Joey Pinz Discipline Conversations

#870 Kaseya Connect 2026: Jim Lippie - 📈 From MSP to SaaS: What Actually Changes?

• Joey Pinz • Episode 870

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What separates a strong operator from a true leader—and how do you scale success across multiple companies?

In this episode of Joey Pinz Conversations, Joey Pinz sits down with seasoned tech executive Jim Lippie to break down decades of experience across MSPs, SaaS companies, and multiple successful exits. From early days in the MSP space to leading SaaS growth and navigating acquisitions, Jim shares practical insights on leadership, metrics that matter, and what most operators overlook.

💡 This conversation dives into the real differences between running a services business and a software company—and why understanding customer acquisition cost (CAC), retention, and urgency can completely change your trajectory.

Jim also offers a clear perspective on leadership: it’s not about managing tasks—it’s about building other leaders and winning hearts and minds.

🔥 Top 3 Highlights:

  • 📊 Why CAC and net retention matter more than most MSPs realize 
  • 🧠 The mindset shift from operator to true leader 
  • ⚡ How urgency and accountability drive scalable growth 

If you're an MSP owner, SaaS founder, or tech leader, this episode delivers practical insights you can apply immediately.

 

 

Join us for enlightening discussions that spark growth and exploration. 

Hosted by Joey Pinz, this Discipline Conversations Podcast offers insights and inspiration.

 

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Discipline. How does it play a role in your life? How does it drive your decisions? Do you have too much or too little? Every profession, hobby, or passion requires a level of discipline. I have used it in weight loss (+130 lbs.), family death, and found a +25 year business. Am I an expert? Absolutely not! Please join me, as I speak to interesting people and find out how discipline affects their career, life, goals, and decisions. Join me as I talk to interesting people in: #Health, #Fitness & #Wellness: #Business, #Technology & #Science: #Art & #Culture: Website: joeypinz.com All social media @TheJoeyPinz Do you wish to Sponsor? Get the prospectus here: www.joeypinz.com/sponsor

 

 

 

 

 

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SPEAKER_00

Kaseya Connect 2026 in Las Vegas. What a wonderful, wonderful event. Lots of energy, lots of new things coming on the platform. The new CEO was great. So much energy. Vendor Hall was really, really involved and just really well-run operation. Really enjoyed the event. I've been going to them when I was an MSP and now as you know, not an MSP as a as a media, as a as a vendor, etc., since 2007. A really great event. Um I'm going to say it was the best ever. Three great conversations. First with Andrea McLaughlin. Oh my goodness. Great conversation with Andrea. Andrea works at uh is at Movila and uh account manager there and does an incredible job talking to MSPs about how to run projects, how to use their great platform to do so. She's open, she's insightful, she's honest, she's uh energetic. Really enjoyed the conversation with Andrea. Thank you. And then I spoke with Aaron McLean, an Olympian. She's CMO over at Cyanomi, great cyber security platform. Aaron, I thank you so much for your time. Uh from the Olympic softball stage, I mean the Canadian Olympian to the chief marketing officer now. Great energy, really enjoyed talking with you. And then last, Jim Lippy, the CPO of Kaseya. I've had the pleasure of knowing Jim for at least 10-15 years. He was an MSP, and then he was uh a SaaS vendor and came out of it, and now he's been in Kaseya for all this time. We go in deep about some of that transition, some of the great new things that are happening at Kaseya. Great conversation with Jim. Wonderful experience there at Kaseya Connect 2026. Thanks for watching. Thank you for thank you for all my great guests. Hi, I'm Joey Pins, and here's my 45-second introduction. After starting my business in the 90s, I started developing poor habits of eating and my diet because of working way too much, found myself at 340 pounds. The doctor told me if I don't lose the weight, I'm not gonna see my daughter graduate. I took the next seven months, lost 130 pounds. People ask me, how'd you do it? What's the secret? I need to lose weight. How'd you do it? How did I lose the weight? Just one word. Discipline. I've had other successes in life, and I attribute them all to discipline. Now I'm not the king of discipline, but I believe that it can help all of us. Friends convinced me to start a podcast. The podcast mission: How do we better ourselves and society? I talked to interesting people in health, fitness, sport, wellness, business, technology, science, art and culture. And I eventually asked them how discipline plays a role in their life. Podcast vision, growth through learning from others. Once a week, that's not enough. That is the problem, isn't it?

SPEAKER_02

And it's only in a week.

SPEAKER_00

Can you tell? Can you uh ask anybody about that to help you out and be able to squeeze more golf in?

SPEAKER_02

Um I don't know how long that will go over.

SPEAKER_01

Nah, so I I did you play like when you were up in Boston?

SPEAKER_02

Yeah. No, but you know, I the main thing that I do that just kind of relieve stress is I work out. Yeah, I know you do. Yeah. And for me, that is really helpful. Yeah. Um it allows me to just decompress. So it's important for my mental sanity.

SPEAKER_01

Yeah, because on your regiment looks great.

SPEAKER_02

Yes. He's lost 15 pounds. Yes. Thanksgiving. And uh he calls it uh mixed up.

SPEAKER_01

That's true. He does, yeah. Yeah.

SPEAKER_02

You've always been civil, right? For the most part, I played college football. So um uh at Boston Pops. Boston University. Boston University, yeah. So I'm you know, um, so I've always been in that kind of mindset of working out, and it's really important. I have a I have a twin brother. Yeah, you're in New Hampshire. And he is in wellness. And he always says if you took all the benefits of exercise and put it into a drug, a pharmaceutical, it would be the highest selling pharmaceutical cycle in the history of the planet by an exponential amount. Yeah, uh so and the great thing about it, it's for free. You just have to dedicate the time, you know, commitment, and you you can get all the benefits. So I I really that's the one thing I would make sure I make time for at least some of that.

SPEAKER_00

But walking out of that gym, man, there's that there's no feeling like that. Yeah, it's so good. It's so good, yeah. I edit walking in, you're hemming ha, and you're going through it is tough, but walking out of there is just man, you feel like young ucks.

SPEAKER_02

Yeah, through the first five minutes. That's right.

SPEAKER_00

Yeah, and it's all downhill.

SPEAKER_02

It's all mental. It's like just getting there is more than half that. You started your MSP when? So I joined the MSP industry in 2003.

SPEAKER_00

Okay, that's right.

SPEAKER_02

Four staples. These four staples. 2003 I joined Thrive Networks in Boston as director of business development. In the summer of 2005, they named me CEO. December 22nd, 2006, I filled the staples. I had an opportunity to then run that business for Staples for six years. Uh as president and CEO. And then eventually I also became S Staples GM of Central Services, which was basically their version of Geek Squad, you know, Best Buy is Eek Squad. Right. And Eaton. By the time I left, I'd I'd taken ownership of that as well. And then uh that was August of 2012. Wow. And then Staples started to cut back on their technology initiative. So once that happened, I just felt like it was time to move on. So I joined Independence IT in 2013. And that was my first entry point into selling software. Tim SEs. But it's where I met Chip Block and Seth Bostock, my two co-founders of Sassorts. So uh we went in our separate ways for a while after Sassorts, or excuse me, after Independence IT was sold. And uh they came to me with the idea for Sassart sold.

SPEAKER_00

Wow. And independence was built by who?

SPEAKER_02

CloudJumper at the time, and then CloudJumper kind of selling it to NetApp.

SPEAKER_01

Wow, how many times have you sold? That's a good question.

SPEAKER_02

So Thrive to Staples, yeah, independence IT to CloudJumper. Well, first SaaS search to Insight. Ah, that's right. We did a majority recap in 2022. It's like 54%. So typically um two bytes to Apple on that one. So Insight and then ultimately to Caseya.

SPEAKER_00

Wow. And the difference between running an MSP and running a SAS platform is a good question.

SPEAKER_02

I've learned so much in the software space that I wish I could take back to run my MSP. Like I did a presentation a while back in the SaaSHurse days, called the MSP Time Machine. And the entire premise was based on I if I could take everything I learned in the software space in the second app quicker and bring it back to my MSP, I would be so much better of an operator on the MSP side. And it really comes down to a few principles. One is urgency. There's a lot more urgency than software.

SPEAKER_00

Really?

SPEAKER_02

In general.

SPEAKER_00

How so?

SPEAKER_02

Well, because for the most part, most software companies have some sort of investor structure. So when you are taking money from somebody, you're expecting a return. There's a level of pressure, therefore, urgency associated with that. And it makes you operate and think differently. As opposed to most MSPs, you know, realistically are owner-operated. Right. Um up until you know the last 10 years, private equity equity wasn't really in the MSP space. So it just teaches you a different set of disciplines and the urgency is the first one. And then I would say I think being able to look at the cost of acquisition, customer acquisition. So CAT. In the software space, that is something that you track very closely. And at Thrive in our MSP days, we looked at it and we tracked it, but not nearly with a level of scrutiny as we do in the software space. So I bet if you ask most MSPs, they don't really know what their CAC is. So you need to understand your CAC for a new logo. But then one of the great things about the software space is that if you're doing it right, there's opportunities to upsell and cross sell. And I really learned the upsell or cross sell motion in the software space. And that motion is what I wish I knew back in my MSP day. Because that's what I would be taking back.

SPEAKER_01

And then by doing so.

SPEAKER_02

So net retention, what comes from that, is a real focus on net retention. Because net retention is essentially upsell, cross sell minus churn equals net retention. And that is a number if I was an MSP that I would be much more focused on than most people do. Most MSPs, I know I personally, yeah, I never looked never looked at net retention. Yeah, I don't think we did either back in the ILSP games. But software is a good deal. And you know, uh Sasslerx, we had you know between 130 and 160 percent net retention. Today, it's 162% net retention Sasslurks. Um, those are great numbers.

SPEAKER_00

Yeah, and I just think that is something your brand deserves to be in front of the right audience decision makers, entrepreneurs, and professionals who are ready to take action. That's exactly who listens to the Joey Pins podcast. Thousands of engaged business leaders and consumers tune in every week. Millions of views and listens across YouTube, Apple Podcasts, and Spotify. Sponsors see real impact, higher engagement, brand trust, and conversations. We offer strategic partnerships tailored to your goals, including targeted ad placements, branded guest appearances, multi-episode and event sponsorships. Make your brand part of the conversation. Let's grow together. Visit JoeyPins.com slash sponsor to explore sponsorship opportunities or email us at sales at joeypins.com. The Joey Pins Podcast, where brands and thought leaders connect.

SPEAKER_02

Again, I would take back to my MSPAs. I thought I'd be a much better operator.

SPEAKER_00

And for those MSPs, I know I ended up creating an app. We used it internally, and then I brought it to market. Your advice for those MSPs that are actually because a lot of the vendors out here are former MSPs. Your advice to them from what you've learned are to look pretty much look at these statistics you're citing.

SPEAKER_02

Yeah, you're talking about the software vendors. Yes. Yes. Uh yeah, there's a number of them that were former MSPs, but not as many as you would think. Oh, really? Yeah. Um and I think it's important for me, anyway, to have experienced that, to understand the challenges that ultimately ultimately now my customers, you know, MSPs face every single day. It gives you a perspective uh that you I think you really need. Yeah. To understand your customers as as well as possible. And I also think that the MSPK appreciates it as well.

SPEAKER_00

I think they do too. When they know that somebody's been in the trenches like them. Jim, what's the difference between a leader and a manager?

SPEAKER_02

One of the things I say about leaders You're not really a leader. I think you can make someone else a leader. Um managers tend to focus on I think supervising people to get certain uh activities, which is fine. Yes. We need that. We need that. Yes, yes. One of the keys to leadership, in my opinion, is the ability to win over hearts and the you really need to forge a vision. Get people to understand why that vision is important, answer the why. Like, why do we exist? Why is what you do so important? Get them to buy in to exactly what we're doing and why we're doing it, and make sure they feel a sense of ownership of that. And that goes a long way, like I said, in winning hearts and minds. And I think that is a great trademark of a leader.

SPEAKER_00

My MSP, I've had to have had to have a couple bad or tough conversations with managers who thought they were leaders. Because the ego can get in a little bit there, you know. And um try to train them a bit. I mean, can a leader be born? Can it be trained? What do you think? Is a leader born? See that.

SPEAKER_02

It's a great question. Uh and there's certainly you can debate it because there's good arguments on both sides here. But for the most part, I think there's people who are born with certain instincts in a leader. And you can certainly learn a certain amount of it. But I think the best leaders combine the instincts they're born with with learning from their environment and their past experiences. Very, very cool. And I'm fortunate, you know, to work with some really, really great people. Yes. Years going back to my MSP days at Thrive, and I look back and there's a lot of folks that we had our executive leadership that are now leading other companies, but leading divisions of companies and doing well. Uh, but for now that's one of the things that gives me the most satisfaction about my career. Yeah, that's nice, huh? Is knowing that so many people that I've worked with in the past have gone on to be successful other places.

SPEAKER_00

We're here to say Connect 26. I heard you on stage saying there was 19 of them.

SPEAKER_02

Yes.

SPEAKER_00

And you're this the 15th? My first was in 2007 when it was at the Mandalay Bay, and now it's back there next year, yeah. And uh the founder, that's still when the founder was was running in Blackie, yeah, yeah. And uh things have changed, things have changed dramatically.

SPEAKER_02

Technically, that was a four season.

SPEAKER_00

That's right. There was a four seasons, like the top four floors or something. Yeah, yeah.

SPEAKER_02

His wife had report for Mendeley Bay or four seasons or had some sort of interesting.

SPEAKER_00

Because it was always there. Yeah.

SPEAKER_02

Uh so yeah. Yeah, because they had put on, you know. It's always had a reputation putting on good events here in Vegas. Out of the 19 Connects, there's only been two, not in Vegas.

SPEAKER_00

San Diego?

SPEAKER_02

San Diego. Where else? Or in Lana.

SPEAKER_00

Oh to Orlando one year, I think I remember that.

SPEAKER_02

That was a bad year.

SPEAKER_00

Yeah, not a good year.

SPEAKER_02

I'm guessing.

SPEAKER_00

Ooh. Ooh. Ooh.

SPEAKER_02

It was uh that was here in 2015, I believe.

SPEAKER_00

Wow. I also remember the women in the balls there.

SPEAKER_02

Yeah, that was at Orlando.

SPEAKER_00

No, that was here. Yeah, yeah, that was here, yeah. Yeah.

SPEAKER_02

That was uh I think they unleashed that trick in 2013.

SPEAKER_00

It was that late.

SPEAKER_02

Oh yeah. I remember that specifically because we were independence IT, we were the Platinum sponsor. Uh the lead sponsor of that one event.

SPEAKER_00

So was your motivation to get that dug? Did you have an influence on that decision?

SPEAKER_02

Oh, it's been a platinum sponsor.

SPEAKER_00

Oh, division for the and for the entertainment, you know. Yeah.

SPEAKER_02

So but one of the nights was a uh a concert at House of Blues.

SPEAKER_00

Yes.

SPEAKER_02

Well, they uh getting covered there.

SPEAKER_00

I remember this.

SPEAKER_02

Oh, very good.

SPEAKER_00

And I went backstage with your team too. Yeah, the team was great. Yeah, yeah, yeah, yeah. I do remember that. Yeah. Yeah, good times. Yeah, yeah, very good times. So your goals this week, Jim.

SPEAKER_02

Meet with as many customers as possible, deliver great messaging on stage and in individual meetings, and make sure our customers understand, our partners understand uh that we're doing what we committed to doing and continue to uh drive that level of credibility uh in the industry that you know we will continue to innovate and create great products for them.

SPEAKER_00

You were on stage after the keynote by the CEO Reyna is her, I believe it was her first Connect.

SPEAKER_02

Yeah, this is Ronia's first connect.

SPEAKER_00

Incredible. I mean, great energy, the passion for the platform for products. I mean, it was really, really she's got really great energy. It must be really cool.

SPEAKER_02

Yeah, it is. I go on great with Ronia, yeah, and I always tell her that she really only has one mode, and that's the excitement. Is that for right? Yeah. Wow, wow.

SPEAKER_00

Yeah, because it's been a tough ramp-up for her, right? I mean, to be submerged like this, I mean, it's not an easy gig, right?

SPEAKER_02

Yeah, what's interesting. I talked to her before we, you know, before she became CEO, this time last year, actually. And had a fantastic conversation with her, and I knew her, I felt her energy for uh for it then, and she didn't really know much about the MSP space at all. And then she joined in June, first week of June, uh, end of 2025. And I remember saying to her in December, um it's amazing how fast she's picked up the business. Yeah, she's obviously a very smart individual, and she's been able to really submerge herself in the company and in the industry, and she's picked up you know the entire industry and our product set and what we do extremely fast.

SPEAKER_00

Incredible.

SPEAKER_02

New CTO, new CTO, the team.

SPEAKER_00

Yeah, he was really impressive up there as well. And incredible things happening with this company. I it's it's um it's it's refreshing. I mean, I'm no longer an MSP, but I I see all these products, I see what you do. I think, wow, I wonder what I can do with this platform if it's on MSP.

SPEAKER_02

Yeah, yeah. It's it's so you use the right word, platform. Right. And it's no longer just a collection. Oh, that's right.

SPEAKER_00

Yeah.

SPEAKER_02

Yeah, I I will say, like, you know, it's been a journey. One of the things I said on stage yesterday was you know, Caseya was at the forefront of helping MSPs win on the managed services transition, going from break fix to managed services. Yeah, because RMM really launched. First tool I use services is Caseya RMM. Yeah, but you bought 2005. You know, and then you know, quite honestly, Casey struggled from 13 to you know 2015. And then Fred deserves a ton of credit. Yeah, ton of credit. Uh and he and it was his vision for IT complete. I'd say, and did a fantastic job of acquiring a lot of really great actors, which ultimately brought us to Gaseya 365, which was a yeah, it's a giant commercial success. And then we're able to parlay the wiki complete message with three sixty-five and roll that right into the next evolution, which is intelligence.

SPEAKER_00

Yeah, big launch yesterday and uh it's really exciting. Jim, is there a questi question you wish more people asked you?

SPEAKER_02

No. There's none. I mean people ask me a lot of questions. Yeah. So I can't think of any one question that I wish people asked me because I feel like I feel a lot of them. Um but it's all good. I like answering questions.

SPEAKER_00

Yes, yeah, sure, you sure do, yeah. And uh and when I started the MSP, Jim, I was working way too hard. Yes. You were two, 16-hour days, not paying attention to myself, not working out. I'm at the doctor, she tells me I'm at 340 pounds. I don't know if you know this.

SPEAKER_02

No, I know it.

SPEAKER_00

I don't I don't think I I never knew you when you were that big. 340, 46 inch weight. She says this to me, if you don't lose this weight, you're not gonna see your daughter graduate. Scared to life. I knew I was getting big, but I didn't know I was that bad. Next seven, six, seven months lost 120 pounds.

SPEAKER_02

Graduated off.

SPEAKER_00

Kept it off. You know, you can't look at the finishing line. These are people ask me how I always say discipline. Yes, focus, motivation. How does discipline play a role in your life?

SPEAKER_01

Yeah, pretty much everything.

SPEAKER_00

You don't say everything. I mean being a football player, being Yeah.

SPEAKER_02

I mean, I learned at a pretty young age that discipline and commitment is really important. And one of the things I tell my son all the time, 21-year-old college student at Suffolk University in Boston, Cam. I tell him good decisions plus great effort equals desired results. And I just don't tell him that for the sake of telling him that. I really believe it because it's proven to be a successful formula for me. Oh my god.

SPEAKER_00

Sure has. Jim, thanks so much for your time today, man. Nice seeing you again. Thanks for finally having you on. Great to see you, Joe. Thank you. Always a pleasure. Well, thank you for listening and/or viewing Joey Pins Discipline Conversations. Please share this episode with one or two of your friends who you think may benefit from the episode. Our website, www.joeepins.com. There you find lots of resources, and you could join our mailing list. Please follow us on all our social media Instagram, Twitter, and Facebook. Podcast information, the video version of our podcast is on YouTube. Please subscribe. Audio is on all major podcasting platforms. Please follow them. And if you like it, please consider giving five star rating. Would really appreciate that. Thank you again for listening or watching Joey Pinn's Discipline Conversation.