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Pitch Playground

Pitch Playground

By: 4.0
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 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.© 2024 4.0 Economics Leadership Management & Leadership
Episodes
  • Winner Announced!!!

    Winner Announced!!!
    Jul 16 2025

    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 up. Drawing on his experience as an educator on the Pine Ridge Reservation, Jonathan created Liber to center the voices of rural and Indigenous communities often left out of education reform. Through coaching, storytelling, and the POWER framework for school redesign, Liber helps leaders build more inclusive and culturally responsive learning environments—starting at the margins and working inward.


    With the $50,000 prize, Jonathan plans to build a group coaching model and expand access to Liber’s tools so that even the most remote communities can benefit from their approach to transformative, community-led education.

    To everyone who voted—thank you. Your engagement made this season truly special. Stay connected by signing up for the 4.0 newsletter and be the first to hear updates on Jonathan’s journey and announcements about Season 2 of Pitch Playground. We’re just getting started. 🛠️🎙️

    Links & Resources:

    • Jonathan Santos Silva
    • The Liber Institute

    About the Host, Nicole Jarbo:
    Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about 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 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.


    We Want 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 pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts.

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

    Call to Vote: Which Idea Should Win $50k?
    Jun 10 2025
    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 | EpisodeLisa 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 | EpisodeJonathan 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 | EpisodeJaime-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 | EpisodeVictoria’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 | EpisodeUnCommon 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 | EpisodeJonathan 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 | EpisodeEvan’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 | EpisodeErin 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 | Episodejacob’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...
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    16 mins
  • Building a Better Childcare System: How Jaime-Jin Lewis’s AutoEnroll Simplifies Childcare Operations

    Building a Better Childcare System: How Jaime-Jin Lewis’s AutoEnroll Simplifies Childcare Operations
    May 27 2025

    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 workflows that help small providers stay compliant—and stay open.


    Jaime-Jin’s journey to Wiggle Room began long before she ever wrote a line of code. Raised in the racially segregated South by a mother who ran a preschool out of their church basement, care was embedded into the fabric of her childhood. From organizing casseroles for neighbors to vacuuming tiny chairs after school, she grew up in a world where caregiving wasn’t just labor—it was love. That perspective stuck with her and resurfaced in full force during COVID, when she launched Workers Need Childcare, a hotline and mutual aid network that matched families with emergency caregivers during the chaos of school shutdowns.


    Now, Wiggle Room is tackling the other side of the care equation: empowering providers. Jaime-Jin shares how she cold-called 6,000 home-based programs in New York City, listened deeply to what they needed, and tested every feature with her toughest user—her mom. With 100% adoption across 65 current daycare sites, Auto-Enroll is already transforming how providers and parents navigate care. She pitches her work to Jin-Soo Huh, partner at The Learning Accelerator, and together they explore what it means to scale trust-based technology, expand across state lines, and stay grounded in community-led design. They also dig into pricing strategy, long-term sustainability, and the power of building with users, not just for them.

    Episode Highlights:


    02:46 Jamie Jin's Background and Influences

    07:45 Birth of Wiggle Room

    09:08 Challenges and Solutions in Childcare

    14:52 Developing AutoEnroll

    19:05 Pitching to Jin-Soo Huh

    29:17 Final Thoughts and Takeaways


    Links & Resources:

    • Jaime-Jin Lewis
    • Wiggle Room
    • Jin-Soo Huh
    • The Learning Accelerator

    About the Host, Nicole Jarbo:
    Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about 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 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.

    We Want 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 pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts.

    Remember to Vote!
    At the end of this season one of these entrepreneurs will receive $50,000 towards their idea. We want to hear from you, yes YOU, to cast your vote for the idea you think should receive the cash. Sign up for our newsletter at 4pt0.org to stay tuned on when voting will open.

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    31 mins
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