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Democratizing Luxury

Rent the Runway and JetBlack cofounder Jenny Fleiss on starting a unicorn company that has transformed the retail industry

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If you’ve been paying attention to the news, you’ve probably heard a lot about the economy – and the looming threat of a recession. While no one can predict with complete accuracy when, or if, a recession will hit – financial markets have signaled the possibility that our nearly 10 year streak of economic growth is coming to an end.

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 the most severe economic recession the United States has seen since the Great Depression. When everyone else was panicking in 2008 and 2009, Jenny and cofounder Jennifer Hyman saw an opportunity.

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 by allowing women to rent designer clothing, online, for a fraction of what it actually costs.

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. But to put this in perspective, nothing like this existed at the time.

In this episode, Jenny shares how she and her cofounder got Rent the Runway up and running – and how they grew the business to where it is today.

And it doesn’t stop there. Jenny left Rent the Runway in 2017 to start up JetBlack, a personal shopping service that is part of Walmart’s first-ever technology incubator, Store #8. You’ll also hear Jenny’s philosophy on how she approaches hiring talent at JetBlack, 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?

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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