In short
Gabe Stengel’s Rogo AI automates investment-banking workflows, aiming to replace parts of deal execution and accelerate M&A/capital markets from months to days, while reshaping jobs and business models.
Guest backgrounds
Gabe Stengel is a former Lazard investment banker (M&A; covered healthcare and consumer/cosmetics). He studied computer science, built early finance AI assistants, and co-founded Rogo with John. He quit Lazard at 23 to start the company.
Key claims
Rogo now has 35,000 bankers using it; Lazard became a paying customer. Early adoption failed for two years until LLM “step changes” enabled credible demos. AI will automate whole deal lifecycles and reduce repetitive workflows, but humans remain for emotional/relationship-heavy parts. Venture investor Keith Rabois backed the A round after seeing the market potential.
Notable examples
A CEO refused an acquisition offer double the public-market value; Rogo automates tasks like deal screening, buyer outreach, and data-room diligence; SpaceX IPO S-1 discussion (context).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Transformation of Investment Banking
0:00 to 0:21
Discussing the impact of AI on investment banking workflows and job roles.
“With Red Bull Summer All Day Play, you choose a playlist that fits your summer vibe the best.”
The Transformation of Investment Banking
0:54 to 1:40
Discussing the impact of AI on investment banking workflows and job roles.
“Gabe Stengel built a$2 billion AI tool to automate his old investment banking job.”
Gabe Stengel and the Future of AI on Wall Street
3:04 to 4:12
Interview with Gabe Stengel about his AI tool Rogo and its implications.
“And now for a dispatch from a very different corner of the AI boom.”
Understanding Investment Banking Workflows
4:12 to 6:40
Explaining the daily tasks and roles of investment bankers.
“Because one of those things is I think there are going to be a lot of people watching this who are going to be like, well, I've never worked on Wall Street.”
Personal Experiences in M&A
6:40 to 7:58
Gabe shares insights and anecdotes from his time in investment banking.
“worked with large healthcare companies to think about what businesses they should buy.”
The Emotional Side of Business Transactions
7:58 to 8:34
Discussing the emotional aspects involved in M&A deals.
“I started my career covering consumer M &A.”
The Birth of Rogo and Early Challenges
8:34 to 10:34
Exploring the inception of Rogo and the struggles to gain traction.
“Rogo, my business now, AI platform for high finance, was actually based on my thesis in undergrad of AI assistants for finance.”
The Shift in AI Acceptance on Wall Street
10:34 to 12:28
Chronicles the change in perception of AI tools on Wall Street.
“What were those early conversations like, or were there no conversations at all?”
From Rejection to Success: A Turning Point
12:28 to 14:00
Gabe reflects on the pivotal moment that changed Rogo's trajectory.
“Now walk me through the sequence of no's and how that felt and what it actually meant to finally get a yes.”
The Shift in Venture Capital Relationships
14:00 to 17:45
Explore how the speaker's journey with venture capital evolved and the pivotal moments that changed their approach.
“But when you sort of think about the momentum you've gained since then, when did you know that the momentum had shifted?”
Show all 18 chapters
Automation and the Future of Finance
17:45 to 23:38
Learn about the ongoing transformation in finance through automation and its implications for private markets.
“Now, you named Felix after a very famous banker, Felix Roatan.”
Transforming Investment Banking Jobs with AI
23:38 to 27:53
Discuss the impact of AI on the evolution of investment banking jobs and the potential for new opportunities.
“And that's when you started to see the emergence of agents and the idea that these systems were not just thinkers, but they could become embodied and use different systems.”
The Historical Context of Investment Banking
27:53 to 28:05
Understand the historical evolution of investment banking roles and how technology has changed them.
“I think as the sort of volume of dealmaking explodes over the next decade as a result of this technology, I think there's probably more bankers.”
The Evolution of Investment Banking Jobs
28:05 to 29:24
Explore how technology is changing the nature of investment banking jobs.
“But I do think that the job is going to change.”
AI's Role in Wall Street
29:24 to 31:43
Discuss the potential and limitations of AI in the finance sector.
“Okay, so the answer is within reason, kind of everything.”
Building Rogo and Market Expansion
31:43 to 33:58
Learn about Rogo's development and its plans for market expansion.
“And we work well with OpenAI and Anthropic and Gemini.”
The Impact of Historical Perspectives on Finance
33:58 to 36:28
Understand how historical contexts shape current finance practices and technology.
“There's a huge, huge market of folks who want to participate in capital markets.”
The Future of Wall Street in a Digital Age
36:28 to 40:22
Examine Wall Street's future relevance and its role in the global economy.
“banks themselves, the data providers, the exchanges.”
Transcript
Automatic transcript. May contain errors.0:01Allie Garfinkle:Ready to soundtrack your summer? With Red Bull Summer All Day Play, you choose a playlist that fits your summer vibe the best. Are you a festival fanatic, a deep end DJ, a road dog, or a trail mixer? Just add a song to your chosen playlist and put your summer on track. Red Bull Summer All Day Play. Red Bull gives you wings. Visit redbull.com slash bright summer ahead to learn more. See you this summer. so good so good so good everything you want for summer is at nordstrom rack stores now and up to 60 off stock up and save on the brands you love like vince sam edelman frame and free people join the nordic club to unlock exclusive discounts shop new arrivals first and more plus buy online and pick up at your favorite rack store for free great brands great prices that's why you There are certain types of workflows that will never need to be done by a human again, and I think that's a good thing.
0:58Allie Garfinkle:Gabe Stengel built a$2 billion AI tool to automate his old investment banking job. But for two years, no one was buying it. The early days were pretty terrible. I probably had 30 passes that round. Now more than 35 ,000 bankers are using his tool Rogo, which does in minutes what used to take them a week. And Lazard, the bank that Gabe quit, is now a paying Rogo customer. I can do all of these workflows in one-tenth the time with one-tenth the resources. Last week, two of the world's largest banks signaled major AI-driven job cuts. Investment bankers are especially in the crosshairs as the job is indisputably changing.
1:35Allie Garfinkle:And the work your banker did last year could now be an email. Welcome to Termsheet. I'm Ali Garfinkel.
1:44Allie Garfinkle:And on to this week's news. The SpaceX IPO is upon us. After more than 20 years as a private company, SpaceX is officially going public over the next few weeks. Now, regardless of how you feel about Elon Musk, about SpaceX, about Tesla, this will be a genuinely historic event. It will be, by every account so far we've heard, the largest IPO of all time by a substantial margin. Last week when the S1 dropped, it revealed some genuinely shocking things. I would go so far as to say it was a banger of an S1. Three things that you should know from it. Number one, revenue is up at SpaceX, but so are losses to the tune of billions.
2:26Allie Garfinkle:Number two, Elon Musk pay package is tied to and among other things establishing a colony on Mars of at least a million inhabitants. And number three, Anthropic and SpaceX have an existing deal to the tune of billions, which is genuinely surprising given that Musk has previously described Anthropic as, and I quote, evil. SpaceX is widely considered to be going public in the vicinity of June 12th. And this is also happening at a time when open AI and Anthropic are also widely rumored to be considering going public. Now, I'll believe that when I see it. But what do you think? Are we headed for a red hot IPO summer?
3:03Allie Garfinkle:Let me know in the comments. And now for a dispatch from a very different corner of the AI boom. Here's Gabe. Gabe Stengel, thank you so much for being here. Thanks for having me. Rogo is bringing AI to Wall Street. But what does that actually mean? Like walk me through a day in the life of an analyst, for example, using this tool. I actually think in some ways it's easier to think about the market and the firm perspective versus just the analyst. It's pretty easy to imagine a junior banker, you know, working in Excel more effectively, working PowerPoint more effectively. for us, bringing AI to Wall Street means transforming what high finance looks like and thinking about reinvention of M &A and capital markets and making them radically more accessible, you know, radically more efficient.
3:46And to me, it's helpful to think about the macro, i.e. if it takes three months right now for a banker to go to a company, maybe it's Glossier or someone else and say, hey, how do you get ready for a process that might take three months and then another three months to consummate an acquisition. And I think five years from now, that sort of M &A process can take 48 hours.
4:07Allie Garfinkle:Now walk me through a couple of use cases. Because one of those things is I think there are going to be a lot of people watching this who are going to be like, well, I've never worked on Wall Street. Or even if you have, they may not be able to necessarily imagine this. What a banker does is very different from what an investor does. Some of the underlying workflows are the same. but what a banker is doing is helping a company sell itself or helping a company buy another company or raise equity or raise debt. It's less about, you know, investing your own personal capital in a business. But if you're going to help a business sell, you need to help that business value itself.
4:44Think about what are similar businesses that have been bought and sold so that when you're presenting it to the market, you have reference points for how to value that business. And that kind of valuation work, positioning work, strategic work to understand, the value of a business is very similar to what investors do. But for a banker, the kind of end to end process is the value add, not just that analytics work. And so if you're a great investment banker, it's about finding clients, i.e. how do you go into market and find companies that want to buy other companies or companies that want to sell or companies that want to go public and raise equity?
5:14Great. Once you've done that, it's how do you help value them? How do you help actually think about what the business is worth? And then how do you find requisite buyers who are prepared and agree with your valuation, either to buy that equity in a public offering or to buy the whole business. And that's still, you know, abstracting away a lot of the complexity. But if you think about that full life cycle, what a junior banker is doing is less often speaking with clients, finding deals, speaking with potential buyers. It's more often the blocking and tackling around saying, you know, what does this business work?
5:44How do I get their financials, get a full picture of who they are, and then value, you know, the price per share. And so that happens in Excel, and then it's presented in PowerPoint.
5:53Allie Garfinkle:Now walk me through your life as an investment banker before this, because you actually do have experience with this. Yeah. So I began my career at a kind of storied independent bank, Lazard, that is known for M &A advisory. Did you always want to be a banker? No. What did you want to be when you were a kid? Probably astronaut is the cliche answer or MBA player. But I studied computer science. I loved engineering. I interned at a quant training firm, interned at a big software engineering firm. And then I kind of serendipitously met an MD at Lazard who pitched me on, hey, why don't you come in and serve as a data translator between the M &A teams and between the data science teams and help us think about reinvention of this business.
6:35And when I was an M &A banker, I kind of loved it. I covered healthcare companies. So we worked with large healthcare companies to think about what businesses they should buy. One engagement, we were speaking with the CEO of a$100 billion healthcare firm, and he wanted to buy an oncology company. I did not know what oncology was when I began at Lazard, but it's
6:53Allie Garfinkle:basically - You were what, 22? 22, something like that. But you got to sit in the rooms with these business executives who shaped markets, who shaped companies and industries, and think about real business strategy tied to financials. And so I spent a lot of time doing the valuation for the companies they were interested in buying. But then you also got to overhear your sophisticated banking MDs speaking with these CEOs about the approach, negotiation, how to value the business, why it fed into a strategic mandate. And that was fascinating. What was the most surprising thing you ever heard as a listener in one of those rooms?
7:25We advised a company that was trying to buy another business, and that business was worth a few billion dollars in public markets, and they offered double that. And the CEO of the business that they were trying to acquire just said no. And it was shocking to me that someone could offer twice what the business was worth, but this founder was so mission-driven, believed so much in what they were doing, that even though they would have had a billion and a half dollars wired to them directly the day that acquisition closed, they could say no. And to me, it made it clear, well, M &A is a lot more than just valuing businesses.
7:56It's personal. It's emotional. There's negotiation.
7:59Allie Garfinkle:I started my career covering consumer M &A. I did a lot of cosmetics M &A sort of at the height of the cosmetics M &A boom a few years ago. I guess, gosh, the better part of a decade. But to your point, a deal is never just a deal. It's never just about money changing hands. It's emotional. It sounds like from the way you talk about the story, you actually admire it even now. A deal is always emotional. I mean, even think about buying a house, right? It's just a transaction at the end of the day. But will people do that without thinking it through, without feeling it, without calling their parents?
8:27I mean, the whole thing can be emotional.
8:29Allie Garfinkle:So you quit Lazard when you were 23? 23, yeah. 23? Why? Rogo, my business now, AI platform for high finance, was actually based on my thesis in undergrad of AI assistants for finance. And while I was at Lazard, while I was doing the banking job, it became so clear that what I had worked on as an undergrad would be relevant in my life as a banker. And GBD3 came out. And I went to my co-founder, John, and said, hey, John, that kind of crummy tool that we made could now actually be pretty good. And so we left to start this business. How did you know the technology had gotten there? So the original versions of our tool and these kind of NLP techniques for parsing natural language utterances and turning them into instructions for a machine was really a you know called semantic parsing and it was based on context-free grammars and these kind of like almost rule-based systems where if you said you know run a model on this you picked up the word model and you said great let's run this python code gbd3 was a radical reinvention of of that kind of technique and it was completely different and it was more about you know the scaling of deep learning and these algorithms that were clearly going to work at kind of massive scale versus these kind of janky rule-based systems.
9:43Allie Garfinkle:Now, the early days, what were they like? Because I can't imagine it was easy getting some of these folks to talk to you. Yeah, the early days were pretty terrible. How terrible. We both didn't know how to sell. We didn't know how to build. We didn't know how to hire. We didn't know how to talk to investors. John and I used to joke that it was the most expensive form of business school. And we also used to joke that we should get back in contact with the associate VC who did diligence on us and asked who he spoke to that wanted the product because we couldn't find anybody. And so it was pretty miserable.
10:14And the reality was that the market wasn't ready for it, right? ChatGBT actually hadn't come out. It was just GBD3. And so that kind of wave of AI hadn't washed over the industry and made it clear that it was going to be transformative. And so you just had John and myself, who really had just only spent a few years in investment banking, trying to evangelize what AI was going to do to Wall Street.
10:34Allie Garfinkle:What were those early conversations like, or were there no conversations at all? No, there were early conversations, but it was just, you know, that magic moment, it was hard to show people. Like, the technology wasn't quite there, so unless you had a deep kind of empathy for how different LLMs were from prior techniques and how well they were starting to work, it wasn't clear that you could extrapolate towards everything that was going to happen, right? And even back then, our vision was kind of more blinkered, right? It was, how do you make junior bankers a little bit more productive, a little bit smarter?
11:05It wasn't, how do I radically transform what M &A and capital markets look like? I mean, even we had a hard time thinking about, you know, what does this actually mean? What are the second order effects? And it was very hard for us to kind of communicate that to, you know, bankers, investors as well, too.
11:19Allie Garfinkle:Well, it sounds like part of the challenge was just that you couldn't show that aha moment, but it also sounds like the conversation around AI, I mean, we forget now what the world was like before chat GPT but I remember when chat GPT came out and everyone was like what is this thing and it sounds like Wall Street had that moment too after you'd been trying to have the conversation for a while oh for sure I mean we John and I never used the word chatbot or AI because there this been this prior wave of technology where chatbots were kind of a letdown and so if you came and said hey we're you know this AI chatbot tool people were saying well we tried something like that four years ago and they kind of sucked and so we you know we did all this mental gymnastics to like not say it was AI because, you know, didn't feel like people - What did you say instead?
12:01Natural language interface. It was a terrible marketing term.
12:05Allie Garfinkle:So that went over great. Yeah, yeah. It was pretty good. So when did it change? When was the first customer? About two years ago. And it was really, you know, kind of the 4.0 model, GBD 4.0, where the quality of the LLMs was strong enough to do tasks that were credible and you could see and you could demo live. Before that, the models weren't quite smart enough. Now walk me through the sequence of no's and how that felt and what it actually meant to finally get a yes. I would say it was, you know, the kind of delta between momentum and lack of momentum to me. It is very clear when people say yes, why they are saying yes.
12:52And when you have the wind at your back, why there is wind at your back, right? Is it the product? Is it the moment in time? Is it the zeitgeist? Is it a specific buyer? When things are not working, it's very hard to piece out why, right? Is it because I'm bad at selling? Is it because the product isn't good? Is it because I've misidentified the problem? And so it's very demoralizing because you actually don't know what's going wrong. Is it me? Is it the market? Am I an idiot? Like, you know, there's all these things. And so that two-year period of us constantly pitching, changing the pitch, building, being unable to convince people, you know, it's hard to identify what the failure is.
13:24And so it's feels like you're constantly doing this breath first exploration exploration they just get lucky right like how do you have a lucky break that then you can double down on um and that lucky break didn't come until we started demoing and positioning a very specific version of the product
13:40Allie Garfinkle:um yeah about two years ago it's funny i remember covering a very early round for you guys um the market was completely different then and it was kind of like oh this is going to be a really helpful tool for some bankers on Wall Street, maybe. It was before the partner and compete model in AI had fully emerged. But when you sort of think about the momentum you've gained since then, when did you know that the momentum had shifted? And when, how did your relationship with venture capital evolve through that process? Which was the round you covered, the A or the C? I think it was the A. The A was when we were starting to get kind of branded.
14:18Allie Garfinkle:It was clear you were going somewhere, but if I'm honest, I was a little surprised by how quickly everything picked up. I don't know. Is that all steel? No, no, no, no. I mean, it was, look, Keith Raboi from Coastal Ventures led our A. I probably had 30 passes that round and Keith was actually the only yes. It wasn't like, oh, great. We had a bunch of term sheets and we picked Keith because he's a legendary investor. I love Keith. He is a legendary investor. He is the only person who said yes. I actually remember sitting down with Keith because I could only schedule with him, you know, about a month and a half after I started my process because he was so busy that I couldn't get time with him.
14:52But because it was so late, everyone had already said no, right? Like I had already gone to IC with a bunch of firms and they had all said no. And I sat down with Keith and Keith just goes, all right, Gabe, I get it. AI for Wall Street. It's consensus. It makes sense. I don't like consensus bets. Like I like to be contrarian. And I was like, Keith, well, if it's so consensus, why did everyone just say no to it? And he kind of perked up. And that was kind of the moment that changed in my conversation with Keith. And he saw what we were doing and he understood it in a way that other folks didn't.
15:23And I actually think the kind of mental tar pit that other investors fell into is they said, we're investors, we work in finance, we should be able to use this product today and get the value out of it. And they didn't have vision for where it was all going. And so they ran one question or one workflow and said, oh, this doesn't perfectly address all of my needs as an investor today. It's not going to work. Whereas Keith was just like, oh, this is obviously a huge market. There's really no one else situated well to address it who has the finance background and the technical background. I'll bet on that.
15:55Allie Garfinkle:To your point, there is also a lot of investors, particularly in venture, have at some point been bankers. So there's probably the idea of, well, I know this space. I know this product. I know what it can be. And I'm going to bring back something you referenced towards the beginning, because I think this is an interesting market when it comes to articulating the future. You sort of draw a distinction between where finance has been and where it's going. Where do you think it's going? I mean, I think high finance will kind of emulate what has happened to other parts of the fintech financial services ecosystem.
16:26And I think M &A and capital markets will become more and more efficient and automated. And I think if you, you know, work in private markets and you want to think about selling a business or you own a private market business, it's going to be much easier for you to tap into capital markets and transact. And what happened to public equities over the last 20 years, where it become easier and easier to just buy a share of a business. And so the second order effects are now you can buy an ETF for 50 basis points that bundles all sorts of different products. Those sorts of things are going to happen in private markets as well, too.
16:58And I think people perennially underestimate both the need for kind of human in the loop in fintech, but also underestimate the size of these markets. And to circle back to the kind of buying a home example, 20 years ago, you would not have ever thought about buying a home without speaking to someone, right? Like, I'm about to get a mortgage. This is a huge decision. I need to speak to my local bank branch about that mortgage and what it's going to look like. Now, you know, you can go to Rocket Mortgage and get that in 20 minutes. And actually, there's just as many people that deal with human real estate brokers because they're still emotional parts of the transaction.
17:33But so much of the actual financial services can be provided, you know, programmatically.
17:38Allie Garfinkle:This is actually a great segue into sort of the questions around humans, jobs, AI. I think we should start with Felix. Now, you named Felix after a very famous banker, Felix Roatan. Why? Felix Roatan was famously both a great investment banker, but also served the public good and was a great New York citizen. He saved New York City from bankruptcy. Save New York City from bankruptcy. You know, Felix kind of typifies that prior era of investment banking that was about apprenticeship advice, working with clients, forming relationships versus just the kind of like factory model that sometimes capital markets becomes of just churning out deals.
18:24And as we think about the next decade of high finance, we think there's going to be a return to this apprenticeship model where you invest in people and relationships and differentiated insight and advice. and the type of work that bankers are doing has changed radically over the last 20 years and as it changes what stays consistent is that the best bankers are relationship driven have high trust etc and you know one of the things Felix uh would say if you could if you could find him on the floor at Lazard and I was not around to do this but uh Rahul Recky on our team what was was that you know originally a lot of bankers used to call up their clients at 9 a.m on a Monday and say, this is where your share price is trading.
19:05And that was the kind of novel data that they provided because it was very hard to access that. That is obviously not part of the value proposition of being a banker today because anyone can access that on Google Finance. And yet you still need investment bankers to help you deal with an order of magnitude of harder problems than just finding where you're trading.
19:22Allie Garfinkle:You said something really interesting, that the job of an investment banker has changed over the last 20 years. Walk us through exactly how. You used to have to print out the kind of PowerPoint pages into a book and deliver those books to people before meetings. Now you can send it over email in a PDF. Crazy. Well, but seriously, it's like, imagine if 10 years ago, someone said, hey, guys, we're going to automate the printing out and delivering of these books. People might have said, well, what are the analysts going to do? It's like, well, I don't think analysts are doing that today. And I don't think they're any less busy as a result.
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19:56I think the jobs change. And this is an industry that's competitive, that wants to add a lot of value, that wants to do more deals. There's always more to do.
20:05Allie Garfinkle:Now, Rogo has started as something that you thought would be a helpful tool. And now it's automating whole workflows. How has that changed for your customers? Both Wall Street banks, but the kind of all enterprises writ large, have seen how transformative of AI is going to be, but are still trying to square the circle on, you know, are we seeing revenue uplift? Are we cutting costs? Like what's actually happening to our business? And I think, you know, Wall Street is the early days there too, where it's clear, oh, wow, I can do all of these workflows in one-tenth the time with one-tenth the resources, but what does that mean for how I change my business?
20:44And I actually think the same way that what we're seeing in the SaaS-pocalypse, where part of that is just about how do you have these SaaS businesses that are per seat completely reinvent their business models to be consumption-based, same thing's going to happen for professional services organizations and Wall Street banks. How do they reinvent themselves to take advantage of this technology to realign their business models for the future? And I think it's early days there. And so a lot of what we do is partner with these firms, not just to help them harness the technology, but to think about what needs to change from an org perspective, from a business model perspective, to make sure you can ride that current of AI.
21:20Allie Garfinkle:So you guys get data from PitchBook, FaxEd, S &P Global, but you also are in a situation where you have another partner and compete model kind of happening where they are launching their own tools. How do you think about that tension and what sort of prevents them from cutting you off in a worst case scenario? Look, those are data providers that have really valuable, unique data that people need. But in the same way that you would never hire an investment banker who only has access to one data source, how can you have an AI investment banker that only has access to a single data source? They are structurally impaired to a certain degree to be able to reinvent the kind of full operating model for finance because they can only give you the snapshot of the data that they have.
22:05And then at the end of the day, you know, we are actually helping them unlock more usage of their data. We're putting it into more hands. We're helping distribute it. And then we're helping maximize all of the kind of derivative works and value you can create on top of it. And so, you know, in a lot of ways, we can help them, you know, monetize that data much more effectively. But it is a kind of confused moment in market where everyone just sees this ballooning AI spend and wants a piece of it. But the same way that, you know, the large banks are going to have to figure out how to reinvent themselves and take advantage of the moment, so are these data providers.
22:40Allie Garfinkle:So at the very beginning, you were describing Rogo as kind of a helpful tool that was going to make people smarter, but now you're running deal screening, buyer outreach, data room diligence. What changed? There's been three step change moments in the underlying LLMs that have unlocked at each moment in time new sorts of capabilities. The first was, in my opinion, in kind of the chat GPT moment, just GPT 3.5 and 4.0, where it was clear that these things could generate natural language and start to think. They couldn't really do workflows, but they could start to think. That's where we got started.
23:16And so we said, hey, these tools can help you gather a little bit of data, help you answer ad hoc questions, be kind of a speed up Q &A tool. Moment two was 01 in the introduction of reasoning models. And those were profound in that they allowed the models to think before they acted. And as a result, they could start to use tools. So it wasn't just answering a question. It was going out into the world, running a screen, searching the web, updating a file, and returning that result to you. And that's when you started to see the emergence of agents and the idea that these systems were not just thinkers, but they could become embodied and use different systems.
23:54That really didn't take off until Opus 4.5, Cloud Code, OpenClaw, and the combination of both these architectures for handling the models, but also the increasing reliability and intelligence of the underlying reasoning models. And that was probably early December where it became clear, not only can these models quickly query data from FactSet and then update in Excel and then send out an email, they can pair together 500 actions over the course of an hour to do something end-to-end that would have taken you a week. And so it was really those step change moments in the technology that allowed us to kind of broaden our vision for what we could do.
24:32Allie Garfinkle:Now, I'm really interested in where this takes investment banking jobs over time. I found a statistic that really interested me. Goldman's New York equity trading desk had 600 traders in 2000. By 2017, there were two left, supported by 200 engineers. Why are you laughing? What's left? You don't look surprised. It's an interesting stat. There were 200 engineers, you said? Yeah, 200 engineers. two left on the equity trading desk by 2017. AI boom hasn't happened yet, supported by 200 engineers. Could you see something like that happening in investment banking? I would be curious what the aggregate Goldman Sachs headcount is, right?
25:13It's probably ballooned since then. And so there's certain functions and titles that no longer exist in title, but the aggregate number of bankers is probably way up. And so are people doing that exact same function that they used to? No, there's probably a new title for someone who's related to equity capital markets that exists today that didn't before. And so I do think the jobs are going to completely transform and reinvent themselves. I think there's going to be more and more a need for people as there's more deal making, right? Partly what AI allows for is now it's easier to serve a huge part of the market that's historically been underserved.
25:48There's 300 ,000 American businesses that have never spoken to a Wall Street banker that probably don't know what a Wall Street banker provides. and now there's going to be a whole crop of younger enterprising bankers that can say, hey, I can leverage a tool like Rogo and go do business for myself and explore untapped parts of the market. And so I think it's about reinvention. But certainly, there's certain types of workflows that will never need to be done by a human again, and I think that's a good thing.
26:13Allie Garfinkle:So there's a lot that's really interesting in that. The first is it sounds like you almost have this vision of something kind of entrepreneurial, where there are people who would have been maybe small-town bankers before who can kind of do larger and larger transactions. Is that fair? Yeah, I think that's 100 % true. I mean, when I look at the kind of crop of financiers that helped reinvent Wall Street, they were almost all entrepreneurial and invented new types of financing devices or new types of deals, whether it's Henry Kravis, KKR, or anyone else. I mean, a lot of the kind of spirit of Wall Street was entrepreneurial, and I think AI will allow folks to do that again.
26:51Allie Garfinkle:That's really interesting. The other thing, too, is I'll come out and say I do think the natural end point of this is probably fewer investment banking jobs. I imagine there are a lot of people out there who are not like, oh, no, fewer investment bankers. But is that fair on my part? And I guess the implicit question is why do investment banking jobs matter on a societal level if they do? I mean, investment bankers help companies get liquidity. They help companies restructure. They help businesses and even governments and whole economies rethink how to shape themselves. It's a very important part of society.
27:29I mean, let's draw a page from public equities. And there's fewer kind of folks who sit in the bank coordinating those transactions. But now there's a lot more participants in public markets, right? And so at the end of the day, the folks that are valuing public equities and investing in them versus helping broker buying and selling of equities, It's very similar underlying work, but now it's just you've transferred where they sit within society, whether they're within the bank or within investment firms. I think as the sort of volume of dealmaking explodes over the next decade as a result of this technology, I think there's probably more bankers.
28:04And there's more bankers to go out into the world and bring online parts of the economy, parts of emerging economies that have never accessed these high finance capital markets resources. But I do think that the job is going to change. And I think the kind of fundamental value proposition will get increasingly served by technology.
28:23Allie Garfinkle:Well, and I do think in the way you articulate how jobs have changed on Wall Street over the last even 25 years, a lot of them are technological changes. You actually were telling me about House of Morgan, and I recently bought House of Morgan. It is a very different job that David Solomon has than J.P. Morgan had, let's say. Or is it, actually? I mean, in some ways, the kind of job of J. Pierpont Morgan of helping bring investors from the UK into U.S. capital markets to finance railroads and industry and infrastructure, that is what investment banking should be, right? The financing of innovation and growth and emerging economies.
29:04and a lot of bankers do spend their time helping coordinate deals like that, but a lot of bankers spend their time on the drudgery of just doing the kind of underlying analytical work, PowerPoint, Excel, coming through data and can't be kind of enterprising in the way that the original investment bankers were.
29:21Allie Garfinkle:One thing I think about a lot in terms of the AI for anything important conversation is what AI shouldn't do. What shouldn't AI do on Wall Street? That's a good question.
29:43I don't have a good answer to that one.
29:45Allie Garfinkle:Really? Okay, so the answer is within reason, kind of everything. There's nothing that you're like, it's not like healthcare where there are certain things that people are like, absolutely not. This is one of those things where we actually, you're kind of like, there's free reign. Look, there's certain things where you value the human touch, right? So it's like, yeah, healthcare is a great example where even if the diagnosis is done by a computer, I'd probably rather be sitting with a human to give me the diagnosis. I think a lot of parts of the deal-making that we spoke about, the human parts, the emotional parts, humans are better situated to do that work.
30:18But at the end of the day, you have to think about what is the job to be done, what is the service you're providing, and what's the most efficient way to deliver that to the market.
30:25Allie Garfinkle:Now, on the Rogo tool itself, you can toggle right between Anthropic, OpenAI, Google. You're squarely in the partner and compete model of AI. What is your relationship to that tension? Because, I don't know, you have some pretty big potential competitors. In some ways, it is partner and compete. But in other ways, we have a very distinct vision from any of the labs. We want to radically transform Wall Street and high finance and help automate the full end-to-end deal lifecycle. And that means building a tool that's not just a large language model and an AI intelligence, but is deeply integrated into capital markets, into the systems of record of dealmaking, into the outputs and actually helping coordinate transactions.
31:11And that's very, very different. And so the reality is for an org to get the value that we're providing, it's either DIY, where you mix best of breed of LLMs, OpenAI, Anthropic, Open Source, so that you can train your own. You have to connect them to all the systems that matter for you. You have to build custom agents on top of it and take the muscle memory of how you do work and put it into prompts and skills and agents. And then you have to enable it throughout the org and actually rethink the org structure. And to do that, it's either build or work with us. And often we're a key part of that work together and partner story.
31:46And we work well with OpenAI and Anthropic and Gemini. And for those guys, I mean, they are incentivized to maximize the number of tokens that people consume. And so if we're a partner to help them actually, you know, have Wall Street consume more tokens, they're very excited by that.
32:01Allie Garfinkle:Do you worry about a Claude Code situation for Wall Street? Yeah, I mean, Claude Code is one of, if not the greatest product of all time today. I mean, a lot of enterprises are now waking up and saying, oh, my God, did I just spend$50 million on Cloud Code? Am I and I am maybe not seeing that reflect in my top line growth or my product development? So we'll see what actually happens. But Cloud Code is so intimately tied to what Anthropic cares about deeply, which is automating software engineering and AI research so that they can see that kind of fast takeoff. It's a very different type of product than what Wall Street banker needs.
32:36And at the end of the day, so much of what happens on Wall Street is the coordination and the deal making and the transaction, which is a whole different type of product and software surface area than just LLMs that are very, very good at contributing code in an automated way.
32:51Allie Garfinkle:One thing I also found really interesting as I was looking at your list of customers is among them is Lazard. What was it like pitching your former employer? You know, Lazard, led by Peter Orszak, has always been very forward and future-minded on what this technology is going to do. And they've been both very experimental, both very open-minded to how to reinvent their business. And so they've been great partners. The day I left, the product wasn't ready. And so it was always, you know, let us know how this goes, keep us in the loop. And when we came back, it was because we were ready. And they saw, wow, this is something that is going to be transformative.
33:27This is going to be something that's hard to build. You know, we know Gabe. Gabe used to work here. He understands our workflows. You know, maybe this is something we should take a look at. And they started small and then expanded. And, you know, they're still great partners.
33:39Allie Garfinkle:One thing I've wondered about, too, is there are only so many Wall Street banks, right? How concentrated is your business? And what do you think about as you consider expansion? Is it bigger contracts? Is it more customers from different places? What does that look like? It's a little bit of both, right? So we have hundreds of customers. We probably have 300 customers as of today, which both represent the majority of bulge bracket banks, the longer tail of independents and middle market banks, but then private equity firms, private capital firms, asset managers, hedge funds, public equity firms.
34:15There's a huge, huge market of folks who want to participate in capital markets. And so when we think about the kind of group of customers we want to serve, it's just all of those participants.
34:27Allie Garfinkle:Henry Kravis, KKR co-founder, finance legend, put money personally in Rogo. How did that come to pass? You know, Henry and his team met with me at a number of rounds before investing, actually. And so they were along for the story. They saw how we were developing, and they were trying to form a thesis on a lot of those questions you just asked of, you know, what is the need for a vertically focused company in finance? Is Rogo that company? What is Gabe like? And I think it became clear to them over time, wow, this is not just a technology that's going to be a plug-in in Excel and PowerPoint and help, you know, automate PIBs.
35:06This is going to be something that helps reinvent what private markets can look like, and it's strategic to us as KKR and us as Henry Kravis in thinking about private markets. And it's so clear that the only way to do this is to intimately understand finance and intimately understand AI and Rogo's best position for it.
35:23Allie Garfinkle:It's funny. You and I have talked about your round, but we've mostly talked about financial history. And one of the things I think is very interesting is a lot of folks in tech are very interested in the future. Whereas I feel like you have a real relationship to the past. and unlike venture capital which as a job is 80 years old or less maybe 60 or 70 depending on how you count um banking is a job that is hundreds of years old um what are you reading right now i'm reading house of morgan you're seeing you and i are going to both we're gonna be sitting here in like two years it's a long book we'll both be still reading ron turno's house of morgan probably.
36:08Yeah, it's great though. I mean, I do, I kind of, you know, go back and forth between science fiction and fiction and historical, you know, nonfiction or historical fiction. But finance, to your point, is a, you know, storied industry. And it's a very hard industry to break into, right? There's a lot of antibodies from all sorts of organizations, whether it's the banks themselves, the data providers, the exchanges. And so understanding how we got here, and why Bloomberg is the$100 billion business it is, or why the New York Stock Exchange exists, or why JP Morgan is the preeminent bank on Wall Street, it's very important to learning how to approach the whole industry.
36:48One thing I think is really important is,
36:53Allie Garfinkle:I don't know if we have real evidence for a 100-year SaaS company being able to exist necessarily, but there are 200-year banks. Banks can truly be multi-generational endeavors. What does it mean to grow with a bank? These banks are cemented within the fabric of the U.S. economy, the global economy, and they constantly have to reinvent themselves. And so for me, it's a fascinating moment because I can help them take advantage of AI and think about that next reinvention. And these are not organizations that change overnight and change quickly, and that's partly why they're still around. they are steadfast in what they offer.
37:36But this is a moment in time where if they don't radically reinvent themselves, they might not be around in 100 years. And so to be that partner that helps them think through how to harness technology and kind of take advantage of the moment is fascinating.
37:49Allie Garfinkle:All right, we're going to bring it all together. The moments around the past and the present, as you kind of think about both, what do you think this is most akin to in terms of a historical moment? Like if there's a good historical parallel for where we sit right now in finance, what is it? There's two that come to mind. One is the kind of flash boys moment in public markets, where, you know, it became increasingly clear that you could automate a lot of the exchange work and a lot of the, you know, floor of the New York Stock Exchange work. And as a result, there are a lot more participants in public markets.
38:28And there's been all these second order effects on, who can actually be a part of that ecosystem. And I think that's going to happen for private markets too. And then the second type of historical moment I think about is just the kind of invention of investment banking and the idea that this was originally an industry and a practice to help connect folks with capital to folks that needed capital or to connect businesses with businesses they wanted to buy. And a kind of return to that moment of what was the original purpose of high finance and a focus on that.
38:59Allie Garfinkle:And I think the place I want to end is sort of about Wall Street itself. You know, Wall Street is this really interesting place in the cultural imagination. It is both wildly famous and deeply mistrusted. And one thing I've been sort of turning over in my head that I would love to hear from you is, in 2026, why should the average person still care about Wall Street? Finance is kind of the lifeblood of the global economy, right? The way money moves around both at the kind of micro scale, how do I Venmo you to say thank you for buying me a coffee, versus how does a business literally think about buying another business?
39:44Or how does an economy think about raising capital or raising debt? I mean, that's how we kind of fuel global expansion and progress. And it is, you know, those are the arteries of innovation. And sometimes it happens behind the scenes. And sometimes people think that that's kind of a crass way to justify the greed of Wall Street. But I think at the end of the day, you know, that is really the value it provides.
40:10Allie Garfinkle:And that's it for Gabe. I think the tension around how investment banking jobs will evolve in the age of AI is a tension we are going to see play out for white-collar workers across America in the years to come. That's it for Term Sheet. I'm Allie Garfinkel, and we'll see you soon.
From the publisher
Gabe Stengel studied computer science at Princeton and started his career as an investment banking analyst at Lazard. Then he did something a lot of bankers think about but never do: he quit at 23 to build the AI that would automate his old job. After 30 VC passes and two grueling years, his company Rogo just raised $160 million at a $2 billion valuation, and 35,000 bankers at firms like JPMorgan, Bank of America, and his former employer Lazard now use it. Fortune's Allie Garfinkle sits down with Gabe to talk about the future of M&A, why some Wall Street workflows will never need a human again, and what AI means for the next generation of investment bankers.0:00 The Banker Automating Wall Street0:16 What "AI for Wall Street" Actually Means3:13 Inside the Billion-Dollar Deal Rooms6:07 Quitting Wall Street at 237:35 The Brutal Early Days & 30 Rejections14:45 Meet Felix, the AI That Never Sleeps19:55 Will AI Kill Banking Jobs?25:52 Competing With OpenAI, Anthropic & Google 30:08 Why a Finance Legend Bet on Him35:30 Does Wall Street Still Matter?
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