Ep 16 - Andrew Tobias - The Only Investment Interview You Will Ever Need (And How Money CAN Buy Happiness)

Your Money Guide on the Side

What if the only investment guide you ever needed... actually was?

This week, I sit down with personal finance legend Andrew Tobias—bestselling author, Harvard Business School grad, long-time political advocate, and the brilliant mind behind The Only Investment Guide You’ll Ever Need. His book was literally the first financial text I ever read, and it remains one of the few I return to over and over again—for its timeless principles, relatable tone, and surprising humor.

In this conversation, we cover:

• The unlikely path from Slavic literature major to bestselling financial writer
• Why “don’t be boring” might be the best writing advice you’ll ever get
• The epic laundry list of startup investments that went very sideways (and what he learned from each)
• The true cost of chasing returns vs. chasing happiness
• Why retirement isn't a finish line—but a lifestyle with the right people
• His most embarrassing investing losses—and how they became his favorite teaching tools

Andrew doesn’t just teach people how to manage money—he shows us how to think about it, with warmth, wit, and an honesty that’s rare in finance.

🎧 If you’ve ever wondered what makes financial advice stick—or how to build a life rich in meaning as well as money—this episode is for you.

🔗 Subscribe, rate, and share if it resonates. And thank you for joining me on Your Money Guide on the Side.