Ep 20 - JL Collins - The Simple Path to F-You Money (And Why You Need to Ask Your Boss for a Paid Leave Today)

Your Money Guide on the Side

Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Path to Wealth, a personal finance classic that has empowered hundreds of thousands to think differently about investing, independence, and freedom.

In this conversation, JL and I explore the real meaning behind financial independence — not retiring early, but reclaiming your ability to say no. We go back to the moments that shaped his life philosophy: the bold four-month leave he took just two years into his first job, the decision to convince his wife to leave her job while he wasn’t earning a paycheck, and the early desire to build what he calls FU money — not to quit work, but to buy back control.

We revisit Black Monday in 1987 and how that shaped JL’s views on market volatility, risk, and emotional discipline. He shares how a humbling mistake helped hardwire the importance of staying the course, and how index investing eventually became the core of his life’s message: simplify.

We also talk about the new edition of The Simple Path to Wealth, what’s changed, what hasn’t, and how his daughter went from being the reluctant listener to co-pilot on the updated edition.

This is a conversation about money, yes — but more than that, it’s about living deliberately. JL reminds us that wealth isn’t about what we can afford — it’s about what we no longer have to worry about.

You’ll hear about:

• How JL built his investing philosophy through trial and error
• Why VTSAX and chill remains his core guidance
• What it means to live in a world where, eventually, everything is "free"
• Why simplicity is a radical act in a noisy, complex world

And why, if you get the money stuff right early, you can spend the rest of your life not thinking about it at all.