TL;DR
- Technology stocks offer explosive growth but brutal volatility; covered calls turn that chaos into income
- The tradeoff is real: you cap upside to collect premium, but you still face full downside risk without circuit breakers
- 2020-2023 proved this works: Mark’s Tesla position ran 500% while generating consistent call premium
- The key is probability stacking: right stock, right chart setup, right market, then layer the income
- Boring beats exciting: David V.’s 47% returns came from in-the-money calls, not hero trades
I watched a man lose everything in 2008. Not a stranger on the news. Me.
I had been trading my own account through 2006 and 2007, making good money, feeling smart. Then the floor dropped out. I lost a bunch. Not because the market was unfair, but because I was an emotional trader like everybody else. That was the fork in the road. I could keep being emotional, or I could build a system. I chose the system. I went back to the books that had actually worked: Edward Thorp’s probability thinking, William O’Neill’s growth-stock methodology, everything I had learned since I was a kid sneaking looks at my dad’s copy of Beat the Market. I amalgamated it into something repeatable. That is how Cash Flow Machine was born.
The system I built was designed for one thing: stack probabilities in your favor. Right stock. Right market. Right chart setup. Then layer covered calls on top for income whether the stock goes up, down, or sideways. Technology stocks became my favorite hunting ground, not because they are safe, but because they are volatile. And volatility is what you sell when you write covered calls.
Why Technology Stocks Are Different
Most investors misunderstand what they own when they buy a tech stock. They think they own a piece of the future. They do. But they also own a vehicle for emotional whiplash.
Technology stocks compress decades of business cycles into quarters. A company can go from market darling to pariah in a single earnings report. Revenue can double. Margins can collapse. The narrative can flip overnight. This is not a bug. It is the feature that makes covered calls on technology stocks so powerful.
Implied volatility, the market’s prediction of future price swings, runs consistently higher in tech than in utilities or consumer staples. That volatility is priced into options. When you sell a covered call, you are selling that volatility to someone else. They are betting on the explosion. You are collecting the premium while you wait.
The catch, and it is a real one, is that technology stocks can move against you fast. Covered calls do not protect you on the way down. The income you collected means nothing if you ride a high-flyer from $300 to $100 because you believed in the story. This is why my 2008 lesson became an absolute rule: no trade enters my book without a circuit breaker. A defined exit. A line in the sand. You can borrow my certainty and my experience and put that as a rule in your trading plan.
The Growth vs Income Tradeoff Explained
Here is the tradeoff nobody wants to talk about. When you sell a covered call, you are selling the right to your upside beyond the strike price. If the stock rockets 30% in a month, you keep the strike plus the premium. The buyer of your call keeps everything above that.
On a technology stock, that can hurt. These are the names that double in a year. The ones that make careers and retirements. Selling calls against them feels like leaving money on the table when they run.
But here is what I learned from 50 years in markets, from 1987 through dot-com and 2008 and 2020: technology stocks do not rocket 30% every month. They rocket 30% in some months. The rest of the time, they consolidate, they correct, they grind sideways while the market digests the last move. Covered calls get paid during that 80% of the time. You catch some upside when they run. You hedge the downside better than buy-and-hold because you are collecting premium while you wait.
The 2020-2023 period proved this to me in real money. I caught Tesla at the right spot and ran covered calls through the entire run. The account was up 500% during that period. Even with covered calls capping some upside. The key was the entry, the circuit breakers, and the discipline to keep writing calls through the volatility. Not hero trading. Systematic execution.
Learn the mechanics of this approach at our covered call strategy page.
How Probability Changes the Math
Most investors approach technology stocks as a bet on the future. Will AI transform this company? Will the product catch on? Will the CEO execute?
I approach them as a probability distribution. Charts are emotions on parade. Certain spots on the chart, stocks go up. Other spots, they are more likely to stall or reverse. I am not guessing. I am stacking edges.
The first edge is the stock itself. Real growth characteristics, not story stocks. The second edge is the market. You cannot fight the tide. The third edge is where the big money is buying, the market makers pushing it higher. Only then do I layer covered calls for income.
This is the lineage from Thorp and O’Neill: move probabilities into your favor, then let time work. Technology stocks give you volatility to sell. The system gives you the discipline to sell it at the right times, in the right amounts, with protection underneath.
Watch how this plays out in real market conditions on the Covered Calls YouTube channel.
The David V. Principle: Boring Makes You Rich
I have a student named David V. who has been in the program a little over a year. He is up roughly 47%. He plays only in-the-money covered calls. Always conservative. Always sticks to the plan. He plays a lot of golf.
David’s edge is that he does not stray. The brain wants to be excited. It wants the hero trade, the story you tell at dinner. David ignores that impulse. He runs the system. Boring makes you rich. Exciting does not make you rich.
On technology stocks, this is harder than it sounds. The names are seductive. The narratives are compelling. Everyone you know is talking about them. The temptation is to buy more calls, sell fewer calls, reach for upside you have already sold away.
Resist. The income from covered calls compounds. The protection from circuit breakers keeps you in the game. The discipline to stay mechanical is what separates the 47% returns from the blown-up accounts.
Building Your Technology Stock Covered Call System
If you want to run this strategy, start with the framework, not the stock pick.
First, define your circuit breakers before you enter. Where do you get out if the trade moves against you? Not emotionally. Mechanically. Write it down.
Second, choose your strike and expiration based on the chart, not your greed. In-the-money calls give more downside protection. Out-of-the-money calls give more upside participation. Match your choice to your read of the probability, not your hope for the outcome.
Third, size appropriately. Technology stocks move. A 10% position in a volatile tech name is not the same as a 10% position in a utility. Respect the volatility you are harvesting.
Fourth, roll when it makes sense. Sometimes the right move is to buy back the call and sell another. Sometimes it is to let the stock get called away and redeploy. The system has rules for this. Emotion does not.
Do covered calls work during tech crashes?
They work until they do not. The premium you collect cushions small declines but will not save you from a 50% drawdown. This is why circuit breakers are mandatory. The income helps. It does not replace risk management.
Should I sell weekly or monthly calls on technology stocks?
Monthly is my preference. Weekly options on volatile tech names tempt you to overtrade. The commission drag and the emotional churn erode edge. Monthly gives you time to be right and reduces the urge to micromanage.
What percentage of my portfolio should be in technology stock covered calls?
That depends on your total exposure and your circuit breakers. I have seen too many investors concentrate in “just one more” tech name because the premiums looked juicy. Position sizing is individual, but respect the fact that technology stocks correlate during stress. They do not all move together until they do.
Technology stocks will keep offering volatility. The question is whether you are equipped to harvest it systematically or whether you are hoping the next one is the big one. I have been doing this since before most of today’s commentators knew what an option was. The system works. The discipline is what you bring to it.
If you want to learn the complete framework, from probability stacking to circuit breaker design to the specific mechanics of rolling and adjusting, join the Options Mentorship Program. We show you what we do. How it can be done. And what actually works after 50 years of market cycles.
This is education, not financial advice. Past performance is not indicative of future results. Consult a qualified advisor before making investment decisions.