#163 - Guest host Larry Pershing from Optimum Retirement Planning talks about managing and reducing concentrated stock holdings

Andy and Justin Pritchard from Approach Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: The pros and cons of target date funds ( 11:05 )Their thoughts on the recent presidential executive order allowing private and illiquid investments to be offered inside 401(k) plans ( 23:26 )Can you make up for insufficient retirement savings by investing more aggressively ( 31:51 )Understanding your advisor's succession plan and how to try to make the succession transition successful for you ( 39:35 )Things to consider when firing an advisor or changing advisors ( 46:39 )Whether people should consider getting a living/revocable trust ( 56:22 )Things to consider if you're looking to hold cash in banks in currencies other than US Dollars ( 59:53 )Links in this episode:Justin's firm - Approach FinancialJustin's YouTube channel - Justin Pritchard, CFP® on RetirementTo send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy summarizes some helpful IRS tools and interesting IRS and tax return-related information after his recent attendance at the annual IRS Tax Forum/conferenceLinks in this episode:IRS Taxpayer Online Account - hereID.me - hereIRS IP PINs - hereIRS Document Upload Tool - hereIRS Interactive Tax Assistant - hereTenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.comTo send Andy questions to be addressed on future Q&A episodes, email [email protected]

Listener Q&A where Andy talks about: How to account on your tax return for the basis in inherited IRAs ( 7:00 )Is having large Required Minimum Distributions ("RMDs") really a bad thing ( 12:04 )Is there any merit to using a break-even analysis to help decide when to start Social Security ( 15:59 )When does it make sense for someone to consider working with a financial advisor ( 18:14 )Are Roth contribution and conversion rules the same across all of the various types of employer retirement accounts like 401(k)s, 403(b)s, TSP, etc. ( 26:18 )Are there separate five-year holding periods for Roth conversions done in employer retirement plans ( 27:37 )Do in-plan Roth conversions each have their own five-year holding period to waive the 10% early withdrawal penalty ( 30:36 )Can Roth conversions be done before taking any distributions or doing Qualified Charitable Distributions ("QCDs") in the year someone turns RMD age ( 31:49 )If receiving Restricted Stock Units ("RSUs") or deferred compensation in years after you stop working, is that considered earned income eligible for making Roth IRA contributions ( 34:38 )Does taking a really large Health Savings Account ("HSA") distribution make you a higher audit risk in the eyes of the IRS ( 39:19 )Is there a way to invest in broad stock market exposure but without the ongoing dividends such index fund pay out ( 42:27 )Does the progress toward meeting the five-year rule within an employer Roth retirement plan port over to a Roth IRA or other employer Roth plans when doing a rollover, or vice versa ( 46:08 )How to plan and account for an inheritance that a person is rather certain to receive, but the timing of receiving it isn't certain ( 49:43 )To send Andy questions to be addressed on future Q&A episodes, email [email protected] in this episode:My company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com

In this slight twist to the "real" person episode format, Andy doesn't interview a real person but instead addresses the most common retirement planning questions he gets from "real" people. The questions addressed are:Do I have enough to retire?When can I retire?How much cash should I have?When should I start my Social Security?How do I get money out of my portfolio?How do I pay taxes?Should I do Roth conversions? If so, how much?Links in this episode:Tenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Andy and Mark Rosinski from Dunes Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Thoughts on common withdrawal strategies and what they use in each of their firms ( 12:04 )The level of impact of some of the changes in the One Big Beautiful Bill Act ( 30:51 )Things to consider when doing rule of 55 distributions from your employer retirement plan ( 37:56 )Their thoughts on how many funds and holding the stock portion of a portfolio should have ( 45:40 )When or if there are benefits to having multiple accounts of the same type, such as multiple IRAs, multiple brokerage accounts, etc. ( 57:31 )How to actually take distributions from a portfolio; from which accounts, in what frequencies, etc. ( 1:06:02 )General information and considerations about reverse mortgages ( 1:12:10 )Links in this episode:Mark's firm - Dunes FinancialMark's previous appearance on the show - Episode #146Retirement Income Style Awareness ("RISA") assessment - herePortfolio Visualizer - hereTo send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy summarizes the recent 2025 annual Social Security trustees report, including what it would actually mean if the system's trust fund were to deplete, and what changes can be made to ensure that doesn't happenLinks in this episode:The full 2025 Social Security trustees report - here My company's August 1 2025 newsletter summarizing the 2025 Social Security trustees report - hereThe newsletter contains the links I mentioned to the various other newsletters, podcasts and YouTube video's I've done on the topic of Social SecurityTenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com To send Andy questions to be addressed on future Q&A episodes, email [email protected]

In this special guest host episode, Larry Pershing from Optimum Retirement Planning talks about how to reduce and manage concentrated holdings in your investment portfolio. Particular emphasis is given to the tax implications and tax management of trying to reduce highly appreciated positions in normal brokerage accountsLinks in this episode:Optimum Retirement Planning's website - https://www.optimumretirementplanning.com/Tenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Listener Q&A where Andy talks about: Why you know the return you'll ultimately realize if you hold a bond to maturity, but can't know the return you'll eventually realize if you instead hold a bond fund ( 7:13 )A commonsense intuitive answer why bond prices decrease (increase) when interest rates increase (decrease) ( 9:56 )His thoughts on holding only fixed maturity instruments such as CDs, bullet ETFs, individual bonds and MYGAs for a fixed income allocation instead of traditional open-end bond funds ( 13:56 )How to distribute money from a 401(k) when you can't pick which particular investments to sell within it ( 22:44 )Will U.S. income tax rates eventually increase, and by how much ( 31:23 )How to make an investment policy statement ( 43:41 )What distribution plans and strategies typically look like for his clients ( 51:23 )Links in this episode:Morningstar article - How to Create an Investment Policy StatementTo send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com

Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Jan. They talk about a wide array of retirement planning topics such as leaving the workforce early due to family caregiving needs, how health changes have impacted retirement, how to distribute money from an IRA particularly when looking to do Qualified Charitable Distributions, and more!  Links in this episode:Tenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com To send Andy questions to be addressed on future Q&A episodes, email [email protected]

Andy and Lauren Hunt from Daybreak Wealth share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Their thoughts on the takeaways from 2025 annual Social Security Trustees report ( 7:17 )Some of provisions in the pending One Big Beautiful Bill Act that are likely to impact most people's tax returns ( 16:12 )Whether or not to get a loan or pay cash for a new car or house. Or, similarly, to pay down or pay off an existing loan ( 32:27 )Whether buying a 30 year Treasury bond is a replacement for a traditional income annuity in retirement ( 38:19 )When to consider getting a living/revocable trust ( 46:43 )Why the stock market keeps chugging ever-upward, even with so much seemingly uncertain in the world and the economy ( 54:38 )What longevity assumptions we use, and why, when doing financial planning and projections for client ( 1:07:45 )Links in this episode:Lauren's firm - Daybreak WealthLauren's prior appearance on the Retirement Planning Education podcast - Episode #098The 2025 Annual Social Security Trustees Report - hereTo send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com