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Explore 24 Hours Inside a $47M YC AI-native Insurance Startup with 313,927 views, 3,402 likes, and 376 comments. Experience the impact of this video content that has captured audience attention.

In this episode, I go behind the scenes with Harper, a YC backed AI-native commercial insurance brokerage built by founders Dakotah Rice and Tushar Nair. The founders have raised $47M in combined seed and Series A funding, led by Emergence Capital, with backing from Y Combinator and Peak XV Partners. A traditional broker takes five to seven days to source quotes and place a business with the right cover. Harper does it in one to two, matching small and mid-sized businesses against more than 160 carriers for insurance products like workers' compensation, general liability, and professional liability, and many more. Dakotah grew up around his family's insurance brokerage and watched the system fail small business owners in real time. He and Tushar had already built and shut down an investment platform called Poolit, which raised $10.6M in seed funding, before reuniting to start Harper in 2024, going through Y Combinator's W25 batch. The company is adding roughly 1,000 new customers a month, a volume no human sales team could touch. The question Harper is trying to answer in real time, can two founders rebuild an entire industry's back-end fast enough with AI to capture that demand, without the whole thing breaking under its own growth? Inside this episode: - Harper's 5:15am sales briefing and the push to close quotes before deadline - A live bug where a parsing error made customer quotes look like pure "fees and taxes" - Dakotah walking through Harper's AI voice agents taking over intake across new verticals, live - The internal debate over which metric actually signals growth, first-pass rate or quote speed - A funnel review naming 38 stuck applications, one by one - Dakotah and Tushar on surviving a failed company, letting go of founder mode, and what it actually takes to build at venture scale Harper has automated its way past nearly every bottleneck a traditional broker runs into. The one that's left is the founders themselves. Harper is hiring: https://link.willphillips.co/harper-jobs Join my founder newsletter: https://link.willphillips.co/newsletter Let's connect: X: https://link.willphillips.co/Twitter Instagram: https://link.willphillips.co/Instagram LinkedIn: https://link.willphillips.co/LinkedIn 00:00 Introduction 01:36 Inside Harper's morning 02:17 Harper's 5:15am sales briefing 04:11 Funnel review meeting 05:06 Live parsing bug on a customer quote 06:11 Debating the right growth metric 06:43 Coffee and energy drinks with the team 07:20 How Harper uses AI to track everything 08:34 Team taste-tests C4 09:07 Growth meeting: scaling voice AI verticals 10:43 Turning voice AI into an R&D priority 12:11 Will debriefs on the voice agent rollout 13:12 Reviewing a $242 lead 14:34 Is this a normal morning? 15:59 Will on Dakota's focus 17:20 All-hands meeting 18:31 Reviewing 38 stuck applications 19:51 Founder advice: "get into the arena" 21:08 Closing thoughts

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