We’re excited to introduce you to the always interesting and insightful Jessica Redmon. We hope you’ll enjoy our conversation with Jessica below.

Jessica, thanks for joining us, excited to have you contributing your stories and insights. We’d love to hear from you about what you think Corporate America gets wrong in your industry and why it matters.

The Covid pandemic and shutdown happened on my watch as Vice President of Creative Services at Nashville’s Visitors Bureau. My team of graphic designers and project managers adapted quickly to the new work-from-home arrangement. We could efficiently complete our tasks as long as we had our MacBooks and Adobe Creative Cloud subscriptions. We never missed a deadline during the months of working in our pajamas.

When we were given the mandate to return to the office five days a week, my team of Creatives pushed back. We had a months-long track record of never dropping the ball or slacking off. Some of our greatest campaign ideas came from Team Zoom calls. Our productivity increased once drive-by-cubicle requests were no longer an option, and pointless meetings shifted to shared Google Docs. Creative designs were birthed from mid-day walks and playtime with our pets.

We read about other marketing teams moving to hybrid models and made our case. The old-school mindset prevailed. We were instructed to strap on a mask and return to the office every day or quit.

Productive, creative days were traded for long commutes and inter-office isolation. Managers were not interested in or willing to learn why working from home worked for us. Their idea was that employees, no matter their role, must be at their desks or not be working. The mental health and creativity of my team and I declined, and I decided to leave a few months later.

Corporate America gets it wrong when they enforce strict office hours for those of us in Creative Industries. Good ideas do not come from staring at a screen. Innovation comes from happy Creatives who are allowed to wander.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

A classic tale of a boy and a girl swiping right on Bumble, dating long-distance for two years, getting married, and combining talents to start a business together.

We (Jess and Justin Redmon) formed Apple & Anchor in January 2022. We are a husband and wife graphic design and illustration team providing flat-rate design support for marketing firms, small businesses, agencies, and in-house teams.

As a design professional for over 16 years I, Jess (“Apple”), recently served as Vice President of Creative Services for Nashville’s Visitor Bureau. There, I managed a team who branded a Nashville pop-up store in Manhattan, created a Music City-themed experience at the Bonnaroo music festival, and designed illuminated traffic lights for the NFL Draft.

Justin (“Anchor”) is a natural-born illustrator. Starting with pencil and brush works of vintage cars, his passion for design deepened through his 13 years traveling the world while serving in the U.S. Navy. Today, his chosen medium is digital illustration. Its flexibility in color and form challenges the boundaries of design and allows him to channel emotion through art.

After simultaneously feeling the need for a career change, we left our jobs in 2021. Our first client was a commercial real estate firm whose Creative Director would be on maternity leave for three months. We filled her absence with professional-level, temporary design support (and they’re still a client to this day). The experience opened our eyes to a need in the marketplace that we built Apple & Anchor to fill.

As we see it, there is a spectrum of design support. Freelancers and UpWork contractors are on one end, and full-service Agencies are on the other. While Freelancers can provide temporary design support, their level of customer service, reliability, and design knowledge can be limited. Agencies are capable but often have long onboarding processes and are pricey. We see ourselves in the middle of the spectrum as “Agency-Light.” We offer professional-level graphic design, reliable turnaround times, and transparent, flat-rate pricing.

Many of our clients rely on us as their outsourced design department. We can create any marketing deliverables, such as:

– Digital designs for websites, ads, and social media
– Direct mail
– Events materials such as save the dates, invitations, banners, signage, table cards
– Apparel design
– Branding and re-brands
– Custom illustrations and portraits
– White-labeling

Let’s talk about resilience next – do you have a story you can share with us?

On July 5th, 2021, we arrived at our rental cabin in the Georgia Mountains. As cell service picked up, a long, scathing text message pinged through from my boss. “Where was I?” “Didn’t I know there was a major event she was at today?!”, “Why wasn’t I available to tell her where the logo was on the server?!”. I burst into tears and knew I was finally done as VP of Creative at Nashville’s Visitors Bureau.

I had just come off a long weekend of hot, sweaty work preparing for and working at Nashville’s July 4th event in downtown Nashville. The Georgia vacation with my husband and daughters had been planned and approved months earlier.

Although my job was fast-paced, exciting, and fulfilling in many ways, my boss had never accepted that someone my age deserved a seat on her Marketing Team. I felt I could never do anything right in her eyes, and the stress of walking on eggshells was constant. The gray walls of my windowless closet they’d emptied to serve as my office closed in on me as I tried to balance her requests to be visible around the office and complete design requests with extreme turnaround times.

As a newly single mom, I’d taken the job for its steady paycheck and sense of stability. Adding the daily in-office tension to the 45-minute commute and constant, nagging guilt for missing my daughter’s school functions, I summed up that the price I was paying for my paycheck was too high.

I began applying for Creative Director roles and quickly landed a first interview with a Marketing Firm. That interview turned into a third, where I was to prepare a 45-minute presentation selling myself to their large team of decision-makers, followed by an hour-long Q&A. I worked on the pitch every night and weekend for two weeks. Seeing it as my ticket out of my miserable job situation, I poured my heart and soul into selling myself when the day came.

I left the interview feeling like leaving a first date where I’d come off as needy and desperate for them to like me. I did not get a callback. In fact, like a turned-off date, they ghosted.

After an agonizing week of no reply, I told Justin I needed a change of scenery to clear my head. We headed to Bardstown to plot our next steps with the aid of some Kentucky bourbon.

Our trip ended Saturday night at Log Still Distillery. Over neat glasses of “Monk’s Road,” Wally Dant, the distillery’s founder, and his business partner asked Justin and me what brought us to their distillery that evening. We told them about my career woes and Justin’s discontent with the Navy. Both seasoned, multi-millionaire serial entrepreneurs attributed their successes to taking risks. They advised us that we were at a point where we should do the same.

The seed for Apple & Anchor was planted, and we set our plan in motion on the drive back home. We embraced the risks, and I’m proud to say we will celebrate our one-year anniversary in January.

How’d you meet your business partner?

Justin’s childhood friend (Niko Moon) asked him to drive up from Pensacola to be in his music video in Nashville. After spending the weekend being teased for being single and not getting back “out there” after his divorce, Justin woke up Sunday morning and created a Bumble account while his friends slept.

I was one of the (many) happy ladies in Nashville to see Justin’s new profile pop into my 25-mile range setting. I opened with, “Hello, fellow Graphic Artist,” and we chatted for his entire six-hour drive back to the Naval base.

After a week of face timing, we met in Birmingham the following weekend, and he drove me down to his place in Florida. We both said “I love you” that weekend and were engaged two years later. We started our business together in January and married in April this year :).

Contact Info:

• Website: https://appleandanchor.com/
• Instagram: https://www.instagram.com/appleandanchordesign/
• Facebook: https://www.facebook.com/Apple-Anchor-106132558624617
• Linkedin: https://www.linkedin.com/company/apple-and-anchor/about/
• Other: https://linktr.ee/appleandanchor