IAM736- Firm Owner Leads in Delivery of Technology Services

Dave is regarded as a leading expert in the delivery of technology services, with broad experience in both technology and business. He owned and operated an IT Solution Provider and MSP for over a decade, both acquiring other organizations and eventually being acquired. This firm was a winner of multiple awards, including Kaseya’s Cutting Edge and ConnectWise’s Best New Idea, as well as being a finalist for Microsoft’s Worldwide Partner of the Year in the Small Business Specialist category. After his MSP experience, he has worked for multiple vendors at such companies as Level Platforms, GFI, LogicNow, and SolarWinds, leading community, event, marketing, and product strategies, as well as several M&A activities. He is also the host of “The Business of Tech,” and he also is a co-host of the “The Killing IT Podcast.

• CEO Hack: I outsource a lot and use automation tools
• CEO Nugget: Breath a little
• CEO Defined: Leadership role and getting obstacles out of the way of your team

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[00:00:02.20] – Intro

Do you want to learn effective ways to build relationships, generate sales, and grow your business from successful entrepreneurs, startups, and CEOs without listening to a long, long, long interview? If so, you've come to the right place. Gresham Harkless values your time and is ready to share with you precisely the information you're in search of. This is the I AM CEO Podcast.

[00:00:29.80] – Gresham Harkless

Hello. Hello. Hello. This is Gresh again from the I AM CEO podcast, and we have a special guest on the show. We have Dave Sobo of the Business of Tech podcast. Dave, it's awesome to have you on the show.

[00:00:37.70] – Dave Sobel

Oh, it's great to be here. Thanks for having me.

[00:00:39.79] – Gresham Harkless

No problem, Dave. Super excited to have you on, and we had a phenomenal podcast. We want to drill down a little bit deeper. But before we jump in, I want to read a little bit more about Dave so you hear about all the awesome things that he's doing. Dave is regarded as a leading expert in the delivery of technology services with broad experience in both technology and business. He owned and operated an IT solution provider in MSP for over a decade, both acquiring both organs both acquiring and organizing other organizations eventually being acquired.

This firm was a winner of multiple awards, including Kaseya's Cutting Edge and ConnectWise's Best New Idea, as well as being a finalist for Microsoft's Worldwide Partner of the Year in the small business specialist category. After his MSP experience, he has worked for multiple vendors at such companies as Level Platforms, GFI, LogicNow, and SolarWinds, leading community, event, marketing, and product strategies as well as several m and m and activities. He is the host of the Business of Tech podcast, and he is a cohost of the Killing It podcast. Dave, are you ready to speak to the again, to I AM CEO community?

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[00:01:42.79] – Dave Sobel

I totally am. This is exciting. Thanks for having me.

[00:01:45.20] – Gresham Harkless

No problem. Super excited to have you on, and we had a phenomenal podcast. But I wanted to hear a little bit more because you had a really phenomenal story on how you guys started winning your business. Could you take us through again your CEO story for those who may not have listened?

[00:01:57.09] – Dave Sobel

Yeah. I always start from this place. If I'm an engineer, I mean that, like, despite the fact that I feel like I sometimes have drifted from it in terms of leadership and sales and marketing. I'm an engineer at my heart. I have a computer science degree. I'm super proud of that. And I was starting my career as an engineer, as a developer, writing code, developing software, helping companies directly hands-on with technology. That ran into the reality of the two thousand two downturns when the organization I was look working for let go of all the tech people, And the sales and management people stuck around.

The lesson I took away from that was, that the people in charge, even if they're incompetent, seem to be the ones sticking around. So I can drive a company into the wall just as good as they can. Yeah. And that was my that really was my takeaway. And so I started my technology services firm based on the core idea of I'm just gonna help people with technology. Gonna figure out small businesses, we're gonna get involved with that. And it started like a rocket ship, and it was a great ride. And as a CEO, as an owner, it's you're on your own little island.  don't you can't tell your customers about your problems. You can't tell your employees about your problems. And I didn't I was an engineer. I don't know how to run a company. I'm figuring it out as I go.

So I reached out a lot, and I reached out a lot in a digital ton of networking, and then I got super involved in peer groups and collaborative communities to work together with other IT people who were suffering from the same problem. And that also I quickly moved to not only participating but being a leader. And I launched some peer groups in Europe, and I got involved in launching communities for cup tea. I've done all that kind of stuff, but I loved it. And so when I had the opportunity to sell the solution provider business, I sort of said, you know, let me figure out if somebody will pay me to do that, and let's make it a business thing.

And the core lesson of that was if we empowered our customers and we made them better, they sold more of our software, and that made us money too. So if you invest in your customers and help them grow, you can accelerate their growth. That and thus, they grow, we grow, and it was a great machine, particularly as you think about subscription model software and you think about the way it's being transformed, that's great for everybody. That was my role. I loved doing a super helping people is just fun work. Right? And then when it's also paying everybody, it's even better. Exactly.

You know? And when, when it was all done and we'd sold, you know, with on the final sale, you know, my former CEO and I were talking and he goes, you know, he introduced me. He goes, well, this is the guy who helped, put a hundred billion dollars of value into the business. It's like, okay. That tells you the power of investing in that kind of thinking. And that's how I got to where I'm at now, and my thinking is I wanna change with education. I wanna change by changing the conversation that we have because a lot of small companies don't have a resource that's an analyst like a Forrester or a Gartner, something like that. These small companies don't have somebody sticking up for them. I can do that. I can complain about it or I can do something about it?

[00:04:50.80] – Gresham Harkless

Yeah. Absolutely. you start to scratch your own itch and, obviously, by scratching your own itch, a lot of times you're scratching the issues with so many people and you're helping to provide them something. And I think, when we had the podcast, I talked so much about more so much about the engineering kind of mentality and how they're such great entrepreneurs because you're able to kinda see a problem and you're able to kinda solve that problem as well. But I know one of the things that we talked about, when we, connected or reconnected, I should say, is how you were able to leverage, technology to be able to connect with people that probably weren't in the same physical room as we're starting to experience today. So could you talk a little bit more about how you're able to do that and some of the maybe ways you were able to execute that on and best practices around?

[00:05:31.89] – Dave Sobel

Yeah. It's funny because, you know, obviously, everyone else is I like everybody's catching up. Welcome to work from home, everybody. I've been doing it for, like, fifteen years. You know, it's it's I've I've always been a geek. I love the toys. I love the tech. I've always had a video camera. I've always had the great stuff. I've done all these these bits. And, you know, when I moved from being a local entrepreneur to going to work for large software companies, those companies weren't here. So I and I didn't wanna move. I love this I love the DC metro. It's my home. I love this area. Yeah. Go Nats. Go Caps. Like, this is home.

And I didn't wanna leave. And so it was up to me to solve that problem. It wasn't that you know, they they wanted me to move, but it was up to me to solve that problem. And I made the commitment. I told them, I said, look. I'm gonna do the job for you without having to move, but that means I'm gonna put the time and effort into being effective. Sure. I traveled, like, I would go to I would visit offices. I would show up, you know, periodically, but I wasn't physically there. And I built a virtual team. I built my entire team across, you know, not only multiple offices, but multiple cultures and, time zones.

You know, my at the at its largest, when when we were running, I was running a global events and community team, and I had people in the US, the in Canada, in the UK, and in Australia, all collaborating all remotely. And the and the trick to that was people. You have to go the extra mile and invest in people. I laughed ago because everybody is learning this now. Video mattered. I imposed video calling on all of my team a decade ago when it was still and the reason was simple. I could see their facial reactions and they could see mine. And they and we would stop talking over one another because you could see somebody engaging or disengaging from the conversation. My team would always tease me and I go, Dave, we could totally read your face.

We knew if this if the idea wasn't working, you would and we knew it. We could just tell you we're about to say no. Like and they but you get that by the overinvestment in people. Right? And the tech enables that. You use these technology tools and go all in. Use collaborative what-you-know, online whiteboards, use video, use, you know, all of those extra bits, and then go the extra mile. I did virtual team meetings. I did virtual happy hours. Why? Because people are people. And if you invest time in them, they will respond to that. The tech is just the enablement of it. And so, you know, from for me, it's it's it was all about that. You can do all of the things that you do, and then you just leverage the tech tools to make it happen.

[00:08:10.89] – Gresham Harkless

Yeah. Absolutely. That's extremely powerful. Overinvest in people. And I think that it's so funny because I see the synergies and kinda we talk how kinda how we talked about that customer focus when we talked about your secret sauce on how it's so important to have as, like, that North Star, so to speak, to make sure that you're helping out your customers and your clients' clients' customers, you know, just understanding the people aspect of it. And I think so many times, you know, especially with everything that has changed and adjusted, we sometimes forget, oh, because I'm on a Zoom call because I'm on a conference call or whatever that might be, that means I can't have that connection. I really can't do that. But it's great to hear how you've been able to do that way before, you know, everything like this has happened and how we can kinda remind ourselves on how we can still invest in each other as people, as individuals so that we can have that success.

[00:08:58.00] – Dave Sobel

Yeah. You're it's all team building. I'll quit and I go, I hate I hate virtual Zoom backgrounds. Not because I don't think they're funny, but because I actually wanna see people's space. Mhmm. Like, I want because because you need to connect to them to understand their their place. If they're hiding in a Zoom background, maybe things aren't great at home. Maybe they are in an awkward situation and work from home. Maybe it was forced. You need to know that as a leader, as a person to engage them in a good place. I mean, I have a crazy background here. Why? Partly because I actually always enjoy hearing what people identify with. Oh, is that a Nintendo Power Glove? Oh, is that an Overwatch figure? Like, because it actually humanizes everybody. Right? And I go instantly find out, oh, that's what your interest that's that's where your interests are. We share something in common. I like that portion of it. And it's don't hide it. Be you. It's authentic. It builds people, and it builds teams.

[00:09:49.70] – Gresham Harkless

Yeah. Absolutely. That makes so much sense. And so I wanted to, ask you now for what I call your secret sauce, and this could be for you personally or your your podcast and everything you're doing. But what do you feel kinda sets you apart and makes you unique?

[00:10:01.29] – Dave Sobel

You know, it's funny, but the thing that I've come at it is by being really core to that lens of what the value of technology services is. You know, I've always anytime I put people or the customer at the center, I've always done well. And anytime I've strayed from that, I've got that's when I've been at my least effective or made my most mistakes. And I don't mean it as, like, this cliche because lots of people talk about, like, focusing on people. I don't mean it that way. I mean, it's about the lens of perspective. Like, I think all the time about who the customer is and what they're doing. For me, the customer is the technology services organization. But, that also means I gotta go one level deeper and understand their customer too, the consumers of the technologies. And every time my little secret sauce of life is to think that way and to think about who that customer is and everything flows from that.

[00:10:58.00] – Gresham Harkless

Yeah. Absolutely. That makes so much sense. So I wanted to switch gears a little bit, and I wanted to ask you for what I call a CEO hack. So this could be like an Apple book or a habit that you have, but what's something that makes you more effective and efficient?

[00:11:09.29] – Dave Sobel

So I outsource a lot. I am an I mean, I have to laugh and go, look. My core business has always been I you outsource your technology to me, I better believe in outsourcing. Okay. You know? So I always say my hack is always the, like, I there's so many things I can't do. That means I surround myself with people that can totally do that. I leverage both technology tools and people heavily for that. I love Fiverr and Upwork and automation tools and everything that I can do to focus my attention on the thing that I'm good at and find everything else with somebody who with good at that can teach me or make me better. So I say that is outsourced. Outsource as much as I possibly can. That means giving that to the expert and leveraging their expertise. That's my hack.

[00:12:00.39] – Gresham Harkless

Absolutely. Love that. So I wanted to ask you now for what I call a CEO nugget. So this could be a word of wisdom or a piece of advice. It might be something you would tell somebody who's listening to your podcast or engaging with you and talking with you. Or if you hopped into a time machine, you might tell your younger business self.

[00:12:17.10] – Dave Sobel

I think for me, it's I almost wanna say it's the breathe a little. Like, you know, it's it's it's you're you're super hard on yourself, and that's good. That drives you to succeed but breathe a little. It's it's okay. It'll you can there is I I always fall back a lot. I quit because my father always said it all the time. This is measured twice and cut once. And he liked to like, his hobby was he would be a woodworker, and he always sort of said that. And every single time, I always go measure twice and cut once. It's okay to be thoughtful. It's okay to shut up sometimes. Sit back and listen. Like, it's if you don't if you don't have the answer, that's okay. That's okay. Breathe. It's okay. It'll come. Everything feels super fast. It usually isn't. You know, I like deadlines. I like the swishing sound they make as they go by. Like, because because oftentimes, it's arbitrary. It's stuff I've put on my own self. If I look at it and say, like, it's okay. Slow down. Your thoughtfulness will get you there way better. It may seem slower, but man, it gets you there so much faster.

[00:13:16.79] – Gresham Harkless

Awesome. I love that. So now I wanted to ask you my absolute favorite question, which is the definition of what it means to be a CEO. And we're open to our different quote-unquote CEOs on the show. So Dave, what does being a CEO mean to you?

[00:13:26.89] – Dave Sobel

So it's funny because the law the more I do this, the less worried about titles I've gotten over my career. I think, ultimately, I look at it as very much a lead just a leadership position. And the best leaders are the ones that are empowering the people around them to do their best work. I always look and say, you know, when I've led large teams or my most effective teams if my job was getting obstacles out of their way, then I was really in my best place. And I look and say, so a CEO their job is to get the obstacles out of the way for the entire organization and make their and and make sure their people know where they're going and have the most clear and new vision. And that even means all the way down to when you're a super small organization, even down to a one person, you're still setting a vision and a direction and you're making getting obstacles out of the way for the people around you to be effective. So for me, that's the definition. It's a leadership role, and that's when it's most effective.

[00:14:24.70] – Gresham Harkless

Yeah. That makes so much sense and is extremely powerful because as you said, you can be an art leader really in a lot of ways in every action that you take, whether you're a solopreneur or you're the traditional, quote, unquote, CEOs and leading large team in a large organization. But as we talked about that trickle-down kind of effect and things that happen, a lot of that happens as a result of the leadership and the vision and executing and being able to empower those around you, in so many different ways that to be able to kinda reach those goals and hit those, those metrics and those marks.

[00:14:51.89] – Dave Sobel

Yeah. Totally. And when you put yourself in that place and even now you say this entrepreneur, you're still leading and helping your customers or helping the people that you're serving. If you're getting obstacles out of their way, that's what's being that leadership role.

[00:15:08.10] – Gresham Harkless

Yeah. Absolutely. Well, Dave, truly appreciate that definition. Appreciate your time even more. What I wanted to do is pass you the mic, so to speak, just to see if there's anything additional you want to let our readers and listeners know, and, of course, how best they can get a hold of you, subscribe to the podcast, hear all the awesome things that you're working on.

[00:15:22.70] – Dave Sobel

Yeah. I appreciate the time. You know, again, my lens is always how technology services can make a difference, and that's the quest I'm on is to try and change the way we talk about that. All of my resources are at m s p radio dot com. The podcast is about the business of tech. It's available every business day. It's on all the podcatchers. All the subscribe links are right there at m s p radio dot com. Please reach out, and I love questions and insights from the audience. I do editorial pieces that directly respond to questions from my audience about what I think some direction is. For me, it's changing the conversation and being kind of a different kind of almost consultant or analyst. It's because I wanna be super available and accessible. Just throw me stuff and I'll go work on it.

[00:16:06.60] – Gresham Harkless

Yeah. Absolutely. You being able to kinda do that on a daily basis related to what's going on and happening is a great way that you're able to show that on a regular basis. So truly appreciate that. We will have the links and information in the show notes, but I appreciate your time again, my friend, and I hope you have a phenomenal rest of the day.

[00:16:20.60] – Dave Sobel

You too. Thanks for having me.

[00:16:22.50] – Outro

Thank you for listening to the I AM CEO Podcast powered by Blue 16 Media. Tune in next time and visit us at iamceo.co I AM CEO is not just a phrase, it's a community. Be sure to follow us on social media and subscribe to our podcast on iTunes Google Play and everywhere you listen to podcasts, SUBSCRIBE, and leave us a five-star rating grab CEO gear at www.ceogear.co. This has been the I AM CEO Podcast with Gresham Harkless. Thank you for listening.

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