Value Options Letter
Education
Long-form guides on options income strategies, written for investors who want the discipline, not the hype. Research first. Value first.
Strategy · 10 min read
Cash-Secured Puts 101
Getting paid to wait for your price. How cash-secured puts work, when value investors should use them, and the three mistakes that turn a patient strategy into a painful one.
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Strategy · 9 min read
Covered Calls 101
Generating income on businesses you already own. How to think about covered calls as a value investor, and why most retail investors get this trade exactly backwards.
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Strategy · 12 min read
Iron Condors 101
A defined-risk strategy for range-bound conviction. When iron condors make sense, the math that actually matters, and why they're a tool, not a default.
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Tax · 14 min read
A Plain-English Guide to Options Taxes
Short-term versus long-term. Qualified covered calls. Section 1256. Wash sales. The IRA question. What matters, what doesn't, and the record-keeping habits that save you at tax time.
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Setup · 11 min read
Getting Approved for Options Trading at Your Broker
Options approval levels explained, broker-by-broker walkthroughs for Schwab, Fidelity, Interactive Brokers, tastytrade, and E*TRADE, plus the answers that actually get you approved on the first try.
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Setup · 12 min read
How to Place Options Limit Orders
A practical, broker-by-broker walkthrough for entering options limit orders on Schwab, Fidelity, and Interactive Brokers. Plus the diversification framework, common mistakes, and the eight-point pre-trade checklist that prevent the most expensive entry errors.
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Strategy · 11 min read
The Wheel Strategy: A Value Investor's Take
The most popular options-income strategy on the internet, properly understood. Why most YouTube versions are dangerous, and what a value-first approach to wheeling actually looks like.
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Risk Management · 10 min read
Position Sizing for Options Income
The single biggest determinant of long-term results that almost nobody writes about properly. A practical framework for sizing cash-secured puts, capping ticker and sector exposure, and avoiding concentration creep.
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Philosophy · 12 min read
Why We Rarely Roll Options
A contrarian view on the most popular loss-management technique in options-trading content. We think rolling is usually a behavioral cope masking a bad initial trade. Here's our reasoning, and the rare cases where rolling actually makes sense.
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Methodology · 11 min read
Implied Volatility for Options Sellers
What IV actually measures, why sellers love it, and the seductive trap of optimizing for IV at the expense of everything else. A value-first investor's guide to using implied volatility as a confirming input rather than a primary trade selector.
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Strategy · 9 min read
What to Do When You're Assigned
Assignment is not an emergency — it's the natural outcome of a put you sold. The first-24-hours playbook, the four most common mistakes, and how to re-evaluate the position with fresh eyes.
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Methodology · 12 min read
The Greeks for Options Sellers
Delta, theta, vega, gamma — what they actually mean, which ones matter most for cash-secured put and covered call sellers, and how to use them without getting trapped in spreadsheet thinking.
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Methodology · 11 min read
Building a Value-First Watchlist
The single most important piece of preparation for an options-income program — and the one most investors skip. How to build a list of 10-25 businesses you'd genuinely want to own at lower prices, and how to maintain it over time.
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White papers
Longer-form pieces that go deeper than an article. Free to download — no email required.
White Paper · ~2,200 words · PDF
Portfolio Sizing for Options-Income Investing
How much capital does it take to run the VOL approach? A practical framework for thinking about account size, position count, and reserve buffers — with explicit guidance for accounts above and below our suggested $100,000 starting point.
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White Paper · ~5,400 words · PDF
Income Without Speculation
The wheel strategy, applied to value investing. The mechanics in plain language, the three preconditions that separate disciplined wheeling from yield chasing, a worked example, and an honest accounting of what can go wrong.
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See it — or hear it — live
Two surfaces beyond the article library: real wheel cycles in progress with running income figures, and an invite to our next educational webinar.
Live data · Public
Wheel cycles, in progress
Each cycle ties together the cash-secured puts and covered calls on the same shares, with cumulative premium captured and capital at the underlying CSP strike. See the cycles in motion before you subscribe.
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Educational webinar · Live Q&A
Get notified about the next session
Practical sessions on running options income against businesses you actually want to own — position sizing, when assignment is the right outcome, picking strikes against a value anchor. Live Q&A so you can pressure-test the framework against your own portfolio.
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