Russ Perry is the founder of Design Pickle, one of the top flat-rate graphic design services in the world. Launched in 2015, Design Pickle has experienced unprecedented success helping small businesses focus on what they do best. Before Design Pickle, Russ worked at Apple supporting sales and marketing efforts for both the original iPod and iPhone launches. He enjoys traveling with his wife, Mika, and their three daughters.


Russ Perry has come a long way from his stint handing out sealed pickles in conference hall food courts to promote his graphic design agency — dressed as a giant pickle no less. The hustle did not go unrewarded; his business, Design Pickle, transitioned quickly into online acquisition. What followed has been a lesson in marketing, leadership and even software development, all in the name of a dream to make hiring a dedicated designer pleasant and easy. A frequenter of marketing conferences worldwide, Russ asserted that the key to scaling his business to six figures in less than half a year was recruiting a core team with haste — people of all backgrounds, many of whom work remotely. MODERN ONTRAPRENEUR’s Landon and Russ reminisced on the triumphs and pitfalls of their entrepreneurial ventures in this insightful back-and-forth you’ll want to play back at least twice.


2:53 - Hustler in a Pickle Suit
Design Pickle’s rise from guerilla marketing at conferences to a disruptive business model

​​​5:49 - Mission, Vision, Values
​​​​​​​How these three little words changed the game for Russ’s leadership of his new team

8:57 - DIY Scaleable Solution
​​​​​​​Design Pickle’s impressive workload of 400 design jobs a day rests on their proprietary software.

11:47 - Free Graphic Design Education for All
​​​​​​​Russ’s legacy goes far beyond providing a service as a graphic design agency.

13:45 - Overdeliver or Disappear
​​​​​​​Companies fail because they prioritize their product over their rabid fans.

LR Welcome to MODERN ONTRAPRENEUR. Today, we have Russ Perry who is the founder of Design Pickle, the number one unlimited and flat rate graphic design service in the world. Launched in 2015, Design Pickle has experienced unprecedented success by helping small business focus on what they do best. Thank you so much for being here.
The most cliche things that I swear by now: mission, vision, values - swear by it.
RP Thanks man. Excited.

LR ​Design Pickle is a design shop that does a, like I just said, a flat rate service where you pay monthly and you get unlimited design resource access.

RP Yeah. You get matched with a dedicated designer. We pair you up with of our full-time staff, and you request what you need. That's it. Super simple.

LR They get it done. Cool. How you have you been doing that?

RP Since January 2015.

LR Just bran-spanking-new basically. Tell me what you feel like your unique skillset is.

RP Other than ridiculous branding, which we've done a lot of at Design Pickle, I think it's really systematizing and creating simplification out of complex processes. I ran a creative agency for eight and a half years, and we were so complex with how did everything. Then when I closed that, it was really like trying to make it easy for people to get creative and access creativity. I found out sort of a method and a methodology to put all of that together into the startup that we have today.

LR Something about how to systemize the creative brief really. Getting customers to be able to actually tell you what they want so that your designers can do it without having to go back and forth 400 times.
RP Well, and sometimes you have to. I think a lot of people are afraid to get professional help with design because they've been burned in the past, and so our first order of business was just making it easy to just get started. That's where I think a creatives, they throw a wrench in the system. They want to meet you. They want to talk to you. They want to have focus groups, and they want to do all this stuff. In reality, people, they don't even know. They couldn't even tell you what they wanted, so, for us, and really in design in general, it's just like, "Let's get started." Then, "Are we on track, or are we off track?," and, "Let's go from there."

LR You created a process out of that, and it just kind of worked?

RP Yeah.

LR Awesome. You launched just a couple of years ago, and you've had pretty significant success. What has worked to get you business? How did you grow this thing?

RP We joke a lot about the pickles, but honestly the first marketing event we ever did was at a conference in Arizona, the Infusionsoft Conference, and they were out of booth space. I wanted to be there. That's where we're from, and so I negotiated a sponsorship where I got to be in the lunch area handing out pickles. We wrapped them with our marketing materials. I was like, "Okay. This is cool, but I want to level this up more," so I got a $30.00 costume on Amazon and dressed up as the pickle, a pickle, and handed out pickles everywhere. It's actually very notorious. People still to this day talk about it, but the thesis of that just like hustling.


Getting out there, e-mailing, hustling, telling people about it, that got us a lot of momentum. Then we transitioned quickly to online acquisition, so Facebook ads. We do a lot of events, and really just like getting the word out there that, "Hey, there's a new model, a new way to do design." Thus far, it's worked.

LR Basically a pretty, I don't want to say traditional because this is all relatively modern, but the currently traditional setup, which is Facebook ads to probably landing pages, converting them to leads, following up?
RK  We actually tried doing a lot of landing pages, and weirdly enough it overcomplicated the sales process. Now, we have people go to site that it's sort of like, "Hey, do you need design? Yes or no." We found that to be easiest thing. We [inaudible 00:04:20] cycle.

LR You sign them up directly?

RK Just sign them up.

LR Dispense with all the nonsense.

RK We don't know if you're going to be a good client or not. We don't know if you can write a good e-mail, if you know what you want, so we just want to get you in the system as fast as possible. If you suck ... I should take that back. If you don't know what you want and are difficult to work with, we'll boot you out. I would say 90% of the people who get in like it because it's new and we're friendly, and we really are committed to that outcome, which you don't sometimes get with the design community.

LR Interesting. It's Facebook to direct to sign up, which is less traditional, and then hustling, getting out, meeting people, shaking hands, making relationships.

RK Handing out pickles.

LR Handing out pickles, obviously. It's worked well. You've grown to how many people on your team now?
RP We started off with me and a designer and a project manager in 2015, and we just got back from our annual conference in the Philippines, and we had 50 people there.

LR Your internal conference?

RP Yeah. That was about 40 designers and 10 of my staff here in the United States.

LR Amazing work. You've gone through a big transition being a guy that was you and a couple buddies to now running a serious business. What is that you feel like you're learning right now? What is the cutting edge for you? What's next?

RP As cliché as this answer is, it's how to be a leader and a manager and a CEO. I can be the guy ... I was talking to one of your team members. I love being the guy handing out the pickles and doing the hustling, but that's not going to be the type of leadership that gets us to the 10 million and 15 million dollar mark.

LR You never know.

RP I do know for a fact that's the key to our success right now is building that core team and allowing those people to grow and succeed. That's been the biggest challenge, because I've never been part of that a large of that organization.

LR What does it look like? What are the challenges you're facing and the skills you're learning around beginning to turn into a real leader?

RP Understanding people's individual styles. We just dove into that recently where we had people do the personality tests and Kolbe tests and really understanding those team dynamics. Communicating regularly. I can be the guy who gets heads down and wants to build marketing campaigns or launch certain ideas or build new products where we've been acquiring a product and doing things, but communicating ideas and vision, which it's always up here, but how do I get that into people's hands and then allow them to be a part of that? That's been a big difference too.

LR Communicating, clarity, making sure that everybody's rowing in the same direction.

RP It's basic stuff that you hear all the time and read in every single book, but then you actually like, "Oh my gosh. That was real. I should actually do that."

LR You just said the story of my life. I've read everything about how to be an amazing business leader, and I don't really realize I read it until after I ran into the problem that it was trying to help me avoid.
RP One of the most cliché things, honestly the most cliché things, that I swear by now: mission, vision, values. Swear by it.

LR Shocker, right?

RP I've heard that so much, and I'm like, "Ah, whatever."

LR You're like, "Whatever. Big corporate nonsense." What does that mean for you now?

RP It's how we guide our team. We have an international team, so many different backgrounds, so many different experiences. I have people who've never even worked in design art. Our head of customer success was an AP high school history teacher. We have this mish-mosh, but everyone's committed, and we're guided by those mission, vision, values to put those out there.

LR It's again about clarity and making sure everybody's headed in the same direction. If you could go back in time and give yourself a piece of advice when you were, say, starting that design agency, what would your advice to yourself be?

RP How far back in time?

LR At the beginning of your career. At the beginning of that agency.

RP Don't start an agency. Get into development and build software. I've learned a lot-

LR Sorry. I'm going to interrupt you right there. You consider your design agency, this thing you're doing now, to be a software company?
RP We're able to achieve our price model and our efficiencies ... We do 400 jobs a day right now, design jobs, because of software. We run-

LR You built it custom?

RP Yeah. We run our own proprietary software that we've built. At the end of the day, it is a service business. It's kind of this mish-mosh. I call it a SaaS as in Service as a Software.

LR What you mean is do something scalable? Not really build software necessarily.

RP Do, but find those simple problems to solve with software. I learned that now later in my career, and I'm now pursuing that more aggressively in other areas. That would be my tip is don't try to do the old thing better. That's what the agency was. The Mad Men agency, I tried to make that cooler. I tried to make that better.

LR How do you make that cooler? It was so cool.

RP Mad Men was cool. A show I had to stop watching with my significant other because I was like, "I promise this is not how it really is."

LR Don't try to do the other old thing better, because everybody's doing that. Try to do the new thing ... What? Completely differently?

RP I would say try to do something new but solve a simple problem too.

LR Solve a simple problem. The simple problem in your case is that design is expensive.
RP Yeah. It's a hassle.

LR It's a hassle.

RP Or was, until Design Pickle came around.

LR  No longer a hassle.
RP No longer.

LR Something scalable, and you feel like software is the access to scalable solutions whether you sell the software itself or whether you use it internally to solve a complex problem like getting design done. That would be the piece of advice is like quit screwing around with hourly work.

RP Exactly. Maybe go out less. That'd be [crosstalk 00:10:31].

LR Maybe go out less.

RP That'd be another tip. Party less. I'm married with three kids now. Those days are a lot, but I went to Arizona State University. Let's just say there was a lot of nights where I could've been building stuff I was out working on other projects.

LR If you look forward to the end of your career or even life, what do you imagine that you'd like your legacy to be? What are you working for?
RP I think about this a lot. Our vision is to change lives through creativity, and I think I want to get to the point where I'm helping distribute free design education. Allowing people to enter into the vocation of design without having to go to an expensive design school, without having to live in a city, a New York or a Chicago or whatever, and allowing that access because it is an amazing career. Everything needs to be designed at some point. To be able to distribute that and make that just massively available, that's where I want to get to.

LR It's so interesting, isn't it, to notice how many people come in here and talk? When you ask them about what their legacy is, they don't talk about their customers. They talk about their team and the difference that they feel like they can make for their people. You're talking about obviously for your people but also for the entire industry. Very interesting. It sounds like you're beginning to build a foundation where you might be able to do that through this business.

RP I'm hoping. So far so good.

LR What do you feel like it means to be a Modern ONTRApreneur?

RP  A modern entrepreneur? I think it's about understanding the entire business lifecycle from the point someone sees your website for the first time to understanding who you are to experiencing those mission, vision, values, and how you deliver on everything that you're trying to sell people on. You cannot succeed today unless you understand that full 360.

LR The whole process from first interaction all the way through the experience-

RP And beyond.
LR And beyond. How do you think business has got away without having that kind of vision in the past?

RP That's a good question. I think there was a lot of margin for error. You had to have a lot of money. You had to be a big enough size, and you could get away with a lot of crap. You could not care about your customer experience, because you were the only game in town.

LR  You weren't competing with the whole world.

RP Exactly. We were chatting before how there's a lot of knock-off competitors that we're having. I don't worry about it because of our complete culture and the experience people have, but I also know I can't rest on that. I have to over-deliver every single time, because I make one wrong move and I can gobbled up. That's now the reality of this economy, and I think it keeps everyone on their toes. If you don't understand that, it's going to be just a couple of years.

LR Amazing for the consumers, right? Amazing the level of service and the level at which we need to be delivering in order to even be competitive today.

RP  People want to care about a brand. They want to like it. It's not just good enough. I can think of a company in my hometown that's not doing so great because they cared so much about their product and not about the experience and not about creating rabid fans and people who are passionate about your vision and meshed with that. You could have an okay product but a ravenous fan base, and that's going to be the difference maker. You can have the best product in the world, but if you don't have something that someone actually is emotionally about, in a positive way I guess, then it doesn't matter.

LR What do you think makes people get emotional about a brand?

RP Being authentic and real and telling the truth and admitting when things suck and talking about things that are hard and doing stuff like this. I mean, this is what people want to experience.

LR Just real people being authentic. Cool man. Really great to have you on the show. Thank you so much for doing it.

RP Thank you.

LR I appreciate it. Will you sign our ... Wait, we didn't talk about your ... What is this?

RP In the spirit of creative marketing, me and my marketing director put out an EP. Go to designpickle.com/rock to get the digital download. It is two fully produced albums about our design services.
LR Songs. Songs.

RP Songs. Two fully produced songs about our design service. I'm just not going to brag too much but ... My wife, when I told her about this, she's like, "What are you doing? What do you do at work?" No joke, later that night she was humming the tune of one of those.

LR Boom. Got you. Will you sign our wall?

RP Absolutely.