Most taxpayers play defense.
We play to win.

Gambit works with individuals and families whose finances have outgrown basic tax prep. Our clients are typically high earners, business owners, investors, or anyone with layered income, assets, or decisions where strategy materially affects their tax liability.

We focus on medium- to high-complexity tax returns. Gambit is a strong fit for W-2 professionals earning over $125,000, taxpayers with a net worth of over $500,000, entrepreneurs, and small business owners (LLC, S-Corp, etc.), who are best suited to take maximum advantage of the tax code.

Most tax firms consider it a success if they avoid errors and file on time. We focus on using the tax code deliberately. That means starting with strategy, modeling options, explaining trade-offs, and helping you make informed decisions, not defaulting to conservative assumptions or simply checking boxes.

We aim to identify at least one tax strategy that can be used on your current or next tax return that drives savings using perfectly legal, IRS-approved strategies.

No. While we do prepare and file returns, Gambit is designed for ongoing strategic partnership. Many clients work with us year-round to evaluate decisions, respond to changes, and adjust plans before deadlines, not after opportunities have passed.

70% of taxpayers who would benefit from tax strategy never use it. Many of the most impactful decisions, such as entity elections, timing of income and expenses, loss harvesting, and depreciation strategy, must be made before deadlines. Once a return is filed, those opportunities to save thousands are often gone. That’s why Gambit focuses on proactive planning throughout the year, not reactive fixes after the fact.

Your introductory strategy call is a working session, not a sales pitch. In this 15-minute conversation, we assess whether your situation is well-suited to proactive tax strategy and whether Gambit is the right fit for you. We’ll discuss your income, assets, and upcoming decisions, identify where strategic leverage may exist, and answer your questions directly so you leave with clarity either way.

If there’s a strong fit, we’ll ask you to upload your prior-year return. From there, we prepare personalized recommendations and review them with you on a 45-minute Discovery Call, where we also walk through scope and share a fixed price for strategic tax preparation.

We pursue strategies that are intentional, defensible, and aligned with your goals and risk tolerance. Every recommendation includes context, upside, and tradeoffs so you can make decisions confidently.

Gambit advocates for aggressive optimization of your tax return, but we don’t view that as risky. The tax code is written law, but applying it to real financial lives requires expert interpretation. Gambit brings the experience needed to navigate those gray areas responsibly, enabling you to make informed decisions with clarity and confidence.

We work across personal and closely held entity returns, including LLCs and S-Corps. Common scenarios include business income, equity compensation, real estate, multi-state considerations, and complex planning decisions, but the unifying factor is thoughtful strategy, not a checklist.