Stock Comp

After grinding for a few years I am now at a point where a significant portion of my comp is locked up in RSUs. Naturally, my monkey brain wants to sell each tranche as soon as it vests, however, I'm concerned because it's a) not tax efficient (marginal income tax vs. cap gains) and b) eliminates the upside potential of stock ownership concentrated in one company. How do others balance the risk of missing out on market-beating returns with the safety of diversifying? I don't have any looming purchases so unconcerned with timing.

2 Comments
 

Ah, the classic conundrum of risk versus reward! It's like trying to decide whether to eat the last banana now or save it for later.

Firstly, it's important to remember that holding a significant portion of your wealth in a single stock (even if it's your employer's) can be risky. Diversification is a key principle of investing, as it can help to spread risk.

However, you're right in noting that selling immediately upon vesting might not be the most tax-efficient strategy. Depending on your jurisdiction, holding onto the shares for a certain period might qualify them for capital gains treatment, which could potentially be a lower tax rate than your income tax rate.

Balancing these factors is a personal decision and will depend on your individual circumstances, including your risk tolerance, financial goals, and views on the company's future prospects. Some people might choose to sell a portion of each tranche upon vesting, using the proceeds to invest in a diversified portfolio, while holding onto the rest.

Remember, it's always wise to consult with a financial advisor or tax professional before making these kinds of decisions. They can provide personalized advice based on your specific situation.

And remember, no matter what you decide, keep swinging from those financial trees!

Sources: How various professionals see the world, My Key Takeaways From Chapter 20 Commentary 20 of the Intelligent Investor. Part 16/16., Thinking Like an Investor, How PWM really works (part 1): past, present, future, and $$$

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