Gainsight’s Nick Mehta on Creating the Customer Success Category, Building Culture at Scale, and Finding Balance as a CEO

Nick Mehta co-founded Gainsight in 2013 when there were only about 1,000 customer success managers worldwide. Today, that number has grown to hundreds of thousands, making Gainsight one of the rare companies to successfully create an entirely new job category.

In this conversation, Nick shares the playbook behind category creation, how they attracted top-tier investors like Bessemer and Lightspeed, the reality of building company culture while scaling to hundreds of employees, and his personal journey toward finding balance as a CEO. Plus, why Taylor Swift’s business acumen offers valuable lessons for entrepreneurs.

Here’s the full conversation:

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. They acquired a whole bunch of tier-one 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 are you doing today?

Nick Mehta:

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

Mark MacLeod:

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, before Gainsight, people were just called customer support reps. And then you created this category called customer experience. Just your visibility as a founder, so many things.

But let’s start with the most important topic, Taylor Swift. What’s up? Like, why is she such a big deal for you specifically?

Nick Mehta:

Well, it’s funny because, you know, whenever 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.

Mark MacLeod:

Yeah, I can see that.

Nick Mehta:

You can see a little bit over here, you couldn’t see, but, well, you can see a Steeler helmet back there. Because I grew up in Pittsburgh. Steeler fan. So I mean, to a lot of different things, but certainly one of them is music. But the reason I love Taylor specifically is two things. One is that she is an incredible business person and marketer, and just a leader, and things that we can all learn from creativity, community, and all that.

And then two is I love writing, and I love creativity and creative writing. And she’s an awesome lyricist. So, there’s my two things. She puts just her heart and soul into what she does. And I think I really respect people who do that, whether it’s in sports or in science or music.

Mark MacLeod:

I love that. You know, my daughter is out of the kind of peak Taylor Swift age. I don’t know if she ever had a big Taylor Swift phase, but I guess there was enough because I also have a shared passion of music, but very underground music. I was a rave DJ since the 1990s, 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 six in the morning.

Nick Mehta:

Wow, cool! Yes. Yeah, nice.

Mark MacLeod:

But I’ve. 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.

Nick Mehta:

So smart.

Mark MacLeod:

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.

Nick Mehta:

Totally, yeah. And it’s positivity, but I think it’s also. I think it’s just one of the things that will probably translate well to business. It’s also just very authentic, honest, and vulnerable. And so what I really appreciate is that she’s able to take her feelings and express them in incredible writing. And I love poetry, I like fiction. It’s just that person who 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, I can feel like their heart being written on paper.

Mark MacLeod:

I love that. Now you said a thing that I 100% believe, which is that there are many layers to Nick. I forget your exact words, but you’re not just a Taylor Swift-loving person. But I feel like I’ve certainly gotten to know one of your layers just through how you put yourself out online.

I’m curious, have you taken any specific inspiration from Taylor or the persona you’ve created online? Does that come from just another place?

Nick Mehta:

No, I don’t think so. Well, I think all of us take inspiration for everything. So it’s an ambient, inspiration’s everywhere. So, the short answer would be having inspiration from so many places, absolutely. You know, anyone that I interact with, follow, or read about becomes part of who I am.

But I wouldn’t say it’s that. I think it’s actually more like seeing that, 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.

But it turns out, if you put your heart out there, some people might find it authentic and interesting. And so, I wouldn’t say that was from one person. It’s frankly more just experimentation. I remember we had this conference called Pulse, which is kind of the big industry event for customer success. And we’ve been doing it since 2013.

And it’s always been a little different because 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. Now I’m like, okay, thank you. I appreciate it. It was my great honor.

But it’s always been a little different. It’s kind of zany and funny and silly. And I remember Pulse 2016, almost a decade ago. We’re in Oakland, California, and I’m planning to close out the event, and I decided to kind of channel Brene Brown and 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, a few of our employees were like, I remember one of our employees put an 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. And it’s okay. That’s what they feel. That’s fine too.

But a lot of people resonated 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 feel privileged and lucky that I could 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.

Mark MacLeod:

Yeah, well, I’ll tell you, it compelled me to want to have you on this show. It’s a magnet, for sure. And like, in a sea of companies, it creates a connection, right? It creates a meaningful human connection.

So, haters are going to hate. Nothing you can do about that feedback you got. But 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 impostor 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 you’re just putting yourself out there because it gives others permission to do the same. I think it’s really important.

Nick Mehta:

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

Mark MacLeod:

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

Nick Mehta:

That’s exactly right. Exactly. Nailed it.

Mark MacLeod:

Thank God there isn’t a playbook. But speaking of playbooks, Gainsight is one of the few companies that stands out for creating a new category. 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; was that your intention from the start? Did that just sort of evolve over time? And how did you reverse engineer the playbook that you created in doing that?

Nick Mehta:

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

Mark MacLeod:

I didn’t know that. Okay, I’ve always associated it with you.

Nick Mehta:

Yeah, yeah. We talked about this book, we wrote the blue one back there. We talked about the history, but you’re right that it was pretty small. Like, we launched in 2013, and in 2013, we didn’t know it at the time, but if you go back and look at the historical data, there may be a thousand CSMs in the world on LinkedIn, and now they’re depending on what titles you look at, a few hundred thousand. So it’s pretty big growth.

And yeah, I always joked that, back then, if we knew that there were only a thousand or something, we would have never done the company because it was shrinkingly small. It was horrible. But we didn’t know.

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 early SaaS companies. And we knew that the old model of market, sell, and support the customer when they call you was insufficient for all the reasons that are obvious now.

Now 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 because we had an old playbook that came from what people refer to as the on-premise software world, which I say referred to because some people watching may not totally know what that means.

Basically, people would sell 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, 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 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. Our market didn’t exist. And so we had to help kind of evangelize it and sort of ferment it into something significant.

That’s why we created a conference on customer success, which thousands and thousands of people have been to, wrote five books on customer success that hundreds of thousands of people read. And so, all of that was out of necessity. I wish it were some genius idea. It was, frankly, probably objectively not doing enough research on the TAM early on and saying, well, people are getting to our software and not realizing, well, actually, you need people that can actually buy it.

And then one thing led to another, and 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 natural. And people are still figuring out what it actually means.

But the idea that you need to focus on retaining customers is no longer a new idea. In fact, when I explain to 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, but wasn’t obvious then.

It’s kind of cool to work on something that is now obvious because that means the people who worked on this were kind of pioneers. Not just us, everyone that back then in 2013, they were pioneers.

Mark MacLeod:

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, five books, that feels like a lot. Does that mean you are personally the author of five books? You may have had co-authors, but like you are in Amazon. I can go search for Nick Mehta, and I’m going to find your books?

Nick Mehta:

Yeah, four out of the five I’m an author on. But credit where credit’s due, the first one, which is that blue book in the back, you can see right in the background, it’s called Customer Success, very generic. But it became kind of the authoritative book.

Dan Styman, who was our first chief customer officer at Gainsight, and truly deserves a huge part of the credit for the early days of Gainsight, 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 the big picture of the impact of customer success on business, which was called Customer Success Economy. I wrote that with our COO at the time, Allison Pickens. Then we did several more beyond that. But yeah, there are four books on Amazon, although the credit should really go to the co-author in all of them.

Mark MacLeod:

And then you also brought up advocacy. I don’t know if you use that word, but you’re advocating. And my understanding is 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 a pie chart of your time, how much of your time goes to that?

Nick Mehta:

Yeah, it’s kind of interesting. Early on, it was proactive and intentional, and eventually just started becoming part of 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 supply and demand. So the demand is for companies that are trying to figure out their customer success strategy, and then supply is people in the CS profession, particularly leaders.

And so lots of my calendar is the CEO saying, hey, Nick, can I get your advice on restructuring my customer success team or hiring a CCO? Do you know anyone whom you might recommend? And then the supply side is, hey, talk to CCOs that are looking at their next thing or trying to figure out where their career is going.

And yeah, I mean, literally the day we’re recording this, Mark, I did two conversations this morning, and that’s pretty normal. Like, my guess is it’s one or two a day for more than 12 years now. And it’s been awesome because I get to really hear what CEOs and boards are thinking, where 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 it should report into a CRO and all those kinds of things.

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. So, you can 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’s kind of funny.

Mark MacLeod:

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

Nick Mehta:

Yeah, it’s interesting. I think objectively probably is, and it’s never been a thing of that transactional. I remember there was one time there was a customer who our new executive came in and she took over for an executive who was a big Gainsight fan. She 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 literally right away. And we were like, oh, that’s awful. Anyone who’s in a business that never feels good.

A few weeks later, she linked me that she got laid off from her job 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. It was just like, yeah, it’s fun to try to be helpful to people. You know, I discovered for my own satisfaction in life, being useful to other people feels really good to me. Not some saint or something helps me. So yeah, when somebody messages me looking for a job or something, it’s a great honor, to be honest.

Mark MacLeod:

I love it. When I onboard new CEOs. I only work with growth-stage CEOs. One of the questions I ask is, “When’s the last time you spoke with a customer? How often do you speak with customers?” And often, they are actually pretty far removed from the customers, and they’re just a little caught up in all the internal matters.

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? What did you do to preserve that ability to keep so much of your time with customers?

Nick Mehta:

Yeah, it’s interesting. I think part of 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, outside of work, as an example, I will naturally do anything for my family or naturally want to go exercise or something. But there are certain things, like figuring out how to fix the water heater or something I’m not good at and don’t know how to fix, and things that’ll just hang out on my to-do list forever at home. 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, talking to customers or people, our ecosystem, it happens naturally. I love it. Like, it’s fun. I really enjoy it. And then there are other things where I got better at it, but I had to push myself to do it. It was the thing that wasn’t as natural for me.

So, an example would be really thinking hard about cost structure, margins, and all that. By the way, I think we’re pretty good at that now. But where it wasn’t something that I was like, oh, my God, I can’t wait to tear open this spreadsheet.

And I remember going on a business trip, and there was this CEO who’s there, and he was the CEO of a publicly traded company most people watching would know, at the time. He’s not that CEO anymore. And I was like, oh, what’s your favorite part of your day? And I kid you not, this CEO said, I love reviewing expense reports.

Mark MacLeod:

That’s a low-leverage activity.

Nick Mehta:

That wouldn’t even make the top thousand for me. And for him, it lets him see how operationally disciplined his company is. His company was pretty big at that time, and he would dig in and see where money is 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 figure out 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 one of the things I’m not going to do is I just need great people around me for.

So, for example, I love talking to customers and I love working on products and a business strategy, product strategy. Those are the two things I love to do. But if there are 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 only do that.

So, that’s actually been a really good way for me to kind of hack my own psychology. If you’re not somebody who naturally gravitates towards customers, an interesting question is, what’s the way you force yourself to have to do it? What’s the 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 I need to do to 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.

Mark MacLeod:

I love it. Yes, they do. You know, what I’m about to say perhaps doesn’t survive a hundred percent contact with the real world, but it’s kind of one of my principles, which is like, the CEO should build his or her role around their 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 want to 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.

Nick Mehta:

Yeah, Harley does that, yeah.

Mark MacLeod:

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

Nick Mehta:

Yeah, that’s it. I mean, there’s a line where it’s like, okay, things that you don’t need to be done, but you can’t do them at all. And things that you naturally do, and there’s a gray area in between. You know, when I 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. In an ideal world, you’re operating in the center of those. You’re doing the 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. Sometimes a company needs things for me that aren’t the things I love. But I’m with you that Tobi’s absolutely the role model.

I don’t know him at all, but he’s the role model, as in he’s structured his company in a way that he can do the things that are legitimately awesome. And he’s the pioneer of using AI and e-commerce and all these amazing things. And he’s got RV and other people to run the rest of it.

For me, what’s been interesting is bringing in my present Chak 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 are certain things that we really kind of synergize on together, for example, strategy and all that.

And then there are certain things that he’s super deep in. Like, he came in and marketing pipeline, I think, in every single company is always a constant source of “We need to do better, whatever.” And he came in and just grounded out, worked with the team, looked at the data, and that’s something I could have done before and should have done before, and I didn’t.

So, that’s a good example where it’s like, okay, is there enough overlap between you and your team where there are certain things you can do together, but also certain things you can divide and conquer on?

Mark MacLeod:

Yeah, so important, right? Because your kryptonite is somebody else’s absolute zone of genius, right?

Nick Mehta:

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, I would say, all of the people that work for me, we have some shared interests, and then some divide and conquer.

Mark MacLeod:

Yeah, that totally makes sense. There are many more questions I could ask specifically about the people who work for you, but we’ll see if we have time. But I want to move on, so maybe let’s talk about the team generally. In the past, Gainsight has been voted the number one place to work by Glassdoor.

And many of my CEOs have a love-hate relationship with Glassdoor. Like, 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.

Nick Mehta:

It is hard. I mean, because you talked to some of you CEOs too, Glassdoor is funny. It is the 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. But 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 customer feedback. And I always joke that with NPS, the people who love companies that love NPS are the ones with high NPS. And the causality is the opposite of what you’d think, they have a great business as NPS, therefore, they love it.

And the same thing’s true at Glassdoor, where I think some of it is that, yes, it captures the outliers. You know, most people don’t fill out the Glassdoor survey. So the people who do are the ones who 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. In peak bubble times in 20, 21, or 20, when we won the award we were like a 4.9 on Glassdoor. That was our all-time high, but we’ve got bad reviews too.

Like, I remember the first time we got a bad review for Gainsight. So, this was probably like 8, 9, 10 years ago, and we were this little baby company, and when you’re a little company, all your Glassdoor reviews are good because everyone is like brand new and they love it.

And we got this first review and 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. I mean, I don’t think we actually are, but okay, let me listen. And you know, it was a small enough company. Like, I knew who wrote it. By the way, the person really cared. That person stayed several years after, and he was very kind.

He eventually shared the specific feedback, whatever, but I remember getting that and being like, you know what? It’s like you can’t just overreact on one thing because your job isn’t just popularity. 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 are just 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.

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 the bubble abated? Absolutely. I think we’re probably 4.2, 4.3 now.

I think the thing that I do take away about Glassdoor is, to me, the thing that’s interesting is when the company is doing okay, like when it’s not crazy gangbusters, your score is a reflection on almost the floor of your culture. So, I think 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’re killing it or crushing it. And then things that come back down to earth, and then you go up again, and all that. And so what you find is some company’s floor is like in 2.5. And the problem is then, employees are only happy if everything is going awesome.

If things aren’t going great, 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, people watching if you’re in SaaS, it’s not great in SaaS right now. It’s not.

I mean, it’s good if you’re like a giant company, or it’s great if you’re OpenAI, but for most SaaS companies, it’s not great. I mean, if somebody tells you that’s just not true.

And so that where your culture is now, whether it’s measured by Glassdoor somewhere, represents a little bit the floor, the backbone. When times are awesome.

Mark MacLeod:

So, Gainsight has these five core values. I’m curious, when you look back, what role values have played in the success of the company?

Nick Mehta:

Yeah, totally. And I think, like everything in life, they can become strengths, and you have to watch out for the shadow side of them. Both sides. So we’ve had five values from near the beginning. In the very beginning, we had three, and we added two.

So the first three were the 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 for customers and employees. Childlike joy, which means bring the kid and you to work every day. That’s the one that became kind of like our silliness if you follow us online. And then we added in shoshin, which is the Japanese word for beginner’s mind, and stay thirsty, which is all about ambition. So those became our five.

And we’ve had the first three were in 2013. The next two were in 2015. So we’ve had those values for a decade. And I will say that one of the most common things when we hire new people, and we say, hey, what surprised you about Gainsight? The most common answer once they’ve joined is, wow, you guys actually live the values. That actually is real. You care about them, you talk about them all hands.

It’s not just you talk about them. People just live them day to day. They open a meeting with a silly icebreaker because of childlike joy. They respect the opinion of new people because of shoshin, a beginner’s mind. They think about all stakeholders because of success for all. 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, those five values, how do you 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 that they, in the industry, people use weaponizing values, which is like in the value to say, well, if it’s success for all in Golden Rule, how could you possibly ever fire anyone? Like, well, yeah, that is tough, because that does affect that person, and you feel for them. But what about everyone else in the company?

And so, yeah, the values are really interesting. I think the key thing for me is values are real if you’re wrestling with them every day. Because real values are 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 do think is important is really thinking about them every day.

Mark MacLeod:

Yeah. I mean, I think back when people were in offices all the time, my complete sweeping generalization was that 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.

Nick Mehta:

That’s exactly right.

Mark MacLeod:

Yeah. By the way, we could really go deep on that, but just trying to pack everything in here, the Nick highlights. Let’s talk about venture capital. So, I only coach CEOs of tech companies that have raised venture private equity and therefore have high expectations on their shoulders, shooting for a giant outcome, the kind of outcome you’ve realized.

I used to be a VC a long time ago, before the hair was white, and I often talk to CEOs just about making sure they really understand the bet that they’ve made. And understanding the kind of expectations that VCs are shooting for. 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, how did you navigate that? And just like all those giant expectations that you signed up for.

Nick Mehta:

Yeah, it’s really interesting. First of all, our investors are awesome. I’m super close to all of them; our VCs are just amazing people. And so that’s one thing I got lucky with, and I think that’s a little bit just situational to who you end up working with and all that.

But you’re right that I think one of the most useful things, in fact, I was planning to write about this. If you want to understand the company, you have to understand its shareholders and their expectations. And that’s whether it’s public or private equity backed or venture backed and backed by a huge fund or a small fund and seed fund, all these things. The incentives matter a lot.

And so, a couple things that I learned. One was our first investor was Battery Ventures, and then Bain Capital Ventures, Bessemer, Insight, and Lightspeed.

Mark MacLeod:

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

Nick Mehta:

And you know, and I think some of this also comes down to having 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 or majority of the Vista, and you know, we’re about a $235 million company revenue now. So you know, definitely gotten probably further than the average company of our era with the amount of capital we raised.

Even though at the time it seemed like a lot of money. And I think we could have been way more efficient. We could have gotten here with even less than $100 million, but that’s a story for another podcast. But one of the things that was helpful was just really being aligned with the opportunity with the investors about 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, things like that, and then be aligned with the personal aspirations of each of your investors, too.

Because one of the things I would look at if I were a founder raising money or whatever is not just the fund and the size of the fund, but that person.

Mark MacLeod:

Yeah, person over fund, I would say.

Nick Mehta:

And we got lucky that our first investor, Roger Lee, our next investor, AJ Edwal, and then Byron Dieter, and then Jeff Lieberman. Those guys, they’re all hyper successful. And so I joke that if Gainsight went out of business, it doesn’t make a difference for them. They’re doing this because they want us to be successful, and that’s very different than if you are working with a brand new partner at pick whatever firm you want, and this is their career maker, and they’re going to have a different mindset, right?

Or a partner that’s about to retire, and they’re going to have a different mindset. We just happened to get lucky that we work with people who were like in the Goldilocks zone of like uber successful but still working super hard. And I could be more thankful to all of those folks.

The other thing is understanding the size of the funds and the dynamics. You’re right, yes, the math is very important to understand, definitely. Like, 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 a ton of money, for them it’s a hundred million dollars. 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 friend of mine was a partner at an extremely well-known VC firm, and I remember he joined and he was brand new at this firm, and he went in as an experienced partner, like he was a founder before. And he met the head of the firm, who is ultra-famous. I’m just keeping the names out for anonymity. And they had just sold a company for like a billion dollars that day.

And my friend said to the head of this firm, hey, congrats, that’s amazing. And the guy’s like eh, that was what, a billion dollars? And so, it’s important to be aware of the dynamics and also where you are in the cycle.

It’s kind of interesting, when we sold at the end of 2020, 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 want to do, if you want to keep running it, if you want to 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 we sold. And then in 2021, I had so much FOMO because all these other companies that didn’t sell were worth like 3, 4, 5 billion dollars.

And then a year after that, our investors were like, oh my gosh, against that return was great because actually we got real cash out of it. It wasn’t some public stock that cratered or whatever. And so I think the other thing to be aware of is 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 Ethereum investors appreciate it, and luckily, we all have good relationships still.

Mark MacLeod:

Yeah. Well, kudos to you. What you didn’t say in all of that, and I would double click, but I want to move on to one final topic, but 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.

Nick Mehta:

Yeah. It wasn’t all perfect, but thank you for saying that. Yeah, thank you.

Mark MacLeod:

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. By the way, what we’re about to talk about isn’t just a male thing, but like we are both males, and a lot of my clients are men, and if I stereotype, 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 I was just wondering if you’d be willing to share kind of the journey you went through, and you may still be formulating your retrospective on this, but what retrospective, if any, you may have?

Nick Mehta:

Yeah, totally. And by the way, things evolved even since we’ve exchanged interactions and all that. I think, without going to specifics of what I’ve gone through, the oversimplification is exactly what you said, CEOs 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’s been like that for me.

I’ve got partnership with family, my wife, kids, everything else. But definitely, it’s probably the biggest learning for me is I’ve always been somebody who gives a lot of time to family, to everyone around me, but over time, is there a world where you get less attached to your identity and outcome as a CEO?

So, I think that’s probably, for me, it’s not that I don’t think this is universal for everyone, but the learning I’ve had so far, and actually I’m just talking to my coach about this, is that there’s a certain detachment that can happen naturally in life, where at some phase, how much you’ve raised or how much your company is worth, or where are you on some list of some 40 under 40 or 50 under 50 or 20 under 20, 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. 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 it’s not like a learning of, hey, I wish things were different. It’s more just like, 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 who has achieved some amazing thing, before, I’d be like, how come I haven’t achieved that amazing thing? I’m human, and 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 being there for my family, for other people. That’s the thing that gives me joy, you know? So, yes, it’s been all kinds of ups and downs in 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, I see Ganesh behind you there…

Mark MacLeod:

And on my arm. Ganesh is my hope. He’s my home.

Nick Mehta:

I’m not a super religious person or anything, but this idea that there are phases of your life when you feel really attached to something, and the reason I quote Ganesh and some Eastern religions or religions in general, there could be a notion over time you get less detached to things. And I do find myself less attached to external success, and it’s interesting. Again, I don’t fault it.

When I was more attached to it, that’s fine too. But I’m noticing that I am changing in that way. So, 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 enjoyed is noticing how I am changing, evolving as a person.

Mark MacLeod:

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

And Gainsight has been around for many years, but still a minority of your life, right? And then you’ll be here, you sold it in 2020. You must still be enjoying life because 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 to zoom out and have that broader perspective. Like, I literally wrote my obituary in 2021 just to help me have that more long-term perspective.

Nick Mehta:

Oh, there’s so much to say about that. This is where I really get engaged because I love philosophy. And I think there is an element where it’s a question of, can you hold two conflicting ideas in your head? Can you be like, I am so obsessed with Gainsight 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. They will all be gone, 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, if I could wish everyone in the world would read 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 a person walking through the desert and seeing the head of a statue. And it has an engraving on it. And the engraving is a statue of 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 the idea is that the head’s fallen off in the sands of the desert, and basically the rest of the statue’s gone.

And the idea is like, yeah, it’s all going to be gone eventually. And so how can you both hold in your mind that I’m going to be all in on whatever this thing is, whether it’s my company or my family or my life, and also accept that eventually those things do fade away, they do. And can you hold both ideas in your head at the same time? For me, I try to.

I also recognize that eventually, if 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 powerful infatuation with the moment. This moment, what is it right now? OpenAI, Anthropic, blah, blah, blah. Google is a dinosaur, that’s what you’ll see people online say sometimes. You know, Google generates $100 billion of profit a year.

Mark MacLeod:

Yeah, exactly.

Nick Mehta:

I’ll take that dinosaur any day.

Mark MacLeod:

Still very much alive. Not a dinosaur either.

Nick Mehta:

BlackBerry 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 nights through Blockbuster.

Mark MacLeod:

Yeah, very much not a failure.

Nick Mehta:

Couples went on, watched movies, and maybe built kindled relationships. People communicated with their clients and bosses through BlackBerry. I love that BlackBerry thing. It was an awesome device, you know? I started my relationship with my wife on AOL Instant Messenger, and these things matter.

So one of the other things I try to embrace is that 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. And that’s a little hard to appreciate because tech is so in the moment, the only thing that matters is right now. But there’s some benefit to remembering that there’s a history, too. And those things mattered as well.

Mark MacLeod:

Yeah. So, this topic could be a podcast into itself. So I’m using every ounce of my willpower to wrap this up, because I know we’re at time. 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’re humble about it, but 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, I wish you continued success, and will be cheering you on from the sidelines.

Nick Mehta:

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

Mark MacLeod:

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 X account @markmacleod_, 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!