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

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

In the SPECIAL EDITION episode, Andy summarizes the key provision of the recently signed into law One Big Beautiful Act that are most likely to impact you and your tax return. The topics summarized are:Permanency of the current federal tax ratesPermanency, and a slight increase, to the current standard deduction amountsA new temporary personal exemption up to $6,000 per person 65 or olderPermanency, and a slight increase, to the lifetime gift and estate size exemptionPermanency of the current Alternative Minimum Tax exclusion amount, but reduction/reversion of its income phase out levelsPermanency of the $750,000 limit on residential mortgage principal against which interest can be deductedPermanency of the elimination of miscellaneous itemized deductionsTemporary increase to $40,000 for State and Local Tax ("SALT") deductionsA new permanent charitable deduction for people who use the standard deductionA new minimum AGI-based floor on charitable donations before donations can be itemized deductionsA temporary exclusion from income tax of up to $25,000 tip incomeA temporary exclusion from income tax of up to $25,000 of overtime incomeA temporary deduction of up to $10,000 of interest loans to buy cars whose final assembly was in the U.S.Recissions of multiple "Green New Deal" tax credits such as electric vehicle credits and residential clean energy creditsCreation of new "Trump" savings accounts for children under 18And the bill having NO changes with regards to how Social Security is taxed (i.e. the bill did NOT make Social Security not taxable)Links in this episode:Final text of the One Big Beautiful Bill Act - hereMy written summary of the key individual income tax provisions of the One Big Beautiful Bill - 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 discusses the main ways in which investment custodians like Scwhab, Vanguard and Fidelity make money (even when you often don't outright directly pay them anything...)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]

Listener Q&A where Andy talks about: A short explanation of bonds and "the bond market" ( 2:48 )Are actively managed bond funds better than passive bond funds ( 21:53 )What are the pros and cons of making all of the year's estimated tax payments in the first quarter ( 30:30 )Why insurers don't offer a long term care product with a 2-3 years elimination period or deductible to cover just LTC needs beyond a few years ( 34:07 )His thoughts on getting retirement income from dividends, Treasury interest and municipal bond interest ( 37:20 )Are there any advisors who specialize in working with couples where only one couple is involved in the household finances ( 42:47 )Are there any disadvantages to converting ALL pre-tax account balances to Roth ( 46:20 )Is disability income considered "earned income" and eligible to make IRA or Roth IRA contributions ( 55:30 )To 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 three different "real" people to discuss how they handled the non-financial/emotional transition from working to retirement, and what they do now to provide a sense of fulfillment, meaning and purpose and in retirementLinks 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 Larry Pershing from Optimum Retirement Planning share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: The pending "Big Beautiful Bill" tax bill that recently was approved by the House; what's in it, what's not in it, practical planning considerations around it, etc. ( 8:12 )Potential concerns about US debt US government bond defaults ( 34:50 )Talking to kids and heirs about your estate planning and wishes for after you're gone ( 50:02 )Estimated tax payments for people who recently retire ( 59:40 )Sources and tools to consider using to do tax return and estimated tax estimates ( 1:02:27 )The level of the S&P 500's concentration to the top few companies and the technology sector ( 1:06:04 )Whether 1.75% of assets is a reasonable fee for a financial advisor to charge ( 1:19:07 )What to know and consider when keeping money behind in a 401(k) vs rolling it over to an IRA ( 1:26:01 )Links in this episode:Larry's firm - Optimum Retirement PlanningLarry's previous appearance on the Retirement Planning Education Podcast - #081 – Retirement planner chat, with Larry Pershing from Optimum Retirement PlanningTax Foundation's summary of the Big Beautiful BillStephanie Kelton's book - The Deficit MythThe DinkyTown 1040 estimatorThe IRS Tax Withholding EstimatorTenon Financial's August 2024 newsletter about - Employer plan-to-IRA rollover pros and consTo 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 discusses what financial firms do for their fee, using his own firm, Tenon Financial, as an exampleLinks in this episode:Tenon Financial's website - https://tenonfinancial.com/Tenon Financial's June 2025 newsletter - hereAndy's article explaining how it's impossible to quantify the value of advisory services in - How Much Are Your Services Worth?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]