Scaling Up a Service Business: From Idea to $400k in Monthly Recurring Revenue (Greatest Hits)

22 Feb 2024 · 45 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Podcast Notes: The Side Hustle Show

Episode Title

Scaling Up a Service Business: From Idea to $400k in Monthly Recurring Revenue (Greatest Hits)

---

Episode Overview

  • Host: Nick Loper
  • Guest: Russ Perry, Founder of Design Pickle
  • Main Topic: The journey of scaling Design Pickle from inception to achieving $400k+ in monthly recurring revenue within three years.
  • Key Themes: Business model innovation, marketing strategies, operational efficiency, and customer retention.

---

Background of Design Pickle

  • Founding: Established by Russ Perry in January 2015 after closing his creative agency.
  • Service Offering: Unlimited graphic design services for a flat monthly fee.
  • Initial Struggles: Perry transitioned from a traditional agency model, which he found suffocating, to a scalable subscription model.

---

Key Insights from Russ Perry

  1. Transition from Agency to Subscription Model
  2. Pain Point: Perry felt trapped in his previous agency, experiencing burnout and dissatisfaction.
  3. Strategy Shift: He sought to create a simpler, scalable service that decouples income from time.
  1. Marketing and Customer Acquisition
  2. Initial Marketing Efforts: Engaged in extensive guest blogging and direct outreach through email campaigns.
  3. Sponsorships: Participated in trade shows, dressed as a pickle for visibility, and engaged in B2B marketing.
  4. Target Audience: Focused on small to medium businesses looking for ongoing design support, avoiding those who just seek one-off projects.
  1. Pricing Strategy
  2. Flat Rate Offering: Initially offered multiple plans, but simplified to one plan to reduce customer confusion and streamline sales.
  3. Value Proposition: Targeted clients who recognize the value of ongoing design work at an affordable price point.

---

Operational Strategies

  1. Hiring and Team Management
  2. Outsourcing: Built a dedicated team of designers, primarily based in the Philippines, compensating them well above average rates.
  3. Culture Building: Emphasized mission, vision, and values in hiring and team operation to foster a positive corporate culture.
  1. Customer Service and Retention
  2. Churn Reduction: Focused on finding the right clients upfront to reduce churn and improve customer lifetime value.
  3. Direct Communication: Maintained open channels for feedback and provided options for clients to switch designers if needed.
  1. Infrastructure Development
  2. Custom Software: Developed an internal tool for managing design requests efficiently, which was later spun off into a separate SaaS product called JAR.

---

Takeaways

  1. Proactive Marketing: Success requires active marketing; establishing visibility is crucial for attracting clients.
  2. Remove Yourself Early: Transitioning roles from the operational level to a more managerial perspective is essential for scaling.
  3. Sell Your Tools: Once a successful internal tool is developed, consider offering it as a product to other businesses.

---

Future Endeavors

  • Upcoming Book: "The Sober Entrepreneur" focusing on Russ's personal journey and the broader themes of sobriety and entrepreneurship.
  • Continued Growth: Design Pickle has continued to grow and adapt, achieving significant revenue milestones and evolving its service offerings.

---

Conclusion Russ Perry’s journey illustrates the potential of transforming a service-based business into a scalable model through innovative marketing, effective team management, and a strong focus on customer satisfaction. The episode serves as a guide for aspiring entrepreneurs looking to establish and scale their service businesses.

---

Additional Resources

  • Design Pickle: [Website](https://www.designpickle.com)
  • Russ Perry's Book: [Sober Entrepreneur](http://soberentrepreneur.com)
  • JAR: [JAR HQ](http://jarhq.com)

---

Notes Compiled By

[Your Name]

Date

[Today's Date]

Reference

[The Side Hustle Show Podcast Episode]

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Let's be real. Nobody starts a business for the joy of calculating tax withholdings. That's where our partner Gusto comes in to take the stress out of payroll, benefits, and HR, so you can focus on why you started your business in the first place. Gusto is online payroll and benefits software built for small businesses. It's all-in-one, remote-friendly, and incredibly easy to use. So that means you can pay, hire, onboard, and support your team from anywhere. I'm talking about automatic payroll tax filing, simple direct deposits, health benefits, commuter benefits, workers' comp, 401k, you name it.

0:34Gusto makes it simple and all with no hidden fees, no surprises. Plus, if you have any questions, their team of certified HR experts are standing by to help. It's no wonder why more than 400 ,000 small businesses already trust Gusto and why it's the number one rated payroll software for fall 2025, according to the review site G2. So try Gusto today at gusto.com slash side hustle and get three months free when you run your first payroll. That's three months of free payroll at gusto.com slash side hustle. One more time, gusto, G-U-S-T-O dot com slash side hustle. Here's an oldie but a goodie from the archives from the Side Hustle Show Greatest Hits Collection.

1:17Scaling up a service business from idea to$400 ,000 in monthly recurring revenue. What's up, what's up, Nick Loeber here. Welcome to the Side Hustle Show because your idea of success might not coincide with your bosses. Our recurring revenue theme for the month rolls on this week with the crazy story of a side project that's turned into a multi-million dollar a year business in a little over two and a half years with just one service offering. You've probably heard of productized services before. These are businesses that take skills normally sold on a project basis or an hourly basis and it sells them like their products with flat fee packages and they're often sold on a monthly subscription model.

1:58Like most recently, we heard from Gabe Arnold from Copywriter Today, which sells article writing as a monthly subscription. And when we caught up in episode 205, he was up to$20 ,000 in monthly recurring revenue. But today, I want to introduce you to Russ Perry, who took this model and took some inspiration from another Side Hustle Show guest and created a really cool business called designpickle.com. The service offers unlimited graphic design tasks for a low flat monthly fee. And maybe the exciting part is, as you'll hear Russ say, is that he sucked at design. It was never about him doing the work.

2:33So I invited Russ on the show to learn, look, how did he get his customers and how did he build up his team to deliver consistent quality results? The pain point for a lot of entrepreneurs and side hustlers in the freelancing or consulting world is how to decouple their income from their time, right? how to stop trading hours for dollars. That's something I think Russ has done extremely well, and I invite you to listen in to hear how he's scaled the unscalable, a service business. Notes, links, and a free PDF download with all of Russ's top tips from this conversation are at sidehustlenation.com slash Russ.

3:07It's R-U-S-S. I'll be back with my top takeaways from this chat with Russ after the interview. Ready? Let's do it. The best place to start is after I had closed my creative agency. So I had an agency here in Arizona and on paper, it seemed like we were doing good from the outside. It seemed like we were doing good, but personally I was falling apart. I was depressed. I hated the business. I hated my clients. I felt like I was in a prison of my own creation, which is not a good place to be in. So I closed it all. And in late 2014, found myself with a sizable amount of freelancing clients, considering I was just me going from 20 employees of my agency to down to no employees and a laptop and a coffee shop and ended up like kind of creating the systems around Design Pickle that were the foundation of what we do today.

4:04Because I was fearful of creating another agency. I was on this path. I was like, oh crap, I'm getting these clients and now we're doing this design work. And pretty soon I'm going to have to hire people. And it was this flashback, like, no, I don't want to do this again. I'm just following the same abusive path that I just escaped from. And so I actually then took a moment and stepped out and kind of created a little automation, a few really simple things between a ticketing service and a generic email address and a couple of freelancers that became the bones of design pickle to manage inbound design requests really seamlessly and pull me out of those weeds.

4:46And it wasn't until December, well, probably late November, 2014, when I read seven day startup by Dan Norris. And I was like, dude, this is my business. Like he has the same thing, but he's doing WordPress updates and I'm doing design. I need to brand this sucker. I need a launch. I need to go, which is of course the feeling you get after you read that book, you're like ready to launch anything. And we did. And we launched in January. Had you connected with Dan before the book? No, dude, I didn't even know. I think I knew of him because of the Dynamite Circle content and connections, but I didn't even know.

5:21I didn't know him personally. I just picked up the book and I was like, this is a great book. And this is really, really applicable to where I'm at. A couple notes here. Dan was a guest on the Side Hustle Show in episode 132. If you want to check that out. We talked about the seven day startup book and his experience in running several different businesses, including WP curve, which offered unlimited WordPress support for a flat monthly fee and was ultimately acquired by GoDaddy about a year after we recorded that episode for an undisclosed sum. Also the dynamite circle that Russ mentioned is a private membership community that focuses on location, independent businesses, location, independent entrepreneurship, and it's run by the hosts of the Tropical MBA podcast, one of my longtime favorites.

6:10All right, let's jump back in. Yeah, because it sounds like he kind of came from a similar background of having this web design agency that sucked. And despite getting more and more clients, like having to hire more and more people to service those clients and just going backwards, like not making any money, not having a good life. And maybe we can really strip this back, simplify it and say we offer one thing. Yeah. And it's the path I think every creative agency type person wants to go down and ends up some are successful on that path. But ultimately, I think what you see people really break out and, you know, just not design people, I've seen people break out with niche photography service, niche copywriting services.

6:55It's like finding an angle and a niche and making it super streamlined, making it really smart how that experience is driven. And that kind of is the name of the game now. You know, that like to me is you see a lot of products, whether they're SaaS products or service-based where you have somebody who escaped and now just does one little piece of it really, really well. Yeah. Was it primarily design that people were hiring you for? It was a really broad spectrum. Initially, I was doing design, but I was doing website buildouts for WordPress sites. And I was doing branding and logo design and brand strategy and trade shows.

7:31So these little projects were annoying. They were important when the CEO of your consulting gig that's paying half of your life's expenses needs a business card. But at the same time, I mean, I was out of the design game for a long time. I hadn't cracked open Illustrator in years because I always had a team. So I was like, well, the truth is I kind of sucked at design. So I was like, man, I need to find someone else to do this. Otherwise, I'm going to give them a really crappy business card. And that ultimately was when I hired some freelancers. But again, I was like, I'm not going to just, I'm not going to be that same model.

8:09How can I be smarter about this? And I thought, well, ticketing tools, they're really helpful. I use them in customer support situations all the time. What if a client could just email this generic tool and some backend support could grab it, design it? And if it was overly complicated, that's when I would jump in and be like, help out a little bit more. Okay. Yeah. So maybe beyond that, that's all it was. And that's what it remains to, to this day. It was just, let's just create a really focused, really reliable way to get this piece of design done. And ultimately when I took a step back, when I had all this spectrum of design work, then creative work and branding and consulting and marketing that I was supporting, I said, hey, it's not that sexy just to focus on Facebook ads and brochures and trade show graphics and the blah, blah, blah design.

9:00But dude, that's running really well. And then of course, when I saw the model that existed with WP curve, I was like, I got to go for this. I'm going to try to go the scale route and try to go down a path that I think I could provide this. And then I closed out, it took me six months actually from January 15 to July 15 to unload all of my consulting clients fully. But that was because Design Pickle was growing and growing and growing. So we ended up getting to a point where I could swap out all my income with Design Pickle and went full pickle, as I call it, in July 2015. Those first six months, dude, anyone who would listen to me speak.

9:45I was speaking at the Hispanic Latina business conference and every angle of every business. Were you at Icon in that spring, 2015? I was. Yeah. I was dressed up as the pickle. That was our first marketing event we ever did. Okay. And we were too late to get a booth. So I negotiated a pickle handing out sponsorship where I could stand on the tile in the convention center. I couldn't leave the tile. I was like a dog. It was like hot lava. Okay. Yeah, exactly. Exactly. The hot, if I step on the carpet, I burn to death. But I could stand on the tile and hand out pickles. And as far as marketing and branding, it was massively successful.

10:31But I couldn't even talk about Design Pickle because I was by myself and everyone wanted pickles and it was like a madman rush for the pickles. Wow. So I totally remember seeing the pickle guy there. This is Infusionsoft's conference in 2015. And it turns out it was you. It was me. I'm now retired though. Now you got people to put on the pickle costume for you. Okay. Well, let's dial it back a little bit. Tell me about your first customer. Who hires you specifically for this service? Well, my very first customer was a friend of mine named Will Humphrey And he owned a physical therapy clinics, actually a few of them in Arizona, more rural Arizona cities, not necessarily in Phoenix.

11:13And he, to this day, I know there's still a client and they use this every day. And it was just to help out with an office marketing collateral. So they have a promotion, a special on, you know, back massages or whatever products go on in physical therapist offices. And they had the front desk girl that was doing the design. She was not a designer. She was designing, I think, in Microsoft Word and with whatever resources were available to her. And he wanted to kind of level up his, you know, he had a cool website, a nice brand, good logo, but just not the need for a full-time designer. And we were able to kind of come in and give him a dedicated professional designer, but at a rate and a commitment financially that isn't going to just, you know, crush a small business.

12:03Right. After that, what happens in terms of signing on more people? You say, hey, I got somebody to pay me for this. They put their money where their mouth is. And what happens next? Well, one of our keys to success was charging a lot of money relative to software. Now, it's not a lot relative to a full-time designer, but getting$370 a month, which technically early days, we were only$195 and we upgraded. But even that, getting a couple hundred bucks in immediately, and I get 10 of those clients. It's actually, I think I got 15 clients the first month. That's cashflow. Like, I'm like, oh my gosh, I actually have cashflow.

12:41I can pay myself. I can buy Facebook ads. I could invest it in a sponsorship, which we ended up doing the second month in Infusionsoft. So the price point was so instrumental to our success because we just had money immediately. Now, where'd those 15 clients come from? We did a lot of guest blogging. I did a lot of spamming. In fact, I got blocked by Gmail for a while because I just was like BCCing my entire contact list emails. They did not like that. I'll admit, I got every list of every marketing lead I could find and just blasted them and just said, Hey, we're new. Here's what we do. Check us out if you want to sign up.

13:25And we didn't have a software. We didn't have... I was every job except for design. And it was, we had three different plans, which that was a big mistake. Cause it was, it was all the same thing. I just was like made up some plans that looked different with different limitations. Cause I thought that's what you did when you were a company selling stuff online. Tell me about that. Cause that's an interesting observation on the pricing because yeah, the traditional sense is like, Hey, I have a small, medium, large, cause you never know. Some people are going to pick the large one, you know, but you said, no, we're going to do one service, one price.

13:59I think there are reasons why that works in particular with pure SaaS products or let's say really complicated service models that there's a lot of exposure of risk for the person providing it where they would need to have different limitations because they don't want to just lose money on a client. But for us and what I found was my initial reason to break up these plans. And I created a lot of false limitations because I was afraid of getting taken advantage of. And I didn't really know what to charge truly either. I didn't know what the right price point was. So ultimately, the real simple decision why I eliminated tiers and plans was because all of the differences were Russ Perry made.

14:47They were limitations I had just created for no real reason. And it was creating a lot of sales questions I didn't want to answer. Okay. I was like, well, what's the difference between this plan and this plan? What's the difference between this plan and this plan? And when you're the sales guy and the accountant and the tech support and the customer support and everything else, I just was like, dude, I want to eliminate these sales questions. Here's one plan. There you go. No more sales questions on the difference between plans. Yeah. Fair enough. And it worked. And at that point we had enough data because we did lower, we had the low price, we increased it to 370.

15:20Then we went up to 495 and really saw a drop off. And then finally just settled at 370. And we've been there ever since because it's enough, but it's not too much. You could put that on a credit card and not necessarily raise any flags. Hey, just a heads up that plans and pricing have shifted a bit since we recorded, but the basic value prop remains the same. Sidehustlenation.com slash design pickle is my direct referral link if you want to check them out. And I'll be right back with Russ after a quick word from our sponsors. A lot of side hustlers suffer from what if-itis. What if it doesn't work?

15:52What if I don't have the skills? What if I pick the wrong path? But one thing 100 % of our amazing guests have in common is they took their shot. They phased down those what-ifs and they got their answers through taking action. Our partner Shopify helps turn what-ifs into why-nots. Shopify is the commerce platform behind millions of businesses around the world. From household names to the very guests on this show. What if I can't design a website? Shopify's got you with ready-made templates to match your brand style. What if people haven't heard about my brand? Shopify helps you find customers with easy to run email and social media campaigns.

16:26And what if I get stuck? You can tap in to Shopify's award-winning 24-7 customer support. Let's turn those dreams into and give them the best shot at success with Shopify. Sign up for your$1 per month trial and start selling today at shopify.com slash side hustle. Go to shopify.com slash side hustle. Shopify.com slash side hustle.

16:53As a business owner, you worked hard to make that phone ring, but missing a business call, it's like watching money fly right out the window. That's why today's episode is brought to you by Quo, spelled Q-U-O. It's the smarter way to run your business communications. Quo is the number one business phone system built for 2025, not 1995. In fact, it's rated the top choice for customer satisfaction with over 3 ,000 reviews on G2. Quo works right from an app on your phone or computer, and it means your team can share one number and collaborate on calls and texts, just like a shared inbox. And here is what is really cool.

17:30Because if you can't answer the phone, Quo's AI agent can. It can qualify leads, it can route calls to the right person, and it's going to make sure no customer is ever left hanging. Think of it like having 24-7 support without the 24-7 payroll. More than 90 ,000 businesses are already running on Quo, from solo operators to growing teams. Try it free when you go to quo.com slash side hustle. that's q u o dot com slash side hustle you can even keep your existing number quo no missed calls no missed customers do you find that's kind of where clients are they're you know within some corporate structure that doesn't it they definitely don't have the need for an in-house design staff but they have they have an ongoing need for design yeah and everyone's paid a few bucks for a design job in the past.

18:22They, at least the clients we want. So everyone spent that enough, that amount, like two or$300 on some project in the past. So they have a point of reference. And that's another thing that I learned in terms of pricing. If you're selling something like design, my customers have a lot of experience buying design. If I was to sell, say this like Zencaster software we're using for your recording, well, you know, maybe people have experienced podcasting, but more people don't. So you're really having to sell why there's these features and benefits and why you're different and why you even need to do podcasting.

18:59I never needed to do that for sales. In fact, sales for us was really easy. It's like, hey, do you need design? Okay, here's our price. And again, if you've had that price, if you've bought, say you hired a guy, a freelancer, and he charged you a couple of hundred bucks for a brochure, then you see our offer and you're like, well, wait a minute. I paid just as much of that for one project and you're telling me I can get, I can use you whenever I want. And if the price doesn't change. So those sales, that's that price point was really important to have price context. If I want to call it that I'm just kind of making that up, but like pricing context where there's experience around whatever it is you're trying to sell.

19:37Okay. Have you gotten pushback from people about like, well, you're, you're commoditizing my art or real design can't be done for this price. Yeah, I call that the underemployed graphic design community that hates on us. And it's kind of like, yeah, we've had all sorts of funny things. We actually had a protest, like a coordinated protest from some podcaster in California. and it and they're like form of protesting us was having his listeners dress up as a pickle like a photoshopped pickle and they put their faces in and everyone's giving thumbs ups so it was like this bizarro like avant-garde protest that ends up just like really branding us really well because everyone's dressed up as pickles but yeah people push back and you know unfortunately the reality is if they were making any kind of real money in their life and doing something meaningful, they wouldn't really care about us.

20:35But in fact, they're not, and they're probably broke. So they, they attack us. And my argument is like, it's probably worthwhile, like going to getting clients versus attacking us because truly, because people want to use a design service that doesn't have an attitude and doesn't have an ego and is actually friendly and helping. Now we don't do everything. And that's the other non-chip-on-my-shoulder argument, because he clearly can tell I care about this. It's like, dude, we're not creating responsive websites and we're not creating mobile apps and we're not designing brand structures and hierarchies and content strategies and all these things that creatives can do that we're not for.

21:14But if a dude really wants to go toe-to-toe because he's really passionate about designing Facebook ads, then yeah, we're totally f***ing up his world. And I'm sorry, but that's like, pick a different design niche because we're going to totally eat you for breakfast. Let's talk about the people who are delivering the work. Who's actually doing the design? Like, tell me about your team and kind of the hiring that you've had to do to scale that up. So this is why I'm so passionate. And especially like when people do attack us, because there's a lot of trolls online. I'll light them on fire. We have the most amazing full-time team out in the Philippines.

21:51And we are like, they're our brothers and sisters. We talk with them every day on Slack. They work for us full-time. I mean, technically, they're 1099 contractors from a structural and legal standpoint because they work from home. They meet every box in the 1099 requirement, but they're working for us. We make it a point. We want to be the best employer in the Philippines for graphic design. So we actually pay three times the average salary. We provide health reimbursements. We provide training. One of our team members had a baby recently and we supported her through that process. So it's like a massive big family and we just recruit through word of mouth.

22:31And we have a big event once a year in Manila that we host everybody at. We've done it two years in a row and we're going to do it again this March. But But that's the other thing is like to the designers that hate on productized services for design, the 99 designs and the Fiverr's of the world actually have kind of messed things up for everybody because those business models are designed to increase volume. It's like a credit card company. Credit card companies just want more people to use credit cards because they take a percentage. Fiverr doesn't really care about the quality of the work. They just want more volume.

23:05Whereas we're the opposite. We want quality. We want a good experience. We want everybody together working together and having a great experience because we're going to get paid the same regardless. Like if you use us more, I'm not going to get paid more. If you stay longer and you love us, then I'm going to get paid more because you're going to stick around longer. So that's the big difference. And so that's why we have such a commitment to our team and what you really experience when you sign up for our service. Have you found any specific, I mean, you don't have to give away like, you know, all your hiring secrets.

23:35Do you send somebody over to interview people in person? What's that look like? Managing a remote team, I imagine, is a sizable number of people at this point. What does that look like, trying to scale that from halfway around the world? Yeah, I mean, we're at, I believe by now, over 100 people over there. And dude, the answer I'm going to give you is one that I can't even believe I'm about to give you because I used to just scoff at this kind of stuff. But it's all about mission, vision, values. I kid you not having mission vision values our vision is to change lives through creativity Our mission is to be the most helpful creative company in the world And our values are friendly smart working service and truth And we live by those we hire by those we talk about them we train on them You could have a great portfolio as a designer, but if you're not a friendly person You will get fired or you won't even get hired.

24:26You won't even an interview So it's all about just creating that culture and then I have a look I have a local team and local management team out there. So of those hundred people, about 80 are designers and the other 20 are people running those designers. And that was really important from the beginning is I'm not going to mess with that. I don't know the culture. I don't speak the language. I'm going to have someone who I can work with directly and then they can work with the team. Okay. Okay. If I submit a design request, does it go through that management layer? Does it go directly to my designer?

24:59It does go directly to your designer, but there is layers in case things aren't going well. We have layers of control and we actually have full-time customer support people here in the US. So right now we have four full-time people in the US where we have 12 team members total here in the US, but we have four of them. Third of them are dedicated to the clients. So when something does go wrong, we can take a look, chat with them because our Filipino team works in the middle of the night US time. So if something, you know, you can't really, the communication is asynchronous. So if something goes wrong, it's not like 3am email.

25:36You're like, Hey, what's up? So we have that team here working US hours so that they can chat and diagnose. Anytime something goes wrong, it's communication. Our designers are really good. Most designers who make it into the design pickle system are good designers. it's always like the request that says, Hey, make this awesome. And you kind of are like, all right, well, awesome. Like game of Thrones dragon. Awesome. Or awesome. Like touchdown football. Awesome. Like, or unicorn. Awesome. Which awesome do you mean? And once we can peel back that and understand what the client actually means, then we can get back on track.

26:15Are you communicating directly with the designer and they're sending the file back to you and then you request provisions? Yeah. You know them. You know them by first name. They wish you happy birthday. You get to know them. You love them. You hate them. You love them when they're doing great. You hate them when they stress you out because a link was broken or something. But yeah, you're working directly with them. And our designers manage a pool of clients and work on your stuff every day. So they're only going to be able to get done depending on what the total volume of that pool of clients submits in a day.

Read the full transcript

26:51But sometimes things are slower and they can get a lot done. Other times things are busy and you may only get like a couple of things done in a business day or may take a couple of days. So that that velocity and that flow is very unique. And we never promise anything because we just don't know. And people are good at emails. People suck at emails. That's how you communicate is always via email. Yeah. That largely determines like what you experience. Did you find it was tough to hire for such a subjective skill? Like, oh, this is going to be somebody's portfolio could look totally different than somebody else.

27:27I don't know. Like I've always had a hard time making design hiring decisions. It ends up becoming an advantage because we don't focus on a large spectrum of design. The design that we do, we can, like you get a lot of reps at Design Pickle as a designer. we're breaking 800 design jobs a day that we're doing. We're getting close to 900 jobs a day. So if you can make it through training, which is a lot about you as an individual and takes about two or three weeks, it might be a little rocky out of the gates, but after a week or two of working, you've gotten a lot of practice. And so the design, again, we're not doing this like high cerebral conceptual design.

28:08It's, Hey, I have this file. I don't know where the design files are, but here's a picture of it. Can you recreate it, please? Yeah. Okay, cool. And I mean, I could do that not as fast as my designers, but if you have a rough understanding of the tools, you can do it. And then we do have some designers that are just amazing. Here's the challenge for international designers in general, anywhere in the world. I've traveled really except for, I'd say like the UK and the US major English speaking countries. Design is a vocation in other countries, like a tradesman job. So it's not well-supported in the university.

28:44So most of the designers that you find in other countries are self-taught or they are in some type of commercial engine where they're just producing like a sweatshop factory. And so when we can pull them out of that environment and put them in our environment, they can really thrive and blossom because they're treated with respect. They are paid well. They have time to learn. There's training, there's advancement opportunity. And that's ultimately why we've been successful is about the people. It's not about the design skills that are required because it's not a lot of design skills that we're asking for.

29:23It's a lot of heart. It's a lot of hard work. It's a lot of culture and that's harder to find. Yeah. Now it obviously didn't start this way, But to process 800 or 900 design jobs a day, like there's got to be some infrastructure, some, like you said, some automations and some systems to deal with all of that. Okay. At what point did you start to implement this stuff or were people emailing you right away and you would forward it to the people? Like, I'm curious how the systems have kind of grown and evolved with the company. Yeah. So the point I need it. So we do run custom software. In fact, we just started a new company, Jar, jarhq.com, where we actually now sell our software.

30:03So you can be any creative team, any team at all, and check it out and white label it and put your own logo and manage your own requests. Whether you're doing design, you're an in-house team, you're copywriting, whatever. This was something built in-house. And you say, well, there might be other people that would have use for it too. Totally. Yeah. Now, it's a slightly different version than the one we use at Design Pickle, but it's the same bones. And we're actually, you know, it's a new company that we're launching because we decided that everyone who's creating anything for anyone should use a tool like we have because it works really well.

30:33But I knew we needed to do something else when the secret for about the first six months of Design Pickle was that you didn't even need a paid account to submit a request. Like if you just knew the email address, you could just submit it in and it would get done. Now we were small enough that we knew who were paying clients and who weren't. But at a certain point, I was like, dude, this is not scalable. We need to figure something out. This is like a big backdoor problem that we're going to have. So then we started building our own custom software. And initially, it was built on top of a ticketing API.

31:07And then the new jar that's at jarhq.com, that's total 100 % custom everything ourselves. But we've actually built it on top of Box's file service, box.com. So what's really dope about it is it's like really seamless file management and integration. So if you are dealing with a lot of creative assets for clients or coworkers, it doesn't really matter. All that's integrated and built in. So you don't need to manage like a separate disorganized folder. And the whole team has access to that instance of box within jar. So everybody's on the same page. Like you're not hunting down stuff if you're using our tool.

31:43Very fancy. Extremely. Took a long time. It took a while, a learning process to build a SaaS app. Well, all of this is, I mean, you know, we're only two and a half years deep into this and you're already spinning off other projects and things are going crazy. So it's really kind of exciting to see from the outside, looking from this random dude in the corner of the expo hall in a pickle costume, you know, at the Infusionsoft thing a couple of years ago, all the way to this. More with Russ in just a moment, including how he gets customers to stick around month after month and the most effective marketing channels he's found so far, right after this.

32:16Did you know there's a disease running rampant alongside hustlers and new entrepreneurs? It's called superhero syndrome. Symptoms include a feeling like you got to do everything yourself, thinking you're the only one who can do it right, and struggling to let go of certain tasks. Does that sound familiar to anyone? But the good news is there is a cure. Our sponsor Indeed can help you find the best candidates for the roles you need to fill and find them fast. Stop struggling to get your job posts seen on other job sites. Indeed's sponsored jobs help you stand out and hire fast. With Sponsored Jobs, your post jumps to the top of the page for your relevant candidates so you can reach the people you want faster.

32:53It's true. Sponsored Jobs posted directly on Indeed get 45 % more applications because every superhero needs an amazing sidekick. That's why for my next hire, I'm using Indeed. There's no need to wait any longer. Speed up your hiring right now with Indeed. Side Hustle Show listeners get a$75 sponsored job credit to get your jobs more visibility at Indeed.com slash Side Hustle Show. Just go to indeed.com slash side hustle show right now and support the show by saying you heard about Indeed on this podcast. Indeed.com slash side hustle show. Terms and conditions apply. Hiring Indeed is all you need.

33:29I'm curious on the, I guess on the membership front, you know, one of the silent killers of any kind of recurring revenue business or subscription business is the churn. I'm curious if you found anything particularly effective outside of the communication, delivering quality product to reduce that churn or improve that customer lifetime value. It's finding the right clients on the front end in the first place, because if you hit our pricing page and you don't see the inherent value and be like, wow, that's a good deal, then you're going to be a bad client. Because creativity, the sad part is, and the frustrating part about our business is it's super subjective.

34:07You're going to have a different experience, Nick, than my coworkers than my mom, than a client in Idaho. And so we can't really change that. And I've literally in the same day gotten a cancellation request saying my designer sucks. I hate them. You suck. I mean, like the most receiving email and then another email, no joke, same day from another client saying, I love my designer. This is the best. Thank you. And it was the same designer. And so like, it's mine. I mean, I had to stop reading these like articles on how to reduce churn and five hacks for churn because it was totally irrelevant for our business.

34:50Like it was like, this doesn't work. So it just comes into, are we targeting the right people who are going to see the value? And if things get a little sticky, they're not going to bail. They're actually going to communicate and tell us what's up so we can help. And that's why we communicate a lot. There's so much emails and communications and people and onboarding calls and all of this, because we're just literally trying to weed these people out the first few weeks. And if they can stick around to a month, then most likely they're going to stick around three months. And if they can stick around three months, then most likely they'll upgrade to like a prepaid plan, whether that's a six or a 12 month plan.

35:25Oh, okay. By that point, they have integrated you deeply enough into their systems where it's like, Hey, I'm relying on these guys to produce design content. If somebody, if you get that email that says, Hey, my designer sucks, do you try and reassign them to somebody else? Like, Hey, would you like to take this other guy for a test drive or, or it's just like, ah, this is not a good fit. Yeah. That's the standard protocol for the customer success team. Maybe like I've never did online dating that like was before my time. Like I did the old fashioned take girl to bar dating, but it's like online dating, you know, we match you when you sign up.

36:00And sometimes we get it, but oftentimes you just don't like them. And it's not, no one's at fault. It's just not a fit. So yeah, if we can intercept them and reassign them, that's great. But sometimes clients, they're weird. They don't even ask. They don't even know. And they'll just cancel. And you're like, Hey, what happened? Like you seem like a great client. And there's no feedback. They've done 10 jobs with zero feedback. They just get the files or they say thank you or something. And they're like, Oh, my designer sucks. And you're like, dude, dude, you got to tell us these things. Clearly there's a value here that we're providing, but if you're not happy, you don't like it.

36:34And you know, people don't like conflict and sometimes we have to hammer them. And I've recovered people because every cancellation kicks out an email for me saying, Hey, what's up? What's going on? And those that do reply, I read every one and I've recovered people. Cause I'm like, Hey, did you know you could try a different designer? Or did you know that this is what should be expected? And people are pretty amazed sometimes. And I'm amazed too, that they don't even complain. Yeah. So you mentioned targeting the right clients on the front end, people who are going to look at this price point and say, Hey, this is a great value.

37:05What do you found as far as effective marketing channels at this stage in the game? So how are we finding the right clients? Is the question like through what channel? Yeah. I imagine it spreads through word of mouth because business owners talk to other business owners, but I'm curious if you're doing any like proactive marketing, like are you still doing guest blogging? Are you still BCCing, you know, your entire contact list and what's going on on the marketing front. Yeah, no, we do. It's usually 60 % organic. So that then is podcasts like this. We do a lot of trade events with generate organic traffic after it's hard to track a direct investment in a trade show.

37:40We still do a bunch of marketing shows this year. We're going to like a church conference this year or this month in Atlanta. Okay. So we're testing out that. And then like 30-ish percent paid advertising, paid acquisition with the majority of that through Facebook. No one is like the guy who's on Google typing in, how do I hire a designer? I need a designer. That is not the guy we want or gal. That person is like the worst possible client for us. Google, while I want to crack it, is like really hard for us to crack because our ideal client is probably set at the moment with the designer. They know somebody, they have somebody, they are a coworker, maybe they are a designer.

38:22So we want to interrupt them on Facebook and Instagram and be like, hey, here's who we are. Here's who we are. Here's who we are. Here's who we are. And then when a problem happens or something's going wrong or they need extra help, then they're like, oh, that pickle guy. I'm going to go check those guys out. Okay. So that's kind of the Facebook strategy is just kind of an awareness play at this point. Or does it lead directly to a sign up for a trial? Or what does it look like? Yeah, just sign up. We don't mess around. just direct sales ads. We've tried, you know, we have a lot of top of funnel stuff around the marketplace.

38:56We are actually the 2017 national pickleball tournament sponsors. So if you've ever heard of the sport pickleball, it's like tennis with paddles. We are the presenting sponsor on CBS sports this fall for their national tournament. Kind of an experiment in B2C marketing, but we're going after that. And yeah, we just want awareness and brand awareness. And then if it's relevant to you and you need design, then the idea there is you're top of mind. Okay. I'm definitely curious to see how that one plays out. That's a great tie-in. It's funny. Yeah. A bit of an older demographic to traditionally than what we're looking for, but it wasn't that expensive of a sponsorship.

39:39Let's just say that. You never know. You never know. It's not like the Olympics. That's right. Well, Russ, what's next? And you got a book coming up? I do. The sober entrepreneur. I feel like there's a backstory there. Well, I used to drink a lot. That sums it up. Yeah, no, honestly, in all seriousness, I did have, I was an alcoholic. I drank a lot. A lot of my agency years, you know, I quit in 2013, but it was a struggle and it was a struggle as a man, a struggle as an entrepreneur, a struggle as a husband. And so I wanted to write a book really sharing my story, but also really talking about this larger topic of sobriety.

40:20Cause if it's not alcohol, it could be your business. If it's not your business, it could be food or porn or any, you know, like there's a lot of stuff out there that consumes us and kind of takes us to different places. And so I wanted to write a book telling my story, but also opening up this conversation of around, like, what does it mean to live sober and how can you live a more sober, clear life, which in my definition is just being in full control and super authentic, just being who you are. So that book's going to be coming out and we'll see where that goes. Very cool. Sober entrepreneur.com is the landing page there.

40:55That's right. Yeah. And everyone listening, you can download the first chapter for free there. Just shoot me your email and you'll get it right away. Sounds good. Sober entrepreneur.com jar HQ.com for the new SAS product. And of course, designpickle.com for the unlimited design service. Russ, awesome to chat with you. Lots of fun takeaways and kind of nuggets. Dude, I've never been able to talk about all three things in one podcast. This is like the triple crown podcast today. Well, before I let you go, we got to wrap this thing up with your number one tip for Side Hustle Nation. I'm going to go back to pricing.

41:32If you're not charging enough, you will not succeed. You will lose motivation. You'll get burnt out. You'll grind yourself into death without a paycheck. So I would venture to say double or triple your prices immediately out of the gates. That cashflow is literally the elixir of life for your motivation and everything else that's ahead. Cashflow is the elixir of life. I love it, Russ. Thank you so much. We'll catch up with you soon. All right. Thank you. Okay, lots to unpack from this episode, including Russ's obvious passion for this business and his lean startup style launch. I like the part about how anyone could have been able to submit a design request if they guessed the email right.

42:14But here are my top three takeaways from the chat with Russ. Number one is to market your thing. There was no build it and they'll come. This wasn't, oh, I'm going to set up a website and I'm going to hope that customers find it. Russ was out there in a freaking pickle costume. He was speaking at events. He was emailing his contacts. He was getting in trouble with Gmail, but he was getting the word out. He was marketing his thing. Even today, I see Design Pickle at conferences. I see their ads on Facebook. They're sponsoring the National Pickleball Championships. And they're still out hustling for more customers.

42:47And like Russ said, it's the pricing and it's the lifetime value that allows them to invest in that growth. Takeaway number two is to remove yourself as early as possible. One thing I thought was cool is that this was never Russ's awesome design service. He was never selling his own skill or his own expertise. He was just finding other people who could deliver the goods and then matching them up with customers in need of their help. You could do that, right? And then all you have to do is rinse and repeat over and over again until you're at 400 grand in monthly recurring revenue. Takeaway number three is to sell your tools.

43:21So Russ's new software project, JAR, is a great example of taking a page out of Amazon's playbook. And what I mean by that is, for example, their AWS infrastructure, their cloud hosting, was originally built for their in-house use. They said, hey, we've got this fast-growing e-commerce platform. How do we handle all the traffic? And then once it was built and functional, they said, hey, we could turn around and sell access to this to external customers. And now everybody hosts on Amazon, it seems like. At least most startups seem to host on Amazon. Another example is they built their logistics network.

43:53and then they open it up to FBA sellers. They say, hey, we've already built this. Why don't we open the floodgates and now we can take a fee on that. So I think JAR is an example of selling your internal tools. Hey, we built this for in-house use, but I think it has a broader application. It's also, I think, an illustration of, for those who have a phobia of service businesses, of the hustler's path that we've talked about from freelance to agency to product. You don't always know what the product is going to be when you start out, but we've seen it over and over again on the side hustle show that more time leveraged business models emerge from something else first.

44:32Hey, it's 2024 Nick with a little business update since this original 2017 recording with Russ. When we recorded this call, Design Pickle was around$400 ,000 in monthly revenue or around$4.8 million annually. By 2020, that was$21 million, and by 2023, likely at least double that based on their continued and consistent presence on the Inc. 5000 list of the fastest growing private companies. It looks like the JAR project is no longer active, so apologies if you were looking forward to checking out that tool, but Design Pickle very much still is. In fact, in 2022, the company took their first outside funding, a$25 million venture investment to fuel ongoing growth and operations.

45:15Again, sidehustlenation.com slash design pickle is my direct referral link. If your business could use some ongoing graphic design help from a team in business that's been doing it for a really long time at this point. But the real reason for re-airing this episode is to showcase what's possible in taking a fragmented service industry. By that, I mean one without a clear national or regional dominant market leader, and then adding a branding layer, a consistent process layer, a compelling, convenient pricing layer, and then building something that really has some staying power. And we've seen examples of this in content writing, in video editing with Justin Tan from Video Husky, in offline businesses too, in residential house cleaning with Chris Schwab and Anthony and Janilka Hartzog.

46:04I think there's an opportunity here to productize any number of different services following the design pickle playbook. That's why I wanted to breathe some new life into that original conversation. And to get the ideas and inspiration flowing for you, you can even download 101 different service business ideas at the show notes for this episode at sidehustlenation.com slash Russ. Now, I think the funniest thing in re-listening to this one was the Pickleball Tournament Sponsorship. Amazing brand tie-in, right? But Russ still felt the need to explain a little bit, well, here's what Pickleball the last six and a half years, pickleball has definitely gone more mainstream.

46:45So I don't know if they're still sponsoring, but I imagine those rates have gone up quite a bit since then. In any case, big thanks to Russ for sharing his insight. Thanks to our sponsors for making this content free for everyone. You can hit up side hustle nation.com slash deals for all the latest offers from our sponsors in one place. Thank you for supporting the advertisers that support the show. That's it for me. Thank you so much for tuning in until next time. Let's go out there and make something happen and I'll catch you in the next edition of the side hustle show hustle on

From the publisher

Three years ago Design Pickle didn't exist. It wasn't even an idea in founder Russ Perry's head yet.
That's why it seems crazy to me that today the unlimited graphic design service is doing $400k in monthly recurring revenue!
Back in 2014, Russ was running a creative agency, but he started to hate everything about it. “I felt like I was in a prison of my own creation,” he said.
By January 2015, he'd shut down his agency and started working as a freelancer. Not wanting to build a similar prison again, he sought out a different business model -- one with a simpler service offering that was designed to scale.
From taking on a friend as his first client to now completing more than 800 design jobs a day, it’s been an incredibly quick ascension and a great example of how to scale a service business.
Tune in to hear how Russ grew his business from zero to $410k+ in monthly recurring revenue in less than 3 years.
We cover his marketing strategies, his hiring best practices, and what Design Pickle does to keep customers coming back month after month.
Full Show Notes: Scaling Up a Service Business: From Idea to $400k in Monthly Recurring Revenue (in Under 3 Years)
New to the Show? Get your personalized money-making playlist here!
Sponsors:

Squarespace - Start building your professional website today!

Factor — Get 50% off America's #1 ready-to-eat meal delivery service w/ code sidehustle50!

Indeed – Start hiring NOW with a $75 sponsored job credit to upgrade your job post!

My First Million — Explore new business ideas based on trends and opportunities in the market!

More from The Side Hustle Show

All 247 episodes
Scaling Up a Service Business: From Idea to $400k in Monthly Recurring Revenue (Greatest Hits)The Side Hustle Show · 45 min
Listen in VO