I have six moves for you this week... one Rebound trade for anyone holding the Lyft shares assigned Friday, and five new PUT setups spanning an AI server maker riding a record order backlog, a satellite radio company Wall Street just woke up to, a Latin American bank compounding at nearly 40% a year, a document-signing giant that just posted blowout numbers, and a small AI-infrastructure story sitting on a $2.5 billion contract most of the market hasn't priced in. But first, let's settle up from Friday.
Friday's finish line. Our Chewy $23 PUT expired worthless (remember, that's a GOOD thing for us as the seller of the contract). CHWY closed just above the strike, and the $24 was already yours the day you sold it... escrow home, full stop.
One trade got assigned. If you sold the Lyft $17 PUT, your broker used your $1,700 on Friday to buy 100 shares at $17. Lyft closed a little under that. Not a problem... this is the other half of the strategy working as designed. You bought below where the stock traded when we started, and you'd already banked a premium on top. Those shares go back to work TODAY... that's R1 below.
And SpaceX came all the way home. The rolled $135 CALL from two weeks ago expired Friday with SpaceX trading well above the strike, so your shares were called away at $135, your full basis, and the $175 roll credit was already banked. Cycle complete, capital home, zero SpaceX left on the board. That $13,500 of escrow is part of what's funding this week's picks.
Quick status on the rest of your book: Under Armour sits just under our $5 strike with 10 days left... either it climbs back above $5 by September 18, or we buy at $5 and start selling Rebound CALLs. Kraft Heinz sits almost exactly on our $25 strike with 38 days left... same fork, no rush. Petco and Advance Auto Parts both dipped today but remain above their strikes. Everything else on the book is above its strike this morning. Status on every position in the snapshot at the bottom.
Remember, this is a menu, not a basket. Maybe your cash is already working. Maybe a company isn't your style. Trade what fits your account and your Investor DNA, and skip the rest with zero guilt.
And there's no rush. These numbers come from live Tuesday-morning prices. Set a GTC limit order at our number and let it work for a day or two. If it fills, great trade. If it doesn't, there's always another one coming.
See our current model portfolio at the bottom.
Returns are figured off the floor price on each trade, so reality should beat the number, not fall short of it.
One note on premiums before you fill. More premium than we quoted isn't always a gift. On Super Micro, the stock jumped almost 4% this morning, which pushed today's premium up... check the stand-down note in that pick before chasing a richer fill if the stock gives that move back. On the wildcard this week (Gorilla Technology), a fatter premium than quoted usually means the stock has dropped toward the strike... check the stand-down note there too. On the other value picks (SiriusXM, Nu, DocuSign), the opposite is true: a cheaper entry is welcome, because we're happy to own them lower.
R1
Lyft Handed You Shares Friday. Today They Go Back to Work at ~33%.
REBOUND TRADE This one is only for you if the $17 PUT put 100 Lyft shares in your account on Friday. Everyone else can skip to Pick 1.
⏱ The 30-second version
- The trade: you own 100 Lyft shares per contract at $17 from Friday's assignment. Sell the $17 CALL expiring September 18 and collect about $20 to $23 cash per contract today.
- Your return: yours the moment you sell... about 33% annualized at the floor on the $1,700 of capital in those shares, better if your platform fills you at the live bid.
- If Lyft finishes above $17 on September 18: your shares are called away at $17, the full price you paid... capital home, every premium banked along the way.
- If Lyft stays under $17: you keep the shares AND the cash, and we sell the next CALL. The machine pays either way.
Why the $17 strike and nowhere else
We sell the Rebound at the price we paid. Never below it. That way there is no ending where we sell our shares at a loss.
Lyft trades near $16.29 this morning, a little under your basis. The market will pay us $20-plus today for the right to buy your shares at $17... and either branch of that deal is one we already like.
One more thing worth knowing about the company you now own a slice of: Lyft just posted a genuinely strong quarter. Free cash flow ran $319.6 million for the quarter and $1.1 billion over the trailing twelve months. Gross bookings were up 23% year over year to $5.5 billion, active riders hit an all-time high above 30 million, and revenue grew 16% to $1.84 billion. This isn't the "still burning cash to grow" Lyft from a few years ago... it's turned into a real cash machine. So while we collect CALL premiums month after month, a company actually throwing off cash sits underneath us the whole time.
🔔
Cash Flow Options Alert — R1 (Rebound)
SELL -1 LYFT 18 SEP 26 17 CALL @ .20 LMT [TO OPEN]
Here's what that line means, in plain words:
- Ticker
- LYFT (Lyft, Inc.)
- Contract
- September 18, 2026 — $17 CALL (covered by your 100 assigned shares)
- Limit price
- $0.20 or better
- Current Stock Price
- ~$16.29
- Days to expiration
- 10
- Premium collected
- ~$20 to $23 per contract
- Capital working
- your $1,700 of Lyft shares
- Annualized return
- about 33% at the floor, up to 38% at the live bid
- If called away
- your shares sell at $17... full capital home, every premium kept
Sell one CALL per 100 shares you were assigned. This is the whole Rebound play: get paid while a great company works alongside you.
Pick 1
Super Micro: Paid ~50% to Own the AI Server Boom Below Its Own Backlog
CORE · VALUE PICK ⏱ The 30-second version
- The trade: sell the Super Micro Computer (SMCI) $37 PUT expiring September 18. Collect about $66 to $70 cash per contract today.
- Your return: yours the moment you sell... about 50% annualized at your floor on the $3,700 you set aside.
- The catch: the stock jumped almost 4% this morning, so it's an aggressive name trading close to its stand-down price. Read the note below before you chase a richer fill.
- If assigned: you buy SMCI at $37, about 26% under my estimate of the business value, and we sell Rebound CALLs for more cash flow.
Want it laid out? Skip to the alert box. Want the why? Keep reading.
The company
Super Micro builds the server racks and cooling systems that AI data centers are built out of... think of it as the company selling shovels and pickaxes to everyone digging for AI gold, except the shovels cost six figures apiece and come with a service contract.
Why the premium is this rich
Two years ago Super Micro went through a real credibility scare... an accounting and audit mess that spooked the whole stock. That memory is still why shares trade at a discount to other AI infrastructure names, even now.
But the numbers since then have been extraordinary. Full fiscal 2026 revenue hit $39.1 billion, up 78% from the year before. The fourth quarter alone brought in a record $60 billion of new orders, pushing the backlog to an all-time high heading into the new fiscal year. Management is guiding to $65 to $72 billion of revenue for fiscal 2027. The number of customers each generating over $1 billion a year for Super Micro grew from four companies to nine in a single year.
My estimate of the business value is around $50 a share. Our $37 strike sits about 26% under that, even after this morning's pop.
So a fund manager sitting on a big AI-infrastructure gain wants a floor under the rest of the position, and pays us well for it. We're glad to take the other side... either the escrow comes home with our ~$66 banked from day one, or we buy a $50 business for $37 and start selling Rebound CALLs on it.
Why we'd be glad to own it at $37
- About 26% below my estimate of business value
- Record $60 billion order backlog heading into fiscal 2027
- Nine customers now each worth over $1 billion a year in revenue, up from four
- Earnings behind us (August 11)... nothing due inside our window
Risks at a glance
- The old accounting scare is a real scar, not ancient history. Any fresh governance headline would hit this stock harder than a cleaner peer.
- Hardware margins run thin (non-GAAP gross margin 17.6% last quarter). This is a volume-and-backlog story, not a fat-margin one.
- Stand-down price: if SMCI slips below $40.22 before you fill, you're near-ATM on an aggressive name... check that the story hasn't changed before chasing a richer premium.
🔔
Cash Flow Options Alert — Pick #1
SELL -1 SMCI 18 SEP 26 37 PUT @ .66 LMT [TO OPEN]
Here's what that line means, in plain words:
- Ticker
- SMCI (Super Micro Computer, Inc.)
- Contract
- September 18, 2026 — $37 PUT
- Limit price
- aim for $0.70 — never go below $0.66
- Current Stock Price
- ~$41.07
- Days to expiration
- 10
- Premium collected
- ~$66 to $70 per contract
- Cash to secure it
- $3,700 per contract
- Annualized return
- about 50% at your floor — up to 53% if you catch the ideal fill
- If assigned
- You buy the stock at $37 a share, then we sell Rebound CALLs for more cash flow
Pick 2
Gorilla Technology: A $2.5 Billion Contract, an $18 Stock's Worth of Promise, and a $12.50 Entry
🎲 WILDCARD · STORY PICK This is our wildcard this week. Small dollars, bigger swings. Run ONE contract, and only with cash you can leave parked.
⏱ The 30-second version
- The trade: sell the Gorilla Technology (GRRR) $12.50 PUT expiring September 18. Collect about $25 to $30 cash per contract today.
- Your return: yours the moment you sell... about 56% annualized at the floor on the $1,250 you set aside, better if you catch the ideal fill.
- The catch: this is a small, fast-moving stock whose biggest news is contracts that pay off years from now, not this quarter. Treat the escrow as patient, speculative money.
- If assigned: you buy Gorilla Technology at $12.50 a share, about 31% below my estimate of the business value, and we sell Rebound CALLs for more cash flow.
Want it laid out? Skip to the alert box. Want the why? Keep reading.
The company
Gorilla Technology builds AI infrastructure and surveillance/security software, and lately it's been signing deals to lease out AI computing capacity the way a landlord leases office space... except the tenants are AI companies renting GPU horsepower by the megawatt.
The stock sits near $14.42 because it's tiny, thinly traded, and most of the market hasn't caught up to what it just signed.
What the market is glossing over
In the space of about six weeks this summer, Gorilla announced three separate AI data center deals: a Thailand campus site targeting $1.5 billion of annualized revenue starting in 2028, a capacity agreement with NeutraDC scaling toward 18 megawatts by November, and then the big one... a five-year, $2.5 billion AI compute contract, with the first phase alone (about 1,000 Nvidia B300 GPU servers) worth $1.3 billion.
That's a company trading like a penny AI stock that just landed contracts worth many times its own size. My estimate of the business value, discounting hard for how much of that is still promise rather than booked revenue, is around $18 a share. Our $12.50 strike sits about 31% under that.
About the risk, plainly
I want to be straight with you on this one. These are long-dated contracts, and revenue from them shows up over years, not quarters... 2028 targets don't help this quarter's numbers. Execution risk is real; landing a contract and delivering on it at scale are two different things. And the stock trades on headlines, so it can swing hard in both directions on thin volume. This is exactly why it's our wildcard and not a core pick.
Why we'd be glad to own it at $12.50
- About 31% below my estimate of business value
- Three AI data center contracts signed in six weeks, headlined by a $2.5 billion five-year deal
- Real institutional counterparties (NeutraDC, a global tech firm) putting money behind the story
Risks at a glance
- The big contract dollars are years out. Don't mistake a signed deal for booked, current-quarter revenue.
- Thin volume means the stock can gap hard on any news, good or bad.
- Wide valuation uncertainty here... this is a story stock, not a spreadsheet stock. Size it like the wildcard it is.
- Earnings dates on this one are still unsettled between trackers, sometime in October or November... either way, it lands after our September 18 expiration, so we're clear.
- Stand-down price: if GRRR slips below $13.59 before you fill, you're near-ATM... check that nothing's broken in the story before chasing a richer premium.
🔔
Cash Flow Options Alert — Pick #2
SELL -1 GRRR 18 SEP 26 12.5 PUT @ .25 LMT [TO OPEN]
Here's what that line means, in plain words:
- Ticker
- GRRR (Gorilla Technology Group Inc.)
- Contract
- September 18, 2026 — $12.50 PUT
- Limit price
- aim for $0.30 — never go below $0.25
- Current Stock Price
- ~$14.42
- Days to expiration
- 10
- Premium collected
- ~$25 to $30 per contract
- Cash to secure it
- $1,250 per contract
- Annualized return
- about 56% at your floor — up to 67% if you catch the ideal fill
- If assigned
- You buy the stock at $12.50 a share, then we sell Rebound CALLs for more cash flow
Pick 3
SiriusXM: Deutsche Bank Just Woke Up to This One... We're Still Getting Paid ~25%
CORE · VALUE PICK ⏱ The 30-second version
- The trade: sell the SiriusXM (SIRI) $28 PUT expiring October 16. Collect about $78 to $83 cash per contract today.
- Your return: yours the moment you sell... about 25% annualized at your floor on the $2,800 you set aside.
- The catch: the strike sits close to today's price, so plan on the possibility of owning this one and size the escrow accordingly.
- If assigned: you buy SIRI at $28, about 26% under my ~$38 estimate of the business value, and we sell Rebound CALLs for more cash flow.
Want it laid out? Skip to the alert box. Want the why? Keep reading.
The company
SiriusXM is the satellite radio in your car, plus Pandora streaming in your pocket. Millions of people pay a monthly bill for it whether the economy is booming or not... it's the kind of subscription people forget they're even paying for.
What just changed
Six days ago, Deutsche Bank upgraded SiriusXM from Hold to Buy and raised its price target from $31 to $45, calling the stock mispriced relative to what the analyst thinks the company can do in 2027 and 2028. The bull case centers on SiriusXM becoming YouTube's exclusive U.S. audio advertising representative, a relationship Deutsche Bank estimates could add roughly $2 billion of annual revenue by 2029. The stock popped 6% on the news.
My own estimate of the business value, well short of Deutsche Bank's $45, still lands near $38 a share... deliberately conservative because this is a mature, slow-growth business getting paid mostly for a shift into digital audio that hasn't fully shown up in the numbers yet. Our $28 strike sits about 26% under even that conservative number.
So an income investor who's owned this one for years and doesn't want to sell into a Wall Street upgrade wants protection under the rest of the position, and pays us well for it. Either the escrow comes home in October with our ~$78 banked from day one, or we buy a business Deutsche Bank thinks is worth $45 for $28 and start selling Rebound CALLs on it.
Why we'd be glad to own it at $28
- About 26% below my own conservative estimate of business value... 38% below Deutsche Bank's
- Fresh analyst upgrade with a real catalyst behind it (the YouTube audio ad deal)
- A subscription business with fanatically sticky customers
Risks at a glance
- The strike sits close to the money. Size the escrow like you're buying the shares, because you might be.
- The YouTube deal upside is a 2027-2029 story. Don't expect it to show up in next quarter's numbers.
- Next earnings land October 29, after our expiration, so we're clear... but the stock can still move on the growth-vs-mature-media debate at any time.
🔔
Cash Flow Options Alert — Pick #3
SELL -1 SIRI 16 OCT 26 28 PUT @ .78 LMT [TO OPEN]
Here's what that line means, in plain words:
- Ticker
- SIRI (Sirius XM Holdings Inc.)
- Contract
- October 16, 2026 — $28 PUT
- Limit price
- aim for $0.83 — never go below $0.78
- Current Stock Price
- ~$28.95
- Days to expiration
- 38
- Premium collected
- ~$78 to $83 per contract
- Cash to secure it
- $2,800 per contract
- Annualized return
- about 25% at your floor — up to 26% if you catch the ideal fill
- If assigned
- You buy the stock at $28 a share, then we sell Rebound CALLs for more cash flow
This one may take a day or two to fill at our number... the option was trading in the low-70-cent range as recently as yesterday and has been climbing with the stock. Set your GTC limit at $0.78 and let it work.
Pick 4
Nu Holdings: Paid to Wait on a Bank That Just Cleared $1 Billion in Quarterly Profit
CORE · GET PAID TO WAIT ⏱ The 30-second version
- The trade: sell the Nu Holdings (NU) $15 PUT expiring September 18. Collect about $18 to $20 cash per contract today.
- Your return: yours the moment you sell... about 34% annualized at your floor on the $1,500 you set aside.
- The catch: the strike sits close to today's price, so plan on the possibility of owning this one and size the escrow accordingly.
- If assigned: you buy NU at $15, about 17% under my ~$18 estimate of the business value, and we sell Rebound CALLs for more cash flow.
Want it laid out? Skip to the alert box. Want the why? Keep reading.
The company
Nu Holdings is Nubank, the digital bank that's become the default checking and credit card app across Brazil, Mexico, and Colombia. No branches, no teller lines... just an app that 139 million people now use for their everyday money.
Why it's worth a look here
Nu just posted its first-ever billion-dollar profit quarter. Net income hit $1.1 billion, up 49% year over year. Gross revenue climbed 39% to nearly $5.9 billion. The company added about 4 million new customers in three months, its credit portfolio grew 37% to $39.4 billion, and its risk-adjusted net interest margin hit a record 12.4%. This isn't a story about hoped-for growth... it's already happening, at scale, with real profit falling to the bottom line.
My estimate of the business value is around $18 a share against a price near $15.51. Our $15 strike sits about 17% under that estimate... short of my usual 20% bar, but this is a business compounding fast enough that I'm comfortable being a little closer to fair value than usual.
Why we'd be glad to own it at $15
- First-ever $1 billion profit quarter, up 49% year over year
- 139 million customers across three countries, growing every quarter
- Record risk-adjusted net interest margin of 12.4%
Risks at a glance
- The strike sits close to the money. Size the escrow like you're buying the shares, because you might be.
- This is a Latin American consumer lender... currency swings and regional credit cycles are real variables, even with growth this strong.
- Next earnings land mid-November, clear of our window.
🔔
Cash Flow Options Alert — Pick #4
SELL -1 NU 18 SEP 26 15 PUT @ .18 LMT [TO OPEN]
Here's what that line means, in plain words:
- Ticker
- NU (Nu Holdings Ltd.)
- Contract
- September 18, 2026 — $15 PUT
- Limit price
- aim for $0.20 — never go below $0.18
- Current Stock Price
- ~$15.52
- Days to expiration
- 10
- Premium collected
- ~$18 to $20 per contract
- Cash to secure it
- $1,500 per contract
- Annualized return
- about 34% at your floor — up to 37% if you catch the ideal fill
- If assigned
- You buy the stock at $15 a share, then we sell Rebound CALLs for more cash flow
Pick 5
DocuSign: The Market Cheered the Earnings Friday... Then Gave It Back Today
CORE · VALUE PICK ⏱ The 30-second version
- The trade: sell the DocuSign (DOCU) $60 PUT expiring September 18. Collect about $60 to $71 cash per contract today.
- Your return: yours the moment you sell... about 28% annualized at your floor on the $6,000 you set aside.
- The catch: this one may take a little patience to fill... the bid-ask spread is wider than usual on this contract.
- If assigned: you buy DOCU at $60, about 25% under my ~$80 estimate of the business value, and we sell Rebound CALLs for more cash flow.
Want it laid out? Skip to the alert box. Want the why? Keep reading.
The company
DocuSign is the company behind the "click here to sign" button on nearly every contract, lease, and offer letter you've signed online in the last decade. It's expanded from e-signatures into a full agreement-management platform, using AI to read, track, and manage contracts after they're signed, not just at the signature step.
The whipsaw that got us this price
Last Thursday, DocuSign reported a genuinely strong quarter: revenue of $876 million, up 9.4% year over year, and management raised full-year guidance to a $3.50 billion midpoint. Non-GAAP operating margin is guided to 31%-plus. The stock popped almost 4% the next day, closing Friday at $68.41.
Then today it gave more than that back, down about 5% to $64.90, on no fresh news I can find... just the market doing what it does after a good-news pop, taking profits and moving on. That kind of round trip, up on strong numbers then back down on nothing, is exactly the gap between price and value we're built to exploit.
My estimate of the business value is around $80 a share. Our $60 strike sits about 25% under that... a bigger discount today than it was Friday afternoon, for a business that just told us its own numbers are getting better, not worse.
Why we'd be glad to own it at $60
- About 25% below my estimate of business value
- Revenue growing 9.4%, guidance just raised, not cut
- Non-GAAP operating margin guided to 31%-plus... a genuinely profitable software business
- Earnings behind us (September 3)... nothing due inside our window
Risks at a glance
- The options here trade a wider spread than our other picks. Set your GTC limit and expect it may take a day to fill.
- Software valuations across the sector have been under pressure all year; a rising tide of sentiment against growth software could pull DOCU down with it even on good fundamentals.
- This was a "sell the news" move today, and those can occasionally run more than a day or two before they stabilize.
🔔
Cash Flow Options Alert — Pick #5
SELL -1 DOCU 18 SEP 26 60 PUT @ .60 LMT [TO OPEN]
Here's what that line means, in plain words:
- Ticker
- DOCU (DocuSign, Inc.)
- Contract
- September 18, 2026 — $60 PUT
- Limit price
- aim for $0.71 — never go below $0.60
- Current Stock Price
- ~$64.90
- Days to expiration
- 10
- Premium collected
- ~$60 to $71 per contract
- Cash to secure it
- $6,000 per contract
- Annualized return
- about 28% at your floor — up to 33% if you catch the ideal fill
- If assigned
- You buy the stock at $60 a share, then we sell Rebound CALLs for more cash flow
This contract trades a wider spread than most of our picks (bid near $0.45, ask near $0.71 this morning). Set your GTC limit at $0.60 and give it a little patience... there's no rush, and the floor is still a strong trade on its own.
