Tag: options-selling

  • June 2026

    Heyyyy, sorry I’m late.

    Things are picking up… which is pretty much the same thing I said in last month’s episode.

    But, hey, we need to talk.

    My approach to trading and my perspective on the market have evolved and matured (hopefully) since I started this site and pretending to know what I’m talking about. I’m less swayed by the daily noise and have little problem waiting for the better trades and the bigger moves. This can lead to less exciting content as these opportunities can take their own sweet time to arise.

    I’ve come to realize that posting less fits more appropriately with my style of trading these days, and it also takes quite a bit of pressure off of me, honestly. This will allow me to show you the full life of a trade instead of having to recap and update on the same dang trades every month.

    This is what I mean: this here is a little graphic I made of The Wheel Strategy.

    I did Step 1 there at the top, “Sell Puts Get $$$”, back at the end of last year. I was assigned and forced to buy the shares, like, 8 or 9 months ago. I’ve been on Step 2, “Sell Calls Get $$$”, ever since and have yet to be assigned and have my shares called away.

    If I waited to show you the whole life of the trade, you could see all the ups and downs, how much I was able to lower my average cost over that time, and the total amount of premium received, plus any lessons I learned along the way. I would be able to show you the whole picture. This stuff is confusing enough, probably even more so if you’re only seeing a few threads of the quilt.

    I’ve tried some new strategies, like hedging… you know, what options are actually meant to be used for? I’ve also been buying some stocks with the intention of holding onto them for a bit, with a portion of the premium received, instead of putting it all back into the same cash pool to sell options with.

    Very exciting, but it’s difficult for me to report on changes or results when I’m only looking at such a short time frame. I also don’t want to write about something I’ve only just implemented and don’t have much of a feel for yet. Ya know?

    Plus, it never hurts me to practice the art of talking less.

    Monthly Roundup

    Here are my trades. I made $143 in June.

    Clicking the image will take you to my Theta Gang profile where you can view more details and notes on all of my trades.

    But wait looooook, just to prove things are picking up, I’ll go ahead and show you my trades from July as well, where I made a few bucks shy of $1000.

    Seeee?!

    So, this isn’t goodbye. I’m not quitting the race; I’m just changing my cadence. I’ll be back, and with greater numbers. Feel free to reach out on here or social media if you have any questions. You can click the subscribe button below and be notified when I post.


    Be excellent to each other,
    Chris

    Lend as little as $25 to create a more equitable world.
    Donate directly to the poor.


    If you’d like to give trading on Robinhood a try, you can click my referral link HERE and we’ll both get some free stock.

    This is not financial advice. Unless you’re into losing money.

  • May 2026

    I’ll keep this one short with just a brief recap and a quick update of how things are going.

    Click here if you would like a simple primer on what I’m doing here. I’m selling Cash Secured Puts until I am assigned shares. Then I sell Covered Calls to sell the shares, collecting premium along the way. This is known as The Wheel Strategy.

    You’re Probably Wondering How I Got Here

    By the end of last year I wound up with a lot of shares of SOFI and HOOD through selling Cash Secured Puts. The problem now is that both of these stocks continued to drop, losing almost half their value for most of this year.

    With their current stock prices being so far below the price I paid for them, the premium I was collecting back in their heyday has now completely vanished. These past few months, I’ve been forced to sell contracts for just a few bucks at a time as I wait for the stock prices to recover.

    Thankfully, both stocks are finally starting to bounce back. HOOD has almost returned to my cost basis and it feels good to sell juicy contracts again. I opened two Covered Calls recently for a combined premium of over $670. A pale comparison against the $30 or so I was collecting just a month prior.

    These mistakes that I made have had long-term consequences. I made these errors back in October and I’m still dealing with it and course-correcting to this very day. However, I do know that when I come out of the other side of this, I will be a better, more seasoned trader. I will be a Bishop in the Chapel of Extreme Experience.

    I won’t sugarcoat it, it has been difficult. I haven’t been able to trade as much. In May, I went through a brief period of being too gun-shy to take on a trade or found myself closing winning trades early, fearful of losing more money. It’s challenging, at times, to keep chipping away, penny by penny, to crawl back out of the hole I dug. It’s humbling to do it publicly.

    Ultimately, I was left with 2 choices. I could either decide the road to recovery was too long and difficult and throw in the towel and return to passive investing.

    Or, if I thought about it for a minute, I could project myself into the future, even just a year down the road, and see myself being proud that I stuck it out. The tricky part is trusting the process. Or maybe it’s having the patience for it. Maybe it’s Maybelline, what the hell do I know?

    Now I don’t want anyone getting the wrong idea that I lost all my money or anything, turning you away from trading. Like I mentioned in my video last month, I made around $25k in the market last year, I’ve just given a lot of that back now, is all. The reason for the loss is because I strayed from the plan that was working just fine.

    I’ve already advanced about half an inch since last time!

    Like a nice vacation, some time away can help to put things in perspective. When I return, I notice the urgency has been stripped away from life along with all the little things that I thought were important or absolutely crucial. I can see things with fresh eyes.

    We just returned last night from spending most of the week in the mountains in Georgia. Had a nice, little cabin by the creek.

    Monthly Roundup

    Here are my lil baby trades for May. I made $92. Man, I’ll tell ya, I’m just now seeing this number for the first time, just like you are. Not great lol. Not great.

    Clicking the image will take you to my Theta Gang profile where you can view more details and notes on all of my trades.

    Welp, that’s all for now. I’m excited that things are picking back up in my portfolio. Remember, kids, don’t buy options. Sell options.

    I promise more exciting times are coming. Once I’m able to get out of these two stocks, I will free up almost $30k of buying power in just one of my accounts. This will allow me to wreak havoc once again. Man is a creature with an apocalyptic view point who responds best to violent change.

    Until then,
    Chris

    Lend as little as $25 to create a more equitable world.
    Donate directly to the poor.


    If you’d like to give trading on Robinhood a try, you can click my referral link HERE and we’ll both get some free stock.

    Subscribe if you want to be notified when I wait till the last day of the month to talk about things that happened last month.

    This is not financial advice. Unless you’re into losing money.

  • April 2026

    Trying something different this month. I hope you enjoy it.

    Monthly Roundup

    A little behind, I’ll be back with the numbers. I can tell ya … they ain’t pretty.

    Chris

    Lend as little as $25 to create a more equitable world.
    Donate directly to the poor.

    If you’d like to give trading on Robinhood a try, you can click my referral link HERE and we’ll both get some free stock.

    This is not financial advice. Unless you’re into losing money.