Inspiring Women: Meet the Co-Founder of Winnie, a Yelp-Type App for Parents

We talked to Sara Mauskopf about the decision to start her own company and how being a parent has changed her career.

Inspiring Women: Meet the Founder of Winnie, a Yelp!-Type App for Parents
Courtesy Sara Mauskopf

Imagine this: You become and mom and decide to quit your corporate executive position to start your own company building an online resource center for parents just like you. Amazing, right? Then, five months after starting this new endeavor, your husband is diagnosed with an aggressive cancer. That's what happened to Sara Mauskopf. She's the co-founder of Winnie, an app geared towards families — think Yelp! for parents — and an inspiring example of what it means to balance your personal and professional lives. Instead of throwing in the towel on her new company, she managed to navigate being a new CEO while caring for her young daughter and supporting her husband through his cancer fight.

The good news is things are "much calmer now." Mauskopf's husband is cancer-free, they're about to celebrate their daughter's second birthday, and Winnie is now a community of over 25,000 parents. These moms and dads in the SF Bay Area and beyond use the app to ask each other advice and conveniently review recommendations for local childcare, kid-friendly restaurants, shopping centers, and more. In fact, Mauskopf used Winnie as a much-needed guide for her own daughter while her husband was sick.

Mauskopf has an impressive Silicon Valley resume — she's an alum of Postmates, Twitter (in its startup days of only 200 people), Google, YouTube — and shared with us her unique perspective about career, motherhood, and not taking anything for granted, especially your health.

Livingly: Why was it important for you to start Winnie?

Sara Mauskopf: When I became a mom, there was so much information I needed and not a good centralized place to get it. I needed to know everything from where to change my daughter’s diaper when I was out of the house to how to find the best local childcare to why the heck is my baby crying. Winnie was created to help parents get relevant information for every age & stage and connect with other local parents.

How has being a parent changed your career?

Being a parent is what made me realize that Winnie needed to exist in the world and that I was well positioned to build it. I quit my job to start Winnie and I definitely would not have had the inspiration or motivation to do so if I wasn’t a mom. I also think becoming a parent has made me a lot more confident. If I can create another human life and be responsible for its survival, then surely I can start a company!

Do you think you'd be where you are today if you were living outside of Silicon Valley?

I think Silicon Valley is a really special place where you meet incredible people and have access to the funding, talent, and networks to make your dreams a reality. I certainly owe the success of Winnie to the incredible team of engineers I was able to recruit, the investors who backed us from the beginning, and my co-founder Anne Halsall. Most of these people I met in Silicon Valley or through connections in Silicon Valley. I also met my husband while we were both working at Google in Silicon Valley so it’s also a special place to me for that reason.

That said, I think there are advantages to every city. I’m from the East Coast and every time I go back home to Philadelphia or pay a visit to New York City, I realize these cities have so much to offer as well. I went to school near Boston at MIT and that’s an amazing place too with tons of really smart people. So I certainly don’t think Silicon Valley is the only place that you can find success.

I also think Silicon Valley is a bit of a bubble. If you’re only solving problems for people who live in Silicon Valley, you’re not really building something worthwhile. From the beginning, we always knew that we wanted Winnie to be for everyone, so we have built it to work nationwide. We have Winnie users in over 3000 cities throughout the United States.

Where do you see yourself in 5 years? 10?

I don’t know where exactly I’ll be in 5 or 10 years but I hope I’m still working on something I love and spending time with the people I love. I know that my daughter and my husband will still be the most important things in my life and I’ll be doing everything in my power to keep them happy and healthy.

Inspiring Women: Meet the Founder of Winnie, a Yelp!-Type App for Parents
Courtesy Sara Mauskopf

As far as Winnie, I see it becoming part of the standard toolkit for all parents. In the next five years almost all new parents will be millennials — we’re already up to 90% — and this is an enormous opportunity. As this new generation of parents “comes online”, we want to be there to help them get started and become a trusted and reliable companion on their journey.

And it's a long journey! Parenting is a huge part of your life for many, many years. We've already seen incredible long-term loyalty in the people who use Winnie. I wouldn't be surprised if many of them are still there in 5-10 years, looking up camps instead of daycares, and discussing acne instead of diaper rash!

What advice do you have for other female entrepreneurs?

Don’t wait for the perfect time to follow your dreams. If you have an idea for something you want to exist in the world, go out and build it. Don’t wait for anyone to give you permission or the timing to be perfect. It turns out there’s never a perfect time.

By the same token, don’t wait for the perfect time to start a family. You can absolutely start a company and have a baby. You can absolutely raise kids while building your business. Would it be easier for me to work on Winnie if I didn’t have a child to raise? Sure. But I also would not have had the idea for Winnie nor would I have had the same determination to run through walls to make it happen.

What are three things that got you to where you are today?

I used to think I got where I am because I’m a really hard worker but I have more recently come to realize an insane amount of privilege has gotten me to where I am today. Success takes hard work but I also had a wonderful upbringing, supportive parents, and a great education. It would be ridiculous to think that I could achieved even a quarter of what I’ve achieved without this incredible foundation.

The second thing is my husband, Eric Mauskopf. I really could not ask for a better partner in life. Not many men would be cool with their spouse quitting their job after having a new baby, not to take care of the baby but to start a company. He’s an incredible guy, the best dad, and the smartest, most level-headed person I know. To have someone like that to come home to every night is the secret to my survival.

The final thing that has gotten me to where I am today is my attitude. Life has not always gone my way, but it’s just made me more determined than ever to be successful. I have been knocked down too many times to count but I always seem to get back up and keep going, each time stronger than the last.

What is the most surprising thing you've learned in your life or career so far?

People matter the most. When raising money for Winnie, the most important thing was the connections I made and my co-founder Anne made through the companies we’ve worked for. How you treat people counts for so much so it’s really important you not only do good work but you’re someone who people want to work with.

Sara Mauskopf and Anne Halsall
Sara Mauskopf and Anne Halsall

It's seemingly hard enough to be a new mom + CEO, then your husband was diagnosed with cancer. How were you able to get through this time? Did you ever want to throw in the towel?

When my husband was diagnosed with cancer, I immediately assumed I’d need to throw in the towel and focus on his health. I told my co-founder Anne that I wouldn’t be coming into the office for an indefinite amount of time while I figured out his precise diagnosis (the most important thing in treating cancer is knowing what kind of cancer you are dealing with) and got a treatment plan in place. But what happened next was kind of incredible. The team got so much done in the two weeks I was out I realized that they didn’t even need me. In fact, they were more productive when I wasn’t around! It made me realize there was no need to throw in the towel and I could jump right back in.

During this time, I was fortunate to have a lot of support from my family. Ironically, it was also Winnie too that was a big help to me, especially when I was acting as a solo parent for much of this time. I had a lot of one on one time with my daughter so finding places I could take her was important to me. I needed to keep her out of the house for most of the weekend so my husband could rest (we have a small apartment) so I used Winnie often to find new playgrounds and museums we could explore. I also wanted to maintain some sense of normalcy, so I’d frequently go out to dinner just me and my daughter who was a year old at the time. I used Winnie to find restaurants where we wouldn’t cause too much of a ruckus.

What is the best part of your day?

Arriving at the office is my favorite part of the day. I’m always so excited to get to work for the day and focus on making the world better for parents. Although I’m not spending time with my own daughter, having time and space apart to work on something I love allows me to be a better mom to her when I’m with her.

Inspiring Women: Meet the Founder of Winnie, a Yelp!-Type App for Parents

At Livingly, our motto is "live life beautifully." What does living beautifully mean to you?

Living beautifully means treasuring every day and enjoying even the smallest moments. After my husband’s cancer diagnosis, we realized that life is not guaranteed. We enjoy every moment we spend as a family whether it’s a family trip to Disneyland or a simple trip to the park. Cancer is a really ugly disease but it made me appreciate the beauty of being alive and being healthy and I will never take that for granted again.

The Director of Editorial Operations at Livingly Media and lover of all things sprinkles.