How Business Goodwill Is Taxed When You Sell
When you sell a business and allocate a portion of the purchase price to goodwill, the IRS classifies that goodwill as a Section 1231 asset.
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Raffle Tickets and Tax Deductions: Understanding the IRS Guidelines
Many charitable donors are shocked to learn that their well-intentioned raffle ticket purchases might not qualify for the tax deductions they’ve been claiming all along.
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Capital Gains Tax on Farmland: Rates, Recapture, Rollovers
Selling farmland held for decades can generate a federal tax bill exceeding 23.8% of your gain before a single state dollar is added.
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Capital Gains Tax on Deferred Comp? It's Ordinary Income
The short answer: almost always ordinary income.
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Do You Pay Capital Gains Tax on Life Insurance Payouts?
The short answer: no. Death benefits paid to a beneficiary are excluded from gross income under IRC Section 101(a).
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Do You Pay Capital Gains Tax on 401(k) Withdrawals?
The short answer: no. The 401k capital gains tax question trips up a surprising number of high earners, but the mechanics are straightforward once you understand them.
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Does Hong Kong Tax Capital Gains? The Trading-Profit Trap
Hong Kong imposes no capital gains tax. That single fact attracts billions in annual foreign investment and makes the city structurally different from virtually every other major financial center.
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Does California Tax Capital Gains on Out-of-State Assets?
California's taxation of out-of-state capital gains follows one rule above all others: residency.
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Which Countries Actually Tax Unrealized Capital Gains
Unrealized capital gains taxation is no longer a fringe idea debated in academic journals.
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Does Singapore Have a Capital Gains Tax? Not Quite
Singapore's Income Tax Act does not impose a capital gains tax. Profits from disposing of shares, real property, and most other capital assets are generally not subject to income tax.
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Are Indexed Universal Life (IUL) Premiums Tax Deductible?
IUL premiums are not tax-deductible for individuals. That is the short answer. The longer answer is that IUL tax deductibility is the wrong thing to optimize for.
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How Capital Gains Tax on Vacation Homes Works at Sale
Capital gains tax on vacation homes is one of the most mishandled tax issues for high-net-worth property owners, and the mistakes are expensive.
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How to Avoid Capital Gains Tax on Stocks
The standard advice on capital gains tax on stocks is written for someone with a $200K brokerage account.
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Are Company Events Tax Deductible?
Most business owners know company events can generate tax deductions.
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Capital Gains Tax in Spain: Residents and Non-Residents
Capital gains tax in Spain combines progressive rates for residents (19% to 28%), a flat rate for non-residents, and a holding-period rule that can push short-term gains into income tax territory at rates approaching 47%. If your gains routinely exceed €300,000, the headline 19% rate you see in most
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How UTMA Capital Gains Get Caught by the Kiddie Tax
UTMA capital gains tax follows the child's ownership, not the custodian's.
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The Best Tax Strategy Books for a $5M+ Portfolio
The best books on tax strategies for high-net-worth individuals cover territory that standard filing guides never touch: qualified opportunity zones, QSBS exclusions, charitable remainder trusts, entity restructuring before liquidity events, and the mechanics of multi-state domicile planning. If you
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Are Season Tickets Tax Deductible? The Post-TCJA Rules
If you're holding courtside seats or a luxury suite license and wondering whether the IRS will share the cost, the short answer is: almost certainly not.
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How Massachusetts Taxes Non-Residents on Capital Gains
Massachusetts taxes non-residents on capital gains from Massachusetts-source income, including real estate sales and business asset dispositions.
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Is ActBlue Tax Deductible? Why Political Donations Aren't
ActBlue tax deductibility follows a simple rule: political contributions processed through the platform are not deductible on your federal return. Full stop.
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Top Fee-Only Wealth Management Firms: Navigating Financial Success
Money talks, but finding a wealth management firm that speaks your language – without hidden commissions or conflicting interests – can transform your financial future.
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Do Non-Deductible Expenses Increase Your Tax Basis?
Most tax planning focuses on deductions you can take today. That framing misses half the picture.
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Tax-Deferred vs Tax-Deductible: What's the Real Difference?
The distinction matters more at high income levels than anywhere else. Tax-deductible contributions reduce your taxable income in the year you make them.
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Which State Taxes Capital Gains on Out-of-State Property?
Selling out-of-state investment property triggers capital gains tax in at least two jurisdictions simultaneously: the state where the property sits and, potentially, your home state.
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Vermont Capital Gains Tax: Rates and the 40% Exclusion
Vermont taxes capital gains as ordinary income at the state level, with a top marginal rate of 8.75% on income above $213,150 for single filers in 2024.
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When Is SBLOC Interest Tax Deductible? The Tracing Rules
SBLOC interest tax deductibility is real, but it is not automatic. The IRS determines deductibility based entirely on what you do with the borrowed funds, not what secures the loan.
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Does Momentum Investing Survive Taxes on a $5M+ Portfolio?
Momentum investing has three decades of academic support and a real implementation problem for large portfolios.
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Why the 2026 Capital Gains Tax Brackets Compress Your Gains
The 2026 capital gains tax brackets are not a distant policy abstraction. For anyone holding $5M+ in appreciated assets, the TCJA sunset creates a concrete, time-sensitive planning window.
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Netherlands Capital Gains Tax: A Deemed Return, Not Real
The Netherlands does not tax realized capital gains for most individual investors.
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What Non-Residents Owe in Colorado Capital Gains Tax
Colorado taxes non-resident capital gains at a flat 4.40% state rate on Colorado-sourced income. That number sounds manageable in isolation.
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Do You Still Owe FICA on Retirement Income?
For most FATFIRE retirees drawing from a $5M+ portfolio, FICA taxes are largely a non-issue.
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How Non-Retirement Accounts Are Taxed at FatFIRE Income
Non-retirement accounts generate three distinct categories of taxable income: interest, dividends, and capital gains.
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Inherited Roth 401(k) Distribution Rules After SECURE Act
An inherited Roth 401(k) is one of the few assets where the tax benefit genuinely transfers to the beneficiary. Qualified distributions come out entirely tax-free, contributions and earnings alike.
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What Percentage Should Go to Roth vs 401(k)?
The roth vs 401k question is not really a binary decision at the $5M+ level.
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Are Roth IRA Distributions Taxed by Your State?
The federal government exempts qualified Roth IRA distributions from income tax entirely. Your state may not.
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Does California Tax Your Roth IRA Distributions?
Roth IRA distributions and California taxes follow the same basic federal framework: qualified distributions are tax-free at both the federal and state level.
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Which Countries Recognize the Roth IRA? 2026 Treaty Guide
The short answer: fewer than you'd expect, and the ones that do come with conditions most generic expat guides never mention.
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International Students and Roth IRAs: Eligibility, Benefits, and Considerations
While chasing the American dream as a student in the U.S., your path to financial security might take an unexpected turn with a powerful retirement tool that many overlook.
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Do Capital Gains Count as Income for a Roth IRA?
Yes, capital gains count toward your MAGI for Roth IRA contribution purposes.
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How to Report Roth IRA Contributions on Form 1040
Here is the short answer: Roth IRA contributions do not appear as a line item on Form 1040, and you cannot deduct them. Your IRA custodian reports them to the IRS on Form 5498.
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Are Roth IRA Dividends Ever Taxed?
Roth IRA dividends accumulate entirely free of federal income tax, and qualified withdrawals are tax-free as well. That two-part advantage is what separates the Roth from every other account type.
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What SCHD in a Roth IRA Does for the Tax Math
Holding SCHD in a Roth IRA is one of the cleaner asset location decisions available to high-income investors.
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UBTI in a Roth IRA: When Your Account Owes Tax
UBTI in a Roth IRA is a real tax liability, not a theoretical edge case.
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