207. “I’m 40, burned out, and don’t know what’s next in my life”
Courtney (40) and Ray (41) have spent their entire adult lives in the structure of military life—but with retirement on the horizon, they’re about to face a future filled with choices for the first ti...
6 Maj 20251h 16min
206. “I quit my job to care for our son, but can we afford it?”
Anna (33) and Will (37) are married with two kids, including a young son who was born with a serious heart condition. Between unexpected medical expenses, emotional stress, and inconsistent financial ...
29 Apr 20251h 19min
205. “I've been homeless before…I'm terrified to spend money”
Jennifer (37) and Steve (41) have been dating for over five years, but they’ve never spent more than $100 on a shared purchase. Jennifer is a self-made business owner with a clear vision for the fut...
22 Apr 20251h 17min
204. “We make $226K—but our kids think we’re broke”
Lisa (37) and Marcus (38) have been married for 14 years, raising four kids and building a life together—but when it comes to money, they couldn’t be further apart. Lisa homeschools their kids and dre...
15 Apr 20251h 11min
203. “He makes 3x more, but wants to split everything 50/50”
Katie (28) and Robin (35) live together in Tennessee and are planning a wedding. They earn a combined $386K, but don't split bills proportionally—even though he makes three times more. She feels judge...
8 Apr 20251h 22min
202. “She racked up $50K in debt — why should I trust her with money?”
Emma (39) and Dave (39) make $258,000 a year—but they’re stuck in a toxic money dynamic. She built a financial plan during maternity leave. He didn’t believe her. Now, they’re battling over trust, $50...
1 Apr 20251h 23min
201. “I make $40k… but I own 100+ suits”
Today’s episode takes us to New York City, where I sit down with not two, but three couples live on stage at my Money for Couples event. First, meet Antonio (23) and Devonta (23), a young couple who i...
25 Mars 20251h 10min
200. “Should we pay off our massive debt? Or invest more?”
Wilson (46) and Shannon (35) have built a strong financial foundation—owning a vacation rental, maxing out Roth IRAs, and earning solid incomes. But when it comes to their next move, they’re at odds. ...
18 Mars 20251h 33min
