Harley Sugarman

Harley Sugarman is the founder and CEO of Anagram, a New York security company rebuilding employee security training around behavior instead of boredom. A Stanford computer scientist and former Bloomberg Beta investor, he scrapped his original product and rebuilt it into a TikTok- and Duolingo-inspired microlearning platform that cut client phishing failure rates from 20% to 6% and won over Disney, Thomson Reuters, and MassMutual. Anagram raised a $10M Series A in 2025 led by Madrona.