OpenAI Ventures into Cybersecurity with Pioneering First Investment

OpenAI Ventures into Cybersecurity with Pioneering First Investment

OpenAI has made its first investment in a cybersecurity startup. Its startup fund co-led a $43 million Series A round for Adaptive Security, a New York company that helps businesses defend against AI-driven social engineering attacks.

Summary

• OpenAI’s first investment: The OpenAI Startup Fund co-led Adaptive Security’s $43 million Series A with Andreessen Horowitz, announced in early April 2025. OpenAI confirmed to TechCrunch that it is the fund’s first cybersecurity investment.
• What Adaptive does: The startup simulates AI-generated attacks, including deepfake voice calls, texts and emails, to train employees to spot them.
• The threat: Generative AI has made social engineering attacks such as spoofed calls from a CEO far cheaper to run than they were even two years ago.
• Use of funds: Adaptive plans to spend most of the money on hiring engineers.

The Investment Move: Adaptive Security

OpenAI’s startup fund and Andreessen Horowitz co-led the $43 million round in Adaptive Security. Launched in 2023, Adaptive has over 100 customers, according to co-founder and CEO Brian Long. Long previously co-founded mobile ad startup TapCommerce, which he sold to Twitter in 2014, and ad-tech firm Attentive. Unlike many earlier OpenAI fund bets, this one targets the security risks created by generative AI itself.

Fighting AI-Powered Social Engineering

Adaptive focuses on attacks that trick employees into doing something they should not, like reading out a verification code or clicking a bad link. These basic tricks have caused huge losses. Axie Infinity lost over $600 million in 2022 after a developer fell for a fake job offer. AI makes this worse. An attacker can clone an executive’s voice in seconds. Adaptive’s platform spoofs calls, texts and emails, scores which parts of a company are most vulnerable and trains staff to spot the risks.

What the Founder Says

AI tools have made these attacks easier than ever, Long told TechCrunch. His tip for employees worried about voice cloning is short. Brian Long said: “Delete your voicemail.”

A Crowded Field

It isn’t alone. Cyberhaven raised $100 million to stop staff from pasting confidential data into tools like ChatGPT, and deepfake detection startup GetReal raised $17.5 million. Investors clearly see defense against AI misuse as a growth market.

What It Signals

For OpenAI, it’s a bet on a problem its own technology helps create. Fakes are now cheap.

Backing a company that trains people to resist those fakes is a logical next step. Expect more investment in tools that test employees against realistic AI-generated attacks.

Fred Templeton, CISA, CASP, SEC+

Fred Templeton is a practicing Information Systems Auditor in the Washington DC area. Fred works as a government contractor and uses his skills in cyber security to make our country's information systems safer from cyber threats. Fred holds a master's degree in cybersecurity and is currently working on his PHD in Information Systems.