David Rudder is the founder of Enroute 2 Success, an entrepreneur with over 30 years of experience in business and community service. A committed advocate for youth empowerment, he has developed impactful programs that provide life skills, mentorship, and opportunities to support their growth and success. Through Enroute 2 Success, Rudder offers chess and golf lessons, financial literacy workshops, motivational seminars, and other enriching experiences—all with a strong emphasis on physical and mental well-being. He has also volunteered as a coach for kids’ basketball and baseball teams, extending his mentorship beyond structured activities. Most recently, Enroute 2 Success organized a meaningful stage production honouring Gloria Baylis, the Barbadian-Canadian trailblazer whose landmark legal victory helped reshape Canada’s workplace equity laws. From Chess Fest to youth-focused initiatives, Enroute 2 Success continues to deliver unique, skills-based opportunities that empower young people throughout the Greater Toronto Area (GTA) and beyond.
Describe your charity/non-profit/volunteer work in a few sentences.
Enroute 2 Success is a non-profit organization dedicated to supporting youth on their route to success by providing unique experiences that expose them to fundamental life skills, mentorship, and engaging programming. Our organization has a sole focus on using golf and chess to develop essential life skills like patience, problem-solving, and confidence.
What problem does it aim to solve?
Enroute 2 Success addresses the lack of positive mentorship and structured development opportunities for youth. Many young people face challenges such as limited access to role models, low confidence, and difficulty developing critical life skills like focus, patience, and decision-making. By using chess and golf as powerful teaching tools, we provide mentorship, guidance, and safe spaces where youth can grow at their own pace in both character and skills, helping them overcome barriers and prepare for long-term success in school, sports, careers and life.
When did you start/join it?
I started Enroute 2 Success in 2022.
What made you want to get involved?
I wanted to get involved because I’ve seen firsthand how powerful golf and chess can be in shaping a young person’s future. Too many youth grow up without consistent guidance on valuable life skills, essential for one’s future, and I believe chess and golf are unique tools to fill that gap. They teach patience, focus, resilience and discipline. By combining mentorship with these games, I knew Enroute 2 Success could make a real difference in building confidence and creating opportunities in youth in our community.
What was the situation like when you started?
We originally started our chess lessons in a small section of a local restaurant. The room fit 6 to 8 people, and some weeks there was only one student.
How has it changed since?
In its short time, Enroute 2 Success has demonstrated the need for an organization like this in the community. So far, we have provided free weekly golf and chess lessons, taken students to golf tournaments around the GTA, and hosted workshops that have left a lasting impression on the community.
What more needs to be done?
We would love to expand our reach to serve more youth across the GTA and beyond. It would be great to offer our programs in partnership with schools and other community organizations to provide even more impactful experiences.
How can our readers help?
Readers can make a meaningful difference by getting involved in a few ways.
- Volunteer: We are always looking for people who want to help with our mission.
- Support financially: Donations help provide equipment, training programs, and safe spaces for participants to learn and have fun.
- Spread the word: Help us reach more families and youth by sharing our mission and encouraging youth to join our programs.
Do you have any events coming up?
Chess Fest Tournament, SIP n Paint and Black History Month film screening and fireside chat
Where can we follow you?
Instagram | Facebook | Email | Website
PAY IT FORWARD: What is an awesome local charity that you love?
Kids Help Phone. I love Kids Help Phone; I think it’s an amazing charity because it provides 24/7, confidential, and bilingual mental health support to youth across Canada. Their commitment to accessibility, inclusivity, and innovation aligns with our mission to empower young people through free programs like golf, chess, and mentoring. By ensuring no young person feels alone, Kids Help Phone plays a vital role in building stronger, healthier, and more resilient communities.
