The Exchanges

Q totally agree with you. I guess you're saying there about kind of choosing the three percent that didn't like it over the 97. I mean, it's brutal on yourself, but it goes to a kind of a question of you questioning yourself. When you think about questioning yourself, do you feel like you're enough, and how do you feel about the constant pressure to be enough and to be more?

A Oh, my God. This is so, this is such a deep rabbit hole, so I'll give you the quick, quick version. Do I feel like I'm enough? Absolutely not. Not at all. Not at all. Now, do I realize that I need to manage that emotion? A hundred percent. I'll tell you my journey there. So it starts as a kid, like everything. So go back to my parents, amazing parents from India. You know, the psychology of immigrants, and particularly, you know, from some countries, there's sort of this desire to strive and to be great and successful, and some element of, like, comparing yourself to others, and my parents definitely had that And so I kind of grew up around all of that, like them comparing themselves to their friends, you know, how they're successful, they all are, but then also the number one thing, which is comparing your kids to each other. And I remember when I was a kid, I was like eight or nine years old, Pittsburgh, Pennsylvania. My dad shows me a Time magazine and it has Bill Gates on the cover, founder of Microsoft. At the time, he's the youngest billionaire in the world or youngest self-made billionaire. And my dad said, maybe you could do something like this someday. And I was like, that was when the bar Was set infinitely high. I still remember that moment so well. And then through all of my childhood, it's like, oh yeah, did you see what this other kid is doing? He got into college…

AI assessment note: “Do I feel like I'm enough? Absolutely not. Not at all.”

Q often feel like I have to be strong, you know, my mother's got MS, and there's, you know, some, it's challenging there, and I feel like I have to be strong for her, and I can't show those chinks in the armor. Do you, as a father, a husband, feel like you have to be strong for them, and you can't be all revealing, because you are the strong one?

A With the kids, I do feel like that, you know, so I do feel, not that I have to be strong, because we're big into, you know, vulnerability as a family, but that I probably can't share everything, because I don't know if they're ready for it. Like, they have their own stuff they're dealing with, so we connect on some of these things, but more, like, at the level that I feel like they're comfort at. Our kids are, you know, 1512, and nine, so, you know, they're still developing as people With Monika, I don't feel like I have, my wife, I don't feel like I have to be strong, but I feel like I can't just dump everything on her, right? So that's that. But where what you said makes total sense is, at work, I do feel like there is an element of leadership that's about confidence, right? Confidence is infectious, you know? And so I think if the leader doesn't seem confident, then it may be a fait accompli, right? That things just aren't going to happen. And so, The reality is I'm not always confident about everything, including, by the way, as we were talking before, not confident about the nature of reality, right? So, okay, how can you be confident about anything if you're not confident about that? And so, as a leader, I feel like I do sometimes have to be strong. Now, I have tried to mix in, as we can talk more about, vulnerability into my leadership, and so we're big on it at Gainsigh…

AI assessment note: “With the kids, I do feel like that... With Monika, I don't feel like”

Q totally agree with you. I guess you're saying there about kind of choosing the three percent that didn't like it over the 97. I mean, it's brutal on yourself, but it goes to a kind of a question of you questioning yourself. When you think about questioning yourself, do you feel like you're enough, and how do you feel about the constant pressure to be enough and to be more?

A Oh, my God. This is so, this is such a deep rabbit hole, so I'll give you the quick, quick version. Do I feel like I'm enough? Absolutely not. Not at all. Not at all. Now, do I realize that I need to manage that emotion? A hundred percent. I'll tell you my journey there. So it starts as a kid, like everything. So go back to my parents, amazing parents from India. You know, the psychology of immigrants, and particularly, you know, from some countries, there's sort of this desire to strive and to be great and successful, and some element of, like, comparing yourself to others, and my parents definitely had that And so I kind of grew up around all of that, like them comparing themselves to their friends, you know, how they're successful, they all are, but then also the number one thing, which is comparing your kids to each other. And I remember when I was a kid, I was like eight or nine years old, Pittsburgh, Pennsylvania. My dad shows me a Time magazine and it has Bill Gates on the cover, founder of Microsoft. At the time, he's the youngest billionaire in the world or youngest self-made billionaire. And my dad said, maybe you could do something like this someday. And I was like, that was when the bar Was set infinitely high. I still remember that moment so well. And then through all of my childhood, it's like, oh yeah, did you see what this other kid is doing? He got into college…

AI assessment note: “Do I feel like I'm enough? Absolutely not. Not at all.”

Q Final one. What do the next five years hold for you, Nick? What's the grand plan?

A I would love to take Gainsight public because, and I have no idea if it will happen or not, but because, I mean, certainly there's an ego part of it. There's a part that I really believe in our business and I want to do it. Part about pleasing my parents, so that's certainly one thing. A second thing is coping with my kids growing up. That's going to be very hard, um, way in the distant future for you, Harry, but nothing at all at work is at all anywhere comparable to the, the fear I have of the kids growing up and like, you know, them moving out of the house. And we still have a number of years, but that's one that I'll be soaking in a lot. And then I think leaning even more from a work perspective into what these things that I'm really passionate about, you know, I'm passionate about companies being authentic and being themselves and people trying to be what we call a human first business, trying to be more of your real human self. And I would love to just like see that materialize even more. We've leaned into it a lot, but I just like to take that to the next level. We've even toyed with the idea of writing a book on some of these topics. So who knows?

AI assessment note: “I would love to take Gainsight public because, and I have no idea if”

Q That is a total nightmare. I think one of the results of me being unpopular when I was younger was like, now I'm just like this inherent people pleaser, and I like to say yes to everything, but it's a real problem for me, Nick, because I let people down because I say yes to everything. Are you a people pleaser? How do you think about that today?

A Oh my god, Harry, like, a hundred percent. It's funny that it's really, I feel seen talking to you because I absolutely want people to like me and constantly Am not sure whether people really like me or not, and therefore really, really try hard to be whatever people need to have them like me. There's actually, this is so cheesy, but there's a Taylor Swift song called Mirrorball, and it's, I'm a mirrorball, I can be anything you want, that you want me to be. The idea is you reflect like a mirrorball reflects, you know, in a disco ball, right? It reflects the light coming at it from all sides, and so I just want to be whatever people want me to be that will make them like me, you know, and so there's that, there's that feeling. Now, I have to, Like you, Harry, I can't imagine that. I'm a CEO. I've, like, run a company. It can't just be about people liking me, right? Gotta make good decisions, and sometimes those aren't about people liking me, so I have to check myself, but my natural inclination from this sort of childhood is to want people to like me, hundred percent.

AI assessment note: “Oh my god, Harry, like, a hundred percent.”

Q I want to touch on the loneliness, but while we're on that, you know, do you feel the weight of responsibility? You are the conductor, and you are the one driving this, and there's a huge amount of responsibility and weight. Do you feel that?

A Oh, yeah. All the time. I definitely feel it. It's interesting because we, as you mentioned, did a financial transaction where we knew investors, and, you know, because of that, all of our employees were able to, you know, get very well-deserved liquidity, and some of our early investors did as well. So that made me feel a little bit more like, okay, this isn't going to be a total failure. Cause I, I'll be honest, even when, you know, we're like a hundred and something million of AR now. And even when we were like, is this going to be a total failure? Is it going to go nowhere? And I think a lot of CEOs feel that much more fear of failure than aspiration for success. And so now I have a little, just a little bit less fear of failure, just a tiny bit, which actually is allowing me to feel like, A little more strive for the success, like go big, like how to make this huge, you know, but it feels like it's on my shoulders. It totally does, you know, and it's, that's not true. We have so many people here, but sometimes it feels like that.

AI assessment note: “Oh, yeah. All the time. I definitely feel it.”

Q often feel like I have to be strong, you know, my mother's got MS, and there's, you know, some, it's challenging there, and I feel like I have to be strong for her, and I can't show those chinks in the armor. Do you, as a father, a husband, feel like you have to be strong for them, and you can't be all revealing, because you are the strong one?

A With the kids, I do feel like that, you know, so I do feel, not that I have to be strong, because we're big into, you know, vulnerability as a family, but that I probably can't share everything, because I don't know if they're ready for it. Like, they have their own stuff they're dealing with, so we connect on some of these things, but more, like, at the level that I feel like they're comfort at. Our kids are, you know, 1512, and nine, so, you know, they're still developing as people With Monika, I don't feel like I have, my wife, I don't feel like I have to be strong, but I feel like I can't just dump everything on her, right? So that's that. But where what you said makes total sense is, at work, I do feel like there is an element of leadership that's about confidence, right? Confidence is infectious, you know? And so I think if the leader doesn't seem confident, then it may be a fait accompli, right? That things just aren't going to happen. And so, The reality is I'm not always confident about everything, including, by the way, as we were talking before, not confident about the nature of reality, right? So, okay, how can you be confident about anything if you're not confident about that? And so, as a leader, I feel like I do sometimes have to be strong. Now, I have tried to mix in, as we can talk more about, vulnerability into my leadership, and so we're big on it at Gainsigh…

AI assessment note: “With the kids, I do feel like that”

Q I ask another one, which is, you mentioned kind of, like, egotistical element there. Another thing that a lot of people denote importance and success Because attitude is obviously money. How do you think about relationship to money in particular? It's one where I often think, and you know, like, bluntly, I'm happiest when I'm, you know, walking with my mother and my brother, and that's free, and they're family.

A Yeah, it's interesting, because I think that, I know there's, there's obviously discussions on both extremes here. Like, one extreme is, it doesn't matter at all. Another extreme is, it matters infinitely, and the more you get, the more happy you'll be. I personally come down somewhere in between, where I think there's a lot of the things that I like in life that are completely free. And just like you said, hanging out with her kids or, you know, spending time with my parents or exercising most, you know, not free, but relatively inexpensive listening to music and so on. But I also know the privilege that like, you know, we've very privileged and we have money and all that stuff. And so I'm not worried about the next, you know, paycheck or somebody getting sick and not being able to afford it. And so I think there's definitely like a level of comfort that money brings. And I think that's a big privilege for people to have it. And I have so much empathy for people who don't have that. So it's hard for those people to talk about personal development and vulnerability and loneliness, because they're literally just trying to figure out how they're going to get their kids fed or get them into pay for their school or whatever, you know? And so I think there's a level where you feel comfortable. And then beyond that, yeah, I'm with you.

AI assessment note: “I personally come down somewhere in between”

Q That is a total nightmare. I think one of the results of me being unpopular when I was younger was like, now I'm just like this inherent people pleaser, and I like to say yes to everything, but it's a real problem for me, Nick, because I let people down because I say yes to everything. Are you a people pleaser? How do you think about that today?

A Oh my god, Harry, like, a hundred percent. It's funny that it's really, I feel seen talking to you because I absolutely want people to like me and constantly Am not sure whether people really like me or not, and therefore really, really try hard to be whatever people need to have them like me. There's actually, this is so cheesy, but there's a Taylor Swift song called Mirrorball, and it's, I'm a mirrorball, I can be anything you want, that you want me to be. The idea is you reflect like a mirrorball reflects, you know, in a disco ball, right? It reflects the light coming at it from all sides, and so I just want to be whatever people want me to be that will make them like me, you know, and so there's that, there's that feeling. Now, I have to, Like you, Harry, I can't imagine that. I'm a CEO. I've, like, run a company. It can't just be about people liking me, right? Gotta make good decisions, and sometimes those aren't about people liking me, so I have to check myself, but my natural inclination from this sort of childhood is to want people to like me, hundred percent.

AI assessment note: “Oh my god, Harry, like, a hundred percent. It's funny that it's really”

Q I want to touch on the loneliness, but while we're on that, you know, do you feel the weight of responsibility? You are the conductor, and you are the one driving this, and there's a huge amount of responsibility and weight. Do you feel that?

A Oh, yeah. All the time. I definitely feel it. It's interesting because we, as you mentioned, did a financial transaction where we knew investors, and, you know, because of that, all of our employees were able to, you know, get very well-deserved liquidity, and some of our early investors did as well. So that made me feel a little bit more like, okay, this isn't going to be a total failure. Cause I, I'll be honest, even when, you know, we're like a hundred and something million of AR now. And even when we were like, is this going to be a total failure? Is it going to go nowhere? And I think a lot of CEOs feel that much more fear of failure than aspiration for success. And so now I have a little, just a little bit less fear of failure, just a tiny bit, which actually is allowing me to feel like, A little more strive for the success, like go big, like how to make this huge, you know, but it feels like it's on my shoulders. It totally does, you know, and it's, that's not true. We have so many people here, but sometimes it feels like that.

AI assessment note: “Oh, yeah. All the time. I definitely feel it.”

Q I totally get you. And I understand that kind of the liquidity in some respects helps a little bit. You mentioned the loneliness. How and why do you feel lonely? I guess I look at me and it's like, you know, as I said, I've kind of isolated myself from most parts of the world in the last few months. Um, like why do you feel lonely, my friend?

A Yeah, it's interesting. It's a great question. I really, if you observed my life, you'd say there's no way that guy is lonely, because he's on, runs a business where he has, you know, a hundred and something meetings a week with different people all around the world, and he's connected to all these people, and on the weekends, I hang out with my kids and my wife, and I see some friends, so why do I feel lonely? I'm not sure, like, I think part of, there's two emotions probably that are there. One is, there's still this emotion of Hey, do those people really like me or not? So like, am I really in the club or not? Am I, am I really their friends? You know, and in business, you probably get this area where it's like, well, maybe not. A lot of people have an incentive to want to like me because I can do stuff. Right. And then the second kind of feeling is, do I feel like I fit in? In other words, do they care about what I care about? And especially when I talk about like this conversation, honestly, it's making me feel a little less lonely because I care about all this stuff, but not Not everyone seems to emote that. And actually what I figured out is actually those people under the covers do care about it, but they don't always feel open to talking about it. So what, basically what ends up happening is a lot of conversations that don't feel very real, right? That are about people…

AI assessment note: “there's two emotions probably that are there. One is, there's still this emotion of”

Q go for beers with their buddies, and they have a great time, and they start at nine, and then they have the weekend off, and they earn okay, but not great, and they're just super chilled and super happy, and I look at them, and I'm like, why can't I be like that? Because I'm on the other side, but I'm never fucking happy. Like, do you ever feel that?

A Oh, totally, but I guess I've, I have felt that, and I still feel some of that, and I've kind of come to a conclusion, which is I am a person that is unique on my own, just like everyone else is, right? They all are unique, and this identity of all of these things about loneliness, and wanting to be liked, and not feeling like enough, and pleasing my parents, and everything else is who I am. There is no other alternate reality, and I have one choice, Which is, I can either know who I am and love who I am, or I can hate who I am and try to be something different. And the only thing I've done personal development-wise, I haven't changed any of it. I'm just as, like, egotistical and wanting to strive and not feeling enough as I've ever been. Maybe more. But I know it, and I can see it, and I can manage it when it's getting, like, unhealthy. Like, I can disconnect from the internet stuff, and I can check myself out, and I can hang out with the kids and But I know that I'm not going to change it, and I don't really want to. I love myself. That's the thing that's the bottom line of this, is as much as all these things sound sad, the development has been, for myself, I'm the best version of myself I can be. And that's what I want. I don't want anyone else.

AI assessment note: “Oh, totally, but I guess I've, I have felt that, and I still feel”

Q that's actually important, unlike Venture. But I do want to start with kind of a little bit of a different one, but it's like, obviously we're going to talk about mental health on this show. So I want to start with the question of like, when did you realize that mental health was Was a challenge for you, and something that you had to be really mindful and cognizant of?

A Yeah, it's interesting. I think if you had asked me in my twenties, all the way to maybe 30, is, like, mental health something you think about? I'd say, no, not at all. I know, I know people struggle with it. It's not something I think about at all. I generally consider myself, and I still do, an optimistic, positive person, so no, I never thought that it was something that I was thinking about, and then I actually got into a lot of self-development. I joined a CEO peer group International group called YPO, Young Presence Organization, and some folks listening probably heard of it, and you might think it's some business networking, talking to other CEOs about your business, but it turns out to be, at least the group I'm in, extremely, extremely about personal development, and we bring in professional facilitators and try to be very vulnerable and candid about our lives, and so I just kind of unearth a lot of stuff, and we'll talk about it later. It's not stuff that I judge or that needs to be fixed, but stuff that just Is who I am and help me understand the different emotions and feelings that I have. So that's one thing that happened. The second thing, which we can talk more about too, is this is an area my wife is super passionate about. She actually went back to school to get a master's in educational psychology, and she started an online community for kids to talk about men…

AI assessment note: “I think if you had asked me in my twenties, all the way to maybe 30”

Q Don't laugh. Do you have like commonalities in when you feel lonely? So I often feel lonely 11 till one, 11 p.m. to one a.m. I feel really lonely then. There are commonalities of when you feel lonely.

A Yeah, it's interesting, because it's, like, basically evenings, when all of, you're going back to your whole being on stage, when the lights have turned down, the stage is gone, the band's gone away, and especially, like, if the kids are doing something, my wife's doing something, yeah, that, that's, like, lonely. That feels very lonely, you know, but Harry, what's interesting is, If I'm exercising, or reading a great book, or just doing something that brings me in zone, I don't feel it. You know, like, actually, the other day, I went to dinner, which was awesome, having a real dinner again, with one of our, one of my people that works with me, and I, and I went to dinner in my town, I biked home, like, I was a little bit buzzed, I had, like, one, you know, one glass of scotch or something, and I was biking home, and I felt bliss, because it's that feeling of, like, the endorphins and the energy, even though I was, like, alone again. I felt this bliss listening to music, and so when I'm able to use the time alone to feel that, be in the zone, I feel great. If I'm alone with my thoughts, that's when I feel lonely.

AI assessment note: “basically evenings, when all of, you're going back to your whole being on stage”

Q Totally. I read one of your posts earlier, and this is unfair of me, and so you can kill me for it, but it's like, I was kind of pissed off that people didn't respond well, and obviously, 99% did, but even the one percent that didn't respond well to the vulnerability, I'm like, seriously?

A Yeah, it's, it's interesting, Harry, so that, this post talks about me, you know, basically talking about vulnerability. It was the first time I stepped out on this, into our customer kind of stage. We have a conference every year, and so in front of 3000 people, I talked about loneliness and high school, and All these things. And here's another problem. In this post, I talk about the, like, three people that said, oh, you know, I really wish our, you know, CEO would just, like, be, like, tough and strong and just talk about winning and stuff like that. And then, you know, I didn't talk about the 97% of people or whatever that were like, that's amazing, and you're so brave for doing it, because I always remember those three percent of people or the one percent of people. Now, I think over time, Harry, that post was, like, six years ago. Over time, I think some of those people have actually changed their mind. And that's one thing that gives me so much, like, happiness and gratitude, is watching people over time embrace this vulnerability concept, even if they were skeptical early on.

AI assessment note: “because I always remember those three percent of people or the one percent”

Q Because you're never satisfied. And so I guess my question to you is, like, when you reached any of the milestones that you got, whether it was getting to the good college, getting the good job, becoming CEO, did it ever feel as good as you thought it would?

A It feels good. So it's actually not like I always feel bad. It's more like I'm always reminded of, like, there's always more, right? And I actually believe that there's something, some part of this that's healthy. Some, I'm sure many people see, you know, Hamilton, Alexander Hamilton, and like, The play and the musical is all about him never being satisfied, never being enough. It's like, I mean, his whole strive is about wanting to do more. And so what I feel, Harry, is like, when those things happen, like when we announced our big, you know, financial transaction with Vista Equity Partners, that felt awesome for like a day. And then it still feels like some pride, but it was like, okay, now I need to do more. Because now it's like, well, yeah, a billion dollars, but that's, that our company, you know, valuation was a billion, but that's just a billion dollars. What about the companies that are ten billion? Or a hundred billion, right? And so it's, it's like you feel those kind of highs, but then you're reminded back to reality. I don't necessarily think it's all bad, because it also makes people like you and me strive, right? And actually, when I was a kid, so my brother, who's, I'm super close to, he's three years younger than me, he's always been way more wise and ahead of the times than me, and I remember him telling me that the goal of life is not always just happiness. L…

AI assessment note: “that felt awesome for like a day. And then it still feels like some pride”

Q positive, and the chip on the shoulder can be great. Can I ask one final thing before we go into a quick fire? And it's just like, do you feel that there's, like, enough vulnerability at all in today's ecosystem? Do you think they're hiding it? Do you think they're unaware of it? And what can we do to be more welcoming of vulnerability and, like, realness in this ecosystem?

A Oh, yeah. I mean, that's why I'm so glad you're doing this, and I'm very honored to be part of it. Is I just hate it. I hate the lack of openness and vulnerability. I think it holds everyone back because everyone feels like they have to pretend and always just be acting all the time about how successful and awesome they are. And especially right now, Harry, where it's like every single day, it's like, oh, wow, this company went public. This one raised this huge round, et cetera. And all these huge valuations, which is awesome. I'm so happy for people, but I know those people are wondering the same things that I were was, which was Do we really deserve that? Are we really going to ever be worth anything? Is this going to be successful? My parents are going to be happy with me. Do my employees like me? All the same questions that you and I have. I think a lot of people have them, but because we don't talk about it, we all feel lonely, right? That's the problem. Because we don't talk about, we see everyone else crushing and killing it. And so one thing I try to do is just throw it all out there. This complete like word vomit of everything I've said in the show, right? It's just everything about who I am And I, I think other people have those same feelings, and going back to that conference, where I spoke for the first time about this, the 97% of people that came up to me and said,…

AI assessment note: “I hate the lack of openness and vulnerability. I think it holds everyone back”

Q Okay, so speaking about kids fitting in, I, I read one of your pieces, and you said that you were unpopular growing up, and I wanted to start on that, and it's like, why do you think that was, and how do you think that impacted you?

A Yeah, it's interesting, because people that know me only now are usually pretty surprised that I was a total introvert growing up, and I think, I don't know exactly why it happened, but I have some hypotheses. The facts are this, which are kind of sad. I grew up in Pittsburgh, Pennsylvania, For whatever reason, I never felt like I fit in, so I ate alone at lunch, which kind of, lunch is like the litmus test, especially in American school, probably all around the world. It's the litmus test, like, are you with, like, all the friends around you laughing, or are you, like, on your own, and I was ate alone every day, kindergarten through 12th grade, like, the entire time, all the way before college, and never felt like I fit in. Frankly, I felt so embarrassed that I was eating alone that I would go hide in places to eat, like, I go to the computer lab and, like, pretend to be programming and just eat my lunch, and there was no iPhone or, you know, music back then to listen to, so you were just kind of, like, really, like, living in your own loneliness. Now, why was that? I'm not sure. Obviously, today, I'm very comfortable with people and probably much more extrovert than the average person, but I think there was probably a few reasons. One of them, I think, was probably just, like, feeling like I didn't fit in because I was the, like, the only, like, Indian kid and probably the on…

AI assessment note: “feeling like I didn't fit in because I was the, like, the only, like, Indian kid”

Q that's actually important, unlike Venture. But I do want to start with kind of a little bit of a different one, but it's like, obviously we're going to talk about mental health on this show. So I want to start with the question of like, when did you realize that mental health was Was a challenge for you, and something that you had to be really mindful and cognizant of?

A Yeah, it's interesting. I think if you had asked me in my twenties, all the way to maybe 30, is, like, mental health something you think about? I'd say, no, not at all. I know, I know people struggle with it. It's not something I think about at all. I generally consider myself, and I still do, an optimistic, positive person, so no, I never thought that it was something that I was thinking about, and then I actually got into a lot of self-development. I joined a CEO peer group International group called YPO, Young Presence Organization, and some folks listening probably heard of it, and you might think it's some business networking, talking to other CEOs about your business, but it turns out to be, at least the group I'm in, extremely, extremely about personal development, and we bring in professional facilitators and try to be very vulnerable and candid about our lives, and so I just kind of unearth a lot of stuff, and we'll talk about it later. It's not stuff that I judge or that needs to be fixed, but stuff that just Is who I am and help me understand the different emotions and feelings that I have. So that's one thing that happened. The second thing, which we can talk more about too, is this is an area my wife is super passionate about. She actually went back to school to get a master's in educational psychology, and she started an online community for kids to talk about men…

AI assessment note: “if you had asked me in my twenties... I'd say, no, not at all.”

Q Because you're never satisfied. And so I guess my question to you is, like, when you reached any of the milestones that you got, whether it was getting to the good college, getting the good job, becoming CEO, did it ever feel as good as you thought it would?

A It feels good. So it's actually not like I always feel bad. It's more like I'm always reminded of, like, there's always more, right? And I actually believe that there's something, some part of this that's healthy. Some, I'm sure many people see, you know, Hamilton, Alexander Hamilton, and like, The play and the musical is all about him never being satisfied, never being enough. It's like, I mean, his whole strive is about wanting to do more. And so what I feel, Harry, is like, when those things happen, like when we announced our big, you know, financial transaction with Vista Equity Partners, that felt awesome for like a day. And then it still feels like some pride, but it was like, okay, now I need to do more. Because now it's like, well, yeah, a billion dollars, but that's, that our company, you know, valuation was a billion, but that's just a billion dollars. What about the companies that are ten billion? Or a hundred billion, right? And so it's, it's like you feel those kind of highs, but then you're reminded back to reality. I don't necessarily think it's all bad, because it also makes people like you and me strive, right? And actually, when I was a kid, so my brother, who's, I'm super close to, he's three years younger than me, he's always been way more wise and ahead of the times than me, and I remember him telling me that the goal of life is not always just happiness. L…

AI assessment note: “that felt awesome for like a day. And then it still feels like some pride”

Q I totally get you. And I understand that kind of the liquidity in some respects helps a little bit. You mentioned the loneliness. How and why do you feel lonely? I guess I look at me and it's like, you know, as I said, I've kind of isolated myself from most parts of the world in the last few months. Um, like why do you feel lonely, my friend?

A Yeah, it's interesting. It's a great question. I really, if you observed my life, you'd say there's no way that guy is lonely, because he's on, runs a business where he has, you know, a hundred and something meetings a week with different people all around the world, and he's connected to all these people, and on the weekends, I hang out with my kids and my wife, and I see some friends, so why do I feel lonely? I'm not sure, like, I think part of, there's two emotions probably that are there. One is, there's still this emotion of Hey, do those people really like me or not? So like, am I really in the club or not? Am I, am I really their friends? You know, and in business, you probably get this area where it's like, well, maybe not. A lot of people have an incentive to want to like me because I can do stuff. Right. And then the second kind of feeling is, do I feel like I fit in? In other words, do they care about what I care about? And especially when I talk about like this conversation, honestly, it's making me feel a little less lonely because I care about all this stuff, but not Not everyone seems to emote that. And actually what I figured out is actually those people under the covers do care about it, but they don't always feel open to talking about it. So what, basically what ends up happening is a lot of conversations that don't feel very real, right? That are about people…

AI assessment note: “a lot of conversations that don't feel very real, right?”

Q So like, when you think about your identity tied to game site, how do you think about that? And is that a challenge for you, like it is for me?

A Oh, a hundred percent. Yeah, first of all, it's funny. We all have like aversion to words, and there's a word that I hate, and everyone says it as a compliment, and I hate the word, which is exit, exit, exit. I always tell people, look, we didn't exit Gainsight. We had a new investor. I'm just as all in as I've ever been. It's totally true. And I want to see this true as long as I can. And part of it's because I really believe in the business and why we do it in the mission. But part of it, Harry, is exactly what you said. It's my identity. I couldn't imagine not doing Gainsight. Like, it is so tied to me. And I think the more you lean into some of the external stuff, the more that that happens, right? Like, it feels like, oh, Gainsight's me. I'm Gainsight, right? That's not totally true. We have 800 people at Gainsight, and they work so hard, and we have tens of thousands or hundreds of thousands of customer people, people like our customers, and so it's not just me, but sometimes it does feel like, okay, it's on my shoulders, it's my identity, and I have a hard time imagining myself without Gainsight. Now, I don't hope I ever have to, because I'd certainly love to do this as long as I can, but I'm also not naive that things don't go on forever, right? Like, they don't. Like, I don't, do you know Ozymandias? Have you heard of Ozymandias?

AI assessment note: “It's my identity. I couldn't imagine not doing Gainsight. Like, it is so tied to me.”

Q Don't laugh. Do you have like commonalities in when you feel lonely? So I often feel lonely 11 till one, 11 p.m. to one a.m. I feel really lonely then. There are commonalities of when you feel lonely.

A Yeah, it's interesting, because it's, like, basically evenings, when all of, you're going back to your whole being on stage, when the lights have turned down, the stage is gone, the band's gone away, and especially, like, if the kids are doing something, my wife's doing something, yeah, that, that's, like, lonely. That feels very lonely, you know, but Harry, what's interesting is, If I'm exercising, or reading a great book, or just doing something that brings me in zone, I don't feel it. You know, like, actually, the other day, I went to dinner, which was awesome, having a real dinner again, with one of our, one of my people that works with me, and I, and I went to dinner in my town, I biked home, like, I was a little bit buzzed, I had, like, one, you know, one glass of scotch or something, and I was biking home, and I felt bliss, because it's that feeling of, like, the endorphins and the energy, even though I was, like, alone again. I felt this bliss listening to music, and so when I'm able to use the time alone to feel that, be in the zone, I feel great. If I'm alone with my thoughts, that's when I feel lonely.

AI assessment note: “basically evenings, when all of, you're going back to your whole being on stage”

Q Does that hurt when you hear your parents say that?

A It hurts, but it's not, you know, I think all these things are about what you're saying to yourself. It's not about like my parents. They're, they're wonderful people. They're just trying to You know, they are who they are, right? It's actually about what am I judging myself? It's about last night, Harry, you know, worst thing you can do is pull out Twitter, like, before you go to bed, like, there's very few things that are worse in your life, and, like, Twitter is just, like, an advertisement of all the people that have done things that you haven't done. So yesterday, it's like, and by the way, like, these people are, I've never met her, the CEO of, like, uh, Vimeo, that Vimeo just went public, and she's 37 years old, that's younger than me, and, and so he's, like, the youngest Indian-American woman To ever go take a company public, right? Every single day, there's those reinforcements of not being enough, no matter who you are, no matter how successful you are, unless you're Jeff Bezos. Even then, Jeff Bezos, I saw the CEO of LVMH just passed him in wealth, so there you go, right? And so it's me, it's my problem. I always feel like, in general, whenever I externalize something and say, oh, that person's not doing enough, or they're telling me to do something, or it's my parents, it's no, it's me judging myself. I judge myself about not being enough every single day, and I hav…

AI assessment note: “It hurts, but it's not, you know, I think all these things are”

Q go for beers with their buddies, and they have a great time, and they start at nine, and then they have the weekend off, and they earn okay, but not great, and they're just super chilled and super happy, and I look at them, and I'm like, why can't I be like that? Because I'm on the other side, but I'm never fucking happy. Like, do you ever feel that?

A Oh, totally, but I guess I've, I have felt that, and I still feel some of that, and I've kind of come to a conclusion, which is I am a person that is unique on my own, just like everyone else is, right? They all are unique, and this identity of all of these things about loneliness, and wanting to be liked, and not feeling like enough, and pleasing my parents, and everything else is who I am. There is no other alternate reality, and I have one choice, Which is, I can either know who I am and love who I am, or I can hate who I am and try to be something different. And the only thing I've done personal development-wise, I haven't changed any of it. I'm just as, like, egotistical and wanting to strive and not feeling enough as I've ever been. Maybe more. But I know it, and I can see it, and I can manage it when it's getting, like, unhealthy. Like, I can disconnect from the internet stuff, and I can check myself out, and I can hang out with the kids and But I know that I'm not going to change it, and I don't really want to. I love myself. That's the thing that's the bottom line of this, is as much as all these things sound sad, the development has been, for myself, I'm the best version of myself I can be. And that's what I want. I don't want anyone else.

AI assessment note: “Oh, totally, but I guess I've, I have felt that, and I still feel”

Q So like, when you think about your identity tied to game site, how do you think about that? And is that a challenge for you, like it is for me?

A Oh, a hundred percent. Yeah, first of all, it's funny. We all have like aversion to words, and there's a word that I hate, and everyone says it as a compliment, and I hate the word, which is exit, exit, exit. I always tell people, look, we didn't exit Gainsight. We had a new investor. I'm just as all in as I've ever been. It's totally true. And I want to see this true as long as I can. And part of it's because I really believe in the business and why we do it in the mission. But part of it, Harry, is exactly what you said. It's my identity. I couldn't imagine not doing Gainsight. Like, it is so tied to me. And I think the more you lean into some of the external stuff, the more that that happens, right? Like, it feels like, oh, Gainsight's me. I'm Gainsight, right? That's not totally true. We have 800 people at Gainsight, and they work so hard, and we have tens of thousands or hundreds of thousands of customer people, people like our customers, and so it's not just me, but sometimes it does feel like, okay, it's on my shoulders, it's my identity, and I have a hard time imagining myself without Gainsight. Now, I don't hope I ever have to, because I'd certainly love to do this as long as I can, but I'm also not naive that things don't go on forever, right? Like, they don't. Like, I don't, do you know Ozymandias? Have you heard of Ozymandias?

AI assessment note: “Oh, a hundred percent... It's my identity. I couldn't imagine not doing Gainsight.”

Q Do you talk to your wife about feeling lonely, and a lot of the, the mental health aspects, like, do you open up to like, listen, I'm really struggling right now?

A Yeah, it's interesting, so that's an interesting one too, so like I mentioned, she is super deep in this, because she runs this community called The Normalizers, all about mental health for kids, and identity, and you know, especially for LGBTQ kids, So the short answer, it's interesting. The short answer is, yes, I do. And by the way, like, obviously she understands all of this in depth and knows me in depth. And when I figured out though, and this is a conversation we just had this past weekend, is like, I can't just throw it all on her, right? So it's a little bit too much for somebody else to take. And so that's where the idea of like therapy or having other mechanisms for coping is very helpful. In fact, I, one of the outputs of this past weekend was like, you know, I really shouldn't see a therapist. Because it's not like I can just share all that with her. She has her own stuff she's dealing with, too, you know, and so a therapist, the benefit is, like, their job is to, like, let you just unload everything going on. So short answer is yes, but I've learned that I can't do it all, because I don't think any partner, it's not like their job to take every single thing you're dealing with.

AI assessment note: “The short answer is, yes, I do.”

Q Okay, so speaking about kids fitting in, I, I read one of your pieces, and you said that you were unpopular growing up, and I wanted to start on that, and it's like, why do you think that was, and how do you think that impacted you?

A Yeah, it's interesting, because people that know me only now are usually pretty surprised that I was a total introvert growing up, and I think, I don't know exactly why it happened, but I have some hypotheses. The facts are this, which are kind of sad. I grew up in Pittsburgh, Pennsylvania, For whatever reason, I never felt like I fit in, so I ate alone at lunch, which kind of, lunch is like the litmus test, especially in American school, probably all around the world. It's the litmus test, like, are you with, like, all the friends around you laughing, or are you, like, on your own, and I was ate alone every day, kindergarten through 12th grade, like, the entire time, all the way before college, and never felt like I fit in. Frankly, I felt so embarrassed that I was eating alone that I would go hide in places to eat, like, I go to the computer lab and, like, pretend to be programming and just eat my lunch, and there was no iPhone or, you know, music back then to listen to, so you were just kind of, like, really, like, living in your own loneliness. Now, why was that? I'm not sure. Obviously, today, I'm very comfortable with people and probably much more extrovert than the average person, but I think there was probably a few reasons. One of them, I think, was probably just, like, feeling like I didn't fit in because I was the, like, the only, like, Indian kid and probably the on…

AI assessment note: “feeling like I didn't fit in because I was the, like, the only, like, Indian kid”