A Playbook for Going AI Native: Dan Guido Live with Tim O’Reilly
Published by O'Reilly Media, Inc.
To succeed with AI, first change the system
Trail of Bits has secured code for clients from Facebook to DARPA since 2012. In 2024, cofounder and CEO Dan Guido pushed the firm to go fully AI-native. Most of the team didn't buy in.
Eighteen months later, Trail of Bits has shipped 94 plug-ins, 201 skills, and 84 specialized agents (as of April 2026). On the right engagements, AI-augmented auditors find 200 bugs a week. Their new dimensional-analysis plug-in raised security-issue recall from 50% to 93% on its target benchmark. Their autonomous vulnerability finder, Buttercup, placed second in DARPA's AI Cyber Challenge, finding 28 real bugs and earning $3M. Many of these tools are open source.
Dan outlined the playbook at [un]prompted on March 3. Tim O'Reilly called it "one of the best technical talks I've ever seen, and far and away the best framework and discipline for going AI native." Tim invited him to this episode for the O'Reilly encore.
Dan will give a version of the same talk, then take about 40 minutes of audience questions on what worked, what didn't, and what is still unsolved. As he puts it: "AI works. Most companies are using it wrong. They give people tools without changing the system. That's the gap between AI-assisted and AI-native. One is a tool, the other is an operating system."
Join Dan and Tim to find out what’s changed since [un]prompted and where the playbook is heading next.
Recommended prep or follow-up:
- Read “How We Made Trail of Bits AI-Native (So Far)” (the written companion to the talk)
- Read “Try Our New Dimensional-Analysis Claude Plugin” (a concrete example of what AI-native tooling produces)
- Read “Attack of the Killer Script Kiddies” (why 2026 demands an AI-native defense, with Dan as the lead voice, from The Verge)
Schedule
The time frames are only estimates and may vary according to how the class is progressing.
Thursday, July 9, 2026, at 8:00am PT / 11:00am ET
- Interactive discussion and Q&A (60 minutes)
Your Hosts and Guests
Tim O'Reilly
Tim O’Reilly is the founder and CEO of O'Reilly Media, Inc. His original business plan was simply "interesting work for interesting people," and that's worked out pretty well. He publishes books, runs online conferences, invests in early-stage startups, urges companies to create more value than they capture, and tries to change the world by spreading and amplifying the knowledge of innovators. He’s perhaps best known for his role in shaping big ideas like open source software, unconferences (Foo Camp), Web 2.0, and government as a platform. His 2017 book WTF? What’s the Future and Why It’s Up to Us explored the role of human agency in shaping the future in the face of the coming AI wave. These days, he’s focused on mechanism design for the human-AI economy. Mechanism design is sometimes described as “reverse game theory”, whereby you start with the outcome you want and then figure out what rules of the game will produce that outcome. He explores these ideas at the non-profit AI Disclosures Project, which he co-founded with Ilan Strauss. He writes frequently on Substack at the O’Reilly Radar, the AI Disclosures Project’s Asimov’s Addendum, and his own Conversations with AI.
Dan Guido
Dan Guido is CEO and cofounder of Trail of Bits, a cybersecurity firm focused on security research and software assurance for critical technology. Since 2012, he has grown the company to more than 140 engineers specializing in cryptography, AI, and blockchain security. Trail of Bits was a finalist in DARPA's Cyber Grand Challenge and the AI Cyber Challenge, and in 2023 spun out iVerify, a mobile security tool for detecting spyware such as Pegasus. Dan advises startups, government, and policymakers on technology and cybersecurity. He serves on the boards of three startups and has contributed to policy work with the Council on Foreign Relations, RAND, and Harvard. He founded Empire Hacking, a community of 1,800+ NYC cybersecurity experts, and created Algo VPN, which has 28,000+ GitHub stars. He holds a CS degree from NYU Tandon, is enrolled in Harvard Business School's OPM program, and was inducted into CISA's SFS Hall of Fame in 2021. Earlier, he was NYU's founding Hacker in Residence, where he helped build its cybersecurity program and taught more than 300 students.