Compensation
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Posted on September 9, 2024 by Dan Pascone
Maximizing Employee Stock Purchase Plans (ESPPs): A High Earner’s Guide to Wealth Building and Risk Management
TL;DR Answer Box An Employee Stock Purchase Plan (ESPP) lets you buy your company’s stock using after-tax payroll deductions, often at a 5%–15% discount, sometimes with a lookback that prices shares using the lower of the offering-date or purchase-date price. ESPPs can be a powerful wealth tool, but the biggest risk for high earners is […]
Posted on August 24, 2024 by Dan Pascone
The QSBS Advantage: How to Turn Startup Equity into Tax-Free Wealth
TL;DR Answer Box Qualified Small Business Stock (QSBS) is a special tax rule under IRC Section 1202 that can let eligible investors and employees exclude up to $10M in federal capital gains (or 10x your cost basis, whichever is greater) if they acquire shares directly from a qualifying U.S. C-corp and hold them for at […]
Posted on July 29, 2024 by Dan Pascone
4 Financial Factors to Consider Beyond Salary
TL;DR Answer Box A great job offer isn’t defined by salary alone. High earners should evaluate the total package: equity (RSUs/options/ESPP), bonus terms, retirement plan design (match, vesting, after-tax/Mega Backdoor Roth support), and benefits (health plan structure, HSA eligibility, disability/life coverage). Many “perks” are distractions, focus on what compounds your wealth and reduces risk over […]
Posted on July 11, 2024 by Dan Pascone
Upgrade Your Pay: How to Get the Best Compensation Package
TL;DR Answer Box Your compensation package isn’t just your base salary, it’s a full system: equity, bonuses, retirement benefits, healthcare, HSA, PTO, remote work flexibility, and professional development. High earners build outsized wealth by negotiating the parts that compound (equity + retirement + tax advantages) and by avoiding hidden “gotchas” (vesting schedules, option windows, RSU […]
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 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 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 […]