
Sell Me This Podcast
Sell Me This Podcast is a deep dive into the intricate world of enterprise technology sales and procurement. Hosted by Keith Daser, each episode unravels the strategies, tactics, and human psychology behind how business-oriented technology solutions are bought and sold. Designed for corporate buyers, technology sales professionals, and business leaders, the podcast provides actionable insights to help maximize the value of tech investments. Expect engaging interviews with industry experts, real-world case studies, and practical advice. Tune in to demystify the tech sales process and gain invaluable tips for navigating your next big purchase.
Sell Me This Podcast
Leadership and the Future of Managed Services with Shawn Freeman
In the first episode of Season 2 of the Sell Me This Podcast, host Keith Daser talks with Shawn Freeman. From starting and scaling organizations to navigating leadership challenges, Shawn shares what he’s learned from years of building teams and driving growth in a changing industry.
They discuss how the MSP model is evolving, what strong leadership looks like in today’s tech landscape, and how forward-thinking companies can adapt to new client expectations and technologies shaping the future of service delivery.
Whether you’re leading a growing business, mentoring others, or exploring what’s next for managed services, this episode offers grounded insights and a real-world perspective from someone who’s lived it.
Find Shawn on LinkedIn: https://www.linkedin.com/in/shawnfreeman-/
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If you believe you deserve more from your technology partnerships, connect with the team at:
https://www.deliverdigital.ca/?utm_source=videodescription&utm_id=youtube
Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.
This episode of the Sell Me This Podcast was filmed in the Social Launch Labs studio. SLL delivers top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.
Find the team at Social Launch Labs at:
www.sociallaunchlabs.com
Sell Me This Podcast is brought to you by the team at Deliver Digital, a Calgary-based consulting organization that guides progressive companies through the selection, implementation, and governance of key technology partnerships. Their work is transforming the technology solution and software provider landscape by helping organizations reduce costs and duplication, enhance vendor alignment, and establish sustainable operating models that empower digital progress.
If you believe you deserve more from your technology partnerships – connect with the team at:
www.deliverdigital.ca
This episode of Sell Me This Podcast was expertly edited, filmed, and produced by Laila Hobbs and Bretten Roissl of Social Launch Labs, who deliver top-tier storytelling and technical excellence. A special thanks to the entire team for their dedication to crafting compelling content that engages, connects, and inspires.
Find the team at Social Launch Labs at:
www.sociallaunchlabs.com
Now let's focus on the better conversation around how do we use all the technology you have now more effectively, how do we empower your people, a lot of times how do we train your people to use it better, um, and just really set your business up for success that way.
SPEAKER_01:Welcome to season two of Sell Me This Podcast. For our first episode of the year, I am super excited to welcome Sean Freeman. Sean runs Always Beyond, which is a managed service company right here in town, but also has a ton of experience that he shares around leadership, around building organizations, and around the future of the managed service industry. We're super excited to share this story with you. Have a listen. We are so excited to kick off another episode, um, and really the first episode of the new season of Sell Me This Podcast with a really special guest today. I'm excited to introduce you to Sean. Um Sean, we're gonna dive right into things, and why don't you introduce yourself and tell us a little bit about who you are and where you came from?
SPEAKER_00:Awesome. Thanks for having me on, Keith. Uh, super excited to kick off the new uh season with you. Um yeah, Sean Freeman, I'm born and raised in Calgary. Uh, you know, there's a few of us around still. Um yeah, my history is in IT services. I I think uh I'll rewind it all the way to maybe when I was 13. Um my dad got me my first uh computer, 386, so not not not too far back. But uh I put it together myself with his help, and uh that really sparked my interest and got me really into tech and computers, uh, found me found me something that I was passionate about. Um and from there I just built on that. I my parents actually went through divorce and and so I you know got into the computers and really leaned into that. Um I was horrible in high school. I barely passed, did the minimum required uh which is which is interesting. You know, I gamed a lot and uh you know got C minuses on everything and even including math and and then I was like, okay, what do I want to do with my life once that was over? And um and I decided to uh go to Mount Royal College, but at the time it wasn't a university yet, and so went into the computer information systems course there and uh that I could qualify, had good enough grades. Uh that you know they let a rebel like me in. And uh I really found uh something that I loved and and like in school, like I never really loved school, but now that I was focused on computer stuff and uh making things and had some really amazing teachers there. Um I did really well. And in my first semester, I think I got a 3.88 GPA, like just blew it out of the water, and I was like, okay, I guess I I'm good at something. Uh and that was pretty cool. It was a really good motivation builder for me. Um and then I started to think, like, you know, I kind of want a degree, like I don't just want a diploma, and went down that path, talked to the counselors, and they said, Well, you could do the university transfer, but your math sucks because you sucked in high school, right? And I was like, Yeah, of course. And so I had to go back at that point, upgrade my math, my my grade 12 math, and do that. And it's really funny because I got a 64 and I needed a 65. Uh so I went back to the prof and I was like, hey, you know, I need a 65 to get into calc. Um, you know, is there anything that maybe was great and maybe you missed, or maybe, you know, like and he's like, okay, yeah, yeah. I found something there for the round. Probably was a little bit mean on you there, and and so he made the change and uh I didn't have to do it again. And so that's that's kind of nice. Um, you know, kept the momentum going. Um and it was in 2007, and I remember the year pretty vividly that I'd gotten accepted into the University of Calgary. I was gonna transfer and start the computer science program um because in August, uh August 15th of 2007, I was in a pretty bad car accident. Um it was in the afternoon, I was just driving along, mining my own business, and uh a car they were street racing in the middle of the afternoon for some reason. Uh lost control, came across the meridian and hit me head on. Um I was in my grandma's 1984 Volvo. Um luckily it was a big tank. Didn't have airbags, so I ended up with a broken jaw in two places the front and the back, and and my cheekbone broke as well. Uh shattered my knee uh on the dash and I was in pretty rough shape. Um and that was interesting because people asked me, like, you know, how do you feel about that being so far away from it now? Um and and I I I was always answer the same. My answer is like I wouldn't uh if I could pay money and have that not have happened, I wouldn't. Uh it was probably a really good thing for me. Um, you know, gave me something to come back from, work hard, did all the physio. Uh I actually ran a marathon about two and a half years after. Uh, and so put in a lot of work to do that. It's funny, the the lawyers on the other side of the case, they were like, Here's some photos from Instagram of you running a marathon. I said, Yeah, I did that so I could prove to myself I did everything I could for physio. And I straight up said that to her face, and that was the reason. Um, and then they had no more questions. Yeah. That was it, you just shut them up at that point. Yeah, like I was like, Do you want me to be a victim and you know, just pretend to milk the system or not? And and so then uh that got closed out pretty quickly after. But um, you know, that was a pretty pivotable change in my life, and and I remember I went to the U of C and then a year later I did uh I did a semester in Australia, uh, which I probably would have never done. I thought I thought long and hard about it, and I was like, you know what, life is short. And it just instilled in me this belief that life is short, right? And even to this day, I'm like, if I'm ever like, ah, should I spend the money and do the thing? No, do the thing, make the memory, right?
SPEAKER_01:Well, and I think you hear that story a lot for people that have gone through you know some of those really trying experiences where they've had some of that hardship, they've had something they've had to overcome, where a the perspective is completely different, but also when they look back to your point, it becomes so formative in that that hardship in who they are today, yeah, that that most of them that you talk to wouldn't change it as much as it would in the moment if you you know, probably if you caught you three weeks afterwards while you're you know in physical or in the hospital or something like that, you're like, you know, get me out of here.
SPEAKER_00:Yeah, drinking uh protein shakes for a straw because uh my jaw was wired shut.
SPEAKER_01:Like in the moment, I'm sure it was one of the most challenging things you've been through, but you know, that perspective probably really shapes who you are today.
SPEAKER_00:100%, yeah. And and that's the thing too, all these experiences, you know, I I've become a big believer of everything happens for a reason, the good and the bad, right? Um and so leaning into that and and just really knowing that, uh, because as you're you know building a business, you're gonna go through good and bad and uh you're gonna have to persist.
SPEAKER_01:Yeah. And so before we jump into your business journey, there's one other thing you mentioned that I found really interesting that I think is a little bit of a common thread sometimes, and it's not the um, you know, if you're kind of a crappy student in school, you become a successful entrepreneur. But I think that there seems to be a common thread of people that struggled in maybe a very traditional education setting and become successful entrepreneurs. Yeah. Is there something to that connection that you can think of?
SPEAKER_00:Yeah, I think for for me it was just, you know, really I I was smart enough to know the things I didn't want to do and weren't going to be useful to me in the future. Um, but I hadn't found that thing I was passionate about yet, right? And I didn't didn't see how it could make me money, or you know, this is before the time when e games could make you lots of millions of dollars, right? Or I might have leaned into that some more. Um, you know, when I went to university, I actually gave up gaming because I was like, I won't, I won't do good if I keep that in my life. Um so so I chose to focus. And and it's funny too, the the accident actually probably helped me in my school because uh, you know, I wasn't really able to, I was I wasn't super mobile for probably six months. Like I had mobility issues and you know, had bones to heal and all that sort of thing. And so that helped me focus. I actually took some of my hardest courses that first semester, and I was, you know, I had nothing better to do, so I went to all the the after hours help that the profs gave and um one of them was math, and it was uh it was a pretty challenging math course, and I got an A plus on it. Like it was it was discrete mathematics. And like I went from barely passing calc, I think I got a C minus in Calc, but I got it uh and it got into UFC to A plus in a math course, which was pretty amazing, uh, and probably because that focused.
SPEAKER_01:That's amazing, yeah. Like I I definitely feel like that's a big turnaround on the math front, and I promise I won't ask you any uh multiplication right now. This is the calculus section of the podcast.
SPEAKER_00:Yeah, yeah. And it's interesting as I learned like why math is important. Um really I've summed it up to like if you can understand logic as a technology person, that's really where the value is.
SPEAKER_02:Yeah.
SPEAKER_00:Um I don't need to understand how algorithms work. Uh if I can work a logic tree, that's usually gets me most of the way there and pretty pretty important for business, right?
SPEAKER_01:Yeah, and I think there is something to the practical math side of things where you know the ability to be in a meeting and kind of do some rough numbers on the back of a napkin. But uh, you know, if you're starting to do, you know, um advanced prediction or regression models in your head, I feel like we're we're having a different conversation.
SPEAKER_00:100%. Yeah. Yeah, you need some definitely some accounting skills for sure.
SPEAKER_01:And and so then you've taken some of the, you know, you've gone through school, you've gone through really a life-changing experience. How did you get into building your own business? Was it just kind of the progression out of school, or kind of how did you find yourself in that?
SPEAKER_00:Yeah, there's a lot. I'll dig into that a bit more too. And and so as a summer student, I had gotten a job at an oil company. I was at a company called CCS at the time, now Turbita, um, but recently got acquired by Secure Energy. And so I was there for a few years as a summer student. I had gone to Australia on this trip doing a semester abroad, and so that was amazing. Um, and it's interesting. Uh I knew I didn't have a job lined up to come back to because CCS wasn't hiring at the time, and I was out for a run, uh, as you do in beautiful Australia, and I was like, why don't I just start up my own like little computer repair company? You know, there's the student painters out there, and I was like, I'm just gonna call student geeks. And so I went and bought the domain, put up a silly little website, uh, and in no time I got like two calls. And a couple people called me and said, Oh, yeah, we could use some IT help. And um, you know, this is when SEO apparently was good, and I didn't really do much, and I got some calls, and um out of that idea grew uh a whole bunch. And so uh lo and behold, I actually got a job coming back to Calgary because that wasn't enough um income to keep me keep me afloat. And so I got a job in another company that some people from CCS went to. Um, so I signed up for that before I came back uh as a as an IT helper. Um we were it was me and my boss for the IT department at that company when I started. Um and I kept student geeks on the side. I had a couple little little clients that I was helping in my free time, and um and interestingly enough that kept growing um and that that kept snowballing uh sort of on the side, a little side hustle, right? Everybody, uh now it's the the me the big thing. And so came back, worked that job, secure energy grew from a hundred and so people to over sixteen hundred people in about four years uh while I was there, and I learned a ton of what I I took into my business and doing IT services for small medium businesses. And so, and over those four and a bit years, my student gigs started to grow, and I I you know I had six, ten clients, and I was like, okay, I can't manage both and feel good about it anymore. Uh, you know, obviously I wanted to maintain my reputation and keep doing the job I was getting paid for. And I said, okay, I gotta I gotta leave secure, and I was like, I'm gonna take the jump and make the leap. Um, and that was in 2011, uh, you know, right before the 2012 uh downturn in oil and gas. And so um luckily it worked out um because you know, I was talking to myself, I was like, do I take the leap? And I'm like, worst case I can get another another job, right? Like the market's good. Um, but then it wasn't. And so um, but it was good for being an owner of a company uh in the managed services world because people were like, how do we cut our costs? How do we outsource a few things? And IT was one of those expenses that a lot of people looked at. And so I was able to say, hey, you can outsource it to me, it's a bit cheaper, you still get everything you need, uh, and it's flexible as you kind of grow back out of this. Um and then I built a business off of that.
SPEAKER_01:And so one of one about being it's a 2012 year you're building that, and this would have almost, if I'm kind of looking back to, still being very much like IT is a cost center, IT is uh yeah, everybody wants to pay hourly still.
SPEAKER_00:Right. Um and so so what I did is actually um I did two things right at the beginning. I I I said I'm not gonna charge 50 bucks an hour. Um I'm not gonna, you know, just price myself really low just to get work. Um and I'm not gonna charge hourly. I said, you know, there's gotta be a better way to make it more predictable. And so I would go in and I'd say, okay, you've got this many users, you've got this many computers, um, here's here's a a one-monthly fixed fee, right? And most people were like, oh, that sounds good. And they're like, okay, so we don't have to worry about our bill changing every month. And so I kind of like stumbled into managed services um before it was a thing and starting to become a thing. Um and and that worked out really well because it set me up with a good foundation to hire from and and build a business off of. Um and that recurring revenue is obviously gold, right? Uh helps you start, right? Yeah, that's that's where we started off. Um, luckily, too, out of that downturn came a lot of people got getting laid off and then starting their own businesses. And a lot of those people that I built relationships with and became friends with at places like Secure Energy started companies. Right. They hired me because they're like, Well, who knows IT? Sean. Like, we know he was great at secure and he's gonna be great with our business. And so all those relationships turn into business for me. That downturn probably boosted my business more than I could have ever with some sales and marketing tactics, right?
SPEAKER_01:Well, and that's one thing I've always admired about you as well, is I I think that you put such an important focus on that community. Um, and so if you were to kind of be giving advice to someone that was building their business or even building their starting their career, uh how important is community um as you're growing both kind of professionally but also in terms of just the your life?
SPEAKER_00:Yeah, I mean it's it's amazing. I look back now and it's just I've got friends that I've made through business, I've made through just being out in the community, helping people when you know I didn't need anything from them, right? If you give give to others, it'll come back, whether it's from them or other people, right? Uh the law of reciprocity, right? Uh and so really focusing on that, um, you know, the the best time to plant a tree is yesterday, right? And so and that's the thing too, like there's all these there's all these sayings, um, you know, your your network is your net worth, but how do you build a network? You you build friends, right? Um as I built up TWT Group, which student geeks got renamed to because we figured we should professionalize it after I graduated, um, you know, I built I just built friendships and they turned into customers. And and and that's super valuable, and and that's translated into so much success over the last 15 years for me. Um, and I've been able to help a lot of people as well, right? Uh and what goes around comes around.
SPEAKER_01:Well, and and you know, I'm more on the front end of the journey, but I think that the having that community around you as well just makes it so much more fun.
SPEAKER_00:Oh, yeah, like I think I get to work with people that are great to work with and they value what I do. Uh I value what they do, I I support them, they support me. Like, what's better than that, right? Calgary is Calgary is this unique city a little bit. Um, everybody knows everyone, right? Uh it's interesting. I've I've gotten clients just because I was friends with them, they're like, Yeah, our current guys are fine, but like you're my buddy, I'm gonna buy from you, right? Um, and and honestly, like to be an MSP on the other side sucks, but like sorry, like I can't, they're my friends. I'm I'm just making friends. And so that's the advice I tell any business owner, um, especially if you're in B2B, right? Just make more friends, and then it turns into business. Um and then you get to enjoy it better. You're not just another commodity or another vendor.
SPEAKER_01:Yeah, yeah. Well, and I think that you're spot on. There's so many people that are so laser focused on the goal that they they miss getting to know the person. Yeah. And you know, one of my favorite quotes that I've I've heard recently is in order to be interesting, be interested.
SPEAKER_00:Yeah, it's uh yeah, curiosity is amazing. Um it's super valuable. And and the other thing too is I always tell people, if you want something, give it to somebody else. Yeah right. If I want more clients, how do I help somebody else get more clients? Like, you know, like Keith, think about you. If I want clients, I'll how do I get Keith more customers? And then you're just gonna you're gonna have the same thoughts. You're like, how do I help Sean? He's helping me so much. Like that's just how humans are.
SPEAKER_01:Well, and that's what I think, especially like, and I think people are like that for sure, but Calgary specifically, I think you're you hit the nail on the head, does have a very specific feeling in terms of how people want to see everyone around them succeed and and want to see that whole ecosystem propel. And you have a unique perspective, like there's not too many Calgary born and raised, you know, you are a little bit of a unicorn. Yeah. Um has it always been like that? Like I I'm I'm a you know, I consider myself a Calgarian, but I've been here for 20 plus years now, so I I feel like I can wear the badge with honor. Yeah, but but has it always been like that since since you were remember?
SPEAKER_00:Yeah, it's as long as I remember, and and honestly, in the business world, it even gets more because if you think we're a city of 1.7 almost, 1.7 million, um, you know, business owners make up one, maybe two percent of that. Yeah right. So it's a small amount of people at the end of the day. Um, and that's but it's enough to build a really good business, it's enough to really help uh help other people's businesses, but then also like pair some community impact on top of there, give back to the community. You know, it's a city that really rewards that, right? Like caring about the community, caring about other people. Um yeah.
SPEAKER_01:Yeah, and I feel like there as much as there sometimes is a scarcity mindset, I feel like maybe it's the oil, the oil backing, or maybe it's the kind of entrepreneurial backing of the city where I think people are less afraid to to help someone in fear that they might be losing something themselves.
SPEAKER_00:So yeah. And honestly, uh one of my favorite quotes of 25 is like the universe is not on a budget. Right? We we just get in these scarcity mindsets and it's totally manufactured in our mind. Um, you know, but again, if I want if I want something, how do I help other people get it? You know, it'll come to me, right? It can't not. The universe is gonna be like, oh, you're you're out there helping other people, figuring out like we're gonna take care of you, right? And if everybody operated with that mindset, like imagine the where we would be as a society.
SPEAKER_01:We would just do incredible things, yeah. And we are doing them, which is we could do more, yeah, and faster. Exactly. So do you feel like you developed that mindset through your career, or is this something that even if you look back to um you know, starting your first businesses and and starting to, you know, kind of the the scrappy underdog.
SPEAKER_00:Oh yeah, no, we were scrappy at TWT. Yeah, um, people did not like to compete with us. Uh yeah, we had that reputation, and and honestly, um it's interesting nowadays, like people still don't like to compete with us because they know like if I have a relationship, they're never gonna win the business. No, because I've had that relationship for a decade. Yeah, right. And and maybe they weren't even a client before, but now they are because they're like, you know, we just you know, you're we're doing such amazing things, we're helping people out, they want to be a part of that, right? Like we've just built this amazing, I don't know what to call it, but but I think that's I've learned that skill set over my time, right? Like, you know, when you're trying to pay your bills and you know, make the rent payment, like you've gotta you gotta find the revenue one way or another. And so um I would call them mistakes. I've made mistakes where I've you know done something that you know I'm I'm not proud of today, but I got the business. Um, but you know, we all we all learn. We're all gonna we're all gonna figure it out. Uh I forgive myself and uh you know and and now how do I get back? How do I help others, right?
SPEAKER_01:And and so tell me more about the TWT story then. So you I feel like there's a there's a couple more chapters in that book.
SPEAKER_00:For sure. Yeah, we can we can dig into that. So started in 2011, uh, you know, from from student geeks, uh side hustle turned full-time job, snowballed into a business. Um you know, we we grew that uh up until January 2020 uh to about a five million dollar company, 23 people, really amazing team, um, like super amazing reputation in Calgary. Uh and we were approached in 2019 by a national company um called Fully Managed, and I really looked up to them actually. We we had been kind of friends and shared ideas, um, you know, we had really good cultures. And they came to me and said, Hey, would you would you think about would you want to think about joining us? Um we're here's our plan. We want to grow, we want to go acquire some other businesses, take all the impact we're doing, and just scale it across Canada. Uh, and that sounded really cool. And I and I thought that was gonna be amazing for my team. Um, you know, definitely looking back, uh, there there was uh some good and some bad. Uh you know, um lots of good came out of it. We we did really good things. COVID hit in a month, two months after we finished the acquisition. And so um, yeah, that that was a pretty cool journey to to sell a company um, you know, before I think it was 35 at the time, um at 5 million, you know, the price was right. My team all got stock options at the end of the day. Uh, you know, the the vision of what those would turn into was pretty amazing, um, didn't totally come to fruition. Um, but you you can't like you can't get it all right. You you do your best, you're uh you're you're doing the right thing with the information you know at the time, right? And that's just like a theme through business. You're you're just figuring it out as you go, right? There's no playbook. Um so we sold TWT uh and I stayed on through COVID. I stayed on for almost three years. Um, two years after Fully Managed acquired TWT group, um, TELUS acquired Fully Managed as a whole. And uh as a part of the initial deal, I actually kept some ownership in Fully Managed, and so I was that uh I believed the the vision that much. I kept some skin in the game, um, and then TELUS bought it. Uh and about 11 months later I realized I'm not a TELUS employee, as you could imagine, and so um nothing against them, but uh decided to leave and uh you know had another year non-compete, so I kind of waited that out and people were knocking hard uh and saying, where do we go? We don't like what's going on here. Um all those relationships came back, and even the ones that had already moved on are like, oh, we see you're back in business, like we'd love to work with you again. We moved somewhere and they're okay, but you were you were always better. Uh and so here we are in those relationships again, right? Um, and so put the team together uh and started another company called Always Beyond. Um, so IT services company. Also, alongside that, um, prior to launching that, I created uh a coaching program for MSPs. And so what I said is like, what could I have used five years ago as an MSP owner? Like, what would be useful? And so I built this uh online platform, a community uh mastermind group, and I coach MSPs. And I I coach other MSPs that are competitors of mine in Calgary, like geographic competitors, and they love it because they're like learning all my secrets, um, which a lot of them aren't tricky. They're very they're very simple, but some of them take time. Planting seeds, building relationships, building networks, um, you know, helping others before you ask them to help you. All those things, uh, and and then obviously all the tactical things that I learned um on the technical side of running an MSP properly and and profitably, um, being able to help them scale. Because you know, you're you've been in the MSP game, there is a variety of levels of quality of MSP um because it's unregulated. And so I was like, how do we just raise the bar? Um and if I can if I can raise the bar for my competitors, it's gonna make me better, right? Against that that abundance mindset um is pretty amazing. And honestly, there's so much business and market share, and the market's growing in the MSP space. Like, even if I don't get another customer, my business should double, right? Like that's the market is doubling every five years at if if not faster, right?
SPEAKER_01:Yeah, the the MSP market's a fascinating one, and I I agree with you that there's such a wide variety of MSP types, delivery philosophies, everything from you know, two people in a computer in their mom's basement not to feed into a stereotype, to to some of the large, large like multinationals. And you know, it's not a one-size-fits-all. Like we do some work with kind of helping people find the right fit for MSPs, and and I liken it to to dating, right? It's it's not all about the technology, it's not all about the processes. Those things are important, and if they're not there, those should be some giant red flags.
SPEAKER_00:Yeah, for sure.
SPEAKER_01:But it's you know, who who are you gonna be friends with? Who are you going to um when something happens um and something will happen?
SPEAKER_00:Whose advice are you gonna take because you trust them?
SPEAKER_01:Yeah. Who who's gonna who do you want in the trenches with you as you make those business decisions that require technology? And and I'm also uh you know, for better or for worse, a big proponent. How do you make it fun, right? I I think that it doesn't have to be this um median that you'd read once a month or once a week or once a quarter.
SPEAKER_00:100%. Um, I mean honestly, like MSPs, you know, when you call in and you have a problem, like we're kind of part technician, but we're also part like psychologists, right? Like we're walking people off the the edge. It's like it's okay, we're gonna solve it, it's okay. Um so people are in pretty you know vulnerable emotional spots when they call in, especially if it's like a big issue or you know, they had a fishing issue or they got hacked or something. Like we become those rescuers and um it's a pretty a pretty cool business that way. I don't think there's no industry that's like that, right? Um and so yeah, just really raising the bar of quality, helping these folks like myself that accidentally ended up with a business actually know how to run a business, right? They know the tech, they're doing great. One or two person show can do, you know, run circles around a a big MSP because they're more technically rounded and and they just know what they're doing. But do they know how to run a business properly so that they're alive in a year, right? Uh do they know what cash flow means, right? Versus, you know, profit. Uh they're totally different. Uh and sometimes one will sync you even though you look profitable on the books, right? And so really helping people figure these things out, um, plan ahead, create visions of what their business could be, right? Because you know, they're running a$500,000 or a million dollar or million and a half dollar company and they're thinking about the next hundred K in revenue. They're not thinking about where do I want to be in 10 years, right? Uh and if you don't do that, what I've learned over my time is you just end up with what you end up with, and it's not intentional. So just uh yeah, really trying to support other people. Uh we've got people in my coaching group across Canada, across the US. Um, and it's really cool. A lot of the problems are the same that people face.
SPEAKER_01:Yeah. And and so how are you coaching these MSPs? Like I because I know the exact type you're talking about, right? They're they're brilliant technically, and it sounds like you followed in those footsteps where you you grew up with the technology in mind, not the business in mind. And and flipping that switch is way easier said than done. Um what advice would you have to someone that's listening that is, you know, we'll start on the MSP side. They've built an MSP and they're at that exact fulcrum where they now, you know, they're they're true teetering on that revenue number, they have a couple um team members and they're starting to have to learn to run a business versus um support customers. I know the answer could be join your mastermind. Um, but but is there any uh thoughts you have?
SPEAKER_00:At the end of the day, your business is a mere reflection of your leadership abilities, right? And so if you if you have leadership abilities of a million dollar MSP, then you're gonna be stuck there. You know, I've I've talked to people, they're they've been a million dollars for five years, and we went from zero to five and eight, right? And so like and and I, you know, five million dollars is my my mirror, right? How and how do I get past that? How do I grow past that? So really realizing at the end of the day that you're accountable for exactly where you are, uh, and it's and technology is not gonna help you scale past a million, right? Better a better stack, you know, um hiring another tech, a lot of those things that you might need to do, sure, but that's not gonna unlock the five million or the ten million. It's becoming a better leader, it's getting out of your own way, um, you know, s some really significant skills that people have to learn. Uh and if you don't learn it, you're just gonna be stuck is my micromanaging, delegation, right? Um the one mistake I see a lot of MSP owners make their first hire is the tier one tech. And I I I personally In my coaching group, they're like, I need to hire a tier one. I'm like, okay, tell me how much of what you do today you can delegate to them within two months. Onboard them, get them comfortable, show them all your systems. How much of what you do today can you give to them? They're like, Oh, maybe 20 or 20, 30 percent. I was like, so you're gonna free up 20 or 30 percent of your time, but that's not enough. Like your first hire needs to be somebody you you can give 80% of what you're doing. Um, and if you can't do that, then you need somebody more technically savvy. Those early days that really high tech, you can just delegate it to them and trust that it'll get done and you don't have to babysit are super important. And so just a couple small tactical moves. Um, you know, they they have a hard time swallowing the pill of like, oh, I I'm gonna have to pay 80 instead of 40. Right? It's like okay, well, but it's gonna unlock so much more for you, right? You can go focus on only what you can do as as the owner of the business, and that's the sales, the strategy, creating a vision, your tenure vision, all those things. You can't hire a tech to help you with that stuff, right?
SPEAKER_01:Yeah, and definitely unlocking that time because time is the most uh valuable commodity you have, and that that leverage of what you can do with that time.
SPEAKER_00:In those early days, you gotta use a lot of that time to learn those leadership skills. You gotta you gotta learn the strategy, you know, find a business coach. Doesn't have to be me, like any business coach can help you figure out your mission, vision, and values, right? Um you know, and so go find those people, lean on them, you know, go to your accountant, ask them your ask them every question you can think of until you understand your books. People under a million have no idea what their PL says or means. They don't even know what their cash flow is. So figure that stuff out. Because if you don't, if you don't know how to run your financials and you're at a million dollars, you will never get to five. You cash flow will hold you back the whole time.
SPEAKER_01:Yeah. Well we'll loop it back to your math conversation at the beginning. Like I think that those are some of the skills, whether or not you're an entrepreneur, the ability to understand money, the ability to understand financials, yeah, is a much rarer skill than than I anticipated. Yeah. Um, and there's not a lot of people in the world that that really understand how the money works on that front.
SPEAKER_00:100%. And if you don't have a CFO, your job as a CEO is to make sure you have enough money in the bank. Uh that's number one job. Don't run out of money. And number two job is to make sure that your sales are strong, right? Like you know, if you don't have a salesperson, that's on you. If you can do those two things, then you have a really good foundation for scaling an MSP. And being able to hire those techs that are, you know, the right fit, the right technical expertise that you need.
SPEAKER_01:For for sure. What about on the other side? So we we talked about the MSP side of things um and how you level up. What if you're the customer of of one of those MSPs where you're working with them, they're they're awesome people, but but they're struggling turning that corner as well. And you know, is there any advice you have for the people that consume MSP services around kind of picking that right partner?
SPEAKER_00:Yeah. Yeah, good question. I think you I think consumers of MSP services, so other businesses, um you know, they don't have a lens into our world, right? They they get all these buzzwords and they get excited and a you know, AI this, cybersecurity that, and they come to the MSP and they're like, what do we do? And your MSP probably gives you, oh, here's a couple ideas. Um, but they're you have to realize they're probably figuring it out like you are, right? Because things are moving so fast in the MSP space. Um, and so I've been really fortunate that my clients have given me the grace to learn and figure it out and obviously be ahead uh of them in most cases, um, but sometimes you just can't be, right? There's so much going on in the MSP space. I think what businesses are slowly shifting towards now, and like you alluded to earlier, is that technology and IT services are really drivers of business outcomes. So if you can get really clear on what your business goals are, and whether that's profit, growth, efficiency, um, and you can bring that to your IT provider, this is the conversation a lot of companies avoid because they're like, I don't want to tell my IT guys that here's our growth, you know, here's our growth goals and here's our efficiency goals because you know it's just like too internal, too secret. But if you don't tell them, then how how do you expect them to help you with technology to solve those problems? Because nowadays the answer is more and more becoming the answers technology, right?
SPEAKER_01:100%. And I I feel like there was this giant push over the last 10 years in the MSP world to really standardize everything. So there was a ton of MA, um, there was a ton of best practices, and there's there's a uh you know a few voices that have said, here's what an ideal MSP looks like. Yeah. And and a lot of them have started to really mirror each other in terms of those best practices. Yeah. I think to your point, where that starts to fall apart a little bit and where companies start to hit some of that friction too, is when you start to go outside of the standard to some of their core applications or the things that make them money as a business, um, there's this friction point when it's out of scope. Um how are you seeing that shift in terms of service delivery within your own business, but also in the industry as a whole?
SPEAKER_00:Yeah, I think um all of that outcome work is becoming projects and and really people are starting to think about is like how can I spend another five grand a month with my MSP um to come in and do business process optimization, look at a problem we have and help us navigate what technology makes the most sense to solve that. How can I spend five grand to bring them in every month, get them involved in my business, um, and turn that five grand into a huge ROI, right? Because you could easily any MSP can easily come in, you give them five grand a month to focus on this stuff, um, they can save you more than a full-time equivalent of hours in a year. And then after that year, it's just gravy. So you're uh you're investing and you're seeing an immediate return on results on that on that investment, and then you just compound that, right? It's the you know, you constant improvement. And so that's the shift of MSPs. All the operational stuff, the cybersecurity, the setting up new users, all that stuff is just operational. And so we're seeing this split. MSPs are like, yeah, we can do operational IT all day, every day in our sleep. There's per user fee. Um, off you go. And then now let's focus on the better conversation around how do we use all the technology you have now more effectively? How do we empower your people? A lot of times, how do we train your people to use it better? Um, and just really set your business up for success that way, right?
SPEAKER_01:I I really like that analogy used of the ROI, especially when it comes to some of the intangibles, like the business process stuff, where it's it's tough, you know. I guess you can have a book of like knowledge-based articles at the end, but it's it's tough to see in a traditional sense sometimes how that turns the lever from an ROI standpoint, right? Like I think if you um in a very crude example, if I go buy a tractor, I can see how that makes me money. Yeah. Um what do you wish business owners or business leaders knew about some of the technology ROI that's just a hard hill to climb right now for them with just the way that business has been done for the last X number of years?
SPEAKER_00:Yeah, I think two things. I think business owners need to get more comfortable with change. They can't just be like, oh, these systems work, they're fine, we'll just put put another body in. They just need to be like, okay, we're comfortable with change. And then number two is the CEO and like the executive leadership teams have to be the drivers, right? You can't just delegate your IT to your office manager and then hope you get results and get ROI. It needs to come from the top, and it needs to be a part of your business plan, right? You need to be like, okay, um, Amazon's throwing robots everywhere. Uh we're not doing that. Uh, and we have a warehouse. Why are we not? Okay, how do we dig into that? Where do we start? Your MSP might not be the person to sell you the robots, but they can sure help you navigate where to go, what to think about, the things you might need to upgrade to be ready for it. A lot of people have a ton of technology debt. If you have a server in a closet in your office, you're probably at least five years behind technology already. You need to take that old ERP that still relies on a server and you need to upgrade it yesterday. Um, you know, yeah, it's gonna cost you 100 grand. You have to do it. It's otherwise you you will get run over by your competitor, right?
SPEAKER_01:So I'd love for you to paint that risk a little bit more as well. Because I I agree with you 100%. There there's this hesitancy to act, um, but the we're not slowing down. No, uh, you know, the genie's not going back in the bottle. Um and the things that I love are that AI, security, technology are now becoming part of the, you know, I'm a popular guy at barbecues now. Um but at the same time, you you can't go back. And we're not going back, like we're not going back to on-prem servers, we're not going back to some of these legacy technology philosophies. How do people start to make some of those shifts and we're really what like what happens if they don't?
SPEAKER_00:Yeah. I think the the biggest hesitation I see from a business leader in saying we don't want to change our ERP or like our core line of business application, we're gonna keep the one that's on a server, we're gonna just keep living along, is they don't want to cause more work for their people. Right? It's a sh it's the short term, it's that 12-month project that's gonna be really painful. Um, and but once you get past it, uh the light on the other side of that tunnel is awesome because now you can integrate tools, you can streamline things, you can ask your people what do you hate doing every day, and you can figure out a way to automate it, right? You can make their jobs easier, you can have them focus on higher value things. Um because the the problem is if if you don't rip that band-aid off, uh you will have to eventually. And then the other thing too is that as a leader, you you need to train your people that change is okay. Um, but you also need to set them up for success and you have to give them a bit of time and give them the resources to do these projects, right? Say, okay, we're gonna bring in one or two people as consultants to help out, we're gonna take that off your plate so you can focus on this project. Um, you need to figure out that plan and and make it work for them. Um at the end of the day, even back to the MSP comment I made before is like you're you're ultimately accountable as a business owner for the success of your company, right? And I don't see a future in 10 years or even five years where companies running a line of business app or a ERP on a physical server are around anymore. Like, like I think their profitability is gone, their competitors are eating their lunch because they're doing it ten times more efficiently, because they have you know better systems, better processes, their people are doing more valuable things. Um and so you need as a business owner to look at that. Um, you know, and the other problem too is there's all these folks that own a business that are like teetering on retirement or selling. And so they're like, well, what I'm not gonna do it because I'm selling in three years. Or and it's like, okay, well, if I'm a buyer of a business, I'm probably aware of that. And uh either you're gonna take advantage of that and that's gonna be factored into the price. Um, or or if you're ahead of it, maybe you get more money and your team is set up for better success on the other side of that.
SPEAKER_01:I agree. We've started to see some of those discussions where it does get factored into your enterprise value of what is what is the backbone of your organization and how have you integrated technology to differentiate.
SPEAKER_00:Yeah, we're I'm talking to clients that are doing MA, and I'm like, you should do a technology audit as a part of your due diligence, which hasn't been a thing of the past, but now it's like, oh, you have some serious tech debt, like all your computers are six years old, so we're gonna have to come in and spend a half a million bucks on computers. Yeah. Like that comes off the purchase price, right? Um, and and not only like how you do anything is how you do everything. So it just shows how the business is run. Because if you don't have, you know, if the the welder doesn't have a good welder, you know the product's not coming out well, right? Same on the IT side, right?
SPEAKER_01:Well, and I think that just especially as the workforce starts to turn over as well. You know, I just uh you hear these stories of someone walking into their um you know Windows, and this is probably a little bit dramatic, but their Windows 95 desktop computer, you know, the big like the old CRT monitor and just like just walking out the door on there for me, this is not for me. Um because that's the you know it's the way of the dodo on those ones.
SPEAKER_00:I've had I've seen a I've seen a client give a a new employee a five or six year old computer and that person leave two weeks later. Yeah. And our tech was like, hey, like, why'd you leave? And they're like, they won't give me good tech, like all their systems are like hard to work with, like I just can't do it.
SPEAKER_01:Well, and it becomes an expectation, right? And like I've had this conversation as well um with our own team, which is you know, the the output, um, especially for some of these kind of digital natives. Yeah, um, the people that have grown up with this technology is insane. But if you also give them an abacus to do your books, um it's not gonna last very long.
SPEAKER_00:But if you embrace that, you get the ROI out of it, right? Like, you know, people they they make the argument to me that like, oh, Macs are so much more expensive. I'm like, yeah, but they're faster, they never have issues, so I'm always productive and they last for five years at least. You know, people are using 10-year-old Macs and they haven't slowed down, right?
SPEAKER_01:I'm I'm glad I have a fellow Mac brethren here because um, you know, I feel like we're the only two MSP people that use Mac computers.
SPEAKER_00:Every person in my MSP has a Mac.
SPEAKER_01:Oh my goodness, you're speaking my language.
SPEAKER_00:And and you know the reason is because they all know PC.
SPEAKER_01:Yeah.
SPEAKER_00:And we're gonna have a client that's mostly PC, and the one or two folks are gonna be the CFO and the CEO with a Mac. And if that person calls in and you're fumbling around like you don't know what you're doing, who's getting a new MSP soon?
SPEAKER_01:Well, and I I've heard that this is getting way too specific with the story of, you know, um the the the support ticket where they're like saying click well, just click the close button on the on the right corner. If you're on a Mac here on the uh you're a little lost there.
SPEAKER_00:Yeah, exactly.
SPEAKER_01:So we've gone um almost 45 minutes without really diving into AI, and it's something that I do want to understand. Um, you know, not I'm not gonna ask you to pull at your crystal ball for what happens with the world, but I am gonna ask you with some of your predictions around what happens to the MSP space.
SPEAKER_02:Yeah.
SPEAKER_01:Because there's been a lot of conversations around how that changes service delivery, how it changes the client experience. What's your prediction in terms of what people can expect from their MSPs in the upcoming years because of AI?
SPEAKER_00:Yeah, I think you'll see um MSPs differentiate themselves by using automation, using AI tools, streamlining things so that they can increase their gross margin and their cost of goods delivered. Um the thing about support is I think support as a whole is going away. Right? If um if you have a client that's fully modern, fully cloud-based, modern technology, good laptops, um, the ticket amount should be very low, and any of the tickets that come in should be at least a tier two level and probably soon a tier three level, right? Those those tier one problems are gone, right? They're just disappearing. So support as an MSP offering is just disappearing slowly, right? So I think that's one prediction I have. I think two is that AI, you know, obviously there's all the scare tactics and podcasts that are, you know, in two years we're gonna we're gonna all be on uh basic uh you know. And and so, but I don't I don't think that's true. I think these adoption curves for businesses specifically are like a decade. So I think the adoption curve of AI is gonna be ten years. There's gonna be the companies like Amazon and Google and Meta that are really way ahead, but all the small, medium businesses and you know, folks that are doing physical things, manufacturing and trades, and like those things are gonna take a lot longer to to really adopt technology. Um but MSPs are leading that, right? So MSPs have to be ahead of it, they have to do it internally, and they have to build that muscle, and then they have to go to their clients and say, here's how we can help you, here's what we've done for our business. You know, accounts receivable is all automated now, fully automated. We don't have a person. Um, let's do that for you. That's gonna save you a full FTE, right? And let's get that person doing more valuable accounting work. Right. So I think that's the prediction over the next five years. That's gonna be the big focus. Um, and then there's gonna be the MSPs that are like, uh, you know, I don't want to do the effort, I want to put the effort in, and they're gonna you know hang on to the physical servers and keep telling people that cloud's not secure, and uh we're gonna leave those folks behind, right? And you know, hopefully they're close to retirement.
SPEAKER_01:Fingers crossed. So yeah, it's an interesting discussion, especially when you think about the the revenue mix and even the margin mix around kind of service versus some of the other elements of the business. Yeah, there definitely is gonna be an evolution in the MSP space, and you're spot on. The ones that don't keep up um are really gonna have some challenging years ahead.
SPEAKER_00:Yeah, and even software too, right? You say you look at all these vibe coding apps and you're like, build me a CRM, and it builds you a decent CRM. Right? So I think there will also be a shift where MSPs can be like, oh, you're paying X, you know, you're paying whatever for HubSpa. Like we could vibe code you one in about 15 minutes. Right? Let's sit down and we'll do it for you.
SPEAKER_01:What 100%. And then there becomes the support of those things potentially, and the the circle continues. But I think it was Satcha and Adela that said, you know, Sash is dead. Yes. Um and and I think that you're right, like the use case of I can buy this specific platform for thousands of dollars a month, or I can build my own fairly seamlessly.
SPEAKER_00:Yeah, for sure. Especially they're giving you the tools that are um you know built on their el their learning models, right? And it's like, when can I go to Copile and say build me my own 365?
SPEAKER_01:One day.
SPEAKER_00:I don't want to use Microsoft to host my email anymore.
SPEAKER_01:I'll censor that part out so we don't get uh I think this is going on YouTube.
SPEAKER_00:So perfect. We love Google, yeah.
SPEAKER_01:There we go. Um so I feel like you and I could um continue this conversation for another three or four hours. If someone wanted to get a hold of you to learn more about you, learn more about either your consulting or always beyond, um, what's the best way to get in touch with you, Sean?
SPEAKER_00:Yeah, find me on LinkedIn, uh just look up Sean Freeman um or seanfreman.ca is my website, and uh yeah, love to connect.
SPEAKER_01:Amazing. Well, it it has been an absolute pleasure to have you on. Um, this has been a phenomenal discussion, and I thank you so much for for taking the time today.
SPEAKER_00:Yeah, thanks for having me on and uh let me share my story.
SPEAKER_01:Cool.
SPEAKER_00:Appreciate it.
SPEAKER_01:Awesome, have a good one. Thank you so much for tuning in. That was an awesome discussion, and really grateful that Sean joined us. If you've made it this far, like and subscribe on YouTube, or follow and leave a review on your favorite podcasting platform so you don't miss any future episodes.