Square Pizza

Hosted by SchermCo

Entrepreneurship EducationInterviews guestsExplicit

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Episodes

145

Latest episode

Aug 2026

Language

EN-US

About the show

The Square Pizza podcast focuses on the intersection of education, innovation, and diversity. We host and interview leaders doing incredible work around the country to ensure all students have access to an equitable education. The Square Pizza podcast is hosted by SchermCo, a social-impact implementation firm that offers strategic implementation and project management services to schools and education-focused organizations across the country.

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60 recent

August 13, 202643 min

John White, CEO - Great Minds

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! Dad. Husband. Marathoner. Deputy Chancellor, New York City Department of Education State Superintendent, Louisiana Department of Education Teach For America Board Member Chief Executive Officer, Great Minds John White has spent his career working at nearly every level of the education system, giving him a unique perspective on leadership, reform, and what it takes to create meaningful change at scale. In this episode of the Square Pizza Pod, Greg and John discuss lessons from Louisiana, the growth and future of Great Minds, the role of artificial intelligence in education, and why strong leadership requires both ambition and trust. John also reflects on how sports shaped his approach to teamwork, how his leadership style has evolved, and why the most important parts of teaching and learning must remain deeply human. In this episode, you’ll learn more about: How John’s experiences across classrooms, districts, states, and organizations shaped his leadership philosophy The lessons he took from Louisiana’s education reforms and open-enrollment model How Great Minds is balancing rapid growth with quality, implementation, and student outcomes Where artificial intelligence can support teachers and students—and where human interaction still matters most Why listening, trust, and coalition-building have become increasingly important throughout John’s career How sports, running, and team experiences continue to influence the way he leads Support the show

July 31, 202638 min

Alesha Washington, President and CEO of the Seattle Foundation

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes Alesha Washington, President and CEO of Seattle Foundation, for a powerful conversation about philanthropy, courage, and what it means to move money like it truly matters. Alesha shares how her experiences across policy, advocacy, economic development, and philanthropy have shaped a leadership philosophy rooted in joy, community voice, and the belief that nonprofit leaders deserve the trust and resources to do their best work. Alesha also pulls back the curtain on how one of the country’s largest community foundations approaches long-term grantmaking, impact investing, affordable housing, transit, childcare, and the growing pressure on nonprofits in today’s political and economic climate. Along the way, she offers a candid look at courageous leadership, board alignment, risk, and why foundations must be willing to stand firmly in their purpose rather than retreat when the work becomes difficult. In this episode, you’ll learn more about: Why Alesha believes philanthropy should “move the money like it matters” How Seattle Foundation centers joy, belonging, and community voice in its work Why affordable housing, childcare, and transit are deeply connected to the future of thriving regions How impact investing can help foundations take smart risks, unlock capital, and support community-led solutions What courageous philanthropy looks like when real money, power, and institutional risk are on the table Why strong boards must understand their role, make space to serve, and stay focused on mission rather than management Support the show

July 1, 202633 min

Tahira Stalberte, APR Assistant Superintendent for Communications & Community Relations

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes Tahira Stalberte, Assistant Superintendent of Communications and Community Relations at Union County Public Schools, for a thoughtful conversation about leadership, trust, and what it really takes to communicate well in public education. Drawing from more than two decades in communications, from the television newsroom to one of the largest school districts in North Carolina, Tahira shares how relationship-building, consistency, and a willingness to take smart risks have shaped her approach to the work. Tahira also opens up about the real complexity of leading communications in a modern school district, from crisis response and community trust to family engagement, artificial intelligence, and the everyday challenge of making sure families feel informed, heard, and supported. Along the way, she offers practical insight on why communication and family engagement are not the same thing, what strong two-way communication should look like in schools, and how districts can better connect with families in ways that actually improve outcomes for students. In this episode, you’ll learn more about: What makes a great communicator and why trust, listening, and risk-taking matter so much in leadership How Tahira thinks about balancing the many audiences a school district serves, from families and staff to media and community stakeholders Why communication and family engagement are distinct, and why both are essential to student success What Union County Public Schools has learned about building stronger family engagement systems and two-way communication with parents How Tahira and her team are approaching artificial intelligence, crisis communication, and storytelling in a fast-changing school landscape Support the show

June 10, 202654 min

Dan Porterfield, President and Chief Executive Officer of the Aspen Institute

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes Dan Porterfield, President and Chief Executive Officer of the Aspen Institute, for a wide-ranging conversation about leadership, educational opportunity, and how ideas can scale far beyond a single institution. Drawing from his upbringing in Baltimore, his years leading Georgetown and Franklin & Marshall, and now his work at Aspen, Dan reflects on the experiences that shaped his belief in talent, public service, and the power of institutions to expand opportunity for more people. Dan also shares why “scaling an idea” can sometimes matter more than scaling an operation, how the Aspen Institute grew from a postwar humanist gathering into a global platform for dialogue and leadership, and why he still believes deeply in the talent that exists in every zip code. Along the way, he offers thoughtful insight on philanthropy, higher education, nonprofit leadership, succession planning, and what it looks like to bend systems toward the public good without losing sight of the people they are meant to serve. In this episode, you’ll learn more about: Why Dan believes scaling ideas can sometimes create more impact than simply scaling operations How his work at Franklin & Marshall helped spark the American Talent Initiative and expand opportunity for low-income students across top colleges What leaders can learn from the founding story and evolution of the Aspen Institute Why partnerships with aligned donors and institutions can be transformative when building enduring change How Aspen’s new Center for Rising Generations is rethinking civic dialogue, leadership, and opportunity for young people What Dan has learned about board leadership, succession planning, and building strong people-serving institutions Support the show

May 8, 202640 min

Shamaiye Haynes - Co-Director, QC Family Tree & CMS School Board Member

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! Shamaiye Haynes is more than a school board member. She is a longtime community leader, family engagement advocate, and one of the voices helping shape the future of a $2 billion public school district. In this episode of the Square Pizza Pod, she shares how years of grassroots organizing and showing up for families prepared her to lead at the district level, and why family engagement, advocacy, and community trust are still at the center of meaningful change in education. In this episode, you’ll learn more about: Why Shamaiye believes family engagement is the missing link to stronger student outcomes How her journey from active parent advocate to school board member prepared her to lead at the district level What it looks like to operationalize family engagement so schools better serve whole families, not just students How she thinks about school choice, charter schools, and what a stronger public education ecosystem could look like How Charlotte-Mecklenburg Schools is approaching issues like artificial intelligence, cell phone policy, and support for teachers and families Support the show

April 24, 202639 min

Jacob Adams, Founder & ED - Inner Spark Learning Lab

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes Jacob Adams, Founder and Executive Director of Inner Spark Learning Lab, for a powerful conversation about what happens when schools stop asking students to fit the system and start redesigning the system to fit students. Drawing from his own journey as a first-generation college student, student athlete, Teach For America educator, and nonprofit founder, Jacob shares how his lived experience pushed him to challenge compliance-driven models of education and build something more human, adaptive, and deeply rooted in student voice. Jacob also opens up about the real work of building Inner Spark from the ground up, from taking the leap on his first school contract to designing learning environments where students help shape curriculum, choose resident teachers, and explore issues that actually matter to them. Along the way, he offers a compelling vision for why belonging, relevance, and flexibility are not extras in education, but essential conditions for real learning and long-term change. In this episode, you’ll learn more about: Why Jacob believes schools should adapt to students more than students should be forced to adapt to school How his own experiences as a first-generation college student, athlete, and teacher shaped the vision behind Inner Spark Learning Lab What he saw inside high-performing schools that made him question whether test scores alone tell the full story How Inner Spark creates learning spaces where students help shape projects, select teachers, and drive more meaningful engagement What it looks like to build a nonprofit from scratch while staying focused on depth, belonging, and real systems change Support the show

April 17, 202631 min

Aneesh Sohoni, Chief Executive Officer of Teach For America

March 20, 202640 min

Cory Carlesimo, CEO & Dewey Norwood, Senior Advisor, Prospect HQ

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes Corey Carlesimo, CEO of Prospect HQ, and returning guest Dewey Norwood to talk about Prospect HQ, a purpose-driven hiring platform built to connect current and former student athletes with employers who value leadership, resilience, and cultural fit. They break down how Prospect HQ is rethinking the hiring process by helping athletes reflect more deeply on their values, strengths, and long-term purpose while giving employers a more authentic way to identify talent that can strengthen workplace culture. Cory and Dewey also share why they believe student athletes are uniquely prepared to lead in today’s workforce, how their own experiences in sports and corporate leadership shaped the vision for the platform, and why culture, authenticity, and community matter just as much as credentials in helping people find the right opportunities. In this episode, you’ll learn more about: Why Cory and Dewey believe student athletes are one of the most overlooked and high-impact talent pools in today’s workforce How Prospect HQ is helping athletes move beyond just finding a job to discovering a clearer path to purpose What makes the platform different from a traditional job board, including its focus on cultural fit, reflection, mentorship, and authentic storytelling How sports, coaching, failure, and teamwork prepare student athletes to thrive far beyond the field, court, or diamond Support the show

March 13, 202633 min

Show Me The World Co-Founders, Samantha Lurie Carroll & Sylvester Chisom

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes Samantha Lurie Carroll and Sylvester Chisom, co-founders of Show Me The World Project, to share how a single school trip idea grew into a multi-city nonprofit helping high school students from under-resourced communities see – and shape – the world. They walk through the journey from a “show me Costa Rica” classroom project to a yearlong program that blends leadership development, entrepreneurship, workforce skills, and first-time international travel, plus the student-driven coffee business that emerged from a visit to a Costa Rican farm. Samantha and Sylvester also open up about the real behind-the-scenes work of going from scraping together $2,500 grants to securing six-figure investments, building a trusted brand, and “responsibly replicating” their model beyond St. Louis without losing their roots in student voice and community. In this episode, you’ll learn more about: How students’ reactions to an inequitable “school swap” experience sparked the original vision for Show Me The World Project What a yearlong leadership, entrepreneurship, and global learning journey actually looks like for high school students in St. Louis and Kansas City How a visit to a coffee farm turned into a student-led social enterprise and the Show Me The Cause fundraising platform The mindset shifts and concrete steps that helped Show Me The World move from tiny grassroots grants to major foundation investments Why honoring your word, embracing “no” as fuel for innovation, and adding earned revenue are core to building a resilient, mission-driven nonprofit Support the show

March 6, 202625 min

Taylor James, Director of Strategic Implementation

GIVEAWAY - send us a message and let us know your favorite thing about the Square Pizza Pod. We are giving away SchermCo swag to the first three people that send us a note! In this episode of the Square Pizza Pod, Greg welcomes back Taylor James for her fourth appearance on the show and her first since earning her MBA and stepping into the role of Director of Strategic Implementation at SchermCo. In this episode, you’ll learn more about: How Taylor’s journey from classroom teacher to Director of Strategic Implementation shapes the way she leads complex strategy and project management work How earning her MBA while working full time strengthened her “measurement muscle” and helped her shift from completing tasks to truly owning outcomes for clients What it really looks like to design and implement programs like the Flight Forward aviation internship program and She Built This City’s pre-apprenticeship expansion How Taylor approaches relaunching programs, managing stakeholders, and moving ideas from concept to execution Why time management, trusting the process, and building real relationships remain core to meaningful social impact work Support the show