We finally hit $1,000 a month. --April Dividends

 

We finally hit $1,000 a month.

Five years of buying, holding, and reinvesting — and April just made it real.

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May 7, 2026Monthly dividend recap

April total

$1,075.93

More than last April

+$307.02

Growth since 2021

+141%

I'll be honest — I wasn't sure this month was going to do it. But there it was on the statement: $1,075.93. Over a thousand dollars in dividends. In one month. I had to read it twice.

When I started tracking this back in 2021, the total was $446.87. That felt like a win at the time. And it was — but it also felt like this big, abstract goal was still way out in the distance. A thousand dollars a month in passive income seemed like something other people did. People with more money, more time, more of everything.

Turns out patience is the only thing you really need a lot of.

"Every dividend reinvested, every boring Tuesday where I didn't sell anything — it all added up to this April number."

The $307 jump from last April is what really gets me. That's not just the portfolio growing — that's the compounding actually starting to show up in ways you can feel. An extra $307 a month is a car payment. A grocery run. A weekend trip somewhere. It's real money doing real things.

So where did the money come from?

A big chunk of the growth this month came from positions I added more recently — HOOY kicked in $71, NVDW added $40.59, TSLW brought $36.54, and PLTY contributed $32.46. These are higher-yield instruments and I'm watching them carefully. High yield can mean high risk. But for April, they showed up.

The real backbone though? FXAIX at $161. The boring index fund that just quietly keeps growing its payout year after year. It was $75 back in 2021. Now it's $161. That's what compounding actually looks like — not exciting, just relentless.

FXAIX

$161.00

STWD

$88.11

HOOY

$71.00

CINF

$59.78

MO

$53.82

MO (2)

$49.78

NVDW

$40.59

The ones that quietly showed up, as usual

I keep a few positions that don't get talked about much but never miss. KO raised again. O (Realty Income) jumped $3.60 year-over-year — small but steady. JPM, CSCO, ITW — none of these are flashy, but they all grew their payouts without any drama. That's exactly what I want from the core of this thing.

FXAIX

$161.00

▲ $18.84 from last year

STWD

$88.11

▲ $8.40 from last year

HOOY New

$71.00

▲ First full month

CINF

$59.78

▲ $5.72 from last year

MO (lot 3)

$53.82

▲ $5.47 from last year

NVDW New

$40.59

▲ First full month

TSLW New

$36.54

▲ First full month

O (Realty)

$15.71

▲ $3.60 from last year

WDS

$0.00

Exited — moved on

WDS is worth a quick mention. That position wound down after paying $13.25 last year and zero this April. Same with LADR, which went quiet in 2025. Cutting positions that stop performing isn't fun — there's always a little second-guessing — but the capital that came out of those went somewhere better. The numbers bear that out.

What I'm watching going forward

The new higher-yield positions are the ones I'm keeping my eye on. HOOY, NVDW, TSLW, PLTY — these aren't your grandfather's dividend payers. They generate big distributions, but those distributions can move around a lot month to month depending on what the underlying assets do. April was great. I'm curious to see how May and June look before I get too comfortable with those numbers.

The core positions — FXAIX, MO, CINF, JPM, KO, CSCO — those I'm not worried about. They've been growing quietly for five years and I expect them to keep doing exactly that. Boring is beautiful when it comes to dividends.

"$446 in 2021. $1,075 in April 2026. Nobody did this overnight. And that's kind of the whole point."

If you're early in this journey and staring at a $40 or $60 monthly dividend, I get it — it feels like it's never going to be meaningful. But it will be. You just have to keep going and not mess with it when the market gets weird. April was proof of that for me.

See you next month.

Options Results and Review

 

In last week’s preview, we described the portfolio as a "masterclass in Delta and Theta management." This week, the market provided the ultimate stress test: a high-stakes earnings double-header and a surge in volatility.

By staying disciplined as a "landlord" of these assets—collecting rent even when the underlying value fluctuated—we have closed out the May 1st cycle with significant realized gains and strategically repositioned for the month ahead.

The Performance Summary (P/L Breakdown)

Ticker	Trade Type	Outcome	Realized P/L
GOOG	PMCC (Long $310 / Short $350)	Massive Win	+$2,495.00 (Net)
ASTS	Covered Call ($83 Strike)	Premium Retained	+$548.89
MSFT	PMCC (Short $455 Leg)	Expired OTM	+$296.00
TSLL	Equity Assignment ($13 Strike)	Called Away	+$99.00
SOFI	Covered Call ($20 Strike)	Defensive Hold	Premium Kept
TOTAL REALIZED			+$3,438.89

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Major Trade Highlights

1. Alphabet (GOOG): The "Grand Slam" Exit

Google was our star player. As the stock moonshot past our short $350 ceiling following earnings, we chose to capture the massive gain on the long leg rather than risk assignment. By selling the $310 long call for $59.50, we secured a $3,812 profit on the equity side, easily absorbing the $1,317 cost to buy back the short leg. This trade alone defines the power of the Poor Man’s Covered Call (PMCC).

2. TSLL: The Profitable Exit

Our strategy for TSLL was clear: if it hit $13, we were happy to walk away. With TSLL closing at $13.07, the shares were called away. We secured 100% of the upside and the full premium, clearing out a position that had previously been in the red. We are now sitting on fresh cash to "wheel" back in at a lower entry.

3. AST SpaceMobile (ASTS): The Rollover

ASTS proved once again to be a cash-flow machine. Despite the stock dipping to $70.89, we didn't just sit on the loss. We closed the $83 call for a massive 93% profit ($548.89 realized) and immediately "re-rented" the shares for next week, selling the May 8th $82 call for another $109.94.

4. Microsoft (MSFT) & SoFi (SOFI): Defensive Stability

Microsoft’s safe finish at $414.20 allowed us to pocket nearly $300 in "rent," further lowering the cost basis of our long-term position. Meanwhile, SoFi remains a challenge on the equity side, but by retaining 100% of our option premium, we continue to "chip away" at the entry price while we wait for the sector to rotate.

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Final Thoughts: The Power of the Rent Model

This week was a perfect illustration of why we trade this way. Even while some underlying stocks (like SOFI and ASTS) faced downward pressure, the portfolio realized over $3,400 in actual cash profit. We aren't just speculators hoping for a green day; we are landlords. Whether the market goes up, down, or sideways, we collect our rent. With TSLL called away and fresh premium already sold on ASTS, the "Retire on Dividend" machine is already geared up for the next cycle.

Stay tuned for Monday’s "New Lease" update as we look for our next entries.

The Strategic Landlord: How Retireondividends Navigates Earnings and Expirations

 In the modern trading landscape, the "Buy and Hold" mantra is increasingly being replaced by a more active, income-oriented approach. This week, we are pulling back the curtain on a portfolio that perfectly illustrates this shift—a mix of Poor Man’s Covered Calls (PMCCs) on Big Tech giants and Defensive Covered Calls on high-growth, high-volatility names like AST SpaceMobile (ASTS), SoFi (SOFI), and TSLL.

With a massive earnings double-header for Microsoft (MSFT) and Alphabet (GOOG) looming on April 29th, Retireondividends is navigating a complex web of "what-ifs" while managing a portfolio currently balanced between unrealized equity losses and massive option gains.

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The Big Tech Chess Match: Leveraging the PMCC

Instead of tying up hundreds of thousands in capital, Retireondividends utilizes Diagonal Spreads to capture upside while generating weekly "rent."

Alphabet (GOOG): The Performance Leader

• The Setup: Long $310 Call (Exp 5/15) vs. Short $350 Call (Exp 5/1).

• Current P/L: The long leg is the portfolio's "star player," currently up $1,800.

• The Strategy: If GOOG stays under $350 through Friday, Retireondividends pockets the premium while maintaining that massive $1,800 unrealized gain. If earnings trigger a moonshot past $350, the spread is closed for a "max profit" exit.

Microsoft (MSFT): The Recovery Play

• The Setup: Long $425 Call (Exp 6/18) vs. Short $455 Call (Exp 5/1).

• Current P/L: The long leg is currently down $97.

• The Strategy: Unlike Google, MSFT needs a post-earnings rally. Retireondividends is using the short $455 call to lower the cost basis of the long position. A move toward $450 would be the "Goldilocks" scenario—turning that $97 loss into a profit without breaching the $455 ceiling.

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The Volatility Trio: Equity P/L Breakdown

While the Tech giants handle the leverage, the growth portion of the portfolio is focused on share-backed income. Here is how Retireondividends’ underlying equity positions stand today:

Ticker	Average Cost	Current Price	Equity P/L	Strategy Strike
ASTS	$79.13	$75.05	-$4.08 /share	$83 Call
SOFI	$24.35	$18.80	-$5.55 /share	$20 Call
TSLL	$12.01	$11.47	-$0.54 /share	$13 Call

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Managing the Undercurrents

AST SpaceMobile (ASTS)

Despite being down $4.08 per share on the equity side, the ASTS position is a cash-flow machine. Retireondividends is showing an unrealized gain of $487.00 on the current call contract. This premium acts as a powerful buffer, effectively lowering the "breakeven" price closer to the $75 mark.

SoFi Technologies (SOFI)

SOFI represents the most significant challenge, with the equity down 22.7% from the $24.35 entry. However, by selling the $20 strike, Retireondividends is essentially "getting paid to wait." While the goal isn't necessarily to be assigned at $20 (which would realize a loss), the weekly premium collection is the primary tool for chipping away at that cost basis.

TSLL (Direxion Tesla Bull 2X)

This leveraged play is nearly at breakeven, down only $0.54 per share. With the $13 strike in sight, any Tesla-fueled rally this week could turn this into a profitable exit for Retireondividends, clearing the way for a fresh entry.

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The Friday Outcome: Binary Realities

As the market prepares for the Wednesday earnings reports, this portfolio faces two distinct paths:

• Scenario A: Worthless Expiration. The ideal "Income" outcome. Retireondividends keeps 100% of the option premiums and all long positions remain intact to be "rented out" again next week.

• Scenario B: Execution (Assignment). The "Exit" outcome. Shares are called away at the strikes. For ASTS and TSLL, this is a win—locking in a net profit. For SOFI, it’s a defensive exit.

Final Thoughts

This portfolio is a masterclass in Delta and Theta management. By combining the capital efficiency of PMCCs on Google and Microsoft with the raw premium of ASTS and TSLL, Retireondividends is no longer just a victim of market direction—they are a landlord of their own assets, collecting rent regardless of whether the market goes up, down, or sideways.

The real test begins Wednesday night. Will the earnings "IV Crush" work in Retireondividends’ favor, or will a massive rally force a portfolio-wide liquidation? Stay tuned for the Friday wrap-up.

How I Built a Barbell Strategy on MSFT — and Why Earnings Change Everything

 I'm holding two Microsoft calls into an earnings report four days away. One has a ceiling. One doesn't. That asymmetry is entirely intentional — and here's exactly how I built it.

The first trade — pure momentum

It started with a simple read: Microsoft had wind at its back, and I wanted maximum exposure to a continued move. I went deep in the money with the June 18 $415 call, paying $24.23 per contract.

The logic is straightforward. A deep ITM call carries a high delta — meaning it moves almost dollar-for-dollar with the stock. You're not betting on a miracle; you're riding a trend with the leverage of options and the safety net of intrinsic value. Within sixty minutes of entry, the contract hit $26.40. Nearly 9% while my coffee was still warm.

Strike

$415

Entry price

$24.23

Current

$26.40

Gain in 1hr

+8.9%

This position has no ceiling. If MSFT reports a blowout quarter and gaps to $470, every dollar above $415 is mine. At $455 it's already a $1,577 profit on a $2,423 bet. At $470, that becomes $3,077. The $415 call is my high-octane play — the one that benefits most from a genuine earnings surprise.

The second trade — income on top of upside

I also hold the June 18 $425 call, entered at $21.80. Slightly higher strike, slightly less delta, but still a strong directional bet. On its own, it's a clean swing trade. But I didn't leave it on its own.

Against the $425 long, I sold a May 1 $455 call for $304 in premium. This transforms the position from a naked long call into a bull call diagonal spread — sometimes called a Poor Man's Covered Call. The idea is elegant: I collect rent on my long position while I wait for MSFT to move.

Long leg6/18 $425C @ $21.80

Short leg5/1 $455C — collected $304

Adjusted net cost$1,876

Max profit (above $455)$1,124 (~60% return)

Breakeven reduction$304 cushion built in

Even though the $425 long dipped slightly on the day — from $21.80 to $21.48 — the trade as a whole is still green. The $304 I collected upfront absorbs minor fluctuations and lowers my effective cost basis. Theta is working for me on the short side while I wait for the June move.

"Getting paid to wait is not a strategy — it is a philosophy."

Why April 29th changes the math

Microsoft reports Q1 earnings on April 29th. Four days away. That single date reshapes every risk/reward calculation across both positions.

The pre-earnings period is usually kind to long call holders. Implied volatility rises as the market prices in uncertainty, inflating option premiums regardless of which direction the stock moves. My $415 call in particular — sitting deep ITM with no short leg to cap it — benefits directly from this IV expansion. I am getting paid twice: once by delta as the stock drifts higher, and once by vega as the market gets nervous.

The key risk to watch

The short $455 call expires May 1st — just 48 hours after earnings. If MSFT gaps above $455 on a blowout report, the diagonal spread hits its cap and the short leg faces assignment. The decision: do I buy back the $455 call before the 29th to uncap the trade, or accept the guaranteed $1,124 max profit and let the $415 long carry the upside?

The barbell in practice

Taken together, the two positions form what I think of as a barbell. On one end: the $425 diagonal spread, structured to deliver a reliable, hedged ~60% return if MSFT cooperates. On the other: the $415 naked long, positioned to print aggressively if earnings surprise to the upside.

If MSFT clears $455 by May 1st, the spread maxes out at $1,124 while the long call is already sitting on $1,577+ and climbing. Combined: over $2,700 in profit across both positions — on a total outlay of roughly $4,300.

If MSFT disappoints? The $304 premium on the diagonal cushions the blow. The $415 call loses ground but retains intrinsic value given how deep ITM it sits. Neither position is a lottery ticket vulnerable to total loss on a flat or slightly negative print.

The decision I have to make before Tuesday

Every trader with a position into earnings faces the same question: hold through the print, or take the profit now and sidestep the IV crush that follows the announcement?

For the $415 call, I'm leaning toward holding. The pre-earnings run is part of the thesis, and deep ITM options are more insulated from IV crush than OTM lottery plays. The intrinsic value floor is real.

For the $455 short leg on the diagonal — that's where I need to stay sharp. If MSFT rallies toward $450 before the 29th, I'll seriously consider buying it back to uncap the $425 long. At that point, the premium paid to close it will be expensive, but so will leaving a ceiling on a stock about to report.

The barbell is built. The earnings date is set. Now it's Satya's turn.

The 24-Hour MSFT Rebound

 

Headline: Quick Gains in Big Tech: My 16% Microsoft Swing Trade

In the current market, patience is a virtue, but speed is a weapon. Yesterday, I spotted a high-probability entry on Microsoft (MSFT) as it tested support levels during a brief dip.

The Setup On April 20, MSFT showed some weakness, sliding toward the $416–$418 range. Believing this was a temporary pullback rather than a trend reversal, I picked up the June 18 $420 Calls for $2,190. Using a June expiration gave me a "safety net" of time value (theta), though my goal was a quick scalp.

The Exit The thesis played out perfectly. Tech sentiment shifted overnight, and MSFT surged back above $424 today. I didn't wait for a home run; I hit a clean double and sold the position for $2,540.

Trade Analysis

• Asset: Microsoft (MSFT) $420 Call, Expiring June 18

• Entry (Apr 20): You bought the call for $2,190.00.

• Exit (Apr 21): You sold the call for $2,540.00.

• Profit: $350.00 (a 16% return in ~24 hours).

Key Takeaways:

1. Buy the Fear: Snagging calls during a red day often provides the best risk/reward.

2. Strike Selection: Choosing a $420 strike when the stock was under $420 meant I was buying slightly out-of-the-money, maximizing the delta gains as it turned in-the-money.

3. Discipline: A 16% gain in 24 hours is an annualized return most funds would dream of. Take the profit and move to the next setup.

How retireondividends Turned a Capped Alphabet Options Spread Into a High‑Stakes Earnings Play

 

The Alphabet Options Experiment: A Full Breakdown

In a developing options case study, retireondividends navigated a multi‑phase transformation of a Bull Call Diagonal Spread on Alphabet Inc. (GOOG). What began as a hedged, income‑generating structure has now become a leveraged, high‑volatility position heading into earnings — with a newly introduced short call adding another tactical layer.

Phase 1 — Establishing the Diagonal Spread

The initial setup used a Poor Man’s Covered Call, a lower‑cost alternative to owning 100 shares of GOOG:

• Long: GOOG $310 Call (Exp. May 15)

• Short: GOOG $330 Call (Exp. May 1)

This structure aimed to capture moderate upside while reducing cost through short‑call premium.

Phase 2 — Stock Rally Creates a “Hedge Conflict”

As Alphabet climbed to $337.53, the spread entered a classic equilibrium:

• The long $310 call gained roughly 49%.

• The short $330 call showed a –246% paper loss.

With GOOG trading above the short strike, the spread’s profit potential was fully capped. Gains on the long leg were neutralized by losses on the short leg, leaving the net return at approximately –$1.00.

The hedge had become the obstacle.

Phase 3 — retireondividends Uncaps the Trade

To break the stalemate, retireondividends bought back the short $330 call for $1,406, converting the position into a pure long call.

Revised Position

• Long GOOG $310 Call (Exp. May 15)

• Total Capital Committed:

$$2138-427+1406=3117$$

The trade now carried full upside — and full downside — exposure.

Phase 4 — Position Recovers to Profit

The long call later rose to $3,183, placing the position at a +$66 unrealized gain.

Capital preservation was achieved, but the hedge was gone. The position now behaved like a leveraged stock holding, highly sensitive to GOOG’s price movements.

New Development — A Fresh Short Call Sold

In a tactical move, retireondividends introduced a new short‑premium component:

• Short: GOOG $352.50 Call (Exp. April 24)

• Premium Collected: $83

Why This Matters

• Slightly reduces the effective cost basis

• Caps upside temporarily at $352.50

• Expires before Alphabet’s April 29 earnings

• Allows premium harvesting without fully compromising earnings‑related upside

This marks a shift toward active income generation while still positioning for a potential post‑earnings breakout.

📊 Timeline of Events — GOOG Options Case Study (retireondividends)

Date / Phase	Action Taken	Position Details	Impact / Notes
Phase 1 — Initial Setup	Establishes Bull Call Diagonal Spread	+1 GOOG $310 Call (5/15)
–1 GOOG $330 Call (5/01)	Creates a leveraged synthetic long with income. Lower cost of entry.
Phase 2 — Stock Rallies to $337.53	Spread becomes a “wash”	Long call +49%
Short call –246%	Gains and losses cancel out. Net return ≈ –$1.00. Hedge becomes hostile.
Phase 3 — Tactical Pivot	retireondividends buys back short $330 call for $1,406	Position becomes: Long GOOG $310 Call (5/15)	Upside uncapped. Total capital committed recalculated to $3,117.
Phase 4 — Position Recovers	Long call value rises to $3,183	Unrealized P/L: +$66	Capital preservation achieved. Full delta exposure restored.
New Development	retireondividends sells new short call	–1 GOOG $352.50 Call (4/24)
Premium: $83	Reintroduces income. Slightly reduces cost basis. Caps upside until 4/24.
Upcoming Catalyst	Alphabet earnings on April 29	Long call remains open	High‑volatility “binary event” ahead. Potential for large gain or rapid decay.

Conclusion

The GOOG options experiment has evolved from a conservative diagonal spread into a dynamic, multi‑phase strategy. With the introduction of a new short call and earnings approaching, retireondividends now stands at a pivotal moment.

The next move will determine whether this becomes:

• A successful blend of premium harvesting and directional conviction, or

• A high‑volatility gamble with $3,117 of capital at risk

Either way, the case study offers a clear window into how options structures can shift rapidly as market conditions change.

March 2026 Dividend Report: Income Growth, Portfolio Rotation, and Five‑Year Outlook

 Dividend income for March 2026 totaled $4,037.08, the highest March figure recorded in the six‑year dataset. The continued rise reflects a combination of dividend increases from long‑held positions, the introduction of new high‑yield instruments, and the removal of several underperforming or discontinued payers.

Year‑Over‑Year Performance

March dividend totals have increased steadily:

• 2021: $1,460.97

• 2022: $2,037.38

• 2023: $2,664.57

• 2024: $3,116.15

• 2025: $3,633.21

• 2026: $4,037.08

This represents a 176% increase over the 2021 baseline and an 11% rise from 2025 to 2026. The upward trajectory has remained consistent despite portfolio turnover and market fluctuations.

New Contributors in March 2026

Several securities appear for the first time in the March 2026 column, indicating recent additions:

• AVGW – 19.58

• NVDW – 45.57

• TSLW – 44.84

• HOOW – 33.78

• HOOY – 58.86

• PLTY – 50.09

• TOPW – 20.28

• GOOG – 25.08 (reflecting the company’s new dividend program)

These positions collectively contributed more than $250 to the March 2026 total, signaling a shift toward higher‑yielding or newly dividend‑initiating assets.

Positions No Longer Contributing

Several holdings that previously generated March income show no dividends in 2026:

• BTG – last paid in 2024

• BBL (second line) – last paid in 2023

• VFC – last paid in 2023

• FLO (first line) – no 2026 entry

• VIIIX – no 2026 entry

These absences suggest sales, dividend suspensions, or reallocations into higher‑conviction or higher‑yielding positions.

Continuing Core Contributors

A substantial portion of March 2026 income continues to come from long‑held, dividend‑growth companies, including:

• Visa, Southern, Johnson & Johnson, Chevron, Target, Microsoft, Union Pacific, Broadcom, Wells Fargo, ADM, Amgen, Lockheed Martin, Home Depot, Honeywell, UPS, Prudential, AFLAC, Discover, Hershey, Consolidated Edison, Dominion, Unilever, PepsiCo, Gilead, Shell

Index and fund positions also remain significant contributors:

• VOO, SCHD, VMCIX, VMCPX, VSCPX

Notably, UnitedHealth Group (UNH) delivered $227.07 in March 2026 after showing no March dividends in prior years, becoming one of the largest single contributors.

Trajectory: How the Portfolio Has Evolved

The six‑year record shows a clear structural evolution:

1. From traditional dividend growth to a hybrid model

Early years (2021–2022) were dominated by blue‑chip dividend growers and broad‑market funds. By 2026, the portfolio includes a second layer of high‑yield, cash‑flow‑oriented instruments, significantly increasing monthly income.

2. Rising payouts from long‑term holdings

Companies such as AVGO, LMT, UNP, TROW, HSY, ED, PRU, AFL, AMGN, and VMCIX show multi‑year increases, contributing to steady baseline growth.

3. Reduced reliance on any single payer

The 2026 income stream is more diversified, with contributions spread across dozens of securities rather than concentrated in a handful.

4. Strategic pruning

The removal of BTG, VFC, and other discontinued payers indicates a shift toward higher‑quality or higher‑yielding alternatives.

What March 2026 Suggests About the Next Five Years

Based on the current structure and trajectory, several implications emerge:

1. Income growth is likely to continue

With both dividend‑growth companies and high‑yield instruments in the mix, the portfolio is positioned for continued expansion in monthly income, even if individual positions fluctuate.

2. High‑yield additions accelerate cash recovery

The introduction of AVGW, NVDW, TSLW, HOOW, HOOY, PLTY, and TOPW has materially increased monthly payouts. If maintained, these positions could significantly shorten the time required to recover invested capital.

3. Dividend‑growth names provide long‑term stability

Companies such as MSFT, JNJ, V, UNH, AVGO, HD, HON, UPS, and PEP have long histories of raising dividends. Their continued presence suggests a stable foundation for future income.

4. Fund exposure may become a larger driver

Positions like SCHD, VMCIX, VMCPX, and VSCPX show rising payouts and may play an increasingly important role in smoothing volatility and providing consistent growth.

5. Portfolio resilience has improved

The combination of diversified sectors, multiple asset types, and both growth‑oriented and income‑oriented holdings reduces reliance on any single company or industry.

Conclusion

March 2026 marks a significant milestone in the portfolio’s development. The month’s record dividend total reflects:

• consistent year‑over‑year growth,

• the introduction of new high‑yield contributors,

• the continued strength of long‑term holdings, and

• strategic adjustments that removed weaker payers.

If current trends continue, the portfolio is positioned for further income expansion over the next five years, supported by both dividend‑growth companies and high‑yield instruments that enhance near‑term cash flow.