Proactive tax planning can protect investment returns years, or generations, down the road. As your wealth increases and the network of those depending on it grows, the cost of getting it wrong increases exponentially.
Tax strategy at Arrowroot Family Office is planning work, not filing work. Entity structure, the timing of gains and gifts, asset location, and multi-year projections get handled before decisions are made rather than reconciled afterward. Because the same team runs the family's investment and estate work, tax considerations are present in every decision rather than bolted on at year end. The strategy is built to hold up across decades.
.avif)
.png)
Tax conversations begin with an introduction, often after a significant event. The first discussion is about the family's current tax picture and where planning has been reactive. You leave knowing what proactive strategy could change.
The family's full tax position comes into view. Returns, entities, trusts, jurisdictions, income sources, investments, and estate positions all get mapped. The result is one picture of how the family is actually taxed — often it exists in one place.
A tax framework gets built around the family's situation and coordinated with the investment and estate work. Entity structure, the timing of gains and gifts, asset location, and multi-year projections get designed together. You end with a strategy that anticipates decisions rather than reacting to them.
Tax strategy is continuous, not seasonal. Decisions get checked for tax impact as they arise, gains and gifts get timed, projections get updated, and the family's CPA gets coordinated where needed. The family directs the strategy rather than waiting for the annual reckoning.
Tax strategy spans transitions and generations. The framework carries through sales, transfers, and next generation hand-offs, adapting as laws and circumstances change. The relationship continues so the planning stays ahead rather than behind.
.svg)
Tax strategy only works when the person planning it sees everything else the family is doing. The senior advisor handling your tax work is the one coordinating the investments and the estate, not a specialist consulted once a year. That vantage point is what lets tax get planned into decisions rather than discovered after them.
Behind that advisor is the rest of the firm. Investment management, estate planning, and business succession all happen inside one team, so tax is never an afterthought to the decisions that drive it. Concentrated client books keep the advisor close enough to act on opportunities while there is still time to use them.
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)
.avif)
Works in concert with governance and next generation planning, giving the structure a place to come alive in person. A retreat turns the framework into a conversation the whole family takes part in, away from the day-to-day. What surfaces there feeds directly into the decisions the family makes in the year that follows.
Connects the operating company to the personal financial life it eventually funds. Succession is rarely a single event, and the years around it carry tax, estate, and liquidity decisions that compound. The framework coordinates the company side and the family side so the handoff happens on the family's terms.
Touches the family's businesses, cash flow, and reporting at the operational level. Daily financial oversight is where small issues either get caught early or quietly compound. The framework keeps the operating numbers connected to the family's longer financial picture.
Carries the administrative weight that complex financial lives generate. Bill payment, document management, and the logistics of multiple properties and entities take real time and attention. The framework absorbs that load so the family directs the operation rather than running it.
Anchored to the obligations the portfolio has to meet across the family's lifetime. Holdings fund retirement income, gifting, philanthropy, and the unexpected on schedules that match real life. Risk gets calibrated to the work the money has to do, and tax runs through every position.
Touches every other practice the moment something changes. Estate structures only work if the tax, investment, and ownership positions behind them stay aligned. The framework keeps documents and entities current as the family and the assets shift.
Threads through every investment decision, every entity, and every estate document. Tax efficiency at this level depends on timing and coordination as much as the individual choice. The framework is built so the math holds up across decades rather than a single filing year.
Protects what the family has built when something goes wrong. Coverage and exposure get sized to the real picture across businesses, properties, dependents, and estate liquidity. The framework keeps protection matched to the situation as obligations change.
Connects the family's philanthropy to its tax position, its estate plan, and the next generation. The structures built around giving outlast the impulses that began it. The framework keeps the giving coordinated with everything else rather than left to the side.
Pairs with family governance and estate planning to prepare the people who will inherit. Readiness is built over years, through gradual involvement rather than a single handoff. The framework brings the next generation in on a cadence that respects where they are.
Most of our relationships begin with an introduction. If you've been sent our way, or you've simply decided it's time, this is where to reach us.
.jpg)
.png)
.png)