Episode 48 | You're not unmoored. You're unchained. | Nick Mehta

[00:00:07] Nick Mehta is a serial founder and CEO, an entrepreneur in residence at Bessemer, a tech advisor to multi-profit companies.

[00:00:30] Nick Mehta, The Meg and Amy Show, and a co-founder at the New Work Foundation with Clara Shai. But most importantly, he's the tech world's foremost Taylor Swift scholar. Today, Nick talks with us about the identity shift that comes after you give up the title, the difference between feeling unmoored and feeling unchained. And he breaks down the rise of the forward deploy engineer and the wild economics of token maxing, and what both tell us about where AI and the enterprise goes next.

[00:01:00] Hey, this is William Tencup. Listen, we did a series for iSolved called Heroes of HR, where we talked to HR practitioners.

[00:01:09] And these are just your run-of-the-mill, everyday, slogging it out, 300 employees, and Cedar Rapids, HR pros. Mostly, it's centered around iSolved, and they're what they do with iSolved. But also, they talk a lot about kind of the day-to-day rigor of HR. If you're curious about that, search for Heroes of HR wherever you get your podcasts. Thank you.

[00:01:34] As we finish up Pride Month of 2026, Amy and I would like to dedicate this episode to The Trevor Project, an organization that provides information and support for LGBTQ youth. Please consider joining us in making a donation. Details are in the show notes. Welcome. It is so awesome.

[00:02:03] It's so awesome to be here. I've known you guys for so long online. It's great to see you online. Even better online. Exactly. Well, Nick, we follow your various stories about your mom, and it just is so much fun to watch. Probably more fun for us on the outside than you actually living it. But I just was wondering if you had any recent stories about this wonderful woman.

[00:02:29] Oh, I love my mom. I just spent a couple days with her yesterday. She's amazing. But yeah, she's become like a very minor celebrity with because I've kind of shamelessly used her in videos for my last company, Gainsight and like talk about her online. She's so I'm Indian American. So obviously she's Indian and she has a lot of the classic traits of an immigrant mom.

[00:02:49] Very much focused on success and comparison. It's just kind of deep. It's natural when you come from another country. Like it's tough. You know, you got to got to focus on making money and things like that. So I'll tell you two quick ones. One was my brother and I are super close just three years younger than me. And we're on a text thread. My mom, my brother and I, because my dad's not with us anymore. And my mom texted me the other day. She says, do you guys ever arm wrestle?

[00:03:13] And I'm like, that's the most random question I've gotten in like a year. I am 49 years old. The answer is no. I have not arm wrestled in a long time. And then my brother was like, well, he's arm wrestled his little kids every now and then. And then my mom's like, no. Have you guys arm wrestled each other? You guys should do it and tell me who won. And I'm like, oh, my God, I need to just send the text message to my therapist. This explains like everything.

[00:03:38] I don't know. I think you should sell tickets. I've been seeing your guns lately. I think I don't know. Your brother might be in for some trouble there. OK, all the compliments. Thank you so much for that. Wow. I love it. I love it. Yeah. And I want to know who else is going to recommend that you arm wrestle. Like I think that's it's an interesting question. You know, it's funny, though, because it's at least a more achievable goal. Like the other problem I have is my mom knows this person who's an incredible person in Silicon Valley.

[00:04:08] And I won't name her, but very incredibly successful and super early at like some huge tech companies. Like so obviously incredibly wealthy and every dimension like just does everything right and just awesome. Has a husband who's incredibly successful, famous venture capitalist and my mom's friends with her mom. And then unfortunately, this person also, in addition to all of that, cooks her mom's meals every day, like every day. And I'm like, so my mom tells me all that every single time.

[00:04:36] So I was talking to a friend of mine who knows this same entrepreneur woman. And he's like, you got to get your mom to be friends with people who have kids that are not successful. Yeah, exactly. Lower bar on like who are your mom's friends? Kids. They don't they don't call their mom all the time. They never talk to them. They dropped out of college. They never got a degree. I need more people. Everyone has recommendations of friends for my mom.

[00:05:00] So another another strategy, Nick, might be to pay this woman to do a video of you beating her in arm wrestling. Oh, my God. Honestly, Amy, she would probably just beat me in arm wrestling, too. Well, that's why we have to pay her. I didn't assume you'd win. OK, I like it. Honestly, honesty. We're all about strategic problem solving here on the Megan Amy show. I love it. What is the Megan show about now? And I don't even know. Is it about arm wrestling? Is that what it is now? Is that what you're talking about?

[00:05:30] It is now. Yeah. Yeah. OK, so on to the real meat of the day. So you recently stepped out of the CEO role after 13 years and you framed it as the end of the pre-written story. But you're not necessarily the best at chilling out. You said that as well. We've also somewhat recently made the operator to advisor leap ourselves.

[00:05:56] And we have lots of friends of the show that are mid-transition into something similar. And so I'm just kind of wondering, how do you decide it's time to hand off the thing you built? Like, how did you come to that decision? And how did you pick the person to hand it off to? We launched Gatesite in 2013, so a long, long time ago. And it was an amazing journey and so many ups and downs and venture-backed.

[00:06:26] And then we were really lucky to sell to a private equity firm, Vista, who was awesome and signed a great exit. And so there was this period when we sold to Vista at the end of 2020 when I was like, do I want to keep doing it? And I wanted to, mainly because of loyalty, you know, Vista had paid a lot of money for the company. Our employees had done such great work, our customers. So I wanted to keep doing it a few more years and learn. But I knew eventually I'd want to go hand it off. And then I did it a few more years. Underneath this, I was CEO of Gatesite at an awesome time. I guess 11 years is probably when I started thinking about it.

[00:06:54] And I was like, a couple things went through my mind. One was every leader eventually has a shelf life. You bring this energy and creativity to a company. But at some point, you know, it's very possible that somebody else could bring the next level of that, right? Especially when you go through a transition and some inflection. Number two was I was actually super excited about AI and like the new world. So I was kind of like a little bit like, oh my gosh, look at that stuff out there. Honestly, I was kind of like excited about that. And then number three was I was dealing with and have dealt with last few years a lot of tough personal stuff.

[00:07:24] And so I was looking for a head of product management. And the recruiter who was doing the search for us, Riviera Partners, said, I've got this guy. He's probably way more than that. But I think you know him. His name is Chuck Gunapathy. And Chuck and I had this weird story where like the first time I met him was literally 1999. I started a company. I was recruiting, trying to recruit people from Stanford Business School. And apparently, I don't remember this, but apparently I was like at the career fair at Stanford Business School. And I met Chuck. And he turned us down from Chip Shot, my first start.

[00:07:54] And then I, then we met many times. Like I was doing another startup and he was at Salesforce. And we were trying to partner together. Then I was an entrepreneur residence at Excel. And he was an entrepreneur residence at Excel. So all these different times we kept meeting. And I just love the guy. He was so great. And so then the recruiter said, hey, this guy Chuck Gunapathy, I think you know him. I was like, oh my God, I know him. There's no way he'd want to work for us. Like, what are you talking about? He turned me down once. Of course he's going to turn me down again. Yeah, there's no way. Like he just sold his company. He started a company.

[00:08:23] He wants to do something that's not CEO for a while. And so the number one value proposition of this job for him was he doesn't have to be CEO. There's an epilogue to the story you'll hear in a second. But I hired him in February 2024 and as president. And the idea was eventually he could be a successor. And I didn't say that officially, but it was kind of obvious to everyone. I gave him a lot of parts of the company. And then he's just amazing. Amazing human. Absolutely brilliant. Like incredible learner. So passionate. And so I saw this like growing passion in Chuck.

[00:08:53] I saw his ability. And then unfortunately my personal stuff got tougher. And so in 2025, January, I mentally decided I wouldn't do the handover. Talked to the board. They logged Chuck. So they were sold. And then talked to Chuck. And he's like, dude, the main reason I joined Gainsight is I don't have to be CEO. Now you're saying I need to be CEO. But he was such a good sport about it. We transitioned and handed over in August of 2025. So just come up on a year.

[00:09:17] I found a lot of joy in figuring out the succession plan for myself. And being able to nurture my team to step up when I departed and seeing them really flourish as a result. And that helped me a lot with my separation and keeping my identity as well. I love that. It's so true. Like that there is a lot of joy in doing it well.

[00:09:46] In fact, I'm super into like musicals and stuff. And so the confidential doc that was like the project plan for the handover, which is extremely detailed, was called Project Washington. Because there's a song one last time in Hamilton where they say he's a lot of say goodbye. So smooth. And mainly the main reason it was smooth is Chuck. And the second reason is our incredible employees and customers. Like we planned every detail. Who do you tell first? And when do you tell them? How do you communicate externally? And showing like we really are a partner together. I'm still on the board.

[00:10:16] It was so good. And so I didn't have any of that typical founder feeling of like, oh, God, I'm like that ended too quickly or I'm sad I'm not doing it anymore. I was like, I am so proud of Gainsight and Chuck and all the employees and customers. Much like, you know, if your kid goes to college and there's some sadness, but you're also just like happy for them. Right. I'm really happy for my daughter who's in college right now. You know. And where in the plan did you sing the song? Ah, this is the one thing.

[00:10:42] I have a face for radio and I have a voice for blogging. So I have neither of the face nor the voice. I'm a decent writer. So I wrote all of it. But you definitely have the charisma for the stage for sure. I would say so. Obviously, people are drawn to you, Nick, and I know you know this. And I think they're drawn to you for your openness and authenticity.

[00:11:11] And I think they're drawn to you because you really live in the fullness of who you are. And I think that's wonderful in any moment. But right now and in this moment where so many people feel unmoored in their identities and especially those of us that have storied careers where it's easy to wonder, what does my job look like in the future, etc., etc.

[00:11:37] And I think when you can show up with that level of authenticity and help other people see that the fullness is there for everyone, not everyone is willing to share. And so I hope you realize that's such an important gift in your journey is that you're living that journey out loud. That's something Amy and I really take seriously as well. I can tell you guys do. And I love that you said that. Thank you for saying that.

[00:12:05] And I think there is some incredible power to just authenticity, being open, being yourself, vulnerability, Brene Brown, all that. All that is like real. And, you know, it's honestly, I think it's easier to do when you're like a leader. I empathize with people. It's like harder to be themselves for many, many different reasons. But if you're able to, like it's so powerful. It causes people to really connect more with you. They open up to you. It's been like the story of kind of gainsight in general, just being open.

[00:12:32] And then your word of unmoored is interesting because that's a word I reflect on a lot. I mentioned I went through a lot of personal stuff that largely left me feeling very unmoored. But then there's this other word that is almost like the same, but with different meanings, which is unchained. Unmoored, a ship is like chained to a dock. Unchained, a ship is unchained to a dock. Like the same thing. But there's some feeling I think that people have now where they can feel unmoored career-wise right now with AI and everything happening. And I have a lot of empathy for that.

[00:13:01] And I hope that I've seen some people kind of get to the other side that they feel unchained and they find this new thing that they're able to do and some creative outlet, some owning their own business or whatever. And hopefully more people go through that. What sort of strategies did you employ to kind of deal with the identity shift? There was a work identity shift and they went through a lot of personal identity shifts at the exact same time. I think in some ways when you're going through like an identity shift, like there's some rip off the band-aid thing.

[00:13:29] I actually think that there's like a challenge when it's more gradual. It feels more comfortable to make it more gradual. But for me, for Gainsight, like, yes, August of 2025, we did the announcement and I was done. I wasn't on any more management meetings like the next week. There was this like super powerful time when we literally recorded it in a studio in Redwood City. This like goodbye live all hands kind of thing. And we did one for our customers. So Chuck and I were like in the studio.

[00:13:57] And then we like stepped out. And some of the other executives were like in the same studio in other areas. They're all on their laptops. And they're on Zoom. I was like, they're in the executive meeting, the one I used to lead. And I'm not on anymore. And I've never been on it since. And I think there's this like sometimes there's this thing of, oh, I want to kind of cling to it. I want to follow the company. For me, it's not like, oh, my God, good riddance. It's like more like that was beautiful and it's over. And now I'm on to other beautiful things, you know.

[00:14:25] And so I think there's something really powerful about that. Now, I think it's easier if you believe that there's something new to go to. Right. So if you believe that that was it and, you know, that's sad. Right. If you believe that like, oh, my gosh, there's something new that's going to be calling me. That's where I think the identity shift is easier. And I think it gets to the mindset that is really available to all of us. How you frame it to yourself.

[00:14:53] Is this a moment of ending or becoming? Is this an opportunity or whatever? And it doesn't mean that you remove the grief. Of course, there's the transitional grief. But if you can allow yourself to create the framework of I'm unchained, I'm exploring, I'm going into new places that I know are going to be magical for me.

[00:15:20] I think that gives you more agency towards making that future true. So, again, love that you're modeling that. I love that. Yeah. And so you kind of answered this before when you were saying that you were just interested in, you know, everything that's happening with AI. But ultimately, at least for now, you decided on an entrepreneur in residence opportunity, right? Yeah. At this summer. So how did that come about?

[00:15:50] How did you decide to jump in in that way? Yeah. I mean, first of all, entrepreneur in residence is the most made up, it's not a job, it's a made up title. It's like, it's only in Silicon Valley thing. I mean, conceptually, it's somebody that has worked with a VC firm before. They want to spend time with them on figuring out what their next thing is. And so that's what I'm doing with actually a couple of firms, Bessemer and also a firm called Chemistry. And Bessemer was one of our first investors at GainSite. And there's a guy named Byron Dieter who's like one of the lead folks at Bessemer.

[00:16:17] He's an amazing person, amazing business person. And he's like, hey, as you think about what you want to do next, you want to just spend time with us. What that practically means is like they look at companies and they have meetings with the companies and they talk about all the deals they're looking at. And they include me in some of those meetings. And that lets me learn a lot about what's happening in different spaces I'm interested in. For example, you know, health technology, mental health technology, AI for like the services world. And so I'm just joining lots of meetings, meeting tons of entrepreneurs.

[00:16:46] It's so fun. Like today, I think I have like seven meetings with founders. It's awesome. And I haven't figured out what I want to do yet, but just helping me understand like what's in the world, what's possible. And also just get inspired. It's tied to this identity shift of like, oh my gosh, like there could be a new identity for me. There is a thing of, yeah, I did Gainsight for a long time and I definitely post a lot on LinkedIn. So therefore, there is this Nick made a CEO of Gainsight. Nick made it equals CEO of Gainsight. Nick made it equals Gainsight equals customer success.

[00:17:15] And I'm like, that's not my identity anymore. Nick made a former CEO of Gainsight. Nick made a former customer success guy. What's Nick made his present identity? That's being written. So Amy and I are doing some similar things.

[00:17:29] And I really double down on the getting in the room and talking to other entrepreneurs and innovators is a great way to sort of spark your energy, give you ideas, help you learn things, but also contribute in a way because you have experiences that are valuable to those leaders that can be really beneficial in those early days. Having lived in worlds that oftentimes founders haven't lived in yet.

[00:17:59] I love the idea of made up jobs and I love the idea of maximizing made up jobs with personal agency to turn that into something powerful.

[00:18:08] One of the things that I see in the market right now, and I think we even had a little bit of an exchange on Twitter about this, is I believe that one of the most difficult jobs right now are those SaaS CEOs that the world has changed and that they have to figure out how to navigate. And it's not that we haven't seen disruption or change or new entrants or new models come through.

[00:18:39] But I think we all realize that right now the pace and the way this is happening is a lot of whiplash and a lot of volatility for being a leader. But you're also a little bit removed from it and so you don't have the emotion. What is that bigger lens that you would offer to those CEOs? Where's the hope? What should they anchor on in telling themselves that opportunity story?

[00:19:09] And how is this a great moment for them versus the most vulnerable? The best thing in the world is to be a former SaaS CEO right now. Yeah. It's changed a lot, by the way. SaaS has bounced back a lot getting the stock market. Yeah, exactly. Two weeks. So it's like, it changes every day. And I think in general, what's going to happen in the business world is, I believe, is volatility is just going to be even more than it's been.

[00:19:33] You look at what's happening in AI and every time, Anthropoc released a huge model yesterday and everything changes again. There's no steady state. There's no constant. We've been living this as business people for a long time since, you know, great financial crisis, COVID, et cetera. But it's accelerating. And so I think there's some element of just like, hey, this is just it. And there's this amazing blog post that when I read over and over again by Ben Horowitz, it's who's an interesting Horowitz founder. It says nobody cares at the title.

[00:20:04] And basically, the idea is like, yes, you can consternate as a CEO or founder about all the challenges and all the ups and downs. What do you do? Or you can just take all the energy and try to do your job. Now, it's not intended to mean nobody cares. People do care. But like there's some element of spinning that is counterproductive. Right. And so I think that when I talk to these people, I think there's like two ends of the spectrum. On one end, the aspirational is it is possible to transform. It's hard, but it's possible.

[00:20:32] And Intercom is like probably the poster child of this. Like really, you know, Owen, the founder, like came back and he's totally pivoted the company to AI and like radically better valuation, revenue growth, everything else. Right. On one end. And then also that's not going to work for everyone. And it's not going to be as easy because one of the challenges with the poster child is everyone points to it and says, hey, you should do that. And unfortunately, it doesn't always apply in every space, in every business, every product or based on your cap table or your debt or whatever. It's not as easy for everyone.

[00:21:00] So this empathy for your current situation, if you're a private equity owned, it's harder. If you're a debt, you have debt, it's harder. If you are in a category where agents don't work as well, it's harder, you know. But at the same time, it doesn't mean you shouldn't try. Find a way to go do it, you know. And I think that one of the upsides of the market not valuing SaaS as much right now is there's more opportunity to go transform. When things are highly valued, it's actually hard to transform because you're like, oh, my God, I'm giving up all this value.

[00:21:30] When things have low value, you're like, what am I going to lose? Right. Like, that's it. That's a great point. Yeah. Yeah. And I do think that your broader recommendation of there is some merit to just doing what you're doing better. And yes, there's also great opportunity for transformation. And we can call your mom to help those CEOs understand how they're underperforming against their... That's a great idea.

[00:21:59] How the arm wrestling against intercoms going. Yeah. Not well. Not well. Maybe we should turn that into some service, right? Oh, my God. That's the best business idea for a long time. But I do believe that to your point about when things, when you're already at kind of value, undervalued, you do have some degrees of freedom to really run your business well and to not fall

[00:22:28] prey to the compares, but to the book that Doug Merritt recommended, The Chop Wood, Carry Water, like, just do the work is... There's a lot to be said for that. And then I think the other thing is if you don't want to... That's fine, too. And then obviously just, like, own up to that and say, OK, let's get somebody else to go do it. The worst thing is you're half-heartedly doing it. You're trying to transform, but you're also holding on to the past. And you're kind of not in it anymore. There's a lot of founders like that right now.

[00:22:58] Some of them get that second wind. You know, another example, a friend of mine started a company called Boomage, Raj Dadada. And he, like, started this company. It was like in one business. That business became less relevant. The revenue went from, like, I don't know, 100 million to zero. And he created a new business. And then that went to, like, a few hundred million. And now he's creating a third business that's like an AI business. They're entrepreneurs like that that are just able to reinvent. They're truly inspirational. So I would say, like, either you want to go do all that chopping the wood, and that's awesome and you can do it, or you don't and you should go do something new.

[00:23:28] And either one's fine. The worst is, like, stuck in between. Especially for the people in your care. I mean, I do think that that's the important thing to remember, that this AI transformation is a skill-building opportunity for the teams that are in your care. And by not having a clear understanding of how you want to make that work for your business, you're actually stagnating the talent that you should be building at this moment. You're so right. You're so right.

[00:23:58] Everyone suffers. When a leader is not in it, the CEO is not in it, the founder is not in it, everyone suffers. Customer sufferer, employees sufferer. It's like the worst possible situation. So you're, like, unintentionally harming people when you're in that situation. So as a part of this new role and new identity, you're involved in a number of very interesting ventures that I want to hear a little bit about. So one is the New Work Foundation with Clara Shai.

[00:24:27] Can you tell us a little bit about that, Nick? Yeah, totally. So Clara Shai is an entrepreneur and a total phenomenon. Another person where I hope her mom never meets my mom because the bad news, Stanford and then early, like, Google and early Salesforce and then executive Salesforce and basically created what now is Agent Force and then was at Meta running Enterprise AI. So she's done all the business things you can do. I met her, like, 10 years ago when she found the SaaS company. And so anyways, I saw her online posting about just, like,

[00:24:56] the questions around jobs and AI, right? I saw things she wrote. I was like, oh, that's awesome. It's really cool. And then we just started texting again. We hadn't talked for a while. And then she came to some events I was hosting. And she was like, I'm starting this organization called New Work Foundation, an organization to help Gen Z college students, college grads, recent grads, try to help navigate the world of work in given AI. Just everything from, like, how do you figure out the right career and how do you find the right training and mentorship?

[00:25:26] And it's very early. But she started this idea, this nonprofit, and she literally decided, okay, she could do anything, and she's going to go work on this problem. And then she said, hey, Nick, do you want to come on as a co-founder? And so we've just been working together, you know, six weeks or so. It's brand new. The basic idea is to build AI products. They'll help people run career decisions and, you know, interview prep and things like that, as well as content, which Claire's already done a lot of content. She's done podcasts, a lot of podcasts.

[00:25:54] She's done interviews, et cetera, to just educate people. Not to say, like, this is not a, oh, my God, all the jobs are going to go away because of AI. Because nobody has any freaking, edit my word there. Oh, no, you're allowed to swear on the Megan Amy show. And nobody has any fucking idea. And then on the other side is, like, everyone's like, oh, no, all jobs will be fine. And technology always creates more jobs than destroys, and it'll all be fine. And honestly, nobody knows. Probably both those extremes are wrong. But nobody knows how it's going to work. Also, how it's going to work over time.

[00:26:23] Maybe things, jobs are lost and new ones are gained, but it takes a while for the generations that were in between. They could have, like, lost career opportunity. And so, you know, when you talk to college students and recent grads, they're not as rosy. Take a look at all the recent speeches by AI people at graduations, right? It's not, like, all roses. I'm literally, actually, my rising ninth grader is going to go to private school, and there was, like, the open house kind of thing for, like, the new students. And so I went to it, and they had artwork from all the different students displayed,

[00:26:52] the existing students. And so there was all this beautiful art that these kids were doing, and this one student had an artwork that just said, in every part of it was written, fuck AI over or again. And then after that, they had, like, a talkback where all the artists were on stage explaining their work, and somebody said to that student, hey, explain what you meant by your work. Yeah, it wasn't clear. Fuck AI, and anybody that works on AI is evil, and I never felt more unsafe in my life.

[00:27:22] I was like, I gotta leave this space right now. They better both do any LinkedIn searching on me. But the point is, like, yes, it's not as rosy for, at least emotionally, for younger people as it might be portrayed for a lot of people in Silicon Valley. And so nobody knows what the truth is, but we need to have, like, the conversations, and that's basically what New Work Foundations about. It's interesting. So yesterday, actually, Meg and I did a live show,

[00:27:49] and this woman came up to us afterwards, and she's like, how do I get Gen Z folks in my, because this is an HR person, in my company to start embracing AI because they're so anti? And then she also had kids in college who were rejecting it and all that kind of stuff. And so I have a bit of a, like, contrarian position on it, which is that I actually think it's really good

[00:28:17] for kids to be anti-AI. And the reason is because I think, like, there's some sort of bodily reaction that they need to build competence before using AI. If they were to just jump straight to AI and use it for all of their work and for their thinking, like, it would be very easy to just offload every single bit of learning to AI.

[00:28:46] And there's just something in them that's saying, that would be really bad for me. So I'm just going to say AI sucks altogether. Like, I just decided that McDonald's smelled disgusting. Yep. And that was good for my body to believe that, right? Like, obviously there needs to be some sort of reckoning when they're, you know, when they meet the work world and there's expectations

[00:29:14] and they need to compete and all that, you know. So bridging that gap between like, okay, build confidence and competence and stay away from AI, but then you got to leap into it and this is how. So I love this concept. That's kind of what it sounds like you're doing. I like your interesting counter, you know, counter-conventional thinking there. I do get it. Like, I get it both from a, like, a fear perspective and I get it from what you're saying of like, there's some element of developing your own self.

[00:29:44] Like, it's a weird thing where like, we can't generalize to everyone in the world based on what entrepreneurs do. Like, yes, entrepreneurs all use the AI, but we're also like people that have already gone through all the learning and all that stuff, right? And so, yeah, that's a common Silicon Valley mistake is you take what, you know, people in San Francisco think in the tech world and you assume all humans need exactly that same thing. I think this is a good, good, true, it's true in AI. In fact, there's a good podcast, Strategity, some probably a lot of people do it.

[00:30:13] And like Ben Thompson, the guy who does it, said just yesterday, he's like, one mistake Silicon Valley people think is like that everyone is obsessed with productivity in their life. And the truth is, honestly, most people are not. They like wasting time. They want to watch TV. They want to like get on social media. They want to just like chill and have fun and like have a good life. And I think there's like a big mistake we make when we assume everyone is like us. I had that realization, not that this is turning into mom therapy, but I had that realization,

[00:30:43] I don't know, maybe about five years ago. So I have this big job. I have like no time. I carve out a day to spend with my mom to do something. We were doing something together. And I realized there was a very significant tension because her intentionality was to waste as much time as possible within, from every possible task in every possible way. And I am thinking, oh my God, I have exactly one day off. I have this massive job. I'm always traveling, whatever. And I'm trying to spend time with you.

[00:31:12] And the last thing I want to do is waste every possible moment, being the least efficient in our day as possible. And we need efficient bonding finds. Exactly. And well, I mean, we were just like driving from here to there and then back again, as opposed to planning our day to make any sense. I was really struggling between the, do I just take over the reins and say we're doing it this way? Or do I relax and like let us do it the dumbest possible way? And you know, whatever. And I realized I was completely missing the point.

[00:31:41] The point is we're just spending time together. And so what? We're spending time in the car, going back and forth. Fine. It's fine. Just relax about it. So that entire thing about presuming that other people have your orientation is always dangerous. And it's so hard to remember somebody else's lived context is different than yours. It's just, it's not malicious. It's just really hard. It's so true. I fully endorse everything you said, except when my mom spends like 10 minutes

[00:32:11] trying to order her food, a waiter at the restaurant. That's where I draw the line. I think there we need more productivity efficiency. I will just do the ordering. Is it for the servers making money on tips? We need her or him to get to the next table. So I want to go back to customer success a little bit since we have the, the, you know, father of customer success here. Maybe that could be your identity. I'm glad you said that. Some people said grandfather. I don't like that. Oh yeah.

[00:32:41] No, no, no, no. You're not old enough for that. Sorry. Not cool. So there's been, you know, a lot of narratives about forward deploy engineers and, and you've written extensively about it. Meg has a, has a great concept that she'll probably get into that we we've just started back at the EDS model again. So we'll, we'll have her talk about that too. But I just wanted to pick your brain a little bit on, is this something new?

[00:33:11] Is this something old? Is this the new face of customer success? What are we really talking about here, Nick? Yeah. And just for people's background, like, you know, so the term forward deployed engineer was kind of coined by Palantir because they were selling software to the government and to defense department. Obviously the term forward deployed comes from, you know, military. And in their case, you know, the software defense is such a complex area that they need to be able to kind of customize it per kind of organization they were selling to.

[00:33:40] And so they would have a team of, it sounds like from my understanding, two people, one that really understood the military processes, one that was an engineer, and they would actually modify the code per, per customer at early days, and then kind of eventually merge it back into the main branch. And that's kind of heretical for traditional software companies where it was like, okay, we have one product, everyone uses the same thing, right? In SaaS, that was the whole deal. You might have professional services to maybe configure it, but you wouldn't change the code. Now, the issue with that

[00:34:07] is that software then became pretty good for everyone, but not great for anyone, right? Like that's kind of like the general experience most people have with almost all enterprise software. And now you start selling AI where it's infinitely configurable, inherently based on what it does, but it's also like requires you to reconfigure not just the product, but actually your business, right? So to really use AI, well, everyone knows you got to rethink your business processes and how you work and your team. And so if you just give somebody cloud code

[00:34:35] or, you know, codex from, you know, OpenAI or, you know, any other product, they can get somewhat far, but often they'll build things and they don't get used or they won't really change the results and the revenue doesn't go up and you're seeing companies have more concerns about this now. What you need to do is get them to change their business, right? To really operate differently. And you see this really starkly when you meet a startup versus an AI native startup versus a big company in the same space. And the AI native startup will literally be generating

[00:35:04] 10x more revenue per employee because everything from day one was designed around AI. And the bigger company has a hard time changing. And so what's happened now is people said, well, Palantir did this thing. Maybe we can apply it to all AI companies, right? Where we can have four deployed engineers, which the term engineer is a little bit of a misnomer. It could either be a business consultant who's just helping with the process, like a McKinsey type, or it could be an actual engineer, a little bit of both. And they go to the client and they say,

[00:35:33] okay, you bought our AI software. We're going to help you redesign your processes and configure our product to really take advantage of it. And so you're seeing this pretty much in every AI software company now has adopted this mindset, every agentic software company. And is it customer success? Well, in the most generic sense, yes. Because the definition of customer success was, one of the originals was, hey, we're going to make sure the product you got helps you get to your business outcomes. And we're going to do whatever it takes to get there, right? Now, CS people, historically, not all,

[00:36:03] but many, weren't always super technical. And in addition, they were often assigned out at a high ratio. So one CSM might have 20 customers or 50 or 100. So no matter how good they were, they couldn't go super deep with the client. So there's some differences where FDE is much, often much more intense, like smaller number of clients. Frequently, it's more technical. In addition, because the company, many of the AI companies are paid based on token spend, like basically consumption, it's in their interest

[00:36:32] to get as much deployment and value as possible. In a SaaS model, the challenge was, it might be in your interest when that contract renews, but the contract might not renew for three years. So for three years, you're like, look, I'm just going to give them a bare minimum because I want to maximize my profit margin. And so now the vendor has a financial interest. AI creates kind of a compelling event because you have to get them to really change in this new world. And you're bringing in more technical oriented people. So those are the changes that make a little difference.

[00:37:02] Yeah. And to some degree, I mean, it's also just maturity as well, right? So everything's so new. There's a lot more to be educated on, a lot more to learn. One of the things that I hadn't really heard, but makes complete sense is the fact that it is changing business models rapidly, like meaning like how work processes are done and so on. Whereas with SaaS, it was really about

[00:37:30] fitting existing processes into new technology. With AI, you really need to rethink the business processes. So you really do need a lot more handholding potentially to do that. Yeah, right. Before you think about like the actual handholding and business process work was just on the customer. They also had to do it. But really back then they would change through ops people and change management, internal stuff. And by the way,

[00:38:00] some cases they just wouldn't change and they wouldn't use the software well and then the users hated the software, right? That's just how we got to where we're at. It's like a new relationship between a vendor and a customer in the AI world. And I think this shifts really nicely to this world where we all kind of understand that there's a need to recognize new patterns, right? So if you look at the pattern of software development, if you look at the pattern, the way that you deliver

[00:38:30] solutions to customers, and if you look at the pattern of how the customer's business needs to evolve, you're going to recognize opportunity differently. And so I think a lot of what these forward deploy engineers are offering is a pattern match that creates a little more confidence in the customer. So it's a little bit about educating, but it's also a little bit more confidence about, okay, you might not see this pattern, but I have seen this pattern and therefore here are some ways

[00:38:59] that we can kind of nudge you towards the future. That's exactly right. And these are such, the other thing that's tied to that is these are such new paradigms. You know, people say, you know, AI is non-deterministic, meaning like it doesn't always work the same time every time. And so there's all these new things and conventions and agents and models. And so there's so much that people are like, I don't know where to start. Like most people have this experience as consumers now, like it's like with AI, where do you start? What's the best way to do this? And so like somebody that comes in

[00:39:29] says, yeah, I've done this for three other companies and, you know, give you the confidence. You're totally right. Confidence is a big part of it. So another thing that you just mentioned with that was the economic incentives. And that gets back to like budgeting for tokens and so on. And I know that's also another company that you're deeply invested in and something that we've been talking about on the show as well. So I was wondering if you wanted to talk a little bit about that. So the company you're referring to is a company called Laridin,

[00:39:59] L-A-R-I-D-I-N. I joined the board of the company in I think February of 2026, so just a few months ago. It's backed by Andreessen Horowitz and the two founders are people I've known for a long time, great entrepreneurs. And they basically decided to try to work in this problem space of, okay, companies need help to figure out how they can get the productivity benefits of AI and also manage the costs. And what's been interesting just watching the journey for them and for AI in general is we've gone through

[00:40:28] kind of like three eras so far. So one era was when agentic coding just started, but not everyone knows this, but a lot of the pricing was still in a subscription model. And so therefore, you're like, awesome, there's a model called Opus 4-5, which from Anthropic kind of like really opened up agentic coding. And so somebody's using something called Cloud Code or Codex and they're like, awesome, use it as much as you want. It's fine. It's like 200 bucks a month for a company that's affordable. And then those companies,

[00:40:57] the model providers were like, oh, we need to switch to charge for a token because it's just exploding, right? And by the way, people assume the token costs would just plummet as things get cheaper over time and they haven't. And so then we get to the second phase of what people affectionately called token maxing using the Gen Z maxing term. And that's the idea of, okay, how do companies really adopt AI? Well, let's just get everyone to build stuff, right? And use as many tokens as possible and create leaderboards of how much tokens each engineer has used.

[00:41:26] And that's the measure of success. Pay people bonuses based on that. And so we had, we'll call, the first phase was like, this phase is really short, but the first phase was like December to February, December 2025 to February 2026. It's almost like we were paying people to win the hot dog eating contest. 100%. That's it. Joey, Chester, whatever. So February 2026, I love the analogy, February 2026 to call it like sometime in May 2026, we have this token maxing period. Everyone's posting things about token maxing and people are bragging

[00:41:56] about how many tokens they use and da, da, da. And obviously then there was all of a sudden, it seemed all of a sudden, CFOs started seeing the bills. And the thing is, they're used to budgeting with like fixed budgets. And this thing was not budgeted. And so then they're all like, oh my gosh, we need to look at how we manage it. And so you enter this third phase, which is I think just a more rational balance where you're like, I want adoption, I want productivity benefits, and I also want to do it with the right cost profile.

[00:42:26] It's a business. And so Laredin basically does both sides. So they measure the productivity of AI by looking at what are you doing with it, with AI and without AI and what processes could be AI and all that. And that was their first product. And then their second product is, okay, how many tokens are you spending? How much money are you spending tokens by model provider? How can you reduce the cost? Because there's all these good things you can do, like sending simpler workloads to cheaper models or open source models, all this stuff people are going to start doing. And so the economics of tokens is what this company is all about. But I think it underlies

[00:42:55] a bigger story, which is AI and enterprise has to be about business ultimately, not just technology. Fortune 500 CEOs can get away for a year-ish of like, hey, we're investing in AI. And then shareholders are going to be like, okay, earnings per share, you know, what's my revenue growth? Like the real things that matter to investors. And the CEOs are going to start getting asked those questions very soon. And so we need to take this much more seriously from a business perspective. So what I love about this is not only that

[00:43:25] there's a solution out there, which is fantastic, but my arc of this was at the beginning of this journey, I kept asking everybody, all the CFO friends, all of my software friends, all of my innovator friends, how are people accounting for this? Where is the budget and where is it being applied? And I got the equivalent of crickets. It was like people would say things, but you could tell nobody was thinking about it. So I'm like, well, maybe I'm wrong. Maybe I'm worried about a problem that won't exist. Maybe it won't blow up in our face.

[00:43:54] And so then when the token maxing thing happened, I was like, one of these days I'm going to trust myself when I know there's a problem coming that people need to be taking more seriously. So, yeah. I think a lot of this happens in any kind of very ebullient cycle. I'm not calling it or frothy, not bubble, but whatever this is. We're just, you know, we all are like, is that right? Does that make sense? Right. And then it's like, oh, it didn't make sense. Right, right. Learning the same lesson over again.

[00:44:23] If it doesn't make sense, it doesn't make sense. My dogs are great. What could be wrong with a hundred hot dogs? Yeah. Well, thank you so much, Nick, for joining us on the Meg and Amy Show. We are so grateful. You guys are the best. I love talking to you. So fun. It's been a blast. Thank you. And call my mom and tell her I did a good job on this. Is that okay? Oh, I will. Absolutely. All right. Thank you. All right, Meg, you ready to leadership corner? So ready. Let's do this thing. Okay.

[00:44:54] Here we go. I made director right before maternity leave with my second kid. I'm back now and I'm pinging back and forth every day between three options. Jump to an AI startup where there's more runway, double down where I am for five more years and try to maximize what I can earn, or downshift to be with my kids now and build some kind of consulting practice. AI is making the choice more urgent and harder at the same time.

[00:45:23] The labor market is unsettled and honestly, there's some real burnout for me. How do I stop pinging and actually decide? Oh, well, first, bless you for recognizing that you're swirling a little bit. I think that's super important. Having been there, this is a big moment. I totally understand the angst. Obviously, the weight is a lot higher here, but when I came back, I had, with my second child, was right when Oracle had recently acquired PeopleSoft.

[00:45:53] So there was a tumultuous moment and I definitely remember that feeling of, like, how do I find my place? So I really am feeling your energy here, both in your question and in my own past experiences. So I think I have a couple things to tell you and some ways to think about this. I think the very first thing and the most important thing is it's going to work out. You're going to make a decision and then you're going to make that decision right.

[00:46:23] And so I think agonizing over it is not helpful and also I think it's indicative of a slightly different challenge than the questions that you're asking. And I think the second order effect of that is the clue where you said, well, my choices are go work for an AI company, stay here for five more years or start my own thing. I think you're creating choices that might not

[00:46:52] necessarily reflect the totality of choices you have. In other words, I don't know that you are making a five-year choice if you choose to stay. I think it's perfectly fine to make a one-year choice to stay and decide what to do next. I think it's perfectly fine to go see if there is a job at an AI startup that wants to hire you so that you can compare a real thing versus an imagined thing. I would say the place that I have the most hesitation for you is not necessarily

[00:47:22] based on doability but just based on energy with kids and that's the choice of doing your own independent. If you have a line on clients already and a path for that then I say sure that's a completely viable and great solution. If you don't there's a different type of energy in having to both sell the work and do the work in independent that I think adds an additional burden especially on someone who might be doing that with an intention of

[00:47:52] investing more in your home life and so I think it's a little bit misinterpreted of whether that would actually give you more time at home or not and so it would really depend on you but to be honest I believe in you enough to know that you would make that work out too so again I'm just right back at the beginning of where my advice was which is the fact that you have choices is fantastic the fact that you have clearly a good path to make something

[00:48:21] great for yourself is fantastic I think what you need to do is you need to feel okay with whichever choice you want to make and then just make it and I think if there's any way that we're helping you with that hopefully just to know that we believe you will be successful no matter what you choose to do and so it really it's going to be fine and this is not the only moment that you will find opportunities to work for an AI startup or to do independent work those opportunities

[00:48:51] will be available to you as well so what is your thought Samie all right so yeah I love so much of what you said Meg so first of all I absolutely agree do not think about the next five years think about the next year and I have maybe a couple of follow-up questions and I'm going to have to make some assumptions so first off have you already been offered a job at the AI startup are you thinking about looking for a job at an

[00:49:20] AI startup I'm going to assume it's the latter and if that's the case then it takes a lot of energy and time to look for a new job and that may not be the best use of your time I had a friend a former employee of mine that came to me with a similar situation what I recommended to him was that you really take the time that you would have invested in trying to

[00:49:50] find a new job of maybe even doing a new job and apply that to your current situation to get like really AI pilled it's possible you're already super AI pilled but I'm guessing that in it today and build stories and build your own internal resume that you can leverage

[00:50:19] for a role elsewhere so after you spend the next you know three to six months doing that you can decide if okay is where I'm at right now am am I still learning am I still growing is this enough or do I want to then take all of that learning and spend the time to find something new the other thing that I would be curious about is what's your home

[00:50:48] situation and what time and energy do you have available do you have a supportive co-parent at home that is able to take on a lot of the workload are you able to put a tremendous amount of energy and time into your career right now or is it going to be very difficult to do that for me personally I did and so when I came back from

[00:51:18] maternity leave and got the director job I was able to keep going and moving up and that sort of thing but I if you do already have that job lined up and you have tremendous support at home and you're like super jazzed about it go for it but assuming that none of that is true I would take your current situation and

[00:51:48] make it just really work for you so that you set yourself up so we got new questions coming in so please do keep them coming yeah absolutely okay so Meg Nick was just a bundle of energy and joy just so much fun what are your thoughts on

[00:52:17] today so you know I've just been a fan of Nick for so long and we've been eager to get him on the show for quite some time and we've had a few rescheduled so it was just really lovely that he was able to carve out time for us I know he's really busy right now and it was I think exactly what I expected in the sense of he is using this time in a similar way as we are Amy which is to get

[00:52:47] super curious to challenge what he knows and to think about where the future vectors of innovation are but at the same time also thinking about how can he support and help others and so I think that was such a great way to see someone role modeling that we have so many friends that are in these transitionary states and I think you couldn't find somebody better to follow in that using

[00:53:16] this time to make really important things happen while you're out of an operator role yeah I love that it's great let's invent the future together everyone I believe in us let's make every day count