Episode 1: From Sleeping in Closets to CEO | My Journey with Classical Conversations

Robert shares his journey from being homeschooled through high school to becoming CEO of Classical Conversations.


Refining Rhetoric with Robert Bortins


In this first episode of Refining Rhetoric with Robert Bortins, host Robert Bortins discusses his background and what listeners can expect from future episodes of the show. Using the fifteen tools of classical learning, Robert shares how he built a strong resume in high school with professional work experience, paid for college by himself while sleeping in friends’ closets, worked in manufacturing for five years, and finally became CEO of Classical Conversations, the world’s largest homeschooling support organization.

“I did have a few phone calls from my mom asking if she could borrow money from me so she could go buy inventory for a homeschool convention and sell some books and then pay me back, of course. But I would tell her, ‘Mom, my friends call their parents for money, not vice-versa.’ It was definitely interesting times, and I’m better because of that.”

Robert Bortins


  • Intro to episode and this new podcast series [0:16]
  • Overview of the fifteen classical tools of learning [1:31]
  • What is Classical Conversations? [3:00]
  • Robert describes being homeschooled through high school [3:21]
  • Ad: Schoolhouse Rocked: The Homeschool Revolution [3:53]
  • Having the freedom to work part-time during high school [4:32]
  • Choosing to pursue a degree in industrial engineering and a unique college experience [5:56]
  • Ad: Senators of Rome and Exploring the Heavens with Uncle Paul [11:20]
  • Early career experience with UPS and Easy Gardener [11:45]
  • Did Robert always want to work for Classical Conversations? [12:15]
  • Finding meaning in creating more flourishing lives for people [12:51]
  • Realizing that God was calling Robert to work for Classical Conversations [14:27]
  • What to expect from future episodes of Refining Rhetoric [16:22]
  • Classical Tools Recap [17:01]
  • Upcoming episodes of the show [18:43]
  • Outro [20:02]