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Three years ago I played Red Rocks twice with Zach Bryan's tour, and at the after party in Denver I couldn't stop thinking about one thing. Why does one artist break through while my friends who are just as good stay unknown?
I've done over 250 consulting calls with creatives in the last five months, and the ones who stay stuck under 10k a month are almost always making the same five mistakes.
The time money treadmill. The identity swap, where you slowly become the bookkeeper and the account manager and barely touch the craft anymore. Pricing paralysis. The founder monkey trap, which comes from a real trap hunters build out of a gourd and a handful of nuts. And the commodity trap, where you become one apple in a basket of apples and the cheapest apple wins.
Underneath all five is one root cause, and it isn't talent.
Free 18 question audit: audit.wealthycreatives.co
Connect with Jonathan:
- Instagram: @jonathandavidray
- LinkedIn: https://www.linkedin.com/in/jonathandavidray/
- YouTube: https://www.youtube.com/@jonathandavidray
If you're a creative service provider who's tired of being talented and stuck, check out Wealthy Creatives Coaching → [link]
Chapters:
Creators and Guests
What is Wealthy Creatives Podcast?
Most creatives didn't start their business to burn out.
Wealthy Creatives is a conversation with videographers, photographers, designers, musicians, and creative service providers who are building businesses that actually give them their lives back.
Hosted by Jonathan David Ray — a musician, creative director, and business coach who's spent 21 years in the trenches — each episode explores what it really means to be wealthy as a creative: not just financially, but in inspiration, margin, freedom, and the kind of work that makes you come alive. Expect honest conversations about finding inspiration to create your best work, pricing your work, building a client base that values your craft, and living a creative life as an entrepreneur you don't need a vacation from. If you're a creative who's tired of being talented and broke, this is your show.
00:00:00 @jonathandavidray
Most creatives don't have a money problem. They have a business problem dressed up as a money problem. Now, three years ago, I had the opportunity to tour with Zach Bryan, the Americana and country artist, and even play Red Rocks for two sold-out shows with my wife and some of my best friends playing electric guitar. It was definitely a mountaintop experience for me. I'm for sure never gonna forget it. And after our second Red Rocks performance, we were at an after party in downtown Denver with Zach's team and ours. And as I was hanging out with everybody, I honestly was hit with this thought: What makes this one artist succeed?
00:00:30 @jonathandavidray
Over another. I mean, I know tons of talented, amazing musicians and songwriters, friends of mine who could hold their own against any other artist at that Red Rock stage, but they stay unknown while this 20-plus year old was making millions of dollars touring the world, living his dream. And honestly, since then, that question has always stuck with me. Now, I've spent 20 plus years inside the creative world as a musician, a speaker, a writer, a creative director, and now as a coach to creative founders and agency owners. And in the past five months alone, I've done over 200 and.
00:01:00 @jonathandavidray
50 consulting calls with creatives, and watched many more from the outside for the last two decades, and I finally have an answer to why so few creatives break through to real success and financial growth, while most of them stay stuck under 10k a month, booked out and broke, on the hustle hamster wheel for years on end. You see, the ones who stay stuck almost always are making the same handful of mistakes, the same patterns, the same blind spots, and almost none of them are the ones that you're going to guess. You might even be stuck in one of these right now.
00:01:30 @jonathandavidray
And honestly, it can be hard to see from the outside what you're living inside of right now. Now, there's five patterns, and underneath all five, there's one root cause that explains the rest. So, for the next few minutes, we're gonna walk through the exact patterns I keep seeing, why each one feels like the right move from the inside, how much it's actually costing you, and what to do differently if you want to break out of that cycle. So, stick with me to the end because the root underneath all five is the part that actually unlocks everything. Now, the first pattern I see almost every week is what I call.
00:02:00 @jonathandavidray
The time, money treadmill. This is the creative who's fully booked, working every weekend, and still not earning enough. Every month starts back at zero. No retainers, no recurring revenue offers, nothing compounding. These creatives they stay busy, but they also stay broke. Here's why it feels like the right move from the inside. Most of us learned to link paying work to progress. Back when we first started, when I was a musician and I didn't have any gigs, I felt like I wasn't going anywhere. Getting gigs made me feel like I was actually building something and making progress. So we attach that. Feeling of success to being busy, and when you land in a spot where you're slammed busy but you're still broke, you just work harder because being busy feels like you're making progress, but you actually build a loop that keeps you stuck. And then you got no time to get unstuck because you gave all your time away to the work that's keeping you stuck, and that costs you more than you think. Someone sells a thousand dollar project and thinks, "Oh, awesome! It's only three or four hours to shoot, and five or six hours to edit. So worst case scenario, I'm making a hundred dollars an hour, which sounds.
00:02:59 @jonathandavidray
Sounds great, but they're not counting the cost of the gas for the drive, the hour and a half each way, the extra round of edits that the client always asks for, the new piece of gear that they had to rent because something broke on the last gig, the meals they paid for on the road, the amount in taxes they're going to pay at the end of the year. They're just looking at the job and the hard costs, and they think, "Wow, that's it. All the extras are just part of the job." Before Four-figure number sounds like a lot of money, so they tell themselves they're doing well, they're doing great. They never see how much that gig is actually costing them, and some of these costs you can't even put a number on. Miss family time, for example, not being there for the kids, because even when you're in the room, your head is on the edits, on the emails, is on the updates. Not to mention the ulcer that that contractor is giving you because he just graduated college and doesn't know the meaning of the word deadline. That thousand-dollar job actually costs you hundreds more in extra time, gas, stress, and family dinners that you actually never see.
00:03:53 @jonathandavidray
The way out of this loop runs against everything that feels safe to us. It isn't working harder, and it isn't booking more gigs. The creatives stuck here are almost always pricing the wrong thing. They price their time, the hours to shoot, and the hours to edit. So the only way to earn more is to add more hours, but they're already out of hours. The ones who get free price what the work is actually worth to the client instead. Watch what that does to the math. Ten $1,000 gigs is a Full calendar and a bleeding bank account, but three or four gigs at three thousand is the same revenue and your life back, your time back. Nothing about the deliverables changed, only what you decided to charge for it. I'm an example of this. When I first started my coaching practice, I was charging three thousand dollars for a three month relationship. Now I charge fifteen thousand dollars at the time of shooting this video for six months, so two and a half times the monthly rate. And because of that, I can carry fewer clients, give away more attention to the ones I do have, and still make more money.
00:04:49 @jonathandavidray
And you know what? It's more valuable to my clients because I have the margin to make sure they get the best version of me, which leads to the best results for them. The question I ask myself now is simple: Am I pricing on my time, or am I pricing based on how much this unlocks for my client? The day you confidently flip that question, you get off that treadmill. Now, that mindset shift matters more than just pricing because the next pattern is what happens when you never make it. I call it the identity swap. This is when the creative becomes the marketer, the account manager, the bookkeeper, the ops person, the email.
00:05:19 @jonathandavidray
All at the same time. I mean, look, you started this thing to do what you love, but now it's the smallest part of the job, which makes you feel constantly anxious and roll your eyes every time a client email hits your inbox. I have friends who are successful musicians, and they talk about quitting like literally all the time. Not because they lost their love for music, but because all the work they hate slowly swallowed up the work that they actually want to do. And there's no point of singularity where everything just gets added onto your plate at one time. It's this slow drift of days and months and even years.
00:05:49 @jonathandavidray
Of you taking on more and more and more until you wake up one day running a business that you hate, built around a creative love that you barely get to do anymore. I've literally seen this ruin creatives and organizations firsthand. And the reason you get there is actually way easier than you think. The craft, the work you love to do, is the one thing that feels easy to you, so it never feels like the part that needs protecting. The business stuff, on the other hand, though, feels like the real work, the grown-up stuff, right? So you give it your best hours, and you just let the craft that you love fit in the cracks. Nobody decides to.
00:06:19 @jonathandavidray
Stop being the artist. You just keep. Feeding the parts that feel urgent and starving the parts that made you start in the first place. Every task feels small. Every task feels like staying on top of your business, but each one is one more thing pulling you off the work that only you can do. You got into this to be a creative, right, and to live out your vision, to live your dream. And then one task at a time, you trade that dream for a to-do list that looks urgent but leads nowhere. You turn yourself into an employee inside your own company. Now the people who break out of this stop thinking like an operator and start thinking like an owner. They say, "I'm not the person."
00:06:51 @jonathandavidray
The person who runs everything. I'm the person who owns it. The operator measures themselves by how much they can personally hold, but the owner measures themselves by whether the business is built around the work that only they can do. The day you make that switch, you stop drifting away from your craft and start building back towards it. So here's an easy test for you that I run with all my clients. I want you to look at your week. How much of your time actually goes to the thing that you love to do? If that number is small, you're not running a business. Your business is running you. This leads us straight to the next pattern, pricing paralysis. This is the creative who knows.
00:07:24 @jonathandavidray
They're undercharging, but they just can't stop raising prices. Feels like threatening the calendar, risking losing more gigs. So you quote lower than you should, making sure that you're not outpriced by the competition, and then you drop it even further when the client pushes back. Now, this is one of the most important things I'm going to say in this whole video, and you got to understand that to you, your work looks like this old shoe. It's the boring thing you've been doing forever. Because you feel that way, you worry that you need to prove its value to potential clients. So you can't charge too much because you're.
00:07:54 @jonathandavidray
You're gonna lose them, but to the client, you're doing something incredible that they simply can't do. They can't make a video like you can. They can't design the way that you can. They can't play an instrument like you can. In fact, they wouldn't even know where to start if they wanted to. That skill that feels totally normal and familiar to you is the exact skill they can't produce themselves in any way. It's like wizard work to them. You're fricking Gandalf the Grey, and they're Frodo Baggins. Or if you're the Harry Potter crew, you're a wizard, Harry. But you're pricing based on.
00:08:24 @jonathandavidray
How it feels to you, how it looks to you. For you, it's this old shoe, but to them, it's magic. Now, you might think, "I'd never pay that much for that. It's too expensive." But you're not selling to you. You're selling to them. When you price off of what they would pay, you're not protecting the client. You're protecting yourself. You're protecting your ego, honestly. And underneath that, there's something even older. A lot of us grew up learning that our work had value because someone else said so—a teacher, a parent, a good grade, a client's approval. We learn to wait for that pat on the back.
00:08:56 @jonathandavidray
Before we believed it was good. So when it's time to price, we literally do the same thing. We wait for the market to tell us what we're allowed to charge, instead of deciding it for ourselves. And I know it feels humble and it feels safe. It feels like not getting ahead of yourself, but it's the same old habit, letting somebody else tell you your worth. And that mistake is going to cost you twice. First, the energy drain of underpriced work, and we know how this feels, right? You're going to finish drained, frustrated, not proud of it, but instead just glad it's done. And secondly,
00:09:26 @jonathandavidray
You're going to miss the clients you actually want. I want you to think about this for a second. The ones who are ready to pay for the magic, they're not hunting for a deal. They want the best, and a low price is signaling them that what you do is cheap. So your price is actively pushing away the exact clients you wish you had. Okay, here's an example, a version of this that'll make sense to you. Say you're making a brand film for a business. One way to price it is like this: you make a professional video about who they are and it tells their story. Okay, it looks great, and they can put it on their website and their.
00:09:56 @jonathandavidray
Socials, so it's worth a couple thousand dollars to them. Or you sit down first and ask what this film is actually supposed to do for the business. What are they hoping for? What's their desired goal? Well, it turns out they're launching a new campaign, and a film that drives that launch could put two hundred thousand dollars on the bottom line in new business. Same crew, same camera, but one is a video and the other is a growth lever. And the price should never solely be about the work, as you see it. It should always be a reflection of the outcome that.
00:10:26 @jonathandavidray
The client really wants creatives who finally break free from this get clear on who they're serving and what their work actually unlocks for that specific client. They stop. Pricing the work by how familiar it feels to them, or how afraid they are of how the price will be received, and instead they start confidently pricing it by what it's worth to the person who can't do it without them. I want you to stop asking what everybody else charges and start asking what is it worth to the right client to have this problem solved. Now, if you're already seeing yourself in one of these patterns so far, hopefully you don't feel like I'm reading your mail. We're often honestly blind to these patterns because we live in them more than we see them, and the reality.
00:11:06 @jonathandavidray
Is that you can't. Fix what you can't see. That's why I've taken all the diagnostic work that I do with all my paying clients in our first session that helps them see where their business is really stuck. And I built it into a free quiz to help you see what's invisible to you and holding you back from your goals. It's only 18 questions. Honestly, takes about five minutes, and you can do it at audit.wealthycreatives.co, or you can just click on the link in the description. Okay, I want you to bookmark it to take after the video if you want a really clear picture of what you need to fix first. Then keep watching because the next two parts.
00:11:37 @jonathandavidray
Are the ones we literally always can point out and see in somebody else, but it is a struggle to catch it in ourselves. Knowing what your work is worth only helps you if you can actually deliver at scale, which leads us to the fourth pattern, the founder monkey trap. And before I explain to you how it works, let me tell you the story that captures it better than any framework could, and explains the crazy name. Somewhere in the bush, hunters have figured out a way to catch a monkey without a net, a rope, or even having to stick around to watch. So this is what they do: they literally take a gourd and they hollow it out, and they cut one hole on the side just big enough for a monkey's open hand to slip through. And then inside, they drop a few nuts, and then they wedge the gourd into a crack in the rock so it can't move, and they literally walk away. Then a monkey.
00:12:21 @jonathandavidray
He comes around and smells the nuts. So what does it do? It reaches in, grabs a handful of nuts, and then goes to pull them out. And what happens? Nothing. It's stuck. The hole was just big enough for their empty hand, but the full hand's not going to come out. So that monkey pulls harder. It screams. It yells. It braces against the rock for hours, fighting to drag that fistful of nuts through that gourd. And the whole time, we know on the outside looking in, the way out is simple: open your fricking hand, right? Drop the nuts. Walk away. But it doesn't. It would rather stay stuck than let go of what it's holding on to. And there's no trap holding that monkey. There's no rope. There's no cage. The only thing keeping it stuck is its.
00:12:58 @jonathandavidray
Own grip. That's the founder monkey trap. The nuts, your nuts, are the work that you won't let go of because letting go feels like losing control of the business. So you hold on to all of it. No systems, no documented process, no one else who can do it like you. Which means if you stop, the business stops. So the result is this: you're not building a business. You're building a trap with your name on it. Now most creatives run their business the same way they make their art, with total control over every part. And with art, that makes.
00:13:28 @jonathandavidray
Sense right because art is an expression of self, it's who you are. But a business isn't art. A business is a vehicle for your art. And the more you try to personally control every piece of it, the Faster you hit your own limits. I talked to someone last week who's going to be coming on as a client. He had just lost a retainer worth thirty-six thousand dollars a year, okay, three k a month, because he couldn't deliver consistently. Not because his work was bad, because everything ran through him, and because that one client had a bad experience, that was it. They were gone. Then there's a second cost that most creatives never see. When you need to control everything, you don't.
00:14:03 @jonathandavidray
Hire people who are better than you. You hire people who are easy to manage at cheap rates. But the best people don't want to be managed. They want to be led, then turned loose to lead themselves. So you fill your business with people who need constant direction, and then you spend all your time directing them instead of growing. A player should unlock more growth for you. So the way out is to actually hire, delegate, and unlock resources. And the way you find where to start is by asking these four questions. Okay, I ask every founder I work with these four.
00:14:33 @jonathandavidray
Questions and the answer always tells me exactly where the ceiling is. Here are the four questions. Number one: What are things only you can do? Your areas of genius. Number two: What are things you do that could be automated? I mean, have you heard of AI? Kind of thing. Number three, what are the things you do that could be delegated or hired out? And number four, what are you doing that just needs to stop entirely because it doesn't move the business forward? Now that last question, almost nobody asks themselves. I want you to answer all four of them honestly, and the trap becomes visible when you actually see where your time is going. When you free yourself from that trap, the fifth pattern is right underneath it. It's called the commodity trap. This is the creative who prices like everyone else. Sounds.
00:15:17 @jonathandavidray
Looks like everybody else, looks like everybody else, and then wonders why do clients treat me like everybody else? I want you to picture this: you send a proposal, and so do three other photographers, and the client picks the cheapest one. Not because your work is worse than any of the other ones, you just gave them no other basis for choosing you. You become just another apple in a basket of apples, and the cheapest apple wins. And the reason most creatives end up here is that staying in line with the market it feels logical. The fear of losing work has you watching what everybody else.
00:15:47 @jonathandavidray
Charges and using that as your cue. There's a floor you're not going to go under, but you're not going to push the ceiling either. You want to stay in line with the room, and it feels like the smart, safe move. But matching the room isn't a strategy. It's fear masked in logic, masked in reasons. If you're a premium provider, which is what I want for you, your whole job is to make it impossible to compare you on price. You cost more, and the reason you cost more is what you deliver is genuinely different. The experience of working with you is different. The delivery.
00:16:17 @jonathandavidray
Is different. The outcome the client sees on the other side is different. So when they line you up against the three other quotes, they can't compare. They got quotes from three apples and one orange. That's you. Three apples are all selling the same thing: a video, a logo, a website, priced against each other because there's nothing else to go on. But the orange, you, is selling the change waiting on the other side, and there's nothing in the basket to compare that to. The creative who gets out of this pattern decides what their work is worth before the market gets to vote for them, and that.
00:16:47 @jonathandavidray
Move from selling the deliverable everyone else sells to selling the outcome only you can name is the first domino that knocks over everything else. Now, every one of these patterns looks different on the surface, right? The time money treadmill looks like overwork. Identity swap looks like burnout. Pricing paralysis looks like undercharging. The founder monkey trap looks like overwhelm, and the commodity trap looks like being invisible. But underneath all of them is the exact same thing: you never decided exactly who you're for. You've never committed.
00:17:17 @jonathandavidray
To the one outcome you sell, and you've never built a system to deliver it and sell it the same way every single time. That's not a creativity problem, and it's not a talent problem. That's a design problem. And the good news is that a design problem can be fixed. So before you close this video, I want you to sit with one question: Which of these patterns is costing you the most right now? Don't answer it for everybody else. Don't answer it for who you were three years ago. Answer it for the person sitting on the other side of the screen right now. Because the pattern you can name out loud.
00:17:47 @jonathandavidray
It's a pattern you can actually do something about. A problem you can see is a problem you can fix. So now you know the five patterns that keep creatives stuck between five and fifteen thousand dollars a month, and the one root cause that's sitting underneath all of them. But knowing the pattern is only half of it. Doing something about it is the other half. Now, if you want the actual plan, the exact steps I take myself to break out of these patterns and build a creative business to a million dollars in 2026, I walk through that whole thing in this next video right here. What to fix first, what to.
00:18:17 @jonathandavidray
How to charge, how to position, and how to build the system that compounds instead of restarting from zero every other month. If you want to check that out, click on the next video and I'll see you over there.