Joey Pinz Discipline Conversations

#818 Jason Magee: 🚀 From Platform Builder to Cybersecurity CEO: What Real Leadership Requires

• Joey Pinz • Episode 818

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In this wide-ranging and deeply thoughtful conversation, Joey Pinz sits down with Jason Magee, former CEO of ConnectWise and current CEO of Cynet, to unpack what leadership really looks like when the stakes are high and the noise is constant.

Jason shares his personal journey through a major health challenge, a high-profile CEO transition, and the mindset shift required when moving from leading a global platform company to scaling a fast-growing cybersecurity organization. Together, they explore the difference between leaders and managers, how to spot real growth versus empty visibility, and why disciplined decision-making matters more than ever.

The conversation dives deep into AI, automation, cybersecurity, and the realities MSPs face today—from talent shortages to increasing threat pressure and consolidation. Jason also opens up about motivation, legacy, burnout avoidance, and how leaders can stay grounded while navigating complexity.

This episode is a masterclass in modern leadership, focus, and long-term thinking—for CEOs, founders, MSPs, and anyone responsible for building teams, platforms, and trust in a rapidly evolving industry.

 

🔑 Top 3 Episode Highlights

  • 🧠 Leadership vs. Management — why titles don’t define influence
  • 🔐 Cybersecurity + AI Reality Check — separating signal from hype
  • 🧭 Sustainable Growth — how leaders stay proactive instead of reactive

 

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Jason Magee Live-Mix.m4a
Thu, Jan 8, 2026

0:01 - Speaker 1
Yeah, and so your shoulder now, are you 100%?

0:03 - Speaker 2
Well, it was the neck. Oh, that's right, I'm sorry. No, I'll never be 100%.

0:08 - Speaker 2
Really, ever?

0:11 - Speaker 2
No, I mean, because I had three vertebrae fused together, so my range of motion will be, I don't know the exact percent. They actually tested me today, and since I started physical therapy, my range of motion improved significantly from what it was two, three months ago. Backing out of a parking spot. I couldn't really even turn right. I had to turn my whole body right, so But yeah much better now, but I'll never be a hundred percent to someone who didn't have the surgery And there wasn't one particular act that started this it's just you're sleeping wrong.

0:45 - Speaker 1
You just felt pain you think you said Waits act that started it happened.

0:53 - Speaker 2
Yeah, no idea It could have been from when I got hit by a car when I was 10 11 years and just, you know, never got diagnosed and never really became an issue until, you know, this time last year, right? At the time when it was going on, I don't know if you and I had this conversation back then, but January, everyone does dry January, or not everyone, but you know, it's a big thing, right? Or, hey, I'm gonna get on the health kick. And so I decided last January, going to do dry January for most of January. Then I was going to stop drinking caffeine. I got my coffee, so I like my caffeine. I was going to walk three to five miles a day. And I was going to do a 20-minute daily calisthenic thing. And new me transitioned between ConnectWise and what was to be next. I get three, four days. And I started to feel discomfort in my neck. I'm like, oh, I'm pushing myself too much. But I'm like, I gotta do the full month of what I'm trying to do. And I kept going. And actually, when I was active, it actually wasn't bothering me that much. It was when I stopped. And then mid-January, it was really bad, and then it started to get better. And then when I started, then I'm like, I'm not doing dry February. I couldn't wait to get my Dunkin' Donuts coffee. And the calisthenic 28th thing I was doing, day thing I was doing, I completed it. So check, check, I was feeling good from that standpoint. But then my neck and shoulder, and I thought it was my shoulder at the time. It was just like a lot of pain and discomfort, and I couldn't sleep, and this and that. Pinged my doctor, went in. Doing all these tests, gave me a cortisone shot thinking it was just like, I forget what it is, but build up of stuff in the shoulder. And yeah, did all that, nothing was working. It was getting worse and then got to a point where I think at one point, they gave me like, I don't know, and I'm probably exaggerating, but it was like 15 different injections into different areas of the shoulder and back. Cause it was that like, you know, bad. I remember early February when I started at Cynet, we were up in Boston for sales kickoff and we were doing an all up thing. And I mean, I was walking around like this, like, cause if I put my head and neck and shoulders back, that's when it really hurt. And yeah, then, you know, came back from that trip and he's like, all right, let's get you in for MRIs on your shoulders. Did the MRI on the right shoulder and they just saw the normal stuff. I forget what it's called, not spurs, but like build up a calcium or whatever. They're like, that wouldn't be causing the, you know, neck and the numbing of your hand and all that. And then they sent me back to do a MRI on the neck. And that's when they saw that I had a severe compression at C5 F6-7 area, mainly in C6, and that's when they said the surgery that needed to happen was ACDF, it was called. Yeah, it's the Peyton Manning surgery.

4:29 - Speaker 1
Peyton Manning had it, really? Oh boy, you know it's bad when somebody gets named after it.

4:34 - Speaker 2
Yeah, but the difference between he and I, and you know, I'm still too early in my recovery, is he went through intense rehab and then won a Super Bowl, you know, not that long after. So, there's hope.

4:46 - Speaker 1
said there certainly is hope. Yeah, but I mean, I remember talking to you like you couldn't even sleep.

4:52 - Speaker 2
Fast forward to today, I do have a sleep challenge. But it's because my wife will tell you this, you know, prior to all this, I was pretty aggressive sleeper tossing and turning like, at times like, you know, I'm sure it feels like, you know, bouncing around. But it's more of a mental thing now that I'm like, Alright, well, I can't do that because I don't want to injure my neck or mess up all the, you know, I've got a plate and screws and all that, you know, as the bone is fusing together. And so it's more of a mental thing that I'm like, all right, well, I gotta turn. So I wake up and I'm like, oh, I gotta turn. And then I turn and go back to sleep. I do that probably five, eight times a night. So sleep is still a hard to come by thing. But that's more of a mental thing. You know, not a year, but April 15th or 17th will be a year since the surgery. So, um, and depending on everyone's different, right? Full recovery is somewhere between North of six months, but up to 12 or so months. And by recovery, the bone fusing together.

6:01 - Speaker 1
It was all here at Tampa Bay general.

6:03 - Speaker 2
Tampa TGH TGH.

6:06 - Speaker 1
This community here in Tampa is very proud of that hospital. It's a very interesting dynamic of this great city. So you left ConnectWise around November of 24.

6:17 - Speaker 2
Yeah, I think November 11th, I stepped off stage at IT Nation and stage exit left, right, something like that.

6:28 - Speaker 1
Yeah, never came back. And so then you didn't start SignNet until February. So what were those two months? Or six weeks like from 100 miles an hour busy to almost three months.

6:41 - Speaker 2
So three months. Well, the thing people don't tell you is when you do have a time in between is you do wind up doing more work, really, right? Because you're looking right, you know, at that point, I wasn't still 100%. Hey, it's I net. So went through the process of interviewing and I was few times a day doing interviews, right? You know, look, it was it was an overwhelming positive response of the amount of people who reached out that wanted to interview me to be CEO and lead their company to the next level in the industry by industry managed service provider industry channel outside of the industry, large companies, public companies, mid sized companies, you name it, and so when you're doing that process, it's a full-time job, right? You're doing a couple of calls a day, you're getting on planes, interviewing people, going in person to interview people, or them to interview you, and then at the same time, going through the side net process, and then obviously I'm still on a couple other boards and doing advisory work and everything else I'm connected with.

7:57 - Speaker 1
So during that process, Jason, are they interviewing or are you interviewing them?

8:02 - Speaker 2
It's both, right? I mean, any good interview process, it's always, you know, bi-directional, right? It's, you know, hopefully, you know, it doesn't matter what level of role or position in a company, you know, you've got to want to work at that company, right? Because if you go through the process and you didn't do your diligence and you land somewhere, again, regardless of level or position, you'll be unhappy, right? And then there's impact on not only your professional and performance at the job that you stepped into, but also at home because you're unhappy there and then that bleeds over and so on. So yeah, I mean, no different going through that process, right? Yeah, I'm interviewing, kind of seeing what the game plan is, what the board or investors or the executive team are aligned behind. What is team dynamic? What's the culture? Is it something I'm passionate about, right? You know, what they're doing, what they're solving, what's their mission and vision and all that good stuff. So yeah, it's a, you know, it's both. That must have been me interviewing them. Yeah, both.

9:10 - Speaker 1
That must have been something. I'm sure you had a lot of, a lot of offers, a lot of options. Why did you choose SignNet?

9:17 - Speaker 2
Yeah, again, it was a great, I was flattered. It was a lot of positive response. And yeah, I had lots of offers, offers, papered offers, and all that good stuff. And look, I get asked this question a lot, Joe, around why SyNet. The funny thing about the SyNet one is it's the one that I engaged with first before I even knew that I was gonna step away from ConnectWise. And it was, you know, a bunch of reasons, and I'll get into some story in a second. But the why behind it is a the chairman, Doug Brockett, Douglas Brockett, he and I known each other and work together when he was running things over at storage craft. And we had the partnership at connect wise, and so on and, you know, mutual respect and did a lot of business together and so on. So he was there. As I was going through the process, he validated a lot of things in terms of the company and their approach and direction and so on that intrigued me. But regardless of Cinet, when I knew that I was going to make a change and go through a transition, you start asking yourself, what is next? If you go to my wife, she'd be like, retire. If anyone knows me, you know me, I'd get bored probably pretty quick, right? So I said, what is next? And obviously, you know, we're at this point in time, and, you know, not just technology, the world around AI and automation and cyber and threats and increase in threat landscape and all these things. And I'm like, well, let me start with technology, where do I want to be? And I very quickly got to the point of right, well, definitely wanted to be in the cyber world, right? I was passionate about it. It was a lot of things that back in the day, Arnie and I put in motion some years ago at ConnectWise. And then I kept taking that forward at ConnectWise when I stepped into the CEO role to build out a pretty sizable business unit there. So passionate about that, still very relevant and will continue to be for the foreseeable future. And things are getting more complex and not easier, and threat actors will do more, right? And then the whole automation AI craze, and not a craze, but it's the future. So I'm like, all right, got to be in those areas. I'm a platform guy, right? What we built, what we were building and reinventing and reimagining over at ConnectWise before I left was another platform. So big on platform, platforms win. Look at Salesforce, look at ServiceNow, look at Microsoft, look at all the big technology, Amazon, you name it. They're all platforms. Platforms win. And had to make sure that wherever next, regardless of technology, solution, industry, whatever, it had to be a platform play. And then the added thing that I was looking for, right, cuz I wanted to be able to make immediate impact on whatever the company was and what was going to be next. And what I didn't want to do was step into a company that had a customer perception or brand problem, right? Because I didn't want to have to go in and step in and spend, you know, 12, 18, 24 months on fixing that, right? Because that's, you know, it's fixable. Don't get me wrong. It's just sorry for those We're suppressing our expectations and what's possible and things like that. And then you get to the fun and focus on growth and doing the great things and be an innovator and all that. So it had to be someone that was in good standing with the customers and good feedback from the social world and people interacting with the company. And as I continue to go through the process, and chat with the great investors we have, the founder, who was the prior CEO that I've succeeded, Doug, the chairman. It was apparent that when I went down my checklist, right, yes, it's a cyber company, great. You know what, they've got an AI and automation component. Wow, two birds, one stone, right? I'm getting both, right? So check, check. Platform, it's a unified all-in-one platform that does not just endpoint, it has a little bit of network and a little email, a little of posture management and all these other things, right? And platform concept, right? And we'll continue to build out on that platform concept, you know, in the roadmap in this new calendar year and fiscal year and so on. And, you know, so it had all the things that I wanted to look for. And then I started to do, right, social search, right? What's being said, right? No company's perfect, right? So it's not like I didn't find anything negative or indifferent and so on. But it was few and far between, right? And some of that's size and scale and so on. But even some of the comments were around, they were great, right? Had no problem. They didn't have the name, right? The brand name. Now, not a brand problem. Just didn't have the name, right? No one knew them, right? I'm like, all right, that I could work with, right? Then I'm looking through all the materials that Doug and one of the lead investors sent to me. You could see track NPS score, high NPS score, so validating some of the external stuff. Started to chat with people, right? Yeah, customers, partners. They had great things to say about it, right? Again, constructive feedback, everything like that, which you would expect. And then there's this thing called MITRE, ATT&CK Evaluations happens annually. Scinet performs pretty well every year for now five years after the least recent, right? You could go look at it, you could see where we score and perform in all the categories. So more and more, I'm like, that's pretty nice. Again, cyber. Automation, it's a platform, really good customer sentiment, right? So it started to come together and even then, I'm like, all right, why would I do this? And I remember when I was having the most fun in my career, right? And even my early tenure in ConnectWise where I was having the most fun We were a bit smaller, more agile, and focused on growth and all these other things about moving an industry forward and so on. And I'm like, that's it, right? So I had all of what I was looking for in the next company. And then when was I having the most fun in my career, right? So ConnectWise, I had that, and other stints in my career, I had that. And that's when I'm like, all right, Doug, let's do this. And yeah, look, it was an easy process. I started chatting with, I think, the recruiters and Doug in June of 24. Possibly earlier, but I think it was June. I made a decision literally the week after, I think, IT Nation. I'm like, all right, Doug, let's start really chatting. I think we came to terms. You know, sometime before the holidays. And that's all while I'm, you know, traveling, interviewing, getting offers from others, and so on. So yeah, that's kind of the story, the, you know, the why behind Sinet.

17:40 - Speaker 1
And the transition of you becoming CEO at Sinet, how different was it? Then you mentioned Arnie before Arnie Bellini, when he left when the founder left, and you became CEO at a company you've already been at. The transition was very different.

17:54 - Speaker 2
Yeah, so I'm not going to say vastly different, but different for sure. Because at ConnectWise, leading up to the partnership with Tomo Bravo, leading up for Arnie to hand the torch over to me, I was the COO of a company. And prior to that, on the go-to-market side, doing my thing over there. So I knew I knew a lot about the company, the culture, the people, the who's who, the leaders in the company, the customers, the partners, all that, right? So I wasn't starting from zero, right? So from that point by itself, that's the difference, right? Versus coming in here, obviously, I knew their aspirations and their desires and how I could help them and Obviously, I know how to take things that are a bit on the early stage side and scale them. So my transition here was all about that, the maturity and figuring out what was not working, what wasn't even in place. Cuz small company, we don't have everything, right? There's gaps and so on. So part of my transition was, so December we come to terms, and yep, this is what we're doing. I put all the other activity on the side, and then immediately, even though I haven't started yet, now I'm transitioning already with Eyal, who was the founder and the current CEO. We're doing calls a couple times a week. He's filling me in as to the things that I had already known that Connect was. So I jumped pretty much head first, prior to starting, so I had a starting point. So that's probably another aspect of the difference. And yeah, look, I mean, there's only so much I was gonna be able to do, and yeah, you step in anywhere, there are surprises, right?

20:01 - Speaker 1
Did you have to unlearn anything?

20:07 - Speaker 2
I wouldn't call unlearn, but obviously, look, I mean, I'm not perfect, right? I've made mistakes, right? Whether at ConnectWise, you know, in life, you know? So it's, all right, let's make sure that I don't make the same mistake, right? You know, the great thing about experiences and my journey, professional career journey, whether me or anyone, right, you have those experiences to draw from And, you know, most people draw from the good experiences and the bad, right? And the bad is, all right, let's stay away from doing that, right? A pattern recognition now, right? Hey, I've tried that, been there, done that, not going to work, right? So I could get in with the team, help educate them, and so on. So not so much unlearn, but leverage the experience, the journey, the pattern recognition to make sure we don't make the same mistakes. And then leverage the good. I mean, if I purposely unlearn things, in my mind, that's me purging it from memory, which means history will repeat itself and I'll make the same mistake twice.

21:16 - Speaker 1
And for those making that kind of transition, Jason, so they're going from one company to another, whether it's a smaller scale, a larger scale, the way you did it, what advice do you have for them?

21:29 - Speaker 2
Well, so this may or may not answer your question, but I think I'll touch upon pieces. Look, large scale and, you know, it kind of joke even with my team now, right? And even when I'm talking to people who were at larger companies going to smaller, right? And look, the benefit I had, you know, in hindsight I had was I did the journey, right? I was part of the journey early on at ConnectWise and helped make it a big market leader and so on, right? Thing is when you're large, growing, profitable, you have teams of people assigned to pretty much, you know, anything you could think of that a company needs to be doing, right? When you get to a smaller company, all right, who does that? Well, you gotta remind yourself, you gotta look in the mirror and be like, ah, that's the person that's gonna go take care of that, right? So you gotta get more creative, you gotta roll up the sleeves, you gotta be a bit more involved in areas that, you know, larger companies, you may not have, right? You may have had a person that would have been able to handle that for you and do it. And here and any smaller company, right, you're not going to have all the resources available, so you've got to learn new experiences. You've got to go through it.

22:50 - Speaker 1
Yeah, and it seems like you do a really good job of, I can just imagine these large pros and cons list you must have had, right, with all these options and trying to weigh that out. What makes a great leader, Jason?

23:05 - Speaker 2
Have you figured that out yet?

23:06 - Speaker 1
I haven't. Let me ask you this, what's the difference between a leader and a manager?

23:16 - Speaker 2
Yeah, so these aren't technical definitions and responses, just to be clear, right? But manager is managing things in people, right? Tasks, projects. Goals, yeah, you name it. Now, leaders care about all that stuff, right? And they want to hold people accountable to deliver on that. But leaders are hopefully inspiring, motivating. They are leading the way, right? Like lead by example, right? Don't just sit in an ivory tower. A lot of what I believe in, and you go back to anyone who's been on a leadership team with me, I don't believe in the ivory tower leader model, right?

24:04 - Unidentified Speaker
No, you don't.

24:05 - Speaker 2
Everyone has to be involved. You got to know the business, not just your business. You got to know what's going on with your peers and the other functional orgs and so on. So lead by example, know the business. Don't just be someone that's looking at numbers and saying everything's wrong. No one's perfect. Everyone has their challenges, right? Leaders understand that and they go in with a collaborative mindset. Seek to understand and whatnot. I'm not saying managers don't do any of that, Joe, but the day-to-day function is just materially different from that standpoint. Things people don't necessarily like also, and again, this is my opinion, leaders have got to be available. They're always on. I hate to say it, but for me, it is part of the expectation. And please for all managers out there, because I was in a management role at one point in time. You're doing a function and yeah, sometimes a little bit easier to say, hey, I came in at eight left at six and kind of clocked out. Again, been there, done that very important. It's what makes a company do what it does and make things happen. But leaders, right? I mean, if that manager, if someone has something going on in the evening, weekend, or whatnot, you got to make yourself available at times. So I guess, you know, outside of that example, I think leaders have to be ready and available, right? When something hits the fan, you know, you go into action. Again, you pull in the team that managers are and so on. So yeah, I mean, that's kind of my view of some aspects of what's different between manager and leader. And look, there are technical differences. As you could look, ChatGPT, Gemini, whatever your AI choice is.

25:59 - Speaker 2
Yeah, I've had managers.

26:01 - Speaker 2
And by the way, not every manager or person who has direct reports or leaders, and not every individual contributor, I'm botching this a little bit, but even an individual contributor can be a leader, right? A leader is a person it's again, a person people want to follow, right? Individual contributors could play that role, right? So that's the other part of, you know, what's the difference, right? You know, you've been in companies, you ran companies, owned a company, you have multiple initiatives and companies going on, right? And everyone has them, those go-to people in the company, right? That managers in, you know, C-level go-to, right? Their peers go to them, right? Those people, assuming that it's in the positive way, they're leaders, right? They're just leading in a different way because they don't have the C-level title or VP or director level. But yeah, so that's another aspect.

27:09 - Speaker 1
Yeah, I've had managers who thought they were leaders and they weren't. And sometimes managers look down, like they look up to a leader, like it's different. Both are very important, and we need managers to run companies, and we need leaders to lead. It's just a very kind of different skill set, and it can be a hard discussion sometimes.

27:30 - Speaker 2
Yeah, and again, leader doesn't have to be high up in the orchestra.

27:34 - Speaker 1
Right, it can be anywhere. Are leaders born, or can they be trained?

27:39 - Speaker 2
Yeah, look, I don't think I was necessarily born a leader, Joe, right? People have passions and desires, and they get motivated by seeing what other people have done, and how they've done it, and their experience in it, because they report to managers or leaders that they say, hey, I respond well to that versus not, and then they kind of help train and educate themselves. A lot of what I bring to the table, I think, as a leader, is I've Read in business books, I've Read in annual reports and how people conduct themselves, and so on, right? And then learning from the leaders that I've been around. But yeah, I don't think I was necessarily born a leader. I think it came with, in my mind, where I wanted to be in life and get to and so on. When I became the CEO of a company, I always wanted to be the number two to any leader that I worked for. So whether it was an executive sales leader, I wanted to be the number two to them. I wanted to be the COO. So when I got promoted to the COO role at ConnectWise, I'm like, that's the ultimate number two job. And then, yeah, I mean, then it turns out that I do the CEO stuff pretty well as well.

29:16 - Speaker 1
Were there things that you learned about leadership back then that you disagree with now?

29:25 - Speaker 2
I wouldn't say disagree with now, right? Because there's points in time that different things are needed, right? And then there's the generational stuff, right? I'm not going to say dictate or mandate, but they help things evolve, right? So you've got to learn to lead in different ways, right? And ways that I was leading 10 years ago, am I doing it all now? Well, probably not. It's different generation, different people, different ways, or aspects of the globe that I interact with and so on. So, again, I think most leaders, assuming they're the good aspects of leadership, things that they've used and done and whatnot to lead at certain points in time were appropriate at that point in time. And then as things evolve, so do leadership styles.

30:26 - Speaker 1
Yeah, you have to keep growing. When a company is growing versus just getting louder?

30:32 - Speaker 2
What do you mean by louder?

30:34 - Speaker 1
More visibility, you're seeing them more, but they're actually, is that growth?

30:41 - Speaker 2
Well, I think from an external standpoint, you know, if it's not a public company, right, you know, probably harder to tell the difference between what you're hearing and seeing on the outside, because someone could be a great marketing engine. And create a whole bunch of fan base out there, you know, touting and so on, and that could be, you know, thought of as, wow, that company's growing. In some cases it is, right? That is an indicator. If you're on the inside or if it's a public company, right, easy to tell who's growing, right? There's numbers and, you know, what's their financial profile. And then, you know, outside of that, is indicators, right? So if I just look at Scinet, right? When I came on board, one of the main things that we're orchestrating is how do we accelerate growth, right? Well, if you look at, all right, here's the goal, how do I know the things that we're putting in place are starting to work, right? And there's a whole lot of things that lead up to it, right? Which I close deals and more revenue, equals more year over year and turns into that growth percentage. Well, key indicator to that is what's your pipeline doing? Qualified pipeline to be exact, right? We're clear. So I look at how is the pipeline, right? And if you continue to see growth in your pipeline, qualified pipeline, that's a good indicator that you're going to start growing, right? If you have that trend, right? You're looking at it, you could say that company's growing, right? Because ultimately, you know, there's what's your win rates? You know, what's your pipeline coverage? If you got the appropriate pipeline number to have your coverage, and you have the win rates, you're going to deliver on your numbers, right? And delivering on numbers and keep investing in go to market resources, whether it's demand gen dollars, whether it's add SDRs for additional inbound outbound, whether it's adding more quota carrying sales reps for capacity to run more deal cycle and all that stuff. You know, there's lots of indicators in there that can tell you if a company is growing. There's other ratios and sales efficiency metrics. You know, LTV to CAC ratio can tell you if a company is healthy and growing. Sales efficiency, what's the productivity of a sales rep and all that stuff. Customer retention is a big aspect. Better to keep your partners and customers, right? This way you don't have to go and spend as much to fill the top of the funnel.

33:31 - Speaker 1
And growth just in services and maturity and the engine as a CEO, how do you, how do you maintain all those different areas and make sure they're all growing?

33:43 - Speaker 2
Well, how do, how does one maintain? Well, it starts with the other, right org structure, the right team and people, people that know what good looks like and what needs to be done, right? Because the key thing is, I want to make sure I'm surrounded with the people that, you know, have that pattern recognition, know what needs to be done and how to go do it, make sure they're looking at the key metrics, right? I have a so every week, my leaders and I come together, we look at, you know, our scorecard, right? Key metrics of the company, call it 20 to 30, right? But when you double-click, they have a whole lot more, right? And what I mean by that is, yes, I'm looking at pipeline as a key indicator, right? Every day, did we generate enough pipeline? Every week, did we? Every month, every quarter, right? You got to win the day, the week, the month, the quarter, right? Because you can't generate enough pipeline the last day of the month or quarter to make up for it. And then there's, hey, time to close, right? So if you do it all in the last day, you're going to miss your quarter. But I'm looking at pipeline. And if pipeline's slow, that's when I'll go to whether it's, all right, what's going on? If they come back that, hey, marketing has all their stuff together, then it becomes, all right, then I turn to my sales leader and say, hey, what's going on, right? But yeah, so I'm looking at those key things that's high level enough But can tell you all right, which direction do I need to walk? Hmm What's a what's a bad day like for you and how do you reset and make sure you don't you know act react, you know impulsively What's a bad day, I mean a bad day is you know On the personal side of let some of my family down or you know something along those lines that you know I disappoint or bad day, you know, professionally is we let a customer down or a partner down, or some something in the, you know, system that we're, we've put in and will continue to evolve, you know, false, right? That's when I start to have a bad day, right? Otherwise, like, I love what I do, right? It's why, you know, it's why I didn't retire wife's like, Hey, will you consider retirement and things like that? No, never. But no, that that's when I have a bad day. Otherwise, look, you know, going back to leaders and managers, and so on, right? We all have a responsibility to be problem solvers, right? Things are going to come up, right? Breaches are going to come up, someone's going to screw up and fail and this and that. And you know, yeah, you learn from those things, right? I don't ever get pissed. It's like, all right, there is the problem. Are we going to go solve it? What are the options we have? And as long as everyone understands that and we come together and we're united behind, all right, let's go solve this. It's not a bad day, right? It's a learning experience. Now, I don't always like having a whole lot of learning experiences pile up on the same day and week, but those could add up to be like, all right, it's time to go, you know, let's go grab a bourbon somewhere, Joe.

37:06 - Speaker 1
Nothing wrong with that. How do you prioritize and stay proactive versus, you know, of course I run a company like you mentioned, a lot smaller, but it seems like a lot of my time is putting out fires. And so how do you stay, you know, prioritized so you're proactive so you're not doing that and you're not always reacting?

37:26 - Speaker 2
Look, there's always gonna be a part of reacting, right? There's a balance and look, this is one of those things that evolve over time with I think most people, right? You tried new systems, you tried new things, and so on. I kind of use your thing, to some extent, it's discipline, right? And what do I mean by that? It's like, all right, what's, how are you setting up your day, right? So you have the time where you're thinking strategic, more proactive, and then you're spending X amount of time on the proactive stuff. I think that's probably the best thing that works for me because otherwise everyone could open up their email inbox and be inundated with reactive, the things that pop up and the escalations and can you help me with this and can you give me an answer? You get consumed by it, right? Respond to the email, then you get three emails deep. They respond, so then you respond and you get caught in that, right? The only way out of that is make sure you carve out time to work on the important stuff, right? Leading the companies, being strategic, thinking about the future, some of the fun stuff, right? So I think that's the best way, right? In terms of how do I not get consumed by all the fire drills and so on. And in terms of prioritization, it's about having a plan, right? And I work with my team on this quite a bit, right? Will there ever be a true North Star or The answer is no, right? There are milestones, and then there are things that you're marching towards, right? Think vision, right? There's vision you're marching towards, you may never get to the vision. But at least it gives you a place that you're trying to go to. So then when things come in, and you have to prioritize, be like, all right, well, out of these three things, which thing is getting us closer to there, right? Whether it's financial metric, whether it's a, you know, product roadmap, and hey, we want to build this platform to do x, y, z, right? Well, now you know what x, y, z and the platform needs to be, right? What are the key things that you have to do along the way that will get you closer there. And if there's something that's not, maybe gets put on a long list, maybe it goes into a different sprint at a later time, and so on, right? No perfect system, but that's what helps me prioritize, right? So, you know, I kind of know, with my go to market, right? Hey, we're striving for over the next 18 months. And that's kind of the North Star. All right, well, hey, all the things that come up throughout the day and questions asked and the wants and needs and you know, shiny objects, right? Well, will this stuff help us get there? Right product, we know where we're taking our platform over the next three years. And look, it's always North Star is always subject to change. We Live in a hype industry, just think of what AI has done in the last three years, right? It's transformed everything, right? And if you didn't adjust, right, and move quick, people are being left behind, right? Northstar has just helped you from the prioritization standpoint, and it helps with alignment as well, right? Because if you don't have a destination of sorts, it's hard to drive towards alignment, right? How can I get a product leader or an engineering prospect to come work for us, if they don't know what we stand for and where we're going towards and the exciting stuff that they're gonna be able to work on and contribute and so on, it's a lot harder, right? So, you know, that North Star, the destination, whatever you wanna call it, the goals, right, that helps you prioritize, drive alignment, get people motivated and excited and so on. So I said a lot more outside of the presentation.

41:18 - Speaker 1
Yeah, yeah, it's exactly right, but it's easier said than done. A lot of times, right? Because, but if you align it all properly, talk about innovation, Jason, how do you know where to innovate and kind of ignore the hype and where to focus? There's so much, you know, that CES is going on right now. And I keep getting inundated by all these things. And most of them are completely unnecessary, by the way, but kind of fun. But how do you know where to innovate in Sinai?

41:47 - Speaker 2
Yeah, look, I mean, innovation's not easy. And it's not easy for a few reasons, but the main thing on how do you, right? First starts with listening to customers and partners, right? Listen to the market, the audience, the customer profile that you help serve. In our case, protect and serve and all that stuff. They may not be seen as the innovators and the thought leaders, But they're the ones that are encountering the problems all day long that need solutions. And your current solution, whether it's side net, elsewhere, or whatever, may not solve those needs today. And that's where some good ideas and innovation could come along, right? So it starts with that, right? And then, yeah, I mean, there's the innovators in the world that Elon Musk, just look at all the stuff he's touched in innovation and so on, right? It's just a lot, right? Those are different breeds, right? But I think most companies, most leaders, most innovators start with customers and partners, listening, seeing what gaps they have, what people aren't solving for, what could make their lives easier, and taking that feedback and seeing what's possible.

43:15 - Speaker 1
Where do you think AI and large language models are going, Jason?

43:21 - Speaker 2
Yeah, I mean, they're not going away, right? Now, look, this is still early innings, right? So just look at how far and fast it's progressed between when Chachi BT hit mainstream a little over three years ago until today. So it's not going anywhere. It's here and stay. It's only going to continue to move faster, get smarter, for some people scarier. You know, I have a different philosophy on all of the AI robots and so on. I can see why people get concerned and scared. For me, I look at the human race. We've evolved and adapted pretty much every key point in time that we needed to, industrial revolution being one of them. And people are going to lose jobs. And you know what? Well, hey, there may be a short blip, but ultimately, long run, better for everyone. Think of the internet and dot com, right? Earlier version of this, right? Oh, change the world. Oh my god, I'm going to be out of a job, and look what it did, right?

44:35 - Speaker 1
Created more and different ones.

44:37 - Speaker 2
And we evolve, and we become. Different versions of ourselves, and we were doing this task today and meeting this group today, and now we're doing that differently in a different fashion tomorrow. I think level one engineer writing code, well, now they have an opportunity to leverage AI, write code, and become a manager of bots and LLMs and AI and making sure that the output that they're providing is producing better quality and so on. So people who evolve and learn and educate and get educated on this stuff will elevate themselves. So that was a little bit of rabbit hole of the question, but my mind is we're going to evolve, we'll be good, and AI and automation, all that, not going anywhere. It's only going to get more integrated into the way life, personal, professional, the educational systems will embrace it and adopt it, you name it.

45:45 - Speaker 1
Is it, should it be further than it is now or is it right where it should be? Or has it gotten here too quick? Where do you think we are with it? They say, last I heard it was like a middle school. They're saying like, we're right at middle school. Did I hear that correctly?

45:58 - Speaker 2
We're early stages. Yeah, we're still early stages. I mean, but look, AI, And I forget who said this, it's not a new concept, right? I mean, there's plenty of companies have been around and people talking about it forever, right? Probably 50 years, right? Look at IBM Watson, right? They poured a lot of money into it before I think people were ready. And then there became the consumerism, commercialization of it. When Chachi BT hit mainstream, right? I think I may be off, but zero to 100 million, you know, users like overnight adoption ever. Um, so I, I don't know how to answer whether we lead or too early. It was probably meant to happen when it did.

46:48 - Speaker 1
And how is AI used with sign that is in everything that you do?

46:55 - Speaker 2
I mean, well, hard for me to say it. Everything you do. From day-to-day stuff that all the colleagues are doing for their day-to-day work and task and project work, people are using AI. Our engineers are using AI to help generate code and advance the product and platform and lots of documentation being leveraged with AI from the HR department to product to education and release notes and you name it. Is the core of the product, right? So how we're able to deliver some of our best in class stats and ratios of SOC analysts to endpoints within the MDR portion of what we do. And just be clear, we're a platform first, right? So we have the technology platform. And then for those that need and have lean teams, we have the MDR aspect. That they could leverage as well. But a lot of what we do is through AI or correlation of data, behavioral analytics, and stuff like that, right? And the great thing is this predates me, right? This is where talking about innovation, Eyal and the founders, you know, when they launched the company, they saw a need and, you know, built AI and automation as the foundation of it and why we're able to do we do and compete against some of the biggest players in the world, and in some cases do better than they do, right? And it's because of the automation and AI. So yeah, I mean, I'm not gonna say 100%, it's everywhere, but it's in a lot of what we do, how we do it, from the platform to behind the scenes, in the sales organization, from generating leads, you name it, it's everywhere. How should MSPs, do you think, how should they be using It's where I should say, go to my keynote from a couple of years ago.

49:01 - Speaker 1
How has it changed since then?

49:04 - Speaker 2
Yeah, I mean, since then, and like anyone who like, you know, was speaking about it, you know, years ago, all still relevant content that we all said, yes, it's the terminology, the use cases got refined and fine tuned. Less about, you know, you should be able to to people are and just faster and, you know, more options. And again, more use cases, right?

49:39 - Speaker 1
Was the full question again, what how should MSPs be using AI?

49:42 - Speaker 2
So I mean, there is front of house, there's back of house, there's in the service, right? Not just MSP, you should be using it everywhere, right? And part of it is you gotta train and educate your people, right? So for people out there trying to sell AI, right? You gotta eat your own dog food, maybe you've gotta spend a little money on getting your teams educated and trained on the latest tools and platforms that are best suited for their function or their needs. And so on. So whether you're an MSP or not, training, right? So I know CompTIA, and full disclosure, I'm still a board member of CompTIA. They've got their certifications on AI and doing some great things there to help educate and train some of the masses out there. So they should be training their people. They should be upskilling their people on, hey, level one techs, right? Make sure that you're more productive and efficient. You're going to be able to do more. Your job of what you're doing is going to get a little bit easier. And then we're going to teach you on how to make sure that you're making sure checks and balances, quality control of what the AI and the automation is producing. And you're going to help fine tune it when you see errors and train the models and make sure that that stuff reduces the error rates of what's going out the door, and so on. And again, no different than what I rattled off of what we're doing here at SideNet, Joe. That's what MSP is, right? Whether it's in the help desk, service desk, level one, level two, whether it's in the finance department, billings down to their customer, automation, so they eliminate the daily chore and the mundane tasks. I always preach, and I'm a big fan, that all that productivity improvement and savings of dollars, because you don't have to hire as many people, reinvest, reinvest into the company, reinvest into your people, and so on. So there's a lot, right? Now, I also speak a lot on the topic, it's overwhelming. So what often happens, again, not just MSPs, pretty much every company, is, where do I start? And I always say, look, start with just looking at your org and saying, hey, what makes sense? What is the low-hanging fruit? What is easy? It's a great use case. It's easy. It's not too technical to make stuff like that happen. And documentation is from marketing to project work to process automation to, you know, you name it, right? Like, start with the easy stuff, right? Work your way up to fully automating tasks and things within your help desk and your SOC and whatnot, right? Because otherwise, it's too overwhelming, right? You're going to try to do too much at one time, and then you're not going to do anything, right? Because you're too overwhelmed.

53:08 - Speaker 1
I'm a former MSP. I talk to MSPs every day. And generally the last five or six years, even pre-COVID to now, the three things that keep them up at night have been pretty consistent. Number one, cybersecurity. They're worried about their clients getting attacked. Then if they get attacked, they have to allocate resources to them. They're probably going to get fired. They're going to lose money because they've, you know, they're fixed rate. They might even get sued. You know, so they're really worried about cybersecurity. Two is human capital. How am I going to keep my current engineers happy? How am I going to get new ones? The unemployment in IT, even with all this AI, is still in the States, certainly less than 1%. And then third, PE has poured in hundreds of millions of dollars. Their friends are selling their MSPs, buying nice cars. How am I going to grow this MSP? How does SyNet help?

54:00 - Speaker 2
So the question is, how does Cynet help grow an MSP?

54:03 - Speaker 1
And those three, those three things that keep MSPs at night, can Cynet help in any of those? Security, human capital, growth.

54:12 - Speaker 2
Yeah, I mean, Cynet, we play in all of that, right? Obviously, what we do is cybersecurity, right? We help protect, prevent all that good stuff. So we do help provide that peace of mind, and we help provide it pretty well, as do many others. Obviously, I'm a little biased there. The human capital aspect, right? A lot of what we do does cater towards lean team, right? So people who decide to partner with SideNet and come along on the journey with us, you don't have to build out your sock as much as you would if you were doing it all yourself. So not only do we have that platform and a very powerful platform, if you wanted to fully say, hey, turnkey and leverage, or MDR, or SOC, which we call CIOPS, and threat intel, and threat hunting, and all that stuff, we have all that, right? So that means you don't need to hire as many people, and your people could be focused on more strategic stuff, which, you know, then you're looking at, you know, what are the high-value things their people could be working on, which helps with the human capital aspect, plus cyber, right, still one of the to go recruit and hire for in the MSP space, right, so talent shortage globally, you know, across all businesses in all regions, then you apply that and it's a, you know, it's a bigger number for the SMBs and MSPs, right, because, you know, why not go work for a Fortune 500 or a mid-market company doing cyber that's going to pay me a whole lot of money, right, and they're also going to have the budget do all these things. So in the S&B MSP world, right, that's a bigger problem as well, right? So partnering with someone like SyNet, we help with that, right? Because we do have the people, we do have the ability to provide the protection and prevention and remediation and stuff like that. What was the third part? Yeah, so obviously growth, MSPs, I don't have the exact stats, but I'm sure you have them, or, you know, people can just research them. MSPs that do cyber and subsequently AI now, right, tend to be showing in their numbers, they're growing fast.

56:33 - Unidentified Speaker
Yeah, right.

56:35 - Speaker 2
So you've got that aspect, right, you partner with us, we help because you have that. But not only do you have cyber, you got multiple aspects of cyber, you got endpoint network, detection, deception, posture management, email, ITDR, and the list goes on and on, right? And then, you know, our sales team, our go-to-market motion is also working with MSPs to sell them to their customers. So if they don't have the skillset and know-how, they could partner up with our sales organization and we could help them sell cyber into their customers. And we've got a partner program for non-MSPs on the reseller side and so on. So yeah, I think we, pretty well to both of those needs.

57:21 - Speaker 1
When an MSP is looking for a security partner, what questions should they be asking?

57:31 - Speaker 2
What questions should they be asking?

57:33 - Speaker 1
There's lots of security providers out there, so what should they be asking when they're selecting the one they want to partner with?

57:40 - Speaker 2
Yeah, I mean, so for me, I wouldn't be asking the vendor necessarily. I would be going out to the social world and seeing what is being said, positive and negative, right, or negative and positive, and just see what people are saying, and really look for third-party validations. In the cyber world, there's many, right? Gartner has stuff, Forrester has stuff, you got the MITRE stuff, G2's always a good one, right, because you can see multiple customers submitting stuff, you could go to the social depths and see people talking about, hey, this vendor had this issue and this vendor did a phenomenal job thanks to SyNet, right? Whatever, right? And why do I say all that, right? Because they'll tell you if that cyber vendor, like SyNet, is driving the outcomes, right? And look, we got to the point years ago that it's not an if, but it's a when, right? So everyone understands that. So when the boom happens, is it the vendor that's gonna be there with you to make sure that you're up and running and minimize it a bunch, right? So that's kind of what my recommendation is, and that's kind of what we kind of talk with our prospects and customers on. Just look at the results, right? Is it driving the outcome that you're looking for? No one's going to be 100%, right? But in the event that it's not 100%, how do they respond?

59:21 - Speaker 1
You mentioned earlier Comptia. Jason, you sit on many boards, some right here in Tampa, University of Tampa, the Stratus Theater, a lot of other boards that are publicly listed. What is the value? Why give back as much as you do with everything on your plate?

59:38 - Speaker 2
Yeah, so I mean, to your right there, give back, right? So, University of Tampa is me helping give back to the community, to an extent, right, in different ways. Strathcenter, Performing Arts, Performing Arts Center. You know, it's just a different way, right? And, you know, I'm on several committees there, and in some cases, talking technology and helping out when they have questions on certain things. You know, it was part of, we went through strategic planning on, you know, what's the future for Stratus Center, where are we going? A lot of talking about the, you know, reimagination of the Stratus Center. And yeah, it's me just being able to give my time back, right, in those areas. And a lot of that stuff is about time. University of Tampa, what's really cool, because we are in this, you know, point in time that will be in history, right, like the Industrial Revolution, the dot com, and so on, it will be the AI spoken about. And a part that I'm playing in, because I am on the strategic planning committee for UTAMPA, and we were talking a lot about how do we weave AI and automation and even cyber into the fabric of all things curriculum. There's several goals that universities and higher ed have, right? And one of them is making sure that their people are employable when they graduate, right? So if you come out of college and you're already versed not only in a major, right, like marketing or business and or human resources or whatever, it's that much better if you come out and, hey, I'm also versed in AI and automation tools and I know how to use them and, you know, coming out a level where I'm going to be more productive than people who came from schools that don't. So I'm pretty passionate about that stuff, and that's a big part that I play in. And then some of the other boards are, if you look at what I do, I'm on a couple of MSP boards. One MSP board, I'm an advisor to another. The one I'm an advisor of is born in the AI world type MSP, and we've done our first two acquisitions. We've got two more that I think we're currently under LOI, fingers crossed. And it's really, we've got this AI platform that we're able to plug pretty much any MSP into and see night and day difference in efficiency, productivity levels, and so on across the company. The other one's a large P-back consolidator. And it helps me provide my knowledge of the industry and what good looks like and be able to contribute to make sure that those are best-in-class companies. And a lot of that is me giving back, cuz just enjoy learning that aspect of it as well. And then I'm learning, but also connected to my customer base, right? Cuz we do 30% our our 30% customers are managed service providers globally. So it's just another avenue for me to keep in touch with the base because I get a more intimate look and view of what's going on and the operations. And I could use that to help solve problems, whether at Cinet or elsewhere. Yeah, but I'm having fun. You are.

1:03:22 - Speaker 1
Yeah, and you look good. If we replayed this conversation, Jason, years from now, what would you hope aged well?

1:03:30 - Speaker 2
What would I hope aged well?

1:03:32 - Speaker 1
Hopefully me. And me. But I mean, what we discussed.

1:03:37 - Speaker 2
You mean the topics and everything?

1:03:39 - Speaker 1
Any particular topic, yeah.

1:03:40 - Speaker 2
Well, look, AI is here now, here to stay. It's the future, but it's going to look vastly different.

1:03:46 - Speaker 2
It is.

1:03:48 - Speaker 2
So I think that's considered age well. I think it's just going to look vastly different. And we'll understand the impact a lot more in five years, right? If you look at just the dot-com boom, right? I mean, in the late 90s, right? I mean, shot up money in the dot-com boom, and then we had the crash, right? And then it leveled off, and then it picked back up, and then it came into its own, right? We're going through that. It's just going to be a quicker point to hit the top, have a little bit of a dip, and then it'll accelerate faster. As well in terms of what it actually looks like, So we'll know it for sure in five years what the impact is. And things that people are fearful for or not, we'll know if it's a reality. So yeah, if that's how you define age well, sure. But yeah, I think every aspect. I mean, leadership and things will evolve. The born in the AI world, of employees coming out of, you know, high school and college, you know, these years, five years from now, right, leadership's gonna have to change, they're gonna have to adapt, right? So yeah, I think everything we've spoken about will age well. If I'm understanding your question.

1:05:11 - Speaker 1
Yeah, you answered it very well, like you do everything quantum, where's quantum gonna be, you think? Is it right around the corner? Is it hiding? Is it there?

1:05:18 - Speaker 2
Look, I mean, no different in AI, right? People talking about AI 50 years ago, or however long, people have been talking about quantum for a while. And there's lots of companies that are, you know, trying to crack the code on that. And, you know, various levels of success and things. Yeah, I mean, at some point, that'll become a reality when there's enough people trying to solve that problem and make that innovation happen. And enough money is flowing into it. And it is because I'm, I know a hand full of investors that are very active in quantum computing and so on, it'll have its day, right? I mean, it needs to have its day. It's partially what's needed to drive probably the second wave of AI, right? Because just think of all going on and the speed and processing power and all the data center build outs and all this, right? My guess is that fuels the money flown into of people trying to solve the quantum equation.

1:06:21 - Speaker 1
It's an exciting time. What advice do you have for rising leaders that are rising right now and avoiding to avoid burnout? What advice do you have?

1:06:33 - Speaker 2
I may not be the best person to answer this.

1:06:36 - Unidentified Speaker
You're not burned out. No, I'm not burned out.

1:06:37 - Speaker 2
I love what I do. Yeah, I know. That's part of my problem. I probably wouldn't even know what burnout is because I just love it. I'm not saying I don't have bad days of sorts, right, and feel tired and exhausted. But I think to that point, and hopefully this doesn't come across like no duh, goes back to the question about the interviews. That's two way, and I said to some extent, yeah, you are interviewing them, and you wanna make sure it's a place that you get behind and align behind where they're taking it. Excited about what they do. And, you know, tied to your question, right? If you like what you do, and you're enjoying it and having fun and surrounding yourself with good people and a good mission and vision, you're less likely to experience burnout. Because you know, what you're doing is driving towards a certain thing, no different than my North Star comment, or my, you know, here, here's where we're going, right? The goal, it provides you that, alright, here's why why I'm doing what I'm doing, right? I often find people have burnout or experienced burnout when they don't know what they're working towards or why they're doing what they're doing, and they just feel like they're doing busy work, right? So my advice to people that are early in their career or whatnot, make sure you go to a place that you're passionate about, you're aligned behind what they're doing, how they plan on getting there, right, ask a lot of those Make sure you understand you're what you're doing is actually contributing, right? Because if you're, if you don't feel like it's contributing, right, you're gonna feel like you're in that rat race, like just doing mundane tasks, and then you're gonna get burned out, you're gonna be bored, you're not gonna be happy, that's gonna spill over into your personal life, and so on. So yeah.

1:08:32 - Speaker 1
You're inspiring me, Jason, what gives you optimism about our industry?

1:08:37 - Speaker 2
Optimism, yeah, I mean, look, AI is going to progress things fast, but things are going to just get more complex. As they become faster, that's an aspect of complexity. This first part's not what's inspiring me about the industry, but I'll get to what threat actors are going to do more, and they're not going away anywhere, but with that, provides lots of opportunity for the managed service provider industry and the stuff that we all do. So that creates growth, that creates opportunity, that creates innovation, and so on. So I guess the, you know, what I'm trying to say is that, you know, there's always people talking about is, you know, this the end of MSPs? I'm a believer that it's just the beginning.

1:09:26 - Speaker 2
Yeah, right.

1:09:27 - Speaker 2
And when you follow the money, that's where things really start to get in And yes, you've got the Evergreens, the New Charters, the Coursers, the Titan MSPs. You've got all the big PE back roll up plans out there, companies out there. That's just the start of money coming in. There's many other VCs, PE, people who have money that see this as really viable. Business model starting to come into the Mix. And as there's more money flowing in, that funds lots of new things, exciting ideas, creativity, ways for the MSPs become the epicenter of solving these problems, right? And, you know, restaurant owners need to be focused on delivering great service, great product and experiences and all that stuff. Let them focus on that and let managed service providers handle and handle everything else from a technology standpoint and more, and become those advisors. So I think we're in early innings, and I think as the industry evolves, technology evolves, that creates tremendous opportunity and tailwinds for MSPs and the industry.

1:10:48 - Speaker 1
Jason, the best leaders you know have what one thing in common?

1:10:54 - Speaker 2
Can I steal your thing?

1:10:55 - Unidentified Speaker
What is it?

1:10:58 - Speaker 2
And look, every leader, myself included, I mean, I had to learn, right? I mean, you need the discipline. You can't do everything, right? Use frameworks, right? Whatever it may be, right? If you have no discipline, if you're all over the place, if you have nothing that you're driving towards, use the concept, guiding principles, none of this stuff, right? Your organization's gonna be all over the place, right? You're not gonna be helping and tying into your burn question. You're gonna burn a lot of people out, right? So the discipline to know where you're going, try to stay on course. It'll never be perfect because we're in a fast-paced industry. You'll have to pivot. People need to understand that. The discipline to, hey, no, you can't go from point A to point Z overnight. And the discipline is, all right, I'm going from point A to B. When we make that happen, we're gonna go from B to C, C to D, and so on. Yeah, patience as well.

1:12:17 - Speaker 1
Jason, is there something you firmly believed in 10, 15 years ago, firmly believed in that that you no longer believe in now?

1:12:24 - Speaker 2
I don't think I've ever been asked that question, Jeff. I'll have to think about that one.

1:12:33 - Speaker 1
There's, you know, it was only 10 years ago, so 2015 so.

1:12:37 - Speaker 2
This one's about me. I thought I knew everything 10, 15, 20 years ago.

1:12:39 - Speaker 1
Did you really?

1:12:41 - Speaker 2
Now I know that not to be true.

1:12:44 - Speaker 1
I find that as I get older, I have more questions than I have answers, by the way.

1:12:48 - Speaker 2
Well, I think, I mean, I joke, but this, going to say that's my answer. But look, you when when you're younger in your career, to some extent, you do think you have all the answers and ideas. And look, some people do and they go on and have great careers and do great things, right. But even those people aren't perfect, right. But then you do learn and you evolve and realize that it's not about the individual, it's about it is about the team. And the you know, the experiences and skill sets and things that the team bring to the table. And it's about making sure that you lean on the experiences of others because they have the pattern recognition, they've been there, done that, the know-how, and learn from it, right? So, you know, whether it's 10, 15, maybe even longer, right? Yeah, you come out of college, you know, I was no different, I'm gonna conquer the world, right? To show everyone and then you have a little humble pie and be like, oh wow, this is what it really is, right? You don't have that understanding in college, right? So I joked about it, I used it as an example, probably not my final answer, it may come back, but that's probably something that I thought I knew and then had the humble pie and realized and evolved. And to an extent, I do, and I did it even with my new team over at Scinet when I first came on at Scinet, and I used it once upon a time at ConnectWise when I just brought together a new team. I do this exercise, it's a series of exercise, but one point we go through, hey, write down on a piece of paper things that you most accomplish or feel most accomplished and proud of, milestones and things you've achieved and experiences that you love telling people and we go around the room and everyone reads off their stuff and they're proud and they should be, right? Some great stuff. And then I do a thing where I'm like, all right, now take it in one of your hands, crumple it up, throw it away. And then there's a moment of silence and shock factor and all that. And then I say, why did I do that? I said, look, the great thing is those are experiences, right? Experiences, milestones from the past, things that you want to draw on, what worked, what didn't, what not to do and learn from the mistakes and all that stuff, right? I need you to bring that in here so we don't make the same mistakes, we don't go down the same path and have the same failures. And the things that worked, make sure that we find a way to put it in here, make it better. I said, but now all of your peers just heard the great things and experiences and knowledge that you bring to the table that, hey, when they have a need, they'll know, hey, Joe is well experienced and have done these things in the past. Now, hey, I'm gonna go to Joe if I got a question on a topic that I'm less comfortable with, right? So it's really about bringing the team together and understand how they could lean on each other. For what experiences and knowledge and expertise and all that stuff. So I've used that a couple of times. Again, it's all part of the journey I had, because once upon a time, I thought I did know everything, right? And I could keep going on and on and that stuff, right? I could tell you stories of the exercise.

1:16:29 - Speaker 1
Yeah, that's a really cool one. I like that one a lot. So you know the story, Jason. Back in the 90s. I was working way too hard, not paying attention to myself and not exercising anymore. I'm in front of the doctor and she tells me I'm at 340 pounds. So I gained all this terrible weight, right? And she says to me, if you don't lose this weight, you're not going to see your daughter graduate. So it scared the life out of me. So you would think that motivated, but it just ended up angering me, right? So I spent the next six, seven months, lost about 130 pounds and I kept it off, right? This isn't finishing lines, right? These are lifelong changes. So you've alluded to it many times. When I tell people this story, they always say, what's your secret? What'd you do? And I just say discipline, right? You've mentioned it more than once, right? Focus, willpower, routine, I consider all under the discipline spectrum. So we talked a little bit about how leaders have discipline and what it means, but specifically, what does it mean to you, discipline? How does it play a role in your life?

1:17:32 - Speaker 2
How's it play a role? It plays a role in lots of areas of my life, personal and professional, right on the personal side. You know, and I'll use the health thing, right? You know, I'm not going to say exact, but close. No, not even close to or exactly similar. Yeah, right. Hits. I, you know, running a big over a handful of years as COO and a year into my CEO tenure at ConnectWise, and I put on some weight, I guess. And up till COVID, I didn't realize it, right? And COVID hits, and yes, COVID, crappy thing globally for everyone, right? But there were some benefits, right? And for me and my family, Hey, I was home more. But also, my wife's like, hey, let's go on a walk. And I'm like, all right, and so we started going on a walk, and literally got two-tenths of a mile in, and I'm like, Rach, I can't do this. And keep in mind, at that point, I was actually sick. May have had COVID, I will never know, because I lost test results, and retook the test three weeks later, and whatever. But I just, it was like, that was my point, right? I didn't have a doctor tell me, But at that point, I'm like, holy cow. And then I go home. I look in the mirror. I'm like, holy cow. And then from that day for, I don't know, four months, five months, I forget exactly how long, I just started walking. About 2 mile, 1⁄10 or a quarter of a mile, went up to a mile, went up to two miles, went up to three miles, went up to some days 4 and 1⁄2 miles. And then I was swimming. My pool in the backyard, right, in between conference calls. And when I had breaks, I'd go and do this stuff and jump in the pool and come out looking like a shower on the next call. And, you know, discipline of waking up every day and doing that and fast forward to, you know, I mean, I lost 30 pounds when I did that I've maintained. And so part of discipline in my life is making sure I maintain and that, you know, I'm aware that I'm not going to get back to that level. And, you know, I, I'll tell you, it's a few times a year that I'm asking my wife to pull up. She has side by side. It's like five months apart, four months apart, you know, um, a picture of me at the connect wise holiday party and then a picture on 4th of July. So six, seven months apart, um, night and day different. And so I've maintained that, you know, ebbs and flows and I'm not upset at my when, not a bad day, but call it cheat days. And I go and eat and drink and so on, right? But then I know, all right, let me get it back down to where I like it. And right now I'm a week plus into, I've got ten more pounds that I set to lose back then that I didn't go fully through with. And now I'm trying to be disciplined to make that work, right? And there's lots more. More disciplined personal life and how do I do it? It's walking again. It's making sure that I'm eating healthier and the discipline of, yes, I see all that candy and stuff I want to eat and devour or drink. And I'm like, right, well, you know, instead of having a 200 calorie, you know, beer, I'll go with the Coors Light or the Michelob Ultra, things like that. And then, you know, professional life, I mean, you know, and look, I'm not perfect at it, Joe, just to be clear, right? Because I too sometimes over-rotate on, we got to do this, otherwise we'll be left behind. And that's why you got your team and you hope your team is a great team to manage up and hold you accountable too, right? That's part of the whole process, right? And I think that even ties in the discipline of an individual or an organization as the system put in place. But it's making sure that, I do a check probably weekly, all right, am I putting too much on people? Are my expectations too great? You know, that's one aspect. Another aspect is we have our destinations. And if we don't have a destination, right, there's one area in my org that, you know, not 100% clear on the destination. So we're doing continuous meetings until we land on where that, you know, current point in time destination will be. So we have something to march towards. It helps with prioritization, all that stuff. And then there's the KPIs and metrics, and again, discipline from a pipeline standpoint. Well, you could probably miss a day and make up for it on day two, but if you get a weekly goal and you wait to the last day, right? Well, so it's discipline of looking at your metrics and goals on an appropriate level, whether that's daily, whether it's weekly, monthly, quarterly. So there's a lot that goes into it from a professional Discipline is, you know, trying to stick to, you know, how do you avoid all the fire drills and detracting from, you know, the strategic, you know, proactive side of things, right? Well, you know, can't worry about the emails that are sitting in your inbox. If there's something important I've learned, people will call you, right? They'll text you, they'll teams you, be like, hey, sent you an email. I know you haven't responded, probably haven't seen it. Can you go, you know, going to take a look, I need an answer. And then getting to them when you need to. And discipline is making sure that I'm empowering my teams and leaders and that I'm not micromanaging. Now, when I say that I'm not, doesn't mean I won't. But if I am, that means something's wrong, right? And I educate. I had a call with one of my leaders today and I educated, hey, if I'm doing this or asking these questions, just let's be That's because I think there's something wrong, or not right, or I'm not getting the answer, or I don't feel good about something. Yeah, I keep chatting through things. Not all of it ties into discipline. I think most of it does.

1:23:57 - Speaker 1
As a kid in your household, was discipline exemplified? Was it talked about? Was it just assumed?

1:24:01 - Speaker 2
Yeah, I mean, me and my brothers grew up in the 70s, 80s. You know, early 90s and so on.

1:24:12 - Speaker 2
Colleen mother.

1:24:13 - Speaker 2
Yeah, Irish father, my father was, you know, in the army for a few years when he was young. We had chores, we had all these things, right. So I feel like there was the right amount of discipline. I feel you know, I am who I am today because my parents right instilled, not just discipline, but work ethic. And if you're going to do something, do it right. Don't mail it in. Put your all into it. So growing up, a lot of that was instilled in me from my parents, for sure.

1:24:58 - Speaker 1
Is there a question, Jason, you wish more people would ask you? Question more people would ask me you wish people would ask you I don't know that's a good question what motivates me maybe that's my next question what does motivate you was that really your next yes it was honestly my next question. Yeah, honestly.

1:25:39 - Speaker 2
Well, first, let me go. That's probably a question that people don't ask enough. Because you can tell a lot from a person by some of their answers. And it's probably why you asked. But what motivates me and my family motivates me, right? I mean, my wife will tell you and you know, we just went through it. It's the holiday season. I don't really have needs, Joe, right? Like in granted, partially, yeah, I've done well, so I could do what I want when I'm Liberty, so on, right? But she's like, What do you want for Christmas? What do you want for your birthday? Like, I love what I do, right? You know, my hobbies are, you know, the advisory, the board, the running company, sign that, you know, I go to sporting Tampa Bay Lightning, Tampa Bay Buccaneers, watch a lot of sports on TV. There's not much I need from that standpoint. So that stuff doesn't motivate me. What motivates me is that I'm able to make sure that my kids and their kids and the broader family is impacted by all the hard work and and, you know, stuff that I've done to be able to provide. That's a big part of my motivation, right? My motivation is, you know, tying back to, you know, giving back, you know, doing the stuff I'm doing at UTampa and the Stratus Center for Performing Arts. And, you know, when I take a call from an ex-colleague or I take a call from a, you know, MSP business owner or a vendor in the MSP space that's starting out that, you know, has questions or, hey, my board's giving me issues, do you have any advice, right? That stuff motivates me because I'm able to give back. What motivates me is, you know, like protecting, right? What motivates me is doing what we do, whether it's at ConnectWise or now here at SyNet for managed service providers, right? You know, vendors that are in the space that are doing at right are impacting lives, right? And even look at, you know, pre the private equity, right? I mean, a lot of, you know, early people in the vendor space, and many still in the Tampa area, right? You know, change lives, right? Just look at even what Arlen did. And it's one example around peer groups. Yeah, Arlen Sorensen and peer groups, right? Changed lives with, you know, back then, and then IT Nation Evolve. And if you look at even where many of the early onset of private equity, right, you know, they started to do stuff within the IT Nation Evolve peer community. And that was a lot of the mergers and acquisitions going on as people sitting in rooms and bonding and forming relationships. So, you know, and that stuff predates me to some extent, obviously. While I was CEO at ConnectWise, but that's the stuff that motivates me.

1:28:56 - Speaker 1
I know what you mean by the gifts, by the way, Jason. My family always, what kind of, I don't want any more possessions. I want experiences is what I tell them. I want dinner. I want to do something. If I want something, I just buy it. So it's not, you know, and I have enough by the way. So yeah, more experiences. So given your motivation, you mentioned your family legacy, impact, it was what I gathered, and giving back, and protecting. How do you measure success?

1:29:24 - Speaker 2
The smile on people's faces.

1:29:26 - Speaker 1
You just put a smile on my face.

1:29:28 - Speaker 2
Well, again, partially joking, but not really, right? I mean, if you have an impact that positively impacted that person, you're gonna see it in their demeanor, their facial expressions, their life, right? Or it could be a business and how they operate and so on. That's a good sign, right? That's the stuff that you can't really see in numbers and so on, right? But yeah, I mean, I could go through examples, right? All right, well, when President Dahlberg at UTampa came on board. We did a launch, you know, one-on-one. She's like, you know, what would you like to see? And I was passionate about AI being embedded within the curriculum. Well, now everyone's talking about it, right? So to me, that's a sign that, hey, you know, it's going in the right direction. And then here's what has been rolled out, right? More signs, right? And it's not just one department or major. It's across multiple. That's, to me, leading indicators, leading towards that that will be a reality. So everything's probably a little bit different of measurement and how I measure and see progress is happening. I do so many different things, again, whether it's personal with my family or the stuff I do.

1:31:02 - Speaker 1
Has there been anything in the last month or so you changed your mind on?

1:31:07 - Speaker 2
Yeah, probably. A thousand things just while I'm sitting here, Joe. Well, define and change my mind on it. Like, just anything? I could use the example of yesterday. I went to Tampa Club with Alan Comet, my chief revenue officer, and I was going to grab a drink and change my mind and said, look, I'm going to make it eight days without a drink this month.

1:31:35 - Speaker 1
Look at that. Do you change your mind often?

1:31:41 - Speaker 2
Do I? No, I don't think I mean, I'm flexible. And yeah, I've got opinions and passions and emotional about things. But I am a reasonable person. Yeah, I'll keep an open mind. That if there's a better way, different way, a way I wasn't thinking, I'll definitely explore and try and change my mind, you know, to go do things for sure. Goes back to what I you know, learned, you know, over the 10 15 years or changed, right, where I thought I knew everything. And I had all the answers. I realized I got right. So not one person has all the answers. So yeah, I changed my mind probably often. Yeah, right. And when my when I have the right team in place, and they're managing up, yeah, I changed my mind.

1:32:34 - Speaker 1
And when you're selecting your team, Jason, what does that So when you interview somebody, this is an art versus science question, so you kind of get their resume, you see where they've been, all the kind of scientists, the metrics. Is the last judge your gut? Do you play your gut into it at all?

1:32:52 - Speaker 2
Yeah, I mean, I think gut always comes into you, right? Because, look, I'm not going to be one of those people who says, my gut the 100% time. But generally, I mean, and it's not the last. Your gut feeling usually happens pretty quick, right? Gut feeling aside, when you're interviewing leaders or any team member for that matter, you generally know within the first 10 15 minutes if they're the right person for the company and then they're the right person for me, right? Because there's personality aspect too that comes into things. Generally, good interviewers are able to figure that out in the first 10 or 15 minutes. And then the rest is validation and seeing how they interact and communicate the questions they ask and so on. So that's a lot of doing the interview. And I try to get a sense pretty quick. Now, on the flip side, when you get to that 10, 15 minutes and realize, yeah, not for me, and you don't want to be the person that cuts it short, then you're sitting there for another 40, 45 minutes, and you're like, all right.

1:34:04 - Speaker 2
Tough one.

1:34:05 - Unidentified Speaker
Tough one.

1:34:07 - Speaker 2
I forget the original question, but in interviews and what I look for, is that what it is?

1:34:12 - Speaker 1
How often do you use art versus science? Your gut versus?

1:34:15 - Speaker 2
And then there's questions, right? And I won't go into the details, but there's, all right, do they have the experiences? So you got to vet that out, right? What they said on their resume, are they able to talk to it? And again, and generally you can figure it out really quick. If they're just reiterating the bullet point that's on a resume, chances are they can't speak much to it. If they show emotion in their voice and passion, you know they've been there, done that, have that life experience and bring that experience and pattern recognition to the table so you get the validation. Then there's the culture fit. Are they gonna work with the team? What questions can you ask that will bring that out? About a time this. What personalities do you work best with? What personalities do you work less well with, right? What are your pet peeves on, you know, working with the team? Who is your team, right? You know, if they say the team is the team I'm leading and managing, most of the time that's the wrong answer, right? The team is generally the team that you're a part of And, you know, everyone has different opinions, so I'm sure people that will be listening to be like, no, he's wrong on that. But I kind of look for that. The team that you're on, that you're going to go to battle with, that you're going to go build something really great, that you're going to go make that positive impact in the world with, that's where you've got to make sure they fit in. And then there's questions around, hey, are we going to work well together, personality-wise? Tell me about your style, your work ethic. If the laptop is shut at night, what do you do, right? And so on. What are their values, right? Family, you know, you name it.

1:36:06 - Speaker 1
Jason, we've been talking about having this discussion for years. And it finally came together. At least, right? You would see. Easily two, yeah. Easily two years, yeah. And shout out to Ms. Janine Edwards. We got everything together. And I thank you so much for your time. We're here in Tampa.

1:36:23 - Speaker 2
going to continue to grow in this Tampa area as well you love it here yeah yeah we're so I was Tampa or employee colleague number one at side net in Tampa I think by the end of this month we're in a week or so we got another new hire starting I think we'll be 14 15 on Tampa we've got you know I don't know we've got four offices right now that fit anywhere between you know three four five people in office in a co-work space in downtown Tampa.

1:36:55 - Speaker 1
Yeah yeah great location and love it here. Jason thank you so much for your time my friend I really appreciate you doing this I know you think you're not good at it but you're excellent at it and I really really appreciate your time.

1:37:07 - Unidentified Speaker
Well I appreciate it Joe thank you.

1:37:09 - Unidentified Speaker
Thank you so much.