The Exchanges

Q It totally is. After 3000 interviews, there are a few people that I haven't met, but Oren is a special one for sure. But I do want to start on you, Ariel. So tell me, How did you make your way into the wonderful world of startups, but especially how did you come to found TripActions, and what was that aha moment for you?

A I'm originally from Israel, and I moved in oh nine to the US, and the main purpose, I've moved through HP after we got acquired in HP, but I've moved because I really wanted to move to the entrepreneurship side and really start startups, and I thought that the best place to do it is here in, you know, in Silicon Valley, and that was my goal, and I found myself in Jive, which was back then, it was a Startup. Then, you know, went through that and started a fairly small startup with my co-founder, Ilan Twig. We sold it back to Jive very fast after nine months, and the really good thing that happened there, it showed me what does it mean to be an entrepreneur, but it also created a lot of lifelong connections. So Oren Ziv, which you've mentioned, was also an investor in our previous startup. Arifjan Muhammad from Lightspeed was an investor in our previous startup. So it kind of created this relationship That eventually brought us all together to start trip actions. And trip actions, it's really, I think, based on my experience, right? I was, throughout my career, experiencing travel from both sides. I was a road warrior, so just someone that traveled a lot for business, and had a lot of experience around the, a lot of frustration, to be honest. Takes a very long time to book your trip. When you need support, it's, you need to hustle a lot, and so on. So there was that side. And on …

AI assessment note: “created this relationship That eventually brought us all together to start trip actions”

Q It totally is. After 3000 interviews, there are a few people that I haven't met, but Oren is a special one for sure. But I do want to start on you, Ariel. So tell me, How did you make your way into the wonderful world of startups, but especially how did you come to found TripActions, and what was that aha moment for you?

A I'm originally from Israel, and I moved in oh nine to the US, and the main purpose, I've moved through HP after we got acquired in HP, but I've moved because I really wanted to move to the entrepreneurship side and really start startups, and I thought that the best place to do it is here in, you know, in Silicon Valley, and that was my goal, and I found myself in Jive, which was back then, it was a Startup. Then, you know, went through that and started a fairly small startup with my co-founder, Ilan Twig. We sold it back to Jive very fast after nine months, and the really good thing that happened there, it showed me what does it mean to be an entrepreneur, but it also created a lot of lifelong connections. So Oren Ziv, which you've mentioned, was also an investor in our previous startup. Arifjan Muhammad from Lightspeed was an investor in our previous startup. So it kind of created this relationship That eventually brought us all together to start trip actions. And trip actions, it's really, I think, based on my experience, right? I was, throughout my career, experiencing travel from both sides. I was a road warrior, so just someone that traveled a lot for business, and had a lot of experience around the, a lot of frustration, to be honest. Takes a very long time to book your trip. When you need support, it's, you need to hustle a lot, and so on. So there was that side. And on …

AI assessment note: “I moved in oh nine to the US... That eventually brought us all together to start trip actions.”

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

A I think, and that's kind of what I told you, that with money, you can, you gain more time. Invest the time in your kids. Five, six years ago, I didn't. In the last three years, I have. And there is nothing, you know, we talked a lot about navigating One mission, and vision, and private jets, and all of these things. There is nothing more rewarding than that. Like, I have twins that are 18. My relationship with them is so good, so deep, and I also, I have also a 12 years 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, and I'm not doing it anymore. I'm really, really spending the time with them.

AI assessment note: “Invest the time in your kids.”

Q Respectfully, In a world where your stripes and your data bricks is and everyone push 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, go out at this time? And how did you reflect on the right timing?

A Yeah, there were a lot of reasons there, by the way. I think the first thing is that I am someone that I'm going on a certain trajectory. I'm following through. So the decision of taking a company public, that had a lot of reasons. You've called out one, which is basically our capital structure and the way that the balance sheet work post COVID, but there are other reasons. For example, in the payments business, I think there, there is huge, huge advantage to be a public company in the way that you are actually raising capital for that part of the business compared to being a private, a private company. I think if you kind of go too long in the payments business on being private, you may end up Not where you want to be. So that's kind of a, was definitely a driver, but it's also, you know, we have been starting to take, share in the enterprise segment, assigning more and more and more customers, and for them, 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 will be around. So there is a list of things to be public. Timing, you know, you start You are on the road, right? And the amount of times that the market has changed while we are going public, we are actually starting a non deal road shows in April on the same day that the, the tariffs were annou…

AI assessment note: “You've called out one, which is basically our capital structure and the way that the balance sheet work”

Q So, so just so I understand, so then you see change management, like now's the time, you see logos convert, like amazing logos like you mentioned, and then you go to the board and say, hey, look at our sales, look at our logos, they're up and to the right, we want to raise a new round? How did that catalyze a new round?

A Yes, so I actually went, ah, and back then, ah, ah, Greenox and, ah , and Neil actually looked at this, and, you know, it was the first time I didn't know him before, but he looked at this, and I basically told him that story. Hey, listen, we don't have revenue. We are, ah, burning a lot of cash, because the company, think about a fairly scaled, ah, company, but here is our plan, and if you believe in our, like, ability to execute, The only thing that you will need to bet on here is that travel will come back. So just decide, do you think the travel will come back or not? If you think the travel will come back, I think we are a really good investment right now, because obviously it was in better terms than what you would have gotten if COVID was not around us. And that resonated. Now, I will tell you, you know, we've talked probably with 30 investors. 28 of them told us that travel will never come back. Uh, I've talked to one of the, you know, the biggest VCs here in Silicon Valley, right, and a very famous one and known one, and, and, you know, very good conversation, but they told me eventually, you know what, we actually don't think the travel will come back. And I said, okay, so if travel will not come back, it will be very hard for me to make a case for you to invest in the company, right? So, so, but the ones that had the courage back then too, I think it was only one bet…

AI assessment note: “The only thing that you will need to bet on here is that travel will come back.”

Q Can I ask, do they not just become sales machines though? They invest so heavily in sales and then change management and stickiness is strong. And that's why they keep growing. Like, look at the numbers. They keep growing.

A Yeah, first of all, if I look at the numbers, I think both Salesforce and SAP actually specifically now are not growing and in fact declining, right? So that's specifically now. I think they do grow through M&A. That's the only power that they have. So it's basically M&A and the channel. I'm going to use my connection into, into IT, into enterprise IT, uh, to continue and push whatever I purchased yesterday, uh, through this channel to that And you know, I used to work for HP, and that was the play there, right? The HP software, that was the play. Let's keep buying companies, and then push them through the channel. Over time, there are massive changes, right? For HP, it was the entire cloud. There are massive changes, and you are not going to survive it. And I think the massive change right now, again, powered by AI, is that companies want to have Software that solves this problem without the need to enforce it, without the need to fight with their employees all day long. So, I think, yeah, I respect, actually, their, uh, channel, these sales organizations that they've created, the ability to do M&A, but eventually, over time, innovation, technologies, breakthroughs, always winning.

AI assessment note: “I think both Salesforce and SAP actually specifically now are not growing”

Q So, so just so I understand, so then you see change management, like now's the time, you see logos convert, like amazing logos like you mentioned, and then you go to the board and say, hey, look at our sales, look at our logos, they're up and to the right, we want to raise a new round? How did that catalyze a new round?

A Yes, so I actually went, ah, and back then, ah, ah, Greenox and, ah , and Neil actually looked at this, and, you know, it was the first time I didn't know him before, but he looked at this, and I basically told him that story. Hey, listen, we don't have revenue. We are, ah, burning a lot of cash, because the company, think about a fairly scaled, ah, company, but here is our plan, and if you believe in our, like, ability to execute, The only thing that you will need to bet on here is that travel will come back. So just decide, do you think the travel will come back or not? If you think the travel will come back, I think we are a really good investment right now, because obviously it was in better terms than what you would have gotten if COVID was not around us. And that resonated. Now, I will tell you, you know, we've talked probably with 30 investors. 28 of them told us that travel will never come back. Uh, I've talked to one of the, you know, the biggest VCs here in Silicon Valley, right, and a very famous one and known one, and, and, you know, very good conversation, but they told me eventually, you know what, we actually don't think the travel will come back. And I said, okay, so if travel will not come back, it will be very hard for me to make a case for you to invest in the company, right? So, so, but the ones that had the courage back then too, I think it was only one bet…

AI assessment note: “The only thing that you will need to bet on here is that travel will come back.”

Q 3000. How do you retain that innovation and agility?

A I think it's about decisions. I think, you know, we kind of starting to feel comfortable with travel innovation, right? That we really thought that we figured out How to create this magic between the company and the employees. How to book fast. How to support yourself fast. And Ilan and I looked at this. Ilan is my co-founder. Uh, and this was like five years ago. And we said, you know, if we would have started drip actions again, we wouldn't do it like that. And out of this came everything that we did around payments and expense management. And two years ago, uh, we looked at this again. And this is, and we said, you know, today with machine learning, you can achieve a much better service by servicing people fast. Like, you know, you cancel your flight. Are you going to get your tickets back or not? It's very hard to automate it, but we've managed to automate it with a lot of uses of, of smartness inside. We are calling it, we have an internal board, we call it Cati's IQ. And this is this thing that keeps learning. And therefore keeps generating value for the users. So again, we kind of killed what we had and recreated it. So I think you keep this innovation if you have the courage, first of all, to look at the mirror and come and say, okay, what we had done up until now was relevant back then with our understanding that in the technology back then, but maybe it's time to kill…

AI assessment note: “you keep this innovation if you have the courage, first of all, to look”

Q Speaking of doing what you believe in the right thing for the company, you also mentioned killing projects. How do you determine which projects to kill?

A Yeah, first of all, you know, I think that, uh, I will bring it back to, uh, maybe kind of the lean startups kind of concepts, right? And I think what I really like in this concept is that you start something with hypotheses, and you start to measure it, right? And your entire purpose is not to develop the product, but to actually examine your hypotheses. And I think if you're strict about it, you cannot lie to yourself, right? You have an hypothesis, You're saying, hey, this is what I think that this product will do, or this feature will do, or this project will do, and this is how we think that the market will accept it, and then you put the right metrics and measurements in place, and you keep asking the question, is it happening or not? Is it happening or not? And you can do some pivots, and you can do some, uh, right, so it doesn't mean that your first implementation will be the right one, but if you operate like that, It's not that hard to bring the team into a room and say, you know, we had this hypothesis. Uh, it doesn't work. Let's move on. Let's do something else. I think if you do that, you are, you are very capable of killing projects.

AI assessment note: “you put the right metrics and measurements in place, and you keep asking the question”

Q Ariel, you mentioned, you know, the time when COVID happened and your revenues went to zero. I, I just want to understand, like, take me to that moment. How did you respond? That is a, oh shit moment.

A Yeah, first, first of all, you know, um, I personally, and sometimes, you know, you could perceive it as maybe cold. I can, uh, can move on fast. I can come and say to myself, okay, the, the, the plan that we had, In that company that we had, ok, is not relevant right now. Ok, and so what does it mean? For me, and I'll get back to, I will mention this magic again and again, because it's really the core of, uh, of Novan. For me, you know, March, we lost all of our revenue. Obvious to me that we lost product market fit overnight. Nobody needs this product anymore, right? So, for me, it got, it got back to the basic question. I do believe that there is this new category of business software that is designed for people, basically creating people-centric product. That's something that I believe, like we started the company with that belief. And I do believe that travel and expense is an important part of this. And I also think that people will travel in two years from now, right? Again, March, 20, 20. So all of my beliefs are still there. This new type of software. T&E is important. People will travel in the future. So now what do you do? Do you kill the company? Do you hibernate the company? Or do you double down? And if it's just random, probably you need to hibernate the company or kill it. But if you still have this set of beliefs, and everybody around you, your investors, a big…

AI assessment note: “So you make some tough decisions. You cut costs. You know, we did... Pretty big layoffs.”

Q Can I be blunt? Yeah. How did you expand the business? And how did you raise at, you know, like, double valuation for, like, at the time, predominantly a travel company in the middle of COVID? Like, I, it's, it's incredible, but how?

A It comes down to this set of beliefs, right? So I remember, you know, in March, 2020, the issue was not only that, uh, obviously we were going down very fast, But at that point, people thought that the entire economy will go down. Then, you know, there was a change, and tech, I think, actually led the way of the economy to actually show that you're not going down as an economy, right? Um, but at that point, there was so much pessimism, and, you know, I came to the team and to the board and was saying, okay, we're gonna definitely stabilize. We're gonna cut costs, right? No, no, no question about it. But we're gonna stay in the market and sell Travel, right? And in fact, we're going to expand to expense management and sell, sell to any, T&E. And of course, the reaction would be, oh, and we're going to raise money. And of course, the reaction would be, but how are you going to do that? You're going to call a CFO right now and tell them you need to kind of use a, you know, the trip actions for a, for a, for travel, and they will tell you we're not traveling right now. What are you talking about? But think about it. If you convince them, it was not hard to convince, the travel will come back. What's better than to do change management from this antiquated, you know, Comcare and GBT, you know, American Express GBT. Nobody likes it. The only reason that people are staying with that i…

AI assessment note: “Nobody's traveling. Nobody's expensing. Change now. And that was our pitch.”

Q Can I ask, do they not just become sales machines though? They invest so heavily in sales and then change management and stickiness is strong. And that's why they keep growing. Like, look at the numbers. They keep growing.

A Yeah, first of all, if I look at the numbers, I think both Salesforce and SAP actually specifically now are not growing and in fact declining, right? So that's specifically now. I think they do grow through M&A. That's the only power that they have. So it's basically M&A and the channel. I'm going to use my connection into, into IT, into enterprise IT, uh, to continue and push whatever I purchased yesterday, uh, through this channel to that And you know, I used to work for HP, and that was the play there, right? The HP software, that was the play. Let's keep buying companies, and then push them through the channel. Over time, there are massive changes, right? For HP, it was the entire cloud. There are massive changes, and you are not going to survive it. And I think the massive change right now, again, powered by AI, is that companies want to have Software that solves this problem without the need to enforce it, without the need to fight with their employees all day long. So, I think, yeah, I respect, actually, their, uh, channel, these sales organizations that they've created, the ability to do M&A, but eventually, over time, innovation, technologies, breakthroughs, always winning.

AI assessment note: “I think both Salesforce and SAP actually specifically now are not growing”

Q What makes OpenAI so much more effective than even your internal tools that you built for years and everyone else's stack? What makes it so much better?

A Yeah, I think, you know, people have a lot of opinions about it. I think it comes down to the data set. I think that, you know, there was a lot of time, including with us, that was used to train your AI to be smart, right? So we used to call this thing Erva's IQ. So what is Erva's IQ? It's this kind of, it's the brain, right? You do, you know, we support somebody, and that support was successful or not. You can measure it through CSAT, Through, are they going to repeat and calling the call center again? Stuff like that. So, basically, you need to give the system the signal, was it successful or not, was the answer. So, this training, I think, was the old way of doing AI, right? And that's how we operated, and I think that's, by the way, how 98% of the companies that did AI did it. I think what OpenAI did is that they can, they proved that if you put a huge data set, Right? Inside the, inside this thing, magic will happen. I'm not even sure if, if the, I actually don't know how this magic happens, by the way, but I think that magic will happen, and we see it, right? We started to ask, I'll give you an example of the magic. Uh, you could have gotten to the bot that we had before OpenAI, and asked to book the Westin in New York, ok? And what Ava will do at that point? She would ask you, she would ask you, What do you want to book? But I just told you, the Westin, right? If you go …

AI assessment note: “I think it comes down to the data set.”

Q Do you worry about having such a core part of the business and margin structure, I'm sure, over time? Do you worry about having that provided by an external provider?

A I think that eventually the bot can do one thing. It can answer questions based on all of the data that they have. Eventually you need to operationalize it. You do need to change that flight, right? You do need to book that flight. You do need to have the supplier's relationships. You do need to do to have all of these things. So I think the moat That we've created is actually not around that technology. The moat is around all of the infrastructure here that allows us to go globally, to service our customers globally, to provide one T&E report for all of the companies that are using us. That's the moat. Now, the other moat is more of a cultural moat. Do you have the courage to keep killing everything that you did because a new technology showed up and connected to our infrastructure? And I think if you do that, Uh, whether it's external or internal, uh, vendor, it's not important. Uh, you know, you can ask the same question about AWS, right? People used to employ DBAs, and I don't know, a lot of active people that were connecting, like, some, some cables to servers, and they stopped doing it, so I think it's the same thing.

AI assessment note: “whether it's external or internal, uh, vendor, it's not important.”

Q Can I ask, you mentioned there about kind of speaking with the people you trust. Obviously for me as a VC, I want to be the best that I can be for our founders in this environment. Help me out here. What does the best investor do to help you in this time? What would you most want from your investor in this time?

A Yeah, I think that investors, and we kind of briefly touched it, right, but I was fortunate to have really good investors, right? We've talked about Oren and Arif already, but I also have Ben Horowitz, which he, you know, he lived through something like that, right? He ran a company in O-one, right? And even took it public at that time, right? He wrote a book about it. So having someone that really went through that on the culture level, on how do you communicate with employees, how do you deal with cash, how do you optimize the moment, and really focusing on the right things, that's super, super powerful. And what I've noticed about our investors, Throughout this crisis, it starts with trust, right? For me as a CEO, as an entrepreneur, it's very important to see, to feel that our investors trust me to weather the storm, but also challenge you, asking you some questions, right? Why are you doing that? Why are you doing the other thing? And I think that if you feel that the challenge is coming from mistrust, that would be extremely not effective. If it's coming from a discussion, hey, we trust you, but maybe you didn't think about that. That's very, very powerful. So for me, having investors that A, are just really good people, but B, also believe in the long term of trip actions, and believe in me, believe in Elon, believe in the team, that helps a lot.

AI assessment note: “having someone that really went through that... it starts with trust”

Q So I think secretly I've always wanted to be a psychologist, but we mentioned children there and psychologists always give everything to your childhood and how it impacted you. I do think everyone is a function of their histories. What do you think you're running from, Ariel?

A If you take a step back, I think the one that comes in mind always for me is Salesforce and SAP, which are not innovating. I think the last time that SAP innovated something was in the nineties, and the last time that, that Salesforce innovated was in the beginning of 2000. And I'm looking at this, and besides the fact that I think it's embarrassing that companies that are located in the middle of Silicon Valley have not been innovating for years, it's also what I'm running from. The one thing that scares me Is that one day, Navan will be that kind of a company that the only way that you innovate is through M&A, and through using your market dynamics and your power in the market to basically sell, and this really scares me.

AI assessment note: “it's also what I'm running from. The one thing that scares me Is that”

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

A 100%. That's what I told you that I think that the tough part that it adds to is that what I've told you is me. Like, am I getting depressed or like in some mania when, you know, it's like when, when the share price is up? I'm not, but do, am I naive about it? Do I think that a lot of the Navan employees are refreshing their, you know, their app all day long and checking where it is? They are, and it is my role to actually bring them along to the journey and keep pointing to what I know about the company, what the employees here know about the company, and you know, we kind of talked about it in Q-three. Think about, like, we are going like crazies in the PLG market, and we are going like crazy by signing new deals in the enterprise market, and we pointed to examples in Q-three. The employees have all of the information to make their decision, and yeah, then there is the share price, and I'm sure that it impacts them, and it's my role to kind of tell them to look at this in a, Two years time frame, three years time frame, and probably 10 years time frame, and think about, like, where we could be. You know, there is this famous kind of letter that kind of Bezos sent his investors, right, when their share price was, I don't even remember what was the number, but very, very low, and he was pointing to the business, and to the business that is doing great, and guess what happened l…

AI assessment note: “100%. That's what I told you that I think”

Q Ariel, you mentioned, you know, the time when COVID happened and your revenues went to zero. I, I just want to understand, like, take me to that moment. How did you respond? That is a, oh shit moment.

A Yeah, first, first of all, you know, um, I personally, and sometimes, you know, you could perceive it as maybe cold. I can, uh, can move on fast. I can come and say to myself, okay, the, the, the plan that we had, In that company that we had, ok, is not relevant right now. Ok, and so what does it mean? For me, and I'll get back to, I will mention this magic again and again, because it's really the core of, uh, of Novan. For me, you know, March, we lost all of our revenue. Obvious to me that we lost product market fit overnight. Nobody needs this product anymore, right? So, for me, it got, it got back to the basic question. I do believe that there is this new category of business software that is designed for people, basically creating people-centric product. That's something that I believe, like we started the company with that belief. And I do believe that travel and expense is an important part of this. And I also think that people will travel in two years from now, right? Again, March, 20, 20. So all of my beliefs are still there. This new type of software. T&E is important. People will travel in the future. So now what do you do? Do you kill the company? Do you hibernate the company? Or do you double down? And if it's just random, probably you need to hibernate the company or kill it. But if you still have this set of beliefs, and everybody around you, your investors, a big…

AI assessment note: “make some tough decisions. You cut costs... double down on innovation”

Q What makes OpenAI so much more effective than even your internal tools that you built for years and everyone else's stack? What makes it so much better?

A Yeah, I think, you know, people have a lot of opinions about it. I think it comes down to the data set. I think that, you know, there was a lot of time, including with us, that was used to train your AI to be smart, right? So we used to call this thing Erva's IQ. So what is Erva's IQ? It's this kind of, it's the brain, right? You do, you know, we support somebody, and that support was successful or not. You can measure it through CSAT, Through, are they going to repeat and calling the call center again? Stuff like that. So, basically, you need to give the system the signal, was it successful or not, was the answer. So, this training, I think, was the old way of doing AI, right? And that's how we operated, and I think that's, by the way, how 98% of the companies that did AI did it. I think what OpenAI did is that they can, they proved that if you put a huge data set, Right? Inside the, inside this thing, magic will happen. I'm not even sure if, if the, I actually don't know how this magic happens, by the way, but I think that magic will happen, and we see it, right? We started to ask, I'll give you an example of the magic. Uh, you could have gotten to the bot that we had before OpenAI, and asked to book the Westin in New York, ok? And what Ava will do at that point? She would ask you, she would ask you, What do you want to book? But I just told you, the Westin, right? If you go …

AI assessment note: “I think it comes down to the data set.”

Q Do you worry about having such a core part of the business and margin structure, I'm sure, over time? Do you worry about having that provided by an external provider?

A I think that eventually the bot can do one thing. It can answer questions based on all of the data that they have. Eventually you need to operationalize it. You do need to change that flight, right? You do need to book that flight. You do need to have the supplier's relationships. You do need to do to have all of these things. So I think the moat That we've created is actually not around that technology. The moat is around all of the infrastructure here that allows us to go globally, to service our customers globally, to provide one T&E report for all of the companies that are using us. That's the moat. Now, the other moat is more of a cultural moat. Do you have the courage to keep killing everything that you did because a new technology showed up and connected to our infrastructure? And I think if you do that, Uh, whether it's external or internal, uh, vendor, it's not important. Uh, you know, you can ask the same question about AWS, right? People used to employ DBAs, and I don't know, a lot of active people that were connecting, like, some, some cables to servers, and they stopped doing it, so I think it's the same thing.

AI assessment note: “whether it's external or internal, uh, vendor, it's not important.”

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

A 100% not, yeah. I think that the market has, I would say, two Uh, observations about us that are incorrect. The first one, ah, it is very hard to compare it in a van business, to find a comparable, to, to compare it to anything else. Because on one side, it is a tech company, and we are, the value that we are creating is for travelers and their employers. So it makes it look like a SaaS company. On the other side, our business model is very much consumption. You come to the platform, we only make money when you use us. And the way that our business works, we sign agreements today, we pay commission today, so all of the go-to-market cost is going today, and in the next years to come, you are going to make a lot of money in a very, very, very healthy way. So what investors see in our P&L is a huge investment in go-to-market, and they don't see the immediate return. Well, I can tell you without getting to the details, because we are not sharing these numbers, that we have an extremely efficient go-to-market, And we have an extremely efficient churn profile. It's actually rare that companies are leaving the van. So one side is like, we don't fully understand their growth algorithm or their go to market. And I think we need to do a better job explaining it. So that's one side. But I think that just over time and over the quarters, people will see our delivery. On the other side to y…

AI assessment note: “I think that the market has, I would say, two Uh, observations about us”

Q It's totally the same as me. Cass, does that impact how you advise your children when it comes to how they pick up and learn new things?

A 100%. So I have three kids, uh, two of them, they are twins, a boy and a girl, they are 15, right? So they are starting to think, you know, what would they do next, and so on. And one of the things that I've told them, hey, you do whatever you want to, but my advice to you, don't even at age 18 have this pressure to go to college, because I don't think that you know what you really want to do with your life at age 18, and I know that a lot of people are doing ski peer And I like traveling, and a lot of my conclusions are happening while I'm traveling and meeting people, so my advice to them, what you're gonna do with your life and school and all of these things, uh, it will get figured out, but first, kind of, you know, take the time to really, uh, learn, to really understand what, uh, you know, what interests you, and I think that in any case, we are in such a interesting, uh, time in our lives, With the, the development, and I know that we're gonna talk about it, but with the developments of, ah, machine learning and AI. So I'm not even sure that the things that we are learning today are not kind of obsolete. So, uh, my advice to them, don't take this too seriously. Do whatever you want to with your life.

AI assessment note: “100%. So I have three kids... my advice to you, don't even at age 18”

Q Speaking of doing what you believe in the right thing for the company, you also mentioned killing projects. How do you determine which projects to kill?

A Yeah, first of all, you know, I think that, uh, I will bring it back to, uh, maybe kind of the lean startups kind of concepts, right? And I think what I really like in this concept is that you start something with hypotheses, and you start to measure it, right? And your entire purpose is not to develop the product, but to actually examine your hypotheses. And I think if you're strict about it, you cannot lie to yourself, right? You have an hypothesis, You're saying, hey, this is what I think that this product will do, or this feature will do, or this project will do, and this is how we think that the market will accept it, and then you put the right metrics and measurements in place, and you keep asking the question, is it happening or not? Is it happening or not? And you can do some pivots, and you can do some, uh, right, so it doesn't mean that your first implementation will be the right one, but if you operate like that, It's not that hard to bring the team into a room and say, you know, we had this hypothesis. Uh, it doesn't work. Let's move on. Let's do something else. I think if you do that, you are, you are very capable of killing projects.

AI assessment note: “we had this hypothesis. Uh, it doesn't work. Let's move on.”

Q How long do you give it? Because there's that kind of, um, you know, you can't do it too quickly. You need enough data, but then too many founders are afraid to kill it and give it way too long.

A I think it's, it's based on how important it is for your strategy. If it is Fundamental for your strategy. You define your strategy as a company, and you are saying this thing. I'll give you an example. Uh, we give rewards for employees to save company money. So you come to our product, you try to book a hotel, uh, it's in policy, and then we are telling you, but if you book something that is lower than the policy, we're gonna give you rewards. Right, it's part of the Navan Rewards Program. We are rewarding you to use us. We are, we are rewarding you to save company money. Uh, we also, you're also getting your, you know, your Marriott's loyalty points. Uh, so you get it all, right? You, I'm calling it, uh, you triple dip, right? Or with your credit card, if even you, you dip four times. So you're happy as an employee. Uh, but when we started the company, Uh, we had the same idea. Nobody used it. Nobody used it. Nobody would click on the stuff that will give you the rewards, and nobody would actually redeem these rewards. So, now the question is, are you pivoting, or are you doubling down? And this, uh, feature, today feature, back then it was the entire company, was so important for, for our strategy, That even though the hypothesis was incorrect, right? Nobody was using it. We're measuring it. We've decided to double down. We've decided to continue to pivot, to change the UI, …

AI assessment note: “I think it's, it's based on how important it is for your strategy.”

Q It's totally the same as me. Cass, does that impact how you advise your children when it comes to how they pick up and learn new things?

A 100%. So I have three kids, uh, two of them, they are twins, a boy and a girl, they are 15, right? So they are starting to think, you know, what would they do next, and so on. And one of the things that I've told them, hey, you do whatever you want to, but my advice to you, don't even at age 18 have this pressure to go to college, because I don't think that you know what you really want to do with your life at age 18, and I know that a lot of people are doing ski peer And I like traveling, and a lot of my conclusions are happening while I'm traveling and meeting people, so my advice to them, what you're gonna do with your life and school and all of these things, uh, it will get figured out, but first, kind of, you know, take the time to really, uh, learn, to really understand what, uh, you know, what interests you, and I think that in any case, we are in such a interesting, uh, time in our lives, With the, the development, and I know that we're gonna talk about it, but with the developments of, ah, machine learning and AI. So I'm not even sure that the things that we are learning today are not kind of obsolete. So, uh, my advice to them, don't take this too seriously. Do whatever you want to with your life.

AI assessment note: “100%. So I have three kids... my advice to you, don't even at age 18”

Q How long do you give it? Because there's that kind of, um, you know, you can't do it too quickly. You need enough data, but then too many founders are afraid to kill it and give it way too long.

A I think it's, it's based on how important it is for your strategy. If it is Fundamental for your strategy. You define your strategy as a company, and you are saying this thing. I'll give you an example. Uh, we give rewards for employees to save company money. So you come to our product, you try to book a hotel, uh, it's in policy, and then we are telling you, but if you book something that is lower than the policy, we're gonna give you rewards. Right, it's part of the Navan Rewards Program. We are rewarding you to use us. We are, we are rewarding you to save company money. Uh, we also, you're also getting your, you know, your Marriott's loyalty points. Uh, so you get it all, right? You, I'm calling it, uh, you triple dip, right? Or with your credit card, if even you, you dip four times. So you're happy as an employee. Uh, but when we started the company, Uh, we had the same idea. Nobody used it. Nobody used it. Nobody would click on the stuff that will give you the rewards, and nobody would actually redeem these rewards. So, now the question is, are you pivoting, or are you doubling down? And this, uh, feature, today feature, back then it was the entire company, was so important for, for our strategy, That even though the hypothesis was incorrect, right? Nobody was using it. We're measuring it. We've decided to double down. We've decided to continue to pivot, to change the UI, …

AI assessment note: “it's based on how important it is for your strategy.”

Q Yeah, Ariel, oh no, this is my job. Why are you changing the name, Ariel? Great question.

A And I'm, and I'm, and I'm saying it because I think it is related to your question, but we wanted to actually create this new category to show the way, to lead the way, and show All of the companies around, you have to develop a new kind of software, a software that is more inviting. So Navant, just the name, it's about navigation, navigating the world, and about Avant, right? This is really where the name is coming from, and it's a palindrome, right? So it's really inviting you from all, all directions, right? So it's really about us. It's about us inviting all of the employees, all of the, all over the world, To use Navan, inviting the company to achieve all of its goals, uh, all of the company's goals, while the employees are participating in it. So it's, it's magical. That's, this is really, I, the way that I, I'm thinking about Navan. And if you think about it in these terms, it's not, not only a point solution, it really solves a really big problem. Companies are spending seven percent of their entire budget on T&E, so it solves a really big problem, but it also shows the way To companies that lost that way, to companies like Salesforce, like SAP, it shows the way for all of the companies around the world that today you can create really good software for the company and the employees.

AI assessment note: “it's about navigation, navigating the world, and about Avant, right?”

Q Can I be blunt? Yeah. How did you expand the business? And how did you raise at, you know, like, double valuation for, like, at the time, predominantly a travel company in the middle of COVID? Like, I, it's, it's incredible, but how?

A It comes down to this set of beliefs, right? So I remember, you know, in March, 2020, the issue was not only that, uh, obviously we were going down very fast, But at that point, people thought that the entire economy will go down. Then, you know, there was a change, and tech, I think, actually led the way of the economy to actually show that you're not going down as an economy, right? Um, but at that point, there was so much pessimism, and, you know, I came to the team and to the board and was saying, okay, we're gonna definitely stabilize. We're gonna cut costs, right? No, no, no question about it. But we're gonna stay in the market and sell Travel, right? And in fact, we're going to expand to expense management and sell, sell to any, T&E. And of course, the reaction would be, oh, and we're going to raise money. And of course, the reaction would be, but how are you going to do that? You're going to call a CFO right now and tell them you need to kind of use a, you know, the trip actions for a, for a, for travel, and they will tell you we're not traveling right now. What are you talking about? But think about it. If you convince them, it was not hard to convince, the travel will come back. What's better than to do change management from this antiquated, you know, Comcare and GBT, you know, American Express GBT. Nobody likes it. The only reason that people are staying with that i…

AI assessment note: “we're going to expand to expense management and sell, sell to any, T&E.”

Q How do you get over being afraid? How do you bring people with you as well? Also, when you're deprioritizing something, you don't want those that were prioritized on it to feel like the unloved child. How do you get over that?

A First of all, you never give up. And I, I'll, I'll give you an interesting anecdote. Um, you know, COVID started, um, and we, uh, kind of lost all of our revenue, but decided to continue to be in the market and sell, do M&A, raise money, but the most important thing, innovate, like continue to innovate. Uh, but back then I've decided that the innovation would not necessarily be just about level, but we're actually going to Shift resources. We're going to shift the designers, product managers, uh, developers, uh, from the travel side to the expense management, uh, side. And that was a decision that actually the employees, uh, back then didn't like. Okay. From a lot of various reasons. Again, we've talked about being afraid of change. So in that process, I actually lost most of my product team. Okay. And, you know, two years afterwards, I started to look at the data that showed how much both are picking up, like travel and expense management. And I remember that they, I told my co-founder, you know, sometimes you need to do these decisions, even if it means that you're going to lose the team in the process, because that was the right decision. So sometimes you can bring people along with you. I think most of the cases, Uh, that's what we, that's what I do, and you can do that. But you cannot be afraid of the consequences, of the implications, of doing what you believe, um, intuit…

AI assessment note: “sometimes you need to do these decisions, even if it means that you're going to lose”

Q You spoke about kind of product innovation driving value there. You chose to integrate OpenAI into your chatbot. Talk to me about that decision. What does it mean for the business? Why did you make that decision? And, and I guess broad, how do you see the future of AI integration into your company?

A Welcome to the party, right? Uh, Elon, my co-founder, will go to events, uh, six, seven years ago, a lot in the travel industry, and will talk about, uh, machine learning and AI, and people looked at him as like, what, what is he talking about? And then we were trying to explain it in value terms, so we'd say, you know, our search, when you are, uh, trying to book a trip in TripActions, uh, it takes you five minutes to do that, because we know what would be the first three things that probably you're gonna select, right? So we always set it, and I don't know if people fully, fully understand it. Uh, a year ago, we launched our, uh, first, uh, bot. We are now naming this bot Eva, which is kind of part of Navan. And that bot today handles 30% of our, of our support interactions. Basically, it behaves like a travel agent that will say, change your flight, will handle flight cancellations, will go and get a refund from an hotel. In fact, Navan, Navan's users, when they check out from an hotel, they actually, they don't need to go to the reception and get the receipt. We are, through a bot that we have, are actually calling the hotel, getting the receipt for them, automatically itemizing it, and automatically expensing it, right? That's how much today, right, uh, our, our technology is effective around, around AI and machine learning. So now, um, uh, and, and all of this was not pow…

AI assessment note: “OpenAI did a huge leapfrog... so we decided to do it”