20VC's Therapist Thursday: We Are Not All Crushing It All The Time So Let's Stop Pretending, Working Through Challenges of Self-Worth and Self-Doubt & How To Find Joy in the Striving with Nick Mehta, CEO @ Gainsight

Nick Mehta is the CEO @ Gainsight, the leader in all things customer success helping you put your customer at the heart of your business. Last year, as a result of their incredible success, Gainsight was acquired by Vista for a reported $1.1Bn but prior to that had raised over $156M from Lightspeed, Battery, Bessemer, Insight and Bain to name a few. As for Nick, he has been named one of the Top SaaS CEOs by the Software report three years in a row and holds one of the highest Glassdoor approval ratings for CEOs. Prior to Gainsight, Nick was the CEO at LiveOffice, which grew substantially and eventually sold to Symantec. In Today’s Episode with Nick Mehta You Will Learn: 1.) When did mental health really become a prominent thought for Nick? When was the first time Nick feels he really showed true vulnerability in leadership? 2.) Self-Worth: Does Nick feel like he is enough? What does he do when he questions himself severely? How does he talk to his wife about these challenging thoughts? Where does Nick believe this comes from? What are the dangers of people-pleasing? How does Nick try and counter people-pleasing in his role as a leader? 3.) Identity: How does Nick think about his own identity when it is so attached to Gainsight? In what ways does he try to detach? What has worked? What has not worked? How have children helped Nick in this way? 4.) Striving: Why does Nick believe that hunger and striving are fundamentally a good thing? How does Nick try and factor gratitude and appreciation into the work and success he experiences? How does Nick encourage this same striving in his children? 5.) Relationship to Money: How would Nick evaluate his relationship to money? How has it changed over time? How does Nick try to imbue the same values he had growing up in his children? Does Nick believe it is possible to "change" your children and have that impact?

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

• 0:00Harry Stebbings?

  Welcome back to a very special episode of 20 VC. For those that know me, you know, mental health and awareness around mental health is really important to me and a priority. A friend once told me, "Everyone is fighting a battle you know nothing about." And I always think to that one very often. And so, once a month from now on, 20 VC will do a show that really dives deeper discussing the hard stuff: mental health, insecurities, depression within leadership. And today, I'm so proud of our first episode with Nick Maser, CEO at Gainsight, the leader in all things customer success, helping you put your customer at the heart of your business. Last year, as a result of their incredible success, Gainsight was acquired by Vista for a reported $1.1 billion. But prior to that, Gainsight raised over $156 million from some of the best, including Lightspeed, Battery,

• 0:43Harry Stebbings?

  Bessemer, Insight and Bain, to name a few. And as for Nick, he's been named one of the top SaaS CEOs by the Software Report, three years in a row, and holds one of the highest Glass Door Approval Ratings for CEOs. And prior to Gainsight, Nick was the CEO at Live Office, which grew substantially and eventually sold to Symantec. But before we dive into the show 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

• 1:25Harry Stebbings?

  out at Carter.com. And then another incredible product you have to introduce is SecureFrame. SecureFrame helps companies get enterprise-ready by streamlining SOC 2 and ISO 27001 compliance. SecureFrame allows companies to get compliant within weeks, rather than the painful months that it is today. Join companies like Stream, Husura, Benapass, and unlock more sales with SecureFrame. And 20 VC listeners get 10% off at SecureFrame.com/20vc. And finally, 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

• 2:10Harry Stebbings?

  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 coolie.com and also check out cooliego.com. But that's quite enough for me. So now I'm very excited to dive into this very special episode with Nick Mate, CEO at Gamesite.

• 2:35Speaker 01

  You have now arrived at your destination.

• 2:38Harry Stebbings?

  Nick, it is such a joy to do this one. I always love our chats, but I'm so thrilled to have you back on the show. So thank you so much for joining me.

• 2:44Speaker 02

  Harry, it's just so exciting to be back and to talk about the topic that I really deeply care about. So thanks for inviting me.

• 2:50Harry Stebbings?

  I agree. It's nice to talk about a topic that's actually important, unlike venture.

• 2:56Harry Stebbings?

  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?

• 3:10Speaker 02

  Yeah, it's interesting. I think if you had asked me in my twenties, all the way to maybe thirty, is like, mental health is 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 Presidents' 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.

• 3:51Speaker 02

  And so I just kind of unearthed a lot of stuff and we'll talk about it later. It's not stuff that I judge or that that needs to be fixed, but stuff that just is who I am and helped 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 mental health, their identities, and especially. For kids who are in the LGBTQ group where often they don't feel like they fit in. So anyways, mental health is the number one topic of discussion in our house.

• 4:27Harry Stebbings?

  Okay, so speaking about kids fitting in, I 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?

• 4:38Speaker 02

  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.

• 5:20Speaker 02

  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's 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 only like maybe one of, you know, three, four percent of the kids in our school that weren't Caucasian. And obviously that wasn't anything people were doing to me. I mean, it was nothing, everyone was very nice, but you just felt like you just didn't fit in. And maybe every now and then a kid makes a comment and you just take it the wrong way.

• 6:01Speaker 02

  And so I had this sort of cycle of just feeling like, okay, nobody likes me, nobody wants to be my friend. I was obsessed with trying to become popular. It was comically hilarious. I wasn't the kid who was just like lovably like a loser on the side, but didn't care and was happy to be a loser. I was the kid that wanted to break in and I remember like being in like middle school and realizing like. We were in actually like an affluent suburb and but we weren't like super affluent, we were just middle class. And my parents are Indian immigrants and even though when they made money, they didn't want to spend any money at all. They were very, very thrifty, but I told my mom, the kids at school are wearing these shirts that have a little horse with a stick on it, the polo shirt, Ralph Lauren. And they're wearing it, the popular kids have that shirt.

• 6:42Speaker 02

  And I dragged my mom on my birthday to the polo store in Pittsburgh where I grew up to buy like a $80 shirt, which was unthinkable amount of money for Indian Americans living in Pittsburgh in the 1990s. And so I tried to fit in, I watched what the popular kids did, what music they listened to, everything. I never figured it out in high school and later on in college, I figured out my, kind of my thing and all that. And I think one thing that's kind of cool is nerdiness and kind of geekiness went from kind of uncool when I was a kid to actually becoming the social norm now. So that's changed a lot.

• 7:16Harry Stebbings?

  Man, it's so funny you say about the lunchtimes there. I used to go to, actually it's weird, but I used to go to the bathrooms because the cubicles, no one can see you and you're just like avoid the world.

• 7:25Speaker 02

  Hundred percent. By the way, the only difference, that's the benefit of being the UK. The cubicles in the UK to go to the restroom go all the way to the floor. In America, for some reason, they leave this little opening at the bottom so they can tell that you're in there. So that's why I never went to the bathroom, so.

• 7:39Harry Stebbings?

  That is a total nightmare. Can I ask, 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 and how do you think about that today?

• 7:57Speaker 02

  Oh my God, Eric, like a hundred percent. It's funny to, 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 mirror ball, I can be anything you want, that you want me to be. The idea is you reflect like a mirror ball 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, Eric, I have to manage that. I'm a CEO, I have like a running company, it can't just be about.

• 8:40Speaker 02

  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.

• 8:52Harry Stebbings?

  It's so interesting. You quoted that the Taylor Swift song. There's a brilliant Goo Goo Doll song called Iris.

• 8:57Speaker 02

  Oh, yeah, Iris. Exactly. I love Iris. Yeah.

• 8:59Harry Stebbings?

  I don't want the world to see me because I don't think that they'd understand. And that always is kind of encapsulated in my mind and it's driven a lot of like my external brand. And I do want to talk about kind of this difference between real Nick and brand Nick. And I have it with real Harry and brand Harry. How do you think about brand Nick and real Nick and the divergence?

• 9:19Speaker 02

  Yeah, it's interesting because, Harry, have you ever done an Enneagram test?

• 9:22Harry Stebbings?

  I haven't.

• 9:23Speaker 02

  No, so that's great. I highly recommend anyone listening do it and you should check it out. It's it takes like five minutes. It's a one of those personality tests, probably, you know, conceptually similar to like a Myers-Briggs. E N N E A G R A M. And it's very popular actually amongst CEOs. And this YPO group kind of espouses it. So I've done it. You get a number from one to nine. And the number basically is about what kind of brings you energy and like where you feel like seen and successful and what type of part of your life. And a three is all about achievement, performance and people liking them. And it's all about like being whoever you want people to be. It's about being on the stage. It's about like putting on whatever costume makes them laugh, right? That exact thing. And so I'm a three, like I'm the most hardcore three you could possibly imagine. Maybe you are too.

• 10:07Speaker 02

  It's just you want people to like you and think you're successful, right? That's what they want. And so therefore a lot of your life feels like you're performing. And honestly, it's a kind of a, it's a cycle. It's not necessarily a bad cycle, but it's a cycle, right? Because I'm a three, I want to be seen, I want to be liked. So I lean into things like social media and making funny videos and doing podcasts and speaking. And so then I'm constantly on stage, like all the time, like, like literally two, three times a day in these types of things, right? As you know, and you've read, I really lean into trying to be real and vulnerable. I really try to. I try to talk about things like what we're talking about now. And then every now and then I'm like, wait, is that real Nick or is that stage Nick? And I'm not sure. Now, one of the things I've kind of come to conclusion.

• 10:50Speaker 02

  Is it's all real Nick because there's no such thing as like the real Nick versus the fake Nick. It's not, I think that's actually an overly simplified dichotomy. But how do I make sure I can show all my sides? Not just the ones that maybe please the audience. So an example of a side that doesn't please the audience, not in a bad way, but it's just not something that people are into is like I have this part of me that's deeply inquisitive about existentialism. I know it sounds funny to talk about a podcast, but I actually think a lot about consciousness and reality. And I'm a big into physics too. So like what the universe is and what time is. And by the way, that's kind of not the best. It's kind of a buzzkill at a party. When you start talking about, hey, what do you think about the, the meaning of quantum physics?

• 11:34Speaker 02

  It's like, okay, clear the room really quickly, right? And so there's some element where I want to find outlets where I can be all the versions of myself. You know, so in other words, it's not about there's one real Nick and there's one fake Nick. It's more like, how do I have my life structured in a way where I can have outlets for all the different versions of me?

• 11:50Harry Stebbings?

  I totally get it. Can I ask, did you, and something that I worry about with myself and then more using this as a therapy session. So just, you know, bill me ahead of time. But it's I worry that actually for so much of my life and for so much of my days, I'm brand Harry. And actually I kind of have the ability to lose my own real Harry. Cause I'm just brand Harry so much and like my, you know, my mother will say, Harry, you're not on show now, like you can be you. Do you ever get lost in the brand and lose actually who you are?

• 12:18Speaker 02

  Yeah, I do. And I think that there's a part of my day or my week where I feel like I have no external self judgment or wondering what people think or thinking about whether I'm successful or not. And I, I know it's gonna sound cheesy, but it's when I'm with my kids. When I'm with my kids, I don't actually have any internal monologue going on. I'm not trying to self correct to see whether you're smiling or not in my jokes, whether you like me. Right? My kids aren't gonna laugh at my jokes no matter what. Actually, they do still laugh, which is kind of funny because they're really not that good jokes. But when I'm with my kids, there's this weird suspension of disbelief. And I feel like I'm in some extremely blissful reality that is, it's not like that's more real than everything else, but it feels very genuine.

• 13:00Speaker 02

  So that is the thing that that I have a few things like that. Like another one, Harry, that for me feels very real is like when I read or when I exercise. Those are like three times of my day when I'm just like so present that I don't feel like I'm on stage.

• 13:15Harry Stebbings?

  I I think the beautiful thing with kids, and it's probably something I I learned, but it's like that is real, non tied to professional work. That is real meaning and depth to life.

• 13:24Speaker 02

  That's right.

• 13:25Harry Stebbings?

  That is what all of this is for, and it's why you do what you do, and it's why I do what I do. I guess my my next question is bluntly. When you think about, you know, exiting with Gamesite and when I think about my businesses, I tie all of my identity to my business. I am twenty B C. That is me. It's why I don't take holidays because when I detach myself from the business, I don't even know who the fuck I am.

• 13:47Speaker 02

  Who you are, right?

• 13:48Harry Stebbings?

  When you think about your identity tied to Gamesite, how do you think about that? And is that a challenge for you like it is?

• 13:55Speaker 02

  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. I always tell people, look, we didn't exit Gamesite. We had a new investor. I'm just as all in as I've ever been. That's totally true. And I want to see this too 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 Gamesite. 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, Gamesite's me. I'm Gamesite, right? That's not totally true. We have eight hundred people at Gamesite and they work so hard. And we have tens of thousands or hundreds of thousands of customer people, people that are customers.

• 14:39Speaker 02

  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 Gamesite. 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 Ozzy Madias? Have you heard of Ozzy Madias?

• 14:58Harry Stebbings?

  I I did.

• 14:59Speaker 02

  Oh, my gosh, you got. Okay. So another I'm giving drop at a lot of knowledge here. Ozzy Madias is a poem by Shelley and it's basically about a traveler going through desert and he basically discusses.

• 15:10Speaker 02

  Covers this statue that's in the desert, but all the sand is kind of blown away most of the statue. And the inscription on the statue says, basically, I am Ozzy Mendias, uh, king of kings. Look upon me and weep at my mightiness. So basically this king who's saying he's such a badass. But the statue itself, the head has fallen off because of the, the time that's passed. And so the idea of Ozzy Mendias is, look, everything's going to be gone, right? Eventually, Amazon will be gone, right? Some point. America will be gone at some point, humanity will be gone at some point. And so this weird thing where your identity is tied to something that is ephemeral, right? Your company is ephemeral. It's not going to be around forever. And I do think about that a lot, but it gives me so much comfort, Harry, like, just like your work. It gives me so much comfort.

• 15:52Speaker 02

  I have so much control over it. I love it. It gives me joy. I feel like I'm good at it. So yeah, I have a really hard time imagining a world without it. One really hard emotion, though, and just kind of being vulnerable. Is the company is not just me by a country mile. There's so many people involved, right? But I feel like I've, like, the metaphor I have is, I'm like, it's a train. And I'm the conductor in the front and I've like handcuffed myself to the steering wheel. So I can't get off the train. I'm not going to. I don't want to, but I can't either, right? And the train, I'm going to hopefully take you to the promised land, or maybe it'll go off the tracks at some point, but I'm going to be there the whole time. And everyone else in my company and every one of our customers, everyone else, the whole community, investors are all passengers. And not in a bad way. They're on a train to get somewhere. They want to get to where they need to get to in their career and they need to get to their investment return

• 16:37Speaker 02

  or their business outcome or whatever. And so there's some loneliness when those transitions happen, right? When somebody's been a gainsite seven years and then they move on and I love that person. I'm so excited for them. And oh my gosh, like, it's just me on this train, you know? So that's a loneliness I feel.

• 16:52Harry Stebbings?

  I, 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?

• 17:06Speaker 02

  Oh yeah, all the time. I definitely feel it. It's interesting because we, as you mentioned, did a financial transaction where we're new investors and you know, because of that, all of our employees were able to, you 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. Because I, I'll be honest, e- even when, you know, we're like a hundred and something million of ARR now. And even when we were like eighty million of ARR, I was 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 a little more strive for the success, like go big, like how to make this huge, you know?

• 17:49Speaker 02

  But it feels like it's on my shoulders. It totally does, you know, and that's not true. We have so many people here. But sometimes it feels like that.

• 17:56Harry Stebbings?

  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 they 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?

• 18:13Speaker 02

  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 of 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 here 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?

• 18:58Speaker 02

  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 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 talk 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 crushing it and killing it. And frankly, that makes me feel more lonely. Right. That's like, there's a musical, which I just love. I don't know if you've ever seen it called Dear Evan Hansen. Have you seen it?

• 19:31Harry Stebbings?

  I have.

• 19:32Speaker 02

  Oh, my God. When when Broadway opens up again, you got in London, you got to go see it. I'm sure it's in the West End. And it's basically about, it's a story that's actually, the plot sounds sad. And it's actually funny and in some ways uplifting. But it's basically about this kid who he is super lonely in high school. So I very much identified with him. And he was pretending to be friends with this other kid. And this other kid actually ended up committing suicide. It's a very sad story. This other kid committed suicide. But this friend, who is the protagonist, pretends like he was the other kid's best friend to make his parents feel better. And so this whole thing where the entire show is about this kid pretending he had this friend that actually wasn't real. But the end of the show is all about the idea that everyone feels lonely, like everyone has that loneliness in them.

• 20:17Speaker 02

  And that loneliness is strangely what connects us together. Like, we all feel some loneliness. So basically, I want people to just be more open about that. I would feel more or less lonely if people were more open about being lonely.

• 20:27Harry Stebbings?

  Don't laugh. Do you have like commonalities in when you feel lonely? So I often feel lonely. Eleven till one, eleven P M. Till one A M. I feel really lonely then. Then commonalities of when you feel lonely.

• 20:39Speaker 02

  Yeah, it's interesting because it's like basically evenings when all of you're going back to your hole 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's 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'd like one, you know, one glass of Scotch or something. And I was biking home and I felt bliss.

• 21:20Speaker 02

  Because it's that feeling of like the endorphins and the energy, even though I was like alone again, I felt this bliss. 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.

• 21:34Harry Stebbings?

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

• 21:43Speaker 02

  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 this in depth and knows me in depth. And what 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 should 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.

• 22:26Speaker 02

  You know, and so 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.

• 22:39Harry Stebbings?

  Can I ask, you know, I, I often feel like I have to be strong, you know, my mother's got MS and there's, you know, some is challenging that. 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.

• 22:58Speaker 02

  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, vulnerabilities of 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, fifteen, twelve and nine. So, you know, they're still developing as people. With Manika, 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,

• 23:41Speaker 02

  right? That things just aren't then gonna 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 Gainsight. And I talk, a lot of Gainsight people have heard me talk about all these topics. But there's still some veneer of like needing to have the story still end up with a positive note.

• 24:11Harry Stebbings?

  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 very, and I obviously 99% did. But even the 1% that didn't respond well to the vulnerability, I'm like, seriously?

• 24:29Speaker 02

  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 3,000 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, the, I didn't talk about the 97% of people or whatever. They were like, that's amazing. And you're so brave for doing it. Because I always remember those 3% of people or the 1% of people. Now, I think over time, Harry, that, 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

• 25:10Speaker 02

  much like happiness and gratitude, is watching people over time embrace this vulnerability concept, even if they were skeptical early on.

• 25:19Harry Stebbings?

  I totally agree with you. I guess you saying there about kind of choosing the 3% 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?

• 25:37Speaker 02

  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 hundred percent. I'll tell you my journey there. So it starts as a kid, like everything. So going 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.

• 26:21Speaker 02

  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 at 15. This kid took all these AP tests. This kid did X, Y, and Z. And so I became that hyper competitive about success kid who's just about, okay, what college can I get into? My parents wanted me to go to Ivy League college. Can I be the valedictorian to my school? Tracking like literally what's my GPA versus everyone else's in school, right?

• 27:02Speaker 02

  That all of that stuff because I felt like I need to prove my parents and probably really prove to myself about who I am. And so then all that happened and end up being fortunate, going to good school and things like that. But then I went into the workforce and I've done some things and some have been good and some haven't worked out and it's all been good. I'm pretty happy, but then fast forward to three years ago, I take my mom out to dinner and my mom and dad. And we are driving to a restaurant and my mom knows that outside of work, I'm really into science. And I think she always really wished I'd been a scientist or a doctor or something like that. And I'm driving my mom to this restaurant and my dad and my, and my mom says, it's so great that you're still into science. You know, you read all these books. You're so into physics. That's so great. It's too bad you didn't go into science because you really could have done something with your life.

• 27:44Speaker 02

  And my dad says, trying to help, he's like, no, Mina, no, no, no, no. He's only 40. He still has time to do something with his life. And my mom's like, no, he's too old, but maybe the kids can do something with their lives. And she wasn't trying to be harsh and she's actually just, my mom's super direct. I love my mom. But all the time, like this past weekend, I saw them. I'm very fortunate. They're still around and I go see them every weekend and my mom. Like every time she brings something up that's about comparisons, like she's like, who do you think the most important Indian American CEO is in America? I was like, I don't know. That's not a topic I think about every day. And she's like, no, no, who do you think is? Is it the CEO of Pepsi, Indore Nuri? I was like, I think it's probably Satya Nadella, the CEO of Microsoft. And she's like, who's number two? And I was like, I don't know, uh, Sundar Pichai, Google? Who's number three? And she's like Adobe?

• 28:28Speaker 02

  And she's like, maybe you can be one of those people one day. And so literally going all the way to today, there's that feeling of like being enough. And I, I shall tell you, you probably have some questions. I'll tell you a story that uplifted me from a friend about this. But the short answer to your question is, I never feel like I'm enough.

• 28:44Harry Stebbings?

  Does that hurt when you hear your parents say that?

• 28:47Speaker 02

  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 Vimeo. The 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.

• 29:31Speaker 02

  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 have to manage that. And so actually there's a story that I think was so uplifting. I have to tell it. Which is, we have a pre pandemic, we created this dinner party where the, the only rule of the party was, you're not allowed to talk about the trivial stuff. No vacation plans, no, what are you watching for TV? Every time we start with a question like what we're talking about here, Harry, like a question like that. My wife and I come up with the questions. So about a year and a half ago.

• 30:16Speaker 02

  We came up with a question. It was my wife's idea, which was what if you accomplished it would make you feel completely satisfied when you're 90 years old and, you know, nearing the end of your life? And everyone went around the table and somebody said, you know, something related to their kids and somebody else said something related to work. And it came over to me and I said, honestly, nothing. There is nothing that will ever make me feel like I've done enough. And then I had this, then I made a joke and I said, unless I was so successful that they added a fifth person to Mount Rushmore on that, like in America on the rocks. And they thought that I was such a great all time human being that they decided to rename the moon after me. So people would go outside and say, it's beautiful Nick outside tonight, instead of it's a beautiful moon outside tonight.

• 31:01Speaker 02

  So that was my joke, obviously, that there's no way I could ever be successful enough. There's no enough. And then my friend Anna, who was one of the participants of the gift, gave me this card, which I keep on my desk still. And it says, you are enough, you were born being enough. Nothing you say, do, create, achieve, feel, fear, or conquer will ever add or subtract from who you truly are. And that card is something I've kept on my desk the last, you know, two years and I'll keep forever because I gotta keep reading it.

• 31:27Harry Stebbings?

  I love that card. I think the thing for me is like, and I talked to my therapist about this a lot and he gave me the sobering conclusion last week. And he said, if you continue with this mindset, you will continuously be unhappy.

• 31:37Speaker 02

  I know.

• 31:38Harry Stebbings?

  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?

• 31:50Speaker 02

  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 seeing, 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 stride is about wanting to do more. And so what I feel, Harry, is like, when those things happened, 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. Cause now it's like, well. Yeah, billion dollars, but that's that our company valuation was a billion, but that's just a billion dollars. What about the companies that are 10 billion or 100 billion,

• 32:32Speaker 02

  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, who's three years younger than me, has 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. Like, a lot of the people that actually made an impact on the world were incredibly tortured. And there's a high correlation, probably, maybe causation. And I'm not saying we should try to be tortured. But I also have given up trying to fix myself. I'm not trying to change who I am. What I really want to do is know who I am. That's

• 33:16Speaker 02

  it. Be able to observe it. And then then Harry, like, at various times, be able to, like, read the thing about this CEO who just took their company public, and why haven't I done that? And I'm not enough? And then be able to step out of that and watch myself and kind of laugh lovingly, right? Like, I'm my friend. I love myself. That's what I want.

• 33:32Harry Stebbings?

  Do you ever don't know, it's a weird one. Do you ever like, hate yourself in the way that I look at friends of mine who finish at five, they 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?

• 33:56Speaker 02

  Oh, totally. But I guess 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.

• 34:36Speaker 02

  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. 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 the development has been for myself, I'm the best version of myself I can be. And that's what I want. I I don't want anyone else.

• 35:02Harry Stebbings?

  I I love the realization of like stopping trying to fix yourself. I think I think that's great. Can 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 to 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 their family.

• 35:26Speaker 02

  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 it matters infinitely and the more you get, the more happier 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 our 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're very privileged and we have your 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 very big privilege for people to have it. And I have so much empathy for people who don't have that.

• 36:11Speaker 02

  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 I'm with you.

• 36:24Harry Stebbings?

  I totally get you there. Do you worry about enforcing the same work ethic, hunger, ambition within your children? Well, no offense, we are privileged, we're in a privileged world, but you know, your children are in a privileged position.

• 36:35Speaker 02

  Totally. Yeah, it's it's extremely, you know, they're extremely privileged. Yeah. And it's interesting because, you know, we haven't talked to them about money and they don't they don't know the details. But obviously they know that we've been really fortunate and I wonder. Sometimes about how my parents raised me and how much of that I want them to have, right? That striving, that not feeling like enough, like this is an interesting question, Harry. I know you don't have kids yet, but like if you have a lot of things that are you, do you want those things to be in your kids? And there are two arguments. One is like if you like yourself in your life, then yeah. On the other hand, are those things demons? Can you give your kids all the good without the bad, right? The positives without the baggage, can you do it? What I've learned is I have less control than I think. I don't know, I think a lot of parents learn this. You want, especially if you have multiple kids, because you're getting this little experiment where you're like,

• 37:20Speaker 02

  well, you do kind of the same things with three kids and they turn out pretty different. And like our oldest definitely has a lot of those same things I have of the striving and wanting to be successful and not feeling like enough. And then our, our middle one, our middle one's actually on the autistic spectrum. And so it's been amazing to watch our middle one's thought process and just like how they think really differently. Like they actually just have a totally different mindset. And our youngest is a total people pleaser and wants to be pleased. So I see these things in them and I'm like, do I fix it? Can I fix it? Do I want to fix it? Is, can anyone be fixed? There's all of that. On the actual work ethic itself, I do think that, you know, what I don't want is our kids to just kind of fail to launch in society. Meaning they just can't get started, you know?

• 38:03Speaker 02

  And so we want them to feel that hunger. Cause I do think the hunger, I mean, Harry, I think there's some healthiness to it, right? I think if people feel no hunger in their lives, you don't want people to feel real hunger. I mean, that, that's obviously I'm using it as a metaphor. Real hunger isn't good. We want everyone to feel they can get food and so on. But having some level of striving is I think what gives life meaning. And so I'm trying to find that balance.

• 38:25Harry Stebbings?

  I, I totally agree. I think that there is absolutely a flip side and a 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 Stacey'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?

• 38:48Speaker 02

  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. 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, my parents gonna 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?

• 39:33Speaker 02

  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, oh, my God, that was amazing. And just thank you for being so brave. And by the way, I'm dealing with that too. And by the way, like you said, Harry, like other people were lonely growing up too. Or other people feel like they're not enough, or other people feel like they're not sure whether they want to fix themselves or be themselves or what. It's so amazing to have those conversations. I'll close with a story, which is like,

• 40:16Speaker 02

  when I did that talk about vulnerability, the first time, I actually tested it in front of our company and our all hands meeting. And it was this incredibly transformative moment. That literally is the thing that pushed me over the edge. I was, it was a whim. We were doing our all hands kind of company. It was like an annual big thing. We're in a nice place, all the employees. And I was going to do my speech, talk about how the business is doing, how we're crushing it and killing it. And at the end, I talked about vulnerability. I was like, you know, I just want to close it something different. And people were so incredibly moved, but more importantly, right after that, we had breakout sessions. And there's a product marketing person on her team named Julia, who's still to this day, she's not with us anymore in Gainsight, but still so dear alumni for us. She got in front of everyone, in front of everyone, and she was doing her session about, you know, something, sales, something.

• 40:59Speaker 02

  And she basically, all of a sudden, stopped and she basically talked about her anxieties about, you know, being on stage and presenting and so on. And everyone in the audience started saying, "We love you, Julia. We're here to support you." And that moment was created because I was able to be vulnerable and I created that vulnerability, then Julia was vulnerable, then the people in the audience were vulnerable. Vulnerability is infectious. If we all do it, everyone will do it. And then we'll be more real and we'll feel less lonely.

• 41:26Harry Stebbings?

  My therapist told me, actually, vulnerability is the currency of human connection.

• 41:30Speaker 02

  That's it. Oh, my God. That's such a good way to say it.

• 41:33Harry Stebbings?

  And it's like, you don't actually have true depths of relationship if we continuously just chat about Narcos on Netflix. That's not genuinely a true.

• 41:41Speaker 02

  That's it. I mean, it's a great show, but still, yeah, there's a lot.

• 41:45Harry Stebbings?

  Love it. No, listen, let's do a quick fire round. So I say a short statement and you give me your immediate thoughts. And this is a fun one. I've never done one like this, so this is cool. Are you ready to dive in?

• 41:53Speaker 02

  Let's go.

• 41:54Harry Stebbings?

  What is the advice you give the most that's the hardest to do yourself?

• 41:59Speaker 02

  Oh, yeah. Okay. We are extremely passionate about our values at Gainsight. The number one thing I say and try to do, but it's so hard, is hiring people based on values and really assessing that.

• 42:10Harry Stebbings?

  Mine's being vulnerable. No, I'm just kidding.

• 42:14Speaker 02

  You did a pretty good job, I'd say.

• 42:15Harry Stebbings?

  That's a pretty good one to finish with. And tell me.

• 42:17Speaker 02

  I'm gonna email your mom and tell her how great you are being vulnerable, so.

• 42:21Harry Stebbings?

  Tell me, what's the most prominent lie rich people tell themselves? I got asked this one the other day. I was like, that's good.

• 42:27Speaker 02

  Ah, that's a really good one. I would say you made it all happen, that you yourself are the one that made it all happen versus lots of other things that contributed to that.

• 42:37Harry Stebbings?

  Tell me, what would you most like to change about the mental health ecosystem and the stigmas we have around it in tech?

• 42:43Speaker 02

  The brain A. Brown is the one who started this. I'm just like a fan. It's that, like, talking about this is not a sign of weakness, it's a sign of strength.

• 42:50Harry Stebbings?

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

• 42:54Speaker 02

  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 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 gonna be very hard, 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, we call it human first business, trying to be more of your real human self.

• 43:38Speaker 02

  And I would love to just like see that materialize even more. We've leaned into it a lot, but I'd 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?

• 43:47Harry Stebbings?

  Nick, I can't thank you enough for doing this. It's a it's a very special and unique show for me to do. So thank you so much for agreeing to do it with me.

• 43:54Speaker 02

  Oh, my God, Harry. This has been so one of the best conversations I've had in a long time. So thank you so much.

• 44:01Harry Stebbings?

  I mean, what can I say? I did tell you it was a different type of show, but I want your feedback. I want to know what you thought. I want to know what you liked, what you didn't like. If you'd like to hear more like this, let me know what you think. You can find me on Twitter at Harry Stebbings or on the site, thetwentyminutavec.com. Love to hear your thoughts and feedback. But before we leave you today, did you know that more than eighty percent of US public stock is owned by just ten percent 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 sixteen thousand 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.

• 44:43Harry Stebbings?

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• 45:26Harry Stebbings?

  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. As always, I so appreciate all your support and I can't wait to bring you an incredible set of episodes next week.