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334-Jacob Jones on Leading IT Through Different Company Sizes · You've Been Heard

• 0:01
  Speaker A: Welcome back to today's episode of dissecting popular IT nerds. I'm your host, Doug Kameen, and today I'm talking with Jacob Jones, vice president of information technology at Sellers. Welcome to the show, Jacob.
• 0:12
  Speaker B: Thanks for having me, Doug.
• 0:14
  Speaker A: So, Jacob, you're coming to us. You're vice president of it, but you've got a long history of working in it, in leadership for a lot of years at some really brand name companies. Like you're currently working for a manufacturing outfit with products that like pretty much all of us have probably touched. And in your past roles, like, we've almost definitely been to some of the places you've been doing it for. Can you elaborate a little bit on like, where's your history coming to us from?
• 0:46
  Speaker B: Yeah, so I've actually, you know, one of the things I've had fun with in leadership roles is working in different industries. Part of that is, you know, you're always kind of like, hey, maybe the grass is greener on the other side. And then of course it isn't. Usually you're like, oh my gosh, everyone has tech debt and a lot of the same problems, right? So I've been in, in the medical area, working for health care. I've been in manufacturing. Currently I'm in manufacturing, retail. You know, so some of the, some of the companies I work for, like, you know, Fortune 500 companies like Foot Locker, you know, Manpower Group, I worked for at one point, you know, a large boiler manufacturer that's pretty well known. So yeah, I've been kind of in and out some different industries and you know, it's been a fun ride to experience everything that you learn in each of those places.
• 1:34
  Speaker A: So thinking about jumping back and forth, you know, I mean, Footlocker is a household name pretty much. I'm sure most of our listeners are like, oh, Footlocker, I've been there. I bought my shoes there. I love going there. I hate going there. Whatever the case may be, they know it. Your current outfit that you're working for, Sellers, is in the manufacturing business, but it's in like, uh, I don't even. I, I've drawn a blank for a second on the product category. Are you making towels and other absorbent materials and those types of things? So you're, you're in places like Home Depot and things like that?
• 2:04
  Speaker B: Yeah, that's correct, actually. And the interesting story is, you know, it seems, it's. I'm sure other, other leaders have kind of this trajectory in their career. You know, you maybe start at maybe a Mid sized company or small company and kind of maybe move into bigger companies, who knows, maybe start right at the biggest company in the world and just, you know, company size and culture are so related. And so yeah, when I, when I made the move into sellers, I was really looking for, you know, something that would make an impact. And you know, so I kind of had the option of, you know, some larger, you know, again, staying in the, you know, well over a decade in Fortune 500 companies in leadership. But what attracted me to this was honestly just the impact of the products going back into manufacturing. I hadn't been in manufacturing for, I want to say 15 years. Right. Um, and there's something about when you make something and it's impactful, that it, I don't know, there's just meaning, it's so visceral. Right. And sellers, I'll just say this. You've used the products, you know, white rags in a box, blue shop towels, These things are staples. Like people use them, they don't think about it, but also sellers. And this is one of the things that attracted me is creating things like paper towels, 100% recycled. All the, or I should say 90% or greater recycled. But all the products are recycled products. And this was the kicker. They perform as well or better. And that sounds crazy to say, or better than the competing products that are virgin materials. So for me, like, you know, I've always, you know, you think you, you go to school or college and you, you take like corporate social responsibility classes and things and you're like, yeah, that'd be neat to work for a company that actually makes a difference. But, you know, I gotta make some, I gotta make some money. And you know, frankly, business is business. But I always secretly wanted to work for somebody that did something like that. Not to say the companies I worked for didn't do some good things, but this is really doing a good thing. You know, using all your Amazon boxes and things that, you know, you think are getting recycled. They aren't really. But a company like us will take that stuff and we'll make it into a product. So I don't want to go too deep into it, but I'll just say that even though I had other options on the table, I literally had a, the CEO do a demonstration of the paper towels. For me, these are paper towels that are just now a new product that are in targets. Not fully, just I think maybe like 300 stores at this point, some grocery stores. But it's a new market for the business, but it is the Best paper towel I've ever used. And I've never seen a product that is green because I like to use green products. Right. That outperforms everything else. So I'm like, I'm on board. I was like, I want to support this, I want to help this business grow. And of course it's fun too to be in a, you in a midsize company. You know, if you do a digital transformation, you feel it like, whoa, holy cow, the revenue increases. You know, massive things happen when you're in a Fortune 500 company. I mean some of the things you do there are, they're strategic and they, they move the needle, but not in the quite the same way.
• 4:59
  Speaker A: Yeah, so it's, I'm glad you brought that up because that was, I was actually going to dive down that, that hole a little bit here. The you working for a foot Locker Fortune 500 company, very large enterprise, you're at a mid size organization now and you just alluded to some of the differences between how the impact changes from one to the next. What are some of the other major differences that you've seen in the IT space between how each one either has to operate or chooses to operate?
• 5:34
  Speaker B: So this is going to be an interesting thing to say, but I had kind of forgotten. This is maybe crazy to say, but I kind of forgotten how, how fun it was to execute and deliver. And that's not to say you don't execute and deliver in a Fortune 500 company, but the layers you operate through, the silos you move through, I mean it's great, it's you know, great fun leadership stuff. But you know, what do you actually output? And often it's multi year projects and things don't quite get done.
• 6:02
  Speaker A: The chain is long, basically.
• 6:04
  Speaker B: Yeah, very long. Transitioning into this environment is very fast. And I'll say another thing is, you know, culturally I feel like, and again, I'm not disparaging any listeners that have, you know, that do work for large companies, but there's a disproportionate amount of time at least I'll say for myself that I spent just on, you know, the politics side. You know, obviously you have relationships with people, but you're often navigating silos and trying to get people to come together and how can we diplomatically pull this off and you know, a matrix style kind of collaboration. Right. And I spent, you know, 50% of my time doing that. Now I don't have to spend my time doing that. Why I spend my time on is delivering really, really Fast projects, you know, new E commerce platform in three months. Like that's crazy. I mean I spent years on that, you know, things I would spend years on. I'll just say I'm able to without all of the obstacles and red tape and things like that. And not saying we're doing it sloppy either. Right. I have an enterprise background, enterprise architecture background. So using frameworks and approaches, always having breadcrumbs like a decision matrix and a process that tracks your decisions and how you choose one technology versus another. So I'm versed in a lot of the, I'll call it the things that make a very large company successful. But you can implement those things super fast, super lightweight and get results. And I don't know, for me it's just, it reminded me of how rewarding it was and that's kind of how I got into technology. Right. Like what is cool about technology is you're making almost magic happen. I wanted to make this thing happen and it's like, oh my God, it's happening. That actually works. You know, you don't get that feeling always, you know, I guess you do maybe your woodworking or something. You know, it's like, hey, I made something. But that's how it is to me. It feels like that, hey, I made something and I feel proud of it. At dissecting popular IT nerds, we expect to win. And we expect our IT directors to win in one of those areas where we know that we can help you win. Win is Internet service providers. As an IT director tasked with managing Internet connectivity, few vendor relationships can prove more painfully frustrating than the one with your Internet service provider. The array of challenges seems never ending. From unreliable uptime and insufficient bandwidth to poor customer service and hidden fees. It's like getting stuck in rush hour traffic. Dealing with ISPs can try once patience even on the best of days. So whether you are managing one location or 100 locations, our back office support team and vendor partners are the best in the industry. And the best part about this is none of this will ever cost you a dime.
• 8:43
  Speaker A: Yeah, I hear exactly what you're saying. Like the ability to go from idea to execution in a mid sized organization is so much that, that that line is so much shorter. And the chains of people that you have to get approvals from, your ability to say we're going to do this and this is the steps we're going to take to do it and you turn around to your team and ask. It's like it's, it's, it could Be really gratifying to see those results really rapidly when you're going through those projects.
• 9:13
  Speaker B: Absolutely. And I will say one more thing about culture. And again, I'm not. I don't want to badmouth anybody, but. And I'm not just saying, you know, because I worked for some different Fortune 500 companies. But I feel like everyone says in leadership that, hey, we're transparent, we're genuine. We want to be like this great, easy, relaxed environment. But they aren't really as easy and relaxed in larger corporations. I just have not really experienced it. Now, I'm sure that exists. I'm just saying I haven't experienced it. But that's another thing that I'll say as a difference is there's a lightness to. You don't have to be the only, like. I'll just say one of my leadership, you know, traits I. I would say is I like to be myself. Right? I like to be genuine. I don't always like to use leadership speak. Right. You learn that in large companies, you know, exactly the different things to say in the buzzwords. Right. And I'm not saying there isn't a place for that because you are leading people and there is, you know, you have to set an example. And there are tough situations where maybe you use some of that. But, um, I feel like, yeah, you can just be, you know, more relaxed, more genuine. And then that allows other people to be more relaxed, more genuine. They say, oh, this person can be goofy. You know, I can just be goofy and just do something silly. And they're like, what am I even looking at? This is our head of it. Like, what is that? You know, And I like that because any leaders that I ever worked for that did stuff like that, always surprising me, I'd be like, oh, you know, that's. That's cool, you know, versus, oh, there's this big chasm between, you know, me and this other person that maybe I work for or I work for their person that they work for or, sorry, there's a chain of people going down, you know, and you're like, as you go up the chain, it's sort of like there's a. More of a distance, you know, But I like there to be. To not feel like there is. And I've always appreciated that about. About different. Different folks, you know. I'll give an example. The previous CEO for a footlocker, just, for example, Dick. This is a guy that, when people would meet him, they would actually. They wouldn't. They'd have no idea. He was a CEO because they're like, oh, this guy was so nice. I'm like, yeah, that was, that was the CEO of the company. You just didn't think it because you'd think, oh, he's, he's probably popping circumstance and he's got to have a sort of a game face and things like that. No, he was just like, hey, I'm, I'm Dick and let me just talk to you. And you're like, oh, this guy's really cool and he's funny and you know, just kind of like fun to talk to. But yeah, you didn't really have that. So I can't, so I can't say everything is like that. But just in general I would say that's one of the things that I appreciate and I've seen that's kind of different and makes me go, hey, I like this kind of mid size space. And obviously mid sized companies grow if you do the right things and they can become these large companies. And maybe if you don't like something like what I'm talking about, maybe too much corporate culture kind of stuff, maybe I can influence that as a leader. Right. To make sure that doesn't happen so much as the company enters that kind of size.
• 12:08
  Speaker A: Yeah. Then I think about as a, you know, as an executive leader in a mid size organization, the things that I put high value on. So like, I think about going back to just relating this to your story that you just shared. The ability to be relatable, to be accessible, to be perceived as, you know, a human. And not like, I don't mean like maybe it's not the right way to frame it, but to be perceived as having high empathy, you know, is. Those are really valuable to be successful as a leader in any space. But the pro. I think one of the challenges is that the organization gets very, very large. There's. The executives end up becoming, there's a high risk of becoming. Siloed was one word you use. But strategic. Like you have to be, you have to be like, like strategically ambiguous at all times because heaven, something happened and you're on the wrong side of that conversation or whatever the case may be and stuff like that. And I know that there are executives who have navigated those waters and do it successfully, but it's really difficult, you know, it's difficult to do and to do well and to make yourself appear humanly accessible and empathetic when you are this like distant character in a story for other people. So I think about that as a positive experience, like in being in a mid sized organization and what that brings to the table and like the way that I can show up, you know, I'm currently running like a very large project. Well, you mentioned Enterprise architecture. I'll go back to that. We created Enterprise Architecture where I work, we're probably about the same size corporation. I work in the nonprofit space. We're about 500 employees and we put together an architecture for our systems and a plan for how to get there. So we've been steadily executing to bring ourselves in line with what we want to see. And the biggest project is currently implementing a product, Oracle NetSuite. Well, that's a huge product, touches everything. So we've got this monster, just enormous transformation going on. And alongside with that, if you've been through these types of organizational transformations or implementations, that's only the beginning because once you implement the NetSuite product or another ERP product, you're like, oh, well then this needs to change to fit with that. Or this one is better to interface with this so that it cascades into a whole set of other things. But when you're going through the change management process of executing that project, the implementation, the communication, the things of building the relationships with the teams and everything else, the bigger the organization, I want to say, the harder it gets. But there's like a sweet spot where it's big enough to have teams that you can work with. For instance, I have a director of project management, you know, and if I was smaller, if our organization was smaller, we wouldn't be big enough to support that type of position. But if we were, you know, say, you know, 3,000 or 5,000 employees, we would probably be so big that there would be a whole VP that was in charge of project management and there'd be a team of, you know, 20 under them running it instead of a team of like a handful. So the closeness of the teams to the execution starts, you know, starts lengthening as the organization gets bigger. And it becomes harder to engage the change management process in a way that people feel like they have an investment in the outcome and that they understand what's going on and they feel invested in the goal that you're setting out as opposed to it just being like a big corporate thing that's happening to them as opposed to with them.
• 16:08
  Speaker B: Wow, you just laid so many layers of just awesome concepts right there. There is so much that we can say about the, you know, the architecture and how you put something like a new ERP system in compared a mid sized company compared to you Know, a large enterprise that's maybe, you know, Fortune 500 or, you know, Fortune 100. And I was going to say that, that you almost. It took me back to like maybe some trauma. No, it's not, not really trauma, but maybe around just putting in new systems because, you know, first in architecture, you envision the landscape. You have an application portfolio, you have all these systems. And in any company that I've ever been in, I'm probably sure this is everywhere things happened, how they happened, right? Maybe it was organic, maybe it was this, maybe it was that. But nothing was really, nothing was perfectly planned. And in retrospect, what you do in enterprise architecture, right, you kind of make sense of the landscape. You go, well, look at this, look at that. How do I make product information data centralized and manageable, or customer data or whatever?
• 17:17
  Speaker A: You're planning an orchestra. I just used that metaphor in our all staff meeting that I just hosted this week to convey it to our staff. I was like, what we're doing is you could think of this as building an orchestra. And as we've grown, the orchestra has gotten out of tune and we need to bring in new players. We need to bring in, you know, sometimes new, you know, tune up the instruments we have, sometimes bring in additional instruments to expand to meet us where we're at. And then the enterprise architecture is like the sheet music that tells us how we're going to do it.
• 17:46
  Speaker B: Ah, that is a good analogy, Doug. I love that. That's great. Analogies are good, right? I mean, it's important on these large transformations, right? Because you want everyone engaged and how can they, how can they understand it? The analogy I've used recently is Lego blocks just. And that's one that's been used before, but to talk about the concept of composability. And so in large enterprises, right, that you figure out how to build systems in a composable way. Because hopefully we've learned in the last however many decades of doing it that you can't build like one big system that does it all. We started that way with a mainframe, right? Systems became distributed, but now it's like, how does it all fit together? So the best you can do is create blast radiuses that are kind of nice, right? Make nice API layers around things, build things that are self contained, that do business functions, that interact well with other things that are self contained, do business functions, right? And I was just going to add one little fun anecdote is I used to spend so much time trying to figure all that out and in the midsize company, just the concept of LEGO blocks, it almost works better because, you know, for sure there's less, there's less pieces, but the pieces that exist, they might even be more cobbled together. Right. But they're composable just by virtue of being cobbled together. So when you're doing a transformation, say in a large enterprise like this is my experience, like having done. Spent years doing that previously, you, you know, you're trying to unwind systems that have taken years to kind of get to where they're at, and they're so big and there's so many thousands of people using them and all that stuff, and it's so hard to put the genie back in the bottle. And whereas now in, in a smaller company, right, you still have maybe even worse, you know, Skunk works and things that, that put things together. But the, the design of having a blast radius where you can take, say, these custom applications and these different systems and bundle them together and say, you know what? I'm going to transform just this section of the business instead of the whole business. Like, I think you have more opportunity maybe even in that midsize company. At least that's what I'm finding. Because the transformation work that again, years of work, and you're like, did I move the needle? Did we actually do. What did we actually accomplish? Well, we can do it so much quicker, but it's also because it's more composable. I feel like by the nature of just how the business, maybe this is manufacturing as well. Right. Systems are disjointed and so forth. It's almost like you were rewarded for having built poor systems when you actually do the full transformation. A weird new realization I had in the last year, like, this is awesome. I would have spent years trying to figure out how to, how to transform this and put in new erp. Like you're talking about new systems, but instead it's actually pretty straightforward. You know, like, here's exactly where you would cut this particular area off from this area, and here's these systems and let's couple them together and replace them with, you know, a new, simpler platform. Right. Because you're trying to consolidate still and make things, you know, simple.
• 21:04
  Speaker A: Yeah. And, you know, simplicity in, in your configurations like this. I've actually run into this in our organization, my current organization, where.
• 21:16
  Speaker B: We look.
• 21:17
  Speaker A: At some of the decisions that were made. So at one point we were like, oh, we'll make a decision about how we bill for projects. And then we let this one small Piece of our organization drive how we decided to do it for everyone. And you mentioned about blast radius and stuff like that. So we implemented this process. This was before my time, so I'm now kind of like, I don't wanna say cleaning it up, but I am. You know, this is part of the changeover from our current systems, you know, an older siloed type of environment to a more integrated plan setup where things are intentionally built to work together. You know, if not the same system, but at least to work together with an overarching like idea about how they fit together. And we would make decisions about one thing that had all this other secondary impact. You know, hey, look, we have, we have a team of consultants and they need to be able to build consulting time. So. But we, you know, the. That's only like 20% of our business. 80% of our business doesn't have to do it. But it's complicated enough that it'll give us more visibility if everyone tracks their time. Really detailed. Right. So then all of a sudden we imposed across the whole organization this like, effort to track time. And the consequences of doing it only became apparent as time went on. You know, like you're, you're, you know, a lowering of compliance with like timesheet entry A, you know, how accurate is the time that they're actually submitting and the time cost of doing the entry that they weren't doing before. You know, individually, it's only a couple of minutes a person, but like, and aggregate it turns into a pretty large chunk of the business day. So, you know, I think where I'm going to relate this back to is I'm going to. And I'm going to grab a copy of the book here. You know, the listeners can't see me on video, but do this. But there's a book in this space of Enterprise architecture. You've probably read it. So. Have you read Enterprise Architecture as Strategy?
• 23:22
  Speaker B: I have not read this book, but I've read excerpts from it. From it because it's a Harvard business. You know, there's pieces of that that have been dissen. Yeah, yeah.
• 23:31
  Speaker A: So like that book is like the. It's kind of like the or father book. I don't know how to describe it for Enterprise architecture. It's written in the early mid 2000s and the concepts of it and the tenants were built the idea of Enterprise architecture. But Enterprise architecture itself kind of fell out of favor as a concept through the 2010s. Here in the late 2010s, it was all like, oh, we got to move faster. So it's agile, you know, everybody, oh, we're going to do agile stuff. We're going to do this even fast. And Enterprise architecture and the EA function was, I perceive it fell out of favor because it was viewed as a slow. It encouraged slowness in a certain way. And that's absolutely true because it encouraged intentionality. The goal was to be intentional about what you're doing, not to just do it because you can.
• 24:31
  Speaker B: Right. It's like the pendulum going back and forth. Same with, same with project management, right. How many companies have distributed or just, you know, what's the word broken down or maybe simplified their project management offices. And then you go back 20 years ago and it was the PMBOK and you gotta do it and follow all the rules. And it kind of reminds me of like what you're talking about the time tracking, Right. I've been through that too in different organizations. Like how much rigor and control do you have versus flexibility and speed? And that's always a moving thing. And it's, it's sort of like, it's, it's. I think it's contextual, like with, with the time, the era, the company, you know, size of company. But it has to be right, because otherwise things don't work. And I think that's kind of what happened with the ea, right? It became overbuilt. Of course, when people invest in something, they become like experts. It becomes their discipline, their life, their craft. It's easy to forget, like, you know, that there's other stuff outside of that and what, what that's really impacting. Because, you know, I could see EA practitioners just being interested in getting their documentation done and having all their keys to their kingdom just done just perfectly. But it's a compromise, right? And I want to say that's something that I think a lot of us have learned in recent years, very recent years, is all of the systems thinking. It all has been kind of unraveled through agility, which has kind of permeated every company, right?
• 25:55
  Speaker A: Yeah.
• 25:56
  Speaker B: But then you have to pull it back to have some level of rigor, you know, you have to have some intentionality. I love your, your, your verbiage there. Like, it is about intentionality. And it's so funny to me, the thing that I always reset on if I see this as off as I, as I go, okay? You just need the minimum viable version of that. Like for instance, you're talking about decisioning, right? Like, do you have a breadcrumb? Is there something that Shows you made that decision. If the answer is no, okay, you. You have nothing. So what is the minimum thing that you need? Right. Same would go for a project, right? Oh, we just kind of fly by the seat of our pants. Okay, I understand that you don't like project plans, right? Or big architectures. Right. You know, following these things. But do you have anything? Okay, now what is the thing you have? Then the next step is, is it good enough? Right? Because you probably put a little bit of effort into it and you have to move it just up enough and then it just. Is just good enough. I'm like, look, you could do that with everything that you do. I feel like this could be a philosophy, right? I mean, honestly, it's kind of how I follow because otherwise you kind of waste a lot of time, right? You build so much process and so much organization and structure, which is great, but it does. It's like the effort wasn't even worth it. And it has all these counter influences that are negative outcomes.
• 27:12
  Speaker A: So perfect is the enemy of good, you know?
• 27:15
  Speaker B: Yes. Yeah, exactly. And. But this constant battle with all of these approaches and systems, I think is kind of where we're at. And understanding, like what we're talking about, I think is a, Is a key foundational leadership, you know, capability that I feel like current modern leaders should have. And honestly, some humility too, because you're going to find your off. Like there's, there's a. I ride in on my high horse sometimes on things where I'm like, this is how it's been and I have so much experience and this is the approach. And I'm like, wait a minute, look at how people are responding to this thing. And it's awesome. I mean, technically it's probably the correct thing. It's the, you know, but it's not actually getting the result. And you have to go back to reality. And this is of course the lesson of agility. Right? You go, reality is what dictates things, not me. Just because I came up with all the cool ideas I learned, the frameworks or whatever, doesn't mean they're going to be the right thing to do. Reality is always the one that's teaching us the lesson. And I think there's a. Like, again, I go back to humility. I think there's a humility in that because I've been humbled many times with, you know, cool approaches to things that were, I thought for sure were the way it was going to work. And then actually I had to adjust.
• 28:26
  Speaker A: Yeah, I call those the hot takes. And I'll. And I've learned the way I end up doing it now is I'll come in with certain things and I'll, I'll be like, okay, so my hot take is this. And I'm willing to have my hot take be like, not the way we do it or not the way we go, but that way it kind of injects a certain amount of humor into the whole thing. So it comes in with the idea that it's okay to challenge me if we think it's appropriate. That doesn't mean I'm not going to push back and we're going to have it back and forth. And I think the other piece you brought up how you show up is you coming in on your high horse. And how you show up is critical to the acceptance part of this too. You know, you can have the best idea, you show up poorly. Like, they're like, yeah, whatever, man. That's that, you know, take Jacob's going to hear coming in.
• 29:15
  Speaker B: You know, I love what you're saying too, Doug, about humor. I was, I get reminded of this because sometimes I get kind of serious because especially when you're thinking about like transformations and you're like, we got to get all this done. You know, here's our three year plan. And it's going to, you know, it's business differentiating stuff. Right. It's hugely strategic. It will change the direction of the company and, you know, you'll beat the competition, all that stuff. Where was I going with that? Totally lost my train of thought. There you go. Oh. Oh, no, it was, it was about humor.
• 29:45
  Speaker A: Just.
• 29:46
  Speaker B: That's something I'm always reminded of is like, humor has to be injected into your work. And I also think, of course, like we were talking about culture, right? That's a big thing. But I think it's important just to make sure there's some just really goofy stuff sometimes so people realize it's not because it's so serious. Right. To work often is. Right. So I like, I like what you're saying about just, just making it like lighthearted and even giving people a cue to, hey, it's my hot take. You know, they know they can challenge it. And you. And they know you'll probably make fun of the thing that you, you were, you know, was your edict or whatever out of the, out of the gate. Right?
• 30:22
  Speaker A: Yeah, absolutely. So I'm going to change directions for a second here.
• 30:26
  Speaker B: Let's explore.
• 30:27
  Speaker A: I'd love to explore a little bit more about you and kind of your history. So everyone has different stories about how they came to be in, whether it's your leadership. But I want to talk more broadly about like being in tech. So you know, you're a tech leader, but how did you come to be in it? Did you set out like, like when you were like five, were your parents like, Jacob's got, Jacob's got all the computer knowledge and he's tinkering and pulling apart everything, or were you going to be like an architect and then you fell into it? Like, tell us a story. Let us, let us understand more about how you came to be where you are.
• 31:01
  Speaker B: Yeah, sure. Honestly, I mean, this is probably the case for a lot of people, but video games back when I was a kid, like again, an Atari 2600, that's.
• 31:11
  Speaker A: One of the coolest Pitfall too, man. You play Pitfall?
• 31:14
  Speaker B: Hell, hell yeah. Pitfall all day. Pitfall 2.
• 31:18
  Speaker A: Yeah, Pitfall 2, not Pitfall.
• 31:19
  Speaker B: Yeah, you're right. 2 is definitely the superior one. Yeah, I mean there, there's so many cool games like that, but. But yeah, just always loving, you know, that, that burgeoning technology that happened in, you know, in the 80s, I'd say, like, there's such a big thing as a kid, like, you know, that was what I remember. And so I always loved it and was attracted to. I can't imagine what it's like for kids now. The level of tech they get like with their video games and stuff is just, you know, it's mind blowing. And I still play those video games. But, but so I always kind of liked it. And I remember the moment where I probably the first inkling that I wanted to work on computers is. And you know, I was in one of these like library type of scenarios where our library had one computer. Like, so we're not talking, you know, big city school here, but had one computer.
• 32:06
  Speaker A: Your public library or the school library?
• 32:07
  Speaker B: This was like the school library. Yeah, public library probably only had one as well, but, but it was, you know, I'm sure it was an Apple 2GS or some old, really old computer. I don't, you know, maybe predated that. But they were like, here's what a computer is, class type of thing. And so the whole class of maybe 30 kids or something, they were showing us this program called Dr. Spazo. Now this is one of these really early level text driven programs. But Dr. Spaitso is basically it's a therapist. It pretends to be a therapist. And what it does is it asks you questions and it's like, how are you doing? Oh, I'm doing good. And as you talk to it, it's trying to, like, you know, it's trying to worm information out of you and then basically, like, it regurgitates a lot of it back. So it's almost like a punchline in a way. Because what, you know, a therapist joke would be, the therapist just ask questions and they never really, you know, talk or do anything. They just listen to you talk. Right. And that's the. That's like the process. So it was kind of funny the program was doing that, but I realized, like, the whole class had left and I had been hitting this thing with questions and trying to understand, you know, how it was operating. Like, what the. There's clearly a tree structure and some kind of logic, and how was it doing this? And so, yeah, so I just spent all this time until I kind of understood and found its flaws. And from that moment, right, I was like, wow, that was so cool. And what's ironic about that too, is think about that. That was like pretending to be like, AI, you know, way back in the day. Clearly it wasn't. It was silly comparatively, but. But the same idea. You want to interact with this computer and have it tell you things about yourself or have a conversation, right. Maybe it's intelligent. But that fascinated me. And, you know, from then on, I was just like a computer nerd. So, you know, it was pretty obvious when I got out of high school, you know, I. I started a gaming place with some friends of mine, you know, out on State street in Madison, Wisconsin. So this was this kind of was like the very early, like, you know, we had Doom and then Quake. Right, Those early games where it was, I would say, pre Internet, like this.
• 34:17
  Speaker A: So you set up lamp parties, essentially.
• 34:19
  Speaker B: Yeah, we set up a big old LAN party. And it was funny because people still remember that because it was a marquee landmark kind of thing, because nothing existed like it at the time. So it was ahead of its time. But we were only able to run that for a few years because, well, pretty soon everyone got the Internet. So that wasn't going to last forever.
• 34:39
  Speaker A: It was like those Internet cafes that, you know, you're like, I got a new business. I'm going to run an Internet cafe. Like, by. By like six, seven years later. That was. You were definitely not running an Internet cafe if you didn't do anything else.
• 34:52
  Speaker B: Exactly. I even know people that did that. I'm like, yeah. And it didn't last. But yeah, you just don't know the Technology moves so quick. But yeah, so that's kind of my, I mean, that's kind of part of my story. But, but yeah, I got into, you know, I was on the Microsoft Windows 95 launch team. So that was kind of my first job out of high school. So that's.
• 35:12
  Speaker A: So what does that entail? Like what, what does, what does being on the launch team mean?
• 35:16
  Speaker B: Means like this product hasn't been released, it's going to be released say in a year and there's just this massive ramp up. And I want to say that was a big technology jump at the time, right? Windows 95 was such a big shift in how many people used computers, how you interfaced with the Internet. It had a web browser, you know, all these things that didn't exist before that. And yeah, so, so we, you know, they, they hired a mass amount of people. But, but yeah, I was on that launch team. So that means you're taking calls before it's even released, right? You have the beta releases and things like that and then finally releases and now your technical support. So that was kind of my first, you know, IT job. And then from there I just kind of went through a lot of different jobs. And ultimately I spent probably, I want to say close to 10 years about as an IT consultant just, you know, implementing systems and networks. And you know, you had Microsoft, Novell, Cisco, you know, all the, all the things that rolled up through the late 90s into the early 2000s and then shifted into leadership. So like, that's kind of my leadership stories. I would say I was always the smart, I'll call, you know, a little bit of a computer nerd that loved to build the things. And I would go into companies, a lot of Unfortune, 500 companies, and I would see how, how things were being run. And you know, of course you're, you know, when you're young, you sort of, you sort of overestimate your abilities maybe and things like that. But I kind of saw a lot of middle management that operated these teams and ran these projects. And I was like, why are we doing it this way? It's just so inefficient or sloppy or, you know, just, you know, things that I saw I could improve. And so, yeah, after about, I want to say that 10 year mark, I took a job as a IT manager. And that was my shift, I would say, from, you know, the actual practitioner executor to now leading teams and trying to build, you know, the scaffolding right, to, you know, make scalable systems and you know, all that good stuff.
• 37:17
  Speaker A: That's great. Actually, you jumped. You jumped me right to my next question, which you pretty much already answered, which is when did you feel like you became a leader? I mean, if you want to elaborate a little more on that, be great, but like, you know, you made that transition from being the team member to being the leader. You talk about when you made the official jump, but when did you realize and what made you realize, like, I could be a leader and this is what I could do and why I want to do it?
• 37:42
  Speaker B: Honestly, I think. I think it probably was pretty early on. Just like as a consultant, I guess I did lead consulting projects where you have a team of people, you're selling services, and then you're implementing things for large companies. So just having some of that leadership acumen with those smaller teams in those situations, even though maybe I wasn't managing staff or anything like that, like, I definitely knew I had the skills to think about other people and how, you know, I'll just say, like, one thing that always, if I go back to like a very simple thing that stuck out to me was I was always thinking about, you know, whatever team I was on, how the other team members could work better with me. Like, and I would go above and beyond, right? Hey, let's all use a central repository and let's all work off the same documents. Let's all try to follow this thing that's going to make us all work better together. But I was always so focused on that and it always. And it was strange that not everyone was right. You know, you have all sorts of different types of people, but. But yeah, that was, that was always my vision and sort of impulse because just deep, deep and deep in my heart, you know, like, I, I just want everybody to work together and, and I feel, of course, I believe that, you know, the more people, you know, the less boundaries they have, the closer they work and the more that they work together and can share and feel not like, you know, closed or, you know, holding on to their stuff. Then I think the smarter the team becomes, you know, just like a nodes in, you know, in a brain, you know, like we become a bigger brain if we can work better together. So I was always of that belief like, you know, without really concrete evidence and sort of built that knowledge of that, that does work, you know, in those early kind of years. And that's part of what led me to go, man, I should lead teams, because I enjoy that. I really like, I like bringing people together and, you know, having bigger Outcomes because we've somehow, you know, we've somehow. What's the word? Like, we've, we've crossed over our individual worlds in some and we've become something greater than, than the sum of the parts. Right. And you can feel it in a really high performing team. You can feel it and the energy goes up as well. So obstacles go down, energy goes up, people, people become smarter. It's weird. Like, I know I do, like, like if I have a group of people I'm working with and they all are really open minded and they're really enthusiastic and they're working in that really collaborative capacity.
• 40:19
  Speaker A: Yeah.
• 40:20
  Speaker B: I mean, I'm getting ideas so rapidly from them and vice versa. And we're just coming up with stuff and you go, man, if, if it was each of us going and doing that ourselves, we wouldn't even on like a tenth of what we got as an output, you know, in terms of what was the solution? How do we, how, how fast could we do something? So, yeah, I think there's a lot to say about how those pieces play together, but it's a very simple concept that you can almost feel when you're just a team member on a team. And I always, you know, even those early days kind of felt that, right. You're in a team where it's not cohesive and you don't have that sort of, you know, collaboration and that, you know, vision of how that works or people trying to.
• 41:00
  Speaker A: This is this, you know, to use the, to use one of those executive buzzwords, right? The synergy. The synergy. It is, it is everybody working together.
• 41:08
  Speaker B: Synergy.
• 41:09
  Speaker A: That's right. So just like we're coming up towards the end of our episode here, but just a couple of more questions about things. First I want to ask just a fun question. Is there, can you tell us something that people wouldn't expect of you, about you, you know, something you did in the past, something in history or something like that. And I'll, I'll, I always like throw out an example just to let people know. I was once in the Macy's Day parade as a kid.
• 41:36
  Speaker B: Oh yeah, that's cool.
• 41:38
  Speaker A: So like people would know that. But like, is there something about you? Something you do? Something like.
• 41:43
  Speaker B: I mean, yeah, I mean, I have hobbies, like I play the piano, you know, stuff like that. But, but that's not. I would say what's interesting that probably not a lot of people know is when I was a kid, this is kind of a weird thing to say, but I'm just Saying, I'm gonna give you, I'm gonna give you something. Throw a curveball here. All right. But I actually, I actually died for 10 minutes. I was dead for 10 minutes.
• 42:07
  Speaker A: No way. Yeah.
• 42:09
  Speaker B: Confirmed dead. Like to the point where I was just left in a room to, you know, with Ash and Gray, you know, just dead. And, and everyone had just given up. They were like, okay, I was at a, A smaller, like, hospital clinic just from a head fracture. Yeah. So. So that's why I'm the way I'm. No, but, but, but. No, I. So I was gonna say that was. That's an unusual thing to come back from.
• 42:40
  Speaker A: That is like, you don't mind me asking, like, how old were you when that happened? Like, were you like an infant or. It's like, like 10 or.
• 42:46
  Speaker B: I was 3 years old, so I was pretty young.
• 42:49
  Speaker A: Yeah, that is, that is a fascinating story. Like it. I mean, I'll say it's fascinating because it seems that everything worked out. So, like, you know, that, that part was okay. You get to tell the story afterwards about that. You know, like, that's almost as crazy is. Is like it, it. And I usually don't. I don't use this as an example on the podcast because it's too it. And I'm only going to bring it up because yours is so good. But I delivered. I once delivered. I delivered one of my children in my car.
• 43:19
  Speaker B: No.
• 43:20
  Speaker A: Yes.
• 43:21
  Speaker B: That is bananas. Are you kidding me?
• 43:24
  Speaker A: That's right. So, so now. So I. There was like a podcast like six months ago where I didn't even think about it. And I just kind of used that as an example. The guy's like, oh, dude, I can't even compete with that. And I was like, oh, I'm so sorry.
• 43:37
  Speaker B: That's like, you should have your own Netflix show. You know what I mean?
• 43:40
  Speaker A: But I died for 10 minutes. That is absolutely banana pants. And I'm obviously clearly glad and I think the listeners are clearly glad that it worked out, but what a wild, wild story to be able to share.
• 43:57
  Speaker B: Thank you.
• 43:58
  Speaker A: Yeah, so coming up here now, we're really closing up and coming and coming to the end. But for our listeners, what leadership advice do you have? You've been through a lot of different eras of your leadership journey. You've worked for Fortune 500 company, 500 companies. You work for mid sized companies. What would you love to share with listeners who are other IT leaders about? Like, what's the, what's important about being a leader? What qualities are important? What things would advice would you Give, you know, I'll leave that open ended.
• 44:29
  Speaker B: I would just say get out of your own way. Right. And I'm not picking on anybody in particular. I'm saying this has been my journey. But yeah, it's humbling at times to be a leader because like a phase we go through, of course, is delegation. We're trying to delegate things, and especially a lot of it leaders, I'm not saying all of them, but come from a lot of different backgrounds, but a lot of them are problem solvers, people that maybe did a lot of the jobs that they're now overseeing and managing. Right. So it takes a certain kind of, you know, drive to be that kind of person. And then when you're managing people like that, it's really, it's. It's not always easy to let go of the reins. But, but of course, autonomy and feeling empowered is what drives all of us as humans. Right. I mean, again, I don't. Shouldn't generalize too much. Maybe there's some people out there that have some, some issues. They don't like that. But overall, the best thing you can do is allow people to grow into, you know, stretch in their own way. And even though a lot of times I'm sure you've experienced this, Doug, the output of what they're doing for maybe something you know really well isn't as good as what you yourself could even do. Now, even if your skills got rusty, maybe somebody that's, that's learning, but it's. It's so important to let them just, you know, get their sea legs and figure out how they're going to do it and then let them do it a different way and focus on the outcome. I'm sure most leaders are aspiring to do that, but I think there's importance to being humble and allowing people to do things the way that they need to do them.
• 46:05
  Speaker A: Awesome. That was really insightful. Jacob, thank you so much for investing your time with us on the podcast today.
• 46:12
  Speaker B: You are so welcome.
• 46:14
  Speaker A: So that's a wrap on today's episode of Dissecting Popular IT Nerds. I'm Doug Conveen, and we look forward to coming to you on our next episode.