Compensation
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Posted on September 23, 2025 by Dan Pascone
ISOs Strategy: Avoid AMT & Build Long-Term Wealth
TL;DR Answer Box Quick answer: An ISO strategy for high earners works best when you treat options like a tax and risk project, not a lottery ticket. You may build more after-tax wealth by (1) exercising in planned tranches, (2) modeling AMT before you click “exercise,” and (3) choosing the right sale type (qualifying or […]
Posted on September 17, 2025 by Dan Pascone
10b5-1 Plans for RSUs: From Legal Protection to Long-Term Diversification
TL;DR Answer Box 10b5-1 plan for RSUs: The best 10b5-1 plan is not a compliance checkbox. It is a rules-based diversification system that turns inevitable RSU sales into predictable cash flow, lower single-stock risk, cleaner tax outcomes, and calmer optics when Form 4 filings post. Build it when you are “clean,” use a clear schedule […]
Posted on May 14, 2025 by Dan Pascone
Income Volatility Isn’t a Bug—It’s a Feature
TL;DR Answer Box Volatile income breaks “steady paycheck” financial plans. Fix it with systems: (1) engineer your tax timing (deferrals, equity-event sequencing, Roth windows), (2) build a barbell liquidity stack so you don’t sell long-term assets at the wrong time, and (3) rebalance based on your income rhythm, not just market noise. When the structure […]
Posted on April 30, 2025 by Dan Pascone
Stock Options vs. Smart Money Moves—Vesting in 2025
TL;DR Answer Box Equity compensation is either a brilliant windfall or a minefield—depending on whether you track your key dates. If you’re juggling RSUs, ISOs, NSOs, or ESPPs, you need your grant, vest, exercise, sale, and expiration dates mapped in advance. Track the 4 critical dates: grant, vest, expiration (options), and taxation (vest/exercise/sale). Avoid tax […]
Posted on April 21, 2025 by Dan Pascone
Stock Option Taxes: How to Keep More of What You Earn
TL;DR Answer Box Stock options can build wealth—but the tax rules can bite. The smartest approach is to (1) confirm whether you have ISOs or NSOs, (2) model exercises and sales across multiple years to avoid bracket spikes, and (3) manage ISO AMT exposure by exercising in phases and running an AMT forecast first. Last […]
Posted on March 11, 2025 by Dan Pascone
Financial Planning for Go to Market Leaders and Sales Professionals
TL;DR Answer Box Equity can create life-changing wealth for GTM leaders—but it’s rarely a “quick win.” Taxes (especially on NSOs), vesting schedules, and option expiration deadlines can quietly destroy outcomes. The bigger threat? Behavioral traps like recency bias and social proof from negative stories that cause employees to undervalue or mishandle their equity. The solution […]
Posted on October 28, 2024 by Dan Pascone
Play Defense, Build Legacy: Wealth Protection Strategies for High Earners
TL;DR Answer Box Building wealth is only half the battle. High earners face bigger and more complex risks: lawsuits, health surprises, market volatility, and changing tax laws. The defense is a two-part system: (1) risk management (insurance, liquidity, liability protection) to protect your lifestyle while you’re alive, and (2) estate planning (wills, beneficiary audits, trusts, […]
Posted on October 14, 2024 by Dan Pascone
Retirement and Tax Planning: A Dynamic Approach for High Earners
TL;DR Answer Box Retirement planning and tax planning are inseparable. For high earners, the most durable approach is tax diversification: build wealth across three buckets—taxable, tax-deferred, and tax-free—so you can control your taxable income in retirement year-by-year. Pair that with proactive tax strategy (401(k)/HSA maximization, tax-loss harvesting, tax-efficient funds, and Roth planning like backdoor Roth […]
Posted on October 9, 2024 by Dan Pascone
Structuring a Comprehensive Financial Plan for High Earners: A 4-Part Series
TL;DR Answer Box A real financial plan isn’t just investing—it’s a full system. Start by defining clear goals (short/mid/long-term), then measure progress with net worth. Build a budget that gives you “yes” money, manage debt strategically, and design retirement + tax planning across taxable / tax-deferred / tax-free buckets. Protect your downside with an emergency […]
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 over-concentration: […]