Ramit Sethi — How to Play Offense with Money, Plan Bucket Lists, Build a Rich Life with Your Partner, and Take a Powerful $100 Challenge (#524)

Artist's rendering of Ramit Sethi.Artist's rendering of Ramit Sethi.
Illustration via 99designs

“People’s feelings about how they are doing financially are highly uncorrelated with their actual financial status.”

— Ramit Sethi

Ramit Sethi (@ramit), author of the New York Times bestseller I Will Teach You to Be Rich, has helped tens of millions of people live a rich life with their money, careers, businesses, and psychology. He hosts more than a million readers on his site iwillteachyoutoberich.com, newsletter, and social media. His new podcast, I Will Teach You to Be Rich by Ramit Sethi, reveals real stories about love and money from behind closed doors. Subscribe on Apple Podcasts, Spotify, or wherever you listen to fine podcasts.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. You can also watch the interview on YouTube.

Brought to you by Wealthfront automated investing, Athletic Greens all-in-one nutritional supplement, and Pique Tea premium tea crystals. More on all three below.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear Ramit’s last appearance on this show? Lend an ear to our conversation in which we discussed savvy negotiation, why not all good financial decisions are created equal, sensible expenditures that appear frivolous at first glance, money dials, game-changing conveniences, challenging accepted “truths” about money, the pros and cons of the prenuptial agreement, mini-retirements, and much more.


  • Connect with Ramit Sethi:

Website  | Instagram | YouTube | Twitter


  • Most memorable money conversations with couples in debt that Ramit has had since our last episode together. [06:06]
  • A recent purchase over which I agonized to a degree that seems ludicrous in hindsight. [08:38]
  • How do you think about money? Probably not as closely as the guy Ramit knows who has $8 million in net worth but goes out of his way to save $8 on groceries because he hates “the idea of overpaying.” [09:56]
  • Why did it take so long for Ramit to start a podcast, and in what ways can a listener expect his show to differ vastly from this one? [12:03]
  • Ramit justifies his fascination for toying with trolls, and I share a pro tip for anyone who’s ever being interviewed by a journalist (or podcaster). [14:12]
  • In the last 30 days, can you think of a specific situation where you were not on the same page financially with your partner? [16:08]
  • What is your idea of a rich life? This is a question with wildly varied answers depending on who you ask, but one truth seems consistent: People’s feelings about how they are doing financially are highly uncorrelated with their actual financial status. [17:18]
  • Why Americans’ tendency to compare themselves to their neighbors is completely irrational. [20:16]
  • What does Ramit’s rich life look like? [22:16]
  • Ramit’s money rules. [23:17]
  • What the recent decision to have fresh flowers delivered to my house every week does for my rich life. [24:36]
  • Why asking “What is your rich life?” can be such a magical, transformational question — especially when a partner is present. [25:40]
  • If you’re a bit of an overspender, have you ever said “No” to your partner or family? [27:38]
  • If you were not on the same page financially with your partner at some point in the last 30 days, on a scale of 1 to 10, how big of an issue is it? [28:32]
  • A bucket list/rich life goals vision exercise Ramit did with his wife Cassandra, inspired by Stephen King’s 2003 National Book Club Speech. [30:06]
  • How Ramit and Cassandra have agreed to financially contribute, together, to their eight-year anniversary goal, and how it feels to watch the fund make progress. [34:55]
  • Ramit and Cassandra meet once a month to discuss finances. What does the format look like? [38:21]
  • Ramit’s true, but most embarrassing backlog rich life goal. [41:13]
  • How to make conversations about money positive experiences rather than negative and depressing. [43:50]
  • The typical approach to talking about finances when one half of a couple is an overspender (and/or people pleaser who has trouble establishing boundaries), and what Ramit suggests as a better, more effective alternative. [44:40]
  • What needs to happen for a couple to succeed in solving whatever financial problems they have (and avoid passing along toxic money behavior to their offspring). [49:26]
  • Why it’s not enough just to want to change your relationship with money, and how psychology and tools can easily be used to affect the desired change — with far less effort than fighting with your spouse about money for the rest of your miserable lives. [52:12]
  • An example of a time Ramit saw a 9/10 severity problem with a couple and their money solved simply. [54:38]
  • Thoughts and positive listener feedback about prenups since our last conversation. [57:55]
  • The $100 challenge. [1:00:12]
  • What would result from Ramit’s own $100 (or $1,000 or $5,000) challenge? [1:04:02]
  • What would the result of my own challenge look like? [1:07:17]
  • Gauging the most important lessons that can be learned from the $100 (or more) challenge, and rejecting the coded-for-fear life of frugality that many of us accept as the default. [1:08:32]
  • How Ramit turned a couple’s conversation around a $100+ honeymoon challenge from a downward spiral into an upward one. [1:11:39]
  • Thoughts on how we can learn to spend our money in meaningful ways on enjoying and enhancing a rich life rather than endlessly stockpiling it for some unknown purpose in an unforeseeable future. [1:13:06]
  • Fascinating patterns around the saving and spending of money that Ramit has noticed in his conversations with couples. [1:20:03]
  • Recommendations for further developing the skill of financial comfort and reaffirming the importance of a relationship. [1:24:02]
  • Exercising generosity as a way of becoming more like the people we want to be and reinforcing the positive potential of the money we make. [1:25:07]
  • How Billy Joel impressed the power of generosity and graciousness upon a teenage busboy named Tim. [1:27:23]
  • Parting thoughts. [1:29:42]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 600 million downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.