Are we handing the keys of AI to a generation of "passengers"? In this episode of An Educated Guest, host Todd Zipper talks with Rebecca Winthrop, Senior Fellow at the Brookings Institution and author of The Disengaged Teen.

Rebecca shares her journey from refugee camps to the halls of Brookings, explaining why she believes the current risks of generative AI for K-12 learners outweigh the benefits—unless we change the way we teach. We dive into her "Four Learning Modes" framework to understand the spike in teenage disengagement and discuss the chilling reality of a workforce where "AI agents" are increasingly preferred over entry-level human hires.

From the "Experience Paradox" to the "Cognitive Offboarding" trap, Rebecca provides a roadmap for parents and educators to help students move from being passive recipients of information to intrinsically motivated "Explorers" who can partner with AI rather than be replaced by it.

What happens when you apply the principles of design thinking to the Ivy League career journey? In this episode of An Educated Guest, host Todd Zipper talks with Joe Catrino, the Executive Director of the Dartmouth Center for Career Design.

Joe shares his "circuitous" journey from first-gen history major to ESPN and Yale admissions, eventually finding his calling in "Life Design"—a methodology pioneered at Stanford that encourages students to prototype their way through college. We dive deep into Dartmouth’s landmark $30 million internship endowment, which provides students with grants up to $6,500 to pursue unpaid roles in government, non-profits, and startups.

Beyond the funding, we discuss the "Entry-Level Paradox" and how Joe’s office is leveraging digital tools to help students visualize non-linear career paths from philosophy majors to tech leaders. Whether you are a parent worried about the 2026 job market or a higher ed leader looking to scale student outcomes, this episode provides a masterclass in modern career design.

Can the emotional power of a blockbuster movie actually help a student master organic chemistry? In this episode of An Educated Guest, host Todd Zipper talks with Josh Reibel, CEO of Dreamscape Learn, about the radical redesign of the learning experience.

Josh shares his "circuitous" 35-year journey from being a high school teacher in the late 80s to serving as the CEO of Amplify Learning and eventually partnering with Michael Crow and Walter Parkes to lead Dreamscape Learn. We dive into the "Alien Zoo"—the flagship VR curriculum where students become field biologists in a cinematic intergalactic sanctuary—and discuss why emotional engagement is the key to student persistence.

Beyond the headsets, Josh explains the logistics of the "Immersive Classroom" and how VR can serve as a "departure hub" for students regardless of their geography or socio-economic background. Whether you are a college president worried about the enrollment cliff or an educator looking for the next frontier of student engagement, this conversation provides a blueprint for the future of the 21st-century classroom.

Is a liberal arts degree actually the secret weapon in the age of AI?

On this episode of An Educated Guest, Todd Zipper sits down with Dr. David Watts, the Director of the Davis Institute for Artificial Intelligence at Colby College. David recently made headlines by leaving a top executive role at IBM to lead this initiative at a small liberal arts college.

They discuss why the future of the workforce demands more than just technical skills and why "interdisciplinary" thinking is the new currency. David opens up about the challenge of "cognitive offboarding"—the risk that students might outsource their critical thinking to algorithms—and how higher education must pivot to prevent it.

In this episode, we cover:

• Why "entry-level" jobs are disappearing (or at least, changing forever).
• How to teach AI ethics without it feeling like a "compliance checkbox."
• The surprising intersection of AI, philosophy, and the arts.
• How faculty are moving from grading "outputs" to grading "process."

To learn more about the Davis Institute, visit the Colby College website.

Why does a bachelor’s degree take four years? Is it because that is how long it takes to learn, or is it just a historical accident?

On this episode of An Educated Guest, Todd Zipper sits down with Madeleine Green of the "College in 3 Exchange" to discuss the movement that is challenging the 120-credit hour monopoly. Madeleine explains how the four-year standard was originally created not for students, but for a faculty pension scheme, and why the time is right to redesign the undergraduate experience.

In this episode, we cover:

• The surprising history of the "Carnegie Unit" and seat-time requirements.
• How institutions are redesigning curricula to cut fluff without sacrificing quality.
• The financial and career benefits for students entering the workforce a year early.
• The regulatory hurdles at the state level that are slowing down innovation.
• Why "College in 3" is about rigorous design, not just speed.

To learn more about the institutions involved, visit the College in 3 Exchange website.

How does a university reach 180,000 students while maintaining a billion-dollar research engine and a "perpetual" culture of innovation? In this episode of An Educated Guest, Todd Zipper sits down with Dr. Chris Howard, EVP and COO of Arizona State University, to explore the "Public Enterprise" model that is shaking the foundations of higher education.

Chris shares his remarkable journey from being a Rhodes Scholar and helicopter pilot to leading ASU’s operations alongside President Michael Crow. We dive into the "Crow Transformation," the crisis of belief in modern higher ed, and how ASU is using Hollywood-style storytelling through Dreamscape Learn to revolutionize the way students learn biology.

We also tackle the complex world of college athletics, the legacy of Pat Tillman, and why Chris believes that partnership—not just enrollment—is the key to a resilient workforce. Whether you're curious about the future of AI in the classroom or how military leadership translates to the boardroom, this conversation offers a masterclass in agency, service, and strategic growth.

Is the United States facing a new "Sputnik moment" in education? On this episode of An Educated Guest, Todd Zipper sits down with Jeff Riley, the leader of Day of AI, to discuss the urgent need for AI literacy in our schools.

Jeff, a veteran educator with over three decades of public service, argues that AI is no longer optional—it is the "Fourth R" of education, as fundamental as reading, writing, and arithmetic.

In this episode, we cover:

• Why the U.S. risks falling behind globally in AI literacy by 2029.
• The "Driver's Ed" analogy: Why we need to teach students how to drive the technology before giving them the keys.
• How AI can finally unlock true differentiation and personalization in the classroom.
• The dangerous "knowledge gap" between what kids are doing with AI companions and what parents actually know.
• Practical advice for parents and educators on navigating this rapid technological shift.

To learn more about the free curriculum and tools discussed, visit the Day of AI website.

What happens when you stop asking kids to sit in 45-minute "silos" and instead ask them to solve real-world problems for their community? In this episode, host Todd Zipper sits down with Jeremy Lugbill, CEO of the Career Academy Network of Public Schools (CANOPS) in Indiana, to discuss the radical redesign of the American high school.

Jeremy shares how his network achieved a staggering 98.48% graduation rate by focusing on "durable skills" like communication, critical thinking, and agency. We explore the Portage School of Leaders, where students operate without bells and engage in three-week interdisciplinary "immersions" to tackle local challenges. Jeremy also dives into the power of "blurring the lines" between K-12 and industry through their award-winning partnership with the Boys & Girls Club and their pioneering AI Career Pathway.

Whether it's student-run manufacturing businesses or earning stackable credentials in healthcare while still in high school, this conversation is a masterclass in how to move from "school type" debates to high-quality student outcomes.

It is an all-too-common story: a student graduates with a degree but is rejected from entry-level jobs because they lack "real-world experience." On this episode of An Educated Guest, Todd Zipper sits down with Dana Stephenson, co-founder of Riipen, to discuss how his company is dismantling this barrier.

Dana shares how Riipen connects universities with a global network of employers to embed real-world projects directly into the curriculum. Instead of theoretical case studies, students work on actual business challenges, allowing them to build a portfolio and professional network before they ever leave campus.

Key topics discussed:

• The Origin Story: How a student project at the University of Victoria turned into a global marketplace.
• The Ecosystem: Solving the "chicken and egg" problem for schools and companies.
• Equity in Access: How virtual, project-based learning opens doors for non-traditional students and those who can’t afford unpaid internships.
• The Future of Work: Why 61% of entry-level jobs now require 3+ years of experience and how higher ed can adapt.

Sabari Raja, Managing Partner at JFF Ventures, joins us to discuss her unique journey from founder (NEPRIS, now Pathful) to leading a pioneering venture fund focused on economic mobility. JFF Ventures operates at the intersection of philanthropy and venture scale, proving that investments focused on the middle and low-wage worker can achieve both high returns and massive social impact.

In this powerful conversation, Sabari breaks down the three main investment themes that target the worker's full journey, from skills access to career advancement. We dive into the most difficult areas of the market, including the challenge of investing in wrap-around support like childcare and credit access.

Sabari shares the questions every investor and founder should be asking about AI—is it taking away agency or expanding it? Finally, she reveals a surprising area of alignment for future capital: the $1 trillion investment needed to support the industrial backbone of the AI economy (power grids, data centers, and semiconductors).

Key Takeaways You Won't Want to Miss:

• Impact as an Enabler: Why JFF Ventures views strong outcomes (like reduced transfer credit loss via companies like Advisely) as a direct line to revenue and growth.
• The AI Agency Test: The fundamental question investors should ask to gauge a startup’s longevity: Does your AI give the worker more agency or less?
• The Industrial Investment Thesis: How JFF Ventures is aligning with the global infrastructure boom, targeting the massive labor shortage in energy and utilities.
• The Lived Experience: Why founders with a lived understanding of problems—like the transfer credit crisis or lack of social capital—are better positioned to build mission-driven, scalable solutions.