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Ep. 9: Lynn Perkins Co-Founds UrbanSitter and Learns to Make the Big Ask

Lynn Perkins, CEO and Co-founder of UrbanSitter, shares success tips she learned building a web startup that has helped parents with over a million hours of babysitting. From raising funding to marketing strategies to learning to "punch above her weight class," Lynn's inspirational story is loaded with sage advice for us all.


  • Don't be afraid to make the big ask.
  • Go in person to make the best impression and increase your odds for success.
  • Don't wait for your perfect product; just put it out there and ask for feedback.
  • You can always go back to the corporate world; creating a startup doesn't stop you from going back.
  • Break your large goal down into manageable little steps.
  • Take risks while you're young and don't have kids or a mortgage.
  • It's easier to climb the ladder within an area you're passionate about.

Key notes

  • Lynn Perkins is co-founder of Urban Sitter, a babysitting booking website and app that helps parents find their community's most trusted sitters.
  • Urban Sitter started in 2011 in San Francisco and is now active across 60 cities in America.
  • Urban Sitter secured investor funding even though most male investors aren't involved with securing child care.
  • Lynn made her app and website unique by leveraging the social grid because mothers want to hire based on personal recommendations. 
  • Urban Sitter succeeded in getting PR when it was new by publishing data about cost and hours spent on childcare, which was uniquely available to it due to transactions being completed on the site instead of offline.
  • The most effective marketing tool Lynn used was the sitters who became advocates for UrbanSitter.
  • There is value to visiting in person - Lynn secured a powerful board member by flying to Cincinnati and asking them to join face-to-face.
  • Lynn's life is made easier by using online grocery services which save extra time to spend with her kids rather than going to the shops.


"Aim for excellent, but let go of perfect"

"You gotta stick your neck out there"

"There's value to visiting in person"