: ESPP compounding strategy and taxation? Let me start off giving some of the details of the ESPP my employer offers: Stock Price Discount: 15% Employee Salary Contribution: 3-10% (in whole value increments) Holding Period:

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ESPP compounding strategy and taxation?
Let me start off giving some of the details of the ESPP my employer offers:

Stock Price Discount: 15%
Employee Salary Contribution: 3-10% (in whole value increments)
Holding Period: 12 months (cannot sell before)
Buying Fee: Free
Selling Fee:
Offering Periods: Monthly

I should also note that I work for a large global conglomerate with a good reputation for growth. The stocks generally trend with the DOW.

I have this idea of compounding the profits back into my ESPP to take advantage of the 15% discount.

Let's assume I invest 0 of my own money into the ESPP for a given month, which means that I am able to purchase 2.50 worth of stock. Let's also assume that the stock price does not change at all within 12 months, at which point I sell. Therefore I have 2.50 in before tax/fee profits.

Correct me if I'm wrong, but (as I understand) because I sell before 24 months, this profit is taxed as ordinary income. I am assuming a third of that goes to Uncle Sam and I also must account for the selling fee. Therefore: Profit = 2.50 - 2.50*0.33 - = .37. This means that I now have 0 + .37 = 7.37 in my pocket.

What I am considering doing is reinvesting that 7.37 into my ESPP. This would again take advantage of the 15% discount, which means I have 7.37 + 7.37*0.15 = 8.48 in purchasing power. I plan to sell and reinvest year after year until I match my 10% employee contribution limit, after which point I would continue to do this but reinvest the earnings into other things like regular stocks, ETFs, gold, etc. Basically I would use my ESPP as a source of regular income.

My questions are: is this a sound strategy? How do I calculate the "break even" point at which I should not sell for a given month? Is it better to simply invest 10% of my salary every month and forget about it? What about waiting until 24 months to take advantage of capital gains taxes?

Also, if you can't tell I don't feel like I completely understand the taxation of ESPPs. If the stock price increased, how is that taxed after 12 months? After 24 months? What if the stock price decreased, but still technically profitable due to the 15% discount?

I apologize that this is a long one. This is something I have been contemplating for some time. Any advice would be much appreciated!

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