Episode 267 · 15 January 2026 · 46:24
How to build a business bigger than you, with Dustin Hillis
Featuring Dustin Hillis
How to build a business bigger than you, with Dustin Hillis
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The high-capacity founder trap
Introducing Dustin Hillis and his book Capacity
Why your systems are only as strong as your leadership
interview#systems#leadership#strength
The 'catch-all' problem — how leaders burn out their best people
Why 'boring' executive strategy beats flying by the seat of your pants
interview#strategy#executive#boring#planning
Lessons from Dan Cathy and Chick-fil-A
The Google Experience Center — a culture in contrast
interview#google#culture#contrast#experience
What actually changes at £1m, £10m, £100m and beyond
interview#growth#revenue#milestones#scaling
Practical advice for leaders stuck in the messy middle
What *not* to do — personal mistakes from a dozen companies
interview#mistakes#personal#lessons#companies
Show notes
How to Build a Business Bigger Than You — with Dustin Hillis
Guest: Dustin Hillis — serial entrepreneur, executive coach, author of Capacity: Building Your Business Bigger Than You, and leader who has taken businesses from early-stage chaos to $100m-plus scale.
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.
Dustin joins Al and Leanne to share a simple, uncomfortable truth: 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 — from the "pack mule" days of bootstrapping to the power dynamics that quietly derail teams as money and authority increase.
Top 3 Takeaways
- Check your job description. As your business grows, your role must change — the skills that got you to £1m won't get you to £10m. Leaders who refuse to evolve become the bottleneck.
- Stop turning your best people into catch-alls. When you hand your top performer everything — marketing, executive assistance, operations — you burn them out and build no systems. Train people to do what you do, then let them.
- Pruning is painful but essential. Letting underperformers go is often doing them a favour. If you can sleep at night knowing it's the right thing for the business, it usually is.
More From Dustin Hillis
- Book, Capacity: Building Your Business Bigger Than You: dustinhillis.com
- LinkedIn: linkedin.com/in/dustinhillis
- Website: dustinhillis.com
Connect With Us
Get in touch, book a call, or find Al and Leanne on LinkedIn — all in one place: truthliesandwork.com/connect
Mental health support: findahelpline.com — UK: Samaritans 116 123 · Mind 0300 123 3393 — US: 988 — Australia: Lifeline 13 11 14
Truth, Lies & Work is part of the HubSpot Podcast Network.
Full transcript
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Al ElliottMost 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.
Dustin HillisA 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, uh, they're the CEO and they're the bottle washer all in the same day. 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.
Leanne ElliottOur guest today is Dustin Hillis. Dustin has led a $100 million company and is currently building toward a billion 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.
Al ElliottDustin'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. And 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 5 essential pillars of growth. You're gonna 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.
Leanne ElliottThis is Truth, Lies and Work, the award-winning podcast where behavioural 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 Chartered Occupational Psychologist.
Al ElliottMy name is Al. I'm a business owner.
Leanne ElliottAnd together we help you simplify the science of work and create amazing workplace cultures.
Al ElliottWe'll be back with our conversation with Dustin Hillis after this very quick word from our sponsors. The dirty little secret is that most businesses think they know their customers. They have the data, the records, the history, but it's scattered across 3 teams and 4 systems. And in our case, it's about 216,000 spreadsheets, which means nobody can actually use it.
Leanne ElliottWhat you should be doing is using HubSpot, because why? HubSpot connects it all. Every interaction, every support ticket, every conversation into one platform every team can work from. So when sales talks to a customer, marketing already knows the full story. And when you know more, you grow more.
Al ElliottNice. Check out hubspot.com, the agentic customer platform for growing businesses.
Leanne ElliottWelcome 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 is great to begin with.
Dustin HillisWell, 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, and you don't spend time doing things that you don't need to do.
Al ElliottWell, let's talk about these processes for a second then. I 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?
Dustin HillisIt is a mental shift. Um, 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 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 they're capable of doing more than they think they can.
Al ElliottYeah.
Dustin HillisEncouraging them, training. 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 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, a really talented person becomes a generalist, for example, and you get this person who has high aptitude, and they become the catch-all.
Leanne ElliottYeah.
Dustin HillisAnd 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 2 years later, and you wonder what happened. Well, 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. So, looking at 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 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, And they feel like they're winning, man, that is a formula for success.
Al ElliottIt sounds to me as a very fly-by-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?
Dustin HillisWell, 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 Uh, 16 years and, um, personally coaching hundreds of CEOs and owners and executives, I, uh, I found that, you know, you have a couple of different types of entrepreneurs that start companies, that lead companies. Uh, 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.
Leanne ElliottYeah.
Dustin HillisAnd they're the rainmaker, they're the operations person, they're the marketing person, uh, 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, a mom-and-pop shop, you, your family, your, your wife, your, your sister, uh, somebody knows how to do a spreadsheet, you're the CFO. Somebody knows how to do social media, you're the marketing director. Uh, somebody just really likes helping you. Um, you're my executive assistant. And there you go. There's your team. And, and I think you can get to about $10 million in revenue by sheer willpower, sheer mom-and-pop shop. And, 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 that, 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 5-year plan on how you're gonna get to $100 million. 'Cause what got you to $10 million won't get you to $100 million. And the same is true for those, uh, individuals that are out there listening to the show who might have a $100 million company. 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.
Al ElliottYeah.
Dustin HillisWho have built a billion-dollar business, that know how to get to a billion-dollar valuation, and 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, it's much more fun to shoot from the hip. Um, discipline's actually like a, a naughty word. It's a nasty word for most people. Like, who wants discipline? So the question that you wanna ask yourself in executive strategy is, who, who is on your team? Who are you? What are your skills as a leader? Do 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, and then making sure the 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, 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. You'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. And I think any entrepreneur would say, if I had a company like Chick-fil-A, I'd be okay with that. Even though they say, you know, I don't wanna be corporate, I don't want to have all these things that these big corporations have. I, I look at companies like Chick-fil-A and think that'd be pretty cool to have a billion-dollar company like Chick-fil-A.
Al ElliottWell, 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, set their organization up?
Dustin HillisWell, in the book I tell the story of meeting Dan Cathy and getting to go to breakfast with him and interview him, and it was incredible. So it was a rainy day. I went into Chick-fil-A. The guard met me in the rain and said, you must be Dustin Hillis. And I was like, why, yes I am. And he said, well, Mr. Cathy's 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. Uh, good to meet you. You must be Dustin. Uh, Mr. Cathy's 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. Um, and then it went on and on and, uh, I won't tell the whole story that's in the book, but basically the gist of it is Dan said, it really comes down to our interview processes. It 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, well, he did it to me when I met him. And he did 2 of their interview processes right there in person. And, um, and nobody— and he said, we take the traditional questions that people ask for interviews and, and threw that book out the window. And, and we look for character, uh, 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. Uh, and, and I started adopting some very unique and different interview, um, things. Um, Dave Ramsey's also a mentor of mine and, uh, I've known him for many years and, and do quarterly mentor calls with him, and he has a similar, um, culture and, uh, 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, uh, 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, to, to meet and, and break bread with people like Dan Cathy and learning from Chick-fil-A. If you want to be like an avatar of a company, I think you actually have to physically go there as a leader. I recently drove to, or not, 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? Um, 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. Um, 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, uh, I just, it was too cold. It was too stale. It wasn't personal.
Leanne ElliottYeah.
Dustin HillisUm, it was kind of the opposite of Chick-fil-A when I walked into the Google Experience Center. Um, it, it was cool. It was, it was clean. It was nice. It just didn't feel personal. And so, uh, as we're designing it, we're actually, I have meetings like this week on designing our experience center. Um, I'm gonna 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. But 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.
Al ElliottDo you think that it is a different culture for someone like Chick-fil-A in catering as opposed to someone who's got a highly driven sales culture? Is it a different, totally different—
Dustin HillisVery much so. I spent 20 years in a very high-driven direct sales environment. And, um, you know, it's, it's, it's, uh, you have to be intentional. There are good elements to that high accountability, um, culture, um, especially when you're young. It's kind of like joining the military when you're young. You need that discipline. You need to be told what to do. Um, you need that formation. Um, but then at a certain point, uh, you know, you kind of have the basics down.
Al ElliottYeah.
Dustin HillisAnd 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 put together. So I think your mission is the most important thing. And the mission statement should drive all the decisions.
Al ElliottYeah.
Dustin HillisSo the vision is where the company's going. The mission is who you are and what you do. And then the core values are how you make those decisions. And so distilling your core values and not just having them be 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. They 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—
Leanne ElliottYeah.
Dustin HillisDo 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. And that is all part of executive strategy.
Leanne ElliottYeah. We'll be back with more from Dustin after this very short break. Did you know that the UK's number one management podcast— that's us, by the way— and the UK's number one marketing podcast are both on the same podcast network?
Al ElliottWe actually have a lot in common. We both use behavioural science to help people do better at work.
Leanne ElliottAnd we both had to wrangle Rory Sutherland on an episode.
Al ElliottAnd 2 out of 3 of us are devilishly good looking.
Dustin HillisAnd you're not gonna see Say which.
Al ElliottPhil, host of Nudge, UK's number one marketing podcast. It's brought to you— we need to do this in threes—
Leanne Elliottthe HubSpot Podcast Network, the audio destination for business professionals.
Dustin HillisSeamless, seamless.
Al ElliottTell us about your latest episode, Phil. Uh, we've just done an episode on fake fandom and how New York indie bands are paying agencies to create fake TikTok videos about how much they like their work. And we talk about the behavioral science behind fandom and how that encourages people to enjoy the It is.
Leanne ElliottIt's such, it's such a good show. Of course, you'll hear all the stuff you want to hear about how to grow your business by using behavioural science in your marketing. But there's also just some really interesting episodes that'll be right up your street. Personally, I enjoyed Can Balsamic Vinegar Make Beer Taste Better?
Al ElliottIt can.
Leanne ElliottAnd Are We All Just Status-Seeking Monkeys?
Dustin HillisI am.
Al ElliottGo and listen to Nudge wherever you get your podcasts.
Leanne ElliottBut come back.
Al ElliottYeah, come back. We'll see you next week. Bye. Definitely come back because Nudge isn't as good as this.
Leanne ElliottSo come back.
Al ElliottI'll cut that out. Keep that in.
Leanne ElliottWelcome back. Let's rejoin the interview with Al and Dustin.
Al ElliottSo 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-sized, and potentially a big one? Yeah, this will be fine.
Dustin HillisSo starting a company from scratch is, you have to have a bit of a screw loose in your head to be willing to do it. And so, um, 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 1 out of 5,000 or whatever. I'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 gonna be. Here's the pricing. Um, how am I gonna get the money? Here's some ideas of how I'm gonna get the money to pay for all this. I mean, if you're at that level of entrepreneurship, I've, I've, uh, I have a 14-year-old daughter and I've watched my daughter be born. So I cannot say that I'm a woman who has gone through childbirth, but watching my wife give childbirth, um, and, and the agonizing, uh, experience of, of the whole thing.
Al ElliottYeah.
Dustin HillisUm, that's the only thing I could, could say. Maybe it feels like that on a daily basis where you're, it's like having a baby daily and, 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. Um, I remember taking several weeks off of work, uh, 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.
Al ElliottYeah.
Dustin HillisYou know, move to the side. Like, like you're literally holding its head. You're holding the baby. You're— it consumes you 24 hours a day. You don't sleep. Um, that's how it feels starting a business from scratch. So then you evolve to say a million-dollar business. And, and there is a, a point where, uh, 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. When you're driving down the road, most businesses never get to $1 million in revenue. And then he said, if you did it in your first year, you're light years ahead of where most people— it takes years and years and years for most businesses to get to $1 million. So we set the goal. That helped drive the goal to saying, all right, we're going to do $1 million in our first year. And we did.
Leanne ElliottWow.
Dustin HillisAnd, and I remember like breathing after looking at that financial review going, we actually have money.
Leanne ElliottWow.
Dustin HillisLike, we don't have to just bootstrap and eat ramen noodles. Like, we could actually buy the team, 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.
Leanne ElliottYeah.
Dustin HillisUm, uh, everybody's paying on their own and, and we're just talking about the future and, and everybody's just, you know, their, their, their payment is the belief we're gonna figure this out. At $1 million, you actually start having resources. So I imagine that that feels like, um, you know, you, you have a, a, a 6-year-old kid who I, I ne— I'll never forget. Um, my daughter, uh, we travel a lot. She actually went to 30 different countries before she was 10 years old.
Leanne ElliottWow.
Dustin HillisAnd, um, 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, I, for some reason it was a huge day. The only day that was bigger was the day my daughter could wipe her own butt. So that might be a better example is when, 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, uh, operations person. Um, 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 and I'll do operations and finance? And it's like, oh, all of a sudden we have 2, 2 departments, you know? So at a, at a million, that's about the time that your kid can start wiping its own butt. Um, then at $10 million, that, that's usually the next stopping point that you look back and you go, man, I have a teenager.
Leanne ElliottYeah.
Dustin HillisUm, and I'm about to go into that. And, uh, as an actual father, so my daughter's 14. Uh, we already, um, have the Jeep picked out that she wants next year when she turns 15 to start driving. And, um, 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. And very soon, um, she's gonna be driving and her mom's not gonna have to take her to basketball practice. She's just gonna take herself to basketball practice. So at, at $10 million, I think that's really where you have a teenager and, um, they start driving themselves to school. They start driving themselves to basketball practice. Um, now you need to check in cuz they're not an adult yet. So, so, uh, you, you don't want to just not talk to your 16-year-old for a week, uh, and just assume they're not partying on the weekend. So at a $10 million, uh, leader level, you're still managing the business very hands-on. You still know everything that's going on. You 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—
Leanne ElliottYeah.
Dustin HillisHiring 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 $100 million, that really is finding the A+ people that know how to run their division of your company as if it's a business in and of itself.
Al ElliottMm-hmm.
Dustin HillisAnd 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-20s, is they get a job and they first— and that's when they start appreciating you, 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, you know, 5 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, 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, but 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, uh, like chiefs, like once you have other chiefs, you have a, a CMO, you have a COO, and, and you have a CFO. And it's not just a title, cuz a lot of times people get the title and they don't have the skills. I'm talking a real CFO that really knows how to do a 5-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. Um, 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? And I just went to a steak dinner and I didn't pay for it. That is amazing. And I didn't plan it. My 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 gonna 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, um, that, that's, that's what I experienced was, was there's just people that you don't need to tell 'em what to do. You just check in with 'em once a month. And, and, and the question you ask 'em is, hey, are you good? Is there anything I can do to help? And, and you just look at the, the budget numbers. You just check in really quick. The numbers look good.
Leanne ElliottYeah.
Dustin HillisThey'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, is 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.
Leanne ElliottYeah.
Dustin HillisTo, 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. Um, but you know, he, he doesn't need to be there like he was when you were needing your butt wiped.
Al ElliottTell me, just practically speaking, and I'm sure the answers are in your book, if someone is building, if someone's getting up towards the million to $10 At what point do they need to start building out these teams that you talked about there?
Dustin HillisThere, there are some big businesses out there that, that have very low margins. I think of, um, restaurants, for example. Um, you know, if you're in a low margin business, you, you could have $1 million in revenue and barely be making ends meet cuz there's so much cost in running that restaurant. So, You might not be able to afford a CFO, but you have a million-dollar restaurant and, and you're still like getting a part-time bookkeeper that's helping you with QuickBooks to, to do your finances and do your taxes because you don't, you don't have the, the profit to pay that CFO. So, um, on the other hand, you could have a tech company that has a 50% margin, uh, business and you have 500, uh, $1,000 at the end of the day to, to pay other people with. And that could afford you a couple of executives to, to then grow from $1 million to $10 million. What I find most people, the biggest mistake high-margin CEOs do is they get to $1 million and, and all of a sudden that there's $500,000 left at the end of the year. And guess what they do with it? They buy a Ferrari. That's exactly right. And it's perfectly within their realm to, 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. Um, versus you think of it like a true scaling. Again, this is executive strategy. What are you gonna 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, uh, uh, for a, a million-dollar business, I should probably be paying myself about $200,000.
Al ElliottYeah.
Dustin HillisMaybe $250,000. So 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, hire a controller and give them a vision saying, hey, if you do well over the next year or 2, I'll promote you to CFO.
Al ElliottYeah.
Dustin HillisAnd if you don't do well, um, I'm gonna hire a CFO at some point and it could be you or it could not be you. So you create this, this, this internal system of hiring people and creating a vision. If they do well, you, they could grow into the C-suite. So at a million, that's kind of how I would look at it.
Al ElliottI think a lot of people who, 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, should we be doing?
Dustin HillisI mean, I can just tell you what not to do from personal mistakes that I've made a dozen times, uh, through going through that journey of, of $1 to, to $10 million, um, successfully a few times. Um, so there, there is some traps that you can fall into. Um, one of them is actually giving up power too quickly. So power dynamics is a whole thing that, that I was really unaware of and, uh, was taught the hard way. Um, I actually had a president of one of my companies sit me down and go, look, Dustin, I, I love that you empower people and I love that you have, have given me You know, my job as the president, and you really give me like a lot of latitude to, to run, you know, my, my business within the portfolio. She said, and this feedback is, is probably gonna hurt me, but I feel you need to hear it. And I said, okay. And, and, and she said, you give people power too fast. And, uh, that stuck with me. I'll never forget her telling me that. And, and 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 believed they had what it took. I believed 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, uh, I, I don't, I still don't know if I understand it. Um, But it is true that I could give you like 5 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, and 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, um, it's power dynamics, right? It's, uh, it's like not everybody can handle power. Um, and so, uh, I would say between $1 million and $10 million, you're learning that. And, and the first time you get burned, uh, 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.
Al ElliottYeah.
Dustin HillisI don't know one. Like, I can't. And I know hundreds. Like, I know hundreds and hundreds of people that, that have started their own business, successfully run their own business. Every single one of them have had a business partner attempt to screw them or legitimately screw 'em. 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.
Al ElliottYeah.
Dustin HillisAnd to not take it personal. Um, that's the hardest part, actually. The hardest part is to, to, you get so intimately involved, especially in that $1 to $10 million 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, um, You know, I, I've seen it happen. Uh, I've seen family members die and then the people that, that were the kids, literally they, they don't talk to each other anymore. And I have one specific example. It was over, um, $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.
Al ElliottYeah.
Dustin HillisAnd there is this insane thing that happens with money and power. And I think that struggle is very similar to most businesses at the $1 million to $10 million 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 $100 million 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.
Al ElliottYeah.
Dustin HillisAnd to treat a department as its own company. So 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. Um, 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, Yeah. 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. And 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, there is a pruning process that typically is involved. And what's interesting, like, if you— have you ever seen those little bonsai trees where, uh, people grow the bonsai tree? Uh, well, well, they say that, uh, the pruning is what causes the growth in your bonsai tree.
Leanne ElliottMm-hmm.
Dustin HillisA business is exactly the same way. So if you're in that range of $1 million to $10 million, you are the pruner. And, and pruning typically creates the growth. Now, if you interviewed 100 of your friends, let's say we had 100 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, like, it's the thing that causes me not to want to do it again. And to not 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. And I personally, when I hire somebody, man, I believe in them. When I hire somebody, 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.
Leanne ElliottYeah.
Dustin HillisLike, 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 gotta go. And, um, That is the hardest part of business. That's what most people aren't willing to do. So they keep the deadweight around, they keep the negative people around, they keep the, 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, talks 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.
Al ElliottYeah.
Dustin HillisYeah, 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. And, uh, man, that's hard. It's painful. I hate it. I never wanna do it again. Um, and I probably am going to have to again, and, and I still hate it every single time. I hate it.
Al ElliottYeah.
Dustin HillisUm, if it's the right thing for the business, if you can sleep at night knowing— I mean, and, 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 gonna do, and, and you give them enough time and it just doesn't happen, then it's on them. That'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, Yeah. 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. And 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.
Al ElliottYeah.
Dustin HillisAnd so it's actually doing them a favor by letting underperformers go.
Al ElliottYour book Capacity, who should be reading it and who shouldn't?
Dustin HillisYeah, 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. And 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 $100 million 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. Uh, it's out on Amazon. Uh, you can go to dustinhillis.com and, uh, order the book there. Uh, you could go to Barnes Noble, just walk in and it's sitting there on the shelf. Um, it's available on audio as well, which I'm very excited. The actor actually sounds like me. Uh, and it's a Southern, uh, gentleman that, that read the book and I'm, I'm re-listening to it and I'm like, man, the, the audiobook's really cool too.
Al ElliottYeah.
Leanne ElliottSo 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 weight of letting people go is usually what decides if a business actually makes it.
Al ElliottYeah. 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.
Leanne ElliottTo help you prepare for that next level, here are 3 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 2 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. And 3, 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.
Al ElliottAnd 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.
Leanne ElliottDustin's book, Capacity: Building Your Business Bigger Than You, It 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.
Al ElliottThe 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.