Chelsa and Dennis Crowley on Preparing for First-Time Parenthood

The entrepreneurial couple shares how work, friendships and each other have made them ready for their most important launch yet.
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Updated January 30, 2017
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New York couple Chelsa and Dennis Crowley are no strangers to getting new projects off the ground. He’s the founder of Foursquare, the mobile app and tech company with more than 50 million monthly users; she co-created Stowaway Cosmetics, a portable-size beauty product company. And now, the pair is about to launch their first joint venture: parenthood! Baby no. 1, who they’ve lovingly nicknamed “Lil’ Guac," is set to make an appearance on Chelsa’s Cinco de Mayo due date. We asked the parents-to-be to share in their own words how they’re gearing up for baby’s arrival.

Chelsa’s Story

I was never that little girl who dreamt of my wedding day, let alone having children. In fact, my dad (who was so thrilled when I “finally settled down” at 32) used to say he thought I was too independent ever to get married.

Yet here I am, not only married but 39 weeks pregnant, and I’ve loved the surprises along the way. While some days are filled with anxiety, most are filled with excitement as I get closer to becoming a mother. When I told my mom I was pregnant, she reacted the same as my dad did about me getting married: She was thrilled but never thought I’d let go of my “independent ways” to have children. (To be fair, for years I did tell her only to rely on my brother for her grandchildren!)

That said, I’m so excited—more than I even thought was possible. I’m not sure if it’s because I’m older, more established, feel very stable to bring another life into mine or that I’ve found the person that I want to have babies with, but probably it’s a mix of everything. I feel lucky to have had a great pregnancy without morning sickness or hormonal ups and downs, only occasional aches and pains, and, for the most part, have continued doing the thing I love to do most in my spare time—exercise. In fact, pregnancy has been fascinating to me; watching my body do its thing has left me in awe of the female body and its capabilities.

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I’ve been trying my best to prepare for (what I hear from everyone is) the biggest change of my life. That said, you can only prepare so much. And so far, my anxieties have mainly been around work. As the cofounder and chief creative officer of Stowaway Cosmetics, the company is, in a sense, my first child, and I’ve been spending all my time the last few years focused on “her.” So many people I’ve talked with have commented on how great it is that I own my own business because I can make up my own maternity policy or do things on my own time frame. But to the contrary, I’m worried about my time away and am cognizant about how it could affect our very small six-person team. I plan to check my email and work from home when I can (please don’t judge, but I know I’ll have to do something during those 3 a.m. feedings!), but I think this is one of those unknowns and I’ll navigate those waters once baby arrives.

Among other things, starting a company has taught me patience and how to roll with the punches. Having a good business partner helps with that, and when it comes to the unknowns of motherhood and parenting, having a good partner to navigate those uncertainties is really all I could ever ask for.

I’m most excited to meet this little person that has been kicking, punching and jabbing me for so long. I only hope that my baby grows up to be as strong as some of those jabs, for real. Dennis and I decided to not find out the sex of the baby, and it’s been incredibly fun to think about our life with either a boy or a girl.

One of my girlfriends told me that one of the coolest things about having a child is seeing everything again for the first time through their eyes. Mostly, I’m looking forward to raising a child with my husband. We make such a great team in life and I know we’ll be great at parenting. I’m not saying we will be perfect parents, merely that we will be great partners at raising this little human together and sharing those responsibilities, frustrations and happy moments.

Dennis’s Story

As I sit down to write this, we’re at T-minus six days until “Lil’ Guac” is supposed to arrive. Why, “Lil’ Guac,” you ask? Because our official due date is May 5 (Cinco de Mayo = “Little Guacamole” = “Lil’ Guac”—obviously!). So, before I have to rush to the hospital, a few thoughts:

  1. Holy cow, that went fast! I suppose we should have expected the pregnancy would go by fast since that’s what all our friends told us, but nine months goes by really, really quickly. Breaking it down, you really spend the first three months either not knowing you’re pregnant or trying to keep the news a secret until you’re 100 percent sure. Then you spend the next three months telling everyone who will listen, which is super exciting. And by the time month seven kicks in, you’re thinking, “OMG! The baby is coming! We don’t even have a crib yet!"

  2. Which brings me to “the big question” I keep getting from all my friends and everyone around the office: “Are you ready?” It’s a funny question because, well, can you ever really be ready for your first child? I mean, we bought all the stuff (yes, we finally got that crib—and some clothes, a car seat, the first aid kit, all the pacifiers, bottles and nail clippers) even though I think we had a very minimal approach to our pre-baby shopping; we bought nearly 50 items in a single Amazon order (we actually didn’t once step foot in a baby store!). I think we’re definitely ready from the “We have all the stuff” perspective, though I will admit to still feeling naive about the “Your entire life is about to be totally different!” part. To be honest, I still really don’t know how you prepare for that. But I’m not at all worried about it; we’re both just so excited to meet “Lil’ Guac” and that totally overshadows any nervous energy or doubts I have.

  3. Even though we’re now just a few days away from meeting baby, it didn’t feel real to me until I installed the car seat last week (I needed to make sure it fit!). Carrying the empty car seat down four flights of stairs, across the street and into the backseat of our parked car got me really excited, jittery and emotional all at the same time. After strapping the seat in successfully, I had that moment of “Oh this is very real, and I’m no. 1 dad right now for installing this thing,” which was a great feeling that I won’t soon forget.

  4. We’ve established a great parental leave policy here at Foursquare: eight weeks paid leave, for both moms and dads, which you can either take all at once or split up over baby’s first 12 months. Our plan is for me to take a big chunk of it up front (at least six weeks) and try to spend as much of that time as possible in the Hudson Valley (we have a house near Kingston, New York). I feel fortunate that our parental leave policy is so generous, and I’m really looking forward to getting to spend a lot of time with Chelsa and “Lil’ Guac” as we adjust to being a family of three (or five if you count the cats too!). I’m planning on trying to “disconnect” as much as possible while I’m on paternity leave, and I’m thankful I have such a strong team at Foursquare that makes it possible to not stress about being off the grid for a few weeks.

  5. I know Chelsa is going to make a great mom: She’s smart and sharp and strong, and the perfect mix of dreamer and doer. She’s going to be the perfect role model for “Lil’ Guac.” I can’t even express how excited I am to see her in action with our baby. Meanwhile, I’m really looking forward to being a dad—to show our kid as much of the world as we possibly can, trying to teach him or her something new every day. It’s been nothing short of inspiring watching my best friends turn into parents these past few years, and I’m so excited that Chelsa and I get to experience that together starting, well, any day now!

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