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#834 ITEXPO '26 - Jason Kemsley: 🚀 Winning the MSP Game Through Relentless Standard

• Joey Pinz • Episode 834

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What does it really take to scale an MSP without burning out?

In this high-energy conversation, Joey Pinz sits down with Jason Kemsley of Uptime Global live from IT Expo in Fort Lauderdale to unpack growth, health, vendor trust, and what it means to truly partner with MSPs.

Jason shares how Uptime helps MSPs reclaim their most valuable asset—time—through white-labeled helpdesk, NOC services, and global staffing across five countries. But this episode goes deeper than outsourcing.

They explore imposter syndrome, the reality behind conference glamour, why “being the good guy” doesn’t always win in business, and how personal standards shape professional results.

Jason opens up about health, eliminating alcohol, flying planes, playing padel, and the internal standards required to compete at the highest level.

🔑 Top 3 Highlights:

  1. 🛡️ Why MSPs MUST ask vendors tougher security and long-term strategy questions
  2. 🌍 The untapped opportunity in South African engineering talent
  3. ⏱️ How operational support gives business owners back the time to grow

If you're an MSP owner navigating security, staffing shortages, and growth pressure—this episode is a must.

 

 

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How did you get into Padel? It's pretty new over here. So I spent a lot of time in Spain. And it's the home. It's the Spanish sport, isn't it? So I've had a lot of lessons recently. And the club I go to is the number one Padel club in the world. Is it really? So I guess it's kind of like this industry. When you see people that are excellent at things, your bar needs to become somewhat higher to compete with them. And obviously you burn calories. So that is the best thing. How old is the sport? Oh, I couldn't tell you. I mean, it's to us. It's relatively new here in the States. So I know at the moment is the fastest growing sport in the world. Um, more paddle, paddle courts opening. I keep saying paddle because in the UK, the UK people don't pronounce it correctly. Um, but yes, the number one fastest growing sport in the world. So we like where Where I Live, I Live in a very small town because I'm not there much. And we've had six courts open in the last two months. And they're fully booked. I'd have to book now probably for the last week of the month, like two weeks in advance. So pickleball got crazy around here in the States for a while, but it's kind of fallen off a bit. So my understanding, I don't know how true it is, but my coach said lots of tennis players that couldn't quite make it. Pickleball and lots of racquetball have converted to Padel because there's a real shortage of coaches Whereas tennis, there's coaches all around the world. Padel is so new that it's very difficult to get a good coach because if they're good, they're normally in competing or... And the racquet, there's no net, it's solid, correct? Oh, there is a net. Oh, there is a net? So there's a net in the middle of the court and then the racquet... Usually carbon fiber if it's a good one. I see. With like a foam insert. I see. And then it's got holes in similar to a tennis racket. But it's effectively foam. A tennis is string. There's no tennis, there's no string. No string, no. It's effectively a foam, a foam racket covered in carbon fiber. And it's short, it's the handle, it's right to the handle, correct? The head? So there's like, there's three different types of racket now. They're definitely, the technology is coming out quicker than people can keep up because it's so new. So I bought a really good racket three months ago and it's already very old technology. I've already used two versions more of my racket, which is crazy. And what happens, Jason, when you actually have to leave the court to get the ball sometimes? Because they hit it at an angle and it leaves and you've got to go go through the door and hit it back in? Yeah, only if you're playing good players. Oh, I see. I'm only seeing high-level, I guess, video then. Okay, yeah, so high-level players like Tapio, who's number one, I think, in the world at the moment. So someone explained it to me, my coach explained it to me, as you are trying to just make the rally go one point longer. Because if you try and attack, You open the door for over the net, over the glass. I see. So you're only ever just trying to get one point next, just the next shot, next shot. And are you playing singles or doubles? When I'm having lessons, it's singles, but you typically play doubles. Typically play doubles. Yeah, so you've got to find three people you like, which is probably the toughest thing for me with my diary. And not only that you like, but have to be similar skill level. Because then it's not fun if they're too good. It's not fun for them. They're not as good. It's no fun for you. It's similar to tennis in that way. Yeah, there's a handicap system. You know, you can exchange strokes and things like this. So Brad, who won't like me saying this, the other owner of uptime, I play a lot of him. Oh, my level was unfortunately I say, um, right, but you can still have a good the great thing about, I guess any good sport is you can have fun even if you're not right, quite the same. So I still have good exercise. The Spartan points? No, so we usually will play together and then try and find someone that, but then I have to try and not get upset. He may miss a shot I might get, but then usually it actually ends up being that the slower pace makes it harder for me, because he's playing at his normal pace. I'm trying to slow down my pace to meet, and when I'm playing with a coach, that ball's coming back at me three times the rate. So it's actually quite difficult doing the opposite. I play tennis and you get connected, you know, and if I'm playing a particular round with somebody who's relatively weaker, it then starts to force me, okay, I've got to start hit winners now. I just can't volley it because they're going to go to him and it's going to die. So it shifts your mentality when you're in this space. We've got to do whatever we can to keep fit, right? To keep fit, yeah. And how long are How long have you been a private pilot? Two and a half years. But sadly, I do not get the time to do it that I once had, which I've kind of resigned myself to the fact that it is something that I'm probably not going to be able to upkeep. It was a dream. I achieved the dream. But just realistically, I spend more time as a passenger than I unfortunately enjoy. Something happened to me. I got it. I loved it. But it can't be your fourth or fifth hobby. It's got to be first or second because, you know, there's lives involved. You know, and so because I get the golf courses quicker, you know, I go to the beach more, you know, but then and then if you don't do it for a month, your skills weaken and you can't have that. So we have a law. I don't know if it's in the US, but in the UK where you cannot take passengers unless you've done three independent takeoffs and landings. Same thing. I am so so I normally do five, my rule with myself is five. It's the one, I'm very ADHD sporadic. With this, I take my time. I'm there half an hour early. Then even the earlier that I've set, because people put in their trust in you. That's right. I've taken up Friends Children and stuff and that's a lot of... I think in a moment, because you're concentrating, you don't necessarily realize it, but And there's gratitude, they trust you, which is nice. Yeah, absolutely. And I've been able to make some people smile and have memories for a lifetime. Yeah, that's right. I think if I was to continue it, it would be in some sort of charity fashion. I'd like to do like a charity. So we have a charity near where I Live where disabled people can effectively be sponsored to go and achieve their dreams. And many of them have dreams of, because it might be a mobility issue or something, usually that dream is tied to, I want to go into the sky, I want to fly in a small plane or whatever. So I'd like to do some of that, but it comes back to work, it comes back to work. Yeah, we have something here called angel flight, where people, they're sick or whatever, or an animal or something needs to be taken somewhere and there won't be any charge for it, people cover it. There's plenty of cheer. There's plenty of charities that it's an incredible thing. It's incredible thing. But you know, I think We all spend our lives chasing dreams, right? And then when you actually get the thing, yeah, you realize It isn't what you thought right? It was fun. It was cool. I've ticked it off, but the same burning desire is not there Yeah, and I think I've had to come to terms with the fact that Work is the only thing that is constant. Mmm, like I can And you can have these different goals and micro goals, et cetera, but to pin it all on one thing, it doesn't quite work the way you thought it would when you were younger. Yeah, the pleasure's in the journey, not the destination. Yeah, but we need reminding of that, right? We need reminding. When I walk around these conferences, you don't necessarily know what the person walking past you is going through. That's right, what their story is, yeah. I'm trying to enjoy it more and more, and being somewhere like this in Fort Lauderdale, that helps. Not bad. That helps. I'm told this is a brand new hotel. Brand new. They've been working on it for, it seems, years, yes. Oh, really? Five years, it would seem. Five, six years, yeah. So there's worse places to be. That's right. I like to, I think I'm lucky. I'm actually, I'd love your opinion on this. I'm thinking, so over the year, I've been capturing reality versus perspective photos. Yeah, photos. Because I think that when I speak to friends or colleagues or MSPs or whatever that know what I'm doing or how I'm doing it, I always get the, oh you must be on business class, first class, five-star hotels, everyone does everything. No, the reality is I had to get four large suitcases from the Holiday Inn Express Walking down the road, I had to take two at a time to within eyesight, stop, walk back to get the other two. We're privately funded. We haven't got P.E., we haven't got V.C. Every dollar makes a big difference. And so I'm capturing the photos over the years so I can show, because I think there's a misconception about how joyous it has been on the road. It's not, it's incredibly lonely and tough. It can be, yes. Airports, yeah. If I see another American lounge this year, lounges are not what they used to be. No, they're not. Yeah, yeah. The flight, you flew out of London? Yeah, London, yeah. Five hours? Six hours? No, it was eight hours fifty. Eight hours, that's right. Eight hours back, yeah. But then you've got to add on the two hours waiting for the four suitcases with the exhibition stand, which never go through TSA very well. Yeah, so they always ask about the socks. I've got the uptime socks. And oh, are you here to sell the socks? No, I'm not. These are free. Because if you were selling there'd be tariffs on them or something? Yes, with all selling, I would need a different visa. Interesting, because I'm I guess there's a commercial element to Wow. I remember I was in I was in London doing the podcast and I came back and these little discs that the mic stands around they're very heavy. These little discs and when they went through the when they went through the x-ray they said what are those things I said I don't know I never see my luggage through that you know through this in this means I don't know what they are but well you should know what they are and they took it as oh that's right to the podcast basis they go why didn't you tell me I said well I didn't I don't know I didn't realize that this is solid metal as well it's all metal yeah I know nefarious purposes perhaps but just I just didn't even think of it so I'd be quite a fun job just looking in people's luggage what do you have Do an x-ray. I never see my stuff in x-ray. I don't know what those are. I'm thinking somebody put something in my bag. You just never know. You have to be so careful, right? Especially when you've got a lot of luggage. That's right. And electronics and things like that. So we're here at the big IT Expo. Jason here in Fort Lauderdale. It's mid-February. What are some of your goals this week? So this is our first time at this event. Our calendar for the last couple of years has been fairly static with the type of events we've been to. This year we have a goal to reach further afield and reach some more of the MSP audiences. So this is our first time here. So my primary goal is to meet some new faces and hopefully get the opportunity to tell them what we're about as an organization, but predominantly just meet new faces. I met someone yesterday that said this is the only MSP event he goes to. And like this is a new world for me. I've been in the IT Nation, the Kaseya, the Enable, you know all the big events and this is a like a microcosm of the industry it feels like that maybe we haven't crossed paths with just yet. So I'm seeing lots of new faces. This is my first time at this resort. I'm actually back in two months for another event here. Oh really? It's a great place to meet new people I think. I didn't know there was anything else here. Very interesting. Yes, Enable Empower. Oh, Enable's going to be here. It's in this exact facility. I would love to tell you the dates, but it's some point in April. We'll figure it out. Yeah, April's a busy month. Yeah, a real busy month. So how does Uptime help MSPs? Our predominant goal is to be an operational partner to MSPs so that they have a solution for whatever operational pain they might be feeling. We have onshore options, we have offshore options. We have the white labelled help desk, we have the NOC, we have dedicated staffing. The idea being that we can have a relationship for whatever you might need, but that can then evolve in a month, it can evolve in six months. We can sideways move contracts, we can move from a dedicated person to a white labelled help desk. We're just effectively partnering together, so you've got someone else fighting your corner, when it comes to operations. We're people strong, five countries, and we've reached the right size now where we can give the flexibility back to the MSP so that we can have, I guess, an operationally flexible partnership. So it's not outsourcing a single person. It's the actual entire health. You can do a single person. So we do single people in Sri Lanka and South Africa. South Africa is absolutely flying at the moment. A lot of wonderful engineers and talent out there, which is fantastic. But then we have the white-labeled help desk, which is US, UK, New Zealand, which we're synonymous for now. That's 24-7, you can have it in various commercial models, per ticket, per user, per device, whatever kind of works. We've got routes for most scenarios because we're trying trying to be that. Some MSPs don't build in this way, they build in this way, so have we got a model for them? And then we have the NOC, which comes from some M&A done a couple of years ago of an organization called InBay, but we now have the NOC as well. So I'm proud to say, because NOC is relatively new for me, and we've only had it for two years. Network Operations Center. But I truly think we're the best in the world at it. The M&A, and without taking people back in time too much, the M&A was perfect for us and intentional because it took Uptime, who were the best at Helpdesk, or considered very well regarded, and Knock, which was considered very well regarded, and bringing them two together. Typically, I see M&A as a way for someone to exit, increase bottom line, or whatever. This was about how do we bring a suite of services that are best in class independently together so that people can move sideways between them or partner in a flexible manner. I don't want to sound like we don't have contracts, we absolutely have contracts, but because we're committing in personnel and employees to bolster your operation in whatever way, but if that doesn't work, hey, do any of these other three things work? Can we make sure you get value by getting one of those instead? Just trying to be a good vendor. When MSP is looking to partner with somebody who does outsourcing, does operations, knock and does help desk, what questions should they be asking? This is a great question and I was actually talking about it a little bit yesterday. It incredibly frustrates me how little people qualify their vendors before they work with them. Very easy for me to say. I can say that because I am proud of our answers to a lot of the questions, but it means that people that fall a little bit below the line often are winning things they shouldn't probably be offering, if that makes sense. First and foremost, we should be having a 30-minute hour call about what we do security-wise. I think that's a non-negotiable. Before we even get into does it commercially fit, do I trust you with what measures do you have in place, et cetera. Understanding or asking where that business is heading is usually not an answer you'll get a very honest response to, but I think it is something we need to be asking. If you're going to one of the big guys or girls, you know, the top four vendors or whatever, you're probably not gonna get a response that is meaningful in whatever way. When you're working with certainly an outsourcer, you want to know where they're going to be in two years time. And you want to know, hey, if I need it, are they going to go put in one of the owners or the senior leadership team onto this call to have that conversation with me? For us, we're trying to create long-term partnerships with MSP's. We win when we keep you happy for the longest period of time. So I absolutely can be, and so can any of our leadership team, be pulled into any pre-sales call to explain where we're going. You are giving me so much trust with your customers. Sometimes, in those calls, we realize it doesn't align, but we recognize it in outsourcing, there's a lot of trust. So certainly, where are they going, security, and then trying to get some face time, usually, with someone that uses their service. I could probably, I reckon it is over a year since all three of those is what asked of us. I sit in pre-sales calls and sales calls with our team all the time. I have been asked about security and then we give them our white paper and that's it. No further questions, which usually you would expect a couple more. I don't think in the last year I've been asked where are we heading? What if our business direction looks to change? And I know some people won't be honest about that. But certainly have never been asked for testimonials recently. I talk to MSPs every day, Jason, and it's been pretty consistent last five or six years what keeps them up at night. The three. First is security. They're worried about their clients getting attacked, then they're going to have to allocate resources, they're flat rate, they're going to lose money, they're probably going to be fired, and they're probably going to be sued. So it's top of mind. Second is human capital. How am I going to get better techs? How am I going to keep my techs here? Unemployment in IT here in the States is 1%. I mean, the technicians are swallowed up very quickly by big companies. And then third is just general growth. Private equity has poured in hundreds of millions of dollars. They need to grow. Their friends are selling their MSPs, getting nice cars and growing. How am I going to do it? It seems that you can actually help in all three. Security, we have to be the strongest chain, strongest part of the chain in the link, so whether it's ISO certifications, we've got a full-time compliance manager that handles all of our certs because of how many we have to have, fingerprinting all the offices, there's a plethora of things that we can go through and show there. Human capital, I don't want to be detrimental to our business, but we've just made the investment so other people don't have to. That is our business model. A New Zealand office before we needed it. Because if we don't, then who is going to? And we need to make the investment to then be able to sell it. So we are investing things ready and before an MSP might need them. And that's our business model. I know I mentioned South Africa, but I do truly think that is the most underlooked thing in the US market right now. Some of the case studies we've got in the last three, four months one engineer to 10 engineers. You wouldn't even know they're in South Africa. And still relative cost saving as well, but just this huge opportunity if people just lean in a little bit. And when it comes to growth, we're a tech organization, right Joe? We're not a sales organization. 94, 95% of our personnel are techs, or technical in the job they deliver. And then we've got an account management team and a sales team. That's pretty much us. We don't have the huge enablement budget, et cetera, to give you all the marketing in the box. What we're saying is, we'll come to the party and we'll give you back the time to not worry about operations, whether it's because of a couple of things or one thing you work with us. And so to spend that time doing the thing that we know you will do best, Mr. Business Owner, or Mrs. Business Owner, which is selling yourself. No one sells better than the person that lives it, breathes it. And whilst this is an audio for some people, giving you back time, and we got the new custom Uptime watches just finished. But that is what the goal of what we do for MSP is, try and give you back a bit of time, a bit of breathing space, so that you can attack that marketing sales on all fronts, Because you know, I know, when you're doing this, and then you've got to do that, and then you've got to be here, and then you've got... You don't get consistency with any marketing, any sales. So we want to make that your full-time focus. Jason, is there something that you believed in strongly 10 years ago that you no longer believe in? Or believe is true? I don't want to go too deep. 10 years ago, I always believed that being a good guy would get me very far. It hasn't got me as far as I thought. And I'll tell you why. Taken advantage of Taken advantage of You know, I'm always open and honest. We've had some MSPs that have tried to take advantage of us. I think we have sometimes been the most forgiving part of the chain because we want to be a good, we really want to be a good vendor. I want to sit and have a drink with anybody in this conference and be proud of the decisions that we've made or I've made or whoever's made. But that does mean sometimes that people try and get one over on you. And so in the last two, three years in particular, post the deal that we've done and sort of getting much bigger and a more mature organisation, I've realised that The good guy doesn't necessarily win. Wow Which is sad. I'm not willing to compromise on my values, right? I've just become aware that actually I've been looking at it the wrong way and sometimes a Decision to protect yourself or the business is not always you being a bad guy You're just being a good guy to your personnel as opposed to So it's a difficult one. Yeah, it sure is very interesting. You learned that just generally with maturity so I started the MSP back in the 90s Jason and I was working way too hard 14 16 hour days you're no stranger to that and putting my health in the in the backseat and not playing any more tennis or soccer or anything and working way too hard developing poor eating habits next thing I know I'm in front of the doctor and she tells me I'm at 340 pounds so I gained this terrible amount of weight I knew I was getting big didn't think I was that big but she then tells me and she says, if you don't lose this weight, you're not gonna see your daughter graduate. My daughter was just born. Scared the life out of me. I'm driving home, she didn't motivate me, she angered me. I'm punching the steering wheel, I can abuse myself, I'm in my 20s, I feel like I'm indestructible. I can abuse myself all I want, but it's much bigger than me now. I have others that, so I spent the next six, seven months, lost about 130 pounds, and I kept it off. Yeah, that's awesome. And you can't look at these things as a finishing line many times when people you know that I've gone through it now I can go back to old habits. These are lifelong changes So when I tell this story Jason people always say well, what's your secret? What you do? I say there's no secret. I say discipline right focus, you know routine Willpower all parts, but how does discipline play a role in your life Jason? I'm huge on health huge I've got a sick father from a young age and it's always been subconscious. I'm very paranoid about how much I fly and possible effects, etc. So I have a huge, which I'm not going to take you on the full spill because I'll be here all day, but I've got a huge health part of my life which I have to do these things weekly, daily, etc. That I listen to. Lots of American people have played into that. Gary Brecker and the likes. The US is great for this new sort of cutting edge advice and Tony Robbins has got some cool stuff in there as well. Discipline in particular, I don't believe that I am the most talented person ever in a room, but I believe that I'll outwork people. And I think many people have that thought and feeling. But I have real imposter syndrome, as do many MSP owners, they were a tech and then it somehow into maybe something it wasn't meant to be. So I have Ruh Impostor Syndrome and so discipline wise I just have to tell myself and I could continually remind myself I have to be willing and able to do more than X number of people if I want to achieve what I would like to achieve. So health and effort they go hand in hand but they are me and in a nutshell, to be completely honest. And how does it bleed, or does it bleed over into your professional life as well? I find it very difficult to be fully disciplined because of how, not sporadic, but I can often be in this thing over here and then I need to be pulled here internally. So I find being quite disciplined in the day-to-day and in craziness, so to speak, I find that quite difficult to impart. I've instead gone the opposite way and leaned into my strength of being good at context switching, which is something I think I'm fairly good at. But the discipline of, I want to be on time. I was walking over going, I'm glad I'm not gonna be five minutes late. I'm very disciplined about when I... I'm very disciplined about making sure I make the most of every opportunity it presents itself. yes even if that means you then say no because it turns into the wrong thing. Tonight when the event's finished everyone goes for happy hour I will go to the gym. Ah good for you. I've stopped alcohol completely. A couple of years on the road can quickly make you realize alcohol is not good for you. But I get discipline is all we have. If we don't have discipline then what do we What do we have? Jason, absolute pleasure. Anybody watching, listening, wanting to get in touch with you, what's the best way? Uptimeglobal.tech if you want to speak about uptime. But if you want to speak more personally or even about uptime but would rather a personal conversation, then Jason Kemsley, Kemsley on LinkedIn. Yeah, you're very, very, I see you on LinkedIn all the time. Jason, thank you so much for your time. Thank you for having me. Really appreciate it. Thanks, Joe. Jason, great job.