Scott and James discuss how to best diversify a concentrated stock holding.

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Listener Question:

How do I exit a concentrated stock position?

I’m an employee at a large tech company and I’ve vested RSUs over the last 4 years. Some of my stock has appreciated 4x since I was granted it. My non-company stock brokerage account value is around $700k, and on top of that my vested company stock (APPL) is worth $250k at the moment. I expect to continue to accumulate more company stock through ESPP and RSU grants over time. My current gross income is around $325k ($200k salary + $125k annual RSU stock grants). I would like to take action to diversify this position into other equities (equity index funds). The reason I would like to diversify is to reduce my portfolio risk. Having just seen some other companies like Meta take a 70% stock hit, it feels like a responsible action to take. As I’ve heard in your podcast, I should not have too much of my net worth in one stock, and the only free lunch is diversification. I can sell all $250,000 vested shares tomorrow, but then I believe I would get hit with a large tax bill for all of the gains, which seems like it could be a burden. I am thinking I could start by selling the shares that I’ve held for over a year to make sure to get the long-term gains tax rate instead of the short term tax rate. And then next year, I could sell the stock I got this year, etc. I am thinking of starting a DAF in the next couple years and gifting $10k of appreciated stock to charity (apple does 2:1 promotions where they match up to $10k, meaning I could initiate the DAF with $30k), but the rest I would like to re-invest in a more diverse way to meet my short and long-term financial goals. 

Planning Points Discussed

• Utilizing Time Efficiently
• Capital Appreciation
• Purchasing Power
• Other issues (IRAs, Inflation, Financial Goals, etc.)

Timestamps:

2:30 - We're on YouTube HERE!

5:58 - Tax Consequences

9:16 - Stock Vesting

13:45 - Minimize Your Taxes

16:56 - Best Stocks

25:30 - Aligning Your Financial Goals

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