104: Billion Dollar Corporate Growth Strategies with Kelly Roach

Today, I’m talking with Kelly Roach, the CEO and founder of Kelly Roach Coaching, an 8-figure coaching and consulting company for service-based entrepreneurs who are disrupting industries and scaling businesses.

She also founded The Courageous Brand, a launchpad that helps Gen Z and Millennials build personal brands and profitable businesses in real-time.

Before starting her own company, Kelly spent years in corporate America, rising through the ranks of a Fortune 500 to become the youngest VP in the company. During her time in corporate, Kelly led a team of 100+ employees to record-breaking sales.

In this episode, you’ll hear Kelly’s growth story, including ideas for introducing billion dollar corporate strategies to your business, key changes to make for scaling from 7 to 8 figures, and when it makes sense to intentionally slow the growth of your company.

Inspiring Quotes

• “Relationships are currency.” – Kelly Roach

• “As entrepreneurs, the thing that is really pushed online constantly is customer acquisition, sales, marketing, all of those things. But in essence, leadership, and your capacity to lead — your capacity to attract, retain, and cultivate talent — is everything. It’s your quality of life. It’s the sustainability of your business. It’s your ability to pursue those passion projects.” – Kelly Roach

• “People’s expectation of what it means to be a CEO versus the glamorized perspective that is perpetuated online — those two things are not congruent.” – Kelly Roach

• “The things in our life that we think are our biggest disadvantages are always our biggest advantages.” – Kelly Roach

• “Closing the freedom loop in your business comes down to the quality of your team.” – Kelly Roach

• “I think a lot of entrepreneurs are not aware of how much chaos they create in their companies and how much it stands in the way of their team performing.” – Kelly Roach

• “You have to manage yourself first before you can be a great leader to others.” – Kelly Roach

• Corporate America to entrepreneurship
• Building a 7-figure side hustle
• Internet marketing and the corporate world
• How the CEO role changes over time
• Why businesses struggle to scale past 7-figures
• How to put a great team together
• The danger of hiring from referrals
• Sourcing talent through LinkedIn
• The business-building role of personal branding
• Does it make sense to write multiple books?
• Balancing multiple professional initiatives

Brad Weimert: Kelly Roach, thank you so much for carving out time today.

Kelly Roach: I am excited to be here. Thanks for having me.

Brad Weimert: Absolutely. So, we have kind of three camps of people that I talked to. There are people that are bootstrap entrepreneurs. There are people that are funded entrepreneurs. And then, on occasion, we have somebody that grew up in corporate America and somehow made their way onto the other side of the fence.

Kelly Roach: Yes.

Brad Weimert: And that would be you.

Kelly Roach: Yeah.

Brad Weimert: Can you give me a little backdrop on what you were doing professionally before you dove into launching your own brand, your own companies, etc.?

Kelly Roach: Yeah, absolutely. I’m actually glad that you asked the question because I think, one of the most important things for entrepreneurs today to recognize is that what you did before becoming an entrepreneur is a really important part of your appeal in the market. People want to know. And a lot of times, they choose someone to work with not just because of what they are doing today, but what they did before.

So, for me, I started my working career in a Fortune 500 and the number one staffing firm in the world. And I started off in the most entry-level job that they had, which was sales and recruiting. And ultimately, I got promoted seven times in eight years. So, I moved from being a sales rep to becoming a leader and a manager. And then I ultimately ended up building a team of 100 people.

And as I got promoted seven times in eight years, I went from one branch to managing 17 locations from New York City. Actually, White Plains, New York was my most northern branch all the way down through the Carolinas. And so, all of that experience is the only reason why I’m sitting here today because that’s where I learned sales, marketing, leadership, how to manage a P&L, how to bootstrap, like even inside corporate because we were a publicly traded company, but we were headquartered in the Netherlands. The philosophy of the company was they don’t spend advertising dollars in the U.S. of A.

And so, literally, even though I worked for a Fortune 500 firm, whenever I took over a new territory, a new branch, or I added a staff member, we had to build that market from zero. And we had a foreign name. Most people did not know who we were. They couldn’t even pronounce the name of the company. So, it’s very much like us as small business owners. And so, for me, I learned everything essentially that I know about managing and leading people and growing businesses by managing these 17 locations that essentially were each their own little small business. And now, I have spent the last 11 years teaching people how to take what I learned there and take these billion-dollar corporate strategies, marry them with Internet marketing, and grow small businesses online.

Brad Weimert: Awesome. So, there are lots of questions riddled throughout that story, and one that I want to talk about at some point here is the emotional connection and how that changes from running your own business to being in corporate America because it’s not your money, even if you’re running a P&L, it’s not yours.

Kelly Roach: 100%.

Brad Weimert: But before we get there, I want to talk about the transition, and correct me if I’m wrong, because you can’t believe everything that you read, but you started the business while you still had the full-time job. You grew it to seven figures, just kind of a side hustle?

Kelly Roach: I did. I did. And I say to people all the time, first of all, so I am a self-funded business. I built my company to eight figures without any outside funding, without loans, without debt, without investors, any of that stuff. And I did not want to. I was the primary breadwinner. My husband and I, even when we were dating before we had my daughter, she’s nine now, we had decided that one of us was going to be home full time. We didn’t know which one of us it was going to be at the time.

My husband had a job, he was doing the job. I fell in love with this idea of serving people through growing my own business. So, it just so happened that the way that everything shook out that I was going to keep growing my business and I wanted to, and my husband was going to be home full time. So, for me, when I was starting my business, number one, it wasn’t an option for me to just quit my job and be like, “Oh, I’m just going to start a business.” But more so, more important than that, I did not want to. And I coached people on this all the time. I think that one of the main reasons why most businesses go out of business, and if you look at the chart in 2023, obviously, business closures is the highest it’s been in many, many years, right? Cash flow.

And a lot of people go into the world of entrepreneurship, number one, not aware of the seasons that businesses go through – economic expansion, economic contraction, high highs, low lows. It’s never a straight line. And number two, they don’t have enough cash flow to fund themselves to get to a point where they’re able to invest strategically in the scale of the business to get it to the point supports the income level, supports the lifestyle of the business. So, it was very important to me to keep working. I was totally transparent with my boss and with my company and said, “Hey, listen, I’m going to go do this.” I said, “I’ll do it at night.” And on the weekend, I was a top-performing person in my role. And so, I said, “Listen, you can fire me at any time if my results drop or you don’t see me performing in my day job the way that you need me to.”

And I wasn’t sure on that day when I had that conversation, but I knew I had to be transparent and I knew I was going to go full force. And so, I was like, “They’re going to find out anyway. So, it’s better if I tell them that I’m doing this.” So, I ended up staying on for years and I built my company to seven figures while I was still there. And I think, I guess I love that you asked that question because I think so many entrepreneurs have so much shame around if they need to have another stream of income to invest in their business in order to scale it. And I think a lot of people think you’re not a real entrepreneur if you don’t just burn the bridges. I know that’s the whole mentality.

But for me, I very much didn’t burn the bridges. I’m so happy that I didn’t. Actually, yesterday was my birthday. I got a text from my old boss. I got a text from the person that I mentored that took my job when I left. And relationships are currency, right? But not destroying your family or your psychology, your mental/emotional health as you build a business is really key to the longevity of staying in business. And whatever way you need to set that up for yourself to make sure you have those safeguards, I think, is really important from a longevity standpoint.

Brad Weimert: Well, the integrity and transparency is admirable and disturbingly not common. A lot of people try to do side hustle secretively, and it often is at the expense of their primary activities, so…

Kelly Roach: Oh, thousand percent.

Brad Weimert: I love the way that you framed it. And you clearly were capable of managing both of those things at the same time. A lot of people can’t and a lot of people have a hard time with shiny object syndrome. And even though the side hustle for somebody that really is an aspiring entrepreneur isn’t necessarily a shiny object, the construct is still the same, which is you have a core activity you should be focused on and this thing is potentially a distraction. And if this thing is the distraction, then your core activity becomes the distraction while your core focus is the new thing, right?

Kelly Roach: Exactly.

Brad Weimert: So, I want to talk about how you architected that? Because it’s relevant not only to somebody that’s in corporate America doing and wants a side hustle, but it’s also relevant to an eight, nine-figure business owner that wants to start another thing or wants another investment stream or whatever. So, I want to talk tactics on that. But why did you think about starting anything? You mentioned this phrase marrying corporate America with Internet marketing. What was Internet marketing to you at the time? How did you find it? And why did you think this is what I should be doing?

Kelly Roach: Yeah. Well, it’s really interesting. And there are so many pieces of what you just talked about that I want to explain. First of all, the only reason I was able to build a seven-figure side hustle while I was managing my business, my full-time job, and not let my performance drop was that I spent 10 years working on leadership and management skills, and by the time I started my side hustle, I had developed and cultivated such talent and tenure within my team that my role became very consultative and strategic with them versus where most entrepreneurs sit, which is in the transactional tactics of putting out fires all day. So, that’s why at the beginning of the interview, I said everything that I know today that allowed me to do everything that I’m doing, I learned in corporate because it was the leadership development that allowed me to do that. It was also the leadership development that allowed me to build an eight-figure company and then launch five others and still have them be in a position to grow.

So, the core message that I want to get across from that standpoint is, as entrepreneurs, the thing that is really pushed online constantly and the only thing you really ever hear about is customer acquisition, sales, marketing, all of those things. But in essence, leadership and your capacity to lead, your capacity to attract, retain, and cultivate talent, it’s everything. It’s your quality of life. It’s the sustainability of your business. It’s your ability to pursue those passion projects like you just mentioned. And I constantly see people that they want to scale the business or, like you said, they want to start the side passion project. They want to add the new revenue stream. They want to, want to, want to do more and do different. And that, what I call crown jewel isn’t secure.

So, if you want to start a side hustle, if you want to start a new revenue stream, if you want to split out a new business, I think there’s a couple of really important things to get in place first. Number one is a great leadership team, having great talent that you have cultivated, that you trust, that can take your vision, enhance it, strategically drive it, implement it, it’s everything. That’s number one.

Number two is cash comfortability. If you’re doing the one thing and you’re struggling with the one thing, you splitting your focus and diverting attention over here to another thing is going to do nothing but make you struggle even more. And I see this all the time. People were like, “Oh, my niche over here is getting really competitive. Let me go start something over here.” There’s zero barrier to entry in any niche online. So, going and changing your industry, going and changing your product, going and changing your service doesn’t typically make it easier, right? It typically makes it more complex.

And to answer your other question, I’m trying to go down the list of questions that you had in the question. To answer your other question, I actually did not desire to be a business owner, so I didn’t have a dream to be an entrepreneur. That actually was not my big– I wanted to be a corporate executive. I wanted to make it to the boardroom. I wanted to lead these huge teams in this big company with all this prestige and all of those things.

And as I got up to the top of– I was the youngest senior vice president in a multinational company, traded on the stock market. That was the number one company in its field. And I was sitting around the board table with people my parents age and I was managing 100 people and all of that. And I looked around and, number one, I didn’t feel like I was changing people’s lives. I didn’t feel like I was making a difference. I felt like I was making this one company millions and millions and millions of dollars. And I didn’t really feel like my talent was being used in a way that was changing the world for good. So, that was number one.

Number two, the marriage of the billion-dollar corporate strategies and online marketing, I worked in an industry that still, even to this day, does not understand online marketing. They don’t leverage the power of technology. They’re still very antiquated in what they’re doing. And on one hand, those things that they are doing exceptionally well are not present in the online world. And I’m talking about customer retention activities, renewals, the multi-channel, upsells, cross-sells. All the backend operational stuff that makes a company great, it’s never discussed in the online world. It’s all about funnels and customer acquisition and all of those things, like all the shiny things, right? So, all those things that these corporations have done exceptionally well, which is why they’re billion-dollar companies, they don’t live over here in Internet marketing world.

And on the flip side, these billion-dollar companies that somehow were able to use these antiquated strategies to get to where they are, many of them have no understanding whatsoever of the miracle. I really believe it is a miracle of online marketing that we have accessible to us today. And so, I kind of sit in the middle of that, and I’m trying to bring these strategies from corporate America that are timeless that lasts forever. They’re going to work forever and bring that over and marry it with Internet marketing. And I teach people how to do million-dollar launches and I teach people how to build a scalable team so that they can lead in their industry and all of those things.

But I think that in many ways, the online world is very one dimensional. And I think that leads to a lot of delusion, that leads to a lot of anxiety and depression, that leads to a lot of breakdowns, that leads to a lot of businesses going out of business because people’s expectation of what it means to be a CEO versus the glamorized perspective that is perpetuated online, these two things are not congruent, right? And when you have such a massive incongruency, that’s mentally very hard on people, very hard on people. And it’s not their fault because the story that’s being told is not the reality of what the day to day is, right?

Brad Weimert: Yeah.

Kelly Roach: I hope I answered some of your questions there. I know that was a long answer.

Brad Weimert: I don’t know. There’s no right answer. There’s no wrong answer. You answered how you answered. And I think it’s a really, really, really valuable frame for entrepreneurs to hear. I think one of the challenges for entrepreneurs today is they didn’t come from corporate America a lot of the time. They don’t know what their role is supposed to be, myself included. One of the questions that I ask people routinely on the show is what is your role as CEO.

And the staggering variance in answers is telling of both a lack of structure and guidance of what a CEO is supposed to be, and also the tremendous flexibility in what a CEO is allowed to be in different companies. The size and scope of the company has a tremendous amount to do with that, right? If you are a CEO of a thousand-person company versus 250 versus 100 versus a 10-person company versus a one, the roles and responsibilities are going to be different.

Kelly Roach: 100%.

Brad Weimert: So, when you moved over full time into the role, you left your corporate job and you said, “Hey, I’m doing this thing full time,” you were already at seven figures, what was your role as CEO then? And how has it changed to now?

Kelly Roach: Yeah, definitely. So, then it was really about building infrastructure. It was about figuring out the right roles, getting the right people in the bus, in the right seats. It was really about driving all of the day-to-day behavior and action that was necessary. And I did almost all of the strategy. I did almost all of the vision casting, almost all of the overriding sales. I was much more in the business, right?

And as the business moved from seven to eight figures, my role really elevated up to where my primary focus is, working with the executive leaders that I have, the vice presidents, the president of the company. I have two presidents in two different companies of mine, working with them to make sure that they’re really clear on the high-level vision, more than anything. It’s making sure that they are clear on the vision, where we are going, why we are going there, what the implications are for us and for the people that experience our firm, experience our company, who we want to be in the world, and making sure that every decision that we make and every behavior that is experienced on behalf of our company is in alignment with who we want to be in the world to them, who do we want to be in the world to the people that experience us each day.

So, it’s much more about I provide that high-level vision, I provide that high-level strategy. I set the overall direction of the company and then I give them and empower them with the autonomy to take that vision, to enhance it, to mold it, to communicate it, and then to push it down throughout the organization and translate it into execution, right? So, much less in the business and much more kind of on top of the business.

Brad Weimert: How much of that vision was concrete and explicit when you are doing it as a side hustle? At what point did you say, “Hey, you know what? This has to be crystal clear because I have to portray it to executives”? What was the transition like? When do you spend time on that thing?

Kelly Roach: Yeah. I think my vision was very clear even from the time that I was in corporate. And I always say to people, I think that the things in our life that we think are biggest disadvantages are always our biggest advantages. My biggest advantage as a CEO is that the first five years plus that I was building my business, I basically had an hour before work, my lunch break, which I had never even taken a lunch break in my life. So, I had to train myself to take a lunch break, and then an hour at night. So, three hours a day to build and grow the business.

And so, I had to be so unbelievably ruthless and intentional with my time. And I think that is one of the biggest things that has propelled the company to where it is today and will continue to propel us is that focus on intentionality and clarity. And so, I do think I had that vision when I was working in corporate, and I think that’s what drove the growth in that little incremental amount of time that I had. But of course, your vision is always evolving and changing and, as you grow as a person, your vision for even what you want to create changes, right?

But I think that for the vast majority of business owners, they’re so deeply entrenched in working in the day to day of the business in tactical and transactional items that they don’t have enough time to think. And it’s very, very difficult to cultivate a high-performance team when you as the leader are not constantly the anchor that is bringing the conversation back to vision and inspiration and the compelling future that you’re building because if not you, then who, right?

So, the more that you’re in tune with that for yourself as the CEO, the better performance that your team is going to have. But most CEOs are trying to save money, not pulling themselves out of the roles that they shouldn’t be in anymore, whether it’s fear, whether it’s overwhelm, or whether it’s money or whatever. And so, they’re so kind of in the quicksand, so to speak, that it’s impossible for them to get up above it so that they can then lead people to come up to that next level with them.

Brad Weimert: Yeah, I think that for me and I know others like this, it’s just the dopamine. It’s just that I have conditioned myself. I grew up in sales and I’ve conditioned myself to want that next hit. And if I’m not getting it, I don’t feel like I’m winning. And I got a business coach who, years ago, said, “We need to reprogram you to realize that success is not accomplishing the task if you haven’t trained somebody else to do it at the same time.” And that reframe is just tremendously relevant. And I think it’s hard for people, specifically as you have to be in a different role.

Kelly Roach: Oh, for sure. I always say that I think that the skill set that you rely on to get to taking the business to a million dollars is primarily massive action. It’s selling. It’s you like getting in their guerilla marketing style and just getting it done, right? But then what happens is you get to seven figures. I see it typically with my clients between seven figures and $2.5 million where you hit this wall, where your productivity is capped, your hours are capped, the action you can take is capped, like, you can’t give any more.

And so, at that point, if you don’t start building a new toolset and a new skill set of getting results through others, there’s no amount of efforting that is going to allow you to get that next level because you effort it out, like there’s no more efforting that you have left to give to get better results. And so, the ROI on slowing down to focus on investing in team is exponential because it’s like one plus one equals five. That’s what the outcome of having a winning team is.

But the problem is, is that a lot of people because when you begin to go through that process of building a team, you actually have to slow down in order to speed up. It’s more expensive before it’s more moneymaking. And so, people can’t see past that initial step back to take the big leap forward. And so, they avoid it and they keep reverting back to that same toolset that they use to get that initial dopamine hit, like you said. And so, they kind of just keep cycling in that same place. I think that’s why so many businesses struggle to get to eight figures, nine figures, whatever the case, because you can’t. There’s no doing at that point. It’s being. It’s who you’re being as a CEO, right?

Brad Weimert: Yeah. And I mean, it’s always about being, right? But when you’re getting going, it’s being the type of person that can just f*cking take action. And in sales, that’s the game. In sales, it’s I can outwork you. Even if I’m not as good of a salesperson as you, if I can outwork you, I’m going to win, right?

Kelly Roach: It’s true, yep.

Brad Weimert: So, how do you think about constructing a world-class team in that intermediate step of, hey, I need to transition into the leadership role, I need the right people on the bus? How do you approach orchestrating that step of the business?

Kelly Roach: Yeah. So, I really believe in using an org chart-based growth system. I’ve used this since the beginning of the beginning for me, and that is really looking at when you assess your business from a 10x standpoint versus where it is today. What is the who to your how that is needed in order to 10x your results? Because if you try to make an org chart based on 2x or you try to make an org chart based on 3x, by the time you make the hire to get to the 2x, now you’ve already maxed out and you’re stuck again and now you’re operating back at that same level. So, you look at it from the standpoint of like, okay, what does 10x look like from here? If I was going to take 10x the customers that I have today, do 10x the sales, 10x the marketing, what would that look like?

Map it out on an org chart and then work your way back from there, right? And say, “Okay, who are the people that I have? Are they the right people? Yes or no? Can they be uplevel? Yes or no? Are they the right people for today and also the right people for tomorrow? Or are they the right people for today, but they’re not necessarily going to be the people that are going to bridge me over to tomorrow?” Having those really honest conversations with yourself and constantly assessing the talent that you have.

And then when you look at that org chart and you’re like, “Oh my gosh, there’s holes everywhere. There’s holes everywhere. I need people everywhere. I don’t have the right people,” which is typically the reaction that people have. You just need to say, “Okay, what is the first big rock?” What is the first big rock? What is the first thing that would make a meaningful and consequential difference in your ability to grow, right?

And you start with one big rock and then you layer the next big rock and then you layer the next big rock. But one of the things that I talk to my legacy leader clients about all the time is, when you get to seven figures and beyond, like you always have to be recruiting. You’re always looking for talent, you’re always recruiting. Because what happens is people will come and be with you for a season. But if you’re in hypergrowth, you’re going to outgrow people.

And that doesn’t mean they’re bad people, doesn’t mean that they weren’t the right hire, doesn’t mean anything other than a small business, especially in the online marketing world, is going to go through seasons very rapidly, where the person of today may not be the person of tomorrow. And you’re going to have to keep upgrading your team until you finally get to a place where you have the talent that you can 10x with the talent that you have. And that’s a long journey and it’s a process that requires a lot, but it’s worth it. It’s worth it.

And if you want freedom, I always say, like, closing the freedom loop in your business comes down to the quality of your team. And it’s so true because without that, it just all falls back on you. So, you can say you’re taking the day off, that’s great. But then the work just piled up and you’re doing double tomorrow. That’s the difference between having a great team versus trying to do it on your own.

Brad Weimert: So, speaking of putting a great team together, I have a general allergy to bringing people on who are from large organizations, Fortune 500s, because I feel like there’s going to be a mismatch of expectations in terms of how we execute. As somebody that grew up in a Fortune 500, how do you feel about hiring people from that ecosystem for a small business?

Kelly Roach: Yeah, I think it completely depends on the person and it completely depends on the company that they came from, right? My industry, it was so scrappy and it was so insane and they gave us zero resources. And so, I basically learned how to build my own business when I was working in corporate. In a lot of instances, that is not the case. You’re doing in a day what they’re doing in a month and a half.

So, for me, I think having the diversity of experience and knowledge on your team is really powerful. But I think you definitely need to assess, like you have to ask questions around quantity and around pace and around metrics and around budgets and around expectations and around growth rate to understand if you’re talking apples to apples, right? Because I do agree with you that if you got someone that’s coming from an organization where good looks like this here and good in your company looks like this over here, it’s never going to work.

But there are instances where it can be right person, right DNA, right cultural fit, and it can be great. So, I think it’s very situational. But I do think that you have to take a deeper dive into the specifics so that you are comparing apples to apples in terms of pace and expectation and results.

Brad Weimert: What are some questions that you might ask to help uncover that to see if it’s a good match? And we could use your company as an example, if that makes sense.

Kelly Roach: Yeah, absolutely. So, I mean, a great example is like, let’s just talk about salespeople. What were the metrics that you were held accountable to on a weekly basis? How were you managed to those metrics? How many times a week did you meet with your manager to review those metrics? How is your compensation plan laid out? Did you meet your budget for the last year?

I always, whenever I see a salesperson applying for a job, I’m like, “Where are you versus budget for the year this year?” Almost always, they’re not hidden their budget. They’re not making their commission, they’re not making their bonuses. So, they’re looking to leap and start over somewhere else. That’s an easy no. It’s so easy, right?

Whereas if I interview a salesperson, I ask them about their metrics, I always ask about the volume because what happens is someone can say to you, “I’ve 120% budget for the year.” And they’re thinking, they’re telling you a great thing and you’re like, “Oh, okay, great. So, how many customers did you need to close in order to get to 120% for the year?” “Oh, I closed five.” And you’re like, “We have to close five a day. This person closed five for the quarter.” You already know, like that interview is over, right?

So, you have to dig deeper into just tell me more about that. Tell me about your metrics. Tell me about how did you meet your budget? How many customers did you close to meet your budget? How long did you follow up with that customer in order to get a meeting with that? How many follow-ups did you have to do in order to get their business? It’s so easy. I think the thing that we miss so many times is like we get carried away and we’re clicking with the person. We like their persona, we like their characteristics. We think all the things.

A lot of people interview for experience. They’ll be like, “Oh, this person knows this and they know this and they know how to do this and they can add all these great things to our company.” And it’s like, that doesn’t matter. Ultimately, do they execute? Like, really? Because all those other things can be taught, all that knowledge and expertise can be gained, but you need to know, is this a person that’s going to come in your organization and execute? They’re going to get the job done. Are they going to freak out when you hold them accountable? Are they going to hold themselves accountable, so you don’t need to? Two completely different people, right?

Brad Weimert: For sure. And I think some of those are value driven. Are you the type of person that has that intrinsic driver where you don’t feel successful unless you are executing and doing things?

Kelly Roach: Exactly.

Brad Weimert: I also love digging into the metrics around sales, for example. I look at historical sales jobs and I sort of categorize them, which is, is it tangible or intangible? Is it B2C or B2B? Is it short cycle or long cycle? Is it high ticket or low ticket? And those things inform the velocity of the sale and the way that you’re selling as a result. And typically, an enterprise salesperson and that’s kind of what you highlighted was why I closed five deals, right? That’s the profile of somebody selling an enterprise where they’re talking to multiple people. It’s taking months to close and that person probably can’t perform in a short cycle sale where they’re trying to close people on the spot right away. It’s a different process.

Kelly Roach: Exactly, exactly.

Brad Weimert: I love that. It’s a great way to look at that. So, you came from recruiting. And you’ve been in your own space for many years at this point, so we’re talking a long time ago that you’re doing recruiting. But as you pointed out, it’s a never-ending game for entrepreneurs continuing to recruit. Where do you find the best people today? How do you approach the sourcing element to get the pool of candidates to find?

Kelly Roach: Yeah. And we’ve definitely tried the gamut. And we got our best people from LinkedIn. We used to do a lot of hiring from referrals, which I actually stopped and I intentionally stopped that because I actually– so the way I think about referrals, when you think about scaling your business is they’re pre-sold leads, right? So, referrals are the best clients you could ever get from a sales perspective because they’re pre-sold leads. Someone else was like, this is amazing. You need to work with these people, like they’re advocating for you, right?

And what I found was with referrals coming in, they’re pre-sold leads. I don’t want pre-sold leads. I don’t want someone saying, “It’s so great. It’s so fun here. Come work here.” That does not work out well, right? Because what happens, especially if you’re an online brand, how we are, they see the glossy, edited photographs and they see the beautiful images and the professional videos and the great launches. And it looks like everything is just the life. And it’s like we work tirelessly all day, every day to scrap and hustle and blood, sweat, and tears to create a compelling brand that people buy into. We’re doing our job, right?

But what happens is when someone is pre-sold and they think they’re coming in to this beautiful, glossy, cushy environment, it’s not. So, I don’t want people coming in that are fans of me. I don’t want people coming in that their best friend works here. And they heard it was a great opportunity. I want people coming in that are very serious about their career, that are evaluating us as a business and saying, “Can I build something here? Can I feed my family? Can I grow my portfolio? Can I create a life based on working in this company?” And I want people that are as serious about how they’re looking at us as we are about them. And LinkedIn has really provided some great hires for us, people that are succeeding and doing very, very well.

Brad Weimert: That’s awesome. That’s such a good reminder. It’s so easy for an entrepreneur to have their ego stroked by somebody wanting to be a part of their thing, be a part of the company, the journey, whatever.

Kelly Roach: And very rarely does that work out. Absolutely. And that’s why I bring it up, because I think I can save a lot of people. When you start building a brand online, you’re going to have people that are fans of the brand. I don’t think anyone on my team was a fan of the brand. I have a couple of people that were clients that 10x their results and then said, “I would much rather link arms with a bigger organization and do this at scale than keep building a small thing on my own.” But I don’t think anyone was really a fan of Kelly Roach, and I want it that way. I want people that are business people that are like, “This is my career.” And they’re not doing it because they want to get in the inner circle. They’re doing it because they’re like, “I want to build something here.” You know what I mean?

Brad Weimert: Yeah. Have you ever read Endurance, the book Endurance? Endurance is the story of the attempted crossing of Antarctica by Ernest Shackleton. And it’s actually a recollection, it’s a rewriting of all of these journals that somebody aggregated from all the people that went to go on this adventure. Amazing, amazing, amazing book. But the very beginning is Shackleton has raised money and is trying to get a crew to go across Antarctica, which has never been done before. And this is 1906, horrific conditions, leather and wool and, like, just ridiculous.

And the ad that he runs in the paper says, “This is going to be the most difficult job you’ve ever had in your life. It’s going to be miserable conditions and you have to know how to sing,” which was an odd caveat to this. But the point of the ad was, I’m pushing everybody away because I know that the people that show up really want to be there. And if they can sing, then they’re going to be entertaining when they’re struggling. But it’s beside the point.

Kelly Roach: Yeah, I mean, and that’s it, right? Because you need warriors. You don’t need fans, you need warriors. And I think that’s something to be really clear on, right?

Brad Weimert: Yep, that’s great. So, LinkedIn, tactically, it’s November 2023. Do you run LinkedIn ads? Do you use a tool that does outreach through Navigator? What are the mechanics of how you do outreach on LinkedIn today?

Kelly Roach: Yeah, we put up the posting and then boost the posting, so that it can get more visibility. And then, we’ll have people submit their application and then an application video which, of course, very few people are going to do that. So, that narrows the pool substantially, and then we take it from there. But I mean, the people that have gone through the process that we’ve hired, we’ve had really good success with.

Brad Weimert: So, you use the kind of traditional LinkedIn ads platform?

Kelly Roach: Yes.

Brad Weimert: Got it. And successful for you?

Kelly Roach: Yeah.

Brad Weimert: That’s awesome. I have found it historically to be expensive and not successful for me, but…

Kelly Roach: Well, that’s been our same experience on the sales side. We have not figured out how to, I mean, we run a lot of ads. We do Google ads, we do Facebook ads, Instagram, all of these things. We cannot get LinkedIn ads scaling for the life of us in a profitable way where it competes with other platforms. But we have good success with recruiting with it.

Brad Weimert: Love it. Yeah, we do mass outreach to people, which is super spammy. But you can target so specifically by role, expertise, industry, etc. So, we curate a leads list. And then there are automated platforms. You can use tools that do friend request and connection request. In the connection request, you can put a message. And once the connection is there, you have open dialog, but very cool way to do mass outreach from an internal marketing perspective.

Kelly Roach: Yeah. Very cool. I’ll have to try that.

Brad Weimert: Worth digging into. So, how much of your energy goes into recruiting today?

Kelly Roach: Not as much anymore because now, I have presidents and vice presidents that staff their division and staff their departments. So, I am mostly involved in the final interview at this point after they have kind of gone through multiple levels of the team and stuff like that. But there was a point where that was a huge focus of my energy, like huge, right? So, now, the people that I’m hiring at the level where they would be reporting to me is much fewer and further in between, but it’s still a big part of my leaders’ roles, for sure.

Brad Weimert: I should have asked this before, but can you give me an idea of the size and scope of the enterprise right now? How many employees are there? How many companies are there, etc.?

Kelly Roach: Yeah, so six companies. Each company has their own staff. So, they’re staffed independently, ranging from 3 to 10, and the newer company is 25-ish, give or take, in the coaching and consulting company. And we have a hybrid of offers where we will be super hands on with people and there’s a one-to-one component and things that we can scale with Internet marketing and it doesn’t require more staff.

Brad Weimert: Got it. And how much of your time do you allocate to each of them? Is there one that’s dominant for you that you’re focused on right now?

Kelly Roach: Yeah. I mean, my primary focus is still on the coaching and consulting company. That’s my first company. That was my first company I took to eight figures before I started working on all the other things that I’m doing now. I still get that the most attention, but I am starting to put a lot more energy and effort into my newer companies and what they need and where they are in the process. And it will kind of evolve over time because we have a great leadership team in the coaching and consulting company now. We have a president. They still need me to a certain degree, but it’s an evolution. And I expect by 2025 that I’ll be pretty much out of the day to day of that and really be focused on building these other things. But they’re all interconnected with my personal brand. So, anything that I do is going to then send traffic back because they’re all interconnected in some way, shape, or form.

Brad Weimert: Well, let’s talk about that a little bit, so the personal brand side of things. You started your podcast in 2015 and you’ve got a thousand episodes. Does this sound roughly right?

Kelly Roach: Yeah, we’re about to hit 1,000. Yeah.

Brad Weimert: Wild. You’ve also written four books at this point?

Kelly Roach: I think it might be five and a couple of children’s books.

Brad Weimert: Oh, nice.

Kelly Roach: Four or five, something like that, yeah.

Brad Weimert: So, what is the role of those things in your company at large?

Kelly Roach: Oh, huge. Huge. I mean, the podcast is the entry point for everything, right? Like, a podcast, a lot of people have different strategies with podcasts. I’ve been very focused on just the quality of my content on the podcast since it started. I very rarely bring on sponsors. I very rarely advertise anything. I’m really, really focused on the podcast being the entry point of the brand. And from coming and listening to the podcast, you then start to explore like, “Oh, what are the different ways that I can work with Kelly? And what does this look like?”

And I’ll bring in seasons where I’m talking about The Advance Innovation Society, or maybe I’m talking about our agency, or maybe I’m talking about one of the other businesses or whatever the case. But the podcasts and the books have been massive customer acquisition tools for us, massive brand building tools for us. I mean, they’ve been huge. I mean, I intend to do nothing but write more books and to grow the podcasts as the top entry point to the brand to feed the whole ecosystem of companies.

And I don’t recommend that people have six companies. I’m a business strategist. I grew my business essentially to eight figures with one core launch and one core offer. And then I had a couple little subsidiary things. I think simplicity is so important. For me, once I got the coaching/consulting company to a certain level, I don’t want to be coaching coaches of coaches that coach coaches. That’s not my vision for who I want to be in the world.

And so, I had to really look honestly at how big I wanted this coaching organization to be and who I wanted us to be in the world based on what my North Star is, which I want us to be the number one coaching and consulting company in the world for businesses that want to be sellable and scalable. And by number one, I don’t mean the largest, I mean, the extraordinary result that we can provide for people by very sophisticated and hands-on and custom-tailored strategy.

And so, I had to make a decision when I was doing my 10x org chart. We talked about this earlier. Do I want to take this $10 million company to $100 million? And my answer was no. But I said, do I want to build my businesses to 100 million? Yes. And so, at that point, I decided to continue to work on the sophistication and kind of the positioning and the elevation of the prestige of the business advisory while building out other things that are in many instances, I can maintain quality control by leveraging more with technology than people because I don’t want to have 100 people in my coaching and consulting company. I personally feel that it will impact the experience and result of the customer, which is what I don’t want to do. And there’s lots of different ways that we can help entrepreneurs to achieve their desired outcomes beyond that, which is why I kind of have these different silos that I’m building.

But the brand, the books, and the podcasts, to answer your question, they feed all of them. They feed all of them because once they get in the ecosystem, they’re like, “Oh, you do this, oh, we could work with you over here. We could do coaching and consulting, or we could work with your marketing agency, or we could join your networking organization,” right? There’s all these different ways that they can fulfill the next step in their entrepreneurial journey inside our ecosystem versus just that one kind of siloed way.

Brad Weimert: That’s helpful. And I like the distinction. I like the deliberate choice. I had a feeling that we were going to go there with this, but I like the deliberate choice to not grow it larger. And I think some people say that and it’s sort of a copout, and some people say it because it’s misaligned. So, I like…

Kelly Roach: Yeah, I just couldn’t do it. The delivery and the outcome and results are too important to me. And the thing that we’ve been able to do so exceptionally well is lead with client results. I mean, I firmly believe and I’ve said this so many times and, obviously, we’re not a publicly traded company, so I don’t have every other coaching company stats and results and all those things. But when I look at the number of people that we have helped to build six and seven and now even eight-figure business is like our results are standalone, we are category of one.

And so, as the CEO of a company, I have to decide. Am I willing to risk that in pursuit of growth? Or do I want to reinforce that and then create other ways that we can continue to grow, where the scale will not impact the quality of the delivery and the outcome? And again, I always say to people, I fully do not recommend anyone listening has six companies. I fully understand. I will exit some of these companies. I’ll sell some of them. Some of them may not make it 20, 30 years from now. It’s going to shake out.

But for me, I’m a business mentor. I want to work in different business models. I want to run businesses that are leveraging different marketing techniques. Part of my value to the market as a business mentor is that I am continuing to challenge myself and that I’m doing lots of different things. I’m not just saying, “Well, I know this one methodology.” And if you do this one thing, we all know there’s no one thing, right? But what I can’t do inside an established, existing company is constantly be like, well, we’re just going to stop doing this thing that works because I want to try this because I want to learn it. I want to try this because I want to learn it. I want to do this other thing because I want to learn. That would not be fair to my team. So, there’s also like, you have to understand the amount of chaos as a CEO that you create in your own company and how that impacts your team’s performance. And so, my job is to minimize chaos for my team, not max it, right?

Brad Weimert: I think that that is not the ambition of a lot of entrepreneurs.

Kelly Roach: I think a lot of entrepreneurs are not aware of how much chaos they create in their companies and how much it stands in the way of their team performing. And that’s something that might…

Brad Weimert: Yep. I think that’s another way to say that.

Kelly Roach: Yeah, and it’s something I became really aware of as my company was growing really quickly and I was like, “Wow.” I’m super make or break and this is in not in the way that most entrepreneurs think. They think like I am the talent, right? It’s not like I am the talent. It’s like, no, my emotion and interaction with everyone and everything that I do is so make or break in how they’re going to be able to perform that you have to manage yourself first before you can be a great leader to others. And sometimes that requires a little pull back.

Brad Weimert: Yeah. It’s a beautiful lens. So, a bunch of books, if the books are functionally top of funnel, generating leads for the rest of the business, why multiple books instead of one? Why not doubling down on one and going for massive exposure with one?

Kelly Roach: Yeah. Well, a couple of reasons. So, number one, I am always more interested in building a body of work than I am just in the transaction of anything that I do. Each book that I’ve written is so radically different. One is about building a winning team. One is about the conviction marketing method. So, it’s a marketing book. One is about the live launch method, right? I could go on. The Unstoppable is about 9 Principles for Unlimited Success. So, they’re so different.

And when I think about writing a book, it’s not so much how many book sales am I going to make. It’s the body of work that I’m creating that can give something tangible that someone for only $30, $25 can access. I’ve had so many people come back to me and say, I read your live launch book. And I did a launch using it and I made $100,000, or I made $50,000, or whatever the case. So, it’s just giving a tangible piece of work in the world that can impact people in a positive way.

And so, could I make more book sales if I just went crazy with one book top of funnel? Absolutely. I definitely could. For me, it’s kind of more the creative process of what is a message that I really want to share with the world. So, I kind of think about it from that perspective.

Brad Weimert: Sweet. What is something you wish you would have done differently? What’s a mistake that you’ve made along the way and you would redo given the opportunity?

Kelly Roach: I think when I was building the team, I hired too many producer-level staff members at the beginning and not enough mid-level management and executive leadership. So, I went really wide initially because we were growing so fast and I needed a lot of hands to serve all the clients and to manage all the business coming in. But I wasn’t fast enough with diversifying the leadership team and the management infrastructure.

So, I think just balancing the pacing of how you grow, right? And now, when I look at the company, it’s like they have a very balanced set of tiers so that there’s people that are 100% focused on execution, there’s people that are managing, and then there’s people that are really truly strategic and innovative leaders. So, I think just rebalancing that.

Brad Weimert: It’s probably a good lesson for a lot of people that are getting things off the ground.

Kelly Roach: Yeah.

Brad Weimert: Tell me about The Courageous Brand.

Kelly Roach: Yeah. So, The Courageous Brand is about seven years old now, I think. And I start it with my best friend. And basically, both of us had had really high-level success in corporate and both of us had had really powerful male mentors and both of us had had the experience that in the corporate world, there’s still a scarcity mindset for female leaders of lifting each other up and helping each other. And we looked at it and we said, what are the commonalities of like, why we’ve both had the success that we’ve had? And it was courage and confidence.

And so, we created The Courageous Brand to focus on instilling courage, confidence, and an entrepreneurial mindset in young girls and teens and girls that are college age to really help them to understand the unlock of the power that they have inside of themselves and to kind of go against a little bit of the way of the world, which is about like tweaking or twerking or whatever they do on TikTok and all of these things, like to give an alternative path of this depth of growth as a leader and depth of growth personally and professionally.

And so, The Courageous Brand has two sides to it, it has an educational component, and then it has obviously the retail component. But yeah, that’s the focus there. And it’s really like the give back. It’s like, how do we take everything we’ve learned in some elevator back down for the next generation.

Brad Weimert: As somebody that has multiple businesses and is at a certain level of financial success in life, how do you think about allocation of time towards an initiative like that versus the core businesses?

Kelly Roach: Yeah, I think it’s really important that you have a really strong leadership team, that you have a very cash comfortable situation that’s super stable, and that you have people in place that when you pull your attention off of anything, its performance is most likely going to falter unless you have phenomenal people in place, both producers and leaders, right? So, I always say like your core business is your crown jewel and you have to reinforce the sustainability of that because if you go work on this thing over here and then this thing crumbles, then guess what? You’re not going to get either one because now this is crumbling and now you have to divert your attention off of this, again, to go back over here.

My partner is the managing partner day to day in The Courageous Brand. So, she really runs that company and I serve in a very consultative role there because you can’t be two places at once, right? And so, I think, that’s why I said, and I’ll say it again, like I do not recommend following the path I’m falling. I love it. It’s right for me.

But for almost everyone listening to this show, you would be absolutely miserable. It’s right for me. It doesn’t mean it’s right for anyone else. I love it. I thrive. But it’s not right and it’s not how I built. I built with one thing. I want to be really clear on that. And I feel like that’s why I had the success that I did because I focused on simplicity. I’m at a place now where I’m taking a marathon tour from 10 million to 100 million, and I’m okay with that taking me 10 years. I’m not in a sprint anymore where I was trying to go from six to seven to eight figures really quickly.

So, my strategy in my path is going to look really different than someone listening to this today, that’s like, “Kelly, I want to make $1 million next year.” I’d be like, “Focus on your one thing.” You know what I mean?

Brad Weimert: Well, Kelly Roach, I appreciate the insight. Great reminders for me and a great lens to see business through. If people want to find out more about you, where do you want to point them?

Kelly Roach: Yeah, definitely, check out The Kelly Roach Show. As you said earlier, there’s a thousand episodes. You can go binge it. You can learn so much. It’s personal development, it’s mindset, it’s sales, marketing, leadership, business building, the whole thing. So, definitely, The Kelly Roach Show is the place to go if you want to explore more of what we’re talking about today.

Brad Weimert: Wonderful. Kelly, thank you so much for your time.

Kelly Roach: Thank you. Thank you so much for having me.