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Pitch Playground

How could $50,000 transform learning? On Pitch Playground, we invite education innovators and social entrepreneurs to throw their best ideas at us. From technologies that build empathy to providing affordable childcare and reimagining the way we learn—this is a place for pitches from visionaries. Each episode features an intrepid edupreneur workshopping a $50,000 project to solve a critical problem in education. With support from mentors, funders, and fellow entrepreneurs we'll explore what it takes to turn dreams into reality. At the end of the season, we award $50,000 to the best pitch we've heard on the show. We're inviting educators and social entrepreneurs to play in the sandbox with us and share their vision for the future of education. We encourage these visionaries to be BOLD—don't just think outside the box; reshape the box itself. Draw outside the lines. It's about making good ideas last longer and go further. About the Host, Nicole Jarbo: Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. A serial entrepreneur, former educator, and proud 4.0 alum, Nicole has a track record of building impactful ventures across a variety of industries, including education, financial technology, and media. Passionate about storytelling and innovation, she’s sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun. About 4.0: 4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,600 ideas, and our alumni have impacted millions of students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all. Have a Pitch to Transform the World? We’d love to hear from you! Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at https://pitchplayground.com/ and subscribe to Pitch Playground wherever you get your podcasts.
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Episodes

Winner Announced!!!

We’re here to answer the question you’ve all been asking: who won the $50,000? We’re thrilled to announce that Jonathan Santos Silva of The Liber Institute is the winner of this season’s Pitch Playground prize! 🎉 Tune in to this mini-episode to hear Jonathan’s real-time reaction to the news and what he’s planning to do with the $$$. Jonathan is the founder of The Liber Institute, a nonprofit dedicated to equipping Indigenous students, families, and educators to redesign schools from the ground ...

Jul 16, 20253 minEp. 12

Call to Vote: Which Idea Should Win $50k?

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 suppor...

Jun 10, 202516 minEp. 11

Building a Better Childcare System: How Jaime-Jin Lewis’s AutoEnroll Simplifies Childcare Operations

Childcare is essential for high-functioning societies—linked to better health, education, and employment outcomes. Yet despite its high social return, caregiving remains undervalued, with the labor—paid or unpaid—falling disproportionately on women. Jaime-Jin Lewis, founder of Wiggle Room , is building the infrastructure behind a more dynamic and durable childcare system. Her tool, Auto-Enroll , simplifies back-end daycare operations, turning a 58-page regulation manual into easy-to-use workflow...

May 27, 202531 minEp. 10

Redesigning Rural and Indigenous Education: How Jonathan Santos Silva’s Liber Institute Empowers Communities at the Margins

If we design at the margins, what we learn will help us make education better everywhere. That’s the perspective of this episode’s guest, Jonathan Santos Silva, founder of The Liber Institute. Liber’s mission is to embolden and equip Indigenous students, families, and educators to redesign schools from the ground up. Jonathan’s journey took him from Brockton, Massachusetts to the Pine Ridge Reservation in South Dakota, where he saw firsthand how systemic challenges create barriers to education f...

May 13, 202532 minEp. 9

A Story Behind Every Empty Seat: How Evan Wilsons’ Scaffold Ed is Tackling Chronic Absenteeism with AI

When nearly a third of students stopped showing up to school during the pandemic, it became clear: chronic absenteeism is not just a data point—it’s a crisis. Evan Wilson, co-founder of Scaffold Ed, is working to get to the heart of what’s keeping kids out of school. His AI-powered tool helps schools move beyond attendance charts to uncover the real stories behind student absences. By turning qualitative family feedback into tangible insights, Scaffold Ed helps educators identify and address bar...

Apr 29, 202529 minEp. 8

One Size Doesn’t Fit All: How Danette Buckley’s Dream Tech Academy Offers Personalized Education

How do you create a classroom that meets students where they are? For Danette Buckley, the answer was to build it herself. Dream Tech Academy, her microschool in Petersburg, Virginia, was born from a personal mission to support her daughter during a difficult medical journey. Today, Dream Tech serves 42 students and is rewriting the rules on what education can look like. Many classrooms fall victim to teaching to the middle— large class sizes necessitate a one-size-fits-all approach to education...

Apr 15, 202531 minEp. 7

Hard Hats, Soft Skills: How Aaron Frumin's unCommon Construction Prepares Students for College and Career Success

What if students could earn school credit, get paid, and build a house—all in one semester? Aaron Frumin, founder of unCommon Construction, is making that a reality. Based in New Orleans, unCommon Construction is a nonprofit apprenticeship program that places high school students on job sites, where they learn hands-on construction skills while developing the soft skills they need to succeed in life and work. From teamwork and communication to resilience and professional attitude, students walk ...

Apr 01, 202529 minEp. 6

Beyond Compliance: How jacob adams’ Inner Spark Learning Lab Cultivates Critical Thinkers

What if education wasn’t about compliance but about discovery? jacob adams, founder of Inner Spark Learning Lab, believes students should have the power to question, explore, and create—not just memorize and obey. In this episode of Pitch Playground, jacob shares his journey from being labelled a “troublemaker” in school to reimagining learning environments that prioritize student agency and self-actualization. jacob’s first teaching job was at a majority-Black elementary school in Brooklyn, whe...

Mar 18, 202528 minEp. 5

Consent-Based Education: How Dr. Erin Flynn’s Hedge School Prioritizes Student Autonomy

What if students had full autonomy over their learning? Dr. Erin Flynn, founder of the Hedge School, is reimagining education through consent-based learning. Located in Texas, the Hedge School is a microschool where students have the freedom to choose what and how they learn, creating an environment that fosters curiosity, confidence, and emotional well-being. Erin’s journey to founding the Hedge School was shaped by her experiences as a teacher, principal, and ultimately, her disillusionment wi...

Mar 04, 202531 minEp. 4

Interrupting the School to Prison Pipeline: How Lisa María Rhodes' Alas Advocates for Students

How can educators disrupt the school-to-prison pipeline? Lisa María Rhodes, founder of Alas, is on a mission to ensure students impacted by the criminal legal and immigration systems have a fighting chance at success. Alas creates interventions that support young people facing incarceration and deportation, providing them with legal advocacy, educational resources, and a path to reclaim their futures. By equipping educators and communities with the right tools, Alas is changing the narrative for...

Feb 18, 202530 minEp. 3

Immersive Classrooms in Mixed Reality: How Jonathan Teske's Reframe XR Brings Learning to Life

How can XR headsets empower teachers in the classroom? Jonathan Teske, a former teacher and edtech expert, founded ReframeXR to make immersive, interactive learning experiences an everyday reality. ReframeXR allows educators to create spatial classrooms where students can engage in collaborative, hands-on learning. Imagine an earth sciences lesson where students manipulate the James Webb Telescope in real time to explore the electromagnetic spectrum, or a science class where they conduct experim...

Feb 04, 202531 minEp. 2

Why College Isn’t the Only Option: How Victoria Chen’s BridgeYear Transforms Career Pathways

What are the options after high school for non-college bound students? Victoria Chen, a former high school biology teacher, founded BridgeYear, a Houston based nonprofit, to address gaps in the education system that fail to provide non-college-bound students with viable career options. As a teacher, Victoria witnessed a valedictorian abandon a full scholarship due to family issues and end up working as a cashier. BridgeYear offers a hands-on career exploration for high-demand well paying jobs th...

Jan 21, 202531 minEp. 1

Introducing Pitch Playground

How could $50,000 transform learning? On Pitch Playground , we invite education innovators and social entrepreneurs to throw their best ideas at us. From technologies that build empathy to providing affordable childcare and reimagining the way we learn—this is a place for pitches from visionaries. Each episode features an intrepid edupreneur workshopping a $50,000 project to solve a critical problem in education. With support from mentors, funders, and fellow entrepreneurs we'll explore what it ...

Nov 22, 20241 min
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