Bryan Caplan is currently a Professor of Economics at George Mason University, a New York Times Bestselling author of books such as The Case Against Education. He and Isaac discuss how he got into economics, his work habits, belief in personal bubbles, and explore three of his research areas.

Penelope Trunk is currently a the world's most influential career counselor according to Inc. Magazine, and the CEO of Quistic. Penelope has founded four companies and joins Isaac to talk about her past and current projects. They talk about writing, unschooling, startup mentality, trends in career development, and how to be honest with yourself when it comes to your future. Her latest startup, Quistic, provides online courses that help people manage their careers.

Chad Grills is currently the CEO of Mission.org, a network of business & tech podcasts designed to accelerate learning. This interview with Isaac from 2015, found Chad working as the curator of the Medium publication, Life Learning. He talks with Isaac about his three core passions: Accelerated learning, Antifragility, and definite optimism.

On today’s HIR(ED) show, a panel discussion called “Agile Education: Are Bootcamps Iterating Fast Enough?”, featuring Will Sentance, CEO & Founder of Codesmith; RC Johnson, Director of Software Engineering for Indeed.com; Amir Savar, Founder of Skilled Inc.; and Joe Burgess, Entrepreneur in Residence at Flatiron School.

Jeremy Walsh is the Vice President of Enterprise Learning Solutions for Wiley Education Services. Jeremy asks whether the future of work is a "war for talent", or something else entirely?

Michael Gibson is a General Partner at 1517 Fund. Michael was pursuing a PhD in philosophy when it struck him that the really big ideas weren't being advanced within the walls of academia. He left, got into the tech world, and found himself running investor Peter Thiel's fellowship program for young college opt-outs. He's recently co-founded his own venture capital fund to support young people who want to work on big ideas outside of the classroom. Isaac and Michael discuss his love of literature and philosophy, how he wound up in Silicon Valley, and what it looks like to operate outside the status quo.

Peter Callstrom is the President and CEO of the San Diego Workforce Partnership (SDWP), the local Workforce Development Board for the City and County of San Diego. In early 2019, SDWP launched the first-of-its-kind Workforce Income Share Agreement (ISA) Fund. Capitalized with over $3M from initial philanthropic donations, the fund pays for post-secondary skills training in priority occupations.

Danielle Strachman is a Partner at 1517 Fund in San Francisco, which focuses on supporting young founders starting companies. 1517 partners with founders in a number of ways: mentorship and community building, kickstart grants of $1,000, and capital partnership through investment.

Zak Slayback was on scholarship at an Ivy League school. Deryk Makgill was on the dean's list at a top tier university. They both dropped out, and they're both glad they did. On today's show, Zak and Deryk join Isaac to discuss their experiences and offer thoughts on the university system and what dissatisfied students can do.

Nick Pinchuk is the Chairman and CEO of Snap-on, as well as a member of the Board of Directors of Columbus McKinnon Corporation, the National Association of Manufacturers, The Manufacturing Institute, the Manufacturer’s Alliance for Productivity and Innovation, and Carthage College. Nick served as the Chair of the Advisory Board for Skills for America’s Future at The Aspen Institute.