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Oliver Guide Founders Q and A

Oliver Guide is a crowdsourced travel platform where user share their travel recommendations for the community. It’s founders, Cynthia Pillsbury and Courtney Leary,  are two mothers who love to travel with their families and created a platform to aggregate the information and tips they got from friends. In the spirit of celebrating family and travel and our community they are hosting a sweepstakes for our members to win some of their fave travel accessories.



What is Oliver Guide?


A platform for capturing and sharing travel recommendations.


You are both busy mothers with jobs– what inspired you to create this platform?


A need. We were both traveling a lot and asking friends for recommendations on where to stay, eat and what to do as friends and friends of friends are the people we trust the most when it comes to travel. At the same time were being asked to share our travel information which meant that we were going back to old emails and doing a lot of time consuming cutting and pasting. Oliver Guide solves that– once you create a guide, you can share it with others forever. And, you can access travel recommendations from friends with ease.


Cynthia– as a Second Shift member, do you have advice for any other women thinking about standing up a new business venture but feeling overwhelmed?


Remember to have fun with it. If you don’t love it and believe in it, don’t do it. Also, take it one step at a time, remember Rome wasn’t built in a day and often times the best ideas evolve with time, trail and error (yes error!).


What are your favorite travel destinations?


Courtney: Always love France, Santa Barbara and New York, but someplace new is the best.


Cynthia: I have my stand-bys – Vail and Nantucket, but have made a promise to take my children somewhere NEW and different every year. We loved Belize and Laos.  Next on the list is (hopefully) Greece for kids and Japan for adults.


Best advice/tip you’ve learned through an Oliver Guide?


Courtney: How to do Art Basel, Miami.  It was something overwhelming that turned into absolute fun once I knew what to do!


Cynthia: Traveling with children is not for the faint at heart. I love to go go go, but that does not always work for so we do… a little culture, a little beach (chill time), a little culture, and so on. I also download Google maps before I get to a location and have my Oliver Guide accessible via a screen grab (if I am not able to have cellular) so I have a plan of attack on the days’ activities.