By Rex Wilson, Cyber Florida Brand Manager

Jayson E. Street—the self-described hacker, helper, and human—is known for a lot of things. Not surprising for someone who robs banks for a living. (Legally, of course.) In his world, reputations tend to precede people. But among the many things Jayson is known for, one stands out: the awkward hug.

Before meeting him at Sunshine Cyber Con in 2024, I assumed an awkward hug was just a poorly executed embrace—one where both participants weren’t equally committed. That might be true in some circles, but not in Jayson’s world. When we finally met in person, he asked, “Do you want a little awkward or full throttle?” Like any self-respecting, socially awkward introvert, I went for full throttle. The result? The photo you see in this post—an unforgettable moment I’ll treasure for a long time.

But as much as I loved that interaction, it wasn’t even my most memorable Jayson moment of Sunshine 2024. That honor goes to a simple conversation we had between sessions.

While running around conducting interviews for a documentary, I kept noticing Jayson stationed at a table in a high-traffic area. Every time I passed by, he was engaged in conversation with different attendees—sometimes one-on-one, sometimes with three or four at once. Eventually, I caught a quiet moment with him and asked, Why park yourself in such a visible spot? Isn’t it exhausting to be ‘on’ all day?

“Yes,” he admitted. “But this might be the only chance some of these people have to connect with me in person, and I have to be there for them. Who knows what will come out of that conversation?”

That philosophy—being present, making space for connection—seems to define the way Jayson moves through life. And I admire it. Peopling can be hard, but the right conversations can be life-changing, soul-enriching.

This year, Jayson returns as our keynote speaker, and I couldn’t be more excited for his talk, How to Hack Like a Failure (Like Me!). But that wasn’t quite enough Jayson for us, so we also invited him to join our Do We Belong Here? podcast for a live recording—an epic combination in the making. And as the icing on the Sunshine cake, he’s bringing some of his hacker friends to launch our first-ever Hear from the Hackers track.

Want to experience all of this in person? Register for Sunshine Cyber Con today. It’s an awesome event—even if you’re not an awkward hugger.