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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 equity […]
Posted on August 5, 2024 by Dan Pascone
How High Earners Can Thrive Between Jobs: Smart Emergency Funds
TL;DR Answer Box High earners need a different emergency-fund framework than “6 months of expenses.” Your target should be based on (1) your burn rate, (2) how long it realistically takes to replace your niche role at comparable pay, and (3) your cost structure (especially in HCOL areas). Keep the fund liquid, but don’t let […]
Posted on July 29, 2024 by Dan Pascone
4 Financial Factors to Consider Beyond Salary
TL;DR Answer Box A great job offer isn’t defined by salary alone. High earners should evaluate the total package: equity (RSUs/options/ESPP), bonus terms, retirement plan design (match, vesting, after-tax/Mega Backdoor Roth support), and benefits (health plan structure, HSA eligibility, disability/life coverage). Many “perks” are distractions—focus on what compounds your wealth and reduces risk over time. […]
Posted on July 23, 2024 by Dan Pascone
Maximizing Employer-Sponsored Retirement Plan Contributions
TL;DR Answer Box Employer-sponsored retirement plans (like 401(k)s) are one of the easiest ways to build wealth because they combine tax advantages, automation, and often an employer match. The real power move is not just “maxing the 401(k)”—it’s understanding contribution limits, plan features (Roth, after-tax, match vesting), and using tax diversification across pre-tax, Roth, and […]
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 11, 2024 by Dan Pascone
Upgrade Your Pay: How to Get the Best Compensation Package
TL;DR Answer Box Your compensation package isn’t just your base salary—it’s a full system: equity, bonuses, retirement benefits, healthcare, HSA, PTO, remote work flexibility, and professional development. High earners build outsized wealth by negotiating the parts that compound (equity + retirement + tax advantages) and by avoiding hidden “gotchas” (vesting schedules, option windows, RSU tax […]
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. The […]
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 cap […]
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 flexibility, […]
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 […]