Jayson E. Street can be summed up in three words: Hacker, Helper, and Human. Professionally, he is the Chief Adversarial Officer at SecureYeti, a renowned cybersecurity expert, and hacker. In this special live recording of Do We Belong Here at the 2025 Sunshine Cyber Conference, Tashya and Pam sit down with Jayson to explore his unconventional life journey, the experiences that shaped him, and his philosophy on what it means to be a "good person"—a concept he believes is rooted in choosing to do the right thing. Jayson breaks down the benefits of logical thinking in cybersecurity and how it contrasts with the complexities of emotional decision-making. He also shares his unique take on the "red hat vs. black hat" mindset in hacking, challenging traditional notions of ethical and malicious hacking. Finally, the conversation dives into his belief that everyone is born a hacker and explores the true meaning of "hacking" beyond technology.
Stream the Do We Belong Here documentary on YouTube!
Connect with Jayson: https://www.linkedin.com/in/jstreet/
Join us on social media: @DoWeBelongPod
Chapters
00:00 Introduction to Cybersecurity and Personal Journeys
02:58 The Evolution of a Hacker: From Janitor to Security Expert
06:10 Understanding Hacking: Beyond the Labels
08:59 The Journey of Overcoming Trauma and Finding Purpose
12:08 Hacking as a Mindset: Curiosity and Innovation
14:56 Pride in One's Journey: Embracing Mistakes and Growth
17:57 The Importance of Blue Teaming in Cybersecurity
20:48 Red Team vs. Blue Team: Collaboration for Better Security
23:12 The Importance of Effective Communication in Cybersecurity
26:05 Transforming Negative Experiences into Positive Learning
27:34 Understanding Human Behavior in Security
30:46 The Art of Social Engineering and Ethical Hacking
32:37 Emotional Intelligence vs. Logical Decision-Making
39:05 Challenging Societal Norms and Speaking Out