Leaning into uncertainty to connect and lead with authenticity: Mary Dail discusses essential elements of women’s success
As a pandemic ignited around the world in 2020, many people sought a safe space to live and work while waiting for the time when being together was no longer a risk. A sanctuary space was especially important to Mary Dail, owner and creative director of Big Leo Productions. While the pandemic raged, Dail suffered an unimaginable loss—the death of Mary’s husband Andreas, just 46 years old, from a sudden heart attack. To say his loss rocked Mary’s world would be an understatement. At a time when the world was already upside down, to suffer the loss of her best friend, business partner, life partner, and father to their young son, Loki, and her stepdaughters, was an especially cruel blow.
Yet just seven months after losing Andreas, Mary beams through the screen during our interview, her warmth radiating, donned in a Goonies t-shirt from her husband’s vintage shirt collection. She wears one every day to feel close to him and to remember the joy which filled the time they had together. After nearly 22 years in New York City, Dail, a North Carolinian by birth, and her Swedish husband, decided to put down roots in Richmond, Virginia, a perfect midway point between family and work. The couple split time between Richmond and their apartment in NYC, where they own a bar and Dail manages her photography and production business. But, their Southern home became especially sacred in the aftermath of enormous loss and the uncertainty of a global health crisis. It is from here that Mary spoke with Space for Arts about leading with love and authenticity, and pursuing opportunities that find their way to you.
You moved to New York in 1995 after college, hoping to be an actor and set designer. And now you split your time between New York and Richmond, Virginia, as you navigate life and manage Big Leo. How did you get your start in the photography business?
I started Big Leo after having a job that taught me so much about photography from all angles. I was the photography editor at Martha Stewart Living for a few years and worked for an incredible woman there, Heidi Posner, to whom I attribute so much of what I have built within my business because she was an incredible mentor. It’s one of the reasons I’m so passionate about mentoring and helping other women in the business, and why I am so grateful to be a part of Focus on Women. Heidi was the photo director at Martha Stewart Living; she was probably the first official photo editor at Living which launched in 1990. I started at Martha Stewart as a temp and tried to make myself as indispensable as possible, because I really loved what I was doing and learning. I was organizing the photo archive and doing some billing work for the photo department. I hit it off with Heidi. I looked up to her. When my temp gig was up, she moved me to another department to keep me in the company. Then, the photo department grew exponentially, because Martha Stewart published the Weddings Magazine and Cookbooks, and then launched Baby – a special issue which turned into several, all while the retail sector grew quickly (Kmart followed by Macy’s) and the Martha by Mail catalog was in full production at that time, too. So, there was big growth, all of which required expanding web needs as well. While I was brought back into the department to focus on Martha Stewart Living Magazine, other photo editors focused on the Weddings magazine, and special issues, catalog shoots, and retail or “advertising”.
What kinds of things did you learn in your positions at Martha Stewart?
Mainly the photography essentials. I took advantage of a few education stipends the company offered and brushed up my skills at ICP. I wanted to be sure I knew my stuff! I learned the fundamentals of magazine publishing, too, including how to navigate editorial meetings, where you talk about the stories and ideas with the creative and art directors of each department. We would review portfolios to see who the appropriate photographer for a specific job was. And then we would choose someone and start production.
You took what you learned there and made a jump, which led, unexpectedly, to the formation of Big Leo. Tell us about that.
I was the client of an agent who was looking to start a division of emerging photographers for her agency and with whom I got along very well. We started talking and I accepted the job. As I recall, she kind of wooed me away from my job – it was different, a new skill and I love to learn – and then about six weeks in, she decided that it wasn’t right. I was completely devastated. I thought, “Oh, my God, I just left a job that I really love. And, I have just been let go.” Another former client and agent friend, Cornelia Adams, reached out and asked if I wanted to work with her (savior!). She became another really great mentor from whom I learned a lot about the business of photography. At Martha Stewart, I was on the creative side, and a lot of my job was finding the right photographer for our projects. The new business endeavor involved both creative and business knowledge and Cornelia was a veteran rep. After working with CA1CA2 for about two years, I decided to start my own agency, which briefly carried my own name, but was shortly thereafter named Big Leo, a nod to my astrological sign. I wanted to stay true to my passion and where I excelled at Martha Stewart, which was nurturing food and interiors photography.
Over the years, however, Big Leo has expanded into the beauty market as well, but product, not fashion beauty. For me, beauty products can be approached so much like shooting food because beauty products have become so much more organic, more botanically inspired, through the years. It often feels and shoots like food. Conversely, it’s exciting to see food shot in a very fashion-like or conceptual way, too. There’s a lot of crossover with beauty products and food. Beauty used to be very hard lit “soldiers” where the product is tall and heroic. And now it can be a little softer at times. You’ve got beautifully styled botanicals and ingredients and all the smears and swipes are treated very much like food. Food for the skin!
It takes a certain kind of personality to say, “I’m going to start my own business.” How did you know that you could do it?
If I had sat myself down and said, “You know, I think I’m going to start a business today,” I don’t know if I would have done it. There was something very visceral, very instinctual about doing it. I worked as a sole proprietor first, then after some time created a structure. Eventually, I realized I needed some additional protection and filed all the paperwork to become an LLC and give it a name. It was just me at first, and I had a very small roster. It was easier for me to handle more production then, too. Then I met Willie Mullins, who has been with me for almost 18 years now. He was my neighbor and though he was temping at a law firm at the time (I think?), he was and still is a very talented artist, a performer, singer, and dancer. He started working with me as an assistant, a billing coordinator and then an office manager, and later, when we were looking for someone to run our stylist division, he came to me and said, “You know, I think I’d really like to try this.” A lightbulb went off in my head. I was like, “Oh, my God, of course, he’s been with Big Leo for all this time. He knows all the artists. He knows all the clients, he has a fantastic personality, so of course!”
So Big Leo was born from modest beginnings but you’ve grown it into something quite comprehensive. What are you doing to push Big Leo to the next level?
People are doing really amazing things with, for example, lighting, and they are experimenting and pushing themselves. I’ve learned that there are always clients with whom we connect, and with whom we are a good fit because of X, Y, or Z. But creatives at ad agencies are looking for something new all the time. I’ve heard many times over the years that art producers at ad agencies really like to see personal work and I totally get that, because they want to see noncommercial work. They want to see the way you’re seeing other things, not just a specific product. They want to see the way you see the world through your lens outside of a commercial composition. We have to innovate, we really have to keep pushing so that we don’t run our course with a client. We have to keep sight of why we started in this business—to be creative.
Do you have any notable clients for whom you felt your work was particularly innovative or special?
One of our photographers, Evi Abeler is constantly innovating and learning. She is a refreshing collaborator, continually educating herself on new technology and new equipment all the time. We landed a project with Newman’s Own which I produced, and yikes, it was a lot of work. It was my first time producing after losing my husband, so it was definitely a lot, especially after trying to ramp things up during COVID, too, but it was so beautiful. In photography, shooting pizza is every food photographer’s and stylist’s nemesis and dream at the same time, because it’s hard. The cheese! But, the client was a dream. And the agency was a dream. And the agency producer was a dream. It all really just came together. And, what a fantastic company, Newmans Own. They give their profits to charity.
You met Traci Terrick, one of the other founders of Focus on Women, at a cocktail party. Tell us about how that relationship yielded Focus on Women.
Traci is an incredible colleague. She’s everything I’ve ever wanted in a rep friend. Traditionally, reps have not spoken to each other, which is very frustrating because we have so much to offer one another. Lots of groups were started and then disbanded when people would bow out or hold information close to the vest. But now, information is available to all of us, especially with the internet and technology age that we’re in. You can find information anywhere, so, learning and growing are really focused around your relationships and what you have to offer. Helping each other does not have to be a big competitive thing. Traci is a great collaborator, and I think we view the business and life in much the same way. It has been a magical union. Traci and another rep friend of ours, Andrea Stern, owner of Stern Rep, began speaking as a group every Friday when COVID started, because we had planned to travel to Chicago together for a portfolio review. Well, we can assume how that turned out in early 2020. So, what began as a COVID-era support group turned into much more. What we have and what we’re giving each other every week is incredibly valuable. The support alone—it’s the kind of support we’ve all wanted, needed really.
What is most important to you about Focus on Women?
Women, in general, have always been highly competitive with one another, which I feel is the wrong approach to our creative survival and our soul’s survival. I think that women work so much better collectively. Women who come together really make things happen. Working toward common goals helps us not be undervalued or underrepresented in the industry. We want to highlight amazing women, collaborate with each other, and provide resources and solutions for one another.
What do you envision for the future of Focus on Women?
I’d love to see a real hands-on mentorship program for women continue to develop. In fact, Focus On Women started a mentorship program where I am a mentor and I just completed my first of six sessions with an LA-based beauty photographer. It is really rewarding to give back. The Kelly Montez agency, Apostrophe, offers an incredible mentorship program for the BIPOC community. We have such an opportunity through Focus on Women to serve and mentor women and I hope what we have started continues to grow, whether through classes or one-on-one mentorships.
About the author: Megan Reilley is an editor and writer living in Western Maryland. She holds an MFA in Nonfiction from Goucher College, where she teaches undergraduate writing.
