Episode 137: Elite Entrepreneurs: Moving Past The Common Struggles Most 7-Figure Business Owners Face With David Gilliland


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Have you done many things for your business to grow, but you are still stuck? What are the struggles these 7-figure business owners face? How can you move forward? In this episode, Brett Gilliland welcomes his brother, David Gilliland, the co-owner of Elite Entrepreneurs, to dive into the common struggles most 7-figure business owners face and how to move past them. You can’t keep being the bottleneck of your business. To move forward from that is to be clear on what you are trying to achieve and prioritize. If you want to get unstuck, tune in to this episode because David Gilliland shares some key things to move forward and succeed. After you check out the episode, see how you can help your business even more with our business mastermind group.

I am thrilled to be with you all again. I always get to say that I have a special guest but in this episode, I have a special guest in more ways than one. Not only is he special because he knows stuff that will be very valuable to all of us but he is special because he and I share parents. He is my brother. His name is David Gilliland.

He and I grew up in a large family. He is the closest brother in age to me. We have a sister between us. He and I are the two brothers that get to hang out at work. We have been working together for the last couple of years. We thought it would be fun to riff together on some common challenges we see that seven-figure business owners face, share some fun stories around that and talk about the difference makers, what makes the difference between those who struggle and some of the things that we will talk about and those who are able to move forward, shift gears and grow their business once they pass that $1 million mark.

David is an expert in organizational behavior. He knows business. He has been working on conserving small businesses for decades. He has helped lots of business owners in that seven-figure space figure out how to move forward and move past some of the challenges we will talk about. David, thank you for agreeing to be on the show. I’m glad that you are here.

I’m glad to be here.

I can facilitate with some questions but we agreed that we would have a little bit of a chat. This might be a little different in terms of the format than we are used to doing but it will be fun and valuable for those who can relate to some of the challenges we are going to talk about. David and I have seen hundreds of business owners in the $1 million to $10 million space struggle with some things. Some patterns emerge in our working with these businesses. We are going to talk about some of those struggles.

If they resonate with you, the good news is we are going to share a few key things you can do to start moving forward if you have any of these struggles. David, let’s start with some of the things that we often see seven-figure business owners struggling with that we could almost predict when we meet one. What are some of those things?

We will talk a numbers thing fast. It is popping to mind and it is like, “I have no idea what is going on. We were growing and now we are stuck.” They are flat-lined. Their revenue has stopped. It doesn’t matter. It is like they are banging their heads against a wall and are not breaking through or even more discouraging, they are telling me, “My revenues are going up. We keep making more sales but I make less money on each new sale.” Their margins are dropping while their revenues go up. They are like, “I can’t figure it out. What is different? We are doing the same thing for the same customers and things are falling apart around me.”

We have both seen it more times than we can count. I had a customer, a husband and wife team named the Tricketts. They have a marketing company called Practice Promotions. They put together a little graph. They showed how they had bumped up against an imaginary ceiling. Quarter after quarter, it was like, “We can’t break through.”

The fun thing about that particular chart is they put a place in time where they started to do some work with our company, Elite Entrepreneurs and the chart starts to go up again after that in pretty short order. They had the same thing you are talking about. They hit that spot and no matter what they tried, they couldn’t break through.

I had another one with the same ideas. He had run his business for 20 years and was still stuck going from $700,000 to $1 million and back down enough at this place. He was like, “Maybe that is as much as my business can do.” They start learning their things. To be at $30 million is a fun place to be. You see this like, “What happened in between?” They finally got unstuck. They figured it out. It is fun to see the change but it is frustrating up until then and we get it.

Sometimes we have a little fun with this one, where the business owner feels like he or she is tapped out. They are stretched way too thin. Sometimes we see this in the structure of the team itself, where the business has grown to a place where maybe they have 10, 12 or even closer to 20 people. By and large, they all report to the business owner. The team has grown but the structure hasn’t quite matured or evolved at all. Everybody reports to the business owner. Everybody is going to the business owner with every little decision. You have a fun story around this one I love for you to tell.

You would think the structure was there. They had these leaders meeting together. I’m in their conference room, helping them to set strategically for the year and where they are going. We got 3 leaders and 24 employees. We are working on some hard stuff and thinking through this. In comes an assistant over here. She is over human resources and the office management thing. She was like, “I hate to bug you but I have this question. I got to figure this out.” We were like, “We can stop. Go ahead and ask your question.” She was like, “We have the company party coming up. Would you prefer cookies or brownies?”

After she left, I turned to him and said, “Common questions coming to you are uncommon.” He was like, “We have an open-door policy. We want people to be able to come in with their questions.” I found out people are always coming in with every tiny or large question. It is this endless cue. Everybody was there. How could you ever get anything done? How can anyone ever feel like they can even stretch their wings out and do something great in a company if they feel they have to get approval for tiny things like cookies and brownies?

We see this when a business owner may feel a tremendous weight on their shoulder. Sometimes it manifests as a little bit of overwhelm or burnout risk. If we dive in, we see things like everybody is coming to you with every question. You have team members but you feel they are not able to take things that maybe the right team members could take. You never work with them or look to replace them if they are not the right people. This thing perpetuates where everybody is coming to you for the answers. You haven’t been able to figure out how to organize work and delegate to others stuff that shouldn’t be on your plate anymore.

On the other side, they got the employee whom is one of the leaders talking with him. He says to me that I put forward my ideas. The owner always seems to have more input, a different way of doing it, telling me why this won’t work and pulling back on the reins. I have to wait until he decides to move on something. The people that put in leadership aren’t able to lead at all. Frankly, that individual told me, “If this doesn’t change, I’m out of here. I got more important things to do with my life.” He was about to lose his actual support. It wasn’t that the people didn’t know how to act. He wasn’t letting them at all. It’s micromanaging, not trusting some things.

We often see business owners in the seven-figure space get stuck because they have a hard time relinquishing control. That is because they are the ones that figured it out in the beginning. They got it to this place and it is like, “If I let go, it is going to get done wrong. I’m concerned that so-and-so is not going to maintain the client experience the way I like it.”

EEP 137 | Elite Entrepreneurs

Elite Entrepreneurs: Business owners in this seven-figure space get stuck because they have difficulty relinquishing control.


Whatever fears we have is common. It is natural to feel some of that but if we hang onto it, we have automatically capped ourselves at what our business can do. It can do what it is doing now because we can barely keep all of this together and that is all we can do. That is a big one we see out there for a lot of business owners in this $1 million to $10 million space.

Let’s do something a little bit related to that. The idea of relinquishing control comes when we can trust. We got the right team members. A lot of people we see in this space have a hard time progressing because they don’t know how to hire to the vision of the business. Let’s back up and talk about those who aren’t even clear about the future because they haven’t set a vision with their teams. What do you see in that space, David?

I was wondering from you if you had some experience. I see it a lot when they say, “I wish my team could think like business owners. They don’t seem to make decisions the way I would. They wonder why that is.” They are always looking to hire someone like them, which isn’t always the right solution. They wish they could find someone like them. They feel like it doesn’t exist. I hear a lot of complaints like, “This next generation, I don’t know.” It has nothing to do with the next generation. What are you seeing?

I have a slightly different angle that I see as the one where the whole team feels like, “We can’t do any intentional forward-looking type of work because we are so busy delivering what we are doing. We set up our day-to-day work in a way that has us cranking the machine we have.” There is no intentional time to break out of that mode and build the next thing or make progress in a strategic direction.

Whether it’s this side of it that David is talking about where it feels like, “They won’t think and act like an owner. All of us are stuck delivering requirements, getting and keeping those customers that we have and not building the organization’s muscle or the business of the future,” both of those things lead to staying where we are at.

I had one of those clients who were like, “We are going to have our meeting. We love for you to come to see what we are doing.” At the time, I was doing some of those trips. I went there and showed up. It was a big staff meeting. A little dog and pony show is going on. They are talking about issues. They are circling. “What are we going to do about this?” “That depends on what direction we are heading.” “How are we going to take care of this customer?” “I don’t know what their problem is.”

They were everywhere. People are bringing up parking issues. They are talking about this customer need and this new product they might want to launch. It was all jumbled and talking everywhere. Afterward, I didn’t know who was supposed to do what. I had no clarity of what we were supposed to achieve. I asked them. I was like, “How did that go for you?” He was like, “It went well. Everyone seemed to be contributing. We shared some important information. Business is messy like this. I like to involve them.” I said, “What other meetings do you have?” He was like, “We have this meeting regularly. We will sometimes meet as teams to take care of some things but this is our meeting. This is where we regularly work on the important things in business.” I was like, “What in the world?”

It is like the Battle Royale where everybody is stuck in the case together and we are all going to talk about stuff.

No clue where we were headed and no one else knew what was most important. There were no priorities about anything and no one owned anything leaving the meeting. No point in the report like, “Here is what we are doing next. Here is what we did last time and getting feedback.” I was like, “This was a meeting stuck in the mire. You are not moving in any direction.” They felt it was important to make sure everyone had a voice, which I’m all for everyone having a voice. There are places for that.

The big issue is when we are not clear on how we work together efficiently and effectively to move the business forward strategically in the long-term. Let’s have some intentional meanings around that. We need to meet for some of these operational messes that are going on. We need to fine-tune and keep improving. Bringing those together is a chaotic thing.

There is a time and place for both, which we will get into here in a little bit. We see lots of things but on the list, there are some of the favorites that we wanted to share. Don’t take offense to this if you can relate. This is the way it happens. A lot of these businesses start by hiring family and friends. It is people that you know and trusts. You are in this foxhole mentality together where it’s like, “We are gritting, grinding and trying to survive this startup phase.”

We get to this million plus and the team is starting to grow. There might be 6, 8 or 10 of us. If we bring somebody in from the outside, there might be a revolving door coming and going because we don’t know how to bring them in and integrate them well into this team. There might be some weird family dynamic stuff going on that is hard for other people to play with. We pay people to come in, train them up and move on to the next thing. We are in this vicious cycle of not being able to move forward with our team because we haven’t figured out how to hire well.

They are often saying things like, “I feel like I’m hiring people and training them up to go work for my competitors. I hate this. This isn’t worth it.” They almost think, “I need to find talented, skilled people who can come in and do the work now.” That is a little shortsighted. That happens a lot. They feel stuck because all their profits go to this one activity. They never get around to serving their customers.

Whether it is hitting a revenue ceiling or we see some growth still but our profits are tanking. It is this idea that the business owners become the bottleneck. They don’t know how to relinquish control. They are overwhelmed. They are blending strategic and operational in the business or they haven’t gotten over that point of figuring out how to hire beyond family and friends.

EEP 137 | Elite Entrepreneurs

Elite Entrepreneurs: Business owners also get stuck because they haven’t gotten over that point of figuring out how to hire beyond family and friends.


These were some of the challenges we see over and over again as we are working with seven-figure businesses. Whether any of those things or all of those things, let’s shift and talk about some of the keys that we have seen have helped business owners make that shift beyond that revenue ceiling they were hitting or beyond the chaos and the imbalance in their life. How did they get to a better place with time and money freedom? Let’s talk about some of those keys together. Why don’t you start with one of them and we will jump into that, David?

It sounds like a lot of the things we are talking about have to do with this owner being the indispensable resource that everyone seems to have to tap into. Maybe they are working super late hours to keep up with the growth or are being crushed by it. You can’t be the bottleneck for the business. Somehow, we have to get what is in our minds as business owners and our hearts out. The clarity of where we are trying to go is getting clear where we want to go. Get it out of our heads and into the minds and hearts of our team. That seems to be one of the first things.

If they are going to think and act like business owners and make good decisions, that help us to move forward. We got to quit holding it inside. I don’t think we intentionally hold it inside all the time. We just subconsciously think, “Doesn’t everyone see it like that?” No, they don’t. Your team can’t read your mind. One of the first key things to do is to get clear. We like to call that setting the vision.

We are being clear about why we are in business. Why are we here? What is the big cool thing we are trying to achieve? Who belongs on this team? What are the priorities? The way I make decisions, the things that matter most to me and my key team members that are like, “If I could replicate them, I would.” Amongst us, what are those things that we prioritize? What are the values we base our decisions on so they can get other people who will base decisions on those same values and priorities?

If we can get that far, that is huge to make sure they are the right people. Get it out of our heads. Get it into our people and help them know where we are going. What is the big goal? Why does it matter? They then can get behind that and know, “We are trying to impact this many businesses by this year. We are going to have to do a lot of growth.” Some key thing is nobody is a mind reader, don’t make them do it. Let’s get clear and help them to know it. They want to succeed and please us too. They want an, “Attaboy.” They want, “Wow, I win.” They can only do that if they know the rules of the game.

Nobody is a mind reader. Don't make them do it. Let's get clear and then help them to know it. They want to succeed. Click To Tweet

I love how you talked about, “We got to get it out of our heads and get it clear.” A lot of times, the business owner and the whole team are pulled into the day-to-day machine. There are some books out there you might refer to as firefighting or getting stuck in the weeds. It’s whatever that day-to-day thing that always pulls at you and sucks you in.

Sometimes that is in the form of our inbox, email, the Slack that we have going in our bazillion Slack channels or whatever is going on in social media, calls or texts. That stuff is pulling at our attention. The business owners who figure out how to get past some of these things we talked about are the ones who break out of the chaos of the day-to-day and intentionally set time to get clear with their team.

If you took a block of time that feels maybe too big at first but would be manageable still, maybe you took a 1-hour chunk of your day and spent time trying to get clear, that would be better than where you are or 2 hours on a Friday morning. If you blocked off a little bit of time regularly to get more clarity and started helping your team get clear, that would go a long way in addressing some of these problems that we see all the time.

I love how you talked about that and helped your team get cleared. If you have gotten clear, it can be in the middle of the firefight and solving the challenges going on to be clear and say, “We are trying to achieve the following. This is a way we make decisions. We do the right thing. This may be one of those priorities. Even if it costs us, we are going to do the right thing for the customer and do the things we said we were going to do.” Maybe that is one of your values.

If you say that before, we are like, “How do we solve this problem?” It already sets the stage for them to win. It doesn’t mean that it gave the exact solution but it is going to have them measuring it against what matters most and they are going to go forward with that. That is huge that your team can feel confident that they are in line with what you most care about.

David, one of the risks of putting us together on these topics is that we could go all day on any one of them. There were two more things we wanted to make sure we got into this episode. Let’s go to the next key for solving some of these challenges that we talked about on the front end. That is hiring to that clarity.

You talked about getting clear. We use the term setting the vision. We got to learn how to hire the people who fit within that mold that you talked about. This doesn’t mean you don’t hire any diversity. This means hiring a bunch of diversity in background and experience but oneness or sameness in this set of values in our way of being, how we are going to operate and make decisions. There are got to be clear filters about how we are going to hire people. We only let people in who are going to match this way of being with one another. That is a hard one to transition to.

When you look to hire someone, what everyone ever puts out there is, “Here is my experience. Here is how smart I am. Here is the stuff I have done before.” That is all most of us have pitched when we are looking for someone. We were like, “Here are your job duties. Here is what you have to have done before. Here are your experience levels.” Is that a formula for disaster?

We all go there because we need somebody to do this work. We are like, “Please come do this work.” We fail to recognize the person we are bringing in to do the work needs to be able to feel comfortable to do their best work here. They need to fit in with this team and be excited about this cause that we are all up to together. If we are not bringing in the right person, we get that revolving door of turnover, which is so expensive, painful and time-consuming.

EEP 137 | Elite Entrepreneurs

Elite Entrepreneurs: The person we’re bringing in to do the work needs to feel comfortable, do their best work here, and needs to fit in with this team.


I have seen it over and over again. It is not revolving but you wish that person would leave. They are extremely bright, intelligent, the top person in your space and they are in your company, costing you a ton of money and destroying the morale of everyone around you. They are not serving things the way you want to and trying to make your business something you didn’t even want it to be because they are that competent.

The division that comes through all of it is so much money wasted. Hundreds of thousands of dollars were lost in direct expenses. Forget the opportunity cost and direct expense for these highly valuable people who don’t fit your company. You shouldn’t have been let in in the first place. You will do far better to find someone who fits well, has a desire and some grit and has little to no experience that you train up because they love it there. They are going to stay, be devoted and grow with you. Fit first with culture and then with the role. When you can get both, that is awesome. That is the big win that is such a tough lesson to learn.

We go to family and friends in the beginning because we already have this level of trust and intuitively, if we’re doing this right, we are bringing along those who already share some common values we have. It fits. We then start to hire others that we don’t know how to hire for it. We got to get clear about what it is first. That was the clarity piece. What does it mean to fit well here? How can I interview or screen for that? How can I find out if they share those values and they are excited about the same purpose that we have? That is the second thing.

It is doable. We call it our hiring gauntlet. It is a learnable skill, repeatable and can be done in any industry by anyone. That’s the beauty of it. You got to learn the skill.

Everybody who has built a business to $1 million in revenue has already learned several skills. They weren’t necessarily a natural marketer but they learned how to market enough to get to that place. They may or may not have been natural salespeople but they learned how to sell enough to get to that. Like those skills to get customers, you can learn the skills to get great team members. I love that you said that.

The last thing we wanted to touch on is meeting rhythm. That’s our label for it. It is the idea that you would separate the longer-term strategic items from the day-to-day operational items in your meetings. You wouldn’t throw it all together in a hodgepodge and say, “Here are all the people who need to talk about stuff. Let’s get in and talk about stuff.” That is when we get into the endless loops that David was talking about. What does it look like to separate those things a bit, David? What are a couple of ideas for how to make that better?

If you are going to lead from this point on, you have to learn that meetings are crazy valuables to help you buy more time and focus. Without meetings, you don’t have the time and focus needed to build the business you need to build to succeed and grow the way you want to. First, there is this, “I have to learn to love meetings instead of hate them,” which doers hate them and leaders love them. “I have to learn to get good at them.” That is a personal mindset in there.

The second thing I find important is to set time aside to work on your business. “Annually, let’s get clear about where we are headed and what has to be built. Yes, we are going to talk a little bit about what has to be done in operations and how they have to deliver but we have to talk about building the business we need to be 6 months, 1 year and 2 years from now. We have to do it now. Otherwise, it won’t be there. It doesn’t just happen. We have to build it.”

I love the quarterly rhythm of we are talking about the strategic things only. I leave all operations out where I’m not going to solve operational issues now. We are going to build the future of what we need to do and become to deliver next year, the year after and the year after that. I love the time and clarity it gives everyone. When they are doing their day-to-day, this may be a meeting you have on a monthly, weekly, daily huddle, even 5 or 10 minutes, all that operational stuff. We got to make sure it has done well.

Build the future of what we need to do and become to deliver the following years. Click To Tweet

That can align with where we are heading in the long-term. Everyone knows this is where we are headed. I’m doing this work now. This is how I’m operating the business. Over here is building the new business that we are going to operate in 6 months or 1 year from now. Keeping those separate is super important. You could have more strategic things that bleed in but every couple of weeks, maybe you have a standup check-in with that team that is pulled together to do a special project. We want to have those check-ins. We can have a dashboard that tells us but we don’t want to mix those meetings too much. It gets hairy.

They are separate items. If we do this consistently, we will see significant changes. Imagine going into your meetings and people rolling their eyes or dreading going into another meeting. If you are feeling that way and this meeting isn’t any good, I invite you to hold up a mirror a little bit and say, “How am I not leading this well? How have I confused the strategic and the operational or let those things co-mingle in a meeting where we go around and never get anywhere?” That is on us as leaders. We have to figure out how to separate those things and this type of meeting gets this attention. When we lead it well, people start going, “That was a productive meeting. I got clearer. I feel like we have more alignment. I know what we are doing.” People value that.

What I love is that long cue, the line of everyone who wants to come into your office and ask all these questions. They know what hour of what day is set aside for the meeting that is going to address that. They bring it right then. They are freed up. They don’t have to wonder, “Are they available now? Are they not?” They can work on their work. They put it on their calendar. “There is my note. I will bring it to that meeting.” It is beautiful. They love it. It saves them time. If you love it, it will buy you time like nothing else. Well-run meetings buy you time to do the most important work.

We started this conversation by talking about the thing we often see, the little revenue ceiling. We mentioned a couple of examples but going back to the Tricketts, they brought me this graph. They were like, “Revenue ceiling.” They put a picture of our logo on their graph. They were like, “Here is the point where we came across Elite and learned what we needed to do.”

What they learned is what we talk about. They learned how to set a vision, hire the right people and put a meeting rhythm in place. Within 2 to 3 years, they had tripled. That may seem like a long time but think about it. You could spend 2 or 3 more years in the painful spot that you are now or you could be triple what you are. Not just in revenue but you got more time, space and owners in your business, people who care about what is going on and can take some of the burdens off your shoulders.

I mentioned the Tricketts as one example. We have seen that time and time again where the people who learn how to get clarity and bring the right people to the cause get involved. They learn how to separate the strategic and the day-to-day operations. If they learn how to manage both those things, they start to see the breakthroughs happen and all the things they wanted as a business owner start to come into their life like, “Things are getting better.”

I love how they talk about it differently. They used to be craftsmen or great marketers. They thought growing their business more meant they had to do lots of that. Instead, they learn this new craft of leadership and how to organize the team, build them and deliver results through others. They learn this new craft and this new craft takes a little time to learn.

Once they got it, the sky was the limit there because they had tens or hundreds of people that could do the delivery of the old craft. The work that they do is so much more valuable. That is when you see the revenues and profit margins go up because you are doing more valuable work with your time and you’re helping others be successful in their roles instead of being bottlenecked by decisions.

You see the revenues and the profit margins go up because you're doing more valuable work with your time, and you're helping others be successful in their roles instead of being the bottleneck of decisions. Click To Tweet

It is possible to build this winning thing where everybody benefits. In the mirror, it is usually pointing right back at us. As leaders, we got to figure this stuff out. David, it has been a pleasure to spend some time with you. It is natural for us to be able to jam on topics like this together. I typically ask my guest how people can learn more or connect with them. Let’s do that. Where can they learn more about you and what you are up to or connect with you on social? How can people connect?

You can always go to our website, GrowWithElite.com. You can connect with us there. There are several resources you can grab but if you want to know these basics and understand them, I would suggest you look at our Elite Ignition Program and get in touch with us. You could come to one of our events. You will see those advertised there. You can get to know the community of great business owners who are implementing these things and seeing these successes. Come and learn from and with them.

Thanks again, David. It was a pleasure. For all of you reading, please share and like. Spread the word. We want to help as many seven-figure business owners as possible because these known challenges have known solutions. I’m going to keep bringing wonderful guests to help you in your journey beyond the place you are at now. Thanks for reading. We will see you next time.


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About David Gilliland

David GillilandDavid Gilliland is a business leader who understands the power of people and teams to deliver exceptional business results in both small and large organizations. He helps executive teams align their efforts to deliver exceptional results through leadership, vision, strategy, clear metrics, and effective meetings.

He has the ability to address the elephant in the room and get it out of the way of the team’s success and applies his trade in individual companies consulting with the executive team and coaching the CEO. He also trains through large group executive training and keynote addresses. In 2020, he joined forces with Elite Entrepreneurs as a co-owner to build a solution specifically focused on helping businesses and practices to grow to well over $10 million in revenue with the teams necessary to sustain the growth.

Over the past 18 years, David Gilliland has consulted with over 250 small businesses across the US as well as 40 of the Global 500 including Accenture, Duetche Bank, Siemens, Intel, IBM, Rio Tinto, Walmart, and UnitedHealth Group. His most important work has been at home with his wife and 8 daughters where he has learned more about leadership, team dynamics, change management, and personal development than he learned in his 20+ years in the work place and post graduate work in Organization Behavior/Leadership and Strategy combined. There are principles that apply in all areas of life that help individuals and teams achieve great results while becoming the spouse, parent, neighbor, practice, and business leader they always wanted to become.

A native of Arizona and current resident of Utah, David Gilliland currently serves small business owners and their executive teams through his work with Elite Entrepreneurs to help them break through the natural plateaus that exist every time you triple your team size.


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