June became the first real stress test of the portfolio.
Five separate assignments landed within eight trading days. IONQ, AMZN, ONDS, SOFI, and AKAM all converted from cash-secured puts into owned shares between June 5 and June 12.
A large portion of capital shifted from cash into equities almost simultaneously. That was not a coincidence.
It was the Wheel doing exactly what it is designed to do when multiple option cycles mature at once.
The market did not make it easy.
VIX spiked above 21 mid-month.
SPY lost short-term support.
QQQ broke lower, with growth and high-beta names leading the weakness.
By June 26, the S&P 500 had pulled back roughly 3.5% from its May highs.
The account followed.
That is the story of June: a portfolio absorbing a meaningful pullback while continuing to collect premium on schedule, without forcing a single trade to compensate.
The Numbers
17 trades closed in June, covering Week 22 through Week 27 and including July 2.
12 expired worthless or were closed early for profit.
5 were assigned.
$8,109 in realized premium was collected.
$5,131 came from cash-secured puts.
$2,978 came from covered calls.
Zero realized losses occurred on the options themselves.
Every assignment landed at a strike that had already been accepted before entry.
Portfolio NAV moved from $264,749 on May 29 to $256,709 on June 26.
By July 3, including early July trades, NAV stood at $257,637.
The account return for the period was -2.7%.
The S&P 500 over the same window was -1.4%.
Since inception on April 1, the account is up 3.1%.
The S&P 500 over the same period is up 17.9%.
The gap versus the index widened as capital rotated from cash into assigned shares during the June pullback.
The account is not designed to hedge broad market declines.
It is designed to continue generating premium while positions transition through the Wheel cycle.
June tested that objective for the first time.
What Worked
GLXY — The May Mistake, Closed Correctly
GLXY was the flagged mistake from May.
Premium became more important than structure, and that violated the process.
June closed that chapter correctly.
One covered call expired worthless, collecting $344.
A second call at the $32 strike captured another $480 before the shares were called away above assignment basis.
The position is now closed.
Capital is free again.
The lesson from May was simple: high premium never compensates for weakening structure.
The lesson from June was equally important: disciplined management can still produce a clean exit after a poor entry.
ABNB — Full Cycle, Clean Exit
Assigned in May at $138.
Covered call opened in early June at $141, above cost basis and inside a recovering EMA/SMA support cluster.
Shares were called away at expiration.
$510 in premium was collected plus roughly $600 in appreciation above assignment price.
Total realized on the second leg was approximately $1,110.
This remains the ideal Wheel outcome.
Assignment is not a loss event.
It is the midpoint of a longer trade.
IONQ and SOFI — Repeated Covered Call Discipline
Both names completed multiple covered-call cycles during June, following the same management rules: calls written only above assignment basis, with room for upside, never forcing premium at the expense of exits.
IONQ completed three covered-call cycles at the $65, $65, and $59 strikes, collecting $430, $610, and $310.
Two expired worthless.
Current cost basis sits at $47.95 versus a current share price of $49.12.
SOFI completed two covered-call cycles at the $18.5 strike, collecting $432 and $216.
Shares now sit roughly 13.6% above the $16.06 net cost basis.
Neither position generated a process warning.
Both continue to demonstrate that the covered-call phase remains the portfolio’s most consistent source of premium.
High-APR Short-Duration CSPs
RDDT at the $160 strike, 9 DTE, collected $800 and expired worthless.
BTDR at the $17 strike, 4 DTE, collected $600 with a Real APR above 280%.
HOOD at the $98 strike, 2 DTE, collected $290 with an even higher annualized return.
These remain the preferred entries within the process: short duration, defined support, earnings outside the option cycle, and elevated premium supported by structure rather than desperation.
What Hurt
AKAM — The Largest Drawdown in the Book
Assigned June 12 at the $152.50 strike.
Net cost basis after premium: $149.50.
By month-end, AKAM traded at $113.17.
That was a decline of approximately 24.3% from cost basis, representing an unrealized loss of roughly $7,266.
The setup was graded A-.
Setup Valid was flagged Y.
This was not another GLXY.
The entry followed the process.
The market simply continued lower.
That distinction matters.
It does not change the unrealized loss.
The question entering July is different: at what point does a valid setup become a sizing lesson, regardless of whether the original entry was correct?
ONDS — Still Underwater, Still Speculative
Assigned at $11.
Net cost basis after premium: $9.96.
Current price: $7.41.
Unrealized loss: approximately $3,825.
ONDS has always belonged to the speculative bucket.
One covered call generated $405 in premium before being closed early after capturing roughly 74% of the available value in only three trading days.
That management decision was correct.
The underlying simply has not recovered.
The position remains the portfolio’s second-largest unrealized drawdown.
It reinforces an important principle: speculative positions deserve their own sizing limits, regardless of how attractive the premium appears.
EQNR and AMZN — Capital Parked, Not Losing, Not Working
EQNR: 600 shares at a $36.55 cost basis, currently trading near $32.04.
AMZN: 200 shares at a $251.97 cost basis, currently trading near $242.67.
Neither position currently offers an acceptable covered-call strike above assignment basis.
The correct decision has been to wait.
That patience preserves process discipline, even though it leaves meaningful capital temporarily inactive.
Open Positions Entering July
Shares
Note: 600 shares held at a $39.00 cost basis. No covered call is active yet.
Note: 200 shares held at a $57.00 cost basis. Covered call at $59 remains active through July 10.
Note: 1,200 shares held at a $17.00 cost basis. Position is ready for the next covered call cycle.
Note: 200 shares held at a $262.50 cost basis. No covered call is active yet.
Note: 1,500 shares held at an $11.00 cost basis. No covered call is active yet.
Note: 200 shares held at a $152.50 cost basis. No covered call is active yet.
Open CSPs
Note: RXRX remains the only open cash-secured put, with $600 in premium collected into the July 10 expiration.
Open CCs
Note: IONQ remains the only open covered call, with $310 in premium collected into the July 10 expiration.
Total open exposure: $164,900.
Total pending premium on open positions: $910.
Process Note
No Setup Valid = N.
No Would Repeat = N.
Not a single process violation occurred across seventeen completed trades.
That is the biggest difference versus May.
May contained one trade where premium overrode structure.
June contained none.
Every assignment entered the portfolio at a price that had already been accepted before the trade was opened.
June did not test whether the Wheel can generate premium.
It tested whether the process could continue while unrealized losses expanded across several positions simultaneously.
Realized premium reached $8,109.
The equity book finished the month lower.
Both statements can be true at the same time.
The account finished June down 2.7%.
None of that decline came from realizing bad option trades.
It came from temporarily holding assigned shares through a broad market pullback, the exact scenario the Wheel is built to accommodate.
The gap versus the index widened.
That is the tradeoff being made deliberately: accepting mark-to-market volatility in exchange for systematically collecting option premium without forcing trades or chasing returns.
The book is red.
The process is intact.