EP 110: How Eric Glyman (CEO, Ramp) Runs One of The Fastest Growing Startups

28:05And so I think that building applied AI and engineering teams is super important, but I think building extraordinary data teams, being thoughtful about data models, and then thinking about really tuning your business to not just get insights, but to act on them becomes more important. And so I think it might make organizational design, data structure design more important. And so I think it forces people to think about different areas in their business than maybe they may have assumed. Have you guys changed your hiring at all on the engineering side with some of this tooling that's started to come out or is it still too early to see the impact at a business level?

28:48I mean, I would say it's, I think, informed probably every area of hiring, at least in some set, right? Like, I am, you know, engineering is one, but, you know, look, I'll talk about a few others. Like, when I think about, you know, design, I think one of the things that people inside the industry got a lot of notes and excitement about is I think we were I think we were the first company to run a scaled out-of-home advertising campaign that was primarily powered by MidJourney. And you think about some of those images that were out in the force campaign. If you wanted to produce some of those single shots to get the effect, the lighting, the feel, the props, and kind of the emotion of it, I think some of those shots would have cost into the tens, thousands of dollars.

29:43you know to that would have been a multi hundred thousand dollar campaign to produce it was done over the course of a day with as much as it cost to create a seat for some of that and I think that I think it's more important to find you know people with extraordinary taste what you know can give you a sense of what is a striking image what is going to connect with people emotionally what should I produce that is interesting work but the cost of production I think of artistic and great work is probably as low as it ever been in human history. And so what I'd say has become more important in every hiring or hiring for any kind of job profile is, is this person fundamentally curious?

30:21Are they interested in how the world is changing and how it's going to change their job and how they can do more and do their job differently? I think it's more important to find craftspeople. I think that as companies get bigger, I think something that everyone feels who's been a part of these organizations is, you know, the distance between craftsperson and craftsperson, people making things, gets really large. And there's, you know, a lot of editing and things get diluted down to the point where it's very few people actually working on the actual product. There's lots of people just making the organization and the bureaucracy work.

30:56And I think that companies are going to get a lot flatter. And so finding makers, people who want to learn, who are curious, who are interested in how does something fundamentally work and how will it change your job, I think is more and more important. And so I don't think that's a unique engineering necessarily. And I guess one of the points that we were talking about before we went on that I think is an interesting one as we segue from the AI internal topic is the role of bookkeepers over the last 10 years or so. Maybe can you speak to that point and how bookkeeping has changed as an industry in the number of jobs?

31:35Oh, for sure. I mean, first, just stepping back and thinking about it. I think double entry accounting was invented, I think, in the lead up to the Renaissance in Italy. And some people say, actually, that was one of the precursors that generated a lot of wealth, which could drive to one of the greatest periods of creativity in human history. But I think the reason it exists is that humans make mistakes. You have one set of how your finances are, but when you're interacting with lots of different parties, it's hard to do it without checks and balances in how you ultimately keep your own books.

32:22And that's been the avant-garde of how record-keeping has been done. There's a lot of great things about it for 700 years, something like that. And it became very, very important call it 100 years ago, as companies started getting a lot bigger. It wasn't just regional banks. There was the creation of branch banking. You had national banks that could operate in far flung places. You had large industrials, the rise of Standard Oil, of General Motors, of Standard Chemical, these large companies. And suddenly people needed to be able to understand what was happening in these local branches. How do we have multiple sets of records between what they're reporting, audits against that.

33:11And so you needed to build not just great systems, you could scale like double entry accounting, but swaths of people in order to be able to measure, audit reports, uh, uh, and then act, uh, on this where I think it gets to your question is very interesting. I, I, I think it was an article on the wall street journal. We'll try to dig it out, but I think it was something like, um, you know, it said the stat that looked, um, wild on the face of it is said, you know, there, um, a decade ago, there was 3 million, you know, uh, bookkeepers, you know, professionally, um, or 2 million bookkeepers, especially in America.

33:45And now it's, It's a million less. And it looks like this is crisis until you realize that the number of financial advisors and analysts has gone way up, if I call it a million people. And I think it's indicative of what happens in progress. When you have better tools and systems, it becomes a system people move to more strategic or high level of abstraction is one meta point. I think the second meta point that's a little bit interesting is computers, you know, don't really make mistakes. So there's people that program that make mistakes and you can model things incorrectly, but fundamentally excellent at keeping of records.

34:31And I think in a world in which more, you know, transactions are digitized, it's easier to know with accuracy what ultimately happened. But what I would say today for the reality of someone using, I think for the average business, the regular experience is to buy one thing, you need two tools. You need a credit card and you need an expense management software and you take a digital transaction, you get an analog image of a receipt or a printout. You then take a picture, you redigitize it, you put it on some other app that then needs to determine, does this transaction match this transaction? And you port it.

35:06And so it's just very Kafka-esque. It's very clunky. you know today i think one of the original drivers of ramps product market fit was you don't need two tools to buy one thing you know you put you tap your card we check your expense policy in real time um you know you get your receipt we pull it from the merchant automatically or email or we text you when the receipts in your hand you snap a photo and you're done and so it sort of takes what used to take a month for you to get your receipt in on average on you know on these old tools to 30 seconds is the average on ramp um so it's easier process but as you look and how this is extended, today, as you know, we issue corporate cards, bill payments, reimbursements.

35:45We manage tens and tens of billions of dollars of purchases. And we stitch data from what's happening in our HRAS through what's happening in our HRIP. And where I think this all comes together is that for the average business using Ramp, they're dramatically more efficient. You don't need such large finance teams in order to be able to keep books and records, which is a good thing because it's not high value work. It's actually, I think, very painful parts of people's jobs. And instead, they're spending time on the interesting questions, which is like, where does return on investment come from?

36:15Where should companies be deploying more capital, not just doing lots of work in order to be able to measure what's happening? They're not spending time on downloading a bunch of spreadsheets and running large pivot tables to figure out, okay, this transaction is UBR star 237, UBR star 123, all these say Uber. And so after an hour, you can finally say, this is what we spent on Uber. That's done for you. How your books and records are kept are done for you. And I think that over time, there's been this white whale in, I think, investing of this. There was this idea about a decade ago, people talked to this notion of one day there will be self-driving money and companies and people will have their assets in the highest yielding security or asset at all times.

36:58They're not going to waste a dollar on things that they don't need. And they're going to have better insights on how to live a better financial life. And it didn't happen. But I think that as companies become increasingly digitized, they're connected together and you have a command and control system like Ramp. I think self-driving money is actually kind of a real thing. And in the same way, a decade ago, people were excited about self-driving cars and it's finally here and people are just getting used to it. I think that's happening in the world of finance. And whether it's us or someone, it's going to happen.

37:28And we want to be the company that does that and brings it to people. So as you guys have dogfooded, we spent a lot of time talking about the internal processes that you've made better for AI. And then we also talked about the outcome-based pricing that you've been able to align with your customers. How has that now manifested in artificial intelligence for the end customer of RAMP. And how did you, I realize it was a first principles thing from the start of the business, but maybe take me through as ChatGPT happened and there was this proliferation of LLMs or it went mainstream, how you up-leveled or thought about up-leveling the end customer experience with AI.

38:11For sure. So, I mean, a couple of things. We're always interested in the field of it simply because there have been aspects of machine learning that have dictated how risk and underwriting have worked for decades. Like it's been in production for quite a while. And so very early on, some of our first hires came from Facebook AI Research, Google Brain, like first five people at the company kind of a thing. And so even back in 2019, our receipt matching was finally, you know, driven by machine learning. By 2020, a lot of our underwriting was ML based. You can have human underwriting, but actually you could use data signals in order to inform how a company's finances may perform and how much limit we can extend.

38:57And so there's been aspects of it for a long time. What I would say is, you know, it's certainly not today, but I don't think it has been for years possible to use RAMP without using AI in some way. The difference is, historically, we haven't talked about it a whole lot. You know, you look at... You called it ML and not AI probably in the early days. Yeah, and well, even this, like, you know, we have lots of, you know, most of our businesses are traditional, like their farms, you know, restaurants, hospitals, manufacturers. And if you look at reviews of Ramp, the most common thing you will see is it's really easy.

39:35You know, it's really, really simple. And if you look deeply, it's because there's AI driven in almost every process. Like you snap a foot over your receipt and it's zero touch AI. it just matches to the right thing. You go and you buy something at Costco and you get a text from Ramp saying, we have this suggested memo one, two, and three, click one which feels right or fill on your own. People pick one, two, and three almost every time because we're better able to predict. We're better able to model and tag transactions certainly more quickly, but also for the vast majority of customers more accurately.

40:13And so it's stitched in lots of different places. And so there's a lot of work around, you know, this category of products that we think internally about zero touch AI, where you don't need to call it that. But it just feels smoother, more intuitive, there's less friction in any part of the workflow than normally you're thinking about. That's one. There's another class of more external facing products that we're really interested in that, you know, we think about is agentic AI. And when you think about that, I think probably a use case that blew up on Twitter about a month ago was, it was, you know, similarly development of Tobii that followed the release of GPT-4.

40:56OpenAI released its GPT-4 multimodal model that you could take, you know, images, video, audio, you know, text, and get the output of these large models. And the prompt was one of the top sets of questions that people will ask about RAMP is, hey, they know what they want to do. They know RAMP can do it, but they're not sure how to do the thing. So an example could be, hey, I want to issue a card that only works at coffee shops. And give it a limit of$50, but I couldn't figure out how to do that. of course, you know, number one feedback, we want to make our product more intuitive, make it more easy for people to figure that out.

41:42But we said this actually might be a great application of the GPT-4-0 model. And so, you know, after, you know, a little bit of work, I think about a week of work from, you know, Alex and others on the team did an extraordinary job. What you can do is you can say, hey, Ramp, I'd like to issue a card with a limit of$50 just for coffee. Help me do this. What happens next is very interesting. What you see on the screen is ultimately fed into this model. And so it takes this text prompt inquiry and audits what's happening on the screen as well as other screens that are possible to click through and then shows you how to do it.

42:32And, you know, it says you can click down here, you know, into the cards model, hit new card. We're going to hit controls. You're going to say allowed merchants, you know, coffee shops, it'll pick that, you know, it'll write this. And as it's doing it, it's showing you what it's doing. It's saying, I'm going to click over here. We're going to write this text in and then it's going to click issue. And I think this is really interesting because it's one of the first cases where it's as an agent, it's not just explaining how something is done. It's actually acting. It is doing things as an agent of yours, doing things in this case with you monitoring the outcomes.

43:10But it's very different than how companies' products historically have been done, where they're taking some action in the real world and it does it. Now, of course, I think the easy question is, that sounds great. Why show me the steps? Why don't you just do this? I think some of the answer is these are alpha products. We're testing it. And we want people to kind of monitor and sit shotgun and see. In the same way for Waymos before, they were driving on their own. There was someone kind of there with a steering wheel just to see what's going on. We think that's kind of a good paradigm to see how these go.

43:44But over time, you can kind of imagine, you can learn all the way a SaaS app works and all the tools and knobs and ways to configure it. Or you can say, here's what I want. Loosely, can you go, tool, configure yourself? Can you go do this thing on my behalf? And, you know, tool should be more intuitive to be able to use directly. But also, I think tools are going to act on your behalf, not just in the tool itself, but outside of it, and generally on the internet. And I think that Paribus is an interesting example where it was an app that wrote emails for you and chatted with people at other companies on your behalf?

44:24And I think those kind of use cases are really prominent. How do you get better deals on the software and sets of things that you know you're going to be buying? Can you perform certain analyses for me? And so when I would say over time is the reasoning capabilities of these models increases dramatically, I think that just even the nature of what software can do for people is going to expand dramatically. And I think having a sense and developing taste of where things are great and working as expected really quickly and where they're running any issues, I think is a really worthwhile thing. As you think about that multimodal 4.0 use case, it sounds super interesting and cool.

45:08As these things get done internally and you empower people to do them, you're thinking about the incentives or like what success looks like. And I was just taking down as you were talking, like thinking of what success looks like. And one is that people actually want to operate that way. I think that would be the most idealistic one. People actually like, it's a good functional way of doing this. And that's the most idealistic. Then there's two other ones that I've sort of, or three other ones, I guess. One is employee motivation in some ways that like you're empowering people to do cool things.

45:39And like whoever the engineer was that did that, I'm sure had a really fun time figuring this stuff out. Then there's sort of this, I don't know the right terminology for it, but some obligation in some ways that you are a company at the forefront that has the ability to do these things. And so there's some obligation that maybe you guys feel, I don't know, to continue to push the frontier of these. And then the other one is maybe the most cynical one is PR. And it shows really well and it looks really cool in doing this. As you think about those different components are all of them some factors or does someone you don't even think through these things and someone comes to you and you're like hey yeah this seems like a good idea and we should be at the forefront of continuing to push this stuff forward and so let's do it or does it not even bubble up to you and someone just goes and does it and it comes back and you're like that's cool there's a lot I want to unpack all yeah yeah yeah so I mean so first there a note just about company building.

46:47I think that there are a lot of organizations that are in the business of selling you products and saying we want to sell more of that product. We make Tide Pods and we want to sell more Tide Pods. We're a credit card company. We want to sell more credit cards. We want to have more computers on more desks, that kind of a thing. Ramp started with a very different guiding mission. The way that we all measure ourselves is how much money and how much time have we saved our customers. It's not how many cards that we sell. It's not how many bill payments that we process. It's any of that stuff. It is what is the outcome that we're trying to drive.

47:19And when we do product mode maps, I think we're relatively hazy. Like on it, we say like, this is the future state that we want to drive. If we do this, you know, finances no longer be tedious, monotonous, but strategic and insightful. But how we get there, we actually give live, leave like a lot of discretion to teams in teams themselves are quite distributed. Some of the largest teams like the spend management team at RAMP is on the order of a dozen people, which I think is very surprising for people when they know that RAMP is an 800-person organization. And so when I think you have a clear, we're trying to drive this, you're responsible for this area of the business and improving metrics on it, but how you get there is up to you.

48:04I think you inherently foster creativity. And sometimes people look to and have the permission to take new paradigm shifts. And so it's not really me mandating, hey, we want to do cool. You can always feel it when there's someone with like too much centralized control saying they're going to do this stuff like, oh, we're this AI this or we're pivoting to big data or any of these large stuff. Like, you know, we hardly talk about this stuff. We really talk about like this truism. We exist to save you time and money. Here's the products. Here's how they work. And I think it leaves the place for incredibly bright and curious and just like excited people to say like, I'm going to do this, but I'm going to radically improve the amount of time that we save, you know, and I'm going to implement AI as a tool, but it's not about like, what's the shift.

48:47It's more of what's the problems that people ultimately have and how do we go build against that? One of the things that you did touch on there that I think is, is an interesting one is, is org design. And you touched on this a little bit earlier as well, but there's this balance that exists between autonomy and empowerment of the individual and consistency and centralization of the experience. And those two things are kind of at odds with one another at times. And if you run a dictatorship, the design, the output that someone sees from a company product or design or aesthetic is probably a lot easier to keep consistent, the fonts and the colors and all that stuff, than a decentralized organization that people are making a lot of independent decisions.

49:37And there's this tension between the two that exists. And so how do you think about what are the shared services that the organization has? Hey, we're going to be an AWS shop and not a GCP shop. And that's not something we're going to let individual people make their own decisions on versus, hey, we really do want you to solve the business outcome and how you get there is on you and where the tension or the balance exists between the two? It's, I think, an amazing set of questions. And I'll maybe start, I mean, you highlighted, you know, AWS, Amazon Web Services versus GCP, Google Cloud Platform.

50:16Yeah, sure. Whatever it is. Yeah, yeah. I remember this debate when Ramp was on the order of 40 to 50 people, pretty early days. And we were trying to reason through, would we be a highly centralized, really deliberate? Because we do have a point of view. We are opinionated on products should work a certain way. They exist to save you time and money. If you tightly couple certain products, they work better for certain people. And you're a small company, you have very limited resources versus, you know, do you want to give lots of flexibility? And sometimes you'll have, you know, some wasted effort, but you don't slow people down.

50:55people have a lot of discretion. And I would say probably the most extreme examples of this are probably the organizations you highlighted. Amazon on one end and Google on the other. Where Amazon, if you use and you explore all the tools and services available on AWS, it's like a zoo. Like there's, you know, multiple versions of tools that do the same thing. competing teams where certain teams win and lose out. But, you know, for a long period, like really radical, lots of good stuff and a super thriving ecosystem. Google, I think, is very famously the kind of the opposite way where it's highly centralized decision making.

51:39You know, as products come out, they tend to use the new norms. They sort of, you know, uh turn off products all the time uh and there's these like mega organizations all working towards these one super products and you know that that's an extreme example of reasoning through which one do you want to be do you want to be google you know with like one or two super large products you're going to be amazon where it's like you know it's more of a rainforest yeah like crazy stuff going on in there it's the move fast and break things or the measure twice cut once kind dynamics. Yeah. And, um, I'll tell you like after putting it in, in those terms and really thinking through, I said, you know, like I think Amazon, um, has got to be the way, um, because when I, I think that one of the only, um, when you're a startup, like having really focused effort, high velocity, moving quickly, getting things out and learning often is the way, cause we're wrong a lot all the time.

52:33But if you can understand how customers react to it, you can improve and more accurately point the direction and vector of your product. You get a lot further in the right direction a lot faster if you take these super large bets released in multi-month to multi-year cycles. And so we said, you know what? We are at times going to have many different ways of solving the problems. It's going to create sometimes some clutter. And we think that's a good thing. And we need antibodies and internal mechanisms that are, you know, doing occasional QA in order to be able to not stop the production and the creation of new things, but to be cleaning and sort of sweeping the streets so often.

53:13And so when I think about what that means is like, you actually start to build teams that are both, you have, you know, single threaded teams, or you have people from the beginning and inception and customer research, you know, interviews of the products, to building alphas, to betas, to shipping these productions where it's the same teams, really small groups of maybe a PM, you know, you know, three to seven engineers, depending on the nature of it, maybe a designer. And then as it gets ready, then you later start to bring other people on and we have lots and lots of small teams. And so most of the organization is that.

53:45Then you also have certain horizontal orgs that you really build is how do you make sure that for any developer, I don't care what you're working on, it's easy to develop. You have standard sets of infrastructure. And if you need new tools, we're going to make sure your experience of procuring, working with, and using that is really fast. And SLAs are incredibly important. And you even review people differently. Like when you review products of how well do they do, you ask customers, you look at speed and velocity of productions, you look at outputs. When we are reviewing folks in more infrastructure type organizations and more cross-functional organizations, I actually care very little about what the manager thinks about a particular employee.

54:22I'm really interested in how the cross-functional partners that speed, they impact this ability to do their work to impact. That's probably the most important signal that you get. And so I'd even say it even goes down into like review design and thinking about performance where I would say I wouldn't just pick one. You need a nature of both, but even assessing individual performance, thinking about what are the SLAs, what are you measuring and try to optimize for becomes very important. And what I would say is that where organizations get this wrong is they oversimplify and they say, you know, everyone needs to get reviewed by their managers and all their downward reports.

54:57And that works perfectly signed for some, but it's horrible for others and becomes very bureaucratic. Or you have certain practices that are really well set up for horizontal unctions that don't deal with, you know, single threaded teams. I think that's why, like, you know, I had lots of friends who work at Google and they're like, I leave because I work on something that maybe if I'm lucky, like a year later ships. And that's fine for the horizontal people, but really tough for the vertical people who want to get things out. And so I would say no system is perfect. You know, I've heard of, you know, some organizations that reorg every 18 months, just so, you know, you have some period of time when you get the benefit of changing it.

55:34You know, I would rather not do that and be all one way or another, but sort of thinking about every individual function and how do you structure what it does, how it can operate, the goals you set against, and even later on a performance basis, is how you measure those people. So when you set it up in that way, like maybe a new product initiative or something, you're going to roll out. You guys recently announced travel. And so does that get set up as its own independent entity and with a PM and a handful of engineers and designers? And then ultimately, does it roll back into some more centralized product organization when it reaches maturity?

56:09Is that the typical life cycle of it or does it stay independent and autonomous or does it depend? It's totally right. Travel is an awesome example of this and bill payments and others. But so first, what you said is exactly right. We started with a couple of set of people, which is, hey, I think a few years ago, maybe 10 % of all car transactions on ramp were bookings of flights, hotels, autos, travel, entertainment, that kind of a thing. And we could see very quickly, this is going up and up and up. Today, about 20 % of all transactions on ramp are booking flights and hotels and all those. And there was this customer need.

56:53People were saying, look, I would like to have more control over when an employee is booking a hotel and flight. I would love if your great car controls could actually dictate maybe a booking portal. So if If people ultimately are booking, they see hotels that are in policy. They see flights that are in policy. When the receipt, you know, is the transaction is affected, the receipt is automatically pulled back, right? And so there was a clear customer need. It was building on top of additional product, all this kind of stuff. Now, we didn't go say spend management team, go build travel. What we said is we sort of took off a small team.

57:29We functionally locked them in a room for like a year. And we told the people, don't talk to them. They're just going to build travel. and interviewing customer research and figuring out what's the right form factor to build this. And it was exactly as you described. It was, I think initially, predominantly engineers. I think someone from product joined reasonably early on and it was decisions in trying to do research what were the customer problems, reasoning through the right way to build, and then working with an increasingly large set of first design partners, alpha customers, and all that.

58:01Eventually, we start seeing certain metrics get hit. We see you, you give it to a customer. They like the design and say, great, you like it so much. Would you use it? You build the thing, they have access to it. Um, they start booking with it and they don't just book once they book twice. They book three times, you know, you start to see retention go through and eventually you can start to get to this early set of product market fit, uh, type metrics where you can see this bucket is holding water. Um, customers are getting, um, you know, value off of it to the point where they don't want to use other tools.

58:32Um, and effectively you allow like a young baby child product to start to grow large enough where it's ready to go off to school, it's ready to start to join all the organizations. And so what I'd say is that that team was predominantly interested in development around, you know, travel related products. They were absolutely beneficiaries of existing products that exist, you know, DevOps making standard tooling that makes it easy to create new tools on top of ramp, a BD team that can go and negotiate deals on their behalf as we're working and evaluating different infrastructure partners, spend management, which can go and surface, you know, card data to know what's travel, what's not, a receipt automation team, an accounting automation team.

59:17And so there's, you know, they're effectively building single threaded. How do I build a great travel booking experience or a great, you know, travel insights tool, whatever it is, and sort of thinking about what's the API interaction between this cluster of services and the other ecosystem. But what I think is so important is if you put small orgs that are building new products into the large matrix right away, it's very hard to get resources. People would say, I've got this large product, give me the engineer to go work on this. And I have a large portion of the business. And things die, stillbirths all the time.

59:58And I think even Even if you look at like early history, if you look at some of the breakthrough products that like Apple ever developed, if, you know, under the Scully era, it was all kind of the large teams and they were managing to work on some new products and existing products and it was really challenging to do. And, you know, for, I think largely for better, like Steve Jobs would go and put people in a different building and say, go talk to the, don't talk to these people, let them build that. And we try to model that on it. And so I think there's a lot around product market fit. I think that once you get to a certain scale, you start, the question is not how you get a thousand people to love it, but how do you make sure this is stable, robust, and the foundation is strong for 10 ,000, 100 ,000, a million people to use and love this.

1:00:36And so the nature of things change. The goals are not product market fit. They're more operational, SLA-based. How well the service interacts with and reliable is it? And those can change when it's ready for it. And does that change often the people that are leading it? Do you start with pirates and move to Navy over time or something? The people that like getting it from zero to whatever, almost one versus the people that like rounding out uh do you find those to be different types of people internally it depends what i'd say is is often yes but like i don't know um you're like like the one piece fans out there like people want to be king of the pirates like you know eventually you go from like this little ship to running large organizations and there are some people who are that way love it understand a problem space so deeply and and actually make that evolution and there's other people who like i just want to build the new cool stuff and and you know work on that and so what i'd say is like actually like um i think it's probably like a good meta point even just about like talent like sometimes i think interviews over uh optimize on uh is someone on on skills uh and how capable is someone at building something or doing some job and like I will never fight with anybody about it.

1:01:51You should understand how well is able someone to do the job. You should assess are they a good engineer, are they a good designer? What does it do? They have functional expertise. But I think a lot of times what organizations leave out and frankly I learned, I think it was one of the positive things I learned when I was at Capital One is, you know, everyone is the hero of their own story. Understanding people's motivations, what they want to do, who they see themselves at, where they want to be in years. and not forgetting that and periodically referencing back and checking in and saying, you know, hey, you wanted to start a company one day.

1:02:29You know, the zero to one problem is really, really important. I want to put you on zero to one problems and build that and then check in. Once they get to one, do they want to go from one to 10 and how are they feeling about it? And it's not just, I think, in company and organization and building companies for the long term. Um, you know, if it's true, all the companies, this is a set of people, um, you know, uh, making sure that people are working on problems and feeling like they're progressing against areas in their own life that they want to grow against is, is I think one of the most important things that you can do.

1:02:58And I think that, uh, I think that, um, uh, so many leaders across ramp or, or just excellent at this. Like I think that, uh, Kareem, uh, Jeff, uh, Diego, there's so many people through the organizations that are really trying to understand not just functionally what they're accountable to but but thinking about okay like how are people ultimately doing how are they feeling about it and if they want to go deeper they do it but if not like putting them on types of problems that feels like moves them closer to where they want in their career is i i actually think what makes what gives organizations longevity and i encourage people to do i i want to uh move to to hiring but um and that some of the things you look at there but But before we hop, I'd be curious, as you think about resource allocation within the organization, how much of if you were to split it into 100 percent, how much effort or headcount do you think it's dedicated to like the meat and potatoes of ramp as a core product, the spend management, the card, all of that stuff versus, I guess, new product initiatives?

1:04:02and I don't know if there's a third bucket of moonshots or maybe that's the AI team that you guys have as well. But how do you sort of think about the resource split of what goes where? Yeah, we'll come back to the AI team because actually they work on a lot of optimization of existing processes. I assume it's cross-functional probably at all. Yeah, we'll go into all that. But I think a couple of things. I mean, so first, I think he's very in vogue, but some crazy kind of management recommendations. But I think something that I heard Jensen Huang at NVIDIA say, which I think was really profound, is he believes his role as CEO is to create the conditions by which people can do their lives work.

1:04:52and I think it's amazing right um when you think about the journey of that company um uh you know he describes it one is one of the important things to think through is uh you know first how do you create the conditions how do you find extraordinary people create an environment in which people want to work feel motivated all this stuff that that people um you know obsess on all right maybe this is that that whole you know you have the right talents are they in seed do you have the right culture all that There's a lot that goes into that. And, you know, by which people can do their live work, I think is an important, you know, addition that I think is easy to really glaze over.

1:05:34You know, that company for a long time was making chips for video games and for crypto mining. And multiple times he sort of gambled a company and he said, look, we could go from being like a, you know, a$5 billion company to a 10 to a 20 if we just go deeper in the video game industry. but he said, you know, I've hired people of such caliber that actually I need to be thinking about which work do I select and which do I deselect from the company. And I believe that the opportunity to build GPUs for AI or for biological research and genomic research is much more important. And so one of the important things that he assesses his own effectiveness as a CEO is, are you making sure that people aren't just doing work, but are they working on the right sets of things.

1:06:20And I think that, you know, that company and how deliberately they've taken large bets, gambled, and I think time and time again done right, I think is a testament to his ability to do that. Do you select the right work? And so I think that that's a big part of a CEO's job. I think that the other is, you know, I think we're 1 ,929 days old today. You know, it's less obvious now, but like I remember day zero when we had three people and I was 33 % of the head count. And when there's just three people, it's obvious that all the company is, is a collection of people. And so, you know, if you want to have any shot at building something great, you better find really great people, get them into the company, and then hopefully you can create the conditions for them to do great work.

1:07:05And so I think to actually back into the question you really asked, like I think you still need to spend an enormous amount of time doing it. I think I do spend about roughly a third of my time, whether it's hiring and probably a little more if you look at just trying to inspect what's happening in the business. These really smart people, are they able to produce great things? Are people getting in each other's way? And are organizations working really efficiently, I think is a very large part of it. And I think it's important because I have the power to convene meetings, I have the power to change structures in organizations, and I need to use that at times.

1:07:44And so I think there's a lot, and I have the ability to, you know, now more people are interested in responding to cold email from me than maybe a couple years ago. And, you know, I can meet from and learn from a lot of people. And so I think like, you know, some of my job too is thinking about what are the things that only I can do or maybe do more easily and make sure I'm putting my time on that. And so maybe it's finding extraordinary people, assessing structures, changing things out, and then maybe outside of this third, am I selecting some of the right work? Interesting. And so that's you at a personal level.

1:08:17Organizationally, the, I guess, existing products versus new products, how do you think about that split or that ratio? Yeah, yeah, for sure. So I think it differs based off of job function, right? In some sense, if you're a sales or account management or customer success, you are working on existing products. And that will, you know, I think understanding customers and bringing in to maybe think about where the future is going is an important part, but you are definitely living in the today. I think for things like engineering and design, product, even aspects of like product marketing, brand, you want to be thinking about, structures that exist over many years.

1:09:07And so there's some element of where's the world going and how do I make sure I position myself as best as I can for where that's headed. And so I think these organizations tend to have much larger percentages of these orgs working on the nature of those types of problems. The new stuff. On the new stuff. And so at the beginning, I would say, before a company has product market fit, it's all the new stuff. 100-0. It's 100-0, yeah. I still think today, if you look at still the majority of people-related spend is in R &D and work, and I would say the majority of that is going into whether it's new surface areas or sort of taking existing products to the next level.

1:09:50And I think that's great. And I think that's sort of been what people identify with at Rampage is constantly improving. And that is one of the value propositions is it's not just, you know, uh, maybe the, the best deal in business, the most high ROI, like it saves you time and money. It pays you to use it and it automates your accounting. But, um, I think a feature of using ramp, as you know, uh, every, um, if you're really paying attention, you see it as every day, but, um, you check back every month or so and the tool just gets better. Um, uh, and I think that, that, that is a quality of it.

1:10:21And so, um, I think there is even this essential part of our culture and what people identify about our product is like, this is a tool that gets better and self-improves. And so I think that's part of why I think that we put more effort than most at that. You touched on one of the characteristics that you hire for is curiosity. Is that one of the principal things that you want to walk out of a meeting having assessed from an individual? Is that like the canonical trait that you think of a ramp employee having? Like where does curiosity fit on the Maslow's hierarchy of, you know, whatever characteristics of a ramp employee?

1:11:03Oh, I mean, I actually think it's very high and I don't think this is restricted to who's working on new stuff, right? Like I, at the end of the day, like back to the mission, save people money and time. If you want to save them money and time. Well, every business is different and these are lots of different people. You need to understand where are people spending money? Why are they doing that? Where are they spending time? And so I would argue if you want to provide, you know, build better tools, but frankly, even offer good service, you need to be fundamentally curious, you know, about who is this person at the start of it.

1:11:36And so I'd say it's like, I actually don't think there's a single job at Ramp in which, you know, curiosity isn't a, I think a quality that we look for. So I would say it's about as close to the top of my Maslow's fear of it. How do you assess that out in an interview? Or what are the characteristics that you think, I'm sure everyone describes themselves as curious, but if you're sitting down to a conversation in a meeting, are there certain things that you look for in curious individuals? So there's different manifestations of it. maybe like a meta point just for people building companies thinking about it um and interviewing is i think sometimes people try to do too much in single interviews where you know there's someone who's trying to cover all the bases and that's like tough right um i think thinking about what is the overall like how many interviews are you putting someone through how do you make sure that every interview is very different um i think a lot of companies you know people get relatively probably similar questions across interviews.

1:12:38People aren't that coordinated. And in a great interview process, people are getting very different experiences across different interviews. Maybe with me, I'm curious, maybe I'm playing like, what's your motivation today? And I'm trying to understand kind of desires, your story, how did that meet? That might be one version of interview that I'd give. Maybe you talk with Kareem and he wants to see how you're doing under stress. And maybe he'll disagree with you about anything and see how you handle it to others is more, can you do the job? Right. And so what I'd say is somewhere in there, there needs to be someone thinking about these different traits.

1:13:08I wouldn't try to like combine everything. I would try to have very rangy interviews where everything feels different. One of them should be about curiosity. Not necessarily all would be would be first. Second, when I think about curiosity, it can come in different ways. You know, I think it can. Some of this is not just what people say, but what they've done. You know, show me what you built. Why did you build that? What was the need that you were trying to solve against? Who inspired you in order to do this? And so people kind of demonstrating curiosity in their thought process, but even if they're a builder, do they have the curiosity to use new tools, to try things out in new ways?

1:13:47For people who, let's say, are less in a builder mode, but maybe organizing resources, you'd say, tell me about a project that you feel was particularly successful. Like, why were you working on it? Um, what happened? What were you specifically responsible for, for other people? Did it work? How'd you know it worked? You know, and then you ask a follow-up question after they kind of go through all that. Most people can't kind of give all the details and maybe focus on one. The great ones, you know, you know, can, can go through every aspect of that, um, um, with a high degree of specificity. Um, but then I think where you can start to pull out curiosity of that question is great.

1:14:23Um, what would you have done differently? Um, uh, what worked beyond kind of your expectation?

1:14:31and what went wrong? How would you approach it? If you see people who they're not just thinking about it for the first time but have actively wrestled with this, even in the project they're most proud of, there was something they could have gotten better, I think is when you start to see real curiosity emerge. What I would say about I think great crafts people, artisans, people doing I think a lot of great foundational work, they're, they're never truly satisfied, um, with, um, you know, even on their best day, the best, finest work that they've produced, there's always something deeper that they could have done something better, some level of improvement.

1:15:09And so it could have been the craft of selling, could have been how they organize a product and what they built. Um, but there's many different aspects, but I think a lot of it often resembles around, um, you know, um, uh, what did they build? Why? What went well? Um, you know, I think another simple way is, you know uh uh what are you reading you know tell me your you know your three favorite books or the last three books that you read um i'm not saying books are the only medium in a way to like learn stuff but like it's you'd be surprised a number of people who don't read anything um um and um you know i think just sort of asking people just about like actual not like hobbies but like you know interest in where they've gone deep is is good the the the point on the um the everything can be better in some way and the self-flagellation or the really thinking about the optimizations it's it's such a good point and i think if you look at uh some of the best artists across any medium there's this high uh correlation with depression that exists for a lot of the artists and it's this desire i think a lot of people have to never be satisfied and to keep pushing and it It manifests itself in art and creativity in some ways that can be actually psychologically problematic for people because they look at what anyone else would have determined to be a great piece of art or a great album or whatever it is.

1:16:33Anyone else would have said it's done. And instead, they say it's not good enough and keep pushing or keep iterating or keep working and don't release it past the point that is normal in any way, shape, or form. And not to say that the best entrepreneurs need to be depressed in some way, shape, or form, but I think there's, I mean, if you look at some of the canonical examples of our time, I think Elon Musk has been pretty public about his battles with mental health. And there's this desire for perfection or incrementally improving on everything that I think some of the best employees have, hopefully not to the extent of mental health crises.

1:17:13But yeah, it's an interesting point. I mean, I think it's real. I think that if you want to produce great work, create things that are really timeless, like that's a very, you know, so few people are really, you know, beyond, you know, sets of friends and family and people around them are really remembered. And I think to, you know, build or create or work on anything that actually is transcendent moves, you know the you know um society's human race people forward in some way i think that that bar is so high um um and i can understand you know for someone who wants to have that kind of an impact um and that kind of desire and it's so hard to know will this work be timeless will it actually be for like i can see why um uh you know depression can be a really natural thing and And what I would say is like, I think it's both true that dissatisfaction is, I actually, like, I think there's something both deeply unhealthy about it, as you point out, where, you know, one way of looking at this, you know, as good as you've done, it always could be better.

1:18:22And so, you know, ergo, you know, you should always feel a little bit bad about yourself. And I think that's real. And I think that you're right. I think there's very few entrepreneurs who, you know, I think people usually say like, you know, you're pretty smiley and chipper guy. And like I am, but like, I think like, uh, yeah, there are moments where like, you know, I think you can't help but feel this stuff. Um, I think that the other, um, way to think about it is how profoundly disappointing would it be though, if you truly made the best version that could ever be done in the history of the world of any particular thing, and there was no surpassing it and that was it and there was nothing beyond it um uh and in some sense i think that would be more depressing yeah um and um more profoundly sad and and like and i and i think there's this broader set of points i mean maybe even to circle back to how people think about um you know various all like i'm not a futurist i i don't know um you know how things are certainly going to play out and i you know i'm more interested in how do you help businesses be better today how do you help people with better lives today and that excites me but like there's there's one version of the ai world in which ai gets so good um there's no job that humans can do better um uh and would people um you know live in some utopia where actually you can just hang out and never work and like you know to me that that feels very profoundly depressing um uh because i actually think um you know for me part of um i think we're we're joy and satisfaction and part of what makes life interesting comes from uh is the ability to uh work um and produce something um for other people it's to improve your skills it's that constant kind of pursuit um it's yes i i've got gotten um better and maybe produce something at a new height, but like, uh, there's still further to go.

1:20:18Um, and I still want to keep climbing and I still want to develop better taste and I still want to put out better products. And so, um, part of me thinks that even as tools and capabilities get better, uh, I think that's part of what actually, what makes this deeply human. Um, uh, it's the, um, it's the act of creation. It's the, you know, delivery of service. It's being there and tending to other people. And And so I don't think those ever, ever go away. But, you know, I would say for anyone who's like stuck in the rut and is, you know, worried if things are ever better, like I think that's that sort of line of thought has certainly been helpful, helpful to me and some others that I know.

1:20:55It's such a profound point. And I think it's, I think it's fascinating that there's no hill you'll climb. At least I've yet to find it. And I've talked, I've sat here. I think this will be 110 episodes or something. And I sat with some of the people that I think have built technology in different ways. And I think one of the unifying themes throughout is there is no point in the journey that you're aiming towards that you reach some fulfillment that is like the canonical achievement. and the second you get to the top of one hill, you realize there's another hill to climb or the beauty and the enjoyment truly comes from loving the process and there's always going to be someone that built a bigger company or there's a new room to be a part of.

1:21:53And I remember I always just, I wanted to be a general partner at a venture firm whenever I figured out what venture was, 23, 24 years old. I got there. You got there, yeah. I looked around and I was like, well, I'm here. Now what do I do? It's a funny thing that there's this nostalgia I have still for the process of getting to that climb. Now there's new hills that I found to climb, but the achievement in and of itself wasn't the filling. It was actually the journey along the way that was the true enjoyment. I'm sure you feel that with your company, each incremental fundraise or an IPO when that day comes.

1:22:40It'll be a nice checkpoint of celebration, but the actual inputs in the process is where the true enjoyment comes from. And if you don't like that, then you're not going to find fulfillment, I don't think, at some end state. I think that's really profound, and I think that's really true. it's uh uh i think it's both a i i think it's like an amazing like divine blessing of like this hedonic adaptation like you know you finally get what you want and you know there's in some ways maybe no better feeling and then um well you know it's a few days later you know what's next um it's insatiable yeah um and i think it's both um uh in some ways it can be like really sad and deeply depressive but also i i think it's like one of the uh one of the great things you know it's a pursuit to do more and i think that's a good uh lesson or takeaway for anyone in any job that like if you're not enjoying the inputs and i know you guys focus more on inputs than outputs as a company if you're not enjoying that then that might mean you're in the long line of work or you you have the long the wrong perspective uh of what you're doing in some way shape or form and that might be a call to action to go do something else because there's not some end state that I found anyone that's particularly motivated gets to that they're like okay now I've made it I can hang out or I feel totally fulfilled from this journey along the way yeah for sure um it's uh and it's interesting too I mean I think um I don't know I it's been fun learning from lots of other entrepreneurs but like i think one of the um you know to me kind of movies and documentaries that i like learned quite a bit from and has informed just like even how we build it at ramp but um you know i think about like you know careers and in some ways like i wouldn't go so so deep but like i think it's just worth worth an hour of people's time like i've uh i don't know if we ever talked to this have you ever watched jiro dreams of sushi no um jiro jiro j-i-r-o and I think it came out a decade, a decade and a half ago and it's about

1:24:59his name is Jiro Ono I think he was the first sushi chef in the world to get three Michelin stars and he started this restaurant that's in the basement of a subway station and it's a documentary about him, you know, in the years of what his life was about. And it's very fascinating. I think at the time he was in his eighties and still working extremely hard. What year was this? I want to say this is 2010, 2011. It was contemporaneous. It wasn't, I mean, it looked back, but it was. It was about him. Yeah. It was about him and his process and, you know, running the restaurant and it's not long, it's an hour, 15 minutes.

1:25:45And by the way, he's still working. I think he's in his late nineties now. And he is still, I mean, every night or most nights of the week, still showing up to work and trying to make things better. And it's an amazing documentary. It's worth watching the whole thing. But there's this kind of amazing scene I find with like a lot of lessons for building startups and frankly, working at anything, any kind of craft. And the narrator basically asks him this question, something to the effect of, you know, what does it take to make great sushi, you know, and to make great food? And he answers this in sort of this odd, but actually really obvious way.

1:26:32He says, well, you know, to make great food, you need to eat well. you need to eat and enjoy great fish you know and if you don't develop great taste and your sense of taste is lower than that of a customer then how are you going to impress them and then he goes on and he talks about like is the guy he buys rice from and he's like oh Hiromichi or whatever the guy's name is you know I only buy rice from him he knows more about rice than anyone on the planet it you know and he's going on and moves into this scene and and you know one i think it's like this question of and he's great for crafts people like if you don't actually like use the product enjoy understand the problems better like how are you going to make something that deeply solves something in a new way and i think that most people who like market products build products you know talk don't really talk to customers nearly enough and they should do that more but i think that the other thing you know along the way you know is they talk about um what he's trying to do and he said And he basically says he's been making sushi since he was like 11 years old, something like that.

1:27:36And so, you know, now almost 90 years of every day showing up to do the same thing. And he talks about he's still trying to climb this mountain. And, you know, as high as you go, you're still never going to quite reach the peak. But, you know, it's the pursuit of getting closer. And it's there. And I think it was one of those things. It was filmed in this interesting way where people were interested not just in the quality of what was coming out, but who are these people that are developing it. And I think it's great, but I think, you know, sometimes people looked at him as he's such a stern, impressive guy, but like, I think he's, I think there's a joy to what he's doing and you can see it clearly too.

1:28:11Well, and it's, to hear, and this sort of ties back to hiring people into an organization and on this curiosity point, to hear you talk about the history of double entry accounting, or we did a blog post on the history of dive rank and the implications that came for that, for the fintech industry. uh you can find graft or curiosity in literally anything like i double entry accounting uh might be one of the most arcane mundane topics i think out there but like there's a level of curiosity in in your craft and what you do that allows you to go back and actually learn about the derivative impacts of all of that and i guess uh i've i i don't think i grew up i certainly wasn't like uh uh genetically wired to be fascinated by the venture industry and technology like i don't think i even knew venture was a thing until i was 23 24 but like i've enjoyed learning about the history and all the different people and the players and uh you know how all these things came to be and so it really can be anything it's it's really just finding leaning into and enjoying that and i found that when you interview and i'm sure you've seen the same thing the people that can just go so deep in these things and talk about them forever are the people that persist within highly functioning organizations and they take such a pride in the part of the iceberg that never actually gets seen and if you peel it back a little bit then they can keep going deeper and deeper but you know to your earlier point about like the simplicity of ramp there's a lot of underlying infrastructure that exists to expose something very simple at the from a functional standpoint for the end customer and it's totally right like i um i think one articulation of like really the fundamental problem that startups are going up against that i love was i think justin khan um one co-founder of twitch and um partner at y combinator years ago he basically said, you know, startups biggest battle is people not giving a shit.

1:30:20And he's totally right, right? Like when you think about kind of like your own life, like you get a lot of stresses, it's like want to generate like returns, you know, you have stuff going on in personal life, you're trying to get better, you're trying to find the next deal, there's all kind of stuff going on in some random product marketing deal is like not high on your list of priorities, right? And so you need to be both simple, interesting, direct, and compelling enough that in a period of about five seconds, you know, I can somehow crack into like it is worth some remnant of your time to maybe look deeper into.

1:30:51And so I think it's both deeply important to remember that, you know, in the creation and sales marketing of different products, you want to be very simple, very compelling, very clear. And I think for most people, RIMP is and it feels like, and, you know, I think this is this is fair to say, like it's easy, it's intuitive, you know, and it's a, you know, spend management software that helps your business run better. It saves you time and money. And for most people, that's all you, I think you need to think about. You don't need to think about how it works. You should just know that if you put this in your organization, it's true.

1:31:25You can expect that if you're like the average company, your company will spend 5 % less. We work hard at that and we're going to go and do that. Now, in order to create this simple product that's easy to understand, easy to consume, you need a deep amount of interest in what causes companies to spend time, what causes them to spend money. When money moves, how does it move? When it's accounted, how is it accounting for? What is the history of accounting? Why are things done that way? Is it obvious that things should be built this way and should we be building a car, not a faster horse. And so I think for the practitioner, there's no way if you want to build something better, you have to go deep and you have to do this.

1:32:06And so I think it's both keeping in one's mind. You want to be able to articulate and craft and share this very simple version of the story, but both in how you build and also how you motivate people who are working to want to go so deep that you can find ways to, you know, to use the kind of, I think Elon Muskism, right? Like, you know, the best part is no part. Instead of building something with 20 parts, can you build it down to two, to one, to, you know, that's it and keep it really simple. And if you don't really understand the function of why certain parts are there or were built in this way, how are you going to reduce it?

1:32:48And so I think that's part of the fun of building companies. You got to think about both. Well, Eric, thanks for doing this. Leave it here. That was very fun. We'll need to do round three at some point soon. Thanks a lot, Logan. I appreciate your friendship and investing in supporting companies since the early days. And I hope this was interesting to listen to. Listen, I enjoyed it. I don't know if it's, I think people will like it. So thank you. Yeah, thanks. Thank you for joining this episode of the Logan Bartlett Show with co-founder and CEO of Ramp Eric Kleinman. If you enjoyed this episode, we really appreciate it if you subscribe and on whatever platform you're listening to us on as well as share it with anyone else you think might find it interesting.

1:33:29We'll see you back here soon on the next episode of The Logan Barrett Show. Have a good weekend, everyone.

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