Arun Gupta | Apr 24, 2026

Arun, welcome aboard to the show. Thank you so much for joining us today.

Thank you for having me, Ari.

So during your stu— your teaching at Stanford, you came to the conclusion that there was a gap with the young adults there. Tell me more about that gap. What was the problem that you saw? And I'll give a little bit of a spoiler alert that led to writing of your book. Tell me that story. What was the pain? What were the problems?

So Ari, I mean, it's important to understand the lens I was approaching that class with. So my father was in public service within the Navy for 40-plus years. I was a VC, started Carlisle and Columbia Capital, founded by Mark Warner, Senator Warner, for 20-plus years. I mean, the latter half of that, I was investing at the intersection of mission tech and entrepreneurship, so government and technology. And what I saw there is the magic when you can get the entrepreneurial ecosystem collaborating with government, because you could take the innovation and bring it to scale. But I also saw the challenges. And the challenges usually resided in just culture and talent and trust. But, you know, when I stepped away from venture and I started teaching, I started teaching at Georgetown and Stanford, and the class that you're referring to was called, I titled it Valley Meets Mission. And it was really at the Stanford in Washington program here and talking to them about, you know, how do you take the entrepreneurial spirit of the Valley but not waste it on Candy Crush 3.0? Right? Like, how do we get these students focused on that, by the way? Um, you know, meaning—

let's talk, let's talk about this for a second. I mean, yeah, yeah, the Candy Crush 3.0. We were creating so much stuff that is not driving value to community. But on the other hand, I'm assuming that you got into this niche of because of some kind of salient memory from your father experience. You mentioned his service. What was that moment where you saw— and I know I'm taking you to a personal question here and probably a long time ago, but what is the moment that you saw Dad and you were like, holy shit, this is impactful to me. This is something that I want to give back to Mike.

Look, listening over dinner at the stories of the work he was doing on building carriers, right? And the purpose of those carriers are to protect our country. You know, there's a deeper meaning to the work that was, he was doing each day and you could feel like it was important to the community and important to the country. You fast forward to when I was a VC and the first half of that, I was spending my time doing your typical Valley, you know, consumer deals. And, um, you know, you were focused on eyeballs and looks and, um, you know, getting, getting network effects, but you weren't really prioritizing what societal value does it have as well. And it wasn't until we started investing post-'08-'09 around things like cybersecurity, where they were really addressing needs that were also tied to the federal government, and you were brought into an ecosystem of folks that lived their lives on mission, like a Mike Morell, a General Hayden. And what was amazing to watch through their lens is that they were driven by purpose and they were driven by mission, and the money followed that. But that wasn't what their driver was. It made it hard to want to go back and just do, you know, what I would call a regular venture deal because of being able to see the ability to do both. And it filled, you know, a piece that was missing in you. And so, you know, I think when I started teaching the class and putting the class together was to kind of highlight for these students that there's a way to do both in that we've, created this artificial vocabulary that makes it feel like you have to make a binary choice at the age of 23. Do I want to be on this career path for personal ambition and monetary reward, or do I want to be on a career path which is about mission and personal—

Why? Tell us about this. What were the— what was the pushback or the feedback that you were hearing from students? Like, no, I don't want to work in government, or what was the challenges to make those two come together?

Well, I mean, the challenge is, you know, what was interesting is it starts with like, you know, the, the cross-section of students that you have in the class, right? And so, um, I'm not sure I would have noticed it as much, but I had a broad cross-section. So I had folks that were from the social sciences, um, and you're teaching a class around like how do you create entrepreneurial endeavors in a for-profit way. And I think their initial take is like, well, if you're making money, that's bad. If you're, um, you know, doing something for profit, you're being a sellout. And likewise, you know, we had engineering and tech and business students in the class. And in their mind—

who had the opposite perspective.

Who had the perspective of government, right? Like, it's slow moving, it's not innovative. And it wasn't until you brought people in, right? And I think this is the key. You know, when you humanize it for folks and you bring in government folks that are on the cutting edge and being really innovative. You bring in people financing companies that are being driven by mission, and you bring in entrepreneurs and founders that may have now be running unicorn companies, but when you hear their story, when they started the company, it was about solving a, a mission-driven problem that the money followed the mission, that students were like, whoa, this is kind of like, this is the ecosystem I wanna play in. Now, for me, it was an ecosystem I, you know, had been around for over a decade, but I think what it brought to my attention is that like, we haven't really exposed this at all to students more broadly in an academic environment. And since then, you know, you've seen this become more mainstream, even at Stanford, like the Hacking for Defense has become really popular. The national defense programs and conferences are probably one of the most popular conferences there. And so you've seen a shift take place, but this was, you know, early. When I was teaching the class that you didn't see it.

If I may, you're teaching this class, you're bringing in these guests from outside who are living this life. Do you recall a specific guest where one of the students came up to you and said like, this changed the way, changed my perspective?

Yeah, absolutely. You know, so, you know, Jason Mattini, you know, who had just started CSET, had been on the academic side, and then had gone inside of the NSC in the the Biden administration, and, you know, folks were asking, you know, tough questions about like, you know, how the NSC is, um, how do you support the NSC if people, you know, some people die in the process? And I thought he gave a very measured response, which is like, you know, the way I look at organizations that I join are, do I do more good in the world by joining them or being out of them? And if I can do more good in the world by joining them, you know, that's a place for me to go. If I used the metric of like, is there anything bad that's happening that I could view, I could start to delineate that to any organization. Anyone that's using paper, for example, you know, is having some negative environmental conflict. And I will find myself then saying like, there's nothing I should do. And I would argue that that is actually worse for society than doing something. And it was actually a really enlightening, you know, moment for, I think, a number of the students because at the core, what was getting at is you can't make everything a purity test, right? On either side. Nothing's ever all good and nothing's ever all bad. But we need to move away from at least being able to discuss the nuances, which we moved away from. We now talk in soundbites. And so the easy soundbite is very binary. All good, all bad.

Arun Gupta: Arun, careful. You're, you're approaching one of my biggest pet peeves that kind of pisses me off. This binary simplistic thinking that we're dealing with today. You know, one of the political arguments that I make is that it's not about the left or the right. It's not about regurgitating whoever's side soundbite. It's about actually analyzing and thinking, well, what's good about this? What's bad about this? Let's think how this is adding and detracting and not just like hating everything because the other side said it. And then when your side says it, whatever, 4 years later, it's suddenly good again. What do you see through your students?

At the core, it's about losing the ability to have nuanced conversations. And it's, it's the ability of needing to show that you're right versus being willing to try to get to the right answer. Those are two very different things. I used to say that about, you know, being on boards. You can tell a constructive board, and that's one that is willing to talk about putting all the ideas on the table and figure out what's the right answer. And divorced ego out of that. A nonconstructive board is one where everyone feels like they have to be right with whatever suggestion it is. And then it becomes me convincing you that I'm right and why you're wrong. And we're not really debating the merit of the case. We're really just trying to, you know, focus on who's right. And I think that's the nuance that we've lost, right? And I think some of that is like how we communicate now. You know, if things have to fit in 180 characters, you can't have nuanced conversations. You know, we don't sit and have long-form debates. We have short-form debates. And I, you know, I think that has contributed to it. And, you know, having said that, like what we're seeing with our students when given the opportunity and bringing them into the, giving them the platform and the ability to have longer-term, long-form conversations, they thrive on it. They want it, and they want the ability to have these conversations in a safe space where they're not judged. And I think that's where I get optimism. It's not that people don't want it. It's just we haven't really enabled the mediums again to be able to have it at scale. Like when we bring in our scholars in the work we do, we'll bring in folks from— example, we brought in Matt Pottinger from Trump One National Security Council, and we brought in Colin Kahl from the Biden National Security Council. And they both spoke at the same time to the students. And, you know, I think the students were expecting some kind of food fight to break out, um, because that's what they see on TV. And they instead saw two thoughtful people actually agreeing on a lot of things. Yeah. And then actually being respectful on things that they disagreed on and actually, you know, making you think about it differently. And, um, you know, I think that's at the core of what we're trying to do because I think It's easy when you haven't been in someone else's shoes or haven't been in an organization to demonize the organization. And at the core, that's what we had written about in the book, is we need more, you know, as we call them at Noble Ridge, dual citizens, public-private sector citizens. So when we go to students, we're not saying, hey, come here and be a public servant. We're a pipeline for public service. We say, why not have an experience in public service before you go launch your career? Learn what it's about. Learn where the problems are. Learn what resonates with you. And then go be a builder on the outside or stay on the inside if you feel like you can build on the inside. But the more of those that we have, we can start to rebuild trust. And I think we're in clearly a trust gap right now.

Yeah, I think that's fair. To me, what was really interesting is kind of seeing in the last election, the presidential debate versus the vice presidential debate. I don't know if you saw both of them.

Yeah.

But the presidential debate was kind of characteristic, you know, the stabs at each other. The VP debate would almost seem like it had this feeling that they were working working together, thinking together. They weren't trying to rip each other's, you know, face off. And I was like, this is really nice. Why can't everything look like this? Where we're kind of working together to be successful as opposed to, you know, poking each other. And I think if we can see that happening at the VP level, that's really encouraging to me. That kind of says to me, hey, this isn't that all politics is rotten. It's maybe this is even a little bit of a show that we're putting on for the general public.

You know, just on that point, I, you know, I think where we've also seen this powerful as we, you know, define government or public services, usually people immediately think federal, but if you think state and local, it gives you a better ability to be able to see exactly the dynamic that you're talking about. And we had Governor Stitt, who's the chair of the National Governors Association, speak to our scholars. And I will say, and I told him, like, you know, one of the more poignant moments was him talking about Governor Moore, his vice chair. As a close friend and how his families were, their families were close friends and at a very authentic, personal way. And also acknowledging like, look, we disagree on a lot of things, but at a core we're, we're friends. And, you know, and I, I think you see that especially with governors and, you know, mayors, you know, they can be from different parties, but there's a sense of like, hey, look, we need to operate. We need to be able to get things done. What's working with your state? What's working? And, um, and so I think the more of that people see, the better.

Brilliant. I gotta say, I, I, I love it because I think a lot of people are kind of frustrated with this state of the status quo. And I think in some way, this discussion and perspective, it gives a little bit of optimism into the future of what it could be looking like, and maybe even more so why individuals should have that experience, if not necessarily their career. Tell me a little bit more about the program, Nobel Re— Nobel Prize.

The three stakeholders that we see are obviously universities, industry partners and government agencies. Government agencies, think of them as a place that we are, we're placing our, our, our talent. That's where the need resides. Federal, state, and local. We've now expanded. First cohort we did was at, at the federal level only. Second one, we expanded to 10 states. You know, so that's one cohort. The, the second then is industry. And this has been an important cohort that we've intentionally nurtured and built. And this is a cohort of industry players that you're more your typical recruiters on campus, the name brands. But, you know, having them understand the value of the program that we're creating and the kinds of students that we're trying to bring in and having them participate, you know, to speak to the students, talk to them about leadership, talk to them about AI, talk to them about financial modeling, talk about the skills, but most importantly, to have them feel seen, right? Because the students then feel like I'm in this public service, public sector job, but I'm being seen and valued by the private sector. And I think that's an important dynamic. And then the most important obviously is the students, which is now, you know, at the universities. Thus far, we've been recruiting college graduates anywhere between 0 to 3 years out of school. I think Teach for America, but pointing to public service, not public education. You know, I've chatted with Wendy Kopp quite a bit about this. With the idea like that, that we want to be able to have people come in for a couple of years. Currently it's been 1 year, but we'd like to expand it to 2 years. And, um, you know, go serve and bring their— we've been focused thus far on STEM talent. So tech and, uh, you know, finance, business, math kind of talent, primarily because we're so underserved there in government right now. So there's such a big need. Back to the stat of less than 6% of our tech workers right now are under the age of 30 in government.

Um, so hold on, hold on, hold on. So less than, you said 6% are under 30. That doesn't sound right.

So what's the rest of the pie? Here's the other kicker, Ari. We have 4 times over the age of 60.

Okay. That, that sounds like a problem coming our way.

It sounds like it should be red alert for all of us. Yes. Um, and when we wrote the first book, that's how we felt. Um, which is why we felt like it was the time to try to create a program that could scale to the size of the problem. We needed a systemic intervention whereby we could change the way we talk to young folks about coming into government, but doing it at scale and doing it at a scale that would constantly be refreshing the system in a meaningful way. Um, You know, we've, since then, you know, there's an initiative started by Scott Cooper and at OPM called TechForce. And I first chatted with Scott pre-inauguration, and he was aware of, you know, the kind of program we were running. You know, we both ideologically aligned on this notion of, you know, how do we make, you know, government a desired place to start your career? Internally at Noble Reach, we talk about like, how do we change why to wow? Not why did you go there, but like, wow, you got selected to go there. Right? Because when you're 23, that, that initial reaction has a currency to it. Right. When your peers go like, why are you doing that, Ari? You immediately start to question the decision you made. Yeah. But if your peers go, wow, that's amazing. You're like, you know, you stand up a little straighter, you feel a little bit more confident. And that's what we want to have. And, um, you know, we think, you know, a lot of it's storytelling. A lot of it's telling stories about what you get to do. Same job. But we talk about it differently, and we talk about it with a focus of the experience you're going to have being close to the most difficult problems at a scale that you won't see anywhere else.

So there's the part of the gap in just understanding what it can be and what it can mean. And that's something that you're working towards. However, there are actual problems on the government side, which can be frustrating. What does that side of the problem set look like?

The first thing is trying to identify the parts of government that are willing to lean in and be innovative. And so, you know, it's one of the things things we write about in the book as well, but is that, um, you can't just take all of government and it's not one big uniform homogenous blob, right? Um, it's actually just molecular level is just made up of individuals. It's an organization, right? And so within any organization, there'll be people that are innovative and that are innovators in it. So our first thing really is we're placing young folks in is finding those innovators. And I say that already because their experience is immensely important. Right? It's immensely important that they have great experiences because then that is what excites the next group to want to come in. But beyond placing them in government, to your point, Ari, we also didn't want to just rely on that. We, you know, so we, we, we view our job as twofold. One is to find exciting placements, but the second is to provide them the scaffolding of support while they're in. Because just dropping, you know, a 23-year-old by themselves in an organization where everyone else is 45. Can be isolating by itself. And so what we've been doing is one, you know, when we place scholars in, we place them in, we give them a mentor from the outside, someone that's been in public service before, but it's also in the private sector so that they can have a, you know, a larger perspective of what this experience would be. You know, someone like you would be a great mentor having been at DOW, right? So that you could talk to someone about like, hey, look, I remember that frustration, but like, Here's what it really meant. 'Cause every day's not gonna be great, but that's not true at any job.

That is absolutely.

And then also your mentors are frankly the ones, you know, when you're coming outta school, I think what gets undervalued are it's less about what you do, but who you do it for. 'Cause your mentors, if they're invested in you, they're the ones that help you find your second, third, or fourth things, which are, you know, invaluable. So that's one.

I think a lot of young adults don't kind of, don't understand how impactful a good mentor can be. I see it on myself. I see it on my wife. When you look back to those mentors, they have completely changed our life for the better. So, you know, if it's through a program like Noble Reach or other programs, that's one piece of advice that I definitely want our young adults to hear.

And Ari, to that point, I mean, it was the inspiration for writing this next book, The Mission Generation, which was, you know, trying to advise young folks especially, but, you know, it applies to mid-career and late-career folks as well, of that, you know, When we think about net worth in our society, we right now use one dimension, right? Anyone asks what's your net worth, they're going to give you a number, you know, that old proxy of bank account balance. And, um, we acknowledge, you know, financial security is incredibly important. We're also trying to, in the Mission Generation, highlight that as you're making your decisions, acknowledge that there are other capitals that are equally important. And so we talk about trust capital, which is the relationships and the mentors that you may have. Experiential capital, what's the unique experience that you're getting? Are having. Learning capital, the curiosity, the ability to learn new skills and experiences. Health capital, you know, what toll does it take on you as an individual to sustain this journey? And then finally, mission capital, a sense of replenishment of having impact. Because right now, you know, it's funny, Ari, when I was teaching at the business school at Georgetown, I would have had multiple students like open up spreadsheets doing a DCF analysis of their projected incomes and wanting to select their jobs based on that. And you had to politely ask them to close the spreadsheet and then walk through these questions. But what I realized is that we haven't really given them a language to assess this in, right? They don't think about it in that context. And the reason we use capitals when we talk about it in the mission generation, it's like financial capital. We think, you know, each year you should be investing a little bit in each one, maybe not the same amount like your portfolio. But, and if you do it consistently over time, it compounds, right? And so I'm sure with you and listening to your takeaways with mentors, you invest in relationships early in your life. 15, 20 years later, you have no idea how valuable that's going to be.

Yeah. Here's my problem though. A lot of the good things that happened to me, and I'll admit fault here, were by accident. They weren't intentional. And when I think back to how I kind of saw, yes, I was the guy looking at the cash flow. In fact, I remember that Excel sheet. I showed it to my wife. On the decision if to leave, leave kind of military or stay. Uh, I did that calculation and I felt like one of the things that I didn't understand is these other verticals that you're talking about. It came later in life. How do you bring that kind of understanding to, to 20-year-old Arun? Because I wasn't there.

Yeah. So I think the way you bring it to 20-year-old Arun is like showing stories. Of 50-year-old Arun Gupta. I'm going to guess, Ari, you're 35, but you know, I'm almost 50, man. All right. You look good. I was definitely going to go under. It was just how far under. But my point is you have to show stories. We don't show these stories. We don't talk about it. And that's a big part of the book is that, you know, we're trying to write stories, share these insights, but not as insights, but as takeaways from people's stories in hoping that someone, there's a story in there that someone resonates with and goes like, wait, what Ari did sounds like me. And now what he's doing sounds like what I would want to do. Wait, I would've not thought I could do that, but he did. Why can't I? Right. You know, we lay out in the book as well, you know, to try to really understand what are the resistances that keep you from doing this. And we lay out 4 broad categories. One is internal, you know, what's in your head, you know, imposter syndrome, perfectionism, fear of failure, you know, let's name it, call it something. Or is it relational? Is it family and friends? You know, they may be coming from a good place, but maybe they're stifling you in a way that because they're saying like, ooh, you sure you wanna do that, Arun? That's risky. As soon as someone says that, you know, you, you start questioning yourself, especially if it's a loved one or a close friend. Is it social, right? Or societal? Is it that like, wait, if I go do this, like no one's going to care because they think this is what is prestige and this isn't? Or is it institutional? Like I can't leave the track I'm on.

You're kind of breaking it down and you're saying, hey, this is the framework to think about your, who are you going to be over 40, 50, 60 years and kind of taking it from a very thoughtful manner. That's, that's actually absolutely wonderful. Honestly, I wish I had that when I was in my 20s thinking through it.

And Ari, you know, in each of those things are like, what are the questions that someone asks when they're, you know, and what you realize is those questions stay with you. I mean, the mid-career and late career, they just have a different context. So in your early career, you're, you're asking those questions, but you're asking it maybe from being single, no obligations, but, you know, no idea of what the world could look like. When you're mid-career, you're asking those same questions, but you're asking them from the context of like, I've got two kids. I've got a mortgage. Can I really go do this? But I feel unfulfilled in what I'm doing. And when you're late career, you're asking these questions. Like I, you know, I, I see with, you know, friends that are, are very well to do. And then they go like, Arun, how are you doing what you're doing? You left venture and now you're teaching and now you wrote a book and now you're excited. You seem energized. And I'm like, I don't know, you just do it. And, but they're like, but what if it didn't work? And I'm like, Who cares, right? Like there's a little bit of like, you start kind of having to poke, like, you can do it too, but you're not really doing anything special. I mean, I think part of it is how we've been brought up, right? Like I think there's a sense of, you know, we need to have clarity before we act. I think that's how we were kind of, we were brought up to some extent, like know what you're gonna do, then go apply it. In a world that's changing really rapidly, you know, by the time you get clarity, the conditions have changed again. That you had clarity on. And so then you're always searching for clarity under the new conditions. And so what we talk about is just start doing stuff, 'cause the acting will bring you clarity. That's how you'll get signals, right? And, um, that's what we try to talk about in the book, which is, you know, I think the scripts we've been given thus far have worked in a world that's been relatively stable. Um, but in a world that is really changing very quickly and very rapidly along very, you know, a number of dimensions, geopolitically, technologically, environmentally, informally, um, you know, the only stabilizing force then is going to be mission and purpose. We built our systems to seek stability. Biologically, we're wired to seek stability over even happiness. Studies would show that. However, you know, what we kind of posit in the book is like maybe stability is the new risk. Like it's riskier to do the stable thing than it is to go intentionally do the entrepreneurial thing. So, you know, that's how we think about it.

This isn't This has been absolutely wonderful. I appreciate you. We are already over time. I have one last difficult question to you. If you had to look over, you know, a lifetime and think about your most difficult moment, whether it was 2 years ago or 20 years ago, what would be the piece of advice that you would've given yourself?

I think when I hit, you know, my most difficult moment, was really knowing that, um, the investments I had made in the relationships over the time, by the time I got there, actually had real value. And what I mean by that is that, um, when you're really feeling alone and down, you sometimes think it's weak to reach out to the relationships, but it's actually a sign of strength. And if you've invested in those relationships early on, You know, they'll pull you through those hard times and then there'll be a time when you're pulling someone else through. And I think that's what I would be telling myself, right? Is to, to invest in, you know, lean on those relationships more than I probably did, whereas I was probably internalizing it on myself.

Arun, thank you so much for joining the show today. I appreciate you. This was wonderful.

Well, thank you, Ari. It was great to be with you.