Tax Strategies
Select a Category
Posted on February 23, 2026 by Dan Pascone
Stop Confusing Your Portfolio with Your Plan
TL;DR Answer Box If your “plan” is a portfolio pie chart, a Monte Carlo percentage, and a net worth snapshot, you may not have a plan. You may have an investment proposal. A real financial plan is a living model across six phases that helps you quantify trade-offs (taxes, equity comp, goals, work optional timing) […]
Posted on February 16, 2026 by Dan Pascone
What Is a Real Financial Plan? The 6-Phase Framework High Earners Actually Need
TL;DR Answer Box If you have a comp plan but no 10-year financial plan, you are optimizing income without designing outcomes. A decade plan starts with a clear picture of your life in ten years, then connects equity decisions, taxes, spending, and investing to that target. The goal is not prediction. The goal is a […]
Posted on February 2, 2026 by Dan Pascone
Build an Executive Income & Equity Calendar to Avoid Surprise Tax Bills
TL;DR Answer Box If you get RSUs, a bonus, ESPP purchases, or stock option windows, you need a 12-month income and equity calendar before you need another tax strategy. The goal is simple: map every income spike and equity event for the next 12 months, then attach one of three tax moves to each event […]
Posted on January 26, 2026 by Dan Pascone
Three Simple Moves to Fix The Bonus and RSU Tax Surprise
TL;DR Answer Box Your bonus is not fully taxed yet. If your household income is north of ~$400,000 and you’re receiving bonuses and/or RSU vests, the default 22% federal “supplemental withholding” is often below your true marginal rate. That mismatch is why April surprises happen. Fix it with three levers: (1) increase W-4 withholding on […]
Posted on November 17, 2025 by Dan Pascone
Remote Work Tax Traps for Executives: Avoid These 3 Costly Mistakes
TL;DR Answer Box Remote work tax traps for executives usually come from three places: (1) assigned-office sourcing rules that can treat at-home days as worked in a higher-tax state, (2) city wage taxes where “required” days can create refunds but “convenience” days often do not, and (3) multi-state equity allocation on RSU vests and option […]
Posted on October 27, 2025 by Dan Pascone
Donor-Advised Funds: The Tax-Smart Way to Give
TL;DR Answer Box A donor-advised fund (DAF) lets high earners contribute in peak-income years, potentially take an immediate charitable deduction (subject to itemizing, AGI limits, and other rules), and grant to charities over time on your schedule. When funded with long-term appreciated assets, a DAF can also help you avoid capital gains you might owe […]
Posted on September 29, 2025 by Dan Pascone
2025 Tax Law Changes for Executives: What to Do Now
TL;DR Answer Box 2025 tax law changes for executives are now a real planning input for 2026 and beyond. The point is not to react to headlines. The point is to translate what changed into decisions: income timing, deductions, entity strategy, capex planning, estate moves, and equity-comp coordination. Use the checklist below to prioritize the […]
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 August 7, 2025 by Dan Pascone
Is Your Exit Plan Half-Baked? Here’s How Founders Turn Valuation into Legacy
TL;DR Answer Box A big exit number is not the same thing as after-tax, usable wealth. The gap between a “headline valuation” and what your family keeps is usually driven by (1) QSBS eligibility + stacking, (2) pre-sale estate planning (GRAT/SLAT/defined-value clauses) completed 18–36 months pre-close, and (3) deal + payout sequencing (installments, earnouts, equity […]
Posted on August 4, 2025 by Dan Pascone
The 2025 Tax Overhaul Could Save You Thousands: What Every High Earner Needs to Know
TL;DR Answer Box The “One Big Beautiful Bill Act” reshapes high-income planning. The biggest levers are (1) permanently extending the current individual rate structure, (2) expanding the federal estate and gift exemption starting in 2026, (3) temporarily lifting the SALT cap with a phaseout, and (4) reopening major business deductions like immediate R&D expensing and […]