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AI for America's Small Businesses | Lassie

Explore episode Jul 30, 2026

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The Founding Story: Dr. Kwon's Back Office

At 6:55 · chapter starts 3:20

The origin story of Lassie is one of genuine shock rather than manufactured insight. Steijn Pelle, working at Robinhood and hunting for a hard problem, took Dr. Kwon up on an offer to see how the practice actually ran — and what he saw in the back office stopped him cold. The best-reviewed dentist in the area was spending 200 hours a month on paperwork, processing claims by hand and waiting for patients to pay because he couldn't find anyone to help him. Pelle initially assumed this was an anomaly, a quirk of one particular practice. But a gastroenterologist in Scranton showed him the same thing. Then another practice. The problem wasn't a person; it was a system — or rather, the complete absence of one. What made the insight actionable was that when they asked these doctors if they could come in and do the work themselves, every single one said yes immediately. That desperation — from busy, credentialed professionals — was the clearest possible signal that this was not a nice-to-have but an urgent, unsolved pain.

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