I’ve really been impressed with the framework for enterprise AI adoption and compounding value that Dan Guido talked about at the recent (un)prompted conference. He is the CEO of security company Trail of Bits, and he gives a detailed methodology for overcoming resistance and encouraging organization-wide adoption. I liked his talk so much (it’s only 20 minutes) that I asked him to deliver it again on the O’Reilly platform and then take questions from the online audience. It’s tomorrow at 8 am Pacific. Attendance is free.

A Playbook for Going AI Native: Dan Guido Live with Tim O’Reilly

Source: https://www.oreilly.com/live-events/a-playbook-for-going-ai-native-dan-guido-live-with-tim-oreilly/0642572379827/ View all eventsPublished byO’Reilly Media, Inc.

Intermediate content levelIntermediate

To succeed with AI, first change the system

ScheduleTrail 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.

Danoutlined the playbookat[un]promptedon 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)

• Tim O’Reilly is the founder and CEO of O’Reilly Media. He has a history of convening conversations that reshape the computer industry. He’s played a key role in shaping our understanding of the early commercialization of the internet, open source software, big data, and Web 2.0. He believes that the current AI moment is more significant than any of those. His 2017 book,WTF? What’s the Future and Why It’s Up to Us, raised many of the concerns and opportunities about AI that we are wrestling with today. He writes regularly forO’Reilly Radarand onAsimov’s Addendum, his Substack about AI governance.

• 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.

Skill covered

Artificial Intelligence (AI)