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The podcast powered by the MSP Marketing Edge Welcome to this EASTER SPECIAL – Episode 284 of the MSP Marketing Podcast with me, Paul Green. How one big decision changed this MSP owner’s life Featured guest: Steve Dempsey has been a Managed IT Services owner for over 25 years and only serves small businesses in several different markets in the UJS. In addition he owns a small SEO agency for MSP’s only to help them generate local organic leads for their business. Hello and welcome to this special for Easter. I’m joined today by MSP owner Steve Dempsey, who’s going to tell us his business owning journey. And trust me, you have never heard a story like this before. There are many highlights, one of the best being how he went from losing thousands in his business every month to making thousands, with one key decision. Steve is a unique and generous character, and you are going to love everything he has to talk about. Hey there, I’m Steve Dempsey. I’ve been in the IT business for 25 years and my main IT company is NeoTech Networks. And it’s so cool to finally get you here onto the podcast, Steve. We’ve got our special episode for Easter 2025, and I feel like you and I have both been in lots of the same places at the same time, but we’ve never had a quality conversation. You’re obviously highly active in The Tech Tribe, as am I. We nearly met at Scale Con, which was the big marketing conference in Vegas in October last year. I actually talked to you from the stage and we did some cool stuff where you were in the audience and I was on the stage, but we never found each other afterwards, so it’s absolutely crazy. But I’m delighted to have you here on the show. And the reason I want to have you here, well there’s two things that I want to talk about. The first of them is you are one of the most unique MSPs that I have ever come across and you have a very unique lifestyle and I want to explore today what your life is like and what you’ve had to go through to get to that life. And just as a bit of a tease for the many MSPs that will be listening to this on the podcast or indeed watching this on YouTube, Steve has an enviable lifestyle and it’s nothing to do with having lots of houses, a yacht, cars, anything like that. But Steve is living his best life and also has a great business. So that’s what we’re going to explore first of all. And then secondly, you have one of the most unique approaches to SEO, search engine optimisation, that I’ve ever come across. So I want to explore that because I know you had a huge amount of success for it, and indeed you are helping a small number of other MSPs to implement that in their business. But let’s start with the lifestyle stuff. So first of all, Steve, let’s hear your story. So you said in your intro you’ve been in the tech world for 25 years, which sounds like such a long time, doesn’t it? I’m 50. How old are you right now? I’ll be almost 52. Okay, so we’re more or less the same age then. Talking about 25 years, it sounds a lot and when you realise, hmm, that’s half of my life actually, that’s quite sobering in some respects. Tell us about your tech career then. So how did you get into tech in the first place? How did you start your first business? What’s your journey into this MSP space? To sum it up quickly, full disclosure, I actually never went to college. I only have a high school diploma and I’ve always had an entrepreneurial spirit. My last full-time job was, this is probably embarrassing to admit it’s been that long, my last full-time job was probably 28 years ago. The company went out of business. I always had that just drive in me to do something on my own. And then when I was 27 years old when I was on my own, I started a quote on quote computer company. Let’s just say that I had absolutely no idea what I was doing and absolutely no direction whatsoever. But on the second year I actually did start to get the clients and I actually went to people’s homes and repaired computers and all that good stuff. Yeah, the real old fashioned way of doing it. And when did you make the leap over into managed services? You’re going to love my brutal honesty, Paul, on everything because I am a New Yorker and I think you know me well enough from The Tribe, I don’t hold back and I don’t mince words. Truth be told, a number of years later, 15 years about, I admit I was getting burned out and I did have, and I fully admit this, I had an attitude problem. I had an attitude problem for years. I think just over the work and just dealing with everything, I really let my business slide and it was pretty bad. And then when I turned 40, it’s that whole midlife crisis thing, I got burned by another IT owner in New York City that I was subcontracting for, and then that’s when I had the final aha moment of I need to make a decision. I either need to get serious about my business, or get out. And I’m 40 years old, I’m like, you need to grow up or get out. And it was at that moment that I went full swing into my IT business virtually overnight reinvented my perspective, I got rid of my attitude problem, I saw everything as brand new and I hired my first employee probably about a year later. Amazing. When you talk about that attitude problem, what was that? Was that you being arrogant or was that just being a bit of an arms folded New York IT guy, everyone else is an idiot, that my way is the only way? Or was it something different? Nope, actually the attitude problem was actually I just didn’t want to be bothered. And I did get fired by a couple of clients, and looking back on it I’m very embarrassed by it. I’m sure people picked up on it. I just didn’t want to be bothered, to lift a finger. I think part of it came from just the repetitive work. I mean when you fix someone’s Outlook or printer or whatever for the 500th time, you’re just like, yeah, I just don’t want to be bothered anymore. And it showed, I admit it. Yeah, I think that’s very brave of you to admit that because I’m not a psychologist, but this feels like a therapy session for you, to go back and even to look at an aged fault of something that you are 10, 12 years on from. None of us like to admit our faults and when our behaviour didn’t match up to our values. So thank you for doing that. I think at least one person listening to this will realise that, oh my goodness, that’s me. I’m trapped in that because I’m dealing with the same things and I’m trapped in something I actively dislike. In fact, we have a phrase for it, which is where MSP owners create a prison of their own design and lock themselves inside, and I think it manifests itself in different ways, and that was clearly how that manifested for you. So you got to that point, you had that incident, you made the decision to do it properly or get out of it. Obviously you went in a specific direction. What then happened to the business and take us through the story of how you grew that business. I assume you got more staff, you got more clients. Is it your traditional growth story? It is traditional growth. I did get more. I elevated each year. I got a small office in Manhattan, for the first time in my life I actually had an office and then things grew from there. A couple years later I needed to hire a second tech and get a bigger office. And like I said, I was just on full swing looking back on what held me back at that time. I’m sure other solo IT guys would appreciate this, even for me to hire my first employee, it probably took me, and I’m not kidding, a year to mentally get over the fact that I was paying somebody a full-time salary for work that I could do myself. And the reason why is because I was not a business owner, I was a tech. I was 90% tech – I was not a business owner. And then I finally started to slip over and realise I needed to get other people to do things for me so that I can move on to bigger and better things. That mindset shift from being a tech who happens to be working within their own business, to being the business owner who is working on almost a different level, you’re working on growing this thing and that means having to get people in to do things that even though you can do them. Is that a mindset shift that you could have done earlier or do you think you had to go through that process to get to that point? I think it probably depends on the person. You really need to think big. And I kind of do think big now, but I just wasn’t mature enough or did not have the business sense to think big. But I honestly can say 100% what changed all that was The Tech Tribe, which we knew was going to come up sooner rather than later. Once I joined The Tech Tribe brand new and I started to absorb all that knowledge and then be around not only other business owners, but also other business owners that had 5, 10, 20 staff. Jamie Warner for example comes to mind, who’s a friend of mine now, hearing like wow, he actually has people that work for him and he’s not dealing with his low level stuff. And once that started to rub off on me, it took years, but yeah, that definitely started my transition of thinking like a business owner and not a tech. I love that. And Jamie Warner has been on this podcast a couple of times. He’s such good value because as you say, he’s built an enormous MSP and he’s built Invarosoft as a side project and it’s huge. And Jamie’s just one of the most inspirational people you can speak to, which is great. He is an awesome guy. Jamie’s just a super nice guy too. I don’t know him personally, I only know him professionally, but yeah I bet he is. So what, take us through then to the point at which something changed now, I don’t know what changed for you, I don’t know your story that in depth, but I know that the lifestyle you live today, which we are obviously coming on to talk about, is much different to the classic MSP owning lifestyle that most people live. So talk us through the growth then, whatever it was that caused this change to happen. Yeah, I’ll put it on the table so everybody hears it, right. I was in a cramped Manhattan office, you can imagine how much rent I was paying and I had three other full-time people. I probably had seven or eight people’s worth of work. And we were all just juggling work from one to another and honestly just being a glorified help desk. And I was not doing anything proactively. I was barely working on sales because I was always answering tickets myself and all that good stuff. In the past seven years, I purchased three other IT companies because my road for expansion was absorbing other IT companies. So the first one was a huge financial success and I bought it in Long Island, New York. The second one I bought in Minneapolis, Minnesota, and it was like a so-so success. And then I ended up buying a printer repair company in New York City, and I should’ve had my head examined for buying that, but I can’t take it back. It sounded like a good idea at the time. And that’s that. When Covid hit, and I’ll just fully disclose this, I was a quarter million in debt from the acquisitions and my appetite far exceeded my business sense, and I should never have purchased a printer repair company because I already had debt from the second acquisition, and it was just too much for me to take on. I was just too ambitious. Covid hit, I lost my biggest client in New York City, which was like a 20 chain restaurant client, and that was also 30% of my business. So I was probably, thinking back now, I was probably in the red about $20,000 a month. So in other words, by the time covid hit, I was already losing $20,000 a month. The only thing I was doing was just not paying my credit card. I was paying probably almost $3,000 a month in credit card interest alone. And a couple of months after Manhattan shut down American Express actually shut off my credit card and they wouldn’t let me charge anything else. I was actually in serious financial trouble. And then it was at that moment that I had made a decision just to turn everything upside down within one week. So within one week I closed both my Manhattan offices, I laid off all three of my salaried employees in Manhattan. And then I went full swing into virtual, which I still have many of them today, which was freelance Latin America in Venezuela. And then I hired full-time employees down there for a fraction of the cost. And I would say within one month I went from $20,000 negative to like $10,000 positive within a matter a matter of weeks. That’s incredible. What a story. And there’s so many things to unpack from that. Let’s start with, we’re going to delve a little bit into all of that I think, and then we’ll talk about what you’ve done subsequently. I now understand how the lifestyle you live today is possible. So let’s talk about that that week. I’ve never personally been in a position where I was that deep into debt. So I’ve had bad years, I’ve had good years, I’ve been in business for 20 years myself and especially, I can imagine if you’re that much in debt and then this pandemic comes along and shuts down the city and takes your biggest clients away and then the credit card company say ring and say, cut your cards up, that’s as low as you can go, right? You must’ve been weeks away from personal bankruptcy, nevermind just losing the business. So, talk us through the mindset, and I appreciate we’re talking about something five years on, so a lot of those emotions that are now memories, but what was the thinking and the mindset? Did you become more clear? Did you go out and just try and drown your sorrows? What was your way of dealing with that and reaching that decision of I’ve got to do something so extreme? It could be the end of everything, but actually I’ve got no option. I knew I was in trouble, and the credit cards obviously were the debt and the interest and everything was racking up. So I knew I was on a bad road. My position at the time was actually to work my way out of it. So my day started at 5:00am, I was working until whenever, seven, eight o’clock at night. I was working six or seven days a week trying to get out of this, doing the work of 10 other people and all that other good stuff. So the end result is Covid and Manhattan shutting down and me losing my biggest client was actually the best thing that could’ve happened to me, to be honest with you, because if it did not happen, I did not have, for lack of a better word that I want to use, I did not have the guts to do what needed to be done, which was close the go full swing into a virtual staff. I just do not have the guts. If covid did not happen, if those events did not happen, what I would have done is I probably would have borrowed a ton more money from family, friends, whoever I can get it from, and pretty much pay that off and just move debt from one to another. But looking back on it, it was the best thing that happened to me because it forced my hand and it forced me to do all those things virtually overnight, which has led to my lifestyle here, here and now present day. I don’t think that would’ve happened if those events didn’t happen. Yeah, absolutely. And you mentioned freelance Latin America, it’s a company I’m familiar with, I did a webinar with them actually a few months ago. Really good people, very passionate about what they do. This is now going to end up as a free little advert for them, but then they’re the key thing to you doing what you did. If we actually, let’s not talk about them, let’s talk about the concept of what they do. So you have essentially outsourced your tech work to people not in the US. Is that correct? That’s essentially what you’ve done there. Yeah, that is correct, but almost, I understand what you’re saying about outsource, but they work for me full time and my first couple employees from freelance are actually now with me going on year five. Got it. So let’s take the word outsource then. So you’ve shifted the work from people who sit in an office, s…
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