Segment 1: Brian Speers, Wealth Management Advisor at Merrill Lynch joins John joins John to break down retirement planning strategies across generations, from Gen Z just starting out to Baby Boomers watching their spending in retirement. Brian explains why tackling high-interest debt first, using Roth accounts early, and building long-term saving habits can make all the difference, and why even late-career workers may benefit from part-time income.

Segment 2: Linda Bell, Home Lending Expert, Bankrate, joins John to talk about why so many homeowners are overpaying on their property taxes and how to successfully appeal an assessment. Linda walks listeners through reviewing a property record card, gathering evidence, and deciding whether to DIY or hire help.

Segment 3: James Rodriguez, Senior Reporter, Business Insider, joins John to discuss the rise and fall of “Zoom towns,” the warm-weather cities that saw explosive growth during the pandemic. James explains how migration to places like Austin, Tampa, Phoenix, and Atlanta drove prices sky-high and why cooling demand, increased inventory, and stalled mobility have now flipped the script, keeping Midwest markets like Chicago surprisingly strong.

Segment 4: Matt Adams, principal at Deloitte Consulting, joins John to preview the 2025 holiday shopping season. Matt shares Deloitte’s latest findings showing Chicago consumers plan to spend 11% less this year, explains the rise of value-seeking behavior and gift-card giving, and breaks down why early October deal days and Black Friday/Cyber Monday still dominate holiday spending patterns.