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Episode Summary:
In this episode of Automate or Die Trying, host Wil Ramos sits down with Brian Shea, a security executive, published author, and trusted leader in security, compliance, and technology. Brian shares his journey from military service to leading technology and security teams at Fortune 50 companies like Bank of America, Microsoft, and Salesforce, and now helping professionals pivot into new career opportunities through AI and “vibe coding.”
The conversation dives into the balance between speed and security in technology, the challenges of AI-assisted coding, and the importance of prompt specificity. Brian reflects on his career path, emphasizing transferable skills, adaptability, and the value of disciplined experimentation. He also explores trust in engineering teams, proactive vs. reactive security, and the role of humans in AI-assisted decision-making.
Finally, Brian discusses his AI startup, inspired by helping his wife’s Pilates business, and shares practical advice for leaders seeking to move fast without breaking things, highlighting ethical and thoughtful approaches to AI implementation.
Key Takeaways:
- Why balancing speed and security is critical in tech at scale
- How AI can accelerate coding while requiring disciplined engineering practices
- The importance of prompt specificity to guide AI output effectively
- Lessons from a non-linear career: leveraging transferable skills and curiosity
- Building trust in engineering teams through guardrails, monitoring, and transparency
- Balancing proactive and reactive security strategies in high-stakes environments
- Why humans remain essential in AI-assisted decision-making
- Practical advice for moving fast without breaking systems: plan first, act second
- The inspiration and vision behind Brian’s AI startup to support career pivots
Golden Nugget:
“AI can do amazing things, but humans are still the final line of defense. Plan carefully, act thoughtfully, and use technology to amplify, not replace, our judgment.”
Connect with Brian Shea:
- LinkedIn: linkedin.com/in/brianshea
Listen Now & Subscribe:
Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts.
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Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.
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