Jason Kucherawy — Founder
I connect people with places, plates, pints, and other people. For over 20 years, I’ve been turning city streets into stages, history into stories, and strangers into communities. I’ve led tours across Canada and the U.S., co-founded walking tour companies in Toronto, Ottawa, Hamilton, and Ho Chi Minh City, and trained the next generation of guides to do the same. Along the way, I’ve worked with universities, DMCs, and global brands to design cultural experiences that blend walking tours with comedy, craft beer, improv, and behind-the-scenes access. I also teach tourism, food culture, and public speaking at the college level, where I combine industry insight with performance skills from comedy and theatre. Whether I’m in front of a class, a crowd, or a camera, my goal is the same: create memorable connections that outlast the moment. 🍻 Want to collaborate on a tour, training, or unforgettable experience? Let’s make it happen.
Stackforce AI infers this person is a Tourism and Education expert with strong leadership and community-building skills.
Location: Singapore, Singapore, Singapore
Experience: 29 yrs 8 mos
Skills
- Team Leadership
- Tourism
- Cultural Awareness
- Business Development
- Community Building
- Leadership
- Education
- Marketing
- Logistics
- Human Resources
- Hospitality
- Customer Service
Career Highlights
- Pioneered free walking tour model in Canada.
- Developed Toronto's first graffiti tour.
- Trained the next generation of tour guides.
Work Experience
Tourist Guide Association of Toronto
President (2 yrs 8 mos)
Vice President (2 yrs)
Centennial College
Acting Work Integrated Learning (WIL) Program Coordinator (6 mos)
Part-time Professor (8 mos)
George Brown College
Part-time Professor (2 yrs 2 mos)
Saigon Craft Beer Tours
Co-Founder (8 yrs 7 mos)
Craft Beer Vietnam
Founder (9 yrs 2 mos)
Toronto Urban Adventures
Franchise Owner / Guide (11 yrs 4 mos)
Tour Guys
Company Owner (16 yrs 11 mos)
TUI
Communications and Marketing Coordinator (1 yr 8 mos)
Canadian Forces Morale and Welfare Services
Deployed Operations Travel Coordinator (6 mos)
Impact Educational Tours (now Brightspark Travel Canada)
Tour Guide Team Manager/Trainer (4 yrs)
Breakaway Tours
Human Resources - Destination Staff (4 yrs)
Hostelling International - Canada
Front Desk Agent (2 yrs)
Keating Educational Tours
Tour Guide (5 yrs)
Education
Bachelor's Degree at York University