The Alluring Story of Jennifer Hyman and Jennifer Fleiss’ Visionary Journey with Rent the Runway

Have you ever wanted to wear the latest designer clothes but didn’t want to drop thousands of dollars? Well then my friend, Rent the Runway might just be your new go-to solution. 

Hello, and welcome to Life By Design 360 Phenomenal Friday, I’m your host, Doug Reed, and today, we’re diving into the fascinating journey of two remarkable women: Jennifer Hyman and Jennifer Fleiss, the co-founders of Rent the Runway, a revolutionary and highly successful fashion company. 

Today, I’m going to show you how it grew from a small subscription model to a multi-million-dollar global fashion phenomenon, and what hurdles these founders overcame along the way. 

Let’s start from the beginning. It was 2009 when Jennifer Hyman and Jennifer Fleiss, both Harvard Business School graduates, launched Rent the Runway from a small apartment in New York City.  

The concept? Offering women the chance to rent high-end designer clothes for a fraction of their retail price. Simple, yet groundbreaking. 

But what motivated them to start such a company in the first place? 

Jennifer Hyman’s story begins with her own personal frustration. At the time, she had a closet full of clothes, but none of them felt right for the different events and occasions she was attending. She thought, “Buying something new for every event was expensive, impractical, and wasteful”. 

As she looked around, Jennifer realized that women everywhere were facing the same issue — they wanted to wear the latest fashions, but the cost was just too high. She thought, “Why not rent?” 

This idea was born from a need: the desire to have access to high-end, high-quality clothing without the long-term commitment or hefty price tag.  

But the challenge was, how do you make women feel comfortable about renting clothes that they would normally want to own? 

 

The answer? Trust. Jennifer Hyman and Jennifer Fleiss wanted to create a seamless, reliable process that made renting clothes as easy as buying them.  

They set up a simple website, worked with designers to offer exclusive collections, and started small with just a few customers. 

But as we all know, the road to success is never without its challenges. So, what were some of the obstacles they encountered? 

 

Well, for starters, they had to overcome logistics. Renting clothes at scale requires a highly sophisticated supply chain. Think about it: renting means constant returns, cleaning, and inventory management.  

The founders realized quickly that managing a rental business with such high-touch services meant they had to find a way to deliver impeccable service while keeping costs low.  

And when you’re dealing with high-end designer pieces, there’s no room for error. 

They also faced skepticism. Renting clothing was a relatively new concept, and many questioned if women would truly embrace the idea. After all, the fashion industry was built on the concept of ownership — and now these two women were asking people to let that go.  

It took a lot of convincing, but Jennifer Hyman and Jennifer Fleiss proved that women were ready for the shift. 

One of the major turning points was the creation of their subscription model, allowing customers to sign up for a plan that offered access to a rotating selection of designer dresses and accessories for a monthly fee.  

It was the ultimate solution for fashion-conscious women who wanted variety without the financial burden. 

 

Fast forward to today, Rent the Runway is a $1 billion company. Their revenue continues to grow, and they’ve expanded beyond just dresses to include everyday wear, work attire, and even activewear.  

They offer a subscription-based service for clothes, and their innovation has allowed them to build a loyal, diverse customer base. 

But despite their impressive success, it’s not all smooth sailing.  

The world of fashion is always changing, and Rent the Runway had to adapt, especially as the global pandemic disrupted everything from fashion to retail.  

The company quickly pivoted to an e-commerce model that allowed them to offer rentals and subscriptions to customers remotely, without the need for brick-and-mortar stores. 

 

Let’s take a quick look at the impact Rent the Runway has had today.  

They now have over 11 million members and have expanded their services to include everyday fashion, like jeans, jackets, and tops, on top of their signature high-end special occasion wear. 

In terms of sales, Rent the Runway is generating over $250 million annually, and they continue to grow, despite the ever-competitive retail space.  

The company has not only grown into a global phenomenon but also helped pave the way for a new generation of sustainable fashion. 

As for Jennifer Hyman and Jennifer Fleiss personally?  

They are doing well, too. Jennifer Hyman’s estimated net worth is over $200 million, while Jennifer Fleiss, after having stepped away from the CEO role, also continues to invest in startups and initiatives, with a personal net worth estimated at $50 million. 

 

What can we learn from Jennifer Hyman and Jennifer Fleiss’ incredible journey with Rent the Runway? 

First and foremost: the power of innovation.  

When you see a problem, think about how technology and new business models can solve it.  

Second, adaptability. Rent the Runway’s success shows that even in the most unpredictable markets, the ability to pivot and rethink your model can keep you relevant.  

And finally, perseverance. From the initial struggles to their billion-dollar success, the story of Rent the Runway is one of grit, vision, and determination. 

 

That’s a wrap on today’s episode. I hope you’ve enjoyed learning more about the incredible journey of Rent the Runway and how Jennifer Hyman and Jennifer Fleiss took a relatively simple idea and turned it into a billion-dollar business. And how you can too! 

Throughout 2025 I’ve given you a lot of great stories about others who did it. Some of them you knew and some of them – were new to you. 

Soon I can’t wait to let the world know about your story. What your situation was, how you overcame the challenges of a layoff or a change in your career and turned opportunity into success.  

The best way to get started is to start today. Get your 7-point guide to an income you can’t get fired from and join us on building your magnificent journey. Completely eliminate the worry of being fired or going through a layoff and redesign your life with a reliable monthly income doing something you love while helping people that are truly a joy to be around.  

To get started, go to lifebydesign360.com/guide. Get your guide today and go from a boring job to unlimited opportunity. 

Again that’s lifebydesign360.com/guide. Go there today and join us on your miraculous journey. 

 

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 Thanks for tuning in, this is Doug Reed signing off for today. I’ll talk to you next week at Life By Design 360.