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u/m4vis 3 days ago Question

Downsides to wheeling dividend stocks?

I just want to know if there is something I’m missing here. Normally one of the bigger risks of the wheel is that the stock price plummets so far that it can take a long time to get to your cost basis. If you don’t want to increase your risk or you don’t have the capital to start another wheel at that point to lower your cost basis, you just sell calls with a further strike date but a price still at/above your cost basis and wait. Which can be a long time if the price dropped so much that if you want to sell at a strike price above your cost basis then you may be waiting months for the option to expire. But if you wheel a dividend stock that pays out monthly, in that same situation you can keep reinvesting the cash from the dividend payments + the cc premiums to buy more of the stock and lower your cost basis quicker. Are there downsides I’m not seeing besides the general arguments of dividend stock vs growth stock investing?
3 comments held Reddit says 0 on reddit ↗
  1. u/jvaritek33c 1 3 days ago
    Missing the ex dividend date due to having a csp instead of a share position
  2. u/Mean_Bend_9106 1 3 days ago
    The ex-div date thing is the one that catches people off guard. You think you're set with a CSP and then the stock goes up past your strike, you miss the payout, and someone else gets the dividend you were counting on. It's not a dealbreaker but it messes with the math if you're building a strategy around those monthly payments.
  3. u/ArniePie 1 3 days ago
    Taxes would be the main one. Options typically take into account the dividend payout. When you own the shares, the shares could get called away once you’re in the money and right before the ex-date.