Navigating the Evolution of Mobile and AI in the Business World with Denis O'Shea, CEO of Mobile Mentor

In this episode of The Wireless Way, host Chris Whitaker engages in an insightful conversation with Dennis Osha, founder and chairman of Mobile Mentor. The discussion delves into Dennis's journey from working with Nokia in the 1980s to establishing Mobile Mentor in 2004. Dennis shares how his company has become a global leader in modern endpoint management and security, earning multiple Microsoft Partner of the Year recognitions. The episode covers various stages of the company’s evolution, including its pivot during the global financial crisis, partnership with Microsoft, and focus on Intune. Dennis also offers an in-depth analysis of current challenges and future trends in endpoint management, cloud security, and AI integration, underscoring the importance of unlocking the full potential of Microsoft 365 for optimal business outcomes.

00:00 Introduction and Guest Introduction
01:33 Dennis Osha's Background and Mobile Mentor's Origins
03:05 Transition from Engineering to Business Focus
05:21 Challenges and Pivotal Moments
12:14 Evolution of Mobile Mentor and Partnership with Microsoft
16:57 Current Trends and Future Directions
20:54 Challenges in AI Implementation
21:08 Data Security and Initial Findings
21:33 Skillset and Training for AI Tools
21:45 Board's Inquiry and ROI Model
22:31 Types of Companies and AI Adoption
23:35 Future of Device Management and Security Tools
26:33 Proliferation of AI Tools
27:31 Ideal Customer Profile
33:20 Sales Cycle and Marketing Strategies
36:36 Final Thoughts and Reflections

More on Denis

More on Mobile Mentor

Transcript

chris_1_12-19-2025_131141: 0:00

Welcome to another episode of The Wireless Way. I'm your host, Chris Whitaker, and I am so grateful that you're checking out this episode and I'm equally grateful to, Dennis Osha, my guest today, and just a little bit about him. I met him recently. Great guy. He is the founder and chairman of, mobile Mentor. We're gonna unpack that. What does that mean? it's the global leader in modern endpoint management and security that helps organizations secure and empower their workforce across all types of devices. We're gonna talk a little about that. he started the company in New Zealand, many moons ago. And one of the things I thought was really interesting and did catch my eye was, you know. During this time at the helm, mobile metor has earned multiple Microsoft Partner of the Year recognitions, and that's no small feat. really excited to bring on Dennis. Thanks for making time for us today. how are you doing?

denis-o-shea_1_12-19-2025_121138: 0:52

Great, great. Thank you. I'm doing very well, and thank you for the opportunity to come on the podcast with you. I'm excited.

chris_1_12-19-2025_131141: 0:57

Oh, yes. I'm always excited, especially with new guest people that I've just met. I was sharing with you preshow. selfishly, I'm just excited to have, I mean, I know how busy you must be. you're running a big company, a growing company, and in an area that I'm very interested in. the fact that you're even willing to give me this time to talk about, what you do and how you do it. Yeah, I'm equally excited. So yeah, thanks so much. so we got this, brief kind of bio and, of course check the show notes, folks. As always, I'll have some information and links to, mobile mentor and how to get ahold of Dennis's team. what else can you tell us about your journey to getting to where you are today?

denis-o-shea_1_12-19-2025_121138: 1:34

Well, I'm looking at that phone on the shelf behind your head

chris_1_12-19-2025_131141: 1:39

Yes.

denis-o-shea_1_12-19-2025_121138: 1:39

and that's actually very close to where I started. Is that a Nokia or is that a Motorola?

chris_1_12-19-2025_131141: 1:44

It's an inflatable, probably a Nokia.

denis-o-shea_1_12-19-2025_121138: 1:46

I, okay. Okay. So my story Nokia. my story started in Helsinki back in the eighties working with Nokia, and my first mobile device was much bigger. Than the one you've got on the shelf there.

chris_1_12-19-2025_131141: 2:00

Are you kidding?

denis-o-shea_1_12-19-2025_121138: 2:00

about the same as a car battery.

chris_1_12-19-2025_131141: 2:02

Oh Lord.

denis-o-shea_1_12-19-2025_121138: 2:03

it was a colossal thing with cooling fans. you could walk around and you held it in one hand and you had a curly cable and you'd pick up the phone and you could do remote calls, which was an amazing thing in the late eighties, early nineties. so I've had a long history in mobile technology and wireless technology. spent 15 years at Nokia, working for them in different countries around the world. eventually I landed in New Zealand and I got an idea from my time with Nokia and I decided to leave them, they gave me their blessing. They actually gave me some startup capital and I set up this company mobile mentor 2004. I've been running that business now for 21 years. and now I live in Nashville, Tennessee, and I do a ton of work with Microsoft and some other partners here in the States. I'm delighted to be working with you and your organization and the TSD community, so it's been a hell of a journey.

chris_1_12-19-2025_131141: 2:51

I bet, I mean, you've really seen going from that suitcase, you know, mobile phone, to what we're doing today, what a journey. I mean, what a so many different evolutions of, the product. That's pretty fast. So were you, even as a child, were you interested in technology? I mean, what point in your development to a young man did you like? I love this technology stuff.

denis-o-shea_1_12-19-2025_121138: 3:15

I never loved technology, to be honest. I was interested in engineering and how things worked. So I went off and I got an engineering degree. I got two of them. I got a master's as well, and I ended up working in a lab doing research and development for Nokia and Finland and I got some patents and all that. And through that process I actually learned that I was not a great engineer. I was more of a people person, more of an extrovert. I found the best engineers in our environment were introverts and they were able to go deep and stay deep in something for a long, long time to solve a complex problem. I was much more interested in understanding what's the end user going to do with this product and who is the end user and what are the steps in between and how does this industry work? I decided to get out of being the engineer with the technology in the lab and get out into the world. So when Noia asked me to go to New Zealand to build the world's first cellular network. I said, sure. When's the flight? and I moved to New Zealand and then I went to different places and I ran Nokia, Switzerland for a few years and ended up back in New Zealand. I really followed the growth of the industry, but not so much as an engineer because I didn't think I was a good one, but rather as, somebody who could understand technology and then help customers unlock the full potential of that technology in a business sense.

chris_1_12-19-2025_131141: 4:32

that's fantastic. I can relate to that'cause I generally self-describe myself as a tech enthusiast, but.

denis-o-shea_1_12-19-2025_121138: 4:39

Hmm.

chris_1_12-19-2025_131141: 4:39

as I was listening to you talk, it's like, you know, I'm really more interested in the outcome. I mean, I'm more interested like, Hey, how is this gonna make my life easier and better?

denis-o-shea_1_12-19-2025_121138: 4:48

yeah,

chris_1_12-19-2025_131141: 4:48

years ago I was taught by a mentor about the idea of being efficient and effective.

denis-o-shea_1_12-19-2025_121138: 4:54

yeah,

chris_1_12-19-2025_131141: 4:54

can have one without the other. You really want both. And so I've always lived my life of, you know, is this efficient and is this effective? And how can we use technology to make business outcomes, more efficient and effective? And then when I talk to business leaders of all levels, I mean from SMB to enterprise, efficiency and effectiveness usually equals profitability.

denis-o-shea_1_12-19-2025_121138: 5:16

Yeah.

chris_1_12-19-2025_131141: 5:17

First statement.

denis-o-shea_1_12-19-2025_121138: 5:18

Yeah.

chris_1_12-19-2025_131141: 5:18

it's a good return.

denis-o-shea_1_12-19-2025_121138: 5:19

Yeah.

chris_1_12-19-2025_131141: 5:21

Yes,

denis-o-shea_1_12-19-2025_121138: 5:21

can I tell you a story that was quite pivotal in my development was,

chris_1_12-19-2025_131141: 5:24

please.

denis-o-shea_1_12-19-2025_121138: 5:25

I got my ass kicked, by a customer around 2003. I was in Switzerland. I had found myself in a senior leadership role, where I was heavily involved in sales, and we had just sold a 3G network to orange, a big, telco in Europe. That was a big deal, hundreds of millions of euros and we were trying to sell the next generation of technology. I was in a board meeting. With the CEO of orange and he basically, dressed me down said, why would we buy the next generation of your technology when our customers are not using all the stuff we bought from you over the last few years?

chris_1_12-19-2025_131141: 6:03

Hmm.

denis-o-shea_1_12-19-2025_121138: 6:04

And I didn't have an answer and I went. Back to my, you know, group in Helsinki and we tried to figure it out and we really struggled because what was happening in the industry was customers are going out and buying their first smartphone, spending roughly a thousand dollars on, on this device. And guess what they were doing? They were making phone calls and sending text messages. That was it. There was no mobile internet. there was no app store, there was no social media. getting music on your phone was a nightmare. Um, because there was only an app store really back

chris_1_12-19-2025_131141: 6:33

That's.

denis-o-shea_1_12-19-2025_121138: 6:34

getting email, working with a nightmares pre Blackberry days, you couldn't sync your calendar. so the smartphones were actually not that smart and the networks and the infrastructure was there, and these European carriers are spending, you know, billions on spectrum. And billions on cell sites and infrastructure, and billions on, on all the technology, and people are sending text messages and making phone calls. it was a very, very, um, intense, uh, situation for a while. And, and, you know, we didn't have an answer and I decided to leave Nokia and try and do something about it. the idea was to simply sit down with one business person at a time and help them configure their first smartphone. it working for one person at a time. Set up email, get calendar syncing, transfer their contacts from their old phone, get their music on it, change all their numbers with a plus format so they could go roaming. get all the basics so that you, Chris, if you had your first smartphone, would be able to make you super productive with it as a business person so you can spend a day outta the office, use this device, be productive, not have to go back to a desk. that was the vision. And so we set up Mobile Mentor to do that, and we ultimately did that. We sat down with a million people different countries around the world, Brazil, China, Australia, New Zealand, Japan, UK. We, I think we moved the needle a little bit. We got a lot of people, you know, right up to senior government level, government prime ministers and presidents and company leaders learning how to use, smartphone technology to the way it was intended to be used, and that then cascaded on through their organizations. So it was, and, you know, getting my ass kicked in a boardroom, was really, I guess the genesis of the, the idea to go and do this.

chris_1_12-19-2025_131141: 9:59

Yeah, that will humble you and, wise that you took that as a learning moment instead of, Woe is me moment. You know, what was I guy thinking? I mean, it was a great moment for you. Yeah. I love with even the name mobile mentor. I'm a little, I'm kind of sad. I didn't think of that, I was telling you earlier, you know, that's a double entendre, wireless meaning no attached and no judgment. The ways, the path, the journey, the adventure. But, you know, the origin of this very show was really about how to make. Wireless and mobility, and even internet of things to take the mystery out of it. You know, we're using these technologies every day. Even the least technical person of all of us, they know how to now use their smartphone. I mean, yeah,

denis-o-shea_1_12-19-2025_121138: 10:40

simple now.

chris_1_12-19-2025_131141: 10:41

you know, what percentage of people actually use their smart phones now for phone calls and text versus mostly internet apps like TikTok and social media and things like that.

denis-o-shea_1_12-19-2025_121138: 10:54

Yeah, I'm not sure.'cause we, we really don't do that work anymore. You know, that all changed very quickly around 2008 when the iPhone came out and when the carriers launched.

chris_1_12-19-2025_131141: 11:03

Mm-hmm.

denis-o-shea_1_12-19-2025_121138: 11:04

and wifi became ubiquitous. the need for that in initial service of helping someone set up their smartphone quickly evaporated

chris_1_12-19-2025_131141: 11:10

Yeah.

denis-o-shea_1_12-19-2025_121138: 11:11

the time of the global financial crisis. So we pivoted and we became a managed service provider for enterprises and government departments who had a lot of mobile devices, and they needed help to manage them, to secure them, to build out apps, to do asset management, cost management. So our business very quickly shifted from setting up a smartphone for one hour. To then, managing them 24 hours a day on a long-term basis so organizations could scale mobile workforce

chris_1_12-19-2025_131141: 11:41

You ahead.

denis-o-shea_1_12-19-2025_121138: 11:41

our focus has been mobile workers.

chris_1_12-19-2025_131141: 11:43

Yeah, you were one of the first ones to do it, I would imagine.'cause if you think about the evolution of mobile devices in the corporate workspace, it doesn't seem that long ago, I don't know, call it seven years, maybe, where the only people in the organization that got a phone was the executives. You had to be a VP or some, you know, director. or, yeah, sales if you're a revenue generator, possibly. But even my first sales job, I had a beeper, you know? My first sales job, when I graduated from a beeper to a Nokia. I remember being at lunch, my boss, I got my first Nokia and it was 1999. and I go to lunch and because, you didn't wanna miss a call, I took my Nokia set in the middle of the table, and I. Pull the antenna up because I wouldn't want everyone to know I'm somebody. I got a cell phone.

denis-o-shea_1_12-19-2025_121138: 12:31

now.

chris_1_12-19-2025_131141: 12:32

You don't have a cell phone. I got a cell phone and of course I didn't wanna miss that call.

denis-o-shea_1_12-19-2025_121138: 12:37

Yeah.

chris_1_12-19-2025_131141: 12:37

it was all, when my phone rang, it was always the money line. I just heard, Ching ching. You know, it was a great, a great time. But another funny story, as you're talking about, when Smart phones came on, I was talking to a friend of mine that worked at Blackberry and they were at an all hands meeting that year, and someone raised a hand when they were doing the Q and a with the CEO. He said, Hey, what are we gonna, how are we gonna respond to the app store? Apple has this app store, you know, what's our answer to that? He says, that's just a fad. People business people only wanna make phone calls and receive emails. We have that market cornered that's, don't worry about that. she said, you could hear a collective sigh across the room.'cause everyone knew, oh my gosh, we're in trouble. That's a problem. And of course, they were right. It was a problem for them, which is shame because you're right. Even, you know, during the heyday b Blackberry, man, they, they owned the market too.

denis-o-shea_1_12-19-2025_121138: 13:31

they did for about five minutes. And so it did PalmPilot for about five minutes.

chris_1_12-19-2025_131141: 13:35

That's correct.

denis-o-shea_1_12-19-2025_121138: 13:36

they

chris_1_12-19-2025_131141: 13:36

Yep.

denis-o-shea_1_12-19-2025_121138: 13:36

and Nokia owned it for a while and Blackberry owned it for a while. it's extraordinary to see how businesses have made fortunes and lost fortunes very rapidly, over the years in this industry. It's really, really interesting.

chris_1_12-19-2025_131141: 13:50

so you talked about how you started out with the goal of just being that mobile mentor, helping people set up phones. What did you see in the market or the industry that prompted you to, expand, more into, Modern endpoint management and cloud security.

denis-o-shea_1_12-19-2025_121138: 14:06

Well, first we contracted. Because the global financial crisis changed our business model and we hit to shift, we hit about 250 people at the start of the global financial crisis, and we had to do a rapid downsizing and retrenchment from, from our operations in China and Brazil in particular. So we retrenched, we pivoted, we became a managed service provider in the mobile space. From there, we started building, mobile apps. So we built a software development practice, which we actually spun out as a separate company. Later we got into mobile security. We partnered with AirWatch first. still super proud. One of my guys who chose them as a partner back around 2010 or 11, and they turned out to be the global leader in mobile device management and mobile security. So we worked with them for a long time and Citrix and Mobile arm and. And then we had a fascinating thing happen around 2015. We were doing really well, you know, able to basically go into any enterprise and help them figure out what's the right platform to manage all their mobile devices and secure them with either AirWatch, mobile Iron or Citrix. Microsoft came to us and they said, the first thing they said to me, first conversation I ever had with Microsoft was, you are really annoying us. They said, we're seeing you on all our accounts and we know you're just laughing at our product Intune, because it was a very immature product back around 2015. they said, you know, we would like mobile mentor to consider, becoming a Microsoft partner, helping us to take Intune to market, stop laughing at us, but actually work with us and help us take this immature product to market and help us win some market share, and become a partner. And I told my engineers about this conversation and they all said, no way. No way. It's a dog you don't wanna touch into. And it's totally immature. No, no. That would be a huge step backwards. And so I went and said yes to Microsoft because of the power of the partnership. Not, not the technology, but the power of the partnership.

chris_1_12-19-2025_131141: 15:58

right.

denis-o-shea_1_12-19-2025_121138: 15:59

'cause I had been given different advice from other people about when you form. A constructive partnership with Microsoft, totally change your business. So we decided to set ourselves a North Star, and we said, what if we aim to become the best in the world at designing and deploying Microsoft Intune? As a platform to manage all the devices because it won't just be smartphones, it'll be the tablets and it'll be windows, and ultimately it'll be MacBooks and virtual machines as well, and then servers. So we kind of had this vision. We thought, you know, let's be audacious here. What if we aim to try and become the best in the world at one narrow thing build a great partnership with Microsoft? we had also been schooled at the time with a very sobering number that Microsoft had 400,000 partners. None of them get any attention from Microsoft unless you find a way to stand out. So that really motivated us to figure out, how do we become the best in the world at one narrow thing so that they want to bring us into all their top accounts and position us and introduce us as their premium partner or their best partner for that one thing. So we spent 10 years working on that, and then we won Global Partner of the Year It kind of played out as we hope, you know, they have brought us into the largest accounts in the world. One of our accounts now has over a million devices on Intune. We've got some hugely complex interesting and diverse accounts where, we're now managing millions and millions devices, and Microsoft has turned out to be an amazing partner. I've been invited onto the advisory board for the Intune product line. engineers are part of Microsoft's elite engineering team, so they get insights into what's coming and they have a voice at the table, you know, to share customer concerns, customer frustrations. But also to, to help with prioritization of future products and features So that's been a remarkable journey from being a competitor to Microsoft and clearly annoying them so much that they came to us and said, Hey, let's be friends. to then winning their respect and now being able to work with them and, these amazing accounts around the world. It's, been one of the great highlights of my career actually.

chris_1_12-19-2025_131141: 18:04

I can only imagine to have one of the largest, biggest software companies in the world say you're annoying. I mean that.

denis-o-shea_1_12-19-2025_121138: 18:11

Hmm.

chris_1_12-19-2025_131141: 18:11

You had to feel pretty. Yeah. That was a pretty proud moment. I imagine they even knew who you were. Right? I mean, of all the companies you, when you annoy eight pound gorilla like that, I mean, you must be doing something right? Yeah.

denis-o-shea_1_12-19-2025_121138: 18:23

And remember we were in New Zealand, right? So we were in the second last Rock before you step off the edge of the planet. and for them to notice us at that distance was, was pretty cool.

chris_1_12-19-2025_131141: 18:33

Oh my gosh. So all of this, decades plus experience with working with enterprises and mobile devices. There's really two questions I wanna say. first of all, the problems you were solving 10, 15, 20 years ago. Are they still existing today? They're gone, right? So it's new problems. They've been solved, got new problems.

denis-o-shea_1_12-19-2025_121138: 18:54

new problems.

chris_1_12-19-2025_131141: 18:55

Yeah. give the listeners some idea, what's a common trend when your team, has a new engagement or even existing customer? are you seeing trends of, issues that companies are maybe not giving attention to? some people just accept things for the way they are because they don't know there's a better way. what are you guys seeing?

denis-o-shea_1_12-19-2025_121138: 19:14

Overseeing primarily is people not. Able to unlock the full potential of what they're spending with Microsoft. So Gartner predicted about 10 years ago that 95% of all organizations in the world will end up using Microsoft 3, 6, 5. Gartner was spot on with that. Absolutely spot on.'cause everyone, everyone has an account with Microsoft,

chris_1_12-19-2025_131141: 19:35

Yes.

denis-o-shea_1_12-19-2025_121138: 19:36

Apple, even Amazon, even Google, you know, everyone uses Microsoft products to a certain extent and most people end up using Microsoft 3 6 5 because it's the bundle. It's where the value lies and we do a ton of assessments and what we find is customers on average are only using 44% of what they've paid for. So the work we then end up doing is helping them do more with the licenses they've got. we'll often say Stop buying new stuff, if you're only using 44% of Microsoft, it probably means you're only using 44% of all the other overlapping things you might have as well. All the security tools and management tools and identity tools and AI tools. So the approach we tend to take is, you know, let's help you extract as much value as possible. From Microsoft as a strategic platform, starting with Microsoft 3, 6, 5, and very often starting with Intune because we know we can use that to manage all your devices and you can probably retire two or three other products. if you're using Jam for your Max, if you're using your watch for your mobiles, if you're using SCCM for your windows, let's collapse all those into in June. you're using Okta for identity or CrowdStrike for security or. Proofpoint or whatever we can, we can collapse all of those into Microsoft. So now you get a lot more value from one platform. But as we think about the future and AI in our businesses now, we give ourselves the opportunity to allow AI to reason over all that information.'cause it's all inside a single tenant. if we're using lots and lots of different products, AI can't possibly reach that data and reason over it. to answer your question, most of the work we do now is unlocking the full potential of Microsoft 3 6, 5. And now what's rapidly shifting is Microsoft co-pilot organizations wanting to get co-pilot and not knowing how to extract value from it in a way that they can report up to their board and give them data and say, here's the ROI we're getting based on the way we have deployed it. Here's how we're doing it securely, and here are the agents we're building and here's why it's a sustainable strategy.

chris_1_12-19-2025_131141: 21:45

are.

denis-o-shea_1_12-19-2025_121138: 21:45

gone from mobile devices to all devices to Microsoft 3, 6, 5, and now into the Microsoft copilot space.

chris_1_12-19-2025_131141: 21:51

So if I heard you right, are you now kind of the copilot mentor? I mean, you're, you're helping companies, optimize and leverage that. That's pretty fascinating. You know, I mean, because you're right that is app and you see it all the time. Just like every day there's an article about how people or companies are using AI incorrectly or not to this fullest extent.

denis-o-shea_1_12-19-2025_121138: 22:11

to the fullest extent. And, and also in a way just jumping into it, like we see this all the time. We did this, like, I'll admit we did this. So as a Microsoft partner, we dived into copilot. We gave it to a lot of people. And at one stage I had a come to Jesus moment with our leadership team because we realized we hadn't actually defined our use cases. We didn't know who we should have given it to. we hadn't really analyzed the way we worked to figure out which roles and which types of work would benefit most from ai. We hadn't done the groundwork. We hadn't done our data security work. So when we did the first scan, you won't believe this, but we're a small organization, right? Just under a hundred people. We hit 33,000 sensitive documents that were overshared overprivileged over permissioned 33,000 on the. And then we figured out that, you know, we could all use copilot in the browser. That that's easy. But trying to use it well inside Excel, our word, our PowerPoint, totally different. You need a different skillset set. You need to be able to write prompts in a different way. We didn't know how to do that. And when it came to developing AI agents to do, you know, autonomous work, we didn't know where to start. We really were clueless. Then, you know, when the board asked me, how's the, how's the AI initiative going? Are we getting a return on that? I couldn't answer the question. I didn't know whether I should turn it all off tomorrow and say, this is a waste of time. Or whether I should say yes, give it to everybody. It's amazing. I had no data, so we had to go and solve those five problems for ourselves to the use cases, secure the data, train ourselves on how to use this and learn how to do good prompts. Build some agents, get the plumbing in, place all the APIs and build those agents and then build an ROI model so we can actually see what's working and what's not, who we should pull licenses away from, and who we should assign licenses to. So we had to do all that spade work before we could then take it out and actually help customers do something similar for themselves.

chris_1_12-19-2025_131141: 24:07

Yeah. You know, I gotta believe, yeah, there's probably two types of company, one's that are deploying it, not really knowing how to measure our OI and how to do it the way you described. And then there's some that are like, you know what? we don't know this, we don't understand it. We're just not gonna do it. we're a blocking, no copilot, no ai. I've heard a couple other policies that don't put anything in chat GPT ever on your company. Work computer. You know, there's like, you know, the fear factor, you know, if you don't know, it's easier to just ignore it, it seems.

denis-o-shea_1_12-19-2025_121138: 24:35

Those companies will, We'll have to figure it out.

chris_1_12-19-2025_131141: 24:38

Left behind.

denis-o-shea_1_12-19-2025_121138: 24:38

It's not a, yeah, not doing AI is not a sustainable strategy. Just like not doing the internet would not have been a great strategy, 25 years ago Embracing mobile technology or wireless technology would not have been a great strategy. it's a matter of time and figuring these things out and right sizing it for your own business,

chris_1_12-19-2025_131141: 24:56

So it sounds like you have a knack, you know, for kind of, 20 years ago leaving Nokia, having this vision and, then, running into Microsoft of, how you could help, businesses going forward, from today what do you see for 2026 and beyond?

denis-o-shea_1_12-19-2025_121138: 25:12

A couple of things. I see. You know, where we started with thinking about device technology, mobile device management, mobile security products, I think that market's gonna disappear. I honestly think it's gonna collapse. Intune is going to be such a dominant product all the legacy products will almost become irrelevant. probably end up with a small. Set of use cases that, so OTI will still do well for supply chain inventory management, stuff like that. Air Watch will carve out a small niche jam full, hang around for a while, but I think Intune will just mop up the market. Microsoft will dominate the category in the same way. Microsoft dominates so many other categories.

chris_1_12-19-2025_131141: 25:53

Look at teams.

denis-o-shea_1_12-19-2025_121138: 25:53

is really, no,

chris_1_12-19-2025_131141: 25:54

Yeah, teams. Teams. I remember a time when teams first came on the market, like nobody was using it. It was glitchy.

denis-o-shea_1_12-19-2025_121138: 26:01

It was glitchy.

chris_1_12-19-2025_131141: 26:02

I mean, see more teams than anything it seems like,

denis-o-shea_1_12-19-2025_121138: 26:05

Oh yeah, and Teams probably isn't even the best example because they have a very strong competitor with Zoom and

chris_1_12-19-2025_131141: 26:10

right,

denis-o-shea_1_12-19-2025_121138: 26:11

is not included in the bundle in some markets, but Intune is included in the bundle in every market.

chris_1_12-19-2025_131141: 26:17

I hear that a lot.

denis-o-shea_1_12-19-2025_121138: 26:17

if you think it's free as opposed to paying Jam or AirWatch or Manage Engine or UL Alteris or whoever else, eventually the CFO is gonna say, why are we not using the free one everyone else is? And so that's the first thing. We think Intune will just eventually be the default product for all endpoint management, and the excitement will go out of that market because it'll essentially be a single product market, just like Windows is the dominant always across. Microsoft would just dominate that space. That's not interesting. but I think it's inevitable. What I think is super interesting is the proliferation of security tools that we've seen over the last 15 years. we know now mid-size organizations have an average 52 security tools. large organizations, really large enterprises have 70 to 80 security tools. And, I believe that's happened because we've been operating with a defensive mindset. We've been under attack from bad actors,

chris_1_12-19-2025_131141: 27:21

Right.

denis-o-shea_1_12-19-2025_121138: 27:22

to think about it. You know, if you were to find out how many drone launch systems do you think Ukraine has right now, or how many different missile defense systems have they got right now? I bet you they've got lots. They'll basically buy missile defense from anyone who turns up with a credible product that's willing to sell it to them. over the last 10 or 50 years we've been under attack. So we've been trying to protect ourselves and we've ended up with 52 different tools. Now what I'm seeing is a shift in CIO mindset and CSO mindset to say, instead of having 52 point solutions, let's think about. Consolidating down to a smaller number of strategic platforms that have more integration, more automation, more AI going on and, and so I think we're gonna see a big consolidation in security tooling over the next few years. But when we look out into the future, I think we're gonna have exactly the same scenario play out with ai. I'm predicting, and some people will hate me for this, but I'm predicting that large organizations will end up with 52 different AI tools. Not because of fear, because you know, we armed ourselves at 52 security tools'cause we were under attack. It was, it was one kind of fear. Now it's different kind of fear. It's fear of missing out, it's fomo,

chris_1_12-19-2025_131141: 28:36

Yeah.

denis-o-shea_1_12-19-2025_121138: 28:37

it's organizations and led from the CEO in many cases saying we need to get AI in our business. We need to learn how to work better, faster, cheaper, smarter, et cetera. Uh,'cause our competitors are doing it. And because there's opportunities. I believe organizations will end up with a huge number of AI tools across their business. It'll become a very complex fabric we get to a point where we can even think about trying to consolidate on a smaller number of strategic platforms.

chris_1_12-19-2025_131141: 29:08

What's an ideal customer look like for you?

denis-o-shea_1_12-19-2025_121138: 29:14

there are Microsoft shop. We would be useless if they're an AWS shop or a Google shop. So we're, we're work exclusively in the Microsoft space. Now they have workforce. People in different countries or different offices, different geographies, some working from home, some working in offices. they've got a lot of knowledge workers. They've got a need to be able to work on many different devices throughout the day. They are partway through the journey. Of embracing ai, and they ideally are in some kind of regulated industry where security is mandatory, they're, they're subject to some kind of federal mandate to protect data, financial data, student data, patient data. So they have to take security seriously. know they need to embrace ai, they want to do it with Microsoft. They don't have all the skills in-house and they want a partner to come in and work with them, them deploy the technology with best practice, them automate all the manual processes and do lots of knowledge transfer. know, the word mentor our name is there for a very good reason. We still do a lot of knowledge transfer. It's a very large part of how we work. And helping people become the experts on the technology stack they've chosen so they can extract maximum value from it.

chris_1_12-19-2025_131141: 30:44

Gosh.

denis-o-shea_1_12-19-2025_121138: 30:44

hopefully that describes the ideal customer.

chris_1_12-19-2025_131141: 30:46

No, that does. I love, healthcare,

denis-o-shea_1_12-19-2025_121138: 30:49

Yeah,

chris_1_12-19-2025_131141: 30:49

higher education.

denis-o-shea_1_12-19-2025_121138: 30:50

of our business

chris_1_12-19-2025_131141: 30:51

Insurance. How, how

denis-o-shea_1_12-19-2025_121138: 30:54

it.

chris_1_12-19-2025_131141: 30:54

even, governments, I mean, state, local, federal,

denis-o-shea_1_12-19-2025_121138: 30:57

Oh Yeah. And, and federal, you know, we manage, we manage all the it and all the mobile devices for some, large defense organizations

chris_1_12-19-2025_131141: 31:05

very good.

denis-o-shea_1_12-19-2025_121138: 31:05

and highly secure government organizations. a lot of the work we do in other markets as well.

chris_1_12-19-2025_131141: 31:12

Gosh. where'd it go from there? That, that's a lot of good information and definitely has the gears turning.'cause I, I agree with you. My, I didn't know the last 10 years was so focused on mobility and wireless and all these devices. the one thing that almost always comes up, if you mention copilot, ugh. That's complicated. I can't figure it out. Or we, or I love asking customers. So what's your MDM strategy? Oh, we use copilot. Oh, that's great. How, how's that going? Long pause. Well actually, John set it up four years ago and, and he left, you know, two years ago and I don't think anyone's really managing it.

denis-o-shea_1_12-19-2025_121138: 31:45

Oh. Oh, you're right. I mean, up until last week, Intune had 10,000 unique settings. It was a big product. And then with the announcements last week when Microsoft added five new products into Intune, all included in the, Microsoft 3, 6 5 license. I don't know the exact number, but we're getting closer to 20,000 unique settings just in one product. you know how many years it takes to get an engineer to expert level on Intune and be really, really good at just Windows or Mac or iOS, or deep in the Android area? It's a beast. Intune is a colossal product.

chris_1_12-19-2025_131141: 32:20

Wow. Do you have any insight onto what that's gonna look like going forward? I mean, will it always require someone like you and an engineering staff to configure it properly and then, regularly maintain it?

denis-o-shea_1_12-19-2025_121138: 32:34

Yes and no. You will be able to do basic configuration with best practices, very easily out of the box, properly. Have an AI agent. Set up some policies to align with your favorite regulatory framework. You know, if you're a CIS, whatever, there will be ways of doing that easily with smart tech, but. That will leave a gap in understanding. And so if you need to do something custom or something breaks, or there's a policy conflict between what you've got in entre with your identity or your conditional access policies and the way you've set up your devices, if users are getting locked out or timeouts happening, wrong times and all that, that's where there would be a skills gap. getting started, easy scaling sustainably a bit harder.

chris_1_12-19-2025_131141: 33:25

Yeah.

denis-o-shea_1_12-19-2025_121138: 33:26

liken it to pickleball, right? I'm a huge pickleball, fan, easy sport to get into and start, and you're just having so much fun very quickly, but a difficult sport to master and really play at a high level and,

chris_1_12-19-2025_131141: 33:40

If you're not careful, you'll trip and break your ankle or your wrist

denis-o-shea_1_12-19-2025_121138: 33:44

I broke my partner's nose.

chris_1_12-19-2025_131141: 33:46

I'll put a muscle in my calf, my calf muscle last year. And, you know, because again, if you're not warming up, I mean, just like everything, if you don't prepare properly and you don't have the right training, you're gonna hurt something or somebody's gonna get hurt. It's the same way with

denis-o-shea_1_12-19-2025_121138: 33:59

yeah,

chris_1_12-19-2025_131141: 33:59

like, if, if you're, if you're not, if know, learning from professionals, caring properly, yeah. You're, you're in for a world of hurt.

denis-o-shea_1_12-19-2025_121138: 34:07

Yeah. point, you know, we come across a lot of clients where they say, oh yeah, Jimmy set up in June four years ago, and he's gone. and now we're not sure what it's doing or where we're at.

chris_1_12-19-2025_131141: 34:17

Like, what's the point,

denis-o-shea_1_12-19-2025_121138: 34:18

set and forget.

chris_1_12-19-2025_131141: 34:19

right? Yeah.

denis-o-shea_1_12-19-2025_121138: 34:20

No, no.

chris_1_12-19-2025_131141: 34:21

but that's, you know, I, feel like there's a slow trend that I've noticed just in my limited, view of this space of, companies are like, yeah, we're gonna make Intune work. You know, I'd want to pay another subscription for, you know, pick one. Um, I already have this, you know, Microsoft is a reputable company. They clearly know about software. we're just gotta figure it out, you know, type thing. But, back to the point, unless you have someone on staff that's a specialist in that area.

denis-o-shea_1_12-19-2025_121138: 34:45

Yeah.

chris_1_12-19-2025_131141: 34:45

how long are you gonna fill around in the dark till you figure it out? Why, you know, just go to you guys on that note. So your team identifies a customer that needs your help. what does that sales cycle look like? I gotta believe there must be a lot of due diligence and, a lot of information gathering before you can even begin to configure a proper deployment. is that fair?

denis-o-shea_1_12-19-2025_121138: 35:07

That's a great question. Our sales cycle has just got shorter and shorter over the years, which is really convenient actually as a business owner. And, and that is, yeah, and that's happened for a couple of reasons. we got great advice from a marketing company in Canada about five or six years ago called, Neural impact. they said, as a small company trying to establish ourselves, the more we share, the more transparent we are, the faster we'll be able to establish trust. So their advice was put your prices on your website, share your customer logos, produce lots of videos, share your ip, write blogs, write white papers. Give it all away. And establish trust quickly. So when people come to your website, they get to see, well, this is what you charge and these are the people you work with, and here's some stuff your engineers have published and here's a white paper from your architect. And the customer will very quickly self qualify. They'll either say, no, you're too expensive, or they'll say, your prices are reasonable. Clearly you know what you're doing. You've worked with my peers. I recognize the logos on your website. I like the way you described this thing, or the way you articulated, an approach, I'm gonna hire you.

chris_1_12-19-2025_131141: 36:17

Yeah.

denis-o-shea_1_12-19-2025_121138: 36:17

that helps enormously to break down barriers and get to trust quickly. The second thing that helps is when Microsoft introduces us. says, mobile mentor is our top partner, and they're the guys who do the most complex work and the biggest work and the biggest rollouts. And know, for some of the biggest healthcare providers, biggest defense organizations, biggest retailers, that's how they introduce us. And so those customers just go, okay, that's great. Thank you. We don't have to do an RFP. don't need to spend three months scanning the market. We're talking to the people who. Done it before many times, and we can get into it. You know, we can immediately drop into a very nuanced conversation about their specific use cases and scenarios. Even if they don't buy from us, they're gonna learn.

chris_1_12-19-2025_131141: 37:02

That.

denis-o-shea_1_12-19-2025_121138: 37:03

They're gonna learn a ton about how to approach it.

chris_1_12-19-2025_131141: 37:06

You mentioned that marketing firm in Canada, all the great advice they gave you. I'm just curious, did they mention that you need to come on this podcast by chance, that you should work at the wireless way? I mean, we need to, we, I need to get with that marketing firm recommending that should have been the first advice you Hey, call Chris and get on his podcast. A great conversation, Dennis, I I do have one last question that's kind of, tongue in cheek, but, so it, I, there's a rumor that you, you moved to Nashville'cause you're gonna start a, if this mobile mentor didn't work out, you're gonna become a country western singer. Is, is there any truth to that?

denis-o-shea_1_12-19-2025_121138: 37:39

There's no truth. Sadly. I wish there was. I wish there was, but I'll tell you a funny story. When I moved here, we were still doing a lot of app development. mobile app development. and, you know, very quickly realized Nashville is in the buckle of the Bible belt here in the south. And we were thinking about setting up the app development practice here, we thought maybe, we'll, maybe we'll call it, John the Aptist. We didn't,

chris_1_12-19-2025_131141: 38:08

I was.

denis-o-shea_1_12-19-2025_121138: 38:08

we had a good laugh at that, John the Baptist.

chris_1_12-19-2025_131141: 38:12

Well that is. Is there any last words, anything as we wrap up, is there anything we didn't hit on that you wanna mention or a favorite quote or a book? Anything you can share with us?

denis-o-shea_1_12-19-2025_121138: 38:21

Favorite quote is, future we see is the future we get. It's been my favorite quote for years

chris_1_12-19-2025_131141: 38:26

The future we see

denis-o-shea_1_12-19-2025_121138: 38:27

it.

chris_1_12-19-2025_131141: 38:27

the future.

denis-o-shea_1_12-19-2025_121138: 38:28

we see is the future we get. I believe it's all in the mind's eye. know how we visualize and like I tell my team, you know, we set that vision, let's you know, what would it look like to become the best in the world if we just get up every day and think about that for 10 years? What happens?

chris_1_12-19-2025_131141: 38:43

I,

denis-o-shea_1_12-19-2025_121138: 38:43

we

chris_1_12-19-2025_131141: 38:44

support that.

denis-o-shea_1_12-19-2025_121138: 38:44

get.

chris_1_12-19-2025_131141: 38:45

Some people call it law of attraction. Some people call it positive thinking, whatever you call it. It does work. I mean, I can speak

denis-o-shea_1_12-19-2025_121138: 38:52

yeah.

chris_1_12-19-2025_131141: 38:52

that my whole life, everything well in my life, other than being a matter of prayer and, my belief in God. but, you know, I also have a very positive attitude. You know, I believe if someone else can do it, I can do it. I mean.

denis-o-shea_1_12-19-2025_121138: 39:03

Yeah.

chris_1_12-19-2025_131141: 39:04

if you have a position of, pessimism, don't be surprised when you're just not successful in life.'cause you won't be. You have to be, we have to be willing to learn. You have to be open-minded, but you have to be positive What a great way to end this conversation.

denis-o-shea_1_12-19-2025_121138: 39:17

and that's not my quote Chris. I read it somewhere. but I latched onto it

chris_1_12-19-2025_131141: 39:23

That's right.

denis-o-shea_1_12-19-2025_121138: 39:23

latched onto me,

chris_1_12-19-2025_131141: 39:24

Whoever said it, you know,

denis-o-shea_1_12-19-2025_121138: 39:26

a wise man

chris_1_12-19-2025_131141: 39:27

that's right.

denis-o-shea_1_12-19-2025_121138: 39:27

woman.

chris_1_12-19-2025_131141: 39:28

probably from the stoics or something. I see. Marcus or, or, saying something like that. Dennis, I really appreciate your time. I've enjoyed this conversation. I've learned a lot. please check the show notes and you'll, and I'll have more information there. But, thanks again for making time for us.

denis-o-shea_1_12-19-2025_121138: 39:42

Thank you Chris. I'm delighted to be part of your community.

chris_1_12-19-2025_131141: 39:46

Thank you so much. and thank you for listening to this, episode of The Wireless Way. And as always, if, any of this resonated, if it hit home, you thought about a customer, you thought about a colleague, share this episode with them. go to the wireless way.net. There's a contact us button if you like more information. Of course there'll be information in the show notes and links to, mobile mentor and, learn a little bit more about Dennis, as well. So we'll see you next time on the Wireless Way.