Thinking Like the Attacker

Priced July 17, 2015

Rapid7 bought Metasploit, a widely used open source tool for testing security, and won a large following among researchers. Its own software scanned networks for weak spots, tested defenses and later watched for signs of an attack. When Rapid7 filed to go public in 2015, major breaches had pushed security to the top of company agendas. Companies had more systems to defend each year.

Buying Metasploit

Rapid7 was founded in Boston in 2000 and began with vulnerability scanning. In 2009 it bought the Metasploit project, which brought it close to the community of security researchers. The bet was that defenders needed the same insight as attackers, delivered in software that IT teams could use every day. The company later moved its products to the cloud, where customers could run them without their own servers.

Subscriptions and AI Agents

Rapid7 priced at $16 a share in July 2015 and rose on its first day. It expanded into detection and response and sold more of its products as cloud subscriptions. The company grew steadily, though profit came slowly. Corey Thomas led it as chief executive through most of its public years. Rapid7 remains public, based in Boston. In March 2026 it bought Kenzo Security, a startup that uses AI agents to investigate security alerts.

Cover: Kakegawa: Crossing the Forty-eight Rapids on the Akiba Road (Kakegawa, Akiba michi shijuhachi segoe), no. 27 from the series "Famous Sights of the Fifty-three Stations (Gojusan tsugi meisho zue)," also known as the Vertical Tokaido, Utagawa Hiroshige. Art Institute of Chicago, public domain. Chosen for crossing the rapids.