Each cryptocurrency trade, swap, or exchange is a taxable event. Proper structuring — holding periods, loss harvesting, and entity selection — can dramatically reduce crypto tax liability.
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Book A Free Strategy Call to UnlockSell cryptocurrency at a loss to offset capital gains from other investments. Unlike stocks, crypto is NOT subject to the wash-sale rule, so you can immediately repurchase the same asset.
An investor with $80,000 in crypto gains and $50,000 in crypto losses nets $30,000 in taxable gains — saving $11,900 at a 23.8% long-term rate vs. paying on the full $80,000.
Harvest losses before December 31. Immediately repurchase to maintain market exposure — no 30-day waiting period required for crypto. Track cost basis meticulously.
A UNK client had $45,000 in unrealized losses across several altcoin positions during a market correction. He also had $60,000 in capital gains from selling Bitcoin earlier in the year. Uncle Kam identified the key advantage: unlike stocks, cryptocurrency is not subject to the wash-sale rule. The client sold the losing positions, harvested $45,000 in losses, and immediately repurchased the same coins — maintaining his full market exposure. The $45,000 in losses offset $45,000 of his gains, reducing his net capital gain to $15,000.
Hold crypto with unrealized losses? You can harvest them today and repurchase immediately. Book a call before year-end to capture your losses.
Be the Next Win — Book a CallNo — as of 2026, the wash-sale rule (which disallows a loss if you repurchase the same security within 30 days) does not apply to cryptocurrency. The IRS classifies crypto as property, not a security, so you can sell crypto at a loss and immediately repurchase the same coin without losing the tax deduction. This may change with future legislation, but for now it is a significant advantage over stock tax-loss harvesting.
The IRS treats cryptocurrency as property. Selling, trading, or spending crypto triggers a capital gain or loss equal to the difference between your cost basis and the sale price. Short-term gains (held less than 1 year) are taxed as ordinary income; long-term gains (held more than 1 year) are taxed at 0%, 15%, or 20% depending on your income. Receiving crypto as payment for services is taxed as ordinary income.
Net capital losses (including crypto losses) can offset up to $3,000 of ordinary income per year. Losses above $3,000 carry forward to future years to offset future capital gains or additional ordinary income. There is no limit on how many years losses can carry forward.
Trading one cryptocurrency for another (e.g., Bitcoin for Ethereum) is a taxable event — you must report the gain or loss on each trade. Using crypto to purchase goods or services is also taxable. Simply holding crypto (HODLing) is not a taxable event. Receiving crypto as a gift is not taxable until you sell it (your basis is the donor's basis or the fair market value on the date of the gift, whichever is lower).
You must track: the date of each acquisition, the cost basis (purchase price plus fees), the date of each sale or exchange, the sale proceeds, and the resulting gain or loss. For large portfolios with many transactions, crypto tax software (CoinTracker, Koinly, TaxBit) can automate this tracking. The IRS requires you to report all crypto transactions, and exchanges are required to issue 1099s for transactions above certain thresholds.
Contribute cash or appreciated assets to a DAF, receive an immediate charitable deduction, avoid capital gains on donated assets, and distribute grants to charities at your own pace.
Donating $100,000 in appreciated stock (basis $20,000) to a DAF: $100,000 deduction + $16,000 in avoided capital gains tax = $53,000 in total tax savings at 37%.
Bunch multiple years of charitable giving into one year to exceed the standard deduction threshold. Invest DAF assets for tax-free growth before distributing.
A UNK client planned to donate $10,000/year to her church and local charities over the next 5 years. Uncle Kam introduced the concept of "bunching" — contributing 5 years of donations ($50,000) into a Donor-Advised Fund in a single year. This pushed her itemized deductions well above the standard deduction ($29,200 for MFJ), generating a $50,000 charitable deduction in Year 1. At her 37% marginal rate, the deduction saved $18,500 in federal taxes. She then distributed $10,000/year from the DAF to her chosen charities over the following 5 years.
Planning to give to charity? A Donor-Advised Fund can double your tax benefit without changing how much you give. Book a call to structure your giving strategy.
Be the Next Win — Book a CallA Donor-Advised Fund (DAF) is a charitable giving account sponsored by a public charity (such as Fidelity Charitable or Schwab Charitable). You contribute cash, securities, or other assets to the DAF, receive an immediate tax deduction for the full contribution, and then recommend grants to qualified charities over time. The assets grow tax-free inside the DAF until distributed.
Cash contributions to a DAF are deductible up to 60% of AGI. Contributions of appreciated securities are deductible at fair market value up to 30% of AGI. Excess contributions carry forward for up to 5 years. Unlike private foundations, DAFs have no minimum distribution requirement.
Bunching means contributing multiple years of planned charitable giving into a DAF in a single year to exceed the standard deduction threshold and itemize. For example, instead of donating $10,000/year for 5 years (which may not exceed the standard deduction), you contribute $50,000 in Year 1 to a DAF, take the full itemized deduction, and then distribute $10,000/year to charities from the DAF over the following 5 years.
Yes — and this is one of the most powerful aspects of a DAF. You can contribute long-term appreciated stock directly to the DAF, deduct the full fair market value (up to 30% of AGI), and avoid paying capital gains tax on the appreciation. The DAF can then sell the stock tax-free and invest the proceeds for future charitable distributions.
A DAF is simpler and cheaper to establish (no legal fees, no IRS approval), has no minimum distribution requirement, offers higher deduction limits, and provides anonymity for grants. A private foundation offers more control (you can hire family members, make program-related investments, and set your own grant criteria) but requires 5% annual distributions, has lower deduction limits, and faces excise taxes on investment income.
Defer capital gains taxes indefinitely by reinvesting proceeds from the sale of investment property into a like-kind replacement property.
Selling a rental property with $500,000 in gains at a 20% capital gains rate saves $100,000 in immediate taxes. Deferred indefinitely with proper execution.
Can be chained across multiple properties for a lifetime of tax-deferred wealth building. Step-up in basis at death eliminates deferred gain entirely.
A UNK client had owned a Phoenix duplex for 11 years and was sitting on $600,000 in appreciation. His plan was to sell, pay the tax, and reinvest what was left. Uncle Kam intervened before the sale closed. By structuring a 1031 exchange with a qualified intermediary, the client rolled the full $600,000 in proceeds into a larger 4-unit building — deferring $120,000 in federal capital gains tax and $18,000 in state tax. He now earns $4,200/month in net rental income on a property he controls entirely with pre-tax dollars.
Selling an investment property? Do not let the IRS take 20-30% before you reinvest. Book a call before you close.
Be the Next Win — Book a CallA 1031 exchange allows you to sell an investment property and defer all capital gains taxes by reinvesting the proceeds into a like-kind replacement property. You must identify the replacement property within 45 days and close within 180 days, using a qualified intermediary to hold the funds.
Yes. Residential rental properties, commercial buildings, raw land, and even some types of personal property qualify. The property must be held for investment or business use — your primary residence does not qualify.
The deferred gain carries forward into the replacement property's adjusted basis. You can continue deferring it through a chain of 1031 exchanges. If you hold the property until death, heirs receive a step-up in basis and the deferred gain is eliminated entirely.
After selling your relinquished property, you have exactly 45 calendar days to identify up to three potential replacement properties in writing. Missing this deadline disqualifies the entire exchange and makes the full gain taxable immediately.
Yes — "like-kind" is broadly defined for real estate. You can exchange a single-family rental for a commercial building, raw land, or a multi-family property. The key is that both properties must be held for investment or business use.
Donate appreciated securities directly to charity and receive a deduction for the full fair market value while avoiding capital gains tax on the appreciation.
Donating $50,000 in stock (basis $5,000): $50,000 deduction + $9,000 avoided capital gains = $27,500 total tax savings vs. $18,500 if you sold and donated cash.
Never sell appreciated stock and donate the proceeds — always donate the stock directly. Use a DAF if the charity does not accept stock directly.
A UNK client held $120,000 in Apple stock with a cost basis of $20,000 — a $100,000 long-term gain. He planned to sell the stock, pay the capital gains tax, and donate the after-tax proceeds to his alma mater. Uncle Kam redirected the strategy: donate the stock directly to the university's DAF. By donating the shares directly, the client deducted the full $120,000 fair market value, avoided $22,000 in federal capital gains tax (at 20% + 3.8% NIIT on the $100,000 gain), and the university received the full $120,000 instead of $98,000.
Planning a charitable gift? Never sell appreciated stock first — donate it directly and keep the capital gains tax. Book a call to structure your next gift.
Be the Next Win — Book a CallYes. You can donate long-term appreciated stock (held more than 1 year) directly to a qualified charity or Donor-Advised Fund and deduct the full fair market value on the date of the gift — up to 30% of AGI. You also avoid paying capital gains tax on the appreciation. This is almost always more tax-efficient than selling the stock and donating cash.
When you donate appreciated stock, you get two tax benefits: (1) a charitable deduction for the full fair market value, and (2) you avoid capital gains tax on the appreciation. When you donate cash, you only get the charitable deduction. For stock with large embedded gains, the difference can be tens of thousands of dollars.
You can donate publicly traded stocks, mutual funds, ETFs, bonds, real estate, private company stock, cryptocurrency, and other appreciated assets. The deduction rules vary by asset type: publicly traded securities are deductible at fair market value; private company stock and real estate require a qualified appraisal; cryptocurrency is treated like property.
Contributions of long-term appreciated capital gain property to public charities are deductible up to 30% of AGI. Contributions to private foundations are limited to 20% of AGI. Excess contributions carry forward for up to 5 years. Cash donations to public charities are deductible up to 60% of AGI.
Yes. The IRS treats cryptocurrency as property, so donating appreciated crypto directly to a qualified charity or DAF allows you to deduct the fair market value and avoid capital gains tax on the appreciation — the same as donating appreciated stock. The charity or DAF can then sell the crypto tax-free.
Sell investments at a loss to offset capital gains from other investments, reducing or eliminating capital gains tax. Excess losses offset up to $3,000 of ordinary income annually.
Harvesting $50,000 in losses offsets $50,000 in capital gains, saving $10,000 at a 20% long-term rate. Excess losses carry forward indefinitely.
Avoid the wash sale rule — do not buy the same or substantially identical security within 30 days before or after the sale. Replace with a similar (not identical) investment.
A UNK client had a concentrated stock portfolio and realized $85,000 in capital gains from selling a position in early 2023. Later that year, during a market correction, several of his other holdings were down significantly. Uncle Kam identified $55,000 in unrealized losses across three positions. The client sold those positions, harvested the $55,000 in losses, and immediately reinvested in similar (but not identical) ETFs to maintain market exposure without triggering the wash-sale rule. The $55,000 in losses offset $55,000 of his gains, reducing his net capital gain to $30,000.
Have unrealized losses in your portfolio? Tax-loss harvesting is a free tax reduction available every year. Book a call before year-end.
Be the Next Win — Book a CallTax-loss harvesting is the practice of selling investments at a loss to offset capital gains from other investments, reducing your overall tax liability. The harvested losses first offset capital gains dollar-for-dollar. If losses exceed gains, up to $3,000 of excess losses can offset ordinary income per year. Remaining losses carry forward indefinitely to future years.
The wash-sale rule disallows a loss deduction if you buy the same or "substantially identical" security within 30 days before or after the sale. To avoid triggering the rule, you can immediately reinvest in a similar but not identical security (e.g., sell a Vanguard S&P 500 ETF and buy a Fidelity S&P 500 ETF), wait 31 days before repurchasing, or use the loss to rebalance your portfolio.
No — losses in tax-deferred accounts (IRA, 401(k)) cannot be harvested because all gains and losses inside those accounts are tax-deferred. Tax-loss harvesting only applies to taxable brokerage accounts. This is one reason why it can be beneficial to hold more volatile assets in taxable accounts where losses can be harvested.
Yes — and cryptocurrency has a significant advantage: the wash-sale rule does not currently apply to crypto (it applies only to "securities" under the tax code, and crypto is classified as property). This means you can sell crypto at a loss, immediately repurchase the same coin, and still claim the loss deduction. This may change with future legislation.
Capital losses first offset capital gains of the same type (short-term losses offset short-term gains; long-term losses offset long-term gains). Excess losses can offset gains of the other type. After offsetting all capital gains, up to $3,000 of net capital losses can offset ordinary income per year. Remaining losses carry forward indefinitely.
Assets transferred at death receive a new cost basis equal to the fair market value at the date of death, eliminating all embedded capital gains that accrued during the decedent's lifetime.
A $2M stock portfolio with a $200,000 original basis: if held until death, heirs inherit with a $2M basis, eliminating $360,000 in capital gains taxes.
Do not sell highly appreciated assets — hold them until death for the step-up. Combine with a 1031 exchange chain for real estate to defer gains and step up at death.
A UNK client's father had purchased Apple stock in 1990 for $12,000. At his death, the shares were worth $352,000 — a $340,000 gain. Without planning, the client assumed she would owe capital gains tax when she sold the shares. Uncle Kam explained the step-up in basis: because the shares passed through the estate, the client's cost basis was stepped up to $352,000 (the date-of-death value). She sold the shares immediately for $352,000 and owed zero capital gains tax on the $340,000 in appreciation.
Have appreciated assets you plan to pass to heirs? The step-up in basis is one of the most powerful estate planning tools available. Book a call to coordinate your plan.
Be the Next Win — Book a CallWhen you inherit an asset, your cost basis is "stepped up" to the fair market value on the date of the decedent's death (or an alternate valuation date 6 months later). This means all appreciation during the decedent's lifetime is permanently erased for capital gains purposes. If you sell the asset immediately after inheriting it, you owe zero capital gains tax on the lifetime appreciation.
Most capital assets that pass through an estate receive a step-up: stocks, bonds, mutual funds, real estate, business interests, and collectibles. Assets held in IRAs and 401(k)s do not receive a step-up — they are subject to ordinary income tax when withdrawn. Assets in irrevocable trusts may or may not receive a step-up depending on how the trust is structured.
In community property states (California, Texas, Arizona, Nevada, Washington, Idaho, Louisiana, New Mexico, Wisconsin), both halves of community property receive a step-up in basis when one spouse dies — not just the deceased spouse's half. This is a significant advantage over common law states, where only the deceased spouse's share receives the step-up.
For very large embedded gains, holding appreciated assets until death can eliminate the capital gains tax entirely through the step-up in basis. However, this strategy must be weighed against estate tax exposure (if the estate exceeds the exemption), liquidity needs, and the opportunity cost of holding a concentrated position. Uncle Kam can model the tradeoffs for your specific situation.
Yes — donating appreciated assets to a qualified charity or Donor-Advised Fund eliminates the capital gains tax and generates a charitable deduction for the full fair market value. This is often more tax-efficient than holding until death (which avoids capital gains but may trigger estate tax) or selling and donating cash (which triggers capital gains before the donation).
Invest capital gains from any source into a Qualified Opportunity Fund within 180 days to defer the gain until December 31, 2026, and eliminate all taxes on appreciation after 10 years.
A $2M capital gain invested in a QOF: defers $400,000 in taxes until 2026. If the fund doubles to $4M in 10 years, the $2M appreciation is completely tax-free.
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Book A Free Strategy Call to UnlockInvest capital gains into a Qualified Opportunity Fund within 180 days to defer the original gain until 2026 and eliminate all appreciation on the QOZ investment after a 10-year hold.
An investor with $500,000 in capital gains invests in a QOZ fund. The $500K gain is deferred to 2026. If the fund grows to $1.5M, the $1M appreciation is completely tax-free.
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Book A Free Strategy Call to UnlockDefer and potentially eliminate capital gains taxes by investing in Qualified Opportunity Zone Funds within 180 days of a capital gain event.
Investing $500,000 of capital gains into a QOF and holding 10 years eliminates all taxes on the new appreciation — potentially $300,000+ in tax-free gains.
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Book A Free Strategy Call to UnlockTransfer appreciated assets into a CRT, receive an immediate charitable deduction, avoid capital gains on the sale, and receive income payments for life or a term of years.
Transferring $1M in appreciated stock (basis $100,000) to a CRT eliminates $180,000 in capital gains tax, generates a $300,000+ charitable deduction, and provides lifetime income.
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Book A Free Strategy Call to UnlockFounders and investors in qualified small businesses can exclude up to $10 million (or 10× their adjusted basis) in capital gains from federal income tax when selling stock held for more than 5 years.
A founder selling $10M in QSBS stock (basis $100K) excludes the entire $9.9M gain, saving $1.98M in federal capital gains taxes.
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Book A Free Strategy Call to UnlockQualified Small Business Stock (QSBS) under Section 1202 allows founders, employees, and investors to exclude up to $10 million (or 10x basis) in capital gains when selling stock held for more than 5 years.
A founder who sells $10M in QSBS stock pays $0 in federal capital gains tax — saving $2,380,000 vs. the 23.8% long-term rate.
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Book A Free Strategy Call to UnlockSpread the recognition of capital gains from a property sale over multiple years by receiving payments in installments, keeping annual income in lower tax brackets.
Selling a property with $600,000 in gains. Spreading over 6 years keeps you in the 15% capital gains bracket instead of 20%, saving $30,000+.
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Book A Free Strategy Call to UnlockInvestments in oil and gas working interests allow immediate deduction of 65–80% of the investment as Intangible Drilling Costs (IDC), plus ongoing depletion allowances on production.
A $500,000 investment in an oil and gas working interest generates $325,000–$400,000 in Year 1 IDC deductions, saving $120,000–$148,000 at a 37% rate.
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Book A Free Strategy Call to UnlockInvestments in qualified film and television productions generate state tax credits (25–35% of production spend) plus federal deductions under IRC §181 for productions under $15M.
A $200,000 investment in a Georgia film production generates a $60,000 Georgia state tax credit (30%) plus potential federal deductions — total tax benefit of $80,000–$100,000.
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Book A Free Strategy Call to UnlockUnlike stocks, crypto is NOT subject to the wash-sale rule (IRC §1091) — you can sell at a loss, immediately rebuy, and still claim the full deduction. This is the #1 crypto tax strategy.
Donating appreciated crypto directly to charity lets you deduct the full fair market value AND avoid capital gains tax — worth 20–37% more than selling and donating cash.
Mining income is taxed as ordinary income at receipt — but mining equipment and electricity costs are fully deductible business expenses under IRC §162.
This write-off is commonly used by the following taxpayer profiles. Click to see all strategies for your situation.
