Conversation with Theola DeBose, Co-Founder of GraySide Media Group
Finding the Support You Need & Listening to Oneself
January 17, 2018
1. What is your business?
My business, GraySide Media Group, helps people and organizations tell their stories through strategic communications. Right now we have two lines of business: I host a podcast called “The Gray Side: Life After Journalism,” and we consult for entrepreneurs and undiscovered brands to help them grow their influence.
In the podcast, I interview former journalists who share their stories of leaving journalism and reinventing themselves in new careers. The news business is so difficult these days with buyouts, layoffs due to declining profits, and “fake news” symbolizing a loss of trust. I used to be a journalist, and so I know what’s it’s like to want a change but to be unsure about what to do next. I really want journalists still trying to figure it out to hear the podcast and be inspired to take the next best step for themselves.
To make the podcast I record the interviews on my laptop through Skype and use a program called Ecamm Call Recorder to end up with two separate tracks. I chose to have two separate tracks so that if one person messes up or talks over the other person, then you’re able to edit one person independently of the other. And this way I don’t have to be in the room with the person I am speaking to. My goal is to get on iTunes, but I’m not quite there yet. I started out on SoundCloud and am publishing the podcasts as I finish them. That part is a struggle, to be honest, because at this point I have more episodes recorded than I have published. Juggling my family and podcast editing and promotion is something I’m still figuring out.
On the consulting side, we work with startups on strategies for telling their story in so many different ways — from an informal setting like at the coffee break station at a conference, or in a more official setting, like a media interview on the radio, digitally through social media, or through advocacy in a meeting with a public official.
2. What made you decide to start your business and/or switch careers?
It was two things: the birth of my first child combined with the decline in profits in the newspaper industry. The profit decline had been years in the making–Craigslist’s popularity disrupted the newspaper industry’s traditional revenue model through print classified ads. The growth of digital and the decline of print has meant newspapers have been trying to figure out how to monetize online readership and recoup their advertising losses. When they haven’t been able to come up with a model that produced profit, they had to lay off reporters and restructure. That has led to a lot of pressure on individual journalists because there are now fewer of them to do the job — and, at the same time, the growth of digital has meant an increase in job responsibilities. Reporters are expected to not just write a story but to tweet about it, talk about it on TV, post it to their Facebook page, etc.
And then on top of that pressure, there is personal change as well. In my experience, I reported on a lot of important topics–like going on patrol with U.S. troops in Iraq and covering the Haiti earthquake while pregnant. But when my first son was born in 2010, I found myself identifying more with the people I was writing about, and I wanted to work for causes that were important to me.
3. Was there one moment that gave you the confidence that this was a good idea?
I got the idea once I started working in public relations and I had to manage people. I remember one team member in particular. Like myself, this person had journalism experience, but instead of that being a shared point of collaboration, we struggled to connect. The person still displayed work behaviors and habits from the former journalism career — for example, working in a silo instead of collaborating and freely sharing information with the team. As a manager, my job is to develop people and give them resources to do the job. But in this case, there was no training where I could send the person or a course that this person could take, that was tailored to journalists who had switched careers. The podcast idea is me providing a place for journalists who had made this shift to tell their stories. I want it to be a resource for career transition.
4. What obstacles did you face in getting started and thinking of yourself as an expert in a new setting?
I have a fear of success. It’s weird, even though I have no problem trying something new, once a new endeavor starts to work out I get really nervous. I feel like I don’t deserve the success or that somehow it will balloon up and swallow me, or some other nonsensical emotion that feels very real. So I get stuck. I planned GraySide for nearly two years.
5. Were your family and friends helpful or obstacles in launching your business? How so?
My husband Brian is a co-founder, and he is supportive and a great sounding board. That doesn’t mean that he agrees with everything that I say or do. In fact, 9 times out of 10, he’ll say, “I have no idea what you’re talking about…I don’t understand.”
When you have someone close to you say over and over, “I have no idea what you’re talking about,” you have to look at yourself and ask yourself whether you could be more clear. Having that revelation really helped me because now I think of Brian as my first test audience. He’s also a former journalist. I went through a bunch of podcast names and business ideas. So after eighteen months, when I came up with the concept of the Gray Side, Brian was finally saying, “Yes, that makes sense.” Sometimes, the support you need is actually non-support.
6. Were there any partnerships or advice that were particularly helpful?
I would definitely advise folks to look for support anywhere they can find it. I graduated from Princeton University, and I learned a few years ago that a group of alumni sponsor a professional development program for nonprofit and public sector leaders. I applied for the Emerging Leaders program and was accepted. I was actually pregnant at the time that I applied, and when I started the program I was on maternity leave. The program gave me a lot of support in thinking of myself as a leader and as a communications professional.
7. Was outside funding/cost a challenge to getting your business off the ground?
It remains a challenge. We have used our savings to start GraySide, and consulting is our main source of revenue. Our goal is to diversify our revenue so it includes consulting, speaking fees, trainings, products and other ventures. Since we are a service-based business, right now we’re not looking at outside funding, but someday we might.
8. What are some successes you have had with your business that make you proud?
It’s the small moments when I challenge myself to do something new and uncomfortable. Just recently, my husband and I just killed ourselves to create a pitch deck. We have four children ranging from high school age to preschool, and it was a particularly tough week on the home front trying to balance home and business. When we finally turned in the proposal, we talked about what could have gone better with the project. My husband mentioned how frustrating it is to turn in a piece of work and then wait for feedback from the client. I said the trick is to not wait and ask to set up a meeting or call to get the feedback you need. In that moment I took my own advice and asked the client if we could schedule a call to walk through the proposal. An hour later we were on a call. We didn’t have time to practice our presentation, and we just winged it. It wasn’t perfect but it turned out well. We got some good feedback and will likely land the contract.
9. What would be your biggest piece of advice you would give to yourself ten years ago?
Save more money! Money and my relationship to money is probably the least examined area of my life. When I was in my 20’s, I went to Iraq for the Washington Post for several months. When I went over there, I had student loans, credit card debt, car payments — but I had no expenses. The newspaper paid for housing and meals. And there was no chance for me to go shopping and rack up more credit card debt. So during those months when I was getting paid, I could just bank my check. I had so much more money because I was not spending it. And by the time I got back to the U.S., I was able to knock out most of my debt because of the time I spent overseas.
For the first time in my life, I realized the power of saving money. I think sometimes oh my gosh, if only our family could just live somewhere and not have to pay any housing, we would have much less pressure around money. But you can’t just have money wishes and dreams, you have to have income goals and deadlines toward meeting them.
10. What are your hopes for your business for the next five years?
Not a hope, but a plan. I plan to co-own a seven-figure business that has created the go-to platform for transition and change in the news business, and that supports individuals and organizations in telling their story for high impact.
Date of Conversation: October 11, 2017
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