At this point, the annual “Plan with Me”-style episode feels like a sacred ritual. In today's show:
Thinking through major tax changes, including why I finally ponied up for a CPA and what they’ll be doing
Estimating and planning with irregular income
Identifying new retirement contribution targets
Revisiting the slush fund concept for covering ... Show More
Nov 5
The Leisure Gap, Princess Treatment, and Other Hard Truths About "Soft Life"
There is perhaps nobody in the financial education space who knows her way around the National Bureau of Economic Research quite like Stefanie O’Connell Rodriguez. If Chapter 2 of Rich Girl Nation were sentient, it would probably sound a lot like Stefanie. Today on the show, I’m ... Show More
1h 15m
Oct 22
On Influencers, Beauty Culture & "Corporate Confidence," with Kate Kennedy
I previously joined Kate Kennedy on her show, Be There in Five, to discuss Rich Girl Nation, and we ended up talking about everything from beauty culture to women as breadwinners—enjoy. Get your copy of Rich Girl Nation, recently named one of Barnes & Noble's Best Business Books ... 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 ... 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 11
#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