5 Entrepreneurial Success Stories in Retail to Inspire You

Photo of a Warby Parker Store
 

By Tricia McKinnon

It’s often in the moments when we least expect it a new idea, a new business is born. In the retail sector where there are many stories of struggle there are also many stories of triumph. These founders show what is possible when you believe in an idea and don’t give up until you see it through to fruition. 

If you are hesitant to make the jump into entrepreneurship or have already gotten started but feel like your dreams may not come to pass use these stories as your motivation. If these entrepreneurs can do it so can you. 

1. Julie Wainwright, CEO and Founder of The RealReal

In life sometimes it rains and sometimes it pours. It was clearly thunderstorm season for Julie Wainwright when on the very same day she decided to shut down pets.com, the company she previously ran, her husband asked for her for a divorce. Later on 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, Wainright’s 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 small observation then became the beginning of a great idea. Wainright began to conduct research and determined there was a sizeable opportunity in the luxury market and that an online luxury resale business would be difficult for Amazon to penetrate. Wainwright also rummaged through her own closet and found 60 items that she could resell on her own, a sign of the potential for her idea.

With a great idea in her mind, in 2011 Wainwright launched The RealReal, a luxury consignment business which connects buyers and sellers of luxury items. The RealReal does the due diligence to make sure the Prada purse you want to buy 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 it was worth $2.5 billion immediately following its IPO in 2019.

2. Pat McGrath, CEO and Founder of Pat McGrath Labs

Outside of the beauty world you may not have heard of Pat McGrath but to beauty insiders she is a legend. Over the course of 25 years McGrath is responsible for the makeup on models featured on over 500 magazine covers and has worked backstage at over 3,000 runway shows. 

For many years McGrath was enlisted to help create beauty products for many popular brands including Giorgio Armani, Max Factor, Dolce & Gabbana and Cover Girl Cosmetics. And for 15 years she spoke to makeup executives about creating her own make up line but they discouraged her, telling her that consumers are not interested in wearing the type of bold makeup looks that she creates for runway shows. But then McGrath’s social media followers kept asking when she would launch her own line. That pushed her to do it. 

The makeup artist to the stars launched her own make up line in 2015. It was one of the first direct to consumer makeup brands and by 2018 Pat McGrath Labs is worth over a  $1 billionAs a testament to the brand’s success, within its first month on sale at Selfridges, Pat McGrath Labs achieved the highest sales of any brand during the department store’s storied history.  

Speaking about her success McGrath said“you might always know you’re different, but you should never worry about that and it’s a real game-changing moment when you realize that. A lot of people have their opinions or maybe try to bring you down and I remember being a bit younger and being slightly affected by that. Then you reach a point where you go, ‘You can have your opinion, but I know what I’m doing and I’m happy doing it.’ That’s their opinion, it’s not my life, so onwards and upwards. I know that’s what gives me that empowerment and strength.”

3. Sara Blakely, CEO and Founder of Spanx 

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 Spanx made it onto Oprah’s “favourite things” TV episode and 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.


Do you like this content? If you do subscribe to our retail trends newsletter to get the latest retail insights & trends delivered to your inbox


4. Andy Dunn, Co-Founder and former CEO of Bonobos

If you have ever been on the hunt for a nice fitting pair of pants either for yourself or for a loved one you may have shopped at menswear retailer Bonobos. Like many brands Bonobos started from humble beginnings by selling pants, pants that fit better than most. In the beginning founders, Andy Dunn and Brian Spaly sold pants designed by Spaly out of the back of their car and at house parties

“So here we were running around school having guys try on pants. Guys are like dropping their pants behind parked cars and trees, giving us checks and cash to buy the product. At some point we woke up and we had made tens of thousands of dollars from selling pants and that's when you can kind of humbly say to yourself, 'maybe we're on to something,'” says Dunn.

After selling thousands of dollars in merchandise in a haphazard fashion the co-founders launched Bonobos’ direct to consumer website in 2007. Within the first six months online the brand projected it would make a million dollars within the first year alone.

Speaking about the time near the launch of Bonobos online Dunn said: “it was so exciting what was happening in Silicon Valley at that time. Facebook was coming off the ground and Twitter had just been launched. I really wanted to build something on the internet and here's this guy, my good friend, who's made a better-fitting men's pant. The curved waistband, the right fit in the rise, the right fit through the thigh, really confidence inspiring fit, and I thought, 'Wait a second, maybe this physical product is actually the internet company that I've been looking for.' Maybe by taking this great product and selling it online we can deliver better service, more fit, more size and get out to a much wider group of people than the traditional way retail brands are built.”

After finding success online Bonobos eventually opened up its own stores, expanded into Nordstrom and was bought by Walmart for $310 million in 2017.

5. David Gilboa and Neil Blumenthal, Co-Founders and Co-CEOs of Warby Parker

When David Gilboa one of the founders of Warby Parker lost his $700 prescription eyeglasses on a trip before attending business school at Wharton he did not want to pay a hefty price to replace them. Instead he spent his first semester of MBA school squinting his way through his classes. Then for a year and a half Gilboa and his then classmates and now cofounders talked about how they could offer prescription eyeglasses at a fraction of the price charged by existing brands. 

Those discussions led the quartet to launch Warby Parker, with each co-founder investing their life savings providing $120,000 in much needed startup capital. Since then Warby Parker has taken the eyeglass industry by storm by offering inexpensive prescription eyeglasses starting at $95. Warby Parker is able to keep prices low by designing its glasses itself, avoiding licensing fees and cutting out the middleman. Given the popularity of the brand it’s clear that millions of consumers were also looking for a way to see, and look fashionable on a budget. 

To launch the brand Warby Parker thought it would be best to be featured in the best women’s and the best men’s fashion publications to generate buzz about its business. To achieve this goal it hired a PR company which successfully pitched profiling Warby Parker in GQ and Vogue. Both magazines ran stories bout the brand on February 15, 2010 the day Warby Parker’s website launched. Based on the buzz generated from both of those publications, Warby Parker’s website ended up crashing at launch. But Warby Parker was able to meet its first year sales target within three weeks and within four weeks it sold out of its top 15 most popular styles leading to a 20,000 person waiting list for its eye glasses.

Speaking about getting Vogue to even notice the startup, Neil Blumenthal, co-founder and co-CEO of Warby Parker, said: “I think founders and CEOs often take credit for being the smartest people in the world, but so much is serendipity and timing. We were one of the first of these vertically-integrated brands, so the story was novel.” Warby Parker is now valued at $3 billion.