Ep17 - Kirby Winters — Scout Skills, Leadership Hacks, and Smart Security in the Age of AI
Episode Summary
Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Boy Scouts and entrepreneurship. He covers the evolving threat landscape, social engineering attacks, cyber insurance challenges, and compliance requirements like SOC 2 and CMMC. The conversation explores how AI is amplifying security risks and the growing need for fractional security leadership in small to mid-sized businesses.
Key Quotes
"It's amazing what you can get accomplished if you don't care who gets the credit—a leadership principle that emphasizes team success over individual recognition."
"Out of 50+ cyber insurance claims I've seen over the years, only 5 to 10 ever got paid out—highlighting the importance of having proper security controls in place before a breach occurs."
"The best protection is the best protection you can afford, because even if you buy cyber insurance, your probability of getting a payout is in the 10 to 20% range."
Transcript
Hi welcome to Tales From The Sky Lounge, a podcast about business consulting and venture investing. We get out there in the world, we talk to people who are making it happen and we get their stories. So if you could like and subscribe it helps us to get a message out.
Today in the Sky Lounge we have Kirby Winners. Hi Kirby, how are you?
Great, Todd, how you doing? Thanks for having me today.
Yeah, it's good to have you here. Why don't you tell us a little bit about you and what you're working on?
Sure. I've been around Atlanta for pretty much my whole life. I love living here. I've done some stints outside of the city but keep coming back. And I've done a lot of traveling over the years which is just great for sanity and meeting good people and all that kind of thing. But I started out in Telecom. I spent a lot of time there, did a little consulting, and then over the years it kind of led me into owning my own business. I had a lot of opportunities over time to start some businesses and they either went different ways as they always do. And finally I really dove in and started my own business, did that for eleven years and sold it in 2011. And from there I went back into consulting. And now I'm with TechCXO. So TXO is a great little consulting organization where I lead up our information security program. And we do essentially fractional and interim CESO work and provide compliance services to a lot of our clients. So I really enjoy it.
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