The 60/40 portfolio was the retirement gold standard for decades — so why is it failing so many retirees today? In this episode of the Retirement Risk Show, host Dave Hall breaks down where the 60/40 portfolio came from, why it worked so well for previous generations, and the 5 specific problems causing it to fall short for retirees now.

Dave traces the 60/40 portfolio back to Harry Markowitz's 1952 Modern Portfolio Theory, then walks through why bonds no longer provide the protection they once did, how sequence of returns risk can cost you 15+ years of retirement income, and why a single "one-size-fits-all" portfolio can't handle everything your money needs to do across a 20-40 year retirement. He also covers the bucket strategy approach to structuring retirement portfolios, how taxes quietly erode a 60/40 portfolio's returns, the real lesson behind Warren Buffett's wealth timeline, and a quick update on Trump accounts for kids and grandkids.

Whether you're actively planning for retirement, already retired, or just want to understand whether your current portfolio can support a multi-decade retirement, this episode breaks down what's changed and what to look at instead.

In this episode:

(1:14) The history of the 60/40 portfolio and Modern Portfolio Theory

(4:03) Problem #1 — Your portfolio has to do more jobs than it used to

(5:41) Problem #2 — Bonds aren't the hedge they used to be

(6:43) Problem #3 — Longevity risk and 20-40+ year retirements

(8:27) Problem #4 — Sequence of returns risk

(9:50) The bucket strategy — why one portfolio isn't enough

(11:07) Problem #5 — Taxes and portfolio inefficiency

(13:50) Portable retirement accounts and policy changes

(15:07) What Warren Buffett's wealth timeline really teaches us

(16:58) Trump accounts for kids and grandkids

(18:24) Risk tolerance vs. risk capacity

Want help applying this to your own retirement plan? Visit retirementriskadvisors.com for free tools, our blog, our email newsletter, on-demand webinars, and a no-fee consultation where we'll review your goals and help you figure out what your portfolio should actually look like.

New episodes of the Retirement Risk Show cover the risks, mistakes, and planning strategies that matter most as you approach and move through retirement — subscribe so you don't miss the next one.

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Investment advisory services offered through AlphaStar Capital Management, LLC, an SEC-registered investment adviser. SEC registration does not constitute an endorsement of the firm by the SEC, nor does it indicate that the adviser has attained a particular level of skill or ability. Fixed insurance products are offered through Retirement Risk Advisors, and AlphaStar Capital Management is not involved in the offer, recommendation, sale, or management of commission-based fixed insurance products. AlphaStar Capital Management and Retirement Risk Advisors are separate and independent entities. This episode is for informational purposes only and is not intended as legal, tax, or investment advice, or a recommendation of any particular security, investment product, or investment strategy.

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How do the ultra-wealthy actually plan for retirement? In this episode, CPA and retirement risk advisor Dave Hall reveals 6 things the ultra-wealthy do differently in their retirement and wealth planning — and how you can apply the same strategies to protect your own retirement.

Drawing on years of experience as a CPA working directly with billionaires and high-net-worth individuals on tax planning, Dave breaks down the pattern he saw again and again: the ultra-wealthy aren't smarter or luckier with money — they're following a different system than most Americans ever get access to.

In this episode, you'll learn:

- Why the ultra-wealthy focus on outcomes, not just financial products
- How "family office" style coordination between advisors leads to better retirement outcomes
- Why they obsess over taxes — and why taxes may be the single largest expense of your retirement
- The difference between liquidity and safety, and why chasing one without the other can quietly cost you
- Why they think in generations instead of planning only for themselves
- Why they build a complete retirement system instead of just a portfolio

Whether you're already retired or getting ready for retirement, these six shifts can help you avoid the irreversible mistakes that quietly derail retirement plans in the second and third decades of retirement — long after most people think they're in the clear.

This episode is part of an ongoing series on navigating risk in retirement. To learn more or schedule a meeting with our team, visit https://retirementriskadvisors.com.

If you found this episode helpful, please follow the show and leave a rating or review — it's the best way to help other retirees and pre-retirees find this content.

Investment advisory services offered through AlphaStar Capital Management LLC, an SEC registered investment advisor. SEC registration does not constitute an endorsement of the firm by the SEC, nor does it indicate the adviser has attained a particular level of skill or ability. Fixed insurance products are offered through Retirement Risk Advisors, and AlphaStar Capital Management is not involved with the offer, recommendation, sale, or management of commission-based fixed insurance products. AlphaStar Capital Management and Retirement Risk Advisors are separate and independent entities. This episode is for informational purposes only and is not intended as legal, tax, or investment advice, or a recommendation of any particular security, investment product, or investment strategy.

Topics: retirement planning, retirement risk, ultra wealthy retirement strategies, family office planning, tax planning in retirement, generational wealth, legacy planning, retirement income

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In this episode, host Dave Hall of Retirement Risk Advisors breaks down the four biggest tax traps that quietly derail retirement plans — and the strategies to avoid them before they become irreversible mistakes.

For many retirees, taxes end up being the single largest cost of retirement — bigger than housing, healthcare, or even a long-term care event. Dave explains why decades of "save everything in your 401(k) and IRA" advice built up a tax bill many retirees don't see coming, how Required Minimum Distributions (RMDs) force you to pay an increasingly higher percentage of your account in taxes as you age, why the "Widow's Tax Penalty" catches so many surviving spouses off guard, and how capital gains and investment income are taxed differently than ordinary income — and why that matters for where you hold your investments.

Dave also covers practical strategies retirees can use, including Roth conversion planning, Qualified Charitable Distributions (QCDs), building a tax-efficient investment portfolio, and legacy planning moves that can help you pass more to your heirs tax-free.

Topics covered in this episode:

• Why taxes may be the biggest expense of your retirement
• Tax Trap #1: Large pre-tax retirement accounts (401(k)s and IRAs)
• Tax Trap #2: Required Minimum Distributions (RMDs)
• Tax Trap #3: The Widow's Tax Penalty
• Tax Trap #4: How capital gains and investment income get taxed differently
• Roth conversion strategy, and how to think about which tax bracket to convert up to
• Qualified Charitable Distributions (QCDs) as a way to offset RMDs
• Why Roth IRAs and Roth 401(k)s have no required minimum distributions
• Building a tax-efficient retirement portfolio to reduce "tax drag"
• Legacy and estate planning: Roth vs. traditional retirement accounts for beneficiaries

Retirement Risk Advisors helps retirees and pre-retirees build comprehensive, coordinated retirement plans — addressing investments, income, taxes, and legacy planning together instead of in separate silos. Learn more at retirementriskadvisors.com.

This episode is for informational purposes only and is not intended as legal, tax, or investment advice, or a recommendation of any particular security, investment product, or investment strategy. Investment advisory services are offered through AlphaStar Capital Management LLC, an SEC-registered investment adviser. SEC registration does not constitute an endorsement of the firm by the SEC, nor does it indicate that the adviser has attained a particular level of skill or ability. Fixed insurance products are offered through Retirement Risk Advisors; AlphaStar Capital Management is not involved in the offer, recommendation, sale, or management of commission-based fixed insurance products. AlphaStar Capital Management and Retirement Risk Advisors are separate and independent entities.

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Most retirement advice fixates on one number: your rate of return. But the risk that actually derails a retirement has almost nothing to do with your average performance — it's about when your losses happen. In this episode, CPA and retirement planner Dave Hall explains why structured income, not investment growth, is the real foundation of a secure retirement, and why the financial industry keeps the conversation focused on the wrong thing.

Dave breaks down sequence of return risk — the reason two retirees with the exact same average return and the exact same savings can run out of money 15 years apart, simply because of when the market dropped. He explains why the first 5 to 10 years of retirement are the highest-risk window you'll ever face, why most financial advisors are incentivized to keep your money invested and growing rather than spent down, and how guaranteed income can improve retirement outcomes by up to 30%. Dave also shares the 3-bucket, family-office-style income strategy his firm uses with clients, and the data on how guaranteed income changes not just financial security but how much retirees actually spend, give, and enjoy in retirement.

Whether you're a few years from retiring or already there, this episode will change how you think about what actually protects a retirement plan.

In this episode, you'll learn:

• Why market returns are the wrong thing to focus on in retirement planning
• What sequence of return risk is, and why it can cost you 15+ years of retirement savings
• Why the first 5 to 10 years of retirement are the riskiest financial window you'll face
• Why financial advisors are incentivized to keep your money invested and growing, not spent down
• How guaranteed income can improve retirement outcomes by up to 30%
• Why retirees without guaranteed income spend about 50% less than they safely could, and how guaranteed income closes that gap to 85%
• The 3-bucket family office retirement structure: income, reserve, and legacy
• Why reducing the risk of failure, not maximizing returns, should be the real goal of your retirement plan
• The #1 fear most people carry into retirement, and how to plan around it

About the host: Dave Hall is a CPA and retirement planner who has spent his career helping people move from a do-it-yourself, returns-focused approach to retirement toward a structured, family-office-style income plan built around reducing risk instead of chasing growth.

Connect with Dave and learn more about family office-style retirement planning: Website: https://retirementriskadvisors.com

Subscribe to The Retirement Risk Show so you never miss an episode on retirement income planning, sequence of return risk, guaranteed income strategies, and how to build a retirement plan that actually holds up.

Investment advisory services offered through Alphastar Capital Management LLC, an SEC registered investment advisor. SEC registration does not constitute an endorsement of the firm by the SEC, nor does it indicate the adviser has attained a particular level of skill or ability. Fixed insurance products are offered through Retirement Risk Advisors, and Alphastar Capital Management is not involved with the offer, recommendation, sale, or management of commission-based fixed insurance products. Alphastar Capital Management and Retirement Risk Advisors are separate and independent entities. This content is for informational purposes only and is not intended as legal, tax, or investment advice, or a recommendation of any particular security, investment product, or investment strategy.

Keywords: retirement planning, retirement income, sequence of return risk, guaranteed income, retirement risk, income planning, family office retirement planning, CPA retirement advisor, retirement income strategy, annuity income, retirement red zone, market downturn retirement

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Most retirement plans don't fail on day one — they fail in the middle, ten or fifteen years in, when it's too late to go back to work. In this episode of The Retirement Risk Show, host Dave Hall breaks down longevity risk, the retirement risk he ranks as the single biggest threat to a happy retirement in his book Getting Safely Through Retirement.

Dave starts with the story of a 91-year-old woman whose family called a police welfare check after she went two days without answering the phone — only to find she'd been fine the whole time, just too absorbed in a video game to check in. That story sets up the real topic: why the "average life expectancy" number you'll find online (around 79) is misleading once you've actually made it to 65, and why a healthy retired couple should be planning for one spouse to live into their 90s, not their late 70s.

From there, Dave explains why longevity isn't just one risk among many — it's a multiplier that makes inflation risk, market risk, and withdrawal risk worse with every extra year you live. He covers the retirement planning gap nobody talks about, the "independence illusion" that convinces retirees they're fine right up until they're not, how long-term care risk fits into the picture, and the silent tradeoff between overspending and underspending that traps most retirees who don't have a real plan. The episode closes with a practical framework: guaranteed income, built-in flexibility, reserves for the unexpected, and giving every asset in your portfolio a specific purpose.

If you're within a decade of retirement, already retired, or helping a parent plan for the years ahead, this episode will change how you think about how long your money actually needs to last.

Resources mentioned in this episode:
Getting Safely Through Retirement by Dave Hall — available at https://www.gstrbook.com/info
Learn more or schedule a consultation at https://www.retirementriskadvisors.com

New episodes of The Retirement Risk Show release weekly, covering the risks that actually derail retirement plans — longevity, inflation, market risk, sequence-of-returns risk, taxes, and long-term care — and how a holistic retirement plan addresses all of them together. Subscribe so you don't miss an episode.

Investment advisory services offered through Alphastar Capital Management LLC, an SEC-registered investment advisor. SEC registration does not constitute an endorsement of the firm by the SEC, nor does it indicate the adviser has attained a particular level of skill or ability. Fixed insurance products are offered through Retirement Risk Advisors, and Alphastar Capital Management is not involved with the offer, recommendation, sale, or management of commission-based fixed insurance products. Alphastar Capital Management and Retirement Risk Advisors are separate and independent entities. This podcast is for informational purposes only and is not intended as legal, tax, or investment advice, or a recommendation of any particular security, investment product, or investment strategy.

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5 Irreversible Retirement Mistakes: Social Security, Roth Conversions & Long-Term Care Planning

These are the retirement mistakes you only get to make once. On this episode of The Retirement Risk Show, retirement planner Dave Hall shares a story from early in his career — a real estate deal that taught him a hard lesson about due diligence — and uses it to introduce five irreversible retirement planning mistakes he sees again and again.

Dave covers:

Taking retirement income the wrong way, including why your Social Security claiming strategy matters, how claiming at 62 instead of waiting can mean a 76% cut in benefits, how to think through pension elections and lump-sum options, and how withdrawing from your portfolio during a down market can trigger sequence of returns risk.

Ignoring tax planning strategies, including how a Roth conversion strategy done early and managed annually can reduce lifetime tax drag, help you avoid IRMAA surcharges on Medicare, and protect your beneficiaries from a rushed 10-year withdrawal window.

Failing to plan for long-term care, including why 56% of retirees will face a long-term care event even though only 6% have done any long-term care planning, and when to self-insure versus buy a long-term care insurance product.

Relying too heavily on the stock market for retirement income, including how a lack of income diversity leaves retirees exposed to sequence of returns risk.

Lack of coordination across your retirement plan, including why an accountant, estate planning attorney, investment advisor, and insurance agent working in silos can quietly undermine an otherwise sound retirement plan.

If you're researching retirement planning, Social Security claiming strategies, Roth conversions, IRMAA, or long-term care insurance, this episode walks through all five.

To learn more or schedule a no-fee consultation, visit https://www.retirementriskadvisors.com.

Investment advisory services offered through Alpha Star Capital Management LLC, an SEC registered investment adviser. SEC registration does not constitute an endorsement of the firm by the SEC, nor does it indicate the adviser has attained a particular level of skill or ability. Fixed insurance products are offered through Retirement Risk Advisors, and Alpha Star Capital Management is not involved with the offer, recommendation, sale, or management of commission-based fixed insurance products. Alpha Star Capital Management and Retirement Risk Advisors are separate and independent entities. This content is for informational purposes only and is not intended as legal, tax, or investment advice, or a recommendation of any particular security, investment product, or investment strategy.

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Why do most retirement plans fail? It's not bad investments — it's that the entire system changed in the 1970s, and nobody updated the plan.

In this episode of the Retirement Risk Show, Dave Hall breaks down how retirement in America shifted from a pension-and-Social-Security "golden age" system to a do-it-yourself model built around the IRA (1974) and the 401(k) (1978) — and why that shift is the real reason 46% of Americans die without the money they need to get safely through retirement.

Dave covers the four structural problems this created: the shrinking income floor (Social Security now covers only ~40% of retirement costs, down from near 100% for pension-era retirees), concentration risk (you're now the only one managing your own outcome), uncertain withdrawals (no one tells you exactly what you can safely spend), and the full shift of responsibility from employers to individuals.

He also explains the three consequences retirees face as a result — losing the lifestyle they worked for, missing the window to maximize their legacy, and outliving their money — and walks through the three-part framework the ultra-wealthy use instead: guaranteed income, reserves for long-term care and short-term cash flow needs, and proactive legacy planning.

Whether you're years from retirement or already in it, this episode lays out why the traditional approach falls short and what a more resilient plan looks like.

Learn More @ https://www.retirementriskadvisors.com

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As the New Year approaches, Dave brings back on Brian Britt to tackle essential year-end financial strategies to bolster retirement plans. In this episode offers a wealth of information and practical advice for those looking to assess their financial fitness and ensure their retirement roadmap is on point.

Throughout the conversation, Dave and Brian explore key areas such as managing holiday expenses, setting realistic financial goals, and the importance of maintaining a detailed roadmap for retirement. Brian underscores the significance of having a clear plan, noting that people often lose their initial enthusiasm and drift away from their objectives without one. The discussion highlights the crucial role of regular check-ins with a fiduciary to keep the plan updated and capable of withstanding market downturns, rising taxes, or unexpected health issues.

The episode delves into the critical impact of age and health on retirement planning. Brian and Dave explain the urgency of making certain financial moves while one is still young and healthy to avoid future complications. They stress that if listeners have been delaying contributions to their retirement plans or making Roth conversions, now is the time to act to maximize benefits and minimize future tax liabilities.

Listeners will appreciate the deep dive into personalized financial strategies, as the hosts emphasize that the right plan is one that individuals can realistically commit to and follow through on. Dave and Brian also highlight the distinct difference between securing one’s own retirement lifestyle and planning for legacy. Whether it involves managing Social Security, executing Roth conversions, or ensuring that one’s legacy avoids unnecessary taxation, this episode provides actionable insights tailored to each unique situation.

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