Phil's Tax Hacks

The Truth About Managing Money with Multiple Advisors

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Some people believe having two financial advisors means double the wisdom, but it often means double the confusion. Phil explains why splitting your money between advisors can lead to conflicting advice, missed tax opportunities, and unnecessary complexity. He shares a real listener question about this exact dilemma and breaks down when it might make sense to have multiple specialists on your team.
Here’s some of what we discuss in this episode:
🥚 Eggs in One Basket Myth: the truth about “diversifying” advisors
⚖️ Conflicting Advice: how different strategies can cancel each other out
📉 Investment Overlap: how duplication of funds can lead to unintended risk
💬 Who’s in Charge? you become the quarterback when no one else is
 
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Retirement Healthcare Costs Just Jumped Again (2025 Update)

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Health care costs are rising faster than almost every other expense in retirement, and the latest numbers prove it. Phil breaks down Fidelity’s 2025 estimate showing that a 65-year-old couple retiring today can expect to spend around $172,500 on health care alone, not including long-term care. With Medicare premiums increasing and more retirees unprepared, Phil shares proactive strategies to stay in control of your retirement budget before medical expenses take a bigger bite than expected.
Here’s some of what we discuss in this episode:
📈 Healthcare Inflation: Growing faster than the cost of living
🏥 Medicare Myths: What Parts A & B really cover (and what they don’t)
🧾 Long-Term Care: The major expense not included in most estimates
💡 HSA Advantage: Using triple-tax-free savings for future care
 
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Where Should You Invest $1 Million in Today's Market?

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If you suddenly had a million dollars to invest, where would you put it, and how would you decide? That was the question put to three financial advisors in a recent Financial Advisor Magazine article. Today, Phil reacts to their strategies and adds on several important layers that are often overlooked, but could make or break your plan.
Here’s some of what we discuss in this episode:
⚖️ Risk vs. Reward: How personality drives portfolio choices
🤖 Innovation Bets: AI, tech stocks, and global ETFs
🪙 Alternative Assets: Gold, Bitcoin, and energy exposure
💬 Age Matters: Why advice changes in your 40s vs. 60s
💰 Tax Awareness: Why investment structure matters as much as return
 
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Is It Finally Time to Buy Bonds Again?

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For years, bonds were the “boring” part of a portfolio, but with higher yields, many investors are asking if bonds are finally back. In this milestone 300th episode, Phil breaks down what’s really happening in the bond market, why values fell so sharply in 2022, and how rising rates are changing today’s opportunities. 
Here’s some of what we discuss in this episode:
💼 Why investors are suddenly talking about bonds again
🔁 “Timing” the bond market rarely works
💬 Quotes from U.S. Bank and Fidelity on 2025 bond trends
🎯 How to use bonds wisely within a balanced portfolio
 
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Reacting To Unfiltered Retirement Takes from YouTube

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Forget polished advice. If you want the truth about retirement, read the YouTube comments. In this episode, Phil reacts to the fears, frustrations, and strategies that real people are posting online. He highlights the recurring themes that show up again and again: claiming Social Security early, bridging healthcare gaps and the psychology of money.
Here’s some of what we discuss in this episode:
💬 YouTube comments ≠ your personalized plan
🛠️ A DIY financial plan may end up costing you
🕒 Claiming Social Security early has lasting consequences
💰 Retirement income is about more than averages
 
Erin Talks Money YouTube Channel:
https://www.youtube.com/watch?v=3uLpg-GaUC8 
 
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The 5 Must-Do’s In Year One of Retirement

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Well, you’re retired. Now what? Some people subscribe to the “first year rule,” which says that the majority of your best retirement months will take place in the first year. How can you be strategic during that time and set the tone both emotionally and financially? In this episode, Phil walks through five essential steps for making your first year of retirement a success.
Here’s some of what we discuss in this episode:
💵 Establish a withdrawal strategy  
🧭 Pursue purpose so retirement feels meaningful, not empty
🏃‍♂️ Prioritize health and movement while you can
🎯 Test-drive financial and lifestyle choices to see if they’re a good fit
📆 Use year one to set habits that last
 
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The Truth About Downsizing in Retirement

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Downsizing in retirement seems like a no-brainer, but it’s not that simple. In this episode, Phil tests some of the most common beliefs about downsizing and whether they really hold up. Is moving to a smaller home always cheaper? Does it automatically lower your taxes? Will it actually simplify your life, or just trade one set of challenges for another?
Here’s some of what we discuss in this episode:
🏠 Downsizing isn’t always cheaper than staying put
💰 Property taxes can jump when you reset your tax base
📉 Transaction costs (commissions, moving, new furniture) cut into equity
👨‍👩‍👧 Family dynamics and emotional ties play a big role
🧭 Lead with lifestyle goals, not just financial ones
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The Hidden Medicare Penalty You Might Be Paying

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Think Medicare is free at 65? Think again. Many retirees are shocked to learn about IRMAA- the Income-Related Monthly Adjustment Amount- a hidden surcharge that can quietly add thousands of dollars a year to Medicare costs. In this episode, Phil explains how IRMAA works, who’s most at risk, and which types of income can trigger it.
Here’s some of what we discuss in this episode:
💸 IRMAA can add thousands to Medicare costs
⏳ Why premiums are tied to your income from two years ago
🧾 The role of RMDs, capital gains, and pensions in triggering IRMAA
🛠️ Smart planning moves like Roth conversions to lower exposure
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How to Change Careers at 55 Without Ruining Retirement

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After years in the corporate world, you’re ready for something different. Something hands-on, flexible, or more meaningful. But the big question looms: will it wreck your retirement plan? In this episode, Phil dives into the financial and personal realities of changing jobs at 55, showing how to make the leap thoughtfully while still protecting your long-term goals.
Here’s some of what we discuss in this episode:
📈 Why rerunning your numbers can save your future plans
💸 The real risks of dipping into retirement accounts early
⚕️ Surprising costs you face when you lose employer benefits
💡 Smart business planning for your second-act career
 
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Inflation Is Still Wrecking Retirement Confidence

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Inflation may no longer dominate headlines like it did in 2022, but it’s still a top concern for many Americans planning for retirement. A recent Schwab survey shows how inflation affects confidence and preparedness for the future. In this episode, Phil explains why the psychological impact of inflation often feels worse than the actual numbers and how perspective matters for long-term planning.
 
Here’s some of what we discuss in this episode:
🔥 Why inflation headlines feel worse than reality
🤔 How “recency bias” can influence your financial decisions
⚠️ Why 401(k) loans and hardship withdrawals should be a last resort
🏦 Social Security COLAs: how cost-of-living adjustments help retirees
🎯 The importance of regularly rerunning your retirement plan
 
Schwab Survey
https://www.usatoday.com/story/money/personalfinance/2025/07/29/inflation-retirement-savings-survey/85413630007/
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96
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