Can the post office survive its cash crisis, and is a debt relief program actually making your debt situation worse?
What does the USPS financial crisis mean for your everyday life? Senior news writer Anna Helhoski talks to Elena Patel, co-Director of the Urban-Brookings Tax Policy Center, to unpack how the post office ended up at a critical financial junct ... Show More
Apr 20
AI in the Home Buying Process: What Works, What Doesn't, and When to Call an Expert
Find out how AI tools can help navigate the home buying process and where human expertise still matters most. Can AI help you buy a house with reliable information? What would you do if you had only ten years to live, received a $100,000 windfall, or lost your job with just one m ... Show More
45m 47s
Apr 13
What Does "Rich" Really Mean? Reddit's Personal Finance Questions, Answered by the Nerds
We discuss real Reddit posts that reveal how people actually think about wealth, financial breakups, frugal habits, idle cash, and 529 overfunding. What does it mean to be “rich” in 2026? What can you learn about personal finance from scrolling Reddit? Sean Pyles, CFP®, and Eliza ... Show More
55m 15s
Aug 2025
Smarter Strategies for Retirement, Wealth Building, and Taxes with Michael Kitces
#243: Discover smarter strategies to grow your wealth and create financial flexibility. We dive into when it makes sense to invest beyond retirement accounts, how to access savings early through Roth conversions and 72(t) distributions, ways to reduce taxes with HSAs, tax-advanta ... Show More
59m 45s
Nov 2024
521 | Mailbag: Backdoor Roth IRA, 4% Rule, and 401(k) Strategies
Business owners face a ticking deadline that could cost them $500 per day—yet many have never heard of it. The Beneficial Ownership Information form, due December 31st, is just one of the under-the-radar compliance issues that can derail even the most careful financial plans. In ... Show More
1h 7m
Jan 2025
Ask HTM - Supercharging Retirement as a Freelancer, HSA for Medical vs Retirement, & “Investing” in Your Primary Residence #934
Let’s dive into the week with some fresh listener questions we have lined up for you! And don't just stand on the sidelines- if you have a question you’d like us to answer, toss your voice memo our way. It only takes about 90 seconds to record and you can find a step by step guid ... Show More
52m 22s
Sep 2025
563 | Safe Withdrawal Rates, Drawdown Strategies, RMDs and 50 Year FI Timelines
The 4% rule might be dead—but not for the reason you think. New research suggesting a 5.5% safe withdrawal rate has been making waves in the FI community, and it sounds like great news for early retirees. The problem? The math doesn't hold up when you're planning for a 50-year re ... Show More
57m 25s
Apr 2025
Q&A: The Stock Market Sucks. Is Private Equity Any Better?
#601: Nick and his wife have $100,000 to invest, but they’re worried about the volatility of the current stock market. Should they look into alternative investments such as private equity? Even though Roth IRAs come with tax-free withdrawals in retirement, Josh is worried about h ... Show More
52m 53s
Jul 2024
2814: How to Save Money and Still Invest by Christine Sato with JenHayes on Financial Advice
Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com.
Episode 2814:
Christine Sato, in collaboration with JenHayes.Me, explains how to save money and invest simultaneously, even on a lo ... Show More
9m 39s
Feb 2025
3035: [Part 1] Generating Retirement Income Before Age 59 by Darrow Kirkpatrick of Can I Retire Yet
Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com.
Episode 3035:
Darrow Kirkpatrick explores various strategies, from leveraging taxable investment accounts to taking advantage of Ro ... Show More
10m 4s