The Great Financial Services Debate

23 May 2025 · 49 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

The Newcomer Podcast Notes

Episode Title

The Great Financial Services Debate

Episode Overview In this special episode, hosts Eric Newcomer, Tom Dotan, and Madeline Renbarger discuss key insights from the Breaking the Bank Summit, a financial technology summit held in San Francisco. The episode features interviews with Gabriel Stengel (CEO of Rogo), Jeff Seibert (CEO of Digits), and Josh Reeves (CEO of Gusto), focusing on the evolving landscape of fintech, the role of AI, and the future of financial services.

Timecodes

  • 00:00 - Intro
  • 09:43 - Rogo + Digits Discussion
  • 28:13 - Josh Reeves, Gusto Interview

---

Key Discussions

Event Summary

  • The Breaking the Bank Summit featured discussions on the resurgence of fintech, with a notable emphasis on the role of stablecoins.
  • Attendees included notable figures from the fintech industry, creating a dynamic networking environment.
  • Stablecoins emerged as a central theme, alongside the discussions on how AI is influencing service-based businesses.

Debate Highlights

Rogo vs. Digits

  • Gabriel Stengel (Rogo):
  • Rogo aims to replace traditional investment banking analysts with AI-driven tools for investment analysis.
  • Focuses on augmenting the roles of human analysts rather than fully replacing them.
  • Jeff Seibert (Digits):
  • Launched a competitor to QuickBooks that automates small business finance, emphasizing accuracy.
  • Advocates for traditional machine learning instead of relying heavily on large language models (LLMs) for critical accounting tasks.

Major Themes

  1. AI in Financial Services
  2. The debate around whether fintech startups should pivot towards service-oriented models enhanced by AI.
  3. Matt Harris from Bain Capital Ventures highlighted the significant market opportunities in financial services, valuing it at $33 trillion.
  1. Service-Oriented vs. Software-Only Models:
  2. Companies like Rogo and Digits embody different approaches:
  3. Rogo leverages AI for enhanced analysis capabilities.
  4. Digits focuses on automating traditional accounting processes without becoming a full-service firm.
  5. There are concerns about balancing human oversight with automation, especially in compliance-heavy fields such as accounting.

---

Insights from Interviews

Gabriel Stengel - Rogo

  • Vision: Automate the role of investment analysts to enhance decision-making speed and efficiency.
  • Current Approach: Focused on augmentation, providing tools that support rather than fully replace analysts.

Jeff Seibert - Digits

  • Mission: Create an AI-native accounting software that automates tedious tasks and provides real-time financial insights.
  • Cautious Optimism: Emphasizes the need for accuracy in accounting and the limitations of generative technologies in this space.

Josh Reeves - Gusto

  • Customer Focus: Gusto specializes in serving small businesses by automating payroll and compliance tasks.
  • Future of AI: Believes AI will reshape product development, enabling faster and more accurate service delivery to customers.

---

Key Takeaways

  • Fintech Resurgence: The enthusiasm around stablecoins indicates a renewed interest in fintech, with stakeholders eager for innovative solutions.
  • AI Integration: The use of AI in fintech is evolving, with companies navigating the balance between leveraging technology and maintaining human oversight.
  • Market Opportunity: There is a significant push for fintech companies to explore service-oriented models, but the complexities of managing such businesses remain a challenge.

Reflections

  • The podcast emphasizes that while AI presents exciting opportunities for automation and efficiency, the foundational need for human judgment and accuracy, especially in finance, cannot be overlooked. The discussions also underline the importance of understanding customer pain points and aligning business strategies accordingly.

---

For more in-depth discussions from the summit, visit the [Newcomer YouTube channel](http://youtube.com/@newcomerpod).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Hey everybody, welcome to your episode of Newcomer. Tom Doton here joined by Madeline Renbarger and Eric, Newcomer of Newcomer. We're all in San Francisco right now, but we're not all in the same place. actually. Madeline and I are holed up at our friend Volley's offices, which is as close to Newcomer HQ in San Francisco as you can get. I would say this is the Newcomer Satellite office. Absolutely. You got to come in. We can't all be in the same place for security reasons. We don't want all Newcomer employees together. It was dangerous enough this week. Yeah. Well, right. Good transition to the reason we're here, which is that we are fresh off the Breaking the Bank summit, the FinTech summit annual thing.

0:40Although what is it? The second year you've done it? Well, the first year we called it the newcomer banking summit and we realized FinTech was much more exciting than banking. So in some ways, this was the first year and in some ways it was the second, you know, that was a little awkward on stage. It's like people are coming back, but this is the first time. But yeah, this was our first pure FinTech summit with some returning faces. Right. There were some returning, returning faces like Jackie Rhesus. Yeah, Matt Harris from Bain Capital Ventures came back for presentation round two. Big hit of both events, I would say.

1:12All in all, it was a lot of people across the fintech world. It was fun kind of getting to talk to them in between sessions at the after party as well, which was exclusive. We try not to talk about the after party. Don't tell them. You know, I ran into like the guy who got viral because he was trying to have people take out debt to make investment accounts. I don't know if you saw that the other day. I think it was like basic capital who I had no idea was even going to be there. So that's what I love about these events. You know, we try to get great founders there and then I'm like, oh, yeah, I've heard of your company.

1:45So, yeah, it was a good crowd and then excited about what we have to share about what happened on stage. Conversations ranged from a ton of different topics around fintech. I mean, the premise was, you know, fintech is back, baby. And then, you know, we had to go on stage and really ask, is it back? But stable coins certainly are back. The big resonating theme of the day was everyone is super pumped about stable coins. It's really talking about stable coins is back. Tripe had done a billion-plus dollar acquisition of Bridge. We had the Bridge CEO as the second person on stage. Jackie Rhesus at LeadBank is a bank that's really backed stable coin fintech companies.

2:23So we definitely opened the day strong with people who were excited about it. I mean, later in the day, too, we had, you know, Eric Gleiman from Ramp, who has launched with Stripe and Bridge for a stablecoin card. Yeah. Yeah. I mean, in the background of all this, you know, Tether is making more money per employee than almost like any company in history off of stablecoins. So everybody sees that there's like a ton of money to be made. And of course, Congress was passing legislation right as we were holding the event to make stablecoins much more legal to do or clearly legal. So, yeah, I think that was theme A.

2:58We've decided the selects for this episode will be from theme B, which I thought was equally interesting. Yeah, theme B. I mean, there was a big debate that I feel like is still kind of unsettled, which I find interesting. So we'll hear different perspectives on it later. But around, you know, the idea of AI enabling startup founders to go after service businesses, you know, like accounting, legal tech services. but accounting, especially since this was a fintech summit, and where the merits are around fully pitching your startup as a service business that can be fully enabled with AI, or rather sticking to software and being the software provider for these businesses.

3:35Matt Harris of Bain Capital Ventures gave a presentation which I think captured some of the venture capitalists' sentiment well, which is financial services businesses are enormous. You know, you think about accounting or broader services businesses like law. There are many, many, many billions of dollars of money to be made there. But of course, they're human intensive businesses, the kind that tech companies traditionally shy away from. But the argument is that now, thanks to large language models, startup founders should go after those categories. And Harris was arguing basically definitely good for startup founders, maybe not as good for venture capitalists because they're still going to be, you know, you might out operate a law firm, but you're not necessarily going to build, you know, a Facebook.

4:22So that was Harris's argument. And then as you're going to listen in these conversations, I put that question to Digit CEO Jeff Siebert and Rogo CEO Gabriel Stengel in our first conversation. And then I talked with Josh Reeves, the CEO of Gusto, probably one of the most experienced founders we had on stage, and asked them, you know, do you really want to run a services business? Jeff at Digits had really stood up in accounting practice to build their QuickBooks competitor. And then Josh at Gusto certainly has built some of these services businesses. But again, I think to sort of see if they can build software.

5:01So where did you guys net out in terms of the argument? Matt Harris, back to his presentation, he ended very strong in an interesting way by basically saying, I'm tired of nibbling around the edges of fintech. You know, this is a$33 trillion opportunity, which I guess means all banking around the world. Well, it's also including accounting. It's including accounts receivable. It's including, you know, health insurance, brokerages, as much money as possible that, you know, any money industry. I don't know if you guys heard this, but it elicited a whoop from Jackie Rhesus. I at least heard it. She was right in front of me while he was talking.

5:33She also sent me an email saying she loved that quote too. So yeah, she clearly agreed with that idea. Well, who wouldn't want to be part of a$33 trillion opportunity? But I think that kind of speaks to the challenge that fintech has had, which is like, is this just some sort of, you know, skimming of businesses that the big banks and other financial institutions aren't already taking? Or is it like truly disruptive? Right. Is fintech Venmo transfers, weird loans, helping people, you know, finance their burritos? Or is it, you know, the core of the American economy that big services companies have been able to deliver or a bunch of small ones, honestly, a lot of small businesses doing accounting and law and all these things that they want to tackle.

6:15Right. And like bringing it back to like large language models, like, is this the entry point to this larger business to this larger opportunity? Or, you know, are we still going to be about these kind of marginal disruptive plays that can build real businesses like Klarna or Affirm, but aren't, you know, I don't think are really necessarily taking 33 trillion as the opportunity there. I will say, I mean, the success of Rogo so far, you know, they're basically building an AI agent that can automate the work of an investment making analyst, which is very specific, but has taken off, especially in an industry where, you know, unlike accounting, you can get most of the way there.

6:53And people will say, you know, this is good enough. We got this done. And so that is one place where I can see the service automation be very promising. But that being said, it is a pretty specific service that they're automating there. So we'll see how that expands. Accounting, of course, you know, it's tricky because you don't want to mess that up. I think that's a key point, right? Gabe with Rogo is, you know, they're trying to replace like the Goldman Sachs analyst or even and just give you a sort of cheap analyst that has a rundown on companies you care about. You imagine the banker's already going on ChatGPT and be like, quick, before this client meeting, tell me the download on this random oil and gas company I've never heard of.

7:32And so there, it's like Rogo doesn't need to be 100 % correct. They just need to be better than sort of the lazy version of this. And obviously, they have aspirations to be much higher quality than that. But they don't need to be 100 % correct. They need to help you get pretty broad coverage and be able to move quicker than you can right now. Whereas accounting, as Jeff was saying, you know, you need to get it right. And, you know, a lot of what they would need language models for is sort of the boring business of tagging all your expenses, which somehow is still a task that's like cannot be fully solved by technology right now.

8:09And so he talks about how they use machine learning for a lot of the tagging because he finds it much more accurate. And then when they really can't figure it out, they sort of see if a language model can sort of crack it, but they're not really relying on it. So, Madeline, I think exactly like you're saying, it really depends what business you're in, how much you trust language models that aren't totally consistent. You know, Jeff made the point like, well, ultimately, you can't sue the AI. So if you mess up my accounting books, like you'll sue the CPA. So there's different stakes. You know, the last thing I'll point to before we throw it to you can listen to them.

8:46I did all that reporting on Bench, the accounting firm in Canada that blew up where the founder basically said, oh, if you hadn't pushed me out, this might have turned out differently. And, you know, you can read those stories and it had a lot to do with the particular investors and executives. there was this sort of lesson that building a startup that hires a bunch of accountants is a big headache. And so building a tech company where you're going to try and hire all the people and then slowly figure out how to do it better with software, it's hard to guarantee that you can bridge that gap. And then one day you may find yourself just operating a regular accounting firm and your investors want you to have the margin profile of a hot startup and then you're in big trouble.

9:32Good recap of the event, guys. And I think now we should just kick it on over to two of the highlights of the event.

9:44Very excited about this panel. We're going to have a great discussion about what is possible with artificial intelligence in fintech. We have two of the very well-financed, cutting-edge startups here. Both of you can certainly claim that. Gabe, you want to start with Rogo and just give the quick like what you guys are doing. Happy to. Thanks for having me. I'm Gabe. I'm the CEO and founder of Rogo. We're training an AI analyst for investment banks, private equity firms, and hedge funds. We're a series B company backed by Khosla, Thrive, Eric Schmidt, and a number of other folks deployed at a number of public investment banks, large alternative asset managers, large public equity investors.

10:23And you're replacing the banking analyst, right? Not yet. Not yet. Supporting the banking analyst. Right now, I mean, everything can be broken up into augmentation and automation and we're much more on the augmentation side still, even though, you know, I think we and a lot of folks see that changing quickly. And Jeff, the digits story? Yeah, so two months ago we launched the first feature complete replacement to QuickBooks in 20 years since Xero came out. It was a long build. We started the company in 2018 and we're basically in R &D stealth mode ever since. And so our goal has been to basically automate and make small business finance real-time, intuitive, actually helpful to the business owner, not put them in a position where they're waiting two to three weeks to get a black and white P &L, which is sort of where they are.

11:04You're coming for QuickBooks, basically. Yes, 100%. Yeah. And there are lots of problems with QuickBooks. Some of them have nothing to do with what a foundation model could produce. And some do. How do you break down, yeah, how much of what's making digits different has to do with things foundation models can produce? So it is pretty fundamental. I would broaden it to machine learning. So when I started the company in 2018, our premise was, can we build the first GL, a general ledger for accounting, that's ML native? We honestly got very lucky with this whole AI wave. Now it's AI native. Great.

11:37Okay. But we primarily do traditional machine learning. If you look at accounting as a field, it is predictive. It is not generative. You do not want an LLM hallucinating your books. And so we custom train and run our own models in production. We do fall back to LLM foundation models as sort of a worst case scenario. But our story to the industry is we are automating the bookkeeping. We automate 93 % of it today. And what's unique about the accounting industry is they want that. They are, as a profession, trying to up-level the profession away from bookkeeping and into advisory and sort of client communication work.

12:12And so that's what they're going for. Basically, you use machine learning, tag expenses, get it 100 % right. And then if your tagging system doesn't work, you're like, all right, we'll try an LLM and see if it's sort of more free thinking style can tag it itself. That's the right way to think about it. So if a business has seen the transaction before, our predictive models are effectively 100 % perfect. If the transaction is novel to the business, we then fall back to different tiers of models that ultimately result in an agent. Like what does your bookkeeper do if you have something totally new?

12:42They Google it. What does the agent do? It Googles it. Gabe, I don't take that as the most optimistic view of what LLMs can do. It's sort of like, oh, we have our accurate ones, and then we have our guy who Googles things, and sometimes he's helpful. You're much more leaned into LLMs can deliver real value to bankers. What's possible right now? How accurate is your software? It's funny. Jeff and I were just discussing it backstage because we have two very different products and very different users. If you get financials that are not 100 % accurate, and you are a small business, and you don't know how to go in and audit those books yourself, that's a pain.

13:21If I give something that's good enough for an associate to check, maybe as accurate as their first year analyst who's not perfectly accurate, that's actually very value additive. Part of the benefit we had is that when we went in, folks were used to using products like ChatGPT. And a lot of our early users realized these tools can be very valuable without being 100 % accurate. And so, I mean, the last thing I would ever say when selling is that we are an 100 % accurate tool. What I would say is you can get a lot more value than you think before they're 100 % accurate. You need to be better than someone who's right out of college, and you need to be better than a lazy banker using ChatGPT.

13:56Exactly. And as we learn, right, the way your intern learns to be an analyst, learns to be an associate VP director, when we're at director level, we're not going to get wooed by a better paycheck somewhere else, and all the enterprise value isn't going to walk out the door and go to a competitive bank. And what, I mean, what's the coolest thing you can do today? Like, where do you think Rogo is really excelling? Like, what is the sort of query? I mean, it does things that, so I was an investment banking analyst at Lazard. I did buy-side M &A coverage for healthcare companies, and I didn't know anything about healthcare companies.

14:27And we would help large biopharma companies spend$5 billion to buy biotechs. And it can do almost all the work I did in the analysis of those companies, right? Like, looking at their R &D pipeline, thinking about the different sort of oncology areas that might be additive for Johnson & Johnson or someone similar, and then preparing a presentation on why it would be additive to J &J's overall M &A strategy. I mean, we can put together the materials, diligence the company, look through their financials, do a lot of what these folks are doing. Jeff, I mean, we saw sort of the presentation from Matt Harris earlier, which is like, get into the services business.

15:04And I wrote last year a fair bit about like bench accounting, which tried to sort of do accounting plus the actual accountants. I mean, you're going after QuickBooks, right? You are not building an accountant team. I think you've used some accounting firms to sort of understand your product. But why not go, I guess, whole hog and say, we will be your accountant. We know how to use our software better than anybody. We'll take advantage of it and do the whole thing. This is such a good question. So just to clarify, we actually do have an accounting team. We do have an accounting firm. Some of you may have seen our billboards.

15:36we do full service accounting for hundreds of top startups now. That is not the business that we are not scaling that. Okay. I was like, I didn't think I was that wrong. We do it, but we're not going to do it at scale. So we have capped the client count. The reason we did that is we need to present a model firm to the industry. And so if you look at the accounting industry, they are of course traditionally relatively risk averse, relatively slow to adopt new tools. The cloud transition took them 15 years. I'm not joking. And so we want to accelerate that a bit. And so we did build out a model firm to show you how you can run digits as a practice.

16:08That is not the core business. And so I do think there's been a trap in the space. If you look at some of the well-known sort of previous offerings that have tried to build a services business with some internal tech. And I mean, you even see Atrium that failed at that in the legal space. I think it's incredibly hard to bring together a software business and a services business and actually scale it to high margin. And so we've been really disciplined on, we hire software engineers, it is a software product. Like there is no slippery slope of humans doing any of the work. Why has QuickBooks been able to hold on so well?

16:40Yes. It's a marketplace product, believe it or not. And when QuickBooks came onto the scene in the early 90s, it also had taken them five years to build. They were sort of building on the backs of the personal computer revolution. For the first time, you could really do accounting for your own business, like in your own office. And the problem is you need both the business owner and the accountant to really buy in on I'm going to use this software. And now 30 years later, accountants view it as a career choice. It's a religious preference. Like I'm a QuickBooks accountant. I'm a Xero accountant.

17:10I'm a NetSuite accountant. And so that's the barrier to break down. Fortunately, there is a macro trend in our favor. So 33 % of fewer people are pursuing CPAs. Gen Z does not want to be an accountant, which you may or may not blame them. And 75 % of CPAs are at retirement age. And so they're seeing this talent crisis as the sort of final motivation of, okay, we need to actually change software. We need to automate our role. We need to up-level the profession. So I think that trend is very favorable. Gabe, you know, I want to sort of give a guidebook for other companies. You know, you're sort of at the cutting edge of using language models in your business.

17:48I'm curious how much you think what we've seen with ChatGPT is an endorsement of text-based exchange interfaces like do you think the regular person or your banker customer wants to type in queries and get great responses or do you think that's sort of an entry point over time it's more and more like software look I think we're lucky in that we we have a lot of users who use the product we have today I don't know if that means we have you know any predictive abilities about what that UX should be five years from now for me the abstraction is what is the easiest way for me to communicate with someone on my team, it's probably Slack, email, text message, phone call.

18:27You know, if I ask for a deliverable, I get sent a PDF, I review it. Occasionally, I'll jump into the PowerPoint, the Excel backup myself. I think that's a very human way to work, and there's a lot of throughput in that. You know, you can communicate a ton. I think at the limit, that's what you want these interfaces to look like. If you're building an assistant, if you're building, you know, an analyst replacement, if you're building Jeff's business, you know, I'd rather just have my books integrate directly into whatever systems those need to go into. I don't know anything about accounting, unfortunately.

18:56This is great because this is such a product-specific difference. As a startup founder, business owner, I don't want another person to manage. I don't want another thing to talk to. I just want the accounting done. And so we very explicitly have no chat UI in the product. The data comes in. It is booked. Where the output of Rogo, I mean, an analyst would produce a report. So it's not that unusual. Yeah, I guess. But the way you would iterate might be, hey, why'd you do this? Hey, add a page on this. hey, are you sure that was the post-money valuation for the company in the comp set? But I mean, for Jeff, it's like, I don't want to hire an FP &A person, right?

19:29We're getting to the scale where it's like, we need someone, and I really don't want to do it. I'd rather just have those systems work. And I don't want to talk about it with someone either. Right. Are you an evangelist when you talk to other fintech founders of like, they should be applying foundation models to their business? Or are you more on the side of like, we picked the right area. It makes sense where we're doing it. And like, I don't know if it makes sense for your business. Yeah. I was, I, yesterday at Coastal Ventures is one of our big backers and, and they had a big summit yesterday and, and something that one of the speakers kept hammering was it's very hard for incumbents in a space to innovate, to brainstorm this sort of, you know, not just the incremental way to apply LLMs to your business, but the whole new business model that emerges.

20:10And part, partly why Digits is so fascinating is because it's innovating on the business model in addition to, you know, the actual technology. but I mean I was pushing Jeff in our, we had lunch together to catch up before this and I was saying it sounds like you're not using LLMs enough and he had a great retort and he obviously knows his business better than I do but I mean I think anyone who's not trying to use these tools in kind of a step change way as opposed to an incrementalist way is waiting for someone else to. Jeff, you're an incrementalist. This is great, no I mean to be clear, we do use LLMs, we do use agents, we've been running in production for 18 months now.

20:44I'd say we are extremely disciplined on making sure we can guarantee the accuracy of the output. And so for an example, like where we do use LLMs, we actively prevent them from doing math. Because yes, they've gotten better at math, but they can still slip up. Our team literally wrote an RPN calculator tool that we give to the LLMs, and we tell them, if you need to do math, do not try, use this tool. And so there are a bunch of things you can do to put safeguards around it. What do you think about that? Well, you know, I think it's kind of the analogy I would use, and it's going to be a really strained analogy, so bear with me, but the sort of Jeff Bezos thing of, you know, your margin is my opportunity, your accuracy threshold is someone else's opportunity.

21:24Because they're going to build something that's not going to work today or tomorrow, but all of a sudden the base models will be good enough where you could skip all these layers of complexity and structure to, you know, make up for that accuracy, and suddenly, you know, they will have some of that more human reasoning and be capable of so much more. I don't know if that's right in Jeff's domain. You're saying you're partially betting on the continued improvement of the models, and if you spend too much time fixing the models today, you're missing out on the savings of the future? The problem is how do you thread the needle?

21:51How do you get enough adoption and traction today to validate putting more in R &D for the future? And depending on how accurate you need to be, yeah, you might need to do some anachronistic things or just throw LLMs at every problem, right? You don't just want to use LLMs for everything. But I do think that if you aren't willing to accept some faultiness, some bugginess, some hallucination in parts of a product, someone else will. And then someone else will potentially figure out the new product paradigm or UX that's going to work when the models just get 10 % more reliable. Jeff, we're in this moment where people are like, oh, we don't need software anymore.

22:32You can use a coding agent to build it. like I'm going to build my own custom model, like why isn't the next digits just like a homebrewed version of zero instead of like your company? Right. Now this is a really good question. And can you imagine the models get so good that you don't need the accounting software at all, right? And like could the model just you give it your data and it does your books? Right. I don't think that is the future you want because ultimately this is still a workflow. It's a real business process that you need everyone involved with. You need user accounts, permissioning, notification, sharing, like you need an actual experience.

23:07And so even to the extent we invest in the AI, I do think it comes down to you also need to build better accounting software, right? And it's the same thing I would say with Figma. It's like, okay, I don't think Figma is disappearing. It can help you. It can automate a lot of the stuff, but you still ultimately want a canvas your team can collaborate around. And that's how we view finance. Like if you could picture a Figma for finance, what would it be? So we try to look at it as a broader product perspective where the AI is a core tool, but it's one piece of the entire vision. Just like if you were to build, like, oh, Redis came out.

Read the full transcript

23:39Now do you not need a whole other, like, class of products? You sort of still do. Like, Redis is great technology, but you still need the actual experience around it. Do you think we're close to you having the problem of someone gets an accountant who that accountant is using language models that are trying to interact with your software, and then you're trying to figure out how much to serve them? Or have you started to see that, or are we too early? We're a little too early. The accountants aren't that quite. They're not the cutting edge of agents. But we think deeply about the collaborative flows.

24:09Like the accountant is in the picture. And this is actually an interesting point for folks. As we talk with business owners, they do not want AI accounting, i.e. the AI does 100%. They actually want the AI to do most of it. And they want their books blessed by a real CPA. Because you can't sue the AI, right? You need someone to sue. I need a human. I can blame. And so that is actually really, really important. And that's why the industry is not going anywhere. They will up-level and be able to serve more clients, but you still need that human to have blessed the books. Gabe, the wrapper question.

24:43I mean, we sort of, in the presentation earlier today, we've moved to a point where it's okay to be a wrapper. We don't use that term because it's pejorative. I love to use pejorative words positively. I've been on the case. It's like, no, you differentiate on the product in software, not necessarily on the model. How would you calibrate that in terms of how much you need to have, at some point, your own models, your own thinking, or we're going to be the best at directing ChachiBete and Anthropic and everybody towards our use case? Look, it kind of goes back to how Jeff answered the question, which is even if you have a profoundly intelligent model, you still need the tools to do the accounting workflow, right?

25:23It's like even if you have a robot that can move the way a human hand, they still need a drill to go install whatever they're installing. For us, we're building the tools that some eventual agent intelligence, either owned by us or someone else, might use. Whether that's an Excel interface for an agent, whether that's a PowerPoint interface, whether that's structured financial data querying or unstructured financial data querying, or integrations into the internal data systems of the banks and private equity firms we work with. That said, I think it's very clear that reinforcement learning is working and post-training is working on top of these frontier models.

25:57and with very great specific evals, you can actually outperform the frontier. With post-training alone, you can find a lot of technological differentiation that makes it more valuable. Yeah, I mean, I think that's what early results are showing. I don't know if there's... I mean, actually, Cognition had a great paper that they... I mean, not paper, it was a Twitter thread. But it was a great Twitter thread. That sums up something in the current moment. It was a great Twitter thread. Like, maybe a week ago, They had post-trained a model with RFT for writing like CUDA kernels or something that's quite difficult for O3.

26:32And they got a lot of outperformance with the types of technologies and reinforcement techniques that are now diffusing through industry. And so I think we'll start to see a lot more of that. It reminds me of when folks used to overclock their CPUs. And now CPUs are fast enough where no one really bothers as much. Yeah. No, no. I mean, it's totally possible. I mean, I think the way that I think about RFT in post training is not necessarily that it's going to make the model smarter, but it's going to sort of prune the decision tree and make it better at using your tools, right? So, like, OpenAI is never going to have your tool structure and its training data unless you collaborate with them.

27:04And so the same way if you get a super smart human starting at your firm on Monday, they're going to need to learn how to use QuickBooks and Xero and, I hope, digits. You know, the model, you want to teach it how to use those tools, too. Yep. Jeff, last question, last word. Would you tell a founder today to build a services business powered by AI? You've done the sort of flirtation with having the accountant firm. Do you buy that investor narrative, or do you think it's oversold? I think it's oversold, and it's so tough because it is such a tempting narrative. It's build your services business, look at what's slow, automate that, move on, right?

27:38You can drive a high-margin business. The change management, the actual people management is so challenging because it depends on which profession you're trying to automate, but there's so much built in just like native practices in that profession that in order to really automate everything and build the trust, it's a long journey to get to that margin versus just trying to do it in software. It turns out people outside Silicon Valley, they know their businesses too. They're hard businesses. Exactly. Right. And again, with accounting, accounting is complicated. Like there is no way to simplify that.

28:06Great. Thank you very much. Thank you.

28:12Super excited about this conversation. Two things. One, Gusto's the rare startup where I sort of have a rooting interest in that we are a small business. And every time Gusto solves a problem, I am relieved that you get to take it off my plate. The second thing is it's funny to be hanging out with you with shoes on. Do you guys still, have you gotten rid of your no shoes policy or are you still? I feel like I have to give context to people here. So excited to be here. This is a fun space for me because we had a Gusto holiday party here in 2015. But our three first offices were only a block away, and we were raised by our parents to take our shoes off at home.

28:49So for many years, our offices were shoes off, walking around in slippers, socks. We passed them out to folks. And then when the pandemic started, obviously, people can do whatever they want at their home. Today, it's more of an optional policy. But I do describe it as a tradition that felt right for Gusto at the time. You know, yeah, in some ways it's like you've become this grown-up company. Can you give, you know, obviously payroll is at the heart of it, but talk through just briefly what the pieces of Gusto's businesses are today in terms of the focus and where you're really strong. So something really important to know about Gusto is we obsess over a small business.

29:26So if we have any customers here, we're honored to serve you. And just know that there are more dentist offices in the U.S. than tech startups. And so we really focus on mainstream small business. Of the six million-ish employers in America, two-thirds are less than five employees. And so with that customer focus, payroll is our first product. I always like to say if you don't pay someone, they quit. So it's a pretty non-optional product. So we're really happy we started there. But kind of broadening through the back office would be the way to describe it. We really obsess over customer pull versus company push.

30:04But benefits is a big investment area for us. There's many, many types of benefits. Something I know we're excited to get into more, we have a pretty broad product group inside Gusto called Gusto Money that's focused on things related to cash flow management. For a lot of our customers, their biggest expense is payroll, paying their team. And one of the biggest points of stress is when APAR don't line up and they don't have the money in their bank account at the right moment to fund payroll. So we launched bill payment not too long ago. Actually, next Wednesday, we're going live with invoicing.

30:36So you'll see us do a lot more product investments, more in that B2B FinTech part. But again, really, really focused on small business. And overall business, sort of somewhere between 500 million and a billion in revenue? Yeah, you can describe it that way. We serve over 400 ,000 companies. I mean, one fun way, we always ground it in customer. We're in the range of 8%, 9 % now of all employers in America. And with the business model, that leads to good revenue. We've been free cash flow positive for many years. We reinvest that money back into building new product to solve more pain for our customer.

31:10And I mean, you're an important sort of partner to other fintech companies. I know, I think the Guideline CEO was here at one point. What do you see in terms of like the partnership strategy for Gusso? Yeah, so a big part of our approach to, we're here to build a multi-decade company. We're still early in the journey, even though it's, you know, over 10 years. And that to me is a factual statement, right? We're only at about 8, 9 % of employers. You still have 30 % of companies in the U.S. doing even things like payroll by hand on pen and paper. So with the obsession on small business, a lot of what we're doing is replacing manual process.

31:46But there's just a lot of other pain points we want to help with. And if we're going to get there, it's not going to be entirely through first party products. So we've had a playbook, which we will continue to use, of choosing product by product. Are we going to build? Are we going to partner? 401K is a good example where we've partnered historically. And then there's also, obviously, acquisition. We've done that a few times. We'll do that more going forward for where we deem something that was third party becoming first party. But we're not going to build it all ourselves, and we're excited to partner where it makes sense.

32:16has artificial intelligence changed the pace of product development i mean you're you're an interesting case in that on the one end it's sort of the you know i don't know clarna's the world where they're like well we'll build everything internally like you know payroll could be imagined that way on the other hand it can accelerate your growth like how do you how are you seeing sort of artificial intelligence the ability to build faster impacting gusto today i mean i'm surprised Why has it took this long to get to AI as a topic? I mean, there's so many threads. I think a lot of folks here are technologists.

32:48I'll have to just choose, like, on productivity and how we build. We have 1 ,000-person plus R &D team. I don't think we're that different than most software companies in that it's obviously driving a pretty meaningful shift in how we build, you know, the iteration speed. I think we're going to talk later about, you know, there's the service as a software, software as a service. Everyone gets SaaS. A lot of what we do is taking stuff that involves compliance, involves manual filings, and digitizing it into software. In the past, I said we use paperless cloud mobile. Now, obviously, AI is a key ingredient to that.

33:24But that's on the more internal how we build side. It doesn't mean fewer engineers, just to put a fine line on it. Yeah. It doesn't mean fewer engineers. Given the scope of our ambition, it means the amount of work we can do per Gusti grows dramatically. But probably in the grand scheme of things, it means less hiring than if AI didn't exist. But we're also pretty ambitious, so we're doing a lot of hiring anyways. But it's because we want to go solve more pain points for our customers. And then on the sort of, do you feel the threat of customers building in-house versions of Gusto? Honestly, as a small business, that's sort of incoherent, right?

34:02Because it's like, I'm not going to build an AI team as a five-person startup. It would matter more to your enterprise-level competitors, or how do you think about that challenge? I mean, I don't think too many dentists want to go build software. That said, the reality is most of what we're doing for a dentist office or other small businesses, they haven't had access to in the past. They've been on their own. They've kind of had to do it manually or just not do it. And so for us, AI is enabling products to exist in a small business category that never existed. I think in mid-market enterprise, you're navigating more of this complexity of displacing jobs.

34:38but our due north is to like grow the small business economy right and so we want to bring all of the things big companies have had historically to a small company the only way we're going to do that right with a ratio that makes sense and with a scalability that makes sense is through leveraging technology I mean if I did this still the angst of a small business it's like I want to know that I'm in good standing and I don't know everything I'm supposed to do and you guys are good in the product sometimes we like you know in New York you're supposed to have sexual harassment training. Okay, I'll pay you some money for that.

35:09Do you think AI is going to move us further along of just being able to give me an assessment? Have you done everything you're supposed to do? I call that the am I good question. Our customers, including you, do not want to be stressed or worrying about that. It's our job to make sure you know fully if you're good or if there's something you need to do what that exact thing is. If we can do it for you, even better. But yeah, compliance maps to most of our products, right? Payroll involves a lot of compliance. Time tracking, PTO involves a lot of compliance, local, state, federal rules. And so AI fits in there in terms of like ingesting.

35:48But at the end of the day, it's a compliance engine where accuracy needs to be to the like, you know, six sigma. And that's always been true. Pre-AI, post-AI, that's been true since we started the company. How much do you think your customers want to talk to the product? Like, do you see a move to text interfaces now that they're more capable? Or you're like, we really need to flow whatever advances we have into actually the layout and design of the product? So we always start with, like, small businesses are busy. And it's way too hard to run and build a small business still. You can attest to that.

36:21And so how can we help them? We can help them by saving time. We can help them by taking 5 or 20 or 30 of the hats on their head off their head and doing it for them. Pre-AI, I would say we did that through really clean, elegant, easy-to-use workflows, primarily in a web app or a mobile app. That's gotten us pretty far, right? Like, that's what we're known for. Anyone can use Gusto with no training, no background in running a business. We have high NPS, high customer satisfaction. Our primary way of growing is word of mouth. With AI, it's not about the technology. The interface, that's what we get excited about.

36:55A conversational interface for a lot of use cases that Gusto does is a more intuitive, more accessible way to use Gusto. You like it. You think it's promising. We think it's very promising. Our interface for that is called Gus, which people should hopefully get. I think it's somewhat like this, right? And then, yeah, well, Penny the pig is a little mascot. Oh, that's a different logo. Okay. But then you're, like, cracking Penny in half, but, like, Penny's being sacrificed for the sake of your conference. But yeah, conversational interface, we don't think replaces web app, replaces mobile app. It's just a different surface area.

37:28But we are taking 14 years of functionality and giving Gus those superpowers. So we have customers today, thousands of customers, using Gus to go create shift schedules. You want to go change who's working which day, take Sally off Friday, add 20 hours to Jim. We go do that all for you. You can just tell us that in a conversational interface. Or you can go through and navigate, but that saves time for a small business, which they really appreciate. I wanted to put one of the big themes of today to you. I mean, we saw Matt Harris give a presentation where he's making sort of a case that other investors have also made, that it's like there's now, thanks to language models, this opportunity to go after services businesses and sort of be the services business while being a tech company.

38:15Then later I had Jeff, the CEO of Digits, who's building accounting software. He's hired accountants to figure it out and then software. And I think he was much more skeptical of that sort of you can be a services tech business. Where do you land? You've built a big business and you touch a lot of services. Are you bullish on that argument? So I think we've had a kind of unique perspective to this because the first product we launched, Payroll, mostly if you put aside like ADP paychecks which are a minority of the market the majority of companies in America did payroll by hand or with a local payroll service bureau which was basically a service manual localized business solution so a lot of our journey has been taking and did it with health benefits right we are a broker there are thousands of brokerage firms across the country that mostly do things by hand so we take these complex compliance centric spaces and we do what we do best, which is we digitize the heck out of it.

39:16Because if we're going to go do it for 400 ,000, 500 ,000, a million businesses, we cannot do it ourselves, mainly. So I don't think it's a 0, 100, 100, 0. We have operations teams at Gusto, but we have over 400 ,000 companies today. Our Gusti to employee ratio is over 1 to 1 ,000. That's only possible with technology. Right. So you only want to do it if you can get to the point where it's fairly automated, not sort of for a long time keep the humans sort of trying to figure it out? Or yeah, how long do you spend sort of like, we'll do the human business to try and get to the point where we can automate it before saying, oh, I guess this is sort of, at least with the technology today, a perpetually human business?

39:58Well, we were joking before, right? Like if a company is scaling a service offering to large, large volumes and it's staying service-based, that's to me not a tech company. That's just a service business. Different multiple profile, different overhead costs, different operational complexity. We work backwards from what's best for the customer. For us to solve these pain points, it has to be technology. It has to be digital. It's just more accurate. We process several hundred billion dollars a year of payroll taxes. If we were doing that manually, it would create human error potential. It would be too time consuming.

40:30So we digitize because it's a better experience. But when we're subscale and trying out new products early, early on, I think it's totally fine to start more manual. It's about getting that feedback loop going, getting that learning going. But that's typically with less than 100 customers, right? If we're going to scale something, it better have good unit economics, good CAC, good gross margin. And we should have confidence that it can scale in a technology-enabled way. Otherwise, we're just going to build a huge operations team. Somehow in payroll, you're in one of the wildest categories in Silicon Valley.

41:03You have, you know, like Rippling and Deal, you know, making huge accusations, obviously Rippling and Accusing Deal of spying on it. Have you done an internal check to see whether anyone's spying on you? And what do you make of sort of your high profile sort of same category businesses having so much drama? We just focus on the customer. Have you checked? Have you checked? We have a very, very intense, super, super expensive and worth it security team. Yeah. But that's because we have hundreds of billions of dollars of our customer money sitting in our accounts. And we do tax filings and tax payments.

41:50And we hold social security numbers and a whole bunch of very sensitive data that we take that job very seriously. So I can tell you with confidence, we do not believe anyone is spying on Gusto. But that's because that's what our customers should demand of us, that we're obsessed with protecting them in every possible way. Do you see much competition? I mean, you're very focused on small businesses, and I like that focus, and it gives you a great mandate and sort of a mission to motivate the company. On the other hand, most businesses want to keep their customers. It's like it's much easier to keep the customer you have and grow with them than to find new ones.

42:25How do you think about sizing up with your customers? So we're both in a very crowded space and a very fragmented space. And then, yes, I think it's even very simplistic to say small business, medium-sized business, large business. These are huge cuts. And even within small business, you have different industry types, different geographies. So hopefully everyone gets by now, we are obsessed with small business. We tend to see they're less of the kind of frothy, Silicon Valley tech kind of drama, frankly. But there's still legitimate companies that have lots of good product in market. Intuit is a company we highly respect and we compete with on multiple fronts.

43:09And there's a bunch of other companies. I used to say it was only Intuit, folks that have built really incredible franchises and small business. Shopify has a huge part of their company that's focused there, Square, Toast, HubSpot. So we feel like we're in good company. And I always encourage more entrepreneurs to tackle the small business category. The playbook still is generally for SaaS just to move up market and move to bigger enterprise. And in the past, that just meant small business was left. Do you want 100-person business on Gusto? We have a lot of 100-person business on Gusto. Most of them started on Gusto when they were one employee.

43:44So our focus is on small business, the vast majority will stay small. If some grow bigger, we're honored and happy to serve them. There's probably a point at some point where they graduate, but I like to remind folks, you know, that's very rare, right? Like the number of companies that start at one or two and grow to a hundred in our entire history is less than 0.1%. Is a, you know, we all at the end of the day, live or die by the economy in some ways, and you have a great sort of vantage into a part of it. is small business in America strong right now? What's your read of the mood among your customers?

44:20Yeah, so we have economists on team. We publish a lot of content under Gustonomics, and a lot of folks are interested in the data. I'd say high level, two things we track a lot, new employer starts and then net hiring across our customer base. I'd say on the second, that is quite depressed. New hiring. New hiring, net hiring, so just the propensity of our customers to add more to their team. that's been depressed for a few years now. On the new employer starts, that really with the pandemic got dramatically elevated and it's stayed fairly high. But yeah, it's more interesting to track given our size and scale.

44:56We feel like we're pretty diversified. It's more just net-net a bet on small business broadly and it tends to be a pretty durable segment. Can you talk about the embedded payroll part of your business and sort of, I mean, there is this other trend of API-based businesses right now where it's like, okay, you're helping other people interact with your service, but not necessarily building out the product yourself. How do you think about that as a piece of Gusto's business? Yeah, so we're always going to be driven by customer pull. So I'm very excited. Our direct business will keep growing past half a million, a million businesses in the coming years.

45:33But a couple years ago, we noticed, and maybe some of you are a part of this trend, but Vertical SaaS in particular, we got really excited about, where you have companies tackling a very specific industry. It could be very esoteric. But if you obsess over that one category, kind of build business in a box, you can actually create a viable tech company there. And every one of these folks kept coming to us and saying, we don't want to build payroll. No one really wants to build payroll, because it tends to be quite difficult. But we really want to provide payroll to our customer. And we don't want to just keep routing customers to you.

46:06We want to have it be native, a native product experience. And so we have some great reference points in embedded, in FinTech especially, like Stripe as a good example. And so that was where the genesis of embedded payroll came about. That's what we call Gusto embedded payroll. And we're really excited there. We have a number of partners. On the banking side, Chase payroll is powered by Gusto. We recently announced US Bank will be rolling out payroll powered by Gusto. Xero is another good example on the account tech side. And so anyone that does want to launch or offer a payroll natively within your product, but doesn't want to build it from scratch, please let us know.

46:44We're eager and excited to partner with you. That whole business is more of an infrastructure business. My last question, you know, we have a lot of founders here. You've been at this a while. Like, what's your main piece of advice to somebody starting a company today? Or what would you do differently if you were starting Gusto right now? So I'll answer both. with my main advice I'm pretty consistent with, but I really believe it, it's imagine the 10 ,000th time you're describing what you're doing. Will you be as excited as the first time? Because at that point, you can't fake it. It will show.

47:16And you have to have a deeper interest, passion, borderline obsession with the thing you're trying to fix, the problem you're trying to make better, because that's what gets you through all the ups and downs of company building. And in our case, I was with a team earlier today that's an incubation team launching a new product. And we went around the room, and it was an easy first question. I didn't even have to ask it. Everyone just shared their favorite small business. And so in our case, that obsession with small business comes through hopefully very clearly. It's a big part of our hiring filter.

47:48And as long as they're in pain, we feel like we have purpose, and we have so much to do that we feel like we're really still early. There's a lot more ahead. And if I reflect on learnings from prior chapters, I had a prior startup where that wasn't the case. and that's where you can start a company or maybe join a company, feel like there's a miss there and wonder what's off, right? And I would argue, go back to like, what is the purpose? What is the reason why you exist? And it should not be about you. It should be about your customer. Great. Well, thank you very much. Thank you.

From the publisher

In this special episode, we feature two interviews recorded live during Newcomer’s Breaking the Bank Summit, a financial technology summit held this week in San Francisco.

We’re including two of the most dynamic discussions here, beginning with Gabriel Stengel of Rogo and Jeff Seibert of Digits, followed by an interview with Josh Reeves, CEO of Gusto.

The episode kicks off with a breakdown of the event, highlighting the key debates that emerged between Rogo and Digits around the trustworthiness of LLMs in fintech, as well as Reeves’ perspective on the service intensive business and going shoeless in the office.

After getting our hosts’ reactions, we dive in to live-recorded audio from the event.

For a full selection of discussions from the summit, including video of each talk, visit the Newcomer Youtube at youtube.com/@newcomerpod


Timecodes
00:00 - Intro
09:43 - Rogo + Digits Discussion
28:13 - Josh Reeves, Gusto Interview

More from Newcomer Pod

All 73 episodes
The Great Financial Services DebateNewcomer Pod · 49 min
Listen in VO