Blending Parenting and Work, A Recipe for The Moonshot Generation

Jennifer Carter Fleiss
5 min readNov 1, 2021

This week the company I Co-Founded, Rent the Runway, went public (NASDAQ: RENT). Amidst this epic moment — a day more powerful than I could have ever imagined, the new norms we established as female entrepreneurs taking a company public with a female executive team felt more real than ever. My daughter, my Co-founder’s daughters, and a majority female audience of employees cheered us on as an inspiration to their career adventures. Our brand was built to empower women, to reject the perspective of fashion as frivolous novelty and embrace it as armor that can make a woman feel her best self and tackle her dreams. This week we proved that can happen.

Colleagues sent photos from years ago of my oldest daughter, “Baby Dan Dan,” in the office. I brought her to the office initially to introduce her to her Rent the Runway family. She was the first baby born amongst a team of mostly women who looked to me with their own dreams of having both a career and a family. Baby Dan Dan was greeted with smiles and an added lightness at the office — so I kept bringing her. Soon it became normal to have babies in the office and, as other new moms pushed strollers through our doors, we created a new normal. In doing so we made the business better. Beyond the office spirit, connecting to mothers enabled everyone to better relate to and serve a key customer demographic. We launched a maternity collection and later a girls’ dress collection. We led our teams as mothers who related to the many demands on a woman’s time for things that had for years seemed frivolous. The idea of leaving early to make school pickup, chatting about sleep training, and planning birthday parties had long been taboo in an office environment. At Rent the Runway, these topics proved a source of connectivity, fun, and energy that enabled us to BLEND, rather than balance, our roles as mothers and businesswomen. As parents ourselves, we understood the importance of generous parental leave policies, equal benefits for all of our employees and a culture of compassion. In turn, our employees responded with authentic hard work and passion that built RENT.

I think back to my first job after college — working at an investment bank with a female boss who was one of the top partners at the firm. While this woman should have been a role model, instead she was a traumatizing boss who treated the analysts as means to an end, knowing barely anything about us beyond the quality of our excel models and power point decks. Amidst the many, many hours at that office, I remember most vividly one rainy Sunday morning when I ventured uptown to her apartment to bring her the latest deck I had compiled over the weekend. She opened the door with a crying baby in her arms and a disheveled apartment in the background; all of a sudden she was a real human: vulnerable, tired, and stripped of the daily tough façade. At Rent the Runway we enabled that authentic blend of mom and businesswoman as the norm. With our authentic selves at the forefront, we built true camaraderie, and a unicorn public company.

One of the silver linings of Covid is that it forced a natural blending of work and home life for more businesses. Children raised in a time of remote work will benefit from their parents’ presence and with it the opportunity to inspire their career aspirations. I find myself reaching into my entrepreneurial toolbox with my children on a daily basis– problem solving together amidst the many challenges of Covid, teaching a comfort with making mistakes, testing and learning and encouraging big dreams. Working remotely, I am around to answer their questions as they overhear pieces of my phone calls or see work materials in my home office. We are naturally educating our children on different vocations, showing them aspects of our work, having them overhear us lead through hard times, and manage tricky negotiations or feedback discussions — all this done while preparing lunch for a child or holding their hand. Children who were alongside their parents during remote work will understand that being a good parent and businessperson are not opposite forces. In fact, being a parent, can make you a better businessperson — and vice versa. The questions our children innocently ask can encourage us to rethink basic norms and lend us their fresh eyes at a time when our whole world has been turned upside down. From a leadership perspective, caring for your family’s wellbeing amidst a pandemic provides perspective that you need to navigate stressful business decisions and to be the empathetic leader knowing that many others in your organization are facing the same challenges.

Children themselves have also been forced into a new and more autonomous environment. The necessity of remote schooling introduced technology and the responsibility of classroom management at an earlier time than would have otherwise happened. Staying self-motivated, accountable, and being fast to adjust to new ways of learning via remote lessons pushed our children to be resourceful and entrepreneurial. They saw a world where nobody had the answers — not the President, doctors, scientists, or their Mom and Dad — and with it the opportunity for us to all try to learn and be resourceful together. The power in realizing that nobody has the right answers all of the time makes it okay to be wrong, to try and fail and, as if puzzle pieces, to continue to triangulate the correct answer, often as a team. Navigating new schedules, mask and safety rules, house chores, respect for family spaces, in many instances a move and/or new school– our children became more adaptable. They are growing up in a moment of big change — acceleration of digital businesses, trips to outer space and electric vehicles — a moment of dreams achieved. These are the building blocks of an entrepreneur. I can’t wait to see the change of this moonshot generation will drive.

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Jennifer Carter Fleiss

Co-Founder, Rent the Runway and Jetblack, Investor, Adviser, Serial Entrepreneur, board member, mom, best wife sometimes