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Posted on May 12, 2025 by Dan Pascone
🏗 Engineer Your W-2 Side Hustle Income Before It Hurts
TL;DR Answer Box At $500K+ W-2 income, “maxed 401(k)” is not a strategy—it’s a starting line. High earners reduce tax drag by building infrastructure: (1) an entity that captures income you control outside your W-2 (and unlocks legitimate deductions and better tax treatment), and (2) stacked retirement “shelters” tied to that entity (often a Solo […]
Posted on May 7, 2025 by Dan Pascone
Tariffs, Trade Wars & Your Portfolio: What You Need to Know
TL;DR Answer Box Tariffs aren’t noise—they’re a regime change. In 2025, trade friction can rewire supply chains, compress margins, and create confusing inflation + rate signals. If you’re a high earner with a stock-heavy, passive setup, the move isn’t panic-selling—it’s stress-testing concentration, adding intentional liquidity, and rebalancing for second-order effects (where capital flows after the […]
Posted on May 5, 2025 by Dan Pascone
Your 2025 Tax Playbook: Planning for the End of the TCJA Party
TL;DR Answer Box If you earn $400K–$2M+ and your income includes RSUs/bonuses/options, your “tax plan” needs to be a system—not a spreadsheet. After the 2025 tax law changes, many provisions were extended, but several benefits still have phaseouts and expirations (2028–2029). Your edge comes from timing income events, stacking tax-advantaged accounts, pairing equity sales with […]
Posted on April 30, 2025 by Dan Pascone
Stock Options vs. Smart Money Moves—Vesting in 2025
TL;DR Answer Box Equity compensation is either a brilliant windfall or a minefield—depending on whether you track your key dates. If you’re juggling RSUs, ISOs, NSOs, or ESPPs, you need your grant, vest, exercise, sale, and expiration dates mapped in advance. Track the 4 critical dates: grant, vest, expiration (options), and taxation (vest/exercise/sale). Avoid tax […]
Posted on April 28, 2025 by Dan Pascone
Feeling a Little Burned Out? Here’s Your Financial Rescue Plan
TL;DR Answer Box Burnout isn’t inevitable—it’s optional when you use wealth as a tool, not just a scoreboard. The fastest way to create breathing room is to (1) build a 6–12 month “pause-without-panic” buffer, (2) redesign work pace with hybrid-retirement-style income, and (3) get ruthless clarity on your true burn rate so you know exactly […]
Posted on April 24, 2025 by Dan Pascone
FIRE Without the Burnout: How to Adjust FIRE Targets Without Breaking a Sweat
TL;DR Answer Box FIRE is a freedom strategy—not just a savings strategy. Yes, the classic starting point is the 4% rule (annual expenses × 25). But to retire early and stay retired, you need three upgrades: Real FIRE number: adjust for inflation, healthcare, and lifestyle changes. Tax-aware withdrawals: sequence accounts to reduce tax drag and […]
Posted on April 21, 2025 by Dan Pascone
Stock Option Taxes: How to Keep More of What You Earn
TL;DR Answer Box Stock options can build wealth—but the tax rules can bite. The smartest approach is to (1) confirm whether you have ISOs or NSOs, (2) model exercises and sales across multiple years to avoid bracket spikes, and (3) manage ISO AMT exposure by exercising in phases and running an AMT forecast first. Last […]
Posted on April 17, 2025 by Dan Pascone
Why Smart Investors Never Go All In on One Stock—Even When It’s Soaring
TL;DR Answer Box If your paycheck and your portfolio come from the same company, you’re exposed—not diversified. A concentrated employer-stock position can hit you twice in a downturn: your income is at risk and your net worth drops at the same time. The fix is rules-based diversification: sell a portion on a schedule, rebalance retirement […]
Posted on April 14, 2025 by Dan Pascone
Is Your Portfolio Falling Behind? How to Inflation-Proof Your Finances in 2025
TL;DR Answer Box Inflation reduces your purchasing power and can quietly break your retirement math. The fix is a simple 3-step system: (1) update your plan’s inflation assumptions and stress-test outcomes, (2) diversify into assets that historically hold up better during inflation (not just stocks/bonds), and (3) adapt as interest rates shift so you’re not […]
Posted on April 10, 2025 by Dan Pascone
Work Smarter, Pay Less: Tax Deductions You Didn’t Know You Could Take
TL;DR Answer Box Even high earners miss legal tax deductions every year—not because they’re careless, but because the tax code is massive and nuanced. The biggest “hidden” wins usually come from: (1) overlooked work-related deductions (often at the state level), (2) smarter investing tax tactics (munis, HSA optimization, tax-loss harvesting), (3) strategic charitable giving (DAFs, […]