From Cybersecurity to Vending Machines: How Justin Krakow Built On Point Amenities with AI

Hi everyone, welcome back to another episode of The Human Side of AI. And today I'm talking with one of our Club Jam members, Justin, who spent 15 years in cybersecurity, including a stint at Dell, before walking away to build something completely different: On Pointe Amenities, an AI-powered vending business he runs as a family with his wife and their 3 kids out of Castle Rock, Colorado. Justin's story is one a lot of you will recognize— that feeling of doing work that's technically fine but doesn't fulfill you anymore, and the leap it takes to find that next thing. We get into how he landed on vending machines specifically, how he's using AI to solve real problems in a notoriously outdated industry, from tax compliance to inventory tracking to margin analysis, and even how he's built AI into his own daily routine to manage focus and memory challenges from his time in the service. Wow. This is a conversation about reinvention, about building something with your family, and about what it actually looks like to use AI as a tool for clarity, not just efficiency. Let's get into it. Hello, Justin.

Hey, Flora, how are you doing?

Great. What are you up to today?

Just plugging along with my business operating system here, trying to get it dialed in and making sure everything cleans it up and I get clean numbers at the end of the day.

Yeah, that's important. Where are you calling from?

I am in Castle Rock, Colorado.

Oh, how long have you been in the area?

We moved here as a whole family in 2019. Awesome.

Where'd you move from?

We came from Cumming, Georgia. Oh, okay.

That's kind of a big change then.

A little bit.

Yep. And what were you doing professionally in Georgia?

Um, so from the service, we went from Germany to Virginia. I got my degree in cybersecurity. Um, and then got hired on for, uh, Dell and moved down to the Atlanta area and then through connections found our way out to Colorado. Wow.

Well, thank you again for your service. Um, were you Navy?

My wife and I were both Air Force.

Oh, wow.

Oh, cool. Very cool. Thank you both.

Um, okay. So, so you're in Colorado now. You, you got this cybersecurity degree, you were working for Dell. Talk us through kind of the next steps.

So, I was doing that for about 15 years and I guess the last 5 years of it, actually just moving into Colorado here, it just got kind of boring. It was always a game of attrition and security is a red line in a business, you know, never makes a business money, but it protects the business. So, There's always a little bit of a power struggle of how much money do you spend in security versus, you know, how much is it saving you? And at the end of the day, it feels like it was just a checkbox on, on the audit list. And if it was good enough to pass, then it was good enough altogether.

But interesting perspective. Yeah, I hadn't heard of that. That makes sense though. Yeah.

Okay.

So then, then, then talk us through kind of, so you're, you're just feeling kind of like a checkbox, even that, that doesn't, that doesn't doesn't feel good. So then talk us through kind of the next steps for you.

Um, so it was October of '24. Um, I just kind of had enough and the company needed to trim down and I was a candidate. So found myself on the way out and just kind of turned to what can I try to do to make a living that's got a little honor in it and provide something for the community and has a, I guess, a breath of being semi-passive, right? There's no true passive income, but, you know, how can I do more of a set it and forget it versus, you know, always on, 8 hours or more a day, has to be going. Where, where can I put my thoughts and my creativity into work to keep generating income but not have to be always at the control panel.

So then where did you land with that?

So we started On Pointe Amenities. So it's an AI vending machine, I guess, is the layman's terms of saying it. Yeah. But yeah, it's kind of— I try to say we're bringing Japan to Denver because Japan's vending market is just It's insane compared to what America knows and how it operates.

So how so?

There's any machine you could think of or any item you could think of has been put in a machine over in Japan. So there's a lot of—

I've seen like cupcakes and like makeup. And you're saying like in the States they have like Coca-Cola and Cheetos, right? Yeah.

Okay.

Okay.

And then, uh, some social media posts have shown, you know, there's vending machines out in the middle of, of nowhere, essentially, you know, and being in Denver, there's a lot of trails. So they'll have vending machines out in the middle of, of trails that, you know, carry everything from, you know, the standard water and some protein or some energy, and then all the way down to a pair of boxers kind of deal. So, wow.

Okay. So then how did you land on this niche? That's niche.

Um, just kind of doing a little research and, you know, what's out there, you know. Yeah, you could get into a car wash, but what does that cost you? You could do laundry mats, but what's that cost you? So what was kind of a low entry but medium to high upturn if you get the ball moving? So, um, just, I guess, did my online research with it and fell into a a community that is trying to, I guess, undo the franchise corporate thought process around America's vending machines or amenities in— what's the word I'm looking for— conveniences.

Wow. So, so you land in this, this, this, this space. Talk to us about how AI has been, you know, a part of this journey for you.

So through my research and I guess kind of putzing along through the interwebs, I came across the Jams community and I knew AI wasn't going to go away. I'd keep telling my family, it's, you know, what was the newspaper became the internet, you know, what was the radio became the CD. And so AI is just another flavor of it's not going to go away. So yeah. Why not jump into it and kind of just put your head down and learn what you can? So, and then with the vending industry, it is very archaic. The backends, you know, these machines are using AI to do telemetry on products. So able to see the product as the individual grabs it out of the machine and attribute that product and charge it accordingly versus having to push, you know, a button and hope that it doesn't get stuck in the machine. So you swipe your card or your phone or however your payment options are, and you have access to the entire machine. But even with that technology, there's a gap with knowing what is in your machine or having more of a real-time— the capabilities are there, but the language wasn't built yet.

So, so is OnPoint Amenities, is that the physical vending machines or is it a platform that vending machines use?

I guess neither. That's just the name of our company. Okay. I built just— I call it the OVM. So it's OnPoint Vending Management. Um, so I, I built my own flavor of trying to, um, go into the portals of the, the AI machines that I do have and seeing what I can grab from it. And what I can't, I gotta build on my own. But I wanted to go and find a better way than plugging through, um, spreadsheets and doing it kind of the old way. There, there's no reason for it if AI can help me do it and make it look pretty. It seems like it's worth the effort.

So, so then who is your ideal customer profile? We talk about ICPs a lot, right? So like, who is that? Who is your ICP?

It's property managers, gym owners, industrial parks, somebody that's 24/7, hospitals, schools, anybody that needs the convenience option that wants to kind of upgrade their look, feel, and the, the whole process. So my, my kids go to the, the local rec centers around here, and they have one of the franchises in their locations. And countless times they've come back and said, you know, that machine stole my dollar. And process of getting that money back is you got to reach out to that company and say, hey, it stole from me. And then now you're arguing with corporate Essentially. And it's just kind of a bummer and it's a drag, which gives the vending machine business kind of a sour report. You know, it's— yeah, why do I want to use it? I'd rather, you know, drive 10 minutes down the road to the gas station because one, it'll be cheaper and two, it's not going to steal from me. But well, so position ourselves to, I guess, alleviate that problem.

Yeah. So, so you go from the Air Force to, to university, to cybersecurity, to working Dell, to just kind of pulling all that out and then doing your own research on, hey, what is next for me? And you find this, this, this area of, of the vending machine world. Had you ever even considered this space before?

No, not at all. I mean, I've always kind of felt like there's probably an entrepreneurial bone in my body, but how to utilize it, I've never known. I've always kind of been on record of there's no actual job out there that just calls to me. If it becomes work, I will find a way to not enjoy it. So.

Well, I hope you're— do you enjoy what you do now?

I've told my family that it's controlled chaos that feels comfortable. Yeah, yeah. There's so many different things that, you know, one, I have no idea about business, so I'm learning about that while I'm trying to build this, trying to figure out how to, you know, not necessarily cut corners but round the corners so we maintain speed and efficiency. But I wasn't on the shortlist of, all right, if this fails, let's go do vending machines. But When you look at America and you say, you know, it's supposed to be this first world country and kind of at the peak of innovation and everything, it's kind of lagging behind when it comes to the convenience sector. Yeah.

So, so you listed your ICPs and thank you for that. I mean, to me it's like vast, right? So, so how are you getting in front of them and what is, what is your way to, to pitch to them, you know, to catch their attention?

And so typically it's going in, you know, talking to what we call a gatekeeper, you know, and try to tell them or give them enough information to say, hey, this is something you should consider. And what are you considering? You know, if you've already got a vending machine, why do you want to pivot to me? And the truth is, it's— we offer you an amenity. We don't offer you just a service.

Yeah.

So we run the whole thing. Everything is managed by the family. There's no corporate you're going to. We source everything. So we, we take care of all of it. And there's no, I guess, overhead on any business or any location that says, yes, we would like to have your amenity. But that's what we're We're pitching is it is an amenity and you can increase your, your retention. You can increase your customers and your clients or your employees' satisfaction with what you got to offer. And on top of that, we listen to the feedback of the location. So I put a QR code on every machine that has a form that you can fill out and tell me what you like, don't like, want changed, and Give me a little bit of insight of what you want and I can probably source it for you.

And you care, right? Well, okay, so you're, you're learning this whole new industry, you're learning how to run a business, and then you're also like, okay, I have to learn how to use AI too, right? So talk to us a little bit about how that journey has been.

Yeah, through the Club Jam there, it's been Made a world of a difference. I mean, I can sit here and, and plug away on my own, but having some of the industry leaders and the bright minds to kind of— I've always said it's better to stand on the shoulders of giants than to try to create your own platform. So learning from other people and getting more of a leg up on that has really helped me, I guess, dial in what's important, why it's important, and how to make it valuable and something that is actionable.

So what are some of the things that you are, you know, using AI for?

So yeah, I've been able to get into the both platforms and I actually now I got accurate par levels. So how much of the inventory levels are in each category or product. Being able to assess my margins a little bit better instead of relying on spreadsheets and kind of more doing it live. You know, if things aren't moving, it's a pretty easy click of a button now for me to say, hey, let's drop that down, you know, 5, 10% and change it so they can move. So I'm not losing inventory and coming to waste. I've used it to kind of dial in the tax complexities of this country.

Wow.

So the state has a backend API that I can call on and say, this is where my machine's at, and it'll tell me the rate and what it's charged at. And if it's just a flat fee or— because in the state, in most states, vending machines have an exemption. Oh. In, in Colorado, there's only certain items that have exemptions. So, and then based on where that machine's at, they could say we agree or disagree and further exempt or further don't exempt products. And this is what the charge is now.

Who knew? Okay. And otherwise it would have kind of been a guessing game if you didn't have AI at your fingertips here. And how do you make sure that it's not hallucinating and just like making up numbers for you?

Yeah, that's kind of the game you get to play with AI, right? When it starts to get a little wonky on you, I've been kind of spearheading the community there. You got to tell it, you got to tell it, hey, that's— I don't know where you're going. I don't know why you went there. And a lot of times it'll talk over your head. But if you tell it, you talked over my head and I don't understand, and then keep doing that until you do, it will learn how to stay in line with, I guess, your, your understanding of what you're doing.

So, so when Jam was really getting started with Jam AI, she used to say something that I come back to often, right? And she used to say, you know, I want people to use AI to allow themselves to have more time to be human.

Right.

And obviously I held on to that with this idea of the human side of AI. Right. So Kind of leaning into that, that thought, what are some things that you, you know, use AI for that has allowed more space in your life?

It's given me more clarity. So I've told it that I have some conditions from the service that make my memory retention not amazing at times. So there's a scheduled run I have every day that I'll fill out and say, hey, this is, you know, how much sleep I've got. This is my energy level. This is my temperament., and different toggles down the sheet of, you know, I need to focus on this. And I even have a section in there to say, am I overanalyzing this? Am I underthinking this? Or am I right on course? So I've adjusted my memory and the MD files to absorb all this and runs on a daily so that every, every time I touch the keyboard and we do any work, it'll aggregate what we've done and assess it based on my conditions. And then the next day, you know, if I got something that's still the hiccup, but I've— I'm— maybe it's something that's just beating at me and I need to get it done. But based on what I— my, my frog, if you will, the big fish, the big thing to take care of. Yeah, I'm— maybe I'm in the wrong space, so Being able to do that and know that I can keep myself kind of driving down the road without swerving all the time and flying off the handle because I'm, I'm anxious or—

How did you create that?

Honestly, it was just, hey, this is my conditions and this is what I'm working with and this is my business. You know, I've leveraged the JAMM community and built out my, my business template. You know, this is what I do. This is how I do it. This is my ICP. So. When it knows that stuff, plus knows that, you know, there's times where it's told me, hey, because you have TBI, traumatic brain injury, we should not add this complexity. Or because you think this way with your ADHD and this is how your brain works, we should do it this way because that'll help your brain understand why we're going from point A to point B.

Wow, that's incredible. So, so do you catch yourself being in this place of like, relying so much on AI? Where do you feel like— what would happen if it went out one day or you didn't have access to it? Like, where would that, you know, land you in your business and you personally?

Thankfully, I've gotten to a point now where if AI did crash, everything is kind of self-hosted for me. So as long as the power doesn't go out and I got a little bit of internet, We can keep it moving, but if the power goes out and the internet goes out, my business is already kind of folded because that's what it runs on.

So, but even just kind of the day-to-day, like, you know, I'll give you an example. You know, my, my, my daughter's going through chemo, right? And I try to get a picture of the lab reports before I meet with the doctor because I'm just so impatient, right? And I know that the doctor's about to review these labs with me, right, in about like 15 minutes, but those are really long 15 minutes. So I take a picture obviously, and I run it through my trained Claude and I'm like, okay, give me an assessment of her labs today. But there are times where I don't have strong internet at the hospital and I don't get those. And I truly feel like that I like, I go a little insane. I'm like, I need these, I need these. And that's just one example. But I mean, with this, With this, um, what kind of this emotional check-in, temperature check-in that you, you do with it, I mean, do you feel like you've gotten to a point where you like rely on that temperature check-in to kind of move throughout your day? I, and I asked that because I feel like I would quickly become so reliant on that.

Um, because it's available, absolutely. Um, if it's not, you know, I've I guess in a tongue-in-cheek way, I've lived with this long enough that I know how to do this in an analog style. Yeah, you know, it's, you know, journaling or, you know, self-reflection or, you know, doing a little bit of self-isolation so I can clear my head. But, um, I guess that's what the rest of the humans are for, you know. That's why I'm glad I got a circle to depend on too, that if things failed or I don't have my, you know, artificial human, if you will, to kind of assess me, then there's other people in my life that I know that I can, if I need to, you know, lean on and say, hey, you're, you're doing all right, or you're not doing all right, you know, maybe you should settle down on this or whatever.

So. So where do you see your business being in 6 months?

Uh, I hope we're, we're right at the cusp of being a break-even company.

Great.

So yeah, that's kind of a hard milestone to get to for any business. And we're coming up on 2 years of doing this as a family. So get to that milestone and, um, 6 months from now, I hope we're a little bit more in the positive and able to get to a point where we can do this organically.

Yeah, I love that. And you, you've, you've talked several times about doing this as a family. What does that look like for you guys to do it all together as a family?

Yeah, so I have— we have 3 kids, um, ranging from 17 to 10. So they'll get the, the list of what has been taken from the machine after I cross-check it, make sure that the AI was correct, and make sure the numbers are right. And sometimes they're not, even if I do check it. So then we got to pivot and maybe, maybe we don't fill it all the way that day. But they, they get pretty excited that, Dad, we got anything to do today? You know, is there any work today? Because oftentimes, you know, it's me sitting here trying to get everything kind of dialed in so that, you know, if I do have to go do something else for a time, I'm not worried about what the numbers look like. But Um, yeah, my, my youngest, she's, oh, I didn't get to go to the machine because I had to go to gymnastics. You know, I want to go to the game. So yeah, we got 2 more days and then we can go down there. So yeah, they put in a lot of work and they've been good at, uh, helping me make sure that the inventory is consolidated. So I also created a mobile app through AI to tie back into my, my website here to Hey, this is the inventory. So I've built in a scanner with, with my phone to capture the barcode and map it back the right way so that I can assess the expiration date. So we do first in, first out, you know, so I'm not sitting on stale product or putting something in that's got 6 months left on it, you know, that doesn't need to go yet kind of thing. So, but yeah, it's, it's all dialed in. They get a a spreadsheet, if you will, print it off, and they go in pen and paper. And okay, we got this one, we're out of that one, or we're only down to this many left. So yeah, they're, they're pretty excited and they fight over who's going to fill it. Um, that's if I bring all three. If I, if I only bring one, then they get to do the work and I get to make sure the numbers are right.

So So if someone's listening to this and they're like, the vending machine industry, like, this is interesting. How do they learn more about what you're doing?

I'm part of a community, like I said. So it's called Vendingpreneurs, and that platform is pretty robust too. They've been leveraging AI quite a bit on their side to clean up some of the archaic nature of of the industry. But yeah, that's without those guys too. And then that level of knowledge and insight of, you know, when I go and talk to a person, saying the word vending is kind of a curse word. You shouldn't say vending because the decision makers or the people that are kind of running the show or making the call, when they hear vending, their eyes kind of gloss over because out of a list of 10, we're number 15, you know, we're it's on the bottom of the list. I don't care, just as long as it's working. But that's where we come in. You know, if you got people complaining that, oh, the machine stole my money, or there's my, my bag of chips just sitting there in the window, but yeah, mine's an open cooler or an open closet if it's ambient, or an open freezer. And once you authorize payment, you could take the whole machine if you want to. It'll just charge you.

Well, very cool. No, this is, this is awesome. And I just, I love, I feel like the part of this conversation where you were like, I was just kind of looking for the next thing, I think is going to be so relevant to so many people. Like, I feel like people are going to hear that part and be able to take a, you know, a snapshot in their mind of where they have been in their life when they were kind of looking for their new thing, or even, you know, listen to this and be inspired to look for their new thing. So, um, well, awesome. I do hope, you know, obviously I know we're both in Club Jam, and, um, you know, luckily I get to see, see your face on some calls pretty regularly. But I'm really excited to really do that 6-month check-in with you and, um, you know, make sure you're, you're following, uh, your, the goals that you're working on. And I have no doubt you are.

Absolutely.

Yep. Well, cool. Thanks so much, Justin, for your time today.

Thanks, Laura. I appreciate it.

Take care. Bye-bye.

Bye.