Tax Strategies
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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 […]
Posted on July 28, 2025 by Dan Pascone
How to Legally Pay Less Taxes in 2025: Strategies Every High Earner Should Know
TL;DR Answer Box Tax season shouldn’t be a surprise. Most high-income tax pain comes from under-planning, not under-earning. The biggest wins in 2025 usually come from (1) fixing withholding/estimated payments when you have multiple income streams, (2) maxing the right tax-advantaged accounts (401(k)/HSA/Roth strategies), (3) using business deductions correctly (if applicable), and (4) timing charitable […]
Posted on June 2, 2025 by Dan Pascone
How to Navigate a Career Change Without Losing Financial Ground
TL;DR Answer Box A career transition is a personal-finance pressure cooker, and a rare optimization window. Done right, you can (1) model RSUs/ISOs/NSOs like a portfolio, (2) compress or spread income across tax years intentionally, and (3) build liquidity + domicile proof before major equity events. Most people don’t lose money because they made less, […]
Posted on May 26, 2025 by Dan Pascone
Breaking Down Trump’s Proposed Middle-Class Tax Cuts for 2025 and Beyond
TL;DR Answer Box This proposal creates a time-window mindset. If the “One Big Beautiful Bill” (as proposed) moves forward, the opportunity is not “politics,” it’s planning: lock in smart structures while rules are favorable, harvest expiring credits before 2028, and run forward-looking projections now so you’re not guessing in 2029. Key levers: entity optimization (QBI), […]
Posted on May 12, 2025 by Dan Pascone
🏗 Engineer Your W-2 Side Hustle Income Before It Hurts
TL;DR Answer Box At $500K+ W-2 income, “maxed 401(k)” is not a strategy, it’s a starting line. High earners reduce tax drag by building infrastructure: (1) an entity that captures income you control outside your W-2 (and unlocks legitimate deductions and better tax treatment), and (2) stacked retirement “shelters” tied to that entity (often a […]
Posted on May 5, 2025 by Dan Pascone
Your 2025 Tax Playbook: Planning for the End of the TCJA Party
TL;DR Answer Box If you earn $400K–$2M+ and your income includes RSUs/bonuses/options, your “tax plan” needs to be a system, not a spreadsheet. After the 2025 tax law changes, many provisions were extended, but several benefits still have phaseouts and expirations (2028–2029). Your edge comes from timing income events, stacking tax-advantaged accounts, pairing equity sales […]