Blog
Select a Category
Posted on August 11, 2025 by Dan Pascone
Equity Compensation Explained: How High-Income Professionals Can Maximize Their Wealth
TL;DR Answer Box Equity compensation can be a wealth-building accelerator, but only if you run it with a plan. Start by identifying your award types (RSUs, ISOs, NSOs, ESPP, performance shares), then map the life cycle (grant, vest, exercise, sale) and pre-decide your tax and diversification rules before the next big event hits. The biggest […]
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 31, 2025 by Dan Pascone
How the Wealthy Future-Proof Their Kids (Without Spoiling Them)
TL;DR Answer Box Legacy planning isn’t about “trust funds.” It’s about structure. High-earning families can build real, durable financial advantage by (1) creating legitimate earned income for kids (where appropriate) and funding a custodial Roth IRA, (2) using trusts while you’re alive to transfer appreciating assets intentionally (GRATs/SLATs when fact-appropriate), and (3) funding education with […]
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 July 24, 2025 by Dan Pascone
Oversaving Might Be Your Biggest Expense
TL;DR Answer Box High earners don’t need stricter budgets—they need smarter structures. Use a Lifestyle ROI lens to spend on what actually matters, install dynamic drawdown rules so discretionary spending flexes with markets, and add guardrails to prevent lifestyle creep from quietly stealing your future freedom. The goal isn’t to “spend less.” It’s to spend […]
Posted on July 22, 2025 by Dan Pascone
Taking Social Security at 62 vs. 70: What’s the Right Move for Your Retirement?
TL;DR Answer Box Your Social Security claiming age is a retirement lever. Claiming at 62 locks in a smaller lifetime floor, claiming at 70 maximizes guaranteed income later, and claiming at 67 (FRA) often creates the best balance between portfolio strain and long-term stability. The “right” answer depends on longevity, cash-flow needs, spouse/survivor planning, and […]
Posted on July 16, 2025 by Dan Pascone
Redefining Retirement: The Hybrid Strategy That Makes Work Optional
TL;DR Answer Box Hybrid retirement is a structured transition from full-time work into a flexible, purpose-driven lifestyle—without fully “stepping away.” You blend part-time income with rules-based portfolio withdrawals, use lower-income years for tax-smart moves (like Roth conversion planning), and build a plan that makes work optional while preserving momentum and fulfillment. Last updated: January 26, […]
Posted on July 14, 2025 by Dan Pascone
FIRE Explained: How to Achieve Financial Independence and Retire Early
TL;DR Answer Box FIRE (Financial Independence, Retire Early) is a framework for making work optional by increasing your savings rate, investing in low-cost diversified assets, and building a portfolio large enough to cover your lifestyle. Your FIRE number is often estimated as 25× annual spending (the “4% rule” framework). You don’t have to retire at […]
Posted on July 10, 2025 by Dan Pascone
The Best Retirement Withdrawal Strategy? Why Risk-Based Guardrails Win
TL;DR Answer Box Most retirement plans fail in the withdrawal phase because spending rules are too rigid (fixed dollar or 4% rule) or too operationally complex (buckets). The approach we use with Tailored Wealth clients is risk-based guardrails: a flexible spending range guided by upper/lower thresholds and probability-of-success modeling, so you know when to spend […]