About

Hey there! My name is Jess and I am originally from Atlanta, where I grew up with one brother and one sister. My mother was a school teacher and stayed home with my siblings and I, and my father owned a trucking company. Growing up I enjoyed swimming, riding bikes and music.

In middle school and high school I put most of my time and focus into music. I took 8 years of piano lessons and also became an accomplished flute player and planned to major in music performance in college.

Travel

One day, towards the end of my senior year, my mom and I had been out and were driving home. Out of nowhere I told her I did not want to major in music. I wanted to go to a community college and spend the summer in Nicaragua. (My aunt and uncle were spending the summer in Nicaragua to relieve a missionary family and there was an opportunity to stay with them.) Still to this day I really don’t know where this epiphany came from. It was a huge deviation from a plan I had set in my head for many years. I really have no idea what she thought of this either, because she had to bribe me to take 4 years of Spanish in high school! But being the supportive mom she was, she said “ok” and did everything possible to make it happen.

The summer after I graduated high school I took my first plane ride to Nicaragua. During the 5 weeks I was in Nicaragua I worked in various orphanages. We did everything from painting, singing and crafts with the kids, reading Bible stories and playing futbol…of course! It was literally the best month of my life and sparked a love of travel and learning about other cultures, which came in handy later in life!

When I returned from Nicaragua it was heart breaking. I remember being so sad to leave. The trip was so much fun and I wanted to learn more about the culture. I knew I would go back and visit one day.

The next year, in 2001, I had the opportunity to study abroad in Argentina. I had taken a few semesters of Spanish in college and was about 85% fluent. I really enjoyed my time there, but unfortunately it was cut short due to circumstances beyond my control…another story for another time! Eventhough I did not spend the planned full year in Argentina I learned a lot and was glad to experience another culture. It also enabled me to speak Spanish on a daily basis with native speakers.

Over the course of the next few years I was able to visit Nicaragua (again) and Costa Rica. I was also taking college courses and working part time at a restaurant.

The Grind

After working at a restaurant for 2 years I decided I wanted a more grown-up job so I went to a staffing company to find a full time job. I was placed at a few different temporary jobs and then landed at a large freight forwarder in Atlanta. It was a somewhat familiar setting because my father owned a trucking company. When I was younger I would often accompany him on short trips and once even drove with him to New York to make a delivery.

I enjoyed learning about the logistics industry and all the moving parts. After a few years I realized there was not much room for growth at that particular company. I left to work at my father’s trucking company for about a year and then took a job at another freight forwarder.

It was a smaller company than my first in the industry and I could tell I could have a career, not just a job at this company. I learned all I could about how they worked and always tried to go above and beyond. I was helpful and supportive of co-workers while also learning new aspects of the business. I worked with extraordinary people during my 10+ years and will always be greatful for the knowledge and experience I acquired. I was also able to travel for client meetings that took me around the U.S. as well as Ireland, Panama and Denmark.

Family

In 2007, while working in the logistics industry and taking night classes, I met my now husband. I knew he was different when I met him. He had a drive and focus that you rarely find. I gravatated toward his quiet energy, because I had been very focused on work and education and it was nice to find someone with the same mindset. Damion is not a talker and did not verbalize his plans to many people, but he knew what he wanted, knew how to get it and most importantly was willing to put in the hard work to make it happen.

Damion grew up in Jamaica and moved to the U.S. to work when he was 23. I knew nothing about Jamaica when I met him, aside from Bob Marley, Sean Paul and really fast sprinters! I enjoyed getting to know Jamaican culture, food and music.

Damion and I got married in 2008 and moved to New York, for his job, in 2012. In 2017, we had our first son, Zidane, and had our second son, Julian, in 2019.

Real Estate

From 2012 to 2019 we were focused on saving money and investing in real estate. We created multiple streams of income from various real estate investments in Atlanta, New York and Jamaica. Our first home in Atlanta was a condo which we now rent out. Our home in New York has a basement apartment that we rent out. We bought our first home in Jamaica in 2016, as a retirement home, but it is currently listed on Airbnb.

As you can see, there is a common theme. We make purchases to use for our family, but that can also make money on the side. This is where my entrepreneurial mindset really kicked in!

Transition Phase

I gained a wealth of knowledge while working in the logistics industry 15+ years. Despite my work ethic and contributions I was let go from my job in late 2017, when my company was acquired by another freight forwarder. It was devastating at first, but I used the time to spend with Zidane, who was 3 months old at the time.

I applied to multiple jobs and had interviews until March 2020 when COVID-19 shut down New York. I kept applying for remote jobs during this time, but the job market was so flooded with people that had been let go that it was difficult to get an interview.

SideHustleMama

One day I was driving home from doing some errands and just thought “I should start a blog.” People in the past had told me I should start a blog, but it seemed so intangible and unrealistic that I didn’t give it much thought. I started doing some research and learning more about blogs, how to start them and how to monetize them. The prospect of starting a blog and owning my own business was very exciting.

I had trouble focusing on what I wanted to blog about, so I decided I would start a lifestyle blog that focused on how I had created income while being at home with the kids. Many work from home and stay at home moms want to make extra money on the side to help support their families and I wanted to offer encouragement and share my experiences to help them along their journey. This is when SideHustleMama was born! I learned all I could and took a course that enabled me to launch my blog in May 2020.

I started my YouTube Channel, to accompany by blog, in June 2020. I quickly found that my viewers were more interested in buying real estate and stocks in Jamaica than creating passive income. For this reason my blog is now focused on helping people learn about the real estate market in Jamaica as well as the Jamaica Stock Exchange (JSE).

I look forward to sharing my past and present experiences to help others invest in Jamaica!

I hope you enjoy and benefit from the content. Please feel free to contact me or leave a comment if you have any questions or would like to learn more about a specific topic!

Be sure to subscribe to my blog, so you never miss new content!

Please also check out my YouTube Channel for more great content!