Ruthie Davis — Life & Business Lessons from a Leading Fashion Entrepreneur

Nikos Kokkinoplitis
16 min readMay 30, 2022

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Who is Ruthie Davis?

Is she a shoe designer to the stars? A leading fashion entrepreneur? A guest lecturer at MIT and NYU? A beloved television fashion expert? In fact, Ruthie Davis wears all these hats and many more. During our interview in mid-November, I discovered a persona and ambition that resisted easy characterization. Though I cannot hope to capture Ruthie’s spirit, I hope to have started you on the path to discovering more about this fascinating and enigmatic personality.

Background and Context of the Interview

Ruthie Davis grew up excelling in athletics. She describes sports as being a form of “mini entrepreneurship”, with the product being herself. Her dynamic approach to sports training led her to claim various awards and trophies in skiing and tennis. At Bowdoin College, Ruthie majored in English Literature and Visual Arts, served as captain of the tennis team and covered sports for the college newspaper. At this point, her dream was to become a sports journalist. After graduation, she began working at The Hartford Courant, a daily newspaper, and later, at ESPN for their daily show, Sports Center. Outside of her career, Ruthie developed a small personal training business, which thrived to the point that she decided to open her own gym, which was a combination workout studio/ fitness apparel store. This entrepreneurial experience was pivotal in helping her develop her marketing skills, given that “she had to market herself as the fitness trainer, the instructor, the coach, and fitness stylist…”

The success of the business, coupled with her plan to open a second outlet, fueled her decision to pursue an MBA in Entrepreneurship degree at Babson College. The day before graduating, Ruthie interviewed with Reebok, who offered her the position of Associate Product Manager. Four years later, she was promoted to Director of the Reebok Classic Division. She continued her corporate career as the VP of Marketing and Design at UGG, and later, at Tommy Hilfiger, as the VP of Marketing and Design for Women’s Footwear.

In 2006, she launched her eponymous footwear brand, Ruthie Davis. Her avant-garde designs have become the top choice for celebrities across industries, ranging from A-listers like Beyoncé, Lady Gaga, and Ariana Grande, top-tier supermodels and influencers like Naomi Campbell and Kendall Jenner, and world-class athletes like Lindsey Vonn and Alex Morgan. In recent years, Ruthie has received extensive recognition for her impact and influence, including the American Apparel & Footwear Association’s 2014 “Designer of the Year” award and the 2019 “Collaboration of the Year” award for her Disney X Ruthie Davis collections. In addition to overseeing the operation of her company, Ruthie Davis currently serves as a television fashion expert with regular spots on Bravo, E!, Bloomberg, CNBC, Fox News, and NBC, among others. She is also a recurring guest lecturer at MIT Sloan School of Management, University of Delaware Fashion Department, FIT, and NYU Stern Business School.

Red Heels designed by Ruthie Davis

In November 2021 I had the great pleasure to conduct an interview with Ruthie Davis and learn more about the person behind the brand. I truly believe that her story can be a unique source of inspiration and contemplation for those who dare to pursue passion and authenticity over megalomania and vanity; those who dare to understand the reasons behind their actions; those who dare to craft their own definitions of success without conforming to social norms. You don’t have to necessarily agree with Ruthie’s perspective and views on the world. But I’d encourage you to consider her responses and ask yourself whether they offer some insight into your own experience. Remember, this is not the story of Ruthie Davis. These are the reflections of a person who has achieved paramount personal and professional success and wishes to impart what they have discovered…

Interview

Looking at your career, one observes that before launching Ruthie Davis you pursued many unrelated things. Were those past career decisions part of a long-term plan to create the Ruthie Davis brand?

No, one thing led to the next. First and foremost, from a very young age, I’ve always been somebody who followed my passion. I like to get excited. I like to do things that make my heart pound. So, whatever I did I gave 180%! I didn’t worry too much about thoughts like “oh, this is going to be my career one day…”. I gave it my all and I let it take me there.

Based on what you just said, I understand that your interests didn’t really change over the course of time. You always followed your passion and this helped you connect the dots and made you the person you are today.

Exactly, I just followed my passion and it led me to where I am today. And when I went to Reebok, I did the exact same thing! I started as an Associate Product Manager, worked my way up to product manager, to Director, and by the time I took my next job I had figured out that I really liked designing the product. But I’ve always been someone who liked the kind of designing that collides with marketing — I also like to build the brand. I don’t just design in a vacuum. I design with a consumer target, with a marketing plan. There is a reason for the product to be. For example, at Reebok, I was the Director of Reebok Classic. So, what I tried to do was revamp the shoes to make them more fashionable. I looked at what the kids were wearing and I did my research on the latest fashion trends. In this way, I managed to reinvent the classics. So, this is an example of how I approach things. I always ask myself: what’s the story behind the product? How are you trying to make it more consumer-centric? And I could spend hours talking about this, I don’t want to lose you with all this information. So, the conclusion is that one step led to the next, with passion as my driver. Also, I always approached a job as a potential entrepreneurial venture.

What is the source of your passion?

I’m always trying to do things better. I like improving things. I’m always rearranging stuff. For example, I’m constantly trying to organize, minimize and make my apartment look better. I’m always questioning what’s next? How are we going to make it better? I always have that energy that keeps me motivated. In every job I had, I went way beyond the job description. I couldn’t do something if I wasn’t excited about the product. I always loved shoes because I think shoes make the outfit. I saw how a shoe (ski boot) can transform how you ski, how you play tennis, how you move in your everyday life. I like to feel good! I like to feel hot when I play tennis! I always liked that about fashion, how it makes you feel. It’s a powerful feeling. And I think I first learned that in sports. For example, when I used to ski race in high school, I thought I was going to a black-tie event — I felt chic and aerodynamic and I skied faster in the race!. Or when you go to the gym and you have a great workout look, you will probably have a better workout. Your outfit manifests your success in sports and in everyday life.

So how can someone find his/her passion in life?

It’s a great question. I think you just have to start small and go step by step. Try to find that little thing that excites you today. Ask yourself: what makes you want to get up in the morning? What’s the thing that you have the energy to do without forcing yourself? I think you just need to try to answer these questions for yourself and go from there.

But be careful, don’t get ahead of yourself. A lot of people want to get into entrepreneurship and say “oh I’m going to start a new entrepreneurial venture” and they end up putting the cart before the horse. They don’t know what they’re going to do. They say they want to create a brand or make a widget. “I want to make a product. I don’t know what it’s going to be, but I want to make a product.” I didn’t do it that way. I had a personal need that I could not find in the marketplace. I wanted shoes with the colors, tech, and excitement of a Nike or Reebok coupled with the high fashion glam of a dress shoe. I couldn’t find this so I created them myself. The need is what got me to create the product. I think it’s important not to get too ahead of yourself when you’re figuring out your passion. Just let it grow. You don’t have to be consumed with what the future holds.

I think that from a very young age, our family and our surrounding environment (teachers, friends, professors, etc.) are stressing the importance of pursuing a career that we are passionate about. However, we rarely discuss the steps one needs to pursue in order to get there. What are your thoughts on this?

Well, finding your passion does not require a structured methodology. Take me, for example. Instead of thinking “oh, she is lucky, she gets to live her passion of making these really cool shoes!”, consider that making shoes isn’t my passion per say. Again, the shoes alone are not really my passion; what I am passionate about is putting together a plan, building out a new product, coming out with an assortment, considering how I’m going to market this product. Counting the orders. Getting the sales. Merchandising the shoes. Figuring out what goes where. For example, I organize my shoes so that I can visually see which are selling and which are not. I’m not sure this answers your question, but what I’m telling you is what gets me really excited and passionate! It’s not the shoe itself, it’s building something! I’m an organizer; I’m a planner; I like checking what’s selling and what’s not. If someone says to me “oh I can’t find my passion; I don’t know what my passion is”. If you really think about it, your passion might be cleaning and organizing your room. How do I make a business out of this? People should get away from the thought “I need to find my passion”. Your passion is just something you organically enjoy doing. It’s just different skill sets.

Speaking of skill sets, which aspects of your training/background/life experiences do you think were most vital to your success?

Firstly, I think that the corporate skills I developed when working for Reebok, UGG, and Tommy Hilfiger are irreplaceable. I learned how to make shoes; I went to the factory; I participated in trade shows; I worked with the sales representatives; I learned how to make business plans… So, I think that all of those skills are really invaluable. Also, starting my own business and getting myself out there was an incredibly useful learning experience. When I launched Ruthie Davis, I made my shoes in Italy. I literally had zero connections and zero knowledge of how to make shoes in Italy. I just went for it. So, I just had to learn by doing. I’m also a big believer in knowing your brand, your product, your industry. your market; being really knowledgeable on whatever it is. For example, I consider myself an expert in shoes, you can ask me whatever you want about them. I know everything about my competitors; I know everything about the shoe market; I know how to make the shoes; I know all of the shoe terminologies. I also study the success models of other brands even if they are not direct competitors. So, I’d say that being an expert in your field is a prerequisite for success. This helps me establish trusting relationships with my partners, my retailers, and my clients. They know I know what I’m talking about. And by the way, I know so many people — especially young designers I’ve talked to — who don’t really know their products. They haven’t thoroughly researched their markets. So, the business knowledge you acquire from a business school is an important skill to have, but I do feel that knowing the particular market you are planning to penetrate is even more important. I talk with many young people who think that they have the best new ideas, and if they conducted some basic research, they’d see that their concepts have already been attempted in the past and sometimes failed!

On a scale of 1–10, how satisfied are you with your life and career so far?

Probably right now I’m going to say a solid eight (8). The reason for this is that I always want to leave room to be better. One important thing I want to share with you: I’m a big believer in defining success for oneself. In the past, I used to want to be the next Louboutin, a very successful independent shoe brand. I used to want to be the best shoe designer: famous, admired… whatever you want to call it. But that’s not my goal today. My definition of success now is kind of what we talked about earlier; being excited about my day, feeling enthusiastic about what I do, like I’m still a young kid, loving what I do. You can’t put a price tag on those things. Also, running a business I’m proud of, which means that everybody on my team is inspired in their work and is being paid well and I’m delivering a high-quality product. I make people feel good. I run a nice, clean business. It’s a happy business if you will. I have no skeletons in the closet, and I work hard to pay it forward. Taking time to mentor young designers and entrepreneurs. And I feel good about it. I have a very strong message about my brand. And I am profitable. I can pay my bills. Being in the fashion business is very hard and requires a lot of resources, especially in the footwear industry. So, most small brands in this industry are not profitable and they try to survive with debt until a big player buys them out. But I run a sustainable and profitable smaller business. Maybe I’m making less money, but I don’t need tons of money. That’s not my goal! I want to have enough money to live in a nice place, to enjoy trips now and then. I’d rather run something smaller, tighter, leaner that I have control of. This also gives me more flexibility in my life and to me that’s a success. That’s why I give myself an 8 because I feel proud of the sustainable profitable brand that I created.

Are there any external factors that might affect one’s definition of success?

One major trend that I observe is that young people value experience over ownership. For example, they are not buying cars or apartments; they prefer spending their money on experiences. There is a whole idea of experiential where you choose Airbnb over owning an apartment. The same for cars. “I have to be nimble and agile”. I feel that this idea is redefining success. I have a lot of young nieces and nephews who would rather leave the office on time and cook a nice meal and travel on the weekends. They don’t want to live a life where a career is everything. I think that the definition of success is changing based on this trend. The importance of money will be replaced by the importance of time. “I’d rather have less money and more time to spend on the activities I enjoy”.

Do you have any major regrets in your career?

I wish I had started Ruthie Davis a little earlier than I did. I probably stayed corporate a little too long. But… at the end of the day, everything was a learning experience. I had to go through it to learn it. Apart from that, there is another regret I have that comes back to the definition of success. There was a period in my life in which I wasn’t aligned with my true definition of success. You know… I was a competitive person, I looked at what other people were doing and I wanted to be cool. Everyone has happy benchmarks. The world tells you you have to do this, this and this. So, I hit all of the benchmarks! I had the cool office in New York City. I had the cool employees. I had this, I had that… Because that’s what people think you have to do to be considered successful. The day I turned the corner and said “I don’t care what anybody thinks”, I’m going to do what I think is best for the business, was the day I became truly successful. That day, I got rid of my office in which I was paying 7K / month and built out a home office! Yeah, it was a crazy day. People might have thought “oh, she is not doing well, she went back to a home office”. “This is a step backwards”. But I was ahead of it because everybody is doing it now. I built my home office a year before the pandemic. I had this whole idea of traveling and working off your laptop. I’d rather spend my money and energy being out in the market rather than paying huge rent for an office. And I give this flexibility to the people who work for me. They operate like freelancers. So, I started the remote working culture very early in my company. Because I realized that I was paying for things that the business didn’t really need but I did them because it was considered a benchmark of success. Sometimes you need to do that. You need to have the cool office to convince yourself. But at the end of the day, it really doesn’t matter what other people think. There were some things I did that I wish I hadn’t done. I really did spend a lot of money on things the business really didn’t need. But you’ve got to learn it. You have to go through it. But I try to share this with young designers who end up spending all of their money early in the game and then run out.

What other activities are an important source of wellbeing in your life?

Exercising, eating right, and sleeping well. Feeling healthy in my skin and in my body is very important. I like to feel strong, awake, and healthy. I couldn’t imagine doing my job without a healthy lifestyle. Also, I love the interaction I have with young people. I mentor a lot of students and young designers and I do a lot of speaking. Being involved with people and getting their feedback motivates me and gives me incredible energy!

What advice would you give to a young individual who is making his/her first career steps?

I’d say don’t put so much pressure on yourself. Things evolve naturally. It’s step by step. Don’t pay that much attention to what others are thinking or how you might be perceived from the outside. What matters is to feel good and in control of what you are actually doing. And by in control, I mean having a grasp on the subject. Don’t let it get ahead of you. Don’t feel the pressure to be bigger than you are, do more than you are. Less is more. Do it at your own pace and feel good about the pace. The people who are criticizing from the outside and asking “oh why you are doing this” or “why you are doing that” are the ones who are not doing anything at all. Their job is to critique other people. Usually, those people are not starting a brand. Staying focused on the project at hand is what’s really important.

There is one thing I want to share with you… and it’s really strange. So there comes a day when you are going to be successful and you’re going to do really well. You’ll think that everyone is going to be proud of you. Because you finally proved to your family and friends that you can do it. You think that when you prove to them that you are successful, they are going to be excited and proud. But you know what’s really weird? In reality, nobody cares what you are doing. Everybody is so busy with their own lives. The day you realize that, it’s the day you start doing what you do for yourself, because nobody ultimately cares about what you do, they care about their careers, their lives, how they are going to pay the bills this month. That’s the day you’ll be free. You are not going to disappoint them because they are not thinking about you. You have to write your own book. This is your success story, not someone else’s. You are on your own journey, not someone else’s. Don’t try to mimic someone else’s journey. For example, I don’t want to have a huge company. I don’t want to manage tons of people. I personally don’t want to do that. I am the true entrepreneur that likes to do everything. I am a true, small, niche business and I’m doing it successfully based on my own definition and goals for success. Someone else might be different. Someone else might want to run a big company with hundreds of people. I like a simple life. I like being in control of my day. I like to be hands-on. A smaller business but a great business. Small doesn’t mean you are not great!

Do you have a systematic approach to life planning? For example, do you frequently write down your values, your goals, etc.?

I think it’s a combination. I feel that even having a talk like this today helps me articulate things. After our discussion I might reaffirm my own goals. I discuss a lot of these topics with people, especially my friends and my husband. I’m constantly evaluating where I am and where I plan to go through talking about it. I also am a big “To Do” list person. I write the tasks down and then work hard to check them all off.

Finally, has this discussion helped you reevaluate your goals?

Yes, I think this call has helped me because I have confirmed to myself my initial belief that bigger is not always better. Also, when you asked me to rank my life satisfaction, I said an 8 and I’m curious to look deeper into what’s missing. It’s a new year soon, so I think it’s a good period to reflect and think about the next cool thing I’ll be doing in 2022! One thing for sure that I am excited for is writing a book with the working title, “How to Build a Lean & Mean Fashion Machine.” (Bigger is not always better) Maybe this will get me to a 10!

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