Scout Skills, Leadership Hacks, and Smart Security in the Age of AI | Kirby Winters, Ep 17
Episode Summary
Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Eagle Scouts and entrepreneurship. He covers the evolving threat landscape—from social engineering to AI-enhanced phishing—and explains how fractional security leadership helps SMBs navigate SOC 2, HIPAA, and CMMC compliance without full-time hires. The conversation explores VPN evolution, cyber insurance realities, and the critical need for proactive security planning before customer mandates or breaches force action.
Pull Quotes
On leadership lessons from a Navy mentor
“It's amazing what you can get accomplished if you don't care who gets the credit.”
“Nothing will broaden your capabilities more than starting your own business. You have to do everything. You have to be in sales, you have to be in HR, you have to be in operations. Otherwise the business will fail.”
On cyber insurance payout rates
“Out of the 50 plus claims that I've seen over the years, I've only seen five to 10 that ever got paid out.”
“You don't do an audit because you want to. You do it because somebody told you to. It's a cost. It's a lot of effort. And if you don't have to, then most people don't.”
“The best protection is the best protection as you can afford because even if you buy cyber security insurance, your probability of getting a payout on that is in the 10 to 20% range in my opinion.”
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.
Want to go deeper?
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