#207 – Roth conversion analysis: more than meets the eye

Andy and Mark Ross from the Rock Retirement Club talk about Mark's journey in retiring to become an "encorepreneur" by starting a coaching business, and spending more time creating art. They also address some of standard "real person" planning questions such healthcare before Medicare, Social Security claiming, the emotional transition to leaving the corporate world, and more!  Links in this episode:Mark's coaching website - https://www.nextthinggroup.com/Mark's Instagram site for his art - https://www.instagram.com/next_thing_art/The Rock Retirement Club - https://www.rockretirementclub.com/Tenon Financial monthly e-newsletter - Retirement Planning InsightsYouTube 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]

Andy and Adam Grossman from Mayport Wealth Management share their thoughts on a handful of current events and "hot topics" relating to retirement planning. Specifically, they talk about:How to analyze an existing annuity and whether to keep it, exchange it to another annuity or surrender it ( 11:44 )The different things to factor in when considering retiring to a different state ( 23:18 )What to do with your investments regarding concerns about the U.S.'s national debt, potential inflation, potential market declines, etc. ( 33:41 )How much to try to optimize moving around cash balances between savings accounts, money market funds, Treasury Bills, CDs, etc. to try to maximize the amount of interest you can get ( 43:44 )Their thoughts on individual bonds vs bond funds, what we use, and why ( 54:27 )How we handle and implement inflation assumptions when doing financial planning with clients ( 1:05:37 )Their thoughts on how Artificial Intelligence may impact financial planning, both as advisors and as consumers ( 1:12:55 )What to make of illustrations for permanent life insurance policies, how reliable those illustrations are, when to consider buying permanent life insurance, when not to buy permanent life insurance, etc. ( 1:19:48 )Links in this episode:Mayport Wealth Management's website - https://www.mayport.com/Adam's recent appearance on Morningstar's The Long View podcast - https://www.morningstar.com/personal-finance/adam-grossman-asset-allocation-is-an-investors-best-defenseTo send Andy questions to be addressed on future Q&A episodes, email [email protected] company newsletter - Retirement Planning InsightsYouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com

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 yearLinks in this episode:Vanguard's "Break Even Tax Rate" Roth conversion analysis white paper - hereTenon Financial's June 2026 Newsletter/blog - Roth conversion analysis: more than meets the eyeTenon 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: 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 stock market is a "complex adaptive system," and that it's movement is a "random walk" ( 14:08 )How to determine how much tax to withhold from your Social Security payments ( 17:34 )Why many flat fee financial advisors who focus on working with retirees only work with people whose net worth is generally no more than $10 million ( 21:22 )Bonds vs bond funds, and the pros and cons of using each for money that you plan on needing in three years, for example ( 29:23 )An example of removing "cream from the coffee" with regards to after-tax contributions or basis in traditional IRAs, so you can convert just the after-tax contributions without the pro rata rule making some of that conversion taxable ( 33:44 )Participating in fully paid securities lending programs at your brokerage custodian, where the custodian will borrow some of your securities out of your account and pay you some interest for doing so ( 41:50 )Thoughts about rolling over an HSA from one custodian to another, and whether it's better to do a direct custodian-to-custodian transfer (even if the money is out of the markets for a few weeks), or an indirect 60-day rollover (which will likely be processed and reinvested faster) ( 48:10 )To send Andy questions to be addressed on future Q&A episodes, email [email protected] in this episode:Tenon Financial monthly newsletter/blog - 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 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 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]

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 when clients want to streamline and simplify their holdings, but also want or need to continue to hold some existing positions of theirs ( 46:14 )Balancing optimization and simplicity in financial planning; when is "good enough," enough? ( 58:29 )When in the year to take distributions from Required Minimum Distributions ("RMDs") ( 1:12:19 )A summary of our processes and semiannual meetings at Tenon Financial ( 1:19:02 )Links in this episode:Tenon Financial's website summarizing services and fees - https://tenonfinancial.com/services-and-feesTo 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 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 equivalents)Links in this episode:FDIC insurance calculator - https://edie.fdic.gov/calculator.htmlhttps://www.treasurydirect.gov/Tenon Financial's May 2026 Newsletter/blog - Options for holding cash and cash equivalentsTenon 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]

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 retirement plans, and other unique aspects of 457 plans ( 33:27 )Different approaches for investing money during the period where income from working has stopped but Social Security has not yet been started. Options include total return, bond ladders, bucket strategies, and hybrid approaches ( 46:35 )To send Andy questions to be addressed on future Q&A episodes, email [email protected] in this episode:Mark's company's website - https://www.dunesfinancial.com/Mark's first time on the Retirement Planning Education podcast - #146 – Retirement planner chat, with Mark Rosinski from Dunes FinancialMark's second time on the Retirement Planning Education podcast - #165 - "Hot topics" edition...Andy and Mark Rosinski talk about different withdrawal strategies, rule of 55 distributions, allocating the stock portion of a portfolio and MORE!Andy's YouTube video - IRA after-tax "basis," the pro rata rule and Form 8606Tenon Financial monthly newsletter/blog - 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

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 bank or brokerage account, but with the benefit of doing it via withholdings from the IRA ( 20:30 )Step DOWN in basis when inheriting assets that have declined in value from where the original owner bought them ( 31:46 )When having a pension available, instead of selecting a payment option that lives on for your spouse upon your death, instead taking the payment option that stops when you pass, and using the difference in the larger payment amount to buy life insurance for the benefit of your spouse ( 40:00 )His thoughts on using a TIPS ladder ( 45:29 )Whether to invest money or instead use it to buy long term care insurance. Such as deciding between making an $8,000 Roth 401(k) catchup contribution, or using some or all of that $8,000 to buy long term care insurance ( 50:48 )At what point does larger investable asset size or net worth start to lead to the need to have a more complex portfolio, or to invest in non-traditional assets like private investments, alternatives, etc. ( 54:31 )To send Andy questions to be addressed on future Q&A episodes, email [email protected] in this episode:Tenon Financial monthly newsletter/blog - 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

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 educated guesses and there is no way to create a perfect or infallible retirement plan ( 21:46 )Roth conversions are given too much attention and emphasis ( 28:15 )There are a lot of reasons to not like the financial services industry, and most (all?) of the industry is ultimately out to get you to buy something from them ( 33:30 )Most of the people in the industry are really good people and do really good work, but they just might not be working in a company or structure that prioritizes the client ( 37:52 )There is continued growth and momentum in financial advisors providing planning-focused services at more logical fee structures and service offerings ( 42:17 )Tax planning is getting more attention and more advisors are learning about and offering tax planning ( 43:50 )The percent of assets under management model doesn't make sense. There are other fee structures that are less illogical, less unfair, less arbitrary in what they charge ( 46:46 )The financial services and advisory industry is unfortunately really fragmented between different "factions" of companies, services, products, etc., and it ends up being a disservice to consumers ( 53:12 )Tax return prep is a hard business. Please be kind and considerate in dealing with tax preparers, especially in February, March and April! :-) ( 1:00:36 )Links in this episode:Episode 100 of the Retirement Planning Education podcast - #100 – 100th episode celebration!!! Andy's 100 words of retirement planning wisdomTo 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