Show Notes

Career Downloads Episode 022: Jay Jackson Takes Us Through His Journey from Entry-Level Tech to Project Management Success

In this episode, host Manuel Martinez welcomes Jay Jackson, a dynamic figure in the tech industry whose career spans sales, project management, consulting, and education. Jay opens up about his fascinating path that began at CompUSA and evolved into a successful career in project management and consulting.

Jay shares how his early experience in video games shaped his approach to problem-solving and business challenges. He explains his innovative RAKSE framework for building a professional brand:

• 
  
• Reputation: The foundation of career success
  
• Ability: Understanding and leveraging natural talents
  
• Knowledge: The role of formal education and continuous learning
  
• Skills: Transforming knowledge into practical capabilities
  
• Experience: Building a track record of successful implementations
  

Key Discussion Points:

• 
  
• Converting an entry-level cashier position into a springboard for tech career growth
  
• The natural progression from sales excellence to project management expertise
  
• Balancing teaching with consulting to stay current in technology
  
• Building and maintaining professional networks through authentic curiosity
  
• Real-world project management successes and lessons learned
  

Listeners will gain valuable insights into:

• 
  
• How to navigate career transitions effectively
  
• The importance of building and maintaining a professional reputation
  
• Strategies for continuous learning and skill development
  
• Practical approaches to project management
  
• The value of authentic networking and relationship building
  

Connect with Jay Jackson:

https://www.linkedin.com/in/jayjackson2/

Connect with Manuel Martinez:

https://www.linkedin.com/in/manuelmartinez-it/

Follow Career Downloads:

Website: https://careerdownloads.com

YouTube https://www.youtube.com/@careerdownloads

X/Twitter https://twitter.com/@careerdownloads

TikTok https://www.tiktok.com/@careerdownloads

LinkedIn https://www.linkedin.com/company/career-downloads

Instagram https://www.instagram.com/careerdownloads

FaceBook https://www.facebook.com/people/Career-Downloads/61561144531249

#CareerDownloads #TechCareers #ProjectManagement #ProfessionalDevelopment

Transcript

Manuel: Welcome everyone, my name is Manuel Martinez and this is another episode of Career Downloads. Where each episode, I basically hit the refresh button, bring on a different guest to really learn more about their career. To understand how they navigated it, different lessons that they’ve learned to really try and pull out actionable advice that you can use as you’re managing your own career. So, for today’s episode, I have with me Jay Jackson. So we have crossed paths on two different occasions. He has a very interesting background. He has done a number of things, different areas that we’ll touch on as we kind of go through the conversation. And I’ll let him explain that, kind of his ideas on professional branding, the different and things that he’s done, how he’s kind of navigated through different career choices and different roles. So with that, I’ll introduce Jay Jackson.

Jay: Hey, Manny.

Manuel: How you doing?

Jay: Good to see you.

Manuel: Good seeing you.

Jay: Beautiful house here, Manny.

Manuel: Thanks.

Jay: I like the setup.

Manuel: Took a little bit of work to kind of put it together, but I think overall it’s starting to look semi-professional.

Jay: Starting to, right? Yeah I like it.

Manuel: So what I’ve been doing with the guests is if you can just kind of start off, just give us your current role or position and then just kind of a summary of some of the responsibilities and things that you kind of do in those roles.

Jay: So I’ve got a lot going on. So, you know, cut me off if I’m going the wrong direction. But right now I teach at a local college, a couple of them actually. And my main role as an instructor in the Networking and Cybersecurity program and the classes I teach, I’ve taught are introduction, I like intro classes, because it’s like getting someone interested in a concept, I’ve taught introduction to Linux, Introduction to Information Systems, Project Management, Networking, and Introduction to Cloud Computing and helped develop their AWS Cloud Architect class with someone from AWS. I believe you know him.

Manuel: I do.

Jay: Great guy. [Laughter] So, I’ve done that and I’ve helped with the project management at the grad level here at local college. So that’s my teaching. And then I also consult, because teachers don’t make a lot of money, so it’s good to have that extra income, right? And consulting, I generally do project management. And that’s everything from managing software projects, which I’m doing primarily now, to implementations. I’ve done, as you know, you’ve helped me out on some data center implementations, little data center implementations. And also, if a company has an enterprise application that needed help implementing, people think that I go to Best Buy, buy software, install it, and then we’re done. That’s not how it works, right? [Laughter] There’s a lot that goes on to make the implementation successful. So we do the soup to nuts entire life cycle of the implementation. And really odd things, like every now and then I get a call saying, hey, I need to make a website, and I’ll help out manage it, or I’ll do myself, if it’s really simple. That’s because I’m interested in projects. So whatever becomes interesting, and it sounds great, and I like the person I’m working with, that’s what I’ll do. I also have a couple of companies I’m a part of, I’m a part owner of. One of them is a car dealer wholesaler. And we’re looking to, you know, technology is like evolving so rapidly now. For those people who are leveraging the newest stuff, AI, APIs, they have an advantage over those, especially legacy industries, like car sales, pretty old school. So I’m working on a project where we’re trying to leverage APIs and AI to understand the true value of a car and what it’ll take to get it to a certain level. So working on that project, and I’m also doing house flipping in Indiana with my brother, part of that, which that one’s not really interesting too much, technology too that we’re trying to, but it’s been pretty messy. So, and then I’ve decided hobby stuff that I do every now and then, like refurbish electronics from Amazon Returns at the eBay store. I still do, but I’ve kind of slowed down on that. And everything I do kind of use it as a mechanism to teach students if they’re interested. So I generally will bring a student on to help out and they get the experience and I get the energy from them, the excitement of doing something new. It’s kind of a win-win.

Manuel: It’s very interesting, like how you’re using all these different avenues. And similar to you, right? I see a lot of these businesses and when they’re not leveraging technology, I had another guest on where we’ve talked about it, like where she was working at a hospital, like she got out of tech, started working in the hospital, but she saw a lot of inefficiencies like where technology, process, procedure, like things that were used to, and especially you, you know, with project management, like, hey, here’s steps that we follow, just building a lot of efficiency and you being able to go through. And like you said, the auto industry, like, you know, most people wouldn’t think that that’s somewhere where AI and, you know, APIs would leverage, but the way that you’re doing it, it sounds like you’re trying to kind of, when you say what it would take to get there. So are you kind of understanding, hey, based on mileage, condition, what is it at now? And kind of to bring the value up for the resell, like 10 grand, hey, what are the items that would be needed based on, I’m assuming you’re using AI to just kind of do research for you, right?

Jay: Yeah, so, you know, information gathering and making decisions takes time, right? And also, you know, just to walk through it, you go to the auction, right? You see the car and you need to know the value of the car when you’re bidding on it, because you want to take the car, this is triage, right? I’m sorry, arbitrage, this is arbitrage, which I, you know, I’ve done that for a while. You take something, you add some value to it and sell it for more. And the more value you add to it, obviously the more margin you make. But in order to do that, you need to know the potential of whatever you’re getting, whether it be electronics, car, anything really. And that’s kind of hard to do if you don’t have experience in the domain. And, but the information is out there. And also, an auction is kind of a fast-paced environment. So you need to make quick decisions and very time consuming. And I have a very good friend of mine who kind of showed me the ropes, helped him open up his dealership here in 2007. And it’s a lot of work. You get there early at the auction, you have to like do a bunch of stuff. But all that’s been done forever and there’s data out there that will suggest that. So what if we could do that programmatically? Not only with one auction, like across the country. And then I can make quick decisions. Even if I’m not right 100% of the time. I save all that time and having to go to the auction and so on and so forth. And if you do that, you have a lot more success, I think, than if you do everything in the kind of old school manual way. So the companies now are realizing that, hey, if I want to have a platform, like an online auction platform, and I want to make it attractive to everyone, then I need to be able to share my data somehow. So everyone has API somewhere on the roadmap. And the larger ones already have them out. And that gives a whole new ballgame. So all the dealers who are still going there doing handshake with the auction person, they slip them a 100 to help them out, have someone there scouting which cars or themselves which cars are valuable or not. That’s all going to waste your energy if you can do everything programmatically.

Manuel: I’m going to go back a little bit now And just if you can kind of tell me kind of where you kind of grew up and what eventually got you interested into technology and kind of what started you down your career path.

Jay: Yeah, so I grew up back east. I’m from the Maryland, Virginia area, DC area. And from day one, I’ve always loved video games, right? Still do. I mean, I can’t play them as much, but I always love video games. And true gamers who I consumed as many games as I could, from as many platforms or consoles as I could. It was a game I was interested in it, right? Everything from like text-based RPGs in DOS or Prodigy, whatever, all the way up to, you know, the AAA Call of Duty type games. I’m interested in playing it, you know? So, you know, to understand how to play games again, I’m working. You got to understand technology, especially the high -end computer games. So, an example of this would be Warcraft II. Warcraft II was one of the first games that I played that you could play multiplayer across computers. So, I have six brothers and sisters, and we’re all gamers for the most part. Except for one. I don’t know where she’s not a gamer, but everyone else is. And we want to play each other in Warcraft II, so we had to figure out how to network them. And no one taught me. I had to figure it out. So, we, you know, went to the library. This is like ’93. So, before the internet came out, we had to go to the library, get all the equipment, try a bunch of stuff. IP addresses. Okay, this is a static IP. I need a static IP. Okay, I need a crossover cable, because this cable doesn’t work. And, you know, we grind it out, and eventually we figured it out, and boom. Now we’re playing multiplayer Warcraft II, which is like heaven, you know? So, that got me in technology just because I wanted to play video games, really. And, you know, I like technology. I think it’s cool the way technology works. And then, from a career path, I really didn’t know what I wanted to do from a career path. And we can get into that. That’s like a whole other side conversation. Do you want to get into that now, or do you want to talk about something else?

Manuel: No, I mean, we can talk about it now.

Jay: So, in high school, I just wanted a job. I didn’t care where I worked. So, I worked at McDonald’s. You know, it’s fun. Anyone who’s had to work past food knows how much fun that is. But, where I worked at McDonald’s is one of the busiest ones. In Rockville, Maryland. Very busy area town. So, you get a lot of people coming through. And I was there two years, and, you know, I became like a valuable resource to the store. And I like people. I just do. I’ve always liked people. And there’s a lot of people you don’t like working fast food, but in general, I like people. And, across the street from McDonald’s was CompUSA, which was like Best Buy for computers. Back in the day, you probably remember it.

Manuel: I remember them.

Jay: So, I crossed the street with CompUSA, and one of their managers drove through the drive -thru, and he was like, hey, you always have a smile on your face. I know this job sucks. It’s like, how much do you make? And I told him I’d made $5.70 an hour. And I wasn’t like in a lead. So, I was like, you know, not making a ton of money. He was like, okay, come over to CompUSA. We need cashiers. I’ll pay you $6.50. And I was like, okay, like I decided to do that. And I was graduating high school at this point. So, I was 17. So, I went over to CompUSA, and now I have access to all this technology, because it’s a retailer, and they have discounts, and all this stuff happens. So, that really accelerated my interest in technology, because I get to play with all this stuff, which is so critical, because, you know, we work with students, right? And I asked the students the same question, like, how did you get in technology? And a lot of them say I was just exposed to it, because a lot of the kids are technical, and don’t know they are until they start playing with technology. And it’s expensive hobby they get into. And a lot of the kids don’t have those type of resources. I didn’t. And giving them a way to be exposed to it, so they know that this is kind of my jam, is really cool.

Manuel: A very important part there, right, is exposure. And I think just exposure to, not even just technology, but different things. So, you know, like my dad was not into technology. Like, he was, they did construction, right? So, he was a block layer. But one of the things that he exposed me to early was a lot of the machinery and equipment. Like, things would break, and we’d have to go and help and fix them. So, that mindset of, like, repairing things. And it eventually went into, like, not even just equipment, but even just vehicles. Like, oh, we’ve got to change the brake pads on this. Like, oh, okay, well, how do we do that? You know, showing you that entire process. Hey, how to bleed brakes. How to do all these different things to then, okay, we get home. We need to repair a light switch. So, it’s not technology. It’s electronics. It’s different things, but exposure. So, that when I did get exposed into technology and PCs, I didn’t have the fear of, oh my gosh, you know, like, I don’t know how to take this apart, right? Like, you start to develop, like, a thought process. That exposure, I’m like, oh, okay, well, there’s a screw here. Let me take a couple of these screws. What does this release? And so, when I got into being initially as a PC technician, like, I didn’t have that fear, like, that exposure. I wasn’t confident, but again, you know, not having the resources to buy a bunch of computers, but eventually, you know, like, just kind of doing that correlation of, like, oh, it’s an electronic. I’ve taken apart blenders and radios and different stuff like that.

Jay: You also make a good point, an important point, in my opinion, is, working with your dad, you got access to that knowledge, but also, it was kind of a safe place to learn, because I’m a big fan of mistakes. My wife calls me a professional failure, because you learn from mistakes. Knowledge is really error correction. And if you’re in a place where you can take things apart, and if you don’t put it back together perfectly, you’re not, like, fired, that’s a great place. So, you learn, like, if I tug on it this way, it doesn’t mean I’m breaking it and some things take harder tug, things like that, right? And with technology, you got to know how to break it and put it back together, but not cause damage to the company you’re working for. And, you know, school and working with relatives or whatever, is it, you know, preparing things, really, is a great place to pick up those skills, which is one of the reasons why I always like repairing things, because, you know, they’re already broken, so it’s so hard, you know, and just try to put it back together, right?

Manuel: Right. And almost sometimes, for me, like, to a detriment, right? Like, I see stuff, I’m like, oh, I can fix that. And my wife’s like, yeah, but just have somebody else do it. Like, you can’t repair all 20 or 25 things that you see, right? So, it’s just kind of an understanding to, like, that process. But like you said, you are going to fail a lot. But I think the more that you fail over time, you learn, and you either fail faster, right? Like, you’re able to make those decisions, like, I can tug, you can tell, like you said, like, hey, this, if I pull this a little bit harder, I need to, because this is how it’s going to come off, or if I pull this harder, I’m going to break it. So, you start to kind of build that knowledge base of, like, hey, this is what I should do, and this is kind of how I move forward. So, as you’re exposing students to this, and are you kind of doing the same thing, exposing the technology, and as you’re asking them, like, what are some of, you know, there is a barrier to entry. So, what are they, how are you helping them kind of move past that?

Jay: Well, you know, it’s tough in a formal learning environment, because, you know, you have a structure, and students are kind of been indoctrinated to this style of learning, which is like, you follow instructions, and I’ll give you an A, that I give you. So, my classroom’s a little different, where I put out questions that really don’t have an answer, because I’m hoping that we’ll get the wrong answer, and then we’ll fail to the right answer type thing, and that drives some students nuts. So, you got to really set your classroom up early in a culture that, you know, failure is appreciated, and we’re kind of expecting it. And still, it’s like pulling teeth sometimes with some students. Some students come to me and say, like, don’t call on me, you know, because, you know, I call hoping for the wrong answer. And so, I ask really vague questions, and some students, like, really cause anxiety. I was like, in technology, you got to get over that, because you’re not going to have all the answers. And knowing that, but things change so rapidly, if you have all the answers now, you’re not going to have it next month. So, you got to be okay with having to fumble through getting to the right answer, right?

Manuel: Yeah.

Jay: As a project manager, you kind of have to know a lot about everything, really? So, I really just know, like, I’m in a project, I know who can do what, what I can do, and if there’s a gap, I got to find a resource like you to fill it in. And, you know, the way I’ve known that is by trying, like, oh, this is way more complicated, or, oh, okay, this is easy. Even still, every now and then you get, you know, kind of heart attack moments, because you don’t have the experience. And which is why you got to set things up where you can revert back to a state no matter what, right?

Manuel: And learning to troubleshoot. So, you know, you mentioned that going through the library and kind of playing around with that, having exposure, you know, at CompUSA. So, is did you know that it was troubleshooting and understanding it? Because, like you said, I think a lot of times people are indoctrinated to a specific way of learning.

Jay: Yeah.

Manuel: And when it deviates, that critical thinking or that troubleshooting, a lot of times, I don’t, you know, because I also, you know, similar to you, right? I teach, and I see a lot of this. If I follow these steps, and it’s not working right away, it’s like, step five doesn’t work. Okay, well, why? Right? Like, try and figure it out and understand. So, is that something that you’ve, did you know that you were developing troubleshooting skills? Or is it just something that you were determined to get to, like, an end state? So, how did you kind of manage that?

Jay: If we’re talking, like, back when I was playing games as a kid, I had no formal framework of how I was approaching things. It’s trying to figure it out. We call it grinding, you know? And that element’s missing in today’s world. It really is. If I can’t get to the answer and it’s not linear, people give up. And I don’t know why, other than maybe it’s indoctrinated, they want the quick answer now, pass the least resistance. And, like, you’re missing, like, so much if you grind it out. So, I didn’t know it was formally, that’s what I was doing. But now, all I do, and I kind of look for that. And it’s always this period of rumbling, when you’re learning something new, and you’ve got to kind of expect it, you know, you’re going to climb a mountain, you can’t be like, okay, let’s climb a mountain, and then you start from the bottom and there at the top. There’s always the climb, the struggle that you have to do to figure it out. So, I was like, I actually look for the struggle. If it’s too easy, I feel like I missed something. You know, that makes sense.

Manuel: Yep, it definitely does. So, then now, as you’re working at CompUSA, you’re getting this exposure. What kind of? Sounded like you were graduating high school around that time? So, what was kind of the path forward from there?

Jay: Sure. So, I, like, had no plan. Both my parents didn’t go to college or graduate from college, I should say. So, I didn’t, they weren’t like, go to college or like, do whatever you want type thing. So, I had no path. My McDonald’s actually paid for my first semester of college right before I quit. So, they were super happy about that, because they expected me to hit their management track. So, I had money to go to the college. So, I was like, let me just sign up so I can get this money. So, I signed up for the community college there by the CompUSA, and I was a cashier. And that really framed my career, really. It’s interesting how that works. First of all, I always work hard. That’s been indoctrinated me, and like, I feel like I have to work hard. And I was a cashier, and this is probably one of the top three busiest stores. It was in Montgomery County, and anyone knows the county system in the United States. Montgomery is Maryland, Fairfax is Virginia, and they’re right next to each other, and those are the richest counties in the country. That’s right, the senators live and all that. So, CompUSA was one of the busiest in the country, the most revenue-generating, because everyone has money. So, as a cashier, you’re like working nonstop, because there’s always huge lines. This is before Amazon and the internet, so they could go somewhere to get stuff. This is also when warranties on products came out. So, it’s like, I buy a printer, I can buy extended warranty, three-year warranty or whatever. You know, Best Buy, you know, people ask that question, or someone asks now, it’s on the screen, do you want a warranty? Yes, no, what does that even mean? So, but they asked cashiers to ask that question, and I thought that was part of the job. I didn’t realize that that was something extra, so I did it. And so, someone had a printer walk by, say, hey, we have a three-year warranty, it costs 30 bucks, or something like that. Do you want it? Yes or no? That was my, yes or no, do you want the warranty? And I found out later, for everyone, I found out later that you got paid a commission if they said yes. And so, I was making $6.50 an hour, and I was making $18 an hour selling warranties. That’s when I realized, wow, you make way more in sales than you make in just like your regular job. So, it’s interesting, we had a group meeting, and they’re like, who’s this kid? That was me. And I raised my hand, the general manager came out, and he’s like, you’re like one of the top warranty cashiers in the country, like what are you doing? And I was like, I asked them if they own a warranty, that’s like literally all I’m doing, I’m not like pitching it or anything, to ask them, do you want a warranty?

Manuel: So, you weren’t even giving them an explanation of what was involved unless they asked, so you were just saying, do you want a warranty? Yes or no?

Jay: Pretty much.

Manuel: And that’s it.

Jay: Yeah, pretty much. And they asked, like what does that mean? I’m like, well, if you have a problem, for that particular one, you carry it here, or Warrantech was the company that we used, as like, this is before I knew, like, what the real story is with these warranties. So, again I was naive I was 17, they were like, yeah, you call this number and they help you. Okay. Most people said no, but some said yes. All right. So, $18 an hour is like three to six warranties an hour, depending on the type of warranty. And we’re so busy, I always had people in my line. So, I was like, me, back to the story, General Manager says, who’s his kid? It’s like me. And he was like, you’re like one type of people in the country. So, they had just started a small business sales part of CompUSA, kind of like a corporate part, where you’re selling small businesses, they already had a corporate, but they were trying to separate large companies with small business. So, they wanted to move me to that. So, when I was turning 18, so now I went from cashier to like corporate sales. And I kind of did a grand tour of the store before I got there. So, I went to the parts counter. So, I got to learn about memory and hard drives. Then I went to the back hardware sections, so I could sell computers and learn about computers. And then I ended up in corporate sales, which is wild because 18 year old and you know, as an 18 year old male, you’re still brain still forming. And I had the ability to do things like change margins. And on our company, on our store and other stores. So, like really a trusting role. So, now I’m like going from $6 an hour I’m making like $40 to $60 because it’s commission based, which is crazy. So, I had enough money to move out of my house as an 18 year old. Also, going to college is very tough because I’m like, why am I going to college and making all this money? So, I had to have money to pay for my car, pay for my own stuff. And a lot of that I spent buying cool electronics. I bought the Sony Mavica, I don’t remember that. It was a digital camera on the first ones that used a floppy disk. So, I didn’t have to do all this hoopla to download it. Just boom floppy disk and you got the image. It was like a grand. It’s like some crazy luxury. And this kid has it because he blows his paycheck on it type of thing. So, that kind of shaped my career. It’s like, okay, you make me make a lot of money in sales. And I’ve had the personality for it, which really was tenacity. Because you know, in sales, people think that they’re like, everyone’s a used car salesman. It’s like, no, there’s way different profiles. And with technology, especially, my personality works. We’re just in the facts, information, right? So, that’s kind of where my technology career started was corporate sales for CompUSA. And I failed out of my first semeser of college because I stopped going to class. I’m like, what’s the point of going to class?

Manuel: As you’re picking up this, you know, the sales acumen, right? Going through as a cashier did, and I guess a lot of it’s just naive, right? But was there anything when people would say no to you? Like, did you take offense to that? Or, you know, and especially as you’re moving now from that into a corporate sale. So, how did you deal with, a lot of people will call it rejection. I don’t think it’s rejection. They’re just rejecting that offer, right?

Jay: So, I’ve done a lot of sales. And that type of sales was didn’t burn at all. Because I’m like, giving information. Do you want to warrant it? Here’s what it does. Yes or no. And there wasn’t any pressure for any numbers. So, no one’s saying you have to do this. No one’s saying, oh, here’s how you do objection handling, none of that. It’s just like, whether you want to do it or not. And no one else was doing it, which blew my mind. Because like, just ask them if they want a warranty it and you get $3 an hour extra. That’s crazy. Or more. So, I didn’t feel the burn at all. And when I went to corporate sales, this is the late 90s. So, it’s like ’97. So, it’s like tech boom central. And everyone has a lot of money because the economy is screaming. So, it wasn’t really sales. It’s really order taking. It’s like, how do you take orders best? And I started to learn all the nuances of taking orders. Because, you know, there’s always a higher level than the level you’re on. So, for me, it was, remember, this is before the internet. So, people would call in. And you get access to the main line from that, from where I was. You know, you had a phone and you have the lines on the side. One of them is like your line. One of them is corporate sales. One of those is the main line. So, when I had downtime, people was kind of chitchat, smoke break, you know, hit on the cashier. I would start answering the main line. And if it was a, if it was a, someone from a business, if it was someone from like, have a question about, you know, something commercial or, or have a complaint or whatever, I would just transfer them out to someone else. And sometimes, you know, as an immature person, I’d transfer them somewhere crazy. This is for giggles. If I liked them, you know, it’s like, let me transfer them to like, Uzbekistan. But if they’re a company, I would answer their question because I, you know, I was pretty knowledgeable about the stuff because I made the rounds and was interested. And I’d say, hey, when you come in, I’m gonna have it ready for you. So, that way I got credit for the sale. So, my numbers were bonkers because I was stealing from their retail section of the store because I’m supposed to be selling to companies only. But that was, I was, because I was answering the main line. And I was like, hey, do you work for a company? And then when they came in, I had a cart ready for them with their deal and I had a slip that had my name on it. Boom. I found an angle that, that worked. But, you know, I didn’t have to do that because everyone’s buying. It’s really just like managing who’s buying what type of thing. So, I would even categorize that as sales, really. It was order taking. But I got a taste of how much money you could make.

Manuel: But even though, I mean, like you said, it was order taking. But again, you found that initiative. And I think it’s just that it sounds like you were very curious, right? So, it’s that curiosity of like, instead of, especially at that age, right? Like, you know, like under 20, you know, like you’re probably not even 20 yet, right? Or right around there, 18 to 20, to have that mindset of to go through and say, all right, hey, like you said, I can go do all everything else that other 18 year olds are doing and goof off. But you were like, hey, what can I do to kind of pull it, even though it was order taking, was it just to try and pull in additional?

Jay: Yeah. Stay busy.

Manuel: Okay.

Jay: And that’s one of the things that the gamer mentality I like, is like everything’s a game to me. Like, everything’s a game. So, this is a game. Like, how do I beat it, essentially, because you play a game like there’s always nuances to beat it. And back in the day, you probably remember this was Nintendo, like you played and if you died, you had to start over. So, you really had to map out what you’re going to do if you want to beat the game type thing. And you look for the nuances. Okay, if I go here, this happens type thing. So, everything is, I project everything like a game is fun. And I feel I find the levers and that was one of them, you know. And there’s always like the baseline game, but there’s also other stuff you can do and working glitches, you know.

Manuel: And now when you’re doing this, is it you’re doing something different? Did this similar to when you were a cashier? Did this help kind of put you towards the top as one of the top, you know, small business vendors?

Jay: Yeah, it was. And really, I thought I was lucky. I didn’t think I was the top. I thought, okay, I’m in one of the richest counties in the United States in the world, the United States. And I like lucked into this small business role. So, yes, I’m one of the top people in the country, but not because I’m great. It’s because I happen to be in the right circumstance, which, you know, that’s happened a lot in my career. And then eventually I realized, wait a minute, other people are in this and there aren’t near at the top. So maybe there’s something I’m doing right. But like for the first 10 years of selling, I was like, well, I got lucky that I’m in this role, because I’ve always done well in sales. I’ll tell you that transition into tech, because as you remember, you had a couple good years where things are booming, and then there was a crash, right? And you could see the crash coming. So I was at CompUSA until ’99. So I started in ’97 and ’99, and the tech was crashing. So CompUSA was a poorly run company, it was. So they got bought or someone took over and he’s like, I don’t like the small business idea. So they cut the department and lost all their talent, just like that. So I was out of a job all of a sudden. So I had a friend that worked at a other retailer, Micro Center, and I started working there. But I kind of saw the writing on the wall. And so I was getting tired. I was back in retail. I was in kind of like their parts area. And it paid really well, actually. And that’s why I got introduced to big commissions, because Micro Center was a really generous company. And they, a lot of companies, they dealers, I’m sorry, manufacturers like Xerox will pay extra money for like an end cap or to incentivize people to sell. A lot of times companies will take that for themselves. Micro Center would translate it to the translate would give it to the reps, the people on the floor. So one point, this is the one thing I’ll remember that is one point Xerox had a deal where if you sell one of their printers, you’re SPIF was crazy, like $50 per printer. And our department would pool it. So when I heard that, none of the other printers existed, like your only choice to buy is from Xerox. And we ended up selling a ton, like selling out all of our Xerox. So my commission check was $10,000 as a 19 year old. And I was like, crazy, couldn’t believe I got that. So I got a case of big commissions, and I immediately blew it all. Like terrible decision making. And I got introduced to taxes because I knew it was coming. By the time I guess I spent it in my head already. By the time I got it, my take home, I was like five grand, like cut in half because of my age and where I live. But I was like, man, this is great. But things were going sideways because of the economy. And retail, you know, it’s tough, you’re work long hours and deal with a lot of care need type people. So I was like, you know, understand technology, let me just figure out if I can move to that. And it seems like it’s more interesting. So I got my A+, Net+ and really just by getting, this is what internet was out now. So this is studying online. You recall brain dumps? Remember that?

Manuel: Yeah.

Jay: Brain dumps is great. So brain dumps gives you access to tests. So like when the first like MeasureUp type place. And I just spent like, every night, I would spend three to six hours taking tests. Really, not even understand the concepts. Net+ was tough. Like I didn’t understand what I was memorizing. Like UDP, what is this? But I know it does this because the question says it does. And I’m getting my A+ Net+ in like a month, both of them. And back then that meant something. So I took my A+ Net+ and that with, you know, contact who knew me into a $22 an hour job working for an MSP as a tech. And that was kind of my first like real tech job.

Manuel: And when you say that, you know, you kind of use that contact. So did you like apply for position? Did they just kind of call you in or kind of what was the process to kind of get that job apart from having that contact? But did you know, did they tell you, Hey, get your A+, Net+? Or like you said, you just knew that, Hey, having these is going to open up opportunities for me.

Jay: Well, I like talking to people, you know, and hearing their story in Micro Center and CompUSA had as a tech area, like Geek Squad type thing. And they’re all people who are starting their career in tech, like they wanna do tech. And I like always back then liked fixing broken stuff. So I see what they’re doing. And I one thing I missed out of this is, you know, being friends with them and also the way the retailers work back then, if someone returned an item or is broken, or they abandoned it from the tech shop, there’s a section of the store where they just put it for sale. And that’s a nuance I found. I was like, Oh, and they tell us to get rid of it. They don’t care how much margin they make or anything, because they’ve written it off already. So I would buy like a ton of the broken computers and then fix them and resell them. And I made a lot of money doing that, like a lot. And I knew how to aptitude forward is interesting talking to techs. I that’s where I learned, okay, we’re all trying to get our A+, we’re all trying to get our Net+. And some of them took them years, because they’re afraid to fail the test. Like I, when I decided to do it, I immediately took it and failed it. So I knew what was on it type thing, studied and then retook it, which is still the way I approach test taking really. And so I was like, Okay, well, that’s what that’s what made me decide I need to get my A+, Net+. And then, you know, because I talked to everyone, I kind of put it out there that I was looking for a tech job. And a friend of my dad’s is the one that pulled me in, says, Okay, I’m looking for an apprentice to help who was looking to start their tech their tech career, who’s willing to work hard, and I had reputation of someone who worked hard. So that’s how I got that first position, really.

Manuel: And I want to kind of go back and dig a little bit deeper onto that your test taking process, because similar to you. And I’ve run into other people where they’re just, there’s that anxiety of test taking, I get it, nobody really likes to take a test. But to me, there’s no like if I decide I’m going to take a test, do you go through and actually schedule the exam? Do you study first? People are different. I know that early on in my career, I’m like, Okay, well I’m going to study for this exam. And I would study almost forever, just because I’m studying, but I’m just like, Okay, I don’t want to, you know, it’s not that I don’t want to fail, but I’m just like, Okay, I want to be prepared. I noticed that if I just actually scheduled the exam and put in a dead end date, right? Like, Okay, I’m going to take it in two months. I’m a lot more disciplined at studying. And then similar to you, if I go and I fail, I have a better understanding. So the next time maybe I’m not taking two months, maybe I schedule it a month out two weeks, three weeks, like something shorter, and just that repetitive process. And now I’ve gotten to the point similar to you. I know if I say, Hey, I’m going to take this exam, I’ll book it no more than about a month, month and a half out. And I’ll just kind of knock it out. And I’m not, I don’t have that anxiety of, Oh my God, am I going to pass? I’m not going to pass. Like, and I know some people have that. Obviously, it sounds like you didn’t. Was there a thought process behind that? Or is it just like everything else? It sounds like you’re just, you’re pretty open to just trying things like, Okay, I’m going to go try it. And if it doesn’t work out, I’ll do it again. And I’ll do it again.

Jay: So there’s a little bit leading to that. And to answer your question is, I’m the same as you. If nowadays, I don’t have to take as many exams. But if I don’t schedule it, it’s hard to take it seriously. You know, so I find myself having to schedule it, if I’m going to take it seriously, and tell people. So I just ran the same thing for anything that’s tough. So I just ran this last biggest marathon piece, I’ve run marathons, I don’t schedule it and tell everyone I’m going to run it, then I’ll just like back out, because there’s a lot of training involved in that. So that makes things easier. But back then I just, if I decide I’m going to do it my brain, it’s like a have to do it, you know, type thing, or it’ll start eating at me. So back then I just decided I was going to do it and did it type thing. But so back then it was my process. I had to take it first, because there wasn’t a lot of information out there on the internet. Nowadays, it’s, there’s so much information MeasureUp all these other tools, Udemy. And what I found is if you can get 80% or higher on those tools, you’re probably going to pass the test. So that’s how I know when I’m ready is when I get around 80% on those types of things. And it’s usually pretty right. So that’s my process. Now it’s like, okay, I got to take this, like I got to take some this this fall for the college I’m teaching at. And so I’m going to schedule them during the break. I’m going to do the test things until I hit 80. And it’s a lot of refresher now. So it’s real, it’s easy. It’s not like it’s, I’m learning it from scratch type thing. And then when I had 80, I’ll go take the test type thing. And you can take tests remotely now, which is great. I don’t have to go anywhere. So and usually there’s, you know, availability instantly. So I can take it like 24 hours. So it’s not like I have to plan. So I can just wait till I’m ready and then schedule it. However, if some tests are dragging, then I’ll schedule it and know it’s coming and tell people when I’m taking this. And now the pressure’s on, right?

Manuel: So it goes back to like, like that gaming system, right? So you’re telling people to kind of go through a game and say, okay, hey, is it competitive or is it just to keep you accountable?

Jay: Accountable, not competitive. Although competitive is fun, but you know, you’re going to have a hard time finding opponents. I had one student who just loved taking certifications. And he’s the person that I would try to compete against. And this student was awesome. He, while he was in community college CSN, he got a CCIE, which I had never heard of that before, the CCIE. There’s only like 70,000 globally of that. And before he graduated community college, he went ahead and got his, that’s a maniac. So he was like getting a cert a month, like, which are am I getting this month type thing? And for him, I would compete. Just to keep, you know, feed off each other’s energy type thing. But generally speaking, people aren’t like lining up to get certifications, right? Especially at our age.

Manuel: It’s true because I’ve, I tried that recently, you know, like trying to do some of the AWS certs and, you know, people at first might, you know, get competitive, but like you said, at our age, and it’s more of the experience and everything else that where it’s not as much of a priority. So I find it harder to compete, but that drives me because just telling people, like that accountability doesn’t work for me. Sometimes I’ve noticed that if I almost the exact opposite happens, if I talk about it, and I’ve read that there’s that, there’s something in your brain, right? Where if you think about it, or if you say it a lot of times you get that, like that dopamine hit of like, oh, it’s almost like accomplishing the same thing, right? Like if I say, I’m, oh, I’m going to go buy this thing. If you think about it for a day or two, you get the same hit as if you were to buy it. And I’ve noticed that if I go and tell somebody, like, oh, I’m going to go take this exam, I go take this exam, I won’t do it. Just because I’ve said it, I’m like, I already told people and if I don’t do it, like, I don’t care what they think one way or the other. So instead, I actually have to not tell people and just go and take it.

Jay: Okay. I’m the opposite. So if I tell someone and I do it, then I feel, I feel like they think, oh, this guy’s a liar. You know, he just says things doesn’t do them. So that’s the pressure for me. It’s like, I made the commitment.

Manuel: So now they pull you in. So, you know, you get into this role and working for an MSP. So what is, what are some of the job functions is stuff related to like A+ and Net+? So you’re just doing basic installation networking.

Jay: That’s a great experience. And the people I work with are cool. And you see a lot of interesting people out there. And people who you wouldn’t think are techie, he actually are. So it was building PCs. So back then you built your own PCs. As MSP had a lot of government contracts, which most of them do in that area. So government buys a bunch of PCs. They don’t necessarily want to buy Dell, they’ll buy regular custom ones. So we built those. And I got really good where I could build a PC. Like just, we had an area with all the parts lined up in bins. And then I was put it together. And it took me like half an hour to build a PC from scratch, which was pretty good. I thought at least. And then a lot of what was going on back then was conversion from BNC to coax to RJ45. So I pulled cable. And, you know, they wanted young people to pull cable because it sucks, you know. Summertime, it’s 100 degree heat. There’s like abestos in the roof. We’re at an old school. You got to pull out the old cable and pull the new one. And you got to find someone who’s nimble to go up there and do it. So I pulled cable and punched it down. So that’s kind of the most of the things I was doing with that type of stuff.

Manuel: And then you took that experience and then eventually kind of did what with that. So now ou’ve got sales experience, you’ve got a little bit of technical experience.

Jay: So I got used to sales, which is a really comfortable job, you know, and bigger commission. So I was making $22 an hour as a tech, which is not bad, but I was making more in sales and doing way less work. So I was like, you know what? And I had failed out of college twice at this point. And a lot of my friends weren’t doing cool stuff. And my grandma was moving from Hawaii to Las Vegas. And she’s like, Hey, why don’t you come out here and finish college out here, like get rid of distractions and come out to Vegas. And I was like, you know, it’s interesting. Actually, let me go ahead and do that. So my brother and I moved out of Maryland to Las Vegas, help them move all their stuff from Hawaii into a house here and live with them. And then went to UNLV and CSN. And got my degree in MIS and thinking that I was going to continue on my tech career. And I immediately got a job making like $11 an hour on campus because I have my A+, Net+ which is great. I mean, it’s crazy. $11 an hour is kind of what students make nowadays, like 20 plus years later. So it’s like, how is anyone surviving nowadays? It’s like, mind blowing me. But now it’s out of the student worker. And at night, I would wait tables. I worked at Applebee’s or I ended up selling cars because that made way more money for CarMax. So I worked during the day and then at night I’d sell. And when I graduated, finally, I had a couple opportunities to be a tech. And I just hated it because I got exposed to what tech’s actually do, especially for larger companies like university. And there’s so much downtime made me nuts. I remember when my first week there, and you get your work orders, right? So like plan my day out, get my work orders, knock them all out in two hours. And then the person running the area called me said, Hey, let me talk to you. I was like, Okay, it’s like, he’s gonna give me work orders or give me kudos or whatever. He said, Hey, listen, you got to make those last all day, because I don’t have enough work for everyone. So you got to make those I want to have you just idle. So you got to make those last all day. I was like, What? Like, this is not what I’m used to, you know, in retail, you got to work, you know, and when you’re working like for MSP, you work your butt off. So I was bored most of the time. And, you know, I’m bored because problems start trolling people, you know, so I found all the best ways to troll your coworkers. You know, like, back then it was to get a screenshot of their desktop, and then change the background to match the screenshot. So none of the icon’s work. That was fun one.

Manuel: Changing their background just to something different. I remember doing that. And then still the same thing. So we would change their background. And then, you know, something else, like, you know, like, Care Bears, Hello Kitty, just something, something different. And then do that same screenshot. And they couldn’t click it. They were trying to change their, change it back to whatever it was. And they’re, you know, it’s it there.

Jay: Put tape over the mouse. So the mouse doesn’t work. Change the DNS, the local DNS file. So go somewhere crazy, like Google.com will go somewhere crazy, because it looks locally first.

Manuel: Obviously, that slow pace. And I wonder if just the exposure of like the university, right, because I do know that sometimes, and while it’s not, it’s public sector, right. So a lot of times that public sector is a lot slower for that. And you didn’t, I know you didn’t like being idle, but you didn’t use that time, sound like everywhere else to kind of figure out what else I can do to either grow my knowledge, my experience, my,

Jay: This is my early 20s. And I wasn’t super responsible at that point. And it’s, it’s weird. It’s like, you go to college and you have expectations. So when I was learning technology and being exposed to it, I just wanted to get as much knowledge as I can. Everything was cool. Everything stopped being as cool. When I was in college, I was kind of expecting, okay, I’m going to college and I’m going to have, you know, a comfortable job because they’re going to see I have a degree, which is not true as you know. And like, I’ve always worked somewhere where I was exposed to a lot of people, even the MSP, I was always constantly meeting people and having conversations when you’re a tech, you know, you’re in your office. And I went from being building PCs to, you know, helping troubleshoot professor problems to the NOC and the NOC was awful. Because I just watch blips all day, or maybe go and like recable something. So I was like, it sucks. So I was bored in that respect to it wasn’t having any interaction. And then when I graduated, the type of jobs I was getting, you know, I was going to apply for like 40 grand in the 40 grand to 45 grand range. And I was like, man, I made this when I was like 18. I was like, I don’t want to, you know, what’s up? So I, you know, this is the economy wasn’t great here. This was like early 2000s, 9 11 happened. So it wasn’t a lot of job prospects. So I applied around, got a couple jobs, got a job at MSP, to start off at sales. And it was terrible. So I ended up being there for a very short period of time quitting. I actually went back to CompUSA for a period of time left, because they were mess companies, small business sales. And it’s funny, like you’re with the internet, whatever you did follows you now. So you gotta be really careful. So when CompUSA, I saw they had an opening and for small business sales, and all I had to do was apply because my sales numbers were already saved. So he’s pulled up my sales numbers and hired me on the spot. Because they saw that this in my numbers was were huge. Now, that didn’t translate to Las Vegas. And they were completely disorganized here. And I couldn’t be successful. I recognize that right away. I applied to Xerox. They have an agency here where they have an agency where they kind of have a proving ground before you go to corporate because sales is like high turnover. So I kind of got lucky where I got an interview with no real sales experience because they had this test you would take that was like two hour long test is a personality profile test. If you hit these certain metrics, you got an interview automatically type thing. And this is like the new sales manager. And that was his philosophy, like interview everyone constantly and interviewed and we hit it off and I started selling Xerox products, which is primarily at that point was copier multifunction devices, which was techie enough to be interesting. Because, you know, copiers haven’t changed much in 20 years, but they’re on the network. So I have to understand how to do that piece and they can send information over the network. So it was interesting. So plus Xerox was a big company. So I got exposed to being so even those agencies, Xerox still funded the agency and they spent $30,000 and 90 days training you when you started. So I had to go through formal training process. It was great. So that’s how I started as like a tech sales is where it’s at. So I started back then it was, you get a salary with small commissions or you go on full commission and you get a big commissions. And in my mind, it’s like, if you’re in sales, why would you care about salary? It’s like, because if you aren’t performing, you’re gone. So everyone should be full commission. I didn’t have any kids at the time. So and I made an average 10 grand minimum per month, day one, month one. It was crazy. So I made a ton of money and make Presidents Club all that, working for Xerox and it was rough. And I that’s where sales started.

Manuel: Okay.

Jay: It wasn’t before that was where sales started because it was outside sales. I had to generate my own leads and things. I had to go door to door and I was like awful because I’m kind of introvert, nerdy tech guy. And that’s where you get rejection and to understand how to navigate through that and have the motivation to go out and do that every day type thing. And it was tough, like the first six months, even though I had success, I feel like I got lucky because this is like ’03 time. So we’re getting through 9 -11 and then we’re in Vegas. So Vegas’ housing is starting to ramp up. So the economy starting to boom here all of a sudden. So there’s a lot of movement. So there were sales to be had. It wasn’t like I was trying to squeeze water out of a rock, but I still had to go out and get it. Nothing was given to me.

Manuel: You said that you were kind of an introvert, getting more techy. But prior to that, it sounded like you were also, I mean, maybe not an extrovert, but you were uncomfortable talking to people. So as you’re going through this, is it, is it the fact that you’re going to have to go and generate the leads or kind of what made it awful in the rejection? Just, I mean, I know you, your personality, like maybe you’re not the person that’s like the center of attention, but again, you’re comfortable talking to people, right?

Jay: Yeah, absolutely.

Manuel: So I’m just curious where that kind of, where you felt that you were an introvert and that it didn’t really work out.

Jay: My definition of introvert isn’t like I’m shy, because I’ve never been shy, but it’s been like, I get energy, I recharge alone, essentially, and I’d rather be alone to recharge. So if I’m in a crowd, I’m not going to draw attention to myself and be the life of the party. But if I have to, I’ll talk to anyone, you know, and sales is weird because like, you started to see people as an opportunity to make money versus like someone as a person. So I was like, okay, I’m meeting Manny. I wonder how I can get him to buy this type thing versus, and that like never sat well with me. And that, that was like the turning point was when I was able to mentally understand where I fit in, because they train you like objection handling, solution selling, how to push them to a decision, all this stuff, all salesy stuff, right? And you try that and I was like, awful at that is awful. Like I’d go in and like have the process of my mind have come out wrong. I came in as disingenuous. But what I realized is that’s not true. That’s not sales really sales is a problem solving. And when I shifted where I’m making friends, I’m trying to make friends, make someone’s I know, I know it’s annoying to have to deal with salesperson. So I’m going to try to be respectful of their time and kind of do something funny to interest, make your day interesting type thing. And then see people as your friends versus as a prospect, and then try to give value first before I ask for anything, because you know, you’re making transactions, emotional transactions, making deposits and withdrawals. So I’m going to deposit first. And when I approached it was like, how can I solve this person’s problems? And if they don’t have problems, how about how I leave them alone and move on? And that is what made me successful was when I made that switch. Because then I walk in office and be like, okay, I’m going to solve this person’s problem. So my first big deal was a mortgage company, like they were just have all these problems because mortgage was paper. And I just knew how to solve his problems because I understood the machines. I was like, Hey, I walked in his office and I was like, Hey, I see a machine there. And then we’re just like, Yeah, it sucks, blah, blah, blah. I was like, What’s going on? This is going on. Have you thought about doing things this way? Oh, that sounds makes makes sense. Let me get the owner here. He says this guy says he knows how to do XYZ, which is really my claim to fame, because I wasn’t really salesy. I just knew how the machines worked like cold and all the software and features of them that normal reps, this is weird dichotomy, which is like, if you have something that’s different, not normal in the industry, then that makes sets you apart. So for me, I was technical. Everyone else was kind of salesy. So there were no tech people on our sales team. Tech people were like the implementers, project managers, installers, sales guys were sales guys, but I was like a hybrid of that. And because of that I could go in, I did my own installs, which is where I learned that I really like project management more than sales. That’s what I really liked. I like installing things. I can have a story around that if we have time, because that’s how I got into project management. But anyway, so I that’s what I liked. I was like, the mentality was how do I solve this person’s problems and be respectful of their time and make a friend. And I had a lot of success that way.

Manuel: That mind shift of going back to you being techie, right? And it’s how do I solve this problem? How do I fix this? How do I make this more efficient? Similar to what you’re doing for your own business, but now you’re doing it for somebody else. And they’re seeing that value of, oh, okay, you’re not trying to sell me a printer, you’re trying to sell me a solution. And I think I, in the time that I was a sales engineer, that is something that I noticed was what would kind of get me, again, not better sales, but better interactions with those customers. Because as soon as you start going like, Hey, I want to sell you this thing. Well, what if I don’t need that thing? What if that thing doesn’t? Sure, it’s cool. It does all these cool things, but I don’t need that. It doesn’t solve a problem for me. So finding what that problem is. I understand now why are that really made you successful. So then what, from that point, so now you’re obviously becoming a good salesperson, they’re seeing you as be the install, the installer, you’re doing everything, soup to nuts. You mentioned that that got you into project management, but what part of that is it scheduling the install? Like, I’m trying to see the correlation here.

Jay: Yeah, yeah, sure. So I can tell you, like that same deal. So the way it works is you sell the sales person sells it, and they pass it off to a specialist who does the site survey and all make sure the machine’s ready to go in. And then I’m supposed to be done with the transaction once the customer signs, and I’m on to the next eight, nine sales. So I got that big deal, sold them a bunch of machines, including a big one. And I assumed that specialist was doing the rest of the piece. So project management really is like, you know, a temporary endeavor to produce a result, right? And you got to put all the pieces together. And the big machine required 220 power. And they didn’t have that. So the people came in, took out the old machines, put the new one in, and it’s left. It says, Oh, there’s no power here, and it’s left, left it there. So the guy had no big machine to work off. And I call a specialist, like