.avif)
An equity grant arrives with a vesting schedule, a few pages of explanation, and a sense that something significant is happening. The decisions that follow can stretch over years. When to exercise, how to handle the AMT exposure of an ISO exercise, how much household wealth to concentrate in one company's stock — each one shapes the tax bill, the holding period, and the value of what's left.
We model the equity across the years it vests, the brackets it triggers, and the portfolio it eventually joins. Every thread is traced accordingly, including AMT exposure, sales, charitable gifts, and all that the household has in motion.
Equity unfolds over multiple years: grant, vest, exercise, sale, tax-year boundary. Each decision falls in a different income picture. The plan runs across the whole horizon, with every decision sized against the brackets and the holdings of its year.
Every equity decision has a deadline. An ISO has a ten-year life and a window after departure. A 10b5-1 plan needs filing months ahead of the trades it allows. An NSO exercise has tax-year timing implications. The math gets worked before the window opens, and the decision arrives already thought through.
Equity from one employer concentrates wealth in one stock price. The work is bringing that concentration down on a timeline that fits the tax cost, the vesting schedule, and the rest of the portfolio. Sales get sequenced into bracket years where the tax hit is manageable. 10b5-1 plans get used where trading windows constrain timing. Charitable gifts of appreciated stock get folded in where they fit both the giving plan and the diversification work.
Equity touches tax planning, investment strategy, estate documents, and charitable giving. The plan reads equity as one thread running through all these practices.
Before any modeling, there's a real conversation about what brought you here. Often it's a grant that just landed, a vest coming up, an IPO or tender offer on the horizon, a planned departure with options about to expire, or last year's AMT bill that came in larger than expected. By the end you'll know whether this fits and what working together involves.
Every grant in force: RSUs, ISOs, NSOs, ESPP shares, RSAs, performance grants, deferred comp. Vesting schedules, strike prices, grant dates, expiration dates. AMT carryforwards from past exercises. Existing 10b5-1 plans. Vested shares already held, with their cost basis. The concentration the household carries in one company.
The plan gets modeled across the years the equity unfolds. Income projections show which years run light on the brackets and which run heavy; ISO exercises get sequenced to manage AMT exposure; sales get scheduled into years where the bracket math fits; and 10b5-1 plans get drafted where trading windows constrain the calendar. Trade-offs surface explicitly: holding for long-term capital gains versus selling at vest; exercising and holding versus exercising and selling; and gifting appreciated stock versus selling and giving cash.
10b5-1 plans get filed and put in force. Exercise orders execute on the dates the model set. Sales sequence into the bracket years the plan identified. Charitable transfers of appreciated stock move through to the donor-advised fund or trust. Tax projections update as each decision lands. Beneficiary designations on equity accounts get aligned with the rest of the estate plan.
Equity work runs as long as the grants do. The plan updates whenever a new grant lands, a vesting schedule changes, the stock price moves, an IPO or tender offer arrives, or a departure puts an exercise window on the clock.
.svg)
Owners work with many advisors at once. The senior advisor here is the one keeping the personal picture whole through every phase: the building years, the pre-sale work, the deal, and what follows.
Our team keeps concentrated client books so the advisor stays close to both pictures — business and household — year after year. When a decision crosses into tax, estate, or investment management, 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.
.avif)
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.
.avif)
.png)
.png)
Tell us where you are, where you're headed, and what you're working with. We'll help you get there.
.jpg)