An Educated Guest

Todd Zipper

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. 3d ago

    Ep.85 | Closing the Experience Gap with Cloud for Good's Founder Tal Frankfurt

    What happens when an entrepreneur builds a business not out of a tech epiphany, but simply to survive? In this episode of An Educated Guest, host Todd Zipper sits down with Tal Frankfurt, Founder and CEO of Cloud for Good, to trace the company's remarkable evolution from a one-bedroom apartment to a premier Salesforce implementation partner spanning three continents. Tal shares his candid journey from managing giant, un-scalable spreadsheets for a small youth nonprofit to building an organization that now powers the data infrastructure for 75% of R1 higher education institutions and massive humanitarian networks like Feeding America. The heart of the conversation dives into how Cloud for Good is actively solving the tech industry's "experience gap" through its pioneering Talent for Good apprenticeship program. Strikingly more selective than elite universities, the program completely upends the classic tuition-heavy coding bootcamp model by paying career-changing individuals from day one to learn, get certified, and deploy directly into high-impact client systems. Tal discusses the incredible social impact of this pipeline—which brings massive demographic diversity into tech—without ever compromising on the rigorous quality demands of the modern enterprise workforce. Beyond workforce development, Todd and Tal unpack what it truly takes to scale a healthy company culture in a fully remote environment. From the dangers of "mistake hoarding" to the strategic shift toward becoming an IP-backed services company in the age of AI commodity, this episode is a masterclass in operational intentionality. Whether you are an educational leader navigating digital transformation, an entrepreneur scaling a remote team, or a professional looking to understand how AI will genuinely multiply human capability rather than replace it, this conversation offers invaluable, real-world blueprints.

  2. Jul 22

    Ep. 84 | From Sylvan to Cintana: Doug Becker on Four Decades of Scaling High-Quality Education

    What happens when a high school student decides to skip his Harvard admission to launch a healthcare technology company? You get the four-decade entrepreneurial odyssey of Doug Becker, the founder and CEO of Cintana Education. In this episode of An Educated Guest, we sit down with Doug to deconstruct his legendary career building, running, and investing in some of the largest educational ecosystems on the planet. We trace Doug's journey from his early days co-founding Sterling Partners to taking the reins of Sylvan Learning Systems, where he scaled K-12 supplemental tutoring across North America. Doug shares the lightbulb moment that led to the creation of Sylvan Prometric—pioneering the global infrastructure for modern computer-based testing—and how that international footprint laid the groundwork for Laureate Education, a global university network that scaled to over one million students. We also dive into his historic move to embed a public good mandate into a publicly traded company by turning Laureate into the world's largest Certified B Corp. Finally, Doug gives us an inside look at the architecture of his latest venture, Cintana Education. Operating in an asset-light, alliance-based model alongside Arizona State University and Dr. Michael Crow, Cintana is rapidly expanding high-quality higher education across 30 countries without the need to buy or build physical campuses. Whether you are an educator, a builder, or an investor, this episode offers a masterclass in the realities of balancing academic quality with massive global scale.

  3. Jul 15

    Ep.83 | The Micro-Schooling Revolution: How Grassroots Disruption is Transforming American Education

    What if the future of American education didn’t involve multi-million dollar buildings, century-old factory models, or teaching to the "mythical center" of a 30-student classroom? In this episode of An Educated Guest, host Todd Zipper sits down with Don Soifer, co-founder and CEO of the National Microschooling Center, to pull back the curtain on the fastest-growing narrative in K-12 education. From an accidental public-private partnership during the pandemic to a national movement spanning over a million and a half children, Soifer breaks down what microschools actually look like and why they are exploding in popularity across red, blue, and purple states alike. We dive deep into the unique economics and demographics of the modern microschool. Operating at a fraction of the cost of traditional public schooling—averaging $8,000 per child compared to upwards of $20,000—microschools are challenging long-held assumptions about educational productivity. Far from a playground for the privileged, data reveals a beautifully diversified landscape where 40% of pre-launch founders are Black or African American, and the vast majority of schools are intentionally designed to serve neurodivergent children, students with special needs, and those lagging behind state grade levels. Finally, Soifer explains how these nimble learning environments are preparing kids for the modern gig economy. By utilizing mastery transcripts, project-based learning, and cutting-edge AI tools, microschools are turning passive students into active learners. Tune in to discover the bureaucratic hurdles these micro-innovators face—from archaic fire codes to zoning laws—and why the micro-schooling movement might just be the most sustainable disruption to American education in a generation.

  4. Jul 1

    Ep. 82 | A Conversation with Author Anya Kamenetz on High-Stakes Tests, Student Debt, Generational Justice, Screen-Time and More

    What happens when the traditional promises of higher education, standardized testing, and steady middle-class milestones no longer align with reality? In this episode of An Educated Guest, host Todd Zipper sits down with acclaimed author and journalist Anya Kamenetz for a wide-ranging conversation on high-stakes tests, debt, generational justice, screen-time, and more. The conversation begins with a fifteen-year retrospective on Anya’s landmark book, DIY U, exploring how the concept of "unbundling" higher education has evolved in an age dominated by mobile technology and alternative credentials. Together, Todd and Anya tackle the structural flaws of high-stakes testing in K-12 public schools, the long-tail impacts of the pandemic on student mental health, and why a "learning recession" has persisted despite decades of standardized metric optimization. Finally, Anya shares insights from her latest efforts regarding youth climate anxiety, outlining her guiding philosophy of "generational justice"—the fundamental responsibility we hold to leave a better, more stable world for those who come after us. Whether you are a parent navigating screen time limits, an edtech innovator, or an observer of cultural trends, this episode offers a profound look at how we can rebuild human flourishing into the DNA of modern education.

  5. Jun 24

    Ep. 81 | Unpacking Financial Aid: Shifting from the Back Office to Strategic Driver with Robert Heil of FAS

    For decades, colleges and universities have treated the financial aid office as a dense, back-office administrative function—a labyrinth of tax-code-like regulations to be managed out of sight. But as higher education faces a stark demographic cliff and intense competition for shrinking student cohorts, this legacy mindset is proving fatal. In this episode of An Educated Guest, host Todd Zipper sits down with Robert Heil, CEO of Financial Aid Services (FAS), to discuss why financial aid is actually the chief influencer of student yield and freshman retention. Robert breaks down the hidden risks threatening institutional survival today, highlighting a critical staffing crisis where more than half of all financial aid offices across the United States are operating at 75% capacity or less. He shares sobering data from the field, noting that under-resourced schools that fell out of Title IV compliance in 2025 faced an average of $750,000 in fines, fees, and penalties. Beyond compliance, Robert reveals the exact statistical timeline of student behavior, explaining why delaying a financial aid package past a two-week window drastically slashes a university's enrollment success. The conversation also goes macro, tackling the incoming July 1st aggregate loan limits for graduate programs and the potential of Workforce Pell to fund short-term job readiness. Finally, Robert shares his "Secretary of Education" wish list, explaining how dismantling the 120-year-old Carnegie unit framework could finally spark a wave of modern, affordable, competency-based innovation across higher education. Tune in to learn how forward-thinking institutions are leveraging financial aid as a service to drive net tuition revenue and secure operational stability.

  6. Jun 17

    Ep.80 | Jane Swift on Mending the Broken College-to-Career Pipeline: Why Paid Internships are the New Hardest Application in America's Workforce

    When it comes to the path from education to financial security, the "golden ticket" narrative we grew up with is showing significant cracks. Today, students who work hard and play by the rules find themselves facing a steep experiential paradox: entry-level job listings frequently require multiple years of prior work history, yet securing a competitive, paid internship during college has become arguably more selective than gaining admission to an Ivy League university. This structural failure leaves massive pools of early career talent stranded, widening inequalities across the socioeconomic spectrum. In this episode, we sit down with Jane Swift, CEO of Education at Work and former Governor of Massachusetts, to dissect the friction points spanning K-12, higher education, and the workforce. Drawing from her historical role in crafting Massachusetts' legendary 1993 Education Reform Act and her current appointment to the National Assessment Governing Board, Jane brings unmatched policy expertise to the table. We discuss why state education metrics were sliding long before the pandemic hit, the hidden societal headwinds impacting the adolescent brain, and why wealthy families find alternative academic safety valves while low-income and first-generation students are left behind. Finally, we turn our attention toward actionable solutions for the future of work-based learning. Jane shares how Education at Work is successfully building an instructional workflow layer that partners with Fortune 500 giants to scale paid corporate roles for thousands of students. She also lays out a provocative blueprint for the future: reimagining rigid public funding models and forcing higher education institutions to leverage their massive institutional procurement power to mandate paid career opportunities for the very students they serve. Tune in for an honest, deeply experienced look at what it takes to rebuild the system from the ground up.

  7. Jun 10

    Ep.79 | From Correspondence School to Workforce Training Powerhouse with Kermit Cook, CEO of Penn Foster

    What does the future of the American workforce look like when you bypass the traditional four-year college track entirely? In this episode of An Educated Guest, we sit down with Kermit Cook, the CEO of Penn Foster, to explore how a distance-learning model founded in 1890 to train coal miners has evolved into a hyper-modern platform educating hundreds of thousands of middle-skill workers. Kermit shares his unique personal trajectory from management consulting and Teach for America to the helm of a massive EdTech ecosystem, explaining the passion for equitable career pathways that drives his work. We dive deep into the booming market of online high schools. Kermit breaks down why an online diploma provides far more robust workforce pathways than a traditional GED, and how a student profile that is largely 37-year-old working women is leveraging asynchronous learning to achieve economic mobility. He pulls back the curtain on the real-world economics of their model, contrasting Penn Foster's $1,600 total tuition against the skyrocketing per-pupil costs of traditional public education. Finally, we tackle the highly anticipated role of artificial intelligence in education. Kermit moves past the San Francisco tech hype to discuss practical, continuous-improvement pedagogy. He reveals how Penn Foster is using AI to analyze exactly where students get stuck in difficult courses, boosting completion rates from 20% to 70%, and how automated outreach allows their human coaches to step in exactly when a struggling adult learner needs a lifeline.

  8. Jun 3

    Ep.78 | The Earn-and-Learn Revolution: Can Apprenticeships Save the Entry-Level Worker from AI?

    As the 2026 labor market faces an enrollment cliff and a massive influx of AI automation hollowing out traditional white-collar entry-level work, the "what is college for" debate has reached a fever pitch. Students are increasingly wary of high-debt, four-year degree conveyor belts that fail to guarantee day-one productivity. In this episode of An Educated Guest, we sit down with John Colborn, the co-founder of Apprenticeships for America, to explore how "learn-and-earn" models can reshape American workforce development. John walks us through his career journey and unpacks the current state of apprenticeships, grading the bipartisan political efforts—including a look at how the Trump administration is performing on its milestone goal of reaching 1 million active apprentices. We break down the structural differences between the US market and European "powerhouses," exploring why the UK's policy levers might offer a more realistic blueprint for the US than the classic Swiss or German models. From the role of trusted intermediaries to implementing a systematic "pay-for-apprenticeship" funding mechanism, John shares the major solutions needed to scale the system. Finally, we look at the strategic intersection of higher education and the workforce. John explains how colleges and universities can embrace apprenticeship degrees as a risk-mitigation tool against declining enrollments, and how small-to-medium enterprises can band together to leverage these programs. Tune in to discover the 10-year best-case scenario for the learn-and-earn movement and find out why the ultimate career path of the future might just start with a job, not a degree.

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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
    2026
  • Episodes
    85
  • Rating
    Clean
  • Copyright
    © 2026 An Educated Guest
  • Show Website
    An Educated Guest