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.

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.

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 Influences

04:16 Teaching at Pine Ridge Reservation

05:00 Systemic Issues on Reservations

11:45 Liber Institute: Mission and Impact

13:54 Challenges and Solutions in Rural Education

19:46 Expanding Liber's Reach with Mentor Niloy Gangopadhyay

29:34 Key Takeaways

Links & Resources:

• Jonathan Santos Silva
• The Liber Institute
• Niloy Gangopadhyay
• Teach for America

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.

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 Journey

04:58 Entrepreneurial Beginnings

07:04 Understanding Chronic Absenteeism

11:06 Scaffold Ed: A Solution to Absenteeism

14:19 The Role of Data in Education

18:02 Pitching to Jin-Soo Huh

27:16 Key Takeaways

Links & Resources:

• Evan Wilson
• Scaffold 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.

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 System

04:08 Returning to Education as a Parent

06:00 Homeschooling and Developing a Curriculum

07:18 Growth of Dream Tech Academy

09:55 A Day in the Life at Dream Tech

12:30 Success Stories and Impact

15:36 Challenges and Future Plans

19:38 Mentorship and Strengthening the Pitch

29:20 Key Takeaways and Conclusion

Links & Resources:

• Danette Buckley
• Dream Tech Academy
• Kelly Smith
• Prenda

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.

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 away with much more than a paycheck—they leave equipped to take on life’s challenges and seize new opportunities.

Aaron’s journey started far from the job site. After dropping out of college and joining the Red Cross post-Katrina, he discovered a calling to serve. That calling eventually led him from the classroom to the construction site, and finally to founding unCommon. The organization blends education with real-world experience. Aaron shares how a need to leave a positive “thumbprint” on the world drives his work.

He pitches unCommon to Spencer Sherman, principal consultant at Education First, and together they explore the ins and outs of how unCommon’s new community center can serve as an innovation hub and expand the organization’s reach. They dig into the importance of user-centered design, creating sustainable funding models, and what it takes to truly prepare young people for college, careers, and life.

Episode Highlights:

01:57 Aaron's Journey: Volunteering After Hurricane Katrina

07:25 The Birth of unCommon Construction

10:11 A Day in the Life of a UCC Student

14:29 Impact Stories: Transforming Lives Through Construction

18:50 Expanding the Vision: The unCommon Community Center

20:01 Mentorship and Pitch Improvement

27:19 Key Takeaways

Links & Resources:

• Aaron Frumin
• unCommon Construction
• Spencer Sherman
• Education First

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.

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, where he quickly realized how rigid discipline policies and top-down control stripped students of autonomy. Witnessing kindergarteners being forced into silence, he began to question the foundations of education. His experiences led him to launch Inner Spark Learning Lab (formerly STEM to the Future), an initiative that engages students in hands-on, community-driven learning projects designed to foster critical thinking, self-awareness, and social impact.

If jacob wins the $50,000, the funds will support a Dreamweaver position—a dedicated team member responsible for learning about students, their families, and the broader school community to ensure programming meets real needs. He sits down with Niloy Gangopadhyay, Vice President at Teach for America, to refine his pitch and tackle key questions: What role do community facilitators, or “Dreamweavers,” play in ensuring students feel seen and heard? How can jacob provide measurable outcomes that school leaders and funders will recognize? Tune in to hear jacob’s vision for student-centered education.

02:54 jacob's Early Education and Challenges

05:07 College Struggles and Overcoming Obstacles

06:17 Teach for America Experience

07:55 Questioning the System

10:13 Creating a New Teaching Approach

16:53 Inner Spark's Impact and Future Goals

18:47 Pitching to Niloy Gangopadhyay

25:57 Final Thoughts and Reflections

Links:

• jacob adams
• Inner Spark Learning Lab (formerly STEM to the Future)
• Niloy Gangopadhyay
• Teach for America

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.