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119 - What Should I Do When I Have Large Unrealized Gains in a Concentrated Stock Holding?
Manage episode 303409208 series 2653925
Scott and James discuss what you should do when you have large unrealized gains in a concentrated stock holding.
Listener Question
1. My wife and I have been blessed with good fortune through our ESPP and RSU programs across 4 different employers. Having always been a buy-and-hold investor, these companies now have significant unrealized capital gains and represent almost 50% of portfolio value and a strong dividend cash flow that could provide income during a job loss. We live in CA and are in top tax brackets and would like to effectively diversify without loosing over 50% to taxes.
2. I currently have around 4,500 shares of AAPL. This makes up about 54% of my total stocks. I have 2,200 shares in my investment (non-retirement) account which makes up 100% of this total. I want to reallocate some of the AAPL, but it will have serious tax implications especially with my investment account. What do you recommend?
Planning Points Discussed
- Retirement Planning
- Utilizing Time Efficiently
- Capital Appreciation
- Purchasing Power
- Other issues (IRAs, Inflation, Financial Goals, etc.)
Timestamps:
1:30 - Introduction
3:27 - First Listener Question
5:05 - Individual Stock Example
6:58 - Investing v. Gambling
9:05- Taxes
9:43 - Cost Basis
12:15 - Stock Option Tax Planning
14:22 - Peace of Mind & Tax Strategy
17:55 - Lowest Cost Basis v. Highest Cost Basis
19:00 - Charitable Giving Strategy
21:55 - Second Listener Question
23:00 - Retirement Account Tax Benefits
24:53 - Aligning Your Financial Goals
LET'S CONNECT!
James
Scott
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Leave us a review on iTunes.
Have a money question you want us to answer? Submit one her
193 حلقات
Manage episode 303409208 series 2653925
Scott and James discuss what you should do when you have large unrealized gains in a concentrated stock holding.
Listener Question
1. My wife and I have been blessed with good fortune through our ESPP and RSU programs across 4 different employers. Having always been a buy-and-hold investor, these companies now have significant unrealized capital gains and represent almost 50% of portfolio value and a strong dividend cash flow that could provide income during a job loss. We live in CA and are in top tax brackets and would like to effectively diversify without loosing over 50% to taxes.
2. I currently have around 4,500 shares of AAPL. This makes up about 54% of my total stocks. I have 2,200 shares in my investment (non-retirement) account which makes up 100% of this total. I want to reallocate some of the AAPL, but it will have serious tax implications especially with my investment account. What do you recommend?
Planning Points Discussed
- Retirement Planning
- Utilizing Time Efficiently
- Capital Appreciation
- Purchasing Power
- Other issues (IRAs, Inflation, Financial Goals, etc.)
Timestamps:
1:30 - Introduction
3:27 - First Listener Question
5:05 - Individual Stock Example
6:58 - Investing v. Gambling
9:05- Taxes
9:43 - Cost Basis
12:15 - Stock Option Tax Planning
14:22 - Peace of Mind & Tax Strategy
17:55 - Lowest Cost Basis v. Highest Cost Basis
19:00 - Charitable Giving Strategy
21:55 - Second Listener Question
23:00 - Retirement Account Tax Benefits
24:53 - Aligning Your Financial Goals
LET'S CONNECT!
James
Scott
ENJOY THE SHOW?
Don’t miss an episode, subscribe via iTunes, Stitcher, Spotify, or Google Play.
Leave us a review on iTunes.
Have a money question you want us to answer? Submit one her
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