An Interview with Sara Mauskopf

Sara Mauskopf Interview

Sara Mauskopf, CEO/co-founder of Winnie, has a background in consumer technology and product management, having been a product leader at Postmates, Twitter, YouTube, and Google. She graduated with a Computer Science and Engineering degree from MIT. She lives with her daughter Bryn and her husband Eric in San Francisco.

In this interview, Sara shares how she started Winnie and talks about its mission to solve the common problems parents have on-the-go.

Her advice for entrepreneurs starting a business in California:

Look to users outside of California, even if you’re starting in California, pick a name and domain that’s easy to remember and always incorporate in Delaware, not California. Lawyers can better explain why this is important.

Why did you start Winnie? Can you tell me a little bit about your business and what you do?

I started Winnie in January 2016 with my co-founder Anne Halsall. I had recently given birth to my daughter and I realized there was so much information I needed to know about where I could take her and what I could do with her. Did my favorite restaurant have a changing table in the bathroom? Was there anywhere indoors I could take her to play nearby?

Winnie provides this information and more. It helps parents find great places to go with their children. It gives them local information from other parents about schools, doctors, playgrounds, and so much more.

Is there a competitive advantage that you have over the rest? How did you find it and ‘niche down’?

We realized that there wasn’t any product out there that provided the kind of local information for parents that Winnie provides. There are some products that give information on kids classes, but nothing that tells you about everywhere around you from the perspective of being a parent.

We didn’t want to build a product just for wealthy parents who could afford expensive classes for their kids. And who wants to take their kids to classes all the time anyway? We wanted to build something with real product-market fit, even if that meant we didn’t make any money in the beginning!

How did you find the time and money to get Winnie off the ground? Any advice for entrepreneurs with minimal time or resources?

This is not a side-project for us. We are building a company at scale. We quit our jobs to work on this and raised over $2M in venture capital funding. I would advise entrepreneurs with an idea to take it seriously.

Don’t work on something with minimal time and resources—give it everything you’ve got. Too many people, especially moms, approach building something for parents as a side project. It’s really disappointing.

What do you consider the biggest milestone that you have hit with your business? What was the number one thing you did you get there?

We’ve collected over 1 million locations in Winnie and over 250,000 of which have Winnie proprietary metadata (stuff like whether there’s a changing table or a kids menu). This data doesn’t exist anywhere else. As far as how we did it, we built technology to collect this data at scale and we also crowdsource a lot of this information from our users.

Who has been your greatest influence as an entrepreneur? How did they shape your business?

My daughter has been my number one influence. I thought of the idea because I faced this issue myself as a parent. Being a mom myself I knew that parenting is real work and deserves great tools. Without my daughter, I would never have had the idea for Winnie and also not had the motivation to come into work every day and build something great.

In your experience, what is the best way to find your ideal customer? Are there any mistakes that our readers can learn from?

I think it’s really tempting to start with customers in your local market. For many tech companies that means they focus on attracting customers in the San Francisco Bay Area. When you do that, however, you really limit your idea and your business.

From the beginning, we made Winnie available everywhere and learned a ton about how parents outside of the San Francisco Bay Area want to use Winnie. It helped us see things we would have otherwise been blind to.

As a business owner, what is your greatest fear and how do you keep it under control or harness it?

Earlier this year, my husband was diagnosed with an aggressive form of cancer. That really put things in perspective for me. I really don’t have any major fears about Winnie.

How do you balance life and work to remain connected and available for your loved ones? Any advice for me?

Because both of us founders of Winnie are moms, the importance of family is built into our culture. We do not work all hours of the day. We really focus on getting our work done during working hours and then spending time with our families when we’re not working.

The same goes for our employees. Weekends are precious and we don’t fill them with work. For me, that means I’m always going to the playground with my daughter on the weekend or somewhere fun.

Where do you see Winnie in the next 5 years? Any new products in development?

We founded Winnie to elevate the next generation of parents with tools and information. We’re starting with local information because there’s an obvious gap there but there’s all kinds of information parents need.

For example, we also have an app Baby’s Day by Winnie that helps women track their breastfeeding and pumping and put together a resource to help parents breastfeed on-the-go.

What are the top 3 pieces of advice that you would give someone starting a business in California? What do they need to know from the beginning?

My first piece of advice is to look to users outside of California, even if you’re starting in California. It’s too easy to build for just a bubble of users that aren’t representative of America and the world.

My second piece of advice is to pick a name and domain that’s easy to remember 🙂 We had to do a bunch of work to get but we finally did and it’s made a big difference in terms of people being able to find Winnie on the web after they heard about it from a friend.

Lastly, always incorporate in Delaware, not California. Lawyers can better explain why this is important.