Retirement
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Posted on March 27, 2025 by Dan Pascone
Crush the Rest of 2025: A Smarter, Sharper Portfolio Starts Now
TL;DR Answer Box If your portfolio has drifted onto autopilot, 2025 is the year to realign it. The highest-impact moves are simple: (1) assign every dollar a job, (2) optimize asset location for taxes, (3) stress-test risk before the market does it for you, (4) consolidate and cut fee/overlap drag, and (5) rebalance with a […]
Posted on March 4, 2025 by Dan Pascone
Life After the Big Payout: Wealth Preservation and Growth Strategies
TL;DR Answer Box A liquidity event can change your life, if you handle the first 90 days correctly. Before upgrading your lifestyle, stabilize cash, estimate taxes, eliminate toxic debt, and build a rules-based plan for diversification. Then invest across tax “buckets” (taxable, tax-deferred, tax-free) and use advanced tools like Roth conversion ladders, insurance-based strategies (LIRPs), […]
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 […]
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 […]
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 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 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, […]
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 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 3, 2024 by Dan Pascone
Your Guide to Different Retirement Accounts: Achieving Tax Diversification
TL;DR Answer Box Tax diversification means spreading retirement savings across tax-deferred accounts (pay taxes later) and tax-free accounts (pay taxes now, withdraw later tax-free). Since nobody knows what future tax rates will be, having multiple “tax buckets” gives you flexibility in retirement to control your taxable income and potentially reduce lifetime taxes. Last updated: February […]