20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen

Ariel, dude, I cannot believe. We were just chatting before, and I can't believe that both Navan and 20VC are, like, 11 years old. It is so good to have you back, my friend.

Dude, it makes us really old. That's what it actually—that's the problem with this statement: 11 years in this journey, and probably, at least for me, another 20 years to go.

You created a $4 billion or $5 billion company in that time. I still am doing a podcast. Admittedly, there's more listeners, but still, I would feel better if I was you.

1. Navan Chose To Go Public

I want to start with the big thing that's changed since we last chatted: you've gone public. Before we discuss the post-going-public period, how was the pre-going-public process? Is it what you thought? Did you enjoy it?

It's a good question. I'll tell you what I've enjoyed and what I didn't. I definitely enjoyed bringing your story and what we've built, and almost summarizing it. When you go to do an IPO, you're bringing this story to completely different new people, right? People that we've never met before, a new set of investors, analysts, bankers—a lot of people that actually were not familiar with the story.

It's almost like you need to summarize 10 years in the making into, I don't know, 10 to 15 slides, plus a document—the S-1. Obviously, there are a lot of lawyers involved in this, and bankers and so on, but you do get to tell your story to a bigger audience, and that's the fun part. It also opens you up to a different type of customers because of it, so that's the fun part.

There are a lot of process-related things that you need to do. It changes the way that you speak and talk with your employees, and that you talk with even your board. That's a part that I like less because I do like to be very open and not to think a lot about what I'm saying. So that's kind of the fun part, but also the heavy-lifting part.

The one thing that we've seen is the extended windows of private markets and people not going public.

Yeah.

Respectfully, in a world where your Stripe and your Databricks have pushed it out as much as possible, I don't know how to say this without being rude. Were you forced to because of the debt component to go out at this time? And how did you reflect on the right timing?

Yeah, there were a lot of reasons there, by the way. I think the first thing is that I am someone who's going on a certain trajectory. I'm following through. So the decision of taking a company public had a lot of reasons.

You've called out one, which is basically our capital structure and the way that the balance sheet worked post-COVID, but there are other reasons. For example, in the payments business, I think there is a huge, huge advantage to being a public company in the way that you are actually raising capital for that part of the business compared to being a private company.

I think if you go too long in the payments business while being private, you may end up not where you want to be, so that was definitely a driver. But also, we've been starting to take share in the enterprise segment, signing more and more customers. For that type of segment, it is actually important that you're going to be public. They want the transparency. They want to understand your financials. They want to know that you'll be around. So there is a list of things to be public for.

Timing—you start, you are on the road, right? The number of times that the market has changed while we were going public: we actually started non-deal roadshows in April, on the same day that the tariffs were announced, and the market corrected. I don't even know why. That's when we started, and then it kind of went to the other side.

So I think trying to time a market and say, “I will only go public when the market is having these ideas,” is really, really hard. I think we kind of decided to go for it. We followed through. And timing—I think eventually we are running a really good business, so everything will get sorted out.

Can I ask you, when you think about pricing an IPO, almost forgetting Navan, I'm always intrigued by where you sit on this one. Do you agree with Bill Gurley that you should price it to perfection, so there's no pop and you and your employees achieve the fair market price? Or do you think there should be a baked-in pop to make everyone feel good on day one and make it an incentive to buy?

My thinking about Navan is much less about some price engineering on a certain day, even if the IPO day is very important. It's more about whether you can take a long-term view of Navan. Do you believe that Navan will take the market, right? And the market in the way that we define it.

We define the market very, very differently than everybody else. Everybody thinks about it as maybe we're disrupting Concur and Amex. That's not the way that we define it. We want to service every frequent traveler that is out there.

There is the managed side—you know, Amex and Concur. There is the non-managed side: everybody that's doing whatever they want to. It's actually a bigger market, and we think that we have an opportunity and the right to win in both markets, and that's what matters.

Now, by definition, that means that the point of view that I have is a very long point of view, and it starts 2 or 3 years from now because, you know, you have so many mechanics.

You have lock-ups, VC distributions, this quarter and that quarter, beat and raise, and a lot of mechanics. At the end of the day, I think what matters here is—and that's what I hope the investors who invested in Navan in the IPO have—a long-term view that Navan will take the entire market of frequent travelers.

2. Unknown Competitors Matter

When you think about that entire market, I often think the danger is the danger that you don't see, and I'm totally with you on Amex and Concur. That's the traditional mindset of who the competitor is, but then you have random competitors like Ramp coming out of the blue, and I would be more—

Mm-hmm.

—worried about Ramp than I would be about Concur and Amex. My question to you there is, does someone like Ramp not have an inherent advantage over you by being private, because it can spend on growth, on Super Bowl ads, on crazy stuff, and be margin-negative, while you are really scrutinized for every dollar you spend as a public company? You don't have that same elasticity on customer acquisition.

The first thing is, I actually reflected with one of our executives here, our president, Michael Sindesich, about something really interesting. He was our 10th employee, so he's seen everything with me—almost like a co-founder in the company. We talked about the companies that came and went over the years.

When we started Navan, there was this company, UpSide Travel. We raised $4 million; they raised $200 million in the same year, talking about the same thing we were: “We're going to disrupt corporate travel.” Their founder was the founder of Priceline. If you think about somebody that needed to win against us, that was them: way more financing, the right people, and the right connections. I didn't even know what a GDS was at that point, and they are not around.

Then there were so many companies over the years, including in the fintech industry. You saw the Brex announcement last year, and I love the Brex guys. We are partners, and we know the founders really well. But I don't think that you want to end your journey in Capital One.

People came and went throughout the years. I think our culture is what matters, and that's what will keep us around. That's what will keep us a winner, and probably the winner. The idea that maybe it's better to be in the private market because nobody will look at how I'm defining revenue, or what the gross margins or contribution margin are, doesn't create a good business.

We've talked about these things even 3 or 4 years ago, so we've managed to build a good business pretty early. I don't think it matters. I think what matters is the culture. Do you have what it takes to see it through? I think we do.

I totally get you. Does that mean you don't worry about, say, Ramp?

I never wake up in the morning worried about a known competitor. I'll tell you what the only competitor is that I'm worried about: the one that I don't know about. The one that sits there, like Navan 10 or 11 years ago, ignorant enough about the problem but really, really good, and that will create something with a different point of view that will be very disruptive to us, as we are very disruptive to everybody else in this market.

My paranoia level on that is really high. I'll tell you a story about what made Navan an AI story. We were not an AI story at the beginning, but it's actually interesting. We always used machine learning to prioritize our search results and optimize savings for companies. This was from 2016.

About 3½ or 4 years ago, I was at this conference in Napa, and Sam Altman actually presented ChatGPT before it was released. I remember getting back to our offices and calling Ilan, my co-founder, and 2 other executives, Nina and Michael. I told them, “If we don't build our own platform right now, we are so dead.”

This was after seeing 1 demo, and I was really hysterical about it. I was saying, “We are dead. I cannot see anybody using a…” I think I even talked with you about this notion that software is dead. Actually, I think the last time we talked, I was calling this out—that software is dead—and this was years ago.

I was worried exactly about that: the thing that you don't know. Luckily, we had enough paranoia to build our own AI platform that is really powering everything in Navan today. But back then, we didn't know about this thing coming. Some kids who are building the next Navan right now are the ones that I'm always worried about. I'm not worried about the ones you're mentioning.

3. The Market Misses AI

So what does the public market not see? They're not pricing in an AI story.

100% not. I think the market has, I would say, 2 observations about us that are incorrect. The first is that it is very hard to find a comparable for Navan's business.

On one side, it is a tech company, and the value that we are creating is for travelers and their employers, so it makes us look like a SaaS company. On the other side, our business model is very much based on consumption. You come to the platform, and we only make money when you use us.

The way our business works is that we sign agreements today and pay commission today, so all of the go-to-market cost is going today. In the years to come, you are going to make a lot of money in a very, very healthy way. What investors see in our P&L is a huge investment in go-to-market, and they don't see the immediate return.

What I can tell you, without getting into the details because we are not sharing these numbers, is that we have an extremely efficient go-to-market and an extremely efficient churn profile. It's actually rare for companies to leave Navan. So one side is that we don't fully understand our growth algorithm or our go-to-market, and I think we need to do a better job explaining it. But over time and over the quarters, people will see our delivery.

On the other side, to your question about AI, I think there is this broad feeling right now that everything in software is dead, and therefore it doesn't really matter. Right now, there is not a lot of patience to listen to or see the differences between companies.

I was calling out on your show that companies doing some workflow in a form are not relevant. They're not relevant not just because of AI; they're not relevant because that's not how people want to consume stuff, so they're not relevant anyway. I think I called out Salesforce back then, because I cannot imagine people using something like that in the next 10 years. I think AI accelerates this.

Can I push back on that and just say I disagree entirely when you look at Salesforce? I think they're an incredible buy because I think the only thing that matters is distribution. When you have an AI sales rep that works—“Hey, sales reps powered by AI that make you money while you sleep”—everyone will sign up. Yes, please.

All that matters is that you have distribution from Chattanooga to Chad in Africa, and that is what Salesforce has. So why would Salesforce not be a screaming buy?

I think distribution matters. I think the most important question to ask is, “Is the user who is using me happy to use me?” I've never met a salesperson who told me that they like using Salesforce. If the user is not happy, you will get disrupted.

To your point, there are a lot of moats related to integration into the enterprise and related to distribution. But I worked for HP Software, and it was the same story: distribution was everything. I learned a lot from it. I called it Walmart for selling servers and stuff for data centers.

Over time, disruption will happen if the people using you just don't like using you. I think the new type of software that you see out there is software that people like to use.

I was always calling this out regarding Navan: it is extremely hard to replace Navan. That's why we rarely have churn. I'll give you 1 statistic: in the history of Navan, we lost 6 enterprise customers. 5 of them are back.

If the user loves you—if the employees love you—that's the biggest moat that you can have. I think distribution matters, but you can build it, and that's kind of the battle that we have here at Navan.

Do you think it's your fault on messaging or the market's fault on the negative perception today?

I actually don't think it matters. I'll tell you why. I was in New York over the weekend. The airports were shut down. New York and JFK were completely shut down, so it's not like a flight got canceled. The airport was shut down from Saturday evening all the way through Monday at noon. That was the entire eastern part of the US.

We've managed to support all of our customers in a timely manner. How did we do that? Ava, our AI chatbot, managed to handle it. At that time, you're talking about the hardest thing ever to support: my flight got canceled, and the airport was shut down. I need to sleep somewhere. I need a new flight. I'm in a panic.

Fifty-five percent of the chats were run through Ava. Our call center, at the worst time during this event, had a wait time of 16 minutes—1-6. You'll think that 16 minutes is something horrible, but try to call any other provider in this space during that time, when airports are shutting down. This is the power of Navan.

This comes from AI. This comes because we have our own AI destiny, with our own platform that actually understands how to support you—not in resetting your password, but in changing a very, very complex trip. You're going to see us release Navan Edge very soon. It's a completely new product. I think it's the biggest or most important release that we've ever released, and you will see how much value a user, a company can get by using Navan Edge. Eventually, the market will figure it out, and we'll actually see who has the lead in AI for travel, AI for frequent travelers.

4. Navan Built Ava

Talk to me about Ava, your own AI. Why did you decide to build versus buy and work with Brad Taylor at Sierra or Jesse at Decagon? What was the thought process behind the internal build versus buying externally?

There is nothing even remotely close to what is needed when you go to a complex vertical out there. It's definitely not at the Sierra level, but even if you take it to the level of the APIs—if I'm taking Anthropic and OpenAI—it is not even remotely close to what you need. You cannot have any type of hallucination when I'm changing your flight. I cannot tell you, “Go from Gate B32 to C-whatever because you have a new flight there, and you'll get there,” if that was a hallucination. You cannot do that. You're going to, first of all, lose the customer, but you're also going to get a lawsuit.

You cannot support some free upgrades on something that does not exist, and I can go on and on and on. We are using all of the models that I've mentioned, but we are also using our own data. We are using open-source models. We've built our entire agentic platform to know where to go to the right API in the Navan platform to change your flight and give you credits. The complexity level of travel is so high. All of the cute demos that you sometimes see from LLMs—like, you can book your trip—are really nice, cute demos. Trust me, they're not even remotely close to being there.

If I'm looking at investing in these companies, how do I make that an attractive picture if every company is in its own vertical? If you're a fintech business, you're going to need verticalized fintech support. If you're a travel business, you're going to need verticalized travel support. Is it just for real?

I think we're at the beginning of a huge revolution that will have its ups and downs. We joked about our age. I was around when browsers started to get introduced generally, and then into the enterprise. People moved from client-server apps to browser apps. I'm really old.

Then came, obviously, SaaS cloud, and then came mobile. This one is so much bigger, so much faster, but it will have the same cycles. Do we see crazy valuations that only God knows how you will justify them? Yes. But are people estimating the size of this change correctly? I think they're probably underestimating it. It's a huge, huge, huge, huge change, and I think there are companies that will benefit from this change and companies that will actually die in the process.

What are we underestimating most, do you think? You said we're underestimating the opportunity size. Are we underestimating—

I think it's very, very hard if you sat in 2000 and tried to understand e-commerce, looked at Amazon, and asked yourself, “Is that a one-off with a bookstore, or is that going to change the way that we buy stuff?” I don't think a lot of people—I think maybe Bezos knew, maybe some employees at Amazon knew—but I don't think that a lot of people sat there and knew, “Hey, people will buy stuff, including servers in a data center, AWS, completely differently than the way that they are doing it today.”

People are trying to estimate which jobs are going to become redundant and which jobs are going to be created. It's just impossible to know these things. I think you will need to wade through it. There will be ups and downs, and eventually—again, I'm looking at this more from a consumption perspective—is the experience for all of us going to be better? Is our work life going to be better? I think yes, because I'm an optimist.

Some people think differently. I think the opportunity is huge. If we move from the LLM infrastructure discussion—which I think people are obsessed with, and which I don't think is an important discussion—and go up to what people are getting, are people getting benefits? I think people will start to get a lot of benefits. It's also a very commoditized kind of thing. I see it with Navan. I think in the corporate world, we are probably one of the few companies that are generating real value to companies and users using AI. The opportunity is huge.

Ariel, why is it not an important discussion on the infrastructure level? When I've interviewed the founders of Harvey and Lagora in the last week, both of them said they went from die-hard OpenAI to die-hard Anthropic, and the difference in quality today with Opus 4.5 is very real. That suggests the opposite of commoditization, though.

I'll tell you why I'm actually happy that I'm not an investor—that I'm a founder. I actually don't have a clue how, if you are an investor, you even choose between all of these LLMs, unless you're just spreading around and investing in all of them. It's kind of hard.

How have you seen usage change for Navan between—

From Anthropic?

It's interesting. We've seen our agentic platform, Cognition, play between models based on who will give you the best answer, and actually we saw movement much more to Google recently. A lot of the transactions with Edge, which we haven't released yet, but we have internally, are actually with Google. It's kind of our own model plus Google coming together, giving you the right answer, but it changes all the time.

Anthropic is an amazing, amazing player, and I also think that what they're doing on the development infrastructure is actually a massive, massive change that makes me, by the way, completely rethink how our engineering even operates, and so on. I think that all of these companies are super smart, super aggressive, but you can see them going from the very low-end, commoditized kind of infrastructure to, “I need to create a development platform here,” which is kind of, in a way, similar to what Microsoft did in the '90s. I think right now you kind of see the lead coming from Anthropic, but God knows—everybody has a lot of ambition and there are pretty good companies.

You mentioned open models earlier and the willingness to use them. I'm intrigued to hear how you think about open model usage versus closed, and what drives that.

I think the way that we look at this is that we have these concepts of models supervising other models, and it's for different tasks. For different tasks, you need different things. Our point of view, when you think about PII and security, is that we have an extremely, extremely strong CISO in the company. He is, on one side, very good at telling us what not to do and what the risks are, and, on the other side, finding the right solutions. It's important.

That's why I've said it's actually hard to create software generally in the enterprise, but with new technology to lead into the enterprise, there are so many things that you need to take into consideration. By the way, regulation is one of them. Travel and fintech are regulated, and they are very much license-driven all over the world. So all of these things, we are really good at taking into consideration and completely changing the way that people are thinking about travel.

By the way, that's why I think we're going to win. The reason that I think we're going to win is that we are almost in the middle between, I would say, companies that already perceive risk as “we cannot do anything”—they are very much there—and the fact that we are also not a startup. We are in the middle, and we're going to do the right thing for our customers. That's kind of what drives us.

5. Vibe Coding Changes Engineering

You mentioned the way that developers code and create is changing. How are you seeing that change internally?

An area that I actually think it's almost impossible to disrupt us is the travel side. To create the infrastructure that we've created to bring the content into the platform—the plumbing there—I don't think that people fully understand the plumbing that you need to create and how deep it is to buy an airline ticket in a location, then change the ticket, and then apply unused credits. It is an extremely fragmented space.

You need to be licensed everywhere in the world, which means that you need to be incorporated in the world. So you are running this online platform, but on the other side, you are connected to an infrastructure that we created in the last 10 years, and we are still creating it to connect to everything, to have the ability to change everything.

That’s really a huge, huge moat, right? When it comes to travel, I’m seeing more of the opportunity to sell better, to service our customers better, and to give them more through Ava and through Cognition. You’re going to very soon see our platform book with AI, which will be a completely different experience.

But I gave the team a challenge, and actually Ilan, my co-founder, took it on first and did it over the weekend: to vibe-code our expense product. It took him 6 hours to do that. Ilan completely vibe-coded our expense product over the weekend.

There’s nothing there. There’s a big fintech component, very similar to travel. How do you swipe a credit card and everything is magical? How do you report on the transaction, and so on? But the actual app is super easy to vibe-code.

You think about the ERP, which we briefly talked about earlier. You think all of these integrations are very, very hard to create with some NetSuite or whatever. They’re not. They’re not. You can vibe-code your way to a lot of things these days, and this is dramatically impacting the way that we’re thinking about where and how we invest in engineering.

What platform was he using?

I actually don’t even know, to be honest. No, I think it was probably actually our own platform. I’m not certain about it. I can ask him.

You have your own vibe-coding platform?

Yeah. Cognition is our own platform. But I think that recently they’ve been combining platforms there, so I’m actually not the right person to tell you which platform he used.

Do you think you skip the design process in a world of vibe-coding? Instead of going through mock-ups, designs, and design reviews, do you skip all that?

It’s a good question. It’s a good question. I’m coming from a product background, right? I keep asking myself: is the product person becoming really the most important person? Actually knowing the use case is super, super, super important, probably more important than ever. Suddenly, the product manager gets a tool to come and say—

There’s always been this tension between product and engineering, right? The product people will want to do something, and the engineers will tell them that you cannot do that. I wonder if this tension is going away, with the product person just saying, “I’m going to do this by myself and prove you wrong.”

I don’t think we’re there yet, but I think we’re increasingly getting there. Again, talking about moats, I think the knowledge moat is going to be very, very high. Knowing the nuances—what exactly the users want, what the customers want, and so on—is going to be very important. I think the power dynamics are changing between engineering, product, and design, but cycles will get shorter. I’m certain about that.

How are you seeing developer productivity change?

The first thing—and this is actually really good for me as a CEO—is that you can create way more pressure to move faster because you get to say, “Why can’t you do it faster by vibe-coding it?” I think that—

But it’s also not just vibe-coding. There’s vibe-coding, and then there’s obviously Claude Code and Cursor, which aren’t really vibe-coding.

I’m only referring to Claude, to be honest. I’m mainly referring to Claude. That’s where it’s going. There are still things today that you need to configure, right? You need to connect to your servers. You need to connect to your backend, and so on. But who says that will be the reality 6 or 12 months from now?

I will tell you that Cognition—interestingly enough, Navan Cognition—is doing the configuration for the developer, so we actually remove that part.

How much more productive are your developers today versus a year ago, give or take?

I don’t know how to give you that answer. Ilan will give you a really big number here, which we’ve decided not to share yet, but you can see that if you ask me where most of the engineering investment is going, it’s mainly to AI-related projects. That’s a huge change.

Totally get you.

But also to develop new stuff. Navan Edge, which I’m really waiting to release, is a completely different way to buy stuff. We’re focusing on the travel vertical, but you’ll look at this and say, “Wow, that’s actually an interesting way to think about what I want,” right? As a traveler in this case, but generally, what do I want? How do I want it? How are my needs being met?

Do you see margin degradation as the quality of that increases? You need context windows to expand. You need memory to increase. That costs money today. Inference is expensive. Unless you get more juice out of the end consumer—and this is my worry—unless the end consumer pays more, all of this just hurts margin.

I think about it the other way around, and we’ve always thought about it that way. If you create value, you’re going to get paid.

I’ll give you an example. We were the first ones, and we are the leaders by far on this, to connect directly to airlines instead of going through aggregators. The model in travel says that if you go through an aggregator, you’re going to make more money. But we knew that was the right thing for our customers.

When you connect directly to an airline, you get more information from them, so you can tell customers, “This flight is likely to get delayed.” You can tell them, “This is how the Delta One seat looks compared to the Polaris seat on this airplane, on this flight.” These are things that people value.

When we connected directly to airlines at the beginning, we did take a hit on revenue. Now we are no longer taking a hit on revenue because we have this win-win-win in the platform between the airline or any type of partner, the customer, and the user and the employee. You eventually get paid for that win-win-win. It also creates a win for us, but you need to take the first leap.

I get you on creating value and getting paid for it down the line. As a public company, they don’t love “down the line.” That’s a luxury you get as a private company. Do you not think that the pressing nature of public-market demands means they don’t love the “don’t worry, it’ll come” approach?

Remember what I told you earlier? It’s almost like I have 2 lenses through which I manage Navan. Is the business doing great? The business is doing amazingly. Are we gaining share? You could see our Q3 earnings, and you can see that we are taking a lot of share.

We’ve announced our move into the enterprise market and taking companies as customers like Visa, huge healthcare companies, and enterprises all over the world—companies that are really in the mainstream, doing stuff that is very, very far from tech, and becoming Navan customers.

The business is doing great, and I think as long as we service our customers and our users, the business will continue to gain share. We’re going to take the entire market. I really believe in it.

The market—and the investors—will figure it out. I think that eventually this will catch up to where it needs to be. Again, we need to make the right decisions for our users and our customers, and the investors will benefit a lot from it over time.

6. Public Markets Affect Morale

Jason Lemkin said on a show the other day to me—I’m sure you know Jason from Sasa—“I don’t know one happy public-company CEO. I don’t know one. Not one.” That’s my brilliant American accent. Are you happy?

I told you I’m happy that we’re out there and telling our story. Is it fun? You have this mechanism that makes people obsessed with refreshing their screen and checking what our share price is. It creates a burden to explain things to your employees, basically.

Everything I’m telling you about Navan depends on the employees here being part of this journey. We talked about it in the context of COVID, right? How do you convince an employee to stay in a travel company during a pandemic? You can apply the same thing here.

Everybody is saying everything is disrupted, everything will be different, and no software company that was created in the last 10 years will be alive. An employee will need to decide: is the business that you see inside really good compared to this grade that you take every millisecond in the share price?

That’s the part I don’t like, just because it creates behaviors that aren’t even relevant. I don’t think that people can actually know why their share price goes up in the morning and goes down in the afternoon, and so on. You kind of know when you report and when you deliver an announcement to the market.

That doesn’t make me excited about that part of being public, so maybe that’s the reference point: can you find happy CEOs? But I do like the other parts that come with it.

Does your mood not correlate to price? I interviewed Vlad. He won’t mind me saying this. I interviewed him.

Vlad, and when they were down $15 billion—whatever it was—honestly, Ariel, he was a dead man walking. Then I interviewed him when they were at $100 billion, and the dude was walking on water. He looked younger. He had better energy.

Yeah.

I'll tell you, it's interesting that you bring up Robinhood. I was kind of an investor in Robinhood through VCs, but then also in the IPO. I kind of jumped on it and went through the suffering, right? They popped and then completely crashed, and for a very long time they were down.

He did so amazingly. He was like, “They are growing the company amazingly. They have a really good cost structure that he built while they were going down.” He expanded into new products and new things. I don't know him, so I don't know why he was depressed when the share price was down. I think this is where they actually define the company, build the company, and create something important.

Oh, dude, because every day you're staring at your stock price thinking, “I'm doing everything I can. Everything's right.”

Remember that we talked during COVID—

Yeah.

Everybody was telling me that nobody would ever travel again, and asking, “What are we doing with Navan?” I told you, “I don't know. I'm looking at it. I'm certain that people will travel when the pandemic ends, and I see all of the stuff that we are doing in Navan, all of the stuff that we are building. I'm just waiting for people to come back to travel and to see the new Navan, and life will be great.”

This is an opportunity to think about how to build a better business. It's exactly the way that I'm looking at this today. Maybe that's a different type. I talked to you about our culture. I see the opportunity. I see a huge opportunity for Navan, right?

I'm not waking up in the morning and checking the share price twice a day. I'm checking it when I'm waking up and when the market ends, just to know. People are asking you, and you need to know. But in any case, I'm not selling, or I cannot sell. My employees cannot sell, so I don't think it matters.

I think you need to build value, which eventually the shareholders and investors in Navan will benefit from. But again, start with the customer. Start with the user. If they are happy, the shareholders of Navan will be super happy.

Do you not think, then, that share price correlates to morale within a company?

100%. That's what I told you. I think the tough part that it adds to is what I've told you about me: am I getting depressed or manic when the share price is down or up? I'm not. But am I naive about it? Do I think that a lot of the Navan employees are refreshing their app all day long and checking where it is? They are, and it is my role to bring them along on the journey and keep pointing to what I know about the company and what the employees here know about the company.

We talked about it in Q3. Think about how we are growing like crazy in the PLG market, and how we are growing like crazy by signing new deals in the enterprise market. We pointed to examples in Q3. The employees here have all of the information to make their decision.

Then there is the share price, and I'm sure that it impacts them. It's my role to tell them to look at this in a 2-year timeframe, a 3-year timeframe, and probably a 10-year timeframe, and think about where we could be.

There is this famous letter that Bezos sent his investors when their share price was—I don't even remember the number—but very, very low. He was pointing to the business, and to the fact that the business was doing great. Guess what happened later? The share price more than caught up in that case.

How brutal is the talent war today? It seems like you're either hot and sexy, like Anthropic, OpenAI, Cursor, or any of these companies, and all the talent concentrates there, or you're not. How brutal is the talent war if you're not an AI-first model company or one of the darlings?

I think that the really good employees—and I told you, I have experience with this during COVID—are not built like that. I think they are very resilient. They want to win, and they want to see through the things that they've built. This is what I saw during COVID, and this is what I see now.

People who tend to go to the next shiny thing are not necessarily aligned with our culture to begin with. Again, it's my role to explain the choice to them, to show them the vision, and to show them the roadmap.

During COVID, around the May, June, and July timeframe, we had a lot of employees leaving for Zoom when Zoom was at its peak. I remember talking with them even then and telling them, “Hey, this is at the peak. Where do you think it will go? Do you think that more people than live on this planet will use Zoom? What exactly do you think is going to happen?”

They made their choices, and it's okay. But I want to have people in this company who believe in our mission and believe in our vision, and who check whether we are moving toward that. If we are, they usually stay.

You have the last laugh now.

On that one, yes, but it's not about that. People, by the way, can take their own journeys. Do you know how many career mistakes I've made in my life? People can have their own journeys. Some of them came back.

People can have their own journeys and make the wrong bets, but I actually think values and what kind of a story you want to be part of are more important than jumping to the next shiny thing.

7. Delay Cost Navan Growth

Final one before we do a quick fire. What career mistake do you reflect on most? I'm too interested. I passed on a deal at the seed round at a $10 million valuation instead of putting in a large check.

Mm-hmm.

I think about that every single day because that was a billion-dollar gain. What career mistake do you reflect on most?

Wow. I think that if I knew everything I know today, I would probably skip a startup and actually start Navan much earlier. But I didn't know.

Ilan and I definitely reflected on the Navan idea—the TripActions idea—back then, way before we jumped to do it. We had another startup in the middle. It probably would have been really beneficial. Navan would probably be significantly bigger and more impactful today if we had done it earlier, so that's a pretty big one.

Do you think so, or do you think you needed to have that experience to build the company that you've built today?

I think both of us worked in enterprise businesses. I've mentioned HP earlier, but there were others, so we had the experience needed to build something significant in the enterprise. But for travel, we didn't know anything about it, and Concur back then looked so scary that we probably delayed that journey by 2 to 3 years.

Totally get you. Dude, I'm going to do a quick fire with you. I give you a short statement, and you give me your immediate thoughts. Does that sound okay?

Let's do it.

What's been your biggest mindset shift in the last 12 months?

Think about the long term. Stop obsessing about short-term issues, and really, really think about the long term. Make sure that everybody is with you on this journey.

How did making money change your mindset toward life?

It makes stuff easier in that you can focus more on the things that you care about. You can get much more help around you, which allows you to create a nice balance between building something great and also having your own life.

I think money definitely helps there. But when I'm waking up in the morning, it's about really building this thing. It's not like I'm checking the share price times my holdings and thinking, “This is my money.” I'm not doing that. Actually, that's not how I think.

I think it's about convenience. It's about actually getting more time back.

What do you spend on that has made the biggest change to your life?

First of all, getting help—having people around you who can do stuff that you don't want to do. Fixing stuff in the house, doing things that I'm not good at doing—getting help frees up a lot of time.

To your point, I now live in both New York and here in Palo Alto. That's recent, and I love it. My kids, by the way, live there, but I can also enjoy New York, and I love big cities. We have this apartment in a neighborhood that we love, and that's fun.

How worth it is a jet?

I don't think I'm there yet. Sometimes I'm flying by jet, and sometimes I'm flying commercial. I think it saves time. I think that's what it does. Flying is hard, you know? Time zones are still a thing.

Jet lag is still a thing. I think my wife keeps making fun of me that all of Navan was created because of my anxiety in an airport, and it's so true. No matter what, even with jets, I'm still having the same anxiety.

Dude, I'm going to speak to you in a year, and you're going to have a Gulfstream, okay?

I'm not sure, by the way, but maybe.

I'm certain. You said you have kids. Tell me, what's your biggest parenting advice? What do you know now that you think is most important for being a good parent?

I think that's kind of what I told you: with money, you gain more time, so invest the time in your kids. Five or six years ago, I didn't invest that time. In the last 3 years, I have, and there is nothing more rewarding than that.

We talked a lot about Navan's mission and vision, private jets, and all of these things. I have twins who are 18. My relationship with them is so good and so deep, and I also have a 12-year-old. Again, same thing: invest the time. Invest the time. Don't pay that price. I did pay that price earlier, and I definitely regret it. I'm not doing it anymore. I'm really spending time with them.

You regret it?

But would it have been possible to do what you did without having that regret?

It would have. It would, and that's the price. That's the price.

So do you regret it?

This is very loopy. It's a good question. It's a really good question. I don't know. It's probably something to figure out with my therapist, but I can tell you that nothing is more rewarding than that.

Dude, I want to finish with: what are you most excited about? I like positivity, too. You said you're an optimist. What are you most excited about when you look toward the next decade?

I think almost the opposite of AI. I think people will get much more into fun, spirituality, and experiences. I think you and I talked in the past about my walkabout trips once a year by myself to scuba dive somewhere. I think people will have more time and more ability to focus on that, talking about the price that I've just talked about.

I'm excited to see what will happen there. It's the opposite of tech, the opposite of AI, but I think that's where society will be able to go with a way more efficient kind of life and workplace that we'll have.

Dude, you are the best. I so appreciate you, man.

I had a lot of fun. It was so much fun talking with you.