In this episode, Alisha sits down with Robby Cobbs, an international educator and the founder of Tech My School, a nonprofit organisation dedicated to supporting underfunded schools in Puerto Rico through thoughtful technology integration and teacher training.

Robby shares his personal journey from growing up with limited resources, to teaching around the world, and eventually settling in Puerto Rico, where he witnessed firsthand the deep educational inequities facing local schools. What began as donating computers to a single school grew into a scalable nonprofit model supporting educators, students, and school leaders.

What We Cover in This Episode:

• Robby’s path from international teaching to founding Tech My School
• Why access to technology alone isn’t enough
• The difference between EdTech (technology supporting instruction) and TechEd (student skill-building)
• How AI can support teachers without replacing human connection
• The importance of balancing digital tools with hands-on learning
• Building trust with educators, parents, and school communities

Key Takeaways

• Technology works best when paired with strong relationships and clear educational goals
• Teachers need ongoing support and training - not just new devices
• AI can be a powerful planning and reflection tool when used responsibly
• Student learning improves when technology is intentional, balanced, and culturally responsive

Change with technology doesn’t have to be scary and overwhelming. This conversation explores how technology can meaningfully enhance learning when it’s implemented with intention, balance, and trust.

Rainbows ahead,
Alisha and Ashleigh

Resources Mentioned in this episode: 

Tech My School – A nonprofit providing technology, training, and strategic planning to schools

TechPlan Genie – An AI-powered tool that helps schools create, track, and refine strategic technology plans

Connect with Robby on Instagram 

Check out Robby’s book, Tech Centered, Learning Driven.

APPLE PODCAST | SPOTIFY  | AMAZON

About Today’s Guest

Robby is a life-long international educator who started Tech My School, an educational non-profit dedicated to serving underprivileged schools that has grown from a single school in 2021 to serving over 50 schools by the end of 2025.  In 2024, he authored his first book, "Tech Centered, Learning Driven" and in 2025 he developed his first piece of commercially available software called "Tech Plan Genie".

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