Pizza Pi Delivery Boat Interview


One story that I remember reading about was the couple who dropped everything to move to the Caribbean and start a pizza delivery service – via their boat. They named the boat “Pizza Pi” and set it up in the US Virgin Islands. The captain of the boat, Sasha, graduated MIT and went to work on Wall Street only to eventually leave and set sail for the pizza biz. His wife, Tara, was a special education teacher from Indiana and originally had moved to the islands to become a scuba instructor. The boat is super impressive and to date the duo has sold over 22,000 pizzas.  You can read more about their pizza business here.  There is an after life after the grind.  I saw the boat story as a success to leaving the rate race and becoming an entrepreneur and wanted to share more info about them.  It’s worth noting, that they’ve decided to sell their business after several successful years to focus on their family.  Below are some Q and A’s from my recent interview:

Me:  How did each of you quit?

Pizza Pi:  I was a teacher in Indiana and I quit once I met Sasha while working on boats –it was a no brainer for me. Sasha was working on Wall Street and teaching sailing in the north cove on the weekends. Winter set in and the sailing program ended so Sasha quit his job and moved to PR to continue sailing.

Me: What was going through your mind when you quit?

Pizza Pi:  “There’s got to be a better way to spend our time”

Me:  Do you get back to your home towns often?

Pizza Pi:  We go back to the States to see family and friends for a month every summer.

Me:  How did you come up with the idea of a delivery service on a boat?

Pizza Pi:  Working in the yachting industry for 7 years previous to opening PiZZA Pi opened our eyes to the need. It was niche.

Me:  Favorite thing about working on a boat?

Pizza Pi:  Interacting with and delighting tourists. The scenery is pretty amazing, too.

Me: Do you live on the boat?

Pizza Pi:  Not anymore.

Me: Favorite thing about island life?

Pizza Pi:  The people are amazing.

Me:  What do you do for health insurance?

Pizza Pi:  We have health insurance through a yachting programme.

Me:  How do you save for retirement?

Pizza Pi:  We put cash into Roth IRAs each year.

Me:  Do you have any recommendations for others looking to make a career change and work for themselves?

Pizza Pi:  Do it and never look back!!

Me:  What will you do once you sell the boat?  Family life is our next big adventure.



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