An Educated Guest

Todd Zipper
  • 4.9 (52)
  • EDUCATION
  • UPDATED SEMIWEEKLY

An Educated Guest is a podcast that dives deep into the innovations and trends shaping the future of education. The host is Todd Zipper who has over two decades as an entrepreneur, executive, and investor across K-12, Higher Education, and Workforce Development. He brings together visionaries, innovators, and operators from the education industry to explore the solutions that are transforming learning and work.

  1. 5H AGO

    S3E12 | A Founder's Journey: Matthew Pittinsky on Blackboard, Parchment, and the Future of Ed-Tech

    In this fascinating episode of An Educated Guest, host Todd Zipper sits down with Matthew Pittinsky, a true pioneer in education technology. Matt, the co-founder of Blackboard and former CEO of Parchment, shares his incredible journey from the dawn of the internet to the age of AI. He takes us back to 1997 to reveal the core problem he and his co-founder, Michael Chasen, were trying to solve with Blackboard and how that platform became a ubiquitous force in online learning. The conversation then pivots to his time at Parchment, where he saw a new opportunity to disrupt the antiquated process of academic credentialing. Matt discusses his vision for a digital credential that is more than just a list of courses and grades—one that truly represents a student's skills and competencies. He offers a compelling take on the student debt crisis, the future of the four-year degree, and why he believes the integrity of the credential is the most important mission of any university. This episode is a must-listen for anyone interested in the history of EdTech, the future of credentials, and how AI will fundamentally change how we learn and what we teach. Key Takeaways from this Episode: The LMS Defined: A clear and concise definition of what a learning management system is, its pros and cons, and why it has remained relatively unchanged for over two decades.The Power of the Digital Credential: An exploration of how a student-managed digital record of learning and skills could solve a myriad of problems, from college admissions to skills-based hiring.AI's Role in EdTech: Matt shares his optimistic view on AI as a "sustaining" force that can make learning more efficient and a "disruptive" force that could reorder the entire EdTech landscape.A "Crawl, Walk, Run" Approach to Innovation: Matt's pragmatic advice for universities on how to innovate with technology without disrupting their core mission.A Bold Prediction: Matt's vision for an AI agent that will serve as an omnipresent guide for students, helping them navigate their education and career pathways.About Our Guest: Matthew Pittinsky is an EdTech pioneer and the co-founder of Blackboard, where he served as CEO and Chairman. After earning a Ph.D. from Columbia University's Teachers College, he went on to become the CEO of Parchment, a global leader in digital credentials. Matt is also an active angel investor and a respected thought leader in the education technology space.

    56 min

  2. SEP 10

    S3E11 | K-12's Moment of Truth: Sari Factor on the Evolution of Education and the Future of Learning

    In this illuminating episode of An Educated Guest, host Todd Zipper sits down with Sari Factor, the Vice Chair and Chief Strategy Officer of Imagine Learning, to discuss the monumental shifts occurring in K-12 education. With a career spanning several decades, Sari shares the powerful journey of Imagine Learning, from its early days as a credit recovery provider to its current position as a leader in digital-first curriculum, serving over 15 million students. The conversation delves into the most pressing challenges facing schools today: the end of pandemic-era federal funding, the proficiency crisis in reading and math, and the disruptive rise of school choice. Sari offers both a realistic and hopeful perspective, sharing how a focus on high-quality instructional materials and teacher development is creating a "bright side" to the current challenges. She also provides a compelling vision for the future, exploring the transformative potential of AI to personalize learning, empower teachers, and solve some of education's most persistent problems. This episode is a must-listen for anyone seeking to understand the K-12 landscape and what it will take to prepare a new generation for the future. Key Takeaways from this Episode: Imagine Learning's Evolution: The founding story of a company built on the mission of personalized learning and its growth into a major K-12 education provider.The Post-Pandemic K-12 Reality: A breakdown of the key macro forces—from funding cuts to declining birth rates—that are forcing public schools to reinvent themselves.The Science of Learning: An exploration of what evidence-based practices, such as the "science of reading," are actually working to reverse the proficiency crisis in reading and math.AI's Role as a Co-Pilot: How AI can and should be used to augment a teacher's role, shifting their focus from mundane tasks to the human-centric work of mentoring and motivating students.The Power of Durable Skills: A discussion on why skills like resilience and empathy are becoming more crucial than ever and how schools can teach them effectively.About Our Guest: Sari Factor is the Vice Chair and Chief Strategy Officer of Imagine Learning. With a career spanning over four decades in the K-12 education space, Sari has served as a visionary leader at companies like McGraw Hill and Kaplan. She is a recognized expert on the future of education, technology's role in the classroom, and the importance of professional learning for educators.

    55 min

  3. SEP 3

    S3E10 | Outcomes at Scale: Carl Madi on Stepful's Mission to Close the Healthcare Skills Gap

    In this powerful episode of An Educated Guest, host Todd Zipper sits down with Carl Madi, the founder and CEO of Stepful. Carl shares his journey from Uber and Handy, where he developed a passion for creating career mobility for workers, to building a company that is radically transforming how the healthcare workforce is trained. He explains how Stepful's innovative model addresses chronic shortages in allied health, providing a more affordable and time-efficient alternative to traditional trade schools and community colleges. Carl delves into the core of Stepful's success: a tech-enabled, outcomes-based model that combines bite-sized, interactive learning with hands-on externships and AI-powered feedback. He reveals how this approach is leading to incredible completion and placement rates that are well above the national average. The conversation also explores the future of healthcare jobs in the age of AI, the power of employer-sponsored apprenticeships, and Carl's bold prediction for a new education system driven by employers. This episode is a must-listen for anyone interested in EdTech, workforce development, or the future of healthcare. Key Takeaways from this Episode: Stepful's Unique Model: A deep dive into Stepful's hybrid learning approach that combines online courses, AI-powered simulations, and real-world externships to deliver exceptional outcomes.Solving the Healthcare Skills Gap: How Stepful is directly addressing the chronic shortage of allied health workers by removing key barriers to entry like cost and time.The Future of AI in Healthcare: Insights into how AI will augment or eliminate jobs in the healthcare industry and the new roles that will emerge.Apprenticeships & Employer Partnerships: A compelling case study on how Stepful's partnerships with health systems are dramatically cutting time-to-hire and improving employee retention.A New Vision for Education: Carl's bold prediction for a shift to an employer-centric, debt-free education system that is modular, flexible, and tied directly to career pathways.The Power of People: A discussion on the vital role of human instructors and coaches in the learning experience, even as technology evolves, to ensure students feel supported and nurtured.About Our Guest: Carl Madi is the founder and CEO of Stepful, a company he launched to provide a fast, affordable, and effective pathway into high-demand healthcare jobs. Carl's background includes leadership roles at Uber and Handy, where he developed a passion for creating career mobility for workers. Stepful was recently named the number one EdTech company by Time magazine.

    45 min

  4. AUG 20

    S3E9 | The Expertise Upheaval: Matt Sigelman on AI, The Experience Paradox, and Reshaping the Workforce

    In this eye-opening episode of An Educated Guest, host Todd Zipper sits down with Matt Sigelman, CEO of the Burning Glass Institute, to decode the seismic shifts occurring in the labor market. Matt shares data-driven insights from his groundbreaking research, including the "experience paradox," which reveals why so many entry-level jobs now demand prior experience, and what that means for recent college graduates. The conversation delves into the accelerating pace of skill obsolescence, the rise of AI, and how these forces are creating a critical disconnect between what employers need and what education provides. Matt introduces the concept of the "Expertise Upheaval," offering a look at how AI is transforming careers and what skills will make workers more valuable with AI, not just more efficient. He also makes a compelling case for greater accountability in education, using data to show which credentials and programs actually lead to a real return on investment. This episode is a must-listen for anyone seeking to understand the data, trends, and solutions that will shape the workforce of tomorrow. Key Takeaways from this Episode: The Experience Paradox: A deep dive into the data showing that most entry-level jobs now require several years of experience, and the implications for hiring and education.The Pace of Change: Why skills are becoming obsolete faster than ever, and how this is impacting career trajectories and the need for lifelong learning.The "Expertise Upheaval": An exploration of how AI is not just about automation, but about a more profound shift in the skills required to be an expert in any given field.Education-to-Workforce Accountability: How data can be used to hold colleges and credential providers accountable, ensuring that programs lead to real-world outcomes and economic mobility.A New Kind of Workforce: Matt discusses the shift from a "schooled society" to a "learning society," and how we must prepare for a future where learning is a continuous, lifelong process.About Our Guest: Matt Sigelman is the CEO of the Burning Glass Institute, a fully independent, nonprofit research center that works at the intersection of work and learning. Prior to the Institute, he spent 20 years building a private sector data provider (now called Lightcast). Matt is a recognized leader in using big data to shed light on labor market trends, inform policy, and drive economic mobility.

    55 min

  5. AUG 13

    S3E8 | The Age of AI: Raoul-Gabriel Urma on Education, Entrepreneurship, and a Future of Creative Work

    In this engaging episode of An Educated Guest, host Todd Zipper sits down with Raoul-Gabriel Urma, the founder and CEO of Cambridge Spark. Raoul shares his unique journey from a self-taught coder to leading a company at the forefront of the AI education revolution. The conversation explores how Cambridge Spark is helping individuals and organizations prosper in the age of AI by equipping them with critical data and technical skills. Raoul offers a compelling perspective on AI’s impact on the workforce, arguing that while it may not reduce our workload, it will redirect our focus from routine tasks to strategic, creative, and collaborative problem-solving. He also delves into the importance of a blended learning approach—combining AI-powered companions with human mentorship and social learning to foster a new generation of adaptable workers. This episode is a must-listen for anyone seeking to understand the real-world implications of AI on careers, education, and entrepreneurship. Key Takeaways from this Episode: The Future of Work is AI-Augmented: Raoul makes the case that every job will require AI literacy, reframing the conversation from job replacement to skill augmentation.Beyond the Enterprise Hype: Get a realistic perspective on where AI is currently delivering significant value (cost efficiency) versus where its full potential (new revenue creation) is still unfolding.The Entrepreneurial Shift: Understand how AI and accessible technology have lowered the barrier to entry for entrepreneurs, shifting the focus from coding to problem-solving and opportunity identification.The Power of Blended Learning: Learn why the most effective learning models for the future will combine AI's personalized feedback loops with human mentorship and social collaboration.The Importance of Apprenticeships: Discover why the apprenticeship model, especially in technical fields like data and AI, is a highly effective way to bridge the skills gap and provide immediate career impact.The Coding Evolution: Explore how the role of a coder is changing from writing code from scratch to a more strategic function of owning, maintaining, and architecting solutions in a world of automated code generation.About Our Guest: Raoul-Gabriel Urma is the founder and CEO of Cambridge Spark, a UK-based education company focused on AI and data science. With a background as a software engineer and a passion for education, Raoul built Cambridge Spark with the vision of helping everyone prosper in the age of AI. He is also the co-author of the best-selling book Java 8 in Action.

    44 min

  6. AUG 6

    S3 E7 | Minds Matter: Erika Halstead on Mentorship, Equity, and the Power of People to End Poverty Through Education

    In this deeply inspiring episode of An Educated Guest, host Todd Zipper sits down with Erika Halstead, CEO of Minds Matter National, an organization close to Todd's heart. Erika shares her personal journey from starting her career as a bilingual teacher to leading Minds Matter, an organization that started in 1991 with no full-time employees and has grown to serve 1,100 high-achieving, low-income students annually with the support of 2,000 volunteers across 14 chapters. Erika unpacks Minds Matter's unique multi-year mentorship model, emphasizing why its "people-to-people" approach, focusing on social-emotional learning and expanding students' horizons, remains paramount even amidst technological advancements like AI. She reveals how Minds Matter helps students secure over $2.5 million in scholarships annually, enabling them to attend top-tier colleges while paying significantly less than their peers. The conversation also explores the challenges facing the non-profit sector, including the post-pandemic decline in volunteerism, and how Minds Matter is adapting its funding and visibility strategies, including recent features with celebrities like Jalen Hurts. Finally, Erika shares her bold vision for scaling Minds Matter's impact to end poverty through education, advocating for a nationwide movement that champions talent from underserved communities. Key Takeaways from this Episode: The Minds Matter Model: A deep dive into the unique volunteer-driven, multi-year mentorship program that provides comprehensive college advising, test prep, and holistic student development.Tangible Economic Mobility: How Minds Matter's support translates into real financial outcomes, helping students secure significant scholarships and pay substantially less for college.Human Connection vs. AI: A compelling argument for why human mentorship and in-person relationships remain the most critical lever for student success, even as AI transforms other aspects of education.Navigating Non-Profit Challenges: Insights into the current state of the non-profit sector, including funding dynamics, the post-pandemic decline in volunteerism, and strategies for sustainable growth and visibility.Scaling for Systemic Change: Erika's ambitious vision to dramatically expand Minds Matter's reach, creating a national movement to address systemic inequities and unlock talent from low-income communities.About Our Guest: Erika Halstead is the CEO of Minds Matter National. With a background as a bilingual teacher and a deep personal connection to education's transformative power, Erika has dedicated over a decade to Minds Matter. She has led the organization's growth from the Executive Director of the New York City chapter to her current national role, championing access and equity for high-achieving, low-income students across the United States.

    45 min

  7. JUL 23

    S3E6 | The Kaplan Way: Andy Rosen on Reinvention, Global Scale, and the Future of Outcomes-Driven Education

    In this insightful episode of An Educated Guest, host Todd Zipper welcomes Andy Rosen, CEO of Kaplan, for a deep dive into the evolution of one of the world's most enduring education companies. Andy shares his personal journey at Kaplan, reflecting on over 30 years of continuous reinvention that transformed a test prep company into a global powerhouse in higher education, professional training, and international student pathways. The conversation explores Kaplan's unique "outcomes-first" DNA, its strategic approach to M&A as a tool for capability building, and how its long-term orientation, supported by Graham Holdings, enables strategic patience. Andy provides a compelling look at the future of assessment in an AI-driven world, including Kaplan's innovative performance-based evaluations for high-stakes professions. He discusses the critical role of corporate partnerships, exemplified by Kaplan's work with Amazon's Career Choice program, and reveals how Kaplan cultivates a culture that keeps its diverse global team motivated and passionate, earning it a spot as a Newsweek Global Most Loved Workplace. This episode offers invaluable lessons on leadership, innovation at scale, and adapting to the ever-changing demands of the education and workforce landscape. Key Takeaways from this Episode: The Power of Reinvention: How Kaplan's culture of continuous transformation and outcome-driven approach has enabled it to adapt and thrive through decades of industry shifts.Strategic M&A: Kaplan's philosophy of using acquisitions as a tool to acquire specific capabilities that align with its long-term vision, rather than solely for scale.Assessment in the AI Era: Insights into how AI is redefining the landscape of assessment, moving towards more rigorous, performance-based evaluations that validate uniquely human skills.Optimizing Corporate Education: A deep dive into Kaplan's role in major corporate partnerships like Amazon Career Choice, demonstrating how tailored educational advising can maximize ROI for both employers and learners.Building a Loved Workplace at Scale: Lessons on fostering a highly motivated and engaged workforce in a large, global education company, contributing to Kaplan's recognition as a top "Most Loved Workplace."Global Education Trends: Andy's perspective on the massive demographic shifts driving international education growth and the strategic importance of global alignment in educational development.About Our Guest: Andy Rosen is the CEO of Kaplan, a leading global provider of educational and career services. With over three decades at the company, Andy has played a pivotal role in Kaplan's strategic evolution, expanding its reach across test preparation, higher education, professional licensure, and international student pathways. He is recognized for his leadership in driving innovation, fostering a strong company culture, and maintaining a relentless focus on student outcomes.

    43 min

  8. JUL 16

    S3 E5 | From Princeton Review to Noodle: John Katzman on Reinventing Higher Ed and Fixing K-12

    In this provocative and incredibly insightful episode of An Educated Guest, host Todd Zipper sits down with John Katzman, a serial entrepreneur and one of the most influential figures in education, known for founding The Princeton Review and Noodle. John offers a no-holds-barred perspective on the seismic shifts needed across the entire education landscape. The conversation delves into the evolution of online program management (OPM), why its traditional model is unsustainable, and how Noodle aims to redefine university partnerships. John tackles the soaring costs of higher education, proposing systemic solutions to the $1.7 trillion student debt crisis that challenge conventional thinking. He then pivots to K-12, dissecting its "governance problem" and explaining why top-down reforms continually fail. This episode is packed with John's unique, often controversial, takes on everything from the resurgence of for-profits to the transformative (and sometimes reckless) potential of AI in education, all while offering powerful insights for edtech founders and a glimpse into his vision for the future of learning. Key Takeaways from this Episode: OPM's Future: John's candid assessment of the Online Program Management (OPM) industry, why he believes it's "transitional," and how Noodle is forging a new path for university partnerships.Solving the Student Debt Crisis: A deep dive into the true cost of higher education and innovative, systemic solutions to the $1.7 trillion student debt burden, including state-level incentives.K-12's Governance Challenge: An incisive critique of the American K-12 system, arguing that curricular reforms fail due to a fundamental "governance problem" that requires radical change.AI's Dual Impact: Insights into how Artificial Intelligence can dramatically lower administrative costs and enable powerful, affordable learning simulations, but also its potential pitfalls if deployed carelessly.Why EdTech Philanthropy Falls Short: A frank discussion on why billions of dollars invested in education reform have yielded limited impact, citing arrogance, systemic inertia, and a lack of true R&D.The Power of Data & Networked Universities: Discover how data can personalize student support and why forging strong university networks is crucial for adaptability and innovation in a rapidly changing world.About Our Guest: John Katzman is a legendary entrepreneur and visionary in the education sector, having founded three incredibly impactful companies: The Princeton Review, 2U (formerly), and Noodle. As the Founder and former CEO of Noodle, he has been at the forefront of transforming higher education through online program management and strategic partnerships. Katzman is a frequent commentator on educational trends, policy, and innovation.

    46 min
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4.9
out of 5
52 Ratings

About

An Educated Guest is a podcast that dives deep into the innovations and trends shaping the future of education. The host is Todd Zipper who has over two decades as an entrepreneur, executive, and investor across K-12, Higher Education, and Workforce Development. He brings together visionaries, innovators, and operators from the education industry to explore the solutions that are transforming learning and work.

Information

  • Creator
    Todd Zipper
  • Years Active
    2021 - 2025
  • Episodes
    51
  • Rating
    Clean
  • Copyright
    © 2025 An Educated Guest
  • Show Website
    An Educated Guest

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