#276 John Willett: Rogo’s COO on Princeton, Being Ignored for Years to Winning the World’s Biggest Banks

Hi, I'm Vittit, the founder and host of this podcast, The High Flies. Hey, I'm John Willard. I'm the co-founder of Rogo. John, I'm so excited to do this. It was so funny in my research. I had two perspectives on you. Some people said you are very reserved and you don't talk. And some people said he doesn't shut up. He sings everywhere he goes. So I'm hoping you can tell us which John is real. I can pretty thoroughly debunk the quiet one. You'll see that it's not the dominant personality trait. It was so funny. I love that mix that came up in the research. Hey friends, welcome back or welcome to The High Flies Podcast, where we do re-imagine a high-flyer showcase the brightest and most relatable role models and companies and their journey from sunrise to today. As one of the premier products in our curiosity center, we line up providing on-demand intelligence to help you be one person better every single day. Homie host, Vittitagol, and let's have some fun. Our listeners have called this podcast as a meticulously researched biography unveiling the extraordinary lives and decisions of the most remarkable individuals and companies from around the world. We hope you're enjoying our catalogue of 200+ episodes. Since we launched in 2020, with many of our guests appearing in rare public interviews, it's now time to explore your curiosity. Please enjoy. Let's set some context with the fun facts where we born and where do you live now. Sure. Born in a town called Coventry, Connecticut and Eastern CT, sort of like an hour and a half from Boston. This is the closest city, live in London now, opening our European office. Yeah, and work? What was your first job and what do you do now? First job was I was an SAT tutor when I was like an 11th grade or 12th grade, and then now European and APAC expansion for rogo. And why don't you give us a quick overview of rogo for someone who might not have heard of it? Sure, yeah. We are an AI partner for large global banks and institutional financial firms. You can kind of think of like Harvey or LaGora, but much more tailored to finance. And with a bit probably more of an emphasis on kind of the change management, like we have a big team of four deployed bankers who come in and help build out the custom agents and workflows and actually teach people how to use the product, etc. So we started the company about five years ago. Out of New York, since then we've grown quite a bit, very lucky to be working with a lot of the top banks globally. Yeah. Any investors, I know most of the investors, and I was joking to the other day, it's like the Avengers. You've got all the two investors. Yeah, it's kind of like the like, it seems like it would be sort of this like cigar, smoke-filled backroom just with all these guys across, you know, yes, Sequoia and Thrive and Pliner and Kozla, but it actually it's a very kind of like team group. And we're more together. It's a very tactical squad. But yeah, no, they're awesome. I mean, it took us like two, two and a half years between our precede and raising kind of our first more institutional capital from Keith. So that was kind of a long-ish product market fit journey. But yeah, since then we've been lucky to put together a pretty insane board. Totally. And I want to talk about that in a moment. And John, as you know, the purpose of this show is to reimagine the concept of a high-fly to go beyond people's shop titles. Is there a person you know who you feel hasn't got the recognition they deserve? Mmm. I mean, hopefully I give her a lot of recognition internally, but maybe externally. Allianna Virgi is a woman on my team who started with us about two years ago. Ex-Goldman and Sixth Street did a lot of work with a lot of our early clients. And then she actually moved over here to London with me and this helped build up the office. And she's a 15 out of 10. She's awesome. She must be killing it if you've called her out. Like she must be absolutely smashing. Yeah, she's the best. She's awesome. She's my rock here. Back to the episode in a moment. Something I've heard a lot from business owners and leaders is that speed only matters if you still feel confident in the output. And it's particularly an important point in this world of AI. Zero's answer to that is accountable intelligence. AI that shows you what it's doing and works from your own real data and is designed to keep you in control before anything happens. Has zero puts it? Most AI, I see to trust it. Accountable intelligence shows you why you can. And that's how it works with Jax. Zero's in-platform AI finance partner. So whether you're running the business, advising the client, or working with your board, Jax ensures that you get the upside of automation without giving up any of the control. If you want to see this practice, head over to zero.com/highflyers for 90% off your plan for the first six months. Terms apply and go to the website. That zero xeiro.com/highflyers. Now back to the episode. That's great. That's so cool. All right, let's wind back the clock and go to your Sunrise as I call it. You childed it in and I think this is particularly interesting because you've not, I mean, you've actually not done, is this your first interview? I think you've done one more like mini interview. I think this is my first podcast. Yeah, yeah, yeah. Okay, so we'll see how far we can get into this because I think people are curious about it. Yeah, yeah. It's uncharted territory. Yeah, yeah, which is great, which is, which is great. So you mentioned growing up. Tell me, what are your memories? What are your memories of the environment and family? Yeah, I mean, I had a great childhood, two great parents, two older siblings. Coventry is, it's a great town. It's one of these like, I don't know if you've ever spent time in kind of New England and like the Tri-State area. It's like half of it is like this very sort of like urban suburban affluent, like hedge fund manager type five and then the other half is like weirdly rural and kind of like agrarian and like all these towns and like eastern Connecticut, central mass, upstate New York, that like that was kind of my vibe growing up. And you were telling media that you come from a family of engineers? Tell me about it. Yeah, that's right. Yeah, I mean, my, my, my family was very like kind of well educated. And my dad is a, or was a professor at the local state college Yukon of computer and electrical engineering. My sister has her PhD in chemical engineering from Columbia. My brother's an engineer at an army base in Alabama. So I was kind of a little black sheep to not like directly be an engineer, even though I literally minored in engineering, machine learning and computer science. There definitely was a bit of like my dad impressed upon me from an early age that like the way to make money is to go to finance because he had, and he didn't know much about that world, but all of his friends from university who were with him in like electrical engineering, half of them became like academics and you know didn't make all that much money. And then the other half went to go work at like Citadel and made you know a ton of money. And it's over an early age. He was like, John, if you're really smart, you won't do engineering and you'll do something. Much more lucrative, which like looking back is a pretty hilarious perspective to have, but that was kind of what I was brought up with. When I spoke to Gabe, who's your co-founder for like the other day, he said to me at Princeton, you would finish three hour exams in 30 minutes. I don't know if he was joking. Like, is that true? That's a funny, that's an interesting perspective on it. No, I mean, I may be very, I would have to be very confident in it because there were two kind of competing forces. One is like my, I was good at school, like almost everyone at Princeton. So that was one force. And then the other force is my sort of like Irish Catholic upbringing, which causes me to constantly be paranoid and the kind of second guess and things are going to go wrong. And so like, I feel like just as often as that would happen, I would, you know, maybe finish it in 20 minutes and then spend two hours and 40 minutes like reading over every single answer to make sure it's right. And I probably have that conflicting jackal hide personality at rogo at times as well. I mean, exactly what he actually said is he said, John is one of the highest IQ people have met and a standard deviation above people have met. He was always that way. Did he say always that boy? He literally gave me that, we had a call and he gave me that line and he said, you can quote me. And that was the exact line he said. That's so funny. And curious like to that foam, like clearly he's a big fan of few, which is great. I think he's being very generous and very kind. He gave it extremely smart die. Yeah, I mean, Nami, again, grown up. I was a huge nerd. I mean, so I like, but I wasn't publicly so like, I always, I didn't really like like get about myself, I would say like I literally, I remember in, I think it was sixth grade or something. So I was like 12 years old, 11, 12 years old. I mean, how do that shape your aspirations when you would just about finish high school? So if I met you at age 18, what would I have assumed you do with your life? I think it like this generic sort of like business or finance, like I was so, maybe I was book smart, but I was not good at the kind of extra mile, like getting to know the career paths ahead of me or like networking or, you know, really knowing the topography of these different areas within finance. So I'm probably generic would have been like, yeah, I'll be like a CFO or maybe a CEO of some company and having zero idea what that meant, zero concept of like the path towards that zero concept of like what industry that would be. So like generically, I was like, okay, economics is probably a reasonable first step towards towards that. So that was kind of the random walk that I was on at that time. And it sounds like engineering was not a family influence. No, I mean, I took my first coding class, I only took sophomore, my second year of university at the right at the end. I was late to the game and I quickly realized I'm like, I'd prefer this by a lot to economics and wish that I had done it the whole time. I know you met Gabe at Princeton. Was that pretty early on? Like maybe tell us the story of how you met him at Princeton? Yeah, I mean, we, Princeton is not that big. So we definitely knew each other a bit just from the first few months. We started getting closer kind of maybe halfway through, halfway through college. And it was just a bit like I mean, Gabe's also a big nerd. And so we would just take some of these random like linear algebra or like stochastic systems classes together. And I And I feel like, of the people who were. Going out of getting drunk on a Tuesday, like a fat group, which is not a big group at Princeton gave it I were like the nerdiest of that group and so he sort of like naturally became close through that Do you remember your first impressions like I told you how Gabe described you when I spoke to him the other day? How would you describe Gabe when he first met him so confident like so much just sense of presence sense of self Superfony. I mean out the gate just like hilarious But not like warm and fuzzy. He was a little bit intimidating when I first met him But I was just yeah super smart and sharp and hilarious So how did you break in how did you go from that to becoming friends and then starting companies, right? I think it was classes that we took together and blanking on what the first couple ones were and then yeah We ended up in and some of the same kind of like social clubs within Princeton and then I mean the company thing We did a little bit of independent research together when we were seniors in college more really the story there was So Gabe had taken some natural language processing Classes and we started kind of chatting about it or you know junior years and I had just finished my like junior paper for Economics and one thing we just kept talking about is there are all these people in the economics department at Princeton who like are smart But they're not technical or they're not they don't know how to program and the weird thing about these Independent research projects was that you might spend like two weeks coming up with like a topic like okay I'm gonna do like an instrumental variable study on this and this and then like this is a bit of like collected the data And then a lot of it is just literally like writing the barcode or the Python code to like cleanly do the Analysis clean the data and do the outputs and so it felt like 80% of the work that went into these Financial or economic studies were things that the people weren't good at like they hated it They like figuring it out from scratch and anytime you see something like that it just sticks out right like this is a weird dislocation of Resources so we started looking at I mean LLMs were around but they weren't like that good And there wasn't like an API you could like ping to get like a good you know LLM response And so a lot of it was kind of these more an agronistic grammar-based approaches and if we were pretty impressed with a Rule set that's not so crazy you could take pretty open-ended strings of tax and convert that into more like deterministic like code run So that was basically the the insight which wasn't like a novel insight by any stretch of the imagination that we were really interested in it So kind of the idea that we set for the next year is like, okay What if we can like build kind of a product that allows you to as an economic student just kind of describe what you want Say, hey, here's this big clunky data sack and you remove the outliers and get rid of parts of the data that clearly are mislabeled like those sorts of things like do the cleaning do some of the exploratory analysis and then do the outputs Just describe that and then the system could sort of piece together like a Python script to do that analysis again Like this is all stuff that within a day of gbd3 coming out would have looked so horrible like did not work that well But for the time felt like it was gonna be helpful So we spent a lot of time building that our senior year and then actually after our senior year We had a few months before we started our like investment banking jobs and we did talk a little bit about should we try Like commercializing this was it called roger. This was no this was before so with the original products We called Athena, which is just like the most cliche possible like technology name like every single product is called Athena So from the jump there was no way from a legal or branding perspective that that was that that was gonna work at the time Yeah, it was that how different was that to the first Vroga product that you eventually went with quite different quite different because the first one didn't incorporate LLMs at all It was all like uploaded data and it was all like it was more structured data It was kind of like oh like I have these CSVs or like there's this like data set I'm integrating with and you would do basically just like structured analysis on top of that Whereas the first kind of versions of rogo we're actually much more like we're plugged into all the like market data and like Company fundamentals and company financials and you can ask a question and it would basically just pull those public Pieces of information this was still like fax at and as to be global and else like still we're not picking up the phone So it was all these like random like data bento like these are random third-party market data providers that no one Investment banking would ever use or trust but it was sort of more of a proof of concept and then the first product was also like a Command line interface so it left a lot to be desired in terms of UI UX to say the least it's interesting because when people think of roger today in August 2026 people think of gen AI right yeah back then in 2019 like you said it was pre-chat GPT going mainstream and it was pre AI Disrupting software in general yeah, so I'm curious now with the benefit of hindsight when you reflect on that moment in 2019 I guess what did you know and like what did you maybe misunderstand the latter category is much more than than the former I mean we like we had like vaguely an idea that this stuff was cool like that I think that's probably the extent of our knowledge. There was maybe also a vague sense of like this stuff is both cool and Getting better and there was some concept of like Moore's Law. It was all very vague We were like, okay, maybe this stuff will get better had no idea of the timelines or where things were gonna end up and to give you a sense It's like we started our banking jobs. We did kind of some quickly. We were like, you know what? We do think this stuff could be applicable to our like front-off as banking jobs I'm spending my entire day pulling data from faxad and then from capiq pitch book crunch base Dow Jones all these different data sources And so it felt like some of what we had built could apply But we had basically no urgency whatsoever to start the company like we were like, oh maybe we'll do you know in five to ten years We'll pool some capital and bootstrap this or start working on it at some point Which I think is a pretty good indication like if we were smarter and really knew where the research was and and knew where things were going We obviously would have just quit our jobs and started the company immediately. The reason we ended up doing that was our first investor Is this guy Kevin Ryan who founded? Yeah, MongoDB and this insider and is it kind of one of the best release stage investors Certainly in New York and he recognized it I think a little bit before us and and we were talking about what we were doing We were like hey, maybe we'll apply to like why combinator at some point. He was like no, don't I'll just give you two million dollars. You should quit your jobs now and start the company This thing's going to move a lot faster than you think so that made it a lot a lot easier and he Can you connect those can you connect those dots because by then you had already graduated from Princeton, right? Yeah, yeah, so this was like a year's half into investment banking or something like that I see you were doing this on the like weekends and nights. Yeah, basically we're doing a little bit of time I mean, so like at this point not that much of it was like actual company building like we were working like 80 90 hour weeks And banking so there was very little like product or like selling like we were maybe like Doing small user interviews and stuff but very little it was much more by the end like kind of figuring out like Defining division for what we wanted to build and actually putting together like a pitch deck Which seemed like a very important exercise at the time to have a really long and comprehensive Such an investment banking style pitch deck. I'm just like so detailed about all of our all of our thoughts I was gonna say exactly that when I spoke to your investors They said that's the difference in like your board decks can fit other portfolio companies Is that both of you worked in eye banking? So your like decks are like Very like eye banking style. Oh, that's so because I would have thought that like now we've gotten away from that So if they still think that you guys should see this first one. It was horrific It was also was something like some founders write memos right was I think you guys still do decks Yeah, we we've experimented. I think our series A was a memo. We've experimented with both I don't say I do like the memo but the first deck was so funny about it This is more of an aside, but we were looking at it like a couple months ago It's like we were I don't think either of us had ever like seed of fundraising deck before as it was all like from first principles Like zero clue of like how it should look and we had like our like next 24 months plan and like typically when you look at a founder deck It's like in three months. We're gonna be at like a hundred million of error and then we're gonna like take over Then we're gonna start in Europe and they like and just like this world domination plan. That's like very grandiose We were like so insecure and just so we're like yeah, this probably won't work So like first six months like ideation and then like hire an engineer and then like 12 months later like launch our first product It was literally like by the end of two years. We projected like a hundred gay of ARR or something like that Which like hilariously ended up being accurate, but just because we were so not confident. It's actually it's so funny We'll have to at some point if we IPO will release that deck alongside it and it'll give everyone a good laugh You can do it now like you've got enough runs on the board to share that now like yeah, maybe maybe you're right now Yeah, you're right. We shouldn't I mean, but tell me on the Kevin Ryan point because like he said he built MongoDB I mean he's also done business insider, I think and a bunch of the stuff So clearly he could say he understood software right and he's yeah understands it What did he see in both of you and your I guess your MVP? Yeah, while a product in 2019 that gave him confidence to give you two million I think Kevin probably recognized a bit about I'm sure he'd followed what was happening at open AI and and Google And I'd probably had some pre-existing thesis on a language models the where things were moving and I'm sure that existed somewhere in his brain And then he just loves first time founders That's a big thing with him like he like he loves a young talent and like giving them money and letting them and letting them kind of run wild And up was I don't know if I fully share that thesis, but it worked out incredibly well for us and Kevin's rationale for that My understanding is you know, he was the CEO of double click which was one of the early kind of internet ads companies sold to Google And he ran it incredibly well and he's I do like if double click was like my third company I would not have been nearly as good because I wouldn't have been his paranoia I wouldn't have been up all night thinking about it. I wouldn't have been just kind of as much of a freak about it as I was So he likes the kind of first time founder like no points on the board like leaving nothing to chance Which like to be fair definitely is our person So I see that so I think for him it was probably more the calculus of like interesting Market backdrop of language models first time founders I like them and these guys pass some bar there of drive and whatever and then probably the bare bones like Okay, they worked in banking. They're gonna start something to attack banking. That's often a pretty successful or interesting idea So if I to guess those are kind of the three legs of the stool Well, I mean I was gonna ask like maybe you can't ask there's like what were the terms because his two million will be worth quite a bit now Right. Yeah, I mean, maybe I won't comment specifically on the Devaluation stuff, but yeah, I mean, you know, it's definitely been a successful investment for Kevin and he's Originally he wasn't on the board. It was one of his kind of lieutenant's and now he is on the board He's awesome. He's he's one of our biggest kind of supporters and he's been a great champion for us So you you've alluded a few times so like the early years being really tough I think the line Gabe said to me the other days the first two years are pretty dinky Yeah, he sees were like not interested in you at all till he came along. Yeah, take me inside that because now that seems like a Perfect story, right? Like the dots connect in hindsight and what a rich rags to richer story Yeah, yeah, yeah, we're here like what was it in those two years that I guess gave you both confidence to keep going Oh, that's a great question very little in terms of concrete data points like there was especially the first like year and a half Like there was like essentially no external information whatsoever that would like support the idea that we should be running a company Like like no interest from clients. So that was the that was kind of the the status at the time What kept us going? I mean maybe maybe you know back to Kevin's point There is a first-time founder like kind of a genesis of just like oh, this is kind of cool Like it's kind of fun like even like meeting Kevin. I was like I never really met a billionaire before and that's pretty Pretty fun and then like you know, I remember there were times where you know would go meet with like Blair Efron from Center view and it's like you know if you grow up or you know if you're a young investment banker like Blair Efron And it's like basically a celebrity and so there are all these there are all these moments that at the time being like 23 24 25 Having come from you know the first couple years of our career and banking where like my MDs wouldn't even really like talk to me Like there was no connectivity to like or senior people or or more successful people And so there were enough sort of just moments of that we're interesting and kind of fun I think to to keep us going and and there was a feeling like hey, we're learning a lot like let's let's just keep learning a lot I think going back it would be really hard to do that again But at the time it kind of just felt like I mean I won't pretend there weren't like very dark days But I think what kept us going was just a bit of a sense of like curiosity and and fun and in the small stuff of starting and running a company So I mean the obvious question is when did it start to click because also at this point there's two years Did you quit your job? Yeah, we quit our jobs So you took the two million and you were full-time on real full-time yeah, we were full-time because you know We could be ourselves salary and stuff so right of course all that all that felt you know relatively low Risk, which is really lucky. So yeah, we quit our jobs. We were fully doing it chat GBT coming out November 2022 is probably the single biggest Moment where previously I mean our if you look at our pitch decks to like sales pitch decks from before that We wouldn't even mention AI because it was not a good marketing term it like was distracting People associated AI with like predictive machine learning and like big data was like Oh, you're gonna help us do portfolio analysis It was just did not really like jive with like we were trying to build like front office workflow automation software And like linking that with AI made no sense and there was also just a lot of there a lot of skeletons in the closet and investment banking in terms of Previous I don't want to call any companies out by name But like previous companies that had purported to do like PowerPoint automation in the pre LLM era And I had access to like five of these when I was at Barclays and they never got used because they weren't good enough And so there was a lot of that kind of mental block to to get over Well when chat UVT came out everyone kind of had that aha moment And it still took us another year to like really commercialize Partly because we have to get through like info sack and governance and all these things But we could at least start to talk to guys like Blair and talk to guys like Peter or Zach from Lazard and get to know them and And start to ingratiate ourselves as people who are like really focused on this space and thinking thoughtfully about it And erase some money and are building in it and really kind of pitching ourselves Tell me if you if you had let's as you might work to one of those companies back then Lazardo or JP Morgan or what have you What was the initial opportunity because again, you mentioned at the start about like Ligora and Havya I know both Ligora and Havya really well. They've both been on the show They said like AI changed how enterprise started looking at software, right? I feel I see that every day like across the stack like healthcare, government, accounting firms, law firms, banks Into your point like the chat GPT is made a mainstream where they all seem very Troy software where I don't think they have that desire pre chat GPT in the same extent But I'm curious what was that initial Pitch or that initial opportunity that you were presenting to them and like yeah Maybe you can tell us about the QLE customers and how you got them on board Yeah 100% I mean like the first real customer was was Lazardo and the pitch of them was kind of just like hey These models are incredible. They're going to change how you work That change is going to take a lot of harnessing from a technological perspective and also a lot of like human capital transformation Trust us with both like, you know, we're going to have an engineering team who is fully focused on taking really was open AI at the time and kind of teaching it Prompting it had a do financial tasks giving it access all the financial market data Giving it as much context as possible on how Lazardo works So that was one and then the second part was like literally like myself and gave and a couple other folks like Rachel Friedman Alliana who were ex-bankers and we're like we will just come in to Lazardo every day And we will write all these custom props and workflows and automations and get to know your bankers super well to actually start to embed This stuff into their workflows day today. So that was kind of the original pitch to your point And I'd never I've never sold sass or software in the previous era But you're totally right that investment banks I mean Europe is a perfect example of this like as when I came over here this year I was not sure how European banks were going to be procuring this stuff because there are banks in Milan and Madrid Etc that like basically like missed cloud, right? So they're like very very kind of slow to adopt stuff But they all now have these like a gentick AI task force and they're trying to figure this stuff out And you know, I think with for them it was probably more like the clawed opus four five stuff as opposed to The chat you be team moment that that really puts stuff into focus for them But like they're getting there too. So to your point like these banks. I think I've recognized that whereas previous Transformation cycles have been about cost cutting and maybe about security and and maybe about data organization internally and things around HR and human capital management This one is about existential revenue transformation This is about what are the next five to ten years of the industry look like we think they're radically different and every bank no matter Whether you are JP Morgan Goldman Sachs or some like small regional boutique bank if you don't have a good AI strategy You're putting your entire business at risk and that's something that like we used to need to like sell really hard Now it's something that doesn't even show up in our deck, right? Like that is like so table stakes obvious and the entire conversation is grounded in like how are we going to help you address it? So the urgency is is been completely different. I think from from previous cycles Hmm or even if I think of like I recently had Jesse from Dekegon on up the CEO on the part and even he talked about like they Self do enterprises mostly and and he was saying he's been amazed at how it's gone from like an efficiency Conversation to actually a product conversation. Yeah, like it's not just a cost setting I mean that's a whole topic we can talk about is like cost management Like that's a topical area with token spending and just efficiency Yeah, but it's just down rogo in the early days also your side point you mentioned Rachel and Alyana So you had hired a team by them when you have that I guess by the Lazar deployment It was just Rachel and then yeah, Alyana and some of the folks Nikki Kohli came on kind of over the next 12 months or so And then when did you raise the next round of funding that Keith came on board for Keith Revolge? Yeah, so the the Lazar round the Lazar deal was December 2023 We rolled it out in the first half of 2024 because we were like deploying it like kind of on-prem or in cloud-prem Which was not the best way to deploy the software at the time And so it took a little while and so once that was like successfully deployed and 1500 bankers We're using it day-to-day and and the feedback was good at that point We were able to raise our series a so I think Keith came in maybe in like August of 2024 or something like that And so by that point you had clearly more customers, right? Yeah, yeah, yeah, yeah Yeah, we kind of had like Lazar and then like a feet like three or four Utics that had started on like smaller things, but we're starting to talk about upselling. That was kind of the the shape of it at the time There were like there was enough to show somewhat of a repeatable kind of motion there Tell me about and this we can connect to present day like customer discovery like in the business I run behind the podcast. We yeah, I think I said the other day we work with like JP Morgan and and McCory and a whole bunch of these banks And that can be like a six-month process just to understand what their problems are Yeah, get the right like stakeholder and get the meeting and then fall into their budget cycle and yeah You went onboarding you've done this right? Yeah, what is your six months even sounds six months sounds a good dream for that Yeah, it sounds ambitious, right? Yeah, so tell me how's your discovery process changed again if you met me today And I was your ICP at one of your target customers in Europe. Let's use Europe as an example. Yeah How do you build trust for them and how do you understand their problems to then convince them to buy a robot? Yeah, it's a great question and I think early on so much of the effort was like yeah a spent convincing them AI was like very important that they needed a strategy, then be a lot of it was like very specific workflows. It was like, "Hey, we think that your seniors are spending a lot of time doing this. And your juniors are spending a lot of time doing this." And that kind of med-pick style discovery was really, really important. Now, I think we're just one altitude above. So there's the same type of exploration, but it's much more like, "Hey, what have you rolled out? Like, what are the tools on desk? Like, is it working? Is it not working? Where are the gaps? How are you managing token spend? Are you cross-model? How are you building like firm memory? Is the system getting smarter over time? How is your internal data organized?" So it's much more kind of like CIO, CIO, C-T-O, maybe C-E-O, level kind of altitudes for just the overall AI strategy. And then the pitch is pretty compelling. It's like, "Hey, look, like, clearly you guys need a partner on this stuff and every bank does. We don't think that your partner should be one of the frontier labs for a variety of reasons, including cost economics, vendor lock-in, just overall model risk, security, and domain focus." So you should go with a provider who's fully focused on this space and can help you hot swap between models. And then it's a bit about showing why we think that we're the right people to help you with that. And it's kind of just like, "Hey, we think you guys have a great business. We think you can make it better in these ways. We'd love to connect you with five clients who we've done something similar for in the past. We'd love to get the product into a few users' hands so they can kind of kick the tires and give you some confidence that it does the things that we say we're going to do." And then kind of going from there. And so I mean, a lot of the much more cycles at this point are spent in the just enterprise procurement infosec governance site. Like, that's where the meat of the like deals are at this point. As opposed to like the upfront stage setting or like their need to buy or like why us. It's actually a lot more. Okay, yeah. Rogo seems great. I don't know they're working with these vent, you know, these companies like whatever. It's like, "Hey, which divisions would it make sense to start this in? How is that going to align with like some other initiatives we have? How is that going to align with our internal build?" Like it's those sorts of questions that end up dominating these conversations. When I had Havi's CBO John Haddock on the show, he almost said to me like prestige was their go-to-market motion, right? They had like some iglo firms early on and that became a proxy for trust. And I see that like I think humans work on that like if you recognize a logo. I guess a two-part question. One was that part of the Rogo story like using big logos as a proxy for trust. And two, what they trade off, like one of the conversations I have with a lot of founders today is it's kind of like a carrot to chase the big logo. But as you'd know, it takes a lot of resource and time and money to service them. And I kind of say the founders don't go after the big logos early on because then you have to hire like a sales team just to work on one account. Yeah. And a big churn. You have a big hole in your budget. So I'm curious. Yeah, tell me about the proxy for trust. And then when did you feel big customers were right to service? Yeah, totally. I mean, you're right that going with Lazard and going with some of these other bulge bracket names kind of that I don't have logo rights for. So I can't reference publicly that you can probably guess what they are helped us a lot kind of going down market. It wasn't like that galaxy brain or like intentional. I feel like there was some element of we knew people at these institutions and we've been talking to them for a lot. I also think like the partnership pitch actually works better at a large organization where there's more kind of like stability that's required. There's more like hands-on change management that's required. Security is more important. So having folks who are fully focused on your firm and on your industry is actually more of a selling point than going to like a 10 person private equity firm or boutique bank. So those are the reasons that we started there. To your point was huge risk from a P&L perspective and a huge risk from a product roadmap perspective to serve these institutions early on. Like we were constantly getting pulled into very bespoke features that they that they wanted and we had to have a good nose for where something was helping us find product market fit with other firms versus building something that's that's really really bespoke. And that was kind of a painful thing early on like that whole first year of commercializing where there was really only like one to two big customers and we would occasionally tell them no because we're like hey we don't think that's going to apply to other firms. It did take a lot of discipline. It definitely is paid off overall and every conversation is easier when we can start it by saying hey these are the 10 banks where we have over 5,000 bankers deployed you know at each of these and and you can call the CTO and they'll say good things. But I would say honestly what's what's kind of hilarious and and ironic. What I've noticed in Europe is at times it's almost like an objection we need to handle because they're like oh is rogo one are they two like focus on the American banks and so that's something that we've needed to really start telling the story now we're working with a lot of the big European banks as well and you know really showing that we're building local here. And the second which I never saw coming if you told me this like five years ago to be like this is incredible is like is rogo too big to like focus on our needs as a GC bank in in in the UK. And what did they mean by that? What they mean is it's like okay if they are working with all these bulls bracket banks we don't necessarily want the exact same tool that all those banks are using. We actually want more of a tailored partnership and a build partner who's going to build a lot of custom stuff for us. We don't want to show up to meetings but the same exact pitch book that these large banks in the US are showing up with we want something that's super differentiated et cetera. And so when I hear that I mean I know it's clear that I haven't told the story well because that's just not the right way to think about it. The right way to think about it is a provider like rogo we are in the business of creating tailored versions of the platform for different firms and having tailored partnerships and actually if a banker at Moles and a banker at B&B Paribah ask a question in rogo the answers are going to be very different just based on the firm intelligence that we've created for them all the workflows all the agents all the skills so there's actually more of a divergence than a convergence in terms of the types of answers that folks are getting and the types of materials that we're creating. I want to come to go to market in a second particularly comparing and contrasting the different regions you're building but before that one interesting anecdote came up in my research is how you engage decided who should be CEO and decision making I think the amount of founders I see that stuff up because of that where egos get in the way it's incredible right you see it you're seeing it right now with a lot of the AI labs like it's playing out in public this so much ego play where folks when I spoke to them for research they said you guys were pretty cordial about it and maybe it goes to your this low ego approach to life that we talked about at the start. Was that an interesting conversation on like being because I think you were co-seos initially and then Gabe because when we first started it yeah and then when we raised the first round from Alecorp they were like there were like someone needs to like be the boss day today and they're obviously right about that. It was interesting at first I mean I like the angle that I'm super low ego it was just all easy and probably not quite true I was like I can't believe I'm quitting to start a company I'm not even the CEO and it was pretty clear like if it was going to be one of us it should be Gabe I mean like partly because he had a better investor network and partly because like Gabe is just Gabe is one of these people who like that dude is CEO like he met that guy you're like that guy is going to be the CEO of hopefully it's rogo that makes him like a legendary CEO but if it's not rogo it'll be some other company where he becomes like a Travis Kalanick figure like a Brian Chesky thing he's just incredible in so many ways and so like that was just pretty clear and there wasn't even me being like humble that was more me observing the kind of guy that that Gabe is and then within a few months it's like we're a real company like we've hired a couple engineers we're trying to do stuff and like all my energy and thought are just directed towards how do I actually try to like make this company successful and everything else is just so kind of like stupid to to think about I have more like scope and stress and responsibility and like everything that I know it's possibly do with so there's no there's no assemblies like oh I wish I had like a way more tell me about it on the socials signal point I feel high rings a good example of that as well and like you said before you've hired a lot of ex-investment makers that have left a part that perhaps had more prestige and more financial upside at least back then join rogo how have you gone about that because again I know firsthand like convincing someone to join a company maybe now it's a bit easier because you've got the credit and you've got the valuation yeah investors and all that but maybe the first couple of years like till maybe your series be it might have been tricky again any stories on how you can win some of these like smart people to yeah yeah I'm work for you instead of anthropic or open AI yeah yeah yeah it's a good point or good question I mean like definitely in the early days every conversation that you have with the potential higher it's like you're like raising money like you're doing the full like end and pitch like this is our right to win this is why we're here this is what your equity is going to be worth maybe you can use Europe as an example tell me let's it could be an interesting case study like when you decided you're going to come on the ground in Europe how did you build the team yeah well I mean for the ex-bankers it's a pretty compelling job I think in a lot of ways like there are a lot of folks who are in investment banking who want to have operating roles for a variety of reasons maybe because they want to be operators long term maybe because they want to go to VC or growth equity or tech investing and that's often the best way to to do that and gain kind of credentials in the space and if you're going to be an operator it's a pretty good gig right you get to really apply all of your previous financial experience it's very cross functional it's very commercial very client facing very growth oriented it's also a lot of product and edge collaboration and you're part of like kind of like a you know I don't want to call us a rocket ship but like a you know you're part of a quickly growing company and you know I think for a lot of our engineers it's like if there are engineers are going to have like infinite opportunities to join really fast pace high growth companies that's just the nature of being like an AI or you know good back end engineer there aren't that many opportunities to like join a company like like this, where your skill sets super applicable. And it's like, you know, this adventure scale business that's growing incredibly quickly. So in Europe, it's like, hey, we have all that, we have that backdrop. We have that kind of product market fit. We have the funding. And then here's a chance to do like the early stage thing again and be kind of that startup within a startup, even more cross function, all even more autonomous and help win the geo. What I've seen is there's sort of two different types of folks who join. There's the current rogo user or product and, you know, likes it enough that they're like, I could get behind this for my career. And that's my favorite because any call they join if they introduce themselves as a former rogo user who joined, that's like the, you know, best pocket possible recommendation. And then the second type of person is someone who is in seat as like an analyst or associate at a bank and then becomes sort of like a AI czar within the firm, like they join like the AI committee and they're helping roll tools out and internally and test stuff and build workflows. And often you see someone like that after like a year of doing that, they're like, well, this is 25% of my job. This is the best part of the job by far. I don't like the other stuff. And if I join a place like rogo, I can do that the whole time, except it's way higher leverage. I'm doing it across a ton of different firms impacting way more people. I'm part of a tech company. So this is a very different vibe, less bureaucracy moving way faster and then a lot of equity upside and what I'm building. So for both those two types of people, I think it's pretty compelling. If you plug a random person out of bank, it is a good chance they would never think about quitting and joining a tech company. But for the self-selecting group, I do think it is a pretty compelling pitch. Anything you're seeing on expectations from talent on RAM or ESOP, like it's this very competitive talent market out there. And folks can, like you said, they can go to Harvey, Lagoro, Dachigan or a bridge or one of these like application layer companies that are killing it. How are you getting them to rogo? Like are you offering any benefits? That's above market. VCV, you know, like a Lagoro Harvey, it's probably a somewhat similar, you know, package. I would assume and it's more person to person. And it is going to come down to like, these are the specific problems that we're going to want you to tackle in your in your first year. It's probably more personality compatibility with whether it's me and Gabe or other folks on the team. So I think it's more idiosyncratic. I don't think we figured out like a systematic way to beat, you know, these other app layer companies that I'd getting talent. I think it's just trying as hard as we can on each candidate to tell our story. Like I said before, let's compare and contrast to different markets. I think what's particularly interesting, I say this to you the other day with you coming into Europe is, I mean, all those companies you mentioned, I don't think the founders have moved. The founders are still based in the US and the Lagoro's based in Sweden, but the others are based in the US. They've hired a GM or they've hired a chief business officer. Yeah. Yeah. I'm glad it goes to clearly your belief in yourself to put yourself on the ground and uproot yourself. But I'm curious, how do you campaign contrast US versus Europe versus APAC? Any distinct differences between the three markets? Definitely very different markets in a lot of ways. One concrete difference is definitely like the security cycles are longer here. There's a bit more sovereign cloud stuff that shows up in the US. They'll pile it anything. Like you can go to a bank and be like, Hey, you want to access to the software? They probably have like a lightweight way to like get a sandbox trial go and give 20 users access, get some feedback quickly. So like we'll be in bake off regularly with like five other vendors at once. Everyone has access to all the tools in the run of the same props. And that's a little easier for us, just because our product is good. And so if you use us versus other folks most of the time, you're probably going to be like, Hey, and the guy should really be like the roguel one. And so that's a bit of a, it's a bit of more easy. It's a bit of an easier go to market motion in some ways. If you're up frequently, they will pile it just one tool, maybe two tools because it takes so long to get stuff through info sack. They consider it a risk that even have a pilot. Well, it sounds like they actually view us brand as a negative signal, right? That it's hard to fully draw. Like it varies person to person. There's like a, I think if we can thread the needle and be like, we are a US company with US capital US innovation. You know, we are moving quickly like a US company, but we have the local boots on the ground presence of like ex bankers who are going to help you deploy this. We have local legal folks, local compliance folks, like local solutions, architect security engineers, etc. We're working to adapt the playbook for Europe. That's probably like the best possible pitch if we can show that we're a bit of both. But so in Europe, there's a lot more kind of just value selling up front. Like we need to like be everywhere and be well regarded enough in every single firm to be included into the one to two vendor pilot that goes on. So it's very relationship base as opposed to, you know, product based at times. And APAC anything unique about APAC compared to Europe in US? It's just so sprawling that it's, I mean, they're, you know, of course, like the French market is different from the Spanish market. It's different from the Italian market. In APAC, like Tokyo versus Singapore versus Hong Kong versus Sydney versus Dubai versus India. It's like very hard to even draw like parallels across. They're probably more different from one another than they are similar Singapore is probably the most similar to Europe, you know, that's Western in a lot of ways. A lot of the expansion we're doing there and a lot of our users there are actually just the Asian divisions of the bulge bracket banks that we're working with compared to Tokyo, like our deals there. It's like you need, you know, a native Japanese speaker on hand. It's a culturally very unique. It's a completely different market. So just the, the sprawl and the scale of it is, is, is different. So it sounds like it's, because a lot of these banks you're working with a global banks, right? But you've sell to them by region. So they can buy it for a good globally. Occasionally, what I found this is be drawing a broad, like kind of a characterization that's probably not fully accurate. Frequently, I found the US bulge bracket banks. The US banks have a central procurement where you like sell in New York and then you get users globally. Sometimes in the European banks, it's a separate procurement office, procurement center in Asia. You need to go like get budget approved. It's completely different paper. It's a different MSA, etc. Right. Interesting. It's a pretty boring time. So it's just got a back. Yeah. I mean, I think the takeaways, it's not one size fits all. Yeah. Exactly. Which makes sense. I'm conscious of time. So I want to come to rapid five sprint before I do. We talked a lot of the start about the challenges building. Now things up into the right. If you think in the past 12 months, has there been one moment where you've been tested a lot? And I wonder if you can share it. Yeah. Question. The sheer volume of scaling has been a huge task. We've, like, you know, in the last 12 months, we've gone from like, I think like 40 people to like 200 or something like that. So it's a completely different company. And so when you're 40, it's like, you don't really need any process, right? It's just like everyone just doing everything at the same time. And like as long as we're roughly on the same page, it's fine. Now it's like, we're hiring people who are hiring people who are hiring people. And there are people to company like we don't really know that well. And hopefully we've spent a little bit of time with them. But to be able to create kind of as operational cadence, a set of values, a way of doing things that is not restrictive and still like fosters autonomy and creativity, but keeps people aligned is a big is a big challenge. How are you getting better? Like if I reflect in my own self, like being a manager, people leaders really, like when you were like, you go back to like Princeton days, we all said it, right? We're like, we want to be a manager. We want to have like 20 direct reports. And now I think of it. And I go, no, I don't actually want 20 direct reports because that's 20 careers. Yeah. Yeah. Emotions and 20 egos that I've got a manage. Yeah. How are you getting better at being a people manager? Because I hope I am. Yeah. It's no, it's so it's the hardest thing. I think when you're when you're like, you're really good. That's always like a good listener and the empathetic, which is like a daily challenge, right? Particularly in a startup that's growing so fast. Yeah. Yeah. Yeah. That's really nice. Yeah. I think when you're 20 years old and you picture managing, you picture like everyone's going to be happy all the time. And like you're just going to be a good manager. And there's not going to be these like problems. And yeah, that's never how it is, even with the companies doing well, you know, these things still come up. I think I've just like learned to be so transparent about what I do and don't know about what I'm working on, about what I need from folks with feedback. Like I am just so open book on literally everything. And when we first started the company, like we were 2324, we had people who were like in their 30s reporting to us. And so there's a bit of a pretense of us being like, yeah, we know what we're going to do. Like we have these clients lined up like whatever and you're trying to kind of, you know, show why you're the boss and not them. And as you gain confidence over time, it's like, I would never pretend I know something I don't. I would never purport to like be better at something if someone else is. I'm like, Hey, the story when I when I asked him to join the company is not like, Hey, come work with me as I solve these things. It's like, Hey, like let's grind on this together. And like we are just on the same team. We're just going to run at it. And that perspective, I think, allows you to have just a lot of bidirectional checks and balances throughout the day. People always kind of know where I'm at. People always know, you know, if I liked what they just did, if I didn't like what they just did. When you give feedback constantly, it like deweights it. If there's an endless stream of feedback from me to everyone else, then no one takes it personally when they when they get something. People kind of know that they can hopefully that they can trust me and that I have their back because I'm so kind of open. So that's probably been the biggest lesson is just being myself as much as possible and putting on as little of a presences as I can. It's so interesting because this is probably the first time in tech where there's so many like founders CEOs that are like in their late 20s. Yeah. Right. Running like multi-builders. in dollar valuation companies. We're like again, back to Kevin Ryan. We were like him, we're running those companies in their 40s, right? 10 years ago. It was now you've got like a whole group of you guys in your like literally like in your late 20s and maybe someone like early 30s. That's like fascinating. How that plays out and that probably speaks to the, hopefully the meritocracy nature of tech. And especially what's different, you know, is like where you had these people in their 20s before and like the 2010s running companies, they were typically like consumer companies, social media companies, internet companies. And yet now it's like bank rates, secure enterprise software companies, but that is a big change for share. Yeah, I want to move to rapid-frying spring, John, before I do is anything I have an ask that you want to touch on. There's been fairly comprehensive, but no, it's okay. All right. Rapid-fire is there one non-work investment? Ideally of time and energy is there a course or a hobby or a holiday you really enjoy. I love guitar. It's like my best way to just kind of unplug and kind of doodle around and not really think or do anything after work. Do you still do it? Do you still have time? Yeah, I do it probably like 10 minutes a day. I haven't gotten any better in the last five years. I just plateaued at, you know, house of the rising sun by the animals, but that's kind of where we are. Nice. Is there one thing you want to learn in the next six months? I think more about revenue organizations. I think I'm still, I don't really have an instinct, how to think about territory planning, as we're just really building out a commercial engine. But it's ironic, though, because one would say a lot of the playbooks, a lot of these like senior CRO's have used, don't apply today. That's true, too. Yeah. I'm always blue. I think it's the best people are going to be the people who have the playbooks and then know when and where to apply them. As opposed, like, I don't even have the playbook to begin with. So I would want to, I think you want to study at the altar of these, you know, John McMahon style CRO's. And then maybe throw out 50% of it, but they keep the good 50. Yeah, because that's something I always think about as like, you could hire like a high flying CRO. And this is what I did 10 years ago. But it's like, dude, that doesn't work today, right? Yeah, yeah. Now you're totally right. Yeah. I'll be interesting how you make decisions on that in terms of your exact team. Yeah. Is there one interview question you love asking prospective candidates in a hiring process? I just love really digging into like, if they're leaving the current job like exactly why? And like, we will spend like 30 minutes talking about like, what is going wrong? Where specific personalities at their current job, who they get along with, who they don't, what's been going well, what hasn't been. I've found there's usually a lot more there than their first past answer of like, oh, I'm looking for more autonomy. I really dig in there. Actually, I was going to ask on that. Have you learned anything about how to do good reference checks? Like, this comes up quite a bit at the moment, like, back to talent. Yeah. How are you getting beneath the surface? Yeah. I'm pretty like, I'm kind of quantitative. I'm always like, like, if you're just like, oh, like is this person good? They'd be like, yeah. And I'm like, what percentile are they? Like, what rank are they compared to other people you've worked with in this role? And then boring that. It's like, I literally like, people probably hate me. But I'll be, hey, for the following like 10 traits, rate them out of 10, like raw IQ, coarse power, intensity, ambition, like all these things. I just get literally like numbers on the board that I can use to that I can use to benchmark. Because when you don't have that, it gets kind of fluffy. I found last two, one pet peeve when you're waiting in line at like a coffee shop or something. And the person in front of you leaves a lot of space between them and the person in front of them. And I'm like, dude, you're leaving the flank open. Like we're danger of someone else jumping in that this is me off. I like that. That is so specific. Yeah. Yeah. I think about this a lot. And last one, if you could recommend a question, I should ask the next guest. You, of course, don't know the next guest. But anything I should include in my notes, particularly founders that are coming up. Yeah. Maybe, maybe a regret slash thing that they think they, if they had done differently, the company would be in a, would be in a better spot. Because I think there's a temptation to be like, oh, well, it's all part of the journey. And I say, no, there's definitely things that could have accelerated us and helped us move a lot of that. I mean, hindsight, hindsight's a beautiful thing, right? Like things you could always change things. I'm sure those first two years, you probably do them differently now. Oh my god. I hope so. But you wouldn't have known that if you didn't go through the two years. Yeah. So our, our, our literal like frontal lobes were still developing. But John, you have made it. You have made it to the end of your first in-depth podcast. Thank you. And yeah, super, super excited for wherever I was going and hopefully see you in person soon. Yeah. Thank you so much. Really appreciate it. Thanks for having me. That's a wrap. So it's something in this episode. It's back to thought. Send it to a friend or colleague. And if you're curious about partnering with us and the Curiosity Center, whether it's this podcast, do our reports, events and more and join the ranks of existing commercial partners, including Google, KPMG, Vanta, the University Melbourne. And I lose my details on the show notes. Until next time, I'm Vity Tagawaal. And this is the High Flies Podcast.