Knowledge Base
Tax optimization frameworks for high-net-worth early retirees — capital gains harvesting, business deductions, and the strategies that move the needle at the $5M+ level.
61 articles in this category — page 3 of 6
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. The 2017 Tax Cuts and Jobs Act eliminated the entertainment deduction entirely. No phase-in, no income threshold, no partial credit for business p
Massachusetts taxes non-residents on capital gains from Massachusetts-source income, including real estate sales and business asset dispositions. The state's short-term rate of 8.5% and its 4% millionaires surtax create a combined burden that can push effective rates well above 30% for high-income s
ActBlue tax deductibility follows a simple rule: political contributions processed through the platform are not deductible on your federal return. Full stop. The IRS treats them as personal expenditures, the same category as a restaurant meal. The one exception is donations routed through ActBlue Ch
Most tax planning focuses on deductions you can take today. That framing misses half the picture. Non-deductible expenses frequently increase your tax basis, and at the 23.8% combined federal capital gains rate (20% long-term rate plus the 3.8% net investment income tax under IRC §1411), every $100,
The distinction matters more at high income levels than anywhere else. Tax-deductible contributions reduce your taxable income in the year you make them. Tax-deferred accounts postpone the tax bill entirely, letting gains compound without annual drag. Both reduce what you owe the IRS, but at differe
Aggressive tax planning sits in the space between legitimate tax optimization and outright evasion. For high-net-worth individuals, understanding exactly where that line falls matters more than it does for most taxpayers. The IRS has made clear that people with $5M+ in assets are a priority enforcem
Most retail guidance on ETF capital gains tax stops at "ETFs are tax-efficient." That's true as far as it goes. But if you're sitting on a $3M taxable account with a mix of broad-market and specialty ETFs, the headline story misses the details that actually move your tax bill. The combined federal r
The short answer: yes, several countries impose zero capital gains tax on investment gains. The longer answer is that for most readers here, your home country's tax rules follow you across borders, treaty networks determine your real after-tax return, and substance requirements make genuine relocati
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. For high-net-worth sellers, the combined federal and state tax stack can reach 37% or more on a single transaction be
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. Stack that on top of the 20% federal long-term rate plus the 3.8% Net Investment Income Tax, and high-net-worth Vermont residents face a combined m
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. Use a $3M SBLOC backed by your equity portfolio to buy more investments, and the interest is potentially deductible. U
Momentum investing has three decades of academic support and a real implementation problem for large portfolios. The 1993 Jegadeesh and Titman study in the Journal of Finance documented that stocks with strong 3-12 month past returns continued to outperform over the following 3-12 months. That findi