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Sometimes the ugliest setups hand you the best premiums. I don’t mean ugly like needs a little work — I mean ugly like lawsuits, a failed chart and a hard-to-borrow list.
That’s exactly what drew me to Freshworks (FRSH), and before you do anything, let me be crystal clear: This is a terrible little company. They’re being sued, it’s a failed initial public offering (IPO), so why am I touching it?
Because it’s on the hard-to-borrow list, the chart’s been beaten down and the premiums are inflated enough to make the risk worth considering.
When a stock gets hard to borrow, it usually means shorts are jammed up and scrambling for shares, and that pressure can make premiums squeeze.
That creates the kind of environment where selling both sides pays you just for standing still.
I got into this by selling $19 puts, then boxed the position by selling the $27 calls that expire on Feb. 27.
I’m on both sides, boxed in and letting time do the heavy lifting.
Managing the Mess and Using Tools That Keep You Sane
This isn’t the only trade where managing assignment matters. I got assigned on the Tesla 2x Leveraged ETF (TSLL) in the premarket recently, and it was a perfect reminder of what happens when a stock gets assigned to you.
TSLL is a cleaner trade — directional, straightforward and easy to manage once it’s in your account.
FRSH is the opposite — volatile, crowded with shorts and priced for chaos.
But the principle is the same: If you’re comfortable managing assignment, selling premium becomes a far more flexible game.
Hard-to-borrow names amplify that flexibility. When traders get squeezed and need shares fast, premiums can go vertical.
That volatility is dangerous if you’re guessing direction, but a gift if you’re boxing both sides and letting theta drip into your account.
Tools help too. I lean on Power X Optimizer to stay grounded when a setup gets noisy.
It cuts through emotion and shows whether the expected move, volatility and premium structure make sense before I commit.
With trades like FRSH, having a tool that filters the chaos is worth every penny.
All of this sits against the backdrop of a market that’s been bullish for what feels like 150 years.
Betting against that kind of long-term momentum is tough, which is why I prefer trades where the market doesn’t have to do anything special for me to get paid.
Box the range, let time decay work and stay out of the business of predicting macro swings.
FRSH is messy. TSLL is cleaner. The market keeps grinding upward.
But the strategy stays the same: Sell premium where fear is highest and manage assignment like it’s part of the plan — because it is.
Trade well,
Jack Carter
Jack Carter Trading
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*This is for informational and educational purposes only. There is inherent risk in trading, so trade at your own risk.
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