How This CEO Built a Movement, Not Just a Company with Nick Mehta

Your job as a CEO is not popular with your customers or your employees. For example, if you use customer NPS as an example, if you just are looking at short-term what customers think, you would miss the turn in how the world is changing. Like let's say with AI as an example, right? And so I think the same is true with employees. Glassdoor is not something where it's just the end-all be-all measurement of a company, in my opinion. So when we had the award on Glassdoor, yeah, that was super cool.

Awesome.

But yeah, did our score go down when like The bubble abated? Absolutely. You know, I think, I don't know, we're probably 4.2, 4.3 now. I think the thing that I do take away though about Glassdoor is, to me, the thing that's interesting is when the company's doing okay, like when it's not crazy gangbusters, your score is a reflection on the, almost like the floor of your culture.

Welcome to the Startup CEO Show. I'm your host, Mark MacLeod. In this episode, I sit down with somebody who needs no introduction, Nick Mehta, co-founder and CEO of Gainsight. Gainsight has almost single-handedly been responsible for the creation of a customer success profession and job category. We discussed a whole bunch of elements of their success, how they went about creating a category. Uh, they acquired a whole bunch of tier 1 investors along the way, and so we talked about how he dealt with that. We talked about just some personal aspects and most importantly, we talked about his love for Taylor Swift. I really enjoyed this discussion and I hope you do too. Nick, welcome to the show. It's a true pleasure to have you here. How you doing today?

Mark, it's great to see you. It's, I follow you online and it's awesome to be able to have this conversation.

Amazing. Well, I've been following you for many years and have been fascinated for a variety of reasons. One, your fascination with Taylor Swift, which we're going to unpack. Obviously Gainsight, you know, before Gainsight, people were just called customer support reps, and then you created this category called customer experience. Just your visibility as a founder, just so many things. But let's start with the most important topic, Taylor Swift. What's up? Like, why, hey, why is she such a big deal? And why is she such a big deal for you specifically?

Well, it's funny cuz you know, yeah, of course, like whenever you have, you post online, people always get to know you in a certain lens. So the truth is I have a lot of different lenses. You could see, I don't think you'd see behind me right now, but I've an Albert Einstein poster to my—

yeah, I can see that.

This side, maybe you can see a little bit over here. You couldn't see, but well, you can see a Steeler helmet back there cuz I grew up in Pittsburgh, huge Steeler fan. So I'm into a lot of different things, but certainly one of them is music. Um, but the, the reason I love Taylor specifically is I think that two things. One is, She is an incredible businessperson and marketer and just leader and like things that we can all learn from creativity, community, all that. And then two is I love writing and, um, I love creativity and creative writing and she's an awesome lyricist. So there's my two things. She puts just like her heart and soul into what she does. And I think I really respect people that do that, whether it's in sports or in science or music.

I love that.

Yeah.

You know, my daughter is out of the kind of peak Taylor Swift age. I don't know if she ever had like a big Taylor Swift phase, but I guess there was enough that, cause, cause I also have a shared passion of music, but very underground music. I was a, been a rave DJ since the 1990s. Wow. And I produced music, ran a record label until last November. But like not commercial music, music where you pop a pill and dance till 6 in the morning. Yeah.

Yeah. Nice.

But I've learned that, well, first of all, music generally speaking is a hard place to make money. And I deeply respect Taylor Swift's journey. I mean, I heard about her re-recording her songs so that she had the IP rights. Like, yeah, super smart.

So smart.

And then I'll say that I've not paid a ton of attention to the lyrics, but my understanding is that her messages are very positive and empowering, and we could do with a lot more positivity in the world these days. So totally. Yeah.

And it's, it's positivity, but I think it's also, I, I think it's just one of the things that, you know, will probably translate well to business. It's also just very authentic and honest and vulnerable. And so what I really appreciate is she's able to take her feelings and express them in incredible writing. Right. And this is just, I, I, I love poetry. I like fiction. Like it's just that person that can say, take my heart, rip it open, and in blood write it on paper. And that's kind of when you see great artists that you connect with, that's the feeling I get is I can feel like their heart being written on paper.

I love that. Now you said a thing that I 100% believe, right? Which there are many layers to Nick. I forget your exact words, right? But you're not just a Taylor Swift loving person. But I feel, and so I feel like I've certainly gotten to know one of your layers just through how you put yourself out online. I'm curious, like, have you taken any specific inspiration from Taylor or the persona you've created online? Does that come from just another place?

No, I don't think so. I think, well, I think all of us take inspiration for everything. So it's an ambient, right? Inspiration's everywhere. So sure, the answer would be, have I taken inspiration from so many places? Absolutely. You know, anyone that I, interact with, follow, read about, is— becomes part of who I am. But it's not— I wouldn't say it's that. I think it's actually more, um, like seeing that when, for certain people, when they find their voice and are willing to share it and they feel comfortable sharing— not everyone is able to give them the space and safety to share, but if they're able to, other people really resonate. Not everyone, by the way. Some people might not resonate, but It turns out like if you put your heart out there, some people might find it authentic and interesting. And so that's kind of like the, I wouldn't say that was from one person. It's frankly more just experimentation. I remember, um, we have this conference called Pulse, which is like kind of the big industry event for customer success. And we've been doing it since 2013. And you know, it's a, it, it's always been a little different 'cause we made it not about our products, but actually about the profession. And we don't call it Gainsight event. In fact, sometimes people literally, I get emails from people being, congratulations on being selected to speak at Pulse. I'm like, oh, is that— that's awesome. Really tough battle. I'm like, okay.

Yeah.

Thank you. I appreciate it. It was a great honor. But it's always been a little different. It's, and it's kind of zany and funny and silly. And I remember Pulse 2016, so almost a decade ago, we're in Oakland, California, and I'm planning to close out the event., and I decided to like kind of channel Brené Brown and like have the closing not be about business or SaaS or something, but about being lonely as a kid, which is part of my backstory. And people really resonated with it. And be honest though, like a few of our employees were like, I remember one of our employees put like anonymous feedback that was like, I don't know, I think our CEO should be tough, shouldn't be like, that comes across as a little weak, right? And, and it's okay, that's what they feel, that's fine too. But, um, a lot of people resonate with it. So I was like, wow, this may not be for everyone, but it's definitely for some people. And so then every year, every time, every interaction, I felt more and more comfortable sharing more about myself. Now I say that being somebody who's— I feel, you know, privileged and lucky that I can do that. Some people don't feel safe to do that for a variety of reasons based on who they are and what society they live in. But I feel safe to share a decent chunk of myself and it seems to help. So I'll keep doing it.

Yeah. Well, I'll tell you, it compelled me to want to have you on this show. It's a magnet, right? For sure. And like in a sea of companies, like it creates connection, right? It can create meaningful human connection. And then I, so haters are going to hate, nothing you can do about that feedback, Higon, but like The startup world is so full of bravado, right? You talk to another founder, how are you doing? Oh, I'm crushing it. You talk to a VC, how's your portfolio doing? We're crushing it. It's bullshit. Most startups fail. They're full of comparison and imposter syndrome in their heads. They're not crushing it. They're comparing the 5% they know about a competitor to the 100% they know about themselves. So I love that, that you're just putting yourself out there because it gives others permission to do the same. I think it's, it's really important.

Yeah, it does feel like there's people who feel like they, there's only one way to operate and it's maybe the monochromatic way to operate and that's fine. Like a lot of respect for those people too, but there's a different way to operate and you know, it's a different kind of success and all that. And yeah, we're all, we're all different, but I feel like we sometimes get led to believe there's only one playbook and there might be multiple.

No, there's, there's many. If there was a playbook, someone would have written the book and I wouldn't have a business.

That's exactly right. Exactly. Nailed it.

Thank God there isn't a playbook. But speaking of playbooks, you know, Gainsight is one of the few companies that stands out for creating a new category. You know, kind of HubSpot did that around inbound marketing. There was no notion of customer success. As an employment category before Gainsight. So maybe just walk us through that, you know, was that your intention from the start? Did that just sort of evolve over time? And how did you, like, let's reverse engineer the playbook that you created in doing that.

Yeah. And by the way, I was like to say up front, people kind of say Gainsight created the category, but I think it's more like we fanned the flames, like, you know, everyone Everyone gets too much credit, you know, and including us. And so we're not, we are not the only ones, you know, the Salesforce actually originally when, when they kind of were getting started famously in the early 2000s, like 2004, you know, Mark Benioff said, hey, we need somebody to think about churn. And that, that was where the term CSM came from. So not from us.

I didn't know that. Yeah.

Okay.

I've always associated with you.

Yeah.

Yeah.

We talked about the, this book we wrote, the blue one back there. We talked about the history and then, but you're right that it was pretty small. Like we, we launched in 2013.. And in 2013, you know, we didn't know it at the time, but if you go back and look at the historical data, there may be 1,000 CSMs in the world on LinkedIn. And now there, depending on what titles you look at, a few, few hundred thousand. So it's pretty, pretty big growth. And, um, yeah, back actually, Frank, I was joked that back then if we knew that there were only 1,000 or something, we would've never done the company cuz it was shrinkingly small. It was horrible, but we didn't know. And, but what we knew was like, I, ran a SaaS company before Gainsight, which we eventually sold. And like all of the folks in the early days of Gainsight had worked in like early SaaS companies, and we knew that the old model of like market and sell and support the customer when they call you wasn't sufficient for all the reasons that are obvious now, right? Now that, that's obvious. It's obvious you need to get your customers to adopt your product and you need to onboard them and you have to keep them and all that. But back then that wasn't so obvious 'cause we had an old playbook that came from kind of what people refer to as the on-premise software world, which I, I say refer to, 'cause some people watching may not totally know what that means. Basically, people would sell a company software that they would install on their own servers. And because it was like a one-time purchase, the relationship was very different. You know, you didn't have to worry about keeping your customer, you know, and now you do. And so what happened was in the early days, there was a business problem, meaning customer retention., but people didn't know how to solve it. And so one part of that solution, not the only part, but one part was, you know, this new role called a CSM. And so in the early days, we realized frankly, very practically to sell our software, we needed more people out there to use the software, right? Our market was, didn't exist. And so we had to help like kind of evangelize it and, and sort of foment it into something significant. And that's why we created a conference on customer success, which, you know, thousands and thousands of people have been to, to actually tens of thousands., wrote, wrote 5 books on customer success that hundreds of thousands of people read. And so all of that was like outta necessity. I wish, I wish it was some genius idea. It was frankly probably objectively not doing enough research on the TAM early on and saying, well, people are gonna need our software and not realizing, well, actually you need people that can actually buy it. And then one thing led to another and, you know, kind of now CSM is sort of a universal thing. Every company knows they need it. Frankly, every company has a different version of it, which is, which is natural. And people are still figuring out what it actually means. But the idea that you need to focus on retaining customers, that's no longer a new idea. In fact, when I explain people now, like a new founder, I'll be like, oh yeah, customer success, blah, blah, blah. They're like, yeah, that's kind of obvious, Nick. I'm like, yeah, it's obvious now. Wasn't obvious then. Um, but it's kind of cool to work on something that now is obvious because that means you know, the people that worked on this were kind of pioneers, not just us. Everyone that back then in 2013, they were pioneers.

So just to double-click into some of these things, just so people can really picture, I guess, a bit more of the playbook. So 5 books, that feels like a lot. Does that mean like you are personally the author of 5 books? You may have had co-authors, but like you are in Amazon, I can go search on Nick Mehta and I'm gonna find your books?

Yeah, 4 out of the 5 I'm an author on. But just to give credit where credit's due, so the first one, which is that blue book in the back, you can see right in the background, that's called, it's called Customer Success. So I'm very generic, but it became kind of the authoritative book. Dan Steinman, who was our first Chief Customer Officer at Gainsight, and like truly deserves a huge part of the credit for the early days of Gainsight, he did 90% of the work on that first book. I did a little bit, I wrote one chapter, he did the vast majority. But then we did that book, Then we did a second book on like kind of the big picture of the impact of customer success on business. That was called A Customer Success Economy. I wrote that with our COO at the time, Alison Pickens. Then we did several more beyond that. But yeah, it's, there are 4 books on Amazon, although, uh, the credit should really go to the co-author in all of them.

So, and then you, you also brought up kind of advocacy. I don't know if you used that word, but you know, you're out advocating and my understanding is like you personally have met with thousands of companies and investors to advocate customer success. Can you just tell folks about that? Are you still doing that? If you had like, I don't know, a pie chart of your time, how much of your time goes to that?

Yeah, it's kind of interesting. Early on it was proactive and like intentional and eventually just started becoming part of just my daily routine. So what does that look like? And I'll describe the pie chart. So what it looks like is you can think of like supply and demand. So the demand is companies that are trying to figure out their customer success strategy. And then supply is people in the CS profession, particularly leaders, you know? And so lots of my calendar is a CEO saying, hey Nick, um, can I get your advice on like restructuring my customer success team or hiring a CCO? Do you know anyone that you might recommend? And then the supply side is, you know, hey, talk to CCOs that are looking at their next thing or trying to figure out where their career is going and, you know, Yeah, I mean, I'm literally, the day we're recording this, Mark, I did 2 conversations this morning, you know, like, and that's not, um, that's pretty normal. Like, I, my guess is it's 1 or 2 a day for more than, you know, 12 years now. Um, and it's been awesome 'cause I get to really hear like what CEOs and boards are thinking where they're like, they all know the problem matters, but they're not sure how to solve it and what type of person to look for and how to structure it and should it report into a CRO and all those kinds of things. And then the leaders looking at their next job aren't sure what kind of company they want to work at and what are they looking for in the job. And so I'm the, you could either say I'm an unpaid executive search firm or some people would say I'm like the eHarmony for customer success. Somebody said that once. It was kind of funny, so.

Well, you know, I would imagine that you placing these people is really good for retention of your software.

Yeah, it's funny. It's not a, it's interesting. Yes, I don't, I think objectively probably is, and it's never been a thing of like that transactional. It's honestly sometimes I remember there's one time there was a customer who, a new executive came in and she, uh, took over for an executive that was a big Gainsight fan. She took over, she didn't, wasn't anti-Gainsight, she just didn't know anything about customer success platforms. She thought they could just do it in Salesforce and so she churned Gainsight. Uh, like literally right away, like, and we were like, oh, that's obviously anyone that's in a business, you know, that never feels good. And then a few weeks later, she LinkedIn'd me that she got laid off, um, from her job, you know, for other reasons and it's not unrelated to Gainsight. And so she's like, could I get on a call to get some advice? And so I got on a call with her and made some intros and I don't think my intro was the one that she took, but you know, I was happy to help, you know? And by the way, I don't think she ever bought Gainsight later. It's not like there's some, happy end of the story of, oh yeah, she became a— it was just like, yeah, it's fun to try to be helpful to people. You know, I've, I discovered for my own like satisfaction in life, just being useful to other people, like feels really good to me. Not, I'm not some saint or something, just helps me. So yeah, when somebody messages me and looking for a job or something, it's, it's a great honor to be honest.

I love it. When I onboard new CEOs, and I only work with growth stage CEOs, One of the questions I ask is, I don't know, when's the last time you spoke with a customer? How often do you speak with customers? And, and often they're actually pretty far removed from the customers and they're just a little caught up in what all the internal matters, right? They've got hundreds, in some cases thousands of employees and it's all consuming. How were you able to maintain that focus? Like, do you just surround yourself with operational people and like, You like, yeah, what, what would you do to kind of preserve that ability to be able to like keep, keep so much of your time with customers?

Yeah, it's each, I think part of like, um, learning for myself at least, learning about myself as a leader is learning the things that I'll naturally do no matter what. And then the things I kind of have to force myself to do. So, you know, like, yeah, outside of work as an example, I will naturally do anything for my, my family or, naturally wanna go exercise or something, right? But there's certain things like, I don't know, like figure out to fix some, you know, the water heater or something, something like I don't, I'm not good at, I don't know how to fix. And things I just, they'll just like hang out on my to-do list forever at home, right? And probably people watching have things like that, things you just naturally gravitate to and things you naturally have to force yourself to do. So for me, Mark, like talking to customers or people, our ecosystem, it happens now. I love it. Like it's fun. I really enjoy it. And then there's other things where I got better at it, but I had to like push myself to do it. It was the thing that wasn't as natural for me. Um, so an example would be like really thinking hard about, you know, cost structure and margins and all that. By the way, I think we're pretty good at that now. But, um, where it wasn't something that like I was like, oh my God, I can't wait to tear open this spreadsheet. And I know other CEOs, Paul Quinn, who like, I remember the like going on a business trip and there was this like CEO who's there and he was CEO of a publicly traded company most people watching would know, um, at the, at the time. He's not that CEO anymore. And I was like, oh, like what's your favorite part of your day? And I kid you not, this CEO said, I love reviewing expense reports. And I was like, more?

That's a low leverage activity.

That's not at all— even wouldn't even make the top 1,000 for me. And he was like, for him it lets him see like how operationally disciplined his company is and he he dug in and, you know, his company was pretty big at that time and he would dig in and see like where money's being wasted. And so he loved that. Good for him. Like, that's awesome. And so what I learned was, for me, I had to like figure out what, what are the things I will naturally do? What are the things I am going to do myself because I have to and maybe I'll get good at? And what are the things I'm not going to do and I just need great people around me for? So for example, I love I love talking to customers and I love working on products and a business strategy, product strategy, right? Those are the two things I love to do. But if there's other things that I like to do but I don't love to do, let's say go-to-market structure or think about sales pipeline or processes, all really important things, I will force myself by scheduling an all-day meeting where we just only do that, you know? And so that's like actually been a really good way for me to kind of hack my own psychology. You know, if you're not somebody who naturally gravitates towards customers, an interesting question is what's a way you force yourself to have to do it? What's a forcing function? Maybe it's a conference you hold, maybe it's an advisory board. Is there some way that you could force yourself to do something that maybe just doesn't come as naturally to you? So I think for me, being aware of where I naturally gravitate to and where I naturally don't, and what do I need to do to like force myself into situations that are a little less comfortable. So for me, it's looking at spreadsheets, force myself to look at the spreadsheets. They matter too.

I love it. Yes, they do. They do. You know what I'm about to say perhaps doesn't survive 100% contact with the real world, but it's kind of one of my principles, which is like the CEO should build hers or his or her role around her unique superpower and then hire, delegate, automate, eliminate the rest. And you know, I saw this firsthand at Shopify where Tobi was just like, I wanna spend all my time on product and technology. You know, he runs a public company. He should be the guy doing the Wall Street quarterly stuff, but he's not. His right hand Harley does it.

Yeah, Harley does that, right?

Yeah. So I'm hearing you do some of that, but you're also willing to wade into your uncomfortable zone as well.

Yeah, that's it. I, I mean, there's a line where it's like, okay, Things that you don't, you know, are, need to be done, but you can't do 'em at all. And things that like you naturally do. And there's things, there's a gray area in between. You know, when I, when I, um, talk to my direct reports, one of the things I like to do sometimes is say, let's put up a Venn diagram. Things that you're uniquely good at, things that bring you energy, and things that the company needs, right? In an ideal world, you're operating in the center of those. You're like doing this stuff you're the best in the world at, and it's bringing you energy and the company needs it. And it's not always like that. So sometimes the company needs things from me that aren't the things I love, but I'm with you that Toby's absolutely the role— I don't know him at all, but like he's the role model where it's like he's structured his company a way that he can do the things that are legitimately awesome. And he's at the pioneer of like using AI and e-commerce and all these amazing things, right? And he's got Arby and other people to run the rest of it. You know, for me, what's been interesting is like bringing in, um, my president, Trek Ganapathy, who joined us about a year and a half ago, and he is awesome. And it's like, we are like this where there's certain things that we like really kind of synergize on together, for example, strategy and all that. And then there's certain things that he's super deep in, like, you know, he came in and we, you know, marketing pipeline, I think in every single company is always like a constant source of like, we need to do better, whatever. And he came in and just like grounded out, worked with the team, looked at the data, you know, and that's something I could have done before and should have done before and I didn't. And so that's a good example where it's like, okay, is there enough overlap between you and your team where there's certain things you can do together, but also certain things you can divide and conquer on?

Mm-hmm. Yeah. Oh, so important, right? Because your kryptonite is somebody else's like absolute zone of genius, right? Totally.

And I think if you don't have any overlap, it's a little hard to relate to each other. So it's nice that like, I would say all of the people that work for me, we have some shared interest and then some divide and conquer.

Yeah, that totally makes sense. There's many more questions I could ask specifically on the people who work for you, but we'll see if we have time. I want to move on, maybe just kind of let's talk about the team generally. You know, in the, in the past, Gainsight has been voted kind of number one place to work by Glassdoor. And you know, many of my CEOs have a love-hate relationship with Glassdoor. Like we think sometimes like, I don't know, is employee NPS the right thing to shoot for? Maybe we don't want our people to be fat and happy. So I guess maybe my question is, how did you drive performance, create the results you created while at the same time being voted the best place to work? Because that sounds like a threading of the needle in some ways, you know?

It is hard. I also understand you're right. I mean, because you talk to so many CEOs too, it is— Glassdoor is funny. It is the like, most beloved and hated thing out there for CEOs. And it's beloved if their scores are good and it's hated if the scores are bad, right? But it's, it's correct that it is a little bit biased. It's a lot like Net Promoter Score, which is a survey methodology for measuring, you know, customer feedback, right? And it's, I always joke that with NPS, the people that love, companies that love NPS are the ones with high NPS. And it's not, the causality is the opposite of what you'd think. They're just like, they, they have a, great business, has INPS, therefore they love it. And the same thing's true at Glassdoor where I think some of it is, um, that yes, it's an out— it captures the outliers. You know, most people don't fill out the Glassdoor survey, so the people that do are the ones that either totally love your company or totally hate it. And it's not always representative. But the way I think about it is our Glassdoor has gone up and down over the years. You know, like in the, in peak bubble times in 2021 or '20, whenever we owned the award, You know, we were like a 4.9 on Glassdoor, right?

Wow.

And, um, and I, I think it was 4.9 or something. We were at the, like, that was our all-time high, you know? Um, and, but you know, we've gotten bad reviews too. Like, I remember the first time we got a bad review at Gainsight. So like, this is a thousand years ago. I mean, I was probably like 8, 9, 10 years ago and we were this little baby company. And when you're a little, little company, like all your Glassdoor reviews are good 'cause everyone is like, brand new and they love it. It's this little company. And we got this first review and it was, we only had like 50 people in the company or something. And the review, I'll never forget it. It said modern day sweatshop. And I was like, oof. Oh, well, I mean, I don't think we actually are, but okay, let me listen. And you know, it was a small enough company. You're like, I, I, I knew who wrote it, by the way. The person really cared. That person stayed several years after and he was very kind. He shared, yeah, he eventually shared the specific feedback or whatever. Right. But I remember getting that and being like, you know what? It's like you can't just overreact on one thing 'cause your job isn't just popularity. Your job as a CEO is not popularity for, with your customers or your employees. For example, if you use customer NPS as an example, if you just are looking at short-term what customers think, you would miss the turn in how the world is changing. Like let's say with AI as an example, right? And so I think the same is true with employees. Glassdoor is not something where it's just the end-all be-all measurement of a company, in my opinion. So when we had the award on Glassdoor, yeah, that was super cool. Awesome. But yeah, did our score go down when like the bubble abated? Absolutely. You know, I think, I don't know, we're probably 4.2, 4.3 now. I think the thing that's, I do take away though about Glassdoor is, to me, the thing that's interesting is when the company's doing okay, like when it's not crazy gangbusters, Your score is a reflection on the, the almost like the, the floor of your culture. So I think a, like a low point of your score is the floor of your culture, kind of holds everything up. And the high point ends up being like, yeah, you're doing great at some point, you know, you're killing it or crushing it. And then things have come back down to earth and then you go up again and all that. And so what you find is some companies' floor is like a 2.5, right? And the problem is then comp— employees are only happy if everything is going awesome. And if things aren't going great, every, all the morale goes away. And I think what's cool is if you could build a company with some level of a cultural backbone, it gets you through the times that aren't great. You know, I don't know how, you know, you, people watching, if you're in SaaS, it's not great in SaaS right now. It's not. I mean, it's great if you're like a giant company or it's great if you're a OpenAI, but for most SaaS companies, it's not great. Like, it's not like there's nobody. I mean, if somebody tells you that, it's just not true. And so the, where your culture is now, whether it's measured by Glassdoor or somewhere, it represents a little bit like the floor, like the backbone when times aren't awesome.

I'm curious what, you know, so Gainsight has these core 5 core values. I'm curious when you look back what role values have played in the success of the company.

Yeah, totally. And they've, I think like everything in life, they can become strengths and you have to watch out for the shadow side of them, both sides, right?

Yep.

So we've had 5 values from near the beginning. The, in the very beginning we had 3 and we added 2, so The first 3 were Golden Rule, treat people the way you want to be treated. Success for all, make a business that drives success, not just for shareholders, but also customers and employees. Childlike joy, which means bring the kid in you to work every day. That's the one that became kind of like people got to know that with our silliness, if you follow us online. And then we added in Shoshin, which is the Japanese word for beginner's mind. And, um, stay thirsty, which is all about ambition. So those became our 5. And we've had the, the first 3 were in 2013, the next 2 were in 2015. So we've had for a decade those, those values. And I will say that like one of the most common things when we hire new people and we say, hey, what's, what surprised you about GameSight? Like the most common answer once they've joined is, wow, you guys actually live the values. Uh, oh, like that actually is real. Like you care about them. You talk about 'em all hands. You, it's not just you talk about 'em, people just live 'em day to day. They open a meeting with a silly icebreaker because of childlike joy. They, they respect the opinion of new people because of Shoshin, beginner's mind. They have, they think about like all stakeholders because of success for all. Like these things are just part, like if you listen to our recorded calls, like our internal meetings, you would hear those words all the time. Now, is there a shadow? Yes, absolutely. Like, you know, it, those 5 values. How do you like give tough feedback? How do you do a layoff? How do you let people go? That's like the tough navigation. And sometimes people have this term, uh, that they, you know, in the industry people use weaponizing values, which is like the value to say, oh, you couldn't— well, if it's success for all and golden rule, how could you possibly ever fire anyone? Like, well, yeah, that's a tough— that is tough cuz that does affect that person and you feel for them. But what about everyone else in the company, right? And so yeah, it's, the values are really interesting. I think the key thing for me is the values are real if you're wrestling with them every day.

Yes.

Because real values are not, they're like clues, but they're not answers. And so they're clues on what you might do and it forces you to think. And what I'm, what I do think is important is like really thinking about them every day.

Yeah. I mean, I think back when people were in offices all the time, my complete sweeping generalization where values were cheesy posters on a wall that weren't really lived. But I actually think values are so important that they are at the root of every disagreement or every lack of alignment. There's either a value that's not being lived or a value that's in somebody's head that hasn't been articulated. Like, I think they're that important.

That's exactly right.

Yeah. All right. Let's, uh, we, by the way, we could, really go deep on that, but just trying to pack everything in here, the, the Nick highlights. Let's talk about a venture and venture capital, right? So I only coach CEOs of tech companies that have raised venture or private equity and therefore have high expectations on their shoulders shooting for a giant outcome, that kind of outcome you've realized. And I often talk, and I used to be a VC a long time ago before the hair was white. And often talk to CEOs just about making sure they really understand the bet that they've made, right? And understanding like the kind of expectations that VCs are shooting for. And, and that is generally true and is specifically true with tier ones because there's a very uneven distribution of assets under management and success and returns in the venture industry. And when I look at your funding history, your cap table was full of big swinging dicks. And so I'm curious, like, how did you navigate that? And just like all those giant expectations that you signed up for.

Yeah, it's really interesting. First of all, our investors are awesome. I'm super close to all of them, our VCs. I'm not just even saying that, they're just amazing people. And so, um, that's one thing that I got lucky. I think that's a little bit just situational to, you know, who you end up working with and all that. But, um, you're right that I think one of the most useful things, in fact, I was planning to write about this. If you're like, if you wanna understand a company, you have to understand their shareholders and their shareholders' expectations. And that's whether it's public or private equity backed or venture backed and backed by huge fund or small fund and seed fund and all these things, tho— the incentives matter a lot. And so, um, a couple things that I learned, one was, you know, we, we had, so our first investor was Battery Ventures and then Bain Capital Ventures and then Bessemer. Insight, Lightspeed, those are the big institutions.

Those are big names. Like all of those are big shiny logos, right?

And you know what, I think some of this also comes down to like, you know, you have to raise the right amount of money for the opportunity you have and then make the most of it, right? And so we raised about $150 million-ish pre-selling our majority to Vista. And you know, we're about a $235 million company in revenue now. So, you know, gotten, definitely gotten probably further than the average company of our era with the amount of capital we'd raised, even though at the time it seemed like, wow, that's a lot of money. And I think we could have, we could have been way more efficient. I could have, we could have gotten here with even less than $100 million, but that's a story for another podcast. Um, but one of the things that was helpful was just really being aligned with the opportunity with the investors about what being just super open, like what is the TAM, what is the market opportunity, can we really throw more capital or is this just like, you gotta just grow with it as it goes? You know, things like that. And then be aligned with the personal aspirations of each of your investors too. 'Cause one of the things I would look at if I was a founder raising money or whatever is not just the fund and the size of fund, but that person. So one thing that we get really lucky—

Oh yeah, person over fund, I would say. Totally.

And we got lucky that like our first investor, Roger Lee, our next investor, Ajay Deval, and then Byron Deeter, and then Jeff Lieberman. Those guys, these are different, the funds I mentioned, they're all hyper successful. And so I always joke that like, if Gateshead went out of business, it doesn't make a difference for them. They're doing this because they want us to be successful, you know? And that's very different than, you know, if you are working with a, a brand new partner at, uh, pick whatever firm you want and this is like their career maker and they're gonna have a different mindset, right? Or a partner that's about to retire and they're gonna have a different mindset. My, we, we just happen to get lucky that we worked with people that were like in the Goldilocks zone of like uber successful, but still like working super hard. And I, I could be more thankful to all of those folks. Um, the other thing is understanding the size of the funds and the dynamics. You're right. Like, yes, the math is very important to understand. Definitely. Like you, they'll own X percent of your company. Let's say eventually they own a given fund owns 10%. And that means if your company sells for a billion dollars, which is for many founders, ton of money, for them it's $100 million. And if their fund is a billion, it's good, but it's not like nothing to write home about. You know, I remember a, uh, a friend of mine was at, uh, a partner at a big, extremely well-known VC firm. And I remember he joined and, and, uh, he was brand new at this firm and he went in as like an experienced partner, like he was a founder before. And he met the founder of this firm who, or not the founder, the head of the firm who's ultra famous. I'm just keeping the names out 'cause anonymity. And they had just sold a company for like a billion dollars that day. And my friend said to the, the head of this firm, hey, congrats, that's amazing. And the guy's like, eh, like that was it. Like a billion dollars. Eh, you know? And so like, it's important to be aware of the dynamics, you know? And then also where you are in the cycle. It's kind of interesting when we, we sold at the end of 2020, right? And the market was just starting to heat up again. And for folks that remember, 2021 was this total bubble year in tech, right? And I remember when we sold, our investors were like, Nick, we trust you, whatever you wanna do. If you wanna keep running it, if you wanna take it public, they were like, what about going through public through SPAC if you want to? I was like, I don't know about that. And thank goodness we didn't do that. And then, um, and then we sold. And then in 2021, I had so much FOMO. 'cause all these other companies that didn't sell were worth like $3, $4, $5 billion. And then a couple, and then a year after that, our investors were like, oh my gosh, that gainset return was great. 'Cause it was, you actually got, we got real cash out of it. It wasn't some public stock that cratered or whatever. Right. And so I think the other thing to be aware of is just like, you know, not just the fund size and the partner experience, but where you are on that market cycle, you know, a billion-dollar exit in one cycle. Is great, and in another cycle it's okay, another cycle it's not very good, and it just depends on where you are. So I think ours was pretty good, and, and, uh, I think our investors appreciate it, and luckily we all have good relationships still.

So yeah, well, kudos to you. What you didn't say in all of that, uh, and I would double-click, but I want to move on to one final topic, but what, what is implicit in everything that you've just said is that your results were best in class. You don't get those investors unless your results are best in class. And when I look at the time between rounds, it got shorter and shorter each time, which tells me that was just like a crap ton of momentum there.

Yeah, it wasn't all perfect, but thank you for saying that. Yeah. Thank you.

So final topic, you and I first connected and started chatting online because you shared some big changes in your life and changes that I had been through as well. And let's face it, this is, by the way, what we're about to talk about isn't just a male thing, but like we are both males. And if a lot of my clients are men, and if I stereotype, right, they give 100% of themselves to their company. They find something from the 0% that's left for their kids out of obligation, and they have nothing left for their spouse. And then they're surprised when their health goes down and they get divorced. And, um, I was just wondering if you'd be willing to share kind of the journey you went through and, and what you may still be formulating your retrospective on this, but what retrospective, if any, you may have.

Yeah, totally. And by the way, things evolve even since we've exchanged interactions and all that. Yeah, but not, not better or worse, just, just things change. I think without going into specifics of, you know, what I've gone through, I think that there's Part, like, it's funny, the oversimplification is exactly what you said of like any CEO. It's like they do all of this and they're one part of the life and they don't do as much in other parts. I don't think it was, it's been like that for me. I'm great, you know, partnership with, you know, family, uh, my, my wife, kids, everything else. Um, but, um, definitely like it's prob— probably the biggest learning for me is less. I've always been somebody who gives a lot of time., to family, to everyone around me. But, um, it's more how over time, is there a world you get less attached to your identity and outcome as a CEO? So I think that's probably for me, it's not the, I don't think this is universal for everyone, but, um, the learning I've had so far, and actually I was just talking to my coach about this, is, um, that there's a certain detachment that is, can happen naturally in life where at some phase, how much you've raised or how much your company's worth, or where are you on some list of some, you know, 40 Under 40 or 50 Under 50 or 20 Under 30, 20 or 30, whatever it is, right? Or whether you went public and you have a photo of the NASDAQ and those things are really healthy. I love it. Like, that's awesome. That's part of life. And then at some point you're like, actually, I'm not as attached to that anymore. More, you know? And maybe you had some success and maybe you feel like, okay, I've done that. And so for me, one of the learnings has been, and, and it's not like a learning of, hey, I wish things were different. It's more just like, oh wow, it's fascinating to be like, I'm not as attached to the same things as I used to be. When I see somebody on LinkedIn that has achieved some amazing thing, you know, before I'd be like, how come I haven't achieved that amazing thing? And I'm, I'm human. Every now and then I think about that. But now it's more like, wow, that's awesome. Good for them. Like, that's fun. You know, the thing that gives me joy now is just like being there for my family, for other people. That's like the thing that gives me joy, you know? So yes, it's been all kinds of ups and downs of many parts of my life for the last few years outside of work. But I don't think it's as simple as the hours. It's actually more, what am I attached to? You know, and I think that attachment— I see Ganesh behind you there, uh, so, and on my arm.

Ganesh is my hope. He's my—

I'm not a super religious person or anything, but like this idea that like there are phases of your life when you feel really attached to something, and then, and you know, the reason I quote Ganesh, and some, some Eastern religions or religions in general, there could be like a notion over time you get less detached to things, right?

Yes.

And I, I do find myself less attached to external success, you know, and it's interesting. Again, I'm, I'm, oh, fault it like that. When I was more attached to it, that's fine too. But, um, I'm noticing that I am changing in that way. So, um, I wish I could give you some formula and I'm sure you wish you could give a formula, but the only thing I've, uh, enjoyed in is noticing how I am changing, evolving as a person.

I love that. You know what I tell folks is like, when we're in our companies, they're, they're all encompassing. You feel like nothing else matters. Like when I was at FreshBooks, I had what I call freshmares where I was just like dreaming about work at night and it was so prevalent. I just kept a notepad by my bed 'cause I was solving business problems at night. But now it's in the rearview mirror.

Totally.

And Gainsight has been around for many years. But still a minority of your life, right? And then, you know, you'll be here, you know, you sold it in 2020, you must be still enjoying life 'cause you're still there. But at a certain point you won't be. And I don't know, when you're taking your dying breath, Gainsight will be a chapter or two at most. It won't be your life. So a big part of what I try and encourage my CEOs is just like to zoom out and have that broader perspective. Like I literally, I wrote my obituary in 2021, you know, just to like help me have that more long-term perspective.

Oh, so much to say about that. This is where I really get engaged because I love philosophy. And like, I think there's an element where there, it's a question of, can you hold two conflicting ideas in your head? Can you be like, I am so obsessed with GameSight or whatever you're doing and also realize, yes, eventually that will go away. You know, eventually Amazon will be gone, and Microsoft, Google, and all the things we know, right? They'll all be gone, you know, or in some other form that's less relevant than they are today. And maybe they'll come back and maybe they'll go away. And, you know, there's a— if I could have asked, if I could wish everyone in the world would read, you know, 20 lines of poetry, it would be this poem called Ozymandias. I don't know if you know it or not, but it's by Shelley. It's a poem from, I think it's like the 19th century or early 20th century. And it's basically this poem about, um, a person walking through the desert and seeing, um, a, uh, like a, the head of a statue and it has an engraving on it. And the engraving is like a statue from a king from thousands of years ago that talks about how powerful he was. I'm not doing it justice. You really have to read it. But, um, the idea is that the, the head's fallen off in the sands of the desert and basically the rest of the statue's gone, you know? And the idea is like, yeah, it, it's all gonna be gone eventually. Right? And so how can you both hold in your mind that like, I'm gonna be all in on whatever this thing is, whether it's my company or my family or my life, and also accept that, yeah, eventually those things do fade away, right? They do. And can you do, can you hold both ideas in your head at the same time? Um, for me, I try to, and I also recognize, you know, eventually if you're, you move on from your company or you sell it or it shuts down, it doesn't mean it didn't exist. It did exist. Like in tech, I think we have this, incredible and very like powerful infatuation with the moment. This moment, what it is right now, open air, Anthropic, blah, blah, blah. Google is a dinosaur. That's what you'll see people online say sometimes, right? We know Google generates $100 billion of profit a year, so. Yeah, exactly. Oh, I'd take that dinosaur any day.

Still very much alive, not a dinosaur yet.

Blackberry was a, made the mistake and missed it. Blockbuster was a failure. But you know what? Like I think about it a different way. I'm like, me included, maybe you, millions and millions of families had family movie night through Blockbuster.

Yeah. Very much, very much not a fan.

People sat, watched movies and maybe built, handled relationships. People communicated with their clients and bosses through BlackBerry. I love that BlackBerry thing. It was an awesome device, you know? It was. Um, you know, I've started my relationship with my wife on AOL Instant Messenger and like these things matter. So one of the other things I try to embrace is your company will eventually go away or you will go away from your company or both. And that doesn't take away from the fact that it mattered, you know, and that's a little hard to appreciate because tech is so in the moment. The only thing that matters is right now, but, um, there's some benefit to remembering that there's a history too, and those things mattered as well.

Yeah. So this topic could be a podcast on an, on into itself. So I'm using like every ounce of my willpower to wrap this up, cuz I know we're at time.

I love it.

But Nick, thank you so much for coming on the show. I've really enjoyed it. And yeah, congrats on all of your success. Like, it's pretty rare, you know, you're humble about it, but you know, you truly have created a category, worked with the best of the best on the venture side. Vista is the most successful PE acquirer of software companies, period, full stop. I tried when I was an investment banker. To get their operating Bible and they just laughed at me. So, you know, so I wish you continued success and we'll be cheering you on from the sidelines.

Right back at you, Mark. Thanks for having me on. Great conversation.

Thank you. Hey, thanks for listening to The Startup CEO Show. If you'd like to connect with me, be sure to visit my website at markmacleod.me or follow me on LinkedIn at The Mark MacLeod or Twitter @MarkMacLeod_ Score. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.