Mar 16, 2026 ¡ 36 min ¡ 13 segments
In this powerful episode of Money Mondays, Dan Fleyshman sits down with Garrett J. White for a raw conversation on the real relationship between money, marriage, masculinity, investing, and purposeâŚ
Dan FleyshmanHost
There's lots to unpack there, but one of the first questions I actually have for you is why do you think it's hard for men to talk about money in their households?
So, well, you're gonna have two different levels of hard, right? So you've got hard when you don't have any.
W- when you don't have any, it's hard because scarcity is, like, the dominating energy, and when scarcity's there, the woman feels unstable, unsafe, un- insecure, which means sexual connection goes down, communication becomes tough and hard to have.
Then you have a second phase, which is when you're building something and it's working, and you're obsessed, and your business becomes your mistress and your, your s- your side piece, and that's, like, the game, and you're obsessed with building, and then you face chaos and destruction, and even when-
And then the third level that's hard, I think it's probably the hardest, which is when you actually have money.
Because you start to ask interesting questions, and the question a, a lot of guys have been asking in the, been the last couple of years is, "Okay, so I built this thing.
... or does she just like the money and the world that I've created? And if I went back to zero-

There's lots to unpack there, but one of the first questions I actually have for you is why do you think it's hard for men to talk about money in their households?
So, well, you're gonna have two different levels of hard, right? So you've got hard when you don't have any.
W- when you don't have any, it's hard because scarcity is, like, the dominating energy, and when scarcity's there, the woman feels unstable, unsafe, un- insecure, which means sexual connection goes down, communication becomes tough and hard to have.
Then you have a second phase, which is when you're building something and it's working, and you're obsessed, and your business becomes your mistress and your, your s- your side piece, and that's, like, the game, and you're obsessed with building, and then you face chaos and destruction, and even when-
And then the third level that's hard, I think it's probably the hardest, which is when you actually have money.
Because you start to ask interesting questions, and the question a, a lot of guys have been asking in the, been the last couple of years is, "Okay, so I built this thing.
... or does she just like the money and the world that I've created? And if I went back to zero-
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