Episode 74.5 — Rob Whetstine — Fortune 500 Director of Information Security and a rememberer of kindness

Rob Whetstine, known across the cybersecurity community as BowtieSecurityGuy, is the Director of Information Security at a Fortune 500 organization. A self-taught, high school educated cybersecurity professional who worked his way up from the level one help desk, Rob has built a reputation for turning around failing teams, mentoring hundreds of job seekers for free, and being radically honest about what the cybersecurity job market actually looks like right now.

In this episode, Rob shares his journey from sleeping in his car at 18 and living in the woods to becoming a Fortune 500 security executive. He breaks down why failing teams are almost never a team problem and almost always a leadership problem, why the cybersecurity job shortage narrative is largely a myth, and why passion and communication skills will get you further than any certification ever will.

Producer and Breakout Room host Rex Wilson talks with Rob at Florida Makes in Orlando about servant leadership, the realities of cybersecurity hiring, neurodiversity in the workplace, and why tying your self-worth to your career is one of the most dangerous things you can do. He also shares the story of a 3am LinkedIn message that changed everything he thought he knew about the impact of showing up for strangers.

In an episode full of revelations Rob revealed a couple doozies. He revealed that he plays Dungeons and Dragons every single Monday with a group of friends doing silly voices and has thoughts on why that makes him a better communicator. He also shared how a hat at a cybersecurity conference turned into a friendship, a podcast appearance, and a reminder that zero expectations is the only way to live.

Follow Rob on LinkedIn and across all platforms at BowtieSecurityGuy.