If you’ve built or inherited an investment portfolio alongside the savings in your retirement accounts, you are likely to face some taxation every year on things like interest, dividends, and capital gains generated from the investments.

These might be investments such as stocks, bonds, mutual funds, or ETFs held in a brokerage account to name a few.
While these investments can serve as a fantastic compliment to your other retirement savings, you’ll want to be sure to manage this money in the most tax-efficient manner each year to allow your money to last as long as possible.

In this episode we discuss 6 year-end strategies to help you reduce the annual tax bill from your portfolio.

More specifically, I discuss:

• 7 basic tax rules you need to know when it comes to non-retirement investment portfolios
• Properly offsetting gains and losses
• Properly use long-term losses
• Avoiding the wash-sale rule
• Make use of lower tax brackets
• Donating appreciated stock to charity
• Do not donate depreciated stock to charity

Resources:

• Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
• Ask Cameron A Question!

Key moments:

00:00 Non-retirement accounts have annual tax implications

05:29 Capital gains can be taxed between 0% to 40.8% based on income and nature of gain

09:02 Properly offset short and long-term gains with losses to defer taxes and optimize savings

10:22 Consider strategic tax planning for mutual funds held in non-retirement accounts

15:04 Transfer appreciated stock to family in lower tax brackets

17:22 Donate appreciated stocks if itemizing deductions and charitably inclined

In a recent study published by the investment research company Morningstar, they estimate that the average dollar invested in funds by individual investors over the 10 years ending December 31st, 2023 earned a 1.1% lower rate of return per year than the actual investments they were invested in.

This resulted in individual investors out on nearly 16% of the investment’s actual returns each year, even without consideration of any investment fees.

Morningstar updates this data annually as part of their “Mind The Gap” study, and in this episode I break down why this is happening and what this means for investors.

More specifically, I discuss:

• What investing insights does this research show us?
• The difference in investor return “gaps” per asset classes invested in.
• Investors miss out on 50% of taxable bond fund returns!
• Why are many individual investors earning lower average rates of return than their investments themselves?
• The difference in investor return “gaps” based on the volatility of a particular asset class.

Resources:

• Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
• Ask Cameron A Question!

Key moments are:

00:00 Difference between investment and investor returns.

05:07 Investor behaviors remain consistent over the years despite political and economic uncertainty.

06:37 Return gap varies widely depending on asset class.

12:55 Investors tend to receive about 50% of bond fund returns.

16:33 The more volatile the fund, the more likely investor’s poorly time investment activity.

Kamala Harris and Donald Trump present starkly different tax proposals for the 2024 election reflecting their contrasting economic priorities. And while the exact outcomes of future tax policy are unknowable, you can be better prepared by having a good understanding of the potential changes.

In this episode, I address some of the major tax policies at play if either candidate takes office, and how they might affect your situation.

More specifically, I discuss:

• A basic review of the current tax laws in place under the Tax Cuts and Jobs Act (TCJA)
• What will happen if the TCJA sunsets (expires) in 2026 without intervention from either candidate?
• How might you be affected by the sunsetting of the TCJA.
• Brief overview of Harris’s main tax proposals and what it means for you.
• Brief overview of Trump’s main tax proposals and what it means for you.
• Will the State and Local Tax deduction (SALT) limits be removed before 2026?

Resources:

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

00:00 Political uncertainty surrounds future tax provision changes

04:15 Middle-class tax burden increasing significantly by 2026

08:01 Harris aims to raise taxes on the wealthy, but Trump’s cuts may be too expensive

11:12 Higher corporate taxes could mean higher prices

16:39 $10,000 SALT cap limits state tax deductions significantly

21:05 Existing small businesses may face tax increases in 2026

24:50 Tax proposals may influence voters significantly come November 2024

In today’s challenging and expensive economic environment, many young adults in their 20’s and 30’s are struggling to find stable footing when it comes to their finances.

Whether that’s struggling to find that perfect career that can help them pay off their student debt, saving enough for a downpayment on a first home, or having extra cash each month to pay for childcare.

These common issues are causing many parents in retirement to rethink their own situation by contemplating whether or not they should step in to help, and if so, how?

More specifically, I discuss:

• How to go about making the decision to help your children out financially from your own retirement resources
• Gifting and seeing your kids benefit from financial help while you’re alive, or let them inherit your wealth at death
• Potential financial and tax ramifications of gifting your children money or assets vs. inheriting
• Important things to consider before making the decision to help your children out financially
• Real-life case study of a retired couple with 4 children

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:

02:37 Case Study of retired couple wanting to help children financially

04:55 Capital gains implications and cost basis

07:45 Child daycare for grandchildren, downpayment for a bigger home

10:50 What to consider when deciding whether or not to gift children money

15:01 Consider family dynamics, fair inheritance, and taxes

18:50 Assessing your children’s “wants” vs. their actual “needs” and strategies to preserve wealth

When approaching a retirement from a long and successful career, you’ll likely have a list of big decisions to make in a relatively short time.

One of those decisions will be whether or not you should manage your retirement account(s) on your own after retiring - when you begin to convert them into an income stream to support your lifestyle. This is opposed to looking for outside help from a professional such as a financial advisor or planner, and it’s a decision that comes with both pros and cons.

However, before you decide, I think it’s important to understand what you may be getting yourself into since spending and distributing your retirement savings is much different than saving for retirement.

More specifically, I discuss:

• What does it mean to manage your own retirement savings?
• What common tasks and expertise does managing your own retirement account(s) entail?
• What are some of the pros and cons to the “do it yourself (DIY)” approach to investing?
• Common examples of costly retirement mistakes, even when it feels like you’re making money
• Should you take on the responsibilities of investment management and retirement planning or seek help?

Resources:

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

Chapters:

00:00 Managing your own retirement accounts: what's involved.

05:21 DIY investing can save direct costs but may have larger indirect costs.

09:55 Having accountability from a 3rd party may yield better outcomes.

13:57 Market drops can cause panic, lifestyle, and strategy concerns.

16:24 Have a plan to mitigate potential retirement risks and changes throughout life.

20:45 Examples of costly investment mistakes that feel like wins.

27:09 Managing your investments in retirement is not what you expect it to be.

When you have assets such as rental property that are going to need to provide you with cash flow throughout your retirement years, you’ll want to look into some level of asset protection at some point.

When it comes to rental real estate, the Limited Liability Company or LLC might be worth considering. However, the methods and strategies you use will depend on what you have at risk and certain risks that you might be creating yourself.

More specifically, I discuss:

• Setting up an LLC prematurely
• What is asset protection?
• Determining what assets to protect and how with examples
  
  • Basic asset protection techniques
  • What is a Limited Liability Company (LLC)?
• Benefits when used for rental property
• What does an LLC not do?
• How is an LLC commonly used for rental property?
• How can an LLC provide asset protection? - “Inside” & “Outside” liability
• When might you consider putting rental property in an LLC?
• Having your Revocable Living Trust own an LLC used for rental property
• Asset protection techniques to explore before creating an LLC

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 Asset protection, LLCs, benefits, drawbacks.

04:00 You may not need an LLC for your rental property

05:38 There are no silver bullet asset protection strategies, even LLCs

07:37 Potential benefits of an LLC for rental properties

09:25 Tax return ramifications with an LLC

10:45 Potential drawbacks of an LLC and what they don't do for you as a landlord

13:46 How can an LLC actually give you asset protection (inside and outside liability)

19:17 When might you consider putting your rental property in an LLC?

22:29 Series LLCs

23:30 Consider having your Revocable Living Trust own your LLC

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.