Retired-ish

Having too much of your net worth tied up in one or a couple individual stocks can be a dangerous game to play. It's one that relies heavily on luck and can present a significant risk to your life savings.

Things can either turn out really well, or very poorly. Sadly, many people often let their emotions and the potential tax ramifications dictate their next move, but should they?

In this episode, we discuss the risk of relying on one or two companies' success to dictate your financial future, and how you can begin to mitigate that risk while saving taxes.

More specifically, I discuss:

• Why are large, concentrated stock positions a potential problem?
• What types of investors might have highly concentrated stock positions?
• What if the majority of my compensation is via employer stock?
• The dangers of relying on one company and overconfidence
• How to diversify your concentrated stock position
• Examples of methods you can use to divest of shares
• Tax efficient example of reducing concentrated stock positions, diversifying, and saving taxes
• A little-known strategy to consider if you have appreciated company stock positions inside your 401(k)

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

Key moments:

00:00 Diversify investments to minimize risk and avoid emotional biases

05:34 Active management and stock picking often fails to outperform benchmarks.

07:59 Timing markets is risky; consider long-term goals.

10:31 Diversification benefits

16:44 Expect intra-year stock market declines

18:54 Strategy for controlling taxes and staying diversified in the market with concentrated stock position

Implementing important estate planning documents is critical to leaving your ideal legacy upon your death.

Among the critical estate planning documents are wills and trusts. Often times, many people confuse the differences between the two, the benefits they can provide, and whether or not they need them at all!

More specifically, I discuss:

• Why getting the appropriate estate planning documents in place is so important
• What is a Will? What can it do?
• What is a Trust? What can it do?
• What is the difference between a Revocable Living Trust and an Irrevocable Trust?
• Common uses for Revocable Living Trusts
• Common uses for Irrevocable Trusts
• What Revocable Living Trusts and Irrevocable Trusts don't do
• How the titling of assets can work in your estate plan
• The importance of naming beneficiaries

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

Key moments are:

00:00 Estate planning: wills, trusts, assets, and advice. 05:09 What does a will do? 08:26 Title of property and beneficiary designations. 10:24 What can a trust do? 14:16 Revocable trusts does not offer tax benefits. 20:20 Irrevocable trusts can have significant tax implications, good or bad. 22:18 The importance of naming beneficiaries and titling assets appropriately. 26:35 Estate planning can save your family money.

Retirees and pre-retirees often struggle when it comes to spending down their nest-egg in retirement because of the fear of the unknown. No one wants to run out of money too early, yet most people would also like to enjoy what they've worked so hard for. So how do you find that balance? How can you know what you can spend, and for how long? Living off of your wealth is entirely different than building your wealth. Without a retirement spending strategy, most people are going to either end up really worried about running out too early throughout their retirement, but end up leaving a pile of money on the table when they die, or running out of money too early in retirement – which for some, can be scarier than death itself

More specifically, I discuss:

• Why are retirement withdrawal strategies important?
• The main types of retirement withdrawal strategies
  • Systematic Withdrawal Plan/Constant Dollar
  • Time-Based Segmentation or "Buckets"
  • Floor and Upside
  • Dynamic Spending Strategy
• Variations and examples of real-world withdrawal strategies
• Strengths and weaknesses of the different retirement income strategies
• LISTENER QUESTION: Excess IRA/Roth IRA Contributions

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

Key moments:

00:00 Decades of work for retirement, learning to spend. 05:09 Customized retirement planning requires personalized, flexible strategies. 07:15 Customize retirement income strategy to meet financial goals. 13:57 Constant Dollar Strategy / 4% rule 16:36 Time Segmenting and Bucket Strategy 22:28 Floor and Upside Strategy 27:20 Dynamic Withdrawal Strategy 34:47 Listener Question: Excess IRA/Roth IRA Contributions

Life insurance has become an increasingly controversial topic in recent years due to the opinions of financial gurus on YouTube, insurance salesmen, and media giants especially when it comes to using it as a vehicle to build wealth.

When considering life insurance as a wealth building vehicle, it really comes down to who is using it and how they are using it. Ultimately, when it comes to building wealth, permanent life insurance is a potential option, but only in very unique circumstances.

More specifically, I discuss:

• The two main types of life insurance
• The main types of permanent life insurance
• The structure of permanent life insurance
• The different variations of universal life insurance
• Benefits and downsides to permanent life insurance
• How permanent life insurance can be used to build wealth
• How to structure permanent life insurance policies for wealth building purposes
• Who should consider using life insurance to build wealth, and who shouldn't

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

Key moments:

00:00 Understanding when life insurance can build wealth.

05:58 Permanent insurance costs more than term insurance.

10:05 Universal life insurance allows tax-free loans.

13:35 Insurance policies allow redepositing, not like retirement.

14:58 Limited control over investments, potential for higher returns.

21:17 Evaluate costs and fit for wealth building.

23:11 Future episode will cover life insurance info.

Investing in real estate historically has been a tried-and-true method of building wealth over the long-run, if you have the right wherewithal and mentality to do it – Let's face it, it takes work.

However, as with any type of investment, investing in real estate has its own set of risks.

Without proper analysis, you can lose a lot of money even if you accept what looked like a great deal. Or, you might be generating minimal cash flow that could have been a lot more cash flow if you were better prepared when analyzing your real estate deals.

In this episode, we show you how to analyze a real estate deal and compare it with other investment opportunities.

More specifically, I discuss:

• Real estate is a numbers game
• Some of the risks involved with real estate investing
• The "4 Return Components of Rental Real Estate"
• The potential tax benefits of investing in real estate
• Analyzing a real estate deal
• Using your analysis to help you make decisions

Resources:

Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question!

Key moments are:

00:00 Real estate investing has inherent uncontrollable risks

04:07 Critical components of real estate investment analysis

07:25 Hypothetical 20% return on property investment

11:26 Consult a tax advisor for potential write-offs

14:17 Avoid negative cash flow with proper monitoring

18:27 Using analysis for hypothetical $650,000 inherited property

21:36 Low rate of return, mortgage doesn't matter

23:14 Conservative 4% annual appreciation yields $26,000

27:26 LPL Financial offers advisory services, consult professional

28:57 Municipal bonds tax free, consult advisor, no guarantees

2024 is an election year, and not just any election year, but what could be one of the most controversial election years in our Nation's history.

Given the constant influx of media hype around everything such as: geopolitical tension, political dispersion within the US, inequality, inflation, government spending and the nation's screaming debt levels, the collapse of the US dollar, student debt, the uncertainty of Social Security, all while the stock market has continued to new make new highs - Investors and everyday people saving for retirement are left to wonder, what's going to happen to my investments?

More specifically, I discuss:

• Does the US president influence US stock market returns in an election year?
• Have markets fared better during election years with a Republican or Democratic President?
• Does the political make up of Congress influence market returns in an election year?
• What should I do with my investment strategy during an election year?

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question!

Key moments are:

00:00 Presidents have limited impact on the economy.

03:48 Economy and stock market are driven by many factors.

09:59 Investing not tied to political party affiliations.

12:16 Worrying about market uncertainty can be counterproductive.

14:54 Invest carefully for long-term success in companies.

18:11 Investment strategy should match long-term goals.

Whether you're self-employed or an employee, a Health Savings Account or HSA can provide you with a triple tax benefit! Therefore, if you're serious about saving taxes and building wealth, it's critical to understand the benefits and rules of the Health Savings Account.

If an HSA makes sense for your situation, you can benefit by receiving tax deductions based on money contributed into the account, tax-deferred growth on any interest or gains earned on the investments inside the account, and potentially tax-free distributions from the account that you take for medical expenses.

The HSA is the only tax-advantaged account that has the ability to give you both a tax deduction for the money you put in, and tax-free withdrawals on the way out. Even better than the Roth IRA!

You can also invest the money inside an HSA in a wide variety of investments! In some people's opinion, it is seen as the ultimate retirement savings vehicle, so don't let the name fool you!

More specifically, I discuss:

• What is a Health Savings Account (HSA)?
• The triple tax benefits of an HSA
• The rules and eligibility requirements when utilizing an HSA
• Who should consider an HSA?
• The "13-month" or "last month" rule when contributing to an HSA
• The 3 methods of using an HSA
• Other unique strategies and other opportunities unique to HSAs
• BONUS: HSA strategy for adult children under age 26 with high earnings such as professional and college athletes, entertainers, business owners, and young professionals
• LISTENER QUESTION: HSA contributions and Medicare!

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

Key moments:

00:00 HSA for healthcare savings provides a triple-tax advantage.

03:38 HSA offers triple tax benefits for saving.

09:02 Eligibility for HSA: high deductible health plan.

11:04 Consider plan's deductible, out-of-pocket expenses. HSA criteria.

16:41 HSA contributions and potential penalties explained.

18:08 At 65, take money out - no penalty.

23:00 Be careful of double dipping with taxes.

28:42 Maximize HSA contributions for long-term tax benefits.

30:20 Listener Question from Diane

Are you tired of handing over too much of your money to the tax authorities every year? Or wondering if there's a better way to go about managing your cash flow when it comes to paying your taxes?

If so, it's time to take control of your finances and maximize your wealth building machine. In this episode, I will show you how to adjust your tax withholding to keep more money in your pocket throughout the year so you can create a plan to make more of your money work for you, and not the IRS.

More specifically, I discuss:

• Understanding tax withholding
• Why adjusting tax withholding is important
• Major factors to consider when adjusting tax withholding
• How to determine the appropriate tax withholding or estimated payment amounts
• Steps to adjust tax withholding or making estimated payments
• Exemption from tax withholding

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

The key moments in this episode are:

00:00:00 - Tax Withholding Challenges

00:03:17 - Importance of Adjusting Tax Withholdings

00:06:11 - Avoiding Underpaying Taxes

00:11:56 - Factors to Consider When Adjusting Withholdings

00:15:36 - Understanding Withholdings and Tax Advice

00:16:13 - Tax Implications of Inheritance and Investments

00:17:32 - Tax Considerations for Starting a Business

00:18:57 - Navigating IRS Withholding Calculator

00:25:32 - Options for Adjusting Tax Withholdings

00:31:51 - Qualifying for Tax Exemption

00:32:26 - IRS Lock-In Letter

00:33:04 - Updating Form w Four

00:34:11 - Maximizing Financial Growth

If you are nearing retirement and have your eyes set on that dream day on the horizon (or even if you have recently entered into retirement) you need to know that you're more responsible now - than ever in our nation's history - for figuring out how to save, invest, and convert the financial resources you've spent your entire life accumulating into spending power that will last you a two to three decade retirement.

You are responsible for doing the necessary planning ahead of time in order to fund your ideal lifestyle in retirement.

More specifically, I discuss:

• How your retirement income will drive your ideal lifestyle
• The importance of after-tax retirement income
• The timing of your retirement income and how it can affect your lifestyle
• The risks that can threaten your lifestyle in retirement
• The role of personal preferences when doing your retirement income planning

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

The key moments in this episode are: 00:02:01 - Retirement Income Efficiency 00:04:48 - Risks and Obstacles in Retirement 00:09:03 - Real Estate Investment Case Study 00:13:21 - Personal Preferences and Retirement Goals 00:15:45 - Understanding Retirement Income Streams 00:16:26 - Listener Questions and Newsletter 00:17:11 - Sharing the Show and Learning Opportunities

It seems that each and every year when our firm reviews tax returns in consultations and second opinions we find dozens of missed tax savings opportunities: whether it be missed deductions, forgone strategies, less than ideal business entity or real estate structures, or simply improperly reported figures.

This holds true whether you do your taxes yourself with an online software or use a professional. Sometimes these missed opportunities are due to honest mistakes, other times it is due to tax documents with improper figures such as 1099s from investment firms, but more often than not it is due to the complex tax code and the lack of awareness of the potential strategies available to you and how to properly implement or report them when filing.

Every year we are reminded of the importance of reviewing tax returns to make sure that these savings opportunities aren't continuously missed in future years, and you pay more in taxes than necessary or have to pay penalties that could have been avoided.

In this episode, we review some of the areas of your tax returns you should pay more attention to, and some of the potential strategies to be on the lookout for.

More specifically, I discuss:

• The first steps to take before beginning your tax preparation
• What to look out for when receiving tax documents such as W-2s and 1099s
• Common pitfalls and errors to watch out for when gathering information and inputting it into your individual tax returns
• Commonly missed deduction opportunities for business owners
• Potential carryover losses for beneficiaries of a trust or estate
• What to do with your newfound tax savings

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Free Retirement Jump-Start Analysis
• Ask Cameron A Question!

The key moments in this episode are: 00:00:00 - Missed Tax Savings Opportunities

00:01:29 - Importance of Reviewing Your Tax Return

00:03:05 - Checking Tax Documents

00:08:25 - Providing Accurate Information

00:11:52 - Tax Considerations for Investments

00:16:08 - Understanding Tax Loss Carryovers

00:17:06 - Taking Advantage of Market Decline

00:18:38 - Managing Tax Savings

00:19:35 - Seeking Second Opinion and Getting Retirement Planning Resources

00:20:56 - Investment Risks and Tax Considerations