Working Without Pants - Creative Entrepreneurship

Russ Perry is the founder of Design Pickle, a productized graphic design service. 

Design Pickle can free up your marketing team to work on bigger initiatives, while they take care of things like business cards, brochures, posters, etc. It’s amazingly simple: just sign up and get matched with a dedicated designer for unlimited designs at a flat rate of $370/mo.

You’ll really get some value out of this episode if you want to productize a service. We dive into how Russ started Design Pickle, scaled it to over $100K in monthly recurring revenue in 1.5 years, challenges he’s faced and big insights/ideas he’s discovered. His thought process in starting the business was fascinating.


Highlights of this episode: 

[3:25] Scratching an itch: After closing his agency, Russ sought a simple way to find vetted help for quick graphic design work (ie, business cards, brochures, etc). As a consultant, he developed a system for doing this stuff (ie, business). His clients were having success with it, so he moved into branding this service and launching it to the public. Plus, Russ loves pickles. So, voila, Design Pickle.

[6:00] Starting DP was really scary. Russ was facing unemployment and dreaded getting a job. He thought long and hard about what kind of lifestyle he desired. As a consultant, he discovered that managing production design met most of his lifestyle requirements. The business structure really came out of this clarity about his ideal lifestyle.

[9:25] A financial model is the only business plan you need (how you will make money). Russ discusses how he priced the service, and quickly raised prices, allowing for investments in growth.

[11:40] To acquire initial customers, start with a very simple solution. Then it’s all about getting out there and communicating that value. Russ was the best spammer alive. Almost got kicked out of a professional organization for it. Also, be profitable, so you can invest in strategic growth opportunities.

[14:15] In less than two years, Design Pickle has steadily and consistently grown to over $100K MRR, 1000 signups and 380 active users!

[15:15] Lessons from running a crappy business, and having a strong culture, has allowed Russ to grow the business so quickly. It’s all about the people. Keep it simple and stay the course!

[18:15] On avoiding going into other directions...Why not start Because he’s barely scratched the surface with Design Pickle.

[19:25] Being removed from day-to-day tasks is huge in ensuring the ship is running smoothly and in moving things forward. Russ’s role: Mechanic of the Pickle Machine, Voice of the Brand, Front Line of Sales, Strategic Navigator.

[21:10] On managing a team across the world. Besides the 2 others in Arizona, all the designers and managers are in the Philippines. The team is like a family, though, Russ realized when he was able to go to Philippines for the first time. Moving forward, he’ll be investing in meetups, conferences.

[24:20] Clients’ deserve respect and to be shown that their work is important. Put your all into the work and build relationships.  

[26:15] To grow your agency, get out and meet people in the flesh. Be real. Russ’s secret: he goes to conferences and gives out free pickles. People eat them up.  

[28:20] Everyone want to have fun, connect with real people. Plus, engaging people with authenticity and developing real relationships helps if things go sideways.

[29:40] Going forward, it’s all about finding more people they can help, taking the time to reach them, and communicating the value in Design Pickle.

[32:30] Cash flow is a challenge in expanding with sales/marketing/advertising. Always stay ahead of hiring, so you can handle the work if you take on new clients. The current model can handle doubling or tripling, but beyond that, it may need investments in software and other things to continue growing.

[35:25]Design Pickle offers a 14-day, risk-free trial. If you email Russ and let him know you signed up from the podcast, you’ll get a free pickle!

[37:10] For agencies: You can use DP for client work...but Russ recommends getting a feel first, so the team can get to know you and your brand before taking on your client work.

Learn More: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_Russ_Perry.mp3
Category:agency owner -- posted at: 2:00pm EDT

After growing Solar Velocity from nothing to an 8-figure agency, selling it and getting bored on the beach, Jason Swenk began helping other agency owners. He now teaches the lessons he’s learned along the way at 

Jason shares his incredible insights in this episode, oozing with his spunky personality. 


Highlights of this episode: 

[4:10] It all started with a NSync parody site, then he started making $500 websites, quit his job at Arthur Andersen before they destroyed the world, and in 2-3 years was making $200K websites. So thanks Justin Timberlake!

[6:00] The company really took off once he started examining what we didn’t want to do (working with clients), and put systems in place so the business could go on without him.

[7:20] He kept upgrading the offerings based on what clients needed. As your price increases, so too does the need to communicate how you are unique.

[8:40] To really scale, the Agency Owner (does everything) needs to transition to the Agency CEO (focuses on vision, strategy, coaching). The first step is hiring a project manager!

[11:50] Assume you’re project manager will screw up. If you’re scared of that, get out of business. Jason encourages (one-time) failures for learning purposes. Systems>>Talent.

[14:30] Everyone on his team took personality tests, and they tried to find people to fill in the gaps. It’s more important that a new hire shares the company’s core values, then technical know-how. Value-based hiring led to Solar Velocity’s becoming the Best Place to Work in Atlanta, which snowballed into better & better people applying.

[16:20] He replaced Quarterly Reviews with Quarterly Coaching, because employers are your #1 asset, so management’s job is not to condemn, but to help make employees better and achieve their goals. Your office environment should reflect your personality. Be yourself. He made a fun environment, and those that didn’t like it could leave.

[19:20] Growth revolved around generating the pipeline through 1) strategic partnerships (not just trading leads, but building practice areas to specialize in), 1) outbound strategy, and 2) inbound strategy (gotta capture that info!) and 3) strategic partnerships- which is not just trading leads, but actually building practice areas to specialize in. They specialized in Sitefinity.

[22:00] Partner with an up-and-coming technology (not Wordpress or Facebook). Help them out before expecting anything in return. That’s what they did with Sitefinity- when they had success with it for a client, they made a case study to help Sitefinity communicate their value better. So Finity sent them Hitachi, Legalzoom, and other amazing clients.

[24:35] Successful people make money, but significant people affect other people/businesses by helping, not just taking...Helping>>Selling

[25:40] Don’t reach out to everyone. Go after a select few. Do extensive research. Think about who would need your service (ie, companies spending $10K+ on AdWords)? Provide value in the initial touch, and make a foot-in-the-door offer. DO NOT SEND A PROPOSAL!

[31:40] Chances of making money are 20X after they buy the foot-in-the-door offer, and you can qualify them. There is no bad agency client...only a bad prospect or a bad process.

[32:20] Building processes is about diving deep after a project is completed, to see what went right and what went wrong. Map it out and make adjustments. It takes a lot of f**k-ups.

[33:45] “If something were to happen to me, would this company survive?” worried Jason. Employees are like family, so it’s not just about you.

[35:15] Jason assisted with sales, just to bring in his colorful personality and make sure everyone was doing their job.

[36:10] They sold the business to a strategic partner who wanted to get into what Solar Velocity was doing. Only 0.25% of agencies get sold, so don’t feel like that is what it takes to “make it.” Money doesn’t ensure happiness.

[37:00] When considering selling, if they ask you questions, ask the same questions to them. And if people start asking to buy on the low, go through the process and learn from it. It won’t hurt, as long as you don’t give up valuable secrets. ​

[38:55] If you don’t like the offer, stop there or waste your time. And he explains how to tell if the buyers are serious, or they just want to steal your secret sauce. And don’t get too excited during the due diligence phase--that’s when most agencies go out of business, so assume it won’t go through.

[40:45] After selling, Jason was out in 9 months. He never got his earn out (losing millions), but he learned a valuable lesson and has made that money back by teaching other agency owners through his mistakes.

[41:40] Earnouts are based on growth rate and profit margin. Agencies between $2-10M are hard to sell. Don’t sell if you’re making bank.

[44:10] So why did Jason sell? The business outgrew his partner, and he got bored and wanted something new.

[44:40] Nowadays, he helps agency owners scale, teaching them how we started, grew and sold his agency. His goal is to be the #1 resource in the world for agency owners. Check out his podcast, video show, and the Agency Playbook (12 systems to scale and grow your agency).

[47:15] Jason doesn't read. He learns from doing & failing. Just wing it.


Resources Mentioned in this Episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_Jason_Swenk.mp3
Category:agency owner -- posted at: 12:44pm EDT

David Reske is the founder and CEO of digital marketing agency Nowspeed.

He’s built a phenomenal business over the last 10-15 years. David is incredibly clearheaded and sophisticated about Nowspeed. But the journey has not been without challenges.

In this episode, we discuss his business, what's works, and what hasn't.

Highlights of this episode: 

[3:15] The kind of people you hire creates the kind of atmosphere and culture your company will have.

[3:50] Nowspeed has evolved over the years to use whatever tools are available to drive engagement, traffic and leads.

[5:00] Dave started the company with his wife, which offers great flexibility for her as a working mother. But, leave business outside the shower!

[7:20] The digital marketing landscape has grown much more sophisticated, and it’s much harder now to land the big boys as clients.

[9:00] Nowspeed differentiates itself through platinum level service and expertise that goes beyond the capabilities of most internal marketing teams.

[12:30] In his business, Dave works primarily as strategist, accountability partner, business developer, management coach, and process/service tweaker.

[14:10] It’s risky for a service business to have one customer account for a large portion of the business.

[15:25] The way Nowspeed is structured, account leads communicate and work with clients and strategy, and they manage a team of experts who work in their particular expertise to execute the campaigns.

[17:10] There’s no magic bullet to getting work. They do the stuff they offer- inbound/content marketing,  SEO, PPC, social media- to drive leads. But they are also very active in partnering with other agencies/consultants to drive referrals.

[19:20] Dave spends half of his time doing strategic sales/business development. They only reach out locally, but they have leads/clients from all over the US/world.

[20:45] Dave loves integrating all the pieces of the puzzle.

[22:18] Hiring when desperate = Big Mistake! Instead, Nowspeed hires (mainly fresh college grads) and trains in classes.

[26:30] You don’t know what systems/process you need, until you really NEED them. So it’s a continuous evolution, discovering new challenges/things that need fixing. It helps to get your team involved in this.


Resources Mentioned in this Episode: 

This episode is sponsored by Outbound Creative

Outbound Creative helps agencies and consultancies win their dream clients through eye-catching outreach campaigns. Learn more at 

Be kind and share with others

Direct download: WWP_-_David_Reske.mp3
Category:agency owner -- posted at: 9:35am EDT