Tax Strategies
Select a Category
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 […]
Posted on March 25, 2024 by Dan Pascone
Tax Deductions vs Tax Credits for High Earners: What You Need to Know
TL;DR Answer Box Tax credits vs tax deductions comes down to what they reduce. Credits reduce your tax bill directly, while deductions reduce taxable income and only save you a percentage based on your marginal tax rate. High earners often have fewer credits available due to phaseouts, but may still unlock meaningful credits with the […]
Posted on March 19, 2024 by Dan Pascone
Case Study: The Alternative Minimum Tax (AMT) and Equity Compensation (ISOs & RSUs)
TL;DR Answer Box ISOs vs RSUs taxes can produce very different after-tax outcomes even when the headline “grant value” is the same. RSUs are typically taxed as ordinary income when they vest, while ISOs may avoid ordinary income tax if you meet qualifying disposition rules, but they can trigger Alternative Minimum Tax (AMT) when you […]
Posted on March 19, 2024 by Dan Pascone
What is the Alternative Minimum Tax (AMT) and What You Need to Know in 2024
TL;DR Answer Box Alternative Minimum Tax (AMT) is a parallel tax calculation that can apply when certain deductions and “preference items” reduce your regular tax too far. Many high-earning tech employees run into AMT because of Incentive Stock Options (ISOs), large capital gains, and state and local tax deductions that do not behave the same […]
Posted on March 13, 2024 by Dan Pascone
Tax Implications of Equity Compensation in Tech: Navigating ISOs and RSUs
TL;DR Answer Box ISO vs RSU taxes comes down to timing, cash needs, and risk. ISOs can create powerful long-term capital gains outcomes, but they may trigger Alternative Minimum Tax (AMT) and require out-of-pocket cash to exercise. RSUs are simpler, but they are taxed as ordinary income at vesting and can create a withholding gap […]
Posted on March 4, 2024 by Dan Pascone
What are Capital Gains?
TL;DR Answer Box Capital gains tax planning comes down to two levers you can actually control: your cost basis and your holding period. Tax loss harvesting can reduce taxes today, but it can also reset cost basis in a way that increases future capital gains taxes, so it should be used intentionally, not automatically. High […]