How Ryan Built a Million Dollar Coaching Business

If you were able to get your coaching business to a million dollars a year, what would you do next? In this video, I interview my client, Ryan Roy, who actually hit that million dollar a year mark and decided to scale his business back temporarily. So in this video we're going to talk about the decisions that he made that got him to the 100k per month mark, million dollars a year, and why he decided to scale back. We're also going to talk about a specific book he read early on in the journey that helped him close more sales, the habits that helped him keep going and stay grounded at that 100k. So you can take away the lessons and apply them in your own business. Enjoy. Starting at the beginning. What's the. What's the beginning? When's the beginning? When does the coaching business take shape for you?

Yeah, I in. During COVID It was a, you know, shift for all of us. And I think the, Although it was one of the hardest times and challenges there, there was silver lining and I think it just shook up a lot of things for a lot of people. And I had been thinking about financial coaching for tattoo artists for a few years and all of a sudden I didn't have to go into work every day and do tattoos because I kept thinking, someone should do this, but I'm not going to do it. I'm interested, but I don't have enough time. But I had been taking coaching programs my whole life, so there was always a little bit of like a calling, a little thing in the back of my mind. I was like, you'll do something with that one day. And so that's when I was like, all right, I'm going to go all in. And I'm also the kind of person like, I don't half ass if I'm going to do it, I go all fucking in. And so, yeah, it was 2020 that it started, but I didn't know. I'm just. You're just throwing shit at walls and hoping anything stick. You're just flailing around and. But I think that flailing is really useful in the beginning, but I'm not, I don't. I'm not the kind of person to just flail around for a while. And so after that first, I think it was like about the first year or so, I was on your email list for a little while. Someone had told me about you and I, I always. Yours is one of the few email lists that I would actually open and read because it was perfect. It was short, sweet, to the point, and it Offered value. And I was like, yeah, it was one of the few ones that I actually opened up and read. And so I was like, maybe I'll talk to this guy about it. And like, I kind of already knew that I wanted to work with you. But yeah, it was just. Let's. Let's. Let's step into the next thing, the next unknown. Let's explore what that looks like. Because I had, at that point, I think I made around 300 total coaching, and I had spent probably several thousand dollars on all kinds of this and that and courses and certification programs and stuff like that. That never really helped me get clients. They did give me some maybe confidence, but I. Yeah, I. I needed some guidance on how to do the business, how to actually make money doing this thing and just dive in. I think I learned more from just jumping into sales calls and marketing and actually, like, in the trenches of coaching than I ever did spending months in certification programs. And I think that's something I heard you talk about, and that was my experience as well. So, yeah, I started there. I reached out and I was like, all right, we're doing this. I'm going to invest the biggest investment I had ever made in my life into anything, into my financial coaching journey. And yeah, like we said, I made about 300 bucks at the time up to that date. And I think that was one requirement to work with you was like, that you have to have exchanged some money for coaching.

You're in the game.

You're in the game, right? You're not just thinking about it. You're in the game. And yeah, it was. It was. Confronting sales calls really made me. They weirded me out. And that was really helpful to like, role play stuff and really shift my perspective around it. It's like, I think he said to me one time, you said, just a picture that someone's in a burning building and you can really help them get out. And all you're doing on that sales call is you're just reaching your hand out and you're like, do you want to come with me? Because I can totally help you get out of this burning building. And when I thought about it that way, it really shifted my perspective. You recommended a couple good books that really shifted. Yes.

Spin selling, I think, was helpful.

Spin selling was helpful. Go for no. I recommend go for no to a lot of people. Just in general in life. It's such a good life advice book. If you go for as many no's as you can, you'll end up with more yeses than if you just try to get yeses and try to avoid getting a no and that. That little tweak in perspective. So, you know, I'm. I'm still dancing around. I got a couple clients like, okay, cool. We're. This is, like, starting to take form, take shape. Like, I'm. I am in the business of coaching. So that was like, probably like the first year, and then first two years, you know, kind of doing my own thing, then working with you. And I remember I looked in a notebook. I. I journal a lot, and I do a lot of, like, manifestation journaling and that kind of stuff. And I remember having something where it was like, I. I easily and effortlessly sign on three new clients every month. That was like the mantra, you know? And then when I looked back on that, like, less than two years later, I was signing on anywhere between 18 to 25 clients a month. And the date that I had set that by. It was like, by 2025, so I'd already. It wasn't even the date by which I was signing easily and effortlessly, you know, three clients. I was already doing 18 to 25 clients a month. So a lot changed very quickly. And it's. It's been. It's just been a roller coaster, but that's how it got started. Yeah.

Share what you are helping people with. Because I know that when you say financial coaching, this comes from your own experience. What was the niche? What was the focus?

So it was primarily tattoo. Helping tattoo artists save money. Save and manage money. So there I. I did end up getting my license to become a financial advisor and helping with retirement planning and stuff like that. Tax stuff. But, like, it really all come. All your money problems can really all come from, like, are you living on less than you earn? And everything else can be solved as long as you're living on less than you earn. And tattooers and myself included, I struggled with that for so many years. I made good money. I remember thinking, like, man, I probably made. I probably did, like, 80 to $100,000 of tattoos this past year. This is like, five years into tattooing. Like, I don't have any of that money. How is that possible? And it just definitely shook me. And I looked around at a lot of other tattooers that were older than me doing the exact same thing, and it was just like, looking into my own future. And that freaked me out, honestly. And so that was when I started my own financial journey, reading books and, you know, I thought money was evil and all these weird beliefs that we inherit, honestly, like, if I came to you, and you're a newborn baby and you have no concept of money. I'm like, what would you like to believe about money, Greg? You wouldn't say, oh, that money's evil, because, like, that's a hard life. You know, if. If you have to use money and you think it's the root of all evil, that's a hard life you're signing up for. And so I just kind of started to play around with these concepts of my relationship with money, looking at it, you know, Also, money's the, like, the biggest taboo on the planet. People will talk about their sex life before they talk about their financial life. And so I think I'm one of those people that, like, if you tell me not to go somewhere, I want to go there. And money felt like the biggest. No, no. Like, do not talk about it. Don't look at it. It's evil. It's the name that we do not speak of, you know? And so I was like, I want to go there. I want to go in the. The weird no goes on the. Even the rebels don't want to go there. Like, I want to go there, you know, so that was. That was why. So I. I got that kind of somewhat figured out for myself. I figured out some good systems because, like, I'm. I'm kind of a little bit of an ADHD artist, scatterbrained. So if I rely on self discipline, I'm relying on a flawed mechanism to do the thing that I need done consistently for the rest of my life, which is save and accumulate money for the future. So I realized I need better systems, and I did that for myself. And so that's what I do, is I help tattooers and other people. Outside of tattooing, we have psychologists, we have other entrepreneurs, real estate agents, even hairstylists. I help them set up systems for saving and investing money for the future. And. And I help. I help them take a look at their relationship with money, those belief systems that are no longer serving them. And I, you know, I say, if we can help a tattoo artist save money, we can help anybody save money, because they are.

Why is that?

There's just. The tattooers are. Not to be too general, but, like, there's definitely people that are against the system, against the grain, against the conformity. And what's more conforming than money? It just is like. It's like a conformed unit of time and energy in a tradable format, and it's just like, it's. Yeah. You know, and so I think I. I fell into that category as well. And then you, as a tattooer, you can also make a lot of cash, which then you don't have to claim, and you're making it on a daily basis and it's coming in, but it's irregular. And so it's. The hardest way to manage money is when you're getting sometimes lots of money very quickly and easily, and then sometimes no money at all for long periods of time. It's probably the hardest situation to manage money in versus, like, a stable W2 paycheck and tattooers. Like I said, very quickly in my career, I was making over six figures as a tattoo artist, and in my early 20s, I had no idea how to. I'd never seen that kind of money before. So, you know, it's easy, easily mismanaged. Yeah.

I remember I saw one of your case studies where the person was talking about, every day I would just roll my drawer open, I had cash, like, actual cash in front. So it's like, of course I'm going to go to the nice restaurant, I'm going to go spend it, it's there.

I don't know how much is in there. I'm just going to take the wad out and go somewhere with it. And there's no real sense of that. And then there's the immediate gratification of making money relatively quickly. It's possible. But then there's also this. I remember thinking I wasn't going to live past 25. Like, when I was, like, a teenager in, like, early 20s, I was like, I live fast, die young. And so you're not thinking about, like, I might be 80 years old one day. And I think that realization also hit me in my early 20s. I was like, I got sober when I was 26, and I was like, I'm probably going to live longer than I think. And so if no one does anything about that, like, no one's going to do that for me. No. No one's going to come along and be like, oh, Ryan, you didn't prepare for being 50, 60, 70 years old. So here we are. Here, let's help you out. No one's going to do that. It's up to me. And so, yeah, I now help people. Take a look at that relationship. I view like your inner child. You have an inner elder. You have this older version of yourself that you are right now in this moment, responsible for helping and taking care of them and actually building a relationship with that inner elder, rather than, you know, inner child, too. Do the inner child work do the inner elder work, be a whole and complete human being. And, and honestly, when I hear clients say that, like, dude, money's like, it's kind of fun, like, I actually am enjoying dealing with spreadsheets and profit loss statements and understanding these concepts. I'm like, oh, you got the bug. Like that thing that I got infected with you, you, it's contagious. You, you've been infected, you know, and that's the best thing to serve you for the rest of your life.

Yeah, I love that. I think we touched on this a little bit when I visited you in New York and we got a coffee. It's like, as a coach, one of your main jobs is to make the expertise that you share make it so it's now intrinsically exciting to the person that's the client.

Right.

So for me, if I'm helping people with marketing or sales, at the point where sales became kind of fun or marketing became interesting, let me figure this out. Like, I like getting leads. Like it's cool. I make money. Like it's, it's interesting making content at that point, now you're empowered to go take it on. And so for your niche, it was money, right? If money is a scary thing I don't want to deal with, there's not a lot you can do there. As soon as money becomes fun and interesting, yeah, you can help the person, but they kind of got it, you know, you kind of did your job.

Absolutely. That's what I want people to leave with. So. Yeah.

Yeah. Okay. So we talked about this first phase, which was a lot about sales. That's from, you know, 300 total to what, like 10k per month is about sales, right?

Yeah, I think that was. I remember when I started hitting pretty consistent 10k months, I was like, wow. And like I only needed at the price point. I only needed about two to three clients a month at the time to, to hit that. And, and I was doing one on one coaching and I was like, I, I've got this, you know, I figured this out. I started getting a wait list of clients because there was no one else in tattooing doing what I'm doing. So I'm in a blue ocean, as they say. You know, there's no other tattoo artist who have a tattoo background, financial coach that is helping tattooers do this. So I had no competition. So when people started to hear, and now tattooers also, another thing about them, they're very skeptical. They think everything is a scam. And I don't blame them. Like, I get it, there's a lot to be skeptical about there, you know, so people would group me in, but they needed the help so badly that they were like, ah, maybe Ryan kind of sounds like he knows what he's talking about. He doesn't seem like a bad guy. And so I started to build this wait list of one on one clients and then I realized I, I have a six month wait list because I could only work with like six or seven clients at a time. I was still tattooing a little bit. I have a kid, family, and I was taking half up front. I think I was charging $6,000 for one on one coaching at the time. I would take half up front and then I'd say, okay, cool, see you in six months. And it was just crazy. I couldn't do, I couldn't keep doing that. And so that was when I first was like, okay, I'm going to do a small group program to dip my toe in the, the world of group coaching. And I always say like, the difference between one on one coaching and group coaching is like one on one is like lion taming and group coaching is like dragon taming. And like you're not even taming this dragon, you're just on it and it's going for a ride and you're just like trying to hang on to this thing. Especially an evergreen program, which anyone isn't familiar with. Evergreen. It's like there's no, like, okay, you're okay. Four months of coaching and now we're opening up and launching again. This is every single month you're signing on 18 to 25 clients and they're all kind of looped in and it's just this, it's a beast. It was scary. Again, I had hired, I'd worked with other coaches and other programs to help me make that transition from one on one to group coaching. But yeah, I remember you would help me write a sales page for that first group coaching program. And I remember it felt like this magical thing that I wrote a page, I put these words in a particular order and it other people saw that and that page sold $20,000 worth of coaching without a single sales call. I was like, this is magic. This is like a magical spell, you know, and, and they all got a ton of value out of it. And I was like, okay, that's, yeah, so sort of like learning all these tools as I build my coaching business. Because you can be a good coach, you can be a great tattoo artist, but you're not great at business. And you know, you can be a great coach, but, yeah, you have to learn the business side of things. And. And if you get excited about it, that's. That's even better.

I want to highlight a couple things you said. One that I think is important is this idea of you had filled sort of an unmet need for this specific group of people. And that just, I think, makes the game a lot easier. It seems like it has for you. And I'll also say, and I don't know if you fully remember this, but it actually took a second for you to decide to really commit to speaking to tattoo artists, because there was a phase where it was more financial coaching for, like, more creative entrepreneurs. And it was kind of. There was a hesitancy to really speak to that group. But that's like, you. Like, that's who you could kind of give the most clear value to at the beginning. Of course, now it can still broaden out, but I think there was a turning point where you're like, let me speak to my people even more. And for those people, it was like, nobody was specifically helping them with their finances. Nobody that they trusted, because it was one of them, you know?

Yeah. And actually, I'm glad you're bringing that up, because I. I did forget that. Yeah. In the beginning, I was like, my company's the Artful Dollar. We're here for artists, and it's still the Artful Dollar. But I. Yeah, there was some fear and, like, but I can help those people. But it really. I don't know why we get so afraid to niche down and tighter and tighter and actually, I'm niching down even tighter now. So, yeah, I went from artists to tattoo artists. So then our marketing really just focused on tattoo artists. Now I've realized I shouldn't be focusing on all tattoo artists. I should really be focusing on tattooers that are interested in personal and professional development and really also like, their. Their spiritual practice or their. Their spiritual perspective on the world. Because I take a very spiritual approach to my relationship with money. And there are a lot of tattoo artists that need help with their finances that are not interested in that. And so I built a rather large following. 30,000 followers on Instagram. But I realized a large portion of them aren't ever going to work with me because they aren't actually interested in the work that I really find to be transformative. And so in niching down, in changing our marketing strategy, and I think marketing is all about being authentic. The more authentic you can be, the more you will deeply resonate with your Ideal clients. And the more you will push away, it's polarizing. You'll push away people that you don't wanna work with. I'm actually losing followers right now, and I know that. And I'm actually totally cool with that. I'm very intentional. I'm like, yeah, let's. Let's clear out the people that, yes, they need the help and they like the quick tips and tricks that I share, but they're never really gonna work with me and it's never gonna really transform their life because the work that I know to be the most powerful isn't what they're interested in. So I'm sharing more content on that spiritual perspective. I know people are going to judge it and feel weird about it and whatever. So what I found, and this is my learning and building content and social media strategy, is there's posts that go shallow and broad, they get a lot of eyes, a lot of attention, they go viral or whatever. But a lot of times that content isn't what grows your business. It's the content that goes short and deep, where you only get a couple hundred likes or something, but you get like 13 comments, you get a couple really good shares from people that it resonates deeply with. And so while it doesn't look good in terms of the metrics of, you know, I've gotten things with close to 500,000 views, it actually is better for the business. And so anyone who's working on content, I think you should do both. You should do shallow and broad. But don't forget to go, you know, short and deep with those people that are your. Your real quality followers. Yeah.

Yeah, I like that. What? So pick up at the. You launched that course and it was sort of a group program, but you were saying it was, it wasn't evergreen at that point. It was like this was your first program sales page, learning the power of copywriting, what happens next in your journey or what's the next skill that you've got to stack on top of that.

So then I had to. I hadn't. I had. I'd been doing social media, but I knew I still had a lot to learn, and I still have a lot to learn. But I was looking for a coach that could not just help with social media, but also help me move onto a group and an evergreen program. I didn't realize that I needed or wanted an evergreen program. But when I started to understand the concepts of that and really leaning into social media, which is a powerful tool, but it's also scary and Weird and frustrating as hell. I had found someone to help me with that. And I also, I think what differentiate why I chose that particular program versus others was there's so much stuff out there that talks about running ads and then this was talking more about organic growth and no ads at all. And I liked that idea that like let me focus on the strategies that build that organic growth and following and then run ads later. So we actually only recently started running ads after building a seven figure coaching business, we just started to run ads.

And you were really focused on Instagram specifically. Right. Like that's where you really doubled down when. Which I think makes sense. I'd imagine that that's a big place for tattooers.

Yeah, there's a few reasons why I just focused on Instagram and still to this day, I mean I'm getting more on YouTube and stuff like that. But one is I, I heard that even though there's all these other platforms and there was so much temptation and advice go to TikTok, it's grow blowing up like this to focus on getting really good at one platform at a time. And I don't regret doing that because I learned to really hone my craft on the type of content and the way to engage with people on that platform because it is very different on other platforms. And also Instagram is still like, it's an easier platform to connect with like socially, I feel. Whereas TikTok, even YouTube, you're not like building these conversations and these deeper, you know.

Yeah, like DMing people. Like you can DMing people.

You can DM people. Yeah. You can DM anyone. I mean, I've DM. I've reached out to people that I wanted on my podcast and I was like, oh, this person's never going to answer my dm. And they do. And they come on like it's pretty powerful that you can just reach out to almost anyone. It's, it's compared. I think I heard Gary Vee talk about it in the same way that like when email first came out, like if you had someone's email, you could email them and they were going to, they were going to read it. You know, if you somehow got Bill Gates email when that shit first popped off, like Bill was going to read your email now. No, but DMing is kind of like that still to a certain degree that there's a good chance that people will see it up until a certain point.

Yeah, that makes sense. So what was working for you when you said, all right, I'm going to do the Evergreen coaching program. I'm going to focus on Instagram, and I'm going to focus on supporting tattoo artists with managing their finances. What started to work that allowed you to go up to 100k a month?

I. Well, first, I was just shooting cold dms to random tattoo artists, and I. I remember we were working together and I was like, you were like, what's going to really make a difference for you? Like, we've gotten this far, we've seen these results, but it felt like we hadn't yet, like, crossed a certain threshold of, like, all right, this thing works. You know, we'd seen some results, and I was like, I think I just need to just reach out to people. And I know a lot of them are going to say no or they're going to leave me on unread, but if I just reached out to, like, 10 people a day or something like that, I will slow down.

This is the Lighthouse game.

So this is where The Lighthouse game. Yeah, this is where I came up with the concept of the Lighthouse game. So, you know, we were talking about blogging, I think, at the time, which I think my audience less is. SEO is less of a strategy for them, but it's still a good strategy. But I. I knew I was like, I need to be blogging and I need to be making content, and I need to be reaching out to people, and it all felt hard and weird, and I was just like, maybe I just need to give a point system to everything. If I did one of these per week, I did this every day, and I did this per month. And if I came up with this point system, I'm like, all I have to do is earn 100 points a month. So if I don't do the one thing a week, but I make up for it with the daily thing, or if I don't do the monthly thing, but I make up for it with the weekly thing, or it doesn't matter what combination, I will be shining my light brightly and shining my light regularly. And that's all it takes to market yourself and doing it, you know, regularly, doing it consistently. So brightly. Consistently. That's it.

And you gamified the process of marketing the actions you needed to do to get awareness, turned it into a game.

Yeah. And so what that did was it took my focus off of getting clients or making money, and it just put my focus on the things that I needed to do that would naturally result in getting clients and making money. And so I was like, just earn your points. Just get your point. And Then I actually got this, like, daily satisfaction out of hitting my daily points, hitting my weekly points. That little, like, hit of serotonin, Like, I did it. I did the thing that I said I was going to do. Whereas if you're relying on sales or clients, you're not always going to get that every day. And so it can be hard to be consistent with it because you're not getting your little serotonin dopamine kick.

Yeah, yeah. Did you track this or visually or, like, how were you keeping track of the points for yourself?

I was tracking it. I think I started. I was just texting you, like, every day or something. I was like, greg, I need daily accountability right now. That's what I need. And I started by doing that. I think I had a sheet. And then after a while, it. It just became the habit and it. It stopped. I stopped tracking points.

I remember that. I was like, hey, how's the lighthouse game going? You're like, I don't know. I'm just making a lot of money now.

Yeah. Yeah. At that. At that point, I'm just reaching out.

To a ton of people.

A ton of people. And. Yeah. And so I didn't know at the time that there's this. I didn't know about appointment setting or appointment setters, that that's even a thing. And. And there's a whole skill set behind setting an appointment, building a gap, and in either a phone call or a DM conversation, building that genuine connection and then inviting people on the call. I wasn't building any gaps. I was just like, hey, I do this thing. I know this is weird, but this is how I help people. If that sounds interesting, you let me know. I can shoot you a link to book a call. Thanks. Bye. You know, and just. Just mass blasting that as much as Instagram would allow me to. And. And that was how I got. That's how I hit my first 10k months, was just doing that.

Yeah. And just. So you were searching for tattoo artists, searching for these people and reaching out Instagram dm.

Yeah.

Didn't know. Didn't have a strategy for it, really. Just get the reps in spray and pray.

Just. Yeah. And you know what? I've been in coaching groups, like Facebook groups, where people talk about those strategies and they, like, they like, kind of poo poo it. Like, oh, don't do that. And that's weird. Or that's annoying. And it's like, you know what, maybe five people got annoyed out of it. But, like, on a scale from 1 to 10 like, how annoyed were they? Like, 1 being like, I lightly brush up against you. 10 being like, I stick my finger in your eye. Like they were maybe a two. And then the people that I actually got on a call and then ended up working with, like, how much did it change their life? Like a 10. Like, people that have never saved money historically in their whole lives have saved their first 10, 20, 30, 30, 40, $50,000. So I was like, is that worth it? Slightly? Inconveniencing someone for three seconds of their day in order to completely radically change lives? Like, to me, that trade off felt worth it.

Yeah, that makes sense.

Yeah.

What comes next? So you're doing the cold reach outs. You're starting to get traction.

I'm doing that. And I signed up with this company that helped me understand a little bit more of a framework for, you know, like, creating content that not only educates, but, like, busts commonly held beliefs. So someone already believes something, and then you're speaking about the thing that they already believe, but that it's wrong or that to think about it in this new way that's engaging, that's hooking. People don't like their beliefs challenge. They also don't want to believe something that's wrong. So when you're kind of challenging that, you know, just different frameworks for how to. How to do CTA is how to, you know, really not just provide value, but get people on calls and just strategizing. And so I, I took, I don't know how many sales calls I took in the first month that I launched my evergreen program. This is, I think October of 2022 is when it launched. The. The month. In the two months leading up to that, I did $30,000 off of some of the strategies that they had taught me to, to book calls. And, and then the next month, I did $80,000 of sales myself, taking my own sales calls. And I don't know how many calls I took that month, but it must have been like 40 fucking sales calls or something around there. And I remember thinking like, this is insane. Like, I used to make this in a year, and I just made that in a month. And that was when I was like, all right, I need to hire someone to take sales calls for me. I need to hire an assistant. I need to. Someone had recommended that I hire a COO to just help with, like, building out aspects of the company, which I would have never done that. It was actually Mike Taylor. I don't know if you follow Mike Taylor on Instagram. He's a. Used to be a professional skateboarder, and then he went into private equity investing, and then now he's in, like, local government in California. Super nice guy, super smart guy. And I was just like that. Skateboarding to finance, tattoo to finance, connection. So he was like, you need to hire a coo, someone to manage that, and I'll share something about that in a little bit. But, yeah, I was like, I started to build a team, and that was exciting for me. I was like, this is cool. There's a team being built here. And I was terrified of having someone do sales for me because I'm like, these are tattoo artists. You're going to get on this call, they're going to give you one look and be like, where are your fucking tattoos at? Who the fuck are you? But when I met him, he was so genuine, and he had such empathy and compassion for people. And I was like, this is because there's a lot of weird salespeople out there. There's a lot of weird closers and, like, that whole world of sales reps. No, nothing against them. I think sales is a beautiful art form now. It really is. But it can be a weird world. And so I wanted to make sure that the people that the guy that was representing me was a. A good representation of me. And so I was very fortunate that actually I signed up for, like, an entrepreneur almost call, like, support group or something like that. It was like a. It was like a mastermind, you know, whatever Facebook metric group, a bunch of people doing, you know, 10, multiple, five, six figures a month. And I never really went to many of the classes, but the networking alone in that group was what introduced me to this closer who ended up doing, you know, $700,000 of sales in one year. And I was like, that it was worth the 10k I invested in the entrepreneur program, that I never even participated in. The networking was all. I got all the value out of that. Yeah.

Yeah. I think that's a great takeaway. And you do have to. You have to put your chips in occasionally. Like, you have to be investing in this stuff. I. One of the things I wanted to mention, and then I want to hear your. The CEO thing that you're going to say about hiring that person. But I feel like if someone's listening to this earlier on, they're still in the sales part of the journey.

Yeah.

There's always this thing of, like, I don't want to be pushy or scammy.

Yeah.

Which I get. I'm sure you hear it Too totally. I think what people don't realize is like, if you were good at sales, you wouldn't be that way anyway.

Right.

There's some sense that like, oh, in order to really succeed at sales, I'd have to be pushy. And it's like, no, if you're doing that, it's not working. Not working something up. Right. Because like, really, as soon as that would happen, that would be losing you sales.

Right.

The best salespeople that you'll interact with, you'll never feel like you're being sold to. And so I always just like, once you see that later in the journey, it just almost doesn't make sense when people start saying that's like, yeah, that's not what we're going to teach you anyway, so.

Right, right. Same for marketing, you know, it's like weird, cheesy, you know, salesy marketing is not good. It's not authentic. That wouldn't be authentically you. So therefore don't do that, you know?

Yeah.

The best feeling is when someone signs up for your program and they go through it and they're a month in or whatever and they're like, Ryan, I am so glad I wasn't going to do this. Like, I, I was scared. And you, you stood for me. And they, they might even say the words like, I, I'm glad you pushed me a little bit. Right. They might say those words, but they're so glad, they're so grateful because there is this fear because there's your old belief systems and then you're rewiring and creating new perspectives and belief systems. But you have to jump over that crevice that you know is hard. And that's what you're doing. You're taking a stand for someone, seeing what they're truly capable of and living into that future. And it's a scary moment for them. But if you're honest and authentic, they're going to trust you. They're going to grab your hand and be pulled out of that burning building and they'll be grateful for it.

Yeah, yeah. Well said. What were you going to say if you remember about this COO piece?

Well, one, I was, I remember I put an ad on LinkedIn for to hire like a part time COO and we were, we were doing like on average like 30 to 50k of revenue a month. Here's the other thing I have to just disclaimer. When you make those numbers, you're not taking home that much money. Not even fucking close. And honestly, like I would take home Very similar numbers to when I was doing three to four clients a month, one on one, when I was doing 15 clients a month. And it was very deceiving. So there was a bit of a.

Because the costs are higher, revenues higher, costs are higher.

Yeah. So when I hired the sales rep and the CEO and the assistant coach to fulfill on all this new traffic, my take home was like the same. But I'm. I have all these other people doing stuff. I have more responsibility. At one point, our weekly payroll was $10,000 a week paying out to the team. And it was just like, oh, my God. It was such a heavy. It was stressful, dude. It was so stressful. And there were so many times where I'm like, I should just go back to one on one coaching, because it's way less stressful. And I make basically the same amount of money, so I just have to put that disclaimer in it.

I'm glad you said that.

Yeah, no, for real. And people, I think if I heard that, if I listened to a podcast early on and I heard someone say that, I'd be like, yeah, yeah, yeah. But I'm fucking telling you, like, you're not gonna make that much more money when you start doing six figures a month. And I, I was in mastermind groups with other people doing six figures a month, and they said the same thing.

I think that part of that might be a little bit of the employee mindset hanging on too, because it's like you hear someone saying, oh, the business is generating 100k a month. And you're like, holy shit, this person's making a hundred thousand dollars a month that's going into their personal account. Yeah, it's like, no, no, no, no, no, no. That's revenue.

Yeah, the. I mean, I'll share honest numbers. The we. We ended up doing, and I know I'm jumping around here, we ended up doing a million dollars in 2023 of gross revenue, which blew my mind that that even happened. So from 2021, when I first started work with you, 2022, we did 300k, 350k, and then in 2023, we did over a million dollars. It blew my mind that we even created something that people wanted that brought value and they paid for and seven figures was generated. But I total took home about 250k that year, which is. That's great. Like, that's awesome. But to. I had to generate a million dollars to generate 250k. I could have done that one on one and not worked nearly as Much as I did. Easy, right?

Yeah, no, that's. I think that's really a helpful metric for people to get.

Yeah, so you. You have to. And we were talking about teams. Like, you have to want to work with a team. Like, that really excites me. You were kind of sharing that, like, you had started to do that and you started to feel like maybe this isn't for me, or it's not, at least right now or in your career, but. So back to the coo. So I hired this random woman from Rhode island to help grow this company, and it was instrumental in, you know, dealing with payment systems and processing payments and understanding how. And then automations backgrounds in the software. And I don't know if you use Go high level. If anyone's listening to this and use GoHighLevel, have someone help you with that shit. It is so complicated. And I just needed someone to help with all the backend stuff of running a business so that I could focus on making content and coaching people. And like, those are like the main two things that I do in the company. And I guess what I was going to share is. Which I'll. I'll. I'll gladly share now. Is that it? It ended up turning into a really beautiful relationship and we ended up falling in love with my COO, who I met on LinkedIn. So if Tamaya is listening to this, she's going to freak out that I'm even mentioning her, but shout out to my.

Now something you've shared with the team and everyone.

Yeah, yeah, yeah, we shared with the team. Yeah.

What was that like? I mean, what was that like, starting a relationship with the COO and then being like, is this messy? Can I do this? And then.

Oh, yeah, it was totally terrifying open.

Like, what's. What was that process for you?

I don't recommend it. Like, no, actually, that's not true. It's actually fucking awesome because we are both so passionate about what we do, and we get to share that passion with each other. And it's so much fun to build something really big. And so we share in the highs and we share in the lows. I mean, I. I'm so grateful that it ended up somehow working out this way that I put an ad for a CEO on LinkedIn and ended up meeting, like, the love of my life. Like, seriously, she gets me. She sees me and all the good and the bad, and she accepts me for who I am and vice versa. It's like, it'll either dating someone that you are creating a company with will either be your demise, or it'll be your superpower. And so it's like you're kind of like flipping a coin on that. You're like. And in our case, it definitely has been a superpower. Yeah.

Yeah. Well, a lot of people, I feel like, are. They're doing the online dating thing. They're on Tinder, they're on Hinge. I think the best way is probably to put. You gotta put the ad for the coo.

That's gotta find love.

That's the move in today's world. It's really the only way to find love.

LinkedIn. LinkedIn is the dating app of 2024.

People are overlooking LinkedIn for dating. Um, okay, so that's great. That's really exciting. What else is like, I don't know what. What else has been on your kind of edge right now in terms of things you're realizing, things you're learning with the business?

Yeah. So I. Very proud of what we've created and accomplished. And at the same time, I, you know, there's what I wished. What I. It's weird. It's like there's things I wished I knew then, but at the same time, I don't think I would have done anything differently. So there was this excitement about building this business, and it's growing quickly. Let's invest in this. Let's hire this. It. It was an exciting opportunity. Seeing the numbers get bigger is exciting. Da, da, da, da, da. You know, all this stuff. But it was killing me, like, personally, emotionally, spiritually. I was, like, getting drained. And, you know, I'm a big fan of people like Alex, Rosi and stuff like that who's like, this is the hard stuff, and this is what you do and, you know, do the hard stuff because no one can chase you there, you know, and. And if you can do it and it. And so I'm. I kind of feel like I have to hold two separate belief systems. It's like, one, yes, doing hard things can be valuable and build character and teach you lessons you can't pay for. So I learned lessons in the past couple years that no coach could teach me. And I, at that time, I had reached out to you, or maybe you reached out to me, and we were just chatting.

I reached out to you, you reached.

Out to me, and you're like, hey, I'm, you know, kind of working on this other thing, just like some performance coaching and stuff like that, if you want to talk about it. And I was like, actually, yeah, I do want to talk about that, because I felt like the things that were really needed to stay grounded and keep my energy, my creative energy to do what I was doing. I wasn't in a habit of the practice, the sleep schedule, the work schedule, the meditation schedule. And so we had kind of talked about that and I saw that, like, it was. This whole thing was going to crumble if I crumble mentally. And so I was like, let's, let's, let's look at my schedule. Eventually, managing money. Managing money is always important, but managing time becomes more important than managing money at a certain point.

Yeah. Time and your energy too.

Yeah, yeah. And so that was a life changer in looking at my schedule, realizing where my, like, peak kind of hours for certain activities are. I remember we did that. I stopped taking meetings in the morning. We looked at, like, you know, just simple things like meditation, exercise, those things that will fill the tank, that will keep me going over the long run. And, and so that was crucial, I think, in surviving that year of hitting a million. I think it was right after that that we started to work together again. But, yeah, I was so burnt out. I felt so gutted. And I was like, I can't keep doing this the way I'm doing it. So that was a helpful beginning to shifting my perspective. And then when you build a business so quickly, you're. You don't have time to learn lessons that can only be learned over five plus years. And your industry, my industry at least, and all industries, they change rapidly. So there's been so many changes in the tattoo industry. Our focus has gone not a little bit less on financial coaching, more on marketing education and how to grow your tattoo business while still managing the finances. So our focus changes and I couldn't, I. I couldn't keep working the way that I was, and I had to face that. And that was a scary realization, I think, especially around content. And, and that's what I'm saying. Like how we were niching down more with our content. We were like, in this cycle of, you know, lead magnet, lead magnet, lead magnet, webinar. Lead magnet, lead magnet, webinar, like every single month. And it was seeing great results at first, but you start to see diminishing returns. After any marketing strategy, you will start to see diminishing returns. And there was something that just didn't feel authentic about the whole approach. And while it was producing results, it was starting to produce diminishing returns. I was feeling gutted and I really had to rethink what do I want? What are my priorities? What's actually important to me. I felt like we had built this business with a lot of paper. Like we burned a lot of paper. We got this big roaring fire going and you just had to keep throwing the paper. And as long as you threw the paper in, the fire would keep burning. But we never really built the coals that it could fucking rain and those embers will still survive, you know. And so that's the started to take a bit of a longer term perspective. You came to New York. Actually that book that you gave me. Anything you want.

Yeah. Derek Sivers.

Yeah. I haven't finished it but I started read probably about half of it. It's a short book and that really started to shift my perspective of like I've built this business doing all the things that all the people I look up to do and all the coaching courses told me to do and I did it and it worked and. But something still feels like it's missing. And that book really showed me like you can build a business any way. Like you can do it. Like there are no fucking rules. And you know, some of the themes of like, you know, really do what is best for your clients, always, first and foremost do what's best for your clients. Everything else is secondary to that. I think we've always held a very high standard for the service that we deliver our clients. But you know, if I think of any businesses honest with themselves, there's always more you can do. There's always ways you can improve that. And then like the type of content I felt like I had to make, it felt like it wasn't fun for me, it wasn't exciting. And so if it's not exciting even if I'm good at it and I have this skill of how to grab the attention and build the hook and the copywriting, all this stuff, it's still not going to resonate deeply. Like I was just kind of saying. So after reading that book and we, we decided to let go of our sales rep which was a really scary move and I deeply love that guy. We're still kind of work together in some consulting capacity but I was like we need to. I actually don't want to make a million dollars this year. Like I really don't want. If it happens, I'm not going to be mad at but like I don't even want to try to do that. I don't want. I'm. I am not attached to outperforming financially what I did last year because now my perspective is like I want to build the coals. I just want to worry about building the coals that make this business a legacy. And the same tools and strategies and perspectives that you use to grow a business are not the same tools and strategies that you use to build those coals and nurture those coals. And so that's now been our focus. I don't know that I would have gained this perspective had I not played the game of business the way I did. And I. I always think you need to have the breakdown in order to have the breakthrough you've always been looking for. But if you don't have that breakdown, you'll never have that breakthrough. I needed to have that breakdown so I could say, knowing what I know now, would I done things differently? Maybe not, because I wouldn't have had that very important breakdown emotionally, spiritually, mentally. And although it's scary, we're stepping into some unknowns. It's really exciting.

Yeah. I love that sense of restraint, too, because that's its own type of discipline of saying, yes, there's a place for more, more, more, but there's also a place to slow down and make sure that we have a wide enough foundation that is durable, it's deep, can go wide, it can stay there for a long time.

Yeah.

And also noticing when stuff isn't sustainable for you too. You know what I mean? Like, you can do the meditation every day. You can get that focused work done in the morning, and you do have to do that, but there's also some changes you can make to the business.

Yeah. Yeah. That was probably the hardest part about this whole thing, was recognizing that changes need to be made. And they were basically abandoning the things that we knew worked really well for a while, completely abandoning them, and then having to, like, figure it out almost from scratch. But the truth is, it's not from scratch. You know, we have skills, we have knowledge under our belt. But that was the hardest. The hardest thing so far was that kind of realization in just the past couple months.

This is pretty fresh for you.

This is very fresh.

Did something happen specifically? Was there a moment where you were like, okay, we need to shift things, or did it happen more gradually?

So I would say there's been a series of moments like there was. I mean, you know, we're. We're also. We're a financial coaching company. So, like. But here's the thing. Managing finances and managing a business are two very different things. Very different things. And so, you know, and I had never. I'm still new to managing this level of finance, of money, and I've had to rebuild my systems differently to manage certain levels of. Of revenue. But we. We've seen some big challenges financially for the company. You know, when certain marketing things don't work out or we've had a tax situation and then client, you know, there's just, like, all these, like, different things that come up that every business has to deal with, whether you're a financial coaching business or a tattoo business or anything. And I. There was one time where we, like, we had $10,000 in the bank and we had about $10,000 of payroll due at the end of the week. And I. I, like, I'm almost, like, embarrassed to admit this, but it just. It happens. It can happen to the best of you, you know, of any business. And then. And then we were hit with this, like, crazy tax bill that ended up being nothing. Like, fuck the tax system, because they will scare the shit out of you even if you don't owe them anything, but they'll send you a big bill and they'll just hope that you pay it. And if you contest it, it turns out to be nothing. But I was like, me, how are we gonna do this? Like, it's fucking over. Like, I don't even want to do. I don't want to do this anymore. Managing the team. And then. And then we switched gears. We came up with a new offer. And I remember seeing all these, like, videos on Instagram where the people like, yeah, I was in the hole and this. And then I fucking sold my way out of it. Like, that's what we did. And it was so cool. It was so badass. And we made a better program that helped a ton of people make a lot more money. And it was just, like, awesome. We're getting crazy good testimonials, but it was like that then. Then we kind of ran into, like, similar problems. We didn't have the Kohl's. That was the problem we didn't have. And honestly, when I'm speaking about Kohl's, to be more specific, I think I'm talking about brand.

Yeah.

Like, I'm talking about a deep, resonant trust in you, your product and your. Your brand, your message that you can really only build over time. It's not like you can just trick an industry into building an immense trust in your brand. It's just showing up consistently for a long time, doing the right thing, doing right by your clients, you know, giving people what they want, giving people value for free for a long period of time. Those are the coals. And that's that's what we hadn't built yet. And so I think there was a realization. It was like, we did the thing. We sold our way out of it, and we're still running into similar problems that actually we weren't solving those problems. We were just throwing more paper onto the fire.

Right? Like, do I need to keep. Yeah, I think that's a great analogy. It's like, I can do it again, sell my way out of it again. I'm just going to have to push again and push again versus, like, how can I make it so this becomes easier and easier and easier because of the reputation that's getting built, because of the referrals, because of all that. And you can have negative reputation, which is not what was happening to you, where it gets harder and harder. You can have positive. Where it's just easier and easier. You can have it where you're like, okay, let me slow down and. And build the coals. Like you're saying, I think that's really smart, because I think otherwise you end up in the same situation two months from then.

So that was the realization. The realization was, we. We're not gonna solve these problems. Like Einstein. You can't solve a problem at the level it was created. We can't sell our way into building the coals, the deep trust and brand that we ultimately need. So let's shrink the company. We ended up letting go of some people, pulling back on some people's responsibilities. I lowered my pay. I lower. You know, we damn near lowered everyone's pay at least a little bit, except for our coach, Chloe, the assistant coach. She's such a phenomenal human being. And I was like, there's no fudgeing way. I'm lowering her pay. Like, she's just like, she's too fudgeing good. She's too valuable. I love her. So shout out to Chloe. And I always say, people come to work with me, but they stay to work with her. You know, she's. She's just brings so much value to our clients. And. And I'm. I'm happier. I'm making less money. I'm making content that I feel better about. I'm having better conversations with people. Whether we work together or not doesn't matter. And I'm in a happier place than I was a couple months ago. And that is just a really cool realization. So that's. I was excited to share that with you because we've been talking for a while, and there was some. Yeah, I was. I was pretty. I was an unhappy camper for a while.

But yeah, that's so great. And I'm glad that the, the Derek Sivers book was part of that. I think for anyone, there's a specific chapter in that book that you reference, which is what I always think about when I think about that book. About everything you do is for your customers. Any decision you make, if you're thinking your customers will never ask you to expand, they'll ask you for certain things that may require expansion.

Sure.

But if you ever get confused, go ask your customers what they need. And I just thought that was so simple and so amazing. But the what you've done, which a lot of people fail to do, not to mention, I mean, I think it's like only maybe 1% of entrepreneurs hit the million dollar revenue mark.

Yeah.

But I think what can sometimes happen is people build this monster that eats them alive and then they're done, they're out of the game.

Oh, yeah.

Because they can't say, okay, yes, there's some short term selling I need to do and let's steady the ship, which takes a lot of fortitude. And then let's take a look at what's going on to make this sustainable. And sometimes that means hard conversations. It sounds like, and like ratcheting down people's pay and stuff like that. And that sucks. It's the harder road. But you stay committed to the mission long term.

Yeah. Yeah. So, yeah, I, I always say, like, business is the ultimate spiritual crucible because it forces you to surrender, it forces you to trust. And if I had to put all my faith in Ryan Roy, I would be done. And I have to put my faith in a higher power and take a step blindly into the unknown and just trust. Like, if there's love in my heart and I'm really here to do good things and make a positive impact on the world. Even if you fail, you win. There is no real losing in that. So even if we run into some other roadblock and this company ends up not doing the thing that I wanted to do or expecting it to do, I'm not even afraid of that anymore. And I think that's like a bulletproof fear because I know that I'll find a way to make that impact in some other way, no matter what. You know, I remember when we had, early on we were coaching and I was moving from a tattoo artist to a coach, and it was a really hard transition. And you, we had that deep conversation, Some tears were shed. You were like, are you, are you like a hundred percent in this, are you just like 90%? And I was like, it was hard for me to let go of this identity because I've been tattooing full time for 13 years at the time. And I was like, I want this so bad. I want to change people's lives around money. I don't want people, I don't want artists to live with the burden of money. I want the creative dreamers and thinkers in this world to have freedom around money. And I want that so bad that I'm willing to let go of this strongly held identity. And that was when I. It was like I turned from a cucumber into a pickle. And you can't turn a pickle into a cucumber. And so no matter what happens with this business, it's like my life is in service of making a positive impact and I will walk blindly forward, march forward with that, you know, that intention at all times.

Beautiful. I think that's an awesome place to wrap and love what you're doing. Always love collaborating. Where should people go to learn more about what you guys are up to?

Well, if you're not a tattoo artist, too bad. No, you can find me on Instagram. RyanRoy tattoo R Y A N R O I. People always ask me, is that your real last name? Ryan Roy. Because Roy Roi Return Investment. It's my real last name. I was born with that. My parents Ryan Roy tattoo. And yeah, that's where most of the good stuff is. I also have a podcast, the Artful Dollar. Check that out. People seem to really like it because we get, yeah, a lot of good reviews and stuff like that. So I'm just going to keep sharing it, keep shining my light. I was thinking the other day, I was like, how many points do I earn in the lighthouse game now? Probably like a thousand points a month if I had to tally it up, you know, but it just happens effortlessly now. I'm not worried about earning points. I'm just. I'm just shining my light brightly and regularly. If you like it, great. If you don't, that's cool.

Amazing. Love you, brother. Thanks for taking the time.

Love you too. Thanks, Greg.