Scaling Success: Navigating the Common Challenges 7-Figure Business Owners Experience—Brett Gilliland, CEO, Elite Entrepreneurs

Have you plateaued in your business? Are you trying to figure out how to break through to the next level of your business growth? 

Our guest today is Brett Gilliland, who is an expert at helping leaders break through their current organizational barriers. He shares with us the common hurdles leaders face as they push to the 8-figure revenue marker. 


Go from learning and doing to leading.


Brett Gilliland is Founder and CEO of Elite Entrepreneurs, a company that specializes 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 10 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 along 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 the development of Infusionsoft’s Leadership Model and was serving as the VP of Leadership Development when the decision was made 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 8 children. 


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Dr. Tom DuFore, Big Sky Franchise Team (00:01):

Welcome to the Multiply Your Success podcast, where each week we help growth-minded entrepreneurs and franchise leaders take the next step in their expansion journey. I’m your host, Tom DuFore, CEO of Big Sky Franchise Team. And as we open today, I’m wondering if your business has plateaued. And if it has, are you trying to figure out a way to break through to the next level of your business growth? I know many clients that we work with have hit that point, and that’s why we end up working with them to help franchise their business. Well, if you decide that maybe you want a franchise and grow through that, or maybe you are just a franchisee or another business that’s doing well and you’ve hit this plateau and wondering, how do I get through that? Our guest today is Brett Gilliland, and he is an expert at helping leaders break through their current organizational barriers.

Dr. Tom DuFore, Big Sky Franchise Team (00:53):

Now, Brett is the founder and CEO of Elite Entrepreneurs, which is a company that specializes in giving million-dollar business owners the knowledge, processes, and tools to grow to $10 million and beyond. He’s an expert in organizational development, leadership, and strategy, and spent 10 years helping Infusionsoft, which is now named Keap, grow from 7 million in revenue to over a hundred million in revenue. Brett was involved in the foundational work purpose, values, and mission over at Infusionsoft, and facilitated the strategic planning process for many years. As the leader of Elite business, Brett has helped hundreds of struggling seven-figure business owners overcome their biggest challenges and achieve new levels of success. When Brett isn’t busy helping business owners succeed, he’s a family man who enjoys spending time with his beautiful wife and their eight children. Let’s go ahead and jump into my interview with Brett Gilliland.

Brett Gilliland, Elite Entrepreneurs (01:49):

Tom, it’s a pleasure for me to be here. My name is Brett Gilliland and I am co-founder and CEO of a business called Elite Entrepreneurs. We help former, I’ll call them otherwise scrappy, gritty founder entrepreneurs figure out how to make the transition to capable business building CEOs.

Dr. Tom DuFore, Big Sky Franchise Team (02:07):

That summary is exactly why I wanted to have you on as a guest to talk about this idea of what got you here won’t get you there. And it’s a mantra I’ve actually been sharing within our own business and talking with our own team to say, “Look, what got us here is not going to get us to where we actually want to go, so we need to be making some changes there.” So on one side of the equation, who knows, maybe I’m a potential prospect for you in your business. But the topic is very timely. So what are some common things that you see of the, quote, “What got you heres,” that won’t get you there? What are some of those common things that you see successful entrepreneurs struggle with as they start to make that transition into the CEO and leader of their company?

Brett Gilliland, Elite Entrepreneurs (02:51):

Yeah, I love that question. Thanks, Tom. And if it’s okay, if you’ll remind me, I’d like to set that aside just for a second because I want to emphasize the point that you made that what got you here won’t get you there. It sounds like you’re great at teaching that to your community, your audience. And I just want to plus one that a little bit with something that might be useful to you and them. We put together this thing years ago, and I’m using we loosely. This amazing CEO that I used to work with years ago, his name is Clate Mask. He’s the CEO of a company called Keap. They do small business CRM work. But we were serving small businesses, and not all small business is the same. And some of them were in this… They’re in different stages or different ranges of revenue and ranges of team size and complexity.

Brett Gilliland, Elite Entrepreneurs (03:41):

And so Clate did a bunch of original research on some US Census Bureau data and produced something that we call the stages of small business growth. And so when you say, “What got you here won’t get you there,” I always immediately go to this stages thing. And there’s this really fascinating pattern and it aligns with revenue growth. It’s on the ones and threes of revenue. So there’s a stage between 100,000 and 300,000 in revenue. There’s something there. From 300,000 to a million, 1 million to 3 million, 3 million to 10 million, and so on. We actually grew that business from 10 million to 30 million and 30 million to a hundred million. So we’ve been through lots of these triplings. But every time there’s this little growth or maybe fast growth, Inc. 500, Inc. 5,000 kind of growth. And then it would level off, we’d hit a little plateau, and there was a new thing we had to figure out. Literally what got us there would not get us to the next place. And so would you be interested in the stages documentation [inaudible 00:04:42]?

Dr. Tom DuFore, Big Sky Franchise Team (04:41):

Oh, yeah. Brilliant. I love that. Yes.

Brett Gilliland, Elite Entrepreneurs (04:44):

Yeah. So anybody who wants to get it can just text the word stages, S-T-A-G-E-S, stages, to 480-900-1505. So 480-900-1505. Text the word stages and you’ll get the PDF, you’ll get the access to the actual document. But then you’ll also get access to a little video series that has us explaining the stages.

Dr. Tom DuFore, Big Sky Franchise Team (05:13):

By the way, for anyone who’s driving, don’t text that in as you’re listening to this. I’ll make sure that’s included in the show notes so that people can reference and go back to it if you didn’t get it quick enough. So it’s in our show notes there. That’s excellent, and I’m definitely going to be downloading that report and going through that. So let’s just, I guess, go back then to that initial question about what got you here won’t get you there. And I like this threes and ones, this pattern that you started to see. And I’m sure it’s different across the board, but are there some common threads or some common issues that you tend to see? And would you mind talking through some of those?

Brett Gilliland, Elite Entrepreneurs (05:45):

Yeah. So back to your original question, which was outstanding, and I’m going to focus my comments on that transition. When they go from 300,000 to a million, they figure out how to operate their business, they get it off the ground. Then they often hit a little bit of a ceiling there, it’s around a million. It might be 850,000, it might be 1.2, 1.3 million. Some entrepreneurs are able to push their business model a little further, but somewhere they get stuck between one and 3 million often. And the common thing there, and this won’t be any surprise to you, Tom, and it should ring familiar for many people who are listening to this, but the common thing there is that the business owner hasn’t figured out how to separate themselves or their identity from the business. They’re too inextricably connected to the operation still. They’re part of the machine.

Brett Gilliland, Elite Entrepreneurs(06:38):

And even if they’re starting to straddle the doing and the leading, they’re still too much in the doing. And so their business can only grow as far as their own ability to produce at that point. Even if they start to have some supporting cast around them, they haven’t really figured out how to set a powerful vision that creates a separate identity for the business and allows that business owner to get extracted from there, allows him or her to hire great people and really relinquish control to people in key roles. And when they’re able to do that, then they can go to the next level. So I said a lot, and I may have oversimplified it. But the point is, the common problem is they get stuck in the actual delivery of the product or service and they can’t quite get themselves out into the leadership role.

Dr. Tom DuFore, Big Sky Franchise Team (07:31):

Very interesting. And as I’m thinking about it, it makes me wonder, what are some things, and I’m not asking you to share all your secret sauce with us, but what are some things that you have found that help these entrepreneurs that are converting from that entrepreneur to that leader to make that transition as there is a transition period, right? Because if they pull themselves out all the way right away, they are an important cog in the wheel and that wheel’s going to fall off. How have you found some of your clients and what you’ve seen and companies you’ve led that have grown in this capacity, what have you seen happen in those scenarios for people that have pushed through that?

Brett Gilliland, Elite Entrepreneurs (08:07):

Yeah. It requires, and this is painful for a lot of entrepreneurs to hear, but it requires a little bit of slowing down so that we can speed up. So there’s one heavy part of intentionality that needs to be applied, and then another pretty heavy part of discipline or rhythm that needs to be applied. And so what I mean by that is, and it’s kind of counter to everything that’s inside of us as the business owner operator. It’s like I know what gets growth when I’m the business owner operator, it’s more sales and more fulfillment. That’s how we do it. But once you get to a certain level of success, again, right around that million dollar mark, maybe have six, eight, 10 people at this point that you have to figure out together. And I do encourage this to be a co-creative process with the team to get clarity about what we’re doing together.

Brett Gilliland, Elite Entrepreneurs (09:02):

And I hesitated and said what because I like to start with why. I like Simon Sinek a lot. So let’s get clear on our purpose. Let’s get clear on the how we operate or the values, which is really more about the who, the people that should be involved in this journey. And then let’s get super dialed in on the very destination-oriented mission, like the specific what by when, what we will accomplish by when. And the when in this context is usually three years out. I like three years out as a good mission for a first time mission creation. And so if you were to gather your team together and say, “Why are we doing this? Separate from me as the business owner, why does this business deserve to have life? And what are our values that we share? What makes us unique in how we operate? And we’re going to hire and we’re going to lead and we’re going to fire to these values. They are core values. And then what is the place that we’re going to go accomplish together? What is the summit? What’s the mountain? We’re going to go summit together?”

Brett Gilliland, Elite Entrepreneurs (10:06):

And if you get that kind of clarity as a team, now we can set good strategy and we can start to allocate resources towards an objective. And so that slowing down to speed up starts to matter if we get clarity first and then we build in some meeting rhythms to make sure that we’re working enough on the business and not just in it all the time. So in as short an answer as possible for that kind of a question, that’s what I would say is the key to moving forward.

Dr. Tom DuFore, Big Sky Franchise Team (10:36):

We help companies franchise their business. And for a franchisor that may be tuning in and they’ve gone through their franchising and the franchise lifecycle, there are always going to be high performers, a bunch in the middle, and some laggards behind. And so for these high performers, as a franchisor they probably end up with a bunch of folks that are in this range that you’re talking about that they’re at that million, $3 million, and they’re saying, “How do I get from that 1 million to 3 million and then that three to 10 million number?” And I don’t know if you’ve worked with franchisors or franchise organizations or franchisees in this situation. I’d love for you to talk about that a little bit.

Brett Gilliland, Elite Entrepreneurs (11:17):

We’ve been fortunate to be able to work with hundreds of seven-figure businesses over the past 11, 12 years. So lots of businesses, lots of industries. Across that, there are a handful of memorable franchises that we’ve worked with, so I’ll allude to some of those. One of them was a fitness franchise. It’s called Iron Tribe Fitness. They’re big in the southeast and expanding from there. But these guys figured out how to set this powerful vision as the franchisor, as the mothership or the HQ. And then they learned how to take that vision and help each of their franchises do the same type of work for their franchises, for those franchisees. So that’s one way that they did it is they got the clarity and they built a culture that was really powerful. And they included that culture in how they franchised out.

Brett Gilliland, Elite Entrepreneurs(12:10):

In other instances, we’ve worked with the franchisees who are part of a large franchise. There was a Mosquito Squad franchisee, there was a Maid Brigade, which was a home cleaning franchisee. There’s one right now with the Budget Blinds franchisee. But in each of these cases, these franchisees came and learned how to do some of this work we’re talking about, and then they became the standouts in that franchise. And actually, the franchisor would then go to them often and say, “Hey, share some of your best practices.” And they would start to bleed over into some of the other franchises. But in each case, whether you’re the franchisor or you’re a franchisee, doing this vision-setting work, getting clear about how we’re going to work on the business, not just in it, in a disciplined or rhythmic sort of way, will level up your performance in the team, especially if you build the team around this stuff.

Brett Gilliland, Elite Entrepreneurs (13:12):

And then you’ll see that bump naturally happen from one to three. Because the transition here, Tom, and I’m sorry that I lost this a little bit, but the transition here is about going from learning and doing, so the business owner learning and doing, learning how to market, learning how to sell, learning how to build a team, learning and doing, to leading. That’s the big transition from one to three. It sounds simple, but that’s really it. You got to go from doing to leading. And then from three to 10 it’s about leading leaders. So you have to build a leadership team. And I know some franchise models are not set up to have a $10 million franchise. Some of them are limited to what can happen in each market.

Brett Gilliland, Elite Entrepreneurs (13:56):

And so the business owners who figure this out might grow a normal, let’s say a normal Mosquito Squad from one to 2 million to four or 5 million like this guy did that we knew. But there’s only so much business one Mosquito Squad franchise can do in their geography. And so then you either have to choose to buy other franchises and grow that way or get into some other type of business as well. But hopefully that was enough idea. But moving from doing to leading, that would be my key takeaway, from doing to leading for each individual franchise. And then if it’s a big enough franchise that can grow in their market, then it would be moving from leading to leading leaders, building out that leadership team and growing from there.

Dr. Tom DuFore, Big Sky Franchise Team (14:47):

This learning to doing, I like how you referenced that. You’re going from that learning and doing to now leading in this capacity. And really, as I think about it, it’s, depending on what stage you’re in as an entrepreneur, you’re learning and doing. As you transition to this leader, you’re still learning and doing, you’re just learning and doing something different. It’s still the same general concept for the entrepreneur. So I’m thinking someone might tune in. Sometimes, and the clients we work with, I can tell that the owner, the founder, they’ve become a little stale or almost bored because they’ve really figured out their business, they’ve really mastered it. And they’re looking for that next challenge. And so as I’m hearing you describe this learning and doing [inaudible 00:15:30], well, here’s your next challenge, Mr. And Mrs. Entrepreneur is-

Brett Gilliland, Elite Entrepreneurs (15:34):


Dr. Tom DuFore, Big Sky Franchise Team (15:34):

… let’s learn this new thing that you can go and do and try it with what you’re doing.

Brett Gilliland, Elite Entrepreneurs (15:39):

And some people say, “Well, I just don’t like leading people.” Or they think more employees means more headaches. And so they sort of artificially cap what their business can do. They say, “I feel comfortable here,” and they settle into a routine. But you’re right, they all learned all the necessary work to build the business to where it is now. And the scaling work is learnable. And they have to learn if they want to keep going.

Dr. Tom DuFore, Big Sky Franchise Team (16:08):

It sounds like there’s one thing or something a leader could do every day to grow or to evolve, and what would that be?

Brett Gilliland, Elite Entrepreneurs (16:15):

Thank you for asking. Again, I’m going to cheat a little bit and step back and say, to me, it’s really helpful if you have a framing for what good leadership is before you start trying to work on developing that. So we created something called the Elite Leadership Model. You don’t have to use our leadership model, but there’s lots of ways of viewing leadership out there. So let me just introduce what I think is a good way to think about leadership. I think my role as a leader is, number one, set the vision. And that’s from Jim Collins. He’s a professional hero of mine, I’ll call him, or whatever. Somebody I admire, I like his stuff. So set the vision is the number one responsibility of every great leader is what Jim Collins says. I subscribe to that.

Brett Gilliland, Elite Entrepreneurs (17:01):

The second thing that we teach about being a great leader is building the team. And then the third thing is, as the business owner, it’s making sure that we have the resources. Get the resources or secure fuel for growth. Or the fun way of saying it that we all can relate to is don’t run out of money. That’s the thing is make sure we have the runway. So if you set the vision, build the team, and make sure we have the resources, those are your hats that you should keep as the leader of a growing company. You got to get rid of the rest of the hats. So when you ask me how do we develop ourselves as a leader, I would be working on those three things. How do I develop myself as a leader who’s good at setting vision? How do I develop myself as a leader who’s good at building the team? How do I develop myself as a leader who’s good at securing the financial resources we need to grow this thing?

Brett Gilliland, Elite Entrepreneurs (17:54):

And now I have a little direction around my daily growth efforts. And I would be reading books, I’d be listening to Big Sky Franchise Team, I’d be doing those types of things. We have a podcast called the Elite Entrepreneurs Podcast. There’s lots of good information out there and I’d just be constantly feeding myself with that. But then probably more important than that, I’d just set aside time every week to work on my leadership. And what I mean by that is how do I grow my business? I work on my business. And so how do I do that? I spend time doing that. And most of us just get caught up in the whirlwind of the day-to-day activity and we don’t work on the business. So the best leadership development for you is setting aside time every week to just exercise those leadership muscles. How do I start growing my business?

Dr. Tom DuFore, Big Sky Franchise Team (18:45):

Great description, I like that. Exercise those leadership muscles. That’s a great way to close that out. Well, Brett, this is a great time in the show where we make a transition and we ask every guest the same four questions before they go. And the first question we ask is, have you had a miss or two on your journey and something you learned from it?

Brett Gilliland, Elite Entrepreneurs (19:02):

Yes, I’ve had a miss or two for sure. I’ll say this. In my growing through the stages till we got to seven figures, my miss was wanting to just outsource marketing, outsource sales. I just wanted somebody to come and fix my customer acquisition problem. Let me just pay somebody to do that. And I learned that you can’t really outsource the marketing strategy, that you still have to own that as the business owner. There’s nobody who’s connected to it as well as you are. You know the market, you know your customers. And every time I just wanted to throw that off to somebody else, outsource that thing, it just didn’t go well. So I had to roll up my sleeves and learn and do that stuff that I didn’t really feel like doing.

Dr. Tom DuFore, Big Sky Franchise Team (19:50):

Let’s take a look on the other side. Let’s talk about a make or two. You’ve had a great career and various businesses you’ve been involved with. I’d love for you to share some highlights.

Brett Gilliland, Elite Entrepreneurs (19:59):

Coincidentally, two weeks ago we had our biggest and best Elite event ever. We do these quarterly events and we had the most people we’ve ever had in a room. It was in beautiful Park City. And it was all about leadership development. So in acknowledgement of this transition from doing to leading, our community asks us all the time, “Well, what do we do for leadership development?” So we created a whole event around it, and it was just a personal highlight for me to have the strength of the numbers of people, but also the energy there. The speaker lineup was outstanding. It was just incredible.

Dr. Tom DuFore, Big Sky Franchise Team (20:35):

Great. Well, congratulations on that by the way. Let’s talk about a multiplier you’ve used to grow yourself or your business or both.

Brett Gilliland, Elite Entrepreneurs (20:44):

I use a combination of a coach and a community. I think part of working on myself is to get good outside perspective. So I have a key coach or advisor who I go to every month. I pay him money every month to make sure that I’m getting high-level perspective on my business and that he’s pushing me and my thinking. So that’s really helpful. And then I belong to a community. So this is kind of funny for me because we have this Elite Entrepreneurs community that we’ve been running for many, many years now. And we are that for the business owners that we serve, but I didn’t have one for me. And for years, I just sort of justified that. I’m like, “Well, I’m with all these business owners all the time. We’re talking business.” It didn’t meet the need for me personally. And so this year, actually, I went and joined my own CEO group outside of my world so that I could just get that benefit for me. So a coach and or a community, those would be the multipliers that I would point to.

Dr. Tom DuFore, Big Sky Franchise Team (21:45):

Well, the final question we ask every guest, Brett, is what does success mean to you?

Brett Gilliland, Elite Entrepreneurs (21:50):

So success is so relative. So I love that you’re asking everybody. To me, it’s living our intention. It’s saying, “It’s not just living a default future, but we’re creating who we want to be and we’re creating what we want to accomplish.” And so success is declaring, “Here’s who I am and here’s what I’m about, and here’s what I’m out creating,” and then lining up my life and my world to go pursue that. And making progress towards that, I believe, is success.

Dr. Tom DuFore, Big Sky Franchise Team (22:23):

Brett, as we bring this to a close, is there anything you were hoping to share or get across that you haven’t had a chance to yet?

Brett Gilliland, Elite Entrepreneurs (22:28):

Well, I shared that I’d love people to get that stages document. I think that would be useful. I shared that we have an Elite Entrepreneurs podcast that we just have business owners on sharing their real growing lessons. I guess the last thing would be just please check out our website. It’s, so altogether,

Dr. Tom DuFore, Big Sky Franchise Team (22:53):

Brett, thank you so much for a fantastic interview, and let’s go ahead and jump into today’s three key takeaways. Takeaway number one is when Brett talked about some patterns that he found in the stages of business ownership. And he said it’s this tripling of revenue between the ones and three. So from 100,000 to 300,000, 300,000 to a million, 1 million to 3 million, and so on. And he said he has a great report available, which, by the way, you can text the word stages to 480-900-1505. Thought that was a great takeaway. Takeaway number two is the one thing that you can do as a leader every day is to set aside some time to work on your business. And he said, as you make that transition to the leader, there are three parts of that.

Dr. Tom DuFore, Big Sky Franchise Team (23:42):

Part number one is set the vision, part number two is build a team, and part number three is to have or secure the resources. And takeaway number three I found interesting is a miss that he shared, which is that he tried to offload or outsource his marketing strategy and the vision and direction for that. And what he found is that, as the founder or owner of the business, you are so close to what’s going on that no one understands your customer, your services, and all of these moving parts and their needs better than you. So staying in that to give the direction or the vision for that and let others go and implement. And now it’s time for today’s win-win.

Dr. Tom DuFore, Big Sky Franchise Team (24:30):

So today’s win-win is when Brett talked about this concept as the founder or leader of your company to go from learning and doing, which most owners I’ve worked with over the years have fallen into this, where you go from learning and doing to now leading. From learning and doing to leading. And I know I’ve fallen into that bucket myself, and I do and it’s something I’m working on. So this interview has been very timely for me personally. And what I think about from the vantage point here is you’re learning and doing and going into leading, which is what Brett said one of the key things was to be disciplined on spending time every week to work on your business. So go from learning and doing to leading. That’s our win-win for the day.

Dr. Tom DuFore, Big Sky Franchise Team (25:21):

And so that’s the episode today, folks. Please make sure you subscribe to the podcast and give us a review. And remember, if you or anyone you know might be ready to franchise their business or take their franchise company to the next level, please connect with us at Thanks for tuning in, and we look forward to having you back next week.

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