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Near-term decisions have tax impacts that can extend across generations. An equity grant vesting, a stock sale, a move across state lines, an inheritance, a year when income drops or spikes — each one sets the tax outcome at the moment the decision is made.
We project the tax math ahead multiple years. Income timing, gain realizations, Roth conversions, charitable gifts, and equity comp all get weighed against the bracket math they trigger, before they happen.
The work runs forward across multiple years rather than annual cycles. Income volatility, business sale timing, retirement transitions, equity vest schedules, and state moves all create multi-year tax positions that can't be solved one year at a time. The plan looks five and ten years forward so this year's decisions account for what they'll trigger in the years after.
Tax outcomes get decided inside the moves other practices make. An investment trade, a retirement withdrawal, an estate transfer, an equity exercise, a charitable gift — each carries tax math that gets locked at the moment it happens. Our work is making the tax math visible before the move gets made.
Each year's bracket determines what each decision is worth. Roth conversions get sized to fill the lower brackets, capital gains get harvested when the bracket allows, and charitable gifts get bunched into the years that need them.
Choose to have tax preparation in-house. The advisor who designed the multi-year strategy is the same person coordinating the return at the end of each year.
Before any tax modeling, there's a real conversation about what triggered the look. Often it's a surprise on last year's return, an equity exercise approaching, a business sale getting close, a planned move across state lines, or a sense that the current setup isn't catching the math early enough. By the end you'll know whether this fits and what the work involves.
Tax planning starts with the position that's already in motion. Recent returns, cost basis on every taxable holding, loss and charitable carryforwards, state residency status, equity grant schedules, and the trajectory of pension and required distributions — the planning gets built from where this picture stands.
Tax planning starts with the position that's already in motion. Recent returns, cost basis on every taxable holding, loss and charitable carryforwards, state residency status, equity grant schedules, and the trajectory of pension and required distributions. The planning gets built from where this picture stands.
Tax planning is continuous work across the year: Estimated payments get calibrated each quarter, mid-year decisions on conversions get executed before their deadlines, and year-end moves happen in November and December once the year's numbers are visible.
The tax landscape shifts from both sides. Congress changes the tax laws in your area, and life events change the tax position from inside the household. Each one reopens the multi-year map and resets what comes next. The plan stays current as both keep moving.
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Tax planning is year-round work rather than annual review. The senior advisor who built the multi-year strategy is the same person at each quarterly recalibration, each mid-year decision, and each year-end positioning move.
Our advisors keep concentrated client books so the senior advisor stays close to the tax math across each quarter. When a decision crosses into investments, retirement, or estate planning, the specialists are in-house and one conversation away.
Rob works with founders, executives, and families navigating concentrated wealth, business exits, and generational planning. He founded Arrowroot in 2013 and leads the firm from Southern California.
Cassandra works with clients on retirement planning and Medicare strategy, with deep expertise in healthcare cost planning and the tradeoffs that shape later-life decisions. She is a licensed insurance agent with more than 12 years in financial services.
Crystal works with individuals, families, and business owners on financial planning, investment management, and tax strategy. She is a CFP® and IRS Enrolled Agent with over two decades of experience.
Irene oversees operations and regulatory compliance across the firm. She brings more than 22 years of financial services experience across investments, capital markets, operations, management, and sales.
Mark works with families and business owners on financial planning, portfolio management, and tax strategy, with a particular focus on cash flow and long-range projections. He is a CFP® and IRS Enrolled Agent.
Diane works with individuals, families, executives, and retirees on retirement planning, investment strategy, and long-term wealth management. She is an Accredited Investment Fiduciary® with over 30 years of experience.
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Building a business creates a personal wealth situation the business itself won't manage. Concentration in the company, deferred compensation, an eventual exit, and the retirement that follows each carry their own math. Decisions on the company side get coordinated with the personal plan so the two sides move together.
Threads through every investment decision and every estate document. Tax efficiency depends on timing as much as choice. Decisions get made so the math holds up across decades rather than quarters.
Built around the obligations the portfolio has to meet. Holdings fund retirement income, education, gifting, and the unexpected on schedules that match real life. Risk gets calibrated to the work, and tax planning runs through every position.
At the center of cash flow, tax, and investment decisions, this long phase has its own math at every stage. Income, taxes, and sequence get modeled so the timeline holds up under stress. The work continues across every transition retirement contains, since one phase rarely sets the pattern for the next.
Touches every other practice the moment something changes. Estate, tax, and investment positions stay aligned so the structures still work when the time comes. Documents get revisited as the family and the assets shift.
Protects what's been built when something happens. Coverage gets sized to real exposure across business interests, dependents, and estate liquidity. As obligations shift, coverage shifts with them so the protection matches the situation.
Stock from your employer carries three identities at once: a tax position, an investment position, and a concentration risk. Vesting, exercise, sale, and AMT decisions get weighed together rather than separately. Timing of each gets coordinated against the broader picture.
Financial Planning is the practice that integrates the others into one plan. Tax decisions get made with investments in view, estate work gets shaped by the cash flow strategy, equity compensation gets calibrated against the rest of the picture. The plan holds together because one advisor guides it.
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Tell us where you are, where you're headed, and what you're working with. We'll help you get there.
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