The Full Playbook — Guides, Frameworks, and Calculators

When a single stock makes up a large chunk of your net worth. There’s no magic number, but if one position is 20%+ of your portfolio, you’re taking on more risk than most people realize. The stock might keep going up — but if it doesn’t, your entire financial picture moves with it.

The downside of that bet. If the stock drops 30%, your net worth drops with it. Diversification is the fix — but selling creates a tax problem. That’s where the playbook comes in.

What you originally paid for the stock. This is the number that determines how big your tax bill is when you sell. Low basis means a big embedded gain, which means a big tax hit. Most of the planning we do starts here.

Two options contracts that work together — one protects you if the stock drops below a floor, the other caps your upside at a ceiling. The premiums offset each other, so there’s no out-of-pocket cost. You’ve defined your range. The stock can move, but your exposure is capped on both sides.

You agree to deliver shares at a future date in exchange for cash today. You get liquidity now without triggering a taxable sale. The trade-off: you’re locked into delivering those shares later, and there are minimum net worth requirements to qualify. PVFs are harder to access than collars, but simpler in structure.

A way to borrow cash against a hedged position without selling. If you’ve collared a stock, the box spread lets you pull out up to ~80% of the value as cash — no taxable event. Basically, it turns a locked-up stock into usable money.

Multiple investors each contribute their concentrated stock positions into a single pooled fund. After 7+ years, you get back a diversified basket instead of your original single position. No taxable event at contribution. It’s a way to diversify without selling — but minimums are high and you give up control of timing.

You transfer appreciated stock into an irrevocable trust. The trust sells the stock tax-free, invests the full proceeds, and pays you an income stream for a set period or for life. What’s left goes to charity. You get a partial tax deduction upfront and defer the capital gains. The trade-off: it’s irrevocable, and the charity gets the remainder.

Selling investments at a loss on paper to offset gains somewhere else. The portfolio value stays roughly the same — you’re swapping similar investments — but you’ve created a deduction you can use now or carry forward. It’s not about losing money. It’s about being strategic with how gains and losses show up on your return.

A separately managed account that goes 130% long and 30% short. The short positions are designed to generate paper losses you can use to offset gains from selling or unwinding a concentrated position. Higher leverage versions (150/50, etc.) harvest losses faster but carry more complexity. The account value goes up, but you’re creating losses on paper along the way. That’s the whole point.

Instead of owning an S&P 500 fund, you own the individual stocks directly. Same market exposure, but now you can sell individual losers along the way to generate tax losses — something a fund can’t do for you. It’s like tax-loss harvesting on autopilot.

A charitable giving account. You contribute appreciated stock (not cash), get an immediate tax deduction at full market value, and pay zero capital gains on the donated shares. Then you recommend grants to charities over time. It’s one of the best tools for reducing a concentrated position and getting a tax benefit in the same move.

A legal workaround for people who earn too much to contribute to a Roth directly. You contribute to a Traditional IRA (non-deductible), then convert it to Roth. The money grows tax-free from there. Simple in concept, but the execution matters — especially if you have existing Traditional IRA balances.

Same idea, bigger scale. If your employer’s 401(k) plan allows after-tax contributions, you can contribute above the normal limit and convert those dollars to Roth. Potentially $30K+ extra per year into tax-free growth. Not every plan allows it — but if yours does, it’s one of the best moves available.

If you hold company stock inside your 401(k), NUA lets you roll that stock out into a taxable account and pay long-term capital gains rates on the appreciation — instead of ordinary income rates you’d pay on a normal 401(k) distribution. The difference can be significant. Only applies to employer stock, and the distribution has to be handled correctly.

For founders or employees receiving restricted stock — you elect to pay tax on the value at the time of the grant instead of when it vests. If the stock is worth $0.10 now and $50 later, you’re paying tax on the dime. The catch: you have 30 days from the grant to file it. Miss the window, miss the benefit.

Instead of receiving the full sale price at closing, the buyer pays over time — and you recognize the capital gain proportionally as payments come in. This lets you spread the tax hit across multiple years instead of absorbing it all at once. Works for businesses and real estate.

As an S-Corp owner, you wear two hats — employee and owner. Your salary gets hit with payroll taxes (Social Security + Medicare). Distributions don’t. The IRS requires a “reasonable salary,” but everything above that can come out as a distribution at a lower tax cost.

If you founded or were early at a C-Corp and held the stock for 5+ years, up to $10M in gains (or 10x your basis) can be completely excluded from federal capital gains tax. This is one of the most powerful tax benefits in the code — but the requirements are specific and the planning needs to happen early.

Pass-through business owners (S-Corps, LLCs, sole proprietors) may be able to deduct up to 20% of their qualified business income. There are income phase-outs and restrictions based on your business type, but when it applies, it’s one of the biggest deductions on the return.

Sell one investment property and buy another of equal or greater value within a set timeframe, and you defer the capital gains tax entirely. It’s the most common tax-deferral tool in real estate. The catch: you have 45 days to identify the replacement property and 180 days to close.

A way to complete a 1031 exchange into a passive, professionally managed real estate investment instead of buying another property yourself. You get fractional ownership in institutional-quality real estate — apartments, industrial, medical offices — without the management headaches.

A tax deduction that lets you write off the cost of a property (not the land) over time — 27.5 years for residential, 39 years for commercial. You didn’t spend cash this year, but the IRS lets you take the deduction anyway. It lowers your taxable income now. The trade-off comes when you sell.

The IRS’s way of clawing back those depreciation deductions. When you sell a rental property, the total depreciation you claimed gets taxed at 25% — on top of whatever capital gains tax you owe. On a property you’ve held for 20 years, recapture alone can be a six-figure tax bill.

Invest capital gains into a Qualified Opportunity Fund within 180 days of the sale, and you defer the original gain. Hold the investment for 10+ years, and any new appreciation in the Opportunity Zone investment is tax-free.

An extra 3.8% tax on investment income — capital gains, dividends, rental income — that kicks in when your modified adjusted gross income exceeds $250K (married filing jointly). It’s not huge on its own, but when you’re selling a $3M property or unwinding a concentrated stock position, 3.8% on a large gain adds up fast.

An engineering analysis that reclassifies components of a property (carpet, fixtures, landscaping, electrical) into shorter depreciation categories — 5, 7, or 15 years instead of 27.5 or 39. The result: larger deductions in the early years of ownership.