Tax Strategies
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Posted on October 27, 2025 by Dan Pascone
Donor-Advised Funds: The Tax-Smart Way to Give
TL;DR: A donor-advised fund (DAF) lets high earners contribute in peak-income years, take an immediate deduction (subject to AGI limits), avoid capital gains on long-term appreciated assets, and grant to charities over time, privately, on your own schedule. Last updated: October 21, 2025 Watch/Listen: How Philanthropy Rewires a Life (Podcast, Ep. 26) The Tax-Smart Way […]
Posted on September 29, 2025 by Dan Pascone
2025 Tax Law Changes for Executives: What to Do Now
TL;DR: The new 2025 tax law permanently extends lower brackets, expands the estate exemption from 2026, boosts QBI and SALT, and restores 100% bonus depreciation with higher Section 179. High earners and owners who plan now can lock in savings and build a more resilient after-tax wealth plan. Last updated: September 29, 2025 Introduction The […]
Posted on September 17, 2025 by Dan Pascone
10b5-1 Plans for RSUs: From Legal Protection to Long-Term Diversification
TL;DR: A well-designed 10b5-1 plan turns inevitable RSU sales into a rules-based system that reduces single-stock risk, manages taxes, and protects your market reputation. It’s not just compliance, it’s strategy. Last updated: September 29, 2025 Why a 10b5-1 Plan Matters If you’re sitting on a mountain of equity, you already know to diversify and steer […]
Posted on August 7, 2025 by Dan Pascone
Is Your Exit Plan Half-Baked? Here’s How Founders Turn Valuation into Legacy
Why a Big Valuation Isn’t Enough, and What to Do About It If you’re building something extraordinary, a company, a product, a game-changing solution—chances are, you’re also anticipating a future exit that could reshape your family’s financial future. But while founders often focus on achieving the highest valuation possible, the real wealth often lies in […]
Posted on August 4, 2025 by Dan Pascone
The 2025 Tax Overhaul Could Save You Thousands: What Every High Earner Needs to Know
A Generational Shift in Tax Planning The most sweeping tax legislation in decades has just passed—and if you’re not paying attention, it could cost you tens (or even hundreds) of thousands in missed opportunities. Nicknamed the “One Big Beautiful Bill”, this 870-page reform package reshapes the financial landscape for high-income earners, business owners, and wealthy […]
Posted on July 28, 2025 by Dan Pascone
How to Legally Pay Less Taxes in 2025: Strategies Every High Earner Should Know
Tax season shouldn’t be a surprise, and it definitely shouldn’t be something you dread. Yet, every year, high-income professionals find themselves overpaying or scrambling to cover unexpected tax bills. The truth? Most tax issues stem from a lack of planning and common misconceptions. In this post, you’ll discover how to legally reduce your tax bill […]
Posted on June 2, 2025 by Dan Pascone
How to Navigate a Career Change Without Losing Financial Ground
Leaving a Gig? The Timer on Your Tax Jackpot Just Started Career transitions aren’t just professional, they’re personal finance pressure cookers. If you’re stepping away from a high-level role as a founder, operator, or senior exec, you’re not just updating your LinkedIn title. You’re entering one of the rarest windows of financial opportunity. In this […]
Posted on May 26, 2025 by Dan Pascone
Breaking Down Trump’s Proposed Middle-Class Tax Cuts for 2025 and Beyond
Trump’s 2025 Tax Plan: A 4-Year Window to Build Generational Wealth How High Earners Can Leverage Lower Rates, MAGA Accounts, and Expiring Credits Before 2028 Whether you support it, oppose it, or just want to understand how it impacts your bank account, Trump’s proposed 2025 “One Big Beautiful Bill” deserves your attention. At nearly 400 […]
Posted on May 12, 2025 by Dan Pascone
🏗 Engineer Your W-2 Side Hustle Income Before It Hurts
📈 Personal LLCs, Family Companies, and Why Your “Maxed Out 401(k)” Isn’t Nearly Enough At $500K+ W-2 income, normal rules stop applying. It seems like you’re fighting less for gains but more to survive tax-wise. High earners who thrive grind harder, but also learn to play the system smarter. They build infrastructure, weaponize volatility, and […]
Posted on May 5, 2025 by Dan Pascone
Your 2025 Tax Playbook: Planning for the End of the TCJA Party
⏳ The Final Countdown: Your 8-Month Tax Alpha Window If you’re earning $400K–$2M+ and dealing with RSUs, bonuses, or stock options, your tax situation is more than just a spreadsheet, it’s a dynamic, complex system. And what you do between now and December 2025 could shape your financial legacy for years to come. The Tax […]