IAM1696 – Firm Owner Leads in Delivery of Technology Services

Podcast Interview with Dave Sobel

Why it was selected for “CBNation Architects”: It's always exciting to have other podcasters on the show like Dave. He has a show called the “Business of Tech.” It was great to hear how all the awesome things he started were from just wanting to “help people with their technology.” We also talked about how he was ahead of the curve in understanding how important the people part of the human aspect of the business is.

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Dave Sobel Teaser 00:00

You use these technology tools and go all in. Use collaborative white, online whiteboards, use video, use 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, for me, 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.

Intro 00:30

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.

Gresham Harkless 00:57

Hello, hello, hello. This is Gresh from the I am CEO podcast and I appreciate you listening to this episode. And if you've been listening this year, you know that we hit 1600 episodes. We're doing something a little bit different where we're repurposing our favorite episodes around certain categories, topics, or as I like to call them, business pillars that we think are going to be extremely impactful for CEOs, entrepreneurs, business owners, and what I like to call the CB nation architects, who are looking to level up their organizations.

This month is around technology. We're a technology company that does dot, dot, dot. Technology is no longer an afterthought or something that you might do. It's actually a core part of your business and if you're a real estate investor, you're using it. If you're a financial firm, you're using it, cleaning company, author, or speaker, you are using technology, and if you are in any type of business, you are using technology and if you're not, then you're probably gonna be disrupted by this.

So this month we're gonna look into repurposing episodes that are around technology. Whether that be firms or organizations that are actually investing in technology and have that as a core part of their mission and vision of what they're doing or people that just might be using them as CEO hacks and CEO nuggets in ways that you can leverage them. So remember that we're all a technology company that does dot, dot dot or a technology organization that does dot, dot dot. So sit back and enjoy this special episode of the I am CEO podcast.

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 Sobel of the Business of Tech podcast. Dave, it's awesome to have you on the show.

Dave Sobel 02:24

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

Gresham Harkless 02:26

No problem, Dave. Super excited to have you on and we had a phenomenal podcast. We wanted to drill down a little bit deeper, but before we jump in, I wanted to read a little bit more about Dave so you can hear about all the awesome things that he's doing. And 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 Connect Wise's Best New Idea, as well as being a finalist for Microsoft's Worldwide Partner of the Year in this 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 the host of “The Business of Tech” Podcast and he is a co-host of “The Killing IT” Podcast. Dave, are you ready to speak again to the I am CEO community?

Dave Sobel 03:26

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

[restrict paid=”true”]

Gresham Harkless 03:28

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 got started winning your business. Could you take us through again, your CEO story for those that may not have listened?

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Dave Sobel 03:40

Yeah. I really do always start from this place of, I'm an engineer. Yeah, I really mean that. Despite the fact that I feel like sometimes I've drifted from it in terms of leadership in sales and marketing, I'm an engineer at my heart. I have a computer science degree. I'm super proud of that and I started my career as an engineer, as a developer, writing code, developing software, and helping companies directly hands-on with technology. That ran into the reality of the 2002 downturn when the organization I was 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, 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 well as they can.

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. I'm gonna figure out small businesses, we're gonna get in involved with that. And it started off like a rocket ship and it was a great ride. And as a CEO, as an owner, you're on your own little island, you can't talk to your customers about your problems. You can't talk to your employees about your problems. 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. I reached out a lot, did a ton of networking, and then got super involved in peer groups and collaborative communities to work together with other IT people who were suffering from the same problem. And 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 Captia. I've done all that kind of stuff and I loved it. And so when I had the opportunity to sell the solution part of business, I said, let me figure out if somebody will pay me to do that, and let's make it a business thing.

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 you help them grow, you can accelerate your growth. 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 helping people. It's just fun work, right? And then when it's also paying everybody, it's even better. Exactly. And when it was all said, done, and we'd sold, on the final sale, my former CEO and I were talking and he introduced me. He goes, well, this is the guy who helped with putting a hundred billion of value into the business. It's like, ok, 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 changing the conversation that we have. Because a lot of small companies don't have a resource that's an analyst, like a Forester or a Gartner or 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.

Gresham Harkless 06:23

Yeah, absolutely. So could you talk a little bit more on how you're able to do that and some of the maybe ways you were able to execute that and what best practices around?

Dave Sobel 06:31

Yeah. It's funny because obviously everyone else is catching up. Welcome to work from home, everybody. I've been doing it for like 15 years. 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 great stuff. I've done all these bits. And, when I moved from being a local entrepreneur to going to work for large software companies, those companies weren't here. And I didn't wanna move. Frankly, I love the DC Metro. It's my home. I love this area. 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. They wanted me to move, but it was up to me to solve that problem. And I made the commitment. I told them and 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 visit offices, I would show up periodically, but I wasn't physically there. I built a virtual team. I built my entire team across, not only multiple offices but multiple cultures and time zones and it's largest when we were running. I was running a global events and community team, and I had people in the US, in Canada, in the UK, and in Australia all collaborating, all remotely. The trick to that was people. You have to go the extra mile and invest in people. I laugh though because everybody's learning this now. Video mattered. I imposed video calling on all of my team a decade ago and the reason was simple. I could see their facial reactions and they could see mine, and we would stop talking over one another because you could actually see somebody engaging or disengaging from the conversation. My team would always tease me and they'd go, Dave, we could totally read your face. We knew if this idea wasn't working, and we knew it. We could just tell you were about to say no. You get that by the over-investment in people. Right? And the tech enables that.

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You to use these technology tools and go all in. Use collaborative online whiteboards, use video, use 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, for me, 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.

Gresham Harkless 08:57

Yeah, absolutely. That's extremely powerful overinvesting people. 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 remind ourselves on how we can still invest in each other as people, as individuals, so that we can have that success.

Dave Sobel 09:12

Yeah, it's all team building. I equip and I go, I hate virtual Zoom backgrounds, not because I don't think they're funny, but because I actually want to see people's space. Because you need to connect to them to understand their place. If they're hiding in a Zoom background, maybe things aren't great at home, or maybe they're in an awkward situation and working 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 have a crazy background here. Why? Probably because I actually always enjoy hearing what people identify with. Oh, is that a Nten power glove? Always that an Overwatch figure, because it actually humanizes everybody, right? And I go instantly, oh, that's what your interest, that's where your interests are. We share something in common. I like that portion of it and and don't hide it. Be you. It's authentic. It builds people and it builds teams.

Gresham Harkless 10:01

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

Dave Sobel 10:11

It's funny, but the thing that I've come at is this, by being really core to that lens of what the value of technology services is. Any time I put people or the customer at the center, I've always done well, and anytime I've strayed from that, 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 a lot of people will talk about, like focusing on people.

I don't mean it that way. It's about the lens of perspective. 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 actually, that also means I got to go one level deeper and understand their customer too, the consumer 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.

Gresham Harkless 11:04

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 app, a book, or a habit that you have, but what's something that makes you more effective and efficient?

Dave Sobel 11:15

So I outsource a lot. I have to laugh and go look, my core business has always been, you outsource your technology to me, I better believe in outsourcing. So I always say my hack is always like, there are 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 fiber 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 with what they're good at that can teach me or make me better. So I say that it's outsourcing. Outsource as much as I can possibly can. That means, giving that to the expert and leveraging their expertise. That's my hack.

Gresham Harkless 12:01

Absolutely. I 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 that'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.

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Dave Sobel 12:16

I think for me it's, I almost wanna say it's the breath a little like, it's you're super hard on yourself and that's good. That drives you to succeed but breathe a little. It's okay. I always fall back a lot. I quit cause my father always said it all the time measure twice, cut once. He was a woodworker and he always 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 if you don't have the answer, that's okay. Breathe. It's okay. It'll come. Everything feels super fast. It usually isn't. I like deadlines. I like the swishing sound they make as they go by. Like, 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.

Gresham Harkless 13:10

Awesome. I absolutely 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 hoping to have different quote and quote CEOs on the show. So Dave, what does being a CEO mean to you?

Dave Sobel 13:20

So it's funny cause the more I do this, the less worried about the titles I've gotten over my career. I think ultimately, I look at it as very much, 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 what, 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 is their job is to get the obstacles out of the way for the entire organization and make sure their people know where they're going and be the clearest and new vision.

And that even means all the way down to when you're a super small organization. Even down to one person, you're still setting a vision and a direction and you're 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.

Gresham Harkless 14:16

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 ahold of you. Subscribe to the podcast, and hear all the awesome things that you're working on.

Dave Sobel 14:31

Yeah, I appreciate the time. Again, my lens is always on 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

The podcast is the Business of Tech. It's available every business day. It's on all the podcasters. All the subscription links are right there at Please reach out I love questions and insights from the audience. I do editorial pieces that are directly responding to questions from my audience of what I think some direction is. Because for me it's changing the conversation and being a different kind of almost consultant or analyst. I wanna be super available and accessible. Just throw me stuff and I'll go work on it.

Gresham Harkless 15:11

Yeah, absolutely. And you being able to do that on a daily basis related to what's going on and happening is definitely 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.

Dave Sobel 15:24

You too. Thanks for having me.

Outro 15:26

Thank you for listening to the I am CEO podcast, powered by Blue 16 Media. Tune in next time and visit us at 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 This has been the I am CEO podcast with Gresham Harkless. Thank you for listening.


Dave Bonachita - CBNation Writer

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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