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He Built an AI That Beats Insurance Companies at Their Own Game | Dean Margolis x Red Sky Health

Season 2026 Episode 56 Published 9ย hours ago
Description

Health insurers use AI to deny thousands of claims a minute. Dean Margolis built the AI that fights back, and it doesn't get paid unless the hospital does. Inside this episode: a serial founder with 3 exits and an IPO, a product literally named after "denial," and a business model Gartner is already calling the future of software.

๐Ÿฉบ What we cover:

๐Ÿ’ธ The clerical error hiding inside half of all denied claims, and how AI catches it instantly
ย ๐ŸฅŠ Insurers auto deny thousands of claims at once. Red Sky auto fixes them at the same scale
ย ๐Ÿ” The 4 denial types costing hospitals millions: coding errors, eligibility gaps, missing pre auths, and "not medically necessary"
ย ๐Ÿ”’ Why one compliance mistake could send a CEO to prison, and why Anthropic or OpenAI legally can't touch this data
ย ๐Ÿง  Agentic AI, machine learning, and old school table lookups working together, not one silver bullet
ย ๐Ÿ’ผ 3 startups sold to public companies, 1 IPO, and why Dean says his own ideas are usually terrible
ย ๐ŸŒ Zero office, a team across 10 states and 3 continents, and just 4 engineers because Claude and Cursor write the code
ย ๐Ÿ“Š The 20% outcomes based fee model Gartner is calling the death of traditional SaaS
ย ๐Ÿš€ First hospital network signed, $5M raised, and a Series A already lining up

๐Ÿ”— Links:
ย Watch more episodes of The Index: https://www.youtube.com/@theindexpodcast
Dean Margolis on LinkedIn: https://www.linkedin.com/in/dean-margolis-48935
Red Sky Health website: https://www.redskyhealth.com/
Red Sky Health LinkedIn: https://www.linkedin.com/company/redskyhealth

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