Kerry-Ann and her two Caribbean grandmothers who taught her about entrepreneurship

What My Caribbean Grandmothers Taught Me about Entrepreneurship.

Grandma Among Positive Examples

My Caribbean Grandmothers were important figures in my life. And even though they’re no longer alive, the still have an impact on me. I grew up around a lot of entrepreneurs while living in Jamaica:

  • I had grand uncles who were fishermen; farmer; mason/builder
  • My grand-aunt bought clothes in Falmouth and walked with the biggest and heaviest duffel bag and sold what she bought door to door. Her daughter owned her own salon;
  • I also had several sought after seamstresses in the family.
  • Several of the ladies at my church had their own cook shops (probably considered today as food trucks); another owned an appliance store.

And after I moved to Brooklyn, I was surrounded by even more entrepreneurs:

  • Record shop owners
  • Mechanic shop owners
  • Nail salon owners

But of all these people, I was most inspired by my two grandmothers – Grandma Fletcher and Grandma Reid; and as a result developed entrepreneurship bug from them.

3 picture collage of woman and one with two women hugging. Kerry-Ann with one of her Caribbean Grandmothers

Grandma Fletcher and Me

Necessity + Opportunity

Growing up, they sold a variety of things to make ends meet. After the 1988 Hurricane Gilbert, Grandma Fletcher started a day care in our home which lasted for years. I couldn’t understand why she did it because prior to the hurricane, she was the director of the community daycare center. I was too young to understand that she had lost her job.

Having the daycare at our house was a lot of work and at times, my brother and cousins were annoyed with all the extra work that came with your house being a daycare for most of the day. At the time I don’t remember too many people turning their home into a daycare. Her reputation from running the day care center made it an easy transition for her to start one from home. In addition she sold baked goods (Coconut “drops”) and frozen items (ice and “bag juice”).

homemade jamaican bag juice

Homemade Jamaican Bag Juice

I enjoyed when she made the “coconut drops”. When she wasn’t looking we’d sneak hot pieces from the tray. As we got older, she was less involved in making the “coconut drops” and all the prep work was delegated to my cousin, brother and me which included de-shelling the dried coconut. De-shelling coconuts had on the job hazards like cuts from the sharp edges of the cracked coconut. Try getting a knife between the coconut and the shell…oh Lord.

Jamaican Coconut Drops courtesy of

Jamaican Coconut Drops
courtesy of

My paternal grandmother, Grandma Reid was a full-time nanny and I was told she’d travel to England and Paris with the family she worked for. I was impressed, because this is late 1970’s early 1980s Jamaica. I’m not quite sure how that job ended but I know that she found other things to do. She sold various items – it was like having a corner store at home. And I remember when my brother and visited we would enjoy freebies. We also enjoyed being real “shop keepers” so to speak – giving customers what they wanted and accepting the cash in return.

Kerry-Ann with her Caribbean Grandma Reid

Kerry-Ann with Grandma Reid

What they did was a necessity – they needed to survive. They needed to supplement their income to support their families but there was a clear message I learned from both – there will come a time (or two, or three) where you’ll need to reinvent yourself to survive by finding a need that people have and fill it. It doesn’t have to be elaborate or fancy – as you read in both their cases. As Paul C. Brunson said in one of podcast 28:

“There is truth to being West Indian or to be an immigrant or being from an immigrant family and realizing that fundamentally, there is this need to survive. And really thriving in entrepreneurship is being and realizing that there is a need for you to survive.”

Entrepreneurship All Around

Entrepreneurship isn’t always about finding the next Google, FaceBook, Uber, Airbnb or whatever hot, tech startup “unicorn” or company is in the news now. Like I said on the recent Caribbean Digital Divas panel, entrepreneurs and entrepreneurship is all around us especially if you’re from the Caribbean.

As much as I’ve learned it and heard it repeated – it’s looking at my two Caribbean grandmas that I’m reminded to not let competition scare me away from offering a product or service. After a time, Grandma Fletcher wasn’t the only one selling ice, or coconut drops, or “bag juice” but that didn’t discourage her and caused her to close shop. Grandma Reid was selling items from a basket from the side of her house. Her competitors were the formal shops (aka store) who carried more inventory than she did but that didn’t stop her.

Tap into our innate genius and creativity that our Caribbean American heritage gifts us with. This heritage is our birthright or competitive advantage – be unapologetic about it.

In the spirit of celebrating Mother’s Day I acknowledge my Caribbean Grandmothers and entrepreneurial trailblazers. These 2 matriarchs did what they could to provide for their families and were unapologetic about who they are.

Your Turn

Did your Caribbean Grandmother have a similar impact on you? Who in your family was the entrepreneurial trailblazer?


Kerry-Ann Reid-Brown is Founder & host of Carry On Friends one of the first podcasts dedicated to the Caribbean American Experience. She is leading the way for Caribbean Podcast as the founder of Breadfruit Media, the first Caribbean podcast production company; and founder of the Caribbean Podcast Directory a place to discover podcasts by people of Caribbean Heritage.