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How Lassie Is Automating Healthcare Administration

Alex Rampell and Olivia Moore speak with Lassie cofounders Steijn Pelle and Frédéric Renken about bringing AI to one of the most overlooked parts of the economy: small businesses. Inspired by time spent working inside dental practices, Pelle and Renken set out to automate the administrative work that keeps healthcare providers away from patients. They discuss how AI agents are changing billing, insurance claims, patient payments, and other operational workflows, allowing practices to spend less time on paperwork and more time delivering care. The conversation explores AI agents, software that performs work rather than simply storing information, onboarding AI into real-world businesses, and why healthcare administration offers one of the biggest opportunities for automation. Along the way, they discuss product design, go-to-market strategy, and what it takes to build AI systems that operate reliably in complex business environments. Timestamps: 00:00 - Intro 01:12 - Story Behind Lassie 03:46 - Embedding in the Customer's Office Before Building a Product 05:39 - How the Product Build Has Changed with Better Models 07:23 - Software Never Did the Work but AI Finally Does 17:24 - 98% Automation: How Lassie Got Agents to Actually Run a Practice 22:08 - Startup vs Incumbent in the AI Era 33:35 - The Master Plan: From Dentists to Every Small Business 39:27 - What It Takes to Hire & Build When You're Selling to Main Street 55:59 - How Do You Reach Hundreds of Thousands of Small Businesses? Resources: Follow Steijn Pelle on X: https://x.com/steijnpelle Follow Frédéric Renken on X: https://x.com/fredericrenken Follow Alex Rampell on X: https://x.com/arampell Follow Olivia Moore on X: https://x.com/omooretweets Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Show on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Show on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.

Alex RampellhostSteijn PelleguestOlivia Moorehost
Jul 30, 202658mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:12

    Intro

    1. AR

      AI is overhyped in Silicon Valley but underhyped in Iowa. I would actually argue software just kind of took things that were stored in paper format, and then they made them available first on-prem via green screen computers, but people still had to do the work

    2. SP

      I never forgot what I saw. The number one rated doctor on Yelp spending 200 hours a month on paperwork

    3. SP

      The models are trained on so much data, and they're so large, and yet they actually don't really know how to do any of this work. Initially, we were actually the humans in the loop. We kind of automated away our own problems

    4. AR

      The battle between every startup and incumbent comes down to whether the startup gets the distribution before the incumbent-

    5. SP

      Yep

    6. AR

      ... gets the innovation.

    7. SP

      We come by and we say, "Hey, we actually have built this agent that can provide you already with tens of hours of labor." They then adopt it, like, very quick. They see us as someone they bring in to, like, actually run the practice for them.

    8. OM

      There was a great quote from Dr. Kwan about you guys, which is that Lassie isn't replacing humans-

    9. SP

      Hmm

    10. OM

      ... but, like, freeing them from wearing so many hats.

    11. AR

      It's not like, oh, AI's gonna take the jobs. In many cases, you can't find somebody

    12. OM

      How are you prioritizing what you build, who you sell to? Is there of the world where Lassie for dentists makes Lassie for physical therapists better?

    13. SP

      Hmm.

    14. SP

      The end goal here is that-

  2. 1:123:46

    Story Behind Lassie

    1. OM

      So welcome, and thank you for joining us.

    2. SP

      Thank you for inviting us.

    3. SP

      Thank you.

    4. SP

      Excited to be here.

    5. OM

      Maybe we'll start with the basics. So Steijn, this whole company started with a conversation with you and your own dentist, Dr. Kwan. What did he tell you that made you decide to quit your tech job at Robinhood and go process payments for him by hand?

    6. SP

      Yeah, I did not, uh, know that my American dream would look like this. Um, it was, uh... It was interesting. Like, I, I, um, was at Robinhood at the time. Um, and, uh, I came to this country to start a company. So after six years, um, I moved from Amsterdam to Silicon Valley. Like, I was looking for a hard problem to solve, and then my doctor, Dr. Kwan, um... I was a patient there, so I saw him twice a year, as you do with a dentist, knew that I was looking for a hard problem, and he said, "Do you wanna see how I run my business?" And I said, "Absolutely." Um, and he walked me to the back, and I never forgot what I saw there. Just, like, a small business owner that, like, is the number one rated doctor on Yelp, spending 200 hours a month on paperwork and busywork, so submitting claims by hand. And he had to stick around himself because he couldn't find people to, like, bill the patients. So I'm like, "Wow, it's fascinating." This is, like, a couple of years ago, so I thought that this was a solved problem 'cause in the '70s my mom worked in a hospital, and that's what she did. She brought bags of cash to the bank and then processed payments by hand, uh, but it wasn't a solved problem here. So that's, uh, why this piqued my interest.

    7. AR

      Although I have to ask, when he gave you this offer, were you like-

    8. SP

      [laughs]

    9. AR

      Was it, like, that kind of reclined... Could, could he actually process your answer as yes versus no if your mouth was open and drills were in your mouth?

    10. SP

      Yeah, yeah, yeah.

    11. AR

      Or how, how did that go down?

    12. SP

      Well, uh, up until now I don't have cavities, so, you know, there was no drilling-

    13. OM

      Wow

    14. SP

      ... happening yet. Uh, so you know, knock on wood.

    15. AR

      Examination.

    16. OM

      Yeah.

    17. SP

      Exactly. Yeah, yeah.

    18. OM

      Cleaning.

    19. SP

      Exactly, yeah.

    20. OM

      [laughs]

    21. SP

      Um, um, no, like, he, he, uh, uh, s- uh, took me inside, like, after that.

    22. AR

      Okay.

    23. SP

      Um, because he, he knew that I was, like, looking for this, like, hard problem and was roaming around. Um, and, um, then, like, uh, like, after, like, that appointment, he, he showed me kind of, like, what was going on. Uh, and then I thought maybe it's him, right? But that, that didn't really, uh, make sense to me because he was very, like, well-rated. He used all these modern technologies. So then, um, we started, like, talking to other doctors, like, because maybe this Dr. Kwan was just, like, an anomaly. But then, you know, I also, like, worked for a gastroenterologist in Scranton, Pennsylvania, and we saw the same there. I'm like, "Wait, you're doing this all by hand?" Um, so then we figured out, wait, there are, like, hundreds of thousands of these small businesses that literally, like, do this all by hand. Like, that would be quite, like, a fascinating problem to solve. We knew it was going to be a hard problem, but, uh, we were kind of, like, looking for that.

  3. 3:465:39

    Embedding in the Customer's Office Before Building a Product

    1. OM

      Yeah. The Lassie story is so unique to me because you both spent months, if not years, before kind of fully releasing the product, like, literally in the office of the customers.

    2. SP

      Yeah.

    3. OM

      Um, how did you convince them to let you in [laughs] and to kind of look through the, the heart of the business and get into the financials?

    4. SP

      Yeah, it's a little weird, right? It's like, "Hello-

    5. OM

      [laughs]

    6. SP

      ... I work at Robinhood on Growth on the referral program. Uh, can I get a job, like, here? And by the way, Frédéric worked at Superhuman on product. Can we do the billing for you and take over the finances?" Um, I think that was the first sign that we were onto something big, um, because to our surprise, all these doctors, when we asked them... So we, we first talked to all of them, like Dr. Kwan, because everybody likes to talk about their problems. Um, and, uh, when all these doctors started talking to us for hours, we knew that, okay, this is a, a real problem they have. This is not some vitamin that, you know, maybe it's nice to solve that for them. Uh, but this is, this is something that keeps them up at night. It, it makes them almost quit their job and say, "You know, I got into this industry because of my passion and craft, uh, in this case, like, because I wanna take care of patients." Um, so that was the first time, that these people were not, "No chance that you can come work for me because, you know, like, you don't have any experience running the finances. Uh, what about, like, HIPAA and security reasons that you have access to all this information?" So I think the first sign to us that these people said yes, Dr. Kwan said, "Just come and sit here 9:00 to 5:00. You can do the job." Um, Dr. Shah was in Scranton, Pennsylvania. Uh, he sat us down behind the desk and said, you know, uh, "You can have access to anything you need to have access to. We'll treat you like my son." Um, so that was the first sign that, like, this was very broken, uh, and not a solved, like, problem. Uh, and then I think that triggered, like, our intuition for, okay, we might be onto something 'cause the, this is a real pain that, uh, people are desperately looking for a solution.

  4. 5:397:23

    How the Product Build Has Changed with Better Models

    1. OM

      Yeah. And from a technical perspective-

    2. SP

      Hmm

    3. OM

      ... so Frédéric, you... The business started in 2020, and so much was different then in terms of what was even possible to build. Like- How has your product building process changed over time? How is what you thought possible then different from what you think is possible now?

    4. SP

      I would say when we started the business, we were always obsessed with automating and, and putting, putting the business on autopilot, so that hasn't really changed. Um, back then, the models weren't that good though-

    5. OM

      Yeah

    6. SP

      ... uh, especially, uh, especially reasoning models or didn't really exist in that form. Um, but if you think about what it takes to automate any job, you're really looking at, um, getting context on the work, uh, which, you know, in the case of a doctor office is basically you need to have access to all the historical data, the patient records, uh, that sort of stuff. Uh, and then you need, uh, tools to do the work. Um, you know, this is true if you're a human in the office or if, or if you're, uh, an agent. Um, and so we started building, uh, building the context layer and building the tools, and it, and it's just that the intelligence layer wasn't that intelligent. Uh, but for the first, uh, for the first job, it wasn't that necessary. Like the, the, the most basic kind of, uh, you know, automation didn't require that much reasoning. Um, but then as the models got really good, we, we had this, uh, kind of huge tailwind because we could, uh, we had all, all this context already built, uh, all the tools already built, and we could kind of, you know, as, as the models got better, just replace our intelligence, uh, and, and, uh, the product would just get smarter over time. Um, so in that way, we, we, we got a little lucky, but I think the, you know, the, the core vision hasn't really changed at all. It was always about automating the work and not, uh, not building tools for, for them that they would

  5. 7:2317:24

    Software Never Did the Work but AI Finally Does

    1. SP

      have to use.

    2. OM

      I feel like as the models have improved, we are more and more seeing software do the job of labor, which Alex, I would say you were the first to argue, and famously argue, that that would be the case. Curious, like, how you think about that when you look at companies and maybe how it played into, like, the thesis around Lassie.

    3. AR

      Yeah. Well, so I've given this whole presentation on the origin of software was basically take a filing cabinet and put it into a database-

    4. SP

      Mm-hmm

    5. AR

      ... and kind of pick the, uh, the, the, the time equals zero moment for that with this company, the Sabre Systems.

    6. SP

      Yeah.

    7. AR

      Because airlines would just keep reservations in filing cabinets. Sabre Systems was a joint project between IBM and American Airlines. That's why Sabre is spelled with two As.

    8. SP

      Mm-hmm.

    9. AR

      Sabre. Um, but then this kind of took wind everywhere else. So, like, there were HR filing cabinets, and that became something like PeopleSoft.

    10. SP

      Mm.

    11. AR

      There are legal filing cabinets, and that became, you know, all of these LexisNexis products. There are accounting filing cabinets, and that became QuickBooks, and that became NetSuite. So every s... That was the origin of software. So software just kind of took things that were stored in paper format, and then they made them available first on-prem via green screen computers, because that was a lot more efficient to book an airline ticket and change it if you didn't have to use an eraser anymore, uh, starting with Sabre. And, um, but people still had to do the work.

    12. SP

      Mm.

    13. AR

      So I, I would actually argue that the world didn't get that much more efficient with software because all that software did was, like, take HR, like, did PeopleSoft and then Workday make HR efficient, make, make HR departments more efficient? Like, I don't think so, because the same number of people worked in HR for the exact same size company in, like, 1950 as probably 2000. And instead of using filing cabinets that are ju- you know, that are guarded by Steijn and Frederik, you know, making sure that nobody breaks into the HR files-

    14. SP

      Mm

    15. AR

      ... now you have an IT department and a CISO to make sure nobody hacks into the IT files or the, you know, the HR filing cabinet. So nothing really got more efficient. I know I'm, I'm somewhat exaggerating for effect here, but what you can now do with software is it can do, it can edit the filing cabinet, right? It's no longer just the dumb storage. It's actually, like, the smart implementation of changes against those things.

    16. SP

      Mm-hmm.

    17. AR

      So, like, if it's HR, let's do a background check, right? Or let's do an onboarding, or let's explain the benefits to this person. If it's accounting, what do you do with the financial statements? Like, imagine I'm a dentist, and I see I have all these overdue invoices, and I can look up, look up in QuickBooks. What do I do? Well, I might wanna call and say, "Please pay me." Like, that's what the filing cabinet should be doing-

    18. SP

      Mm

    19. AR

      ... not just giving you the information. So it just turns out that the work is orders of magnitude bigger than the storage of information that the work is done on. Um, so that, that's really the, been the thesis. And the, you know, you need the technology to catch up so it can actually do it.

    20. SP

      Mm-hmm.

    21. AR

      Um, because in 2023, it's like, you know, next word prediction wasn't really good at, like, going and, uh, which is basically what AI is.

    22. SP

      Yeah.

    23. AR

      Uh, that was not good enough to go say, "I'm gonna go run my practice," or, you know, do background checks. I know I'm gonna have statistical, you know, inference play out, and that's how I'm gonna do a background check and make sure that Frederik didn't commit any crimes-

    24. SP

      Mm-hmm

    25. AR

      ... before I go hire him for my company. Like, no. But now things have gotten good enough, and that just massively expands the market size. And if you think about fintech, fintech massively expanded the size of many non-financial markets because now you could, you could bundle in financial products with non-financial products. And what I mean by that is, like, my favorite example of this is Toast. And I know you and I have talked about this a bunch.

    26. SP

      Yep, plenty.

    27. AR

      But, like, Toast could have existed in 1985.

    28. SP

      Mm-hmm.

    29. AR

      Like, you know, everybody had an IBM PC. They worked pretty well.

    30. SP

      Mm.

  6. 17:2422:08

    98% Automation: How Lassie Got Agents to Actually Run a Practice

    1. OM

      Yeah. There was a, a great quote from Dr. Kwan about you guys, which is that Lassie isn't replacing humans-

    2. SP

      Mm

    3. OM

      ... but like freeing them from wearing so many hats. And your launch video had a clip of him talking about how he can actually coach his kids' soccer teams now and go to his, their games, which is amazing.

    4. SP

      Mm-hmm.

    5. OM

      I, there's a gap between wanting that and being willing to adopt AI and actually, you know, having it run payments [chuckles] in a practice, and in fact, doing it so well that most of your growth is word of mouth.

    6. SP

      Mm-hmm.

    7. OM

      So it's dentists recommending it to other dentists.

    8. AR

      They do.

    9. OM

      How did you approach the technical build process for that? What was it like getting the product to, I think you guys are at 98% automation. Like, walk us through kind of that, that journey.

    10. AR

      Yeah. I think, um, a big part of it was-

    11. SP

      ... us actually spending the time in offices doing the work ourselves. Um, I don't think we could've built, uh, built a product that works as well as it does if we, if we didn't know how to do the job.

    12. OM

      Yeah.

    13. SP

      Um, I think another part, we already k- kind of talked about it, but I think a huge difference, uh, between SMBs in general and, and enterprises is that in SMBs there's nobody to, to use the tools. Like, you can b- you can build a tool, but, uh, there's nobody sitting there that, that's gonna use it. And so, uh, I think-

    14. OM

      Dr. Sloop at night.

    15. SP

      Yeah. [laughs]

    16. OM

      Needs to go into the tool.

    17. SP

      We, uh, from the very beginning, we, we focused on, um, you know, initially we were actually the, the humans in the loop, so we, we kind of took over all of the work, and we were like, "You know, we'll, we'll just do this work for you." And, uh, we, and we kind of automated away our own problems. Um, and then at, at some point, you know, we, we got to, uh, a high enough level of automation that, that we felt, uh, we felt comfortable handing it back, back over to the, uh, the remainder back over to the office. And I think now, um, you know, we learn obviously when, uh, when we can't, uh, do something for, for some reason, which is pretty rare, but, but say we, say we, we don't know how to do a certain case, we learn from what, uh, what the staff tells us. Uh, and we also think about, I think, um, you know, like we, we wanna get to, like, a sufficient level of automation across any product to, uh, before we sell it. So, you know, for us, I think that's, like, 95-plus, say, but not necessarily 100. Like, I don't think we're going to wait until we get into, uh, to 100 with one product and then do the next one. Um, I think the, uh, we really think about the business more like as a whole, like how much of the business can we, uh, uh, can we automate and how much of the labor can we, can we do with, uh, with software. Um, and as, as soon as we can take over a job, we take it over, and then we move over to the next one. Um, and then over time we'll just learn, uh, learn the long tail of cases.

    18. OM

      Yeah.

    19. SP

      For a business, it also doesn't matter that much, right? Like if, um, let's make Dr. Sloop famous in this podcast. Let's-

    20. SP

      He's gonna love it. [laughs]

    21. SP

      Yeah. If Dr. Sloop, um, said he can become a customer, so maybe we should talk about [laughs] like someone else that's still active-

    22. OM

      We could reactivate him.

    23. SP

      Yeah. Yeah. We will reactivate.

    24. OM

      Thanks to Alex.

    25. SP

      He might, he might come back.

    26. OM

      Literally, yeah.

    27. SP

      That's how excited he sounded.

    28. SP

      Yeah. Yeah. Dang. That's the Series B story. We've got Dr. back out of, uh, Sloop out of retirement.

    29. SP

      We had a dental shortage, and now we don't.

    30. SP

      Yeah, exactly.

  7. 22:0833:35

    Startup vs Incumbent in the AI Era

    1. OM

      Yeah. From an implementation and onboarding perspective, you guys integrate with existing practice management systems for the most part-

    2. SP

      Mm-hmm

    3. OM

      ... versus kind of making them switch a bunch of software to adopt Lassie. And Alex, you have written and talked a lot about kind of startups getting distribution before an incumbent can innovate. Curious your thoughts on, like, that in the AI era, and then would also love to hear from you guys how you thought about which path to take there.

    4. SP

      Yeah. I mean, I had this epiphany when I was building my company, which is, holy crap, like there really aren't... If you build something, I call this the TiVo problem, and TiVo famously- TiVo and ReplayTV both invented the digital video recorder, so you could pause online television. It, which is an amazing innovation, but a terrible company-

    5. SP

      Mm

    6. SP

      ... because you really have very few outcomes that are good.

    7. SP

      Mm.

    8. SP

      You either end up selling to one of the, the big guys like a Comcast or a Time Warner Cable, but they're not gonna pay you that much.

    9. SP

      Mm.

    10. SP

      Partially because y- if, if Comcast bought you, um, you know, you start TiVo, Comcast buys you, well, all of the comp- all of the competitors to Comcast, they're like, "Well, we're gonna not allow this to work." So, like, uh, you, you have what, what I call a control discount versus a control premium.

    11. SP

      Mm.

    12. SP

      So that's option one. Option two is they copy what you've done many years later, much crappily-er, if that's a word-

    13. OM

      [laughs]

    14. SP

      ... because they have all the customers.

    15. SP

      Mm-hmm.

    16. SP

      Um, or, you know, may- maybe number three, you do a licensing deal with them, and, uh, they take all the economics because they have all the customers. So that, hence, you know, my, my recognition was, like, the thing that a lot of startups should do is they should do the boring thing. Like, they should build, like, the raw pipes, the raw... Like, just own the customer, and then you get to build the fun feature on top. Um, which I still stand by. I mean, I like the vast... And, and this is why, like, maybe four years into TrialPay, I realized what I should build is this thing called Stripe.

    17. OM

      Mm-hmm.

    18. SP

      And this was not, like, revisionist history, because Stripe had five people.

    19. SP

      Mm-hmm.

    20. SP

      It's like, wow, we should, we should do boring payment processing, which is a commodity business, because if we do that, then we own the customer. Chronologically, you get them first. It's a very, very boring thing. But then we have this other thing, which in my case was offer-based payments, which was very lucrative.

    21. SP

      Mm-hmm.

    22. SP

      But you can only do that if you control the pipe, just in the same way that you can only build the digital video recorder if you have digital video to record.

    23. SP

      Mm-hmm.

    24. SP

      Um, so how does this change with AI? It changes with AI because in many cases, these are non-categories. Like, there is no incumbent.

    25. AR

      So for most categories, like imagine that I say, "I have a great idea. I'm going to do background checks for new employees as part of onboarding, and I'm going to integrate with Workday," Workday being the ba- the biggest HR information system. That's a great idea. Um, however, um, it's such a great idea that it's a very obviously great idea that this thing called Workday might copy, and they own all the customers, and that's where it's like, you know, battle between a startup and incumbent. It's like the incumbent might win there because their ability to add things... And I feel like that is actually magnified in the AI era because you can have-- Like why are big companies not good at replicating small companies? There are lots of different reasons, but the ones that-- One of the reasons is they hire very bad engineers, and they have lots of process. But now AI kind of makes a bad engineer into like a pretty good engineer.

    26. SP

      Mm-hmm.

    27. AR

      You know, kind of. Um, so that excuse kind of goes away a little bit. But this is the cool thing about a lot of the AI software companies, or the AI that does the work. Like who is the giant ass incumbent of dental software? You and I know the answer on this.

    28. SP

      Yeah.

    29. AR

      But it's not, it's not the same thing as it's like, ooh, here's Workday. It's a tech company. They already have software, and they can add something to... I, I remember, actually, this is a cool story. There was a company, I think it was called X1. Microsoft Outlook had really bad search.

    30. SP

      Mm-hmm.

  8. 33:3539:27

    The Master Plan: From Dentists to Every Small Business

    1. SP

      Yeah.

    2. OM

      Yeah. I guess to that point, like, there's more you can build and are building for dental practices. Then there's all these other types of healthcare practices that could use Lassie.

    3. SP

      Mm.

    4. OM

      And then there's, like, the broader universe of small businesses that could use you guys. How are you prioritizing what you build, who you sell to? Is there, you think, a world where Lassie for dentists makes Lassie for physical therapists better?

    5. SP

      Mm. The master plan.

    6. OM

      Yes. [laughs] Exactly.

    7. SP

      Are we in that part of the episode? [laughs]

    8. OM

      Yes.

    9. SP

      Um, yeah, I think three steps. Like, the end goal here is that, uh, every small business should run itself, right? And the busy work is done by, uh, agents. Uh, we want to build a agent for the business that then will interface with the personal agent of a consu- consumer, highly likely, that then will interface with an agent at the insurance company or other parties that the business needs to interface and interact, like, with. Uh, but step one is, to Alex's point, like, there are 160,000 dental practices in the US alone, $200,000 in labor that Dr. Sloop and others can't find. So, like, um, serving that market first, you're looking at a $1 billion in, like, recurring revenue as a market. Um, so we're, that's, like, step one. And then, uh, likely, like, we will pick another doctor office type, um, that, like, is not well-served and has a big TAM, um, and, and needs consumer-like product, right? Because what we discussed, the big part of not just you get the AI to work 95% accurate-ish, it needs to really work, and the onboarding needs to be as simple as onboarding on Coinbase, um, or Stripe. Um, so, like, it will likely be another, like, doctor office type, like, um... And then, uh, the last, uh, part there is I think, uh, we've then trained AI agents, uh, to, like, run the small business, and all small businesses at an abstract level, like, have a system of record they need to read and write into. Um, they all have customers. In doctor offices, they happen to be patients. But it's interacting and transacting around payments. You need to book appointments. So I think the end goal is if we served all the, the doctor offices, that we help all the small businesses across the world, uh, because we're just the best in, you know, building AI agents that, uh, salt of the earth people or people in Iowa and Paducah, Kentucky, and hopefully in Amsterdam, like, down the line, where I'm from, um, and Germany, Hamburg, where Frederic is from, can, can start, like, using as well. Um, so that's the, that's the end goal. But I think, again, similar to Superhuman or Robinhood, we worked at, like, laser focus on getting one thing really, really right, um, and then scale it, like, from there. Yeah.

    10. OM

      Yeah.

    11. SP

      But the end goal is to help them all.

    12. OM

      Amazing. I love that as a master plan. It's a good one, a big one. Um, you both have been part of scaling many important companies in the past, Robinhood and Coinbase and Superhuman, among others, and building a company in 2026 is, like, a whole brave new world. It's so different than ever before. What are, like, the biggest things you've carried over? You mentioned some of them already.

    13. SP

      Mm.

    14. OM

      And then what, what have you kind of had to unlearn, or what do you think is new to being founders right now?

    15. SP

      There's a bunch of stuff that, uh, we're applying now that I, I learned at, at Superhuman. Um, I think for one, uh, focusing on, uh, the right ICP and being really strict about who you onboard, uh, to basically guarantee that, uh, they're gonna have a great experience. Um, I think in our case it's, uh, particularly important because if we onboard the wrong practice and say- ... we can't actually automate that much of their work, then now we're kind of stuck with this customer that, uh, you know, we, we claimed we're gonna automate, uh, a bunch of labor for them. We can't do it. Are we gonna do it? Are we gonna off-board them? Uh, it's, it's particularly painful, maybe more painful than, uh, than in a kind of old world product. Um, so there's that. There's also, uh, we talked a bunch about the onboarding already, but, uh, we, we've really obsessed about, uh, getting to, uh, the core product value really quickly. Um, and almost like our onboarding is a, is a little bit like a, uh, you know, it's kind of like a story or a playbook or like a movie. We, we have like set, uh, set points and checkpoints that we wanna reach in certain timeframes, and we make, uh, we make sure it happens every time. Um, and, uh, you know, and, and we measure that, of course. Um, I think one thing that's, that's really different in particular about product building, uh, from, uh, from back then to now is that, uh, if you think about the products that you built, uh, in the past, I think it was much more about kind of functionality or like the ability for the user to do something. Um, and now, uh, we think really only about, uh, like what, what kind of labor can we automate and what, uh... Or like, work can we do, and, uh, where can we save time. So if you're thinking about, say, uh, like patient billing as an example, um, I think previously you would've built, uh, you know, the ability to send a statement and the ability to receive a patient payment. Um, but if you're looking at where does the actual work of patient billing go today, uh, it's really like figuring out is the money or is the, is the statement that we're gonna send the patient the correct amount and... Or like once the statement is sent, um, you know, the patient calls and asks about like, "Why do I owe this amount? Uh, do I really have to pay this? I thought this would be covered." Uh, so if you're just looking at like, where does the time go, it actually goes in like oftentimes the customer communication or, or some other kind of more like, you know, fuzzy, fuzzy part of the work. Uh, and, and when we're thinking about like shipping, say a product like that, we're really thinking about, okay, once we, you know, once we deliver patient billing, the office should not have to spend any more time on patient billing, which is super different to giving them a tool that they then need to use, uh, which doesn't really save them a lot of time.

    16. OM

      And then neither of you, I think, were dental experts before you started the company. Although-

    17. SP

      That, that's safe to say. Yeah, yeah

    18. OM

      ... you go twice a year.

    19. SP

      I do.

    20. OM

      That's pretty good, I think-

    21. SP

      Yeah

    22. OM

      ... for the average patient.

    23. SP

      You're supposed to, right?

    24. OM

      Yeah, of course.

    25. SP

      I'm just doing my, um-

    26. OM

      [laughs] Yeah

    27. SP

      ... another civic duty.

    28. SP

      Civic duty, yes.

    29. SP

      Yeah, I was about to say. [laughs]

    30. OM

      Um, when you're...

  9. 39:2755:59

    What It Takes to Hire & Build When You're Selling to Main Street

    1. OM

      Well, maybe tell us, like how big is the team now? When you're hiring, are you looking for expertise in dental? What are, what are the kind of characteristics of t- of team members that you want to hire?

    2. SP

      Yeah. Uh, which is now mainly on our mind, right? Because like we found this really great product market fit-

    3. OM

      Yeah

    4. SP

      ... in a large market, uh, where you can go after the labor, um, that they can find. Um, uh, we, we, we currently have two takes on that. Like one, not much has changed contrary in maybe take here. You still need people with steep slope, um, that like are very ambitious and, and driven, uh, and have skills that are just like top five percentile, either in engineering or in selling, right? Um, and I think that remains the same. Getting hold of doctor, um, slope, um, is just like the same exercise as before. You could do it in a more AI-like native way, uh, but I think the skills are the same and you're, uh... So I think that has not changed. Maybe the only thing is that the AI built-ness of a person. Uh, I think, uh, we see a pretty clear, a clear division between, uh, across the board. Like, um, the belief that, you know, the way you code will change completely as a result of building a company in this era. Um, building out a finance department, uh, do you think that's going to be completely different, uh, than before? So in that way, we, we interview specifically for, for that, uh, because we wanna build a 2026 version of a, of a, of a big organization, right? Uh, where like we ship twice as much than others. We move like four times as like fast because, uh, we should not only like have AI adopted in these businesses, but the big puzzle for us is how do you build a team, um, that kind of like, um, a- also incorporates AI in all these like functions. So I think that, yeah, on one hand nothing has changed, um, because yeah, the bar is still the bar, right? The... I used to be a track and field runner, um, almost became a professional like track and field runner. Took a different path in life. Um, but my friends went on to the Olympics, uh, and, um, yeah, Olympic like, uh, running is still the same, right? You need to train twice a day. You like, like push it to the edge, and that's not given like to everyone mentally and physically. So like that I think has not changed in company building. I think what you can do and the output you can generate is just like four or five times. But that's the big experiment that we're doing together, right? It's fun to see, okay, how quick can we get to all the dentists in America and build a really good product, um, such that just 200 hours gone. Like how quick can we then bring it to another vertical and then help all small businesses? Um, I think that, uh, that, that is the big interesting experiment that we are gonna do over the coming years.

    5. SP

      If it's so much easier, if everybody can hire Betty, right?

    6. SP

      Yeah.

    7. SP

      Just materialize a Betty.

    8. SP

      Yeah.

    9. SP

      Um, how does that change... I mean, like, it, it could actually work out where like small businesses, it's much easier to start one and run one, but then actually paradoxically it's much harder to be one.

    10. SP

      Mm-hmm.

    11. SP

      Because you do have, if you think about moats in the AI era in general-

    12. SP

      Mm-hmm

    13. SP

      ... we often talk about it with respect to software companies.

    14. SP

      Yep.

    15. SP

      Um, so it's so easy to go replicate X, Y, Z software. I did it on Replit, or I did it on Lovable, or I did it on Claude. Like you hear this right, you know, left and right all the time.

    16. SP

      Mm-hmm.

    17. SP

      Um, much, much harder this time to go replicate Dr. Sloop's practice.

    18. SP

      Yeah.

    19. SP

      But one of the things that makes a small business somewhat defensible is actually it is an accumulation of people that are required to deliver the end product.

    20. SP

      Yeah.

    21. SP

      And it's like, uh, if you know who Yogi Berra is-

    22. SP

      Yeah

    23. SP

      ... you know, famous Yankees-

    24. SP

      Yeah

    25. SP

      ... uh, baseball player that said all these things that make no sense.

    26. SP

      [chuckles]

    27. SP

      And, um, but like-

    28. SP

      Quoted often though.

    29. OM

      [laughs]

    30. SP

      Qu- quoted often, right? And my, one of my favorite ones, "It's so crowded, nobody goes here anymore."

  10. 55:5958:20

    How Do You Reach Hundreds of Thousands of Small Businesses?

    1. OM

      So obviously there are a lot of dental practices that want or even desperately need products like Lassie, but they are distributed, and they're all over the country, and there are a lot of them to reach. How do you think about reaching them? Like, how do you bring agents to kind of these mainstream American businesses?

    2. SP

      Yeah, this is a very different playbook than where currently I think the cutting edge is. It's like you have these models good enough and apply them in enterprises, and you do, like, a few steak dinners.

    3. OM

      Yeah.

    4. SP

      And then you sign a contract, and then you have, like, um, 10 million in ARR booked, right? Um, we literally need to go find, like, thousands, tens of thousands, hundreds of thousands of small businesses. Uh, so it's a super interesting problem to solve because we've built this agent that's really good. Um, and what we're doing right now is, is literally mapping out, like, where are all these dentists in this case, then after that the, the next small business type in the country. Who's the owner? Um, what systems are they on? Like, are there any intent signals that we can find, right? Like, they're looking for a job because they, they say they're on Indeed. Uh, and then get in touch with these, like, people, uh, with a message that resonates with them, um, and that cuts through the noise. I think that's, especially with our, um, um... Customer type is very different, right? Because if you were to sell to, like, me, you, like, find me, you know, in Clay, and, and you enrich it with some Apollo data, and then you look me up on LinkedIn, then you know, "Okay, this is the guy that's gonna buy my HR system." We can't really do that because Dr. Sloot is not in that database. He's often not on LinkedIn. Um, so, like, this is a completely different playbook that we're developing here. Um, and I think that's, that's a- another very compelling kind of, like, thing that, um, we're figuring out basically what is the go-to-market playbook look like to adopt, uh, AI in, like, uh, many, many businesses. Um, so yeah, that's, it's quite an exciting opportunity, and untapped.

    5. OM

      Thank you both so much for, for coming to chat with us today. This was awesome. We are very, very excited for the future of Lassie. Uh, anyone who's listening who might be interested in, in working with the Lassie team to build something generational here, um, check it out at lassie.ai, and you guys are very actively hiring from what I understand.

    6. SP

      Oh, yeah.

    7. OM

      Amazing. Great. Well, thank you guys again.

    8. SP

      Thank you so much.

    9. SP

      Thanks for hosting us. [upbeat music]

Episode duration: 58:39

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