Shira Wheeler

Need inspiration on how to forge your own path? Strategist and entrepreneur Shira Wheeler has already forged several over her lifetime—from starting a new life in France, to launching not one, but two businesses from scratch.

June, 2018

Rollerblading was so cool for a while.
So cool! There used to be this square where you'd rent roller blades and you'd roller blade with all the hot, very tan people of South Beach. [Laughs]

My first couple years in Miami were kind of rough, though. My interpretation of South Beach was from the early nineties when I was a little girl. Going back there to live as an adult was completely different. Lots of clubs and partying. It’s fun for a minute and then it’s not.

I eventually started hanging out with the art and music school kids. Art Basel had just come to Miami Beach and there was an interesting local art scene developing. It was an exciting time. I got an internship at one of the first galleries in the Wynwood district. It was kind of the Wild West in that neighborhood at that time. It was pretty sketchy.

I studied studio art with a double major in advertising, and then I had a minor in marketing. So, oddly, I’m working in the exact field I studied.  

Which never happens!
At the time though I thought I wanted to go into art. My internship at the gallery turned into a job and I stayed an extra year after graduating. I started to realize, after being burned by the gallerist I was working with (long story), that the art world wasn’t really for me.

At the time my parents had been living in Paris for my dad's job. He had retired from Continental after 9/11 and started flying for the Vice Premiere of Lebanon.

Wow. That would have been fascinating!
Yeah. He really enjoyed it. In addition to flying the VP and his family, he got to fly around all these dignitaries including President Clinton and President Bush senior around Africa. They lived in Paris for five years, so after Miami I went to live with them there.

I took an intensive French course at La Sorbonne, and I was tutoring English and doing all these odd jobs, and then… I met a Frenchman.

Well you were living where the French men live …
Exactly. You know it's funny, people always say to me, "Do you miss Paris? Didn't you love Paris?" I did, but the first year was really lonely. Parisians are not the most welcoming. I think deep down, they’re very friendly and wonderful people, but they're not as warm and welcoming as New Yorker's. In New York, when you first meet someone you think, "Oh, she's probably a nice, interesting person. I will introduce myself." In Paris I was already at a disadvantage being an American during the Bush presidency and it always seemed like people already had their friends and/or assumed I was stupid without saying a word to me. It was very humbling.

You had to prove yourself.
Yes! But by the end, I had totally figured out how make friends [laughs] and even how to get people to smile back at me on the street. They found me (and I found them) trés charmant by the end. That was about 10 years ago now.

So what brought you back to the states?
I was working odd jobs in Paris and enjoying the expat life. It's such a dreamy city! It's so beautiful, and the quality of life is so good. Like the food and just the joie de vivre, you know? My relationship had gotten more serious and I had applied to a program there and got in, but they wanted to send me to Lyon. The point was to get to the next step in life, and I kept hearing from French friends who were like, "I'd give anything to move to New York. If only I could get a visa." So I was like, "What am I doing here?" This is great, but there's so much more opportunity for me in the United States.

I had friends who lived in New York so I stayed on a friend’s couch while I was applying for jobs. It was brutal.

Finally, I found a job at Radical Media, a production company. I joined their in-house design department, which they were in the process of developing into an in-house ad agency.

It was at the time when all these companies wanted to become 360 media agencies. Meaning they handled everything for clients—from developing the concept to handling all production—all under one roof. We were the agency on record for Grey Goose and Tommy Hilfiger. I came on as the assistant to the creative director, but it was such a small team that I was also kind of doing studio management. I was running payroll, helping to sort through portfolios, working with the producers and designers and a bunch of other stuff. Once the department had more structure, though, it turned into purely an assistant role. After about a year and a half, I was given a promotion and a raise and they made a new position for me! And then the recession happened.

Ahh yes, that glorious time.
At first I was like, "Whew. I made it!" I got my promotion just before they put on a hiring freeze.  A couple of weeks later I got called to HR and was told I could keep the raise but not the promotion. So it was back to being an assistant.  

Just before that I had met this woman, Roanne Adams, who was a graphic designer and freelance art director. I actually brought her in to interview for a project at Radical, but when we met she had also mentioned that she was looking for a project manager. I’d remembered that after the promotion fiasco and reached back out to her a few months later. After a lot of back and forth (it was the recession after all), she ended up hiring me. It was scary jumping ship from a relatively stable position and taking a chance with this freelance graphic designer/art director who worked out of a basement. But, I really liked Ro and I liked her work. So, I took everything I learned at Radical about building infrastructure (what to do and what not to do) and applied it to helping her create a studio. It was an incredible opportunity to build something from scratch. Eventually we became RoAndCo.

After a few years, I was becoming really interested in strategy. When our clients had first come to us, we were designing lots of print materials, and brand identities and then maybe a website here and there. Clients weren’t sure yet if that was something they actually needed.  

I'll never forget one of our clients being like, "Do we need a Facebook page? We're a luxury fashion brand.” It was a totally new era in marketing and I don’t think any of us imagined how much it would change commerce.

Slowly but surely, clients were coming to us purely for e-commerce. We would build these beautiful websites, but oftentimes, no one would visit them because there wasn't a strategy to get people there. So I started getting really interested in that side of the business.

It was frustrating to see so clearly that some of our clients needed help—with the bigger picture, how all the pieces of their marketing plan worked together. With some of our clients, we had a close enough relationship that we worked together as a team to develop the concept and strategy. With others, we were handed a budget and hired purely for design or art direction. I saw that there was a missed opportunity for smaller businesses to reach a much bigger audience with just a little bit of forethought and planning. I thought, “what if I could help them build their budgets and strategy and then these brands could begin working with awesome design firms like RoAndCo? With social media and the web, small-medium size brands could achieve the same results that you once needed a million dollar ad budget for. So, I decided to go freelance and I started Figure. We had some incredible clients right off the bat.

Was it terrifying going out on your own?
Totally terrifying. But once I put myself out there, let my network know what I was doing and put it out in the world things changed. One of my first projects was Paintbox.

When I met the owners, they explained this brilliant idea to reinvent the nail salon experience. It was a dream project. I helped them build a team and a marketing budget and clarify what exactly they wanted that experience to be like and how to define and reach their audience. We used “your favorite restaurant experience” as a model. We created a very curated menu of looks that were elegant, but also fun and approachable, a super lux studio experience (you’re greeted by a hostess who offers you sparkling water or tea or champagne), and helped create a photobooth that snaps pics of your manicure that you can immediately post to social media. We also helped staff their marketing team to continue executing on our strategy.

They get such great press - it’s an amazing place.
It is! They’re awesome people so it’s been so cool to watch it succeed. I was also working with the equally amazing M.PATMOS and began working on an e-commerce site for her so I brought on Stephanie Draves Dunn, whose expertise was in e-commerce launch strategy. We worked together for about a year and half. It was an incredible learning experience.

We worked with a slew of awesome clients like Bird, Simon Miller, Wright, The Brave Collection among others—helping them with core brand and marketing strategy and e-commerce planning. Eventually though, we decided that it wasn’t the best partnership for us.

Hence the learning part.
Exactly. I think finding a partner is really like getting married. I was so excited about the idea of a partnership, about sharing something with someone. I don't think I went into it with as much forethought as I could have and as I will in the future.

When Stephanie decided to leave Figure, it was like, "Okay, what is it that I really love doing?" It was kind of existential.

When she left, you were like, "Would I do something different?”
That's exactly what I asked myself. I'd always had this idea for a sexy 100% cotton underwear line.

It's really hard to find. I’d gotten really serious about it when I was at RoAndCo. It was my side project for a few years. I created a business plan, the branding, samples—and then Roanne got pregnant and went on maternity leave, and I was like, "Okay, I have to focus on the business. Let's put this aside for now." Even when I started Figure, I was like, "Oh, maybe I'll have the time to do it on the side. Of course, that didn’t happen.

When Stephanie left Figure, it was time.

I went on an inspiration trip with a friend to Portugal, one of my favorite places. On one of the first nights, I had one of those sleepless nights, where you can’t stop thinking, and I realized that it wasn’t so much that I wanted the underwear to be sexy, it was more about exploring what I meant by “sexy” and continuing this conversation that kept on happening when I would talk about the idea—why cotton?

Sexual health experts and gynecologists recommend that you wear 100% cotton underwear, not 95%, not 97%, not just in the lining. The fact that so few women I spoke with knew this opened up a can of worms. What else didn’t we know? Who is defining the conventional idea of “sexy” for us? So I started looking at sex-ed programs and thought back to my own highschool sex-ed program where we learned all about the male anatomy but we never learned about the clitoris or pleasure.  

That was never mentioned in our sex ed at school either.
Yes! I realized that I wanted to be part of evolving this conversation in The States.

That sleepless night in Portugal I had an idea for a manual that explored the language around sexuality, starting with the basics—our anatomy and pleasure—and saw that I could use the business, the underwear and the manual as a tool to help reframe the conversation.

I find that being away helps bring clarity. I realized that the idea was still really important to me and I need to bring it to life. Figure has morphed into more of a consulting business for now.

Soon after I got back I learned about this program called Etsy.org (now called the Good Works Institute), which is a scholarship based business education program for entrepreneurs who want to develop businesses that create good in the world. It's a really special program. The idea is to give support to small businesses, who want to contribute to society rather than just make a profit. I was accepted into the program. It was an intensive 3-month program; I had always considered going back to school, but hadn’t found the right program. This was kind of like, “bingo!” This is what I need.

I had the initial idea for Oddo and an understanding of what I wanted it to be but I was able to use the program to really crystallize and evolve it into what it is today. For example, I wasn’t sure if I wanted to seek out investment or how I wanted to fund the business, and through the Etsy program, I decided that Kickstarter was the best way.

Kickstarter is great, but It’s such a huge amount of work.
I knew that it was work but I don’t think I realized just how much of an investment it was. Just putting together the video was intense. My husband has been incredibly supportive, bouncing ideas around with me since the beginning. He LOVED the idea for a manual—he kept calling it a zine, and offered to help with the video. Another friend helped me go through a thousand rounds of the script. We have another friend, a photographer/director, Vincent Perini, who was in between gigs and was like, "Let's do this together". We all put in so much work and energy, but I was really blown away by how dedicated Vincent was and how he nailed the video.

We launched the Kickstarter in March just after the Etsy program finished and we reached our goal in April.

I have an amazing board of advisers that includes a technical designer, an art director, a midwife, gynecologist, a sexual health expert, an editor and business advisors. It’s been a total pleasure to work closely with the team to build something that I think is really special and GOOD.

What stage are you at now?
We're producing the fabric in Japan. It's so beautiful. It’s being sent to our factory, which is in Brooklyn. It was really important to us to keep everything as local as possible.

We’re also printing all the T-shirts and the manuals. Everything is coming together. I have an amazing art director Jess, who has been involved almost from day one. She's so well informed … she's not only helped to create the visual images of the brand, but she’s helped shape the vocabulary. That part has been really important; we want to elevate the language around women’s health. We want it to feel aspirational, sexy and beautiful but it's really important that it still feels inclusive.

Essentially, we’re selling product to support our content and collaborations. We want to inspire women to learn about their bodies, to join this conversation about sexuality and what it means to be a sexual woman today. The idea with Oddo is to give women who aren't necessarily celebrities or activists or people in the public spotlight the opportunity to be involved in the conversation and feel like they are participating in a meaningful way.

We're actually working on a workshop concept for college students. It’s just in the prototype stage now because we’re knee deep in production.

That's amazing. I like to think I’m pretty informed about my body, but there is always so much more to learn.
That's exactly how I felt once I started digging a little deeper. Have you heard of ‘Our Bodies, Ourselves’? It’s an organization that was started in the late 60s, early 70s, and it’s also a book.

The book is still around and it's an incredible resource. It’s great to have in your bookshelf because it covers everything from anatomy to relationships, to how different women feel about their sexuality. We actually got in touch with them really early on and asked them if they would want to do something together. We interviewed one of the cofounders—she is incredibly inspiring and passionate about so much. It's been cool to involve her in the conversation, and to hear what kind of barriers they were met with back in the 70s.

There’s so much more information available now, but there is also a lot of misinformation; that's why I love the idea of something printed and tangible that you can keep on your bedside table and maybe share with your partner.

How do you feel running your own business in New York? Especially such a progressive subject matter. Does being here influence you in any particular way?
Absolutely. I think New York is far more progressive than other places in the States. I think the amount of creative, intelligent, hard working and inspiring people has been an incredible resource. At the same time, this city is hard. [laughter] Some days you’re riding over the Manhattan Bridge and the sun is setting and you see this golden skyline and it’s magic. You feel like you’ve put all this work and sweat and tears into the city and it’s finally giving you something meaningful back. But then other days, it's raining and you're running around, and everything is going wrong and the city is ugly and it smells.

What is the best piece of advice you could give?
It’s a piece of advice that I was given that I’m still working on ...

You can say anything to anyone, it’s just a matter of how you say it—how you frame the conversation. I’ve had the benefit of building a community of kindred, compassionate and genuine people. It’s easy to explain one’s perspective to someone who is open to receiving it.

It’s when someone is close-minded, self-centered, has some kind of bias or is just plain having a bad day that it’s incredibly challenging. To say something hard, without making someone feel defensive or ashamed is important. It requires being incredibly thoughtful about where the other person is coming from and acknowledging that. It seems very relevant today, doesn’t it? Sometimes I nail it, sometimes I don’t. Sometimes it’s impossible, but at least you tried.

What does New York mean to you?
New York is a crazy place. It’s the opposite of superficial—there’s a depth and a realness to it. You can always dig a little deeper. It’s unpredictable and surprising. But that can also be kind of overwhelming. It’s endless. For me, it’s been important  to find my own peace and rhythm. New York to me means hard work and opportunity and inspiration and love.

Photography by Stephanie Geddes ©