Gambit was built in response to a market gap: tax filing without strategy. Too many capable people were making major financial decisions without clear, proactive guidance. We created Gambit to bring disciplined analysis, transparency, and strategic thinking into every engagement.

The firm’s origins are personal. Co-founder Brian inherited his parents’ longtime tax preparer and, for years, assumed his situation was being handled thoughtfully. It wasn’t until a successful startup exit that he received proper tax strategy and discovered he had overpaid more than $100,000. That experience shaped Gambit’s mission: to make the rigorous, proactive tax strategies of the 1% more accessible well before decisions are locked in.

It means we don’t start with assumptions, defaults, or forms. We start by understanding your full financial picture, modeling options, and explaining tradeoffs before decisions are made. Filing is compliance; strategy is the work that shapes tax liability outcomes.

Candidly, less than 20% of taxpayers can drive meaningful savings through tax strategy. For many, standard software ensures accurate filing and captures basic credits and deductions—that’s table stakes. Gambit is built for people whose financial lives create opportunity: asset owners, business operators, investors, and those making decisions that affect taxes months or years before a return is filed. We work with clients who want to be on the front foot, planning ahead rather than discovering missed opportunities after the fact.

We don’t default to overly conservative positions or unnecessary risk. Every recommendation is evaluated for defensibility, upside, and alignment with your comfort level. We explain the tradeoffs clearly, and you decide how to proceed.

You’ll work directly with experienced professionals, not junior staff or call-center models. Your Gambit Strategist is accountable for your strategy and remains involved throughout the relationship, with support from a broader team as needed.

Gambit operates nationally with a strong California foundation. We maintain three California-based locations—in Los Angeles, San Diego, and the San Francisco Bay Area—where in-person meetings are available by appointment only. Our model is built for multi-state, mobile, and evolving financial lives, with remote collaboration as the default and in-person support available when it adds value.

We aim to be a long-term strategic partner, not a transactional vendor. The goal is clarity, confidence, and continuity, so your tax strategy evolves as your life and opportunities change.

Timing is central to effective strategy. Most tax decisions can’t be meaningfully corrected after the fact, which is why forward-looking planning is essential. The value comes from being positioned early, making informed choices over time rather than discovering missed opportunities once the window has closed.