Self-made millionaire shares the hardest money conversation he and his wife have ever had: 'I'm sweating thinking about it'

Self-made millionaire, author and TV host Ramit Sethi knows a thing or two about money. He's even published books on how to get rich and how couples can manage their finances together.

But his own financial journey hasn't been perfect. He recently sat down with his wife, Cassandra, for a special episode of his Money for Couples podcast where they answered some of the same questions he asks couples every week in an interview with friend Julie Nguyen.

The Sethis have been married since 2018, and Ramit has often shared tidbits about their relationship on his podcast and in his books, highlighting some of the strategies they've used to navigate combining finances, earning different incomes, creating shared goals and more.

On the podcast, Ramit and Cassandra agreed on the most difficult money conversation they've ever had as a couple: negotiating their prenup before getting married.

"I'm sweating thinking about it right now," Ramit said. "[The] first time I brought it up, I remember I had talked to so many people, gotten advice, planned what I was gonna say and I was very nervous about it."

Cassandra received the idea of a prenup well, he said, but things went south from there. 

Many money experts recommend getting a prenuptial agreement, even to those with modest finances. A prenup is a legal contract outlining how a couple wants their finances handled in the event of a divorce. Without one, couples could wind up leaving those decisions — like who gets certain assets or who pays spousal support — up to a judge.

Prenups are for everyone, money expert Suze Orman told CNBC Make It in 2020, and individuals should feel comfortable bringing it up with their partner.

"If you cannot talk money to the person that you are about to marry, you are doomed for failure because money is going to run through your relationship more than anything else," she said.

When Ramit brought up the idea of a prenup up to Cassandra, he had already started his business and written his first book on money. Cassandra didn't know much about them, but was willing to learn. And while they both agreed to get a prenup, their negotiations turned contentious due to differing expectations and understandings of money.

Ramit saw the negotiations as strictly financial and tried to let the numbers speak for themselves. Cassandra, on the other hand, was more tapped into the emotional considerations, which Ramit wasn't really thinking about.

Ramit tried to make a "generous" offer in his prenup proposal, he said, but Cassandra was more concerned with their relationship and ensuring their feelings and emotions were aligned.

"We started going back and forth and I was very confused, very hurt because I'm like, 'I'm not trying to trick anybody here,'" Ramit said.

Cassandra eventually suggested the couple sit down with a therapist and talk through their emotions to figure out where things weren't aligning. The therapist asked how they each view money.

"That really opened up conversations that we hadn't been able to have because my answer was like, 'growth, of course, look at the compounding.' And her answer was, 'safety,'" Ramit said.

Despite the turmoil, the process helped the couple deepen their relationship by revealing not just how they each think about money, but also how they should be communicating those feelings with each other, they said.

While Ramit was more focused on the actual numbers, Cassandra didn't have the financial knowledge to get a sense of security from the amounts in their savings and investment accounts.

"I'll never forget something Ramit said to me during that time. You were like, 'I really need you to get better at money,'" she said. "I took that very seriously because deep down inside I was like, 'I know I'm not that great at money. I could get better.'"

While she worked on learning about prenups and managing money in general, Ramit acknowledged he needed to improve at talking about emotions so he could more clearly communicate where he was coming from and better understand Cassandra's perspective.

"In retrospect, you were not asking me to pull out a f------ spreadsheet. You were feeling this," he said. "Looking back, I needed to listen to what you were saying. I should have been asking more questions."

Now seven years into their marriage, they still consider what they learned from their prenup negotiations the most valuable lessons they've learned from each other, they said.

Cassandra said Ramit's mindset around abundance and trusting your earning power "has been really eye-opening." And Ramit is grateful to have learned from Cassandra the importance of checking in on your feelings and talking about them.

"It has really changed the way that I relate to people a lot," he said.

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