EP015: Blockbusters, Breaches, & Bad Decisions with Jeffrey Wheatman

Nerds That Talk Good
Nerds That Talk Good
EP015: Blockbusters, Breaches, & Bad Decisions with Jeffrey Wheatman
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Episode Summary:

Jeffrey Wheatman, a cyber risk leader, strategist, storyteller, and former VP at Gartner, joins me to talk about bridging the gap between security, risk, and business leadership.

Jeffrey shares his non-traditional path into cybersecurity—from retail management to pen testing—and how he discovered that his true strength wasn’t just in doing security, but in talking about it in a way that actually makes people care. We discuss the pitfalls of cybersecurity messaging, the power of storytelling in risk communication, and why CISOs (and vendors) need to stop thinking they’re the hero of the story.

We also dive into the myths of startup positioning, why founders struggle to take feedback, and how to balance category fit with differentiation. Plus, Jeffrey gives an inside look into Risk & Reels, his podcast that blends risk management with his love of movies.

Resources Mentioned:

Events & Conferences

  • DEF CON – Jeffrey is a long-time “Goon” (volunteer staff) at DEF CON, one of the largest hacker conferences in the world .
  • RSA Conference – Mentioned as a key industry event where Jeffrey will be attending and speaking .
  • Black Hat – Another major cybersecurity event Jeffrey regularly participates in.
  • Gartner Security & Risk Conference – Referenced in the discussion of analyst relations and industry insights .
  • ISACA GRC Conference – Jeffrey is scheduled to present at this governance, risk, and compliance conference.

Cybersecurity and Risk Frameworks

(Note: some links above may contain affiliate links that help support the podcast.)

Highlights from Jeffrey:

On Startups & Founders Trying to Do Too Much

“I can’t tell you how many companies had amazing technology, but the founder just couldn’t let go of the reins. If you suck at sales, let someone else do it.”

On the Danger of Chasing Categories

“If you’re a market of one, nobody’s talking about you. But if you’re just another name in a crowded space, you’re forgettable. You need to fit in just enough to stand out.”

On AI & Threats

“AI isn’t letting attackers do anything new—it’s letting them do the same things, just way faster. And we are not prepared.”

On His Podcast, Risk & Reels

“I wanted to make it fun. So I start every episode asking about a favorite movie, and somehow we always find a way to tie it back to risk.”

If you’re a tech professional, founder, or communicator, this episode is packed with insights you can’t afford to miss.

About Jeffrey:


Jeffrey Wheatman is a cybersecurity and risk strategist, storyteller, and executive advisor with over 25 years in the industry. A former VP at Gartner, Jeffrey has worked with Fortune 500 companies, CISOs, and startups, helping them bridge the gap between security, risk, and business leadership.

Now serving as SVP, Cyber Risk Evangelist at Black Kite, he specializes in third-party risk intelligence, cybersecurity strategy, and communication. Jeffrey is also the host of Risk & Reels, a podcast that blends risk management insights with a love of movies.

When he’s not talking cyber risk, you’ll find him traveling the world, getting scuba certified, and collecting DEF CON badges.

Episode Transcript:

Transcript

Jeffrey: Hey, look, I get the fact nobody wants to be told their baby is ugly. But you need to be open for a commentary and criticism, right? We, I always tell the story of the blind people and the elephant, and I won’t do it ’cause I don’t wanna suck up the time.

But essentially the moral of that story is we get so close to a problem, we don’t see the bigger picture, right? So yeah, you’re right, you may have a perfect solution, but there are other people that do 60% of what you do. What is it you do differently and why? 

Joel: My name is Joel and I’m a recovering nerd. I’ve spent the last 25 years bouncing between creative jobs and technical teams. I worked at places like Nickelodeon to NASA and a few other places that started with different letters.

I was one of the first couple hundred people podcasting back in the early aughts until I accidentally became an IT analyst. Thankfully, someone in the government said, “Hey, you’re a nerd that talks good.” And that spun me off into the world of startups, branding, and marketing, for the same sort of researchers and startup founders that I used to hang out with. 

Today, I help technical people learn how to get noticed, get remembered, and get results.

On Nerds That Talk Good, I want to help you do the same. I talk with some of the greatest technical communicators, facilitators, and thinkers that I know who are behind the big brands and the tech talk that just works. I am super excited to have Jeff Wheatman on today, and we will introduce his alter ego in just a little bit.

Jeff and I go way back and we will probably reminisce on some of those stories. Jeff’s been doing cyber so long, it wasn’t even called that when it got started. He is an experienced cyber risk leader, practitioner strategist, thought leader, storyteller, executive advisor, Goon, and the former vice president in Gartner Cybersecurity and Risk Management Group.

He is now, I think I saw at one point you had a title “Risk Evangelist”.

Jeffrey: Yeah, so that was my original title, but we changed that and I’ll actually share why, ’cause I think it’s relevant to some of the stuff we’re gonna talk about. Word words mean stuff.

Joel: Yeah, that was my title at Emergynt. So, I want to dip into that. Jeff. Thank you for joining.

Jeffrey: Oh my God, Joel, it’s a pleasure. When I saw that you were launching this new podcast, I immediately reached out and said when are we gonna have me on? And then I will, I just gonna open the raincoat. Joel made me fill out a whole questionnaire and a whole bio sheet before he would allow me to come on the podcast,

Joel: I didn’t read any of it. I’m kidding. I’m

Jeffrey: that’s okay.

Joel: So.

Jeffrey: I’m actually super excited to be here. This this will be fun and we do go back a long way.

I’m at the point in my career now where I go back 25, 30 years with some people, which is crazy.

Joel: Yeah. Yeah, it’s phenomenal. Well, let’s go back a little bit farther. I always like to start off, I, you’ve got a podcast which we will talk about. You always start off with the same question. I ripped that off of you, obviously. And I wanna start off with just give us the nerd origin story.

Tell, tell us how you got into tech, how you got into talking about tech and where we find you today.

Jeffrey: Yeah. So I love doing this ’cause my career pathway is definitely not a traditional cybersecurity pathway. Um, So I am, I’m 57 years old, so I’m gonna reference some technology that some of our listeners probably have never heard of. But back in the day when PCs were first becoming known, Radio Shack had the TRS 80, right?

That was the computer. 

Joel: Trash 80. 

Jeffrey: And it was expensive. And my parents were like, yeah, I’m not buying this. So I ended up buying a Texas Instruments TI-99/4A. That was my first computer. And the thing literally came with like a separate, the big five and a quarter, or five and a half inch floppies, and I had to literally install.

Everything from scratch, and it was super painful, but I loved it. And I wrote like a little game and I sold it to a local electronic store. It was like a la lame version of like Space Invaders, but like, we had to peek and poke every single frigging dot on the screen. And I just always have loved technology.

I’ve always been enthralled, I’ve always been a science geek, a science nerd. I read physics for fun. I’m a sci-fi guy and, I continued to play with that. And then when it came time to become an adult I actually ended up in retail. I was managing a hardware store in New York City, and I got tired of coming home and yelling at my girlfriend.

Every single day. ’cause I hated working in retail. I hated working with the people I worked with. And I was just miserable. And I said, I like technology. And I basically put myself through a Novell NetWare training class, learning Novell NetWare 3.11. So again, dating myself. And I did that at night and I literally applied for a bunch of jobs.

I had no experience. I had no background, but I talked good. And I got hired by a guy. Named Robert Ponti, who I actually still am in touch with all these years later. And I ran a team that installed Linux servers for for color printers. I. And I started playing around with Linux and Solaris and Unix and I went, oh, this is like really cool, interesting stuff and Free BSD.

And this was even like before Ubuntu and Linux was still like really new back then. And we were just off to the races from there and I was just constantly teaching myself stuff. And then at one point I was working for a consulting company and the company was on the blocks. So, nobody was signing up for any new business and they didn’t want me to leave, so they tucked me in this job where I literally had four hours of work to do a week.

So I was bored. So I stumbled across a website called 2,600, and I found these articles written by the Happy Hacker, Carolyn Meinel. And I know she’s gotten a lot of crap o over time, but she was teaching people how to do pen testing before it was even called pen testing. Thing, right? So I literally, I learned how to do a pen test and I said, this is way, way more interesting than the shit I’m doing now.

And I decided that day, I am now a security person and I have just never looked back. So I’ve done everything in security. I did network security, I did application security, I did data security, I did pen testing. And what I learned about myself is I wasn’t very good at any of those things. But I could talk about ’em and I could talk about ’em to a business person and a technology person, and I could sit at a table and bring those two audiences who literally could not communicate together.

So I literally have built a career out of talking. I. And if you ask anyone in my family, they will say, that’s good. ’cause I don’t know that you’re good at anything else. So that’s my story. And um, you know, I, and for those of you out there that are looking and aspiring to a career, and Joel and I talked about this before we actually started, first thing, if you want to be cyber, you better love it.

’cause it is a life of misery and unhappiness otherwise. But if you love it, don’t fall into the “Well, I’ve never done that.” I always tell people. Your goal in life is to figure out how to do the job they hired you to do before they figured out you did not know how to do the job they hired you for. That has been my entire career. I walk in and I go, okay, who’s the best at this thing you hired me for? I’m gonna be better than that person and that has been what I’ve done. And I started up some consulting practices. I learned a lot about the difference between security and risk. And then I ended up, I did a 15 year stint at Gartner.

And I know, Gartner can be somewhat polarizing, but I’ll tell you, I work with some of the smartest people. I still have a bunch of really good friends there. That’s where you and I met when you were back at Emergynt. And and I still think you guys had the coolest technology. And I just, I learned really how to build these bridges and have effective communication.

And then about three years ago I was talking to Paul Paget, who is the CEO of Black Kite, where I am now. And I hung up the phone and I said, these guys are doing something really cool. I think I can help them. And I reached out to Paul and I told him that and he agreed and so I’m coming up on, on three years now with with Black Kite.

And if anyone is interested in learning, definitely reach out to me. I’m not a sales or marketing person, but I’ll talk good to you. So that’s my my, my career. And then in there, so you mentioned Gooning and I don’t know, we will talk about that, but I got invited to be a speaker goon at DEF CON.

And you can actually see I have a goon sticker on the back of my phone. So for those of you who don’t know, DEF CON is a very big hacker conference. It’s like 50,000 people and it is entirely run off the sweat equity and backs of a bunch of unpaid volunteers, Goons.

And when I was doing that, I. I had cocktails with Fyodor, the guy that invented Nmap. I hung out with the late great Dan Kaminsky. I just met people who literally came before me. You talked about stealing something from me for the podcast, and what do you think I’d made this stuff up?

I stole from everybody. Newton has a great line “I see far because I stand on the shoulder of giants” and I got to hang out with those people. And I’m friends with those people and that’s, I have a life beyond my wildest dreams. That’s. That’s it in a nutshell,

Joel: I could just tell you’re just smiling, beaming from ear to ear. You smile more when you talk about DEF CON than when you talk about the work stuff. So we’ll get into some of that. 

So I talk about in my workshops or when I’m doing one of my talks, I actually share the Emergynt, not the founding story, but the story of when we discovered what theto the story of the story to, to some extent. And you saw us very early on in those early days when we were still scrambling to figure out how to position this thing. And that’s what I wanna dig into because I do a lot of mentoring with startups.

Joel: I see a lot of early startups. So I’ve gone through that, a lot, but you’ve seen a lot more than I have. And it’s a risk for a very early stage startup to even get engaged with a with a firm like Gartner. But it could be very helpful in shaping the messaging, shaping the positioning.

What’s a red flag that goes off when you meet a founder, maybe a technical founder or that product team, it’s an early meeting and you’re playing the part, you’re playing the role of the executive. ” Give me the pitch. Tell me what what you do.”

What are some of the things that are mistakes that founders make?

Jeffrey: yeah, that’s a great question. I think there are a couple of them. I think the first one is not being open for criticism. Hey, look, I get the fact nobody wants to be told their baby is ugly. But you need to be open for a commentary and criticism, right? We, I always tell the story of the blind people and the elephant, and I won’t do it ’cause I don’t wanna suck up the time.

But essentially the moral of that story is we get so close to a problem, we don’t see the bigger picture, right? So yeah, you’re right, you may have a perfect solution, but there are other people that do 60% of what you do. What is it you do differently and why? So that, that’s the first one is not being open to criticism.

I think the second one, and this is a tough one because for small companies, they can’t necessarily afford this. But I can’t tell you how many companies had amazing technology. And the founder, the creator, never let go of the reins. They wanted to be the CEO, they wanted to be head of sales.

They wanted to be the CRO. And you know what? You’re a technical person. You suck at those other things. And you need to recognize that and you need to leverage people and bring in either advisors or, if you’ve taken in money from an investor, go to your investors. ’cause they have a whole cadre of people that they can bring to bear.

And then the third one, and this. This is always a challenge. There’s a tendency to say, yes, we do that when it’s not in your core. And I always used to coach people go, “what is it you do?” The old GE model, if we’re not number one or two in a market, we’re gonna pay someone else to do it. So focus on what you do really well and be really good at that.

And then look for potential opportunities through partnerships. Maybe you can build out. And we’ve done this at Black Kite, right? We were very specific and narrow when we first started, and we are now starting to push out and kind of branch, but we did it in a very slow, methodical, thoughtful way.

So maybe we missed a couple of things. But in general it’s given us an opportunity to be very iterative and grow. And I, our chief product officer, a guy named Chuck Schaber who is amazing, he said to me something one time, he said, “my job as chief product Officer is to decide what not to do. And not what to do.”

And I, that was like I opening for me. There’s only so much time. ’cause I constantly, like one of my functions at work is. I bring in new technologies, I go, “Hey, I think we could partner with these. These guys have cool data. These gals over here have cool data. We have data we can pump in.” And we have this conversation and they go, “yeah, it’s gonna take us six months and we’re gonna have to pull people off a bunch of other projects to do that.

So we can’t do that right now.” And of course I, stamp my little feet. But I think those are really the three things. So just to backtrack, ’cause I tend to like the sound of my own voice, I think not taking criticism well. The founder technologist, not realizing that they’re not business and sales and marketing people.

And then the third thing is trying to do too much. ’cause if you go to somebody and say, oh, I do everything. They don’t believe you can do anything really well. And that’s what they’re looking for when they’re going to you as a startup. They’re not looking for a solution that solves all their problems.

They’re looking for a specific answer to a specific problem.

And we need to give that to them. And we don’t.

Joel: Yeah, I have had clients say, make us. Tell the CrowdStrike story, make us CrowdStrike. And I’m like, you got CrowdStrike money? You got CrowdStrike capabilities? You don’t, so let’s find the thing that you really do it it’s the shiny object ambulance chasing. And I see that in messaging too.

One of the, one of the criticisms of Gartner is and I’ve used this metaphor before, is. And it’s not necessarily the on them, it’s on the industry. A new category pops up, or a new word pops up, and the entire industry plays what I call bunch ball soccer, right? So it’s like five year olds playing soccer.

Everybody rushes to the ball. Everybody wants to capture the ball and a mature organization or a mature industry knows their positions, but with Gartner, one of the things with Emergynt is we were trying to get in a brand new category, and so everybody was rushing into this category before we even understood it.

I want to pick your brain about categorization. You have to fit into standout. Is it so important to talk about your category or to talk about the problem you solve? The thing you do you have to always use the language?

Jeffrey: Yeah, so that’s a really hard one. And it was something I struggled with when I was an analyst and I still struggle with it a little bit in my current role because. Ultimately, if you’re a market of one, nobody’s talking about you. So, and to your point, when I first started talking to Emergynt and in particular, Dr. Crane, who’s a brilliant guy who I think was one of those founders who recognized that he was not the sales salesperson. So I think it’s very difficult. The optimal answer is focused on the problem you solve. But frequently you don’t get that opportunity unless you can say, “we fit in this.”

And I’ll give you an example from my current role at BlackKite. So people say, “so what do you guys do?” And I say, “well, with third party risk intelligence. And we gather and we do and we present and all this stuff.” And they go, “oh, so you are like,” and they give us two names of the competitors.

And I go, “so we do what they promised to do and have failed at. And let me tell you why,” right? But until I can get them to identify, yes you are in this market, the rest of the conversation doesn’t happen. Now I have an advantage because I have a pedigree and I’ve been around a long time and I’m known and people know that I am very independent.

People know I’m not a sales and marketing person. If I call one of my CISO friends and I got bunches of ’em just like you do, they know I’m not calling them to pitch them. Maybe I’m learning, wanna learn from them, “Hey, what are you doing for this? And hey, I, we are doing this new thing.

What do you think? Is this interesting?” And I think that is a really big challenge. The flip side of that though is. When markets get so big, the differentiation’s not there. And I’m gonna say something that’s a little controversial. GRCI believe GRC as a technical market is a failed experiment, right?

I’ve never met a CISO who got up in the morning and said, “holy shit, I am so glad I spent $10 million on fill-in-the-product. ’cause it solved all my problems.” ’cause it hasn’t. And for my GRC partners out there, we love what you guys do, you’re awesome. But we have to be mindful of over promising.

And I think sometimes markets get so big that is what happens. So the challenge I think, for a lot of startups is that I. If you are not doing something at least somewhat similar to someone else , that 30-second elevator pitch is not enough time. So then you gotta corner people and you gotta get ’em in a slow elevator, or you gotta push the, the emergency stop button and go, oh my God, I, thought I saw a ghost dog.

Something like that. But otherwise, it’s very difficult to do. And the one thing I’ve seen in my three years is I went from, “Hey, I work for this company”. And they go, “oh, I think I’ve heard of BlackKite” to, “oh yeah, we are hearing about you. Show me what you do.” But that took three years and I already stepped onto a train that was already moving.

A lot of startups don’t have that. And I think in particular, going back to Emergynt right. Dr. Crane’s story was very much based on the PhD research he did on swarming animals. Now I get that ’cause I’m a total geek nerd. Most people are like, “what are you talking about?”

And I think that was part of the problem was not just that it was a unique solution, but the setup was too long and complicated.

Joel: that’s one of the conclusions we came to.

Jeffrey: yeah. As opposed to, “we make it easier for you to make these decisions.” Oh really? How do you do that? And then we can talk about it. I think a lot of it is, 10 seconds. That’s what you get to hook somebody. And if you don’t. The rest of it falls on deaf ears. And I always tell people know, I coach people in speaking and presenting all the time, and they always say, if people are looking at their phones 30 seconds after you started, you better restart and get their attention.

’cause you’re gonna lose them.

And that’s what happens in a lot of these meetings.

Joel: I’ve been doing a lot of research in in human cognition and how we process and speaking simply using language very clipped short language sometimes gets poo-pooed and gets ascribed to, being unintelligent. But when you’re in a position where you have a limited amount of time to pitch or to do a setup, you can’t say, ” it’s a self defending artificial intelligence, multi noal network based on the behavior of eusocial insects.” You say “it’s an ant swarm technology that predicts where you’re gonna get hacked next.” Oh, okay.

Jeffrey: And then you have to be able to prove it though. And that’s, the proof is in the pudding as it were.

Joel: And that was the big challenge at Emergynt, it was, show me the swarm, show me the algorithm. And as I’m like, dude, it’s math. It’s like, it’s really hard to explain that. And it wasn’t until I invented the card game that could explain and show in 40 seconds… 

Jeffrey: I still have that card game in my desk. I love that thing. That thing was brilliant! 

Joel: That’s awesome!

Jeffrey: Yeah, it’s sit, yeah, it’s sitting in my desk. Granted, it’s sitting in my desk with all my DEF CON patches, my Goon badges, and my wife is like afraid to go in my office now. 

Joel: That’s, it’s your tr it’s your trophies.
 

I’d love to ask in the position that you are now and I do wanna get the story of “Risk Evangelist”, what are you finding sitting on this side now that people are asking for. So, so now you’re in a position where you’re talking maybe as a, as an analyst, you were talking with the buyers and the CISOs ’cause you needed to understand what the market wanted.

But now you’re in a position where you’re almost exclusively talking to them. Have problems changed? Like are we dealing with fundamentally different things or are they just in different wrappers? 

Jeffrey: There are some areas where I think we’re dealing with different fundamentals, right? I think cloud was a paradigm shift. Moving away from doing everything yourself and hosting yourself, I think that was a paradigm shift and it turned a lot of security people into contract management people, right?

Which is not necessarily what they want to do. But for the most part, I think it’s really more of a framing problem than anything else. The way I always talk about is cybersecurity is only one risk, but it is, it has an outsized impact on the rest of your business and on your partners and your vendors, and your third parties and your customers.

If you get hit with ransomware, you’re down for a week. How long is your actual business down? Probably longer than a week. So I think a lot of it is about framing, and then I think that we still have this very big disconnect between what security and risk leaders are saying and what the business folks understand.

And I feel like there’s equal fault on both sides. I feel like on the business side, they’re poo-pooing it and going, well, that’s your problem, right? It’s a tech thing. But on the other side, and I do this too, right? And I’ve been this communication conduit for 30 years and I still sometimes hang up the phone and I go, yeah, I don’t know why I used all those acronyms.

So I feel like it’s all and I know you had my buddy George Kamide on earlier in, in in the show. And I know he talked about storytelling. I was bummed he stole my topic. ’cause that’s my favorite topic. And he’s excellent at it. But I feel like we need to do a better job of bringing people along.

I always say once upon a time are maybe the most powerful words in the English language. And when I say it, the hair stands up on my arm still. And I talk about storytelling and people go, oh, I can’t do this. And I go, you can though. You do it all the time. You just have to figure out how to create a character and step into the character.

And that’s what I do all the time. So, I know it’s like a very long-winded answer, but I feel like we are. Taking three steps forward, two steps back. I think sometimes we’re going three steps forward, four steps back. I think the political environment, and I’m not gonna get political, but I think that, change in party, change in administration, I think is changes every four years, every eight years.

And I think that’s a challenge. And actually I had Merritt Baer who’s a well known CISO on. On my podcast and, we talked about what should CISOs expect in with the new administration, and we did it without getting political. But I feel like the SEC ruling the new regulation outta the EU, DORA, which is a operational risk management framework, I feel like the businesses starting to get questions from outside parties that they don’t know the answers to.

And I don’t think they always know who to go to. And I think that to me is the biggest challenge. And then, sprinkle in, AI and all the new things and I don’t think AI for the most part is allowing attackers to do anything different, but I think they’re allowing them to do the same things much, much faster and we are not prepared.

So tho those, I think are the biggest sort of challenges that I think that, and I say security and risk leaders ’cause I don’t even, not everyone has the title CISO but. At the end day, you have some ownership in technology and or cybersecurity risk in the organization, and it behooves you to get your business to understand why they should be paying attention.

Even if they don’t listen, they gotta, or even if they don’t do what you want, they have to listen.

Joel: And that’s, that, that risk transference is “you’re gonna accept this. We’re either gonna do something about it or you are going to accept it.” And being very clear about that, it’s not, “well, do you want the server to be patched or not? This is the result.” No, it is. “Do you want this risk?”

And that, that’s where I think, and not to get all philosophical about what risk really is, and I still think we’re using it wrong a lot in the industry. What is a risk versus threat, blah, blah, blah, all that stuff. But I think it, it does get down to the storytelling. And I had a conversation with a former colleague who is a video guy, and I’ll be posting that actually this next week about, storytelling.

So he, he did explainer videos. 30-second explainer videos that had the entire Joseph Campbell hero arc in them. And, it’s like the story and the pathos and going to the unknown and bringing them out. And I’m like, dude, we just have to talk about these features. He’s like, no, these aren’t features.

These are, this is the promise, this is the Temptress, yada, yada, yada. So I, I think storytelling gets underused but also. Talked about too much. I think we still don’t quite understand it as technical people, but it’s like you said, it’s something that we do every day. 

Jeffrey: So, so it’s interesting you mention that because I’ve been talking to people about storytelling for 20 years before it was this big thing. Now everybody’s a storyteller, whatever. But I love the hero’s journey because I actually use that. It’s actually one of the core pieces in my storytelling deck that I use.

And the one key takeaway I always say is, look, you’re the CISO. You think you’re the hero. But you’re not, you are the wise person, you are the mentor, you are the hermit, the hero is your boss, the CEO, the CFO, the board. And that lights a bulb over people’s heads because it leads to a very different story.

And I think it’s great that that other guest talked into it. And I think it’s one of these things where it’s useful to understand, but you can’t leverage a lot of it in what we do because. You can’t tell that whole thing in 30 seconds, at least to do it justice. But I like the fact that people are talking about it and I think the key thing again, is the CISO is not the hero and they continue to think that’s their job and they’re not,

Joel: Or the vendor thinks they’re the hero.

Jeffrey: oh, don’t even get me started on that one. 

Joel: and that’s a great distinction. We will have to dig into that over coffee sometime. I wanted ask you to talk about the podcast a little bit . I had Kristen uh, Demoranville on.

And she has a podcast that is very intersectional between food safety and operational technology, ICS security, right? Risk and Reels, which is your podcast opens with the movie question. And then somehow you tend to tie in to the topic at hand. And, I think using that as a metaphor to talk about story was that, how did you back into that?

Did, was that, were you just like, I want to talk about two things. I can’t decide what podcast I’m gonna do, so I’m gonna do both.

Jeffrey: Yeah, so I gotta think back to this like two years now. I wanted to do something not super traditional, right? I didn’t want to do the, okay, I’m gonna ask you a question then I’m gonna sit here quietly until you’re done and then I’m gonna ask you another question, right? So I wanted to do something a little bit different and I said, well, how can we get to know people a little bit, as people?

So my original premise was books ’cause I’m a huge reader. But I realize not everybody is a big reader and that’s fine. So then I said, well, movies, and, it started out with what’s your favorite movie? And then it started to morph a little bit. And what I do now, so I’ll open the raincoat a little bit.

We do prep calls. Now you and I ha didn’t do a prep call ’cause we’ve known each other forever. But I always do a prep call and I say, okay, so based on what I know about you, here’s what I think might be an interesting topic to talk about. Okay. I agree. All right, so now let’s figure out what movie question we can create that will connect back to that.

And that’s the way we do it. And, it’s very unscripted. I’ve, I had a couple of guests who say, well, can you send me some questions? And I should, I will be happy to do that. I will probably not ask any of them. 

And I sit like with a piece of paper and I scrawl notes, and then I do a recap at the end.

And for me, like. I dunno if anyone out there is a Howard Stern fan and I actually haven’t listened to him in a while ’cause he turned it into a political show and whatever your opinion is politically, I tuned in to hear fart jokes and he was moving away from that. So, but he had his knack.

He could make anyone interesting. He. And I feel like that’s what I wanna do, right? Everybody I think focuses on, oh, let’s get this big CISO and I’m happy to have those people on. But I just had on a student I had on someone who just graduated not too long ago. I had I interviewed an attorney last week who I met at this cyber breakfast club thing that I do.

I stumbled across somebody’s profile on LinkedIn who she’s, she calls herself a DORA expert now. She’s as much of an expert, I think as anyone, is on a regulation that literally just kicked in two weeks ago. But I had her on, she had a really interesting story and I feel like that’s what I want to do, which is just get people to be able to tell their stories.

It’s a huge opportunity for me to learn. I walk away from every single episode knowing at least one thing I didn’t know before. And when I was a kid, my dad said to me. And my dad’s still alive. He said, “any day where you don’t learn something new is a waste of a day.” And I live my life by that.

And that is one of the things that I love. And if you listen to the podcast, and I know you have, and everyone out there should definitely check it out. But I’m excited every time and I always start off with, I’m super excited for my guest today. And that is absolutely true every single time. So, that’s kinda what we’re doing and, I’m always trying to be better and always looking for interesting guests who have interesting perspectives and interesting backgrounds.
 

Anyone that’s interested, please reach out to me on LinkedIn. I’m happy to talk. And yeah, so that’s the story

Joel: Yeah, and I’ll definitely include links to to the show. I’ll drop in I’ll look through. It’s gonna be hard to pick a favorite episode of mine, but I’ll direct link to to a couple of those. 

Just by way of wrap up, again, smiling ear to ear man how you’ve been doing this for so long and you’ve seen a lot.

What do you do outside of work? To stay fresh, to stay connected and to ignite that passion to keep the fires going.

Jeffrey: So I have three kids so I’m like super involved in their lives. One of my son works for a lobbyist firm in DC my older daughter is actually in PA school in Philadelphia, so she’s going into medical profession. And my youngest is a 19-year-old sophomore at UCF in Orlando studying languages in poli sci.

And she’s looking for an internship if anyone’s looking. She’s super, super smart. That’s a commercial. My wife runs her own company. I’m super involved with them. Tonight, I’m actually getting scuba certified over the next two weekends. We are going on a trip with some friends of ours, and my buddy’s a diver and he’s like, “Hey, if you get certified, we can dive.”

So I’m doing that. We, I’m a huge traveler. 

I look at my parents and, they’ve worked their whole lives and now they don’t really do anything because they’re in their eighties and they’re not as mobile. And I don’t want to be that.

So I’ve been to, we figured out, I’ve been to like 80 countries. We were just in the Canary Islands, Morocco and Spain. Last year we were in Vietnam and Cambodia. I’ve been to Africa on Safari. So, those are really the things I do. But I’m a huge reader. And that’s the thing, right?

I don’t know about you, Joel, but a lot of what I read is stuff online about AI, about cybersecurity, about technology, because that’s what I love. So, people ask me like, what are your hobbies? And I go. That I have hobbies in a traditional way I’ve thought about picking up a guitar. But then I am reminded when I was 13 my mom got me guitar lessons and after two lessons the teacher said to my mother, she should save her money.

So clearly, yeah, at the time it was hurtful, but I love music. Doesn’t mean I need to be able to play it. But yeah, I just think I think the world is so interesting and. Most, I always try to stop and smell the roses. We have a couple of dogs. We actually just rescued a new dog named Dexter, who had a leg amputated and he was in a very bad situation and my wife’s like, “I want that dog.”

So we drove down to Miami. I got a flat halfway. I stood out in the rain waiting for roadside assistance. They put the donut on and I drove the rest of the way to Miami. We picked this dog up and he’s now part of my growing family.

Joel: Oh, that’s awesome. I think you might have posted some of those pictures on LinkedIn. So I do love a good dog picture. Dogs seem to be very popular in with cybersecurity folks. I don’t know what it is. My wife won’t let me get a dog. She likes quiet around the house. So I have fish in a pond in the backyard that I never feed because they’re basically wild goldfish.

So not so big on that. So, man, I gotta tell you, you absolutely right. It is so exciting and it is such a pleasure. And I editing my podcast. I find, I say that all the time. I say, awesome. And I say, I’m so excited and it’s genuine. And I think that is one of the things that you need as a technical communicator.

You need curiosity. You need to be genuine. You need to recognize what you’re good at and what you’re not. Even if that’s guitar playing. 

Jeffrey: Lemme just add something there, Joel. ’cause I think that’s an interesting point right? Is about the excitement. About a year ago I had a self-reflective moment where I realized the most common thing outta my mouth was, “that is so fucking annoying.”

And I went, that is such a negative way to lead my life.

And I don’t do it anymore. And we were on vacation with the kids and I said to my daughter, “I would like you to not say for a whole day, something’s annoying.” And she did it right. And I feel like if we’re positive, we bring positivity to us. I think if we’re negative, we bring negativity. I actually just got a new tattoo, which I guess maybe is one of my hobbies ’cause I got a bunch of those.

But it’s based on an old Cherokee parable about the dark wolf and the white wolf. And basically the, I won’t give you the whole thing. You can look it up. But really all it is that. If we feed into the darkness, if we feed into the jealousy, the anger, the hatred, the frustration, that is what we get.

If we feed into the love and joy and friendship and sort of those positive things, that is what we get. And I tell my kids all the time, every day you get to decide whether you’re gonna be miserable or joyful. And you get to pick every day. And too many people pick the misery ’cause it’s easier.

And it’s, you can blame people, so you know that to me is partially where the excitement comes from. 

Joel: Yeah, in internal perspective versus external perspective, I think is awesome. So for people who wanna connect up with you I’ll include the LinkedIn, I’ll include some links out to the podcast, but where else, how else can people follow you?

Jeffrey: Yeah, so LinkedIn is really the best bet. I don’t really do any other social media. My wife made me get off Facebook during Covid ’cause I was fighting with people on a regular basis when I was supposed to be working. Twitter X, whatever you wanna call it, is a frigging cesspool now, so I won’t go on there.

So LinkedIn is really my space. You can definitely check out the podcast. I do some blogging for our website at blackkite.com. Definitely check us out if anyone’s interested in hearing what we do. I’m happy to to have that conversation. I do a thing every Thursday called the Thursday Think, which is just something that makes me go Hmm, you may find some value there.

I also go to a lot of conferences, so I’m gonna be attending this year. So far, I know RSA, Black Hat the Gartner Security and Risk Conference, and the Gartner Enterprise risk Management. I am presenting at ISACA, I forget what they call it now, g. The GRC conference in may, I think. But yeah, check my LinkedIn, I always post where I’m gonna be.

And then also check out the Cyber Breakfast Club. That’s one of my favorite networking groups. They basically say, if there’s a football team, we have a chapter and they meet once a month from 7:45 to nine. Virtual networking, presentation and some sponsored stuff. So that’s it.

I’m around and if you see me in the hall, feel free to grab me. I love talking to people. I know we didn’t really get to the DEF CON thing, but feel free to call me MNKY if that is what you so desire.

Joel: Yeah. And when I think the Gartner thing, one of the Gartner things is always up here in in this area. So I will even if I can’t get into it, I’ll LobbyCon it with you ’cause it would be great to to hang out.

Jeff, thanks. Thanks for joining, buddy. I would I’d love to, to come on and talk movies and Risk and Reels I may introduce you to my my former video colleague who can just talk your ear off about movies.

Jeffrey: All right. Thanks Joel. Appreciate it. Cheers everyone.
 
 

Joel: If you want links to the resources mentioned on the show, head on over to the episode page. And for information on booking a message therapy workshop, getting your hands on the MessageDeck, to check out my upcoming book, or just buy me a coffee, go to nerdthattalksgood.com/podcast. 

 Until next time, happy messaging.
 

 Remember, you don’t have to speak well, you only gotta learn how to talk good.