A 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.

The annual gift tax exclusion is $19,000 per recipient in 2026 (indexed for inflation). You can give $19,000 to as many people as you want each year without filing a gift tax return or using any of your lifetime exemption. Married couples can combine their exclusions to give $38,000 per recipient per year through gift-splitting.

No — gifts within the annual exclusion ($19,000 per recipient in 2026) do not require a gift tax return (Form 709). However, if you make a gift that exceeds the annual exclusion to any one person, you must file Form 709 to report the excess, even if no gift tax is due (the excess reduces your lifetime exemption).

Yes — gifts above the annual exclusion reduce your lifetime gift and estate tax exemption (approximately $15 million+ per person in 2026, permanently doubled under the OBBBA). As long as your total lifetime taxable gifts (above annual exclusions) do not exceed the exemption, no gift tax is due. Only when cumulative taxable gifts exceed the lifetime exemption does gift tax apply at 40%.

Yes — the annual exclusion applies to gifts to any individual, including grandchildren. However, large gifts to grandchildren (or great-grandchildren) may also trigger the Generation-Skipping Transfer (GST) tax, which has its own exemption (approximately $15 million+ in 2026, permanently doubled under the OBBBA). Gifts within the annual exclusion are automatically exempt from GST tax.

Yes — you can elect to treat a lump-sum contribution to a 529 plan as if it were made ratably over 5 years, allowing you to contribute up to $95,000 per beneficiary ($190,000 for married couples) in a single year without gift tax consequences in 2026. This is called the "superfunding" election and must be reported on Form 709.

When 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).

Yes. 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.

Tax-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.

The Retirement Plan Startup Credit (Form 8881) provides a tax credit for small businesses that establish a new qualified retirement plan (401(k), SEP-IRA, SIMPLE IRA, or defined benefit plan). Under SECURE 2.0, businesses with 50 or fewer employees can claim 100% of eligible startup costs up to $5,000/year for the first 3 years — a maximum of $15,000 in total credits.

Eligible startup costs include: plan setup and administration fees, employee education and enrollment costs, and costs to set up payroll integration. The credit covers 100% of these costs for businesses with 50 or fewer employees, and 50% for businesses with 51-100 employees. Businesses with more than 100 employees do not qualify.

Yes — SECURE 2.0 added a $500/year credit for plans that include automatic enrollment features. This credit is available for the first 3 years of the plan and stacks on top of the startup cost credit. A plan with automatic enrollment can generate up to $16,500 in total credits over 3 years ($15,000 startup + $1,500 auto-enrollment).

No — the startup credit is only available for new plans. If you already have a retirement plan and want to add features (like automatic enrollment), you may qualify for the auto-enrollment credit but not the startup cost credit. The plan must be established for the first time to qualify for the startup credit.

The best plan depends on your goals: a Safe Harbor 401(k) avoids discrimination testing and allows maximum contributions for owner-employees; a SIMPLE IRA is easier to administer but has lower contribution limits; a SEP-IRA is easy to set up but requires proportional contributions for all eligible employees. Uncle Kam can model the contribution and tax savings for each option based on your payroll.

A backdoor Roth IRA is a two-step process: (1) contribute to a non-deductible Traditional IRA (no income limit), then (2) immediately convert the Traditional IRA to a Roth IRA. Since the contribution was made with after-tax dollars, the conversion is tax-free. This allows high earners to access Roth IRA benefits regardless of income.

Anyone with earned income can use the backdoor Roth strategy, but it is most valuable for individuals who exceed the Roth IRA income limits: approximately $165,000 (single) or $246,000 (married filing jointly) in 2026. Below these limits, you can contribute directly to a Roth IRA without the backdoor process.

Yes. The backdoor Roth IRA is a legal strategy explicitly acknowledged by Congress and the IRS. It has been available since 2010 when income limits on Roth conversions were eliminated. The strategy remains fully available in 2026.

The pro-rata rule requires you to calculate the taxable portion of a Roth conversion based on the ratio of pre-tax IRA funds to total IRA funds. If you have existing pre-tax Traditional IRA money, converting only the non-deductible contribution will trigger taxes on a proportional share. The cleanest backdoor Roth requires having no pre-tax IRA funds.

The backdoor Roth contribution limit is the same as the regular IRA limit: $7,500 per person in 2026 ($8,500 if age 50 or older). A married couple can each do a backdoor Roth for a combined $15,000/year in tax-free contributions.

A Simplified Employee Pension (SEP-IRA) is a retirement account for self-employed individuals and small business owners. It allows contributions of up to 25% of net self-employment income (after the SE tax deduction), with a maximum of $72,000 in 2026. Any self-employed person with net income can open a SEP-IRA.

A SEP-IRA can be opened and funded up to the tax filing deadline, including extensions. For a sole proprietor, this means you can open a SEP-IRA and make a 2026 contribution as late as October 15, 2027 (with an extension). This makes it the most flexible retirement plan for last-minute tax planning.

The SEP-IRA contribution limit is 25% of net self-employment income (after deducting half of self-employment tax), up to a maximum of $72,000 in 2026. For a freelancer with $100,000 in net income, the maximum SEP-IRA contribution is approximately $18,587.

For most self-employed individuals, a Solo 401(k) allows higher contributions because it includes both employee deferrals and employer contributions. A SEP-IRA is simpler to administer and can be opened after year-end. If you want maximum contributions and are willing to manage payroll, the Solo 401(k) wins. If simplicity is the priority, the SEP-IRA is excellent.

Yes. SEP-IRA contributions do not affect your ability to contribute to a Roth IRA (subject to income limits) or use the backdoor Roth strategy. However, having pre-tax SEP-IRA funds can complicate backdoor Roth conversions due to the pro-rata rule. Uncle Kam helps clients navigate this interaction.

Self-employed individuals can choose from a SEP-IRA (up to 25% of net self-employment income, max $72,000 in 2026), a Solo 401(k) (up to ~$70,000 plus $7,500 catch-up if over 50), a SIMPLE IRA, or a Defined Benefit Plan (which can shelter $100,000+ annually for high earners). The Solo 401(k) is typically the best option for most self-employed individuals because it allows both employee deferrals and employer contributions.

In 2026, a Solo 401(k) allows up to $24,500 as an employee deferral (plus $7,500 catch-up if over 50) plus up to 25% of net self-employment income as an employer contribution, for a combined maximum of approximately $70,000 ($77,500 with catch-up). This is significantly higher than a SEP-IRA for most income levels.

Generally no — you cannot contribute to both a Solo 401(k) and a SEP-IRA for the same self-employment income in the same year. However, you can have a Solo 401(k) for your self-employment income and participate in an employer's 401(k) at a day job, though combined employee deferrals across all plans are capped at $24,500 in 2026.

You must establish a Solo 401(k) by December 31 of the tax year to make employee deferrals for that year. Employer profit-sharing contributions can be made up to the tax filing deadline (including extensions). A SEP-IRA, by contrast, can be established and funded up to the tax filing deadline.

No — retirement contributions reduce income tax but not self-employment tax. SE tax is calculated on net self-employment income before retirement contributions. However, the deduction for half of SE tax reduces your AGI, which in turn reduces the base on which retirement contribution limits are calculated.