Cohort Spotlight: Calvin Robertson of Jubileague – Designing the Future of Learning Through Play
From Visionary Dreamer to Impactful Innovator: Calvin Robertson's Journey with Jubileague and The Boost Pad
At The Boost Pad, we believe that innovation is not just about solving problems—it’s about reshaping possibilities. That spirit is embodied in Cohort 9 alumnus, Calvin Robertson, the visionary founder behind Jubileague, a gaming company that’s redefining how kids learn and create through play.
From Building for Big Brands to Building for the Next Generation
Before launching Jubileague, Calvin spent years crafting digital experiences as a product designer, software developer, and design leader. His work has touched household names like Hallmark, Lowe’s, and Best Buy—but deep down, Calvin knew he was called to build something of his own. Something with purpose. Something that could plant seeds of creativity and confidence in young minds.
That seed became Jubileague—and its flagship platform, Playmaker, is a revolutionary tool designed to teach kids the art and science of game design. It’s hands-on, imaginative, and rooted in the idea that kids learn best when they’re having fun. Calvin calls it the “Montessori of game design,” and it’s already making waves.
Finding Fuel in the Fire: Calvin’s Boost Pad Journey
For Calvin, joining The Boost Pad wasn’t just about getting a leg up—it was about finding a community of builders who believe.
“I joined The Boost Pad because I know that success needs company. What I received was a community,” Calvin says.
Throughout his cohort experience, he found something deeper than business acumen—he found accountability, mentorship, and encouragement. He learned to clarify his message, refine his model, and build a company that could scale while staying true to its mission.
“That guidance has been instrumental in turning my ideas into a winning, executable strategy.”
At The Boost Pad, we watched Calvin take raw creativity and sharpen it into a polished, purposeful business. It’s the kind of transformation that happens when great ideas meet great support.
A Word from Calvin to Fellow Dreamers
To every entrepreneur wondering if it’s worth it, Calvin offers this:
“You don’t have to go through this alone. If you’re building something bold, The Boost Pad is where you’ll find people who genuinely understand your vision and want to see you succeed. We celebrate each other’s wins while pushing each other to be great.”
“The Boost Pad is about building belief. If you believe in your vision, they will believe with you.”
We’re proud to spotlight Calvin Robertson and Jubileague—a company turning curiosity into creativity, and play into powerful learning.
To learn more or support his work, visit jubileague.com
Connect with Calvin on LinkedIn & Instagram
Interested in joining a future Boost Pad cohort and finding your people? Let Calvin’s story be your invitation.
Founder Stories & Startup Wins — The Boost Pad
