We caught up with the brilliant and insightful Theodore Hoskinson a few weeks ago and have shared our conversation below.

Theodore, thanks for joining us, excited to have you contributing your stories and insights. Let’s jump into the story of starting your own firm – what should we know?

My wife and I wanted to help children and families in need and she had chosen a name: Roots and Wings. It was in our will, but unfunded. When my wife passed away suddenly in the spring of 2016, I decided to establish a non-profit under that name to honor her and her vision in the name: one needs to establish a strong foundation (roots) in order to grow and prosper (spread your wings).

I established a 501c3 non-profit with 2 of my closest friends who also felt that helping the under-served population in our area with free educational help would be a hand up and not a handout. That was the correct approach.

We went to one Title 1 public elementary school in our area (Delray Beach) and with the help and guidance of the principal established Project UpLift. Its approach was unique: a free after-school literacy program, taught in the school by the school’s certified teachers. The students chosen were in the bottom 25% of the students and therefore they were reading one or two grades below grade level. Classes were to be no more than ten students. They met for three hours a week after school for 9 weeks in the fall and 9 weeks in the spring which meant that we were offering 54 hours of free tutoring to those that were the farthest behind.

We used our money for that first program which was 30 third grade students, helping them with their literacy skills before they were going to take the reading proficiency test at the end of the third grade year.

Money was not the challenge to start, but it always will become a problem if you prove proof of concept and want to help more children. I always believe in starting small, because you will always need to change or tweek something to make it better.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I lived most of my life in Washington DC where I attended Sheridan School and St Albans School for Boys.. I then attended Tulane University in New Orleans where I received a BA in History, graduating in 1969. The following year I taught 2nd grade at Metairie Park Country Day School. St Albans asked me to return and teach 4th grade the following year, which I did. I taught 4th grade for almost 15 years. I was asked to establish the Office Summer Programs at the school which I did. I helped increase the number of programs offered and the number of students attending. It became so important to the school that I needed to leave the classroom behind to run Facility Rentals as well. I married a wonderful woman who went to Holton Arms School and Smith College, before attending law school at Georgetown University. We were married for 34 years and traveled often.

We had decided to establish a Foundation that would help children and families in need. Anne had named it Roots and Wings, a name she loved because it described for her what we were going to try and do: help children establish strong roots so that they can spread their wings and then soar to a place where anything is possible through hard work and determination.

When Anne passed away tragically in 2016 I decided the best way to honor her life was to establish the organization she wanted, and carry out that mission. We started by creating a program called the Above and Beyond Awards which honored teachers who inspired students. When I asked the Principal at Pine Grove if there was anything else we could do to help education, she said “Help my kids read.” That was the beginning of Project UpLift, a free, small group after-school literacy tutorial program that focuses on public school elementary students who are reading one or two grades below grade level. We created the program and the first year (2017) we taught 30 3rd grade students in one school. Today, the program is in 13 public elementary schools, teaching over 1,000 students. The need is great. We are doing all we can to help address the problem. When we receive additional donations and grants, we continue to expand the program to new schools. If you can’t read you can’t learn! AND Kofi Annan once said, “Literacy is a bridge from misery to hope.” We are helping students hope and dream, and believe in themselves.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

Integrity is the key. You must be honest and believable. You must be a person who people understand and need to be respected. I always ask people what charitable things they focus on. Why waste one’s time chasing someone who isn’t interested in your cause. Now the person says Education or Health Care. You need to show knowledge of that area and tell them that it is a wide area. They need to zero in on their interest. If they say “Not sure” you need to pose a question such as “Did you realize…?” to get them engaged. Show your passion and knowledge of the subject. That person must believe and understand that you are committed to the success of the venture.

What’s been the best source of new clients for you?

Meetings (including breakfasts, lunches and happy hours) where a friend will join me. I support other organizations so that people see that I am genuinely interested in supporting efforts to improve the community in which I live.

Contact Info:

• Website: https://rootsandwingsinc.org/
• Instagram: https://www.instagram.com/rootsandwingsfl/
• Facebook: https://www.facebook.com/RootsAndWingsFL/
• Linkedin: https://www.linkedin.com/company/rootsandwingsdelraybeach
• Twitter: https://twitter.com/i/flow/login?redirect_after_login=%2Frootsandwingsfl
• Youtube: https://www.youtube.com/@rootsandwings5333

Image Credits
I have the rights to use pictures the organization took.