A Real Portfolio.
Fully Transparent.
Zero Black Box.
Expired Options is the public record of my real investment portfolio. I am a long-term buy-and-hold investor who uses covered calls, cash-secured puts, and LEAPS to generate premium and build positions over time.
I have publicly documented my portfolio through weekly updates since July 2023, including performance, options premium, portfolio changes, and trades that do not go as planned.
How the Strategy Works
Buy and Hold as the Foundation
First and foremost, I am a buy-and-hold investor. I build positions in companies I believe have long-term upside and generally intend to hold them through market cycles. My options strategy is designed to work around those long-term holdings, not replace them.
Covered Calls and Cash-Secured Puts
I sell covered calls against shares I own and cash-secured puts on companies I am comfortable owning if assigned. I generally target 0.10 to 0.20 delta and favor shorter expirations, often 7 to 14 DTE. I also pay close attention to earnings, Fed meetings, inflation data, and labor reports before opening new contracts.
LEAPS as a Capital-Efficient Ownership Trial
I began using LEAPS in 2023 as a trial period toward potentially owning shares. I typically buy the furthest expiration available and target approximately 0.70 delta. If the position performs well and my conviction remains intact, my goal may be to exercise the contract near expiration and own the shares.
Defined Capital, No Margin
I do not sell naked options or use margin. My covered calls are backed by shares or qualifying long calls, and my cash-secured puts are backed by cash. I manage risk primarily through position sizing, diversification, lower-delta contracts, and avoiding companies I would not be comfortable owning.
Why Make It Public?
I started publicly documenting my portfolio because I wanted to show the full process, not just winning trades. Since July 2023, I have posted weekly updates showing my portfolio performance, premium collected, and options activity.
The goal is transparency and consistency. Some positions work. Others get assigned, require rolls, or move against me. I believe showing those outcomes provides a more realistic view of long-term investing and options selling.
Community
I share weekly portfolio updates, options activity, and strategy discussions through the Expired Options community. My public posts document the portfolio over time and provide a running record of how I manage more than 100 tickers and a large number of open options positions.
r/ExpiredOptions →Annual Portfolio Performance vs. S&P 500
These are calendar-year returns from my investment portfolio compared with the S&P 500. Portfolio returns reflect overall account performance, including changes in the value of stock and options positions and options premium activity. Deposits and withdrawals are excluded from percentage return calculations. Account balance growth will differ from investment gains because additional capital may be contributed. The S&P 500 benchmark returns represent Total Return, including reinvested dividends.
Past performance does not guarantee future results. Returns reflect closed P&L and premium income. Not financial advice.
From $50.00 to $500,000+
A decade of disciplined real-money execution: from a modest $50 deposit through patient accumulation to high-velocity options compounding.
Started Investing with $50.00
The beginning of the real-money journey. Started with a modest $50 deposit to learn market mechanics and build lifelong saving habits.
$100,000 Milestone Reached
The critical foundation phase. Required 5 years, 8 months (2,071 calendar days) of unwavering discipline, automatic monthly contributions, and market gains through volatile cycles.
$200,000 Milestone (First Doubling)
The compounding engine took over: while the first $100K took 5 years 8 months, the second $100K took only 2 years 11 months (1,065 calendar days) of contributions and compounding—reaching 8 Yrs, 7 Mths total.
$250,000: The Strategic Turning Point
Reached $250K at 9 years, 4 months (274 calendar days after $200K). At this critical juncture, systematic options income (covered calls, cash-secured puts, and LEAPS) alongside regular savings was fully unlocked.
$255K → $300K Options Sprint
First targeted options sprint: added +$45,000 across ongoing contributions and options gains in 59 calendar days (42 market days) reaching 9 Yrs, 6 Mths cumulative using cash-secured puts on dividend-growing companies.
$300K → $350K Options Sprint
Second sprint: accumulated another +$50,000 in contributions and gains in 76 calendar days (54 market days) reaching 9 Yrs, 9 Mths cumulative by systematically reinvesting option premiums directly back into equity positions.
$350K → $400K Options Sprint
Navigated an extended market consolidation period. Added +$50,000 across savings contributions and options income over 150 calendar days (107 market days) reaching 10 Yrs, 2 Mths cumulative through methodical strike selection.
$400K → $450K Velocity Sprint
Rapid sprint acceleration: added +$50,000 in contributions and options gains in 75 calendar days reaching 10 Yrs, 5 Mths cumulative as market momentum and elevated implied volatility boosted options premium yields.
$450K → $500K Milestone 1 Complete
The historic Milestone 1 benchmark: fully completed in 354 calendar days, reaching 11 Yrs, 4 Mths cumulative with an all-time peak of $507,304 across lifetime contributions and investment returns, documented publicly every week.
Road to $600,000 (Active)
The active mission: documenting every trade, weekly review, options expiration, and capital change toward the $600,000 peak.
Want to benchmark your own portfolio against this timeline?
👤 TEST YOUR ROAD TO A MILESTONE →New to Options? Start Here
New to options? I have created free educational guides covering the core concepts I use in my own portfolio, including covered calls, cash-secured puts, LEAPS, options Greeks, and portfolio risk management.
VIEW FREE GUIDES →⚠️ FINANCIAL DISCLAIMER
Expired Options documents my personal investment portfolio and options activity for educational and informational purposes. I am not a registered investment adviser or broker-dealer, and nothing on this website is personalized investment advice or a recommendation to buy or sell any security or options contract. Options involve substantial risk and are not appropriate for every investor. Past performance does not guarantee future results. Any investment or trading decision you make is your own responsibility.
© 2026 EXPIREDOPTIONS // ALL RIGHTS RESERVED