Pitch Playground

• 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 | 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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• 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 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 Influences07:45 Birth of Wiggle Room09:08 Challenges and Solutions in Childcare14:52 Developing AutoEnroll19:05 Pitching to Jin-Soo Huh29:17 Final Thoughts and TakeawaysLinks & Resources:Jaime-Jin LewisWiggle RoomJin-Soo HuhThe 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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• 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 for Native and Indigenous students.Jonathan shares how these experiences shaped his vision for Liber—a nonprofit that uses coaching, storytelling, and design thinking to support transformative change in rural schools. He walks us through the POWER framework, his approach to leadership development and community-driven school redesign. From helping teachers better understand the cultural context of the communities they serve to embedding Indigenous knowledge into curriculum, Liber’s work helps school leaders reimagine education through empathy, culture, and belonging.Jonathan pitches his idea to mentor Niloy Gangopadhyay, a longtime education leader, to explore key questions: How do you preserve depth while expanding reach? Can storytelling via a podcast help bridge the distance to hard-to-reach communities like Havasupai? And what will it take to make rural and Indigenous education a true priority for philanthropy? If Jonathan wins $50,000, he’ll use the funds to build a group coaching model and expand access to Liber’s tools—so leaders in even the most remote schools can create systems that reflect and serve their communities.Episode Highlights:02:34 Jonathan's Background and Early Influences04:16 Teaching at Pine Ridge Reservation05:00 Systemic Issues on Reservations11:45 Liber Institute: Mission and Impact13:54 Challenges and Solutions in Rural Education19:46 Expanding Liber's Reach with Mentor Niloy Gangopadhyay29:34 Key TakeawaysLinks & Resources:Jonathan Santos SilvaThe Liber InstituteNiloy Gangopadhyay Teach for AmericaAbout 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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• 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 barriers—things like delayed work permits or MetroCard access—that often go unnoticed but make a real difference in whether a student shows up.Evan’s personal journey through the education system was shaped by early medical challenges. At the age of three, he was diagnosed with cataracts and spent much of his early life navigating school while legally blind. These experiences—often being overlooked, misjudged, and under-supported—fueled his passion for rethinking how schools engage with students and families. For Evan, data shouldn’t just explain what went wrong—it should help shape what comes next.In this episode, Evan pitches his vision to Jin-Soo Huh, a former classroom teacher and partner at The Learning Accelerator. Together, they explore how Scaffold Ed can evolve from a powerful analysis tool into a true catalyst for change—leveraging AI not just for efficiency, but for equity. They dig into how to build trust with families, the importance of anonymity, and how schools can use real-time feedback to deliver more targeted, responsive support.Episode Highlights:02:04 Evan's Educational Journey04:58 Entrepreneurial Beginnings07:04 Understanding Chronic Absenteeism11:06 Scaffold Ed: A Solution to Absenteeism14:19 The Role of Data in Education18:02 Pitching to Jin-Soo Huh 27:16 Key Takeaways Links & Resources:Evan WilsonScaffold Ed 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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• 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, leaving students who are excelling or who need additional support without adequate resources. Danette’s school empowers students to thrive on their own terms.Danette is a lifelong learner who fell in love with school at age four and never looked back. After immigrating from Jamaica and witnessing the challenges of U.S. classrooms, she maintained her passion for education but saw that traditional schools often fail to meet the needs of every student. A family challenge brought her back to the classroom—this time as a homeschooler—and her vision evolved into a flexible, tech-enabled school designed to serve kids of all abilities and interests, where students could learn at their own pace. Dream Tech is a place where students are grouped by comprehension, not just age, and where learning is personalized, and joyful.In this episode, Danette pitches her microschool to Kelly Smith, CEO of Prenda. Kelly has helped over 1,000 people start microschools. Together, they explore how Danette can create a sustainable structure for Dream Tech, stick to her policies without losing her compassion, and bring her unique, student-first model to more families. It’s a conversation full of heart, strategy, and hard-earned wisdom for anyone reimagining what school can be.Episode Highlights:02:16 Challenges in the U.S. Education System04:08 Returning to Education as a Parent06:00 Homeschooling and Developing a Curriculum07:18 Growth of Dream Tech Academy09:55 A Day in the Life at Dream Tech12:30 Success Stories and Impact15:36 Challenges and Future Plans19:38 Mentorship and Strengthening the Pitch29:20 Key Takeaways and ConclusionLinks & Resources:Danette BuckleyDream Tech AcademyKelly SmithPrendaAbout 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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