Tax Strategies
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Posted on July 2, 2024 by Dan Pascone
Tax Tips for Cash Bonuses, RSUs, and Stock Options
TL;DR Answer Box Bonuses feel like a windfall, until the tax bill shows up. Cash bonuses are taxed as ordinary income and often under-withheld. RSUs are taxed as ordinary income at vest (even if you don’t sell). NSOs trigger ordinary income at exercise; ISOs may qualify for capital gains treatment but can create AMT exposure. […]
Posted on June 25, 2024 by Dan Pascone
The High Earner’s Guide to State and Local Taxes (SALT) & Deductions
TL;DR Answer Box Moving states for taxes can change your net income dramatically, but it’s not just “state income tax vs. no state income tax.” SALT includes income taxes, property taxes, and (in some cases) sales taxes, and the federal deduction has been capped at $10,000 under the Tax Cuts and Jobs Act (TCJA). That […]
Posted on June 18, 2024 by Dan Pascone
Life Insurance Retirement Plans: Turning LIRPs into Powerful Retirement Tools
TL;DR Answer Box A Life Insurance Retirement Plan (LIRP) uses a permanent life insurance policy’s cash value to create a retirement income stream, often through policy loans that can be tax-free if structured and managed correctly. LIRPs can be useful for high earners who are already maxing out traditional retirement accounts and want additional tax-advantaged […]
Posted on June 11, 2024 by Dan Pascone
A Comprehensive Guide to NIIT for High-Income Investors
TL;DR Answer Box The Net Investment Income Tax (NIIT) is an additional 3.8% surtax on certain investment income (like interest, dividends, capital gains, rental/royalty income, and non-qualified annuities) when your modified adjusted gross income (MAGI) exceeds certain thresholds. Most high earners get surprised because NIIT stacks on top of your normal investment taxes. The good […]
Posted on May 28, 2024 by Dan Pascone
The High Earner’s Playbook to Donor-Advised Funds
TL;DR Answer Box Donor-Advised Funds (DAFs) let high earners “front-load” charitable deductions in a high-income year, then distribute grants to charities over time. You get an immediate tax deduction when you contribute, your donation can grow tax-free inside the DAF, and you keep advisory privileges on where/when grants go. DAFs are best when philanthropy is […]
Posted on May 20, 2024 by Dan Pascone
Tax Savvy Moonlighting: Tax Strategies for Side-Hustling High-Earners
TL;DR Answer Box Moonlighting income is usually treated as self-employment income, which means you may owe federal income tax + 15.3% self-employment tax (plus state tax where applicable). Since taxes aren’t withheld, you’ll often need to pay quarterly estimated taxes and track deductible business expenses to reduce what you owe. Last updated: February 12, 2026 […]
Posted on May 13, 2024 by Dan Pascone
Beyond Basics: HSAs as a Tool for Wealth and Health Management
TL;DR Answer Box Health Savings Accounts (HSAs) can offer a rare “triple tax advantage”: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. To contribute, you must be enrolled in a high-deductible health plan (HDHP). HSAs can be a powerful tool for high earners to reduce taxable income today and build a long-term […]
Posted on April 23, 2024 by Dan Pascone
5 Smart High-Earner Moves to Maximize Your Tax Return
TL;DR Answer Box Tax strategies for W-2 employees are less about “finding write offs” and more about using the benefits already available through payroll, retirement plans, and taxable investing. In 2026, the biggest levers for many high earners are maximizing workplace retirement contributions, using Roth pathways when eligible, fully funding an HSA if you qualify, […]
Posted on April 16, 2024 by Dan Pascone
Breaking Down the Mega Backdoor Roth: A Tax-Saving Strategy for High Earners
TL;DR Answer Box Mega Backdoor Roth is a strategy that can let certain high earners move substantially more money into Roth each year by making after-tax (non-Roth) contributions to a 401(k) and then converting or rolling those dollars into Roth. It only works if your employer plan allows after-tax contributions and provides a Roth pathway […]
Posted on April 9, 2024 by Dan Pascone
All About the Backdoor Roth IRA
TL;DR Answer Box Backdoor Roth IRA is a two-step strategy that may allow high-income earners to fund a Roth IRA even when they are over the income limit for direct Roth contributions. The clean version is: contribute to a traditional IRA (often nondeductible), then convert to Roth, while tracking basis correctly on Form 8606 and […]