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Most traders think longer-dated options are safer. More time equals more safety and opportunity, right?
Wrong. Dead wrong.
I’ve been trading and running the numbers on this for years, and the data doesn’t lie — short-dated penny options can demolish longer-dated contracts on percentage gains when the move happens quickly.
It’s not even close.
Let me show you exactly what I mean with real numbers from actual trades.
The Oracle Example That Says It All
Take Oracle (ORCL). The weekly options were showing gains of 50%, 62%, 66% and 69%. Solid moves, right?
But here’s where it gets interesting. November options on the exact same stock were up only 18%, 19% and 21%. December contracts? Barely moving at 15%.
Same stock. Same directional move. Completely different results.
The reason is simple — shorter expiration dates can create massive percentage moves because there’s less time premium baked into the option price. When you’re paying pennies for a contract, even a modest move in the underlying can produce an explosive percentage gain.
Now, to be clear, the trades can also go against you just as quickly. But that’s why I love CHEAP options. If the occasional trade goes against me, I’m fine with it.
I’ve seen this play out repeatedly.
The Kraft Heinz Company (KHC) options ripping 181% and 230%. These aren’t stocks people expect to make dramatic moves — and that’s exactly why the right short-dated contracts can pay so well.
Smaller stocks can also offer excellent upside while requiring far less capital per position. That doesn’t make them low-risk, but it can limit the dollars committed to each trade and create serious percentage potential when the setup works.
Why the Big Names Don’t Work the Same Way
You might be thinking — why not just trade highfliers like Micron Technology (MU) or Microsoft (MSFT)?
Here’s the problem. MU moved up $9 in a single day recently, but the options were down in value. How is that possible?
Because MU was priced for a much larger move. When the stock fails to deliver what the options market expected, premium can fall even as the shares rise.
There’s also a practical problem with mega-cap names. A single MSFT November position can require $2K for one contract. I can’t tie up that much money in my brokerage account in just one trade that sits for a couple of weeks — it’s impossible for me to trade that way. I just can’t do it.
Larger-cap options demand significant capital, which makes smaller names more attractive for capital efficiency and percentage-return potential.
Wolfspeed (WOLF) trades for just $25, and its options have produced gains of 200%, 300% and 333% without requiring the same upfront commitment.
My average hold time on these penny option trades is anywhere from one hour to two days. I rarely hold longer than five days. This strategy is built to capitalize on rapid market movements — quick strikes, tight risk control and profit-taking when the move appears.
The math is clear. Short-dated contracts can deliver far more leverage than monthlies on the same directional move, but speed cuts both ways.
Move quickly, control position size and remember that these contracts can lose value just as fast as they gain it.
Order Flow:
This is for informational and educational purposes only. These are not official alerts issued by Lance, but rather some interesting orders picked by the team at Lance Ippolito Trading.
When you look at these plays, always take the market maker move into consideration.
You can be right on the direction but still lose money if the stock doesn’t move enough. That’s where the market maker move comes in clutch.
With puts, they’re often downside hedges in case a stock tanks, especially around earnings. The further out of the money they are, the more likely they are to be hedges.
Also be sure and check when the company’s earnings date is because many of the plays we post here are centered around earnings!
If a stock is really expensive, consider a spread to lower the cost.
And finally, always remember the golden rule when it comes to buying calls: Buy dips, sell rips — and don’t chase!
If a stock’s moved a ton already today, maybe wait for a pullback.
There is inherent risk in trading. Trade at your own risk.
Note: If no date is listed after the month, it’s the monthly expiration (third Friday).
The team at Lance Ippolito Trading
Lance doesn’t want the CCP spying on him, so you’ll never find him on TikTok. Same goes for other social media sites, which are filled with impersonators, scammers and crypto bros.
You can only find him on his personal YouTube Channel — smash that Subscribe button! https://www.youtube.com/@LanceIppolito
And in his private Telegram channel: https://t.me/+-gVwEIwGJhplMTgx
Important Note: No one from the team at Lance Ippolito Trading, New Money Crew or any of its associated brands will ever contact you directly on Telegram.
*This is for informational and educational purposes only. There is inherent risk in trading, so trade at your own risk.
P.S. I Have a HUGE Announcement to Share at 2PM ET
Tim Sykes and I have an explosive announcement for you at 2 p.m. ET TODAY…
As you might know already…
We revealed how some stocks have been engineered to soar higher right in the final trading hour every day…
And in the process, giving us the chance to target 100% returns right before the closing bell rings.
I must say, the top feedback has been nothing short of amazing…
But we’re just getting started.
Because at 2 o’clock, Tim and I will shock you with a limited-time announcement you won’t want to miss!
No reckless trading guarantees…
But if you don’t want to miss out, meet us here at 2 o’clock…
P.S.: Did you miss the huge announcement? Don’t sweat it, check out the details here.
We develop tools and strategies to the best of our ability, but no one can guarantee the future. Trading always carries a risk of loss. Past performance is not indicative of future results. Stated results are from live tracked signals from 8/27/26 to 10/25/2026. The win rate was 74.4% on the options, with an average return on winners of 128% and an average return on winners and losers of 81.2% over a 30-60 minute average hold time.
