Episode 514: FI-lanthropy Friendly Portfolios, Solving A Transition Quandary, Golden Bow Ties, And Portfolio Reviews As Of May 29, 2026

In this jam-packed crushed-fresh stone-solid hour-busting episode we do a trifecta response to one most excellent email from Rebecca.  We discuss portfolios for FI-lanthropy, options and resources for making a transition from a 100% stock portfolio with tax and ACA subsidy issues, the drawbacks of bucketeering compared with the joys of asset swaps, and the socio-political overhang attached to gold and how that is evolving towards more rational uses of it by big time retail personal finance and others.And THEN we our go through our weekly and monthly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.Additional Links:Fairfax CASA Donation Page:  Donate - Fairfax CASA Father McKenna Center Donation Page:  Donate - Father McKenna CenterWells 4 Wellness:  Wells 4 Wellness - Wells 4 WellnessYield & Spread/FI-lanthropy:  The FI-lanthropy Pledge | Yield & SpreadThe Portfolio Matrix Tool:  Portfolio Matrix – Portfolio ChartsOutline of Financial Advisor Best Practices:  Strategic Retirement Planning: A Summary of Best Practices from Tenon Financial - Google DocsHow To Do An Asset Swap Video from Risk Parity Chronicles:  How to Do an Asset SwapAfford Anything Risk Parity Portfolio Blueprint:  Afford Anything frank-vasquez-risk-parity-portfolio-BluePrint.pdf - Google DriveCatching Up to FI Gold Episode:  I Love Goooooold?! :) | Frank Vasquez | 184Interview of Bob Elliot on the Compound Podcast re Gold (start at 1:10):  The Blue Chips of Junk | TCAF 175Breathless Unedited AI-Bot Summary:You can do everything “right,” follow a simple index plan, retire early, and still wake up one day as an accidental 100% stock investor. That’s what happened to Rebecca and Joe, early retirees in their mid-30s who needed fast cash for a home purchase and ended up selling bonds and leaning on a margin bridge. Now they’re staring at a stock-only portfolio, big unrealized gains, and a real constraint most advice ignores: diversifying could blow up taxes and ACA health insurance subsidies.We walk through a risk parity mindset built for real life, not perfect spreadsheets. We use Portfolio Charts to compare diversified asset allocation models by safe withdrawal rate, volatility, Ulcer Index, and drawdowns, and we explain why portfolios like the Golden Ratio and Golden Butterfly can be surprisingly “philanthropy-friendly” if you want to spend and give consistently. Then we get practical: stop treating taxable and retirement accounts like separate buckets, rebalance the diversifiers inside retirement accounts first, and learn how an asset swap can fund spending while keeping your overall allocation on track.We also tackle the emotional side, especially gold. If gold feels like a doomsday signal, we unpack the uniquely American baggage behind that reaction, why ETFs changed everything, and how gold can function as plain old diversification alongside intermediate and long-term Treasury bonds and even managed futures. We close with our weekly sample portfolio reviews and June distribution updates so you can see the framework in motion.Subscribe, share the episode with a fellow DIY investor, and leave a rating or review so more early retirees can find a calmer way to diversify.Support the show

In this episode we answer question from Rob, Matthew, and Luke.  We discuss the pitfalls of trying to rely on an all-bond portfolio in retirement and better options, the problems with over-valuing financial simplicity over good living, the benefits of the Choose FI podcast, muddled thinking about the concepts of “self-cleansing” and the momentum factor, why reassessing a retirement plan beats obsessing over a perfect forecast, and why that's not likely to be necessary with a risk parity style portfolio due to its lower risk profile.Links:Father McKenna Center Donation Page:  Donate - Father McKenna CenterFairfax CASA Donation Page:  Donate - Fairfax CASAOptimus Bill's Risk Parity Radio Zoom Party (May 31 @ 4 pm EDT):  https://us06web.zoom.us/j/3125439422?pwd=dHh6aFlYRk9TWFZ4c29POTA4OThKUT09&omn=85117353750Portfolio Charts Bond Portfolio SWR:  Withdrawal Rates – Portfolio ChartsChooseFI Episode 570:  State of the Stock Market 2025 Q&A | Brian Feroldi | Ep 570ChooseFI Episode 574 (with Yours Truly):  Top Five Regrets of the Dying | Book Club | Ep 574Comparison of Large Cap Momentum with Other Common Factor Combinations:  Portfolio Backtester for ETFs and Asset Allocation | testfolioBreathless Unedited AI-Bot Summary:A 5% Treasury yield can make a bond-only retirement plan sound like the cleanest solution on earth: buy long-term government bonds, take the interest, stop watching markets, and never rebalance again. We slow that idea down and stress-test it the way a DIY investor should, starting with the basics people love to skip: inflation-adjusted returns, real purchasing power over decades, and the ugly surprise of turning your whole portfolio into federally taxable ordinary income. “Simple” can get expensive fast when taxes and inflation show up every single year.From there we zoom out to the part that rarely makes it into retirement math. We talk about why chasing simplicity for its own sake is a false goal, how fear-based planning can push you toward over-saving and underliving, and what it looks like to use money to actually improve your life. If what you really want is hands-off income, we also explain why annuities are purpose-built for that job and can be cleaner than fiddling with a bond ladder.Then we tackle an investing debate sparked by another show: are small caps “bad,” and what does “self-cleansing” even mean in index funds? We break down why all index funds are rules-based, how cap-weighted funds quietly embed a momentum tilt, and why small cap value still earns a role for diversification even when it lags for long stretches. We finish with a practical retirement planning mindset: instead of worshiping a perfect forecast, rerun the plan as life changes and make decisions based on today’s reality.Subscribe, share this with a friend who loves “simple” investing rules, and leave a review with the one portfolio myth you want us to unpack next.Support the show

In this episode we answer emails from TJ, Jose and Optimus Bill.  We discuss the foibles of trying to catch up via investment picking if you are behind on retirement, debunk CAPE-style and other crystal ball forecasts from "experts" that Level Two investors often fixate upon, lay out practical growth-tilted allocations that can beat narrative-driven investing and invite you all to contact Optimus Bill about your Risk Parity Radio listening habits.And THEN we our go through our weekly and monthly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.Additional Links:FI Service Corp DC Charitable Event:  DC Double PlayFather McKenna Center Donation Page:  Donate - Father McKenna CenterMichael Batnick Critique of CAPE Ratio "Predictions":  Stocks Are More Expensive Than They Used to BeAccumulating With a Golden Ratio Portfolio Article:  Minimize Your Miss – Portfolio ChartsCatching Up to FI Episode 100:  0️⃣ From Zero to Hero: A Late Starter’s Guide to the Galaxy 🌌 | Becky Heptig | 100Half US LCG/Half SCV Portfolio vs. US Total Market:  Portfolio Backtester for ETFs and Asset Allocation | testfolioInternational Half LCG/Half SCV Portfolio vs. International Total Market:  Portfolio Backtester for ETFs and Asset Allocation | testfolioMerriman ETF Recommendations:  Best-in-Class ETFs | Merriman Financial Education FoundationEmail Optimus Bill Here:  [email protected] AI-Bot Summary:The fastest way to get yourself into trouble as a DIY investor is to believe you can “catch up” with a smarter prediction. We start with a listener who’s anxious about high stock valuations, AI hype, and a potential lost decade and asks the question most people are thinking but rarely say out loud: does it really make sense to go all-in on stocks if you cannot afford a big drawdown?We break down why the real accelerator toward financial independence is usually your savings rate, especially when your investment pile is still small, and why a lucky run in individual growth stocks can create a dangerous feedback loop. From there we take a hard swing at valuation crystal balls like CAPE ratio forecasting and explain how to test any market-timing claim against forward-looking evidence and simple base rates rather than headlines and vibes.Then we pivot to practical portfolio construction. If you want growth without betting your future on a single narrative, we talk about diversification that actually changes the ride: balancing large-cap growth with small-cap value, thinking more clearly about international exposure, and knowing when risk parity diversifiers like long-term Treasuries, gold, commodities, and managed futures make sense. We also answer a high-earner question about moving from a real-estate-heavy balance sheet into a growth-oriented market portfolio and why we’re skeptical of robo-advisors when a simple ETF plan will do.If you like clear rules, real-world asset allocation, and a little portfolio performance nerdiness, hit subscribe, share this with a friend who’s chasing forecasts, and leave a review so more investors can find the show.Support the show

In this episode we answer emails from Luc, Deep, and Paul.  We discuss the French Canadian "Sak kosh" portfolio, try to help out the elder Sonia sleep well at night, distinguishing small cap blend funds from small cap value funds, and share how we use AI tools to summarize long investing content without losing the source material. Links:  Father McKenna Center Donation Page:  Donate - Father McKenna CenterThe Superman Portfolio Withdrawal Rates:  Withdrawal Rates – Portfolio ChartsThe Superman Portfolio Drawdowns:  Drawdowns – Portfolio ChartsThe Superman Portfolio Portfolio Matrix:  Portfolio Matrix With The Superman Portfolio.png - Google DriveRPR Episode 436 Summary Video:  RPR Episode 436 Illustrated: The Two Halves of Your Financial LifeAdmiral Ackbar's Best Practices For Retirement Planning:  NotebookLM - Retirement Tactical Briefing with Admiral Ackbar and Tenon FinancialDaniel Plainview's "I Drink Your Milkshake" Best Practices for Retirement Planning:  NotebookLM - Plainview Wealth ExtractionVideo Version:  NotebookLM - The Ruthless ExtractionBreathless Unedited AI-Bot Summary:A listener builds a Canadian “risk parity style” portfolio that looks like a mad science project on paper and then asks the question we all quietly worry about: is this clever diversification, or is it just complexity wearing a lab coat. We walk through the logic behind mixing small cap value, gold, long-duration Treasuries, managed futures, and a small dose of leveraged ETFs, plus the real constraint that changes everything for many investors: you can only buy what your country and accounts actually offer. I share how I think about backtesting when tools don’t support Canadian ETFs, why proxies can be useful, and why great historical results still don’t remove behavior risk.Then we shift to a common real-life retirement planning scenario: someone in their mid-70s sells a home, moves into a retirement community, and only needs about 2% per year from investments. Instead of forcing a complicated portfolio to do the job, I explain why a single premium immediate annuity can be the cleanest solution for a very risk-averse retiree, potentially covering that gap with a relatively small slice of the nest egg and letting the rest stay invested simply and calmly. We also talk about separating mandatory expenses from discretionary spending so the plan feels safe and sustainable.We close with a fast answer on asset location for a saver juggling multiple account types and debating small cap value placement. The punchline: make sure you’re actually buying small cap value, and don’t over-optimize what usually doesn’t matter much. Plus, a quick look at using Google NotebookLM to summarize long podcasts and documents in a way that stays grounded in the inputs you provide. If you found this helpful, subscribe, share the show with a friend, and leave a review so more DIY investors can find it.Support the show

In this episode we answer emails from Geraldo, Rock, Ute.  We discuss how to give well, shifting from big-name school donations to smaller charities with immediate impact, moving from individual stocks to a Golden Butterfly style portfolio with less stress, treating Roth conversions as optional and highly personal rather than automatic, using a conservative Interactive Brokers margin loan as a temporary cash buffer, lowering margin-call risk with diversification and alternatives, and pressure-testing inflation claims for retirees and comparing U.S. data with and older study from The Netherlands.And THEN we our go through our weekly and monthly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.Additional Links:Father McKenna Center Donation Page:  Donate - Father McKenna CenterWCI Podcast Episode re Charitable Giving with Rebecca Herbst:  How to Maximize the Impact of Your Charitable Giving - WCI Podcast #470Referenced Inflation Study Paper:  S1474747216000202jra 85..109J.P Morgan Inflation Study:  JP_Morgan_White_Paper_Three_Retirement_Spending_Surprises.pdf - Google DriveRAND Inflation Study:  Spending Trajectories After Age 65: Variation by Initial Wealth | RANDBreathless Unedited AI-Bot Summary:You can be “right” about taxes and still be wrong about living. We dig into three listener emails that expose a common trap for smart investors: turning retirement into an endless optimization project, while the real goal is a calmer portfolio, a sustainable withdrawal plan, and a life you actually want to spend money on.First, we walk through a practical way to transition from individual stocks to a Golden Butterfly portfolio without getting paralyzed by detail. We talk about why macro allocation matters more than the exact ticker list, how to think about growth vs value exposure, and why simplifying inside retirement accounts is usually easier than in taxable accounts where capital gains can bite. We also share what we’d try to eliminate first when someone is de-risking for retirement.Next, we zoom out to retirement tax planning and charitable giving. We discuss why blanket advice on Roth conversion strategy and withdrawal order often fails, what it means to “disgorge” traditional IRAs before RMD age, and how qualified charitable distributions (QCDs) can be a quietly powerful tool for charitably inclined retirees.Then we tackle margin as a tool, not a lifestyle. We break down using a conservative Interactive Brokers margin backstop, how diversification can reduce drawdowns and margin-call risk, and why assets like Treasuries, gold, and managed futures show up again in risk parity style thinking. We also address a listener challenge on retiree inflation and why country, data vintage, and healthcare systems can flip the conclusion.If you like clear portfolio mechanics with real-world tradeoffs, subscribe, share the show with a friend, and leave a review so more DIY investors can find us.Support the show

In this episode we answer emails from Milo, Scott, and Joel.  We discuss bad advisor incentives and how to classify them by their business models, identify the only business model you want to patronize, and then move on to Treasury STRIPS and rebalancing realities, practical withdrawal mechanics with a test portfolio, and why Bitcoin’s high correlation to tech stocks undermines its role as a diversifier. We also celebrate the final results of the Fairfax CASA matching campaign and share a thank-you message from their executive director.Links:Classifying Financial Advisors By Their Business Models:  Interacting with the Financial Services Industry with SC GutierrezKitces Article on Rebalancing:  Optimal Rebalancing – Time Horizons Vs Tolerance BandsBuilding a Sample Portfolio Video:  We Built a 5% SWR Retirement Portfolio Using Fidelity in 48 Minutes (Golden Ratio Portfolio) - YouTubeVideo on Managed Futures and SDMF:  Simplify SDMF in Focus - YouTubeBreathless Unedited AI-Bot Summary:A matching donor puts $20,000 on the table, the audience steps up, and suddenly Fairfax CASA is funded far beyond what anyone expected. We start with that story because it says something important about this community: you can be serious about investing and still lead with empathy. We share the final campaign results and a message from Fairfax CASA’s executive director about what this support means for children navigating foster care and the court system.Then we shift back to what Risk Parity Radio does best: practical emails from DIY investors who want clearer rules and fewer regrets. We talk about the “67-fund portfolio” problem, why complexity is often a sales tactic, and how to screen out conflicted advice from banks, credit unions, insurance shops, and big marketing-heavy firms. We also dig into the AUM model versus flat fee and hourly planning, plus why smart retirement planning often comes down to tax planning and behavioral discipline more than picking the perfect fund.From there, we get hands-on with portfolio construction and process. We cover Treasury STRIPS funds like GOVZ, why you cannot reliably time the best rebalancing moment during a recession, and what to do instead with partial rebalancing or rebalancing bands. We also answer a nuts-and-bolts withdrawal question using a test portfolio approach, and we close with a straight take on Bitcoin correlation: if it moves with stocks, it is not diversification. Along the way, we explain what “alternative assets” really means and why gold and managed futures keep showing up in risk parity style asset allocation.Subscribe, share this with a friend who’s tired of salesy advice, and leave a review so more investors can find the show.Support the show

In this episode we answer emails from Michael, Jim, and Optimus Bill.  We start with a 67-year-old investor who is all-in on equities and cannot sleep, and how changing portfolio allocations can lead to better rest. We share a framework of "the three H's" for determining whether you are Hustling, Hoarding, or Harvesting your way through retirement, and how that may impact your well-being over time. We also dig into why people chase bond ladders and bucketeering.And THEN we our go through our weekly and monthly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.Additional Links:Testfolio Analysis with Sleep-Better-At-Night Metrics:  Portfolio Backtester for ETFs and Asset Allocation | testfolioOptimus Bill's Bond Ladder Extravaganza Article:  Building a Bond Ladder with Individual Bonds and ETFsBen Carlson's Explanation As To Why Bond Ladders and Bond Funds are Functionally the Same:  Owning Individual Bonds vs. Owning a Bond Fund - A Wealth of Common SenseBreathless Unedited AI-Bot Summary:Your portfolio should not be a nightly stress test. We start with a listener who is 67, 100% in equity funds, and staring down retirement in the next one to three years while worrying about an extended downturn. From there we get practical about “sleep-at-night” portfolio design, comparing volatility, maximum drawdown, and even the Ulcer Index across common setups like an S&P 500 heavy approach, a Bogleheads-style three-fund portfolio, a classic 60 40 mix, and a risk parity style Golden Ratio portfolio.Then we zoom out to the bigger question of what money is actually for. I share a simple framework I call the three H’s: hustling, hoarding, and harvesting. We talk through how each approach affects real life outcomes like relationships, experiences, buying back your time, and giving, and why a portfolio that supports harvesting can matter more than a portfolio that simply wins a return contest.We also tackle a timely question about bond ladder ETFs and why so many ladder, bucket, and time-segmentation products keep popping up. The blunt take: a lot of it solves a fear problem more than a finance problem, and the difference between ladders and bond funds is often smaller than people think. We close with our weekly review of the eight sample portfolios, covering stocks, treasury bonds, gold, commodities, managed futures, and more.If this helped you think more clearly about retirement investing and diversified asset allocation, subscribe, share the show with a friend, and leave a review so more DIY investors can find it.Support the show

In this episode we answer emails from Zach, Brian, Holly and Optimus Bill.  We discuss a way to estimate retirement health care costs using current data, clear up the “index fund” labelling problem and talk about why indexed dogs and cats won't start living together, have fun with milkshakes, and map out what tends to help a portfolio survive stagflation.  But first we celebrate a huge community win for Fairfax CASA with Queen Mary.Links:J.P Morgan Inflation Study:  JP_Morgan_White_Paper_Three_Retirement_Spending_Surprises.pdf - Google DriveBen Felix Interview on Bigger Pockets Money:  Is Small Cap Value Worth It? Ben Felix Explains the Truth About AVUV & Factor InvestingHolly's Milkshake Link:  I can’t believe he didn’t notice 💀 #shortsBreathless Unedited AI-Bot Summary:One spreadsheet can calm a lot of retirement anxiety, especially when the scariest expense is the one you cannot “average” from your current budget: health care. We start with a listener question about forecasting medical costs and how to decide whether an HSA can realistically cover them. Instead of relying on hype filled calculators, we talk through an actuarial style method using real ACA marketplace premiums by age in today’s dollars, then turning that stream into a flat, term premium like estimate you can inflation adjust and stress test.We also tackle a worry we hear everywhere: if everyone is buying index funds, do they stop working? The answer depends on what you mean by “index fund.” We unpack the messy language around mutual funds vs ETFs, cap weighted vs other index designs, and why a better mental model is rules based “algorithmic” investing versus human stock picking. From there, we discuss why diversification often means holding more than just large cap weighted exposure, and why factor investing and small cap value tilts keep coming up in serious portfolio design.Then we wade into the market regime that makes risk parity listeners sweat: stagflation. We explain why managed futures often does the heavy lifting when inflation and rates trend, how commodities fit, why gold can help over long arcs but disappoint on the clock, and why concentrated sector bets in energy or utilities are not automatically the solution. We also share a realistic take on margin loans as a cash flow tool, including why broker interest rates matter if you ever use that lever.If you got value from this one, subscribe, share it with a DIY investor friend, and leave a review so more people can find the show.Support the show

In this episode we answer emails from Kyle, Tim, and Tim.  We discuss dealing with a recalcitrant parent who won’t talk about the straw in their milkshake,  outline flexible retirement withdrawal planning with asset swaps, and explain how to escape TSP limitations.And THEN we our go through our weekly and monthly portfolio reviews of the eight sample portfolios you can find at Portfolios | Risk Parity Radio.Additional Links:Fairfax CASA Donation Page:  Donate - Fairfax CASAFinancial Personality Traits Research Presentation:  Big Five Unified Financial Profiles Presentation.pdf - Google DriveTax Book:  Amazon.com: Tax Planning To and Through Early Retirement: 9798999841599: Garrett, Cody, Mullaney, Sean: BooksAdmiral Ackbar's Tax Book Summary:  Admiral Ackbar's Guide to Tax Planning in Retirement Slides.pdf - Google DriveKitces Article:  Tax-Efficient Retirement Portfolio Spending StrategiesAsset Swap Video from Risk Parity Chronicles:  How to Do an Asset SwapOptimus Bill on Bigger Pockets Money:  The Decumulation Strategy After Hitting Financial Independence | Bill YountOptimus Bill on the Morningstar Long View Podcast:  The Long View: Bill Yount: How Late Starters Can Find Financial IndependenceBreathless AI-Bot Summary:Someone you love is doing “fine” on paper, yet you can’t shake the feeling they’re getting quietly drained by bad financial products or high advisory fees. That tension is where we start: the hard part often isn’t investment math, it’s the relationship dynamics that make a parent shut down the moment money comes up.We read an email from a listener trying to help his retired mom who prefers to delegate and doesn’t want to learn finance. We talk through why children often can’t be “a prophet in their own land,” how to lower the temperature, and why it can be smarter to focus on replacing a poor-fit advisor instead of trying to force a DIY investing conversion. If your goal is preserving peace while improving outcomes, this is a realistic playbook.Next we get into retirement withdrawal strategy and tax planning. The usual media advice about which account to tap first falls apart once you factor in lifetime tax minimization, Roth conversion windows, Social Security timing, ACA subsidy cliffs, and IRMAA. We also explain the idea of an asset swap so you can reduce an inflated holding (like gold in a Roth IRA) while keeping your overall asset allocation and diversification intact.Finally, we answer a newly retired federal employee wrestling with Thrift Savings Plan limits, the case for a TSP rollover to an IRA, how to think about 72T SEPP planning account-by-account, and how to rebalance when not every asset is available in every account. We close with our weekly risk parity style portfolio review and the May distribution rundown across the sample portfolios.Subscribe, share the show with a DIY investor friend, and leave a review on your podcast app so more people can find it. What’s the toughest money conversation you’ve had with family?Support the show

In this episode we answer emails from Thirsty Horse, Mark, and Mike.  We discuss a wise friend and lessons on clarity, happiness, and preparing for the end, how we got involved with the Father McKenna Center and Fairfax CASA, and dig into the real work behind CASA and foster care.  Then we pivot back to practical investing and tax planning without shortcuts. Links:Fairfax CASA Donation Page:  Donate - Fairfax CASAChoose FI Episode on The Five Regrets of the Dying (and Mamie):  Top Five Regrets of the Dying | Book Club | Ep 574Breathless Unedited AI-Bot Summary:You can have a rock-solid retirement portfolio and still miss the whole point. We start with a final push for Mary’s Fairfax CASA fundraiser, then share why a Court Appointed Special Advocate matters for kids in the foster care system and what real advocacy looks like when courts, schools, and social services move slowly. Mary also tells a case outcome that sticks with you: a child moving from neglect and instability to a stable home after a parent does the hard work over years.From there, we answer a listener who asks the question behind so many “financial independence” plans: how do you decide what level of time, emotional commitment, and responsibility you can take on? Frank revisits the story of Mamie McCoy and the urgency that comes with a finite life, then we get concrete about the skills that make a strong CASA and the traits that help foster parents provide stability, empathy, and advocacy for children affected by trauma.We also handle classic Risk Parity Radio topics for the DIY investor: sustainable withdrawal rates, asset allocation, and diversification. We talk through an equity-heavy portfolio that adds long-term Treasuries like VGLT for recession insurance, plus our simple “give away 1% of your portfolio each year” goal for intentional generosity. Finally, we take on portfolio automation, rebalancing, and a big tax-planning mistake: discounting traditional IRA balances by a made-up percentage instead of modeling taxes properly and considering Social Security timing.If you get value from the show, subscribe, share it with a friend, and leave a rating and review. What’s one cause you’d actually show up for with your time?Support the show