I’m Keith. I sell options for income — one strategy, documented live, real money.

Every week I feature three active trades with full detail. The following week I report exactly what happened. No cherry-picking. You see the trades before the outcome.

Every Monday I publish what closed, what I opened, and what I learned. Subscribe below.

— Keith

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

My son’s baseball team made the playoffs. Three weeks of evening games, weekend tournaments, and the kind of chaos that makes it genuinely hard to sit down and write.

So I didn’t write. But the positions kept running.

That’s the whole point of building a system with GTCs — the trades don’t need you. I opened each position with a buy-to-close order already in place at 50% profit. When the price hit it, the order filled. I found out after the fact, usually while standing behind a chain-link fence.

Here’s the full accounting of what happened while I was gone.

What closed at target

AVGO — $360 put, July 17. I featured this one in Issue 014. Broadcom dropped 20% after earnings, premium spiked, I sold a put well below where the stock settled. It never came close to $360. The GTC fired June 18 at exactly 50%. +$2,088 on four contracts, 13 days after entry.

INTC — $105 put, July 17. Intel. I opened this June 17, the same week the AVGO position was working. GTC fired the next day, June 18. +$494. Twenty-four hours.

NKE — $40 put, July 17. Nike. This one had been sitting since late May, grinding toward target while the market moved around it. Hit 50% June 15. +$350. No drama.

TXN — $270 put, July 17. Texas Instruments. Same story. Opened June 8, closed June 15. +$453.

BMY — $52.50 put, August 21. Bristol-Myers Squibb. Slower mover, healthcare name, nothing exciting. Closed June 30. +$210.

Five positions closed at exactly where I told them to close when I opened them. That’s the system working.

What didn’t go as planned

I’m going to give you the losses too, because that’s what documenting this live means.

NFLX — $80 put, July 17. Netflix moved against the position and I closed it June 23 at a loss. -$3,050. I entered at 0.25 delta — meaning there was a 25% probability at open that the stock would be below that strike at expiration. This was one of those times. Not a mistake. The probability played out.

OXY — $55 put, July 17. Occidental Petroleum. Energy had significant headwinds — a US-Iran peace deal in mid-June sent oil prices tumbling as Strait of Hormuz risk premium unwound, and XLE dropped over 10% while SPY gained 13%. I rolled OXY once and closed it June 25 at -$1,052. Closed it, moved on.

NEM — $105 put. Newmont Mining, a gold miner. I put this position on in April with a thesis that gold would hold. I rolled it twice — which is my maximum — as the stock moved against me. After the second roll I closed it June 11. Net loss across three cycles: -$6,008.

This isn’t a story about a mistake. I followed the rules exactly: entered at 0.25 delta, set the GTC, rolled when it made sense, stopped at two rolls and closed. Gold didn’t hold long enough. That’s the 25% scenario playing out across a longer timeframe than usual. The system worked the way it was supposed to — I just happened to be on the wrong side of the probability this time.

What got managed

Two positions were heading into expiration underwater and needed decisions rather than exits.

GOOGL — $360 put, originally July 17. Google had been grinding lower. Rather than take assignment on a $360K obligation with the stock below that level, I rolled it to August 21 at the same strike. The total credit collected across both legs is $16.40 per share. Effective basis on potential assignment: $343.60. The thesis — Anthropic IPO catalyst in Q4, SpaceX liquidity event — is intact. I’m comfortable holding through August.

MCD — $280 put, originally July 17. McDonald’s. Same playbook. Rolled to August 21, collected additional credit. Total credits both legs: $7.68. Effective basis: $272.32. Defensive name, consistent earnings, nowhere near a thesis change.

What’s going to assignment

NVDA — $205 put, July 17. I made the decision two weeks ago: let this go to assignment. NVIDIA is trading above $194 right now, the put is in the money at $205, and the answer to “do I want to own 500 shares of NVIDIA at an effective basis under $199?” is yes. This isn’t a mistake. It’s plan B executing exactly as designed. After July 17, I’ll sell covered calls on 500 shares and the wheel keeps turning on a stock I actually want to own.

Where things stand

Four weeks. Five positions closed at target. Three that didn’t go as planned. Two rolled for more runway. One going to assignment on purpose.

Q2 closed at 20.6% annualized return on capital employed. That includes everything above — the wins, the losses, the rolls. That’s the number that matters.

What to watch: NVDA is heading into assignment July 17. GOOGL and MCD are running through August with room to breathe. The next cycle of entries is being staged now.

All current open positions are live on the → Start Here page.

— Keith

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

Last Tuesday, Broadcom reported earnings. Revenue up 48% year over year. The stock dropped nearly 20% anyway.

That kind of move demands attention. When a quality company drops 20% overnight, you want to understand why before you do anything. Business thesis intact? Yes. Quality company? Yes. Strike at a level I’d be comfortable owning? Yes. Premium elevated from the volatility spike? Very much yes.

So I opened a put at $360 — about 7% below where the stock settled after the dust. Four contracts. $10.45 each. $4,180 collected. 41 days.

If AVGO stays above $360 through July, I keep the premium. If it gets assigned to me at $360, my effective cost basis is $349. That’s a company projecting $100 billion in AI chip revenue by 2027 — with analyst targets above $490 — at a price below where even the post-earnings panic took it.

I’ll take that bet.

Meanwhile, the boring stuff was running its own program.

While I was running the AVGO checklist, two other positions were wrapping up quietly.

CCJ — $110 put, June 18. Cameco. Uranium mining. Nothing to do with Broadcom’s AI chips or guidance raises. CCJ hit its 50% profit target last week and closed automatically. $1,170 collected. I didn’t make a decision. The GTC I placed when I opened the trade did it for me.

CARR — $62.50 put, June 18. Carrier Global. HVAC and refrigeration systems for data centers and commercial buildings. Also nothing to do with semiconductor guidance. Also hit 50% and closed. $750 collected. Same story.

Both names ran their own thesis on their own timeline — completely indifferent to what was happening in the AI trade.

That’s what sector diversity actually looks like.

It’s not about owning a mix of growth and value or balancing your portfolio with index funds. It’s about making sure that when one sector gets hit with a narrative — earnings disappointment, macro scare, whatever — your other positions don’t feel it.

When Broadcom dropped, CCJ didn’t care. Carrier didn’t care. They were running on different fundamentals, different catalysts, different stories entirely.

The AVGO opportunity was worth my attention because it cleared the checklist. The rest of the portfolio didn’t need it.

What to watch

AVGO is already up 13% — the GTC is working. NEM is ITM and running toward July expiration. GOOGL is sitting right near the strike and will need a decision soon.

→ Full scoreboard is live on the Start Here page

— Keith

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

The Oracle position I opened last Tuesday closed on Friday — automatically, at exactly 50% profit.

I didn’t have to make a decision. The GTC order I placed when I opened the trade did it for me.

If you haven’t seen the video I posted about this, it covers why I close at 50% instead of riding to expiry. The short version: after 50% is captured, the remaining upside doesn’t justify carrying 100% of the risk. I left $8,300 on the table on purpose.

But the part I didn’t cover in the video is what happens immediately after the position closes.

$340,000 freed. Redeployed by Monday.

When Oracle closed, $340,000 in collateral came back. That’s not sitting money — that’s the engine of the next trade.

The question in a low-VIX environment is where to put it. VIX at 16 means the broad market is calm, and calm markets pay less premium. You can still deploy, but the checklist gets more selective.

By Monday morning, two names had cleared every filter: Google and NVIDIA.

What I opened

Google ($360P, Jul 17) — $8.90 premium. 6 contracts. $5,340 collected. The $360 strike sits below a business with real infrastructure, real cash flows, and a dominant position in cloud and search. Strong fundamentals are what justify the strike — not bullishness on the stock.

NVIDIA ($205P, Jul 17) — $6.35 premium. 5 contracts. $3,175 collected. Strike sits 6.5% below current price. The AI infrastructure thesis supports the floor. I’m not trying to buy NVIDIA at $205 — I’m collecting premium on a name where the downside has a basis.

Total new premium: $8,515.

The Oracle position paid $8,300. The capital it freed paid $8,515 in the next cycle — in less than a week.

TastyTrade’s research backs this up. Their data shows that closing short options at 50% profit and redeploying the capital outperforms holding to expiry — not occasionally, but consistently. More occurrences per year, higher win rate, and the freed capital goes back to work instead of sitting in a position that’s already given up most of what it’s going to give.

That’s the compounding effect people don’t talk about. It’s not dramatic. It’s mechanical. Close one trade, open the next, keep the engine running.

The full portfolio is live on the Start Here page — positions, strikes, premiums, and where everything stands.

— Keith

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

VIX is at 17. The market is calm. Options premiums are thinner than they’ve been in months.

I opened three new positions today.

This sounds like a contradiction until you understand the difference between one number: VIX tells you how much the broad market is afraid. It says nothing about whether any individual stock is afraid of itself.

OXY and WMT closed

Both at 50% profit. Both automatically. Issue 011 called them as approaching target — both hit their GTCs this week without me touching anything.

That’s what the system is supposed to do. Full detail on the Start Here page.

What I opened — and why

Three positions today: Oracle, Nike, and Netflix.

Oracle ($170P, Jul 17, $8.30 premium) — Enterprise software company at the center of the AI infrastructure buildout. Hyperscalers are signing data center contracts faster than they can build capacity. The business has real tailwinds, and the $170 strike gives 11% of cushion from where it’s trading now. 20 contracts. $16,600 in premium.

Nike ($40P, Jul 17, $1.40 premium) — The brand doesn’t need a description. The stock has been reset to levels not seen in years. The stock is down. The brand is not. 5 contracts. $700 in premium.

Netflix ($80P, Jul 17, $1.90 premium) — Dominant streaming platform with growing ad revenue and live sports coming online. The $80 strike sits below current price. 5 contracts. $950 in premium.

Total premium collected today: $18,250.

Why these three in a low-VIX environment

Here’s the concept that drives entries like this: IV Rank.

VIX is a market-wide gauge. IVR — Implied Volatility Rank — measures how elevated a specific stock’s IV is relative to its own 52-week range. A stock can have an IVR above 50 when VIX is at 17. That means fear has already arrived in that stock individually, regardless of what the broad market is doing.

The rule I apply: if a stock’s IVR is above 50, it’s worth looking at — full stop, regardless of VIX.

Waiting for the whole market to get scared before you sell anything is how you end up chasing. By the time the market is panicking, the quality setups are crowded and the names you actually want to own are getting indiscriminately sold. The calm periods are where you find the better entries — stocks with their own story, their own compression, their own elevated IV that exists for a reason.

Oracle, Nike, and Netflix each have that. VIX being at 17 is irrelevant to what they’re offering right now.

CCJ — still ITM, here’s the decision

Issue 011 flagged CCJ as the one to watch. The $110 put is sitting ITM — stock is at $108.

I’m riding it to assignment if that’s where it lands. Effective basis after the premium collected is $105.32. If I take assignment at $110, I own shares comfortably above effective basis. The wheel turns. That was always plan B — and plan B works.

22 DTE. No panic.

What to watch

NEM and CARR both have 22 days left and are sitting comfortably OTM — no action needed, those run on autopilot from here.

MCD is the one that needs attention. Stock is pinned right at the strike — $280.3 stock against a $280 put. Not in trouble yet, but close enough that I’ll be at 14 DTE in a few weeks with a decision to make.

Full scoreboard on the Start Here page.

— Keith

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

Last week I told you RTX was going to assignment and that was always the plan. It happened exactly as expected. I own 200 shares at an effective basis of $186.34.

The day the shares landed in my account, I sold a covered call.

$190 strike. June 18 expiry. $0.91 premium. Two contracts.

$182 total.

That’s it. And I’ve been thinking about whether I should have done it.

The two schools of thought

When a stock gets assigned and you’re sitting on shares, you have two choices. There’s no universal right answer. Every operator picks their own approach — but you need to know what you’re choosing and why.

School 1: Sell the call. Every time.

This is the Tasty Trade philosophy. You own the stock, you sell the call, you don’t debate it. Holding shares uncovered means theta is working against you with nothing to show for it. $182 beats $0. The premium is thin because RTX’s IV is low right now — that’s not a reason to wait, that’s just what the market is offering. Your job is to show up and collect it every cycle. The process is the edge. Not your opinion about whether RTX will bounce next week.

School 2: Sit on it. Wait for the stock to recover.

RTX is at $175. My effective basis is $186. The stock needs to rally $11 before I’m whole on the shares. If I sell the $190 call and RTX runs to $200, I’m capped at $190 — I miss $10 of recovery for $0.91 per share. The counter-argument: you put RTX in the wheel because you’d want to own it. Defense spending is a long cycle. If you believe the stock is undervalued at $175, selling a call that caps your upside for $182 is a real cost. Sometimes the right move is to let the thesis play out.

The choice I made — and what it says

I sold the call. $190C, June 18, $0.91. Not because I’m certain it was right. But because I don’t know when RTX recovers, and $182 in hand beats a thesis in my head. The $190 strike at least sits above my effective basis — so if the shares get called away, the math works.

What I won’t do: sell a call below my effective basis just to chase more premium. That’s the one hard rule regardless of which school you follow.

Neither choice is wrong. They reflect different things you believe about the stock. School 1 is more systematic. School 2 requires more conviction. Pick one and be consistent.

JNJ turned the same week

JNJ also went to assignment on May 15. 300 shares at an effective basis of $225.69.

Different situation, cleaner call. JNJ at $228.90 — stock is holding above my basis. I sold the $240 call, July 17, at $3.44. Three contracts. $1,032 total. More room, more premium, less debate.

That’s what a clean wheel entry looks like on the CC leg. RTX is the messier version. Both are running now.

What closed

Quiet week. Two closes, both at target.

Goldman Sachs $870 put — 50% profit. IBIT $45 call — 53% profit. Both hit their GTC orders automatically. I was golfing. That’s the point.

Full detail on the Start Here page.

What I opened

Nothing new this week.

VIX is at 17.8. That’s the low end of the range — premiums are thinner across the board, not just on RTX. I have capital sitting in the money market earning yield while I wait for better setups. Deploying into thin premium to stay busy isn’t a strategy. It’s impatience.

New entries coming next week.

What to watch

CCJ is the one to watch. Stock slipped below the $110 strike — it’s sitting ITM right now. That position needs attention and I’ll have a decision to make before the June 18 expiry. More on that next week.

MCD is close to the strike as well. Both are on the radar.

OXY and WMT are both approaching 50% profit with 30 days left. Those GTCs are working.

Full scoreboard on the Start Here page.

— Keith

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The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

Last week I said RTX was going to assignment and that was always the plan.

This Friday it happens. The $190 put expires May 15. I'll own 200 shares at $190. The stock is at $177. That's $13 below my strike.

Here's what I'm doing once I own those shares.

The second leg

Once I own the shares, I'll sell a covered call against them. The strike and timing depend on where things stand at that point — where the stock is trading, what the premium looks like, whether the thesis still holds. Next week's issue shows exactly what I sold and why.

Why the effective basis matters more than the premium

When you get assigned on a put, your cost basis isn't the current stock price — it's the strike you were put at minus the premium you collected. That number is your floor.

Selling a covered call below that floor means you've agreed to sell your shares at a loss if they get called away. Doesn't matter how much premium you collected on the call — the math works against you.

So before I look at what the premium is, I look at where my floor is. Any strike below it is off the table regardless of what it pays.

That one rule changes how you think about the whole second leg. You're not chasing the highest premium — you're finding the right strike above your basis and collecting whatever that pays. Sometimes it's thinner than a fresh entry. That's the real cost of a stock that moved against you.

This only works on stocks you're genuinely willing to own at your cost basis. If the thesis changes after assignment, the right move is to sell the shares and redeploy — not keep selling calls on a stock you no longer believe in.

This is how the wheel grinds back — patiently, above your effective basis, one premium at a time.

What closed last week

Three positions closed at target last week.

Disney $95 put — 52% profit. Newmont $100 put — 56% profit. Oracle $140 put — 50% profit. All three hit their GTC orders and closed automatically. I didn't touch them.

Full detail on the Start Here page.

What I opened

With those three positions closed, two new puts went on last week.

Carrier Global (CARR) — $62.50 put, June 18

Stock at $66. Carrier makes the HVAC and refrigeration systems that go into data centers, commercial buildings, and cold storage. The data center buildout is a real, multi-year capital cycle — and every one of those facilities needs cooling infrastructure. Not a speculative bet. $62.50 strike gives a 5.6% cushion with 38 days to run.

Newmont (NEM) — $105 put, June 18

A new position in a name I just closed at 56% profit. Fresh entry, higher strike, wider cushion. Gold is holding above $3,000 and Newmont generates real cash flow at current levels — this isn't a gold speculator, it's a business. $105 strike, $118 stock. Both have GTC orders at 50%.

What to watch

RTX expires Friday. The assignment is the event. Next week I'll show you the covered call I sold the first day I owned the shares — the exact strike, the exact premium, and whether the math worked out as planned.

JNJ also expires Friday, also ITM. That decision is coming too.

GS $870 put has already captured 35% of the premium with 37 days left. NEM is at 29%. Both running clean.

Full scoreboard on the Start Here page.

— Keith

Subscribe now

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I'm documenting how I personally trade — not telling you what to do with your money.

In last week’s issue I walked through why I hold a put that’s moving against me. The framework: if I’m okay owning the stock at my effective cost basis, I hold.

RTX is the live example of what happens when you hold all the way to the end.

The $190 put expires May 15. The stock is at $174. It’s going to assignment. I’m not doing anything about it.

What closed

Three positions closed last week — all three at a profit.

GOOGL $315 put captured 75% of the premium. General Dynamics $290 put, 76%. Chevron $180 put closed right at the 50% profit target. Different companies, different industries, all three wins.

Full detail on the Start Here page.

The RTX situation

I sold the $190 put on RTX for $3.66. My effective cost basis if assigned: $186.34 — that’s the strike minus the premium collected.

The stock is at $174. That’s $16 below my strike and about $12 below my effective cost basis. On paper, that looks like a loss.

Here’s how I’m thinking about it.

RTX makes the engines for the F-35 and the Patriot missile system. Their backlog runs for years, not quarters — you can’t swap out a defense contractor mid-program. That business doesn’t disappear in a soft quarter, and the geopolitical environment isn’t exactly getting quieter. I’m comfortable owning this stock.

When I get assigned May 15, I’ll own 200 shares at an effective cost of $186.34. The first thing I do after assignment is sell covered calls. If I can get $3–4 per contract on a near-term call, I’ve collected premium on the way down AND on the way up. The wheel keeps turning.

This is not a recovery play. This is the wheel working exactly as designed. The put going ITM was always a possible outcome. The assignment is plan B, and plan B has a clear next step.

I’ll show you the exact covered call I sell next week — the strike, the premium, the reasoning.

What I opened

With GOOGL, GD, and CVX closed, I redeployed the collateral into three new June 18 positions.

Oracle (ORCL) — $140 put, June 18

Stock at $176. A 20% cushion. Oracle’s enterprise database business is one of the stickiest revenue streams in tech — large enterprises don’t rip out their core infrastructure because the market got nervous. $50 billion in annual revenue, and it’s been growing. I’ll take a 20% buffer on that.

OXY — $55 put, June 18

Stock at $59. OXY cut its debt, streamlined operations, and is generating real free cash flow at current oil prices. Not the overleveraged company it was five years ago. The $55 strike sits below recent support with room to work.

Newmont (NEM) — $100 put, June 18

Stock at $108. World’s largest gold producer — actual mines, actual production, actual cash flow. Not a speculative bet on the gold price. I sized this one conservatively given the cushion. If I get assigned at $100, I own a cash-flowing business at a reasonable price.

All three have GTC orders at 50%. Set and done.

What to watch

RTX expires May 15. Next issue covers the assignment and the covered call I sell the same week — the second half of the wheel, executed live.

VIX is at 18. Selective deployment, same rules.

Full scoreboard — all 11 open positions — is on the Start Here page. I update it when things open or close.

— Keith

The Income Wheel | theincomewheel.com

Real trades. Real money. Documented live.

Nothing here is financial advice. I’m documenting how I personally trade — not telling you what to do with your money.

The Start Here page has the full position list with live progress on every open trade.

CAT and WMT both closed at 50% profit this week. The GTC orders fired automatically — I set them when I opened the positions and never touched them again. That’s the system working.

Then there’s Merck. The stock dropped from $121 to $111.90 since I opened the put. The $110 put I sold for $2.04 is now worth $2.85. That’s a paper loss of $0.81 per contract. Most traders would look at that and close it.

I’m not closing it.

Here’s why: the mark on the option doesn’t tell me if I’m winning or losing. My effective cost basis if assigned is $107.96 — that’s the strike minus the premium I collected. MRK is still above my strike. The stock would need to fall another $4 before I even get assigned. And even if I do get assigned at $110, I own a defensive healthcare stock at $107.96. Then I sell covered calls.

The question I ask isn’t ‘is this option losing money right now?’ It’s ‘will this stock be above my strike on May 15, or am I okay owning it at my effective basis?’ If the answer to either is yes, I hold.

That’s the framework. It keeps you from cutting the position that would have expired worthless two weeks later.

What Closed This Week

CAT $700 put, June 18 — closed at 50% profit. $22.20 in, $11.10 out. GTC fired, position done.

WMT $115 put, June 18 — same result. $2.12 in, $1.06 out. Full details on Start Here.

What I Opened This Week

With CAT and WMT closed, I opened two new positions for July expiry to keep the wheel turning:

Disney (DIS) — $95 put, July 17

Stock at $102.60 — 7.4% cushion. Disney is trading near multi-year lows. The studio pipeline is real, the parks don’t close in a soft quarter, and the balance sheet is cleaner than it’s been in years. If I get assigned at $95, I own it at a price I’d buy outright.

McDonald’s (MCD) — $280 put, July 17

Stock at $299.20, $19 cushion. MCD doesn’t need economic tailwinds — it benefits when consumers trade down. Defensive premium with room to work. Both positions have GTC orders at 50%. Set and move on.

One Rule That Keeps You Out of Trouble

When a position moves against you, there’s one number that matters: your effective cost basis. That’s the strike price minus the premium you collected. If the stock is still above your effective basis, you haven’t lost anything — you’re just waiting.

The mark on the option will move against you as the stock drops. That’s normal. It’s not a signal to close. The signal to close is when your thesis on the stock has changed, not when the option mark makes you uncomfortable.

MRK at $111.90 with a $107.96 effective basis is not a problem. It’s just a position doing what positions do.

Where Things Stand

VIX at 19. Premiums are thinner than six weeks ago but the wheel doesn’t stop — you adjust size, keep the same rules, keep running the system.

Full scoreboard — every strike, every cushion, every percentage toward target — is on the Start Here page. I update it when positions open or close, not just on Mondays.

Until next time, keep the wheel turning.

— Keith

The Income Wheel | theincomewheel.com

Nothing in this newsletter is financial advice. I am documenting how I personally trade — not telling you what to do with your money.

The Start Here page has the full position list with live progress on every open trade.

Two closed at target. One I had to catch myself. Here’s the difference.

CAT and GS both closed at 50% profit this week. Neither required a decision on my part — I set GTC buy-to-close orders when I opened each position and they fired automatically. CAT closed at $10.80. GS closed at $9.30, slightly better than target because GS beat earnings and ran higher. The system did its job.

Then there was AAPL. I caught it manually at 51% profit — but only because I was paying attention. There was no GTC in place. That’s on me, not the strategy. I fixed it: missing GTC alerts are now built into my morning dashboard so that gap doesn’t happen again.

That’s the honest version. The system works when you build it right. When you don’t, you find out.

Merck (MRK $110 put, May 15) is still running — 31% of the premium captured, GTC working, 24 days left.

What I Opened This Week

With May positions running toward their targets, I opened two new positions for June expiry:

Caterpillar (CAT) — $700 put, June 18

Same stock, lower strike. CAT is at $796.70 — that’s a 12.1% cushion. $22.20 per contract, already 29% of the way to the profit target in the first week. CAT’s order book doesn’t evaporate overnight. If I get assigned at $700, I own it at a discount and sell covered calls. Plan B works.

Walmart (WMT) — $115 put, June 18

WMT is at $128.10 — 10.2% cushion. $2.11 per contract, 10 contracts, already 27% captured. People don’t stop buying groceries when the market gets nervous. That’s the whole thesis.

Both have GTC buy-to-close orders at 50%. Set it and move on.

Why June Instead of May

45 days to expiration is the sweet spot — that’s where time decay accelerates and the premium-to-risk ratio is best. May 15 is only 25 days away. Opening new May positions now would mean breaking the rule.

June 18 is 59 days out — the nearest standard expiry beyond 45 days. Open at 59, close at 50% profit around day 30. That is the cadence. Same rule, every time.

Where Things Stand

VIX closed last week at 17.48. Lower volatility means lower premiums. That’s real. But the wheel doesn’t stop — you adjust size and strike selection, and keep running the same system.

Full position list — every strike, every cushion, every % toward target — is on the Start Here page. I update it when positions close, not just on Mondays.

Until next time, keep the wheel turning.

— Keith

The Income Wheel | theincomewheel.com

Nothing in this newsletter is financial advice. I am documenting how I personally trade — not telling you what to do with your money.

If you haven’t checked the Start Here page lately, I updated it this weekend — three fresh positions are live. You can always find it pinned at the top of the page.

What Happened to Last Week’s Trades

Last week I shared three open positions. Here is where each one landed.

WMT $115 put, May 15 — CLOSED at 50% profit

This is exactly how the wheel is supposed to work. I opened it, collected the premium, it hit my 50% profit target, I closed it and moved on. No drama. That is the whole system.

GOOGL $270 put — CLOSED at 50% profit

Same result. Hit the target, closed it, moved on. The current GOOGL position is a fresh entry at a higher strike — stock has moved up, so we moved with it.

AMD $190 put — CLOSED at 50% profit

Same story. Hit the target, closed it, done.

Three trades shared. Three closed at the profit target. That is the system working.

What’s Open Right Now

A few weeks ago, VIX spiked above 30 on geopolitical headlines. Everything sold off, and a lot of options traders panicked.

I used that window to enter 12 positions with elevated premiums. VIX has since come back down below 22. That volatility compression is exactly why several of these positions are already approaching their 50% profit targets after just one week.

Here is where I stand: 11 active cash-secured puts and one covered call across 12 different positions. Most expire May 15, a few May 22. Every single one is out of the money. Here are three worth talking about:

Caterpillar (CAT) — $720 put, May 15

Stock is at $783. CAT would have to drop about 8% before I am even at risk. I collected $21.62 per contract when I opened this. It is already at $15 — 29% profit in the first week. Industrial bellwether. A stock I would want to own at $720 anyway.

Goldman Sachs (GS) — $850 put, May 15

Stock at $870. I sold a put $20 below where it is currently trading. GS reported earnings this morning and beat estimates — EPS came in at $17.55 against a $16.86 expectation. The stock is well above my strike and the position is working.

Merck (MRK) — $110 put, May 15

Stock is at $121. Ten percent cushion. Healthcare demand is defensive — people do not stop filling prescriptions in a downturn. Premium collected: $2.04. Currently at $1.21 — 41% of the way to my 50% profit target. The kind of stock I would genuinely want to own at $110 if it got there.

The Week in Context

This is what the wheel is supposed to do in a volatile market. You are not in the stock. You are below it, getting paid to wait. The chaos above your strike is someone else’s problem.

Most of the 12 positions are cash-secured puts — I am in the entry phase of the wheel on those, collecting premium while waiting for the right assignment. The one covered call is on IBIT, where I already own the shares. Covered calls are the second half of the wheel. Both sides are running at the same time right now.

Until next time, keep the wheel turning.

— Keith

The Income Wheel | theincomewheel.com

Nothing in this newsletter is financial advice. I am documenting how I personally trade — not telling you what to do with your money.

Most options educators give you a clean rule. Never risk more than 5% per position. Never put more than 10% of your account in a single trade.

It sounds disciplined. It looks good on a slide deck.

It breaks down the moment you try to apply it to a real account.

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The Problem With Hard Rules

Here is the issue. Cash-secured puts have collateral requirements. If you sell a put on a $115 stock, you need $11,500 in your account to back that trade. That is not negotiable. That is the math.

On a $30,000 account, one position just ate 38% of your capital. The 5% rule is already dead.

On a $200,000 account, that same position is 5.75%. Manageable.

On a seven-figure account, it is a rounding error.

The rule does not scale. The principle behind it does.

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The Principle That Actually Matters

The goal of position sizing is simple: no single trade should be able to seriously damage your account.

Not just hurt it. Seriously damage it. Force a bad decision. Make you panic. Take you out of the game.

That is it. Everything else is just math in service of that goal.

Here is how I think about it in practice:

Be cognizant of sector concentration. If you already have a position in consumer staples, think twice before adding another one in the same week. That does not mean you can never have two positions in the same sector — sometimes a sector is where the best setups are. It means you should know when you are concentrated and make that a deliberate choice, not an accident.

Never double up on the same name. One position per stock. If I already have a covered call on AMD, I am not selling a put on AMD at the same time. Concentration in a single ticker is how you get hurt.

Keep dry powder. I always want cash sitting on the sidelines. Not because I am afraid to deploy it — because I want the ability to act when something interesting appears without being forced to close something else first. Idle cash is not a mistake. It is optionality.

Let the position size fit the account. If you are running a smaller account, you might only be able to run two or three positions at a time. That is fine. Two well-chosen positions are better than eight bad ones. And before you place any trade, make sure you have the capital to handle assignment — if you sell a put on a $40 stock and get assigned, you now own 100 shares at $4,000. That needs to be money you were prepared to spend.

One way to manage collateral on a smaller account is to focus on quality companies with lower share prices. A $40 stock requires $4,000 in collateral versus $11,500 for WMT. That is a meaningful difference when capital is limited. The key: a lower price does not mean a better trade. The stock still has to pass every other criteria — liquidity, IV rank, trend, earnings timing. Price is just one lever you can pull.

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What This Looks Like on a Real Trade

This week I sold a put on WMT at the $115 strike, expiring May 15.

WMT is trading at $125. That gives me over 8% cushion before I am even at risk. The collateral requirement is $11,500. The premium I collected covers roughly 1.8% of that collateral for the cycle.

Is $11,500 a lot? Depends entirely on your account size.

On my account, this is a small position — one piece of a diversified portfolio spread across multiple sectors.

On a $25,000 account, this is nearly half your capital. You would need to think carefully about whether this is the right trade, the right size, or whether a different stock with lower collateral requirements fits better.

The trade itself is the same. The decision around it is not.

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The Small Account Reality

I want to be honest about something most educators skip.

Small accounts are genuinely harder to run with the wheel strategy. The collateral requirements limit how diversified you can be. One or two bad positions can dominate your P&L in a way they never would on a larger account.

This does not mean the strategy does not work at smaller sizes. It means you have to be more selective. Fewer trades, higher quality setups, more patience. You cannot afford to force entries just to feel deployed.

The upside: the skills you build on a small account transfer directly to a larger one. The discipline required to run two positions well is the same discipline required to run twenty.

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Where Sizing Gets Easier

As your account grows, the math gets friendlier. You can spread across more positions, more sectors, more expiration cycles. No single position dominates. The portfolio starts to behave more like a system than a collection of individual bets.

That is the goal. Get there one cycle at a time.

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Next issue I will walk through some of the factors I weigh before entering any position — a way of thinking about setups that keeps bad trades out of the portfolio before they start.

Because knowing how to size a trade is only useful if you are picking the right trades to size in the first place.

If this resonated, forward it to someone who trades options. They will appreciate the honesty.

Until next time, keep the wheel turning.

— Keith

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The Income Wheel | theincomewheel.com

Every Monday. Real trades, real numbers, no fluff.

Nothing in this newsletter is financial advice. I am documenting how I personally trade — not telling you what to do with your money.

Issue 002 stated the profit target is 75%. That rule has been updated to 50%. See Issue 004 for the full explanation of why the math on 50% wins. The new rule is 50% — Issue 004 explains the full reasoning.

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The Setup

What happens when your stock rips past your covered call strike? Most people panic. They either freeze, roll blindly, or close the whole position at a loss.

None of that is necessary. You just need a framework for what to do next.

Let me use a real open position to walk through exactly what I would do.

The Real Position

I own 100 shares of Palantir at a cost basis of $158.23 per share.

Recently I sold a covered call at the $160 strike expiring May 15, collecting $6.75 per share in premium. That is $675 in my account immediately. The obligation: if Palantir is above $160 at expiration, my shares get called away at $160.

Here is what that position looks like today. Palantir closed Friday at $143.06. The stock is down from where I bought it. My $160 call is well out of the money and decaying in my favor every single day. The covered call is working exactly as designed.

But what if it goes the other way? What if Palantir rips back to $165, $170, $180 — past my $160 strike? Here is exactly what I do.

The Two Options

When a covered call goes in the money, you have two choices.

Option 1: Roll it.

Buy back the current call and sell a new one further out in time, at a higher strike, or both. You keep the shares, collect more premium, and stay in the position.

Option 2: Accept assignment.

Let your shares get called away at your strike. You keep every dollar of premium you collected. Then you redeploy into a fresh cash secured put on the same stock or a different one.

How do you decide which one? One rule makes that decision for you almost every time.

The Credit Rule — The Floor of Every Decision

Before anything else, answer one question: can you roll for a net credit?

That means the premium you collect on the new call is greater than what you pay to buy back the current one.

Credit to roll means rolling might make sense. Debit to roll means take assignment and start clean. Every time. No exceptions.

Never pay a debit to roll a covered call. You are adding cost to a position that is already working against your upside. That is how small opportunity costs become real ones.

Using the Palantir position as the example:

· Say the stock rips to $168 and my $160C is now worth $9.50. Can I sell a $165C at 45 DTE for $11.00? Net credit of $1.50 — rolling makes sense. I get paid to stay in with more room.

· Can I only get $8.75 for the new call? Net debit of $0.75 — take assignment. The market will not pay me to stay in, so I do not stay in.

The Judgment Layer

The credit rule is the floor. These factors live on top of it.

Earnings coming up.

Never roll into an earnings event. IV crushes after earnings and your new position loses value immediately. If earnings fall inside your new expiration window, take assignment, wait for earnings to pass, re-enter after.

Sentiment has changed.

If the reason you liked the stock no longer holds, do not roll just because you can. Take assignment and redeploy into a better setup.

What could a fresh position earn you?

This is the comparison most people miss. Do not just ask can I roll for a credit. Ask is this credit better than what I would collect starting fresh on the same or a different stock. If starting fresh pays more, take assignment.

Position size.

If the stock has run significantly, your position may now be oversized relative to your portfolio. Assignment naturally right sizes your exposure. Sometimes that is the right move regardless of the credit.

One More Thing — The 2x Stop Loss Does Not Apply Here

This trips people up. The 2x stop loss rule applies to cash secured puts — when a stock drops against you and losses compound fast. That rule exists to protect you from runaway downside.

A covered call that is ripping is a completely different situation. There is no runaway loss. Your shares are going up. The call being deep in the money is simply the cost of having your upside capped. That is the trade you made when you sold the call.

So we are not managing a loss. We are managing a winner.

The Decision Tree

· Can I roll for a net credit? No — take assignment. Always.

· Is the roll credit better than a fresh position on the same or a better stock? No — take assignment and redeploy.

· Check the judgment layer. Earnings coming? Take assignment and wait. Sentiment changed? Take assignment and move on. Still high conviction with room to run? Roll.

How This Fits the Wheel

CSP to assignment to covered call to called away back to CSP.

Getting called away on a covered call is not a loss. It is one complete rotation of the wheel. You collected premium on the put. You collected premium on the call. Your shares appreciated to your strike. That is the strategy working exactly as designed.

The goal was never to hold the shares forever. The goal is premium income. Assignment is just the wheel completing its cycle.

In the Palantir example: if the stock rips to $168 and I get assigned at $160, here is what I actually made. The $675 in call premium. Plus the $177 gain on the shares ($160 minus $158.23 cost basis times 100). Total: $852 on one position. That is not a loss. That is the wheel working.

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Next issue I will cover the DTE framework in detail — why 45 days is the entry point, what happens at 14 days, and why closing at 50% beats holding to expiration almost every time. That issue came directly from a question in the TikTok comments this week, which tells me it is exactly what you want to know.

If someone you know trades options, forward this to them. They will thank you.

Until next time, keep the wheel turning.

— Keith

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The Income Wheel | theincomewheel.com

Every Monday. Real trades, real numbers, no fluff.

Nothing in this newsletter is financial advice. I am documenting how I personally trade — not telling you what to do with your money.

They lose because they have no rules. And when the trade goes against them, they make it up as they go.

I want to be straight with you: I’ve been studying and refining this system for a while now, but I only recently started running it live with real capital. The research is proven — tastytrade has been backtesting these strategies for over 20 years across thousands of trades and multiple market cycles. I took that foundation, built my own system around it, and now I’m deploying it in real time and showing you everything as it happens.

I didn’t invent the wheel. I’m just disciplined enough to follow the blueprints — and transparent enough to show you every trade.

Here are the 3 rules at the core of that system.

Rule 1: Delta 0.35 or lower.

Delta tells you the market’s implied probability that your option expires in the money. At 0.35, you’re giving yourself roughly a 65% chance it expires worthless — which is what you want.

This is also how you define your risk before you ever enter a trade. You’re not hoping the stock holds. You’re operating inside a probability framework — and you chose that framework before you pulled the trigger. That’s a level of discipline most stock buyers never even think about.

Go higher and you’re chasing premium. That extra $50 or $100 per contract costs you assignment risk you didn’t need.

0.35 is the ceiling. That’s where the math works.

Rule 2: 45 days to expiration.

Time decay — theta — is the engine behind this strategy. At 45 DTE you’re in the sweet spot where premium is rich and time is still working for you.

At 14 DTE or less, most of the decay has already happened. You’re accepting assignment risk for leftover premium. Not worth it.

45 days is the target. That’s where premium and probability align.

Rule 3: Close at 50% profit. Don’t get greedy.

“Why close at 50% when you could make 100%?”

Because that last 50% requires holding 3-4 more weeks of market exposure for an extra $50-75 per contract. The math doesn’t work.

Close at 50%. Redeploy the capital. Run the cycle again. Over 12 months that discipline is the difference between a strategy that compounds and one that frustrates.

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These three rules — 0.35 delta, 45 DTE, 50% close — are the foundation. But here’s what most options education gets wrong: they hand retail traders the same institutional metrics used by portfolio managers running hundreds of positions with full risk teams behind them. It creates complexity without clarity.

Our system is different. It runs on over 100 parameters — stock selection filters, volatility gates, position sizing models, roll criteria, pre-trade scoring. The analytics are serious. But the system is engineered so the output is clean. You don’t need to understand every input. You follow the rules, and the rules are built on the research.

Think of it this way: you don’t need to understand battery chemistry to drive a Tesla well. The complexity lives under the hood. The execution stays simple.

I’ll unpack all of it here — one issue at a time.

Right now I have 3 active positions across 3 stocks — NVDA, SPY, and AAPL. That’s intentionally light. The system uses volatility gates to control when capital gets put to work, and right now those gates aren’t fully open. VIX is elevated, and the rules say you don’t deploy full size into a nervous market. So we wait. When the gates open, position count goes up, premium goes up, and I’ll show you exactly what changes and why.

This newsletter is where I’m building the full picture — one issue at a time.

If someone you know trades options, forward this to them. They’ll thank you.

Until next time, keep the wheel turning.

— Keith

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The Income Wheel | theincomewheel.com

Every Monday. Real trades, real numbers, no fluff.

Not investment advice. I’m documenting how I personally trade — not telling you what to do with your money.

Not because I read a book about it. Not because I watched someone on YouTube do it. Because I spent months back testing a systematic strategy, built the infrastructure to run it automatically, and decided it was time to stop theorizing and start doing it with real money.

This isn't a newsletter about getting rich quick. It's a live document of what actually happens when you deploy serious capital into a disciplined options income strategy — the wins, the losses, the mechanics, and the decisions in real time.

The strategy is called the wheel. You sell cash-secured puts on stocks you'd be happy to own. If they expire worthless, you keep the premium and sell another one. If you get assigned, you own the shares — and then you sell covered calls against them until they get called away. Then you start over.

Simple in theory. Surprisingly nuanced in practice.

The goal is to generate consistent monthly income while staying invested in stocks I'd hold anyway.

Here's where things stand right now:

$128,200 deployed across 4 contracts on 3 symbols (AAPL, SPY, NVDA ×2)

$771,800 sitting in a money market earning ~4.3% while waiting for market conditions to improve

$1,194 realized in the first 6 days

19 open positions across 5 accounts

A fully automated system monitoring every position every 20 minutes

Every Monday I'll publish a portfolio update — what closed, what opened, what the system flagged, and what I decided. No filters. If something goes wrong, you'll read about it here first.

If you're curious how this ends, stick around.

— Keith