it three months later, which could have been stupid, but I I dived in and went into startup life.

• 4:53Harry Stebbings?

  I mean, I absolutely love that. And I think it's more than paid off. So I think you can forget that bonus. There are a couple of elements that 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 of the last, I don't know, 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?

• 5:18Speaker 02

  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.

• 5:59Speaker 02

  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 then modern media had sort of lost its way and Netflix was coming around and they had to reimagine what the future was like. And so when we sold Play-Doh into Disney, a lot of that was, hey, consumers are spending different amounts of time with. Different types of media, we got to understand this. And I think that was Bob who leaned in and maybe it was because he was on the board of Apple.

• 6:43Speaker 02

  You know, really was about this transition into how the modern consumer is going to spend their media time. And this tech transformation and understanding technology and understanding. And if you think about it, it's not too dissimilar from the transition a lot of retail companies have made to go direct to consumer. If you think about Disney, Disney was not really direct to consumer. It was direct to, you know, a cable company, but it didn't really think about the end user. And what did the end user really want to do? And so this idea that like, oh, I'm going to put something out there, the end user is going to respond. And I'm going to change by virtue of that feedback, these real time feedback loops. We were in direct observation with Disney as they were transitioning business models. And that was just a really exciting time to be at the company. You know, oh, and we bought Lucas while I was there.

• 7:27Speaker 02

  So that was cool to, you know, hang out at Skywalker Ranch a few times.

• 7:31Harry Stebbings?

  Pretty pivotal times. I'm gonna just ask one thing though, which is you said about the craft of leadership there. When you blend the different experiences that you've had from the investment banking, Disney, OpenTable, now obviously with Coral. It's so broad, so it's terrible, awful interview question. But like, what does the craft of leadership mean to you today then? Blending these different disciplines and experiences.

• 7:51Speaker 02

  I think, you know, what's embedded in that is scale. And so what's fascinating, or what I felt fascinating about Disney was it was just huge. You know, like it would swell to over a hundred thousand employees during park high season time. The anthropological concept of like, how do you move that many people around was really just fascinating to me. And so I think that was a very interesting, just because the sheer just volume of what it takes. But it also means like, I think all big companies are somewhat alike though. Because in order to move that many people around, the system process, and that's why startups can often win. Because, you know, the, the big company gets stuck in this whole largesse of kind of moving around. I would say investment banking is a totally different thing.

• 8:36Speaker 02

  It's, it's like actually entrepreneurial pods of cowboys, or at least that's the way it was when I was there. And you kind of like gunsling and did your thing to try and make money really quickly. I would say investment banking was not the finest leadership experience that I witnessed. But sometimes I think your best examples come from the worst experiences. You know, I could not bring my whole self to work when I worked in investment banking, you know. I muted every part of me. In fact, I joke sometimes, like I became a dude because I, you know, I showed up, I swore, I did what it took to be successful in that environment. And then I think you get to the smaller company and say, you know, OpenTable was about 700 people when I joined. Corel was about 750 people. So it's enough that I can know a lot of the employee base.

• 9:20Speaker 02

  And every change that you make has a big, big, big, big impact. And so I think it gets back into how you have to modulate yourself depending on the scale of the organization. And frankly, the ambition that sits underneath it.

• 9:32Harry Stebbings?

  Can I ask, when you think about kind of the scales that you said, that you said 700, 750. And when you 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 in terms of scaling with the company?

• 9:53Speaker 02

  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 breakpoint is about 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 breakpoint that I see most companies hit. It means like, and this was exactly what happened to me at Playtime, like we hit 150 and like pre, you know, all the software that's helped companies grow, but like we didn't have an HRIS.

• 10:37Speaker 02

  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? So 150 is a breakpoint. I see 500, 2000, 10,000. 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 change. And if the organization doesn't change with the size of it, you get stuck or mired or worse yet, broken because you just, you keep wanting to do it the way you did when you were at 50. People and you realize my message just isn't getting out. I'm not able to drive people and I'm not really inculcating a culture where people feel empowered

• 11:20Speaker 02

  and unable to go, you know, forth because let me tell you, when you're at, you know, certainly 10,000 people, like you can't dictate every decision. You can't drive every outcome and so you have to build a culture. You know, back to that Dunbar's number concept. And so, you know, culture is how people make decisions when you're not in the room. And increasingly, you're not in more rooms as the company gets bigger. And you have to really adjust and figure out how that transition is going to go.

• 11:43Harry Stebbings?

  How do you handle like what I think is the most challenging element, which is when you're not in the room and the decision is being made. How do you ensure that they're as ambitious as they should be and not 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?

• 11:59Speaker 02

  Yeah, and I will say 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 situation. 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.

• 12:44Speaker 02

  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 feedback? And I was like, all right, yeah, I love feedback. And he said, you know, five of your company values are essentially move faster. It was like progress over perfection. Find the testable hypotheses. Like I was just like, get moving and what? I realized that the the only lever I had as the CEO was what do I reward and what do I not reward?

• 13:28Speaker 02

  And I think what what's interesting is that I had to make it unsafe not to take risk. And so, you know, if you were just gonna sit in your little box and kind of like do your thing, that was going to be a risky position now. Whereas the other people who were like leaning forward and trying new things, and I would evidence frankly grand failure in the company. I would say, look, you know, now, obviously, you don't want to have company ending failure. And, you know, hopefully, you put guardrails up to evolve that. But just giving people the understanding that like those people are the ones that are gonna get promoted. Those are the people who are gonna make it, you know, go ahead. Those are the people who are getting spotlighted in the, you know, the quarterly town hall or the monthly, you know, ask me anythings. And so that was the thing that I had to learn. And I learned it kind of the hard way because it wasn't intuitive to me.

• 14:12Speaker 02

  It was just as simple as that, like, what are you rewarding in this organization? And what reward will drive your outcome?

• 14:18Harry Stebbings?

  How did you imbue that to the organization? Was it by someone taking a big risk? And you very publicly promoting them, moving them swiftly up the hierarchy to show that you could ascend with risk? So how do you go from what do I reward, what do I not reward? To people going, wow, that's what can happen?

• 14:36Speaker 02

  Sometimes it's like as simple as just, hey, you're gonna get like 10 more engineers. You know, you know, it's it's about resourcing. It's about saying, these guys are crushing it over here. Let's expand their remit. They're gonna try more things. And I think to be clear, I mean, you know, there was a point in time where we wanted to understand at OpenTable just the power of how deep the network effect could go. And so I said, we picked a street in Palo Alto. And I said, give it all away for free. I said, I don't care, don't charge anything. I just want to see if we can get 100% of the restaurants on the street. And what was interesting was they came back and we literally couldn't give the product away in that instance, because the restaurant would be like, well, I'm not an open table restaurant. I'm this kind of restaurant. And I was like, huh, okay, like, that means.

• 15:19Speaker 02

  And so the teams that were driving that, you know, it wasn't just me directing, obviously, but it was the team. And it was a spectacular failure, but it taught us so much that like, oh, my God, like, we're solving the wrong problem. We're solving the different. Problem and I think it was just a good lesson and you know that team ended up because they moved so quickly they got to the insert so quickly we kept evolving and iterating and then they got more teams and then eventually their roles became bigger and then they got promoted and so just the whole ecosystem around that swift thoughtful risk you know point of view risk decision making you know they were just much bigger and more important drivers of our overall company and organization.

• 15:55Harry Stebbings?

  It is absolutely conversations like this which is why I love this so much not touching the schedule but I'm so should 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 or girls.

• 16:13Speaker 02

  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 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 Plenum 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 like sometimes market conditions are just not ready for the thing that you want to build right so we had an example of this at OpenTable with like OpenTable Pay where we wanted to you know get rid of the whole like put your check and the whole back and forth and the dance and we had it going but the the point of sale infrastructure was not where it needed to be in order for that to ultimately.

• 17:41Speaker 02

  Be successful. And so we were just early, like had that launch now, I'd be wildly successful because you think see food delivery businesses and other things like that have changed the paradigm of what point of sale looks like in a restaurant. But we were just early. And so that's the other thing that Matt pay attention to is like, are there externalities that prohibit your vision from coming to reality that you don't control? And if you don't control enough of the externalities and they're not where they need to be, you could just be too early on this grand vision, I'll call it. And sometimes when you're too early, you're wrong.

• 18:12Harry Stebbings?

  I totally agree with you in terms of 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?

• 18:32Speaker 02

  I am a corner cutter by nature, I'd say. In fact, I've surrounded myself with like I daughters 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 want people around me who are going to be obsessed about the detail. And so I think it's about finding that complementary skill set for yourself

• 19:16Speaker 02

  such that you can decide, okay, like, these are details that that maybe I can't cause. And they're going to come up to you and say, hey, timeout, 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 questions to ask is, who would make a great number two for this person? And what that reference question is getting at is like, you know, of course, it's like sort of quote unquote weakness, but nobody can spike along every dimension. Nobody can be amazing at every single thing that they do. They have to have an understanding of like, who's a great compliment for this person? Who's going to do the thing that this person may not do? So I find people

• 20:01Speaker 02

  around me who are going to not cut corners and then tell them that they can tell me to stop.

• 20:06Harry Stebbings?

  My personal favorite, the trouble is I work too hard. You're like, aha, yeah, I love that one. Brilliant. I totally love that. Can I ask you, imagine being a thousand miles an hour kind of all the time. I love that and I feel it bluntly 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.

• 20:28Speaker 02

  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 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 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

• 21:09Speaker 02

  because people who are like, you know, like I'm constantly like, I'm moving a lot and they're 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 so that idea of take a minute, invert, slow down, figure out what's important. And then usually by the time I become right again, I know where I am, what I need to be doing.

• 21:51Harry Stebbings?

  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?

• 22:04Speaker 02

  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 it 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?

• 22:49Speaker 02

  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 full fall, I kind of got stuck. And I think that's the most dangerous place for anybody to be, is the stuck state. Falling, fine, all right, I know what I'm dealing with, you know, ugly truth, fine, bring it on, let's go, let's, now I know what to do.

• 23:33Speaker 02

  It's that, that moment before you let yourself fall, that I think is most dangerous, because you're just, you're holding on. And I think when you hold on, you're not your best, you're not contributing, you're just holding on. And so I think allowing the fall, which I wasn't really wanting to do, because I was like, you know, I was like, success oriented, and I was like, I'm gonna succeed, I'll figure it out. But I think what you have to tell yourself too, is like, what's on the other side is always better. And it's like, sometimes orders of magnitude better, and I think that fear of what could be on the other side without knowing, it's like a trapeze. It's like, you have to let go to kind of catch the next one, and then there's this moment where you're like in flight, and it's scary. But I think it's the piece that I've learned, you've got to just let it go and kind of move to the next side.

• 24:16Harry Stebbings?

  Gosh, you should be an inspirational speaker. I feel like I'm so pumped after hearing that it was gonna 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, like a passion and being dampened? What is stuck?

• 24:32Speaker 02

  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 gonna 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 gonna 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, eh, I'm gonna just come in and do my best and hope to not piss somebody off. And inevitably, because of that, you're operating at like sixty percent capacity, right? Like, essentially what was happening, my prefrontal cortex had shut down.

• 25:17Speaker 02

  And I was like, in the lizard brain, my amygdala back here. And we all know you lose like forty, fifty 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 ten 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 psychological safety. And so if people show up and they feel safe, then you can do your best work. And I think the thing that people forget is like, play is an important part of creativity, innovation.

• 25:59Speaker 02

  And if you kind of create this thing where it's all locked down, it's just you're not gonna get the outcome you want. And so that, for me, was how it showed up. I was just a smaller, less happy, less bright version, not even of myself. And I felt unsafe and I do think that my prefrontal cortex shut down. And I think I was dumber, honestly. I think I had lost the fifty IQ points because I was like, it had all shut down. Because I was just, didn't like the environment I was going into every single day.

• 26:23Harry Stebbings?

  I think one of the most important jobs of a leader is to create an environment of safety, where everyone can feel like they're bringing their best selves to work. So I agree. I think people are such a large part of that, though. And I do wanna talk about a tweet that was sent out by Jeremy D, and it quoted And it was one of my favorite tweets and it was a CEO has fifty spinning plates at a time. And her job is to decide which ten to keep spinning and which forty 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?

• 27:02Speaker 02

  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. But 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 plates that people had finished eating along. But I was like, oh, that needs to go. I need to get it back to the kitchen and I need to run. And so there is 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, I was, 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.

• 27:47Speaker 02

  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 I 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, think about my, you know, CRO at Corral right now. She's just like, yeah, and I thought about where this is gonna go and I'm gonna like pull this and I'm gonna do this. And don't worry about this because I got it and I'm gonna solve it. And so like, I was like, great. And like within like ten minutes of her starting, I added, I put customer support into her division. So she's chief revenue officer, but I pulled customer support in.

• 28:31Speaker 02

  And I was like, I know you'll figure it out. And she's like, all right, we got this, you know. And I think she just is leaning in, understand what the market, the organization needs. And she's just going to deliver on where I need her to go. The other critical thing is understanding which decision. decisions only you can make as a CEO. Many other decisions can be delegated. Many other decisions can move down the ranks. There's certain decisions that only you can make. And one of the reasons why this is important is if I'm getting distracted from the decisions that only I can make, the organization is just not going to propel itself forward. Because they are, it's almost like the choke point is my ability to make those decisions. And if I'm busy over here dealing with drama that somehow somebody else could have else handled,

• 29:14Speaker 02

  then we are now limited by my bandwidth and my capacity. And that's the thing that's going to hold the organization back.

• 29:21Harry Stebbings?

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

• 29:27Speaker 02

  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. So 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 the 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.

• 30:12Speaker 02

  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 third thing would really be, you know, kind of how we interface with our board? How are we driving for that conversation? You know, I can't put my, you know, chief people officer in that role. I have to do that role. That is my position. It's our fiduciary duty to communicate and drive

• 30:56Speaker 02

  and make sure that the board is feeling satisfied that we are on the right path. And if I'm focused over here on, I don't know, HR issue number 72. I'm just distracted and I'm not going to be putting my time and energy in where it it best would land. It's funny because like before I became a CEO, I'd hear all these CEOs going, gosh, I just need time to think. I was like, are these people like, who needs like, that seems such a like a dilettantish kind of response to the role. And then I got to be a CEO and I'm like, gosh, I just need time to think. I think it's because of this, you get weighed down by all of these like potentially unnecessary, not game changing, not company ending, not company making decisions.

• 31:41Speaker 02

  And you are not spending your time on the things that are like, like right now, we've been like a key tech decision to be making on our parallels business. I need to go make that, like we need to go drive that. And that needs to be my priority, not, you know, whether or not some, you know, how we in-source or outsource our customer support. Like my CRO, she can actually mean and then just drive that decision. And I think that's an important one.

• 32:01Harry Stebbings?

  You said about the CEO team that I have to dig in on that. The hardest one for me, and I'm asking the easiest of questions to say in my word. And 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?

• 32:14Speaker 02

  It is the really hard 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 stand-up comedian on my good days, but 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? Or 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.

• 32:56Speaker 02

  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 because it could be that like what you're me and this is by the way this evidences a lot in these scale problems. So the person who is amazing from zero to fifty often can't take the next leap. Some people can't. Some people are purple unicorns and they can ride the ride. Like an early salesperson would be a great example where that first wave through,

• 33:38Speaker 02

  they're like the lone wolf. They're figuring out how to sell. They're figuring out what the words are. And then once they figure it out and you get into like lather, rinse, repeat, they either get bored or they're just not that organized because they're super creative people. And so they're just not going to be able to make that leap. And so like, okay, we could we put them on another mission. Could we put them over in this other thing where we can take advantage of this incredible ability they have? Because if it just gets into lather, rinse, repeat, they might put a bullet in their head. So they just don't want to do it. And I think that's the key thing is like you're always looking across the organization and trying to find out where people are out of alignment. And so it does take time to figure that out, though. And I think I spent a lot of time asking an executive like, when do your eyes light up? When you talk about your job?

• 34:22Speaker 02

  And there's these moments where you can just see like that part of their job just brings them immense amount of joy. And I was like, okay, we're gonna find you an opportunity to do that. And if we can do that, then this is gonna be good. Now, it may not be what we need you to do. So like I've often said, I was like, if you're an apple and I need an orange, I can't make you become an orange. And I can make you a juicier apple. That's great. But I can't actually make you be an orange. And so it's not personal. And so the kind thing is to say, hey, let's go find you a job where everybody needs, like where they need an apple desperately and we're gonna, I'm gonna crush it with you. And let's go do that. Let's go figure that out. That's the part where you, as an executive, can waste vast amount of emotional energy trying to convert somebody to being something that they're actually not. Now, that this is more of a comment about people later on in their career.

• 35:07Speaker 02

  If you're like twenty two, people can become anything.

• 35:10Harry Stebbings?

  The final element I do want to touch on before the quick fire is you mentioned the third 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 a 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?

• 35:33Speaker 02

  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 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 re-shift 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.

• 36:15Speaker 02

  And what I really needed was the board to 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.

• 36:49Harry Stebbings?

  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?

• 36:59Speaker 02

  Well, 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 1% 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."

• 37:44Speaker 02

  And usually, the board's like, "Great!" I mean, every now and then you get a, or a 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 like to hope that I'm just trying to understand better. But that, that can happen occasionally where that, that line does get blurred.

• 38:04Harry Stebbings?

  How do you handle that? Cause 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? Be nice.

• 38:13Speaker 02

  In my view, like, boy, is if you feel like it is a, 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. Cause on the one hand, I'm, I'm a big believer in, there's usually a kernel of truth. Even if I disagree with 90%, 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 and I don't think it like, how can it be true? And then 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, like, how dare you? Like, that's obviously not going to be great. And it's certainly not a place of curiosity either.

• 38:58Speaker 02

  Like, I think you want to lean in and be like, 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 a 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 that it's kind of like a stuck state. Back to that other part is if you just let them like, keep asking every meeting and you just don't hit it on the head. You're going to be frustrated, they're going to be frustrated. I would just say like, don't let it continue if it is continuing. Just take some time and knock it down.

• 39:32Harry Stebbings?

  I do want to move into my favorite though, which is a quick fire round. So I say a short statement and then you give me your immediate thoughts. Does that sound okay?

• 39:39Speaker 02

  That sounds great.

• 39:40Harry Stebbings?

  Okay. So what's the favorite book and why?

• 39:42Speaker 02

  I love so many books, but 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 caste 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, and I just opened my eyes on so much 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?

• 40:24Speaker 02

  So for me, it was just this really eye opening and groundbreaking from that dimension. And I think everybody should read it.

• 40:29Harry Stebbings?

  What do you know now that you wish you'd known at the start of your career in tech?

• 40:33Speaker 02

  It's all gonna be okay.

• 40:36Speaker 02

  Like chill out a little. Like, I think I was like, I was so amped and like eager and ambitious. And I wanted the outcomes sometimes didn't slow down and stop and celebrate enough along the way. And I think I was just on to the next thing, on to the treadmill. I mean, I would regularly take the weekend off between jobs. Like that was like, I thought that was a good idea. And I think the idea is like, take a minute, you'll actually be better, you'll be more creative, you'll be fresher. You'll be able to give more if you can take that time in between things and to take a pause.

• 41:09Harry Stebbings?

  What's the biggest lie that rich people tell themselves?

• 41:13Speaker 02

  Oh my God, like there's just so much more capable, like it's not luck that I'm just really that much better than everyone else. I think that's the lie. I, I think understanding the importance of preparation meeting opportunity, i.e. luck. That's an important thing, like where you are born, the time you were born. I think all of that leads into, you know, how people are successful and how money comes to be.

• 41:36Harry Stebbings?

  What advice do you often give but find hard to take?

• 41:41Speaker 02

  You know, I think put your own oxygen mask on first. You know, one of the things I say in my company, like, you know, it'll often happen like somebody's going to a funeral or somebody's mom gets cancer or a kid gets sick. And I will say to them, you know, like self, family, company, always in that order. Because if you can't take care of yourself, you can't give oxygen to the next person. And I find that sometimes I run a little too hard.

• 42:03Harry Stebbings?

  If you could change one thing with the wave of a wand, what would it be?

• 42:07Speaker 02

  You know, I used to say I'd be, you know, I'd like to be able to teletransport. But I think we've done this in the age of Zoom, like my, the superpower I always wanted was that. Honestly, it's climate. I mean, you know, it's 108 in Seattle and my team's there today. You know, I was just in Southern California, it was 100 degrees. I mean, climate change is upon us. I mean, we saw this whole red dawn in San Francisco last September. And so I would heal this planet, we'll stop.

• 42:34Harry Stebbings?

  Penultimate one, what three traits would you most like your children to adopt?

• 42:38Speaker 02

  I would hope that they are kind, curious. You know, I'd say the third one is, is still just joyful. You know, I think life is harder when you don't bring joy to the equation. One of our sayings is joy and laughter belong here. So I think that's an important one as well.

• 42:56Harry Stebbings?

  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?

• 43:04Speaker 02

  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, that time and thought that that could have happened. So a story like that would be just remarkable.

• 43:40Harry Stebbings?

  Listen, Chris, this has been so much fun, Stu. I can't thank you enough for joining me today and it's been such a pleasure.

• 43:45Speaker 02

  I loved it. Thanks so much. Bye, Harry.

• 43:50Harry Stebbings?

  My word, if that wasn't a masterclass in leadership, I do not know what is. Krista was just incredible and I want to say huge thank you to her for being so open and willing to move away from schedule as easily as she did that. If you'd like to see more from us, of course, you can on the 20minutevc.com. But before we leave you today, did you know that more than 80% of US public stock is owned by just 10% of Americans? This divide is even greater in the private markets. Carter makes it as easy to issue equity to your employees as it is to issue payroll, and for employees, as easy to accept it too. More than 16,000 companies issue equity to their employees through Carter. Whether you're just getting started or getting ready to go public, the team at Carter can help. Check them out at carter.com. And then another incredible product you have to introduce is SecureFrame.

• 44:32Harry Stebbings?

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• 45:17Harry Stebbings?

  So to learn more about the number one most active law firm representing VC-backed companies going public, head over to cooley.com and also check out cooleygo.com. As always, I so appreciate all your support and I can't wait to bring you a phenomenal next episode.