Tax Loss Harvesting Debunked (AMA, E95)

Tax Loss Harvesting Debunked (AMA, E95)

Author: Jesse Cramer December 4, 2024 Duration: 59:45

Jesse is solo, answering your questions! Kate, a government worker with $650,000 in IRAs, is wondering how she can best rebalance her portfolio - and when. Dan seeks clarity on bonds' role despite recent poor returns, learning they offer portfolio stability and mitigate market volatility, critical for risk-averse investors. Peter asks about Social Security timing, highlighting the trade-off between early claiming's investment growth potential versus the guaranteed, low risk returns of delayed benefits, with traditional advice favoring security. Lucas, a young investor with a taxable brokerage account, asks about key considerations to include when setting up a dividend reinvestment plan. Lastly, Chris wonders how to judge between three potential advisors. If you'd like a question in a future AMA, send Jesse a message!

 

Key Takeaways:

• How to mitigate your risk by diversification.

• Why a 10% "sandbox" could be the right thing for your portfolio.

• Should you employ a time based or an allocation based  rebalancing strategy.

• When you should or should not use bonds.

• What is "transfer-on-death"?

• How to choose between financial advisors.

 

Key Timestamps:

(00:00) - Review of the Week

(01:15) - AMA: Portfolio Rebalancing

(10:45) - AMA: Understanding Bond Performance

(20:29) - The Role of Bonds in Inflation

(25:59) - AMA: Social Security and Investment Strategy

(29:37) - Understanding Risk-Adjusted Returns

(30:32) - Comparing Social Security to Risk-Free Investments

(32:37) - Potential Downsides of Early Social Security Collection

(37:39) - Lucas's Taxable Brokerage Account Strategy

(50:38) - Chris's Financial Advisor Dilemma

 

Key Topics Discussed:

The Best Interest, Jesse Cramer, Rochester New York, financial planner, financial advisor, wealth management, retirement planning, tax planning, personal finance, Tax Loss Harvesting Myths, Debunked: What You Need to Know Now, The Simple 3-Step Formula to Avoid Excess Taxes in Your Investments, Is Splitting Your Portfolio Between Advisors a Smart Move? Maximize Your Capital Gains: Proven Tax Strategies for 2024, How to Avoid IRS Fines: The Urgent 90% Rule You Need to Know

 

Mentions:

"Why Can't I Take Social Security Early and Invest It?"

 https://bestinterest.blog/why-cant-i-take-social-security-early-and-invest-it/ 

"I Wouldn't Know Where to Start" – 16 Questions to Ask A Financial Advisor https://bestinterest.blog/financial-advisor-questions/ 

 

More of The Best Interest:

Check out the Best Interest Blog at bestinterest.blog

Contact me at jesse@bestinterest.blog

 

The Best Interest Podcast is a personal podcast meant for educational and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.


Navigating the world of money can feel overwhelming, with a constant stream of conflicting tips and trendy, quick-fix schemes. Personal Finance for Long-Term Investors-The Best Interest cuts through that noise. Host Jesse Cramer brings a unique perspective to the conversation, transitioning from his background as an aerospace engineer to his work as a fiduciary financial advisor. This podcast is built on the principle that genuine wealth isn't built overnight through speculation, but through consistent, well-reasoned decisions made over decades. Each episode delves into the mechanics and mindset required for that journey, exploring topics like retirement planning, intelligent investing, and the behavioral aspects of managing money. You'll find discussions that go beyond surface-level advice, examining the "why" behind proven strategies and how to apply them to your own life. The tone is conversational and grounded, avoiding financial jargon in favor of clear explanations. It’s a resource for anyone tired of the hype and seeking a sustainable path forward. By focusing on evidence-based ideas and patient execution, this podcast aims to provide listeners with the tools and confidence to build a secure financial future on their own terms. Tune in for a thoughtful, long-term approach to personal finance that prioritizes your best interest.
Author: Language: English Episodes: 100

Personal Finance for Long-Term Investors
Podcast Episodes
Most People Don't Have a Good "Purpose Anchor" (E98) [not-audio_url] [/not-audio_url]

Duration: 39:26
Jordan Grumet, AKA Doc G, returns to the podcast to share the difference between "Big P Purpose" and "little p purpose" and why you should pursue the seemingly less significant latter. Bringing together his experience in…
How Great-Grandma Makes You a Worse Investor (E97) [not-audio_url] [/not-audio_url]

Duration: 52:03
Jesse kicks today's show off with a monologue on the importance of having the right temperament for investing - it's not really about intelligence at all. Emotional stability and disciplined decision making outweigh expe…
Just Stop! On "Beating" and "Timing" the Market (E96) [not-audio_url] [/not-audio_url]

Duration: 55:44
Talking solo, Jesse tackles two important, ever-present investing questions in today's monologue. Should I try to time the market? How do I beat the market? The truth is, the timeless advice stands: diversify your portfo…
100% Stocks for All Retirement?! (E94) [not-audio_url] [/not-audio_url]

Duration: 47:01
Jesse's running the show solo this week, bringing with him some interesting perspectives on tax tricks, whether you should rent or buy, and college education. In this episode, you'll hear why side hustles might just be a…
Why Teachers Need to Be Careful | Dan Otter - E92 [not-audio_url] [/not-audio_url]

Duration: 46:06
Jesse opens the show by sharing a personal anecdote about a former teacher's challenging investment choices, which were burdened with high fees from their financial advisor. He emphasizes the predatory nature of the fina…
What No One Tells You About Early Retirement | Steve Adcock - E91 [not-audio_url] [/not-audio_url]

Duration: 53:33
Today, Jesse helps us step out of our financial frame and see the broader context of our lives. Quoting from David Foster Wallace's "This is Water" speech, he highlights our self-centered bias and makes suggestions on ho…
No Diversification = Deep Trouble?! | AMA #3 with Jesse - E90 [not-audio_url] [/not-audio_url]

Duration: 54:10
Back with another AMA, Jesse tackles your questions on employee stock incentives, diversification, how taxes affect investments, and more! Our first question comes from Lynn, who asks about when to take Social Security,…