Tax Strategies
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Posted on April 13, 2026 by Dan Pascone
After-Tax Returns: The Number that Actually Matters
TL;DR Answer Box After-tax returns are the number that actually matters because taxes can show up inside a taxable account even when you did not “sell anything.” The fix is not guessing. It is building a repeatable, coordinated system across wrappers, loss harvesting, share selection, and charitable moves. Same market exposure. Meaningfully better net results. […]
Posted on April 6, 2026 by Dan Pascone
The Real Estate Tax Benefits High Earners Misunderstand
TL;DR Answer Box Real estate tax benefits for high earners are real, but they are not uniform. “Real estate” is not one decision. It is multiple lanes with different rules for losses, liquidity, workload, and exit taxes. Use the framework below to classify the opportunity first, then evaluate whether the tax benefit is usable now, […]
Posted on March 30, 2026 by Dan Pascone
How to Build a Hybrid Retirement Plan That Makes Work Optional
TL;DR Answer Box TL;DR: A hybrid retirement plan helps high earners retire gradually by combining flexible work income, tax-aware withdrawals, and time-horizon investing so work becomes optional sooner without making the plan fragile. The goal is not a single retirement date. The goal is a work-optional date backed by a real model that integrates taxes, […]
Posted on March 23, 2026 by Dan Pascone
6 Private Market Investment Questions to Ask First
TL;DR Answer Box Private market investment questions can be answered quickly if you stop starting with performance and start with liquidity, fees, and incentives. The private markets pitch is louder in 2026 because distribution is shifting toward private wealth, not because every high earner needs alternatives. Use the Fit Test first, then ask the six […]
Posted on March 16, 2026 by Dan Pascone
Mega Backdoor Roth 2026: How to Use Your 401(k) Limit
TL;DR Answer Box Mega Backdoor Roth 2026 is how high earners may move after-tax 401(k) contributions into Roth (either inside the plan or to a Roth IRA) so future growth can be tax-free. The catch is that you need three plan features (after-tax contributions, a conversion or in-service rollover path, and clean recordkeeping), and you […]
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 […]