Engineering, policy, and product writing from the CoolBiz® team. New posts as they happen.
In 2025, the U.S. Department of Health and Human Services (HHS) handed out more than twenty HIPAA penalties. Most came down to one thing: companies skipped required AI risk paperwork. And most AI tools claiming "HIPAA compliant" won't even sign a BAA. Here's how to tell the real ones from the rest.
Read →GDPR fines can reach 4% of global revenue. HIPAA penalties run up to $2.19 million per violation category per year. Here's how to tell if your AI chatbot can actually survive the regulators who matter.
Read →Existing financial regulations apply to AI chatbots the same way they apply to human agents. That's the position of the Consumer Financial Protection Bureau (CFPB), and the OCC's model risk management guidance reinforces it. A finance-grade chatbot is built to meet that standard. Here's what that looks like in practice.
Read →Existing professional responsibility rules apply to AI chatbots the same way they apply to lawyers. That's the position of the American Bar Association (ABA), and state bar opinions from Florida to California have reinforced it. A legal-grade chatbot is built to meet that standard. Here's what that looks like in practice.
Read →Existing insurance regulations apply to AI chatbots the same way they apply to human agents. That's the position of the National Association of Insurance Commissioners (NAIC), and a growing list of states has put it in writing. An insurance-grade chatbot is built to meet that standard. Here's what that looks like in practice.
Read →Existing fair housing rules apply to AI chatbots the same way they apply to human agents. That's the position of the Department of Housing and Urban Development (HUD), and the Justice Department has already brought a case to prove it. A real-estate-grade chatbot is built to meet that standard. Here's what that looks like in practice.
Read →68% of AI projects miss their ROI targets, and the average miss runs 47% below projection. Here's how to measure chatbot return honestly, what most companies get wrong, and how to land in the small group that actually delivers.
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