Week 25 Snapshot: Friday Portfolio Developments (13-Jun-2025 to 19-Jun-2025)

Portfolio Update

Week 25 saw no position changes, and a focus on income generation to offset market weakness.

SOFI currently leads the pack with a 63% total return from put-selling. MSTY is up 3.83% due to dividend reinvestment, and ULTY gained 2.55%. 

YMAX (-7.38%) and CONY (-14.04%) remained the primary laggards despite significant dividend income, as both saw declines amid broader market weakness and crypto-linked selling pressure.

Market Update

Global markets turned cautious mid-week as renewed Israel - Iran hostilities on Jun 14 sent oil prices surging nearly 6% and equities futures sliding about 1%, a risk-off reaction that persisted through Jun 18 when the Federal Reserve held rates steady and reiterated two rate-cut forecasts later this year, keeping the S&P 500 flat. On Jun 19, President Trump's upcoming decision on US involvement in the Israel - Iran conflict further increased geopolitical uncertainty.

Key Dates:

• 14 Jun 2025   Israel and Iran launched fresh attacks on each other
• 18 Jun 2025   The Fed held rates steady and maintained two rate cut forecasts later this year.
• 19 Jun 2025   Trump to decide on US involvement in Israel - Iran war in 2 weeks.

Transactions Made:

• Closed 2 CONY $8.00 covered calls to realize over 70% of the premium earned

Realized P&L:

Upcoming Dividends:

Strategy for Week 26:

• Maintain buffer to provide liquidity for volatility spikes. 
• Add to high-yield option income funds like MSTY
• Roll SOFI puts once ~70% premium is captured.
• Reinvest dividends from ULTY / YMAX payouts back into income vehicles.
• Monitor middle east developments and Fed commentary.

Which Strikes and Expiries are you targeting for your option rolls next week? Share below.

May 2025 YieldMax Recap

Big Dividends, Low Volatility and a Game of Precision

📍Introduction: When Volatility Sits Still, Dividends Step Up.

May 2025 reminded us of a fundamental truth in income investing: When the market stops swinging, don't chase. Collect. With implied volatility (IV30) decreasing across the board, options premium dried up. But YieldMax sustained.

Despite a quiet VIX and underwhelming movement from key underlying like MSTR and COIN, we recorded a solid $1,387.26 in net passive income. This proves once again that even when the market slows down, your strategy doesn't have to.

🧭 The Market: Volatility Faded, but the Bulls Returned.

The S&P closed May at 5,911.69, climbing an impressive 6.15% month over month, a sharp contrast to April's drawdown. After bottoming near 5,600 on May 6, markets roared back following the CPI report release showing a softer than expected inflation. The rally peaked near 5,970 mid month, and held firm into June, even as volatility continued to fade.

 🌬️ IV Trends – The Real Yield Story.

• CONY IV collapsed as COIN stagnated, slashing covered call yields.
• MSTY briefly spiked as BTC approached $110K, but gains retraced by month end.
• YMAX IV30 continued to decay, pushing its option payouts to near zero.

With volatility compressed, dividends became the true alpha. YieldMax ETFs didn’t need big moves. They just needed time and payout cycles.

💼 Portfolio Snapshot (End of May 2025 )

📊 Performance Metrics – Real Yield, Real Results 

• Despite a -16.9% unrealized loss, the portfolio is nearly breakeven on adjusted value thanks to strong dividend flow and selective premium capture.
• MSTY is the powerhouse, delivering over $2,400 in total income to date.
• CONY and YMAX, while contributing to the capital drag, have paid for themselves through distributions, reinforcing the portfolio’s income-buffered resilience.

📥 MSTY Accumulation Log – Tactical Scaling in May

During May, I added 300 MSTY shares across four entries, tactically spread over price dips and IV setups. These purchases supported my build toward a 1,000-share foundation while maintaining cost discipline.

💼 Options Tactical Deployment in May

Despite a low-IV environment, opportunistic option selling added meaningful income during May. Timing was critical, and all trades were deployed during short volatility upticks.

Total May Premium Collected: $354.68

Options weren’t frequent, but they were efficient, boosting monthly income by 25% on top of dividends, while maintaining capital flexibility.

💰 May 2025 Income Breakdown 

A new monthly high driven by layering of dividends and option trades.

🧠 Lessons from May 

• IV drives yield, but not price along. Stocks rallied, but IV didn't follow until IV popped.
• Dividends remain the bedrock. Dividends made up 80% of of income.
• Precision beats overtrading. Fewer trades with better entries resulted in stronger yield efficiencies.

🎯 Strategic Adjustments – June 2025  

MSTY (Foundation)

• Accumulate below $22 if IV ≥ 40
• Continue selling CSPs around $21.50–$23 if premiums hold
• Track MSTR strength above $400 for conviction scaling

YMAX (Yield Layer)

• Maintain 100 Share block
• Weekly distributions fuel for reinvestment or short CSP ladder

CONY (Tactical Play) 

• Roll or let $15 CC expire (Jun 20)
• Don’t add unless IV > 50
• Monitor COIN headlines for reactive option setups

🔮 June Outlook 

 📈 What’s Next?

I am still in progress of fleshing out the analytics and I need your input.

• Want dividend heatmaps or income bar charts?
• Interested in tracking rolling 3/6/12-month yield on MSTY/CONY/YMAX?

What would you like to see?

Drop a comment, DM, or email — and let’s compound smarter together. 

Summary - April 2025 (CONY, MSTY, YMAX)

 Introduction

April 2025 extended the multi-month decline in market volatility across all YieldMax ETFs, with implied volatility (IV30) reducing across the board. This trend reflects broader market sentiment, where risk appetite has returned amid improving US inflation data, a stabilizing labor market, and growing expectations of a Federal Reserve cut as early as June 2025.

That being said, a surprisingly strong April jobs report, showing an addition of 177,000 jobs and an unemployment rate holding steady at 4.2% has tempered expectations for an imminent rate cut. The robust labor market suggests that the Fed may delay easing monetary policy, which could influence option premiums and dividend yields in the coming months.

Despite this, the portfolio has generated $583.78 in net dividends for April. While this represents a slight decline from March, it underscores the resilience of the YieldMax strategy in a cooling volatility environment. As we move into May, careful balancing and strategic positioning will be key to navigating the evolving market landscape.

What Happened?

US Equity Market

The S&P 500 closed April at 5,515.72, down 10.2% from it's all time high of 6,144.15 set in Feb 2025. The market face broad-based pressure throughout the month, driven by 2 primary developments:

• The announcement of sweeping new US Tariffs in early April 2025, which reignited trade war concerns and triggered a swift market repricing.
• A VIX spike early April, it's highest level since the pandemic, reflecting heightened fear and demand for downside protection.
• A stabilizing end to the month, as investors digested a strong April jobs report, released late in the month, which reinforced the Fed's case to delay interest rate cuts, further cooling investor sentiment.

By April 30, the VIX had cooled, while still elevated, was well below it's early month panic high, signaling, fading volatility even as equity indices remained under pressure.

Cryptocurrency Market

Bitcoin's April trajectory was volatile but ultimately bullish. After dropping to $76,000 in early April, it then rebounded to end the month around $95,600. The recovery was supported by:

• The announcement of a US strategic Bitcoin reserve
• Renewed institutional interest
• Continued positioning of Bitcoin as a digital safe haven amid fiat uncertainty.

However, despite the bounce, BTC's post halving performance lagged behind historical cycles and crypto equities like MSTR and COIN remained under pressure. 

Market Outlook

As we head into May 2025, markets face a delicate balancing act between cooling inflation, robust employment and geopolitical uncertainty. In spite of legitimate concerns about trade disruptions and delayed Fed action, the rapid VIX retracement also suggests that investors are not pricing in prolonged fear.

Portfolio Overview

Transactions and Options Overview

Total deployed in April 2025 : USD 3,245.79

Averaging into MSTY, anticipating IV recovery and capital appreciation potential as Bitcoin and MSTR sentiment rebuild. Average cost remains favorable relative to long term bullish expectations for MicroStrategy and Crypto in general.

Portfolio Breakdown

The portfolio closed April with a total market value of USD 18,194, down from the total invested capital of  $20,771.37, reflecting a net unrealized loss of - USD 2,577.37 (-12.41%). This decline was primarily driven by price depreciation in CONY and YMAX, while MSTY remained the portfolio's relative outperformer.

The portfolio remains heavily weighted in MSTY (76%) as we build towards a 1,000 share position. While unrealized losses in CONY and YMAX weigh in on the total return, dividend income has softened the drawdown. May's strategy will focus on defensive dividend compounding and volatility  re-entry timing.

Lessons from April

• A high VIX doesn't guarantee high YieldMax premiums -  IV30 is the primary income driver
• Bitcoin's price recovery did not lift MSTY premiums - Direction does not equate Volatility

Project Implications and Strategic Adjustments

• Total returns remain positive, despite a -USD 2,577.37 unrealized loss, thanks to $2,625 in dividends and USD 178 in option premiums resulting in a net gain of USD 226 (+1.09%) on invested capital.
• Dividend income has proven resilient, softening the impact of price depreciation in CONY and YMAX. This validates the income-buffer strategy in volatile conditions.
• Option income contribution remains minor (6.8% of income) due to falling IVs. This highlights the portfolio's dependence on dividends, particularly from MSTY to sustain returns

Strategic Adjustments for May 

• MSTY accumulation will continue cautiously

MSTY remains the portfolio's most stable performer and is supported by MSTR's recovery. Further additions are viable below US 25, provided IV remains above 40. To watch for consolidation in MSTR above US 400 before deploying larger tranches.

• No addition to CONY and YMAX for now

Both remain in capital decline with shrinking IV due to pressure from COIN and tech-linked softness respectively. 

• Deploy options strategically during IV spikes

Favor short duration cash secured puts or covered calls only when IV pops above 50 particularly around:

• April CPI (Release May 13) 
• Federal Reserve Events / Macroeconomic Data release.
• Crypto related market catalysts

Conclusion

The MSTR rebound in April justifies continued confidence in MSTY, but low IV across the board calls for more precision and less passive compounding. May strategy will lean into tactical accumulation, option spikes and watchful re-entry into underperformers only if volatility returns.

📬 Help Improve This Blog

To make this blog more comprehensive, I'm currently seeking:

• 💬 Reader feedback on option strategies or ETF income ideas

• 📈 Requests for visual charts (bar/line graphs of dividends or drawdowns)

• 📊 Suggestions for additional diversification ETFs or hedging tools

• 🧮 Any interest in backtesting or rolling yield projections for CONY/MSTY/YMAX

If there’s anything you’d like to see added, or have specific questions about income ETFs or option strategies, feel free to reach out or drop a comment!

 

Summary – March 2025 (YMAX, MSTY, CONY)

Introduction

March 2025 proved to be a brutal month for markets, and our portfolio wasn't spared. Between surging volatility, crumbling tech valuations, and a sharp crypto correction, the investing environment quickly turned defensive. 

What Happened?

US Equity Market

In the United States, equity markets experienced notable declines.

• The S&P 500 shed 4.6% in the first quarter, marking the worst quarterly performance since 2022.
• The Nasdaq Composite plunged 10.5% during the same period also reflecting investor concerns.
• The Dow Jones Industrial Average declined by 1.3%

Technology were particularly affected, with Tesla and Nvidia experiencing substantial losses of 36% and nearly 20% respectively.

Cryptocurrency Market

The cryptocurrency sector has also mirrored the turbulence seen in equity markets.

• Bitcoin's price tumbled down nearly 25% from its January highs

Market Outlook

The recent market downturns underscore the importance of diversification and strategic asset allocation. Investors should remain vigilant, considering both global economic indicators and geopolitical developments. In the cryptocurrency space, the current volatility may present buying opportunities for long term investors, but caution is advised given the sector's inherent risk.

For YMAX, CONY and MSTY, with the drop in the market, Implied Volatility (IV) surged. This may indicate greater monthly distributions moving forward, which would help cushion the NAV (Price) drop with the stronger yield income.

CONY and MSTY were hit harder, as both COIN and MSTR declined sharply amidst the tech selloff and crypto pullback. In comparison, YMAX held up better as it was diversified across many tech counters.

The following is a breakdown of what transpired in our portfolio, key market insights and strategic adjustments for March 2025.

Portfolio Overview (March 2025)

Transaction & Options Overview

March's trading activity was focused on generating premium income and adjusting positions to align with market conditions. The key option transactions included:

Portfolio Breakdown 

Key Observations & Analysis

• CONY (-49%) Cryto Crash Collateral Damage

March was a nightmare for Coinbase and by extension CONY. As bitcoin's 25% drawdown accelerated by the Bybit hack, centralized exchanges such as COIN faced scrutiny and withdrawal spikes. Lower trading volumes and negative sentiments drove the stock lower, slicing through CONY's NAV despite high premiums and call writings.

• MSTY (-16%) Bitcoin's Whiplash Hits Home

MSTY was spared the worst, but still ended deep in negative territory. MicroStrategy's strategy of holding massive Bitcoin reserves with leverage backfired this month. As BTC slumped, MSTR followed and so did MSTY. The ETF did, however benefit from soaring implied volatility, cushioning the drawdown with substantial option income.

• YMAX (-28%) Tech Gets Tagged

Although YMAX outperformed the others, it wasn't immune. The tech heavy Nasdaq's 10.5% quarterly drop (it's worst since 2022) dragged down YMAX's underlying holdings. However, thanks to it's broader diversification and disciplined call writing strategy, The ETF delivered strong income, softening the blow on total returns.

• Overall portfolio (-28%) loss reflects a month where macro headwinds and sector specific risks collided. 

Lessons from March

• Covered calls work better in a flat or modestly volatile market, but not during sharp drawdowns.
• Crypto-tied ETFs like CONY  and MSTY offer juicy yields, but come with amplified risks. 
• YMAX's diversified structure can offer some shelter, but not immunity. 

Portfolio Implications and Strategic Adjustments

Strategic Adjustments

These changes signal a tactical re-engagement with risk and  potentially a better income trajectory.

Portfolio Implications

March Strategy Paid Off

• The decision to increase allocation captured part of the rebound from oversold levels.
• YMAX and MSTY showed stabilization.

Looking ahead to April 2025

• Bitcoin support at $80k remains key. If breached, expect more downside for MSTY and CONY
• Implied Volatility is still elevated. Excellent for premium income
• Broader markets remain jittery. Look into diversification into CSPX
• Expect modest income recovery in April if tech and crypto stabilize.

📬 Help Improve This Blog

To make this blog more comprehensive, I'm currently seeking:

• 💬 Reader feedback on option strategies or ETF income ideas

• 📈 Requests for visual charts (bar/line graphs of dividends or drawdowns)

• 📊 Suggestions for additional diversification ETFs or hedging tools

• 🧮 Any interest in backtesting or rolling yield projections for CONY/MSTY/YMAX

If there’s anything you’d like to see added, or have specific questions about income ETFs or option strategies, feel free to reach out or drop a comment!

Summary – February 2025 (YMAX, MSTY, CONY)

Introduction

February has been a turbulent month for financial markets, particularly with the crypto currency linked high yield ETF sector. A sharp decline in Bitcoin, stagnation in Ethereum prices and a looming USD $5 billion options expiry were key drivers of  market volatility, leading to heightened uncertainty.

Adding to the complexity, broader economic and regulatory shifts played a significant role. The ongoing US-EU trade conflict, the SEC's decision to dismiss its lawsuit against Coinbase and the USD $1.5 billion Bybit hack further reshaped investor sentiment, intensifying concerns about exchange security and centralized platforms. These events highlight the need for strategic diversification, hedging tactics and a keen awareness of macroeconomic factors.

For CONY, MSTY and YMAX, these factors translated into a challenging month, with notable price declines. However, strong income distribution rates continued to reinforce their long-term appeal, highlighting the resilience of income generating strategies despite short term volatility.

The following is a breakdown of what transpired in our portfolio, key market insights and strategic adjustments for February 2025.