How Much Money Is Enough? Plus, Why AI Won’t Replace Financial Advisors — with Jack Raines

"I still fly economy, but I can fly anywhere I want." That line from a listener question captures the central tension of the episode: the difference between having enough money and feeling like you have enough. Jack Raines, writer of the Young Money newsletter and author of the forthcoming book Young Money: A Field Guide to Wealth and Purpose in Your Twenties, joins Scott Galloway to unpack that tension, along with practical questions about home-buying in expensive cities and whether AI will make financial advisors obsolete. The conversation stays grounded in the psychology of money, not abstract theory.

The Psychology of "Enough" — and Why It's So Hard to Reach

Raines and Galloway agree that there is such a thing as enough wealth. The real problem is human nature. "Humans are kind of status chasing monkeys," Raines says. "Once you get to what you thought was enough, there's always another level." He grew up in South Georgia, where his version of "enough" was very different from what he sees in New York or San Francisco. The question isn't whether enough exists, but whether you can resist comparing yourself to people one rung ahead.