Episodes

Feb. 13, 2023

Can ChatGPT Replace Your Lawyer (or other professional advisor)?

In this episode, we explore the rapidly evolving field of AI and its potential impact on the world of professional advising. Can a machine like ChatGPT truly replace the expertise and personal touch of a human advisor? Today we put …

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Feb. 6, 2023

Listener Voicemails - Answering More Social Security Questions

Answering listener questions is becoming our favorite episode to record. Today we go back to the voicemail to answer several questions on Social Security. Want to ask Devin or John your question? Just visit and look for the tab on …

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Jan. 30, 2023

Finding the Right Tax Advisor

Finding the right tax advisor can be a frustrating experience. Today, we talk to Steven Jarvis, CPA about the steps you should take when looking for a new advisor to help you with taxes. Steven is the owner of and …

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Jan. 16, 2023

Listener Voicemails - Answering (mostly) Social Security Questions

Today we go to the voicemail and answer some of our listeners questions. If you want to leave ask a question, visit and look for the tab on the right-hand side that says, "Send A Voicemail." Although this show does …

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Jan. 11, 2023

Secure Act 2.0

For the second time in three years, a new law has changed many of the rules about retirement planning. In today's episode, we'll dive into the headline items of this new law and then talk about some of the important …

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Jan. 3, 2023

Social Security at 62: Why Filing Ages are Changing

For a long time, 62 was the most popular age to file for Social Security benefits. But in the past several years, data has shown that it has become a less common age to file. There are three main reasons …

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Dec. 27, 2022

Legal vs. Insurable Title (How to avoid screwing up your real estate)

The value of a title policy, when it's needed, cannot be understated. There are some missteps that lead to not being able to get this insurance. Although this show does not provide specific tax, legal, or financial advice, you can …

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Dec. 19, 2022

Managing Tax Loss (AND GAIN) Harvesting with Andy Panko

Managing taxes in retirement may have a greater impact than any other single cost-saving measure you take. Today, we're joined by Andy Panko for a deeper dive into tax loss harvesting, and one that doesn't get a lot of attention...tax …

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Dec. 12, 2022

Listener Q&A: Inherited HSA, TOD Real Estate, Social Security spousal…

Today's episode is all about answering our listener's questions. Join the thousands who have already joined Devin's online workshop, How To Choose the RIGHT Time to File for Social Security. Get registered here Contact Devin’s team...

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Dec. 5, 2022

What Is a 1031 Exchange?

If you’re a real estate investor, you need to understand the 1031 exchange. This IRS rule allows for the chance to reinvest the profits from the sale of a property without having to pay capital gains tax. As long as …

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Nov. 28, 2022

Does Social Security Have An Inflation Donut Hole?

With all the attention given to the latest Social Security COLA, we’ve been getting lots of questions. Among the questions is about the alleged "donut hole" for Social Security inflation adjustments for individuals 60 and 61 years of age. Some …

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Nov. 14, 2022

Crash Course on Annuities

Do annuities deserve the bad publicity they receive? Today we'll do a crash course on the different types of annuities and talk about when one may be right for you. Although this show does not provide specific tax, legal, or …

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Nov. 7, 2022

Encore: The 5 Types of Trusts (and when they are used)

A trust is a legal entity, just like a corporation or an individual person. All trusts will have an exchange of property and three categories of people: the people who create it, called the grantors, or the settlers, or the …

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Oct. 31, 2022

How A Bear Market Can Maximize Your Retirement

For those who are retired, or getting close to being retired, a bear market is an anxious time. In today's episode, we talk about how you can PROFIT from a declining market and set up the rest of your retirement …

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Oct. 24, 2022

Big Changes To Social Security In 2023

In today's episode, we talk about a few of the Social Security changes for 2023 that will have a significant impact to retirees.These changes include: The 2023 cost of living adjustment The 2023 Earnings Limit The 2023 Maximum Family Benefit …

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Oct. 17, 2022

Nothing (Legally) Last Forever

Often described as one of the most complicated legal rules, the "rule against perpetuities" can prevent you from leaving assets to your family forever. In today's episode, we dive into this rule and talk about some of the states who …

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Oct. 10, 2022

Why 2023 Medicare Premiums Are Going Down

In 2023 the premium for Part B Medicare will be going DOWN. In today's episode we talk about how just one drug screwed up the forecasted premiums for 2022, and how that's being adjusted out in 2023.

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Oct. 3, 2022

A Better Approach to Retirement Income Distributions

In today's show we are joined by Benjamin Brandt for a discussion about the 4% rule (and how it goes against human nature), using a dynamic spending approach, and building a retirement budget that actually works. Connect with Benjamin Brandt …

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Sept. 26, 2022

Living In Sin: When Remarriage Causes Financial Harm

Thinking about getting married again? Before you do, it's important to understand the financial implications (that aren't always obvious). Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John...

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Sept. 19, 2022

Should You Use A Break Even Calculator for Social Security?

Can a Social Security break even calculator help you decide the best age to file? Yes! Just know…the results of this calculation alone cannot be the deciding factor when choosing the best filing age. Deciding when to file...

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Sept. 12, 2022

Deadline Looming To Avoid The Estate Tax

The tax code is set to have big changes in 2026. If you want to avoid estate taxes when these rules change, there may be steps you need to take TODAY! Although this show does not provide specific tax, legal, …

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Sept. 6, 2022

Should You Own An Airbnb for Retirement Income?

Airbnb has revolutionized the lodging industry. Today the value of Airbnb is only slightly less than Marriot, Hilton, and Intercontinental PUT TOGETHER! Should you stake your claim in the nightly rental gold rush? Joining us today is...

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Aug. 29, 2022

6 Social Security Mistakes That Can Damage Your Retirement

Some mistakes are easily recoverable. But others can cause long-lasting and near permanent damage. In today's episode John and Devin discuss the 6 Social Security mistakes that can damage your retirement. Although this show does not provide...

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Aug. 22, 2022

Checkbook Control LLC: How To Own Alternatives In Your IRA

The "checkbook control LLC" can be a great tool for investors looking to diversify beyond the traditional investments normally offered in an IRA. PLUS...if this is structured correctly you can retain control of the assets. Although this show...

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