You can’t control it all, right?

Motherhood can be a real revelation for those of us with Type A personalities. As much as we would like to control our own destiny and schedule our lives according to a predetermined plan, parenting simply doesn’t work that way. Life doesn’t work that way. And neither do startups.

Sara Mauskopf was already dealing with the surprises that come from being a new mom back at work when she got the idea for a tech startup of her own. With the financial means to move forward and a supportive partner in her husband, Sara realized that while it was not an ideal time to walk away and become an entrepreneur, it would never get any easier. She would never have fewer responsibilities or less on her plate, so she took the leap. Together with her co-founder, Sara created Winnie, a companion app for modern parents.

Another unexpected curveball

And then her husband was diagnosed with cancer. Resigned to the fact that the new company might die without her, Sara signed off for two weeks to focus on her husband. But when she returned to work, the Beta version of the app was ready to launch. The team had been productive without her, facilitated by the flexible, family-friendly environment in place at Winnie.

Today Sara shares the inspiration for her venture, explaining how the app offers parents timely, personalized information as well as answers to basic parenting questions. I ask her about making the decision to found a tech startup as a new mom and establishing the family-friendly work environment at Winnie. Sara discusses her husband’s illness, how she used blogging to ask for help and process in real time, and how the experience changed her perspective on work. Listen in for Sara’s insight on the compatibility between motherhood and startups and her advice around mentorship and networking with women in tech.

The Startup Pregnant Podcast Episode #030

Some quotes from the episode

  • “Why did I build Winnie? I became a parent, and I think the most shocking thing to me about becoming a first-time parent was that parenting information was so hard to find.”
  • “I have this opportunity to build my own startup where I can show the tech industry that it’s possible to be family-friendly and be successful.”
  • “The fact that I’m really restricted in my time means that I try to make the things that I do really count, and I think that’s actually helped me. It’s helped me prioritize, and it’s helped me get opportunities I might not have otherwise cared about going for.”
  • “There may be women with a technology background that are seeing these problems firsthand, but they just can’t afford to pay for childcare and not make an income for a period of time. I felt like I had all the pieces in place, so how could I not do this?”
  • “I have always been very vocal about this: I pay for a lot of things that I am not doing. I pay for someone to clean my house. I pay for childcare full-time. I now pay to have someone cook for us… The fact that I do it doesn’t make me a worse mom, it makes it possible for me to do all these other things.”
  • “Almost losing my husband and seeing everything hit rock bottom for us made me realize that nothing else is important. My family being healthy is the most important thing, and everything else is just a minor detail.”
  • “Look, I need to keep my family healthy. That’s the number one thing. After that, if I have any time or energy left, I’m going to spend that helping people that need help.”
  • “I’ve actually found that [a tech startup] is probably the best job I can have as a mom because I have the ability to do things my way.”
  • “The thing you learn being a parent is that you really can’t control any of it.”
  • “I would love a routine where I could drink a cup of coffee, or put on makeup, or shower. Usually I just gotta pick one or two of those things, and hope that they get done before it’s time for me to head off to work.”


Sara Mauskopf is the co-founder and CEO of Winnie, a venture dedicated to making parents’ lives easier through technology. Sara graduated from MIT with a degree in computer science and engineering and went on to work as one of the early employee at Twitter. Her impressive resume also includes positions with Silicon Valley powerhouses including Google, YouTube and Postmates.




Thank you to the sponsor of this episode: Aeroflow Breastpumps. They are dedicated to making the hassle of getting your breast pump a little bit easier—actually, a lot easier! Head to to have them help you qualify for a free breast pump through insurance.

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