Apr 9 • General discussion
GARY LeBlanc SPI portfolio AI analysis 4/9/26
SPI SKOOL PORTFOLIO BREAKDOWN
Gary LeBlanc Fund — Real Options Trading in Action
One of the most interesting things about trading is that the screenshots of a portfolio only tell half the story. The other half is how the trader thinks about the positions.
After reviewing Gary LeBlanc’s portfolio screenshots and discussing the trades with him, a clearer picture emerged of what is actually happening inside the strategy.
Gary responded to the earlier analysis with something important:
“I am salvaging a bad position in ISSC. It assumes I own the options to expiration maybe 25% of the time. When you have both a short call and short put working that becomes a market. As the options fluctuate you can move in and out and capture the time premium. Volatility increases premiums.”
This statement reveals something crucial.
Gary is not simply selling options and waiting for expiration.
He is actively trading volatility itself.
That means the goal of the strategy is not always directional prediction. The goal is to harvest time decay and volatility swings.
This is a much more advanced approach than simple buy-and-hold options trading.
The Core Strategy Gary Is Running
Gary’s portfolio shows a consistent pattern across several stocks.
The pattern is:
- Build a core stock position.
- Sell puts when willing to own more shares.
- Sell calls when the stock rallies.
- Trade the option premiums dynamically instead of holding to expiration.
This creates what Gary described as “a market” around the stock.
When both sides are working — a short call and a short put — the trader is effectively trading volatility instead of direction.
That is similar to how professional options traders operate.
Key Holdings in the Gary LeBlanc Fund
From the screenshots, Gary’s major stock positions appear to be:
• Fastly (FSLY) — 2500 shares
• Tilly’s (TLYS) — 4000 shares
• Orla Mining (ORLA) — 1500 shares
• Innovative Solutions & Support (ISSC) — 1000 shares
• FIGS — 900 shares
• Venture Global (VG) — 200 shares
• Smaller satellite positions in WT, NOK, and LXU
This is a high-conviction portfolio rather than a broadly diversified one.
Gary is clearly focusing on a handful of ideas and then trading options around those ideas.
The ISSC Trade — Case Study
ISSC is the most interesting example because Gary openly said:
“I am salvaging a bad position.”
This is extremely common in real trading.
What separates experienced traders from beginners is how they manage those positions.
Gary’s approach is to turn the position into a volatility harvesting trade.
Currently the structure includes:
• 1000 shares of ISSC
• Short May 15 $30 puts
• Short May 15 $25 puts
• Short April $22.5 calls
That means Gary has built a multi-layer premium structure around the stock.
Instead of waiting for expiration, he watches the premium fluctuations.
If the stock rises, the puts collapse in value.
If the stock falls, the calls collapse in value.
Either side can be closed for profit as volatility shifts.
Why Volatility Matters
Gary made another key observation:
“Volatility increases premiums.”
This is the engine of the strategy.
When volatility rises:
• options become more expensive
• selling them generates more income
• premiums can later be bought back cheaper
Professional options traders often make most of their money not predicting direction but selling volatility spikes.
Gary’s approach fits that model.
The Technical Picture for ISSC
The stock closed near the high of its daily range, which is typically a bullish signal.
Closing near the high suggests buyers were still active into the end of the session.
Key levels currently appear to be:
Resistance
$26.50
$28
$30
Support
$24.50
$23
If the stock stays above $25, Gary’s volatility structure works well because both sides of the trade decay over time.
Gary’s Plan for the Next Move
Gary mentioned the likely next adjustment:
“If ISSC goes up enough we will buy to close the May 15 $25 put.”
This makes sense.
When a stock rises, the short puts lose value rapidly.
Closing the put:
• locks in most of the premium
• reduces downside exposure
• simplifies the position
That leaves the trader with more flexibility for the next adjustment.
Strengths of Gary’s Trading Style
The screenshots and explanations reveal several strengths.
Active Position Management
Gary does not treat options like lottery tickets.
He adjusts positions frequently based on volatility changes.
Premium Focus
He understands that options are not just directional bets.
They are time-decay assets.
Conviction
Gary builds meaningful positions in ideas he believes in.
Volatility Awareness
His strategy benefits from volatility expansion rather than fearing it.
Risks in the Strategy
Every strategy has trade-offs.
The biggest risk in Gary’s approach is stacking short puts while already holding large stock positions.
If several stocks drop at the same time, short puts can quickly multiply exposure.
This is especially relevant in a portfolio where several positions are growth or momentum names.
Another risk is concentration.
FSLY, TLYS, ORLA, and ISSC make up the majority of the portfolio exposure.
That means the portfolio can swing significantly in a single day.
What Gary Is Really Trading
After reviewing both the portfolio and Gary’s explanation, the strategy becomes clearer.
Gary is not just trading stocks.
He is trading volatility markets around those stocks.
The system works roughly like this:
- Build a core stock position.
- Sell volatility through calls and puts.
- Close positions as premiums move.
- Repeat the cycle.
This is closer to professional volatility trading than traditional retail options trading.
Lessons for SPI SKOOL
This portfolio highlights several key lessons for options traders.
Lesson 1 — Options are not just directional bets
Options can be traded as time decay assets.
Lesson 2 — Volatility is opportunity
When volatility spikes, premiums expand.
Selling those premiums can generate income.
Lesson 3 — Positions can be dynamic
Options do not need to be held to expiration.
Active management can extract value earlier.
Lesson 4 — Risk still matters
Short puts combined with large stock positions can increase exposure quickly.
Position sizing is critical.
Final Thought
Gary summed up the philosophy well:
When you have both a short call and a short put working, that becomes a market.
At that point the trader is not just predicting direction.
They are trading the fluctuations of volatility itself.
That is a much more sophisticated game — and one that requires constant attention, discipline, and risk control.
But when executed well, it can turn even a bad stock entry into an income-generating trade.
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1 comment
GARY LeBlanc SPI portfolio AI analysis 4/9/26
skool.com/oil-option-trading-101-1282
How to use options to reduce risk in a portfolio. You can use this for all stocks and commodities but we going to trade Crude oil and oil options.
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