#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night. Most people wor...
#678: Anonymous (01:52): "Victoria" is 51, single, and still enjoying their W2 job while building a side business from a passion hobby. They’re thinking about heavy Roth conversions, planning for ...
#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now. The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rat...
#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets? I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 ...
#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018...
#674: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter R stands for Real Estate. This episode originally aired in May 2022, but the i...
#673: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today's second letter I stands for Investing. This episode originally aired in April 2022, bu...
#672: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter I stands for Increasing Your Income. This episode originally aired in August 2...
#671: Welcome to Greatest Hits Week — five days, five episodes from our vault, spelling out F-I-I-R-E. Today's letter F stands for Financial Psychology. And we're diving deep with a conversation t...
#670: As we close out 2025, premium credit cards are more expensive and more complicated than ever. It’s fair to ask whether the points game is still worth the effort. We sit down with Chris Hut...
#669: Slade (01:43) - Slade, 44, and his wife plan to downshift careers in the next five to seven years while raising their 11-year-old daughter. They want to know how to reallocate their $685K bro...
#668: We’re joined in-studio by David Bach, bestselling author of The Automatic Millionaire and The Latte Factor. He’s updated his most popular book (over two million copies sold) and this is his l...
#667: Home prices have outpaced wages for more than a decade, and first-time buyers are stretching further every year. Now a new idea is entering the conversation, the 50-year mortgage. It promises...
#666: In this First Friday economic update, we explore the paradox defining our current economy: record-breaking retail numbers alongside plummeting consumer confidence. In this First Friday econ...
#665: If you’ve ever stared at an insurance quote and wondered, “Is this really worth it?”, you’re not alone. Liability and umbrella policies can feel like an expensive mystery, especially when you...
#664: Have any of these thoughts ever crossed your mind? If I had more willpower, I’d achieve my financial goals. I’m doomed to fail with money. Budgets suck. They only show me what I did wrong ...
#663: We’re living through the first era in which an investor can ask a machine to read a decade of SEC filings in seconds. That sounds powerful, but also a little terrifying. Can we trust it? And ...
#662: Most teams hire for skills. The best teams hire for wiring. What if the reason someone accelerates your organization, or quietly derails it, has more to do with their response time, proce...
#661: When your income drops, debt spikes, and a rental property starts bleeding cash, it can feel like your entire financial foundation is cracking beneath you. Veronica, our first caller, is navi...
#660: Caring for an aging parent can morph into a second full-time job, and even the most financially savvy adults get blindsided. Bank accounts freeze, home sales stall, and family savings disappe...
