Getting the Dirt With Winston Southworth

Winston Southworth is a young entrepreneur, philanthropist, and member of the Class of 2020 at Hingham High School. At the age of 9, Winston started a small landscaping operation that has turned into a full-time business that keeps him and his crew busy seven days a week, and sometimes up to 14 hours per day. During all of this, Winston and his crew (who are also students) also manage to balance their school work and obligations at home. Throughout his landscaping career, which happens to encompass half of his 18 years, Winston has always remained focused on how he can give back. During the COVID 19 crisis, Winston has quietly provided his services at no-cost or low-cost to first responders who had planned to pay him in full and is now donating a portion of his hard-earned profits to Hingham's "FLAG" to thank first responders.

He is a gifted landscaper, a hard worker, a team player, and a good Samaritan.

Hingham, meet Winston.

What are your best/most fun memories from your time growing up in Hingham?

1)    Getting the walk-off hit to win the Major League Little League World Series!

2)    Coming behind from a 12-1 deficit of the first-quarter of the Travel A Team Basketball Championship, and DEFEATING Marshfield. They were stunned!! My dad coached the game of his life that day!

3)    Playing summer Travel A Baseball with this group of players. We spent many summers together and became very good friends often going out to eat after games, having cookouts, and pool parties at the Mulkerrins.  If this team had stayed together in high school, there is no doubt we would have won a State Championship.

4)    Every year on my Birthday, June 17th, we would pick a charity to accept donations instead of gifts to myself. I have a big back yard so we would have up to 250 people in the back yard with an entire day of events, silent auctions, etc. Each year had a different theme. Our charities were: Dana Farber, Horizons for Homeless Children, Seeds of Peace, Save Darfur, the drought in Africa.

What was your favorite subject in school?

My favorite subjects in school were “Walk Down Wall Street,” Economics, English, and Wood Shop.

What teacher made this biggest impact in your life?

Many teachers have impacted my life starting with Ms. Carol Scheig at the South Shore Conservatory; Mrs. Gioioso & Mrs. LeBlanc at South School; Ms. Beaupre, Senora Malerbi, Mrs. Doerr, Mrs. Jacobson, Dr. Struzzierro, Ms. Allen, Dr. Pawlowski, & Mr. Doerr. These teachers believed in me; when that happens, you can achieve anything.

Winston with Mrs. Gioioso when he was in 3rd grade at South School

I would say the biggest impact would be Mr. Doerr, my history teacher junior year who both pushed me to use primary sources and supported me for my National History Day project which went all of the way to the State Finals, one step from Nationals.

Winston with Mr. Hoey (Hingham History Department Head) and his National History Day Project

What is your favorite meal in Hingham?

Chicken pesto sandwich from Stars.

What will you miss most about your hometown when you go to college?

I will miss the historical community, my family, and my friends.

If you could give one piece of advice to Hingham Kindergarteners, what would it be?    

The one piece of advice that I would give to Hingham Kindergarteners is the one that my Mom has instilled in me and that has helped me achieve many things. I am named after Winston Churchill, whose famous mantra was “Never, Never, Never, Quit!”. So I would tell Kindergartners that no matter how hard something is, how tough a day is, even if you feel like quitting, don’t. Getting up every day and just trying your best, and not giving up, is how you will succeed where others fail.

In addition to your schoolwork, sports and extracurricular activities, how was your business created? 

I officially started my business in 2010, when I was nine years old.

9 year-old WInston's first business card

Why landscaping?

When I was around 2 years old, I would stare out the window for hours watching my dad take care of our large lawn and work in the yard. When I was 2 ½ I got a toy John Deere riding lawnmower from Santa. I spent many days “landscaping” with that in my younger years. When I was eight, my number one present request from Santa was a backpack leaf blower, which was under the tree that year.

What is your favorite part of the job?

I have always liked to physically work hard. I have never been much of a video game player. I really enjoy scoping out a yard, making a plan, seeing it through to completion, and witnessing the transformation. It is very fulfilling to see a positive result and to have the client be satisfied enough to write a positive testimonial on a public post.

Why did you decide to start your own business?

I am very fortunate to witness and adopt the work ethic of my parents who have owned their own company, MWI Fiber-Shield, for over 33 years. Less than 10% of small businesses survive 30 or more years, so I am really proud of my parents sweat equity. Most people don't appreciate that when you own a small business, you are always working; even throughout weekends and while on vacation. There is no “back up”; you are the back up. The positives are that whatever work you put into it, you can hopefully realize back. You are your own boss and can create what you want. My parents work very long hours and I do as well. Whether school, baseball, or work, I feel that putting maximum effort and time makes all of the difference. Working long hours is definitely part of being successful. I have been getting up around 6 am every morning, and working until 6 or 7. I try to return calls, do estimates, eat, and get my school work done before bed.

When school was first closed in March, I contacted Senator Patrick O’Connor who contacted Governor Baker’s office to get official permission to work and to be considered Essential. I wear a mask, gloves, and socially distant on all of my jobs. All of my communication, estimates and billing is done on line. I am one the Hingham Baseball Captains, and I was able to hire two other hard working friends who are also Captains; Christian Julian, Basketball Captain, and Joey Iaria, Wrestling Captain. All three of us have all been Patriot League All-Stars. Another friend Mike Gervasi, who plays baseball at UMASS works as well. Sometimes, Luke Mashburn, chips in when I am really busy. All of my guys are hard-working, respectful, and really appreciate the opportunity to get outside, even if it’s cold and raining, to be productive and make some money. They all wear masks, gloves, and practice social distancing.

Are you earning money for something specific?  

The money I am earning is for college. I was fortunate to get an academic allowance for Endicott, but there is still a large balance.

Winston and his crew

We've heard that you and your business are very philanthropic. What type of programs are you doing now to give back to the community?

I am donating a $500.00 gift certificate to FLAG. I wanted to give back to the doctors and nurses who are risking their lives. So much food has been donated, I wanted to do something different. So, I am waiting to hear back from Mrs. Crean about posting on their page. We thought we would have a contest and have people ask for, or have people nominate a health care worker that needed/deserved a spring clean up or lawn care, valued up to $500.00. That is a lot of work, but these people are saving lives, and are probably very stressed out and exhausted with little time for their lawn.


*If you would like to contact Winston about his landscaping services, he can be reached at: 339-226-2892

1 thought on “Getting the Dirt With Winston Southworth”

  1. Wow !!! very impressed you must have the greatest parents. You’re on your way to make a great fingerprint in life. Let’s Gooooooooo!!!!!!💪😎


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.