From Dying Agency to 8-Figure Success: The Design Pickle Story

Welcome to the BizGrowMojo podcast. The podcast where we get into real talk about business ownership, growth, marketing, learning lessons, and advice with real business owners. Here’s your host, Ryan Amen. Now, let’s get down to business.

Finding Success in the “Boring” Work

I’m pumped to get this rolling. Let’s go.

What if the secret to building an 8-figure business wasn’t about being flashy or creative, but about solving boring problems really well? Today’s guest, Russ Perry, took a simple idea, helping businesses with everyday graphic design and turn it into Design Pickle, the largest subscription-based design service. We’re diving into how he pivoted from a struggling agency, why he focused on boring work that was actually working, and the exact positioning strategy that unlocked millions in revenue. Plus, Russ shares the one decision-making framework that gives you a two to three% advantage over your competition, which compounds into massive success over time. If you’ve ever wondered how to turn a simple service into a scalable empire, this episode is for you. Let’s get into it.

All right. Well, I appreciate you coming on to the podcast, Russ, and having your team reach out to to do this. Uh, I’m really excited to get in the weeds with you. I think you’ve got a really interesting story. I’ve kind of checked out a couple of your other podcasts and um, you know, l skim through your book a little bit. I haven’t had time to dive in as far as I’d like to, but um you know, just for the uh the viewers that aren’t familiar with you and your business, let’s start by just telling a little bit about yourself and what your business does.

The Stereotypical Entrepreneurial Journey

Oh man. Well, I joke I ran I’m like the um most stereotypical business entrepreneurial story where I failed a lot and then finally got so frustrated at my life that I found out a very obvious and easy path to success. But um yeah, I mean I’m Russ Perry. I’m the CEO and founder of Design Pickle. Design Pickle is the largest subscription model for graphic design. So we help businesses around the world get uh part-time graphic designers on our platform and then you request, we match you with the best creative and um it’s kind of like a fractional addition to your team. So we’re not really a fit if you just want a logo. uh you could use now AI for those kind of things, but it’s like if you want stuff consistently all the time and uh you find yourself, you know, looking at whatever tools you may be using being like, you know, I don’t I shouldn’t be doing this. I should actually be like handing it off to someone else. And then also really large companies use us because often they’re underresourced and they maybe have one designer supporting, you know, tens or hundreds of people and so we can come in and be added to their teams. But um it’s been a it’s been a ride and you know recently I wrote a little bit about the the path of success with design pickle more on the philosophy and the principles and everything in my book the creative CEO but I I’m still on it you know still learning every single day and still trying to figure things out and very much still very active in the business.

Yeah that’s amazing. It sounds like you really figured something out that a lot of other companies haven’t been able to do with the the model of design pickle. That’s that’s uh you know really cool idea. How did you come up with that idea to begin with to pivot to that direction?

From Agency Chaos to Subscription Clarity

[5-minute mark]

Well, I mean, I think it was a again pretty stereotypical path. I ended up out of college working in marketing and design mainly because a friend gave me a job and I sort of fibbed about my experience and then got into a graphic designer role and was like, “Oh crap, I actually need to learn this.” Um, but it it it it quickly evolved into learning much more about the business and the marketing side of things. And eventually I was naive enough to try to start my own design and creative agency, which had its moments of success over about eight years. And but it was always very bespoke, you know, one-off projects, big typo deliverables, um, a lot of stress, a lot of pressure if a client would leave because that could be like a third of my revenue or a fourth of my revenue. And eventually I just realized that like, hey, I love what I’m doing, but how I’m doing it is not working. There’s got to be some other path. So, I took a little bit of a hiatus. Uh, closed the business that I had. Um, I always joke it’s like, you know, was like putting down a dog that, you know, you know, eventually is going to die, but it’s just kind of miserable. Like, like there was no sale, there was no exit. Like, we didn’t fail tech. like we’re still making money, but it was just like, hey, this this has to go. Um, and then in that season, which was about a year and a half, I was consulting and just kind of like doing a lot of introspection and personal development work with coaches and I realized like, hey, I want to stay in this industry, but there’s got to be a new a new path for me. I don’t want to do an agency again.

The Aha Moment: When the Side Thing Takes Over

And it just so happens that I was supporting enough clients at the time with miscellaneous design, marketing, kind of things here and there. And I kind of needed a little help because I would I would get behind on projects if I was working with one client in like their office for a few days and I wouldn’t attend to the other ones. So I created an inbox system for all my clients to use really just to focus on like the basic design things they may need for trade shows, marketing graphics, business collateral. And that thing ended up starting to work on its own. And I remember kind of having this aha moment. I was like, here I am like running around Phoenix where I live, like going to all these meetings, all these, you know, like like projects and there’s this little thing and it’s kind of just doing its thing. Like someone would email it in. I had a freelance designer and a project manager sort of like observing the inbox. They would get it done without my input. Originally, I would review it and send it. Eventually, they were just like, “Hey, we’re just going to send it, Russ, cuz you’re taking too long.” And so, that was like the moment for me where I was like, “Oh, well, I think I think I think there’s something here, right?”

Yeah. And you know when I talk about this at a macro scale, I feel like in every business, especially companies that have been around a long time, you know, we try to do all these things, but when we look at like what’s like working the best, you know, what’s easy is like I’m making money on it, but also it’s like it’s not stressing me out, you know? And that’s and that’s kind of what it was. I mean, the work wasn’t sexy. It wasn’t, you know, big award-winning campaigns. it was just like we need this business card, we need these graphics, we need these Facebook ads, we need these things. And so that’s when I went all in on trying to build a subscription business around it. Um, which hadn’t been done before. And uh, yeah, hit a hit a vein and it turns out it it worked.

Kind of turned out to be that 20% that was giving you the 80%.

Exactly. Exactly.

The Power of Boring Businesses

[10-minute mark]

And I think too like it’s different today because you know there’s been dozens of copycats of what we do and you know subscription and fractionalized services are everywhere now but 10 years ago you know there that wasn’t that wasn’t a thing like if you wanted like part-time help you could hire a contractor or freelancer in a marketplace but it was also for me a bit of a putting my ego aside to say hey I may not be like the fanciest company out there but I’m just going to do something that’s really helpful. And you know, many years later, I look at all these, you know, entrepreneurs and CEOs and some of the most successful guys I know are in the most boring businesses. They just start doing like I do trash removal and I have a hundred million dollar company and you’re like, what? You know, and so, you know, for me that’s I think like creatives are often don’t want to do boring stuff. They want to do the flashy stuff, the cool stuff. And so for me, once I got over that, I was like, “Hey, this is actually really great. I have happy clients. We’re making money, and I can put a system around it.” Which was actually one of the biggest things that that I learned out of it all was, you know, having a system to deliver the value, which I didn’t with my previous businesses.

Yeah. Yeah. I can really appreciate that. I come from a graphic design background myself. You know, that’s kind of how I started and got into marketing. I worked at a sign company actually out of college for a while. And that was, you know, always I really liked what I was doing. But that was one of the things that I noticed was the business ebbed and float a lot. You know, it would be really busy in the summer and it would, you know, peak and then it would slow down toward middle of winter. Like there was times when I was sweeping the floor literally because we didn’t have anything going on. And I was like, I wanted to break off and kind of do my own thing and and build my own sign company eventually, but I was like, I just don’t know about the stability of this because it’s so difficult to keep a steady flow, you know, and I’m not the best with managing and saving money and that type of thing. So, I don’t know how well that would have worked for me. But, you know, I kind of discovered digital marketing and uh, you know, with like search engine optimization, that sort of thing. It’s just kind of needs to be done all the time. So, you know, most people are used to paying that monthly fee to continue doing it. So I kind of gravitated more toward that. But yeah, that’s kind of, you know, it’s it’s fascinating that you solve that problem and were one of the, you know, first people or if not the first, you know, person to actually figure out that solution to solve that for designers. That’s pretty cool.

The Positioning That Changed Everything

Yeah. And and another piece of it that I talk a lot about in my book is I I I had done branding for many years before Design Pickle. And like I’m talking like half million dollar projects on logos and collateral and launch campaigns. And when I was looking ahead on like how are we going to differentiate ourselves because you know you me you mentioned SEO you mentioned printing and signage there’s thousands of those companies out there. Yeah. And so I decided, look, I’m going to be uniquely positioned not in the work that we’re doing, um, not even in the industry that we focus on, but how you buy what we’re selling. And that was the big thing that unlocked a lot of our original growth was we were the only company that had kind of had two feet in the world of like, oh, this is kind of like signing up for Netflix. I just go online and I put it in. But it’s also kind of like hiring somebody because I get to work with them every day. It’s a it’s a much more fractional cost. So I’m paying, you know, a thousand bucks instead of 6,000. Like when you had that job, I’m sure someone was like stressing about your payroll when you were sweeping floors, you know.

[15-minute mark]

So um so that was that was the thing that I think was you know and I teach a lot of a lot of entrepreneurs today is like do what you do but it there’s always a way to position it in a unique way either in how it’s delivered uh how it’s sold or some other part of your business that other people aren’t doing um and the service maybe it’s the service level or it’s you know whatever else and and I think a lot of times companies when they’re struggling they think they have to be like crazy different or creative and it’s like kind of but in one of those areas you can find a unique lane that your competitors aren’t selling it a certain way or they aren’t delivering a certain you know like it’s a little cliche but think about like online ordering for you and I but we were just chatting I’m like I’m waiting for this carpet guy to show up at my house and I’m like man where where’s the Door Dash app that I could to see where he’s at and know and I’m not having to call someone and text me and do the thing. So, there’s still so much opportunity out there to to to position yourself in other ways.

Yeah. About finding that unique selling proposition and doing something a little bit different. I always laughed, you know, in the agency I worked at, we worked with a lot of attorneys and we were we would try to get them to find that unique selling proposition and a lot of times they’d be like, “Well, you know, I do free consultations for personal injury lawyers.” It’s like, no, that’s not unique. You guys all do that, you know.

It’s just Yeah, it could be a little bit tricky for sure. You know, and I think it depends on the business. It can be trickier than other businesses. But yeah, there’s always something. There’s always something. I love Man, those I mean, I’m in Phoenix and those I I know some metro areas, those personal injury guys just rip it. But I there’s one guy and I forget his name and you know, you see them come and go like they just like buy all the outdoor advertising for a while. And there’s this one guy today. He’s just he has like a 1980s cell phone, bags of cash horribly photoshopped in his hand, and gold chains, and that’s his ad. But I’ll tell you what, it’s probably working because it’s the most ridiculous ad I’ve ever seen for personal injury alert, right?

Yeah. Yeah. So, I mean, you could do it in your advertising also. That’s funny. Oh, man.

Building an 8-Figure Business

So, tell me a little bit about just kind of the size of Design Pickle. I mean, you guys say you’re you’re you’re pretty large. Um, you know, and I’ I’ve kind of got an idea from some of the podcasts that I that I’ve seen you on. Uh, but for the audience, like, what are we talking like? How many employees, like roughly how much revenue, if you’re willing to divulge that?

Yeah, I mean, we are at a at a level where um we don’t publicly disclose revenue anymore, but it’s it’s uh it’s eight figures getting close to nine. Um, we’re in a position serving about 10,000. Uh actually, sorry, that’s I would say roughly about 10 to 15,000 projects a month that we’re funneling through our system. And our client count and employee count has actually held pretty steady over the years, but our revenue has grown because we’ve we focused a lot more on I’d say more mature businesses um you know, companies that just need ongoing stuff. And um and I’m sure with many of the companies you’ve talked to, we found a lot of efficiencies in the even the the recent years like with our engineering team and AI coding tools and stuff. So you know we’ve been hiring much slower than we have, you know, four or five years ago simply because we seem to maintain our deadlines. We’re hitting our targets. Um but it is it is always a question in my mind and you know how far could that go?

[20-minute mark]

Uh and thankfully for you know where we’re at the clients that we work at work with end up staying quite some time because once it’s a into year once a service like ours is sort of in the DNA of the company like hey anytime I need something I just log in and make a request and in the next day I have or sometimes same day I have a draft I have a concept I’m ready to go. becomes very, you know, part of their business growth strategy is like, hey, we always can create. We’re never bottlenecked. We always have someone available. Um, but it does take some time, you know, and we we, you know, the biggest challenge we always face is when someone cancels that’s super happy and has had a great experience because they’re hiring internally or maybe, you know, seasonally they are at a dip and they don’t need our services as much anymore.

Supporting Creatives Around the World

um our creatives around the world. We support anywhere from 300 to 500 creatives seasonally. Um you know, it’s something that is really unique to our model where we’re giving them um their contractors, but we give them guaranteed work for during their contracts. So, the burden is on us to assign the work. So, they’re not billing us hourly or it’s not by project. It’s just like, hey, you show up today, here’s what you’re going to make. Um and it’s and it’s competitive in the markets that they’re in. So, our creatives are in like Latin America, Southeast Asia, and um and it’s a benefit that they can work from home. They can work in their normal hours. Uh they can kind of have a life that isn’t dependent on a huge commute or especially in the Asian countries working graveyard shifts to support Western brands. So that’s something that um we don’t talk a lot about like sensationalize it in our marketing, but something I’m really proud about with the company is just creating those those lives and supporting people to live their lives uh in in countries where there’s not a lot of jobs available.

Yeah. Yeah. That’s awesome. It sounds like that would be quite a uh you know system to uh that would be required to manage all of that.

The Technology Behind the Magic

Tell me a little bit about, you know, what type of a back-end system you have to have to manage, you know, all of your clients and all of your contractors and get them get the, you know, the projects lined up to contractors and kind of how that works.

Yeah, it’s um it’s a monster. Uh so we had to develop our own custom software. We call it JAR just to stick with the pickle branding here. And this software really has two two clients. The first is you know the clients who need design and they can log in and there’s you know really what it is it’s a creative it’s a creative operations platform. So in addition to um you know getting the designs we have AI to help you write the request we have file management brand profiles approval tooling um all the things that often are individual apps we have in one platform. So that just is efficiency for any organization who’s using it. Yeah. And um because you know if you think about it, if you’re not using JAR, you have a project management tool, you have a file management tool. Maybe you have a brand thing, some PDF floating around somewhere. Most often approvals are not being done with a tool. They’re doing done in Slack or email. Uh and uh if you’re real fancy, you have another tool for that. And the list goes on. So we’ve tried to consolidate that and then on the back end is where the magic happens with all of the the automation and assignments.

[25-minute mark]

So when creatives are onboarded they’re assigned to um certain regions and teams to support different geographic clients and then our system every day ingests all the requests gets them automatically assigned to the right teams uh which is complex because if you’re doing motion graphics that’s a different designer than if you’re doing illustration or some other type of design. So, we get all the time. It’s like, “Oh, well, I want to work with the same designer.” And I’m like, “Uh, you kind of don’t actually.” Like, if your designer doesn’t know how to do the thing and is just kind of winging it, it’s not going to be a good quality product. So, we pod up designers so that there’s a skill set expert on each pod and then clients will get assigned to that. Um, but yeah, dude, it’s it’s been a it’s I mean, really, the modern day platform has been under development for about six or seven years. We’re improving it all the time. Um, but it’s it’s it like creativity is complex, you know? So, you’re imagining you’re managing emotions. You’re imagining people’s ability to communicate. Like your version of what’s good is different than my version of what’s good, which is different than the designer’s version. So, um, you’re getting into all these nuances that aren’t really present when you’re just a software company or maybe manufacturing where it’s like, hey, these are the specs. This is how it should work. Is that true or not? For us, it’s like, do you like it? Like, we hope it’s there and, you know, so there’s a little bit of a of a frustration. Um, but it’s on us to make it as easy as possible for clients to create.

AI Tools That Actually Help

And um, I’ll give an example. Our new AI tool we’re launching soon. I mean, it’s it’s it’s it’s great because you basically can go in and be like, here’s what I’m doing. and rather than in like current tools today where it’ll be like awesome you know Ryan here’s all the things I think it does that but then you’re like great send to my designer and then it’ll break everything out into the deliverables and specifications and and you’ll get it to your designer with just this radical clarity so that they can make everything exact rather than you just looking at chat GPT with a bunch of ideas and be like okay now what do I do so um yeah yeah and you know and I don’t know. I always joke like with people who are like, “Oh, there’s these tools are really great in design.” I’m like, “I’m telling you what, the next time you’re three hours in trying to do something with one of these tools, just think of Design Pickle because I guarantee you you should be using that time differently.”

Yeah. Yeah. Right. Yeah. That’s that’s incredible. It sounds like you’ve really got a system in place for, you know, managing this. How what did that take? Like what type of resources did that take to initially get going? And was that kind of the core foundation of getting design pickle going or did you were you doing it more manually before you kind of built the platform in the background?

From Janky to Sophisticated

Oh man, Ryan, it was so janky back in the day. Um, which is to say like man, looking at all of the vibe coding and AI coding tools today, I just could only have dreamed to have that 10 years ago. But um but yeah, it was like off-the-shelf things stitched together, uh customer success ticketing tools, uh Box.com for file management, like it was like tons of step-by-step checklist that just had to manually be followed for the process. But then over time at we started to get to a point of scale where like, hey, this is breaking or will break if we don’t fix this. and like endless security vulnerabilities, not necessarily with like privacy or data, but you could like easily log into the system without a paid account if you kind of could figure out the the emails and things. And so I hired originally a contract engineering team and then brought everything in house. So today we’ve about 10 people on the product and engineering team that are focused on building out the the product every day. And and it is like I said, two clients. It’s like the paying clients and then the creatives because the creatives show up every day to use this tool and so we have to really be thinking about their experience as well.

[30-minute mark]

Yeah. Yeah. That’s incredible. It’s almost like you’ve kind of built your own Upwork system for you know your own clients and and designers and and you know all those people to work together and and come together to make it work. So I can only imagine how big of an undertaking you know that was to start and continue going. But it’s pretty cool that you’ve been able to utilize that into your business and, you know, make that because I’m sure that’s such a huge factor of, you know, your success now is making all this work together smoothly.

Stripping Away the Process Friction

Yeah. I mean, it’s certainly helped and it’s never perfect, but you know, my theory was to make it um like strip out all of the the energy people spend in the process of design so that they can focus just on the design part and the feedback and creativity because you mentioned Upwork, great platform, um similar Fiverr or other tools, but there’s like who do I work with? What is the cost? how what’s the scope now? What are the things? Oh crap, something changed. Now I’m going to get build for it. Like there’s a lot of time and energy that’s spent not in creating the thing you need. And so same goes for agencies, you know, like, okay, we’re going to have this meeting and this meeting and this meeting and eventually all of this adds up either to time and or money. And so I just said, “How could we strip all that away?” So when someone gets signed up, yeah, you got to, you know, it’s good to get onboarded, make sure you know to use it, do, you know, do your call with a rep, make sure you get all the directions, but once you’re done with that, you just create and that’s it. And if your designer is like sick, you’ll never know, you know? And if they’re not great or working on it, you can like call us and talk to somebody about what’s going on. Like I challenge anyone to call someone at Fiverr or Upwork like support-wise like you can’t even find a phone number. So like we really make it just this like extra level of support and combined with just like less decision making, less energy spent. And I think that’s like the other side of the success. The system has to work. If it doesn’t work then we’re sunk. But why do we grow? Why do we keep clients is because they can just focus on their real their role, their business, ship all the creative stuff to us, get it back in however they need, and they’re off to the races. They’re not stressing out about their designer going on vacation for two weeks and like, “Oh crap, what am I going to do?”

Yeah. Yeah. That’s that’s a lot of problems that the that you’ve solved. Um sounds like, you know, in a in a pretty creative, successful way. So, yeah, that’s great.

Building It Incrementally

uh you know how was it difficult to initially build the system in the background? Would it did it take a lot of resources where you were like man this is going to either make or break me or was it like you just kind of tackled a little at a time and utilized you know income coming in and it wasn’t that big of a deal. I’ve always wondered about that because I think there’s a lot of great ideas out there that, you know, people have as entrepreneurs that, you know, they need something like this in the background and it’s such a beast to try to tackle that it kind of stops them from, you know, pursuing something like you’ve done.

It definitely was incremental also because we started bootstrap so I didn’t have a ton of capital available. Um but it was also like testing the system building a little bit testing the system what am I getting back is it working is it not is there confusion and then iterating from there so because creativity is so ambiguous from start to finish and that’s different for everybody I think it would have been impossible for me to just sit in a room with some great designers and great engineers and just make it all from scratch and it be Right? And there’s always like like iterative testing and you know this and that and the other. I think it’s even more true for a company that’s providing a service because the variability of your human client is like a real curveball that you have to understand much deeper than you do if you’re doing accounting software or if you’re doing you know something for like you mentioned like SEO and hey the website just needs to perform this way and rank this way and if it is great and it’s going that direction great and if it’s not then that’s you know we’ll fix it.

[35-minute mark]

creativity is like, you know, you’re we’re parttime like a psychiatrist at times. It’s like, you know, I’m so mad at my designer. It’s like, what? You’re mad at them? Like, why? And, you know, and you have to like have these like these therapeutic conversations because like a color was wrong or something and you’re just like, okay. And you and you meanwhile, they never specified what they wanted. So, now you’re like happy to like be a mind reader, too. Um, but I do think like I wouldn’t have changed like knowing what I know today, the tool itself creation would be easier with a lot of the ability to prototype and create things with some AI coding tools, but I would say the process would still be the same. Just build a little bit at a time. Put it out to the audience. Is everyone having the expected experience? Is everyone getting what you want them to get? And if the answer is yes, keep going. If the answer is no, identify what the problem is and, you know, fix it.

Yeah. Yeah, that makes sense.

Marketing a Unique Solution

Tell me a little bit about some of your uh your marketing and and promotion and that sort of thing. Like how do you get business to you today and what does that look like versus, you know, maybe in the past what you started out doing to try to bring business in?

Yeah. So I actually this is this was a trip down memory lane for me when I was writing uh the book the creative CEO because when we started just our existence got us business and that was an awesome season of life because we were selling it in a unique way flat rate it was subscription it was a you know much cheaper than it is today because we had much smaller company and that was 10 years ago. Everything was cheaper 10 years ago. Um but then eventually we realized well th this is not sustainable and then we start to see competitors and copycats and things. So um we leaned in really heavily into paid advertising and still do to this day with the combination of like outbound and organic marketing um to bring in targeted leads. But I found that like this is a very unique problem we’re solving. not not the thing we’re doing but when someone is ready to buy is very small window generally for the right kind of clients for us. So, you know, working with a designer, if the relationship’s going great, you’re not looking for other designers. You’re not like thinking about solving this problem. It’s only when things aren’t working or you’re facing like some kind of issue that you’re like, well, maybe I need someone else. And that window of time could only really be a week or two long and then it’s closed because you fixed it, you know?

[40-minute mark]

And generally our clients know somebody, they’ve worked with agencies, they’ve hired somebody, they can figure it out, they can solve this problem themselves pretty quick. So what we thought, we we just have to always be out there with brand marketing and stuff and being out there. We just have to be top of mind and it’s why I do podcasts like this. Probably a lot of people aren’t going to need someone right now, but I’ll tell you what, in 3 months from now, they’re like, I remember that pickle guy talking about design. I’m gonna go go look them up because my designer just, you know, crapped out on me. That’s when we want to get you. So, paid advertising has been the way to do that. Just branding, content, creativity, um, and then traditional, you know, funnels to get people in through retargeting and learning more about us. But um but yeah, and you know, we’re we’re we’re in the middle of learning more about what we can do for um organic and the organic ple piece has always been a bit of a of a brains scratcher because anyone looking for a designer through p through search is not a client we want. It’s like, you know, your your grandma who’s like starting a cat clothing business and is like, “How do I fire find a designer?” Like, we don’t want that client, you know? So, search is like a little tricky, but we’re still we get better at it every day. And interestingly, but really, I would say the bulk of it today is our our paid efforts.

Has it always been that way? I mean, you said that you were kind of getting discovered just based on, you know, who you were earlier, but did you do ads early on as well or did you not even need to?

It was pretty early on. I mean, I was in a mentorship and coaching program and I was told by the guy he was hosting an event and he said, “You cannot come to the event unless you start doing paid advertising.” I was like, “Okay.” So, I logged into Udemy at the time and took a Facebook advertising course and then I launched my first campaigns like a few weeks because before this event because I wanted to go. So, yeah, it’s been it’s been from the beginning. Um, I would say that like that may not be how I would do it again, but it’s predictable enough and I think a unique enough content and creativity, which I’m confident we can do, is is still able to drive results.

The Pickleball Championship Flop

Awesome. Has there been any unexpected, you know, marketing channels or, you know, that you felt have also maybe worked a little bit or any that were big failures that you were like, I would never do that again that you learned from in the past?

Yeah. So, um the the ones I love the one I love the most and it’s just really hard from a cash standpoint or event is event marketing. Um we have great success with it. We’re generally usually the only company out there doing what we do and you can just target the heck out of it. You know, going to an automotive marketing conference or a, you know, a a sales and marketing conference for dental practices. There’s just a million choices. It’s just a heavy cash outlay with quite a a delay on the ROI. And if one misses, then you’re you’re hosed. You know, it’s it’s not like you’ll still get something. it’s like you either hit it or you miss it and there’s nothing in between. So, we’ve dialed back on that. Um, also because I think the scale that we need to really move the needle requires pretty large events which are six figures and up in terms of the investments. Uh, the biggest failure was an event and it was sponsoring the 2017 World Pickle Ball Championship in Kasa Grand, Arizona, which if you don’t know is like a retirement community. Uh it’s still on CBS Sports on YouTube. We were the title sponsor of the whole thing. It was like eight years too soon because it was not at all popular like it is today. Uh and the demographic was basically, you know, 60 plus of retirees. So cool branding, cool marketing, wrong audience completely, but at least but to see our logo on CBS Sports as they were televising this and on the courts and stuff was pretty wild.

[45-minute mark]

That’s awesome. Do you feel like there was any confusion or anything where your company name pickle with pickle ball? No. LikeRetry

Like where do you have pickles? Are you pickle company? Do you you design custom pickles? Like I would like to make my own pickle. Like so much confusion. There always is a little bit. But if we’re at a marketing conference, people get it pretty quick.I guess I guess that’s what you get for having a very memorable name though. You know, I think there’s going to be a little confusion about, you know, what is it that this company does with uh, you know, with anybody that doesn’t have a name that’s centered around something related to, you know, exactly what you’re doing, but then it’s more memorable, too. So, you know, you got to you got to you got to take the both sides of it, I guess.

Exactly.

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Systems That Scale: The Foundation of Growth

Uh, what type of systems and operations do you feel like you put into place that has made your business run smoother today? I mean obviously you’ve got a ton of systems you know with your uh like the platform and that sort of thing but just overall in in the sense of business in general what kind of systems have you put in place that have made it easier to scale and grow?

Yeah, I mean I disclaimer have since invested in this company, but a company that I partnered with early on to kind of document and guide all the systems uh and it works so well is why I invested in it is a company called Trainual uh T R A I N U A L and they’re basically help you build a a playbook for your business. So when I was just by myself, even before I launched, I was documenting processes and documenting steps and creating checklists and I think that’s that’s so important in some industries like if you’re a pilot, you live and die literally by these. And if you’re um in a construction, you know, the good ones follow it. And then there’s some industries that they just winging. There’s nothing. And creativity is kind of one of those industries. You know, there’s so many times where people are just winging it and it’s you’re just generally a little bit smarter than everyone else and can get some results and you just do that every time, but that’s not scalable and that’s doesn’t help you improve. So, um I knew if I was going to grow a real business, I needed to have it operate a different way. So, I documented and created processes um from day zero. And then all of that went into trainual. And to this day, you know, a good chunk of our new employee training and onboarding and all this stuff about what it is to work at Design Pickles handled from that as well as other other processes and systems. And so whether it’s that tool or another, I mean, that to me is like the gamechanging thing. You know, I could I could talk to you about some cool piece of software or I could talk to you about come some cool thing, but that’s just going to change in a year or two and there’s going to be something better. the real fundamental DNA of a business that can be grown and also like not causing you to go crazy is that you have your company documented and and and and every company can do that and I talk to creatives all the time like I can’t do that I’m creative I got to do it this I was like no maybe not like one little piece of it that’s like your value but everything else absolutely can be and um and generally when I see problems in businesses is it’s like well show me the show me the communication show me the process and there’s just nothing so it’s like usually the source of most of our challenges as well no documentation

Yeah I hear you um

Writing The Creative CEO

tell me a little bit about your book um what was like your motivation to to write that was it more about you know kind of building more authority and kind of being another channel to you know get out there or was it more about hey yeah I want to write a book and see what I can do with it you know and see what it can do for me just having a book out there as far as selling it.

Yeah. I mean, so I always wanted to write a book about design pickle, but until this thing sells and I’m like on a boat somewhere in the Maldives, I feel like that’s that story is not ready to be told yet. And so what I did realize though is um there were some things some accidental some intentional that that led to our growth and our success. And actually it started as like kind of like a little mini essay I wrote called the creative CEO manifesto. It’s the first chapter of the book and it was just kind of like here’s what the modern-day leader should believe especially if you are touching creativity somehow. Now, my book is written towards someone who’s either like selling, managing, or producing something in the creative world, but I’ve since had like accountants read it, uh, payroll people read it, manufacturing people read it, and they all have been very generous with their feedback and just saying like, “Hey, this works for me, too.” So, um, but the idea behind this this manifesto was like, “Hey, today you really have to like think differently if you want to succeed and really grow.” And then that became sort of the DNA for the book itself, which was focused around um what I looked at when I looked back 10 years of design pickle really distilling down into six pillars of of what has driven Design Pickle to be successful. Any one of these could help a company, but all six really take things to the next level. Um productizing, you know, creating a system around a specific service or deliverable. uh the positioning which we discussed earlier, systemizing and documentation which we already discussed. Um magnetize which is about like how you market, how you message, um optimize which is which is about growing and doing that efficiently and then maximize like more about what outcome you want for your business and life and um and making sure your business serves that. So, the book became kind of this like organic um thing.

Actually, literally just this morning, I published a blog post on how I wrote the book because I did use some AI very uniquely. So, if people want to go to russperry.co, russperry.co, it’s all there. They can just read it. Um, I go through my whole process of how I wrote the book. But really in a weekend I was just like playing around with my notes and some old blogs and this essay and some ideas and an outline. And then like two days later and three days later I come out of the cave and I had my manuscript done. Like it was like bam with it all. And then I just said look I’m not going to just sit on this. I want to get it out there. I want to help other leaders create a better business and kind of get unstuck wherever they’re at in their life.

That’s awesome. Sounds like there’s a lot of good information to, you know, kind of get yourself in the mindset of, uh, you know, thinking about how to build a business.

The Power of Investing in Yourself

[50-minute mark]

What would you say, you know, as far as your success has gone, what would you say the top contributing factors have been as far as, uh, your mind state and habits go?

Um, continuing to invest in programs and coaches to improve them. That has been the number one thing. So many people will invest in all other areas of their life with stuff, with things, with trips, with whatever. They’ll invest rightfully so in their family and their kids and their employees and their teams. And yet they don’t do that for themselves. And so like we shared at the beginning, design pickle came in a season of life when I was doing business coaching with a woman. there would be no design pickle had I not been in that container meeting with someone once a week and talking to them about my challenges. She she didn’t like come up with the idea. It wasn’t that that like that was the the spark, but the space that was created inside of that relationship is what created the spark. So for me, I I unabashedly say my growth and my success has been because I continue to invest in my growth and my success. And some seasons of life I’ve done a really bad job at that and that’s been really hard parts of my life. Uh other seasons I’ve I’ve I’ve done great and things grow really well. But I’m no fool. And I know that what I want 10 more years from now, the guy that you see here right now, there’s no chance in hell that he can accomplish it. So I have to be growing and I have to pull in resources, knowledge, practice, challenging things to get to that point.

Yeah, that’s good advice. Um, tell me a little bit about just, you know, running a business. How has that impacted your life compared to, you know, maybe before you started a business at all?

The Importance of Clarity in Business and Life

I mean, I don’t remember life really not running a business because my first business launched when I was 22, 23, 42 now. So, it’s been almost 20 years. Um, I mean, I think not to repeat any sort of like canned things that people always say about running a business and and running life, I think success is is about the clarity that you have and what you want to get out of it and and the impact that you want to make. And I didn’t have that clear for many years. And it was really really hard to have a business, have a family, have a life, you know. And once I got clear like the business wasn’t easier, but at least sort of like I was able to track my day, my week, my month, my year towards something concrete. And when I was getting closer, it only fueled me faster. And when I was getting further, I would course correct and figure it out. So, I think you know it’s the most rewarding thing ever to create value in a system that you created, which is what a business is. It’s like your ideas, your your processes, your things. Um, but if you don’t have a clear compass for your own life and why you’re doing it, then it could consume everything else around you and inside of you. And um and that’s a far harder position to be in than just going to get a job.

Yeah. Yeah. Uh as far as success goes, I mean a lot of people have different ideas of what success looks like. Um do you feel like you’ve achieved success in this business? What does that look like for you?

Defining Success: Changing Lives Through Creativity

Um yeah, of course we’ve achieved success. Um is it the end goal yet? No. You know we have many years ahead of us. We have a huge vision. Our vision is to change lives through creativity. And I want to see design pickle impact the lives of thousands of creatives around the world who are I mean think about it this way. AI design tools are going to create the most talented designers we’ve ever seen ever because those tools are so easy to use. And if you’re creative mind, but you didn’t have access to Photoshop training, you didn’t have access to working in a job where you can learn all this stuff, these tools are going to going to take these creative minds that have been maybe unable to get the the education they need and immediately they’re going to be able to be create as creative as someone with 10 years of experience in Photoshop. that’s going to unlock these mega mega superstar creatives and you’re going to just see content and quality and storytelling go through the roof. And I want to be the platform that ensures all of these creatives can work with businesses who value their talents and want to bring them into their organizations um and do so in a in a in a managed way. If I can hit a thousand creatives that are are changing their lives for the money they make through our platform, that’s when I feel like the design pickle’s done and I’m on to the next. Um, but I mean, I do think God and the success that I’ve had thus far immensely. And, you know, today was the end of it all, I would have, you know, hey, I just wrote a book last week, so I think I’m doing okay. I got I got I got a lot of the box check ticked off.

Yeah. Yeah, for sure. So, what do you think’s next for you? You know, it sounds like you you still got some goals with Design Pickle, but you know, once you hit some of those, what do you think’s next? Do do you have plans to sell Design Pickle? Maybe you can’t talk about it, you know, either way, but

Yeah. No, we can. I mean, we got an investor a couple years ago and the goal with anytime you have an investor is you return that investment. So, my number one goal right now is being a good steward of their investment and creating a valuable asset for another company to take on and continue our mission and vision. Um, what’s that up to me? Honestly, I have I’m a creative guy. I have like 4,000 hobbies that I don’t do. So, it’s going to be a real interesting time and day when I’m not consumed by this all the time. Um but until then you know it’s continuing to lead design pickle and continuing to lead creatives. Um which is another reason why I wrote the book is so that impact people a little bit like asymmetrically you know like they can get the book they can learn. There’s a course that we’re launching um after uh Halloween uh kind of right around Thanksgiving on about the book that will go live. It’s a six week course to dive deeper and I’m doing all the recording for that now through uh the end of the month of October. So there’s just like the main thing which is DP and then just kind of had this side side quest of just like sharing knowledge, giving resources, helping creatives, helping other entrepreneurs. Um and really just a little bit further than most of them, you know. So just don’t do this. Here’s what I learned. Here’s the thing. like the blog post I wrote today on how I wrote my book in a weekend. That’s the kind of stuff I love doing, too. It’s like, “Hey, I just figured this out. Here’s how you could do it, too.”

That’s awesome. Is there any uh particular direction or project that you’re more interested than others that you think might be like that next thing for you that you’ll go after within Design Pickle or after Design Pickle?

After Design Pickle. Um, I would love to um create like a really insane uh like Jay-Z 2000s hiphop music video like on an aircraft carrier that’s like really extravagant with helicopters. That’s that’s been on my bucket list truthfully for like a decade or more is to create a high budget which maybe I won’t even need to it won’t be expensive by then because you just create all the footage with AI but that’s my goal.

That was definitely not what I expected to hear, but very interesting nonetheless.

The truth.

Awesome. I either have like here’s here’s one of my legs. Like it’s I’m either like everything design pickle or obscure random creative things that drive no value to the market. So I really need to focus on design pickle right now.

So creative, right? Yeah. Exactly. That’s awesome.

The One Tip Every Business Owner Needs

[55-minute mark]

Uh what do you think would be the one tip that you would give to, you know, that you think any business owner needs to hear?

I think it’s actually what I talked about the last chapter of my book, Maximize. Know your path. And what I mean by that is why are you doing the business? Is it to sell? Is it to hand it off to your kids? Is it because you have a chip on your shoulder and you want to prove someone wrong who fired you and you’re starting your own thing? That’s a fine answer. There’s no right or wrong answer. But just be clear of why you’re on the path and what you want that endgame to be. and so many things will be easier along the journey. When I knew design pickle was company I wanted to sell, it just was like all these things started to align. Um when I had an agency with no game plan, no long-term vision at all. It was just chaos every single day. So to me, that is the main thing. And there’s no right or wrong answer. You know, I I know guys who are like fourth generation operators of their family business and they have an incredible life. I know people who buy and sell businesses like every few months and they love what they do. So, whatever it may be, just be clear on it and then the near-term becomes a lot easier in deciding which direction you’re going to go.

What do you think changes when you really know why you’re doing what you’re doing? Like that makes it easier.

The House Edge: Your 2-3% Advantage

Well, we have we never are able to know with 100% certainty what the right choice is pretty much in anything in life. I mean, there’s like 99% certainty things like I shouldn’t give a newborn whiskey, but like I don’t know, there’s some grandmas out there who are like actually, you know, they’re having to do this. But so, you know what I mean? It’s like there’s never 100%. But like in business, it’s often like 5050. Like you don’t really know there. It’s like you’re creating, you’re innovating, you’re doing these things. So when you know the endgame, I feel it’s like the house edge in Vegas. Like the house has only a few percentages of a advantage over the player, but over time that adds up to massive profits. And I think when you’re clear on the end destination, you have that two or 3% advantage of making the right decision, which you’re not going to always do, but over time you’ll get to where you want to go.

Yeah. Interesting. That’s a good take. Um, what advice would you give somebody that’s trying to kind of do something similar to what you did with design pickle? Like say they’ve got uh, you know, an idea that they’re they want to try to do something very different. you know that that can be a difficult uh you know more difficult I would say than just a typical business just growing a business like now you’re going to try to pivot and go a direction you know you’re going to clear a new path what advice would you give to somebody that you know has an idea that they want to do that’s just kind of like that you know clearing a new path

well I want to just disclaimer for the audience Ryan and I did not plan this but he just teed me up to be so self-promotional for my book right now it’s Perfect. My advice is to go to amazon.com and type in thecreative CEO and buy the book for nine bucks on Kindle because that’s exactly who I wrote it for.

Awesome.

It’s to transform and take it that new direction. Um, yeah. And actually, you know what? I’ll tell you what, Ryan. If your listeners want to go to my website, russperry.co, co and send me a note telling me they telling me they heard me on your podcast. I’ll just give them a copy for free. You don’t even need to buy it on Amazon. I hope you do because I like the reviews, but like I care so much about this content. It’s not to make money. It’s not to do stuff. Like I just want to get into the hands of people. So if you go to russperry.co, fill out the contact form, tell me you were on Ryan’s heard me on Ryan’s podcast, I’ll give you a copy of the book for free.

That’s awesome. I appreciate that. Sure. Listeners will too. Um, that brings me back to the book. I just I forgot to ask you, what type of promotional efforts other than, you know, podcasts are you doing to try to get that out there that you found have have worked so far? Or maybe

I mean, honestly, it’s it’s organic. It’s my network, social media. I I don’t have a ton of time to be focused on marketing it. I wanted it in my back pocket for moments like this and sharing it with audiences. Um, but it’s a it’s a long play, you know. I’m not done. I already have the second version that I’m planning to launch next year. As I mentioned, the course is we have a pilot um six week class right now going through the six week course. We’re going to relaunch that after after uh Thanksgiving. So, I’m just again like with design people, iterating, testing, iterating, testing. Um I wish I had a ravenous million person email follower list that I could just buy whatever I sell, but I I haven’t been focused on that.

Yeah. Yeah. Um, so yeah, just about getting the ideas and value out there. I wrote this not to make a buck. I wrote this to help change entrepreneurs and CEOs and creatives. So if I can accomplish that, even with one random person who a year from now is like, “Hey, I read your book and it did this and that,” then mission accomplished.

Awesome. I love it.

Lessons Learned: What Would You Change?

What would you say you would do differently if you had to go back before Design Pickle started and do it all over again? What would be the one big thing that you would change and do differently?

Um, man, so many dimensions to that answer. I think I would I would go a little narrower in our target audience of who we were launching towards. Um, I don’t know if if that would make a huge difference, but again, the more focused if we were to have focused to say like like um fitness studio brands or so, you know, just something where it’d be easier to to allocate capital to reaching them and the messaging and then kind of the network effects you get of referrals and all of that. That that would be the one thing. Um I also would if I started it today would just have saved millions of dollars on software engineering. So that’s like there’s like three versions of design pickle that are in the in the graveyard because we had to rebuild it so many times and that’s like millions of dollars of capital. So, um, just knowing what I know now about software design and doing it the right way would just be not even including AI, you know, programming tools, like it would just help so much more get things to market and do it right the first way.

Final Words of Wisdom

That’s awesome. Well, Russ, I really appreciate your time and I think you’ve answered most of the questions I had. Is there any final thoughts with the audience? Any last things you wanted to go over or talk about or any promotions throw out there? or anything like that. I mean, you already did a little bit, but

No, I mean, I just encourage anyone to Yeah. go to my site, russperry.co. You can sign up for the newsletter. Uh, follow me on Instagram, Russ Perry. That’s where I post mostly. And, um, yeah, like I said, if you want a copy of the book, fill out the contact form on the website and I’ll get one out to you. And, um, thanks for having me. I just really, really appreciate it. It’s been a great conversation.

Yeah, absolutely. Really appreciate it, Russ. It’s been really fun. I think there’s a ton of super valuable information that you’ve given to the audience and uh I’m looking forward to reading your whole book and uh you know seeing a few more of your your podcasts that you’ve done and I encourage you know all the listeners to do the same and go check website and if they need a designer I think they know where to go now. So we plugged that pretty heavy so yeah for sure.

All right, thanks Ryan.

Thank you very much.