The Exchanges

Q I totally agree. And you can build such customer advocates in the early days by actually just being so responsive and so intuitive to their feedback. Totally agree. Tell me, dude, how we're going to get onto learnings from past, but just in terms of zip, Why did you choose this? What was the aha moment for you when it came to founding Zip?

A So it was a problem that my co-founder Lou and I, uh, that we had both experienced. So we had, you know, we, we actually met, we both worked together at Airbnb. Uh, Lou was an engineering leader at Airbnb. I, I worked as a product manager. Uh, and, uh, you know, what happened, uh, was that, you know, I remember actually one day, uh, we, we woke up to, to an email message saying, Hey, uh, Rajul and Lou, uh, you know, So-and-so has left the organization. You guys have been designated, uh, as, uh, the, the business owners, uh, uh, of our contract with this. It was a large, large contract software contract. Yeah. There's a renewal coming up and we were assigned somebody from the procurement organization because it was such a large contract. Uh, and we said, sure, you know, we'll be the business owners, like tell us what we need to do. Uh, and the first thing we heard, we had to, what we had to do was, um, we were told, Hey, you have to go to our ERP system, uh, and create a PR. Uh, and I remember we were both, we both looked at each other. We were like, sorry, uh, what? Uh, and, uh, and the person was like, oh, it's a, it's a purchase requisition. Uh, you know, at the time, the only PR that we knew was a, was a pull request. Uh, and, uh, and so we were like, oh, well, purchase requisition. Okay. I mean, I can understand what that means. And, and so of course I remember we go to the…

AI assessment note: “it was a problem that my co-founder Lou and I, uh, that we had both experienced.”

Q How do you think about the centralization of budget? Yes. You know, with budgets generally contracting or being frozen, a lot of people say CFOs are much more active in terms of the buying process. You're like, actually, that's not at all what we're saying. That's bullshit. How do you think about the centralization of budgets given what we just said there?

A Yeah. Yeah. Uh, it's, it's what I would say is it's decentralization of the initiation of the spend and centralization in many aspects of the review of the spend. Uh, and so, so you're totally right. Uh, I mean, one of the things we see across the hundreds of customers we have today is, you know, our customers control their delegation of authority in Zip, right? So, hey, if it's above, a simple example is, hey, if it's above, you know, a 100,000 dollars, then I want my CFO to review versus another company might say it's a million. Another company might say it's 10,000. Um, and I think it was interesting to see with the macro climate of the last 18, you know, months or, or whatever it's been, you know, delegation of authority certainly came down. Uh, across the board and many, many organizations, um, because they want to have the CFOs to see more.

AI assessment note: “decentralization of the initiation of the spend and centralization in many aspects of the review”

Q How did you learn to explain it for founders listening today who don't feel like it's resonating, who don't feel like it hits? What lessons do you have from that six month period of exploration to your ultimate? It started to hit that you'd share with them.

A Yeah. Yeah. No, it's a great question. So what we actually did, so we were actually quite wrote in our approach here, uh, every week, Actually, initially it was every day because we had so many calls and then we were like, we don't need to review this every day. We did it every Sunday. Uh, we would write out our quote unquote investor pitch, which is like, you know, a couple of sentences of like what Zip does, but the investor view of it, you know, talking about like the market, that kind of thing. And then the customer pitch. Uh, and we would cheap at one point where we're looking at both of those in one Google doc every single day. Uh, and you'd be like, what did we learn today? Like, would we change How we frame it. Uh, and then we would test it for all the calls that we would, we would do the following day. Uh, then it got to a point where we're like, no, we don't need to change it that much. Let's review this every week. And so we basically had this process where we're constantly reviewing. Then as we started to talk to more people, we sort of morphed this and literally built an Excel, like a Google sheet and morphed it into ICP. Like we had different IC, potential ICPs as the row, uh, as each row, because we didn't know, like, are we going to sell to IT, legal, Procurement, which ended up being the case. Finance, right? Like all these people have to approve things that pe…

AI assessment note: “we had this process where we're constantly reviewing”

Q I totally agree. And you can build such customer advocates in the early days by actually just being so responsive and so intuitive to their feedback. Totally agree. Tell me, dude, how we're going to get onto learnings from past, but just in terms of zip, Why did you choose this? What was the aha moment for you when it came to founding Zip?

A So it was a problem that my co-founder Lou and I, uh, that we had both experienced. So we had, you know, we, we actually met, we both worked together at Airbnb. Uh, Lou was an engineering leader at Airbnb. I, I worked as a product manager. Uh, and, uh, you know, what happened, uh, was that, you know, I remember actually one day, uh, we, we woke up to, to an email message saying, Hey, uh, Rajul and Lou, uh, you know, So-and-so has left the organization. You guys have been designated, uh, as, uh, the, the business owners, uh, uh, of our contract with this. It was a large, large contract software contract. Yeah. There's a renewal coming up and we were assigned somebody from the procurement organization because it was such a large contract. Uh, and we said, sure, you know, we'll be the business owners, like tell us what we need to do. Uh, and the first thing we heard, we had to, what we had to do was, um, we were told, Hey, you have to go to our ERP system, uh, and create a PR. Uh, and I remember we were both, we both looked at each other. We were like, sorry, uh, what? Uh, and, uh, and the person was like, oh, it's a, it's a purchase requisition. Uh, you know, at the time, the only PR that we knew was a, was a pull request. Uh, and, uh, and so we were like, oh, well, purchase requisition. Okay. I mean, I can understand what that means. And, and so of course I remember we go to the…

AI assessment note: “it was a problem that my co-founder Lou and I, uh, that we had both experienced.”

Q problem to go after. I'm just so interested. It's a big problem to go after, like, first off from day one. How do you think about the product decision of whether to go in with a kind of feature that solves one specific pain point, or a much broader platform play, which really tries to address a lot of the problems from day one? How do you think about that?

A You'll eventually get to the latter, uh, but I think for first off, like, I mean, given how much capacity you have, which is Basically nothing. When you're starting out, you have to find, and it's actually, it's actually healthy that you don't have that many resources because it's the forcing function to say, what is that one thing? The one pain point that somebody will be like, you're right. I need that thing. And like, it doesn't exist otherwise in the world for me that because what, what actually happens is when you have a platform, other people have platforms too, and they all do everything. But then the question becomes, how do you differentiate your platform from somebody else's platform? And you'll actually always come back to that one thing that you started with, which is, Hey, no, no, no. This is the thing that makes us special in the world. No one else does this at anywhere near the level that we do. That's why our platform is better. We sure we do a lot of things that they do too, but this thing is different. Uh, uh, and it's your wedge. It'll always be your wedge.

AI assessment note: “You'll eventually get to the latter, uh, but I think for first off”

Q is it them? Is it me? Could just be them. It could be you. It's, it's, it's a night, and then you lose time. Can I ask you on the losing time element? I've had so many founders on the show before say, speed is the most important thing in a company's success. It's the biggest determinant of whether they get product. Is that true, do you think? Or not?

A Absolutely. I mean, you know, if you think about it, right, like, you were, you were to bet on, you know, one of two horses. One horse is, like, really thoughtful, you know, is really, like, sort of planing, and they've got a whole strategy, they're, like, you know, they're gonna execute it, but they're slower. And the other horse, like, actually doesn't have the best strategy, but it learns quickly, and it just, like, keeps changing paths. Like, which one's gonna get to the destination faster? Unless the first one is perfectly right, which, Almost certainly it's not, that first horse is not going to be, I would bet on the second horse. Uh, and, and, and I think that's the mindset, you know, we have internal, like I would much rather bet on a, on a zip that, uh, you know, we all, we sometimes joke internally, but, but it's a way for us to push ourselves to get better. We sort of talk about, you know, what if, like, how do we compete with the other zip? Like in an alternate reality, there's a clone of our, like the clone of zip, uh, in the alternate reality. How would we beat that clone? And usually the answer is we do something We would just iterate faster. Uh, like, speed is actually really, really an advantage. Uh, and, and it helps you, like, you're not gonna be right, so you might as well just learn quickly and move on. The other thing is, as companies grow, they just get s…

AI assessment note: “Absolutely. I mean, you know, if you think about it”

Q you have product market fit. I just think product market fits the most bullshit thing ever because you scale to a new channel, you scale to a new audience, you scale to a new pricing level. And fuck, you don't have it again. And so I'd love to just hear your thoughts. Like, how do you think about product market fit having had it with Zip, having seen it firsthand?

A No, completely agree. Product market fit is certainly not binary. Uh, it's like, it's like a, you know, complicated matrix. Uh, and like the first cell in that matrix is like the first set of product market fit you have. But as you distribute, I mean, like you said, you know, we're talking about platforms as you add more capabilities, more products. Right. You have to go through product market fit for every subsequent product that you launch as a company. Uh, uh, and then you have to do the same thing for every persona you speak with, every channel, uh, uh, that you have, uh, every industry. I mean, it can get gloriously complicated, uh, as a vertical, right? You might, you might, you know, if you sell the retail versus you sell the financial services, I mean, just because you have market fit in tech doesn't mean you have market fit in financial services and so forth.

AI assessment note: “Product market fit is certainly not binary. Uh, it's like, it's like a, you know, complicated matrix.”

Q have incredible pull from, I'm just using this as an example, fuck it, large restaurant chains. Uh, they have a huge amount of buyers across different segments and procurements nightmare, just saying, uh, Why not have someone to go after hospitality? It can be a hundred grand a year, quite young person, your job, boof, boof, boof, hospitality. Does it need to be expensive? I'm just, I, I don't know.

A No, it's a great point. I mean, I think you can, I think you can like, I actually think that's the right approach. I think you actually bootstrap it by having like a smart, like zero to one type, maybe an ex founder, right? Like that type of person like figure out, cause what you need to figure out is what's the messaging. Like, are there any like specific systems they use that like we've never heard of, you know, like just get all that stuff working, build up the right assets and positioning just so, you know, your team is, can be successful. But then ideally you can just fold that into the rest of the organization. Uh, and maybe you have a pocket of people that are focused on it if it's very specific. Um, but, but it depends on how, like whether the horizontal messaging fundamentally lands or not. And it depends on the product. Uh, if it's not that horizontal, then you may need to verticalize sooner.

AI assessment note: “I actually think that's the right approach. I think you actually bootstrap it”

Q What does that look like? Like a weekly brain? Like, how does that look in reality?

A Oh, if we've got a problem, like, some hairy, like, complicated problem, what we'll do is try to get, not, not a very large group, right, because then it's not productive, but a good group of, like, pretty diverse, cross-functional people that are working on or touching this problem, in for an hour, and, like, at least what I found worked out is, like, alright, everybody takes 15 minutes and write all your ideas out, you know, one-on-one, And we just go around and then try to whittle that down. And then we end, end the meeting with like, you know, five ideas, maybe, maybe two of them we would have thought of anyways, but there's three, like pretty interesting ones that maybe we wouldn't have thought of. Uh, and, you know, and that's like one way.

AI assessment note: “everybody takes 15 minutes and write all your ideas out”

Q You said number one lesson was do B to B. Um, I had Trey on from Founders Fund, and he said, um, serial entrepreneurs in SaaS are like George Clooney selling tequila in the way that seriously, you have a massive opportunity with your skills and talents, and you decide to do B to B enterprise SaaS. Like, that is not serving the world. What do you say to that?

A Well, I, I would say it's, it's a little bit different than selling tequila. Uh, and I, uh, you know, I actually would say that, like, if you take what we work on at Zip and procurement, I mean, you know, there's like, there's like 11 times as much money that moves hands between businesses than moves hands between consumer and business in the global economy. So it's actually so much, so much money that moves hands. And if you can make that just a tad bit more efficient across the board, You actually create so much value, uh, in the economy that's being lost, and that ultimately, I mean, this, of course, takes so many steps, but that does carry over to consumers. But, but I hear you, I mean, it's, it's, it's like you, you lose the anecdote of, like, the person that got something that made them happy, like, you know, I mean, I guess you have that, but inside of an organization.

AI assessment note: “if you can make that just a tad bit more efficient across the board, You actually create so much value”

Q What do you know now that you wish you'd known when you started zip?

A How hard it is to actually build a world-class product in this space and how complicated it can, it can be. I mean, when, when Lou and I were at Airbnb and we at, at different points in time, we both worked on search. Okay. You go to Airbnb, how about the search experience is like, and I thought that was complicated, uh, you know, search platform and ranking and some of these things. And, and boy, was I wrong. I mean, you know, This can be gloriously complicated. I mean, some, some of our customers in the enterprise, for example, like, you know, Over a thousand types of questions that can get asked with all sorts of different logic based on the thing that it is that you're buying. And you know, 20 plus different types of risk reviews a lot. I mean, it can just be so complicated.

AI assessment note: “How hard it is to actually build a world-class product in this space”

Q Okay. So what have you changed your mind on most in the last 12 months?

A Oh gosh. I think, um, I think it's probably my, like how I manage my day to day. Uh, so there was a, there was a point early on when we, we had like a huge spreadsheet and every single person with company would just literally write out their two dues for the day in each tab in the spreadsheet. Obviously that broke up for like 10, 15 people. My current thing is I have a note card and I actually write out what I'm going to do for the day on the note card. It goes in my pocket, and I cross it out, and I throw it out, and I have a fresh one tomorrow. Uh, we'll see how long that lasts and if I need to change it, but yeah, I haven't figured out why something that works.

AI assessment note: “I think it's probably my, like how I manage my day to day.”

Q terms of sometimes you need to say no to customers. It's like sometimes big early customers can distract your product roadmap, can take you away from what you're actually meant to be doing. I find sometimes early signals can be misleading. Like you said there, the fact that IT people bought you does not mean that they're the buyers ultimately. Procurement is your home. Do you know what I mean?

A A hundred percent. A hundred percent. Um, and it's, you absolutely should, uh, if you need to, and you should not close a certain type of customer, you should fire a customer. It happened to us maybe Uh, when we were about a year old, um, we signed, or not even a year old, as a company, we signed a, uh, our customer that had hundreds of thousands of employees. Uh, and it was, you know, to be fair, it was a, a, you know, sort of a pilot-type engagement, and, you know, I realized, I mean, the company was only at 15 people or so, 12, 12 to 15 people. Very quickly at implementation, I realized, wait a minute, uh, because I would go to every implementation call at the time, We're not going to be able to make this company successful without sacrificing an extremely, extremely large percentage of growth. Uh, and it's just not the right thing for us to do as a company. Uh, and so I had a really great call with our champion there. And, and, and just, no, you're, I appreciate, I respect the fact that you're telling me that you guys can't, you know, make us successful right now. Uh, Call us, uh, when, when you're right. Uh, no, we called them later. Uh, uh, you know, you're after that, but, but that was a tough decision.

AI assessment note: “A hundred percent. Um, and it's, you absolutely should... you should fire a customer.”

Q What do you know now that you wish you'd known when you started zip?

A How hard it is to actually build a world-class product in this space and how complicated it can, it can be. I mean, when, when Lou and I were at Airbnb and we at, at different points in time, we both worked on search. Okay. You go to Airbnb, how about the search experience is like, and I thought that was complicated, uh, you know, search platform and ranking and some of these things. And, and boy, was I wrong. I mean, you know, This can be gloriously complicated. I mean, some, some of our customers in the enterprise, for example, like, you know, Over a thousand types of questions that can get asked with all sorts of different logic based on the thing that it is that you're buying. And you know, 20 plus different types of risk reviews a lot. I mean, it can just be so complicated.

AI assessment note: “How hard it is to actually build a world-class product in this space”

Q By how much in general, is it like a 25% reduction where it used to be, hey, for a hundred K contracts is now 75, or is it like a 75% reduction, generally speaking?

A So I would actually say there's extremes. I think it's like no reduction to extremely substantial reduction. I'll give you one example, uh, that, that, uh, one of our customer champions had shared with me there. Uh, this is a champion of works at maybe a 3025 hundred person company. He said for, for a handful of months, the CFO had reduced, uh, uh, their budget all the way down to 5000 dollars, uh, which is really low, right? I mean, that's really, really low, uh, because the CFO was just concerned we're spending too much money, wanted to just see everything. Um, they then later increased it because it was just, you know, uh, uh, too much throughput once they'd gotten some, some view of it.

AI assessment note: “I think it's like no reduction to extremely substantial reduction.”

Q How did you learn to explain it for founders listening today who don't feel like it's resonating, who don't feel like it hits? What lessons do you have from that six month period of exploration to your ultimate? It started to hit that you'd share with them.

A Yeah. Yeah. No, it's a great question. So what we actually did, so we were actually quite wrote in our approach here, uh, every week, Actually, initially it was every day because we had so many calls and then we were like, we don't need to review this every day. We did it every Sunday. Uh, we would write out our quote unquote investor pitch, which is like, you know, a couple of sentences of like what Zip does, but the investor view of it, you know, talking about like the market, that kind of thing. And then the customer pitch. Uh, and we would cheap at one point where we're looking at both of those in one Google doc every single day. Uh, and you'd be like, what did we learn today? Like, would we change How we frame it. Uh, and then we would test it for all the calls that we would, we would do the following day. Uh, then it got to a point where we're like, no, we don't need to change it that much. Let's review this every week. And so we basically had this process where we're constantly reviewing. Then as we started to talk to more people, we sort of morphed this and literally built an Excel, like a Google sheet and morphed it into ICP. Like we had different IC, potential ICPs as the row, uh, as each row, because we didn't know, like, are we going to sell to IT, legal, Procurement, which ended up being the case. Finance, right? Like all these people have to approve things that pe…

AI assessment note: “we would write out our quote unquote investor pitch... And then the customer pitch”

Q really brings confidence and momentum to, to especially investor bases. I do want to just hone in on like the right problem. I find a lot of founders aren't actually solving the right problem. You mentioned that actually, It was pretty early that approvals was the right entry wedge. What advice do you have for founders on how to know whether they're solving the right problem and that discovery process?

A I think it comes down to repeatability, right? Like really everything about building a company is about, in some ways it's about repeatability. It's like, okay, can you do this? Then can you do more of it? And then can you have other people do more of it? And then can you have even more people do more of it? You know, and maybe quality degrades, but it still works because there's enough fit off of the market. Uh, and so really the question would be, are you able to repeatedly use that same type of pitch and narrative to the same type of person and yield the same type of result? And if the answer is no, then that means you kind of have to figure it out in some way.

AI assessment note: “are you able to repeatedly use that same type of pitch and narrative”

Q you have product market fit. I just think product market fits the most bullshit thing ever because you scale to a new channel, you scale to a new audience, you scale to a new pricing level. And fuck, you don't have it again. And so I'd love to just hear your thoughts. Like, how do you think about product market fit having had it with Zip, having seen it firsthand?

A No, completely agree. Product market fit is certainly not binary. Uh, it's like, it's like a, you know, complicated matrix. Uh, and like the first cell in that matrix is like the first set of product market fit you have. But as you distribute, I mean, like you said, you know, we're talking about platforms as you add more capabilities, more products. Right. You have to go through product market fit for every subsequent product that you launch as a company. Uh, uh, and then you have to do the same thing for every persona you speak with, every channel, uh, uh, that you have, uh, every industry. I mean, it can get gloriously complicated, uh, as a vertical, right? You might, you might, you know, if you sell the retail versus you sell the financial services, I mean, just because you have market fit in tech doesn't mean you have market fit in financial services and so forth.

AI assessment note: “Product market fit is certainly not binary. Uh, it's like, it's like a, you know, complicated matrix.”

Q Dude, you'd be the most mythical CEO if you could actually retain speed with scale, so don't worry about that. I've never met anyone, like, 700 of the biggest CEOs. Never has anyone done that. My question to you, though, is like, as much as one possibly can, what would be your biggest advice on how to retain some form of speed with scale?

A One, it has to come from you. You have to lead by example as, as a, as a founder. Like, the founders have to lead by example. It bleeds into the rest of the company, and you have to reward that. You have to reward that, and call it out, and shout it out inside the company. Like, if somebody does something quickly, and like, they achieve some result, even if it doesn't work out, you should reward them for it, and you should make sure other people see that that happened, uh, and that they were rewarded for it. Uh, that, like, that sort of sets the DNA and the culture. Again, you know, We're just one data point. I don't know if that's quite worked here either. I'm not, maybe even I'm a biased party to ask obviously, but that's at least what we try to do.

AI assessment note: “You have to lead by example as, as a, as a founder.”

Q be fair, this is a case where you could all get pretty sufficiently well. Uh, my second question to you is, I spoke to Ali Raoghani, and he said to me to, to double click on what you just said there, which is the lessons learned from Airbnb. What were some of the lessons learned from Airbnb on, you mentioned what great looks like, so maybe that and any others?

A Oh, it was just so, uh, helpful for me to see Brian Chesky, uh, you know, CEO of Airbnb, just how the level of attention to detail, uh, when it comes to the Airbnb product, uh, I mean, I, you know, you remember, remember design reviews, uh, where to his credit, he would be able to detect that, you know, some of the spacing is off or, right? Like just, just, just on our mobile app or like, just like really, really focus on detail. And what that does is of course, do those extra, you know, I don't know, 10 pixels of white space, In, in of themselves matter? No, but they matter a ton in terms of what that says to the company and what, you know, and where the bar is for quality of the product. Um, just like speed, right? I think, I mean, Product quality design, but like all of that also, I think ultimately is a cultural thing and it comes from the founders.

AI assessment note: “helpful for me to see Brian Chesky... just how the level of attention to detail”

Q Okay. So what have you changed your mind on most in the last 12 months?

A Oh gosh. I think, um, I think it's probably my, like how I manage my day to day. Uh, so there was a, there was a point early on when we, we had like a huge spreadsheet and every single person with company would just literally write out their two dues for the day in each tab in the spreadsheet. Obviously that broke up for like 10, 15 people. My current thing is I have a note card and I actually write out what I'm going to do for the day on the note card. It goes in my pocket, and I cross it out, and I throw it out, and I have a fresh one tomorrow. Uh, we'll see how long that lasts and if I need to change it, but yeah, I haven't figured out why something that works.

AI assessment note: “I think it's probably my, like how I manage my day to day.”

Q Can I ask you, when you think about speed being the most important thing, what was a decision you made with speed that with hindsight should have taken more time and should have had more consideration or thought put into it? I asked someone the other day and they said marriage. I said, you are fucked.

A That's so funny. Actually, I'll give you a great example. Um, so my, uh, so Zip is my second company. So my first company, uh, was a company called Flight Car. Uh, TLDR, we would give you free airport parking by renting out your car to somebody else fully insured. Um, and I dropped out of college to the company, and I remember I called my friend at the time, say, hey, you know, we're both bored, like, are you down? Like, why don't we do a company? Uh, and he was like, sure. Uh, and I remember, uh, I grew up in New Jersey, uh, and so, of course, you know, New Jersey The, sort of, at the time, at least, you know, you would go to Panera Bread. Like, that's where you would go hang out. And so, you know, we were like, all right, let's go meet up at the Panera Bread tomorrow, uh, for an hour, and let's just, whatever the best idea is that we can come up with in an hour, let's just do it. Uh, and I remember that hour, this was in 2012, I think, uh, he was telling me, he was like, hey, there's this thing called Airbnb, and, you know, people are sharing their houses with each other. I'm like, really?

AI assessment note: “whatever the best idea is that we can come up with in an hour, let's just do it”

Q By how much in general, is it like a 25% reduction where it used to be, hey, for a hundred K contracts is now 75, or is it like a 75% reduction, generally speaking?

A So I would actually say there's extremes. I think it's like no reduction to extremely substantial reduction. I'll give you one example, uh, that, that, uh, one of our customer champions had shared with me there. Uh, this is a champion of works at maybe a 3025 hundred person company. He said for, for a handful of months, the CFO had reduced, uh, uh, their budget all the way down to 5000 dollars, uh, which is really low, right? I mean, that's really, really low, uh, because the CFO was just concerned we're spending too much money, wanted to just see everything. Um, they then later increased it because it was just, you know, uh, uh, too much throughput once they'd gotten some, some view of it.

AI assessment note: “I think it's like no reduction to extremely substantial reduction.”

Q Dude, you'd be the most mythical CEO if you could actually retain speed with scale, so don't worry about that. I've never met anyone, like, 700 of the biggest CEOs. Never has anyone done that. My question to you, though, is like, as much as one possibly can, what would be your biggest advice on how to retain some form of speed with scale?

A One, it has to come from you. You have to lead by example as, as a, as a founder. Like, the founders have to lead by example. It bleeds into the rest of the company, and you have to reward that. You have to reward that, and call it out, and shout it out inside the company. Like, if somebody does something quickly, and like, they achieve some result, even if it doesn't work out, you should reward them for it, and you should make sure other people see that that happened, uh, and that they were rewarded for it. Uh, that, like, that sort of sets the DNA and the culture. Again, you know, We're just one data point. I don't know if that's quite worked here either. I'm not, maybe even I'm a biased party to ask obviously, but that's at least what we try to do.

AI assessment note: “You have to lead by example as a founder... you have to reward that”

Q terms of sometimes you need to say no to customers. It's like sometimes big early customers can distract your product roadmap, can take you away from what you're actually meant to be doing. I find sometimes early signals can be misleading. Like you said there, the fact that IT people bought you does not mean that they're the buyers ultimately. Procurement is your home. Do you know what I mean?

A A hundred percent. A hundred percent. Um, and it's, you absolutely should, uh, if you need to, and you should not close a certain type of customer, you should fire a customer. It happened to us maybe Uh, when we were about a year old, um, we signed, or not even a year old, as a company, we signed a, uh, our customer that had hundreds of thousands of employees. Uh, and it was, you know, to be fair, it was a, a, you know, sort of a pilot-type engagement, and, you know, I realized, I mean, the company was only at 15 people or so, 12, 12 to 15 people. Very quickly at implementation, I realized, wait a minute, uh, because I would go to every implementation call at the time, We're not going to be able to make this company successful without sacrificing an extremely, extremely large percentage of growth. Uh, and it's just not the right thing for us to do as a company. Uh, and so I had a really great call with our champion there. And, and, and just, no, you're, I appreciate, I respect the fact that you're telling me that you guys can't, you know, make us successful right now. Uh, Call us, uh, when, when you're right. Uh, no, we called them later. Uh, uh, you know, you're after that, but, but that was a tough decision.

AI assessment note: “you should fire a customer. It happened to us maybe Uh, when we were”

Q really brings confidence and momentum to, to especially investor bases. I do want to just hone in on like the right problem. I find a lot of founders aren't actually solving the right problem. You mentioned that actually, It was pretty early that approvals was the right entry wedge. What advice do you have for founders on how to know whether they're solving the right problem and that discovery process?

A I think it comes down to repeatability, right? Like really everything about building a company is about, in some ways it's about repeatability. It's like, okay, can you do this? Then can you do more of it? And then can you have other people do more of it? And then can you have even more people do more of it? You know, and maybe quality degrades, but it still works because there's enough fit off of the market. Uh, and so really the question would be, are you able to repeatedly use that same type of pitch and narrative to the same type of person and yield the same type of result? And if the answer is no, then that means you kind of have to figure it out in some way.

AI assessment note: “are you able to repeatedly use that same type of pitch and narrative”

Q Were there any other big lessons from that business?

A I mean, so many things, man. Uh, but one was do a B to B SaaS company next. By far. Two, you know, um, I think you don't, this is something that, uh, I think I learned later at Airbnb, but like, you know, the bar of like, what really good does, what a really good product designer is like, or what a really good engineer is like. Like, you know, when you go into a cold, um, you've never worked anywhere. Like you kind of don't really know, uh, you're just feeling your way around things. And so I think understanding the hiring and the talent bar was something that, Working at Airbnb later on, uh, I think really personally helped me with, uh, which is something that I didn't have back, back then.

AI assessment note: “one was do a B to B SaaS company next”

Q have incredible pull from, I'm just using this as an example, fuck it, large restaurant chains. Uh, they have a huge amount of buyers across different segments and procurements nightmare, just saying, uh, Why not have someone to go after hospitality? It can be a hundred grand a year, quite young person, your job, boof, boof, boof, hospitality. Does it need to be expensive? I'm just, I, I don't know.

A No, it's a great point. I mean, I think you can, I think you can like, I actually think that's the right approach. I think you actually bootstrap it by having like a smart, like zero to one type, maybe an ex founder, right? Like that type of person like figure out, cause what you need to figure out is what's the messaging. Like, are there any like specific systems they use that like we've never heard of, you know, like just get all that stuff working, build up the right assets and positioning just so, you know, your team is, can be successful. But then ideally you can just fold that into the rest of the organization. Uh, and maybe you have a pocket of people that are focused on it if it's very specific. Um, but, but it depends on how, like whether the horizontal messaging fundamentally lands or not. And it depends on the product. Uh, if it's not that horizontal, then you may need to verticalize sooner.

AI assessment note: “I actually think that's the right approach. I think you actually bootstrap it”

Q of how we do shows. What obviously every guess is there an individual snowflake, uh, but shows are relatively the same in terms of structure and how that Composed. We can never lose creativity, though. Like, it's so important that our social team is so creative with each show. How do you retain creativity, where people bring fresh new ideas, and they're not just like, Rajul's set the repeatable playbook?

A I think it's a couple of things. I think one, um, and this is much easier stuff than done, frankly, uh, but it's empowering people to, like, speak up and rewarding, like, more, like, More off the wall ideas and like alternative approaches, uh, uh, right and rewarding first principles thinking. Uh, and a lot of that relies on like, what at least I found is that I would much rather invest in the person that has potential that maybe hasn't done the job before, but like has a high ceiling because that person is more likely to think through, they don't have the experience. What are they going to do? They're going to first principle the problem. Uh, and so they're just generally more likely to To have more original ideas. Uh, and so I think a lot of this is like, you can sort of culturally set this up. If you have more managers and leadership in the organization, that's actually cut from the DNA of the company and, and, you know, high potential, but maybe is it like taking a playbook from somewhere else and cutting and pasting it into your company? There's a time and place for that maybe too. So you have to balance it. But I think like, if you only do that, you don't, you don't get as much creativity out of your organization. The other thing we try to do is have a lot of brainstorms.

AI assessment note: “empowering people to, like, speak up and rewarding, like, more, like, More off the wall ideas”

Q Can I ask what have been your biggest hiring mistakes? We talked about kind of, uh, motivating teams to get back into the office. I, I think you learn so much from your mistakes. What have been your biggest hiring mistakes And how did that change your thinking on acquiring and retaining great talent?

A Yeah, I think, I think we touched on this a little bit before, but I think the number And the number one thing is like over indexing on someone that's done it before at like a similar level of scale, right? Like I think, I think for, even for a lot of investors, I think it's like people love the like press release hire or the like, Hey, oh, this person did it. You know, they took them, they did this and they took it from, you know, uh, a hundred to, to two 50 of ARR or whatever it is. And so like, we should just get them and plug them in here. And like, it would be perfect fit and like similar, you know, sales cycle or whatever. Like, I'm not saying that can't work. It totally can. But you incur a lot of risk, uh, doing that. Cause it also, I mean, every business is very different. Every situation is extremely different. Like the same playbook certainly won't work. It's just like, will the person be able to figure out how to change the playbook enough? Uh, uh, right now versus, versus, you know, maybe you bet on the person that like has proven themselves out, uh, uh, in whatever thing they're doing and have a lot of potential to just get, get one level above. Uh, but you, and you have an honest conversation about, look, Hey, You're gonna step into these, you know, bigger shoes. We're taking a bit of a risk here. So are you. And so, you tell me if you think it's not working, and…

AI assessment note: “the number one thing is like over indexing on someone that's done it before”