On My Co-Founder and Friend Jenny Fleiss

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


Jenny was the first true believer in Rent the Runway and in me. When I told Jenny the idea for Rent the Runway during a Monday lunch/gab session at Harvard Business School’s Spangler Hall, her immediate reaction was “This sounds fun, let’s do it!” Jenny has always had fire and almost indescribable energy – and these qualities prompted me to partner with her and never look back. When I reflect on the past eight and a half years, one way to tell the story is that it’s been the most fun adventure of my life. Another is that it’s been a once in a million business success that most did not believe that two women with zero technology, logistics or fashion experience would be able to achieve. But, what is often ignored in the glamorized, edited (and sometimes snarky) stories of entrepreneurship, female co-founders and startups – is that the past eight and a half years has really been a story of a real and everlasting friendship that Jenny and I have built together.

Jenny and I started Rent the Runway when we were both single and in our mid-20s. We had only known each other for a year but we knew that we had fun together and respected each other’s different personalities and ideas. Over the past decade, Jenny has become a permanent member of my family–a sister–and our lives have changed dramatically during this time. I danced with Jenny at her wedding to her amazing husband Andrew and celebrated the birth of her three beautiful children. I feel so privileged that I have gotten to experience Jenny become a mom three times over while still working at Rent the Runway and being our Co-Founder. Jenny is an incredible mom–so fun loving, silly and up for any adventure–I feel indebted to her for being a role model to me and to all women in business for building a beautiful family and a beautiful career simultaneously. I remember the humid July day when Jenny called me to tell me her incredible mother Julia had just passed away, and holding Jenny’s hand at the funeral, and hugging her in her apartment and trying to make her life, which would never be the same, just a little bit brighter for her when she got back to the office by filling her desk with meaningful photos and pink flowers (her mom’s favorite!). I often say that one of Rent the Runway’s most important core values, “Happiness and Positivity is a Choice” that we use to guide our culture and hiring, is modelled after my sister Becky–and it is–but it is also modeled after Jenny’s mother Julia who supported the two of us at every turn and was a constant source of inspiration, cheerleading and positive, beautiful energy.

The most difficult decision I have made while being the CEO of Rent the Runway, was not about our business or our team, but a very personal decision to call off an engagement and a wedding as a 33-year-old woman who very much wanted an everlasting marriage and family – and was fearful that if I called it off–it might be too late for me. Daily honest conversations with Jenny gave me the courage to follow my heart and the courage that I would fall in love again and have my dream family alongside my dream career. She was one of the first to set me up on dates and was constantly scheming 🙂 As I sit here today (in Brooklyn!) writing this tribute to Jenny, so in love with my soon-to-be husband, and nine months pregnant with our first child, I think about how indebted I am to Jenny and so many others for encouraging me to go after my Big Life!

For millennial women like Jenny and me, the Big Life (with all of its amazingness and complications) doesn’t stop because you decide to become entrepreneurs and it’s not just about your career. We were growing up together at the same time as we were growing a business together – the two should not, and cannot be separated. We have made mistakes together, we have fought and resolved our differences through honesty and communication and we have shared so much humor and fun and love and ridiculousness together. I am so proud of the women who we have become and the personal growth we continue to have. I am proud to have created a culture at Rent the Runway that has always and continues to be diverse (our 1000+ employees, and even more significantly our leadership team, is nearly 85% female and minority). I am proud to co-lead a foundation with Jenny that we continue to invest our time and energy into to support thousands of female founded companies scale throughout the U.S. We have created a culture of kindness at Rent the Runway that celebrates our team and values our employees’ whole lives–their lives as parents, as fiancees and partners, as having-a-dream-to-travel-the-world, as continuous learners, and as founders of their own companies–after their time at Rent the Runway.

My relationship with Jenny has taught me that it is possible to have it all and to go after your dreams in life. When we started Rent the Runway over 8.5 years ago, I knew Jenny would start multiple companies throughout her life–as she has that early-years entrepreneurship bug whereas I have the burning flame, the lead-RTR-forever-into-the-heavens bug. I am proud today to support Jenny’s dreams to go back to the beginning, just as she has always supported mine to lead this company to the moon. Jenny will always be the Co-Founder of Rent the Runway and she will always be my friend.


With much gratitude and love,

Jenn Hyman

CEO and Co-Founder, Rent the Runway and Jenny’s #1 Fan!


Here are just a few of my favorite memories with Jenny over the years (read her announcement, here).



Jenny was the first mom at RTR and brought Daniella into the office all the time, which was always my favorite part of every day. This is me and Daniella sharing a special moment after Daniella first learned to walk.




Jenny and I on our way to a prom that RTR donated to a school that had been devastated by Hurricane Sandy. And we had Jordin Sparks sing! It was amazing.We may have had more fun at this prom than we did at our own high school proms 🙂




Dancing at the launch of our first real Rent the Runway pop-up store at Henri Bendel on 5th avenue.




We have always enjoyed #twinning.




Ummm….coolest day ever! Getting Joan Rivers to fall in love with RTR.




Toasting the five-year anniversary of RTR!




Jenny, myself and Brooke (Founding Team Member and Current Chief Product Officer) rented a van, covered it in RTR decals and took a tour of Sororities of the South donning “Have a One Night Stand (With Fashion)” t-shirts, a slogan that my then 18-year-old brother Josh came up with. Let’s just say we learned that UVA and UNC party a bit harder than Harvard and Yale, our alma maters!




Marveling at the crowd at our first year anniversary party at Avenue. And again #twinning.




Blowing kisses at Fox News.




On our second NYE, we decided to have a last minute sample sale in our offices and gave the team 24-hours notice to execute because we wanted to boost sales. This was after a long day of the two of us being salespeople to hordes of random New York women we had let loose in our office.




Michael Bloomberg, our favorite mayor ever, gave us an award for entrepreneurship.




Our first photo shoot for Vogue (ok, just Teen Vogue, but still doesn’t it count that Vogue is in the title?!).




Hugs at Brooke’s wedding.




On my 31st birthday Jenny gave me my favorite food in the entire world: Coffee Dannon yogurt.




Before Jenny had her first daughter, we threw her a big baby shower and made a big poster of love for her from the entire company.




Jenny as a pirate on our RTR boat cruise.


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When we went on the Nate Berkus show and realized that we looked like a commercial for the Easter holiday.



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Every year we celebrate employees who throughout the year have exhibited Rent the Runway Core Values with an elaborate ceremony where we perform songs, have bands play, write skits for them, host game shows etc. We gift each winner a dream vacation for them +1 to anywhere in the world they want to go. This is Jenny and I with our Core Values Winners in 2014.


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Going up to Harvard Business School (where the magic originally started) to teach the Rent the Runway case which is taught to all first year entrepreneurship students.



Coming full circle at the launch of our Flagship store at 30 W. 15th St. in New York City. This was a Cinderella moment for Jenny and I to launch a store that is this beautiful with Jenny’s 1st daughter and my 1st baby (in my tummy!)


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Co-founders and friends forever!