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June 9, 2026 · Note

The whole Trail of Bits story

tl;dr Derek Hsue took me through Long Island, the NSA, the Fed, and fourteen years of Trail of Bits on The Archive.

Also on Spotify, Apple Podcasts, and X.

There’s a lot in here I haven’t talked about anywhere else: how Trail of Bits survived eight months without revenue after the 2013 government shutdown, the day we bought every 32xlarge EC2 instance on Earth for DARPA’s Cyber Grand Challenge, an Amazon tech running through a Sydney data center to find us machines, and how getting robbed in the DAO hack led us into blockchain security. We also get into incident response at the New York Fed, hiring for mastery, and learning to become a CEO.

There are four exchanges worth pulling out.

On how companies will have to adapt now that frontier models can do real offensive work (watch):

“It means that companies have to respond at machine speed to these intrusions, because that LLM is going to be seeking out all these little opportunities, these chinks in your armor, in order to further burrow itself into your company.”

On why North Korea keeps winning against blockchains (watch):

“What you see from them is they’re performing intrusions, assessing the environment they have access to, and on the fly writing novel tools to take advantage of it. They’re writing smart contract code. They’re writing malware. They’re doing things that are really quite sophisticated.

So yeah, I’m impressed. They did a good job. I was an attacker. I have to appreciate good game when I see it.

With the NSA or somebody else in the US, they’re going to have reams of lawyers. They’re going to pull out some huge book of Title 50, Title 10 stuff. They have so much restraint. North Korea and Iran don’t.”

On how Trail of Bits ended up in blockchain security (watch):

“So we all bought DAO tokens and then we all got robbed. And it was this funny light bulb moment when we were like, oh my God, did another hacker just steal money from us?”

And on who Trail of Bits hires (watch):

“We take all comers. One of our most successful employees was a lot like me. It took me six years to graduate college. I had to go back for my final semester and finish physics one, discrete math, and linear algebra.

I was a smart kid that burned out, and I think a lot of people who are highly motivated and understand what they want to do in the world have a similar experience.

At Trail of Bits, the thing that binds everybody together is that we all want to be the best at what we’re doing. It’s team cohesion through competence.”

Use these timestamps to jump into the recording: