Show Notes
What separates a great CISO from a great one? In this powerhouse conversation, Ron invites friend and cybersecurity leader Gary Hayslip, CISO at SoftBank Investment Advisers, back on the mic to discuss what it takes to lead in today’s high-stakes digital world. Gary shares battle-tested insights on accountability, the evolving expectations of the CISO role, and how AI is reshaping leadership without replacing it.
Gary shares stories ranging from military mishaps to enterprise-scale transformation, and makes the case for visibility, trust, and embracing change. His perspective brings clarity to the fundamental responsibilities of a CISO and the mindset required to lead with impact.
Impactful Moments00:00 – Introduction
02:00 – Defining the modern CISO as a business leader
05:45 – Why CISOs should never delegate accountability
07:30 – The danger of staying invisible
10:45 – The $40K UPS explosion mistake
15:00 – How leaders build trust in new teams
19:10 – Visibility is not micromanagement
24:30 – Staying humble while leading big
30:00 – Building “Rocky the Raccoon” internal GPT
34:30 – Hiring for AI fluency in security teams
Links:
Connect with our guest, Gary Hayslip: https://www.linkedin.com/in/ghayslip/
Check out our upcoming events: https://www.hackervalley.com/livestreams
Join our creative mastermind and stand out as a cybersecurity professional:
https://www.patreon.com/hackervalleystudio
Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com
Continue the conversation by joining our Discord: https://hackervalley.com/discord
Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/
Recent Episodes
The Future of Cyber Talent Is African with Confidence Staveley
The world’s youngest continent is also its most untapped resource. Confidence Staveley, Founder of CyberSafe, makes a powerful case for why Africa’s youth are the answer to global cybersecurity ...
Compliance Isn’t the Enemy with Jeff Man
Is compliance just a checkbox, or the backbone of real security? Returning to the show with decades of hard-earned insight, Jeff Man makes the case that compliance, especially PCI-DSS, isn't ...
What Makes a Great CISO? A Playbook from Gary Hayslip
What separates a great CISO from a great one? In this powerhouse conversation, Ron invites friend and cybersecurity leader Gary Hayslip, CISO at SoftBank Investment Advisers, back on the mic to ...
Confidence, Coaching, and the S-Word with Mel Reyes
Want to stand out as a leader? According to our guest Mel Reyes, you need to dress like you mean it and speak like you’ve got nothing to prove. In this episode, Mel shares how he built ...
Purple Teaming Is the New Job Security with Maril Vernon
Cybersecurity isn’t just red or blue anymore... it’s purple, white, and deeply human. Maril Vernon, award-winning ethical hacker and Senior Solutions Architect at NetSPI, returns to the Hacker ...
The AI Gold Rush in Cybersecurity with Chris Cochran
The new cybersecurity pioneers aren’t chasing alerts, they’re building with AI. But what happens when tools meant to assist begin making decisions for us? And what skills do we lose when ...
The AI That Tried to Escape with Ron Eddings
What happens when AI refuses to be replaced? This episode kicks off with a chilling real-world example of an AI threatening blackmail—and only gets more intense from there. Host Ron Eddings ...
Zero Trust Isn’t a Tool — It’s Everything with George Finney
What if Zero Trust isn’t a framework, but the only viable cybersecurity strategy—more about people than products? In this episode, George Finney, CISO at the University of Texas System and ...
Your Two-Year Edge Starts Now with Marco Figueroa
You won’t be replaced by AI—you’ll be replaced by someone using it better. Returning guest Marco Figueroa is back with a frontline report on the AI agent boom. This isn’t a prediction—it’s a ...
Badge Cloning, Alarm Triggers & Getting Hired to Hack with Greg ...
Most people think red teaming is digital—until someone bypasses your locks, plants a Raspberry Pi in your server room, and walks out with your data. That’s not sci-fi. That’s White Knight Labs. ...
WORK WITH US
PODCASTS + SPEAKING + EVENTS
Are you the best kept secret in cybersecurity? Let's change that by partnering together for podcast ads, social campaigns, and your next event or keynote. Send us your details to get started.
Thank you!
We will be in touch soon and reach out to you at