Juan Fernandez (00:00:00)

What I didn’t even realize was going to be an entrepreneurial journey and finding what I call success in a moment that’s so small, it’s a couple of words, and it’s called “I can.”

A lot of people play their business like it’s a slot machine: “I just put some coins in, and I just keep pounding buttons, and hopefully something good happens.”

That’s not a business plan. That’s not a strategy. That’s just luck. And so I decided to open the machine and figure out: Where does the quarter get stuck?

I talk about community as two different things. You’re either “come to be served” or you come to serve. Which one is it?

When you start to think about challenges—and I use this little analogy like the Lego on the floor—if you’ve ever stepped on one of these at 3:00 AM, you know the true amount of pain.

And they just take this freaking Lego and they throw it. And it’s like, “Woah, wait. What did you just do?” Like, that problem that was there, you now threw it out in front of you so that you could step on it again.

John SmallMtn (00:01:00)

Welcome to another episode of Founder’s Growth. My name is John Hill, AKA Small Mountain. I’m the founder of Adapted Growth. Today we have Juan Fernandez on the show. Juan and I have known each other for a while, and I’m super excited to have him on. He is the CEO and founder of Summit Holdings and has got one of the coolest stories about being a founder and being an entrepreneur that I’ve ever heard. I’m excited to dig into that today. Juan, can you give a quick dime-store tour of how long you have been on your entrepreneurial journey?

Juan Fernandez (00:01:30)

Yeah. You mentioned the word “founder” a minute ago. I remember when I was very young, just starting off on what I didn’t even realize was going to be an entrepreneurial journey and finding what I call success in a moment that’s so small when you think about it. It’s a couple of words, and it’s called “I can.”

And that really spawned a whole bunch of opportunities for me. I built an entire career over the last 30 years around that moment of “I can.” I would say that even as I progress in my founder’s journey and all the aspects of leadership, it’s just one of the things that I find an opportunity for us to deliver in. I’ve done a lot of cool things. I’ve written books, I’ve built companies, I’ve scaled enterprises. Just sifting through the ashes of time, finding the unique nuances, and helping people find success is where I’m at now.

I’m really excited to be able to share and, again, thanks for having me, John.

John SmallMtn (00:02:33)

You’re welcome, man. We got to meet at a speaking engagement, and that story that you talked about was so cool. The thing that really blew me away was you got up in front of the whole crowd and you were like, “Hey, which story do you guys want to hear?” Just being that open and asking, “What do you guys want to talk about? What do you guys want to hear about?” really blew me away. I’d never seen anyone do that before. It speaks to how long you’ve been in the space and how authentic you are. It’s not just about sharing the wins and the highlight reel because this is a hard path and people get caught up in it. I’m excited to dive into that.

The first thing that I have a question about is you have been in the IT MSP space for a very long time, and you’re coming back into it with some of the developments. I’m curious, what are you doing differently this time coming back in?

Juan Fernandez (00:03:37)

I don’t know that I’m doing anything that’s really that different. I would say that I’m approaching what I feel is one of the needs of the channel. Being here as—I call myself a resident MSP, if you will, or resident entrepreneur in the MSP channel—one of the things that I do is just like we would anywhere else. You always see those people sitting on their front porch. It’s a good day if they’re on the front porch with a sweet tea, or it’s a bad day if they’re out shoveling snow. It’s a similar thing. We all live here in this wonderful place.

When I think about some of the things that I’ve seen over the years—whether I was building MSPs, building products, taking companies to market, or investing in SaaS companies—there’s a lot of viewpoints that I’ve had. One of the things that I’ve noticed over the years is the requirement for the restabilization of the entrepreneurial ecosystem.

One of the things that I am doing now with Summit, the MSP Owners Group, and all the other companies that we’re bringing to light, our focus is really on the path of empowering the modern leader and focusing on the next generation of entrepreneurism. It’s a gap that I’m trying to fill. Not because I think that no one else is doing it, I just don’t see it being done in the way I think builds more stability for the community. A lot of what I do is share, and I don’t see that as a compounding growth factor in our channel right now. I want to stimulate that nuance.

That’s really what I’m here to do: create what I call “experience centers” to look at how to do things differently, be able to walk through the path, and understand more about how that is different than what I’ve been doing. How do I move myself into the future, and what’s this next generation of this MSP 5.0 thing Juan keeps talking about? I need to create these pathways to success and into the future.

So we’re going through it. I’m doing exactly the thing I say I do: dropping the quarter in and watching the dollar come out. But at the end of the day, I want people to be able to walk along the same path and be able to see those realities. That’s really what I’m focusing on: empowering the next generation of entrepreneurs. It’s not about the tech; it’s about the tactics, the scale, the opportunity, and the focus in terms of what we’re trying to create at the end. It’s not necessarily much different; it just looks different. That’s where I’m trying to help people understand where they’re at, how they can adapt this new mindset of growth, and the things that we need to be focused on for this next era of what I call “managed.”

John SmallMtn (00:06:32)

Interesting. Okay, I love that. One of the things that blew me away the first time I saw you speak—and whenever we were chatting about it afterwards, as well as meeting other people who you have worked with and seeing that kind of impact—is that you’re so focused on building everybody else up. Everyone who works with you, everyone who’s around you. It’s interesting to see that because we sometimes have this idea that to be a founder or entrepreneur, you kind of have to be in it for yourself.

I’m curious: Have you always had that kind of warmth and drive for building other people up? Is it something you found on your path and decided to lean into? Where does that come from?

Juan Fernandez (00:07:23)

I have a lot of stories, and a lot of the stories that I have aren’t always of success. Most of the most amazing moments in my entrepreneurial journey were sifting through the ashes and figuring out what was supposed to come out of that scenario. Why did that not flourish? Or in the case of why it did flourish: Why did that work? I spent a lot of time sifting through moments to understand that.

As a leader, I’ve always thought to myself, “The most important person you have to lead first is yourself.” Being that self-aware leader is my mantra on how I lead: not looking up to people, but looking at the way others treat people. A lot of what I’ve learned is not necessarily what to do, but I’ve also felt my way through leadership because I didn’t have a lot of people to tell me. I didn’t come from a place where I went to school and people showed you what to do, how to run a business, and what you should focus on. I felt my way through it.

With my eyes closed, all I could understand was the words, the sentiment, and the way it made me feel. In my entrepreneurial learning through my entire career, I’ve always picked up things where I said, “I’ll never do that because it makes me feel this way.” I’ve allowed the negative components of my journey through life to shape who I am because I understand, “If I do this, this is how it makes other people feel.”

In doing what I do now, I always say, “I wish somebody would have done this for me.” Rather than make that a wish, I made it a reality and I’m doing the thing that we always hear: “Be the change you want to see.” It didn’t become real until I started doing it.

That’s where I talk about community as two different things: You’re either “come to be served” or you “come to serve.” Which one is it? It sounds the same, but they’re not the same. For me, I’m here to help. A lot of people ask me, “Why do you do this? How do you make money?” I’m not trying to make money off helping others. I’m trying to help others so that we can help each other, and then, in turn, we all are successful.

Have I always been this way? It took me a long time. I’ve always tried to encourage other people to push themselves to go do a thing. Some people were like, “No, I can’t. No, I can’t.” And I’m like, “But you can.”

Whether I’ve been in the leadership role or not, I have a whole thing called “the bottom-up leader.” I’ve always been down at the bottom, and I’ve always led up. I love being in the trenches with everybody. As somebody told me one day, “It’s your blood in the mud, Juan. That’s what’s different about you.” I’m like, “That doesn’t sound good. Am I injured?” And he’s like, “No, it’s a military term, buddy. You’re in with us, and so that’s why we understand.” I’m like, “Okay, it sounded like you guys were getting ready to handle me.”

I’ve always just felt like we can treat people well and that there is a better way to do it. Here I am; I’m just trying to pave that path and teach the people that work with me, for me, and around me that we work together to make this place just a little bit better.

John SmallMtn (00:10:57)

I love that. I also know you to be a pretty high-output individual. Sometimes when you’re a high-output individual, you’re also in a leadership spot, and you’re trying to motivate others to get to that space, it’s difficult to do. How have you gotten better at getting other people into higher gears as far as their performance, work, and effort?

Juan Fernandez (00:11:23)

I say this all the time, and I use this scenario: Look, I’m never going to ask you to do something that I wouldn’t do. I know that’s a very different approach for a lot of leaders. A lot of leaders lead from the front, and I lead in stride.

In the case that I’m working, I always tell people, “Please don’t try to be like me, because I’m a little broken.” I love to build, design, create, and immerse myself in things. I’m very deep in what I do, and I live a very different life. It’s come at an opportunity where I even have other books about how I do things just to help others try to compartmentalize themselves so they don’t get too sucked into the way that I am as a person.

In terms of how I empower others, I always try to assist them in the place that they’re at. I say, “I’ve got 100 keys, and you may not be ready for key 100.” Everyone wants key 100: “Give me the answer to the end of the story.” And I’m like, “You kind of need key number four. Here’s this key. Go open the door, go through the door, and then come back and tell me that experience.” It’s a feedback loop: Go through the problem, understand it, come back, and then teach and train.

One of the things in leadership is letting go of the keys. I have an analogy called: “If the problem equals one, one is the problem.” In that case, everything that I do, if it comes back to me, then I know that I created a problem. I’ve got to create a tweak here. People hear this thing all the time called “people, process, technology.” I realized that in trying to follow that, it’s a fracture. It’s “hire the smarter people so that they can figure it out, and then you can just sit back and do the thing.”

I’m like, “Is that leadership, though? Is that really leadership?” I have to challenge this theory because I realized that there’s a different way to do it. If I take my “if the problem equals one, one is the problem” Rubik’s Cube and change it around, I realize that if you create a process that empowers the people, you can create a great technology, a great company, and a great culture just by the little shift of taking time to help your team understand how to win.

For me, when I think about the most amazing thing that you could ever experience in leadership, it’s not about an exit. It’s not about the money. Trust me, you burn through that, you’ll feel unfulfilled at the end of it, and you’ll end up going back to work and doing other things. Been there. It’s about when your team knows they can. That’s when you unlock them. When they come back and say “it works,” that’s the beauty of it. You can see them unlock.

That for me is really the part where I try to help people: understanding where they’re at, and then helping them step up and step out over their comfort zone. That for me is the moment.

I do things like when you first met me, weird things where people are like, “We want change.” And I’m like, “You want change? I’m going to throw change out there and see.” It was the first time everyone’s ever done a “pick your own keynote adventure.” “Hey, I’m going to ask you a series of questions and you’re going to pick your keynote today. I’m going to rip through one of these presentations that I have ready for you—one of them I really don’t want to do.” Of course, the one that everyone votes for is the one that I absolutely don’t want to do.

It was just hilarious. “Do you want to learn about how to be a success and grow in scale, or do you want to learn how to be a failure, burn, and just die?” They’re like, “We want to learn how to burn and die.” I’m like, “Why would you pick that story?” I made it so unattractive, but that’s the beauty of the human aspect: We all want to learn how not to fail.

That’s where a lot of us in leadership are very hesitant to illustrate the gaps, and those are the pitfalls. It’s like, “Yeah, no, trust me, you can just jump over that chasm.” And it’s like, “Bro, there’s no bridge there. What are you talking about?” “Well, you just got to run real fast and then jump, and then you’ll make it.” There’s no bridge there, dude. That’s too far.

In leadership, we can oftentimes tell ourselves that we don’t want to share the secret of renting a plane, flying to the city, and doing the things. There are different growth trajectories, but understanding those moments is where we have to build the bridges to empower the people behind us. That’s the process we have to create to empower the people.

That’s my methodology on how I do it, and hopefully that helps somebody that listens to this, either today, tomorrow, or in the future. I think empowering others on the entrepreneurial journey has been a journey in that I found every which way to do it wrong. There are only a very few small ways and a combination of ways to do it right. To be honest with you, I see them all. You hear them, but there are a few of them that feel good. At the end of the day, it’s the one that leaves a legacy behind that allows people to know, “That made a difference in my life. That unlocked me, empowered me, and stimulated me to want to go and take that hill.” That’s what I try to focus on.

John SmallMtn (00:17:18)

I love that. One of the things that always resonates with me is just how positive of a person you are. I mean, even when the crowd picked the story of woe, you were just so positive about it. But one of the things we were talking about when we were trying to figure out where to go in this conversation is that hope is not a business plan. How do you balance that positivity, goals, and aspirations with not being too hopeful and still having your feet planted in reality? How do you get better about that?

Juan Fernandez (00:18:06)

I don’t know that you ever get ready for that, but I will say I talk about this often, and I think it’s a lot around mindset. My life is not easy, I’ll be honest with you, but I gauge a couple of things in life around the way I perceive my environment. In that case, where people say, “Dude, you’re always smiling,” I’m like, “I don’t really have anything to be sad about.”

When you start to think about challenges, I use this little analogy like the Lego on the floor. Everybody sees the meme about the Lego that’s on the floor. If you’ve ever stepped on one of these at 3:00 AM, you know the true amount of pain. I use this analogy because it’s easy to assimilate to. In the case that that Lego is there, I found that a lot of people loathe the Lego. They hate it. They’re like, “Oh my God.” And then they get the Lego and they just throw it. It’s like, “Woah, wait. What did you just do?” Like, that problem that was there, you now threw it out in front of you so that you could step on it again.

That’s a misplaced opportunity. It’s not a problem to dislike. So if you find it, put it in your pocket and figure out where it goes. It completes the puzzle instead of becoming a pain in your ass. So many people pick up the problem, and they just keep throwing it and never solve for it. Then they end up with this compounding effect of resentment, guilt, or all the things. For me, I’ll take this little thing, I’ll stare at it, I’ll understand it, and I’ll look all the way back: Where does this go? Why is this still here?

When you think about hope, a lot of times when we think about business, we just hope it works. That’s not exactly how that works. I talk about that scenario similarly. John, when we met, we spoke a number of times together. I talk about the “quarter in, dollar out.” When I talk about quarter in, dollar out, it’s like when you put the quarter in: How does it actually go through the machine? When does the house win, and when do I win? What’s the algorithm? What’s the total number of plays? How do I make this work? I decided to go through every piece of my business and look at it in those ways: dropping people in as quarters and watching them get stuck in the machine because they never get to this place.

During the pandemic, I was speaking on a stage and I said, “How many of you here are struggling to hire people, and how many of you are struggling to retain?” I knew the answer. There are 2,000 or 3,000 people at this show, and it’s the keynote for lunch. I knew what I was about to do, but I did it anyways. The entire audience raises their hand, and you can hear their forks as they put them down. I said, “Well, how many of you have an employee success program?” I thought about half of them would spit their food out.

I said, “To be honest with you, the reason why these employees are not coming, why they don’t want to come to your business, and why they’re leaving is because during this time, they don’t see themselves being successful with you. The companies that I see leaving the most are the ones that I’m worried the most for. That’s because you haven’t gone through the process, no matter how large you think you are, to understand how your employees are going to be successful with you.”

That translates back to the strategy and, again, the hope that we have something figured out. Just because something worked for a period of time doesn’t mean it’ll work forever unless you have gone through the process of understanding what it is you do and how that translates to your customer and employee success.

I gave you two KPIs that I focus on: Key People Indicator and Key Profit Indicator. The Key People Indicator is: Do I see my team smiling during the hard times? If I don’t see them smiling, it’s because they’re probably not going to make it through this time because there’s not a way. If you have a process to go through a hard time, it’s just wind in your sails. It’s just a storm. It’s fine. We’re not going to capsize. We’re not going to turn over. Nothing’s going to happen. We’re just going to hold on because we’ve never felt this pressure before to get through this storm, but they know they’re going to make it. In other cases, that storm is blowing businesses over and they’re falling. That’s creating turmoil, and they’re screaming and they’re scared. That’s when they leave.

When you think about how you curate those “hope” business plans or those strategic business plans, you have to be focused on the process that empowers people, creates a great culture, creates a great company, and creates a technology or whatever you want. That formulation actually spawns a whole bunch of things if you just change the one thing.

This is going to take time. People are going to have a hard time with this, and I’m sure I’m going to get flack for it. But if they try it and go through the process… There are a lot of them that are like, “Look, dude, I just want to grab a business off the shelf, bro, make some money, and leave.” This conversation isn’t for you.

I call two things: cultural leadership and transactional leadership. If you’re a transactional leader and you just want to focus on the numbers, dial it in, send checks, and get out of here, this ain’t for you. But those that care about the people and want to help others, this is for them.

When I think about hope as a business plan, that comes as transactional leadership because I just hope it works. I hope $1 + 2 = 3 = 4 = 7 = 10$. Mine is: Go through the process of understanding how to empower your people to grow a corporation, a culture, and a wonderful outcome. So there’s a difference. I know I dove into some talking points there, but hopefully it helped.

John SmallMtn (00:24:20)

No, that’s great. When you were talking about people smiling in the bad times, if you see someone struggling during those down times or bad times, how do you work with them to try to turn it around? Or is it a lost cause and they just need to be removed? Because if you’re the bad energy on a team, you’re the bad energy on a team, and it can suck all the morale out of the room. In those moments of high stress, what do you do whenever you see someone not being able to stay in the right mindset of being positive and knowing we’re going to make it through? How do you handle that?

Juan Fernandez (00:25:03)

I wouldn’t say that I focus on their positivity more than I focus on their perseverance. In any case, my entire life has been formed around areas where I didn’t become who I am today by easy streets. I recognized early on that I needed to create pressure to do amazing things.

So I illustrate how you have to create these nuances around you to create compounding pressure to really stretch who you are and make you go through these times. The challenge that I have is for people that give up halfway. I’m like, “Man, you could have made it through that.” And they’re just like, “I’m tapping out. I’m done. I’m done. I’m done.” They get in their head and they’re just like, “I’m out.” I can see that moment because they back up and they’re like, “Whoa, whoa, whoa, whoa, whoa, whoa, whoa.”

I have a couple of things that I talk about. I say that I can teach people that want to learn. There’s an adage out there that says when the student is ready, the teacher will appear; and when the student is truly ready, the teacher will disappear. That’s in my world. I can only teach those that want to learn. That’s why I say there’s a difference between cultural leadership and transactional leadership. Transactional leadership doesn’t want to hear anything I’m saying. They’re like, “Dude, I don’t want to hear a damn word you’re saying because I don’t really care about the people. I care about the process, and I care about the profit.” That’s okay. That’s cool. It’s okay.

But I will say that when I see folks that are struggling, I give them an opportunity to understand why. I have these scenarios all the time. I listen actively. I’m like, “Hey, they’ve had that problem twice.” Most people don’t hear that. They’re just like, “Okay, now you’re just being annoying because you can’t solve a problem.” I’m like, “That’s not what they’re saying. They’re saying that they don’t have enough information or education to be able to feel successful in this moment, and that’s coming out as a request for help.”

Rather than helping them, we often shun them, saying, “Well, you’re just not going to make it.” So you have to go back and say, “Hey look, here’s the education that you need to do. I need you to do this around this thing, and then I need you to come back and teach us how to do that.”

Now that move right there is a chess move, bro, that will change everything. Because when you get them to go in, push on the button, give them the access to the thing, and then have them come back and train us, you make them fully accountable for it. Then they have to become immersed in it.

So it creates a really un-noxious pressure, because I’m number one. “What do you mean I had a problem? What are you talking about, man? Now you want me to go teach somebody about this?” I’m like, “Yeah, I do. Because I know you can, because I did it.” You can get through that. Now, if they go through it, that’s all I need to see. That’s initiative. You can’t teach initiative, and that creates positivity, because then they feel excited about the fact that they did it and they’re like, “I did it.” And I’m like, “There’s a smile. Keep going. Go find the next problem, come back, and tell us how you fixed it. Keep going.”

When you find the ones that don’t want to, they’re like, “I don’t want to do this, dude. I’m not going to teach anybody anything.” I’m like, “Either you tell me how to fix it, or…” That’s the check move, right? Like, “Okay, that’s okay. Let’s try another angle. Let’s try a different motivation tactic.” If that doesn’t work, then you’ve got to cut the cloth. You’ve got to move quick, too, because if you don’t prune that tree, you’re going to have big problems at the end.

So you’ve got to find your right… Culture is something so many people take for granted, and most of life’s lessons are staring you right in the face. The word “culture” as a definition means to cultivate: to trim, to prune, to manage, to mold. Most of us say, “Well, we just want to put culture on a shelf and it should just happen.” It’s like, no, you have to be actively engaged in creating that.

That’s where a lot of leaders miss the mark. They’re like, “Well, we’ve got a great culture.” I’m like, “What did you do to prune it?” “What are you talking about? HR did a great job.” I’m like, “That ain’t it. That ain’t it. How invested are you in that? None? Okay, well, there’s the answer.” Just because you’re a good person doesn’t mean it’s a great culture. That’s where, back to the…

John SmallMtn (00:29:39)

100%. And it’s not the ping-pong table or the beers at lunch on Friday and stuff like that. The cultural stuff has been one of the coolest pockets of knowledge I’ve leaned into and studied on my own path. One of the things that I think about is you’re going to have one no matter what, because when you have a group of people together—a team together—there’s going to be an atmosphere. If you’re not intentional about it, there’s probably room to make it better, you know? That’s how I always think about it. Even if you just show up and you’re in GSD mode—get stuff done—that becomes your culture. It’s going to be there no matter what, right? So you might as well put a little bit of effort into making it something that actually benefits you and your team. So I love that.

You said change the direction, and use a different tactic. I’m curious… The teaching thing is so cool, right? Because when you get someone to opt in meaningfully to go in and do something difficult, all the changes happen there. Do you have any other ways that have been useful for getting people unstuck and into the positive mode, other than asking them to go deeper and try to figure it out so that way they can teach it to someone else?

Juan Fernandez (00:31:20)

Yeah. Again, as I talked about in the beginning of our conversation, as a leader, one of the things that I’ve always said is, “I’ll never ask you to do something I wouldn’t do.” That’s an accountability matrix. That’s up to me to really dive in and deliver on.

One of the things in leadership is that you have to sit down with people and help them understand the way that they learn. When we were talking and when we’ve done some things together, I teach and train in a number of ways: I talk, I show, I teach, we learn, you do, I watch, and then I get to celebrate your win.

In those nuances: reading, writing, executing, learning, and teaching are all the angles I take for people to come back in. Even in our business now, everybody’s going through this process, and we’re all going through the quarter in. I’m like, “All right, where are you getting stuck? Where are you getting stuck?” “I’m getting stuck here.” “Okay, well, do me a favor. Write me a process on how that works. Then come back and talk to us about how this is happening. Hey, by the way, now it’s yours. You’re going to own that area.” They’re like, “What? What are you talking about?” “Yeah, that’s all you now.” They’re like, “This is weird and scary and crazy.” And I’m like, “Don’t worry, we got you.”

When you see people that are struggling in a specific area… I say this all the time: The test taker has to take the test, and the test taker has to pass the test. So it is an opportunity for us all, and it’s all about the amount of effort you’re going to put into that. It tells me your deliverance in terms of what you want to accomplish.

I look at it in a number of different ways and find: Okay, are they capable? Yes. Are they knowledgeable? Maybe. Are they passionate? Possibly. I look at all those nuances and say, “Okay, well, here’s the area that we just have to shift and turn, and here’s what we need to do to do that.”

Those are different approaches to working with them to get them to the place. Again, I’ll be fully transparent. What’s etched in the mast of our ship is the definition of success—the first thing we did. It’s literally carved as a center post of this entire ship, and it says: “Our mission for success is when a leader creates and empowers another leader. But success does not come until that leader creates and empowers another leader.” So that is what they’ve signed up for.

I tell them, “If you’re not in for this…” And they’re like, “Well, hey, man, I’ve never led anything.” And I’m like, “Cool. I remember saying the same thing, and here we are.” So it’s not that it’s not possible. That’s the thing that we have to help them do: see the impossible become possible. That’s where you have to find the angle in which you have to go.

But you can’t do that without understanding what you deliver. Back to the process: If I have a process for their success, then they’re successful, and that should be an outcome. That’s where we’re focused.

Every piece of that, there’s a thousand different ways to activate people. It’s just a matter of searching them out and having not just me do it, but the rest of the team: “Hey, have you tried this?” And then they try, and they’re like, “Oh my God, that works.” So it’s like we’re in a nursery of bonsai trees, and everyone’s trimming, pruning, and creating their own little companies and their own little worlds. Some plants are dying, some don’t need water and we’re overcaring for them, and some are being undercared for.

It’s just really cool to watch, and that’s where we get an opportunity. I think everybody should, as a leader, work with their teams to try to find, instead of focusing on the company’s success, focus on the people’s success, and the company will grow from that.

John SmallMtn (00:35:13)

I love that. Shifting gears a little bit, one of the things we were talking about… You said this very interesting thing, and I’m excited to hear more about this. You said that one of the things you’ve struggled with was not exactly imposter syndrome, but you have had some moments of similar thinking. Can you talk a little bit more about how that has shown up for you and how you’ve worked on it?

Juan Fernandez (00:35:53)

Yeah. I’ve always been one of the youngest execs at the table for most of my career—and I mean really young. You’ve got to think, being at the C-level in your twenties, I don’t know how many people get to experience that. I look back at it now—even now, I’m still young and doing the things that I do—and I find myself in rooms where everyone’s much older than I am, and they have a lot of respect for the amount of effort that I put into it.

For many years, I didn’t believe in myself or my abilities to stand on my own two feet. I always felt, with imposter syndrome, just that I didn’t belong. It wasn’t that I didn’t feel like I was capable. I studied hard to become good at what I do, and I was very technical to a depth that was ad nauseam. I had more certifications than most people would ever want to accommodate in their life, and I’ve done things that are completely out of the norm. I took every challenge and everything people said I couldn’t do as something I was going to landmark on that I would do—and I did. It’s not because I did it out of spite; it’s because I did it out of purpose.

People say I can’t do it, so maybe I should try, and I’m going to go do this. Next thing I know… But it was always this fuel. I’ve kept this even now in the evolution of who I am and why I’m still here. People ask me, “Why are you still here?” I’m like, “Because I’m still relevant.” It’s not that I’m here because I choose to be here; it’s because I belong here, because I can still communicate at the level of the place that I live at.

People feel like they don’t belong, and they leave because “I’ve had my time and I did my work.” I hear this all the time. I’ve lived by a preface of this thing that I call “death behind the desk.” It was something that fueled me early in my career when I was watching people: They would get to a certain place, and as soon as they made it to the desk job, they would just stop learning and growing. It felt like their spirit just died there, and they became irrelevant.

The next thing you know, I remember them coming back to me as I passed them technically, moved into other areas, and started running orgs and corporations. They would come back to me looking for jobs, and I’m like, “Yeah, but your skillset died seven years ago, man. I don’t have anything that requires maintenance on a past technology.”

We’re still at that place right now. We’re on the preface of this next explosion of technology, and I’m completely immersed in design, development, creation, and all the things, being on the forefront of it and making myself present in the moment so that I feel like I belong.

That’s where a lot of people… People ask me, “What are you still doing here?” And I’m like, “Well, I belong here. What do you mean, what am I still doing here? I’m creating the future of technology, man. I’m an active contributor.” It’s not that I’m still talking about Windows NT back in the early days. I’ve made myself relevant to the time and the space that we’re in, and that has given me the opportunity to feel more like I belong.

It was an interesting journey to find that because no one teaches you how to stay relevant, how to stay in the moment, and how to be part of the ecosystem. That’s why I spend a lot of time learning, understanding, trying to query the current ecosystem in which we live, trying to curate new methodologies, and trying to create new ways and pathways to success to get to the future. So this is why I’m here, and this is how I became more of what I was afraid of not belonging to. I feel comfortable in the place now, I’m happy to be here, and I’m happy to contribute. It’s an interesting way to think about it, but that was my journey to get here.

John SmallMtn (00:40:14)

The thing you said about dying behind the desk happens so frequently and regularly in sales, because there’s no appreciation for the craft, or maybe you’re just burning yourself out because you’re holding it badly and trying way too hard. You see the sales manager or sales leader role as just a break. If anything, it’s one of the hardest gaps to try to get through: going from being a doer to being an actual leader that gets other people to do. It’s very hard to make that gap and that jump. If you just want to lead because you’re tired of the lower level of the job, you’re probably going to die behind that desk a little bit faster than if you were still willing to go out, eat your own dog food, and get in the trenches. It’s so common in sales leadership, unfortunately.

Changing gears a second: You talk a lot about the customer journey and sales as a process, which kind of blew me away the first time I heard you talk about these topics. I’ve been talking about sales as a process for a while, and normally I don’t hear anybody else talking about this. Where does your passion for the customer journey and having a good onboarding process come from?

Juan Fernandez (00:41:46)

It’s the same as we’ve mentioned a little bit, right? It’s understanding, and that’s why you don’t hear it a lot—because we’re not taught that way. I kept walking down that same dark alley, and I kept running into the same brick wall. It was just the same outcome over and over, and I was like, “This isn’t right. You can make this work, but this doesn’t work without a lot of nuance.”

I was like, “How can I help people simply get from A to B?” The customer journey was curated based on a number of learnings. When I think about sales as a nuance, I say: Build products and services that everybody can afford, and for a price that they can’t afford not to.

When you think about what I’m trying to do in sales, I’m trying to remove the “no.” So I went “no” hunting for years to find all the “noes” that I was getting, figure out how we get to “yes,” and then only ask questions that lead to the “yes.” That’s what created that class called Know the No: knowing the “no” before you get it, and then understanding the customer journey and going through that.

All I did in the customer journey was figure out how to remove the “no” and address the flow. Allowing them to move from point A to point B in succession allowed my team to instill confidence. They could see it, I could see it, and the customer could see it. It was a great waypoint saying, “Look, you’re right here in our process. We’re going here, and this is how this is going to work. How do you feel about this?”

It’s not, “Are you going to do it? Are you going to talk to me about price?” because the value is no longer negotiable. I’m showing you what you want, and all you want is to be successful with me. That’s where we talked a little bit about that. The customer journey has been a big thing for me when I think about how we get the business to grow.

If I have a program and a process that empowers the people and empowers the company, then the customers that walk in here should have the best experience, because they can clearly see themselves being successful on the other side.

I think you heard me use this analogy: It’s just like a diet plan. Why do I try a diet plan? Because I want to lose weight, I want to feel better, I want to feel more vitality, I want to look good in the mirror, and I want to look good at the Christmas party coming up. I want something, and this plan looks like it might work.

It’s the same thing. What we say to customers in our space is that we’re going to get them somewhere, and then they don’t end up there. Why? It’s because you don’t have a plan or a way to get them there; you just have words. “Hey, buy products, and then guarantee this and do that, and you can make money, and your customers get this.” They take that as verbatim, and then we over-promise and under-deliver.

So for me, the customer journey is the true-up. I wanted people to see the reality behind what it looks like to deliver success and how to break it down. I don’t care how you do it, but go through each one of the segments of your business and figure out: How do you communicate what your customer is going to go through? How do your employees know what to deliver? That was really what it was about.

Sales as a methodology has been something where, again, I went back through and studied all the psychology behind why this works. I’m not a traditional sales guy, but I sure as hell can sell stuff. I just say, “You can’t buy anything from me, but if you want something, you’ll go buy it.” For me, it’s all about building something that people want so that you never have to sell a day in your life.

John SmallMtn (00:46:07)

Yeah, exactly. Whenever I’m working with someone and they’ve missed that window or that opportunity, they come in and say, “Okay, John, how do I close this deal?” “Okay, what did they say the problem is?” “Well, John, it’s different.” You’re not asking the core questions. You’re not putting it into play, and so you’re either scared, you’re not sure, or you’re running on some sort of weird sales tactic where you’re not supposed to haul it all out and have the important conversation, you know?

Juan Fernandez (00:46:40)

We think it’s peanut butter and jelly. This is the entrepreneur—I talked about this as the “accidental entrepreneur.” It was a talk that I did years and years ago. I got interesting reviews. Arlin Sorensen and I were chatting about this back in the old days, and one of the things we talked about was, as an accidental entrepreneur—and I can say that because I was one, and it happened in a number of cases where things start up for no good reason—we sell ourselves the lie that everybody needs it. Like cybersecurity, technology, managed services, ABCDEFGHIJKLMNOP. That’s the first lie we tell ourselves.

Then we say, “Okay, well, if I could just sell more of that…” Then we put a sales process on it: “Okay, this is a thing that we think people want.” Then we go out and try to accomplish it by applying a sales methodology that is going to try to connect to a disparate process.

That’s where you forgot the bread. We all associate peanut butter and jelly with an actual sandwich. I just did it two seconds ago. In your mind, you thought you were getting the whole thing. You missed the whole point, bro. You’ve got peanut butter and jelly in your freaking hands. That doesn’t make a great sandwich at all. For kids, they would love to do it—and I, as a kid, would have—but you’re missing the bread. The whole point is: How are you going to actually eat this?

That’s where I think, to your point, we struggle oftentimes. Back to hope, right? We’re just going to pop a few coins into the hope machine and hope something works, and you can’t do that. You’ve got to go through process. You need to understand how to effectively activate a business that is worth buying. That’s where we can go out and sell something worth buying. I think you’re spending a lot of time probably with a number of folks trying to help them understand what it is they do.

John SmallMtn (00:48:44)

Yeah, absolutely. A lot of people want to fight the current. They’ll have people say, “I just wish you did this. I just wish you did this.” In an earlier episode, Dan Bennett was the guest, and everyone was saying, “Will you just do our editing? Will you just do our editing?” And he’s like, “I don’t want to do your editing. I don’t want to be an agency.” Now he’s finally started to slow down, listen to it, and figure out a way through it—kind of the point you were talking about earlier: Don’t throw away the Lego. If people are coming and asking you for it, there’s something there, as opposed to trying to sell them the thing that you think you want them to have. Humans are just so interesting at fighting the currents, as opposed to just leaning into them. I say this as someone who’s fought a lot of currents on my path.

There’s all the room to fight against the current, but if you can find a lane inside of it, it’ll take you to where you want to go. We just have to be open to those conversations and perspectives.

Juan Fernandez (00:49:49)

Yeah. I love that analogy because I often work with MSPs—I shouldn’t even say “work,” I’m more like a friend to them. They’d probably say, “We pay people to do some of the stuff that you help with in your free time.” One of the things I describe myself as is a river guide. I’m like, “Look, we’re going to go over this. Do you guys want to go over the bump, or do you guys want to go around it? Which one?” “All right, let’s go over the bump this time.” There goes Chris. “Okay, grab Chris, put him back in the ship. Oh my God, now we’ve got to stabilize. All right, let’s roll back a few waves. Do you guys want to go over the bump, or do you want to go around?”

You’re right when you talk about currents and the way that we deal with business. It’s always an interesting ebb and flow. We’re always trying to figure out how to get more, but do we always take time to learn how to get more? That’s where I think the opportunity lies.

John SmallMtn (00:50:44)

Absolutely. I’m going to shift gears into some of the rapid-fire questions. We talked about these before. So for someone who’s starting today—they’re going out on their own as a founder, they want to build something and sell it, or they’re building something they’re purposeful and passionate about—what do they need to be thinking about on day one when it comes to IT, cybersecurity, and making sure that they’re set up for long-term success that most people miss when they’re new?

Juan Fernandez (00:51:15)

I think that that’s exactly the part that they miss: the part that’s unsaid. A lot of folks don’t pay attention to a business plan—going back to some of the interesting beginning nuances. How are you going to actually make money?

I think our industry is really interesting because, in the managed services space, you can get in here and make revenue. I talk about two quantifiers: time to revenue and time to profitability. They are two different things, and nobody really pays attention to the latter. They always pay attention to time to revenue as a quantifier for a successful business, and never ever start to dive in until they get to like $3 million. Then they’re like, “Dude, I’ve never made a dollar in my life, and I don’t know why. I’m still working full-time, but I don’t make money.” And I’m like, “Yeah, you got yourself a really great job and provided employment for other people, but is that really what you came to do?”

Focusing on what it is you want to do first, and then focusing on how you’re going to make the money… It’s not about selling products. It’s not about finding pain and doing these other things. It’s about purpose, it’s about your passion, then it’s about your people, and then it’s your profits.

When you look at those things in line, try to assess those, and figure out how you’re going to do it, I would encourage people to build a business plan and put it together. Then, just do a quick test: Go to a bank and try to get a loan. If they wouldn’t give you money for it, then no one else is going to give you money for it. That’s a free assessment right there. There’s a free one. I didn’t even put that on the deck. That didn’t cost you a dollar other than your time. So if you can’t get them to buy it and to fund you, then that’s probably not a good idea in your approach. You probably need to tweak a few things. They’ll help you work with the SBA to figure out the things you need to be doing.

Find the resources, find good people that are willing to give you good advice, search out people that have been through it, and ask them the question: Not “What would you do if you did it over again?” but “What did you screw up, and how did you fix it?”

I would say for those that are starting out, a lot of people are stepping in, grabbing tools, coming to market, and then becoming what we call a value-added reseller. “Hey, I can sell a thing and they’ll buy it.” Again, that’s back to what I talked about: hoping it works, because that’s not a plan. That’s just selling a thing to sell a thing. They’ll end up in one of our classes, John, asking, “How do I now create a sales program to sell more things?” It’s like, you don’t have a business yet. So focus on creating an actual business, and one that will scale.

John SmallMtn (00:54:11)

I love the idea that you can just go to a bank with your business plan and try to get a loan, because it is a really great barometer of whether you have anything. What a cool idea, absolutely free, and banks like opportunities. I used to be a banker, so when someone comes in and says, “Hey, I don’t even know if this is at a place to where we could fund it; could you help me?” I love that. That doesn’t cost anything other than a little bit of time checking your ego and deciding that you should commit it to paper so that way you can go check it. Man, I love that.

Okay, next question: What is a piece of dogma or a tweet on social media around business that you can appreciate now, but you had to learn the hard way?

Juan Fernandez (00:55:16)

How to temper the hustle culture moments. A lot of that pressures you into believing you need to just be doing things, and doing things at a rapid succession: “Burn through every piece of grass that you can find on the way through your entrepreneurial ecosystem, and hope that the fields grow next year.”

It’s just interesting. I did that in my younger years. I thought, “Let me grow this thing, let me grow this thing, let me grow this thing, let’s do this, and let me do that.” You take on too many things, and the next thing you know, you’ve got a lot of farms, man, and all of them start to dwindle. The next thing you know, none of them are really growing anymore because you’re not taking care of them in a way that’s meaningful.

Really focusing on one thing and being really, really good at that one thing… There can be a lot of pieces in that one thing. I got caught up in that, and it took me a minute to back up and say, “Hold on a second. I’m doing too much here.” It caused burnout. It caused stress. I have an ability to become a vacuum of energy, and it drowned my family in it. It drowned my relationships in it, because when I get focused on something, it’s like a vortex, man. Everything in my life just becomes an absolute shitshow, if you will, because of the fact that I’m not taking care of all the things.

A lot of us measure that because we were focused for a period of time in that hustle culture to just focus on yourself, just go do you, just get you, and no matter what, take no prisoners. You just pull it in, and you just get your shit done. There are so many sacrifices that come as learning lessons on the backside of that.

I would say that that was one of the ones that I recognized, and it’s caused me to set boundaries. It’s caused me to try hard. My family now recognizes it. They’re like, “He’s just going to work all the time; that’s what he does.” But even I have started to back up, like, “Hey, I need to take time for my health, my personal space, and my headspace to clear my deck, think clearly, and focus.” That’s probably one of them that got me. I say it got me, and I found a way out of it, but it’s still part of me. It’s now a tempered part of me.

John SmallMtn (00:58:13)

I love that. One of the things that I talk about with people—whether they’re a salesperson and we’re working together, or they’re a founder—is you’ve got to attend all the gardens. You’ve got your family, your friends, your network, your clients, and your team, and they all need different forms of nurturing. But if you’re not present and you’re not paying attention to it, you are by default taking it for granted. You and I both know a bunch of people who are unqualified successes in business, but they’re divorced, or they don’t have much of a relationship with their family. I can get very fixated on what I’m working on as well, and I can just force my head down. So I also have to intentionally cultivate a little balance, because otherwise it won’t be something I lean into.

Last question, Juan: With everything that you have seen in the space—you’ve been on the entrepreneurial path for a very long time, and things have changed a lot—what would be your piece of advice for someone who’s starting today? One piece of advice.

Juan Fernandez (00:59:24)

Focus on your people. One of the things that’s going to change in the future—and right now you can see it… If you take a look at the trend line in terms of the companies that are out there, the dollars that are moving around in the ecosystem in the trillions and billions, and some of the decisions that corporate America is making in terms of this next generation of technology: They’re making early bets on automation or artificial intelligence, and it’s coming at the cost of jobs.

Now, am I a naysayer for AI? I’m developing AI. But I would say that for us in the future, it’s not going to just be about the automation of the technology; it’s going to be about those that effectively use it to interlace with humans to empower them into the future. I call it the “Iron Man suit.” I can’t trademark that because apparently there’s a great comic book around it that will not let me trademark this, and I appreciate that he used it. But we want to create these opportunities for humans to become superhuman.

That’s where I think we’ve got to focus: the people. Focus more on getting them ready for what’s next. Don’t get rid of them now. They got you here, right? They’ve been along the journey with you. Don’t be that leader that starts to get rid of the people because of the profit.

There is a future that is human, and I want us all to think about how we can empower that and make that a motion. For those that are on that journey, I hope they find me, and they can come back later and tell me I was wrong, or they can tell me, “Thanks for that.” But that’s where we’re headed. I’m on that journey personally. I came back in here to do exactly that, and I can only hope that for those listening here and in the future, we continue to remember that there’s something more important than money: connection with people and the way we can take care of this world is important. Hopefully, that makes a little bit of an impact, even if it’s just one-thousandth.

John SmallMtn (01:01:46)

Yeah, absolutely. Juan, thank you so much for coming on, man. I really appreciate it. Like I said at the jump, hearing you speak a couple of times, I’ve just been blown away with your transparency and being open to sharing the good and the bad. If people want to come check you out, figure out what you’re doing, and see if maybe there’s room to work together, where would you send them?

Juan Fernandez (01:02:08)

100%, come find me on LinkedIn. You can come over to my LinkedIn, look me up—Juan Fernandez—and type in “MSP.” There’s not very many of us out there in the world. On the other end of the stick, my calendar is also there, so just find time. I’m willing to talk to anybody and help anybody I can. Click on “find time,” and let’s get on and see what we can do to help improve this world a little bit.

John SmallMtn (01:02:33)

Awesome. Thank you so much for coming on. I really do think that this is going to help some people start with clear intentions and actually get to the levels of success that they’re looking for. Really appreciate you coming in.

Thank you, my friend. Have a great day.

Juan Fernandez (01:02:47)

You too.