Cyber Warfare Startup, Twenty, Exits Stealth Mode, Raises $38 Million in Total Funding
Twenty, a company specializing in industrial-scale transformation of cyber warfare technologies, announced it has secured $38 million in total funding. The Series A round was led by Caffeinated Capital, with additional participation from General Catalyst and In-Q-Tel.
Founded in 2024, Twenty has operated in stealth mode, collaborating with the U.S. military and Intelligence Community to develop and deploy intelligent, agentic, end-to-end systems designed to accelerate the offensive cyber operations lifecycle. By applying advanced software engineering practices to a sector traditionally lacking commercial innovation, Twenty provides military and intelligence agencies with enhanced cyber capabilities aimed at deterring and countering sophisticated adversaries. With a current team of 28 employees, Twenty now has funds available to ramp up hiring. According to Joe Lin, Co-founder and CEO of Twenty, the startup is seeking to recruit AI engineers from Silicon Valley, or seasoned cyber specialists from the NSA or Cyber Command.
This funding announcement comes amid growing concerns over violations of U.S. digital infrastructure and an increased emphasis on the necessity of conducting offensive cyber operations to hold adversarial entities accountable and safeguard domestic interests. Industry experts have highlighted that the United States’ investment in offensive cyber capabilities is lagging behind the rapid advancements of its adversaries, particularly the People’s Republic of China (PRC).
Recent repeated intrusions into critical U.S. infrastructure and telecommunications networks by PRC actors have raised alarms among members of Congress and Administration officials. John Ratcliffe, Director of the CIA, has emphasized the urgent need to modernize offensive cyber capabilities to ensure the U.S. possesses all necessary tools to proactively address emerging threats. This urgency has been further underscored by recent disclosures indicating that PRC state-sponsored hackers leveraged Anthropic’s AI in a highly automated hacking campaign targeting major corporations and foreign governments.
Lin identified significant gaps in offensive cyber operations during his tenure leading the Public Sector at Expanse. He observed that U.S. cyber analysts and operators often depended on manual processes and fragmented toolsets for mission-critical operations - approaches ill-suited for the required speed and complexity of modern cyber conflict.
“We are in an existential competition with the PRC, a highly determined adversary that seeks to remake the global order in its image. Cyberspace is the front line of our competition against China,” said Lin. “To counter the PRC, we must equip our analysts and operators with intelligent and autonomous capabilities needed to conduct cyber operations at industrial scale. We can no longer rely upon bespoke methods to generate mission outcomes in a domain that underpins every element of modern life and warfare.”
Timothy Junio, co-founder and CEO of Expanse (acquired by Palo Alto Networks for $1.25B in 2020) who led Twenty’s Seed round, remarked: “This is the strongest team I’ve ever seen building cyber capabilities for critical national security missions. Joe and Twenty’s co-founders have assembled an extraordinary group of world-class technologists, former operators from military and three-letter agencies, and business leaders who’ve landed over $100M in government contracts. I can think of no better company to build and deploy transformative capabilities for the U.S. government, military, and Intelligence Community.”
Twenty’s government work is particularly timely. Recently, National Cyber Director, Sean Cairncross, announced that the Trump administration’s National Cyber Strategy will transition from a focus on cyber defense to actively targeting nation-state hackers in order to prevent attacks before they occur.
Raymond Tonsing, Managing Partner of Caffeinated Capital, emphasized the urgency of the mission: “As our adversaries grow more sophisticated, the United States must close critical gaps in its cyber operations. Twenty is a once-in-a-generation investment opportunity to help improve our national security. We are thrilled to partner with Joe and the Twenty team.”
The name “Twenty” or “XX” is derived from the British counter-espionage initiative conducted during World War II, known as the Double-Cross System. Historians attribute this program with providing the United Kingdom with a significant strategic advantage.