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.

The ERC was a refundable payroll tax credit for businesses that retained employees during COVID-19 disruptions in 2020 and 2021. The credit was worth up to $5,000 per employee in 2020 and $21,000 per employee in 2021. The ERC program ended in September 2021, but businesses can still claim credits for 2020 and 2021 by filing amended payroll tax returns (Form 941-X). The statute of limitations for 2020 claims closed April 15, 2024; 2021 claims can still be filed through April 15, 2025.

Yes — after the Consolidated Appropriations Act of 2021, businesses can claim both PPP loan forgiveness and the ERC. However, you cannot use the same wages for both benefits. PPP forgiveness is based on payroll costs; the ERC is based on qualified wages not used for PPP forgiveness. Proper allocation of wages between the two programs is critical to maximizing both benefits.

There are two qualification tests: (1) the revenue decline test — a significant decline in gross receipts compared to the same quarter in 2019 (50% decline for 2020; 20% decline for 2021); or (2) the full or partial suspension test — a government order that fully or partially suspended your business operations due to COVID-19 (capacity restrictions, supply chain disruptions, etc.). You only need to meet one test per quarter.

For 2020: 50% of qualified wages up to $10,000 per employee for the year = maximum $5,000 per employee. For 2021 (Q1-Q3): 70% of qualified wages up to $10,000 per employee per quarter = maximum $21,000 per employee for the year. A business with 10 employees could potentially claim $210,000 in 2021 ERC credits alone.

In September 2023, the IRS announced a moratorium on processing new ERC claims due to concerns about fraudulent claims promoted by aggressive ERC mills. The IRS has since resumed processing but is conducting enhanced scrutiny of all claims. Legitimate businesses with valid ERC claims should work with a qualified tax professional to document their eligibility and file properly. The IRS has also offered a Voluntary Disclosure Program for businesses that received improper ERC payments.

A net operating loss occurs when your allowable tax deductions exceed your taxable income for the year. The excess loss can be carried forward to future tax years to offset up to 80% of taxable income in each future year. NOLs generated after 2017 can be carried forward indefinitely.

Under current law, most NOLs generated after 2017 cannot be carried back — they can only be carried forward. However, farming losses and certain insurance company losses are exceptions. During COVID (2020-2021), special 5-year carryback rules applied.

NOL carryforwards can offset up to 80% of taxable income in any given year. This means if you have $500,000 in taxable income, an NOL can reduce it to no less than $100,000 in that year. The remaining NOL continues to carry forward.

Yes — and this is a legitimate tax planning strategy. By timing large deductions (bonus depreciation, Section 179, cost segregation) in a high-income year, a business can intentionally generate an NOL that offsets income in future years when the business is more profitable.

NOL carryforwards generally do not transfer to the buyer in an asset sale. In a stock sale, the NOLs remain with the corporation but are subject to severe limitations under IRC §382 if there is a change in ownership of more than 50%. Proper planning before a sale is essential to preserve the value of NOL carryforwards.

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.

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.

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).

A single-member LLC is taxed as a sole proprietorship by default (Schedule C). A multi-member LLC is taxed as a partnership by default (Form 1065). An LLC can elect to be taxed as an S-Corp (Form 2553) or C-Corp (Form 8832). The S-Corp election is the most common tax optimization strategy for profitable LLCs, as it reduces self-employment tax on the portion of income taken as distributions rather than salary.

The S-Corp election typically makes sense when net profit exceeds $80,000-$100,000/year. Below that level, the administrative costs of running an S-Corp (payroll processing, additional tax filings, state fees) often exceed the SE tax savings. The breakeven point depends on your state, the cost of payroll services, and the reasonable salary for your role.

The IRS requires S-Corp owner-employees to pay themselves a "reasonable compensation" — what you would pay an unrelated employee to perform the same services. The IRS looks at industry compensation data, the company's profitability, and the owner's duties. Setting the salary too low is the most common S-Corp audit trigger. Uncle Kam can help you determine a defensible reasonable salary for your specific business.

Yes — you can elect S-Corp status for an existing LLC by filing Form 2553 with the IRS. The election can be made at any time during the year for the following year, or within the first 2.5 months of the tax year for the current year. Some states require a separate state-level S-Corp election. The LLC remains an LLC for state law purposes; the S-Corp election only changes the federal (and sometimes state) tax treatment.

Disadvantages include: (1) additional administrative burden (payroll processing, quarterly payroll tax deposits, W-2 issuance, Form 1120-S filing), (2) additional cost ($500-$2,000/year for payroll services and tax preparation), (3) S-Corp restrictions (no more than 100 shareholders, only one class of stock, no foreign shareholders), and (4) some states do not recognize the S-Corp election and tax LLCs as corporations regardless.

An HRA is an employer-funded account that reimburses employees for qualifying medical expenses and health insurance premiums tax-free. The employer deducts the reimbursements as a business expense; the employee receives them tax-free. There are several types: the Qualified Small Employer HRA (QSEHRA) for businesses with fewer than 50 employees, the Individual Coverage HRA (ICHRA) with no size limit, and the traditional group health plan HRA.

A QSEHRA (Qualified Small Employer HRA) is available to businesses with fewer than 50 full-time employees that do not offer a group health plan. Contribution limits apply (approximately $6,350 for self-only coverage, $12,800 for family coverage in 2026). An ICHRA (Individual Coverage HRA) has no size limit and no contribution limits, but employees must be enrolled in individual health insurance (not a group plan) to participate.

S-Corp owners who own more than 2% of the company are treated as self-employed for health insurance purposes and cannot participate in a QSEHRA on a tax-free basis. However, they can participate in an ICHRA if the S-Corp includes the HRA reimbursements in their W-2 wages, and then deduct the premiums as a self-employed health insurance deduction on Schedule 1. The net result is a deduction for the full cost of health insurance.

Yes — HRAs can reimburse any qualifying medical expense under IRS Publication 502, which includes dental care, vision care, prescription drugs, mental health services, and many other out-of-pocket medical costs. The specific expenses covered depend on the HRA plan document, which the employer controls.

An HSA (Health Savings Account) is owned by the employee, funded by both the employer and employee, and requires enrollment in a High-Deductible Health Plan (HDHP). An HRA is funded solely by the employer, does not require an HDHP, and is not portable (funds generally do not follow the employee if they leave). HSAs offer a triple tax advantage (pre-tax contributions, tax-free growth, tax-free withdrawals for medical expenses); HRAs offer a double tax advantage (employer deduction, employee tax-free reimbursement).

As a sole proprietor, you pay 15.3% self-employment tax on all net profits. As an S-Corp owner, you pay yourself a reasonable salary (subject to payroll taxes) and take the remaining profit as a distribution — which is not subject to self-employment tax. On $150,000 in profit, this can save $10,000–$20,000/year.

The IRS requires S-Corp owner-employees to pay themselves a "reasonable compensation" — roughly what you would pay a third party to do your job. The IRS looks at industry benchmarks, the services you provide, and the profitability of the business. Underpaying yourself is a major audit trigger.

The S-Corp election typically makes financial sense when your net self-employment income exceeds $50,000–$60,000/year. Below that threshold, the administrative costs (payroll processing, additional tax filings) often exceed the SE tax savings.

Yes. An LLC can elect to be taxed as an S-Corp by filing IRS Form 2553. The LLC retains its legal structure while being treated as an S-Corp for tax purposes. This is one of the most common and effective tax elections for small business owners.

S-Corps require running payroll, filing quarterly payroll tax returns, and paying additional accounting fees. They also have restrictions: no more than 100 shareholders, all shareholders must be US citizens or residents, and only one class of stock is allowed. For most small businesses, the tax savings far outweigh these administrative requirements.

The personal Clean Vehicle Credit (§30D) for new EVs was repealed under the OBBBA for vehicles purchased after December 31, 2025. However, the Commercial Clean Vehicle Credit (§45W, Form 8936) for business-use EVs remains available at up to $7,500 for vehicles under 14,000 lbs. If you are buying an EV for business use, the commercial credit still applies. Book a call to confirm eligibility for your specific vehicle and use case.

To qualify for the full $7,500 credit, the vehicle must be a new plug-in electric vehicle with a battery capacity of at least 7 kWh, have a final assembly in North America, meet critical mineral and battery component sourcing requirements, and fall within MSRP limits ($55,000 for cars, $80,000 for SUVs and trucks). The IRS maintains a current list of qualifying vehicles at fueleconomy.gov.

Yes — starting in 2024, you can transfer the Clean Vehicle Credit to the dealer at the point of sale, effectively receiving the credit as a discount on the purchase price. This is beneficial if your tax liability is less than $7,500 or if you want the benefit immediately rather than waiting until you file your return. The dealer then claims the credit from the IRS.

Businesses can claim the Commercial Clean Vehicle Credit (Form 8936) for EVs used in business, which provides up to $7,500 for vehicles under 14,000 lbs GVWR and up to $40,000 for larger commercial vehicles. Unlike the personal credit, the commercial credit has no income limits and no MSRP caps. Businesses can also combine the credit with Section 179 expensing and bonus depreciation.

The personal Clean Vehicle Credit is non-refundable — it can reduce your tax liability to zero but cannot generate a refund. However, if you transfer the credit to the dealer at purchase, you receive the full benefit regardless of your tax liability. The Commercial Clean Vehicle Credit for businesses is also non-refundable but can be carried back 1 year or forward 20 years.