How I Parent explores the ins and outs of modern day parenting with moms and dads from all over the world, who are raising their own unique families and sharing their best advice and most heartfelt lessons with PEOPLE. Want to be a part of it? Email what makes your family so special to howiparent@peoplemag.com.

By Diane J. Cho
December 01, 2019 09:30 AM
Jenny Fleiss

Name: Jennifer Fleiss
Location: New York City, New York
Occupation: Co-founder of Jetblack since 2017 (previously, she co-founded Rent the Runway)
Family situation: I have 3 kids ages 7.5, 4.5 and 3. I’m married and my husband plays a large role in taking care of our kids. We have nannies from time to time and are also lucky to have grandparents who are very helpful in N.Y.C.!
Parenting “philosophy” in a sentence: Don’t sweat the small stuff and embrace the chaos.

Jenny Fleiss

What was your journey to having the family life you have today?
In some ways, my husband and I got our introduction to parenting about a year after we got married with our Jack Russell terrier, who we still have. I kind of joke that we first got a plant and the plant lived for a year, so we got a dog and the dog was still alive after a year, so we got a baby. That’s pretty much been how we’ve progressed into our responsibilities as parents. But in truth, having a dog was a great way to start to realize that there’s something “bigger.” It’s so easy, especially in Manhattan, to be so focused on work, your career and yourself – so having a pet gave us a sense of what those responsibilities would be like.

The same year my husband and I got married, I had also just graduated from Harvard Business School and launched Rent the Runway, a subscription service that allows shoppers to rent designer clothing for a fraction of the price. Then we had our daughter two years later, our son three years after that and our third child, our little girl, about 18 months after that. I don’t think anyone could have anticipated how big of a success Rent the Runway was going to be but it was clear from the start that my business was going to be a big part of our world, and my husband was really supportive of that.

One thing I felt very early on in getting to know my husband was just how supportive he was of my career and me being a smart, ambitious woman.  His mom ran her own hedge fund, so I think having a strong woman in his life was always respected, admired and appreciated. Although he didn’t totally get the concept of Rent the Runway at first, because he’s not that into fashion himself, he believed in me and knew if I was going to take something on, I would really go after it full speed. By March 2017, I [had moved on to] co-found and launch Jetblack, a members-only concierge shopping service that combines the convenience of e-commerce with the customized attention of a personal assistant, and we’ve been continuing on this journey ever since.

How did your upbringing influence your parenting style?
I am one of three children and growing up, my mom made us her number one priority. It always felt like she was born to be a mom — it was her passion. It was her driving force and she threw everything into it. She passed away three-and-a-half years ago but I’ve taken so much inspiration from her, including the idea to seize every opportunity to live your life with no regrets. So, if you want to have kids and you’re excited about it, don’t let your career stop you. If you want to start a business and you have kids, just go after it.

Jenny Fleiss

What’s your favorite thing about parenting?
My kids inspire me to appreciate all the little things in life. Halloween this year was really the first time my three year old was able to experience trick-or-treating. Each piece of candy was like a treasure. It took us about an hour to go through one block but it didn’t matter. Each moment allowed me to see how she looked at the world with gratitude and excitement. I also really enjoy how creative and fun imaginative play can be. We’ll have actual lemonade stands or just play-pretend lemonade stands and I’ll try to sprinkle in bits about business. It’s something that’s fun for us and helps them understand a little bit more about my life as an entrepreneur.

What’s the hardest part?
There are so many things that are hard. I’m in a phase right now where it’s very physically demanding. It’s also hard having three kids and giving them each enough individual attention, which is a personal struggle I am having at the moment. I missed my daughter’s ballet recital this year and I gave myself a really hard time about it. It can be difficult balancing work obligations while raising a family, but the best way I’ve learned to deal with those situations is to have conversations with my kids. I’ll share with them what I’m doing and why so they don’t feel like I’m making a choice over them. Being aware of the situation allows them to understand that certain work obligations are just a part of our lives. Bringing my kids to the office has also helped them understand what I do and made them feel more aware and part of my work life as well.

Jenny Fleiss

What do the holidays mean to you as a family – are there any traditions you’re excited about sharing with your kids?
The holidays are the best time for our families to get together and appreciate one another. This year, we’ll be spending our time around Christmas at our family home in Southampton, New York. My husband and I are raising our family Jewish so we’ll also celebrate Hanukkah with our kids and extended family.

What’s the best advice you can share with new parents?
Don’t sweat the small stuff, especially if you are debating on having two children versus three. Just give in to the chaos. For example, when your first kid’s pacifier falls on the ground, you throw it away. The second time it happens, you boil it. The third time, you rinse it off. The fourth, you might clean it off with your own mouth. One thing can seem like a huge deal but then you’ll eventually learn to just roll with it. In life, as a mom or an entrepreneur, you will be able to figure it out as you go.

I tell the same thing to many young women who’ve asked me how I juggle work and family. I hear a lot of women say, “I’m going to have a baby, so I’m going to wait to start my business or to fundraise until after I do that.” But what if it takes two years to have a child? You might look back and think, Why didn’t I just start working on my business sooner? When in doubt, I will usually ask them, “What can you do to make sure you’re not going to look back and have regrets?” If it means doing it all at the same time and putting one foot in the front of the other as you go, you can do it — that’s, at least, how I’ve been able to manage it. It’s not going to be easy but we are all able to adapt and adjust in amazing ways. I’m also grateful to have a partner who does a lot of school pickups and organizes play dates. I think it’s a really healthy thing for the kids to see their dad very involved in their lives, as well as their mom.

Jenny Fleiss

What would you want your kids to say about you as a parent?
I would want them to say that I gave my all and put everything into helping them thrive.

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