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Lassie was founded after Stein saw his own dentist spending 200 hours a month on paperwork, and the problem turned out to be widespread across hundreds of thousands of small healthcare practices.

Stein explains how a conversation with his dentist Dr. Quan revealed that small healthcare practices still process insurance claims and payments entirely by hand, a problem he assumed was solved decades ago. ✦ AI generated

Stein · a16z Podcast · 2026-07-30 · original ↗

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

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 busy work. So submitting claims by hand and he had to stick around himself because he couldn't find people to like build the patients... I thought that this was a solved problem cuz in the 70s my mom worked in hospital and that's what she did. She brought backs of cash to the bank and then processed payments by hand. Uh but it wasn't a solved problem here.

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1:18Stein, this whole company started with a conversation with you and your own dentist, Dr. Quan. What did he tell you that made you decide to quit your tech job at Robin Hood and go process payments for him by hand? >> 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 Robin Hood at the time. Um and uh I came

1:40to this country to start a company. So after 6 years um I moved from Amsterdam to Silicon Valley like I was looking for a heart problem to solve. And then my doctor Dr. Quan uh 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 heart problem and he said, "Do you want to see how I run my

1:58business?" And I said, "Absolutely." Um, 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 busy work. So submitting claims by hand and he had to stick around himself because he couldn't find people to like build the patients. So I'm like, "Wow, it's

2:18fascinating. This is like a couple of years ago." So I thought that this was a solved problem cuz in the 70s my mom worked in hospital and that's what she did. She brought backs 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 >> though I have to ask when he gave you

2:35this offer were you like 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 or how did that go down? >> Well uh up until now I don't have cavities so you know there was no drilling happening yet. Uh so you know knock on wood >> examination. >> Exactly. Exactly. Yeah. Um um no like he

2:56he uh took me aside like after that. >> Okay. >> Um because he he knew that I was like looking for this like heart problem. I 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 didn't really uh make sense to me because he was very

3:15like well rated. He used all these modern technologies. So then um we started like talking to other doctors like because maybe this Dr. Guan was just like an anomaly but then you know I also like worked for a gastronologist 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

3:34thousands 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. 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

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