Cybersecurity has always been a cat-and-mouse game, but the cat just got a PhD in generative AI. Enter Adaptive Security, founded in 2023 by Brian Long and Andrew Jones, the duo that already proved they can build billion-dollar companies with TapCommerce and Attentive. This time they are locking sights on AI-powered social engineering, deepfakes, impersonations, multi-channel scams, and they just extended their Series A to $55 million. The round was co-led by Andreessen Horowitz and the OpenAI Startup Fund, with support from Abstract Ventures, Eniac Ventures, CrossBeam Ventures, and K5. The kicker? The OpenAI Startup Fund has only one cybersecurity investment, and this is it. That should tell you everything about conviction.
Brian Long is no stranger to scaling. He co-founded TapCommerce, sold it to Twitter, then built Attentive into an $850 million venture-backed rocket with 8,000 customers and $500 million in annual revenue. Andrew Jones was the product architect, managing teams of 100+ and making Attentive indispensable to the enterprise marketing stack. Now, they are pouring that playbook into the one arena where human error keeps wrecking balance sheets: cyber deception.
Adaptive Security launched publicly in January 2025 and has already secured more than 100 enterprise customers. Banks, healthcare systems, software companies, even the Dallas Mavericks are onboard. Their tech generates deepfake personas with less than 10 seconds of audio, runs phishing simulations across email, SMS, chat, and video, and trains employees in short, sharp modules rated 4.8 out of 5. And yet, the reality is stark, sixty percent of employees still fail deepfake attacks. That failure rate is the opportunity.
The stats are brutal. Email phishing attacks are up 4X since ChatGPT went mainstream. Deepfake attempts now hit the U.S. every five minutes, adding up to over 100,000 incidents annually. Adaptive Security flips those same tools back on the attackers, combining OSINT-personalized simulations, AI-powered risk scoring, and board-ready analytics. They do not sell fear. They sell competence, fluency, and resilience.
This $55 million is fuel for scaling their engineering team, hardening their AI-native defense platform, and expanding beyond their 74-person footprint in New York and Beverly Hills. The adaptive security market itself is projected to nearly double by 2030 to $25 billion. Whoever masters the gray zone between trust and trickery will own the enterprise security stack.
