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Wednesday, July 15, 2026

Tim compares the tax bill of two retired couples with identical Social Security benefits and spending needs. Couple 1 has $2 million in an IRA. Couple 2 has $2 million spread across an IRA, Roth IRA, and taxable brokerage account. $2...

Wednesday, July 1, 2026

Tim breaks down the Roth IRA five-year rules. Navigating Roth contribution and conversion timelines will help optimize your retirement tax strategy. Today I'm going to discuss the Roth IRA 5-year rule - or really, the 5-year rules,...

Monday, April 20, 2026

Tim explores a detailed financial review of a couple with a net worth of over $3.5 million, as they consider retiring at age 60. He covers assets, insurance, healthcare concerns, investment strategies, and tax planning to determine if...

Wednesday, January 21, 2026

Don't let your inheritance get hit with a massive tax bill! Tim breaks down the key tax differences among 3 major investment account types - tax-deferred, taxable, and Roth IRAs - and how each one is impacted when inherited. Today, I’m...

Tuesday, September 30, 2025

What if you had built a $3.5 million nest egg, owned your home outright, and still wondered: Can we really afford to retire at 60 and keep living the life we want? In this episode, Tim puts that exact question to the test for a couple...

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Wednesday, August 20, 2025

Tim dives into a real-world retirement planning scenario for a single professional with over $2 million in investable assets at age 56. He explores whether she can retire now while maintaining her current lifestyle, accounting for her...

Wednesday, June 25, 2025

See how Tim recently helped a couple with $1.5 million retire comfortably through tax planning, analyzing expenses, and determining probabilities. Check out this case study for insights on determining sustainable spending, maximizing...

Wednesday, April 23, 2025

Continuing with the theme of tax planning and how to bring down what you owe Uncle Sam, I’m going to cover a common question I get: Will capital gains push me into a higher tax bracket? Knowing how to navigate capital gains tax rules...

Saturday, November 2, 2024

Tim presents a case study for a couple with a net worth of nearly $3 million and $2.4 million in investable assets. Charlie is retired, while Lucy is considering retirement. See how Charlie and Lucy can best prepare for retirement, and...

Monday, June 17, 2024

Tim walks through a case study of a couple's retirement plan emphasizing tax planning, guardrails, and a war chest while stressing the importance of considering healthcare costs in retirement. Today I'm going to talk about a couple...

Thursday, June 6, 2024

Tim stresses the importance of separating a financial advisor's custodian from their own firm to prevent conflicts of interest and ensure investor protection. See why we feel that smaller, fiduciary firms like Eagle Ridge Wealth...

Thursday, May 16, 2024

Tim breaks down what a financial custodian is and their role in holding client assets. He discusses why his firm chose to partner with Altruist as its primary custodian. I’ve found that there is often confusion over how and where your...

Thursday, April 11, 2024

Tim breaks down everything you need to know about deploying a dynamic guardrail withdrawal strategy for a safe income stream during retirement. He uses proven research by Guyton and Klinger to dig into the details of how you can...

Tuesday, April 2, 2024

Learn how to maximize your retirement savings through strategic Roth IRA conversions. Discover how to thread the needle on conversions each year to minimize taxes over decades of retirement and avoid higher Medicare premiums down the...

Tuesday, February 13, 2024

Tim presents a retirement plan for a couple with $1.285 million in savings. He analyzes their cash flows, expenses, taxes, and withdrawal rates over time to determine if their savings will last through retirement. In a recent video, I...

Tuesday, February 6, 2024

In this video, Tim breaks down whether a $1 million nest egg is enough to retire on at age 65 in 2024. He discusses Social Security, Medicare, and strategies for withdrawing retirement income. Tim analyzes a client's specific situation...

Wednesday, December 20, 2023

Tim unveils a real-life case study of a couple worth $2.4 million. They were sitting on a "tax bomb" set to explode to over $1.7 million in taxes! Tim's strategy of Roth conversions and withdrawal planning could save them $2.2 million!...