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Posted on October 14, 2024 by Dan Pascone
Retirement and Tax Planning: A Dynamic Approach for High Earners
TL;DR Answer Box Retirement planning and tax planning are inseparable. For high earners, the most durable approach is tax diversification: build wealth across three buckets—taxable, tax-deferred, and tax-free—so you can control your taxable income in retirement year-by-year. Pair that with proactive tax strategy (401(k)/HSA maximization, tax-loss harvesting, tax-efficient funds, and Roth planning like backdoor Roth […]
Posted on October 13, 2024 by Dan Pascone
Mastering Cash Flow Management & Expense Planning: A Guide to Long-Term Wealth
TL;DR Answer Box High income doesn’t automatically create financial security. The fastest way high earners lose control is through invisible lifestyle inflation, tax surprises, and poor cash-flow structure—not a lack of income. The solution is simple and repeatable: bucket your cash flow (now / soon / later), automate transfers into savings and investing, and review […]
Posted on October 9, 2024 by Dan Pascone
Structuring a Comprehensive Financial Plan for High Earners: A 4-Part Series
TL;DR Answer Box A real financial plan isn’t just investing—it’s a full system. Start by defining clear goals (short/mid/long-term), then measure progress with net worth. Build a budget that gives you “yes” money, manage debt strategically, and design retirement + tax planning across taxable / tax-deferred / tax-free buckets. Protect your downside with an emergency […]
Posted on September 30, 2024 by Dan Pascone
Smart Tech, Smarter Money: Using Personal Finance AI to Optimize Your Finances
TL;DR Answer Box AI is making personal finance faster and more accessible through automated expense tracking, smart alerts, robo-advisors, and scenario modeling. Use AI to reduce busywork and surface insights—but don’t outsource judgment. The best setup is a simple “stack” (budgeting + investing + Q&A) paired with periodic human review (DIY or advisor-led), especially when […]
Posted on September 16, 2024 by Dan Pascone
Why Trusts Are No Longer Just for the Ultra- Wealthy: A Practical Guide to Protecting Your Assets and Avoiding Probate
TL;DR Answer Box Trusts aren’t just “rich people tools.” A trust is a legal structure that can help you avoid probate, keep your estate private, protect assets, and control how (and when) money is passed to beneficiaries. A revocable living trust is often the most practical starting point for families with real estate, kids, or […]
Posted on September 9, 2024 by Dan Pascone
Maximizing Employee Stock Purchase Plans (ESPPs): A High Earner’s Guide to Wealth Building and Risk Management
TL;DR Answer Box An Employee Stock Purchase Plan (ESPP) lets you buy your company’s stock using after-tax payroll deductions—often at a 5%–15% discount, sometimes with a lookback that prices shares using the lower of the offering-date or purchase-date price. ESPPs can be a powerful wealth tool, but the biggest risk for high earners is over-concentration: […]
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 September 3, 2024 by Dan Pascone
Credit Scores Demystified: The Key to Elite Financial Privileges
TL;DR Answer Box Your credit score is a financial leverage tool—it influences loan approvals, interest rates, housing options, and sometimes even employment screening. If you want to improve it quickly, focus on the biggest levers: pay on time, keep credit utilization under ~10%, avoid opening multiple new accounts at once, keep older accounts open to […]
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 […]