Models of Possibility: How Maurice Cherry Found (and Shared) His Path to Success

Faced with the prospect of being overworked and underpaid, Cherry left to begin the freelancing work that would eventually lead him to open his own agency. Now, after nearly a decade of working on his own terms, Cherry’s really looking forward to one thing.

“I’ll finally have a summer vacation,” Cherry says. “I’ve been hustling and working every summer since I was a kid — summer jobs, 2 internships with NASA in college, and working ever since. This is the first time I’ve seen a summer I could take off for a week and enjoy it.”

That’s no exaggeration — Cherry’s an extremely busy guy. In addition to his day job, Cherry is the creator of the Black Weblog Awards, the web’s longest-running event celebrating black bloggers, video bloggers, and podcasters, and the creator of award-winning podcast Revision Path. Other projects include 28 Days of the Web and The Year of Tea, a short daily podcast in which Cherry sampled and reviewed a new tea each day of 2015.

We caught up with Cherry at Ponce City Market in Atlanta to find out what (besides tea) keeps his relentless motor running.

What were you like as a kid? Were you always creative?

I’d like to think so. I’ve loved to write and draw since kindergarten, and in second grade I started in a gifted program that I stayed in throughout high school. I’m originally from Selma, Alabama, which is a little town in the deep South, so I had the whole “big fish in a small pond” thing going on. Being in the gifted program gave me the opportunity to meet some really smart people, and they’d bus us across town to visit other schools. That’s actually where I got my first taste of working with computers.

But growing up, what I really wanted was to be a writer. It never occurred to me to be a designer — my brother was the sculptor, the woodworker, the artist. I didn’t get any of that. I was mostly writing a whole lot.

So design wasn’t really on your radar?

I never really knew it could be a career option. I got exposed to computers in the mid-1990s, and so I was always on the web in some way. That’s how I taught myself HTML and a little bit of Photoshop. I also started writing music and playing trombone in concert band around that time, so those were really my core interests — computers, music, and writing.

When I graduated high school, though, I needed to figure out how to make money. I had my name out there from getting published a few times, but my mom really wanted me to get an engineering job — this was when A Different World had just gone off the air, so she wanted me to be like Dwayne Wayne. When I got scholarships to attend Morehouse College in Atlanta, that was the direction I was headed.

Engineering?

Computer engineering, specifically, but I hated the program there. I wanted to build things with HTML, but their focus was on learning C++, stuff like that. Finally, I sat down with my advisor and said, “Hey, I want to get into web design,” only to find out that wasn’t an option.

It sounds like your path to agency life was anything but direct.

It wasn’t, but I was always compelled toward the creative arts. The first jobs I took after I graduated were things like selling tickets at the symphony, the theater, the art museum — anything so I could be adjacent to the arts. I was also doing web design on the side, and my mom encouraged me to keep after it. I got my first design job with the Georgia World Congress Center, and after that I left to work for AT&T.

That was the job that pushed me to start my own business, ultimately. There was an issue with backpay, and when they finally paid what they owed me, I decided to take that money and start my own business. I didn’t know what I was doing. All my freelance stuff up to then was on the side, so it was never my bread and butter. Going it alone made my mom nervous. She said, “Don’t ask me for money, you need to get back to work.” But I was like, “I’m going to show you I can do this.”

There’s so much competition for attention out there — what have you learned about standing out?

Social media and email are still really great ways to do that. They’ve democratized your access to clients and audiences. And I’ve also always thrown myself into projects that speak to the spirit of what I believe in and the kind of work I want to do. There are a lot of ways to tell your story, and even if you’re not on Twitter 24/7 you can still do things that communicate what you’re about authentically.

With email, it can be tricky to strike the right balance, but the advantage is that someone’s email address is like a red carpet to their inbox. It’s a direct way to connect. So email becomes most important once you really get the voice of your brand down pat, whether you’re communicating a big message or just announcing a sale.

You also need to research your customers ahead of time, or else you’re going to do your work twice trying to reach a segment of people that your business isn’t meant to reach. It’s important to figure out your ideal customer. For someone like me, it’s that small business owner or creative business.

You mentioned projects that “speak to the spirit of what you believe in.” One of your ongoing projects has been Revision Path, a podcast that spotlights black developers, designers, and creatives. Why has that been important to you?

In 2004, I started the Black Weblog Awards, which at the time was the internet’s only event that recognized black bloggers, podcasters, etc. I’d noticed that similar types of awards were not recognizing any black bloggers. I also realized a lot of black designers weren’t getting the same level of recognition that our peers received.

I wanted to showcase people whose work I’d loved for a long time, and finally in 2013 I had time to pursue it with the podcast. Black designers are still not reflected in design media the way we should be, and our contributions aren’t as recognized. It’s beginning to change, and we’re getting a modicum of visibility, but growing up I had no idea design was a thing I could do.

So there was an awareness gap?

You can’t be what you can’t see. How different would my life path have been if I knew, at 18, that this was an option? With projects like Revision Path and 28 Days of the Web, it’s important for me to give the next generation that platform, so young people know this is something they can do. These are possibility models, as Laverne Cox calls them. Being able to see yourself, or seeing another black person, who’s doing the work you want to do at least gives you a trajectory to shoot for.

How has the show been received?

As of this interview, we’re closing in on 200 episodes, and we’re getting support from places like AIGA, Facebook, Mailchimp, SiteGround, Hover, and more. They believe in the mission and the work we’re doing to reach out to that next generation of designers.

I’m also proud of how it’s giving designers a chance to elevate their platforms, and leading people to get jobs, speaking gigs, and other opportunities. The show’s just one little spark, but no one else was giving them a chance. It’s helped make something grow.

3 reasons to turn away clients

After nearly a decade in business, Maurice Cherry has gotten pretty good at knowing when a new client is a good prospect or not. Here he shares a few reasons agencies should say “no” to clients:

1. They demand constant attention. “It’s important to have good rapport, but some clients don’t understand that we’re not at their beck and call while we work on their project,” Cherry says. Overly demanding clients can lead to situations where nobody’s happy. It’s better to turn them away at the outset than to create a negative working relationship.

2. They’re unrealistic about timeline or budget. “Clients from hell are often the ones that don’t get vetted heavily enough up front,” Cherry says. “It’s important to be clear about what can be done when, and on what budget.” It can be tempting to offer potential clients a lot of flexibility when it comes to timeline and budget if it means winning their business. But if the client expects the impossible, it may be time to say goodbye.

3. You’re neglecting the clients you have. “A lot of entrepreneurs are worried about trying to find more clients and new leads,” Cherry says. “But it’s important to cultivate the leads you have and figure out how to do more for them.” Finding new clients can feel like a win in the short term, but if you start ignoring your existing clients, you may end up paying for it.