Section 1202 and QSBS (Qualified Small Business Stock) refer to the same provision — Section 1202 of the Internal Revenue Code is the statute that provides the QSBS gain exclusion. The terms are used interchangeably. Section 1202 allows non-corporate taxpayers to exclude up to 100% of capital gains from the sale of qualifying small business stock held for more than 5 years, subject to the $10M or 10x basis limit.
Book a Free Call →No — Section 1202 only applies to C-Corp stock. S-Corp stock, LLC membership interests, and partnership interests do not qualify. This is a key reason why many startups are organized as C-Corps (or convert to C-Corps before issuing equity to investors). If you are considering converting your S-Corp or LLC to a C-Corp to issue QSBS, the 5-year holding period clock starts at the conversion date, not the original formation date.
Book a Free Call →Yes — each round of qualifying stock issuance starts a new holding period and has its own $10M exclusion limit (or 10x basis, whichever is greater). If you invested $500,000 in a seed round and $2M in a Series A, each tranche has its own exclusion limit. The 10x basis rule means the $2M Series A investment could exclude up to $20M in gains — potentially much more than the $10M flat limit.
Book a Free Call →Stock splits generally do not affect QSBS status — the new shares retain the QSBS characteristics of the original shares. In a merger or acquisition, if you receive stock in the acquiring company, the new stock may or may not qualify as QSBS depending on whether the acquisition was a tax-free reorganization and whether the acquiring company meets the QSBS requirements. Cash acquisitions trigger the gain recognition and the Section 1202 exclusion applies at that point.
Book a Free Call →It depends on your state. California does not conform to Section 1202 and taxes QSBS gains at the full state rate (up to 13.3%). New York conforms to the federal exclusion. Texas, Florida, and other states with no income tax provide automatic state-level relief. If you live in California and are planning an exit, relocating to a no-income-tax state before the sale can save millions in state taxes on top of the federal exclusion.
Book a Free Call →Small businesses with 100 or fewer employees receive a tax credit of up to $5,000 per year for 3 years for the costs of starting a new retirement plan, plus an additional credit for employer contributions.
A 10-person company starting a 401(k) receives $5,000/year for 3 years = $15,000 in direct tax credits, covering most of the setup and administration costs.
SECURE 2.0 (2023) increased the credit and added a 100% employer contribution credit for plans with 50 or fewer employees.
A UNK client owned a landscaping company with 12 employees and had never offered a retirement plan. Uncle Kam showed him the SECURE 2.0 Act's enhanced startup credit: for businesses with 50 or fewer employees, the credit covers 100% of plan startup costs (up to $5,000/year) for the first 3 years — a potential $15,000 in credits. The client set up a Safe Harbor 401(k), claimed the full $5,000 startup credit in Year 1, and also qualified for an additional $500/year credit for adding automatic enrollment. Total Year 1 credits: $5,500.
Small business with no retirement plan? The government will pay you up to $15,000 to start one. Book a call to set it up.
Be the Next Win — Book a CallThe 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.
When business deductions exceed income, the resulting net operating loss can be carried forward indefinitely to offset future taxable income, reducing taxes in profitable years.
A startup with $200,000 in NOL carries it forward. In Year 3 with $300,000 profit, the NOL offsets $200,000, saving $74,000 in taxes.
NOLs from 2018 forward are limited to 80% of taxable income per year. Pre-2018 NOLs can offset 100% of income. Track NOLs carefully — they are a valuable asset.
A UNK client's restaurant group generated a $380,000 net operating loss during a difficult year. His previous accountant simply noted the loss on the return and moved on. Uncle Kam identified that the NOL could be carried forward indefinitely and used to offset up to 80% of taxable income in future years. As the business recovered, the client used the NOL carryforward to eliminate $380,000 in taxable income over the next three years — saving $140,600 in taxes during the recovery period.
Had a loss year? That NOL is a valuable tax asset. Book a call to make sure it's being tracked and applied correctly.
Be the Next Win — Book a CallA 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.
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.
For a charitable contribution of appreciated stock, the fair market value (FMV) is generally the average of the high and low selling prices on the date of the contribution. This valuation method is outlined in IRS Publication 561, 'Determining the Value of Donated Property.' If the stock is traded on an exchange, this information is readily available. For closely held stock, a qualified appraisal may be required, especially for donations exceeding $5,000, as per Treasury Regulation §1.170A-13. Accurate valuation is crucial for maximizing your deduction and avoiding IRS scrutiny.
Yes, strict record-keeping is essential for a charitable contribution of appreciated stock. For donations valued at $250 or more, you must obtain a contemporaneous written acknowledgment from the charity stating the amount of cash and a description (but not value) of any property contributed, and whether the organization provided any goods or services in return, as per IRS Publication 526. For noncash contributions exceeding $500, you must file Form 8283, 'Noncash Charitable Contributions.' If the stock's value exceeds $5,000, a qualified appraisal is generally required, and a summary of the appraisal must be attached to Form 8283, as detailed in Treasury Regulation §1.170A-13.
If you donate appreciated stock held for less than one year, it is considered short-term capital gain property. In this scenario, your charitable contribution deduction is limited to your cost basis in the stock, rather than its fair market value, as outlined in IRS Publication 526. This means you would not avoid capital gains tax on the appreciation. To receive a deduction for the full fair market value and avoid capital gains tax on the appreciation, the stock must be considered long-term capital gain property, meaning you must have held it for more than one year before the donation date. This distinction is critical for maximizing the tax benefits of a charitable contribution of appreciated stock.
Yes, a charitable contribution of appreciated stock can be made to a Donor-Advised Fund (DAF), and it offers significant tax advantages. Donating appreciated stock to a DAF allows you to claim an immediate tax deduction for the fair market value of the stock, provided it's long-term capital gain property, and avoid capital gains tax on the appreciation, similar to direct donations to public charities. The DAF then sells the stock, and the proceeds grow tax-free. You can recommend grants from the DAF to qualified charities over time. This strategy is particularly useful for those who want to receive an immediate tax deduction but prefer to decide on specific grant recipients later, as per IRS Publication 526 and regulations governing DAFs.
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.
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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.
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LLCs are tax-neutral entities — the tax election determines how income is taxed. S-Corp election saves self-employment taxes; C-Corp election enables retained earnings at 21% rate.
An LLC earning $200,000 net profit: default taxation costs $28,240 in SE tax. S-Corp election with $80,000 salary saves $12,000+/year in SE taxes.
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Founders 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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A dollar-for-dollar tax credit for qualified research expenses including wages, supplies, and contract research. Startups can apply up to $500,000/year against payroll taxes.
A software company spending $500,000 on R&D wages qualifies for a $50,000–$100,000 federal tax credit, dollar-for-dollar against taxes owed.
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Defer 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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Transfer 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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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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Invest 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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A self-directed IRA allows investment in alternative assets including real estate, private loans, and businesses — generating tax-deferred (Traditional) or tax-free (Roth) returns.
A Roth self-directed IRA that purchases a $300,000 rental property generating $24,000/year in rent: all rental income and appreciation grow completely tax-free.
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Investments 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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Investments 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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R&D credits are a dollar-for-dollar tax credit — not just a deduction — and apply to software development wages.
NOL carryforwards from startup losses can offset future profitable years indefinitely.
Qualified Small Business Stock (QSBS) under §1202 can exclude up to $10M in gains from federal tax.
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