Tax Strategies
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Posted on September 3, 2024 by Dan Pascone
Introduction to Retirement Planning and Tax Diversification
TL;DR Answer Box Tax diversification helps you keep more of what you save. By spreading retirement assets across tax-deferred accounts (like Traditional IRAs and 401(k)s) and tax-free accounts (like Roth IRAs and Roth 401(k)s), you gain flexibility to control taxable income in retirement. This lets you manage tax brackets, adapt to changing tax laws, and […]
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 August 20, 2024 by Dan Pascone
The Silver Lining of Lower Income Years: Tax Tricks for Top Earners
TL;DR Answer Box A low-income year can be one of the most strategic tax windows in a high-earner’s life. When your taxable income drops (sabbatical, job transition, business launch, early retirement runway), you may be able to execute Roth conversions at lower brackets, contribute directly to a Roth IRA, exercise stock options with less AMT/ordinary […]
Posted on August 13, 2024 by Dan Pascone
Down Market Tactics: A Modern Investor’s Guide to Tax Loss Harvesting
TL;DR Answer Box Tax loss harvesting (TLH) turns market drawdowns into a tax strategy. When markets dip, you can sell investments at a loss to offset realized capital gains (and up to $3,000 of ordinary income per year), then reinvest to stay aligned with your allocation, while carefully avoiding wash sales. For high earners with […]
Posted on July 16, 2024 by Dan Pascone
Rolling Over Your 401(k): Best Practices for Managing Retirement Accounts
TL;DR Answer Box A 401(k) rollover moves retirement funds from an old employer plan to a new 401(k) or an IRA. The safest move is a direct rollover, where money goes institution-to-institution and you never touch it. Indirect rollovers create risk: a strict 60-day deadline, a 20% mandatory withholding, and potential taxes/penalties if you miss […]
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 June 25, 2024 by Dan Pascone
The High Earner’s Guide to State and Local Taxes (SALT) & Deductions
TL;DR Answer Box Moving states for taxes can change your net income dramatically, but it’s not just “state income tax vs. no state income tax.” SALT includes income taxes, property taxes, and (in some cases) sales taxes, and the federal deduction has been capped at $10,000 under the Tax Cuts and Jobs Act (TCJA). That […]
Posted on June 18, 2024 by Dan Pascone
Life Insurance Retirement Plans: Turning LIRPs into Powerful Retirement Tools
TL;DR Answer Box A Life Insurance Retirement Plan (LIRP) uses a permanent life insurance policy’s cash value to create a retirement income stream, often through policy loans that can be tax-free if structured and managed correctly. LIRPs can be useful for high earners who are already maxing out traditional retirement accounts and want additional tax-advantaged […]
Posted on June 11, 2024 by Dan Pascone
A Comprehensive Guide to NIIT for High-Income Investors
TL;DR Answer Box The Net Investment Income Tax (NIIT) is an additional 3.8% surtax on certain investment income (like interest, dividends, capital gains, rental/royalty income, and non-qualified annuities) when your modified adjusted gross income (MAGI) exceeds certain thresholds. Most high earners get surprised because NIIT stacks on top of your normal investment taxes. The good […]
Posted on May 28, 2024 by Dan Pascone
The High Earner’s Playbook to Donor-Advised Funds
TL;DR Answer Box Donor-Advised Funds (DAFs) let high earners “front-load” charitable deductions in a high-income year, then distribute grants to charities over time. You get an immediate tax deduction when you contribute, your donation can grow tax-free inside the DAF, and you keep advisory privileges on where/when grants go. DAFs are best when philanthropy is […]