What happens when a former English teacher becomes a CFO—and decides to teach everyone around him how money actually works?
In this episode, Tyler sits down with longtime friend and campmate Andy Schneider, a career educator and current CFO at an independent school, for a wide-ranging and deeply honest conversation about what we teach (and don’t teach) about money.
Andy has worn a lot of hats—boarding school English teacher, PWC consultant, MBA grad, educational administrator—and he brings a rare combo of humility, humor, and clarity to the messy overlap between education, money, and life purpose.
You’ll hear:
- Why Andy left the classroom—and why he came back
- How business was “demystified” for him in the least expected way
- What actually drives the cost of college (and why some schools won’t survive)
- The myth of the “money expert”—and how to choose who you trust
- What a CFO wishes more teachers asked him (but never do)
🎙️ Plus:
- The uncomfortable truth about health insurance, school budgeting, and stock-picking competitions in high schools
- Why college needs a Julliard-style reset for the modern world
- And why Psychology of Money by Morgan Housel just might be the most important book you’ll ever read
This one’s for anyone navigating careers, family, and the growing pressure of financial decision-making in a world that feels increasingly complex and expensive. Whether you're saving for college or trying to explain your 401(k) to your teenager, this episode helps add clarity, confidence, and maybe even some joy to the process.
📚 Education, meet real-world finance.
🐶 Also: Tyler’s dogs make a guest appearance with some strong opinions on college tuition.
🔍 Highlights & Resources:
- Book: The Psychology of Money by Morgan Housel
- Concept: Education vs. College (yes, there’s a difference)
- Tool: Why every good CFO keeps a whiteboard in their office
- Framework: You don’t need to be a teacher to teach
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🎧 More episodes at Your Money Guide on the Side
