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14 Sep 2026 · 33m · 19 chapters

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Skipping Two Generations of Accounting Software | DualEntry on Lightwork

In short

Dual Entry’s AI-native ERP and why legacy accounting systems cause long, risky migrations; Lightspeed’s investment; product growth via fast onboarding and AI agents; upcoming “Project Helios” for continuous close using a Kanban-style human-in-the-loop workflow.

Guests

Santi Starris, founder of Dual Entry; previously built Benetago (to ~$100M revenue) and experienced a painful ERP migration that motivated Dual Entry. Sam Eisler, Lightspeed partner on fintech in New York; board director at Dual Entry; investor who evaluates next-gen ERP viability.

Key claims

Legacy ERPs can leave companies unable to close books for ~9 months (50% risk framing). Dual Entry processed $100B+ journal entries in first 18 months; raised a $90M Series A co-led by Lightspeed. AI enables “next-day” migrations and proactive, agent-driven accounting.

Notable examples

14 reference calls in one day; a customer went from one discovery call to signing a five-figure contract and going live. A migration performed while flying (Starlink on a plane) with banks/integrations connected and books reconciled “to the penny” before landing. Project Helios examples include automated lawyer accruals via calendar/estimates and surfacing bank/contract exceptions through a Kanban board.

Written by AI. May contain mistakes.

Chapters

0:00

The Challenge of Legacy ERP Systems

Learn about the issues with outdated ERP software that companies face.

“We're going from legacy 1990s Windows to AI product.”
0:30

Dual Entry's Origin Story

Discover the backstory of Dual Entry and its founding principles.

“All their banks connected, all their integrations live, the books reconciled down to the penny before we landed.”
1:25

Understanding Dual Entry and ERP

Get an overview of what Dual Entry and ERP systems are.

“And we'll go into so many things from your background, how you decided to invest in dual entry, what dual entry even is, and some upcoming, interesting, exciting announcements.”
2:05

Building in the ERP Space

Explore why the founders decided to innovate in the ERP space.

“I think for a lot of folks, they've heard of these legacy ROPs like SAP.”
3:07

The Shift Towards AI in ERP

Learn how AI is transforming ERP implementations and business operations.

“stuck in a nine month migration that ended in a lot of compromises and doing things with workarounds and ultimately a blank screen for the first nine months.”
4:00

Next-Gen ERP Implementation

Discover how Dual Entry simplifies ERP migrations through AI.

“I mean, a next-gen ERP is not a new concept when it comes to the pitches that we've seen over the course of what's called the last decade in venture.”
4:50

Customer Onboarding and Success Stories

Hear about the effectiveness of Dual Entry's customer onboarding process.

“Like we could actually port over data and run these businesses in a way that's extremely streamlined by AI.”
6:00

Customer Insights and Satisfaction

Understand how customers perceive their interactions with Dual Entry.

“Like, it wasn't a great insight that ERP was totally flawed.”
7:35

Building Trust in New ERP Solutions

Learn how trust is established during ERP transitions with new technologies.

“And I think CFOs were getting wiser and wiser about that over time.”
9:23

The Need for Modern ERP Solutions

Discuss the necessity for updated ERP systems in today's market.

“but the problem doesn't end up getting solved.”
Show all 19 chapters
10:25

How Dual Entry Changes the Game

Explore how Dual Entry's product dynamics shift the ERP landscape.

“So you can just plug and play your own different things that you want to plug in, and you can actually see a demo of what it would be like into that ERP.”
11:45

The Importance of Customer Experience

Understand why customer experience is critical in ERP success.

“Insane to think about the fact that until dual entry, they haven't had a product that speaks for itself and you had to have these very manual, if you will, sales processes.”
13:37

Partnership Development and Growth

Discover how the partnership between Dual Entry and investors developed.

“back into the business that the accounting teams can actually spend on driving growth.”
14:00

The Unconventional Partnership

Learn how the partnership between Dual Entry and Lightspeed formed through a unique series of events.

“Obviously, I want to get into how you all decided to partner with each other because I think it's a really interesting story.”
18:26

Evolution and Vision of Dual Entry

Discover how Dual Entry has evolved since partnering with Lightspeed and its future vision.

“Yeah, I mean, I'll say that the first thing is as soon as that happened, it was back to work.”
23:34

Project Helios: A New Era in Accounting

Explore Project Helios and its goal to simplify accounting processes using innovative technology.

“It's one of many things I know the team is working on to give the CFOs back time and be more proactive instead of reactive.”
27:24

The Team Behind Dual Entry

Understand the unique team culture at Dual Entry and the qualities they seek in team members.

“maintain that culture and ethos internally, how can you sell that and try to change that for the whole industry?”
28:00

Flying High: Analogies Between Aviation and Business

Learn how aviation principles apply to modern business practices and customer engagement.

“It was also something that kind of came up later.”
29:52

The Role of AI in FinTech and Organizational Efficiency

Discover how AI is transforming accounting, engineering, and organizational workflows.

“But yeah, it's just been tremendous hearing more about the dual entry story about how lightspeed and dual entry sort of found each other and were aligned in this big vision.”
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Transcript

Automatic transcript. May contain errors.

0:00We're going from legacy 1990s Windows to AI product. Every company runs on an ERP, yet most of them run on software that's older than the people using it. If you were to tell somebody, buy this software and there's a 50 % chance that you're going to end up without being able to close your books for nine months, you would never hit that button. According to them, within their first 18 months, dual entry processed over$100 billion in journal entries, and they raised a$90 million Series A co-led by Lightspeed. I opened up the laptop from the air and got them end to end through the entire migration.

0:34All their banks connected, all their integrations live, the books reconciled down to the penny before we landed. Wow. That was one of the scariest photos I've ever received in my life. Santina Starris built his last company, Benetago, to$100 million in revenue. And his painful ERP migration process is why dual entry as a company exists today. We even had to move our M &A and banking team to help us with our accounting because it got totally out of control. In addition to Santi, we have Sam Eisler, a partner on Lightspeed's fintech team in New York and a board director at Dual Entry. We'll get to have her side of the entire story and why Lightspeed was so excited about this team.

1:12There was also a moment where there was like 14 reference customer calls in a given day. Yeah. And then Sam calls me and I've just finished my 12th call. I was like, oh, wow, I've never seen this before. Sam and Santi, welcome to Lightwork. Well, I'm so excited because this is the first time on the show we're actually having an investor-founder duo. And we'll go into so many things from your background, how you decided to invest in dual entry, what dual entry even is, and some upcoming, interesting, exciting announcements. But before we get into all of that, I think it would be super helpful to even just take a step back.

1:45What is dual entry? What is an ERP? I think some of this very high level on what the company does. Dual Entry is an AI native ERP. An ERP is a fancy word for an accounting system. Every company needs one. And it's where all your financial data lies and where all your finance team members operate out of. Think of it as an OS that enables you to tell a story about your business in a standardized way that anyone from anywhere in the world can understand, and even yourself, for you to understand how your business is doing and make ultimately better decisions that help you grow. I think for a lot of folks, they've heard of these legacy ROPs like SAP.

2:24We know that these exist. It sounds like there are a lot of issues with them. I'm curious why you decided to build in this space. I used to run a prior company that we grew to about 100 million. And we'd spun up more than 20 legal entities to move inventory around the world. And it became slowly, it creeped up and it compounded, but it became a nightmare to operate our accounting. And we ended up having a handful of accounts, but then we even had to move our M &A and banking team to help us with our accounting because it got totally out of control. The interesting thing is when we're running this company, we're trying to cost optimize to get the cheapest ERP.

2:57As a matter of fact, we said, why don't we go and pay for the best legacy ERP out there and that'll solve all of our problems. And in fact, it turned out to be like quite the opposite. We ended up stuck in a nine month migration that ended in a lot of compromises and doing things with workarounds and ultimately a blank screen for the first nine months. And the cost was not just the hundreds of thousands of dollars that we were into this implementation, but also that we couldn't really report the best numbers that we wanted for investors. And we'd raised hundreds of millions. Often, we also had debt, so lenders were very careful about our numbers, and it was very hard to produce the data on a weekly basis.

3:31So we thought to ourselves, we were seeing the whole fintech ecosystem come out and about, and all these tools were so modern and intuitive, yet the ERP and the general ledger was stuck in the past. So we thought there might be a better way to do this, And maybe with a little bit of naivete, we went at it and here we are. Sam, you've obviously been spending a lot of time in the States. And it sounds like, based off even from your company building experience, very expensive, takes a lot of time, lots of friction. Were you seeing the same things? How did you evaluate the space? Yeah. I mean, a next-gen ERP is not a new concept when it comes to the pitches that we've seen over the course of what's called the last decade in venture.

4:13But what's changed, which is exactly what Santi said, is sort of like the blow up of the AI ecosystem and the actual leap forward that you're able to actually make for these businesses and how they run and operate. It's not a secret that NetSuite is one of the most taxing implementations for a large enterprise. And the amount of headcount you have to dedicate in order to make that implementation go through is affecting the bottom line of these businesses. And so this idea that you could do a next day migration or have everything streamlined by AI has always been something that people have been excited about.

4:48But it seems like a technological challenge that was impossible until let's call it like 2023. It really became a reality. Like we could actually port over data and run these businesses in a way that's extremely streamlined by AI. And that sort of set us on our journey to go find the right company to back and to figure out who we wanted to put our capital behind. And Santi will definitely go into a little bit our own journey of when we got to know each other. But it was just really clear to us that the dual entry team was the team we wanted to back. In addition to being founders before, like it was just really impressive to see what they had built.

5:26And I think we met maybe like eight months into building. So to have watched the business go from where they were from zero to eight months, it was hard to deny that there wasn't something here. Yeah. I definitely want to talk a lot more about, you know, the ventral story when Lightspeed and Dual Entry partnered more formally. But even before that, maybe talking even like, you know, that eight months in the company period, why do you decide to walk away from a working company and tackle this? And are there any things that you think people get wrong about building in this space? So there was this preconceived notion that it was a problem too large to tackle.

6:03Like, it wasn't a great insight that ERP was totally flawed. Yeah, like all these companies going off. Yeah. You could have asked anyone out there and they would have. And the interesting thing is almost everyone had an opinion about it that it could actually not be done. So that was the initial receptivity. But the problem was obvious and it was there and it was a very big problem. And those are the things that I personally like to solve because you know that if once you get to the solution, that problem will actually have a meaningful impact in the world. The other thing that we were seeing is like AI was changing completely the difference between what was possible and like what could be possible in a new system.

6:37It was no longer about a better UI and a system that didn't break and something that was faster. It was also now about a system that did the work for you. And then you took the backseat as an approver, as opposed to somebody who were all day long clicking on forms and buttons. And that delta became larger and larger. And then the last thing was what Sam mentioned is the ability to do a next day migration. There's actually two things happening or were happening in the ERP space. One is more companies were delaying the ERP implementation and staying in the starter cloud because they knew it was such a painful process.

7:09and they wanted to wait until they had enough budget or bandwidth in the teams to go and make that jump. So that's the first thing that we went and tackled. And the second thing is there was this preconceived notion of like nobody got fired for hiring IBM. Like nobody got fired for picking a legacy ERP. But more and more people were getting jaded at that because so many implementations fail. Like if you were to tell somebody buy this software and there's a 50 % chance that you're going to end up without being able to close your books for nine months, you would never hit that button. And I think CFOs were getting wiser and wiser about that over time.

7:38So us being able to demonstrate that you can get the data in and you actually had hands-on experience with the software was a big way to build trust early on. And that completely switched the, you know, there was a switch in people's minds that you can actually onboard to a new ERP like dual entry. And like the risk is actually much lower than it is in a traditional legacy ERP. I want to go a bit deeper into, you know, something that Bofi brought up, which is this space has been a well-established problem. But I think what's always interesting to me is like in venture, as we know, there are always going to be multiple teams tackling the same problem set.

8:13Here, it's a very clear problem. For both of you, what were kind of the aha moments? Like you as a founder that this is the right way to tackle this problem and that we have what it takes to become the team that takes us on it. And I think similar question for you. OK, this team is going to win. It's actually very obvious when you're in the inside. There's not a lot of analysis that goes into it when you felt the pain. Like I was in a legacy ERP. Like I was logging in myself and I was the user. I was with my team on it. I had to get familiar with all these buttons and we were out and hiring an administrator for these ERP.

8:44Just talking about it sounds so painful. For us, it was very obvious that that was the issue. But then when we went out into the world, there was a combination of CFOs being jaded as like, oh, that's been tried so many times. Like no startup has ever succeeded. And then investors being jaded the same way. It's like it's such a big problem to tackle that you need to actually create a different product of what they call a wedge. and then once you're in, then you can go and tackle the ERP. But then what ends up happening if you trace the history of these wedges is that they get really good at that wedge and they get product market fit and they start growing and now they become dependent on these ERPs because if they were to compete, then they would lose the connection to the ERP and then they end up being really good and profitable businesses but the problem doesn't end up getting solved.

9:25So the only way to solve it is with the reverse wedge. You actually have to be like going the hard thing first and then get rid of that dinosaur before you can then go and tackle some of the other adjacent problems. And I think that was the big insight that we had. And it's very obvious from the inside, but it can look counterintuitive from the outside. Echoing everything you're saying, I think the thing, in addition to just Santi and his co-founder Ben, just being, you know, really wonderful people that we enjoyed interacting with. It really matters. Totally. What they had been able to shift in the product by the time we actually got in there and started playing around.

9:59It was just really incredible, both in its velocity, but then also in its comprehensiveness. And, you know, in addition to that, and you should definitely talk a little bit more about this, like their ability to onboard customers. Like that's the number one point with all these ERPs, right? It's like the implementation itself is what bogs down kind of everybody in the ecosystem. It's responsible for a lot of this jaded behavior that Santi's talking about. And Satya and Team, in addition to being able to onboard customers in a 24-hour period, they can actually, like, in real time, show you what your data looks like in an ERP.

10:30So you can just plug and play your own different things that you want to plug in, and you can actually see a demo of what it would be like into that ERP. And I think to go from this, oh, six, 12 month implementation sort of mindset to seeing that play out overnight, like no one in the ecosystem had that from who we talked to. And it just feels like the core sticking point of how you win in this market. I mean, to give you an idea, when I took the demo for Legacy ERP back in the day, I would even ask during the call, hey, can you click on these two things that really matter to us? And the person giving the demo said, we're not authorized to go off script in this demo.

11:10Really? We'll take back the question, rehearse it, and then come back to you with a new demo. That's insane. And I was like, and that was a week later, by the way, because they have to get an SC, a solutions consultant resource on the call. There's like all this scheduling that happens. and like i counter-positioned that with we we just signed a customer that took one call one discovery call with one of our a's we didn't hear back from them in a month and we thought well it's a lost deal probably they had a bad interaction but it actually turns out a month later they come back and they say we're ready to buy where do we send the money and we send them an order form they signed and they send the money and like they're they're now live on dual entry and said something must have must have happened here like one discovery call and they're ready to pay a five figure contract like that is that is unheard of and then we went into a sandbox data and we started seeing what did they do with the software during this month and they actually spent 36 hours evaluating the software 36 hours of like playing playing with it plugging new things unplugging trying edge cases this is the first time we've proven that the erp can sell itself if you lead with product versus a demo that you can even ask the salesperson to click on something like it's a totally different way to approach it and that to us has been one of the biggest drivers of growth because we lead with the product, we lead with the quality as opposed to try to hide it away from the customer.

12:22Insane to think about the fact that until dual entry, they haven't had a product that speaks for itself and you had to have these very manual, if you will, sales processes. Sam, you've spoken to customers, you've interfaced with them on a day-to-day basis. Say I'm a CFO, what are some of the customer stories that have brought you the most delight? I like this quote, you know the tech is working when you don't perceive it. I think the ERP, to some extent, there's probably two sides of it. One is the inside side, which you actually do want to perceive. You want to get great insights. But there's also the time that it takes to close the books.

12:58The less time that it takes, the less you're interacting with that part of the software, the better you're doing as a company, as a product. So we actually measure those two metrics separately. And we want one to trend down and the other one to trend upwards. The best stories you can get from these CFOs are very simple. They're like, yeah, I actually don't have to spend this weekend on the ERP. Or yeah, I actually could take this vacation that I couldn't take before. I was planning, you know, the big project for the next two quarters was my ERP implementation. And before the demo was even done, I guess the migration is over and I just now got to focus on some training and like, you know, optimization moving forward.

13:32But I guess that big project is already done. And like, those are the most satisfying things because that's time that's back into the business that the accounting teams can actually spend on driving growth. Like, You now have time to swift through insights to go to your CEO and saying, hey, I found that these parts are doing much better than these others. We should reinvest in these marketing campaigns. That's the thing that the accounts want to be a part of, not on the closing the books part of the work. So, yeah, those are the best stories. I think it just speaks to how seamless that experience.

14:00They don't even know. It just works. It's magic. Obviously, I want to get into how you all decided to partner with each other because I think it's a really interesting story. I hear there was like something that involved an airport or something. You said you met Santiago like eight months into building. How did you all get connected there? And then I want to hear a little bit more about how the relationship developed. Yeah. I mean, we knew of dual entry just because of our work in the market, but we actually hadn't had a chance to interface with them until we were introduced by someone who was already on Santi's cap table.

14:32And we were pretty far along in our work. And in that respect, I think it really helped us understand just how good this team was quite quickly and then enabled us to also move quite quickly. So from the first meeting, correct me if I'm wrong, like we basically were like, hey, don't go anywhere. We're going to just bring in a lot of different people from the firm to like get under the hood here and like try and monopolize your time. After first meeting, we had Tanti come back, I think the next day, and we brought in six different people from Lightspeed. And it wasn't even like a formal investment committee.

15:06It was just like, hey, this is fascinating. Like, take us through it. And I'll let you kind of jump in about what happened once we expressed our interest in partnering with you. Obviously, we knew about Lightspeed. We knew we wanted to work with a firm that was so forward in AI because we saw how AI was becoming more and more important in our product every day. And Lightspeed being so active in these big AI platforms was very appealing to us. And so Sam knocks on our door. We get introduced and very quickly said, you know, started coming up with questions that I would typically expect from someone after they've spoken with them for four hours about your business.

15:41And I was like, clearly they're very ready and they understand the space very well. And they were asking about things that I'm asking my team about, which is usually a great sign. It's very blurry exactly how everything happened. But I remember there was also a moment where there was like 14 reference customer calls on a given day. And then, you know, Sam calls me at the end of this. Like, I've just finished my 12th call of the day. I was like, oh, wow, I've never seen this before when it comes to speed. So you guys do live up to the Lightspeed name. And then I think the next morning I was here in the office.

16:09I think it was actually one of the, Ravi was coming here to see the office opening. And we met with Ravi as well. And it was great. Everything moved very quickly. But as a good co-founder, I told my co-founder, Ben, like, look, we have to go to SF to meet other investors because we weren't trying to raise. Sam said, no, you're not going to SF. We're meeting this morning for breakfast, and we're going to get something done. And I said, I'm willing to meet, but I have to go to the airport. And I remember there was a car waiting for me. He came with his suitcase. I did have a suitcase. I did have a suitcase.

16:41It was real. It had clothes in it. Sam at one point was wondering if it was clothes in there. I asked to see the boarding pass. Oh, my God. So then we ended up on the way to the airport. It was about an hour ride, and there was a lot of phone calls on that call on the way there. more people would join the call and it was the negotiation got a lot more intense to the point that i ended up at in a jfk in front of a tsa agent and i wasn't on the on the party line i was on my on my c36d and i finally made it to the beginning of the line and i'm on the phone and and all these people are throwing away throwing out millions of dollars of numbers left and right i was like if it's not this many million it's not this many million and you're like still on in the line just on the line tsa agent's like look dude can you just like get you Boarding group like eight.

17:26Can you move to the side, please? You got a line here. I couldn't care less about your millions and whatever accounting stuff you're talking about. I need to get through this line. I was like, I'm so sorry, sir. I really don't know if I'm going to get on the plane or not. And then finally, we made it work and I ripped up that airplane ticket and made the way back to the city and met up with the lightspeed team for drinks. So it was a very intense airport ride. It's never felt the same to go to the airport, I'll tell you. Yeah. It was a really good time. That's exhilarating. Honestly, you should have kept the boarding pass.

17:56It's like a nice little souvenir. I know. I regretted it. It was so dramatic how I tore it up. But I'll tell you, it's a good dramatic story. I could have just put it up in the wall and be like, that's my C36D. Yeah, no. No more boarding pass. That's so fun. Since you all have, from the point that you guys have partnered, how has the company evolved? I'm curious, you know, your big vision for this. I want to get to specifically something that I've heard you all are working on with Project Helios, but I think also helpful to understand how it's evolved since, you know, you all have, or we as a firm have partnered with Dual Entry.

18:32Yeah, I mean, I'll say that the first thing is as soon as that happened, it was back to work. Lightspeed started connecting us with the biggest AI labs to try to embed more and more in the product, get to test out the latest features. And I credit a lot of the great work, including what we're going to talk about today around the AI. When we first wanted to tackle this problem, it was first like, how do we make sure that we have the right compliance and the right guardrails that you would expect from the legacy ERP? So we actually took a slightly different approach. And instead of going after small companies, we went after big publicly traded companies.

19:02And we said, if we can get these companies live and happy, that means we've done our work in being as compliant and as low risk as a legacy ERP might be perceived as. The next step is like, then how do we obsess about all these customer journey paths along the ERP so that even the less experienced users can actually get the most out of it and they spend less time doing clicks and filling up forms? So that's more product-like work than you would expect. That has never been, you know, like the thing is we're skipping two generations with ERP. We're not going from great product to AI product. We're going from legacy 1990s Windows to AI product.

19:36So we first have to make the product good and usable. And I think this is where most other new ERPs would spend the time on. The new step that we can now accomplish is like, how do we actually abstract away everything into a single screen where we can manage everything of the ERP in a single place? So one of the things that we were noticing is like when you log into legacy ERP, it's like a collection of database tables and there's no starting point and there's no ending point. Even if you add a beautiful product on top of that, you really have to know, you have to be experienced to know where to start and where to end.

20:06Like, think about a bank fee as a table with lines, and your bills are also lines, and your invoices are also lines on a table. So it's very daunting. You don't know where to go. Even when you're doing a migration, you don't know where to start. Well, one, we want to have an opinionated place where we actually surface the things to you and say, well, this is what you actually have to pay attention to. And an agent has already done and done half the work for you, and now you're just the human in the loop to approve it. And, yeah, I mean, we can talk more about that, but that's what we call today the project that we're going to talk about.

20:34Yeah, I've heard whispers about this. It sounds very interesting. You have a very fancy name for it and very mysterious, Project Helios. Tell us a little bit more about what you guys are launching. So Project Helios is this secret project that we worked on in what we call the basement. And the reason we do it in this, they're not actually in the basement, they're in the office. They just don't get to talk about it with the rest of the team. It's because when you create big groups to solve problems, you end up in consensus solutions. This team was tasked to go and talk to all the accountants that we've ever interacted with and ask them, why are they spending the most amount of time on it?

21:06And why are they getting bogged down on? And the thing that we learned is that all these ERPs, even new ones, they feel very daunting. It's a very extensive product. There's a lot of tables. Everything is aligned on a database. And you don't really know where to start or where your job is finished. And in a world of agents where context gathering is such a powerful thing, we felt there was a better way to do this. So we've come up with this project Helios, which is a big Kanban board. Think of it like a linear where tickets are created by agents or notifications or exceptions. And they're surfaced up to you.

21:38And then you as a human, as the controller, get to approve when something is posted or review when something is posted. and you also get to push out into the world information back into your, you know, whether it's your management team or for the users in your company. So I'll give you an example of like, you know, every month we have accountants that have to figure out how much money you've spent with your lawyers before the lawyers send you the bills because lawyers are not necessarily good at sending bills very late. So you actually want to book an accrual, an estimate, and then revert it the next month.

22:09Normally that an accountant would have to have to log into Gmail or log into your calendar, see how many hours you've spent on this, and then estimate that in the accrual. Well, now with dual entry, you can set an agent via MCP, goes into your calendar, checks how many hours, runs an estimate based on which partner was in that meeting, and then tees up a draft. And you don't even know about this until the very end where the draft is serviced to you in this Kanban board. And then you click approve if you think it's good, or you can give it feedback. Hey, you probably overestimated on this. And then the journal entry gets posted, and it's out of sight and out of mind.

22:43So think of it as this big board where you have tasks and then at the end of, once you're resolving every task, everything is clean and out of mind and that guarantees that you're running on a continuous close. If something breaks, like a bank connection, you don't have to go into bank connections every time to check if everything is okay. We will surface this up to you and then you get to re-authenticate the bank connection. If actually AEs are asking you via Slack, hey, when are my contract renewals happening? We pick up on that. We say, okay, these are the contract renewals. We draft up a response for your AEs.

23:11And you get to tell your sales team, hey, these are the three contracts that are up for renewal. You should go talk to the customers. You click go. That ticket is out of sight, out of mind. And now your A's have their questions answered. So it becomes more of a, think of it like a push notification system as opposed to having to pull and go into every app and seeing if there's anything pending. So what we were discussing earlier, it's just like a seamless experience that is proactive rather than everything being reactive. Sam, did you have any thoughts when Santi was sort of teasing this idea?

23:37I think it makes sense. It's one of many things I know the team is working on to give the CFOs back time and be more proactive instead of reactive. And I think that's exactly what it's doing, like flagging issues before we even know that they're issues. And if anything, putting information in people's hands that couldn't get this information, like the AEs themselves or whomever is running different revenue lines for the business. I think that's the beauty of a lot of these AI native platforms is this paradigm shift that we're entering where like we as humans, we probably shouldn't have to be button clickers.

24:12Like that's like not an enjoyable job. How can we take all of that painful stuff and make the stuff that we want to work on a delightful experience? The other beautiful thing about simplifying of the ERP is that it's no longer this daunting thing that you only get once you have a CFO with three people on their financing. You can get it much sooner. and we've even seen single founders like running their entire businesses out of dual entry. We never intended dual entry to go so far down the market, but we've seen it because we've simplified and we actually see it as a sign of doing a good job that both a publicly traded company can run on our platform and a founder team with no people in their financing can actually still close their books there.

24:48So this abstraction is only possible today because of the work that agents can do behind the scenes for you and the simplification of this Helios project. Sounds like the versatility of it, the product sells itself. Curious how you build out the team period for dual entry, but even the basement team too. One beautiful thing is both the EURPs are platforms by definition. And one core thing that we believe differently maybe than vertical software builders out there is that in accounting, the accounting itself is the vertical software is the thing that needs to be specialized. The way that we build for a real estate company also benefits the way we build for a tech company or an inventory company or a construction company.

25:25What people care about our specific accounting features that are robust under a compliance level and that is risk-free, auditable, with the right permissioning layers. So that's enabled us as founders to create teams that are very modular and that operate independently and move very quickly. If you see big organizations, the reason they slow down is because everyone's working on the same issues. They're stepping on each other's toes. They create a lot of bureaucracy because now that your work impacts mine, so I need your permission to do things. We try to avoid that. And it's something that we've learned from the best tech companies like Ramp here in New York.

25:57And it's worked really well. And the other thing is when you operate in small teams, you actually get to new novel solutions. Then if you work in large teams, everything goes back to consensus and you end up repeating history doing things the same way that they've been done in the past. Are there any specific qualities you look for in people you bring into the firm? It's very interesting because we were doing this assessment of like, you know, we've hired now close to 100 people and we felt that we've punched way above of our weight? What is it that we've done right when we look back at our teams?

26:23And we start to see this weird pattern where people are, our team members of dual entries, they're outliers everywhere else in their lives. So as an example, we have somebody who is a top 150 woman tennis player in the world. Oh, wow. Yeah. We have somebody else who played professional poker for three and a half years. We have somebody who does a deadlift of 600 pounds. And we never interviewed for these things. We would never ask that in an interview. It's interesting that these spikiness kind of come up in different parts of their life. I think the thing that bonds us all together is this deep desire to build and to solve other people's problems.

26:54And we don't like to ask for permissions. We don't like meetings. We don't like to be blocked down in this, like the work of doing work. We like to get the thing done. And it's interesting because that's also what we're allowing accountants to do. Our number one thing that we're saving people is like, we want to minimize the work of accounting. We want our accountants to spend time on insights and saving companies monies and lowering the company risk, but we don't want them to spend time in the work of accounting and getting the books closed. Those qualities have worked really well in dual entry, and I think it's a result of how we've just built so fast.

27:23Yeah, and it's like, if you can't even maintain that culture and ethos internally, how can you sell that and try to change that for the whole industry? Exactly. How can you claim that you're going to save other people's time when your own company is not run like a bureaucracy? And then I learned a fun fact about you. Apparently, fly planes. Is that right? I do. I do. I fly very small planes, four-seater planes. And it made Sam want to get a keyman risk on our docks. He didn't have a keyman risk policy when we met him. Is that part of your spikiness? I'm also curious for Sam's take on this. I will say we have pilots in the team as well.

27:58Oh, okay. You're not the only one? No. And we didn't know. It was also something that kind of came up later. I've always had this passion for flying planes. And there's actually some analogies there where if you look at how a plane looked in the 1980s, there was like the fact that it had so many like knobs was a good thing. But nowadays, the most modern planes, they try to abstract away almost everything so that the pilots can focus on the things that actually matter and will keep you safe. But yeah, it's something that I really enjoy doing. There's no ultimate freedom. You can move in all three dimensions.

28:27It's also proved to be an effective closing strategy, right? Like he's been able to get to customers across the country to get them to ultimately become voluntary customers in a matter of you know a couple of hours as opposed to having to take days to figure out travel schedules i did not think about that yeah we've we've flown to customers yeah gotten them live from zero to completely live okay and then flown back in the same day didn't you also do a migration on the plane while flying we did do a migration on the plane yeah it was it was i was clearly done also for marketing purposes but the fact that that was one of the scariest photos i've ever received in my life was just santi in a plane in the clouds also doing a migration and uh i That is when I asked him, do you have a key man risk policy?

29:09So we got ourselves a tiny Starlink. We put it out in the window. We got a customer that was not, but it was starting from scratch. I opened up the laptop from the air and got them end to end through the entire migration, all their banks connected, all their integrations live, the books reconciled down to the penny before we landed. I don't think that's ever happened in startup history. I don't think so. I don't think it's ever happened in the European history for sure. Yeah, I don't think so. Well, we'll certainly have to try maybe even do it like a light work follow up segment. Yeah. Maybe you can fly and whiteboard stuff while you're while you're flying the plane.

29:41I don't know if I personally want to be. I don't know. Actually, now that you've done the migration, I feel like I trust it. You've already established that you can do a full migration plus fly. But yeah, it's just been tremendous hearing more about the dual entry story about how lightspeed and dual entry sort of found each other and were aligned in this big vision. And maybe to end as a sort of final question, you know, what is, it doesn't necessarily have to be like ERP specific, but curious like what specifically in AI, FinTech, or even just AI and how organizations work excites you and any sort of like forward looking things that you're excited about?

30:18AI has been the biggest enabler. It allows you to do way more with the same amount of resources. And that applies to everything. It allows you to synthesize more context than you'd otherwise feel like a daunting task. Now it seems like something very simple. It takes actions on your behalf so that you only do the things that actually matter. So that is true in accounting, but it's true in engineering. And I think sometimes I feel like founders, they focus only on the effect of AI in their product. But we don't understand that the AI, like the fact that you use AI more productively in engineering also allows you to build better product for your accountants.

30:52And the fact that you're like caught up with the latest trends in AI and then how people build product or software also allows you to deliver those same trends or the latest tools to the accountants in the ERP space. And another interesting thing that's come from that is like, now you can do more powerful things a lot earlier. It used to be that the ERP was like something series B and after, like a whole bunch of seed companies are now running a dual entry. And like that is only possible. And you're getting way better insights. You're segmenting your books a lot. You know, you're running agents and saying, tell me where I have the best product market fit that I didn't have before.

31:25It's just like, it's like 10Xing what you can do with the same amount of denominators. You know, it sounds like there's a lot coming up with Helios. Where can we find out more about that? So it's not going to be called Project Helios. It's just going to be part of the dual entry project. This was the name of it. You know, the hidden basement team that was working on this. The beautiful thing is we give out sandboxes that are fully migrated during our sales process. So if you want to try it out yourself, if you're not sure if it's too early to use an ERP, I'd encourage you to go to dualenter.com, ask for a demo.

31:52You'll leave that demo with a migrated sandbox and you'll get to try this for yourself. And you can actually try to get yourself live without involving from anyone. Or if you want to wait until our team of accountants goes in and sets it up for you, you can also do that. Yeah, that's huge. I'm sure it's going to be a very exciting launch week. And if people want to find out more, dualentry.com. Dualentry.com. Awesome. Thank you both. Thank you.

From the publisher

Santi Nestares joins Claire Zau and Sam Eisler to explain why he rebuilt the ERP from scratch. Santi ran a previous company to about a hundred million, then lost nine months to a legacy ERP migration that left him staring at a blank screen while lenders and investors waited on numbers. His argument is that the ERP looks too big to attack directly, so startups go after an adjacent wedge instead, get good at it, and end up dependent on the system they meant to replace. DualEntry went at the hard thing first. Santi calls it the first ERP created after ChatGPT-3.

Sam explains why this was a team Lightspeed wanted to back, and Santi tells the story of a negotiation that ran from a car to JFK and ended with him arguing millions on the phone in front of a TSA agent, then tearing up his ticket and heading back into the city. He also describes the team he put in what they call the basement, kept from talking to the rest of the company, and tasked with collapsing the product onto a single Kanban board where agents draft the work and a human approves it. Along the way, a customer who took one discovery call, went quiet for a month, spent 36 hours in the sandbox and came back ready to sign. A team of close to a hundred that includes a top 150 tennis player and a professional poker player. And a migration Santi ran from his plane over a Starlink propped in the window, books reconciled to the penny before landing.


Timestamps

0:00 Welcome to Lightwork

1:41 What Is DualEntry and What Is an ERP

2:20 Why Build a New ERP

3:50 How AI Made Next-Generation ERP Possible

5:44 Leaving a Successful Company

7:58 Finding the Right Way to Tackle ERP

12:23 Which DualEntry Customer Stories Stand Out?

14:03 How Lightseed and DualEntry First Connected

18:12 How DualEntry Has Evolved Since the Partnership

20:40 Inside Project Helios

24:59 Building Fast-Moving Teams at DualEntry

26:09 What Makes a Great DualEntry Hire

30:02 The Future of AI, Fintech, and Organizations

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