Latest / Career Catalyst / Ben Ferguson CTO of Defensive Networks : Everything Works If You Do It Well

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Ben Ferguson CTO of Defensive Networks : Everything Works If You Do It Well · Career Catalyst

• Derek Lazzaro: have. So Ben Ferguson, Executive Vice President and Chief Technology Officer of Defensive.com, ⁓ also known as Defensive Networks, right? You got me. right. Well, Ben. ⁓ Ben: You nailed it. That's me. Derek Lazzaro: Yeah, that's a pretty impressive title. And I've known you a while now. You do some pretty impressive things. Why don't you briefly just kind of kick this off? Tell us a little bit about what you actually do and sort of how you got to the role that you currently have. Ben: pretty impressive. Yeah, well, so ⁓ on March 1st, I just celebrated my 16 year anniversary with the company. So I've been there for quite some time. ⁓ I've had quite a few roles at the company with executive vice president and CTO being the most recent. And ⁓ what does that mean exactly? I am in charge of the technical direction of our company as a whole. And I have the privilege of overseeing everything from our partnerships, what technology that we're really digging at the time and want to offer pro services around. And ⁓ I oversee our red teaming, our research, and ⁓ also revenue. So it's all circular in my role. And so it's fun because no two days are the same. Derek Lazzaro: And Ben, I would say that one of the things that sets you apart that I've learned about you as we've known each other is you're a very technical person. You really dive deep into the actual architecture, the sort of magic behind the solutions, but you also are into sales, right? I mean, you're right on the sales calls. You're sort of a sales engineer, sort of super charged version of that basically, right? ⁓ Tell me a little bit about that career path. How did you actually become both so technical but also capable of leading complex solutions, conversations? Ben: become both so technical but also capable of reading complex solutions, conversations. How far do you want me to How far back do you want me to go? You want the origin story? So, yeah, I was raised in a household with a father that's a doctor, a mom that's a nurse. And from about age four or five, it was a, why aren't you a doctor yet? Conversation constantly. you know, and my parents were fantastic, you know, sort of, my dad was, he would tell me, was like, you know. Derek Lazzaro: So, you know. Ben: stay out of corporate America, you wanna get into medicine, you'll always have a job, you'll have flexibility of wherever you wanna live, there'll always be opportunities. And as it turns out, medical schools really limit the number of people that go in there, thus limiting the number of doctors so you can have artificial scarcity. And that's a whole wreck in itself, not here to judge it, but good for them. So in college I studied, Derek Lazzaro: And that's a full record, so I'm not going to judge it. Ben: biochemistry and I had ⁓ a minor in engineering sciences. Turns out there's like only four classes you have to do outside of biochemistry to get a whole nother minor. ⁓ Not that it matters that much, you know, I got some exposure into coding and some other things there. ⁓ What it ended up teaching me was how to learn a lot of really complicated things that you can't see with your naked eye ⁓ really quickly. ⁓ Derek Lazzaro: I guess people are into other things there. What it ended up being was a really complicated thing that's pretty difficult to do. And so that ended up being super helpful to think about. Ben: And so that ended up being super helpful, but if you think about what's a linear trajectory from biochemistry, it's not what I do on a day-to-day basis, that's for sure. And so how did I end up in this role? Through a series of failures. ⁓ So for one, I moved to Los Angeles to work at a biotech company, and I was gonna do exactly a year there, they didn't know this, but exactly a year and then go on to medical school. And... Derek Lazzaro: And so, how do you end up in this role? There's great failures. So, for one, I need to go off the controls. Or, work it out by myself. I was gonna do exactly Ben: It was maybe two days or three days before I graduated, I get a call from probably their HR or something, and it was like, hey, we're so excited for you to start. One little footnote is ⁓ your start date is now up in the air, as we'll call it. And right now we're trying to find a place for you at the company and blah, blah, blah, blah. You're not starting in two weeks as planned. Derek Lazzaro: Maybe two days, I'm going to get to work. I waited, I got a call from Sarah, probably very HR, and she was like, hey, let's actually get started. What I'm looking for now is start getting it done out in the year. was calling her and it's, you know, right now we're trying to find a place for you here at the company. You know, you're not starting. And she just plans basically. I had been a long friend of hers at this company. Ben: Basically, and I ended up calling a friend that was working this company. She was like we just had a 40 % downsize our Our largest shareholders filing bankruptcy. I graduated 2008 by the way So yeah, that kind of checks out right checks out Yeah, what a good way to start the workforce Derek Lazzaro: We just had a 40 % test on it. Okay, yeah. Interesting time to jump into the workforce, right? Yeah. I had some similar experiences, but yeah. Ben: Yeah, and so, 20 nothing year old Ben was sort of like, ⁓ I'll just get a summer job as a bartender or something like that. And that didn't work out for me. I ended up applying to probably over 100 jobs and getting one call back and it was for a tech company. Happened to be the only one that was really growing in 2008, great financial crisis. And ⁓ was it my dream job? Derek Lazzaro: You Mm-hmm. crisis. Ben: Absolutely not was it a place where I would get a paycheck that I would you know be able to feed myself a relatively small amount Yes, so I was happy to just take that ⁓ What it ended up being was it was in tech sales and? They really grind you at this company ⁓ Which is great for character building ⁓ I recommend anyone that's new to the workforce try and find a place that grinds you because you can get in a lot of reps for Whatever you're trying to do ⁓ Derek Lazzaro: What does that mean? Let's actually pause there for a second and pick on that point because, know, I think obviously we're now in the post pandemic era. We're in kind of the work from home, hybrid work kind of era. And there is a lot more focus, I think for Gen Z in particular, but really for everybody on work-life balance. So talk to me a little bit about how your experience sort of in a grinding sort of role. Ben: Okay. And there is a lot more focus, I think, for Gen Z. Derek Lazzaro: You talked about the reps, the ability to kind of learn skills, right? I think is what you're getting at. How does that fit into a lot of people who say, yeah, but I really need work-life balance. Like where do you sort of draw those lines or is your answer just you're young, like now's the time to do it. Ben: that fit into a lot of people who say, yeah, but I really need more. You're young, now's the time to do it, is the reality. ⁓ If I was coming into the workforce right now, knowing what I know, would I be doing a 100 % remote job that gives free massages on the weekends and work-life balance and you can go travel the world? That sounds awesome on paper, and it probably is awesome, let's be honest. ⁓ In reality, I think that the Derek Lazzaro: Yeah. Ben: The financial state of our company is not really allowing for many of those roles anymore. Certainly not an entry level, but yeah. But let's just say that they still exist. ⁓ I would say massive disservice to your future not being in the mix. Derek Lazzaro: And certainly not our country basically. Yeah. Well, let's just say. Ben: I got so much value off of being in the office and that first job, every job really, being in the office around the smartest people and the leaders of a company is more valuable than any little skills, technical skills or whatever you're gonna pick up along the way is just understanding how businesses function, businesses think, understanding. Derek Lazzaro: being in the office at the first job. Every job. Being in the office around the smartest people and the leaders of the company is more than skill, skills, know, skills. However, you're gonna be talking about is just understanding the office is a... Ben: you know working for a company you're cog in a big machine and if you're just looking at your cog and Saying the worst thing which is is this really in my job description? Those are those are not Those are terrible for you Self-limiting choices. Absolutely ⁓ If you're if you're a cog in a machine and you don't understand the inner workings of the whole machinery You're doing yourself a massive disservice. You want to understand Derek Lazzaro: ⁓ Kind of self-limiting choices basically. Mm-hmm. Right. Ben: where the company is going and how you participate in that and how you're doing your part to drive the business forward. If not, you're putting yourself at disproportionate risk of being dispensable of the company, right? Derek Lazzaro: Yeah. No, I think those are great points, especially in an era where, you know, layoffs happen, you know, very quickly, very easily. ⁓ Any concept, I think, of loyalty and frankly, either direction is largely antiquated, right? To your point, if you're not visible, if you're not trying to grow, you're not learning about the company and its mission and where you fit into it, not only now, but where you'll fit in next, right? And you're kind of setting yourself up to be potentially on one of those spreadsheets. Ben: Yeah. Yeah, I mean if you're remote and you're just again a cog in the machine and you're only focusing on your functions of your cog, right? Then it's, it makes you way too replaceable, right? But if you're in the culture of the company, you understand where you're going, you're driving towards that, you're visible, then you're no longer an employee ID number that's going to be emotionlessly Derek Lazzaro: Mm hmm. Mm-hmm. Ben: cut at some point. And so being indispensable. it's also, I mean, let's actually not just give the side of just you need to be a cheerleader for the company for your own safety, for your own job security. ⁓ I think that if you understand the bigger vision and picture of the company, you're helping work towards that. I think that makes you a more happy employee. know, we spend a, I spend the majority of my waking hours working for a company. Derek Lazzaro: Right. It's been a long time. Ben: And if I feel part of the team valued, my inputs are taken into account. And this is not just from a CTO perspective, easy to say that, but from being a bottom of the totem pole ⁓ role, because we all have to start somewhere, ⁓ contributing. and feeling like you're part of something and understanding the vision and saying, is a vision I can get behind, it makes your work day just a lot better, right? Because we as humans, we all need to be on a mission working towards something. I feel like we evolved for millions of years as primates to work together as teams. if you're on an island, maybe... Derek Lazzaro: Yeah. you know, maybe a little. Ben: Maybe a literal island, if you're on an island ⁓ from a workflow enclave perspective, you're just gonna get every little inconvenience of the job, which every job has inconveniences and annoying things, is gonna be a point of fixation. It's just, this is how we're wired as humans. Derek Lazzaro: Right. Yeah, no, it sounds like, ⁓ it sounds like you're really almost drawing a pretty stark set of choices, almost, you know, one side is sort of self-limiting, you're kind of just a cog in the machine, a line on a spreadsheet. You know, the other side is really more kind of activated and actualized, you know, not only in terms of your contributions to the organization, but for yourself as well. I mean, it's, it's actually, I think it's really interesting how you're Presenting it. mean, I think a lot of the work from home hybrid work kind of debate honestly focuses more on some of the logistics, right? And then sometimes some of the better conversations I've heard about it get into mentorship or you topics along those lines But I haven't really heard a lot of people frame it the way you just did where it kind of transcends and even just like Are you maybe actually happier? Ben: But I haven't really heard a lot of people frame it the way you just did. Or kind of say, are you maybe actually happier, really being part of the team and being fully activated and all of that. So that's really interesting. So all right, so I kind of cut you off there. So you're working at the tech company. You're still pretty early level employee. So where do you go from there? Derek Lazzaro: you know, really being part of the team and being sort of fully activated and all that. So that's really interesting. ⁓ So, all right, so I kind of cut you off there. So you're working at the tech company, you're still a pretty early level employee. So where do you go from there? Ben: This was a sales job and in tech. And what I realized early on was the technical win aspect of being in tech sales is often more important than everything else. And so you get these sales managers that, you know, they talk about. all these, you know, sales 101 and closing techniques. And I found the whole bit to be very disingenuous and it's like an acting class, you know, you're teaching reps to like deliver this conviction of if you don't buy my solution, your whole business is going to fail. And. Yeah, right. And I found the whole thing to be gross and disingenuous and Derek Lazzaro: in. I've heard that once or twice on the other side of it. Ben: I knew I was never gonna be able to ham that up. But you can ham that up, and that wasn't for me. Then on the sales engineer side, it was sort of like, all right, you'd find an opportunity and then you let the engineers deliberate and then arrive at a, this is a good fit, let's do it, or this is not a good fit. And I didn't want to give complete control over somebody else who, Derek Lazzaro: Yeah, but, you know. Mm hmm. Ben: you know, didn't know how smart they were. Were they really articulating things well? ⁓ Our engineers at the company were okay. ⁓ And so, but I also, I'm just a curious person, I wanna know how everything works. It's just, I don't know, it's dropped on my head as a child or something like that. Now I have to know how everything works. And ⁓ there's probably, like if you were to, Derek Lazzaro: Mm-hmm. over. you Ben: psychoanalyze it, there's probably a crippling anxiety of just not being a part of a conversation. It's sort of, you get into, if you're meeting with some people and all of sudden they start delivering it in a different language, you're like, I have no idea what's going on. ⁓ so I just, I really want to be in the know. And then you get, you know, Derek Lazzaro: All right. And so I just really wanted to do Ian's presentation. Ben: Back then, Cisco ruled the world. And man, those are some dry courses that I started taking. ⁓ If you ever needed a nap on a Sunday, take CCNA courses at like 3 o'clock in the afternoon. If you have a hard time sleeping, ⁓ it could really replace sleeping drugs for many people, I could imagine. I'm not a doctor. ⁓ Derek Lazzaro: Mm hmm. Thank you, guys. Ben: despite my father's wishes, so I can't prescribe things. ⁓ So that was the tech stuff. The intro things were kind of boring and I just kind of got through them because I was sort of like, ⁓ need to check these boxes if I'm going be taken seriously. And so I went through those courses and got certifications. ⁓ Derek Lazzaro: Yeah. ⁓ Ben: It took a bunch of the generic ones, of Microsoft things, Cisco systems stuff, Fortinet stuff. And then, you know, moving from generalists to being more hyper-specialized, and that's where I sit today. I'm ⁓ hyper-specialized in maybe a dozen things. I'm not broadly specialized in a hundred things. And I think there's probably a good rationale for that for folks listening. Derek Lazzaro: Mm-hmm. Mm-hmm. Yeah. Ben: I'm sure we'll dig into it at some point. But as I got more into the advanced stuff, especially into configuration, then you're like, oh, I'm the artist. This is my canvas. And this is where you can create interesting differentiation as an engineer. And I don't think anyone will ever say this, but I think it's being able to do customized cool things that other people can't do, it's definitely ego. Derek Lazzaro: Mm-hmm. Right. It's definitely cool. But it is cool. It ends up. And I think it's about cool if you Ben: I'll admit that, but it is cool. ⁓ I think for a lot of people, if you can get to that point in your engineering journey where you can do cool stuff that most people can't, it's kind of sick. Derek Lazzaro: Mm-hmm. Yeah. So this hasn't really come up in any of our, our podcasts episodes yet, but I have certainly seen and heard and talked to a lot of people out in the tech space who talk about imposter syndrome. And they kind of talk about, know, I'm surrounded by all these really smart people, all these people that have been doing some kind of tech role for, for 10, 15, 20 years. And I feel like I'm kind of. faking it, right? You I will say this, I've certainly felt that way at various points along my career, but I've also gotten to points where I feel more like what you just talked about, where I really am able to sort of synthesize a whole bunch of things, you know, pull together architectures that make a lot of sense, you know, really solve the problem. I'm proud of it. It's fun. You know, you sort of... building with Legos or whatever you want to call it for grownups basically. I'm curious if you ever did feel that imposter syndrome at any point along that journey and whether or not you have, what sort of advice you have for folks that maybe do feel that way from time to time. Ben: Yeah, so the Dunning-Kruger effect, I think it's called, is absolutely real, and it is a rite of passage, I think. ⁓ It's probably hard-coded in our brains as humans. ⁓ So basically the Dunning-Kruger effect, this is you throw the image on the screen, right? Pull that one up, Jamie. ⁓ It's ⁓ a chart that's confidence versus actual knowledge, and it goes up, and they call this Derek Lazzaro: Thank you. you Ben: peak of mountain stupidity. It's where you have unlimited confidence with just a little bit of knowledge. And then as you learn more, you go into the, I think it's the valley of despair. That is where your imposter syndrome hits. And then you slowly climb as you accrue more knowledge into that ⁓ Kanye West level of confidence. ⁓ So yeah, no, it's 100 % real and I think it's a rite of passage for, you know. Derek Lazzaro: for you. think that's right. ⁓ Ben: anything in life, but yeah, absolutely. What happens is you learn something, you have this excitement and it feels like, oh, I can do everything in this domain, whatever the subject matter is. what it is is you've gotten maybe a lot of hypothetical knowledge and a little bit of tactile knowledge and you're just like, this is an unlock moment and it's. Derek Lazzaro: everything. Ben: enthusiasm, excitement, and confidence. And then you start doing, and then a lot of things don't happen as you draw them up. And then you're like, ⁓ interesting, not as good as I mentally thought. And it's just, the next part is putting in the reps and actually gaining real world experience. going back up the confidence curve is... Derek Lazzaro: And then you. And oh, interesting, not as good as I meant to And then it's to think about. Ben: ⁓ is where you get real sustained confidence in your ability as an engineer. I would expect that in that valley of despair is where a lot of people call it quits and, this is too hard. I'll let the experts figure this out. I'm not as smart as I thought. ⁓ What you need to reframe that as, just, I don't know, Google Image Search. ⁓ Derek Lazzaro: is to get people to sustain confidence during the investment. What does this do? Right. Ben: the Dunning-Kruger effect, and then, ⁓ yeah, that checks out, right? I'm sure everybody can mentally rewind to a couple of those moments in the Valley of Despair. And that's where you can start to differentiate yourself as you go up. It's good to be humbled by things, just in life. It's good to be humbled by things. It's good to do hard things that you fail at. ⁓ those are your most valuable learning experiences. If you can get up from those failures and get back at something, that's when you're going to essentially build your career in something. Until that, you're sort of a job hopper and you become a subject matter tourist across a lot of things and you never build that depth of expertise. tech is great because you could, you know, Derek Lazzaro: Yeah. ⁓ Ben: go through that Dunning-Kruger effect in almost anything, and there's a viable market in TAM for expertise in that field, whether it's AI enabled or not, or just human services. It's such a broad field, and there's so much subject matter expertise needed in all aspects of tech. Derek Lazzaro: expertise in the field, whether it's AI or human. Ben: It's also because probably a lot of people call it quits in that valley of despair. And so it's not a big herd, it's a pretty thin herd that's on the other side of that valley. And if you just find your way to it, here's the other thing is, I think a lot of people are... Derek Lazzaro: Mm-hmm. Ben: Hesitant to specialize now because what's AI gonna do is just gonna eviscerate that market in six months and maybe right I don't have a crystal ball, but I would say that Tech is unique in that I would say 80 % of the most valuable information in tech is gate kept not indexed by the LLMs and so if you are a subject matter expert at something go ahead and Derek Lazzaro: Mm-hmm. Mm-hmm. Mm-hmm. Mm. ⁓ Ben: run, have Claude or a chat GBT run you through instructions on doing something complicated in your line of business that's knowledge-based, gate-capped, you'll find it's absolute trash and will completely screw whatever you're trying to do. Derek Lazzaro: Yeah, no, that's that's true We actually talked about that a little bit earlier today and kind of getting ready for for this episode And I I have certainly found that to be true You know as a working chief information officer myself, but there's absolutely details that that Claude or chat GPT simply doesn't know. Maybe it knows the 2023 version, right? But the specs have changed, the interface has changed, whatever it is. that stuff moves fast and a lot of it is behind, as you said, kind of Walt Gardens, That AI, at least right now, can't sort of see into necessarily, or they're relying on sort of secondary or tertiary sources that are lagging behind, right? ⁓ yeah. Ben: Well, just a point on that is that, know, look at the stock market and every time Claude makes a big update, it's like stocks are cooking, getting cooked. And so what companies are doing on the defensive is they are walled, creating walled gardens of their documentation very purposely, right? If you're gonna use an AI agent to, you know, administer their tool, Derek Lazzaro: Mm-hmm. Mm-hmm. Ben: best believe they're building that agent and they want an agent that's in their sandbox, not sharing information elsewhere. And so everybody's deployed all these anti-scraping, know, as little as a robot.txt file, thou shall not scrape this documentation. ⁓ And so you're going to continue to see all these islands of knowledge ⁓ completely separate from the public corpus of scrapable data. Derek Lazzaro: in years. and Ben: It's already, I see it right now firsthand, it's already happening. second is if you allow these tools to scrape your documentation, you're making yourself way more, as a company, as a software product, way more ⁓ subjected to getting vibe coded out of existence, right? Because if you can see your whole knowledge base, one can probably reason how to put those microservices together to build a lookalike. So companies are doing this defensively and Derek Lazzaro: Mm-hmm. Ben: I don't know, is it a bias all another 10 years of doing tech at a minimum? Derek Lazzaro: to do it that way. That'll be long. Switching gears maybe for a minute in terms of some specific advice for folks, maybe, especially early to kind of mid-career folks who are looking for a job right now or thinking about switching or something like that. ⁓ Do you think there is a particular path, if you are sort of in that situation currently, Is there a particular path, you know, for a while there were obviously like the code boot camps that were super hot. As you mentioned, you know, for, for at least a couple of decades, there've been all these sorts of certs and other things that folks have been pursuing. You know, are, is any of that still relevant? Is it less relevant in the era of AI, you know, work from home, all those kinds of changes we've seen. What are kind of the key, you know, functional choices people can make to level up their careers. Ben: Kind of pricey, but probably worth it. mean, if you could do an in-person, I don't know, AI is all the rage right now, in-person AI, whatever, certification, ⁓ where you can meet like-minded peers that are either working for companies and getting up-skilled by their company, or they're ⁓ also on the job search, right? Then you can kind of network band together, help each other out. I think that's really important. ⁓ Derek Lazzaro: in Right. Ben: Yeah, mean, networking is a non-negotiable, right? Because you can play the, you know, exist in a pile of resumes, and you better have that metadata term of whatever VMware or ⁓ this type of platform or, you know, that's what a lot of them are doing. Keyword matching, yeah. So you either optimize for your keyword matching and then deploy resumes to a large numerator value of places, play that. Derek Lazzaro: Yeah. Keyword matching basically. Yeah. Thank Ben: or you can do the networking angle is just a better angle, right? People, as programmatic as we've become in society, at end of the day, somebody at a company says, hey, I have a candidate. They're vouching for him. For whatever reason, that counts 10x like everything else. so it still does work. Derek Lazzaro: Right, right. Somebody has paid for their app for whatever. And I just like it. And so it still doesn't work. We can do it with this AI. Ben: We can move into this AI automation of all the things. At end of the day, we have millions of years of biology under the hood, and that's not changing anytime soon. So people still trust people. There's the judgment. ⁓ Someone vouches for you. Those are intangibles that folks need to take advantage of. Derek Lazzaro: under the, that's People, there's a child, you know. Yeah. Are there any particular, you know, I remember earlier in my career, there were these kind of user groups right here in the Los Angeles area, know, Linux user group, VMware user group. ⁓ A lot of them were actually in person. You'd meet up either at one of the companies would sort of host the whole group. You sometimes you'd meet up at other locations. ⁓ Do those kinds of organizations still exist? Are there any that you recommend? Or do you think going to educational institutions, like you said, is kind of the way to... Ben: The answer is everything works. ⁓ But I think that there's a way to do things well. if you're gonna join a user group, here's what not to do. Show up with your resume printed in a suit and, you know, hey, I'm trying to get a job. That is the worst way to present yourself in one of these user groups because it's sort of, Derek Lazzaro: Okay. Ben: ⁓ You know imagine hanging out with you know if you're at an HOA meeting and everybody you're surrounded by solar salesmen. It's like you're just never going to like un You know unguard yourself ⁓ You know it feels like there's an intruder in your little tribe you're trying to build so I would say start off with the right intent and Find a user group of something that you're genuinely excited about and want to contribute towards ⁓ Derek Lazzaro: So I would start off. Ben: And don't be disingenuous about it. If you go in with the right intentions, that's where, if you're just sort of chasing a job, like a job to these network groups, it's gonna get sussed out early, and then, you know, it's just not gonna work that way. So I would go there, and I understand that... It's easy to say if you have job security, if you're sitting there unemployed and rent's due next month, whether you like it or not, it's hard to be like, I'll contribute to this open source project for a bunch of free labor. And so that has to be taken into account that you maybe play the resume game, but the longer game is joining a group where you are genuinely excited about what they are doing and want to contribute to the mission. Derek Lazzaro: Right. Yeah. Ben: If not, probably don't join the group. Because I think it's disingenuous and I don't think the group would appreciate that. Somebody that's there actively soliciting people for a job role. You can say, hey, I'm a free agent right now and have stuff that you're working on and of course be mindful of the mission of this group and don't infiltrate it as a solicitor, infiltrate it as a contributor. Derek Lazzaro: Yeah. Right. Mm-hmm. Mm-hmm. Mm-hmm. Ben: And I think over the call the medium term you'll you'll be rewarded for that and Derek Lazzaro: You know, I think maybe part of what I'm hearing in that advice is the best time to build those relationships is when you do have a job. Right. You know, and actually I'll say this in my own career, that's a mistake I've made where I've been so heads down. And I think this is easy for a lot of people with kind of, you know, an engineering mindset, a technical mindset is you. Ben: is the best time to build those relationships is when you do have a job. Yeah. And actually, I'll say this. In my own career, that's a mistake I've made where I've been so heads down. And I think this is easy for lot of people with an engineering mindset, a technical mindset, is you think you're rewarded solely for delivering. Derek Lazzaro: you think you're rewarded kind of solely for delivering code, delivering projects, checking off all that kind of stuff. And it's easy to sort of forget about building relationships and networking and all that kind of stuff. But it is so much easier to do that when you are working and you have interesting projects to talk about and you know. all of the above, right? You've got the corporate email address, et cetera, et cetera, et cetera. ⁓ So I think that's a great point for folks listening to this is invest in yourself, invest in genuine relationships, as you said, ⁓ because it's way harder the day after you've been laid off or let go than it is when you're in the middle of some really cool projects. Ben: ⁓ Yeah, I mean, let's take that, you know, if. Great, you know, know great engineers, I know great engineers, ⁓ you know, great sales engineers. The folks that execute on what we just said, which is while they're working their day job, also, you know, hobbying on some, you know, something technological, ⁓ networking, working with user groups, and giving people the opportunity to see how passionate you are about what you're doing. ⁓ contribute to exciting things, work together as a team. If those people ever get laid off, it's like a shark frenzy for who can grab them up soon as and get them in for an interview. And that's a position people want to be in, is just sought after, right? God forbid something happens at their organization, everybody's like, awesome, big come up for me. ⁓ Derek Lazzaro: And that's the position people want to be in, is just sawing Right? Ben: I want to hire those people, right? People that I've got to see their work firsthand in some sort of, know, whether it's networking or whether it's user group, whether it's having the opportunity to work with their company. ⁓ And when you see engineers that are just love what they do, take pride in their work, you know, you see LinkedIn open to work, it's like, yes, let's go, let's get them on board. And so that's where, you know, again, it's really easy to say when you're, you know, Derek Lazzaro: Yeah, that's the only thing. . Ben: And our places in our careers, when you're early on, and maybe we'll put a pin in that one, but say you're midway through your, in a mid-stage in your career, if you can put yourself in that position, such that you have lots of people that can vouch for you, lots of people that have witnessed things that you can do, then that is the best job security you can have across the lifetime of your career, is again, it's people that can vouch. Derek Lazzaro: Mm-hmm. Right. No, those are really great points. you know, again, earlier in my career, I put zero effort into LinkedIn, right? And, you know, to me, it was like, ⁓ you know, I knew people that sort of just collected friends, connections on LinkedIn and people they hardly knew, frankly, right? And I thought, well, you know, that's not very genuine and like, what's the use in it, et cetera. But what I've realized is, you know, obviously there's nothing as good as the real sort of genuine engagements that you're talking about with people that truly know your work. But, you know, in order to get there, other than the people you work with day to day, It does require, you know, other kinds of engagement and outreach, right? Whether that is sort of a user group type of thing, you know, shared educational experiences, you know, working on some sort of, know, outside your day job project, et cetera. But, you know, the way that you get those opportunities is sort of just by being available, being visible, right? And LinkedIn is obviously part of that, right? It's just one piece, but. but I think it is important. And yeah, I've realized there's a lot of folks that just, you know, they're happy in their current role and maybe they're great in their current role, but they're sort of invisible to the rest of the world, right? And I think that's, again, it's easy to kind of fall into that. ⁓ Frankly, in some ways, the more you like what you're ⁓ in some ways, easier it is to fall into that. But I think it also, it doesn't activate all of those other pathways that you're talking about. Ben: Lactin's an interesting animal. ⁓ I think a lot of people, and myself included, when it's self-promoting, self-aggrandizing content, it's just like yuck. This feels so gross just posting something. As far as personal branding goes, I'm not an expert of it. Don't take any of my advice. What's interesting though is, Derek Lazzaro: Thank Yeah. Ben: I see some of the best engineers, the best tech people I know, put zero effort into LinkedIn, but they're putting a bunch of IRL work in, and the networking. And so you don't have to have a LinkedIn to be successful if you're doing real things in real life. On the contrary, I see a lot of awful engineers that have this whole thought leadership, know, personal brand strategy. Derek Lazzaro: Mm-hmm. Right. Yeah. Ben: And I'm sort of like, ⁓ jeez, yuck. ⁓ But oddly enough, if they get out of the job, they have a new one lined up for them. So I guess it kind of works. Not for me, but I guess it kind of works. Derek Lazzaro: Yeah. OK, OK, OK. So maybe it doesn't pass your genuine smell test, right? And building those real relationships smell test, but it may actually still work is what I'm hearing. All right, well, good to know for everyone listening. yeah. Right, right. Well, great. Ben: Correct. It may actually still work. Yeah, build a personal brand. Yeah, it's not for me, but it seems to work. Derek Lazzaro: Ben, don't, well, actually let me just ask you one or two more quick questions. So it's been a great conversation so far. When you are hiring engineers, you know, here in 2026, what are the skills? And obviously a lot of the work that your company does is around, you know, cybersecurity and solutions engineering and things like that. But what are kind of the absolute top three or four kind of skills, certifications, et cetera, that you look for when you're trying to hire somebody today. Ben: So I do something a little unique and it's kind of funny for me. ⁓ So when I'm hiring an engineer, pre-LLMs, used to ⁓ sort of, you know, I'd quiz people and it might have been a little too much, like if you just, you know, get an A plus in the rote memorization of the content that I asked for, then you could do pretty well. Derek Lazzaro: Mm-hmm. Ben: But it would be a lot of problem-solving stuff and now I do something particularly unique and borderline evil, but what I do is I so I have I have a It's called a bias towards Python engineer thinking so I think that the the way a Python engineer specifically approach problems and Derek Lazzaro: Okay. Ben: just sort of, you know, there's a lot of big data and analytics, which is very important skill set in what I do. And also, you know, kind of predicate this with, we're working in cutting edge tech that is, you know, very much in the analytical space, especially in security. And so I don't go after people with 10 years of system integration experience because they're going to be, have built a lot of reps. You know, I'm not saying I'm, opposed to them. Of course, I'll talk to folks that have those skill sets and that knowledge and expertise. But I'm also open to more entry level engineers that are Python engineers that might not have even dabbled in cybersecurity. Because I look for problem solving skills. Because a lot of the stuff I can, you you can learn, you can go through training and do your rote memorization and build some experience. you for our junior engineers, they'll Derek Lazzaro: But I'm also looking to hear more from engineers that are more highly skilled engineers that might not even doubt the cybersecurity. Because I know all of them have skills. Because a lot of stuff is Mm-hmm. Ben: you know, sort of watch a more senior engineer do it, then the senior engineer will watch them do it, coach, get it, work out the kinks, and then, you know, eventually they'll be doing it themselves. ⁓ And so I worry less about learning, you know, the factoids and the nuances of our business, because the reality is I'm probably, I'm in the cutting edge. I'm not gonna find anyone with a year of experience on a platform that's existed six months. So I throw that out the window. I look for... Derek Lazzaro: Mm-hmm Ben: problem solving. so again, I would say I bias on average to Python engineers ⁓ just because they've had to work that side of their brain a lot to, know, and even a college degree. So what I do that's kind of unique is I give them a challenge that should take them about three hours to do. But here's the interesting part is I've Derek Lazzaro: Yeah. So what I can do is kind of use this as a way to get talent that should take about three hours to do. But here's the interesting part is I trust a lot of the talent to make sure that if you just try to get the right through it, it will waste your time. And you'll never get it. But you can go through it. Ben: I throw it through Claude and open AI to make sure that if you just try to vibe your way through it, it will waste your time indefinitely and you'll never get it. Like you could go for a hundred hours and not get the answer. If you actually look at it and try and go have a thought process on it, it's designed beautifully to basically just put the LLMs through an infinite time waster loop. But the folks that actually go try trying to approach it with their human brain will sort of like, Derek Lazzaro: but the folks actually are. Ben: Hmm, okay, and it's generally not the hardest thing, but you should see the drop-off of people that don't turn it in. Last engineer I hired, ⁓ we gave that challenge out to our final 12, I want to say, or 10, just to see how they did, and we only got three submissions out of the 10, and these are all people with master's degrees, or four or six year... Derek Lazzaro: Four groups this year. That's their mass. Ben: bachelor master's in computer science. ⁓ And so that was kind of unique. I feel like, and by the way, I didn't even, I don't even, like many people, I don't have a master's degree requirement, I don't have a four year bachelor requirement. I have, you know, do you have some Python skills or something similar or security skills? And I'm open to ⁓ talking to a lot of different folks. You know, I think in tech, Derek Lazzaro: And so that was kind of And I feel like, by the way, I don't even, like many people. Ben: specifically, we're probably, as far as industries that are closest to a true meritocracy, I think we're there. Because I don't look at people's, where they went to college or this, that, and the other. I'm looking for intangibles and someone that has technical expertise first and foremost. If you can also communicate with people, awesome. If you're a cultural fit, awesome, awesome, awesome, right? That's kind of... Derek Lazzaro: That's kind of where I started. Ben: where I start the framework from. ⁓ And so, you know, now with the LLMs in place, there's no way I'm gonna give them something that you just pop in a cloud and say, do this, no mistakes, enter, here's your output, right? Because I could just do that myself. I'm looking to add another brain to the team. And so, hence the infinite time waste challenge. So. Derek Lazzaro: Right. Very nice. Well, excellent. Well, Ben, thank you so much for joining. It's been a great conversation. Any closing thoughts or anything you'd like to just share with the listeners? Ben: I feel like we've helped the people that are midway through their career excel maybe. ⁓ I think we should probably talk about people breaking in, because we all started somewhere. ⁓ Where did you start? What was the first job in tech and how did you get it and did you break in? Derek Lazzaro: Sure. Yeah, so my very first job in a tech role was ⁓ working for a very small DARPA contractor. So Defense Advanced Research Project Agency, ⁓ they needed somebody to help run their computers. I was local, I was basically high school at the time, and they're like, OK, this guy's inexpensive, let's use him. We've heard good things about him. ⁓ Ben: They needed somebody to help. Derek Lazzaro: That experience and some of just how quickly I saw tech evolving and how competitive it seemed, oddly enough, caused me to go to law school. So I actually remember telling a guidance counselor, you know, I've decided I don't really want a career in technology. I'm going to go to law school instead. And went to law school, got my law degree. Ben: experience and some of just how quickly I saw tech evolving and how competitive it seemed oddly enough caused me to go to law school. So I actually remember telling a guidance counselor, know, I've decided I don't really want a career in technology. I'm going to go to law school instead. And went to law school, got my law degree, became a licensed attorney, worked as a licensed attorney, ended up in a career in technology. So you saw the rate of change in tech versus, hey, half this was written in 1776. Right, literally. Yeah. So you wanted to go for safety. Derek Lazzaro: became a licensed attorney, worked as a licensed attorney, ended up in a career in technology. Quite literally, yeah. Yeah, know, mean, law, both fields were interesting to me. ⁓ Law, one of the things I actually did like about law is it felt like a platform that, you know, interconnected with so many areas of business, of life. ⁓ politics, et cetera, a lot of things I was just generally interested in. And it kind of felt like a better platform in many respects, to me at least from my vantage point at the time, tech felt kind of more narrow. ⁓ it did, truthfully again, it was also that pace of change issue that kind of worried me. was like, gosh, you know, I... Ben: And did, and truthfully again, it was also that pace of change issue that kind of worried me. was like, gosh, am I going to be in my mid-40s and having to just constantly learn new things? And apparently, yes. Right? mean, so I guess I was thinking ahead pretty far there. But. Derek Lazzaro: Am I going to be in my mid 40s and having to just constantly learn new things? And apparently, yes. I mean, so ⁓ I guess I was thinking ahead pretty far there. But yeah, that was kind of it for me. And then I ended up just being pulled into legal projects that were tech adjacent. And from there, being told, hey, you really seem to have a lot of opinions about the operational aspects of the tech side of the business, maybe that's really where you should be. So that was my journey, yeah. Ben: Sucks you back in. See, I'm like the opposite. The idea of going into a slow changing role would drive me nuts. If I go to a trade show, year one, then go back the next year, and I haven't seen vast product improvements and changes in things happening. Derek Lazzaro: Mm-hmm. Yeah. Great. Ben: I'll just, this was a waste of my time. This industry's moving at the pace, a dinosaur's pace, what are we doing here? So maybe this is better for my, I don't know, undiagnosed ADD or whatever it is, ADHD, but yeah, I think the rate of change is very exciting. And I think that with higher rates of change, you can hyper-specialize in something that you're legitimately super interested in. Derek Lazzaro: All right. Thank and increase. Ben: and it creates little mini TAMs or total addressable markets in that. So there's a lot of sandboxes to play in in tech, is where I'm getting at. And I think that's, it goes back to, or if you're just starting off, you can kind of just start specializing, go through your value of despair, build yourself up. I mean, I think there's a lot of ways of breaking into tech. Derek Lazzaro: Right. Ben: And I don't think it's just applying to 100 jobs that's gonna get you there. I think it's the networking, as we had mentioned, it's going out and doing things. ⁓ Also, the tools at people's disposal right now, it's not what we had when we were coming up. The technology was so gate-capped. mean, case in point, we just did a big experiment over the summer, and I actually did some research on how much it would've Derek Lazzaro: Mm-hmm. Ben: how much it costed us and I'm gonna give incorrect figures but they're roughly correct. I think we spent $1400 on this experiment on eight Amazon Web Services. We probably could have done it cheaper in Versel or CloudFlare developer platform, right? But we just did it on AWS. We knew it had all the things that we needed and we could just deploy it as infrastructure as could. And if we were to build the same thing from Derek Lazzaro: but. Ben: the technology that I had available to me when I started, it would have cost over a million dollars, well over a million dollars. We're talking deploying racks and data centers all over the world, licensing a ton of products. so you kids don't know how good you have it right now. There's really no excuses. When it comes to educational stuff, half these companies are like, give it away, go play with our stuff. Here's $500 in credits. Go, I don't know, have your... Derek Lazzaro: Well over. Heavy iron basically. ⁓ These are like, they're stuff. Right. Ben: or chat GBT or Claw, just go find who's giving out developer and tester credits and for students and stuff like that. I mean, that is, there's so much out there for free or low cost that you can tinker with. And man, I wish I had that. Derek Lazzaro: Yeah. and me. You know, that's an interesting point. So the first CIO, full-blown CIO title job that I ever got ⁓ was at a research institute. you know, not a standard for-profit company, but ⁓ a very interesting place that did a lot of different types of technology research. And They told me before they hired me, or right as they were hiring me, they said, you know, we really didn't think we'd end up hiring a lawyer as the CIO of our technology research institute. But when you showed us the diagram of your home lab, which was a fully populated rack at the time, they're like, we were pretty sure we had the right guy. Ben: They're like, we were pretty sure we had the right thing. Derek Lazzaro: And, know, but, but again, it was literally a whole rack of equipment in my garage at that point. And to your point, you know, you can replicate that same thing in AWS basically for free. So, ⁓ or, know, a little mini computer that you put on your desktop or something. it is that in that regard, it's a very exciting time. ⁓ and I think you're really onto something. I think one of the themes, you I've been kind of trying to sum up. Ben: It is, in that regard, it's a very exciting time. Derek Lazzaro: some of these conversations. And I think that ⁓ one of the really important themes of this conversation that we've had is, know, genuine engagement, genuine engagement with both people and your network, but also with, you know, what I'll call the material that's available, right? The sort of the technologies, the projects that you're working on. ⁓ And I think that that's important, right? And I think that the... Again, you sort of use the phrase hands-on reps, right? And if you're not working for a giant company that has all of that available to you, how do you do it? Well, you can build it in lab, right? Ben: Yeah, mean, here's an example. Like, literally somebody could do this. I don't know when the release date is. Maybe it's past relevance, like open claw or just find out whatever the big thing on X that people are talking about in the space. Derek Lazzaro: open. Ben: I mean, if you were to go out and deploy OpenClaw today and then learn some pen testing or even just find, there's tons of GitHub packages on like AI pen testing, you just have to drop a key in and just start deploying OpenClaw, giving it some decent privileges, connecting to things, and then tinkering your way through trying to hack it and find vulnerabilities, asking OpenClaw to even, Derek Lazzaro: Mm-hmm. or you know. you know, Ben: connect to a decent frontier LLM, just how can you improve your security, build a little, pull all that data, have your LLM just generate a blog on it and put in some screen recordings of doing that work. Put that out there and people are gonna wanna have conversations with you. you can also, if you build it on, let's say you build on AWS or you build on Google Cloud, find researchers that are Google Cloud, Derek Lazzaro: Mm-hmm. Ben: also doing security research and be like, hey man, really cool what you're doing, I wanna show you something I built on Google Cloud. Or if you do it on AWS, hey, really cool what you do for a job, you know, I have my dream job, I wanna show you something that I just built on AWS. Like those people are stoked to talk to people that are building on the platform that they work at and are doing cool things that are relevant in today's world. They're gonna wanna meet you. Derek Lazzaro: and wash it off. Those people are still at top. Ben: Again, these are just easy ways of networking. Take this, copy and paste it to whatever you're interested in or whatever's topical right now. Add to the corpus of knowledge in the world and just do little things, because most people aren't. They're just consuming the data. They're just reading it. Oh, that's interesting. You go to a security conference, people, oh, open call is so insecure. Have you used it? Have you tested it? Go out, get your reps in. Derek Lazzaro: Yep. Right. Right. ⁓ Ben: hey, this is what I did, this is what I found. And you'll find that half the stuff that's out there is like, ⁓ actually it's not as vulnerable to this as people are all talking about. It's actually this over here. Fighting those things, you can make pretty big discoveries by just doing stuff because the people that are doing the most prolific discoveries on average are also busy with a lot of things. We're working, I don't have time, we were actually doing the Open Class Security Project until Derek Lazzaro: Right. Ben: OpenAI bought them and then we're like, yeah, do we need to contribute to Sam Altman's open source anymore? But I mean, if I'm just starting off, I mean, I'm hacking OpenClaw all day for like three days straight and then putting out a paper and then sending it to everybody that I can, if I'm trying to find a job, right? You gotta build a name for yourself. Yeah, thanks for having me. Yeah, cheers. Derek Lazzaro: Right. ⁓ any travel. Right. Nice. Well, cool. Well, thank you, Ben. Excellent. Yeah, this was great. We'll have to do it again. Yeah. Thanks.