From New York City to Lisbon, Portugal, Cha McCoy shares her love for wine, good food and travel. In this interview she shares what led her to leave her successful corporate job for a career as a sommelier, the creation of her company Cha Squared Consulting and why she chose Lisbon as her second home.
Share your international story. Did you grow up travelling or living abroad?
I never thought of my trips as grand adventures or great travel stories until I started public speaking at travel conferences and I am asked this question. I started traveling at a young age to visit family mainly, but it didn’t seem important. But when I share my story traveling cross country twice on Amtrak from NYC to Sacramento at the age of eight with my brother and mother, who had never been to California before, I realized as an adult this was a big deal. We went on several trips after this one to visit other relatives in the summer, and eventually we left US soil for a trip to Nova Scotia when I was in high school. I didn’t realize how much all these trips had an impact on me until I met people who were afraid to leave Harlem, even as adults.
Why did you choose to do your MBA in Italy. How was that experience?
Well, it was a very personal decision. I was in a serious relationship, we had a dog, we had our apartment and great careers started. But I felt too young for such a serious life. I dreamed of traveling more and my relationship was not going well, and to be honest the company I was working for was also struggling. So, I asked the universe for a reset. I was already enrolled in an MBA program as a part-time student for night courses, while working full time. My advisor shared with me about the opportunity to do a semester abroad, I came back one week later and asked, “How can I get transferred to become a full time Rome Campus student?”
The experience was great, life changing even. I enrolled in a study abroad program in London during my undergraduate studies, however I ended up choosing to stay on campus to join my sorority, Alpha Kappa Alpha. So, I feel like this was always in the cards for me to move to Europe. The most memorable parts of my daily life in Rome was just the aroma of pizza from outside my window, nuns walking around at night for a stroll to get gelato, the architecture and of course the access to great wine.

Image courtesy of Cha McCoy
After a career in engineering, what led you to become a sommelier?
When I returned to the US, I took a job at a wine shop making minimum wage after receiving my MBA. My wine life began here. Fast forward after returning to corporate America, during my annual evaluation with my VP, he would give me rave reviews, and my annual bonus but I became bored with this lifestyle (again). I realized I was working just to make money to eat at amazing restaurants, buy great wine and travel as often as possible. Nothing is wrong with this life, but I wanted a life that was fully surrounded by these things. I did not want to feel like I must wait until the weekend or for vacation to enjoy myself. I believed switching careers and creating a life in the wine industry I would truly do what I love every day. I was inspired to learn more about wine from living in Italy. It’s just a part of the Italian lifestyle and food culture. I decided to take the exams to take my knowledge a step further and legitimize myself in the industry more recently and have not looked back. The work is hard and not as glamorous as you would imagine, after watching Uncorked on Netflix. But now I know, I am building my own way beyond being a sommelier and that Black ownership is more important in this industry and needed.
Tell us a bit about your company Cha Squared Consulting. Why did you create it and what is your mission?
Cha Squared Consulting LLC, a gastronomy experience company is focused on the production of wine and food events, tourism and education. Cha Squared’s mission of breaking down barriers in the wine industry originally started through my wine dinner series The Communion, conspiring with female chefs and family owned wine producers on ways to disrupt the hospitality industry. I’m happy to lead a charge getting more people to visit vineyards and understand wine on a deeper level, even from home.
When did you start living between NYC and Lisbon? What led you to Portugal?
My first trip to Lisbon was for a month in 2018. I returned every other month and finally pulled the trigger to quit my work as an engineer to take on the work for Cha Squared full time in May 2019 and came straight to Lisbon. Portugal was booming recently for young entrepreneurs in all industries. There is massive opportunity within both the wine and tourism industry. The foreign attraction to Lisbon was breaking records for visitors and expats. And I also wanted to live close to the beach, being able to just take public transportation and go to the beach on a hot day seemed like a dream. English is widely spoken throughout the country. Wine of course – I wanted to access the vines and connect with winemakers frequently. Visiting vineyards is very therapeutic for me and of course educational for work.
What was your family/friends’ reaction to the decision? Is this something they anticipated or were they surprised?
For me it was easy, they encouraged me to go, I was going through another rough patch in my life and seem to heal better when I am off on my own. And since I lived abroad before I think they all felt like this was very typical behavior for me.
What are some of the benefits & challenges of living in Portugal?
I will start with the challenges. Getting all the paperwork in order to move and stay was exhausting and expensive and confusing. I would say unfortunately, I probably learned more about what I should have done now after working with a consultant and knowing other expats but that took time. And to be honest I don’t know if I would have known the right answers without coming to live here first. So, hopefully I will do all the right things for my next visa application for next year.
Portugal is interesting, unlike Italy or even France, where my cousin has lived for eight years, most documents can be submitted in English. You can call some of the government phone lines for help in English. The cost of living (outside of rent) is affordable still, especially compared to NYC. Portugal is a small country but has many different things to do and see, especially in the summer. Music festivals, partying all night, or spending time chilling on a vineyard; it’s all accessible and reasonably priced.