From Concept to Company: Chat with Diane Loviglio, CEO of Share Some Style

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Wondering if you’ve got what it takes to start your own company? The main prerequisites are stubbornness and confidence (which may actually be the same thing). Join us as we chat with Diane Loviglio, CEO & Co-Founder of Share Some Style about her education, background, and insatiable appetite to learn and do more.  

Tell me a little bit about Share Some Style. Where did the idea come from and how did you go about creating a company?

I started Share Some Style with my husband. We just wanted to change out of our style that we’d had for the past 30 years, but it was really hard. We both felt like we were in style ruts, and we thought all we needed to do was just go shopping and buy new stuff. We started by working with the free personal stylists at stores and asking our friends, but we realized that it’s like going to the gym and thinking you’ll automatically get a six-pack. It just doesn’t work that way; sometimes you need a coach or a mentor.

We’re a style service that helps you meet people in person or online to help you find the clothes that fit you best or pick out an outfit for a specific occasion—these people know what’s out there and can interpret your needs and help you feel super confident.

My background is in user research, so we did a lot of interviewing people, visiting their homes, talking to them about shopping, looking at their closets, and we realized that this is a legit, real thing. Since then we’ve done 100 or more tests to decide who our client really is. It’s a lot of research, talking to people, and observing to understand their behavior.

Did you have any entrepreneurial experience before Share Some Style? What do you think it takes to make it as an entrepreneur?

My husband’s background is in computer science and mine is in architecture and anthropology, but we both had start-up experience before (this is the second start-up for both of us), so I had already realized that I wanted to do my own thing.

The first time, with my green tech start-up, I saw a problem and wanted to solve it. In that case, it was the best way to help people save money on their energy bills. I basically learned on the fly what a start-up was and what the roles meant.

My first start-up was about curiosity—it’s a natural trait of a user researcher, which I realized in retrospect. You don’t have to be tech savvy to become an entrepreneur. You just need to think about what the problem is and what the best solutions are. That just takes trial and error.

To make it as an entrepreneur, you need curiosity (to be interested in what’s going on around you and to identify problems). You also have to be a little delusional. What I mean by that is that when other people say ‘I would do it this way,’ then you have to be able to say, ‘Well, you’re not me.’ You can’t be too delusional because you need to know when to call it quits, but you have to get used to a lot of people telling you how to do things differently. You have to have passion for your idea, because you aren’t taking a salary and you’re trying to solve a problem that no one else is working on, or you’re trying to solve it in a new way.

You describe your current position as CEO and co-founder. How do these roles differ?

The CEO role is about finding where the money’s going to come from, whereas the co-founder role means I’m one of the first people who came up with the idea, but really I do whatever needs to get done. I’m involved in everything from customer support and marketing to operational and logistical concerns.

What is a typical day like for you?

I wake up, check and reply to email, attend partnership meetings, do user tests, coordinate photo shoots and shopping events, work on promotions, and plan and curate content for our blog.

As far as work/life balance, I definitely don’t work regular office hours. But at the same time, you can’t work all the time. For example, my sister is in town, so I’ll have dinner with her and I won’t be checking my email while we’re having dinner. I do still check my email before I go to bed, just to stay on top of stuff. I’ve realized that I like working a little bit all the time as opposed to being fully on and then fully off. Everyone thinks about balance differently.

What drew you to your current profession? Which skills, education, and experience were necessary to get you there?

No particular college class or anything; just the confidence I had that I could do anything and stubbornness—sometimes it’s hard to tell the difference between the two.

In college I designed a 4,000-square-foot green roof as a side project. I didn’t get any credits for it; it was just something that I wanted to do. It took me five years and I had to raise thousands of dollars in grant money for it, but just being able to do stuff like that. I’ve learned how to just start things without asking for permission first. Now I take that proactive approach to setting up meetings with other women who are running businesses or other people I’m interested in talking to. I’ve learned that I can’t wait for them to approach me first; I have to go out and find them.

What was your college major? How does it relate to your career path?

I majored in Architecture and Anthropology at Carnegie Mellon, where I graduated in 2005.

I wouldn’t be a start-up right now if I weren’t so driven about sustainability, which led to my first start-up, which led to what I’m doing now.

The program I did was interdisciplinary, blending arts and humanities. I had to get into both the architecture and humanities schools. I’ve always had to explain what I was doing and why, so I’m used to that. There were only 12 people in the program and at the time we were frustrated that no one got us, but now we’re so good at talking about what we do and helping people connect the dots. In retrospect, having an interdisciplinary degree helped set me up to be on a different path from everyone else and to explain it.

What are your favorite things about your job? Which aspects would you change if you could?

My favorite aspect is that I get to do a little bit of everything (marketing, partnership, user research, getting testimonials), which is awesome instead of just drawing beams. I know that at my age in an architectural firm, that’s what I’d be spending all day doing. I wouldn’t really change anything; I’m pretty happy with how things are going now.

What advice would you give to college students interested in pursuing a career path similar to yours?

Find a mentor—someone who’s actually done it before. The hardest part is thinking you’re the only one because you’re not going into a regular office. Sometimes you’re at home, at a coffee shop, wherever, and you think you have all these problems that no one else has, so it’s important to reach out and find other people like you who can share your ups and downs.

Can you share your favorite tip you’ve learned from a stylist? 

Wear three pieces to get a layered look.  I used to just wear tanks and cardigans, but I learned that a statement necklace on top—or not wearing a necklace and wearing a scarf—totally pulls the whole outfit together.

How has your personal style changed since starting Share Some Style?

It’s still a work in progress, but I’m starting to wear different types of shoes instead of just sandals. I’m also starting to really think twice about an item before buying it. I’ll ask myself, “How many different ways can I wear this?” and if I can think of three different outfits in my head, then I’ll buy it. And I found a tailor who is taking in the tops of my dresses because I have wide hips and a smaller top, so most dresses don’t fit me off the rack.

Homework time! Diane talks about the importance of following her own path, whether it was her college major or an independent project. Think of a way to pursue a topic that interests you and how you can apply this to your career path.

P.S. Need some help with job interview looks or just want a fashion upgrade? Check out Share Some Style on Facebook, Twitter, Google+, Pinterest, and Instagram!

Photo of Diane by JT Trollman

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