How 8 Innovative Female Entrepreneurs are Making Their Mark in Retail

Emily Weiss, CEO and Founder of Glossier

Emily Weiss, CEO and Founder of Glossier

By Tricia McKinnon

Forget trying to break the glass ceiling, instead make it irrelevant. That’s what a number of female entrepreneurs in the retail sector have done.  Female entrepreneurship is on the rise.  Between 2007 and 2018 the number of businesses owned by women in the United States grew by 58% vs. 12% for all firms. That growth has only gotten better in recent years with the number of women owned businesses increasing by 6% vs. 1.6% for all firms in 2018 alone. 

While women are creating more new businesses than ever, (1,821 net new women owned businesses were added in the US each day in 2018) a lot more work still needs to be done to help women to be successful as they take on these entrepreneurial pursuits.  For example, women only secured a dismal 2.2% of venture capital dollars in 2018. That’s in spite of data showing that the ROI for investing in female led business is strong. For example, a study showed that startups founded and cofounded by women had better performance over a five-year period, generating 10% more in cumulative revenue than the startups founded by men.

Despite these challenges there are more and more examples of women taking a chance at entrepreneurship and winning, big.  Here are 8 examples of successful female entrepreneurs in the retail sector to watch.  

1. Julie Wainwright, CEO and Founder of The RealReal

Photo of Julie Wainwright

Photo of Julie Wainwright

Julie Wainwright is the former CEO of pets.com an online company that is famous for not surviving the dot-com bubble. In life sometimes it rains and sometimes it pours. For Wainwright clearly she was having a bad day when on the very same day she decided that she would need to shut down pets.com her husband asked for her for a divorce.  Several years later she thought to herself: “man, this could be a really bad second half of my life. Or I have to figure something out.” Speaking about that time in her life, Wainwright remembers saying to a girlfriend of hers: “I had never created my own business before. I had always been the gun to hire. … But I had to finally say, nobody is going to give me my dream job, so I better figure it out myself.”

On a shopping trip with a friend who was buying second hand luxury clothing, her friend commented that she would never buy luxury items on a site such as eBay because there are too many counterfeits.  Instead Wainwright’s friend chose to shop at a small store she trusted.  That was the beginning of a great idea for Wainwright. She conducted research and determined that there was a huge opportunity in the luxury market and that an online luxury resale business would be difficult for Amazon to penetrate. As a sign of the potential for her idea Wainwright rummaged through her own closet and found 60 items that she could resell on her own.

With a great idea in her mind, in 2011 Wainwright launched the RealReal. It is a luxury consignment business that connects buyers and sellers of luxury items. It does the due diligence to make sure that Prada purse you want to sell on therealreal.com is actually real.   Wainwright has said that the process of building the business into what it is today was not been easy.  For example, she said that: “I think in general, most VCs are trying to do their jobs, but there are a lot of unconscious biases.” Wainwright recalls that one time during a pitch meeting, of all places, a male VC took off his shoes and put them on a table and told Wainwright that he could not imagine “ever wanting to sell them or buy another man’s shoes.” Perhaps now he wishes he had invested in The RealReal given that was worth $2.5 billion immediately following its IPO in June of this year.

2. Jennifer Hyman, CEO and Co-Founder of Rent the Runway

Photo of Jennifer Hyman

Photo of Jennifer Hyman

One day Jennifer Hyman’s sister told her about how she paid $2,000 for a dress to wear to a wedding that left her sister with credit card debt. That lead to Jennifer’s big idea that wouldn’t it be great to rent clothing instead of having to buy it? To see if the idea had legs Hyman teamed up with Jennifer Fleiss, her Co-Founder and they set up a pop up shop on campus at Harvard where they were attending business school. The duo offered 100 dresses they bought from Bloomingdales for rent.  The pop up did really well.  Reflecting on the experience Hyman says:  “[we thought] this can be a business that isn’t just about offering her [women] a rational or smart choice, but it can also be a business delivering something emotional to her, making her feel beautiful every single day.”

When starting the business they famously cold emailed Diane VonFurstenberg to get advice on their business idea and got a meeting. Their big idea turned into Rent the Runway which launched in 2009. It is a platform where customers can rent clothing, accessories and even home decor items. By the spring of 2019 rent the runway was valued at $1 billion.

Hyman is now one of less than 20 females that run a private company that is worth more than $1 billion.  But she didn’t get there without any bumps along the way.  At a recode conference Hyman said: “the major penalty that exists for female CEOs is that: “I have to waste 25 percent of my time explaining what my business does.” Hyman also said that male investors often make industry assessments using an “audiences of one”, such as their wife to provide perspective if they cannot test the product themselves. 

 3. Katrina Lake, CEO and Founder of Stitch Fix  

Photo of Katrina Lake

Photo of Katrina Lake

While at Harvard Business School, as part of a class project Katrina Lake studied ways to make it easier for women to access a range of brands while at the same time catering to their time starved needs.  Her idea was to leverage data to make recommendations on what women wanted to wear.  To test out the concept Lake decided to see if she could accurately select the clothing that 20 of her friends would like based on data gathered via a style quiz that each of her friends had to complete.  Based on the data from the quizzes Lake bought clothing she thought her friends would like and if they liked what she picked out they could keep the items. The idea took off and in the early days after launching the company in 2011 there were hundreds of people that wanted to use the service and the company didn’t even have a website at the time.

Lake recalls that before starting Stitch Fix she worked at a venturing capital firm thinking that one day she might join one of the ventures she interacted with.  Reflecting on that experience she said: “ultimately, I didn’t quite find the company I wanted to join, but I met more than 100 entrepreneurs and realized that all these entrepreneurs were just as unqualified as I was.” “If I wanted to be this retailer of the future, or if I wanted to join the retailer of the future, I could just start it.”

No one at Harvard Business School was overly impressed with her idea and Lake thought: “When you are doing something no one else is doing, you are either the smartest person in the room or the dumbest..” “For years, I didn’t know which one I was.” Clearly she was the smart one. When Lake took Stitch Fix public at 34 she was the youngest female founder ever to take a company public. Stitch Fix, the personal styling company she founded is now valued at over $3 billion.

4. Heidi Zak, Co-CEO and Co-Founder of ThirdLove

Photo of Heidi Zak

Photo of Heidi Zak

Back in 2011 Heidi Zak went on a bra shopping trip that ended up changing the course of her life.  Speaking about that moment back in 2011 Zak said: "I found a bra. It didn't really fit me, but I settled, I bought it, and I left." After Zak got home she thought: “there's got to be a better brand, a brand that really resonates with me." But as many women can relate, there wasn’t. Instead of accepting the problem Zak decided to do something about it. She conducted research and found that: "your average woman has two or three bras she wears 95 percent of the time, and then she has eight others that just hang out but don't fit. She never wears them.” "We believed we could really own the lingerie drawer by having that one high-quality piece." 

Zak quit her job at Google where she was a Senior Marketing manager and founded ThirdLove  a digitally native bra and underwear company with her husband in 2013. One of the popular features of ThirdLove is a Fit Finder.  The quiz provides a recommendation for the type of bra the customer should purchase in as little as 60 seconds after answering questions such as what their current bra size is and if they have any fit issues (i.e. the cups gape a lot). And the best part is that the bra recommendation is done virtually, no more awkward bra fittings.  14 million women have used ThirdLove’s Fit Finder quiz to-date. The data has enabled the company to design and offer 78 bra sizes including bras that come in half sizes, the first company to do so.  Zak has said that the company is trying to create a “bra for everybody”.  

ThirdLove has a valuation of more than $750 million.

5. Emily Weiss, CEO and Founder of Glossier

Emily Weiss worked for a number of popular magazines including Vogue, Teen Vogue and W magazine before launching her own beauty blog, Into the Gloss in 2010.  Weiss was still a fashion assistant at Vogue at the time.  While travelling for a shoot for Vogue Weiss noticed and liked the self-tanning product a model was wearing.  The model, Doutzen Kroes, told Weiss she should try it. Weiss did and she loved the product so much she asked if she could write about it in Vogue even thought that would be her fist time writing about beauty.  Reflecting on that experience Weiss said: “it was a total unlock moment.” “I was like,‘God, I love this. How fun is it to write about beauty? To talk about beauty? I just kind of caught the bug.” Then later that summer she decided to started her blog which she worked on part time until eventually she left her job to focus on her blog full time.

Photo of Emily Weiss

Photo of Emily Weiss

The blog was a hit due to her popular interviews with beauty mavens such as Kim Kardashian who provided insight into their beauty secrets.  Overtime Weiss became known as a beauty expert who had tested and reviewed hundreds of beauty products. The blog also enabled her to gain a deep understanding of what types of beauty products customers want.  Weiss then translated a dedicated millennial readership as well as an Instagram following into a set of loyal customers when she launched millennial favourite beauty company Glossier in 2014.  

Speaking about Glossier’s early days, Weiss has said: “Baby me in 2014 wasn’t sure if we could afford the next hire, didn’t know if anyone would like her idea for a beauty company ... and hardly knew a venture capitalist from a bank teller.” Glossier is now valued at over $1.2 billion.

6. Jen Rubio, Chief Brand Officer and Co-founder, Away; 7. Stef Korey, CEO and Co-Founder, Away

Picture of Jen Rubio and Steph Korey

Picture of Jen Rubio and Steph Korey

Luggage company, Away, was founded by Jen Rubio and Steph Korey.  The duo met while they worked at Warby Parker where Rubio was Warby Parker’s head of social media and Korey was Warby Parker’s head of supply chain.  Clearly a match made in heaven.

Known as the company that sells Instagramable luggage Away’s sleek and stylish luggage has been seen in the most exotic locations in world with some of the most famous celebrities and influencers.  As with most great ideas the idea for Away came to life by accident.  Speaking about that lucky accident, Away Luggage Co-founder and CEO Steph Korey said: “Jen had just been in Zurich and her suitcase broke and all the contents of it exploded everywhere.” “She was frustrated and asked me, ‘why isn’t there a luggage and travel brand that makes super high-quality products and that is affordable?’”  

That question was the impetus for the creation of a great brand. But how did the two end up reinventing the highly commoditized luggage industry? They interviewed hundreds of people to find out exactly what their pain points were with existing luggage brands with the hope of creating the perfect suitcase.  After their exhaustive research they designed a suitcase with many practical and in demand features such as: a built-in battery for phone charging, an interior compression pad that allows you to pack more in, and the ability to personalize a customer’s luggage with, for example a monogram.

Speaking about their successful venture Rubio has said: “I never set out to become an entrepreneur, but I’d always pursued roles that allowed me to work on things I was curious about. It wasn’t until my suitcase broke that my curiosity manifested into a business plan.” “I’m a problem-solver at heart and, in this case, the problem was that the brand and products I thought people needed just did not exist. Steph and I felt so strongly about it that we were compelled to do it ourselves.” It looks like they were on to something Away, which launched back only in 2015 is now valued at $1.4 billion.

8. Sara Blakely, CEO and Founder of Spanx - what year was it launched?

Photo of Sara Blakely

Photo of Sara Blakely

After graduating university, unable to get into law school, Sara Blakely took a job in sales.  For seven years she undertook the challenging and surely at times mundane task of selling fax machines door-to-door.  Speaking about that time in her life Blakely said: “during my fax-selling stint, I would spend much of my free time trying to figure out what I really wanted out of life and what my strengths were.” “I knew I was good at selling and that I eventually wanted to be self-employed. I thought, instead of fax machines, I’d love to sell something that I created and actually care about.”

One night the beginnings of Blakely’s dream would come true while she was getting ready to go to a party. Speaking about that time Blakely says: “in the hopes of looking better in my fitted white pants, I cut the feet out of a pair of pantyhose and substituted them for my underwear.” “This allowed me to benefit from the slimming effects of the pantyhose’s ‘control top’ while allowing my feet to go bare in my cute sandals. The moment I saw how good my butt looked, I was like, ‘Thank you, God, this is my opportunity!’”

Blakely then launched Spanx her shapewear company in 1998. She worked hard to get her shapewear product to take off and after two years she decided to quit her job and dedicate herself to the business full time. Two weeks after she quit her job she made it onto Oprah’s list of “favourite things” TV episode to show off her Spanx.  Needless to say the rest is history.  

For all of you struggling or aspiring entrepreneurs Blakely has said: “I didn’t realize that selling fax machines door-to-door was really laying the groundwork for me to be able to be an inventor and create a product that had never been done before and bring it to market, because doing something like that requires hearing the word ‘no’ a lot.” “The cold-calling to sell fax machines was an amazing training ground for hearing ‘no.’ I just learned that there’s a formula, you have to go through a certain number of ‘no’s to get to a ‘yes,’ so don’t let it discourage you.”

In 2012. at the age of 41, Spanx founder Sara Blakely was named the youngest self-made female billionaire in the world by Forbes.  All of this due to figuring out how to make a woman’s but look better in a pair of white jeans.

Additional Sources:

https://www.businessinsider.com/the-fabulous-life-of-spanx-billionaire-sara-blakely-2015-5#today-their-relationship-is-not-exactly-typical-over-dinner-with-friends-itzler-found-out-that-blakely-had-put-their-la-jolla-california-house-on-the-market-and-forgotten-to-tell-him-i-trust-her-to-do-whatever-she-wants-he-told-marie-claire-11

https://www.cnbc.com/2019/04/03/self-made-billionaire-spanx-founder-sara-blakely-sold-fax-machines-before-making-it-big.html

http://nymag.com/vindicated/2016/10/how-selling-fax-machines-helped-sara-blakely-invent-spanx.html

https://www.cnbc.com/2017/07/20/a-60-year-old-entrepreneur-took-her-business-from-zero-to-500-million.html

https://fortune.com/2017/06/06/the-realreal-female-founder-funding/

https://www.renttherunway.com/about-us/story?action_type=footer_link

https://fortune.com/2019/03/22/jennifer-hyman-rent-the-runway-unicorn-pregnant/

https://money.cnn.com/2018/07/31/news/stitch-fix-founder-ceo-katrina-lake-interview/index.html

https://www.inc.com/magazine/201611/liz-welch/busting-out-feminine-product-revolution.html

https://fortune.com/2019/06/28/wall-street-likes-the-realreal-stock-after-ipo-luxury-consignment-designer-resale/

https://www.cnbc.com/2017/09/26/3-success-tips-from-rent-the-runway-ceo-jennifer-hyman.html

https://www.elle.com/fashion/a15895336/katrina-lake-stitch-fix-ceo-interview/

https://www.nytimes.com/2018/06/01/business/katrina-lake-stitchfix-corner-office.html

https://www.cnbc.com/2019/03/20/how-emily-weiss-took-glossier-from-beauty-blog-to-1-billion-brand.html

https://www.thecut.com/2018/01/glossier-emily-weiss.html

https://www.vogue.co.uk/article/katrina-lake-stitch-fix-interview

https://techcrunch.com/2019/02/26/thirdlove-the-direct-to-consumer-lingerie-startup-gets-a-55m-boost/