How I'm Skirting the Rules

I’m Not Waiting for Permission to Do What I Love

Olga Vidisheva moved to Los Alamos, New Mexico from Russia at 17 with $100 in her pocket. Now the 30-year old is running a multi-million-dollar company as the founder of, a unique platform that connects women with local boutiques around the globe.

Olga has been finding a side door to her dreams her whole life. Her first job in the US was as a waitress at a sushi restaurant, where she says she learned her first English word, cucumber. In just a few years, she mastered English, gained acceptance into Wellesley, and helped pay her way through modeling. She didn’t even know the word ‘Goldman’ before she applied for a job at Goldman Sachs her junior year, but she got hired. After being one of the top analysts at the banking firm’s Technology, Media & Telecom group, she went for her MBA—at Harvard.

When Olga started back in 2012 right out of business school, the company had 25 boutiques.  Now, four years later, the platform sells from 5,000 boutiques in six countries and counting. Olga thinks one secret to her success is retail’s continued disruption as more of us seek our fashion online, which has democratized the playing field. And she isn’t the only one winning: By sourcing truly local shops never before available online, fashion lovers don’t have to hop on a plane for traditionally hard-to-find pieces. Female boutique owners are empowered, enabling their goods to reach more women and helping support their local economies. She radiated optimism and ambition when we met her at a recent Skirting the Rules and Chantelle “Art of Being” salon. Read on to find out how this skirter turned her passion into profit.

I am Skirting the Rules by fundamentally questioning the dogma I grew up with. In the former Soviet Union, we didn’t have many choices about what to buy—everything was the same. I never liked feeling like I was the same as everyone else. Then I moved to the US, and thought that somewhere along the line I think women began to believe that luxury must be high-priced. This definition of luxury felt off to me. I think real luxury is instead about being able to be one of a kind, being yourself.

So one of my favorite things to do on business trips while working at Goldman Sachs was shopping at small boutiques for something different: whether it was a gift to bring home or a dress to wear to the next event. Much of the local products wasn’t expensive. I’d find these unique shoes in a tiny Paris boutique and would want to buy more after returning home, but couldn’t find the boutique anywhere online. Opening my closet to all of these special pieces collected on my travels brought back happy memories and inspired me to start Shoptiques. I wanted to bring local boutiques online to make them available to more women.

I believe the most powerful feminine strength that helps women get ahead is creative passion. At Goldman Sachs there was an amazing intellectual energy, but what was often missing was the passion to go to work. The small store owners we partner with are passionate about their craft; they are not trying to be the next Macy’s. They are trying to create something different and unique, true to who they are. My mom was a musician and so I understand that mentality of being passionate about what you consider to be your art. Being around this kind of creative passion every day is inspiring and contagious. When you love what you do, you are going to be a thousand times better at it just because you love it!

My biggest rebel move was starting Shoptiques because it was a great unknown. I had absolutely no retail experience, but I decided to figure it out. There were so many logistics, such as how we would affordably ship the pieces from small boutiques around the world to our customers all over the world or how we would photograph items that are only available in small quantities?

To make it doable, I had to break it down into steps. It can get overwhelming to think at scale, so I put it into more digestible stages. First was the private beta launch. If I achieved that, I would keep going. Having these little milestones makes you see that you can do it. After private beta, my goal was to get funding. Once we did that, then scaling the number of stores. I think it’s important to set goals and then celebrate all the little achievements along the way.

An example of how listening to my intuition has helped me is following my gut to launch my company right out of business school even though the more traditional path might have been to get more working experience first. At the time, I was graduating HBS and had loans from financing my school. However, I felt like there was a disconnect: small boutiques had products women loved, yet they couldn’t figure out how to be online and compete with large retailers.

I really believed in what I was doing so I told myself it would be okay if I failed. I think women need to allow ourselves to take big risks. You have one life and if you don’t pursue what you love, then when else will you do it?

My secret talent is my ability to cut through the noise. Time is the most precious commodity in today’s world. Whether it is a casual conversation or an interview, I have, what I consider, a very valuable skill: To be able to read between the lines, read someone’s expression and understand their true self, drive, and motivation. I am able to quickly digest the situation, assess all of the facts, and make a decision.

A woman is most powerful when she feels good about herself. For example, I feel so much better during a big meeting if I love what I’m wearing. You want your clothing to be a reflection of who you are, to be unique! As Mary Kay, founder of Mary Kay cosmetics once said, “While clothes may not make the woman, they certainly have a strong effect on her self-confidence, which, I believe, does make the woman.”

The female disruptor who most inspires me and why is a woman named Pauline Brown who is currently a Senior Lecturer at Harvard Business School. Prior to joining HBS, Pauline was the Chairman of North America of LVMH, and prior to that worked at Carlyle Group, where I almost went to work before attending Harvard Business School. Pauline is a friend, a mentor, and honestly like a sister to me. People dream of being different or leaving a mark in the world, but most are too scared to pursue a path less traveled. Pauline pursues her own definition of success. Name me another woman who started in beauty, moved to finance as a Partner, then became Chairman of one of the most recognized luxury brands, and then left to become a professor. Pauline is fearless and inspires me to listen to my gut over pursuing something that doesn’t feel natural to me, but looks good on my resume. She is brilliant, fierce, yet gentle and kind. She never had a mentor and found her own path.

My advice to my younger self would be to work with people you like—it will kill your day (and your productivity and happiness), if you’re not enjoying the company of people around you.

My favorite ‘mini-skirt’ is to surround myself and the office with inspirational quotes and uplifting images. I really believe in the power of visual cues to shift your mindset.  Call me cheesy, but I have a puppy calendar on my desk in the office because you just can’t help but smile when you see a sleeping puppy. My notebooks have quotes on the covers, like “Crazy just might work.” Our walls have posters with quotes like “What will blow our customers’ minds?” These visual cues remind us throughout the day what to focus on and to stay motivated.

Another mini-skirt is to do quick moves that release endorphins because it makes you happy. For example, one of our staffers encourages everyone in our office to break at 4 pm to do pushup or squats instead of drinking coffee for a pick-me-up.