Podcast Feed

154. “We’re drowning in debt, but I drive a BMW”

154. “We’re drowning in debt, but I drive a BMW”

Kevin and Michelle, 32 and 30, joined me live in New York City earlier this year for our very first in-person interview. They have one young child an…

153. “We’re married. Why do I have to ask him for money?”

153. “We’re married. Why do I have to ask him for money?”

Allison is 36 and Dan, 37. They’re married with two kids living in a HCOL mountain town—a market variable that’s influenced them to sell her condo an…

152. “The world is going to end. So why bother investing?”

152. “The world is going to end. So why bother investing?”

Fernando and Anushka, 30 and 31, live in San Diego and earn high incomes—matching $135,000 salaries, in fact. They have healthy investment and saving…

151. “Our gas is about to get shut off, but I refuse to sell any of my 7 cars”

151. “Our gas is about to get shut off, but I refuse to sell any of my 7 cars”

Peter and Megan, 36 and 37, are married with no kids but severe financial stress threatens their future together. Peter has grown to resent Megan’s u…

150. “We’re broke, but I spend $350/mo on clothes” (Part 2)

150. “We’re broke, but I spend $350/mo on clothes” (Part 2)

In part two with Elizabeth and Jonathan, 36 and 38, we continue unpacking their complicated personal backgrounds with money as they relate to current…

149. “We have no savings but bought our kid a $500 toy for Christmas” (Part 1)

149. “We have no savings but bought our kid a $500 toy for Christmas” (Part 1)

Elizabeth and Jonathan are in their mid-thirties, have been married for 13 years, and share a young daughter. They bought a starter home after gettin…

148. “We have 2 kids and $0 invested, but refuse to get 9-5 jobs”

148. “We have 2 kids and $0 invested, but refuse to get 9-5 jobs”

Callie and Travis, 36 and 39, have two kids and live in southern Texas near the ocean. They’ve made a conscious decision to run their own small busin…

147. “I don’t trust him with money, so I check his cc accounts”

147. “I don’t trust him with money, so I check his cc accounts”

Ashley and Christopher, 30 and 28, recently got engaged and look forward to planning a wedding, having kids, etc. But Christoper has lived with credi…

146. “I'm jealous when I see friends' vacations on Instagram”

146. “I'm jealous when I see friends' vacations on Instagram”

Erik is 44 and Andrea is 43. They’re trying to determine what to do with a bump in income. Andrea wants to save for college tuition, because that’s w…

145. “Am I a bad mom if we can’t do a $7k Disney trip?”

145. “Am I a bad mom if we can’t do a $7k Disney trip?”

Kristin is 32 and David is 38. They share five kids in a blended family and David is getting close to military retirement. The problem is their spend…

144. “We make $245K. Why do I have to ask my wife for dinner money?”

144. “We make $245K. Why do I have to ask my wife for dinner money?”

Brad and Angie, 55 and 56, are each 10 years into a second marriage. With six adult children out of the house, they’re planning to buy an RV and tour…

143. “I maxed out my credit cards on our $45k wedding. Are we broke?”

143. “I maxed out my credit cards on our $45k wedding. Are we broke?”

Amy and Tori are in their late 20s. They recently got married and honeymooned in Greece, racking up tens of thousands of dollars in credit card debt.…

142. “We have a $2.3M net worth—but we cut coupons”

142. “We have a $2.3M net worth—but we cut coupons”

Brian is 56 and Rachel is 51 and they’re both lawyers. She’s lost thousands on a financial advisor and he can’t stop paying his daughter’s rent. Bria…

141. “We only have $2k in savings but she can’t stop going to the mall”

141. “We only have $2k in savings but she can’t stop going to the mall”

April and Kevin are in their mid thirties with two kids. They’ve been married for twelve years and Kevin recently came across a good book on finance—…

140. “He put our $1M into one risky investment. Will we lose it all?” (Part 2)

140. “He put our $1M into one risky investment. Will we lose it all?” (Part 2)

Sandra, 46, and Brad, 48, return for Part 2 as we get our hands dirty with their incredible decision to invest $1,000,000—their entire net worth—into…

139. “I’m afraid he’ll leave if I don’t stop stressing about the budget” (Part 1)

139. “I’m afraid he’ll leave if I don’t stop stressing about the budget” (Part 1)

Sandra is 46. Brad is 48. They have four children and are living a high lifestyle as a result of two generational income explosions tied to Brad’s wo…

138. “My wife doesn’t want me to take a $720k job offer”

138. “My wife doesn’t want me to take a $720k job offer”

Mel and Babu are both 33 year-old doctors. Babu’s nearly done with his training, putting a huge decision in front of them about where to live and how…

137. “MLMs, crypto, real estate—I can’t stop falling for get-rich-quick schemes” (Part 2)

137. “MLMs, crypto, real estate—I can’t stop falling for get-rich-quick schemes” (Part 2)

David, 33, and Halima, 37, return to follow-up on last week’s episode, where we learned about their debt, painful backgrounds, unrealistic expectatio…

136. “We have $500k in debt. Can I retire early?” (Part 1)

136. “We have $500k in debt. Can I retire early?” (Part 1)

David's 33 and Halima's 37. They’re been married for one year, a second union for both. The deep emotional (and financial) scars from those past rela…

135. "It could cost us $50k to have a baby. Can we afford it?"

135. "It could cost us $50k to have a baby. Can we afford it?"

Kait is 36 and Em is 35. They’re married and pursuing IVF as a means to expand their family. But a misalignment on money stands in the way of a truly…