healthcare.gov
The website whose initial failure prompted the creation of the U.S. Digital Service, highlighting the need for better government tech integration.
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Videos Mentioning healthcare.gov

Tim O'Reilly Interview | The Tim Ferriss Show (Podcast)
Tim Ferriss
A government website that experienced a major failure in 2013 due to poor implementation and testing, highlighting issues in policy execution and technology procurement.

Matt Cutts on the US Digital Service and Working at Google for 17 Years
Y Combinator
The website whose initial failure prompted the creation of the U.S. Digital Service, highlighting the need for better government tech integration.

The AI Architect: Bret Taylor
Latent Space
A government website that famously experienced a disastrous launch and security vulnerabilities, highlighting the need for robust software systems.

Work at a Startup Expo 2019
Y Combinator
The backend system that powers HealthSherpa, giving them direct API access, which is a unique market position in the consumer health insurance space.