Behind The Scenes


Jenny Fleiss' Behind The Scenes

“When working women ask me about how to time having kids with their career, my response is ‘there will never be a good time.’”

Jenny Fleiss is full-time-busy-as-can-be, but she still finds time to support other moms. Wife, mother of three, co-founder of Rent the Runway and now head of concierge shopping service, Jetblack, Jenny is no stranger to a hectic lifestyle. We popped into her office to hear from her on how she managed to feel like herself again post kids, and why she knows that for new moms, community is key.

Leaving Harvard Business School to start everyone’s favorite designer dress rental company, Rent the Runway, Jenny took on three other projects during the rise of RTR – her kids. If that sounds a bit…ahem…busy, rest assured: for Jenny, chaos is embraced, managed and enjoyed.

One way she covers her bases? With the help of her newest baby, JetBlack, a concierge service designed to help people (especially busy moms) shop by text for pretty much anything they could ever need to buy. Kids = chaos, it’s just a fact of life, and Jenny tells us how she handles her new and chaotic normal.


For Jenny, being productive, both at home and at work, has always been priority. “Productivity is my thing,” she shares. “Being productive fuels me.” But when Jenny had her first baby, she admits she underestimated the impact it would have on her planning time. “I had kids pretty early in life which meant that I had no close friends who had gone through it, and no real context for what to expect,” she says. “I entered into major shock.” Essentially overnight, Jenny had to figure out how to be productive in a new way, no easy feat when you have a newborn at home.

“To feel like myself again post kids, I had to find new and realistic ways of feeling productive in a world with kids,” Jenny shares. “Planning for time to be productive then setting the mental expectations that time with the kids is their time, not time for me to check off my to do list, has been key.”

Another new normal for Jenny? Figuring out how to get sh*t done while also being tethered to her home. “I was tied to the house in a new way, having to forward think and plan at a new level, and the big wammie – how to be productive in getting anything else done amidst all of this.” You know that old adage to sleep while the baby sleeps? Let’s just say as a working mom, that wasn’t Jenny’s game plan.


It’s safe to say for Jenny, pretty much “nothing felt normal” after having her first child. “Life for me, post kids, was an emotional roller coaster” she says, “and I really didn’t know what to expect.” The first of her friends to enter motherhood, Jenny has a vital piece of advice. “I think,” she says, ”the more mamas feel supported and can find natural forms of community who understand the journey of parenting, the better.” Find that tribe, wherever you can, because moms need to tackle all these new normals together.

Today, Jenny’s new normals tend not to phase her. “Where to begin – crayon on the walls, pacifiers in my pockets, having to keep a stocked fridge, waking up with arms and legs in your face from kids who climbed into bed that night, bathroom parties…” All manageable these days.


Waiting for that “perfect moment” to start a family can be futile. There is always going to be something that you can convince yourself needs to get done first. Travel more. Buy a bigger house. Pay off your student loans. Or, as is the case for many entrepreneurs and businesswomen, find the perfect time in your career. The thing is, that “perfect moment” will likely never come. And, if you are as busy as Jenny, you might not even have time to consider it.

“I always wanted to be a parent, but when starting Rent the Runway I wasn’t married yet and wasn’t thinking about having kids just yet,” Jenny says. “[Then] Rent the Runway took off like wildfire…time for life reflection and processing how this business would fit into my role as a mom was non-existent.”

Now that she has been through the entire process (three times!) Jenny’s point of view on ‘when to fit in baby’ is clear: “There will always be something happening and this is a part of life you can’t plan. You need to roll with it, otherwise you’ll risk having regrets,” she advises. “When working women ask me about how to time having kids with their career, my response is “there will never be a good time.”


Jenny’s little ones may be out of the baby stage now, but that doesn’t mean she is any less busy. At JetBlack, Jenny’s going full swing to make life easier for working moms (like herself!). “Jetblack was born from real pain points and tactics I used as a busy working mom. I set out to see if we could get time back by making shopping for our family easier and more delightful,” she explains. “We have created an entirely new concept that enables consumers to get exactly what they need through the convenience of text messaging and the freedom of a nearly unlimited product catalogue.” And while she is working as the co-founder and CEO, Jenny is always trying to find ways to keep her family life and work life in harmony. “I look for opportunities to integrate my life and family with work,” Jenny says. “Whether that’s bringing my kids to the office, talking to them about a business trip or digging into the pain points my perspective as a working mom has given me.”


Christy Turlington

“I like to say that I became a global maternal health advocate the day I became a mom.”

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Mara Martin

“I literally thought it was going to be this picture perfect scenario. Like these pictures I see – even in my childhood – of like, all of us in the hospital bed, smiling.”


Rebecca Minkoff

"Evolution. I went from a singular focus to a mother, and that opened up the 4th dimension for me of senses and love and seeing my heart outside my body."