Making Risk Make Sense with Rob Black

“There’s a 5% chance of a $5 million loss. Is it exactly right? No. But it’s way better than saying medium, because medium means nothing.” Kenny sits down with Rob Black, Founder and CEO of Fractional CISO, to break down how to translate cyber risk into language executives actually act on: probability, dollars, tradeoffs, and clear acceptance instead of vague labels that disappear into a slide deck. We also get into the “magic genie” myth of GRC tools, what vCISO looked like back in 2017, and the origin story behind Rob’s legendary wig videos. Key takeaways: • How to quantify risk without pretending it’s perfectly precise • Why “high/medium/low” breaks the conversation with leadership • Where humans are still required (even with great tools) Learn more about Rob Black here:  https://www.linkedin.com/in/blackrob/ Learn more about FractionalCISO: https://fractionalciso.com/ Learn more about Kenny: https://www.linkedin.com/in/kenny-g-scott/ Learn more about Paramify: https://www.paramify.com/