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255. "I’m 40 and work 2 jobs. How are we still broke?"

7 April 2026
Ramit Sethi of I Will Teach You To Be Rich talks to Gabriella, 36, and Chris, 40, a married couple from Pennsylvania with four kids, zero savings, and $32,000 in credit card debt. They both work multiple jobs. Chris travels all week and picks up extra shifts on weekends. Gabriella juggles three income streams while running the household alone. And yet their fixed costs sit at 109% of their income and the debt keeps growing.
What Ramit uncovers goes much deeper than the numbers. For years, Gabriella has been managing everything alone, building budgets Chris never looks at, covering purchases she never agreed to, and quietly losing hope. Chris has been avoiding the conversation entirely. And buried underneath it all is something neither of them mentioned in their application: they've been here before. They filed for bankruptcy. And now, with four kids in tow, they're on the exact same path.
In this episode we uncover:
Why two incomes and two extra jobs still aren’t enough when your fixed costs are 109%
The treadmill purchase that broke Gabriella's trust
What Ramit means by "95% of your money relationship is in the shadows"
The bankruptcy reveal that changes everything
Why Chris can't give a straight answer and what it's costing the marriage
The moment Gabriella admits she stopped doing everything just to see what would happen
How Gabriella's new $70K job changes the numbers overnight
The Florida plan and why Ramit says it won't fix anything
What it looks like when a couple finally starts working as a team
Chapters:
(00:00:00) "I've never not worried about money in our marriage"
(00:07:10) Do you have trust issues around money?
(00:15:18) "What if you just stopped doing it all?"
(00:17:32) "95% of our relationship with money is in the shadows"
(00:22:17) Ramit reads the separation ultimatum from her application
(00:34:00) The power dynamic: who earns more, who leads?
(00:46:05) "So you all are broke"
(00:52:27) The bankruptcy reveal
(01:00:36) The Florida plan and why it won't fix anything
(01:03:31) Gabriella's new income changes everything
(01:05:57) "I'm too tired of being alone"
(01:58:09) Follow-ups
Calling LA couples: Apply to be coached for free on this podcast at https://iwt.com/apply
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If you or your partner get stressed spending $150 on dinner, or are covering up spending, I'd like to help. Apply to be coached for free on this podcast at iwt.com/apply
Connect with Ramit
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