Is Renting Actually Better Than Buying a Home...

#274: Chris walks through the complete history of points and miles and breaks down the $140 billion machine behind them, so you can get more out of every point you earn. He covers the legal accidents that made credit cards wildly profitable, why loyalty programs are worth more th ...  Show more

#273: Learn to stop overthinking and make better decisions. Chris and Derek discuss how optimizing can go wrong, a coin flip trick for making decisions, journaling as a superpower, how your actions might reveal what you actually want, and more. Derek Sivers is an entrepreneur, wr ...  Show more

Sunnie (29) and Jazmyne (30) are a queer couple trying to build their life together—buy a house, bring a child into their family, and create long-term financial security. But with just one primary income and a major surgery planned for next year, every decision feels high stakes. ...  Show more

I’ve been that multi-millionaire who rents, proudly defending why homeownership wasn’t the right choice for me—until now. At 31, I bought my first house, and in this episode, I’m sharing everything I learned along the way: the emotional rollercoaster of finding “the one,” the fin ...  Show more

Class is back in session! In this special ‘Study Hall’ episode, I’m breaking down one of the biggest decisions you’ll ever make––home buying. We’ve packed this episode with some of our best conversations on renting vs. buying—including insights from Ramit Sethi, Kate Wood from Ne ...  Show more

If you’re holding out for the “perfect” deal, you’ll always be on the sidelines. Today’s guests weren’t afraid to take on a challenge with their first rental property, and it paid HUGE dividends. Not even an expensive market or extensive rehab could stop them from making money an ...  Show more