StrikeDesk

Mag 7

ETFs

S&P 500

My Tickers

PMCC — Poor Man's Covered Call

Ticker

LEAPS Expiry

LEAPS Strike

Short Call Expiry

Short Strike

📊

Select a ticker above, choose your expiry dates and strikes, then click Analyze to see live options data and strategy metrics.

Breakdown

Cash-Secured Put / Sell Put

Ticker

Expiry

Strike

Contracts

Covered Call

Ticker

Expiry

Strike

Cost Basis / Share

Shares Owned

📦

What is a Box Trade?

Think of it like a bank loan using options. You use 4 option contracts to lock in a fixed interest rate — completely independent of where the stock goes. The profit is mathematically guaranteed at expiry.

📥 Buy a Box = Lend Money ✅

Pay less than settlement value today. Receive full settlement at expiry. You earn the difference as interest — you are the lender.

Example: Pay $302,731 today → receive $315,000 at expiry → earn $12,269 interest

📤 Sell a Box = Borrow Money

Receive more than settlement value today. Pay full settlement at expiry. You pay the difference as interest — you are the borrower.

Example: Receive $302,731 today → pay $315,000 at expiry → pay $12,269 interest

💡 Compare to T-Bills: Only makes sense if the implied rate beats the current T-Bill rate (~4.5%). Otherwise just buy T-Bills.

⚠️ Important: Box trades only work safely with European-style options (SPX, XSP) which can only be exercised at expiry. Using American-style options (SPY, AAPL etc.) risks early assignment — the other party can exercise early, breaking your locked-in rate and causing unexpected losses.

Box Trade Calculator

How it works — 4 legs, 2 strikes: You pick K1 (lower) and K2 (upper). StrikeDesk automatically uses all 4 legs: 📗 Buy call at K1 📗 Buy put at K2 📕 Sell call at K2 📕 Sell put at K1

Ticker — Use SPX or XSP for best results

Expiry Date

Lower Strike K1 — Leg 1 & 4

Upper Strike K2 — Leg 2 & 3

What do you want to do?

Contracts

Price You Paid/Received (per share) optional — for accurate rate

From IBKR: Total paid ÷ (100 × contracts). e.g. $302,731 ÷ 300 = $1,009.10/share

Breakdown — 4 Legs of the Trade

🏦 My Box Loans

Track your active box loans — cost, expiry, and when to roll.

Ticker	Legs	Amount	Rate	Annual Cost	Opened	Expires	Days Left	Status
No box loans tracked yet. Click + Add Box Loan to add yours.

Other Strategies — Quick Analyzer

Ticker

Strategy

Expiry

Strike 1

Strike 2

📡 My SPX Calls — All Contracts

Enter current mid from IBKR to see live M2M · Click row to load

Contract	Entry Date	Days Held	Entry Mid	Current Mid (from IBKR)	M2M Loss/GainMark-to-Market Loss/Gain Actual change since entry date. Entry mid − current mid × 100 × contracts. Negative (loss) = SPX went up → you can offset this many dollars of capital gains on Dec 31 this year.	Harvest CapacityAnnual Harvest Capacity = SPX × 7% growth × 100 × contracts Estimated M2M loss per year going forward. How many NVDA shares to sell: shares = Harvest Capacity ÷ gain per share e.g. $52,000 ÷ $180/sh = 288 shares → $0 federal tax Use M2M (left column) for this year's actual limit.	Purpose

📈

Index Call Harvest — Deep ITM Call + VOO Strategy

Sell a deep in-the-money SPX call (strike 2000, Dec 2031). Use the premium + a box loan to buy VOO shares. The VOO position hedges the call. Section 1256 marks the call to market each Dec 31 — generating tax losses to offset capital gains from ISRG, NVDA, TSLA exits. Works in all market conditions.

📥 Step 1 — Sell Call

Sell 1-3 SPX/XSP Dec 2031 2000 Call. Receive premium. Take box loan for the balance.

📤 Step 2 — Buy VOO

Use premium + loan to buy 1,081 VOO per contract. VOO position hedges the call obligation.

💰 Step 3 — Harvest

Each Dec 31: Section 1256 MTM loss offsets gains. Sell ISRG/NVDA/TSLA tax-free.

Strategy Calculator

Index Ticker

Strike

Expiry Date

Contracts

Call Mid Price ($ per share)

VOO Shares to Buy (auto-calculated from premium + loan ÷ VOO price)

Box Loan Rate (%/yr)

VOO Price

📊 Performance Since Entry

Entry Date

—

Days Held

—

Entry Call Mid

—

per share at entry

Current Call Value (from IBKR)

Enter current mid from IBKR

IBKR → Portfolio → SPX Dec18'31 2000 Call → Last price

Theta Collected

—

time decay since entry

M2M 1256 Loss/Gain

—

Scenario Analysis — P&L at Expiry

Shows net P&L at expiry for each market scenario. Call P&L + VOO P&L − interest = Net. XIRR = annualized return on VOO invested capital.

SPX at Expiry Projected index price at expiry. 30 scenarios from 0 to 3.75× today. `x × (index_today / 8)`	VOO Value VOO position value at expiry with quarterly dividend reinvestment. `voo_cost × (SPX_exp/SPX) × (1+div)^qtrs`	Call Payoff Amount you OWE to settle the short call at expiry. Zero if index stays below strike. `max(SPX_exp − strike, 0) × 100 × contracts`	VOO − Call Your net asset = VOO value minus call obligation. `VOO_value − Call_payoff`	Dividend Part How much of VOO value comes from dividend reinvestment. Extra return vs just tracking the index. `VOO_value − (voo_cost × SPX_exp/SPX)`	Loan Interest Compound interest cost on the box loan over full period. `LOAN × ((1+rate)^years − 1)`	M2M 1256 (Harvest) 🟢 NEGATIVE = YOUR LOSS = HARVEST ✅ SPX rose → call worth more → you lost → harvest against stock gains → $0 tax 🔴 POSITIVE = YOUR GAIN = OWE TAX ❌ SPX fell → call worth less → you gained → sell fallen stocks to offset Section 1256 marks to market each Dec 31. `Premium_received − Call_current_value`	VOO Unrealized VOO unrealized gain vs your cost basis. Offset by M2M 1256 gain for net tax position. `VOO_value − VOO_cost`	SPX XIRR Annualized return from simply holding the index (benchmark). `(SPX_exp/SPX_today)^(1/years) − 1`	VOO XIRR Annualized return from holding VOO with dividends (benchmark). `(VOO_exp/VOO_cost)^(1/years) − 1`	Call XIRR Annualized return on the call alone. Invest premium, receive call payoff. `(Call_payoff/Premium)^(1/years) − 1`	VOO-Call XIRR (Gross) ★ Matches spreadsheet exactly. Return on LOAN before deducting interest. Interest shown separately. `(VOO−Call / LOAN)^(1/years) − 1` Typical: 12–20% ✅	VOO-Call XIRR (Net) ✅ True after-cost return. Return on LOAN after all costs including interest. `((VOO−Call−Interest) / LOAN)^(1/years) − 1` Typical: 9–15% ✅

📊 Breakeven Chart — Strategy vs Alternatives

Net P&L at expiry across all scenarios. Shows where strategy beats just holding VOO or SPX.

VOO-Call Net P&L VOO only SPX only Break even ($0)

🌾 Tax Loss Harvest Calculator

Enter your concentrated stock details. Calculator shows exactly how many shares to sell to fully offset the Section 1256 M2M loss — paying $0 tax on the sale.

Stock Ticker

Cost Basis ($/share)

Current Price ($/share)

Your Tax Rate (%)

Scenario M2M Loss ($) auto-filled on hover

Shares You Own

📅 Annual M2M Harvest Journal

Log what you harvest each December. Tracks cumulative tax savings over the strategy life.

Year	Date Logged	M2M Loss	Stocks Sold	Proceeds	Gain Realized	Tax Saved	Carryforward	Notes
No harvest entries yet. Click + Log This December after each year end to track your harvest history.

Live Call Chain — SPX

Deep ITM calls near your selected strike. Select your expiry above then click Load Live Chain.

Strike	Bid	Ask	Mid	IV%	Delta	Theta	OI	Use This

📊 Portfolio Projection

See your portfolio value across different market return scenarios. Includes harvest plan, VOO accumulation, tax savings and debt ratio.

Retire / Wind-down Year

Max Debt Ratio flags years over this

Year-by-year Debt% turns red ⚠ when it exceeds this

Combined LTCG Rate (%) fed 23.8 + CA 13.3

Initial Call Mid ($) — your actual fill

SPX Contracts max total

Entry timing

At expiry

Box loan needed: $200,000 · Harvest: ~$40K/yr

New box loan in late 2026 after boxes settle

Deploy into VOO after Oct+Dec boxes settle

MARKET RETURN SCENARIOS — click to highlight

⚠️ Crash Stress Test

Apply a sudden market drop to one year — see margin headroom & phantom tax for your contract count.

Crash year

Drop %

🎯 Glide Path to Retirement

Ramp toward a target mix by your retirement year, then see safe withdrawal income.

Retire year

Target mix

Withdraw %

💰 Borrow to Live — Buy, Borrow, Die

Take box-spread loans instead of withdrawals. Portfolio grows untouched. Tax = $0 while alive. Heirs inherit at stepped-up basis.

Loan mode

Loan rate

State

Effective rate —

🏛️ Go to Equity Exit →

🏛️ Equity Compensation Plan – ISRG

ESPP • RSU • NQ Options – harvest plan to diversify into VOO via SPX strategy

State

Ordinary / LTCG — / —

Total ISRG Value

–

Tax If Sold Now

–

without SPX strategy

Tax Saved w/ SPX

~$261K

over 5 years

Sellable Now

–

Unvested Coming

–

Concentration Risk

100%

in single stock

📊 Equity Net Worth — All Categories

Category	Shares	Cost Basis	Current Value	Gain / Loss	Gain %	Tax	After-Tax Gain

💳 ESPP – 637 shares

15% discount purchase plan • All lots sellable

Purchase Date	Shares	Cost Basis	Current Price	Gain / Loss	Total Gain	Tax (LTCG)	Harvest Priority

📊 RSU – Restricted Stock Units

Basis = FMV on vest date • Ordinary income already paid at vest

Grant	Grant Date	Granted	Vested	Unvested	Avg Basis	Current Value	Gain vs Basis	Tax @ 23.8%*

*RSU: ordinary income paid at vest. Capital gains tax (23.8% LT or 40.1% ST) only on appreciation after vest date.

🔧 NQ Options – Non-Qualified Stock Options

Exercise = ordinary income on spread

⚠️ SPX Section 1256 losses are capital losses — they cannot offset ordinary income from NQ exercises. Each exercise creates W-2 income taxed at —. Plan carefully to spread income across years.

Grant	Grant Date	Strike	Exercisable	Unvested	Intrinsic/share	Total Intrinsic	Tax (ordinary)	Expires	Urgency

📅 NQ Exercise Schedule – Spread Ordinary Income Over Years

Goal: keep NQ ordinary income under ~$80K/yr to avoid bracket creep • After exercise hold shares 1yr → then SPX-harvest as LTCG

Year	Grants to Exercise	Shares	Ordinary Income	Tax (ordinary)	Net Cash After Tax	Hold→Sell Next Year as LTCG

🚀 Complete Exit Plan — ISRG → VOO (2026–2031)

Values at today's ISRG price · actual proceeds will differ

Year	Actions	Shares → VOO	Proceeds	Tax This Year	Progress

📅 Upcoming Vest Schedule

🎯 SPX Harvest Plan – ESPP + RSU Sales → VOO

Each December: SPX call MTM loss (capital loss) offsets LTCG from ESPP/RSU sales → $0 tax ✅

Note: NQ exercise income is handled separately above — these are LTCG sales only

Year	Action	Shares	LTCG Gain	Tax Without SPX	Tax With SPX ✅	Proceeds → VOO	Notes

📈 Diversification Progress – ISRG ➜ VOO

📊 Go to Projection →

💰 Portfolio Income Dashboard

Monthly income across all active strategies – P&L, targets, and allocation

Monthly Income

–

from active strategies

Annual Run Rate

–

Capital Deployed

–

Active Strategies

–

Unrealized P&L

–

$500/mo Target

–

📊 Strategy Breakdown

Strategy	Ticker	Type	Capital	Entry Credit	Current P&L	DTE	Monthly $/Capital	Status	Action
Loading strategies...

📊 Income by Strategy Type

✅ $500/month Target Progress

Progress to $500/mo –

📅 Upcoming Expirations – Action Needed

No expiring strategies in next 30 days.

💼 My Holdings

Track positions. Each December, harvest tax-free using SPX strategy losses.

📊 Total Net Worth

Stocks & ETFs

—

Options P&L

—

Cash

—

VOO Hedge

—

SPX Liability

—

SPX Net

—

Total Net Worth

—

Enter SPX call value in Index Call Harvest tab

📈 Stocks & ETFs

Live prices · 🌾 to harvest tax-free

Ticker	Lot / Notes	Shares	Cost Basis	Current	Gain/Share	Total Gain	Gain %	Action
Loading...

📋 Option Positions

Equity options ●live · SPX/XSP: enter from IBKR

Ticker	Description	Side	Contracts	Entry	Current	P&L/Contract	Total P&L	Action
No option positions.

🗓️ Each December — Harvest Checklist

1. Go to Index Call Harvest tab → enter current call mid from IBKR
2. Note the M2M 1256 loss amount
3. Come back here → click 🌾 Harvest on chosen stock
4. Calculator pre-fills → shows exact shares to sell → $0 tax ✅
5. Execute in IBKR before December 31

Strategy Tracker

Name	Ticker	Entry	Current	P&L $	P&L %	Status	Date	Actions