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How to Build and Measure Confidence in Your Business, with Damien Stevens


Damien Stevens 1

How to Build and Measure Confidence in Your MSP Business, with Damien Stevens

Confidence. It’s that semi-elusive, hard-to-measure thing that we all want.

We want it personally, and we definitely want it in our business.

But how do you get confidence? How do you become confident as a business leader or CEO in your business? And then, how do you inspire confidence in your clients and customers to keep growing and expanding?

There’s no magic solution, but there are lots of steps you can take as a business leader to build and maintain confidence. We spoke with Damien Stevens on a recent episode of the Stride to Freedom podcast to hear his insights into confidence in your business.

Here’s what he told us.

Damien’s Story

Damien has a fascinating story. He’s open about the fact that he was both a high school and college dropout because of a necessity to take care of his family financially by working.

And despite many people telling him he won’t amount to much, Damien refused to listen.  Today Damien is the CEO of Servosity, a cloud back-up and security solution for MSP’s.

Damien’s path to business success was difficult and, in many ways, defied the odds. Because of this, he’s always had a unique outlook on what is possible if you have a bit of confidence on your side. He routinely hires people who don’t have the traditional degree-plus-experience path and rejoices when he gets to champion someone and see them operate in their zone of genius.

His perspective on confidence is important to the work at Servosity, too. Serving primarily MSP businesses, it’s their goal to “make the MSP the hero in the fight against data loss and ransomware.”

They do this with guaranteed tested backups because, as Damien shares, if you don’t have tested backups, you’ve essentially shredded them.

Damien and his team’s commitment to regularly tested backups builds confidence in their clients. They know that their data, and therefore business, is safe. And with that confidence, both Servosity and their clients can successfully grow and expand their businesses.

6 Tips to Build and Maintain Confidence

Confidence is not just about a few things you do, it’s about everything you do in your business. It’s how you operate your business.

There are a lot of ways to build confidence as a leader and inspire confidence in your clients. Here are six ideas Damien discussed with us:

  1. Focus on recruitment: Confidence starts with hiring the right people and bringing them into your organization. The right people help you sleep easily knowing things are being taken care of.
  2. Audit people’s zone of genius: Not only should you bring in the right people, but constantly check that they are operating in their zone of genius—the thing that lights them up.
  3. Remember confidence is a mindset: It’s important to check in on what stories you are telling yourself—is it truth or just a story that’s not going to serve us?
  4. Set realistic objectives: Damien is a visionary leader that can inspire people around an idea. But all vision and no action steps to get there can be discouraging for people. Inspire confidence by laying out a clear plan and objectives to follow.
  5. Invest in systems: Damien and his team have built high-quality, rigorous, and well-tested systems into their operations at Servosity. This is important in building confidence because it ensures they deliver on their brand promise to clients.
  6. Measure: Make sure you are looking back and measuring gains—what have you done well? What has the team accomplished? This helps team members move forward with confidence knowing that they are making positive strides.

Of course, this is just an overview of some of the main points Damien shared. If you want to get into the meat of our conversation, listen to our full interview on the Stride to Freedom podcast.

You can also get in contact with Damien on LinkedIn or visit Servosity’s website to learn more about what they’re up to.

The Stride to Freedom podcast is hosted by Stride Services.  Contact us today We offer back-office accounting and CFO services, including stable and efficient bookkeeping, cash flow management, and actionable analytics for growth. You’ll enjoy this Podcast episode with Damien Stevens.

Listen Now

We are fortunate to have Damien available to spend time with us on this edition of Stride 2 Freedom. If there is a speaker you’d like us to interview, click here and let us know. Stay well. Stay safe. Stay healthy.

Show Notes and Links From Episode:

Damien Stevens: LinkedIn

Servosity: Website/LinkedIn

Damien Stevens Email: dstevens@servosity.com

Damien Stevens: Top 10 Takeaways

Episode Transcript:

Russell Benaroya: Hey, everybody. Welcome back to another episode of the Stride 2 Freedom podcast where we help leaders get and stay in their zone of genius. What is your genius zone? It is that thing that you do that feels effortless for you, where you are super efficient, where you light up, and where, if that is what you could be doing all the time, you would. But we all know that as leaders, we get drawn into other areas of the business that tend to drain our energy.

I am your host, Russell Benaroya. I started the Stride 2 Freedom podcast, to create opportunities for business leaders to get exposed to individuals who run businesses that are in the business of helping you get and stay in your zone of genius.

Today, we are going to touch on a topic that is hard to measure, but incredibly important. That powerful metric is confidence as a measure of how to help you focus on achieving your highest and best use. When you have confidence in the execution of your services and your team, it massively frees up your mind space to stay looking out on the horizon, build strategy, and create an organizational design in service to that strategy.

I don’t want to minimize this metric because it dogs most of us a percentage of the time because it’s hard to measure. So here’s how we’re going to tackle it today. I have invited Damien Stevens on the podcast. Hey, Damien.

Damien Stevens: Hey, Russell. Good to be here.

Russell Benaroya: Nice to see you. Thanks for joining me. The reason that I think Damien is such an interesting guest to have on is because he is not only the founder and CEO of a really interesting business called Servosity, but the business that he runs, and the service that he offers is designed to give clients a lot of confidence.

Servosity is a backup and disaster recovery solution that’s provided to IT MSP owners to give them confidence that their clients’ data is safe. That’s a big piece of confidence today for many business owners, but especially for MSPs, whose reputational risk is on the line. Damien is also the CEO of his business. So he’s also trying to build a business where he has increased confidence so that he can be focused on the horizon.

We’ll get a chance to talk to him about it. I find Damien to be quite open to being vulnerable and sharing authentically about his 17 years or so journey of being the CEO of Servosity. What do you say we jump in?

Damien Stevens: Let’s do it.

Russell Benaroya: Okay. Damien, what’s going on in Greenville, South Carolina today?

Damien Stevens: We got a break from some rain. It’s a beautiful day. I’m very blessed to have a remote team. Some of the things you’re talking about, I think, interweave. Not everybody focused on confidence for their team and I think it can sometimes be more elusive when you don’t see the people physically. Remote work is great. It has some challenges on the cultural side.

Russell Benaroya: We’ll get to that. That’s interesting. What are one, two, or three hacks that you have found to be effective at building a bridge with a remote team that gives you confidence that the machine of the business you’re building is running well?

Damien Stevens: My view is that the people are the team; people create the value. Therefore, it starts with the hiring process. It starts with being intentional about what you’re looking for, which is always hard. If you’re an earlier business owner, I know in the beginning days, it was like, “My job description should have just said unicorn. You can do anything, you know everything. You never need to rest and take days off for those.”

I’ve realized I’m certainly not anything like that, and neither is any other person that I’d want to work with. So it starts with the process in the beginning of running through more rigorous than average. I believe that you’ll get out what you put in. I think that starts at the beginning of the hiring process. If you do what everybody else does, you get what everybody else gets. And in this economy, and in this remote work-anywhere workforce, I think you’re going to end up with the average, or maybe even leftovers for the folks that put in a little extra.

One of them is your recruiting process. Even the job description, we found, has driven if we put more work into that. Look, I’m in a rush, and I need somebody, and I just want to copy Russell’s brilliant job description and put it on my site and say I need one of those.

What I’ve learned is that’s a mistake because we have a unique culture. We’re looking for unique things. We’re looking for unique abilities. If we don’t describe that, we won’t capture it. I’m sure you can relate to this, Russell. It seems obvious to me because this is how we work. But it’s not obvious to anybody that hasn’t joined us.

We’ve had to distill that down. It starts with the job description. It starts with the hiring process. Those are the first couple. Then remote work, we’ve blended light check-ins so we don’t have heavy meetings, and easy updates so that everybody knows what others are doing. I mean, across different teams because it’s easy for support to know what support is doing. But sales or billing or development or some other team has no idea.

We try to be cross-functional. Then we’ve recently been experimenting with culture meetings, the entire 45 minutes of our meeting devoted to it. That freaks me out when I say it because it makes me nervous when I say a culture meeting for two reasons.

One, I’m afraid I’ll screw it up, just being candid. The other is I feel like it’s hard because you don’t want to reinvent the watercooler talk that we had around the watercooler. It doesn’t work that way.

Fortunately, we’ve had folks on our team that have raised their hand and said, “I want to lead this.” It started with everything from what’s your favorite movie or song to playing games and doing things you might get to do working together. I think that builds the bonds that help you understand the person outside of you know how to do this, and when I call you, can fix this issue.

Russell Benaroya: Any systems that you’ve put in place, pieces of technology/software that have facilitated connection among a remote team?

Damien Stevens: We’re evaluating a few. What we’ve done, everybody uses Teams or Slacks. We’ve packed together using Zapier, an automated tool that we’ll do Monday morning. Basically, we ask three questions. What did you learn last week? Are there any blockers we could help with? What are you expecting to accomplish this week?

Then we start with one of the most important ones, which is, what did you learn? Not, what did you accomplish last week? The reason that’s important to me is, I feel like if you’re not growing and you’re not learning, you’re taking a huge career risk. Of course, I want everybody who works as part of my team to do a great job. Who wouldn’t say that? But I want you to learn.

I want you to be able to learn more than anywhere you might ordinarily go. That’s why we ask that. And frankly, if we’re being honest, sometimes it’s not as much as another week. But we’ve learned that by asking it, it makes you reflect and go, “You know what, I actually did learn this last week.”

And of course, a lot of us, me included, being technical, you want to put like I brushed up on my PowerShell or something deeply technical, but sometimes the best ones that folks have shared have been, “I learned that not everybody thinks like I do, and this is another way I could relate to somebody in this situation.”

For example, most of the techs I talk to want to learn tech things. Getting outside of your comfort zone and learning things that are not natural are some of the best lessons, I feel.

Russell Benaroya: What I’m hearing is, for you, there’s an important element of confidence, which is knowing that your team is committed, engaged, communicating, open and vulnerable. So that you can go to sleep at night not concerned that you have individuals that are at risk of leaving.

Damien Stevens: That’s exactly right. I mean, it was competitive before, but if you think about the remote, you can work anywhere. That means your competitors are everybody. It’s not just the MSP across the street, or the MSPs in your city anymore. It is anywhere. Your tech could leave and work for my company or Russell’s.

It’s not just a limited set anymore. I don’t do it out of fear of competition. I think that’s wrong. It is like you said. They’re not only committed but enjoying it. The word you said was powerful: vulnerable. I am not perfect, I’m very flawed, but I do try to lead by example and be vulnerable. So I try to bring up things I’m not doing well, things I am scared about doing, and things I am not even comfortable with.

I’ve had a few that I’m like, “Hey guys, I’m not really comfortable admitting this, but I need to. The truth is, I procrastinate in this way and I really don’t want to do this thing.” Of course, I have my own head trash that says, “Gosh, as a founder and CEO, I need to never procrastinate.” But the truth is, for certain things that are not in my skill set and not my genius zone, I would tend to procrastinate more.

We’ve very much been focusing on determining what’s in our 20% or our genius zone. What is the percentage that has to get done and how can we either batch that or perhaps delegate that? Or in the case of your company, Russell, perhaps hand that off?

There are so many places where you can get help, and hand off the things you’re not in your genius zone. And then I’ll be less likely to procrastinate and much happier at work. I know if that goes for me, it will go for others. I feel like I’ve talked to a lot of CEOs. They get it for them, but they don’t understand that the same thing applies for their team. They think, “I hired this person to do these 20 things. They haven’t told me they’re upset, and they still get a paycheck. So they love it.”

That’s the thought process. In reality, half of those things, they’re tired of doing because they’ve been doing them for five years and they’re ready to level up. I don’t necessarily mean a formal promotion, but they’re ready to learn in different ways in a new capacity. So trading that off with somebody else internally or externally can be just the thing that everyone needs to stay in their zone of genius.

Russell Benaroya: Good segue because you’re in the business of MSPs handing off something really important to you to help give the MSP confidence when they’re servicing their clients for backup and disaster recovery work. Do you want to talk a little bit about what that is, how you do it, and the effect or impact you’re trying to have on the clients you support?

Damien Stevens: I think it’s critical. Obviously, it’s different, but nobody would want to hand off their accounting. That’s very serious. The IRS will get a hold of you if you don’t do that properly. So your business is very serious. But I feel like that’s better understood by handing off backup.

I will be vulnerable and indirect. I didn’t start the company with that idea. I started it because I was an MSP and I was managing the backups and they gave me a few green dots and little success emails and said they were successful. My biggest client called, all the servers had crashed. I thought, “This is going to be a long night. This isn’t a fun day and night. But it’s also successful. We’ll get them up and running.” Long story short, we couldn’t. The best-of-breed tool that had been telling me success day after day after day wasn’t able to recover.

I was backing up corrupted data. Spoiler alert, every backup system to this day still does that. And frankly, talking about being vulnerable and feeling alone, I thought I was the only person on planet Earth that was that dumb and that would end up in that situation. I must be the worst person.

I finally started talking to other MSPs. I realized, fortunately for me, and unfortunately for everybody else, I was far from alone. Most MSPs will admit that they have either lost data or had a really near miss. I started looking at the why. I said, “There’s no process. There’s no proof. There’s no audit. There’s no transparency.”

Basically, what it boils down to was we lacked the people and the process. Those are two things. We had the technology for. We lacked the people and the process to have predictable testing to lead to predictable results. If you don’t test your backups, in my opinion, you have shredded those backups. We have a box, we don’t know what’s in there. We don’t know the state of what’s in there. if we don’t know, we’re really betting on our clients’ business, and to a large degree, your own business on, will the backups recover?

I don’t care how little or much they’re paying, they expect you to do recovery. I even talked to some that say, “Well, I sell the premium solution that has more stuff in it and more ability to have insights. And if they really balk at that, then I sell them plan B. But I have them sign a waiver.” I think that sounds great, and I’m not an attorney. Maybe that removes some liability. But at the end of the day, they still expect you to recover.

I’ve never met any client that was paying for any sort of backup or disaster recovery, that didn’t expect you to be able to recover them. Forgetting about the recovery point, they do expect you to recover. So there’s this huge gap.

For most MSPs I’ve talked to, I say, “How often do you test your clients?” I’ll probably get an answer like, “We do a test annually.” I’m like, “That’s actually good. So you test every single client every year?” “Oh, no, for two of our clients. They paid extra.” “What about the rest? Never?” How much data do you think they could lose before you would be in hot water? And do you really trust their backups? I don’t trust them if they haven’t been tested. How much data do you think you could lose before you’d be in hot water with your client?

Somewhere around a day, give or take. A few hours, maybe two days on the other end, but call it a day. So we have this challenge in the industry, in my opinion, that we are not testing. The client doesn’t really pay enough and they’re not willing to pay extra, but they expect you to be able to recover.

And when I say a challenge, I think it’s not entirely the MSPs’ fault. I think they don’t have the time, the people, the process, and the tooling, and the vendors haven’t, including us, we still need to make it easier. After many years of being in the business and talking to so many of my MSPS and giving them more and more tools and more processes, it ended up being more and more time.

We learned the hard way that it seemed like we were never going to get around to it. So it would be like if nobody ever audited your books and never did a closing process. You didn’t adhere to GAAP financials. There are all these things that exist in the financial world. We just don’t exist any sort of that in the backup world. I don’t care which binder you use.

In fact, let me just stop for one second.

One thing that I want to help MSPs is, whether they decide to hire us or not, if you want to have tested backups, you can do it. I have a free download. I call it stealing my process. Yours is an MSP and then there’s AP here running this company helping so many MSPs with 1000s and 1000s and 1000s of recoveries and seeing so many different use cases.

I know this is against the tech-guy code to say this. It’s not the software. You don’t have to hire us. It may sound counterintuitive. You can steal the process. I call it, steal it, download it. It details what we do to test every single day, every single week, every month, and every quarter. You can decide if you’re going to follow that or not. You can take part of it if you’d like.

You talked about confidence. I want confidence in recovery. I’m unwilling to take anything less because of seeing not only my later loss, but 10s and10s of other MSPs. And frankly, it broke our hearts because, for most of the time we existed, we didn’t do the testing for the MSP, maybe a screenshot, which a lot of software does. But that’s not really testing and it’s definitely not enough.

We would see where they were doing these things and probably would be referred to as best practices like I was, yet you still couldn’t recover. I talked to them, and they didn’t have the confidence. So going back to the confidence, test it you have the confidence.

And I don’t trust any backup, or any software until it’s tested. Just like you wouldn’t trust books that aren’t balanced. There are some mechanisms. If you know things are well-tested, you have all the confidence that you can recover.

If you lose a client, probably the best case scenario is they talk bad about you in your market. Maybe the worst case is their insurance carriers doing something in terms of litigation. This is a very bad scenario, your company could be at risk. But you don’t want to put them in that scenario. I’ve seen it in MSPs and clients. In some cases, one, in some cases, both.

Ultimately, the business goes out of business. In every case I’ve seen, they were not asleep at the wheel, MSPs doing best practices, and they were good people. They weren’t these guys that promised the moon and didn’t deliver. Yet, at the end of the day, the employees at the MSP suffered because they had to either shut down or lay off people. The company that ended up either going out of business in some cases or nearly laying off staff.

You need confidence. If your support team, sales team, marketing team, or any other teams don’t see that you have the confidence in the ability to do the job you promised, which, whether you realize or not, you thought you sold then backup, but you really sold them recovery. That tears apart the whole fabric of trust and working together.

Russell Benaroya: You’ve talked a lot about confidence in your team and being thoughtful on the front end around how you recruit and then building a culture of connection. You’ve talked about some systems confidence that is important, specifically your application for MSPs. That’s one example of systems confidence.

What are other areas of confidence that you think are important as a leader to address or shore up to free you up to focus on what it is you’re uniquely expected to do, which is to drive the growth of the business?

Damien Stevens: There’s a couple of things there. I think it’s people and process. If you don’t have people, the process doesn’t matter, or you end up making processes for idiots. Every time you hire one idiot, and if you have too many people like me, you end up hiring an idiot. You don’t realize that you’ve hired somebody horrible. Then you go back and you try to make processes.

What I’ve realized is you really can’t make enough processes for somebody that’s disengaged, doesn’t care, and doesn’t put in effort. You can’t make a process to compensate. So it starts with the people. Again, the recruiting process is a process. That process can turn to the right people. From there, you do need to have the processes along with the people.

I don’t care if it’s accounting, sales, or marketing. IT security obviously should be a process. Compliance has some process. There needs to be a process in there along with the right team.

Then finally, we regularly go through and ask our team to individually go through and say, what is in your genius zone? That’s 20%. What’s 80%? You may have to do it as part of your job, but it’s probably not your genius zone. It doesn’t mean every time we identify that we can immediately get rid of your 80%. It’s not like, I’ve got 10 people on a support team and half of them don’t like this part of the job. I can’t obviously immediately say, “Boom, we don’t ever have to do that.”

Sometimes that goes back into the process where we change what we do and how we deliver an offering. But it often ends up being, okay, this is where you are, and for you to grow and for you to learn, we want you to end up getting rid of that. You’re going to graduate out of that.

And it doesn’t mean that it’s beneath you. It just means it’s not in your zone of genius. I’m a big believer, looking at it from the 80/20 principle, that, for example, there were things a year ago that were in my 20% now they’re not. It’s not that I’m too good, it’s that the business has changed. There are new demands as a CEO as we have more people.

For example, if somebody’s being onboarded, we’re still small enough that I get to be part of that from an introduction and a culture perspective. But I no longer need to create every account in every system. Even though I’m competent, it’s not my zone of genius. A couple of years ago, that would have still been something that I would have had to do.

We try to regularly audit that as a process, for the whole team, and then we can all share. It’s not that we’re all trying to shed work. It’s just trying to identify, I’m unique in this way and I’m great at this. I’m a competitive person, but it’s not about competition. It’s about, I’m better at this, and you’re better at this.

I have folks who think more creatively than I do. They can write copy in far shorter periods of time than I can. Why don’t they do that instead of me spending half a day or an entire day trying to write three good paragraphs for something we’re trying to communicate?

Russell Benaroya: What would you say is your responsibility or maybe broadly the responsibility of CEOs or business leaders, that has the unintended effect of undermining confidence? Meaning you are a participant in any resulting outcome. Where do we trip up on ourselves as leaders, and end up with the unintended effect of undermining confidence, when, in fact, that is what we are in pursuit of?

Damien Stevens: That’s a great question. This will depend on your leadership style, but I’ll speak about myself. I tend to be a visionary type of leader. We’re going to go here, and we’re going to do this. We’re going to get from one peak to another peak and climb this mountain and get to the next summit.

I’ve learned to be more specific, break that down in a process, and do those sorts of things. There are still times that I’ve set up this big vision, and everybody’s excited about it, and we reach for it, there are times when I’ve set it just too far out of reach. There’s a difference between a big, hairy, audacious goal and no chance you can reach it. And maybe you can, but not in that timeframe.

What I’ve learned is, if it’s 14 months, instead of 10, or 12, it’s less about the quarter or some other metric that it has to fit within a quarter or a year, that we actually did accomplish it. I would say, as a leader, it’s setting too lofty of a goal, and then allowing myself and my team, when we got 80%, or 90%, or 95% there, to feel defeated because we grew incredibly. All I’ve done, it set us up for feeling like failures.

We grew revenue faster than we ever did. Our customers are raving more than they ever did. We built this product. We delivered this thing. We innovated in this way. We’ve hired these folks on our team that are crushing it. They’re growing in this way, all these things that matter. We’re doing so well. Yet, if you look at it backwards, almost arbitrarily, the date was picked. I think dates are good for a forcing function. So I’m not saying you shouldn’t have them. But I think that’s where we can trip up and say, “We didn’t hit this quarter’s or this year’s goal. Therefore, we’re failures.”

And especially as a visionary CEO, 20% or 10% doesn’t get me excited. But the truth is 80% is incredible. I’m not saying that you can’t hit those. I think that’s a common one. I can easily set myself up as an individual to say, “Man, I’m a failure.” And even if I don’t tell the team, “I can’t believe you didn’t hit this,” I think they feel similarly. They go, “We said we were going to get to this and we didn’t. We do care a lot about what we say. If we say we’re going to do it, we expect to.”

Russell Benaroya: What I’m hearing you say is, we can sometimes sabotage ourselves or sabotage the team in our pursuit of achieving some lofty aspirations. Then if we don’t hit them, culturally, it might feel like there’s a lack of confidence, or maybe as a leader, you have some disappointment. But what I’m hearing you say is, lofty aspirations in the absence of a shared agreement with the team on the how and when — how we’re going to do it and when we’re going to do it — is so critical to establishing a cadence of consistent confidence. That’s, I think, the piece that’s often missing, the how and the when.

Damien Stevens: As a visionary, it’s too easy for me to say, “We’re going to the moon.” While that is great to inspire you, it lacks a lot of specifics. And even if you say by the end of the year, or whatever the date is, it’s sometimes just not that realistic.

This hit me like a ton of bricks. Unfortunately, in retrospect, we had the best growth year ever. The team and I still felt like it wasn’t enough. Of course, we’re going to push ourselves to do more the following quarter or the following year, don’t get me wrong, but we just had the best year in all sorts of ways and we just felt like we didn’t hit the mark. Just because the mark was essentially arbitrary because when you’re setting future goals, you’re trying to predict the future. I know that I’ve done that.

One thing I would say is, even if I haven’t said, “I’m so frustrated, we didn’t hit this,” we all have the shared agreement that we were going to do this. So anybody that’s driven, is, at best frustrated, and perhaps worse, demoralized. On that note, the thing that we started doing is, instead of measuring the gap from where we are, we started measuring some of the gains that we’ve made backwards.

How far have we come in the last week or month, or quarter? It helps us have confidence. Look at these wins. We’ve won this way, by shipping this new product. We won these customers in this way. They’re elated. We’ve added these new team members, and they’re so excited.

There are wins that we have. When you look at the wins, you feel a lot better than when you go, “Well, it’s only about halfway through the year.” It’s hard to know. If you’re halfway or so, maybe you’re on track. If you’re a little ahead, great. But unless you’ve hit the entire year’s goal, it feels like a marathon. It’s good to have something that says, “Look how far we’ve come.”

As an individual, I keep wanting to go closer and closer to the goal. I keep measuring that gap between the goal instead of how far I’ve come.

Russell Benaroya: You also have a podcast today called the MSP Mindset. It feels like this might even be a topic that you would host on your podcast. I’m curious if you’d share a little bit about that podcast and what you’re trying to accomplish with it. Congratulations, by the way.

Damien Stevens: Thank you. MSP Mindset was born out of, one of the things I love when I work with MSPs, they start off, “We need to do what we promised. We need to manage their backups and test them.” But as the relationship grows, one of the best compliments is when they call and they ask me all sorts of stuff that has nothing to do with backup. Sometimes it’s cybersecurity. It’s pretty close.

But really, it’s about how do I build culture? How do I grow leads? How do I do sales or marketing? How do I put in a better process? I don’t know all those answers, but it is wonderful when they will be open and admit I need help.

It went from MSPs calling and asking me to make introductions. Like, Russell’s really great in this area, let me introduce you to him. Russell can solve accounting, and he could solve several other areas for you. But Russell could talk to you about confidence also and your team. So even if that’s not something that he’s offering as a service, Russell could help you.

That’s where this transformed. I realized a lot more in this piece needs this help than are emailing or calling me. I needed this, more importantly, as an MSP. That’s how the show was born.

Now I interview MSPs and other interesting people, folks that have built a business generally through incredibly hard times, and really struggled. They will share those struggles. It drops slightly as a podcast, but I do a live show. We do take comments. That keeps us on our toes because whatever I think will resonate, the comments usually are vastly different.

It’s fun for me because I get to interview some of the most amazing people in the industry and ask them a lot of tough questions. I can contribute, but I don’t have to be the expert. When I want to figure out culture more, or when I want to understand how do I build this process, or what are we going to do with all this upcoming compliance that’s coming down the road, or whatever that is, I can get an expert.

This is my responsibility because I probably have more time than the average MSP to do this sort of thing as you are so thick in it. You have to be an expert in so many things. So I look at it as my responsibility. Take the time with my team to get some of the best experts and interview them. You can ask questions and you can take away from that.

I love it because I have learned so much. Some of it on the show and some of it backstage. I love it because just like we’re doing here, you learn a lot about people that you didn’t often know about one another.

The best people are the ones that are vulnerable and talk about real issues. That’s where I get pulled in. The people that I can’t learn from or I struggle to learn from the ones that were born on third base, but they thought that they hit a triple. Those people, it’s hard to learn from. It’s the folks that have really struggled and built it from nothing.

When you can raise your hand and say, “That’s me, and I’m trying to figure out that process right now, or I don’t know what to do what is cash flow.” Whether it’s hiring, whether it’s clients and I’m overwhelmed, time management. We do two very different things in terms of what Stride and Servosity does, but they are fairly similar. Both of us take a lot of work off of somebody’s plate so they can focus on what they do best.

In both cases, it’s got to be right. There’s got to be some verification in there. There’s got to be some, some way to prove. It’s not just we did it, and we hope. In both of those cases, there has to be a lot of trust to do that. I enjoy getting to learn from what I believe are the experts in the world in all these different areas.

Russell Benaroya: Speaking of learning from others, and getting under the hood and a little bit vulnerable, one of the things that you are seemingly quite open about is you’re both a high school and college dropout. I’m curious if you could share how you’ve channeled your inner confidence in a non-traditional path to get where you are today.

Damien Stevens: There’s a lot to that. My story starts out with we were incredibly poor. At one point, we were homeless. So I was going to high school and working. And as you can imagine, as a kid 15, 16, minimum wage, fast food, that kind of stuff. Nothing glorious, nothing pretty, but I was working 30-35 hours a week and trying to go to high school. One of those put food on the table and high school didn’t.

At that point, it became clear. My family at that time was my mom and my sister. If we were going to be able to survive and eat, I was going to need to continue to do that. I had a mother that was disabled. I had a sister that was younger, there was no father in the picture. So out of necessity, I can work, I’m old enough now.

I’ll never forget dropping out. The teachers, I think they meant well, but several of them were like, “Don’t drop out, you’re going to end up on welfare.” One of them said that after they signed the consent form, which I thought was not the most motivational speech. But I dropped out because I had a practical need to feed my family.

It started with something that simple. I knew that I wanted to do more. I didn’t have clarity of exactly what that was going to look like, but I did take the next step. I dropped out, and I immediately scheduled taking the high school equivalency, the GED.

The first time that was available, I took it. I was fortunate enough to pass it. The odd thing is I have less than 40 days of high school total. I was quite young. I was 15. And because I passed, I had another plan. It’s always good to have a plan, which was to enroll in a Technical College. They didn’t have any IT-type stuff and I was into it. The closest thing they had was robotics. Robotics also happened to be one that paid better than a lot of other things. So I said, “Great, let’s do that.”

By the time I was 17, I was about to graduate with my associate’s degree from college. So that’s what I went for. But there are so many battles, just being vulnerable. I can take that label and say, “You’re a high school dropout, you’ll never be anything.” And not only did my teachers say that, lots of people said that.

I could have let that keep me from getting my equivalency. I could have let that keep me from getting my high school or enrolling in college. I could have finished college. I actually dropped out because I was impatient again and started my first business. I kept moving on to things because I had the belief that I could do better. I could do more than I was doing and I could work harder.

And not that I knew it all, but it was that I could do more than I was doing. That’s what led me. But I’ve got to tell you, anybody that tells you they don’t struggle with that kind of thing is probably lying.

I can identify and label myself as a successful CEO. We have an amazing team, amazing partners, and all these other things. I’ve received this award and that award. I’m the host of MSP Mindset and all these other things that are wonderful, and most importantly, an amazing wife and three kids. Or I can identify and label myself as a high school dropout, a college dropout, and lots of other things.

But at a certain point, you have a decision to make. Am I going to let that define me? Am I going to take that view of the world and say that’s all I can do? I could have said, “You know what, they said I’ll be on welfare. I’m going to believe them. I’m going to go into welfare. I’m not going to try to get my high school degree, nevermind try to get into college, nevermind try to start my own business.”

I look back to when I started my business and I still don’t know a ton, but when I started my business, I really knew nothing. But you know what, I started my business not only because I wanted to, it was a dream but I started it because you know what I’ve learned? Many people when they talk about hiring me, or even folks I interview, do you know how many ask, Do you have a degree? Zero.

Nobody cares if I have a degree now because I’m running the company and I built the company. That’s permeated lastly in our culture just it tie it back in. Meaning that it’s wonderful that you’ve gone and got that degree, not taking anything away, but we have gone out of our way to design a recruiting process that looks for what I would call unique individuals or diamonds in the rough people that maybe don’t have the certain degree you’re looking for, or a degree at all, or maybe they don’t have the tech stack you’re looking for.

It’s because I’m not that guy and you would have skipped me over. So, why would I do that? Secondly, because I have a very strong belief that if you’re not looking harder than the average person, or the great people that are out there but they just don’t meet your filter, a four-year degree from good college, and it had to be in business or computer science or one of those filters you’re putting out there.

Well, sure. Maybe that makes your job easier sorting through the resumes, but you’re sorting through the same ones everybody else is sorting through. You’re overlooking some amazing people. One of the blessings is I get to choose who I work with. Some of the best people I’ve ever hired, I got to be the first person to bet on them, nobody had.

They had a dead-end job, not in IT, and I got to bet on them. Those folks just do amazing things. They go places that most people would not believe they could go. So that’s been one of the blessings is getting to bet on them. The other one is getting to the see.

I get pure joy watching them go to incredible heights and develop such mastery. And some of those folks outwork the folks that got the degree. Not all of them, but some of them have a little bit of a chip on their shoulder to prove. I know I was that way when I was at that stage.

If that’s you, don’t let that stop you . You have the choice to let your past define you, or what I recommend, which is let your future define you. Get clear on your future and define it.

Russell Benaroya: I have one last question for you as we go out, but let me summarize a few things I took away from our conversation. Number one, a lot of confidence starts with recruiting and the way in which you evaluate and bring people into the organization. Right people, right roles, mapping to the strategy that you’re executing.

Number two, I heard to consistently audit people’s zone of genius. “Hey, where are you getting energy? What’s draining your energy?” And doing it with a level of consistency that allows the organization to say, “How can we mitigate or eliminate those areas that drain because your drain may be somebody else’s gain?” That’s number two.

I heard, number three, that confidence in many ways is a mindset. We tell ourselves stories that don’t always serve us. It’s worth checking in on ourselves where we are in our minds, and what is really fact versus story. I heard that while you sell a solution at Servosity, what you really guide on is confidence. What you really sell, the brand promise that you sell is liberation at some level, for an MSP owner to be free to focus on other areas of growth and opportunity, not backup and disaster recovery.

I heard about setting realistic objectives and being aware that people can sometimes feel defeated if the objectives that you set are not accompanied with the plan of how you’re going to get there, the how and the when. When those two are disconnected, you could set super lofty goals. You didn’t hit them, but you hit a lot of great things, but you still feel defeated.

I heard that investment in systems is really important for delivering on your brand promise. You’ve built Servosity in service to MSPs. What you’re asking MSPs to do is invest in the requisite system because the brand promise that they’re delivering is one of confidence to their clients. And systems investment is often something we put off or kick own the curb because it has an unclear ROI and we don’t want to spend the money but that can come back to bite us.

Then the last thing I heard is creating systems of measurement. So measuring the gains, measuring what we have accomplished as a method to increase our confidence that we’re moving in the right direction. Does that feel like a resonable summary of key points that you shared?

Damien Stevens: I think you nailed it. That’s really good, Russell.

Russell Benaroya: We’re going to work to distill that down and make it actionable for the listeners. My last question for you is, what is your zone of genius?

Damien Stevens: Great question. My zone of genius is trying to help others get where they need to go. I think that applies to MSPs and it’s a little bit like what you said. We’re there to liberate them so they have the confidence for their team. Because I seriously doubt the owner or any of their engineer is like, “Backup, that’s my thing, that’s my jam. It’s the only thing I want to do.”

It’s probably a lot like accounting. Most MSPs are not great at accounting. It’s not their zone of genius, nor do they necessarily want to do that. But both have to be done extremely well. You know how it is. You could have inaccurate books for a little while, but eventually, it’s going to cost you one way or the other. Whether it’s IRS, whether it’s a vendor, whether it’s a missed client.

It’s the same thing with backups. You can get away with it, perhaps for a time, but eventually that will come home. So I want to liberate you from it and I want to help. I don’t care if it’s an MSP, I don’t care if it’s working with you, Russell, or if it’s one of the folks on my team, I want to make sure that you are growing and you’re getting in your zone of genius. Part of mine is being able to understand where you’re going and help connect you.

That’s why whenever I talk with people, in some cases, maybe it makes sense to hire us to help you liberate yourself and your team up so you can focus on what you do best and grow your business dramatically. If you don’t, that’s why we literally let you steal our process. Go for it, do it yourself.

I’m not trying to hoard that. I don’t need to. There are plenty that will hire us to do it for them and others that won’t. Either way you can win, I want you to take value out of it. So anybody that engages with me or my team, I want you to go, “That was a win. That was valuable, and I’m better for it.”

The same thing with my team. I’ve actually helped some of my team, and over the years realized they need to graduate and go bloom in a different garden. I know a lot of people look at me when I say that, but I don’t mean like they’re no longer fit. That’s different. What I mean is sometimes you’ve just outgrown this. We don’t have that role.

Earlier on, I had a financial person, but they grew out of a controller and were headed towards CFO. I was like, “We have nothing like that in the near term for our company.” They were willing to stay. They were loyal. But I had to help them see, this is not the best path for you. I didn’t say, “You have two weeks, get out.” But I helped them see and then they started looking into it. They started thinking about it.

What that did was it gave them confidence. They were confident here because they knew us. They had really developed all these skills. I saw their skills better than they saw their skills. I realized they were ready to go to the next level. They probably should have joined your company or somebody like yours, Russell. I helped him realize that.

The odd thing is I’ve helped some of our great team members decide they should leave. I want them to stay, don’t get me wrong. But I realize you need to grow. One of the best gifts I can give you is helping you figure out how to get there. Whether that means as a client, and we’re not the right fit. Whether that means that as a team member, and you really need to bloom somewhere else. It doesn’t mean you couldn’t come back one day, maybe we have that role. But you need to be in a different spot.

And every single client or team member that has ever said, “This is not quite the right fit, go bloom here,” sometimes they’re a little frustrated by that. But they think about it and generally just raving about that. They’re like, “This is amazing. I’ve gone to places.”

Going back to that first thing, they didn’t have the confidence to grab the next rung on the ladder and go from there. They’re not job hoppers that move around. They’re loyal people like all of us want. Sometimes they realize that a little move here or there in the right way could do wonders for you and challenge you to learn like you haven’t in years.

If you’re starting to stagnate, I’m going to challenge you. And you’re going to love that here or you’re going to not love it here. We try to be very open about that.

Russell Benaroya: Awesome. Damien, thank you so much for joining us today to talk about a topic that’s often very elusive for founders and CEOs. Which is harnessing that feeling of confidence so that they can stay in this place of highest and best use.

And the journey to get there is multifactorial. We touched on a few areas that CEOs can pay attention to in their quest for confidence, which is designed to be ultimately an accelerant to the dreams that they have set before them.

Thank you for laying some tracks today. Thank you for being candid and honest. Thank you for not only sharing about the business of Servosity, but also your business of building the business of Servosity. I really appreciate you. Thank you.

Damien Stevens: Thanks, Russell. I appreciate you having me.

Russell Benaroya: Thank you so much. Thanks, everybody. Look forward to the next episode of the Stride 2 Freedom podcast. Have a great week. Talk to you later. Bye

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