Tax Strategies
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Posted on April 30, 2025 by Dan Pascone
Stock Options vs. Smart Money Moves—Vesting in 2025
🎉 Your Vested Wealth Is Growing, But So Is Your Tax Bill. Let’s Fix That Equity compensation is either a brilliant windfall or a minefield, depending on how you play your cards. If you’re juggling RSUs, ISOs, NSOs, or ESPPs, you need to know your key dates like you know the passcode to your phone. […]
Posted on April 21, 2025 by Dan Pascone
Stock Option Taxes: How to Keep More of What You Earn
💸 Stock Options ≠ Cash, Until You Get the Taxes Right Stock options often feel like a hidden financial superpower, until tax season rolls around.Exercising and selling equity compensation isn’t like a regular paycheck, it’s more like navigating a financial minefield. With the right strategy, you can turn those stock options into long-term wealth without […]
Posted on April 10, 2025 by Dan Pascone
Work Smarter, Pay Less: Tax Deductions You Didn’t Know You Could Take
🥳 You’ve Earned It—Now Let’s Maximize What You Keep If you’re maxing out your retirement accounts, donating to charity, and itemizing business expenses, you might think you’ve nailed tax season.But here’s the truth: even high earners with solid strategies miss key deductions every year. The U.S. tax code is massive—and full of completely legal ways […]
Posted on October 9, 2024 by Dan Pascone
Structuring a Comprehensive Financial Plan for High Earners: A 4-Part Series
In the words of personal finance celebrity Dave Ramsey: “You must gain control over your money, or the lack of it will forever control you.” Creating a solid financial plan is more than just a spreadsheet exercise—it’s a strategic roadmap that directs how your wealth grows, is preserved, and, eventually, how it supports your life’s ambitions. […]
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
If you didn’t grow up in a family with a private jet and a nameplate estate, chances are you’ve heard of trusts but have never given them much thought. Trusts tend to carry an air of exclusivity—something only the ultra-wealthy need to worry about, right? Not so fast. While trusts are often associated with billionaires […]
Posted on September 3, 2024 by Dan Pascone
Introduction to Retirement Planning and Tax Diversification
Retirement planning is a critical aspect of financial management that can often seem overwhelming. However, its importance cannot be overstated. Proper planning ensures that your golden years are not only comfortable but also financially secure. One of the key components of an effective retirement strategy is tax diversification. Understanding how different types of retirement accounts […]
Posted on August 24, 2024 by Dan Pascone
The QSBS Advantage: How to Turn Startup Equity into Tax-Free Wealth
Imagine a world where you can invest in a promising startup, hold onto your shares for a few years, and then, when the time is right, sell those shares and keep a significant chunk (and maybe all) of your gains out of the taxman’s reach. Qualified Small Business Stock (QSBS) refers to shares in a […]
Posted on August 20, 2024 by Dan Pascone
The Silver Lining of Lower Income Years: Tax Tricks for Top Earners
Picture this: you’re a top earner who has spent years climbing the career ladder, accumulating increasing salaries, bonuses, and stock options, each year greater than the last. Then, life throws you a curveball. Maybe you’ve decided to take a sabbatical to travel the world, pursue a passion project, or simply recharge. Perhaps you’re navigating a […]
Posted on August 13, 2024 by Dan Pascone
Down Market Tactics: A Modern Investor’s Guide to Tax Loss Harvesting
It’s August 2024, a snapshot in time when tax loss harvesting could have been used to significant effect. The S&P 500 saw its biggest single-day drop since September 2022. The Dow shed more than 1,000 points. The Nasdaq 100 erased almost $1 billion in market value. The Nikkei 225, Japan’s benchmark stock index, saw its […]
Posted on July 2, 2024 by Dan Pascone
Tax Tips for Cash Bonuses, RSUs, and Stock Options
Companies typically offer various types of bonuses, such as cash bonuses, stock options, and Restricted Stock Units (RSUs), and each comes with unique considerations. These bonuses, typically awarded annually, quarterly, or even as performance-based incentives, are a welcome windfall, but the tax implications can be an unanticipated cold plunge. Let’s break down the key points […]