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When the business is the focus, the personal plan can fall behind. Bridge the gap while building, before a sale, or after one. Concentration in the business, deferred compensation, executive insurance, and the planning around an eventual exit all need their own framework.
We build the personal plan that determines whether the business grows, shrinks, or sells. Our focus is on managing broader holdings, sequencing compensation against tax math, sizing real insurance exposure, and planning deals before a major sale.
The business is usually the largest exposure on the owner's personal balance sheet. The wealth around it gets built to absorb that risk: diversified holdings sized to the concentration, liquidity reserved for the years it's needed, and risk calibrated to what the household can carry.
The decisions that determine after-tax outcomes from a sale get set up years before the LOI. Trust structures, gifting strategies, charitable vehicles, entity restructuring, and the tax positioning that frames the transaction all need time the deal doesn't give.
The sale of a business is the largest single planning event of an owner's life. Tax positions, estate documents, investment allocation, and retirement income all reset at the moment proceeds land.
Selling the business is the end of one financial life and the start of another. Liquidity arrives all at once, the household identity shifts, retirement reshapes, and philanthropy and new ventures become real options.
Before any company analysis, there's a real conversation about where you are with the business and where the personal side connects. The company growing faster than the planning around it, an LOI on the desk, a sale just closed, a deferred-comp election approaching, or a sense that the concentration has gotten bigger than the rest of the picture. By the end you'll know whether this fits and what working together involves.
On the company side: ownership structure, current valuation, capitalization, deferred comp schedules, buy-sell arrangements, equity grants outstanding. On the personal side: cash, investments, real estate, retirement accounts, other interests, family structure, tax history, existing documents. The plan reconciles to both.
The personal plan gets built around the owner's situation and the company's life cycle. Trade-offs surface explicitly: in gifting interests before a valuation jump or holding for control, restructuring entities for tax positioning or keeping it simple, deploying liquidity into diversification, or reserving for the next venture.
During a sale, the M&A team handles the deal and we handle the personal side. Trust structures get established with the attorney; gifting interests happen before valuation events change their value; and entity restructuring, deferred-comp elections, and executive insurance get put in place on the schedules they require.
The business produces events the personal plan has to respond to. For instance, funding rounds, new equity grants, valuation jumps, term sheets, due diligence, and closing. Life events arrive on their own schedule too — marriage, divorce, birth, the death of a parent, or a state move that changes the tax math.
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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 advisors keep concentrated client books so the senior 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.
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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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