Ep. 108 - How This CEO Scaled 36 Companies to $300M in Just 3 Years w/ Staci Gray

🎯 From devastating news of her mother's stage 4 cancer diagnosis emerged an unstoppable force in business transformation. Staci Gray took her father's 7 businesses from chaos to freedom, then scaled that success to help 36 companies raise $300M in just 36 months.

In this raw and powerful episode, Staci reveals her proven 3-step framework for breaking free from the entrepreneurial trap. Learn how to stop sacrificing your freedom for success and start building a business that actually works for you.

Key Takeaways:

• The exact process for transforming chaos into systematic success
• How to escape the "entrepreneurial trap" crushing your freedom
• Why most business plans fail (and what actually works)
• The critical mindset shift that unlocks true scale
• Simple steps to start regaining control today

🔗 Connect with Staci: Website: https://organizetoscale.com/ Facebook: https://www.facebook.com/stacigray.organizetoscale Instagram: https://www.instagram.com/staci_gray/ LinkedIn: https://www.linkedin.com/in/stacigray/ YouTube: https://www.youtube.com/@staci_gray

As always we ask you to comment, DM, whatever it takes to have a conversation to help you take the next step in your journey, reach out on any platform!

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DISCLOSURE: Awards and rankings by third parties are not indicative of future performance or client investment success. Past performance does not guarantee future results. All investment strategies carry profit/loss potential and cannot eliminate investment risks. Information discussed may not reflect current positions/recommendations. While believed accurate, Black Mammoth does not guarantee information accuracy. This broadcast is not a solicitation for securities transactions or personalized investment advice. Tax/estate planning information is general - consult professionals for specific situations. Full disclosures at www.blackmammoth.com.

Chapters

• 0:00 Introduction and Guest Welcome
• 0:42 Staci Gray's Background and Family Business
• 2:09 Scaling Businesses and Achieving Freedom
• 5:07 Personal Stories and Modern Family Office
• 6:51 Entrepreneurial Journey and Business Scaling
• 13:10 Emotional Rollercoaster of Entrepreneurship
• 18:51 Creating and Trusting the Process
• 27:29 Final Thoughts and Takeaways

Transcript

Stoy Hall: 0:07

Welcome back on another amazing episode with another bad ass woman who is a business owner, involved a little bit in real estate, knows a thing or two. Staci Gray, welcome to the show.

Staci Gray: 0:17

Oh, so great to be here. Thank you for having me.

Stoy Hall: 0:20

Yes, I'm excited because what you do and what I do they integrate very well, seamlessly together. And then my background of real estate is always fun to deal with. So I'm really excited to have you on, tell your story, what your company does. And then we get to get down and dirty with how people can either use our services one, but second, get involved and take that next step in their wealth. So without further ado, start with your background and how in the world you got into this.

Staci Gray: 0:48

Yeah, well, Let me tell a story. So, my mother was diagnosed with stage 4 cancer, and my father had a lot 7 businesses, a lot of businesses that he was operating and running, and he called me and said, hey, will you come run all the family businesses because your mom has cancer, and I want to have time to spend life with her, because we didn't know how long that was going to be, and I said, yeah, I'll come do it, and I, backstory, I had already ran the businesses before, so me stepping back in wasn't. A huge lift. However anyone who's started in organized businesses knows that even when you hand it off and you put other people in place, sometimes the transition materializes in other ways. And he actually found himself working. 16, 18 hour day, seven days a week, and really was trapped in the business. And that's one of the things that really pisses me off is most people set out to build businesses to create freedom. And then they end up trapped in the very businesses designed to create their freedom. And I don't think it has to be that way. And I think people get trapped because their passion consumes them or they lack system. And so in his case, his passion consumes him. He loves what he does. He enjoys it so much. But when my mom got sick. He, it was, that was more of a priority, spending time with her and family and making memories and being there to research, what doctors, what treatments, what can we do? And so I came in and I helped organize to scale those businesses and hired and trained a team, put systems in place, operations in place, playbooks in place, meeting cadences, scorecards, KPIs, metrics, accountability, all the stuff that makes a business really streamlined and. Operationally efficient, and it was really successful. So it increased revenue, increased profit margin, increased culture, increased clients, all of the things that we measure businesses success. And then my mom, sadly, she passed away in December of 2019. However, all of our clients of our family businesses saw what I had done. And they were capital raisers, real estate brokers, mortgage professionals, property managers, construction workers. All those types of businesses, real estate related businesses, and asked me if I would pawn ornaments to scale their businesses. And I'm like, I have no idea if I can do that. Like I could do our family businesses, but I don't know if this, what I did is scalable. I don't know. And so I had a few friendly people who said, Hey, I'll be your guinea pig. And so I went in with them and I said, Hey, I'll bring my processes. I'll bring my frameworks. I'll bring my playbooks, but you've got to bring the IP for your particular business. Like your niche, you bring, I'll bring process framework turned out to work. So I did 36 businesses and 36 months and from a capital raising perspective, they raised 300 million and it was lots of investors. And you understand that from investor relations and onboarding and all of those things. Yeah. So that's actually how I got started in organizing to scale businesses. And my heart passion for it is freedom because most people want freedom. They want time freedom. They want financial freedom. They want location freedom, the ability to do what they want, when they want, how they want, with whom they want. And the sad thing is they end up sacrificing all of their freedom to gain freedom. And their dinner tables are suffering, their families, their relationships. They're on the verge of burnout, insanity. And I, it pains me because you have kids, like the next generation is looking for leaders and the best leaders are entrepreneurial in nature because they're innovative and they're thought leaders and they're creative. And you don't even have to be an true entrepreneur to be entrepreneurial. Salespeople are very entrepreneurial. Corporate people are very entrepreneurial. I like to call them intrapreneurs. They are inside, but they actually are innovative. And when we can bring that around our dinner tables and really speak wisdom and growth and critical thinking and but budgeting or financial planning or conscious wealth. Into the little hearts and minds around us. It makes a difference for future generations. And I think we can all say right now that we're witnessing the gap in that. And I hope to be a part of the crusade to restore it.

Stoy Hall: 5:06

Absolutely. I love that. And I love the story. Obviously it's not you had to go through that story, but ultimately you're going to do. More for people than probably you would have thought to do for before. And that matches the same for me. Right. So, I grew up in an, in a not very good scenario. My single mother, father wasn't in the picture. She worked 12, 18 hour shifts. Right. So I grew up in that knowing I didn't want that for my kids. I wanted to be a business owner. So I know like my hours today are usually I get them on the bus or. The bus being mother mother drops them off around eight. I pick them up at school at 2 55 and essentially I'm done. Right. I might have a little bits and pieces, but it was so important for me to make sure that I'm in their life. Right. And. You nailed it because there's a gap, there's a huge gap in between those scenarios. And I think it's so important that we try to attack that situation as much as possible. You're also in line with what I have now deemed a modern family office is we are now attacking what has been traditional, right? Traditional processes, traditional models. Financial planning investments, and we're adding something else into emotions and care about people. Over money will come if you take care of everyone correctly, and that's more of a process based. That's more of a culture based. But if you care more about people, the money will come. And I think that's where we're seeing the most from all of our society. I think that's where we're seeing. A change. So I'm glad you're you're quarterbacking that and leading that charge too.

Staci Gray: 6:41

Yeah. Money's a tool. And Zig Ziglar said, if you help enough, other people get what they want, you'll get everything you want.

Stoy Hall: 6:50

Absolutely. All right. So how's about your business? Okay. You've, you stumbled your way and figure stuff out and all of a sudden, holy crap. I've got a scalable business to help people. Talk us through from the entrepreneurial side, the business owner side. Okay. I decided to do this. What was your next step in scaling?

Staci Gray: 7:10

I just took the next aligned action every single day. And this is actually something that people often ask me is like, how did you do it? How did you do it? And then so many people want to have a forever business plan and you really can't predict forever. You can just do the opportunities that are in front of you and be the best kind of leader that you can be at each day. And I've done it really well and I've done it terribly. I have been both sides of the coin and business puts you in a pressure cooker. It stresses you, it tests you, it puts temptation in front of you in the way of revenue or money or opportunity, and it helps you develop better character. So how I did it was I took those first few clients and did really well for them. And then they started telling people, and then I took those next clients and I did really well for them. And then they started telling people and it was just a ripple effect. And then where I went wrong is I probably wish in hindsight that I would have had a waitlist. I did have a waitlist, but I kept trying to expedite my way through my waitlist. And sometimes that puts pressure on the infrastructure before you're really ready to scale. And for me, the success of just the fulfillment, the product, the deliverable of it was enough for word of mouth. That's all I really do is word of mouth. And. I, our process, it's like the cobbler's shoes, right? I needed a me for me and then I got it. So I, spoiler alert, I got the person. I got the me for me and it helped me scale. But wait, have you read the book traction? Oh, you're going to love it. Okay. So traction is this entrepreneurial operating system and it's a business operating system. And they talk about two types of profiles for entrepreneurs. You have the visionary, who's the idea person and they have 20 ideas every single day. Yep, you're probably a visionary. And then there's the integrator, and the integrator is the person who takes the vision and turns it into reality. And I have built most of my businesses as the integrator. I'm really good at taking a vision, turning it into reality. I've done it over 50 times. The transition for me from integrator to visionary was a struggle. Because I was stepping into I ideate, like the best integrators are co visionary, so I ideate really well. However, letting go, like the process of letting go, and surrendering control, and empowering the next layer of leaders, and understanding what that looked like, how to make decisions based on data, instead of just my intuition or being in the weeds, that was a big transition for me. And I, again, I did it right and I did it wrong, but I just kept going. I think that sometimes it's in entrepreneurship. We want to have the forever business plan and we want to predict what's going to happen. And many entrepreneurs are labeled control freaks for this very reason. And I like to say, we're not really control freaks. What we are is we would like to have a plan. What's our roadmap. What are we doing? And so that then fulfilled inside of our organizations, that model. Like, how do we account for the person? Like you were saying, emotions, how do we account for the people? And so we need to account for the fact that most of us are control freaks. We want to be in control of things. It gives us a sense of stability. And so our three step process in the business framework is first we architect and then we build and then we operate. And so what architect looks like in our world is a three day. And so day one is where we build the vision. Day two is where we process map the seven to 10 core functions that make that business work. So how do you market your product? How do you sell your product? How do you collect money? How do you fulfill on your product? How do you build and lead a team? How do you do financial management and reporting? How do you do the key functions that make the business work? And then, what infrastructure do you need to set up, to run those playbooks? And so that, is, on a 3 day, and then, the build phase is where you lay the foundation, you build your infrastructure you maybe get your website, your logo, you hire a key person, you get your first 3, 2, 3, 4 beta client, get them going, get rave reviews, and have that ripple effect start. And then operate is where it's predictable, right? In real estate, you plug a property manager in place. You have tenants, you have landscape, you have house cleaning, and they do the repeatable tasks. Many of my mistakes in business have been where I've taken someone who's like a property manager and asked them to architect, or I've taken somebody who is an architect and asked them to be a property manager. And either way, they want to poke their eyeballs out because one's I don't want to do routine work. And the other is I don't know how to create something out of nothing. Right. And so we have to get the right people in the right seats doing the right things and then so that all happens and then in order to, what gets measured gets done. And so every 90 days, you're running a 90 day. Playbook, and so you have an execution plan of what are my 5 priorities for this quarter? And, cause you can't move 12 footballs down the field at the same time. You're gonna move everything a yard, and a yard, and you're never gonna feel like you're winning. Or you're making any real progress, so you gotta choose what your priorities are, focus on those, and move on forward. And then when, shiny penny syndrome kicks in, or chasing all the rabbits kick in, you have a process for that, and so we put it on a spreadsheet that's called future priorities, and any idea that's a good idea, we say, yay, that's great. And it doesn't fit our 90 days. So we'll put it on the spreadsheet and we'll talk about it in 90 days and it helps us stay focused.

Stoy Hall: 12:51

That's such a great way of thinking about it because it happens, right? I have about a hundred footballs right now in play. Right. And you're always trying to figure out which one needs to move and in what direction. When you've been building this you've done it a lot, right? What can you say to the emotion side of it? Because everyone's probably seen your social medias, they've worked with you and they're like, badass, she's always successful. But, talk us through like the emotions that you specifically have gone through and go through still today, that maybe you have tools to address them now, but you still go through.

Staci Gray: 13:26

Yeah, and I don't think anyone who is successful is always successful. I think most of my lessons have come from falling flat on my face. I like to say if you're gonna run hard, you're gonna fall hard. And so don't be shocked when you fall and the ability to get back up. So as an entrepreneur, you're going to hit a ceiling. Can you're always going to hit a ceiling that is predictable. And when you hit the ceiling, whether it's usually a psychological ceiling. So how you're looking at the situation, you have not yet become the leader that you need to be. To have the business you want. And that was said, I can't remember who, but somebody can put in the comments or something. Who said that? But it's an emotional rollercoaster. Like on my desk, I'll share it. I have a coaster and it literally is a rollercoaster. And it's my reminder that you're gonna go up on your ride, right? And you're going to feel like, okay, I'm excited. This is going to be fun. It's going to be a little bit scary and you're nervous and you're holding on. And then you're like, whoa, plot twist, black swan. I didn't see that coming. Oh my gosh. I'm going to throw up. Oh, well, let's do it again. That is what building a business feels like. It's it's a roller coaster and it's hard to have a stomach for it. And some people legit don't get on roller coasters because it's hard to stomach. So the emotional ride of it is real. And I think one of the things that I've learned to do is to manage and regulate my nervous system and to treat both success and failure as the imposters that they are, because they're not me. And so I think the way I manage my emotions around my business is that my business is not me. And when I have attached my identity to the business, when the business is doing well, then I'm doing well. When the business is not doing well, then I'm not doing well and when my bank account is doing well, I'm doing well. When my bank account's not doing well, I'm not doing well. When my team is happy, I'm happy. When my team's not happy, I'm not happy. And so we get on this roller coaster because we are, we attach our identity so closely to it. And so I like to think of identity in two ways. You have like your innate value, which is your God given value that nobody can take from you. It's a part of you that exists beyond space time circumstance. Yeah. And then you have your market value. And that's what the external world dictates. And that will change because society is fickle. Have we not learned that yet? Right. So. If we attach our identity to our market value, then it's, the ride is much more challenging. When we sit in the seat of our innate value and view our business and our bank account and our team and the plot twist and the rollercoaster of building a business, for the ride that it is, we get to enjoy it and learn the lessons and build the character. Versus overly attach it to me, mean something about ourself.

Stoy Hall: 16:19

Do you feel like on this roller coaster, right? We all get caught up in more of the day to day, like the short term. I say, I get this a lot with my clients and we talk through it. It's you are on a journey, like life journey. We all are, right? Cause we're alive. But like your wealth journey, your life journey, your business journey, are all a long term thing that have short term issues that have to be dealt with. And I feel like a lot of us get caught up in just those short term issues being the end result, right? And we don't know the end result. You had to attest to that, too. You can't we can't plan for the next, well, we can't even plan for the next year, really. But we definitely can't look out 15, 20, 30 years because you just, You don't know, how often do you speak to your clients about, Hey, this is a journey and we need to be looking at it from an overview perspective, not just like what happened today, this week, or even this month.

Staci Gray: 17:14

Yeah, we have a process that we do called my partner and I. She's she's the one that created it and is amazing at it. It's called Reason for Being. And it really helps clarify what it is that you, how you're being. Because you, How you're being and what you're doing is the doing, is the gift, and is the container. And so when we can get our focus into how we're being, instead of the one week, two week, five week, ninety day, five year, ten year, thirty year plan, our focus changes. It's I'm focused on my direction right now. I'm focusing on creating space and grace. I'm focused on community. I'm focused on hitting this metric and we can be committed to the process and trust the process, which as humans, sometimes we have a hard time doing, but learning to trust the process. And I think we spend a lot of time talking about that. And, but then also the mind likes to find meaning in things, and that's just human nature. So we can give it meaning in the doing, then it usually lifts the veil for the burden or the pressure of the immediate from taking over and anchoring back to your why or who you're doing it for. can allow you to view the circumstance as just an obstacle or a path or an opportunity versus it being a make or break in the process.

Stoy Hall: 18:47

So I'm going to get back to trust the process because I got an analogy I want to use for that. But before we can even trust the process, we have to create the process. A lot of business owners right now, entrepreneurs, feel like they don't have enough time to even write down and figure out their process. How do you help them or what is an idea that they can at least carve out the time, figure out the time, or start to actually have a process that they can then trust?

Staci Gray: 19:14

People say this all the time, right? And this is one of the ceilings we hit is the way I'm operating is not working. We all can agree, right? However, I don't have time to fix it. And that's the story we tell ourselves is what I'm doing isn't working yet. I don't have time to fix it. So it's well, when will you make time when it becomes an emergency? When your mom gets diagnosed with cancer, and you have to figure it out, when there is a financial plot twist, and you have to figure it out, when you experience burnout, and you have to figure it out, how much more prepared will you be when it's a crisis, than when it's a crisis? You're in your awareness when you have the mental capacity to figure it out. Many of us wait until it's a crisis and I call that your enough is enough moment. I can't keep operating like this. I got to do something different. So if someone is hitting the ceiling of what I'm doing, isn't working, I know I need to create a process, but I don't even know where to begin. There's one thing that I encourage people to do, which is take a yellow pad and a pen and go sit somewhere that is not where you typically work. Don't bring your cell phone. Don't bring your computer. Do not have Wi Fi. And go sit there, and dump your brain on paper. Everything that you think you have to get done, that is worrying you, that is keeping you up at night, that you're concerned about, and this is personal and professional, so it could be like I'm disconnected from my spouse and that's really draining my energy. I have all of these household chores and errands that I need to do. Taxes are on the, I keep delaying my taxes and I really need to get that sorted out. This team member is really not working out, but I don't know how to address it. Get it all out. And what happens is, we walk around with all these tabs open in our brains. And we're just like, draining us, and draining us. And it's bigger in our brain than it is when it gets on paper. Once it's on paper, the weight off of us is Okay, now I know everything that I've been carrying around. And then, go through that list. And put a mark next to everything somebody else could do. And then really look at what it is that only you could do. And then the ones that only you can do, ask yourself, what meaning or significance validation am I getting from it? And challenge your own sense of self worth against your to do list, because a lot of times we cling to our to do list because it's self validating and it creates this sense of self worth, like I'm doing something, so I'm valuable. And it's this, what I call the performance perfection trump. And just that small action starts to open your mind to view the awareness around it. And from there, then you can start ideating solutions. I'm a big journaler. I've been journaling since I was eight years old and I have every journal that I've ever had since then. And a lot of times as entrepreneurs, there's things that worry us. There's things that keep us up at night. And so instead of pretending like they're not there, I like to actually give voice to it. So I write out what's worrying me. And then I ask myself, what am I making it mean? What story am I telling myself about this thing? And then, what is the root problem? What's the real problem? Not the circumstance, not the fluff, not the blame game or the narrative I'm giving it, but what's actually the root? Is it because I'm not able to say no to opportunity? Is it because I'm saying yes to too many of the wrong things? Is it because I have relationships or partnerships or clients or collaborations that are draining me? Therefore, I don't have capacity for the things that I need to be focusing on. What is the root problem? And then when I get to the root problem, I say, what are five possible solutions? And I even allow myself to write ones that are ridiculous, like I'm shutting the whole business down. I'm firing everybody. I'm just, whatever it is. Let yourself have that cathartic release, and then pick one, and that day, not tomorrow, but that day, action it. So, a lot of times, I lean into accountability, heavily, because it helps me stay aligned, it helps me stay in forward motion. So usually one of my five solutions is, call my coach. Call a mentor, ask an advisor, and I seek community because I know once I get that accountability and that connection, I can't ruminate and self sabotage. It forces the conversation, and so if anyone's hitting that ceiling, They can go with a yellow pad and a piece of paper, no Wi Fi, dump their brain, and then write what they're worrying about, and come up with five solutions, and then take an action in that day. Because when we put it till tomorrow, what happens is procrastination creeps in, and when that creeps in, our self concept decreases. Because, We told ourselves we were going to do something and then we didn't do it and so our self respect goes down and then our self confidence goes down and our self trust goes down. Therefore, we cannot trust the process because we don't trust ourselves to move forward the thing that we know we need to move forward.

Stoy Hall: 24:33

That was deep and I love the hell out of it. And you hit a lot of points and I think a lot of it were similar and athletes are similar in general. We talked about off camera athletic families in football. But ultimately, to trust the process, there must be a team, like accountability. You talked about a coach, be a coach. It could be an advisor, personally, professionally, it could be a colleague, it could be your best friend. It doesn't matter. Like having a team around you whether it's a team, a tribe, whatever you want to call it, allows you. To have accountability to trust your process. And then when it comes to trusting process, I use this analogy a lot. The former athlete going to have to do that in football, we play games four months out of the year. We have 11 opportunities in college football, minus playoffs and extra stuff. And then I felt I have 17 opportunities. You are training all year round for these 11 to 17 opportunities. You not trust the process. Right? You cannot in the middle of March when it's freezing, just be like, I've got time until the season. Right? You have to be able to put a plan in place and just trust it to see it through. And some of these athletes and some of these teams we develop, we're not talking about this year. Right? I'm not worried about this 11 games this year. I know I need to develop over the next two to three. Games. Four years, five years, depending on your situation. And so when you're thinking about trusting your process, you need to think about it that way too, is I am training every day as hard as I can in this process. For those moments in time in my business, probably not 11 a year, but there's going to be a handful of times in your business that it's game day and you need to step up. But that process and preparation has allowed you to be successful that day. If you don't put those in, that's when you do fail and then self doubt and then self creeping and all those things start to happen again and now you're stuck. So I love using that analogy and I love athletes from that perspective because they yeah.

Staci Gray: 26:40

And you're really speaking to planting seeds, right? There's that quote that says success is when preparation meets opportunity. And to use your football analogy, you don't know when your pass is going to get thrown to you. You don't know when the you're going to get an interception. You don't know when that game time opportunity is going to present itself. But you've been planting seeds. And so when it did emerge, you were athletically ready to capitalize on it. And the same is true in businesses. We're just planting seeds. And part of the ability to plant seeds is to create soil that you can plant seeds in, and part of that is a brain in an emotional capacity. To not be overloaded with things that you don't need and keep it fresh and nourished and watered and Nutrient dense so that you can sprout the things that need to be sprouted when the time is caught

Stoy Hall: 27:29

Absolutely as we get to the end of episode we ask every guest this question is what is one thing? Maybe it's a resource concept an idea a step whatever you want it to be That our listeners today can take home today to make that next step forward, wherever they are in their journey.

Staci Gray: 27:49

I would think about what it is that you want to wake up in one year and your life look like, and then write down five things that you could do today to move that forward and then do the one thing today and do it, just do it.

Stoy Hall: 28:07

Simple like Nike. Just do it.

Staci Gray: 28:08

Yeah, just do it. Just don't overthink it. Just do it. Just do

Stoy Hall: 28:12

it. Just take that step. I appreciate you, everything that you do. We're probably going to have you on next year as well. Next year, we are focusing on 2025 female business owners specifically for the whole entire year and more about how they operate both mentally and physically. In running a business. That being said, I always ask our listeners to share, and comment, not because of the algorithm. I don't give a shit about that. What we want you to do is comment. So that way we can help DM Staci, DM me, reach out, have conversations publicly, because the more conversations we can have publicly, the more people that it will help take that next step in their journey. So thank you. I appreciate you and everything that you do. I look forward to more episodes and more fun to come.

Staci Gray: 28:57

Thank you for having me on. I appreciate it.

Black Mammoth: 29:01

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