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Capital Gains Harvesting | Never Pay Taxes Again
Episode 018R

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Episode Guide

Episode Summary:

Capital gains and losses offer strategic ways to enhance your financial independence (FI) journey, especially through tax-efficient investing. The hosts, Jonathan Mendonsa and Brad Barrett, delve into actionable insights on leveraging these concepts and tools like personal capital for tracking investments. They discuss travel rewards, showcasing success stories including an impressive hotel stay for just 12,000 points. The dialogue emphasizes the importance of making small, intentional financial decisions and planning for major life events, like trips to Disney World and welcoming new family members. The episode also touches on how effective planning can allow for tax-free capital gains and set you on a trajectory for lasting financial freedom.

Episode Timestamps

Leveraging Capital Gains and Tax Loss Harvesting for Financial Independence

Achieving financial independence (FI) requires strategic financial planning and an understanding of key investment concepts. Two vital tools in this journey are capital gains and tax loss harvesting. By mastering these strategies, you can optimize wealth accumulation and minimize tax liabilities.

Understanding Capital Gains

Capital gains occur when you sell an asset for more than you paid for it. For those pursuing FI, capital gains can significantly affect your investment returns. The key is to understand how these gains are taxed:

  • Long-term capital gains, which apply to assets held for more than a year, benefit from lower tax rates compared to ordinary income. If your taxable income places you within the 10% or 15% marginal tax brackets, your capital gains may not be taxed at all.

The Power of Tax Loss Harvesting

Tax loss harvesting involves selling securities at a loss to offset capital gains taxes. This strategy can be particularly beneficial in the following scenarios:

  • To reduce the taxable amount of gains you realize from profitable investments.
  • To allow reinvestment of funds into different assets without a significant tax burden.

By combining these strategies, you can enhance your investment efficiency and preserve more wealth over time.

Case Study: Strategic Investment Planning for a Couple

Consider a couple with a combined income of $120,000 who are financially savvy and capable of maxing out their 401(k) contributions. They have enough net income left over after expenses to invest in a taxable account, which presents an opportunity to leverage capital gains and tax loss harvesting effectively.

Investment Breakdown

  • 401(k) Contributions: After fully funding their 401(k), they have about $76,000 for other investments.
  • Taxable Account Investment: They decide to invest $29,000 annually in a taxable account with an expected annual return of 8%.
  • Financial Goals: Over ten years, these investments might appreciate significantly, creating a sizable unrealized gain.

Encouragingly, if this couple channels their investment returns intelligently through tax strategies, they can substantially enhance their financial freedom.

Implementing the Roth Conversion Ladder

To further optimize their tax strategy, this couple can utilize a Roth conversion ladder. Here's how it works:

  1. Convert a portion of their 401(k) funds to Roth IRA annually, up to the income limit where taxes are incurred.
  2. Given they fall below certain income thresholds, they might convert around $34,000 annually without tax implications.

This strategy allows them to draw funds from their Roth IRA tax-free after five years, providing them access to additional resources during early retirement.

Harvesting Capital Gains Strategically

While investing in a taxable account, this couple can maximize their tax efficiency in several ways:

  • Identify Winning Assets: They can periodically sell assets that have appreciated significantly to realize gains. Given their low tax bracket, these gains may not incur taxes.
  • Reinvest After Realization: After selling their high-performing investments, they can reinvest in similar assets without altering their portfolio's risk profile. This is an efficient way to liquidate investment gains while adhering to tax laws.

Practical Considerations for Investors

Investing in taxable accounts requires vigilance. Here are critical actions investors should take:

  1. Track Tax Brackets: Be aware of how your income affects your tax bracket and plan your withdrawals or investments to stay within the most favorable brackets.
  2. Utilize Financial Tools: Tools like Personal Capital can help track your investments and net worth. By aggregating data, you'll gain insights into your financial progress and areas for improvement.
  3. Document Everything: Maintain detailed records of investments and transactions for easier tax reporting and to substantiate your realized capital gains and losses.

Realizing Financial Independence

The goal of employing these strategies is to propel yourself toward financial independence. By understanding capital gains, effectively harvesting losses, and utilizing tools like the Roth conversion ladder, you can build a sustainable financial future.

Key Takeaways for Financial Independence

  • Get Familiar with Investment Terms: Understand the nuances of capital gains, tax brackets, and the implications of different investment accounts.
  • Engage with Financial Communities: Sharing experiences and strategies with others on similar journeys can provide fresh insights.
  • Regular Reviews: Periodically reviewing your financial situation, goals, and investment strategies will keep you aligned with your intentions for FI.

Reaching financial independence doesn’t happen overnight. However, by implementing clear strategies around capital gains and tax loss harvesting, you will position yourself to create a more substantial, tax-efficient investment portfolio. Start today by examining your investment strategy and identifying opportunities to optimize your financial future.

Podcast Episode Summary how to harvest long term capital gains tax free.

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  • Friday Roundup 7
  • Review of Monday’s episode with Jeremy from Go Curry Cracker
  • Brad and his family just visited Washington DC for the weekend and used Chase Ultimate Rewards points to stay at the Hyatt Place National Mall
  • Brad’s trip to Walt Disney World with his family, parents and in-laws
  • Jonathan now understands harvesting capital gains and losses after the episode with Jeremy
  • Unconventional choices: Jeremy and Winnie haggling at the farmer’s market near the close of business. Brad going to Disney World before Molly turned 3 so they could get her park ticket for free. Jeremy taking his son on a flight the day before he turned 2 so he could be a lap child on a business class flight
  • Quick hit takeaways from the Jeremy episode: He told his mom he had a ’60 year emergency fund’; he opened a Roth-IRA for his son for earned income on the website.
  • The power of having money and financial independence enabled Jeremy to walk out of his job instead of doing something that he didn’t want to do.
  • Brad’s story of when he left his job and taking the power back from corporate America
  • Investing philosophy and the importance of taking your brain out of financial decisions
  • His financial freedom clock started when he ‘got to broke’ and paid off his student loans

Capital Gains Harvesting | Avoiding long term capital gains tax

  • Case study: Married couple with one child. 30 years old.  $120,000 of income and maxing their 401k ($36k in total)
  • Qualified dividends and long-term capital gains are taxed at 0% if you’re in the 10% or 15% marginal tax bracket
  • Understanding how marginal tax rates work for income taxes
  • The definition of FI: having 25 times your annual expenses saved up and invested

The long term capital gains tax

  • The long term capital gains tax  defined & explained
  • How the Roth-IRA conversion ladder would work for this couple and how they can harvest long term capital gains tax free by using advanced FI techniques

Itunes reviews and questions from the community

  • Reader case study from Kevin: How to work with a spouse from an ultra-wealthy lifestyle and bring them over to the FI lifestyle
  • Find what makes you happy in life and what you value and spend accordingly
  • Kevin’s scenario is almost exactly like our case study on this episode
  • Travel Rewards question: How to maximize hotel points with Hyatt and Starwood hotels
  • What’s coming up on ChooseFI: JL Collins talks about the Stock Series, the Stapes of FI, JD Roth and Kristy from Millennial Revolution, the true cost of car ownership

Links from the show:

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