One of the entrepreneurs who came on Pitch Playground this season will receive $50,000 to take their idea to the next level. Which idea do YOU think deserves the cash? This episode takes you on a tour of ten bold education entrepreneurs—spanning equity in education, career readiness, cutting-edge technology, and student agency.

🗳️ Head to pitchplayground.com from June 15–30 to cast your vote.

Here’s a summary of the ten ideas:

Alas | Lisa Maria Rhodes | Episode

Lisa Maria founded Alas to support students navigating the justice system. Alas provides direct support to students entangled in these systems—offering advocacy, connection, and care. With $50K, she’d support 10 schools and 1,000+ students who might otherwise fall through the cracks.

The Liber Institute | Jonathan Santos Silva | Episode

Jonathan is working to transform education in Indigenous and rural communities through The Liber Institute. Through coaching, storytelling, and design thinking, Liber empowers leaders in Indigenous and rural communities. The money would expand the reach of their work through their POWER Framework.

Wiggle Room | Jaime-Jin Lewis | Episode

Jaime-Jin's Wiggle Room simplifies back-end operations for daycare providers and helps families access affordable care. Their tool, AutoEnroll, translates confusing regulations into smooth workflows, making it easier for daycares to scale and survive. The $50K would help Wiggle Room bring their tools beyond NYC, starting with anchor events across New York State.

BridgeYear | Victoria Chen | Episode

Victoria’s nonprofit BridgeYear helps students test-drive high-paying careers that don’t require a four-year degree. With programs like Career Test Drive and MorePathways, they connect young people with meaningful futures on their own terms. The funds would go toward enhancing MorePathways and building a self-directed, student-friendly experience.

UnCommon Construction | Aaron Frumin | Episode

UnCommon Construction is a paid apprenticeship where students earn credits and build houses together, learning teamwork, communication, and problem-solving in the process. After selling the house, students get scholarship-matched paychecks. $50K would support their new 5000 sq ft UnCommon Campus in New Orleans to serve more students and expand programming.

ReFrameXR | Jonathan Teske | Episode

Jonathan wants to make extended reality (XR) practical and accessible for classrooms. His platform ReframeXR brings immersive, mixed reality learning into the classroom—without the barriers of traditional VR. The money would support building out infrastructure to grow the XR education ecosystem.

ScaffoldEd | Evan Wilson | Episode

Evan’s company ScaffoldEd uses AI to analyze family feedback and uncover patterns behind chronic absenteeism. With these insights, schools can act on real barriers—like when a parent needs to use a student's metro card to keep their job. $50K would help them integrate AI agents to help districts not just identify issues, but implement solutions.

Hedge School Cooperative | Dr. Erin Flynn | Episode

Erin started Hedge School Cooperative—a consent-based microschool model built for safety, autonomy, and agency. Based in Texas, the school offers a radically student-centered alternative, where learners have real control over how and what they learn. With the grant, Erin would launch new satellite campuses and support other educators who want to join the movement.

Inner Spark | jacob adams | Episode

jacob’s Inner Spark is rooted in critical thinking and community action. It helps Black and Brown students explore who they are, what they care about, and how to make change. With $50K, jacob would hire a Dreamweaver—a community-connected role that identifies the unique needs of each school and builds partnerships to meet them.

Dream Tech Academy | Danette Buckley | Episode

Danette created Dream Tech Academy, a flexible microschool in Petersburg, Virginia, that personalizes learning for each student. With $50K, Danette would offer more scholarships, invest in classroom tech, and raise teacher salaries to serve more families.

Want to hear more? 🎧 Listen to full episodes at pitchplayground.com, and don’t forget—voting is open from June 15–30. Help decide which bo...