Well, here we are—for the last time, for now. A couple weeks ago, I wrote an end-of-year letter that functioned like a little “status update” on how I’m feeling moving into 2026. In this episode, I invite back five of my favorite guests for their own check-ins. We talk about:
What it feels like to finally pull the “F.I.” rip cord (and whether it “works” ... Show More
Dec 17
Why We Judge Women’s Spending, What We Hide, & What We’re Afraid to Admit
Today’s guest won’t surprise you if you read the introduction to Rich Girl Nation, which recollected the 2018 event that made me think personal finance might not be solely for people with brown bananas and pocket protectors. Lindsey Stanberry, founding editor of Refinery29’s Mone ... Show More
56m 3s
Dec 3
How to End Low Wage Work—Forever
How do you solve a problem like the disconnect between “wages employers are willing to pay” and “wages employees need to survive”? If you’re my guest this week, the answer is: a wage subsidy. Today on the show, I speak with Ben Glasner, an economist with a PhD in public policy an ... Show More
1h 18m
Oct 2024
Why Following Your Passion Might Be Holding You Back with Scott Galloway
Ever wonder what true wealth is? In today’s episode, I sit down with Scott Galloway, a fierce thinker, NYU professor, and one of the most influential voices on business, technology, and modern society. Scott pulls no punches as he redefines what it means to be truly wealthy—and w ... Show More
1h 3m
Jul 2023
Juliet Schor, "After the Gig: How the Sharing Economy Got Hijacked and How to Win It Back" (U California Press, 2021)
When the "sharing economy" launched a decade ago, proponents claimed that it would transform the experience of work--giving earners flexibility, autonomy, and a decent income. It was touted as a cure for social isolation and rampant ecological degradation. But this novel form of ... Show More
54m 49s
Jun 2025
Breaking the Breadwinner Mold: How Role Reversal Can Supercharge Your Wealth with Tiffany Irving
In this candid conversation, wealth advisor Tiffany Irving shares her journey as the breadwinner in her family while her husband has been a stay-at-home dad for over 20 years. We explore the financial strategies, mindset shifts, and relationship dynamics that make this arrangemen ... Show More
45m 16s
Sep 2025
#1 Negotiation Guru Reveals the Secrets of Negotiation & Influence - with Giuseppe Conti
Most people fail in negotiations because they don’t prepare, confuse influence with persuasion, or push when they should pull—Giuseppe Conti, the world’s #1 Negotiation Guru, shows you how to avoid these mistakes. Buy the book Negotiation + Influence = Success: Quick Lessons to H ... Show More
1h 3m