Leading the retail industry transformation

Rent the Runway’s Jenny Fleiss on the importance of passion and innovation

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If you’ve been paying attention to the news, you’ve probably heard a lot about the economy. Just as no one can predict with complete accuracy when a recession will hit, no one can predict exactly when the economy will recover. While over time the economy does follow certain patterns, right now it feels unpredictable and extremely uncertain.

For most people, an uncertain economic environment creates a feeling of fear. You might be fearful about your company going out of business, or laying people off. If you’re just entering the workforce, you may be afraid you won’t be able to find a job. Or, perhaps you’re scared of the hit your portfolio will take – that your retirement savings won’t be enough for the lifestyle you want. And if you’re a business owner, you may worry that your business won’t survive a recession.

Regardless of your situation, a challenging economic environment requires one thing: innovation. In both good times and bad, innovation is a critical piece to moving forward. And what many people don’t realize is that recessionary environments have yielded some of the most innovative companies of our time, like FedEx, Airbnb, Disney and Microsoft.

You’re about to hear from an entrepreneur who started her business right smack in the middle of a downturn. Jenny Fleiss created Rent the Runway, a company now valued at $1 billion, in the wake of a severe economic recession. When everyone else was panicking in 2008 and 2009, Jenny and cofounder Jennifer Hyman saw that a retail industry transformation was happening – and they saw an opportunity. In this episode, Jenny shares how she and her cofounder got Rent the Runway up and running, then grew the business to where it is today.

Who is Jenny Fleiss?

Jenny Fleiss is an entrepreneur, business owner, venture fund partner and mother of three. She’s certainly busy, and that’s exactly the way she likes it. Jenny started Rent the Runway right out of college, setting up a pop-up shop and eventually evolving the business to what it is today: an online service that allows women to rent designer clothing, online, for a fraction of what it actually costs.

Jenny has won every award you can think of: Top 30 under 30, Top 40 under 40, Forbes Entrepreneur of the Year and more. Yet eventually, she made the choice to step away from a company valued at $600 million. Why? She says, “I have always been a serial entrepreneur at heart … I missed that startup stage. I was ready for the next adventure.”

Jenny left Rent the Runway in 2017 to start up Jetblack, a personal shopping service that was part of Walmart’s first-ever technology incubator, Store #8. 

Jetblack was discontinued in 2020 and Jenny chose to find fulfillment in a new, equally impressive way: as the first female venture partner at growth equity firm Volition Capital.

The retail industry transformation

Today, the rental, or sharing economy is booming – companies like WeWork, REI, and Zipcar make it possible for us to experience something without the cost of ownership. Rent the Runway was at the forefront of the trend. Jenny saw that consumers were starting to think differently about how they consumed clothing and were becoming more proud of consuming in smart ways.

The problem they were trying to solve was simple enough: Looking into your closet and realizing you don’t have anything to wear to an important event, like a wedding, but don’t have the budget to buy something new. So they innovated, and created an entirely NEW way to shop. That’s what radical innovation is all about.

The importance of passion

Rent the Runway has received more than $400 million in venture capital and earned an early partnership with legendary designer Diane von Fürstenberg. Jenny credits this impressive start to one thing: passion. Her personal experience informs everything she does and, she says, gives her “the passion that is needed to constantly go after your dream and vision day after day after day.”

Rent the Runway evolved alongside Jenny’s life, eventually expanding to everyday wear like blazers, pants and skirts as she found that she was no longer going to as many fancy events. Jenny now has three children under age ten, and she’ll share her views on work-life integration and why she wants to inspire her daughter with her work.

It doesn’t stop there. You’ll also hear Jenny’s philosophy on how she approaches hiring talent, which is not only critical when you’re starting a business, but also when scaling it. The interviewer for this episode is Scott Harris, a coach, mentor and a speaker at many of Tony’s events, including Business Mastery.


[03:50] Rent the Runway explained – “closet in the cloud”
[04:28] The problem of having nothing to wear
[04:57] The importance of passion in entrepreneurship
[05:30] The evolution of Rent the Runway
[06:08] Starting Rent the Runway after business school
[06:50] Consumer shopping changes with recession
[07:10] Testing and learning from customers to refine concept
[07:56] Story of the gold dress – you’re really selling an emotion
[08:50] Clothing is emotionally transformative
[10:00] Decision to go back to the trenches
[10:34] JetBlack – personal shopping over text message
[12:07] Being freed from your to-do list
[13:33] Importance of hiring for flexibility
[14:20] Why taking big leaps is critical
[14:47] Jenny’s test for positive mindset
[15:20] Where to find good hires
[16:10] Success in business is a series of failures
[17:37] Best way to balanced kids and work
[18:46] How to bring entrepreneurial spirit once startup phase is over
[19:06] Intrapreneurship at Walmart
[19:49] Moving fast with small dynamic teams
[20:33] Take stock of your life path to identify opportunities
[21:03] Women drive online consumption
[21:30] Audience Question: How do you get back up after failure?
[23:32] Audience Question: How do you get into business before college?

Jenny Fleiss has blazed her own path from the retail industry to venture capital, achieving both professional and personal success. She has built business empires and seen her share of failure – and she never gave in to fear. So what’s holding you back? Whether it’s an uncertain economy, fear of failure or lack of time or money, the truth is that these are all limiting beliefs. And once you overcome them, you’ll become truly unstoppable.  

Team Tony

Team Tony cultivates, curates and shares Tony Robbins’ stories and core principles, to help others achieve an extraordinary life.

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