In this Q&A episode, we tackle three questions that sit right at the intersection of money, time freedom, and life design. We start with a listener who’s planning a self‑funded sabbatical and needs to decide how much risk to take with savings earmarked for a very specific timeline. From there, the conversation widens into a…
Will you still have a job in five years? Zack Kass, a former OpenAI executive and 16-year AI veteran, joins us to unpack the question that keeps many knowledge workers awake at night. But instead of focusing on layoffs or wages, Zack reframes the conversation around something deeper and more unsettling: identity. We want faster…
What if paying off debt wasn’t the end of your financial journey, but the beginning of something bigger? In today’s episode, we meet three listeners at pivotal crossroads, each wrestling with how to align their money with what they truly want from life. First, we talk with a couple who’s about to crush $100,000 in…
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 rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages. The Not-So-Good: Health insurance…
In this Q&A episode, we tackle three listener questions covering portfolio efficiency, tax rules, and global diversification. We start with a deep dive into how to rebalance a seven-figure portfolio without triggering unnecessary taxes. Then we clarify a common (and risky) misunderstanding about dependent tax status and health insurance subsidies. Finally, we explore whether holding…
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, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth….
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 insights on long-distance investing remain just as relevant for anyone feeling priced out of their local market. We tackle the five biggest challenges…
![#673: Why Young Investors Focus on the Wrong Things [GREATEST HITS]](https://affordanything.com/wp-content/uploads/2025/07/OvkksR-6gJxgVZ0bYkYXoCofEFUwBkF4JrJaBf22RjA-768x1075.jpeg)
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, but the framework remains one of the most practical guides we’ve shared for building wealth at any age. Nick Maggiulli joins us to reveal why…
![#672: The Hidden Information That’s Costing You Money [GREATEST HITS]](https://affordanything.com/wp-content/uploads/2024/08/Jeff-Wetzler-Headshot-Std-res-for-sharing.jpeg)
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 2024, but the strategies are more essential than ever. Jeff Wetzler, Ed.D., reveals why the people around us withhold crucial information — and how asking…
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 that changed how thousands of our listeners think about money. This episode originally aired in November 2022, but the insights feel more relevant than ever….