Episode 18: “Living The Dream” By Getting Focused, With Brett Gilliland

Brett Gilliland is the Founder and CEO of Elite Entrepreneurs, a company specializing in giving $1M+ business owners the knowledge, processes, and tools to grow to $10M and beyond. Brett is an expert in organization development, leadership, and strategy and spent ten years helping Infusionsoft grow from $7M in revenue to over $100M. Brett was involved in the foundational work of Purpose, Values, and Mission at Infusionsoft and facilitated the strategic planning process for many years.

One of Brett’s favorite professional accomplishments is co-creating Infusionsoft’s Elite Forum with Clate Mask and building the Elite business inside of Infusionsoft. As the leader of the Elite business, Brett has helped hundreds of struggling seven-figure business owners overcome their biggest challenges and achieve new levels of success. He also played a central role in developing Infusionsoft’s Leadership Model. Brett served as the VP of Leadership Development when deciding to spin the Elite business out of Infusionsoft. As the new owner of Elite Entrepreneurs, Brett can’t think of anything else he’d rather be doing professionally. When Brett isn’t busy helping $1M+ businesses succeed, he is a family man who enjoys spending time with his beautiful wife, Sharon, and their eight children.

What the podcast will teach you:

  • How a recent encounter with an old acquaintance prompted Brett to wonder why we are so desensitized to living our dreams that “living the dream” has become a sarcastic reply
  • Why the 3-5% of entrepreneurs and business owners that have achieved the $1 million in revenue mark are often worn down, exhausted, and deflated
  • Why a business owner’s job is to cut through the chaos and lead themselves and their team to a place of less stress
  • Brett relates a story of taking his wife and eight kids fishing at a mountain lake and the frustration of no fish biting, and he shares how this parallels running a business.
  • How to turn a chaotic and disorganized company into a well-organized, coordinated, and efficient business
  • Setting a clear vision through purpose, values, and mission is the first step to turning chaos into order.
  • Why it is necessary to establish the right team in your company to turn your vision into reality
  • Why a consistent and regular meeting rhythm can help you more effectively plan your business strategy and execute your plan
  • Why dedicated business leaders can double or triple their revenue in just 18-24 months as long as they take the proper steps to get their organizations focused


I’m excited to spend a little time with you, sharing some insights that I had. Those of you who’ve been reading these episodes week after week, you’ll know that I try to mix it up and I have some guests come in who are seven-figure business owners. We learn from their real-life experience, some of the challenges they faced after they got to $1 million in revenue, and some of the things they did to move forward. We also like to bring in an expert from time to time in various subjects that are relevant to seven-figure businesses that are trying to grow. About once a month, I try to do a solo cast where I share some insights from my experience in working with hundreds of businesses over the past decade-plus.

Living The Dream

Here’s what I’m sharing with you. It starts with a story. I was walking from my desk to the front of the office where I work. I passed somebody that I hadn’t seen for a long time. It could have been months. I’ve known this person for years. I enthusiastically said their name. He said, “How’s it going?” I said, “How are you?” Without skipping a beat, we were passing each other going opposite directions, he said, “Living the dream,” and he went on. It didn’t hit me at the time, but as I was thinking about what I would share with all of you, that experience popped right back into my head in real-time high-definition color there.

That phrase is tossed out by lots of people. “I’m living the dream.” Most of the time, there’s a hint of sarcasm, if not, a strong dose of it. It causes me to wonder, how in the world that we get so desensitized to the idea of living the dream that we throw it out there like some sarcastic comment? In this case, he clearly meant, “I’m in this 9:00 to 5:00 job. Things are rough. I’m doing my best to hold it all together,” but he uses the phrase, “I’m living the dream,” to communicate to me that life is tough and there’s not much we can do about it. There was a little bit of defeated attitude in there, some skepticism, and some sarcasm.

What I want to talk about is what it’s like for business owners who get to that $1 million dollar mar, to seven figures, which we know is an elite space. If you’ve heard me talk, you’ll know that only 3% to 5% of businesses that ever start make it to $1 million in annual sales, at least here in the US, which I imagine is probably more favorable results here than many other places in the world.

Anyway, it’s elite space. Those businesses get there and the business owners probably feel some level of accomplishment. Many times, they often feel beaten down, deflated, and exhausted. They may have started out with a dream, like my friend that I saw. They may have started out with high hopes or aspirations or some big vision of what they were going to go out and accomplish, but now they find themselves beaten down, deflated, and exhausted, despite the successful road that they’ve traveled to that point to get their business to that $1 million mark.

How is it that we start out with a dream many times in business, or at least optimism and hope, and then we find that we may be living more of a nightmare than a dream? When I say nightmare, hear the words financial challenge, maybe physical health isn’t what it needs to be, mental strain, if not mental health challenges, maybe all of the social and family and loved ones, interactions are suffering.

Business owners take on a lot to go make their dream possible. They give and sacrifice a lot. Sometimes, even if their business has made it to a place of “success,” they find themselves hurting or lacking financially, physically, mentally, and socially in many ways. That doesn’t seem right. All of you have worked hard to go do something great. You find yourself wondering sometimes, “How did I get here?”

There may be bragging rights for getting to $1 million or more in revenue, but you might feel like, “All I did was to put more weight on my shoulders. The business got bigger. It’s more responsibility. It feels heavier to me. There are more people problems. In many instances, there may even be less take-home pay. When it was at $500,000, maybe I took home more pay, and had fewer people issues and headaches. It was a better life balance. Everything was better then. Why don’t I go back?”

We see many times business owners who retreat back to a place of more comfortableness or a place that feels more normal to them. We don’t feel like that’s right. We know that there is a way to grow a business and reduce chaos at the same time. You don’t have to feel more weight on your shoulders if you grow the business to a higher point. You certainly shouldn’t be sacrificing benefit to yourself financially. You certainly shouldn’t be sacrificing yourself for other things you want to do with your life.

How in the world did we get so desensitized to the idea of actually living the dream that we throw it out there like some sarcastic comment? Share on X

Building A Business Is Hard

There are lots of things here where we want less stress, fewer headaches, and more take-home pay, yet the reality seems to be the opposite of what we want. There’s no secret here that building a business is hard. Building a business naturally creates chaos and confusion. There’s a reason why the Franklin Covey folks who wrote The 4 Disciplines of Execution liken the day-to-day life of doing business to a whirlwind. It feels like a whirlwind. It is high speeds of wind violently pulling at you from several directions. It’s hard to make sense of it all and keep control or stay ahead of everything.

Your job as a business leader, as an owner, is to take that natural state of chaos and confusion that business brings. You have to lead people to a place of clarity and confidence. You have to help them cut through all the noise, all the chaos, and get to a place of clarity and confidence so that you can move forward together and do things that are possible.

I want to reiterate to you that it is possible to both have the business that you want, have growth in your business, and have less chaos, less stress, and less challenge. It’s more of what you want, less of what you don’t want. That is possible. Let me tell you a quick story to illustrate. My wife and I have eight children, lots of kids. We have 6 boys and 2 girls. We love to get out as a family and do things outdoors.

One of the things we’d like to do is go fishing. You might imagine with six boys and even our girls are good sports about fishing with us as a family. We try to go out and go fishing. We live in the desert in Phoenix, Arizona. Cactus. It’s brown. The treats we have, most of them have thorns. They’re prickly in some way. It’s not beautiful forests, mountain lakes, and trout fishing and all that. We have to drive a little bit. Thankfully, within 90 minutes, we can be up several thousand feet in elevation, beautiful mountain lake, rainbow trout, and pine trees, with much cooler weather. That’s what we do.

We try to get out. We go to this place called Woods Canyon Lake. I want you to picture this beautiful mountain lake scene. There’s this crazy big family along the banks of the lake. That’s us. We’re pulling out our fishing gear. If you’re a parent of a kid who likes to go fishing, you can maybe imagine with me what it’s like. I’m moving up and down the banks because we have five poles in the water at once. I’m going around, setting them up, and trying to help them get them out to be patient and wait for the fish.

Anyway, I’m doing this routine where I’m helping my kids fish. The goal is to pull in that prized rainbow trout. That’s what everybody’s excited about, to have that tug on the other end of your pole and your kid is fighting the fish and everybody’s excited. That’s what we’re after. 15 minutes, 30 minutes, 1 hour goes by, and no rainbow trout. You can imagine the energy levels of my kids are going down. The frustration’s rising. Maybe a little more complaints.

The sun is feeling hot. Maybe people are getting tired of waiting. We keep at it because we know there are fish in there. We’ve caught fish there. Probably about every time we’ve gone there, we’ve caught fish. We know how to do it. We try everything. We try fishing with bobbers. We try with lures or spinners. We try with bait, worms, power bait, salmon eggs, everything. We try all these things to get the fish because that’s the prize we’re after. Nothing. Another hour goes by. Now, it’s so painful. You guys know math. You’re good business people. 5 fishing bodies times 2 hours is 10 fishing hours of effort, with 0 results.

I don’t want to call you out and say you’re like the Gilliland family fishermen or fisher people, but sometimes in your business, I would suspect you know what it takes to run a business and you’re thrashing from the side of the lake, trying to get the result. You think if you keep at it, it’s bound to eventually happen. That’s what we were doing. We’re trying and trying. We thought it was going to happen, too. This time it didn’t. Ten fishing hours, no result. Let’s introduce a new character in the story. Pops into the picture in your mind, a character called an osprey.

An osprey is like an eagle or a hawk. It’s a bird of prey. The osprey jumps off of its perch. On the other side of the lake, we see this big bird leave the tree, circle above the water for maybe 1 minute, 1.5 minutes, for sure less than 2 minutes. All of a sudden, the bird dives and comes out with this big rainbow trout. You can imagine that on the side of the lake, my kids’ jaws have dropped.

They’re like, “Are you kidding me? We’ve done this for 2 hours times 5 poles, 10 fishing hours, and no results. This bird, in less than two minutes, circled, saw the prize, dove, and came out with the fish.” It was incredible. It was one of those beautiful mountain wildlife scenes. You wish you captured it all on camera. It was incredible.

EEP 18 Brett | Living The Dream

Living The Dream: If you want to get next-level results for your company and less chaos and frustration, you’ve got to figure out how to lead people in a way that they can take targeted, coordinated action.


What does any of this have to do with you or your business? I hope that you see some of the parallels without me drawing them out. Since we’re having a little bit of a one-way conversation here, let me invite you to consider with me how that osprey is like a fine-tuned business and how my family was like a chaotically-run business or a business where it feels like there’s way too much effort, not enough results.

Steps To Taking Targeted Coordinated Action

If you’ll spend a little more time with me here, I’m going to share with you ways that you can turn your business into that osprey. Like this osprey, if you can lead your team to take targeted coordinated action, you will receive significantly higher returns. You will achieve significantly higher levels of performance. In other words, if you want to get next-level results for your company and less chaos and frustration, you’ve got to figure out how to lead people in a way that they can take targeted coordinated action like that osprey.

Think about that osprey. What did it have at his disposal? It has these amazing eyes, the ability with the wings to get up above the water and use those powerful eyes to see clearly. It has this tail feathers and wings. They all coordinate perfectly to take that bird from circling to a fast dive. It’s got those amazing talons that rip through the water, grab the fish, and then the bird is flapping those big wings to get out of the water.

Eventually, that beak is going to be put to use as well with that fish. Every part of that bird is perfectly designed to work together to get the desired outcome. What I’m inviting you to do is to think about, “How might I better organize the resources I have? I’ve got a team. We’ve got good raw material. There are people who probably want to do a good job, probably know a few things about what they do.”

Hopefully, they’re the right fit in your company that they fit with the purpose and the values of your company. Regardless of whether or not they’re a great fit, there’s a group of people doing work. How do we better bring them together to act more like that osprey as one unit that can take targeted, coordinated action to achieve amazing results in an efficient amount of time?

How do we do that in business? I’m going to share with you three things. If you’ve read before, none of these will be necessarily new. These are three things that you can do to have your business become like that osprey. The first thing is you must set the vision. Not only you personally must see clearly, but you must help your team collectively see clearly the same thing. We call that set the vision. There are three parts to it, purpose, values, and mission. When you get super clear on purpose, values, and mission, now you can move together in a targeted fashion, a targeted, coordinated effort.

The second thing you must do is you must build the right team. If you think you have the talons and the beak, but you don’t have the tail feathers or the wings, that’s a problem. You can’t do this if you don’t have the right team to make it happen. All the vision in the world and all the elevated viewpoint in the world leads to no improvement in outcome if you don’t have the right group of people to go execute them. That’s obvious. Sometimes if you hear it said by somebody else or said another way, it might be able to click in or sink in for you.

You have to get the right people involved. Jim Collins talks about that is getting the right people on the bus. Equally importantly, or maybe even more importantly, getting the right people in the right seats on the bus. It’s not good enough to have everybody on the bus. We’ve got to make sure they’re in the right place so that we can take that coordinated action like the osprey.

First, you start with setting the vision. You get super clear on the why of the business, which is the purpose. That’s the driving force. That’s the thing we’re passionate about in this business. It’s the reason this business exists. We get clear on the values, which is how we operate. It might be described as a good mix between your core beliefs and the operating norms or our way of being.

If you grow the business to a higher point, you certainly shouldn't be sacrificing yourself and other things you want to do with your life. Share on X

When we have a purpose-driven values-based company, we’ve got the basis or the foundation of a great thing. It unlocks a ton of potential in any organization when they get clear on a purpose that is burning within everyone that’s involved with that business. They share a set of values or a way of being. It’s behavioral. You can see this in the daily walk and talk of team members when you get this right. Purpose and values, and then a clear mission.

That osprey knew exactly what it was after it. It wasn’t circling the water, trying to figure out what it would do next or, “Should I go after a mouse, a squirrel, or a fish?” It knew exactly what the mission was. There was no question. The destination was clear. From that, it can use its unique abilities to take care of business. Go down and make that happen. You need that clear vision and then you need the right team, the right group of people that you’ve assembled to go make that vision a reality.

That’s parts number one and two of becoming more like the osprey, to set the vision and then build a team. If you want to push yourself a little bit, add an adjective, like build a world-class team to go make that happen. The third thing I want to spend a little bit of time on is called building the meeting rhythm. In other words, how do we bring people together in a way that we can take targeted, coordinated action in a way that doesn’t take a lot of motion, figuring out, wobble, confusion, or inefficiency?

A good meeting rhythm becomes the way that you do the planning and execution cadence in your business. In that meeting rhythm, you would have an annual and quarterly planning cadence, and then monthly meetings to make sure we’re doing everything that we said we were going to do in the annual and quarterly plan and also to maybe bubble up some more tactical issues that come up in our weekly meetings, but then we shift from strategic to operational in the meeting rhythm.

Annual and quarterly would be strategic progress-oriented items. A daily and weekly meeting cadence would be more operationally focused where we want results. We want to get good at the day-to-day results. The monthly meeting would be something in between where we can deal with bigger issues that come up in the operational excellence side of running our business. We can also check in on the strategic progress side of things.

A good planning and execution rhythm enables the team to function as one. You know the human tendency to drift. If I use the analogy of true north or center, people tend to drift away from the center and drift away from true north. As a leader, you’re constantly needing to bring them right back to where we’re headed. There’s the mission. We’re not getting distracted by shiny object syndrome, the emails that are coming in, or all of the Slack messages, text messages, or phone calls, you name it. In the many ways that we get pulled away from our focus, we need to get people right back to clarity and alignment. We do that through a good meeting rhythm.

If you want your business to become like that osprey and get exceptional results in the least amount of time possible, not like the ten fishing hours that my family was exhibiting, but more like the two minutes that the osprey was demonstrating, then you must set a clear vision and assemble the right team to go make that real. You must create mechanisms, a meeting rhythm inside of your company that becomes like the heartbeat of planning and execution so that you can all stay on the same page, clarity on where we’re headed, and then row together in the same direction.

There are all sorts of analogies, phrases, and examples we use for seeing all the same way and all pulling in the same direction, but that’s the key. When you do that, it’s pretty magical. You get osprey-like results in your business. In the businesses we work with, it’s not uncommon for us to see them doubling or tripling in 18 to 24 months. You might say, “That’s a long time to do all this work.”

If you think about what it takes to set the vision properly, assemble the right team, and get good at this meeting rhythm, it is going to take some time and effort to build those things. The sooner you get started, the sooner you get the benefit. The longer you wait, the more burnout you get. The more of the same old, same old that you’re going to get from what you’re doing.

EEP 18 Brett | Living The Dream

Living The Dream: All the vision in the world, all the elevated viewpoint, leads to no improvement in outcome if you don’t have the right group of people to go execute it.


Success is awesome. We get to $1 million dollars. Plus, you feel great about the accomplishment. Not many businesses make it there, but then we feel all of that weight and the frustration of having team members who don’t act as we would and don’t seem to have as much ownership in all of this as we do. They don’t have equity. They don’t act and think like owners. They don’t take care of customers the way that you would. You get frustrated with some of the things they do sometimes. You might even describe it as boneheaded. “Why in the world did they do that? What were they thinking?”

Most of the time, the problem comes right back to the person you’re looking at in the mirror every day. You haven’t led them to clarity and alignment. They can’t take targeted, coordinated action together as one unit because you haven’t led them that way. I hate to say it in your face, brutally honest, but that’s what happens. We are the problem as business owners.

The good news is we can change that. We can lead in a new, more powerful way. You can do this. I’ve seen it happen over and over again. Relatively soon, at 12 months, 18 months, or 24 months, people are breaking through previous growth ceilings. They’re doubling or tripling their business. We’ve even had some companies 10X their business over the course of 2 to 3 years, doing the things that we’re sharing with them through our Elite programs.

As always, I’m trying to bring you some real, usable content here, the information you can use as a business owner to change the way you lead. That all starts with enrolling your team in the process of creating a much more powerful vision than you have and then making sure that you have the right team and leveling up the ones that are there that can stay with you on the journey. Finally, putting in place a meeting rhythm where you guys can get together and talk about what’s happening from a strategic progress standpoint and an operational excellence standpoint so that you can take targeted, coordinated action together like that osprey.

My wish and hope for all of you is that you become osprey-like in your businesses. You can do it. I’ve seen transformations over and over again, where they were thrashing on the side of the lake, like my family and I. As they’ve done this work, they transform their business into an osprey and yield amazing results, much fewer headaches, and a lot better life. You can have the business that you want and the life that you want. It is possible. It starts with becoming like an osprey. Thanks for humoring me and reading this.

I have a hard time sometimes wondering who would like to read this, but I hope that you found something valuable in what I shared. I will share things every single month. I’ll keep bringing great business owners in as guests and great experts that are all aimed to help you grow your seven-figure business. Keep reading. Share this with others. Review it, rate it, and give us feedback. We love that you are forming as a community of elite entrepreneurs. We love being able to serve you. Thanks, everybody. We’ll see you next time.


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