Overview
Teaching you all about IRAs & Roth IRAs, employer retirement plans, taxes, Social Security, Medicare, portfolio withdrawal strategies, annuities, estate planning and much more!
210 Episodes
Andy discusses the various areas of consideration and analysis that go into deciding whether Roth conversions might potentially be of value. Furthermore, he explains why it's impossible to actually quantify how much tax savings, if any, Roth conversions might potentially create. And what to consider when figuring out how much to convert in any given year Links in this episode: Vanguard's "Break Even Tax Rate" Roth conversion analysis white paper - hereTenon Financial's June 2026 Newsletter/...
Transcribed - Published: 4 June 2026
Listener Q&A where Andy talks about: Claiming your own Social Security benefit at 62 and then later switching to collecting a spousal benefit after your spouse starts their benefit ( 5:45 )It's said by comedians that there are just a small number of basic jokes and everything else is just a variation. The same could be said about financial planning, where there are just a few core topics, and everything else is a variation on a core topic ( 11:18 )What is meant when it's said the st...
Transcribed - Published: 28 May 2026
Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Daryl. They talk about a wide array of retirement planning topics such as when he started getting serious about planning for retirement, how he's gotten comfortable spending from his nest egg, what he's doing for health insurance since he's not yet on Medicare and what his claim to fame was with being on television... Links in this episode: Tenon Financial month...
Transcribed - Published: 21 May 2026
Andy and Brad Flood from Tenon Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Portfolio withdrawal strategies for addressing sequence of returns risk ( 10:44 )Using financial planning software and dealing with its limitations ( 26:25 )Thoughts on Medicare surcharges known as IRMAA, and how much they should be factored into tax planning ( 40:25 )Dealing with legacy investments in client's accounts...
Transcribed - Published: 14 May 2026
Andy discusses the different options for holding cash and cash equivalents (i.e. things that are principal protected, offer some amount of interest and are highly liquid and readily accessible) The options are: Physical bills and coinsChecking accountsSavings accountsCertificates of Deposit, or CD'sMoney Market Mutual Funds or Exchanged Traded Funds that invest like Money Market Mutual FundsMulti-Year Guaranteed Annuities, or MYGA's (but hear why he doesn't fully consider them cash equivalent...
Transcribed - Published: 7 May 2026
Guest host Mark Rosinski, CFP®, CPA, RICP®, from Dunes Financial does a "hot topics" episode where he talks about: US Government obligation interest and what to look for on your consolidated 1099 to make sure you properly reflect the state income tax treatment on your tax return ( 9:06 )Understanding and tracking after-tax "basis" in inherited IRAs ( 20:14 )Required Minimum Distribution ("RMD") aggregation rules ( 25:03 )Potentially doubling up contributions to governmental 457 employer retir...
Transcribed - Published: 30 April 2026
Listener Q&A where Andy talks about: Correction to a previous Q&A episode regarding taxation of lump sum Social Security benefits paid in one year for benefits attributable to the prior year ( 9:54 )His thoughts on artificial intelligence and how it can impact the financial planning industry ( 13:00 )The "withhold and replace" method of paying taxes when doing IRA distributions or conversions and using the indirect 60-day rollover approach to ultimately pay taxes out of your ban...
Transcribed - Published: 23 April 2026
Special edition 200th episode where Andy shares some of his observations about the financial services industry from his time working in it: Creating good and consistent content is hard to do and do well ( 9:32 )A lot of content is just clickbait to get your views and/or advertise something to you, and not actually good content ( 13:15 )Personal finance is a lot more personal than it is finance ( 17:40 )The vast majority (all?) of long-term retirement planning is ultimately just a lot of educa...
Transcribed - Published: 16 April 2026
Andy and Jonathan Vance from Vance Financial Planning share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Given current world affairs and their impacts on the markets, should you do anything different with your investments, or are there any other planning opportunities to consider ( 14:20 )Tax updates for 2026, and some recap of tax takeaways for 2025 now that the 2025 tax return season is mostly behind u...
Transcribed - Published: 9 April 2026
Andy discusses the pros and cons of taking a lump sum vs taking monthly payments for your pension, questions to ask yourself to help figure out if it might be better for you to take one vs the other, and other considerations to keep in mind in making the decision Links in this episode: www.ImmediateAnnuities.comwww.PBGC.govTenon Financial's April 2026 newsletter - Whether to take a pension as a lump sum or monthly payments Tenon Financial monthly e-newsletter - Retirement Planning Insights...
Transcribed - Published: 2 April 2026
Listener Q&A where Andy talks about: How often to check your accounts for rebalancing, and how often to check on your bigger picture finances and plan ( 2:32 )What to do with old positions you no longer want in a brokerage account but they all have large unrealized gains ( 16:03 )How Medi-Cal benefits interact with a high deductible health plan and an HSA (spoiler alert...I don't know!) ( 22:20 )Are there any good reasons to leave old/prior employer 401(k) plans where they are ( 25:...
Transcribed - Published: 26 March 2026
Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Jim Kellerman. They talk about a wide array of retirement planning topics such as when he started getting serious about planning for retirement, how he now spends his days in retirement, what he's doing for health insurance since he's not yet on Medicare and why he's at the local prison each week... Links in this episode: Puritas tax prep software (including for ...
Transcribed - Published: 19 March 2026
Andy chats with fellow retirement planner Bradley Hilton, CFP®, TPCP®, MBA from Sonas Financial Planning. In this episode they talk about a wide array of retirement planning topics such as tax planning, distribution strategies, investing, annuities, long-term care insurance, what consumers often overlook in retirement planning and much more! Links in this episode: Bradley's advisory company website - https://www.sonasfp.com/ or https://www.sonasfinancialplanning.com Tax Foundation summary o...
Transcribed - Published: 12 March 2026
Andy discusses the ins and outs of gifting, the annual gift exclusion, gift splitting, gift taxes, gift tax returns (IRS Form 709) and more! Links in this episode: Tenon Financial's March newsletter/blog about gifting - hereIRS Form 709 - here 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 Plann...
Transcribed - Published: 5 March 2026
Listener Q&A where Andy talks about: Income tax treatment of buying bonds in a normal non-qualified brokerage account when you buy or sell bonds in between coupon periods ( 8:37 )When still working, are 50 or older, are maxing out your 401(k) contributions, and are high income and therefore would need to have your catch-up contribution go into your Roth (instead of pre-tax) 401(k), would it be better to skip the catch-up and instead put that money in a normal brokerage account ( 14:...
Transcribed - Published: 26 February 2026
Andy chats with a real person (not an advisor) doing their own retirement planning. This week Andy is joined by Kevin Sebesta from the Rock Retirement Club Kevin retired at 43 as part of the FIRE (Financial Independence, Retire Early) concept. He shares his planning and retirement journey, and discusses more about FIRE including the FIRE community and thoughts everyone (not just FIRE folks) should consider when planning for retirement. Links in this episode: Kevin's blog - ww...
Transcribed - Published: 19 February 2026
Andy and Jason Cutitta from ToBa Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: How to incorporate a potential inheritance into your retirement planning ( 12:30 )Limitations of the "Die With Zero" concept ( 18:55 )The upcoming ability to do in-plan Roth conversions in the federal Thrift Savings Plan ( 29:06 )Whose retirement accounts to take from first when spouses have a big age disparity ...
Transcribed - Published: 12 February 2026
Andy does a deep dive into everything about "backdoor" Roth contributions, which is where you make an after-tax contribution to a traditional/pre-tax account, and then convert it to a Roth account. Looks simple on the surface, but there are a lot of angles and gotchas to watch out for Links in this episode: IRS Form 8606 - hereCongressional meeting summary from December 2017 meeting on the Tax Cuts and Jobs Act - here Tenon Financial monthly e-newsletter - Retirement Planning InsightsFac...
Transcribed - Published: 5 February 2026
Andy shares his background and how/why that shaped his views, beliefs and approach to providing tax-efficient retirement planning and related content through the Retirement Planning Education website, podcast, YouTube channel, blog and Facebook group 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 Planni...
Transcribed - Published: 29 January 2026
Listener Q&A where Andy talks about: Can a spouse claim spousal benefits while delaying the start of their own benefit ( 10:40 )What's the best way to view your accounts in terms of how much of them are actually yours after accounting for eventual taxes you have to pay on them ( 14:08 )Can a minor be named as the beneficiary of a retirement account ( 23:28 )His thoughts on dividend stocks and funds ( 26:55 )Follow up thoughts about combining retirement account, in response to a prev...
Transcribed - Published: 22 January 2026
Andy chats with a real person (not an advisor) doing their own retirement planning. This episode is a bit different from our normal real people chats though. Andy is joined by Kevin Lyles from the Rock Retirement Club. Kevin is a retired corporate lawyer who has since become a certified retirement coach, focusing on helping people with the non-financial aspects of retirement. In the episode, Andy & Kevin talk about six "Retirement Truths:" You never know when you have enough; there are ...
Transcribed - Published: 15 January 2026
Andy and Cody Garrett from Measure Twice Financial share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Affordable Care Act ("ACA") tax credits and income "cliffs" in tax planning ( 08:13 )Doing Roth conversions vs tax gain harvesting ( 22:30 )Paying taxes in retirement; estimated payments vs withholdings ( 31:33 )Rushing into Roth conversions ( 38:50 )When to start doing HSA distributions ( 51:31 )Should ...
Transcribed - Published: 8 January 2026
Andy shares his thoughts and commentary about 2025 returns and events for: U.S. stocksInternational stocksU.S. bondsGold & SilverBitcoin 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 questi...
Transcribed - Published: 1 January 2026
Listener Q&A where Andy talks about: Potential advantages or disadvantages of consolidating retirement accounts ( 4:28 )Paying taxes through IRA withholdings vs making estimated payments ( 13:08 )Whether a minister's housing allowance impacts Affordable Care Act subsidy eligibility ( 26:11 )When Qualified Longevity Annuity Contracts ("QLACs") might make sense to consider ( 30:27 )When following the 4% "rule" for distributions, can you reset your initial distribution if/when your por...
Transcribed - Published: 25 December 2025
Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Jill. They talk about a wide array of retirement planning topics such as leaving the workforce relatively early, keeping expenses moderate yet still doing and enjoying a lot in life, what she wishes she would have known and done sooner for her retirement planning, and more! Links in this episode: Tenon Financial monthly e-newsletter - Retirement Planning Insights...
Transcribed - Published: 18 December 2025
Andy and Kevin Thompson from 9i Capital Group share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Thoughts on how the One Big Beautiful Bill Act complicates 2025 tax planning. And in particular whether people 65 or older should try to keep their income low to get some or all of the extra $6k bonus deduction ( 7:41 )What's up with the markets??? Should we be worried about the stock market? ( 17:33 )Their vie...
Transcribed - Published: 11 December 2025
Listener Q&A where Andy talks about: A correction on something incorrect I said last week regarding deciding which spouse's pre-tax account to distribute or convert from ( 3:28 )Pros and cons of using a single total global stock market fund vs multiple other funds such as just US and just international ( 8:17 )What's in the calculation for Modified Adjusted Gross Income ("MAGI") for purposes of determining eligibility to contribute to a Roth IRA ( 14:49 )Deciding when to start...
Transcribed - Published: 4 December 2025
Listener Q&A where Andy talks about: Starting Social Security benefits early so your minor children can claim dependent benefits, and how the earnings test can come into play if you're still working ( 5:53 )Social Security spousal benefits, and what happens when the lower earning spouse starts their own benefit early at a reduced amount, then later switches to spousal benefits ( 10:35)Social Security survivor benefits and whether the surviving spouse should start their own benefits ...
Transcribed - Published: 27 November 2025
Andy chats with a real person (not an advisor), Beth Pinsker, a columnist for MarketWatch, about her new book, My Mother's Money, A Guide to Financial Caregiving. In the book, Beth details her personal experience in becoming her mother's financial caregiver, both during her mother's end of life and health decline, and beyond her mother's death and through the estate administration process. The book provides tons of practical knowledge, insight and recommendations for how to ensure your financ...
Transcribed - Published: 20 November 2025
Andy and Ben Brandt from Retirement Starts Today share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about: Thoughts on Monte Carlo analysis; the good, the bad, the ugly ( 9:10 )Why all retirement plans are ultimately wrong as soon as they're made, and need to be agile and adaptable ( 13:30 )How to try to help people get comfortable spending the money they've accumulated ( 22:53 )Should people care how financial a...
Transcribed - Published: 13 November 2025
Andy shares some year-end tax planning tips, deadlines and things to consider around the following topics: contributions to qualified accountsRoth conversionsdistributions from qualified accountsRequired Minimum Distributions ("RMDs")charitable donationsQualified Charitable Distributions ("QCDs") from IRAsgiftingtax loss and tax gain harvestingdoing a projected/pro forma 2025 tax return Links in this episode: Tenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group...
Transcribed - Published: 6 November 2025
In this special guest host episode, Brian Tegtmeyer from Truly Prosper Financial Planning talks about how to address and plan for the non-financial aspects of retirement such as intellectual engagement, purposeful activities, health and fitness, relationships and more. And he also shares a quick exercise to do to see how you can measure your satisfaction in these various areas, and how to help intentionally address the ones you feel need improvement Links in this episode: Truly Pros...
Transcribed - Published: 30 October 2025
Listener Q&A where Andy talks about: The CAPE (Cyclically Adjusted Price to Earnings) Ratio as a measure of whether the US stock market is overvalued or undervalued, and drawbacks with the CAPE Ratio ( 4:32 )The meaning of Benjamin Graham's quote "In the short run, the stock market is a voting machine, but in the long run it's a weighing machine" ( 17:07 )Helping clients overcome their frugality habits to enjoy more of their deferred spending from their nest eggs ( 19:18 )Understand...
Transcribed - Published: 23 October 2025
Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Jackie Cummings Koski. But Jackie isn't just the typical "real" person doing her own retirement planning. She went the F.I.R.E. (Financial Independence Retire Early) route and left her corporate job in her late-40s. She's since expanded on the financial knowledge she gained during her F.I.R.E. journey to get a masters degree in financial planning and coaching, obtain the CFP® ...
Transcribed - Published: 16 October 2025
Andy chats with fellow retirement planner Allen Mueller, CFA, CFP® from 7 Saturdays Financial. In this episode they talk about a wide array of retirement planning topics such as tax planning, distribution strategies, investing, annuities, long-term care insurance, how to know when people have enough to retire, what consumers often overlook in retirement planning and much more! Links in this episode: Allen's advisory company website - 7 Saturdays FinancialAllen's blog - hereAllen's LinkedIn P...
Transcribed - Published: 9 October 2025
Andy shares his views on the few different ways in which people in the financial services/financial advisory industry can receive revenue: Commission-onlyFee-onlyHybrid or fee-based Links in this episode: My article in Rethinking65 - 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 Demys...
Transcribed - Published: 2 October 2025
Listener Q&A where Andy talks about: How to calculate how much money you can gift or donate in retirement without running out ( 8:47 )Does the five-year rule met by a previous Roth IRA carry over to a new Roth IRA ( 17:03 )Is it better to draw down an inherited IRA and delay starting Social Security, or vice versa ( 19:39 )Can distributions from an annuity in a 403(b) be used to meet Required Minimum Distributions in IRAs ( 23:37 )How to get cash flow or income from illiquid assets ...
Transcribed - Published: 25 September 2025
Andy chats with a real person (not an advisor) doing their own retirement planning. In this episode, Andy talks with Scott. They talk about a wide array of retirement planning topics such as leaving the workforce early than planned during COVID and later reengaging in part-time work to have social interaction, managing income for purposes of Affordable Care Act premium tax credits, how life and financial plans always change even in retirement, and more! Links in this episode: T...
Transcribed - Published: 18 September 2025
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 adviso...
Transcribed - Published: 11 September 2025
Andy summarizes some helpful IRS tools and interesting IRS and tax return-related information after his recent attendance at the annual IRS Tax Forum/conference Links in this episode: IRS Taxpayer Online Account - hereID.me - hereIRS IP PINs - hereIRS Document Upload Tool - hereIRS Interactive Tax Assistant - here Tenon Financial monthly e-newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Plann...
Transcribed - Published: 4 September 2025
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 re...
Transcribed - Published: 28 August 2025
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-newsle...
Transcribed - Published: 21 August 2025
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 h...
Transcribed - Published: 14 August 2025
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 happen Links 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 vid...
Transcribed - Published: 7 August 2025
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 accounts Links in this episode: Optimum Retirement Planning's website - https://www.optimumretirementplanning.com/ Tenon Financial monthly e-newsletter - Retirement Planning Insi...
Transcribed - Published: 31 July 2025
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...
Transcribed - Published: 24 July 2025
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 P...
Transcribed - Published: 17 July 2025
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...
Transcribed - Published: 10 July 2025
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 curren...
Transcribed - Published: 8 July 2025
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.RetirementPlanningE...
Transcribed - Published: 3 July 2025
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