267. How to build a business bigger than you, with Dustin Hillis

15 Jan 2026 · 46 min · 19 chapters

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In short

Scaling a business beyond the founder by shifting from “bottle washer” to leader through executive strategy, systems, team alignment, and “pruning” underperformers.

Guest background

Dustin Hillis has led a $100M company and coaches hundreds of CEOs/owners over 16 years. He’s building toward a billion-dollar valuation and wrote Capacity: Building Your Business Bigger Than You.

Key claims

Founder burnout happens when one person handles operations, marketing, strategy, and more. Talent isn’t the limit; systems and leadership capacity are. To reach $100M, you need a five-year executive strategy—what works for $10M won’t scale. Hire for character/values alignment, not just resumes. Teams grow only as fast as the weakest link; pruning is required. Power must be given gradually to avoid misaligned leaders exploiting control.

Notable examples

Chick-fil-A interview process (Dan Cathy emphasizes character traits during interviews; Dustin recounts meeting him). Dave Ramsey interviews spouses. Dustin contrasts Chick-fil-A’s personal culture with Google’s “experience center” feeling “cold” and unwelcoming.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Identifying Bottlenecks in Business

0:45 to 2:06

Discussion on how high capacity business owners often become bottlenecks.

“Dustin has led a$100 million company and is currently building toward a billion dollar valuation.”

Introduction of Dustin Hillis

2:06 to 2:35

Overview of Dustin's background and professional achievements.

“the award-winning podcast where behavioral science meets workplace culture.”

Building Effective Systems for Growth

3:11 to 4:22

Dustin discusses the mental shifts needed around systems in business.

“Let's join the interview where Al is asking Dustin how to build a professional system that will facilitate growth without killing the creative spark that made the business great to begin with.”

The Importance of Executive Strategy

4:22 to 5:35

Dustin emphasizes the necessity of having an executive strategy for business scaling.

“So a lot of leaders miss the fact that their role is to train people how to do what they're supposed to do to set those expectations and to make sure you don't have the right the wrong person on the bus.”

Characteristics of Successful Teams

5:35 to 6:17

Discussion on team dynamics and aligning skills with responsibilities.

“They want you to give them that guidance, that framework so they can excel.”

From Small to Large Scale

6:17 to 7:35

Dustin explains the transition from small to larger businesses and the need for strategy.

“It sounds to me as a very fly with the seat of my pants kind of guy.”

Learning from Successful Companies

7:35 to 11:19

Dustin shares insights from Chick-fil-A's organizational culture.

“And I do think that you can get a lot of results, though, as a one man band and mom and pop shop, you, your family, your your wife, your your sister.”

Designing a Unique Company Culture

14:00 to 18:05

Learn about creating a company culture that reflects personal values and mission.

“I recently drove to or I flew and then rented a car and then drove to the Apple headquarters, the Google headquarters and literally walked around as an actual just visitor.”

The Journey of Growing a Business

18:44 to 28:00

Explore the stages of business growth and the evolving responsibilities of leadership.

“Let's rejoin the interview with Al and Dustin.”

The Executive Team Experience

28:00 to 29:29

Learn about the dynamics of an effective executive team as shared through a personal story.

“My daughter just came home from work from New York and said, hey, dad, can I take you out to dinner?”
Show all 19 chapters

Building Teams for Growth

29:30 to 32:19

Discover when and how to build effective teams as a business scales from million to ten million.

“There are some big businesses out there that have very low margins.”

Power Dynamics in Business Growth

32:20 to 35:38

Understand the importance of managing power dynamics and authority in leadership roles.

“Imagine you're talking to a group of 10 people all in that region of 1 to 10 million.”

Navigating Personal Relationships in Business

35:39 to 37:59

Explore the challenges of personal relationships and conflicts in a growing business environment.

“The hardest part is to you get so intimately involved, especially in that one to ten million dollar range.”

The Pruning Process for Growth

38:00 to 41:04

Learn about the necessary pruning process in businesses to foster growth and maintain health.

“And what's interesting, like, have you ever seen those little bonsai trees where people grow the bonsai tree?”

Firing Underperformers: A Difficult Necessity

41:05 to 42:00

Discuss the emotional challenges of letting underperforming employees go for the benefit of the business.

“And here's the thing, when you do it the right way, they know it too.”

The Importance of Letting Go

42:00 to 42:44

Learn why sometimes letting underperformers go is a favor to them and the organization.

“They find something that actually is more fulfilling to them.”

Who Should Read 'Capacity'

42:44 to 43:48

Discover the diverse audience that can benefit from reading Dustin's book on leadership.

“building the capacity of what you can do.”

Key Takeaways for Business Growth

44:06 to 45:15

Explore three crucial strategies for founders to avoid burnout and enhance their teams.

“And for those of you listening who are currently building towards that 10 million mark, Dustin's message isn't that you're doing it wrong.”

Empowering Leaders

45:15 to 45:59

Understand how structured systems can help leaders empower their teams effectively.

“Dustin's book Capacity Building Your Business Bigger Than You is a really deep dive into how to actually build these systems.”
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Transcript

Automatic transcript. May contain errors.

0:00Most business owners pride themselves on being high capacity. You know, that person who handles the operations, the marketing, and the strategy all at once. We rely on sheer willpower to get things off the ground. But there's a very specific point where that do-it-all attitude actually becomes the bottleneck for the entire organization. A lot of common themes you'll see is somebody that's super passionate about what they're doing, somebody that has high charisma, somebody that has high capacity kind of naturally, innately in them. They're a go-getter and they're the rainmaker, they're the operations person, they're the marketing person, they're the CEO, and they're the bottle washer all in the same day.

0:40That leads to burnout. And if you're doing it all, then there will be a point where working harder does not equal more results.

0:50Leanne:Our guest today is Dustin Hillis. Dustin has led a$100 million company and is currently building toward a billion dollar valuation. He spent 16 years coaching hundreds of CEOs through the messy, often painful psychological shifts required to stop being the bottle washer and start being a leader. He argues that your growth isn't limited by your talent, but by the systems you are willing to put in place. Dustin's book, Capacity, Building Your Business Bigger Than You, is actually out right now. It was released yesterday or day before, I think. It really is a masterclass on scaling teams, creating the right strategy to grow, and is written for you, the overwhelmed business owner.

1:32And if you enjoyed this interview, I really would encourage you to go out and buy it, especially this week, because you know, as a new author, then the first week is the most important week for sales. We get into the grit of scaling today and Dustin talks us through the five essential pillars of growth. You're going to learn the pruning process required to keep a team healthy. And Dustin also shares a sobering statistic about business partners and betrayal. If you want to scale your business to 1 million or 10 million, or even 100 million or even a billion, then this episode is for you.

2:05Leanne:This is Truth, Lies and Work, the award-winning podcast where behavioral science meets workplace culture. Brought to you by the HubSpot Podcast Network, the audio destination for business professionals. My name is Leanne. I'm a charter occupational psychologist. My name is Al. I'm a business owner. And together we help you simplify the science of work and create amazing workplace cultures. We'll be back with our conversation with Dustin Hillis after this very quick word from our sponsors. HubSpot makes impossible growth impossibly easy for their customers. And here's a perfect example. Lee, your turn.

2:38Leanne:Morehouse College needed to reach new students with fresh, engaging content. But with a massive 900-page website, even the tiniest updates took 30 minutes to publish. Breeze, which is HubSpot's collection of AI tools, helped them write and optimize their content in just a fraction of the time. The results? 30 % more page views and visitors now spend 27 % more time on their site. If you're ready for impossible growth like this, visit HubSpot.com.

3:11Leanne:Welcome back. Let's join the interview where Al is asking Dustin how to build a professional system that will facilitate growth without killing the creative spark that made the business great to begin with. Well, that's the reason I wrote the book. And I really think that the strength of your systems is in direct proportion to your capacity. So the more that you create a system, the more that you build people around you that are able to help do things that their God-gifted abilities have in store for them. and you don't spend time doing things that you don't need to do. Well, let's talk about these processes for a second then.

3:59I think a lot of particularly creative people or entrepreneurially minded people would feel that systems and processes are constraining what they're doing. That you're telling them, right, do X, Y, Z and you'll get A, B, C. Bosh, go ahead and do it. How are you reconciling that? It is a mental shift. A lot of leadership, you're dealing with emotions, you're dealing with psychological barriers more than you are literal technical limits. And so as a leader, you have to realize that that a lot of people are operating out of some baseline of fear and you helping them have that confidence to break through that fear, to understand that that they're capable of doing more than they think they can, encouraging them, training.

4:52So a lot of leaders miss the fact that their role is to train people how to do what they're supposed to do to set those expectations and to make sure you don't have the right the wrong person on the bus. And then once you have the right people on the bus, that they're in the right seats. So sometimes, you know, a really talented person becomes a generalist, for example, and you get this person who has high aptitude and they become the catch-all and you start giving them everything. and they're doing marketing, they're your executive assistant, they're doing operations and they get burned out and they quit two years later and you wonder what happened.

5:30Well, that's your fault as a leader to not have an executive strategy, which is the first chapter of the book capacity to create those processes where people want you to have that process. They want you to give them that guidance, that framework so they can excel. Um, so looking at, um, their strengths, looking at their weaknesses, looking at their past experience and past performance, and then setting up a process, setting up a structure where they're optimized, where, where they're thriving. And if you got a team full of people that believe in your mission, their skill sets is aligned with what their job is to do every single day.

6:12And they feel like they're winning, man, that is a formula for success. It sounds to me as a very fly with the seat of my pants kind of guy. Executive strategy sounds boring. I don't want to do that. But I feel like I'm wrong. So school me. Why should I have some kind of strategy? Well, you know, sometimes it could be boring counting all your money, but it might be a good idea to do. And so, you know, after running a global consulting company for 16 years and personally coaching hundreds of CEOs and owners and executives, I found that, you know, you have a couple of different types of entrepreneurs that start companies that lead companies.

7:00A lot of common themes you'll see is somebody that's super passionate about what they're doing, somebody that has high charisma, somebody that has high capacity kind of naturally, innately in them. They're a go-getter, and they're the rainmaker. They're the operations person. They're the marketing person. They're the CEO, and they're the bottle washer all in the same day. And so that leads to burnout. And if you're doing it all, then there will be a point where working harder does not equal more results. And I do think that you can get a lot of results, though, as a one man band and mom and pop shop, you, your family, your your wife, your your sister.

7:45Somebody knows how to do a spreadsheet. You're the CFO. Somebody knows how to do social media. You're the marketing director. Somebody just really likes helping you. You're my executive assistant. And there you go. There's your team. And I think you can get to about$10 million in revenue by sheer willpower, sheer mom and pop shop. And there are a lot of examples out there of these mom and pop shops that get to$10 million off of just discipline, work ethic, passion, and persistence. However, what gets you to$10 million will not get you to$100 million. And if you have aspirations to grow to a$100 million business, it's virtually impossible to not put an executive strategy together to map out a five-year plan on how you're going to get to$100 million.

8:36Because what got you to$10 million won't get you to$100 million. And the same is true for those individuals that are out there listening to the show who might have a$100 million company. You know, I was CEO of a$100 million company, and it was a much different experience than being president of a$10 million company running a$100 million company. And right now, my aspiration is to go from$100 million to a billion. And I'm literally going through a pretty painful process of growth as a leader, putting a new executive strategy together that are doing things I've never done before and surrounding myself with people that I've never been surrounded by who have built a billion dollar business that that know how to get to a billion dollar valuation.

9:21and I'm having a lot of fun in that growth process. But I think it's up to the entrepreneur. It's up to the leader. It's up to the owner, CEO, whatever your title is, to be willing to change and to be willing to go through the process of thinking about what you're going to do before you do it. It's much easier to wing it. It's much more fun to shoot from the hip. Discipline is actually like a naughty word. It's a nasty word for most people. Like who wants discipline? So the question that you want to ask yourself in executive strategy is who? Who is on your team? Who are you? What are your skills as a leader?

10:01Do you have a job description for yourself within the company? And am I doing the things that I should be doing or am I doing a bunch of stuff I shouldn't be doing? And then making sure that people on your team are in alignment with they are doing the things that they should be doing. Then what's missing? What are the gaps? And what are the people that you need to go out to the market, find them, hire them, empower them. And ultimately, over time, this creates departments. So you'll have, you know, an executive suite. You'll have a business development department. You'll have a marketing department.

10:36You'll have operations. And most mom and pop shops, they don't think that way. And the way that you feel good is you say that's just not us. Culturally, that's not us. So there's a lot of things that can creep in. But the example in the book is Chick-fil-A. I think Chick-fil-A is one of the coolest companies ever. They have an amazing executive strategy. They have an amazing corporate culture. I think any entrepreneur would say, if I had a company like Chick-fil-A, I'd be OK with that. Even though they say, you know, I don't want to be corporate. I don't want to have all these things that these big corporations have.

11:13I look at companies like Chick-fil-A and think, that'd be pretty cool to have a billion dollar company like Chick-fil-A. But without ruining too many secrets that are in the book, would you be able to talk us through what specifically you like about how Chick-fil-A have set their organization up? Well, in the book, I tell the story of meeting Dan Cathy and getting to go to breakfast with them and interview them. And it was incredible. So it was a rainy day. I went in to Chick-fil-A. The guard met me in the rain and said, you must be Dustin Hillis. And I was like, well, yes, I am. And he said, well, Mr.

11:50Cathy, so excited to meet you. Yeah, go on and park and go through this door. And can I get a high five? And I was like, sure. And so he gives me this high five and I'm driving through the rain thinking that's the most pleasant experience of a guard at the front gate that I've ever had. I pull in a lady at the front desk, runs around the counter, opens the door. Good to meet you. You must be Dustin. Mr. Kathy is so excited to meet you. And I'm like, I've never had somebody run around the front desk and open the door for me like that. Then it went on and on. And I won't tell the whole story that's in the book, but basically the gist of it is Dan said, you know, it really comes down to our interview processes.

12:32It really comes down to making sure we hire the right people. And we have certain things that we do. And in the book, I give specific examples of he did it to me when I met him. And he did two of their interview processes right there in person. and he said, we take the traditional questions that people ask for interviews and threw that book out the window and we look for character traits that are displayed during your interview. We see if you have the character to work at Chick-fil-A and I'll never forget that. And I started adopting some very unique and different interview things. Dave Ramsey is also a mentor of mine.

13:18And I've known him for many years and do quarterly mentor calls with him. And he has a similar culture and process that Dan Cathy and Chick-fil-A have when he interviews people. He'll take them and their spouse out to eat. And he actually interviews the spouse. And that was the first time I ever heard of that. So I think learning from people like people that have cultures and very large companies like the Ramsey organization, you know, getting to meet and break bread with people like Dan Cathy and learning from Chick-fil-A. You know, if you want to be like an avatar of a company, I think you actually have to physically go there as a leader.

14:00I recently drove to or I flew and then rented a car and then drove to the Apple headquarters, the Google headquarters and literally walked around as an actual just visitor. And I just wanted to, like, see how do I feel about this? I didn't really like it, to put it bluntly. It was very not welcome. It was the opposite of Chick-fil-A. And as a tech leader, and we're buying it, we're opening a new office this week here in Nashville, Tennessee. And it's going to be called the Tennessee AI Center of Excellence. And I don't think I'm going to go down the road of the Google Experience Center. And I just it was too cold.

14:41It was too stale. It wasn't personal. It was kind of the opposite of Chick-fil-A when I walked into the Google Experience Center. It was cool. It was it was clean. It was nice. It just didn't feel personal. And so as we're designing it, we're actually I have meetings like this week on designing our experience center. I'm going to lean more towards the Dave Ramsey Chick-fil-A experience versus the Google Experience Center. So I think you have to know what you want and you have to look for other examples that are out there that you can pull snippets from. You don't want to carbon copy anything. You want your own identity.

15:18but I think there's elements of it where you can set a culture that you want and maintain those values that are important to you as a leader to build that company culture. Do you think that it is a different culture for someone like Chick-fil-A and catering as opposed to someone who's got a high, highly driven sales culture? Is it a different, totally different kind of fish? So I spent 20 years in a very high driven direct sales environment. And, you know, it's it's it's you have to be intentional that there are good elements to that high accountability culture, especially when you're young. It's kind of like joining the military when you're young.

16:02You need that discipline. You need to be told what to do. You need that formation. But then at a certain point, you know, you kind of have the basics down and you need to empower people. You need to equip people and you need to create a culture. I think Chick-fil-A's is the most caring company in the world was the mission that they they put together. So I think your mission is the most important thing. And, you know, the the the mission statement should drive all the decisions. So the vision is where the company is going. The mission is who you are and what you do. And then the core values are how you make those decisions.

16:48And so distilling your core values and not just having them be, you know, arbitrary and something that you just put on the wall and you never talk about, but they're real that you talk about them every day. When you're interviewing people, you actually look through your core values and go, does this person align to not only our vision and our mission, but do they actually live the core values we have? Because if there's misalignment with your core values, it's not going to work with that team member, no matter how talented they are. So a lot of times people get stuck with somebody's resume and they talk about how smart somebody is or how they went to a certain school.

17:25They have all these things on their resume and it's like, yeah, yeah, yeah, that's great. They're smart. And yeah, they did some interesting things. But do they match our culture? Do they match our core values? Do they do they believe in the same things we believe in? Because if you surround yourself with people that believe in what you believe in, man, that's powerful. That becomes fun. That becomes, you don't even feel like you're at work. You just feel like you're accomplishing something big together as a group of people who believe in the same things. And that starts with the leader having clarity about their mission, about their vision, about their core values.

18:02And that is all part of executive strategy.

18:04Leanne:We'll be back with more from Dustin after this very short break. Billion Dollar Moves, hosted by Sarah Chen Spellings, is brought to you by the HubSpot Podcast Network, the audio destination of business professionals. Join venture capitalist and strategist Sarah Chen Spellings as she asks the hard questions and learns through the triumphs, failures and hard lessons of the creme de la creme so you too can make billion-dollar moves in venture, in business and in life. Maybe start with episode 124, where you're going to hear how industry giants from Canva to YouTube define leadership. Listen to Billion Dollar Moves wherever you get your podcasts.

18:43Leanne:Welcome back. Let's rejoin the interview with Al and Dustin. So as someone who has led a$10 million company and then currently or has led a$100 million company and then in a couple of years time will have probably even sooner will have led a billion dollar company. What is it actually like the differences between running a smaller company, a medium size and potentially a bigger? Yeah, this will be fun. So starting a company from scratch is you have to have a bit of a of a screw loose in your head to be willing to do it. And so it's incredibly hard. The amount of times I mean, even recently having family members call me saying, you know, statistically, the odds of your success are like one out of 5000 or whatever.

19:30I'm like, thank you for sharing the stats with me of how unlikely it is that we're going to be successful. And so you just have to be willing to go through the gauntlet to start something from scratch where it's a blank piece of paper and you are literally like on a whiteboard. you are writing down your ideas for here's the concept, here's the name of the company, here's what the product's going to be, here's the pricing, how am I going to get the money, here's some ideas of how I'm going to get the money to pay for all this. I mean, if you're at that level of entrepreneurship, I have a 14-year-old daughter and I've watched my daughter be born.

20:13So I cannot say that I'm a woman who has gone through childbirth, but watching my wife give childbirth and the agonizing experience of the whole thing. That's the only thing I could say. Maybe it feels like that on a daily basis where it's like having a baby daily and not just the pain of the childbirth. It's more the taking care of the baby, like in that first couple of weeks where they're so dependent on you that you can't do anything else. I remember taking several weeks off of work and just being like, you have to look at that baby 24 hours a day to make sure it doesn't fall, to make sure its head doesn't move to the side.

20:59Like you're literally holding its head. You're holding the baby. It consumes you 24 hours a day. You don't sleep. That's how it feels starting a business from scratch. So then you evolve to, say, a million-dollar business. and there is a point where the first business I started, I remember somebody telling me, hey, if you can get to the point where you do a million dollars a year in revenue, you're above 90 % of the companies that are out there. You know, when you're driving down the road, most businesses never get to a million dollars in revenue. And then he said, if you did it in your first year, you're light years ahead of where most people, you know, it takes years and years and years for most businesses to get to a million.

21:42So we set the goal that helped drive the goal to saying, all right, we're going to do a million in our first year. And we did. And I remember like breathing after looking at that financial review going, we actually have money. Wow. Like we don't have to just bootstrap and eat ramen noodles. Like we could actually buy the team dinner. you know, dinner. Now we, we might need to go to Shoney's and, and everybody needs to get, you know, the, the fixed menu at Shoney's still. Um, but at least it's not, you know, um, straight commission, um, uh, everybody's paying on their own and we're just talking about the future and, and everybody's just, you know, their, their, their payment is the belief we're going to figure this out at a million dollars.

22:29You actually start having resources. So I imagine that that feels like, you know, you have a six-year-old kid who I'll never forget my daughter. We travel a lot. She actually went to 30 different countries before she was 10 years old. And I used to be the pack mule. So I'd have my wife's bag, my bag and my daughter's bag. And we'd be going through Europe, going from Estonia to Latvia to Lithuania. And this is this crazy Eastern European track and going on these trains and I just felt like a pack mule. And I remember the day that my daughter could carry her own bag. And it was just like, for some reason, it was a huge day.

23:13The only day that was bigger was the day my daughter could wipe her own butt. So that might be a better example is when your kid can wipe their own butt, that's probably how it feels having a million dollar business where your team actually can do things outside of you. That's probably where the capacity you start thinking, hey, I could have a marketing person. Hey, I could have a operations person. Man, I might even be able to have a finance person. And you start to have these loose, they might be part time, they might have a couple of different roles. You know, your co-founder might all of a sudden go, hey, why don't you handle business development?

23:51And I'll do operations and finance. And it's like, oh, all of a sudden, we have two departments, you know. So at a million, that's about the time that your kid can start wiping its own butt. Then at 10 million, that's usually the next stopping point that you look back and you go, man, I have a teenager. And I'm about to go into that. And as an actual father, so my daughter's 14. We already have the Jeep picked out that she wants next year when she turns 15 to start driving. And I've already given her some driving lessons and we go to the church parking lot and she drives in circles. I teach her how to park.

24:34And very soon she's going to be driving and her mom's not going to have to take her to basketball practice. She's just going to take herself to basketball practice. So at 10 million, I think that's really where you have a teenager and they start driving themselves to school. They start driving themselves to basketball practice. Now, you need to check in because they're not an adult yet. So you don't want to just not talk to your 16-year-old for a week and just assume they're not partying on the weekend. So at a$10 million leader level, you're still managing the business very hands-on. You still know everything that's going on.

25:14You probably still know every customer's name. You probably still know every team member's name. you probably um are in every meeting you're probably like still feeling i think that that's kind of the breaking point for a lot of leaders is like they still think they have to do everything so they're they're hiring people but they're not really building the system to let that grow and scale um then then once you get past 10 million uh and you get to the 20 million to the 50 million to the hundred million, that really is finding the A plus people that know how to run their division of your company as if it's a business in and of itself.

25:55And so that's like an adult. So I haven't, I don't have an adult kid. I have friends that have adult kids and they said one of the coolest points in time, maybe in the mid twenties is they get a job and they first, and that's when they start appreciating you is, is once you have a team that understands the sacrifice you made as the leader, where you were personally paying payroll and you personally were losing five years of your life. You didn't go on a vacation. But then they look at you as somebody running a$20 million company who can take nice vacations now. And once you have a team that's mature enough to realize you deserve it and that that doesn't affect them and you don't feel this internal pressure from your team like, oh, I need to be here all the time because I'm setting the example.

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26:41but you have other leaders that are in the company setting the example. And they're like, look, boss, you need to like chill a little bit. Like you need to like take care of yourself. You've already put in the, the, the 10 years that, that got us to this 20 million,$50 million business. Let me, let me take this and run with it. And, and like, I'm here, let's set our goals together. Let's set our budget together. But I got this. And once you start having like, like chiefs, Like once you have other chiefs, you have a CMO, you have a COO, you have a CFO. And it's not just a title because a lot of times people get the title and they don't have the skills.

27:20I'm talking a real CFO that really knows how to do a five-year financial forecast. They actually know how to run a financial review. They actually know how to hire other financial controllers and treasury people that they're managing to build the finance side of your business. They know how to go negotiate with bankers without you there to set up your terms. like a real CFO. That's when all of a sudden you have an adult kid and it's like, man, my son or my daughter just paid for dinner. How cool is that? You know, I just went to a steak dinner and I didn't pay for it. That is, I mean, and I didn't plan it.

28:00My daughter just came home from work from New York and said, hey, dad, can I take you out to dinner? And you're like, sure. and she booked the reservation, she paid for it, and she ordered a nice bottle of wine that I didn't even order. And she knew what wine was going to be good. Like, that's the experience of really having an executive team. And I think that when you're at that$100 million level, that's what I experienced was there's just people that you don't need to tell them what to do. You just check in with them once a month. And the question you ask them is, hey are you good is there anything I can do to help and you just look at the the budget numbers you just check in really quick the numbers look good they're like no I'm good or they're saying hey yeah there is this thing I need your help with I'm having this one problem and you kind of become you become kind of like the grandparent so I'm imagining that's what it feels like to be a billion dollar leader and this is the journey I'm on now is as I'm imagining the infrastructure is so well established and the companies are so well run that it's like that old grandpa that you that you call and you do need in your life to to come in when there's a really big problem and you're going through a divorce and it's messy and you've never gone through a divorce before but you just feel like grandpa knows what to do during the divorce and so you call grandpa and you're like hey man can I talk to you and he steps in and he gives you that sage wisdom that makes all the difference in your life.

29:25But, you know, he doesn't need to be there like he was when you were needing your butt wiped. Tell me, just practically speaking, and I'm sure the answer in your book, if someone is building, if someone's getting up towards the million to 10 million, at what point do they need to start building out these teams that you talked about that? There are some big businesses out there that have very low margins. I think of restaurants, for example, you know, if you're in a low margin business, you can have a million dollars in revenue and barely be making ends meet because there's so much cost in running that restaurant.

30:03So you might not be able to afford a CFO, but you have a million dollar restaurant and you're still like getting a part time bookkeeper that's helping you with QuickBooks to do your finances and do your taxes because you don't have the profit to pay that CFO. So on the other hand, you could have a tech company that has a 50 % margin business and you have$500 ,000 at the end of the day to pay other people with. And that could afford you a couple of executives to then grow from a million to 10 million. What I find most people, the biggest mistake high margin CEOs do is they get to a million and all of a sudden there's 500 ,000 left at the end of the year.

30:51And guess what they do with it? They buy a Ferrari. That's exactly right. And it's perfectly within their realm to keep that money. They don't plow it back into the business. And boom, there you go. You've got a million dollar business with a guy driving a Ferrari for 10 years and the business doesn't go anywhere. versus you think of it like a true scaling. Again, this is executive strategy. What are you going to do with that$500 ,000? Put yourself on a CEO pay plan. Don't put yourself on an entrepreneur pay plan where you scrape all the money at the end of the year. Say, hey, for a million dollar business, I should probably be paying myself about$200 ,000, maybe$250 ,000.

31:29So pay yourself$250 ,000, have a nice life, be disciplined, take the rest of that money and go hire a chief, an operations. You don't have to hire a chief. Hire a director of operations. Hire an operations manager. Hire a controller and give them a vision saying, hey, if you do well over the next year or two, I'll promote you to CFO. And if you don't do well, I'm going to hire a CFO at some point, and it could be you or it could not be you. So you create this internal system of hiring people and creating a vision. If they do well, they could grow into the C-suite. So at a million, that's kind of how I would look at it.

32:12I think a lot of people who have built a business to a million to 10 million, they're like, I don't know what I'm doing. It's that dog meme where they're on the computer going, I have no idea what I'm doing. So school us more. Imagine you're talking to a group of 10 people all in that region of 1 to 10 million. What other gold can you teach us? What other things should we be doing? I mean, I can just tell you what not to do from personal mistakes that I've made a dozen times through going through that journey of one to 10 million successfully a few times. So there is some traps that you can fall into.

32:49One of them is actually giving up power too quickly. So power dynamics is a whole thing that I was really unaware of and was taught the hard way. I actually had a president of one of my companies sit me down and go, look, Dustin, I love that you empower people. And I love that you have given me my job as the president. And you really give me like a lot of latitude to run my business within the portfolio. She said, and this feedback is probably going to hurt me, but I feel you need to hear it. And I said, OK. And she said, you give people power too fast. And that stuck with me. I'll never forget her telling me that.

33:43And I thought back of how quick I would promote people and start like a new company and then bring in someone who was completely unqualified. But I just I just believed in them. I believe they had what it took. I believe they had the natural skill. But then I gave them the authority that they weren't used to too fast and they couldn't handle it. And to me, I don't I still don't know if I understand it. But it is true that I could give you like five examples where I have personally created a division or started a company and then brought somebody in and quickly gave them control of the budget, control of comp, control of the model.

34:33And they turn it sideways. They get selfish. They find a way to pay themselves more money. The margin goes down. So the business suffers, but they gain. and it's power dynamics, right? It's like not everybody can handle power. And so I would say between 1 million and 10 million, you're learning that. And the first time you get burned, most entrepreneurs throw their hands up and they say, that didn't work. I'm never doing that again. And so it's inevitable. I don't know one single entrepreneur that hasn't had a business partner try to screw them. I don't know one. Like I can't, and I know hundreds, like I know hundreds and hundreds of people that have started their own business, successfully run their own business.

35:22Every single one of them have had a business partner attempt to screw them or legitimately screw them. And I'm talking out of millions of dollars. And so just knowing that that's part of it, I think can help you sleep at night and to not take it personal. That's the hardest part, actually. The hardest part is to you get so intimately involved, especially in that one to ten million dollar range. Everything feels like a family. You call each other family. You you you eat dinner together. You know their kids. They know your kids. And it feels like this big, happy family. And then when money starts getting involved, you know, I've seen it happen.

36:05I've seen family members die. And then the people that were the kids, literally, they don't talk to each other anymore. And I have one specific example. It was over$30 ,000. So somebody died. There was a house that had$30 ,000 of equity and a brother and a sister still to today, they don't talk to each other over the$30 ,000, the way the house was settled in the estate. and there is this insane thing that happens when money and power and I think that struggle is very similar to most businesses at the 1 million to 10 million dollar range people are like jockeying people are positioning it's a bunch of people that aren't that seasoned they haven't ever like run a hundred million dollar business so they don't they don't know who's who in the zoo and they don't know what what is normal and what it feels like to just be comfortable within a role and to be comfortable within a responsibility and to treat a department as its own company.

37:05So they try to take over the whole company. And then the person in their way is the CEO and the leader, and they're the ones closest to you. So they see all your flaws. So it's easy for them to point out what's wrong with you. And that's real painful when you have a team member sit down and tell you all the things that's wrong with you. And you just have to rise above that and realize you don't have to say it to their face, but in the back of your head, you have to be like, you wouldn't be here if it wasn't for me, but I'm not going to say that to you. I'm just going to listen to you and let you feel heard.

37:35And I need to determine if you're the right person moving forward or not, or I might have to, I might have to replace you. Like there are certain places where somebody can mentally go into this cancer realm. And, and, um, if you're going to grow from 10 million to 100 million, there is a pruning process that typically is involved. And what's interesting, like, have you ever seen those little bonsai trees where people grow the bonsai tree? Well, they say that the pruning is what causes the growth in your bonsai tree. A business is exactly the same way. So if you're in that range of 1 million to 10 million, you are the pruner and pruning typically creates the growth.

38:23Now, if you interviewed a hundred of your friends, let's say we had a hundred people sitting in a circle that are in this category and they're wanting to learn like, okay, what's the difference here? And I said, what's the number one thing that you hate about being a business owner? I bet 90 % of them would say firing people. It's my least favorite part of the job. Like, I genuinely hate it. Like, it's the thing that causes me not to want to do it again and to not, like, pick up my bag and pick up the bat and go back to the plate is inevitably knowing, hey, if I hire 10 more people, not all of them are going to make it.

38:59And I personally, when I hire somebody, man, I believe in them. When I hire somebody, like I saw the potential in them. I thought they had greatness in them. I thought they were going to do what they said they were going to do. I thought they were going to achieve all the goals. Like that's why you hired the person. And to then give them time and then to actually see the performance or the lack thereof and to have some moment of time in the future where you have to make a decision and go. The expectations didn't equal the actions, which didn't equal the results. Therefore, in order for the business to grow, you got to go.

39:41And that is the hardest part of business. That's what most people aren't willing to do. So they keep the dead weight around. They keep the negative people around. They keep the dead limbs on the tree. And the dead limbs stymie the growth of the healthy limbs. And a team will always grow to the, they will always grow to the limit of the lowest common denominator. So you as the leader of whatever you allow to be acceptable within your culture, everybody else will look at that as the bar and say, well, at least I'm not as bad as this asshole. and and so as long as you have the asshole who talks to you disrespects you talk shit about you behind your back and and and everybody else looks at that person and goes well the leader hasn't fired this person and yeah i could do better yeah i could work harder yeah i'm subordinate just a little bit but i'm way better than this guy who's completely off the rocker and a lot of times it's like a leader's buddy and they have some kind of personal connection and, and they're just not willing to fire their, their best friend.

40:50And, uh, man, that's hard. It's painful. I hate it. I never want to do it again. Um, and I probably am going to have to again, and I still hate it every single time I hate it. Um, if it's the right thing for the business, if you can sleep at night knowing. And here's the thing, when you do it the right way, they know it too. Like if you give somebody the proper expectations, if you give somebody proper training, if you give them the proper tools and then they just don't show up, they don't go to work, they don't follow through and do what they say they're going to do, and you give them enough time and it just doesn't happen, then it's on them.

41:34That's not on you as the leader. You're actually doing them a favor by letting them go. Now, is it emotional? Hell yeah, it's emotional. It's emotional every single time. And very rarely does somebody take it well initially. But once they get past that initial separation, they look back and they go, they find something that actually they are willing to work harder at. They find something that they actually thrive in. They find something that actually is more fulfilling to them. And they look back and they say, thank you. Thank you for letting me go because otherwise I wouldn't be doing this thing that actually I am more excited about.

42:14And really, I was sticking around because of you. I'm loyal to you and I love you. So that's why I never quit is because I just, I'm your friend. And so it's actually doing them a favor by letting under performers go. Your book capacity, who should be reading it and who shouldn't? Yeah. I would say anybody who is a leader and wants to improve their leadership abilities should read the book Capacity, Building a Business Bigger Than You. So a business could be your household and you're building the capacity of what you can do. You could be a church leader building the capacity of a church. You could be an organizational leader within your community and you want to build the organization that you're leading within your community.

42:59And then obviously entrepreneurs who are running actual, you know, for-profit businesses of any size, of any scale, this is just about taking it to the next level. So if you're already running a, you know, a hundred million dollar company all the way to the person who has an idea where they're starting a company and it's still on a piece of paper, this book is for you. It's out on Amazon. You can go to DustinHillis.com and order the book there. You could go to Barnes & Noble, just walk in and it's sitting there on the shelf. It's available on audio as well, which I'm very excited. The actor actually sounds like me and it's a Southern gentleman that read the book and I'm re-listening to it and I'm like, man, the audio book's really cool too.

43:47Leanne:So there is a real refreshing bluntness in the way Dustin talks about the gauntlet of leadership. It is easy to get obsessed with revenue numbers, but the human stuff, the power struggles and the emotional way of letting people go is usually what decides if a business actually makes it. Yeah. And for those of you listening who are currently building towards that 10 million mark, Dustin's message isn't that you're doing it wrong. It's that you're likely reaching the limit of what sheer determination can achieve. To help you prepare for that next level, here are three big takeaways from today. one check your job description high capacity founders often end up as the catch-all for everything from marketing to HR and this is a fast track to burnout so you need a strategy that defines your specific role so you can actually empower your team to own theirs number two is the pruning paradox it sounds tough but a team only grows as fast as its weakest link If you keep people who don't perform or don't fit your values, you are basically stunting the growth of your best people.

44:56Leanne:And three, hire for reason, not just resume. A talented person who doesn't believe in your mission will never help you build an unstoppable team. If you don't have a structured, scientifically valid way of measuring competency and character, you're holding yourself, your people and your business back. and I'll be honest I'm a kind of a fly by the seat of my pants sort of person and I always thought executive strategy sounded a little bit boring but my big takeaway today is that these systems aren't there to stifle us they're there to give us our lives back it's about moving from being the person who does everything to becoming a leader who empowers others to use their own unique gifts.

45:36Leanne:Dustin's book Capacity Building Your Business Bigger Than You is a really deep dive into how to actually build these systems. So if you have enjoyed today's episode, you should definitely check it out. It is available on Amazon, all major bookstores and on his website, dustinhillis.com. The book is out as of today. I think it came out yesterday, actually. So definitely go and check that out. This is Truth, Lies and Work. We'll see you next week.

From the publisher

Most founders pride themselves on being “high-capacity”.
The person who can sell, operate, strategise, and firefight all at once.

But there’s a point where that strength quietly becomes the problem.

In this episode, Al and Leanne are joined by Dustin Hillis, a serial entrepreneur and executive coach who has led businesses from early-stage chaos through to $100m-plus scale, and is now building again at a much bigger level.

Dustin’s core message is simple, but uncomfortable:what gets you to your first milestone will not get you to the next one.

Unless leaders change how they work, think, and let go, they become the bottleneck that holds everything back.

This is a long-form, honest conversation about growth, power, systems, and the emotional reality of leadership that rarely gets talked about.

🔍 What you’ll learn in this episode

Why working harder eventually stops working, and what replaces it

How leaders unintentionally burn out their best people by turning them into “catch-alls”

Why systems don’t kill creativity, but reduce fear and create capacity

What actually changes at £1m, £10m, £100m and beyond

The power dynamics that quietly derail teams as money and authority increase

Why “pruning” underperformance is painful but essential for healthy cultures

How to stop being the centre of everything without losing control

Dustin acts as a guide through the messy middle of growth, grounded in lived experience rather than theory.

📘 About the book

Dustin is the author of Capacity: Building Your Business Bigger Than You, a practical exploration of how leaders build organisations that no longer depend on them to function.

🔗 Connect with Dustin

LinkedIn: https://www.linkedin.com/in/dustinhillis/

Website: https://dustinhillis.com

💬 Connect with the hosts

Al Elliotthttps://www.linkedin.com/in/alelliott/

Leanne Elliotthttps://www.linkedin.com/in/leanneelliott/

🎧 Connect with Truth, Lies & Work

Website: https://truthliesandwork.com

Email: hello@truthliesandwork.com

LinkedIn: https://www.linkedin.com/company/truth-lies-and-work

Instagram: https://www.instagram.com/truthlieswork

Have a workplace dilemma or question? Get in touch — it may feature in a future episode.

🧠 Mental health support

If this episode brings up difficult feelings, support is available:

UK: Samaritans — call 116 123 or visit https://www.samaritans.org

US: Suicide & Crisis Lifeline — call or text 988 or visit https://988lifeline.org

Australia: Lifeline — call 13 11 14 or visit https://www.lifeline.org.au

Elsewhere: https://findahelpline.com

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