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Mother’s Day

#LADYBOSS, Fashion, Great Places To Work, Mother's Day

Heymama Mother’s Day #LADYBOSS: Jenny Fleiss Co-Founder Of Rent The Runway

May 7, 2016
Jenny Fleiss Rent The Runway

Jenny Fleiss, is the Co-Founder and Head of Special Projects at Rent the Runway, the company that has, since it’s founding in 2009, made designer dresses accessible to every woman with an internet connection. Jenny and her co-founder, Jenn Hyman, sought to create a company that filled a gap in the retail industry and gave every woman the chance for a “Cinderella moment.” Jenny has been listed on Inc.’s 30 under 30 list and Fortune’s Most Powerful Women Entrepreneurs (you go mama!).

To celebrate Mother’s Day we’ve asked mamas for the best advice they ever got from their own mamas. It’s easy to see the impact this #LADYBOSS’s mama had when she said “why not do both?” Jenny, the mama of two, and soon the be three, seamlessly integrates  family and business. At Rent The Runway, they have created a workspace that empowers women, allowing kids to visit the office, and even arranging fun activities and events for them. Mamas are supported and encouraged to rejoin the workforce, as an appreciated and important part of the Rent The Runway team. We’ll be putting Rent The Runway high up on our list of great places for parents to work (coming soon).

Check out our interview with Jenny below for some RTR insight and inspirational advice to get you motivated.  

Tell us your startup story. Was there an ah-ha moment that told you ‘this is something I can make a business out of’? Did you raise money?

Jenn and my real a-ha moment came when we put together a rental pop-up and watched real customers first hand interacting with the designer rentals. The first girl tried on a gold sequined dress, twirled around in the mirror and said “I look HOT!” Her entire persona was transformed and it was then that I realized the service we were providing was to make women feel confident and happy in their lives. Everyone deserves a Cinderella moment became our mantra and we built a service business around this concept that to date rings true. We raised money right out of the gates from Bain Capital Ventures and were the youngest female co-founders to have been funded by them. We have now raised a total of $126M from various top venture firms.

How did you meet your co-founder Jenn Hyman? What made you two click?

Jenn and I went to Harvard Business School together and were in the same section, which meant we took every class and spent every day together. We became very close, very quickly, and loved discussing entrepreneurial ideas together. We also realized that we brought different skills to the table; I came from a finance and strategy background and Jenn brought her sales and marketing background to the table.  We also realized that we enjoyed spending time together, which is important since you spend a ton of time with a co-founder!


What was the hardest part or biggest obstacle you had to overcome to get RTR up and running?

We faced initial difficulty when pitching VC firms. They were predominantly men and just didn’t understand or get the demand for this type of service. We needed to figure out how to frame the message so it would make sense to our audience. To do this we started our pitch showing VC’s footage from the trunk shows we hosted to test our idea that captured the emotional connection the women had with the designer dresses they were trying on. The VC’s were able to see firsthand the changes in the way the women carried themselves and how they interacted with their friends as they showed off the dress.

What’s the best advice you received from a mentor, peer, or family member when you were first starting out?

It sounds simple, but the best advice I’ve received is just to go for it – whatever “it” is to you. So many aspiring entrepreneurs have amazing ideas but let the fear of failure get in the way of going after them, testing and iterating, and making it happen. Jenn and I also constantly remind one another that ‘No doesn’t mean no, it just means not right now,’ a spirit and fortitude that has enabled us to persevere through the inevitable ups and downs of entrepreneurship.

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Can you speak a little bit about your decision to take RTR from an online platform to opening stores; I believe the first was in Bendel’s on Fifth Avenue. Tell us about that process.

We are constantly listening to our customers about what more we can do to provide them the best Rent the Runway experience. We continued to hear them ask for a physical location to try on dresses and see them in person. Like everything we do in our business, we tested the concept first on a shoe string budget, so that we could learn and iterate. With a small dressing room studio in our office and then one inside Henri Bendel’s we found that retail spaces would provide us with a new way for us to connect with our existing customers, gain exposure to new ones and really bring life to the brand. We were also able to prove out that the economics would be favorable and that we could use the stores as service centers to also let customers pick up and drop off their rentals. We now have retail stores across the country in New York, DC, Chicago and Las Vegas.

I know RTR is involved with the Project Entrepreneur Competition; can you speak about that a bit? Why and how you got involved, and what do you love about it?

We launched Project Entrepreneur in partnership with UBS because we wanted to empower other female founders and give them the tools, training, and networks needed to build scalable, economically impactful companies. It’s extremely important to me to offer my guidance and mentorship to other female founders.

In March, we hosted our Project Entrepreneur weekend intensive where over 200 female founders came to New York to participate in the program. Twelve finalists were selected to pitch their businesses to a panel of experts. From that group, three were chosen to receive funding and also invited to participate in a five-week business accelerator program hosted at the Rent the Runway offices.

Jenn and I felt that doing this now, while we were still in the midst of startup life would enable us to offer the most valuable program to women. We additionally found that our brand resonated to consumers as an icon of women run businesses, which we wanted to celebrate and put further meaning behind.

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Any mantra’s you live by? Words to live by?

You’re never fully dressed without a smile. Whether it was the first customer who tried on a rental dress and showed us the transformational emotional power of designer rental, or our injecting real customer photos onto our site, this mantra is meaningful to me everyday. I also find that in leading and inspiring a company, bringing a positive attitude into the office is incredibly important – a smile goes a long way.

No doesn’t mean no, it means not right now. Persistence and perseverance are key in entrepreneurship as is keeping a positive outlook.

What advice do you have for women trying to make that transition from the financial industry into other careers?

Go for it. Even if you fail you will learn a ton on the way. If you aren’t ready to start your own company, try working at a smaller company to get the feel for it. If you aren’t happy in any role I advocate that, rather than sticking it out as resume builder, you should try something new. It’s not worth spending your life doing something that doesn’t make you happy.

What has been the most rewarding part of starting your own business? Any specific moment in time stick out for you?

Watching the company grow from just an idea to an 850-person company has been incredibly rewarding. I’m also very proud of the entrepreneurial spirit that still permeates the Rent the Runway company culture. Everyone feels like a founder here as we are constantly interacting with our customers, testing things out, and injecting new ideas into the company. It has also been amazing to see how our brand has evolved in its meaning to our customers who feel a true connection to the female-empowering business we have built.

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Why did you get into fashion entrepreneurship, could you see yourself doing anything else?

I have always been an entrepreneur at heart, from my early childhood lemonade stand to an online tutoring service I built in college. It was never as much about the industry as it was starting and building something from the ground up, innovating on an industry, and providing a new form of consumer value! I also love spending time advising other early stage companies.

What makes someone a good boss?

Giving your employees ownership over their projects and empowering them to take that opportunity and run with it. Hiring the right people to begin with – who you feel will be a fit with your personality and culture is also important in setting someone up for success. And, when all is said and done, celebrate the wins!

What are you keys to success?

Taking advantage of every minute of every day, whether that means multitasking a meeting and a manicure, running to or from the office for exercise, or having my daughter visit the office after school. I have also had a bias towards action; great things can happen when you just go for it!  Success isn’t just about business for me, it is about being able to enjoy and appreciate every aspect of my life.

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Can you give us any inside scoop of what to expect from RTR?

A lot of exciting things are happening right now at Rent the Runway; we just came off of the launch of our new subscription service Unlimited, which allows you to select three pieces from our inventory and swap them out as many times as you like, giving you access to an endless closet with endless options. This program is exploding and truly revolutionizing the fashion industry!

Our three Project Entrepreneur winners are setting up shop in the Rent the Runway’s office at the end of May to begin their five-week business accelerator program. We are constantly evolving and looking for new ways to innovate!

In light of Mother’s Day can you tell us the best advice your own mother gave you?

‘Why not do both’ was something my mother often said to me encouraging me to go after every opportunity and find a way to fit everything into my life to create fullness and composite happiness. She also constantly reminded me to slow down, smile, and enjoy life.

Photos by Stevi Sesin

Give Back, Lifestyle, Mother's Day

Heymama Hosts A Mother’s Day Breakfast With Fridababy, Hatch & FEED

May 6, 2016
heymama. Hatch, Fridababy, Lauren Bush Lauren

We gathered our mamas at the serene Hatch showroom to celebrate Mother’s Day and the launch of Fridababy‘s new Bitty Bundle of Joy Kit with our beautiful community of strong, smart, and creative women who are shaping this world with their passion and energy. We felt so lucky to have three of our members Chelsea Hirschhorn of Fridababy, Ariane Gold of Hatch , and Lauren B Lauren of FEED co-host with us at the gorgeous Hatch showroom.

Lauren B Lauren at hey mama Mother's Day Breakfast

On top of the smiles we got from seeing our friends we laughed at the jokes of Dena Blizzard of One Funny Mother .

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Struck a pose in the photo booth by Sharing Box.

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Refreshments from Whealth & Co and Montauk Juice Factory juices were a plenty and our mamas took advantage of all the fun activities set up throughout the day…

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Got smart on all things mama and baby with celebrity pediatrician, Dr. Tiffany, who was there to answer all our burning questions.


Gave back, every mama received a FEED bag giving 25 meals to kids in need.

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Took some time to pamper ourselves with makeup and nail stations by GLAMSQUAD.

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Mamas had the chance to win our kick-ass #YouGotThisInTheBag Raffle raffle including:

Hatch diaper bag and dress, Kiehl’s pampering mama and baby centric beauty items, Tenoverten mommy & mini gift card, Mignonne Gavigan feather earrings, Bauble Bar gift card, Tickets to Dena Blizzard’s One Funny Mother, a Maman brunch gift card and Fridababy’s FeverFrida.

If you haven’t yet had a chance to enter, you still have time. But not lots. We’ll be announcing the winner on Mother’s Day!  Just use the hashtag #YouGotThisInTheBag and tag @fridababy_hq @heymamco @hatchgal.


Gift Bag

#YouGotThisInTheBag goody bag: every mama took home one stuffed with their dream diaper bag essentials.

Fridababy‘s Bitty Bundle of Joy Kit; Rose + Rex hand puppets; Munchkin snack catchers, Latch bottles and Sterilizer Bags (for on-the-go); Supergoop!  sunblock, FEED pouches that give 25 meals to kids in need; Erzo Pre-Natal Vitamin Cookies;  Earth’s Best diaper wipes pack; Ella’s Kitchen organic squeeze pack for baby; Barley & Oats lactation cookies; Hello Sitter gift card; Monica and Andy swaddle; Sawyer passport pack.

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Earth's Best


Photo credits:@stevilou.

Blogger, Lifestyle, Mother's Day

Your Soul Style: Two Moms and a Baby

May 4, 2016

In honor of Mother’s Day we caught up with heymama member, Jenny Greenstein, wife, mother, and all around good soul, who shares what being a mom is like in her two-mama household. Jenny is a freelance stylist, consultant, style coach and founder of the Your Soul Style blog, which she uses as a platform to empower others to find their OWN rhythm, become their OWN style-makers and be the most beautiful version of themselves (ROCK ON MAMA!).  

Jenny is looking forward to a Mother’s Day of pampering with a massage and some good food, but admits that what she’s most excited about is spending undistracted time with her two girls, daughter Vida and wife Dina. Read below to hear more from this soulful mama as she shares her experience raising a child in a same sex household. #GIRLPOWER.

I recently got super emotional while going through my iPhone and finding a photo which included not one, not two, but three positive pregnancy tests. I was trying to free up space on my camera roll for more photos of my beloved daughter, Vida, but this was one I couldn’t part with. Despite her being nine months old, a flood of familiar feelings came rushing in from that day. Since we are a lesbian couple, it had been close to two years of planning for this moment. There was so much to set-up before we even started the clinical part of the process. When I found out I was pregnant, I remember screaming, crying, and jumping around my apartment like a crazy person. In the truest sense, it felt like a dream come true. Up until then, I was losing hope that motherhood would actually happen. And there was nothing more in this world that I wanted than to become a mama. I craved it so deeply and it occupied every inch of my mind and body. Thankfully, on our sixth round it worked, and the soul we were waiting for found us; she was perfect and worth the wait.


Motherhood has easily been the best thing that’s ever happened to me. I like to believe that all mamas feel this way, but with more planning to consider as a gay couple, I think there is naturally an extension of gratitude. It was a long, hard, and taxing process, but I don’t resent it. It was a blessing in disguise and has contributed to my overall experience. I’m not sure I’d be the same type of mother had it come easily. Don’t get me wrong, I face typical challenges that all women do as first time mothers, but the deep-rooted gratitude helps me manage those difficult mama moments. It reminds me to remain selfless, focused, and grounded when I think I’m losing it. It always brings me back to my center. Perhaps that’s one of the benefits of parenting in a same-sex relationship; because it is impossible to follow a traditional, biological path, it requires us to step outside of the knowns. It took a huge investment of time, emotions, physical commitment, money, and resources to make it all happen; we wouldn’t have gone through with it if Vida wasn’t truly and deeply wanted.

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Life with two Moms is the same, but different. While I don’t believe that men and women in modern day society should conform to stereotypical parenting roles, there is cultural defining behind genders. However, the lines are blurrier when it’s two women. Dina and I tried to figure out who would handle what when I was pregnant, but like many parents find – planning ahead of time was useless. You just can’t know until you know, which has been my daily mantra since giving birth. Once Vida was here, we organically fell into our roles; me, the primary caregiver and Dina, the second parent. I sort of predicted that would happen, but we still exhausted the conversation beforehand. Although our current individual responsibilities are more concrete now since I nurse Vida and manage her sleep/nap and eat schedule, there will be constant shifts as she gets older. If there is anything I’ve learned as a parent, it’s that everything changes, and nothing stays the same! A week could go by where Vida is close to sleeping through the night and Dina and I go on and on about how we’ve finally hit our stride, but then the following week she’s up 2-3 times a night for days straight and we’re crying over exhaustion. It often seems there is no escaping the great baby sleep debacle whether you’re two moms, two dads, one dad, one mom, one of each sex, or whatever! We do experience crossover of responsibilities and become territorial about what we each are handling, but I assume that happens in all relationships. Or maybe that’s just par for the course when dealing with two of the same sex?


It gets a little tricky when Vida calls, ‘mama’ since we have no idea if she’s talking to one of us or both of us, but eventually she will understand she has a ‘mommy’ (me) and ‘mama’ (Dina). For now, we both respond. I joke with Dina and tell her that there are too many cooks in the kitchen, but in all seriousness, I do believe that who we are to Vida has everything to do with who we are as individuals (rather than what our gender is). I also believe this is how it should be if you were a man and woman too. Every couple finds their own version of balance, and although we’re not a perfect system (who is?), we have created one that makes sense for our family.


Since I became Vida’s mommy, I’ve crossed over into another side of life. While Vida was the one who arrived earth side, I experienced my own rebirth too. I’m not the same person anymore. A light which I never knew existed was turned on and my purpose here has changed. There are moments when I think about the future and wonder what life will be like growing up with two moms. Both Dina and I have a father and a mother so won’t necessarily be able to relate to Vida’s experience, but that will be integrated into the values we teach her as she evolves, demonstrating that it is our own uniqueness which makes us beautiful, and what makes you different is what makes you, YOU. Being the daughter of two strong, confident, and empowered women is more than I could ever ask for my child. As far as I’m concerned, Vida having two mommies makes her the luckiest girl in the world.



Photos by Sari Wynne @sariwynneruff

Gift Guide, Give Back, Mother's Day

A Give Back Guide: What Mama Really Wants This Mother’s Day

May 4, 2016
Mother's Day Gift Guide

Mother’s Day. It’s the one day a year when you can sleep late and then wake to breakfast in bed while getting covered in kisses from your sweet minis and lover. Or, if you’re like me, that’s what you dream will happen. This Mother’s Day, I’ve decided to actually ask for what I want, instead of assuming he knows. To help make me feel less guilty asking for what I want, I’ve found 10 amazing presents that are both good for you and your soul as they give back to the world too. So, whether you’re a mama shopping for your mama, a mama shopping for yourself, or just shopping for a loved one this Mother’s Day, these #FEELGOOD #GIVEBACK gifts are sure to get the job done, because what mama really want this year is happiness (for all).


Cause you are truly, such a babe. Bonus: Winden casts these amazing pieces in recycled gold and silver.


A t-shirt for everything you do; perfect with jeans and heels or your next workout. Bonus: these limited edition tees are made from pure USDA organic cotton.


Hugs, kisses and a place for your precious pieces. Bonus: handmade in NYC and  5% of every sale goes to fighting New York City hunger.


From the playground to a formal dinner, it’ll do it all. Bonus: a luxury bag that’s also cruelty free, chemical free, and uses recycled materials. They also donate a percentage to the amazing Sheldrick Wildlife Trust in Kenya.


What mum doesn’t love flowers, let alone this beautiful bouget, which is more like a full forest, by her bedside. Bonus: blooms which support US farmers.


Diamonds will forever say it all. Bonus: Mociun always uses sustainable business practices, including sourcing antique diamonds.


The difference an hour or two alone in a salon makes on your soul is simply EVERYTHING. Bonus: vegan, cruelty free, and toxin free polish.


As women, we all deserve some time to focus on ourselves, to decompress and breathe fresh air into our souls. The Great Jane is a progressive retreat for mama entrepreneurs taking place May 20 to May 22. A place to inspire, be inspired and connect with amazing women while getting some time away from your minis and lovers. Bonus: Network with other entrepreneurial mamas to form lasting friendships or even business partnerships!


Mom’s still deserve to look hot underneath it all. Bonus: Naja uses fabric made from recycled plastic to help eliminate waste in the ocean.


Your hair may have baby food in it, your clothes wrinkled, but your skin always deserves precious care. Bonus: botanically-based, cruelty free products with recyclable packaging.

Curated gift guide above compliments of heymama member, Nicole Fasolino. To learn more about Nicole check out her Instagram handles @Nicolefasolino & @girlswhodressboys.