Lessons from the ex-CIO of Microsoft, Disney and the U.S. Government

Tony Scott is the CEO of Intrusion, a publicly traded cybersecurity company. Before joining Intrusion in 2021, he served as the Federal CIO of the United States under President Obama, as CIO at VMWare, CIO at Microsoft, CIO at Disney, and as CTO at General Motors. Yes, let that sink in.

In this episode, we talk about what Tony learned from working with Bill Gates, Obama, and other world leaders, what it actually takes to land a C-level role at a Fortune 5 company, and why he predicts a major AI disaster is coming in 2026.

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We discuss:

* The three most stressful weeks of his career (and there were many)

* Why he chose to become CEO of a struggling cybersecurity company after serving as the Federal CIO

* What Bill Gates really meant when he said “that’s the dumbest thing I’ve ever heard” in meetings

* How to actually get a C-level role at a Fortune 5 company

* Tips for founders trying to sell into the enterprise or government and the phrases that immediately kill deals

* Why he predicts a major AI disaster in 2026

* What flying taught him about business

* Why someone who’s already “made it” still invests in LinkedIn

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Connect with Tony:

LinkedIn: https://www.linkedin.com/in/tony-scott-intrusion/

Intrusion: https://www.intrusion.com/

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Connect with Finn:

LinkedIn: https://www.linkedin.com/in/finnthormeier/

Project 33: https://www.project33.io/

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My personal takeaways:

* What gets you a meeting with a CIO at a Fortune 100 company is doing your homework & finding a top 3 organizational problem they're trying to solve. If you come to pitch on innovative tech, you won't get far. And if you start the conversation with "what keeps you up at night?" you've already lost. It shows you did zero research. Tony had a secret signal with his assistants to get rescued from bed vendor meetings. That question was usually the trigger.

* Tony's prediction for 2026: there's going to be a very big disaster as a result of the abuse, misuse, or accidental use of AI. Something attention-grabbing. And people are going to go "oh my god, we didn't know that could happen." We're building so much on top of AI without understanding all the points of failure, so when that failure occurs, it'll bring on a bunch of governance and regulatory inspections. It happened with every big invention we've ever had.

* What impressed Tony most about interacting with Obama: his questions. He’d ask surprisingly deep questions about technical topics. When Tony’s team would send in a draft white paper (about something cybersecurity related), they’d often overnight get back a markup from the president with all kinds of notes & questions in his handwriting in the margins.

* At Microsoft, Tony interfaced with Bill Gates, who would often say "that's the dumbest thing I've ever heard” in meetings. Tony saw it as a test to see if the person had done their homework on their idea/proposal/opinion, and were able to stand their ground. Problems happened when other executives tried to copy that style without context and without being Bill (Tony decided not to emulate it)

* None of the things Tony did in his career were direct predictors of the thing he was gonna do next. He went from Sun Microsystems to startups to being the CIO at Microsoft, Disney, VMware, then Federal CIO under President Obama, and finally, CEO of a public cybersecurity company navigating headwinds. Recruiters kept finding him because he had an unusual combination of tech experience + a law degree. That made him stand out. His advice if you want unique opportunities: build a unique skill stack.

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