Ep. 263: Xero CEO Sukhinder Singh Cassidy on When FOMO Beats Fear of Failure

追加: 2026-05-14

[00:00:00]without fail. When you are, you know, willing to be imperfect and vulnerable, people give you grace. People give you grace. And so, I would rather model imperfection than model perfection because I think if that's the standard you set for everyone else, man, it's really hard to be honest about a problem or to show frustration. And trust me, I show plenty.

[00:00:24]Welcome to Corporate Competitor presented by Forbes Books, the podcast where executives share how the lessons they learned playing sports shape their leadership. With me for today's episode is Sukkinder Singh Cassidy, CEO of Zero, a global accounting software company serving more than 4 million subscribers with a team of nearly 5,000 employees worldwide. She's a seasoned global executive with leadership experience at companies like Google and StubHub and has served on the boards of organizations including Trip Advisor and Urban Outfitters. But her perspective on leadership isn't shaped by business alone. As a kid, she spent time figure skating before later finding her rhythm on a tennis court, a place she still returns to today to sharpen her focus and reset her mind.

[00:01:23]Sinder, thanks so much for joining us.

[00:01:26]>> I'm excited to be here.

[00:01:27]>> Well, I in studying you, preparing for today, um I love it. Born in Tanzania, right? And then right on the Indian Ocean coast. how beautiful that must have been. And then you spent the first couple of years of your life there before moving to Canada.

[00:01:44]>> Um where your parents were both medical doctors.

[00:01:47]>> Now, how did those how did those early years and that that large culture shift that had to occur obviously for you um as a child? How how did that play a role in maybe helping you as you progressed in life and and even into a leadership role that you have today?

[00:02:05]>> Yeah. Well, even more than a culture shift for me because I was two when we moved. It was a culture shift for my parents. So, my parents moved from Africa, but I witnessed it. So, maybe it had an indirect effect. My parents moved from Africa late in life, right? They were settled. They to your point. They had a beach house or beach cottage. I'm told, you know, on in Darlam. They had a amazing life. My father was in fact born in East Africa. My came there after marriage from India. So I think they had this great life but I think they really a stopped political instability and b wanted sort of a better education system for their children. So first of all they picked up and they left a very kind of wellestablished life and a lot of their things and moved to Canada where you know from what I understand my parents both had to re-qualify for their residency. They have three young girls like you know at the time I'm two I might think my oldest sister's nine all in between they go back into medical residency you know the reason why they're doing night duty so like one of the things I remember is you know my parents moved from Toronto to uh Hamilton to ultimately a small town in Canada called St. Catherine's I remember my dad and mom would take us to the hospital overnight because one of them was doing night duty, you know, and the other one would take care of the kids.

[00:03:20]So, um you know, people my mom always used to tell me the story that when she had to do night duty and again like she's now in her 40s, right? My dad's almost 50 at this point. She would laugh and tell me that you know you always knew the day that my mom was on night duty cuz my dad would have to send us to school and my piggy tails were like very like uh messily braided. You know that his like reading >> as a dad I as a dad my my my my my daughter's friends can all tell when my wife was out of town too. Yes.

[00:03:46]>> Yeah. Exactly. And other times I remember my mom taking us to the hospital to see my dad because he was on night duty and so the way we were going to get to see him is like go have a meal with him and then we'd come home. And so my distinct memories of our are parents who like you know that classic like even though they were very well educated, uprooted, better life, incredibly hard work ethic, whatever's necessary, premium on education, um very thrifty, you know, we lived in uh two apartments before, you know, my parents bought a home in St. Catherine's um and they didn't have to do those things. So I don't know classic hard work ethic uh value of education yeah doing kind of whatever is necessary >> well to achieve what you achieve today in business you've probably had to make enormous sacrifices of your own and so if you can look back at that and say I saw sacrifice early right I understood like this is I understood that that was the way to the dream that the only way to the dream is through sacrifice >> sacrifice vocation, purpose. They all kind of live together in the same sphere. Like I don't know that you get one without the other. Like fulfillment, purpose, sacrifice, vocation. Like these things are of a kind for me. They're not like your vocation's over here and purpose is over here. That has just never been the way I philosophy.

[00:05:08]>> Wow, that's awesome. You know, you you authored a book um choose possibility, take risks, and thrive even when you fail. A lot of great lessons there, right? And one of my favorites was in chapter 3 of your book and which you talk about the importance of putting the who before the what and it was really interesting. But can you unpack that a little bit for for listeners those who might try to understand what do you what exactly do you mean by that?

[00:05:33]>> Sure. Well I think I learned this lesson twice um pretty hard in my early years.

[00:05:39]So the first example um when I graduated college I tell the story that I had I didn't have a job even though I graduated you know very good grades used to being an overachiever undergraduate business school in Canada you know kind of pretty close to the top of my class and all my classmates are going off and getting investment banking consulting jobs what have you and so it takes me almost a year to get one I do ultimately get the job of my dreams at Maril Lynch and at Maril Lynch and then I'm asked to sort of pick you know where I want to slot like and I'm like, I want to go work for a media company. How exciting.

[00:06:12]I want to go to LA. I want to work for like I want to work in the entertainment side of investment banking. Um, and I don't get that offer. Instead, I get placed in New York, but in the financial institutions group under a guy named Henry Michaels working on, wait for it, savings and loans. Now, if you ask Exactly. Ask any 22year-old if they want to work on the SNL industry and not Saturday Night Live.

[00:06:36]>> Not Saturday Night Live, >> right? not Saturday Night Live and I'm like but you know thrifts I didn't even know what they were and financial institutions was the least exciting thing to me but Henry and by this time remember I've had this year at trying to get a job I finally get one so by the time I get the job my dream I'm dreams I'm a year behind my classmates and I'm really grateful actually that I managed to secure it so I walk in there you know hungry to prove myself but not super excited about financial institutions and then Henry is this you Now he is this pipe smoking mid30s MD who likes to tell me how he was the youngest person at Merrill ever to make MD and it was all about hard work very eccentric quirky what have you but Henry thinks he's something in me and I am hungry to prove myself and so we end up working on a lot of things directly together and why is that important because often there's a lot of hierarchies so you know usually a managing director has a you know a vice president and then an associate and then the lowly the analyst. And so Henry early on started working with me directly and skipping those layers. So what was that for me? Him and I was just like, I'm going to work as hard as I can. I'm going to listen to all these stories, you know. So I put everything into it and Henry put a lot into me and as a result, I had a great experience in Mel. I was the top of my class despite the fact that I was competing with all these kids from, you know, Ivy League schools and so on, which I did not have.

[00:08:03]I went to a public university in Canada.

[00:08:06]you know, they ultimately send me to London. My career like takes off and that's all because of Henry Michaels and that very boring savings and loan industry example and his investment in me. Um, and so like that was an early example. I'm like, okay, you can have the what, but like the who matters more.

[00:08:22]And then that showed up again in life for me because uh when I moved to Silicon Valley, I joined a startup. I had at this point had, you know, lots of experience. It was startup in interactive television. Super sexy. I was like, "Oh my god, I'm going to work in TV for my first operating role." Um, and I was out of there in 6 months. I found the culture to be one in which they didn't really appreciate maybe my fairly aggressive, intense style and I kept getting told told I needed coaching, which I'd never been told in investment banking. Um, and so I was miserable and I thought I was going to leave the valley. And then I interviewed with a startup called Jungle Eye. Once again, the subject matter did not interest me. Their tagline was the internet is the database. I was like, I'm not even sure what that means. But the three founders were dropouts from Stanford uh computer science. They were all Indian and they were so sharp. They were so smart. And so I met with them and I was miserable in this other job which was in a very sexy industry again part of technology again. And I quit and I joined Jung Lee. And um within I think the first day of my job, not only were they not telling me I was not too intense, they were leaning into that intensity and they were like, "Hey, we know we hired you to do product management, but we really need you to do business development, which is like really, you know, calling these retailers and convincing them to like pay us for our shopping links." And so I was like, "Sure, uh, sure, I'll try that." And I did it. And six months later, Amazon bought the company because of those relationships and because Amazon wanted to build a marketplace and saw Jungle as the first generation. So like two stark examples of like where I was initially attracted to the what, but the who was the differentiator, who I got to work with, who shared my values, who saw value in me um and my strengths.

[00:10:07]Uh those have been very enduring lessons for me. And then from that point on, would you argue that most of your as you were navigating a a fantastical career?

[00:10:18]I mean, some of the things you've done are really amazing. That that that you latched on to the who that you started saying, I I can make really amazing things happen in a really boring space as long as I've got the right who.

[00:10:33]>> Absolutely. I am extraordinarily proud.

[00:10:36]Uh I think you know bar none of the quality of people I've been able to work with, learn from, hire, help succeed.

[00:10:44]That is probably the enduring thing I'm proud of across all the experiences I've had, whether that's Zero or StubHub or Google um or Joyous or Yodily, even Polyvore, which was not a successful career move for me. Just extraordinary people all the way through. And I think that's because I learned to value that and you know and I was drawn to that. Um so yes it is for sure the lesson of my career.

[00:11:08]>> And so what a great lesson that is for all the rest of us that too often we are we need a title. We want to make sure you know that we're getting um we want we want to we want to work for the sexy place right? I mean it all sounds good but at the end of the day if you're not working for the right people >> you won't you won't last right? you won't be happy in your dayto-day. You won't last. You won't feel like you're valued. You won't feel like you can learn. I mean, so I think the magical combination, at least for me, is finding somebody whose values you share. You overlap on. And when I say values, I mean like what you think is ultimately kind of just and fair in the world, right? Like I'm somebody who's pretty um canderous. So I really like cultures of transparency. I like people who are transparent. I don't really do well with maybe, you know, leaders who don't show me just directly what they're thinking or, you know, or just aren't blunt with me or maybe, you know, what's going on in the system. I do I I wouldn't say I do well with highly political kind of leaders, right? So, I'm attracted to people who are transparent as an example. But I think the magical combination is share values, diverse, right? So, they look at me and be like, "Wow, she has something that we need."

[00:12:16]and I look at them and I'm like, man, that person is at least a few things I can learn. Um, that tends to be a pretty magical combination.

[00:12:23]>> That is the combo. That's awesome.

[00:12:25]That's really great. And it's amazing you were able to find it truthfully so early in your career. One of the other more powerful ideas from the book um that I wanted to highlight is an equation you use, right? When FOMO, when fear of missing out is greater than the fear of failure equals action. Mhm.

[00:12:45]>> I love that. Right. But what advice would you give to listeners, people that that are that are trying to hear you explain that on how they can apply that into their their pathway, their leadership, their leadership journey.

[00:12:59]>> Sure. Well, I think the reason I sort of created that equation is because I think people overfocus, which is going to be ironic, on positive visualization, right? When people, you know, when people say, well, you need to take a risk, right? Everybody, you know, talks about like imagine success, imagine success. But, you know, it's not that people who don't make a leap lack ambition. I mean, I think what they're more fearful of is like the failure mode, right? So, if you only imagine success, you're only imagining one side of that equation. But, if you can't overcome your fear of failure, it doesn't matter how big your FOMO is, right? That's why I said you you have to invisibly shrink your fear of failure.

[00:13:39]And so, how do you do that? I will say to people like premortal failure not success and maybe I've learned this because I've been you know before I was a CEO I was in business development and sales so you know in sales you learn to fail right in business development I always give people the best example cuz in in Silicon Valley business development is like creating a business model where none exists or like getting the first partnership of a kind or what have you. So it's all vision I mean in business development more than sales the product doesn't exist. So it's all vision it's all positive. It's like imagine the possibilities, you know, zero decide to deal with anthropic, right? Super excited about it. It's all about the possibility of what we can do with them. So that's great. Okay. So as your bisdev executive in the quoting process, it's all vision, vision, vision, vision. What do you think happens when you hit the contract process? It is the exact opposite of vision. Like I'm a beast of a negotiator. Why? Because all you do in a contract, all you do is premortem failure. Everything in a contract is like indemnification. term you know right to get >> what state we're what what court system we're going to use right >> what court system is that about pre no it's about premorteming failure and getting all the failure states identified so you can get the deal done right so I think I have been trained on both and I really say to people can you please premortem the failure state because most failures are not catastrophic and you can and think through what you would do in if these failures came to pass and then I think you can shrink the failure enough for that equation to really get you to action Well, and I think you're starting there on the So, I I made a note that one of the lines you had here. Sorry, I make a lot of notes while I'm interviewing.

[00:15:13]>> Um, is you you asked the question, how do you shrink your fear of failure? And and so this sounds like it's the it's the tip of the spear in in that in the answer to that question. You begin by by saying, "What are all the things that could go wrong?"

[00:15:28]>> All the failure states, list them out.

[00:15:29]List them out and get them into action.

[00:15:31]You know, in the book I also talk about Alan Eustace, who's one of Google's earliest engineers and heads of engineering. And a little known fact about Allan, you think, well, wow, the most amazing thing he's ever done is he was, you know, one of the early engineering leaders at Google. And that would be true. I was there with him.

[00:15:47]However, what you don't know about Allan is he has set the world record for the fastest freef fall and longest freefall from space. From space. So that is like if you've never heard of a daredevil move, I would call that a daredevil move. So how did Allan do that? Well, Allan when he was he took a sbatical from Google and he imagined making a you know he's an engineer after all. Imagine making a flying suit and so he worked with the team and ultimately that dream transformed into rather than a flying suit he looked at the idea of getting to the edge of the stratosphere be able to get there and fall to earth and only one other guy's done it. Unfortunately, this is what I need about stories.

[00:16:28]Unfortunately, that guy who set that Felix Bombgartner who set that world record before Al has passed actually.

[00:16:34]Um, so happened in the last couple years. So Allan set this goal for himself and then he ultimately and he is now in the Guinness Book of World Records after years of creating, you know, the system for suit that could hold the pressure, you know, and then how to get up to the stratosphere. He used a hot air balloon. He then free fell like I can't remember how many minutes. It's crazy to earth and set uh the world record. There's I mean there you can find video on Allen's fall from space. So I interviewed >> for this for the book.

[00:17:04]>> You interviewed him for the book. Okay.

[00:17:06]>> I interviewed him for the book. But Allan's key point was by the time I'm at the edge of the stratosphere I have I have premorted every failure state. So his heartbeat remained steady throughout that multi-minute fall even though of course he was at risk for his life. And like I said, this is a bespectled engineer. Like when you see a picture of Alan Eustace, you're not going to think, you know, like skydiving, you know, you know, high-f flyier. So, so Allan's whole point was by the time I got there, I had premorted with the team every failure state. I had tested, I had tried. How did I take one of the biggest risks of my life and arguably a big risk for anybody, including a daredevil?

[00:17:47]Well, you pre-born failure.

[00:17:49]>> That's amazing. Um, I think a lot of leaders don't realize that the systems and the processes that they put in place can actually discourage risk-taking.

[00:17:59]What are the intentional things you do as a leader to create an environment where people feel safe, maybe even encouraged to take to take risks, to step to to to go just a little further than anyone previously has done? How do what are what are some of the things you do as a leader to create that environment? Uh if you ever saw me uh speaking to our employees uh in an all hands or speaking on stage to our customers at ZeroCon, I am a pretty um I don't know pretty raw leader.

[00:18:34]Even if I wanted to uh perfect myself, it would be pretty hard. I swear. I try, you know, and sometimes when I swear, it's just out of exuberance. Often it is. Um, but I also want to model to employees that showing up as you are is completely okay. Like I think that this idea that there is a perfect CEO, that there's a perfect executor, that there's a perfect executive. So honestly, I I mean, we're all pretty flawed. I kind of think I am more comfortable than maybe the average bear or CEO at being like, hey, you know, this is how I do it. I run my own Slack channel at work. And the entire the entirety of that is like stream of consciousness. It's not written by anybody else. It's not like so I'm just like look like showing up imperfectly no offense. It's much more interesting. It is much more and so I kind of want to make people feel very safe personally I would say. Remember one of my one of the things I said earlier to you is like one of my values is cander and transparency and along with that comes a lot of like comes theoretically risk right what if you say something? What if you step out of line?

[00:19:36]Well, I was going to say in a in a public company company especially you I mean there's just you know they've all every everyone's had had all the uh the cander beaten out of them. They have right but I would say historically even internally I say many things to my employees right I like I said I have a slides share like and without fail when you are you know willing to be imperfect and vulnerable people give you grace people give you grace and so I would rather model imperfection than model perfection because I think if that's the standard you set for everyone else man it's really hard to be honest about a problem or to show frustration and trust me I feel plenty. So, look, I think even if I wanted to be perfect, I couldn't.

[00:20:20]Um, but I think a very personal tactic for me, which has, I guess, served me well as a leader, is I'm like, when people ask me a question, I don't know the answer, I'll be like, I don't know the answer. Like, I'm not quite sure. I I have no problem saying that. Like, I think it's this, but it could be this. I reserve the right to say like a month from now if I get more information, you know? And I also say, hey, even when I come on really strong and I'm like, we got to do this, you know, like you've got to take it all with a grain of salt.

[00:20:46]Like I'm trying to show you my intention. So don't take it so literally. So look, um there's plenty of, you know, things that are uh challenging about being as transparent or as canderous or maybe as, you know, uh showing all of my vulnerability. But the one thing that serve it serves well is people understand that like you can show up to work um imperfect and you know that's the way we all roll. I I love the I'd rather model imperfection.

[00:21:12]Um I would because by the way uh the one thing that does it it's it's quite freeing, right? I mean you uh you suddenly >> maybe too freeing. Well, but but at the same time, I mean, if you're constantly worried about I've got to be perfect, got to be perfect, got to be perfect, you're overthinking you're overthinking everything and and it and it probably keeps you from being able to properly more um naturally communicate with people.

[00:21:37]>> Yeah. But and I think that the bigger thing which I think you know it frees me, but what I really am trying to do also is free my people, right? Because I think the biggest risk as a CEO and it still exists despite all of the things I've just said. It's a thing I I battle every day. Of course, I want people to come prepared, but I all, you know, so I don't want sloppy work. No, I don't want sloppy work. I want thoughtful work.

[00:22:00]>> You don't want them showing up and saying, "I don't know the answer all the time." Like, "Hey, but boss, but boss, you said that's okay."

[00:22:05]>> Yeah. Yeah. But I So, you know, you don't want people who come in and just like, let me all hang out and I'm not giving you any solutions here. What you want is that really lovely balance of like, hey, I was thoughtful. I was anticipated. I thought about all these things. Here's the things I'm sure.

[00:22:19]Here's the things I'm unsure of. You know, here's the range, right? Like, I want to free people up to have that conversation. That's a way more powerful conversation than like, here's my perfect deck. Here's my perfect slide.

[00:22:31]Please don't ask me anything that goes out the boundaries of this. Because then if I didn't present perfectly, and if the slide wasn't perfect, then I failed.

[00:22:38]I'm like, no, no. Failure is us not having that conversation. Failure is you not being prepared. But failure is certainly not like I gave you the perfect answer, Sukinder.

[00:22:50]Like Yeah.

[00:22:50]>> That's it. That's it. Stop asking, right?

[00:22:53]>> Yeah. Yeah. Yeah.

[00:22:54]>> So, one of the most important, you know, important and powerful tools in leadership is storytelling. We we we we talked about this a little bit briefly.

[00:23:03]Uh but I'm doing a lot of work right now, you know, around the business of storytelling. I was sharing with you that I was just at Nvidia just u for their GTC a couple of weeks ago um teaching at their to their sales folks and um and obviously uh you you already took the time to write a book so you understand what storytelling can mean and and the value in it but when did you first realize storytelling was more than a nice to have skill set. It was actually a leadership tool. you you you were able to actively use to help bring others along with you.

[00:23:41]>> Yeah. Well, maybe the example I'll give you think like you think there's this light bulb moment, but sometimes the light bulb moments don't come from you, they come from somebody else. So, um uh so maybe I'll I'll tell you a lesson about a story that was told about me.

[00:23:55]And it only really occurred to me how powerful it was because it just keeps getting repeated. Okay? And I'm not sure if it's on the internet or not, but certainly. Um so at Google I was a uh you know a young uh mother. I was you know mid-30s. I had a stepson and then I was pregnant with my daughter but I was running a pack and ladam. So I'm running like twothirds of the world geographically and I need to uh I need to I I need to travel >> right? So, we have a sales offsite in China because China was in my remitt entering China at the time. You know, we have hundreds of salespeople in Beijing and we decide to go visit the Great Wall. So, like we're hiking the Great Wall. So, I'm 5 and a half months pregnant, almost six. And I just keep going like I'm like I want to get as far as I can. And so I, you know, we have leaders who stop on the way and, you know, sales people like just people on my team, you know, because there's hundreds of us doing this. And I just keep going. And unbeknownst to me, the team's like, "Wow, Sue Kindra's like keeps going." She's like, "That's right." And she's like, "No, the top of the Great Wall of China or whatever part of it, the route we were doing, right?"

[00:25:03]So I'm like, "I don't think anything of it, right? I I really don't." And you know, we take a picture at the top, what have you. And then all through that sales conference and later the stories that get told about me are like uh Auntie Kinder like she made the great wall with China when she was like 6 months old. I'm like I never intended that to be a story. I didn't even know it was a story. Like why is it a story?

[00:25:21]Right? So you'll learn sometimes the power of storytelling like in unconscious ways. So of course there are other times but like that one sticks with me because people are like so people will still tell that story about me right like 25 years later I'm like wow is it that big a deal? But clearly it was. It sends some very simple message. I'm sure that message was about toughness or resilience or whatever that story is, right? So sometimes when a story gets told to you repeatedly and that has happened throughout my career.

[00:25:47]So how did I learn it? Because often times somebody somebody will come to me and be like remember you said that thing. I'm like did I did I really I said that thing to you? Okay. And it gets repeated back to you. And so what have I learned? I've learned about the power of small moments not big moments.

[00:26:04]Small moments, right? that when told and repeated and of course they've been big moments of storytelling my group but it's often the small gem the small story right the small phrase that is repeatable right so um so how do I translate that yes when I am trying to land a phrase or concept I look for the little nugget not like the big arc does that make sense >> totally because I think that's a great I think that's a great challenge too many people think if I'm going to tell a story it has to be fantastical, right?

[00:26:38]It has to rival uh, you know, a weekend night at the movies, right? It has to The truth is the best stories are often in little moments. It's they're in the the opportunities to to understand someone through a a walk on the Great Wall of China, right? I I know something a little more about you because of the story that would have been shared with me before I would ever meet you. But to your point, it's a very small moment, right? And so, and so I think sometimes as leaders when we think about storytelling, I think most most people want to pile on more messages. Me, I'm like, can you just strip this thing down? I think like because I think people think that like the story is about the width of the story, the breadth of the story, the size of the story. Often it's about the simplicity of the story, right? So, we have a we have a strategy zero, you know, we're in we're at the end of our three-year strategy period. We shared our strategy with investors, you know, in February of 24 um about sort of where we're headed for these three-year chapter. You know, this you know, one of the key tenants of our whole strategy is called the 3x3, three markets, three jobs. What do you think is the one thing investors and zeros, my board, my employees all remember the 3x3? Now, by the way, the 3x3 was nothing other than saying, "Hey, at zero, historically, the company I arrived at is amazing, but we're trying to cover s too many surface areas. Too many jobs to be done for the small business, too many markets. We can't do it well if we're trying to cover this much surface area." And I showed zero like, "Hey, just you know, if you times all the jobs we play in times all the markets times all the customer segments, we end up with something like 600 boxes." It was crazy. So, I needed a way to shrink the world to be like, "Hey, we're going to focus in this period." So we picked the three largest well the three most strategic markets and largest TAM the US UK Australia and we picked the three biggest jobs for SMBs accounting payments and payroll and we're like our strategy is the 3x3 so that's not about maximizing the surface area of the storytelling it's about minimizing it right but it's that plus a very simple story a very simple message fewer words please something catchy does matter like so like these are all the ways maybe I think about storytelling Shrink it. Shrink it to an equation.

[00:28:57]Shrink it.

[00:28:59]>> Wow. So, um, we love D diving into sports on this show, as you know. And I know as a kid, you spent time figure skating. Uh, I guess that's a Canadian thing. You got to do that if you're going to live there.

[00:29:10]>> You got to do that if you're Canadian.

[00:29:11]As importantly, I ran StubHub, which is was which was pretty fun prior to Zero, which had a lot of live sports exposure.

[00:29:18]>> Yeah. No, that's awesome. But you also picked up tennis. Yes. which >> and both uh it's actually funny both disciplines you were u you were described as a ridiculous overachiever in the mindset that you brought to both of those things. Um when you think back to those years, is there a specific moment from athletics uh that still sticks with you today?

[00:29:43]>> Yes. Well, I'll let you in on a secret.

[00:29:45]I was a terrible athlete as a kid. I mean, in fact, if you had seen me in gym class, you would have I was a classic person, picked last. Um, because in like the classroom on anything academic, I was picked first. In the gym, I was picked last. So, maybe the more relevant question is from tennis because I picked up tennis. So, I learned I was more maybe had more coordination than I thought. In my 20s, I learned how to ski. I became, you know, much more fit.

[00:30:09]Um, you know, just like I live in California where everybody's out all the time. And I picked up tennis more specifically during co. So I had learned to play tennis when you know I was I had young kids if I couldn't didn't have enough time then co of like I just became my thing. So I now play tennis three times a week. Maybe maybe the most important thing for me about that experience. Um first of all like anything building confidence but number two in tennis like you know I am pretty intense people I wouldn't say I'm getting any better by the way. I mean I'm just very consistent. Um, but the thing I've learned about tennis is, you know, in trying to master it, I read all those books, you know, winning ugly, you know, the inner game of like I've read them all, you know. Um, and I'd say the most important lesson for me that is in tennis, but also transcend transcends tennis. Um, first of all, Brad Gilbert's like winning ugly. I love that. Like you know remember I this idea of imperfection so often like you know when I am winning let's say I'm up five games to two in a set and then all of a sudden I find myself at like 55 and I'm like what happened I had this right then I just think about Brad Gilbert's winning ugly. He's kind of like it doesn't matter how you win, just just win, you know? I mean, so I love this concept that like you have to sit down, you have to reset. You know, you can think you're far ahead and the minute you do and you lose focus, you somehow find yourself falling behind. And in that moment, don't curse yourself for being behind.

[00:31:34]Just like just remember winning is almost always ugly. So that helps me a lot. Um, and then the second thing about tennis is, you know, I think it comes from the inner game of tennis. I think they said I I think I think there's a phrase that goes something like you know we play tennis to learn how to focus and I you know and I think that's true cuz tennis is a game of focus but I also now believe the reverse which is by playing tennis I learn how to focus better for my job. So I think this other idea that like tennis is incredibly about like you have to forget the last shot think about the next shot and just learn how to kind of focus on only this shot and kind of forget the past and you know even forget the future. I just really love that and it it really does help me. Uh, you know, I think it's another lesson that sort of transcends sports like I mean I will tell you like you know I say to my team like hey you know I was really I've been really grumpy for the last month like I can feel it. I know it right. So like while I can curse myself for being grumpy about something at work and enduring like I'm irritated about you know some situation whatever enduring I can also just say that be like okay I have been I need to park it and I need to move forward. So like I think this idea of giving yourself grace, you know, to have had those bad moments and then sort of just like remind yourself you can still win ugly. I which means it doesn't have to have been perfect. It just matters that you reset. And it's never too late to reset. Okay, you had like one bad day, you had one bad game, you had five bad games, you had five bad weeks. It kind of doesn't matter, right?

[00:33:01]Like it is what it is. You kind of have to take a m You have to take this moment to reset.

[00:33:05]>> Can can you fast forward that to your time at zero? You're now here you are.

[00:33:10]You're a leader.

[00:33:12]>> Maybe a moment when you when this idea winning ugly became u was something you were able to kind of use as you kind of helped the company helped helped your team navigate uh an opportunity.

[00:33:25]>> Sure. Sure. Yeah. I mean there've been a few moments at zero you know one that was painful but necessary and what I think the team understood when I arrived at zero it was winning but not winning enough. So the company was growing very fast like over 25% year-over-year but unprofitable and I arrived at the company in 2022 just right after the co boom you know where everything's worth a lot but companies are starting to look at profitability so you can see outside of the company like the market is starting to it's already maybe turned and is starting to crash is companies that are high-flying and big but unprofitable you know kind of fall from glory their market caps what have you so I you know I came into zero I'd already obviously had this thesis in my boarding interviews, but I was like, I'm pretty sure we're going to need to do a layoff, you know, like we're just over our skis in terms of the number of people like many other tech companies we hired. And so before um so I arrived in the I guess I was hired November. My first official day in the seat was February 15. It was February 1st. So I had 3 months to learn. So by the time I had come into the February 1st, you know, take over the CEO, I had already met with over maybe a thousand people at zero like surveys, not just met with like meetings, surveys, teams. So like like I had a quarter of the population, you know, that I'd interacted with in some way. I visited all our offices. I'd had Mckenzie come in and do an entire benchmarking study on the size of our groups, you know, to validate whether or not we were as over our skis as we thought. And so on my first day on the job, I did an all hands and I talked about how amazing Zero was and I shared benchmarks on how we were doing relative to SAS. I was like, "Hey, this is what I've learned over there. This is what you've told me. These are things we do well. These are things we do poorly. And now I want to show you how we stack up against other global SAS players." And I showed them benchmarks on how we graded some benchmarks and really poor on others. So I kind of set the stage on my first all hands that like this is what I assessed and found and and the very first questions I got from people were like and silently were like is she going to do a layoff? And a month later we laid off 800 people.

[00:35:32]>> Wow. Laid them off. So that was brutal and painful. But by the time we laid them off, people understood that like to win like we're going to do need to do more than just grow fast and add people because they had seen the data. So that was like a winning ugly moment. Like did it feel like winning? No. You were like affecting hundreds of people. But did Zero see the necessity of it ever having after having done that first all hands and just like ripping off the band-aid?

[00:35:59]It was brutal. You know, our NPS went from, you know, in very positive territory to negative overnight. I was 6 weeks into the job. But we just like but people but you know that day I also got into my private Slack. I got, I don't know, 20, 30, 40 DMs from employees I'd never met saying things like, "How are you? Are you okay? I could tell that all hands where you announced layoff was really hard for you. Um, thank you for doing that. That was really painful. We all know it needed to happen." So I had all of these messages of support checking in on me, you know, thanking me for making the hard decision, thanking me for sharing the data, uh recognizing the necessity of the moment. And in fact, of course, we turned profitable and, you know, and the company had money to then invest in new, you know, uh areas of opportunity while staying profitable. Um so that's an example of a winning ugly moment. In the moment, it was not winning. It was, but it was a necessary to win move and it was ugly.

[00:37:03]>> I I'm sitting here and I'm like intensely like fired up now just because you you you bring that it's it's so many people you have these wonderful just casual conversations and it's all good but like you I could feel like you were bringing you're bringing a spirit to it.

[00:37:16]Um I just want to I I I'd really like to thank you for being a corporate competitor with us today and uh thanks for bringing all that energy.

[00:37:23]>> Thank you for having me.

[00:37:27]Man, there was so much energy on the other side of this call. I I I felt like I could run through a wall for Sukindra.

[00:37:32]What what a what a leader and and I love the way she just is she acknowledges her energy and she's she's so and the fact that her competitiveness and her creativeness allow her to kind of probably bring people further than any of them expected when they came to work for her. Um I could I could see so much so much to be gained there. But there were three amazing takeaways for me, three things that I uh made notes of and will uh post on my wall because they were so good. I loved that entire discussion about the who matters more than the what. If you're looking to advance in your career, you're looking to make a move so that you are heading in the right direction. um the who who are you going to work with who not not the company but but the people that you're going to be around are they going to do are they going to open doors for you in a way that maybe intellectually not just physically opening doors but the idea that they the who will drive more about what you'll get out of a relationship and experience than what it is you do or where it is you'll work right find others whose values you share um who you can have a mutually beneficial relationship with because that's really what's so important. What a what a great lesson that is. Too often we're we're caught up in the title or the the size of the company or the the wow factor. Be focused more on who it is you get a chance to work with. Uh my second big takeaway actually came right at the beginning of the conversation when she talked about the importance as you're thinking about what you want to do next, right? And and there are so many things out there that we want to try, but our fear of missing out has to be greater than our fear of failure. Which means, you know, uh if if we know we want to do it, we can't really increase that anymore. That that's that is what it is.

[00:39:20]We have to reduce our fear of failure.

[00:39:24]And I love the way she talked about that and the idea that um you have to premortem the failure states that would come from uh from from actually cha uh chasing something. Actually note what it is that could happen to you if you uh if you weren't successful. Um and you know if it's not you sometimes might realize it's actually not as traumatic as you as you might have thought. So thinking about it and reducing those fears one by one really great. My last great takeaway was in our conversation around storytelling. She was so good there about talking about the power of small moments, right? It's not the width of your message. It's not the breadth of it. It's not the the grandiose nature of it. Sometimes the best stories you can tell are simple. It's the simplicity of it. She said, "It's the small moments when they're created and when they're when they're shared with others, they're the most repeatable. They're the ones that others will remember. And thus they're the best stories. I gained so much from Sakinder today. I hope you did as well. And I appreciate you.