Phil's Tax Hacks

A Market Strategy for Type A Investors: Why Doing Less Might Be Your Best Move

Today Phil’s talking about Type A personalities. If you’re driven, competitive, and goal-oriented then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire.
In this episode, Phil unpacks the tension between action and restraint when markets get choppy. He explores why high achievers often feel anxious during downturns, even when their long-term plans are sound.
Here’s some of what we discuss in this episode:
🧠 Why Type A investors struggle with staying still
💥 The hidden risks Type A personalities often overlook
🔍 How over-managing can backfire in volatile markets
🤝 Why the right advisor should match your mindset
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Why The Psychology of Money Says Your Emotions Matter More Than Math

Today Phil’s kicking off his new Financial Book Club with The Psychology of Money by Morgan Housel. This book isn’t just about money strategies. It’s about why we make the choices we make, even when they don’t seem to make sense. You might find that your mindset is a bigger advantage than any investment tip. If you’ve ever wondered why it’s so hard to stick to the “smart” plan, this conversation might hit closer to home than you expect.
In this episode, Phil explores four powerful ideas from the book, starting with the bold claim that no one is crazy when it comes to money.
Here’s some of what we discuss in this episode:
💭 Why your money story begins in childhood
🏠 The emotional math behind paying off your house
😬 “Never enough” syndrome in retirement planning
📉 Planning for market volatility and life’s curveballs
🚧 Why your retirement roadmap needs flexibility
 
The Psychology of Money by Morgan Housel: https://shorturl.at/bjzCl
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Can Real Estate Boost Your Retirement Plan?

Can real estate actually boost your retirement plan? Is renting a property a reliable source of income, or just added stress? The short answer: it depends. In this episode, Phil breaks down the many ways real estate can support- or complicate- your retirement strategy. From rental properties and house flipping to reverse mortgages, REITs, and home equity lines of credit (HELOCs), this episode covers the most common approaches people consider and the mistakes they don’t always see coming.
 
Here’s some of what we discuss in this episode:
📉 Rental property pros, cons, and tenant trouble
🔁 What to know about 1031 exchanges
🏦 HELOCs as an emergency tool
📊 REITs: real estate investing without the property headaches
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Turn Your Savings Into a Real Retirement Plan

You’ve worked hard, saved diligently, and now you’ve got a solid 401(k) and a few other accounts... but now what? In this episode, Phil answers a common question submitted by one our listener’s: How do I turn my savings into a real retirement plan?
We’ll walk through how to shift from accumulation to distribution, and explains how to organize your financial "stuff," take inventory, and define what retirement will look like for you.
Here’s some of what we discuss in this episode:
🗂️ Why a financial inventory is the first step
🛠️ How to use your savings as tools—not the plan itself
📆 When to start serious retirement planning (hint: it’s not the year you retire)
💵 Why income—not your total savings—is the number to watch
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Is 2025 a Bad Time to Retire?

Thinking about retiring in 2025? You're not alone, but the timing might feel a little... complicated. With stock market swings, whispers of a recession, economic uncertainty, federal layoffs, and tariffs making headlines, it's no wonder many are feeling uneasy. But what if you had 2025 circled on the calendar long before all this? Is it still a smart time to step away, or could it be the worst possible moment?
Here’s some of what we discuss in this episode:
🔄 Market dips, rebounds, and what they really mean for retirees
📊 Why your 401(k) settings from 20 years ago might need a fresh look
🛑 The risk of panic-selling and how to avoid it
💼 The value of advisor conversations in times of uncertainty
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Stop Sacrificing Your Future For Your Adult Kids

How much support is too much when it comes to helping your adult children financially? A growing number of retirees are facing the dilemma of supporting adult kids at the expense of their own retirement goals. Let’s talk about how to prioritize your finances and why keeping your kids on the payroll could erode away everything you’ve worked for.
Here’s some of what we discuss in this episode:
👨‍👧‍👦 Supporting adult kids? It might be more than you realize
📉 Unplanned help can quietly erode your retirement savings
💸 “Little things” like phone bills and insurance can add up fast
📊 Build financial support into your retirement plan on purpose
💬 Open conversations with your kids—and your advisor—are essential
 
Check out the Fortune article: https://fortune.com/2025/03/26/millennial-gen-z-adult-children-parents-monthly-payments-retirement/
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Caring for an Aging Parent: Financially Smart or Emotionally Costly?

Caring for aging parents is something many of us will face—but few are fully prepared for the financial, emotional, and logistical challenges that come with it. In this episode, we will tackle this common scenario for Baby Boomers and discuss what happens when you're part of the “sandwich generation”—caring for both kids and aging parents.
Our question today comes from someone whose 93-year-old mom has fallen twice in the past month, and he’s weighing two options: bring her to live with him or pay for in-home care out of his own pocket. Which choice makes the most sense, both financially and for his family’s well-being?
Here’s some of what we discuss in this episode:
🏡 In-Home vs. Facility Care – What’s cheaper, safer, and more sustainable?
💸 Tax Implications & Medicaid – What you need to know before paying expenses
📉 The Retirement Impact – How caregiving can affect your financial future
⚠️ Asset Transfer Risks – Why giving away the house can backfire without a plan
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

The HSA Secret: Can You Really Build a Tax-Free Retirement Fund?

Are HSAs one of the best tax-advantaged accounts out there? Can you really stockpile a massive balance and use it tax-free in retirement? This is what a listener wants to know so we’ll analyze whether that’s a potential pitfall or if she’s maximizing this planning tool.
Here’s some of what we discuss in this episode:
💰 HSA = A Supercharged Roth IRA? – Why it’s better than traditional retirement accounts🧾 Save Your Receipts! – The secret to accessing tax-free funds later📊 Investing Your HSA Funds – Should you keep it in cash or invest it?⚠️ Avoid Common HSA Mistakes – Withdrawal rules & penalties explained
 
0:00 – Intro
1:19 – Today’s question
1:46 – Yes, it’s true
3:36 – Better than a Roth?
7:25 – Investing HSA contributions
10:44 – What are qualified medical expenses?
12:22 – Other considerations
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Gold Rush 2025: Should You Get In?

Gold prices are surging, JPMorgan is making a massive $4 billion gold delivery, and people are wondering if they should invest in gold. Gold has long been promoted as a safe haven in times of uncertainty, but with markets shifting, inflation concerns lingering, and a possible trade war on the horizon, is now the right time to add it to your retirement portfolio?
Here are some of the key topics discussed:
📈 Gold at record highs – Is it too late to invest?
💰 Physical gold vs. ETFs – Pros, cons & key differences
⚠️ FOMO investing – Why jumping in now could be risky
🔄 Gold as a hedge – Smart ways to use it in your portfolio
 
0:00 – Intro
1:03 – Gold on the rise
4:04 – Downsides
8:55 – Owning gold
9:56 – Portfolio diversification
12:35 – Final thoughts  
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96

Trade War 2.0 - What Could It All Mean

With so much happening domestically and abroad from a financial standpoint, this week’s show is going to look into the implications of Trade War 2.0 and its potential effects on the economy and markets. Phil will break down the latest economic data, tariff announcements, and which sectors might respond positively to the changes.
Here’s what we discuss in this episode:
0:00 – Intro
1:08 – Market instability & tariffs
5:23 – Apple’s $500 Billion Investment
7:23 – Reactions to tariffs
13:11 – Tariff winners
16:46 – Gold
18:37 – Final thoughts
 
For more, visit us online: http://philstaxhacks.com
Watch the video podcast on YouTube: https://bit.ly/3WdDG96