A clearer picture
Frequently Asked Questions
Company stock. Taxes. Retirement. Working together.
Find answers to the questions that matter to you.
No matching answers.
Try a broader term, such as “stock,” “fees,” or “retirement.”
01
Is Eight Oaks right for me?
Who does Eight Oaks Financial work with?
Eight Oaks Financial works with executives (C-suite, vice presidents, and directors) who have concentrated employer stock or complex equity compensation and a retirement or career transition coming into view. Many are in their late 40s or 50s, are feeling tax pressure from equity awards, and want company stock, taxes, investments, and retirement income coordinated in one plan. We also work with recently retired households turning legacy company stock and other assets into income. We're probably not the right fit if you want a one-time stock tip or a product rather than a planning process.
Is there a minimum to work with Eight Oaks?
Eight Oaks is generally best suited for individuals and families with approximately $1 million or more available to invest who want an ongoing planning and investment relationship. Every situation is reviewed individually, and a separate planning-only arrangement may be available in some cases. If you're unsure whether you qualify, the short See if we're a fit questionnaire is the quickest way to find out.
Does Eight Oaks have an office I can visit?
We don't have a walk-in office, but we are open to meeting in person. We can meet with clients by appointment throughout Southern California and in Middle Tennessee. If you live elsewhere, we're happy to discuss traveling to start a long-term relationship. The vast majority of our meetings are virtual. Fill out our short questionnaire, and we'll figure out together whether meeting in person or virtually makes sense.
Do you work with clients outside Orange County and Middle Tennessee?
Yes. Eight Oaks serves clients across the United States with a virtual-first approach. Andy spent more than two decades living in Silicon Valley, where RSU- and ESPP-heavy compensation is common, and many of our clients are based there. Others have moved from the Bay Area to communities across the country. Our virtual approach allows those relationships to continue wherever life takes them.
02
Company stock & equity compensation
How much of my net worth should be in my company's stock?
There's no single right percentage, but the more of your net worth that sits in one company, the more your retirement depends on that one company. When your paycheck, bonus, unvested awards, and investment portfolio all rely on the same employer, a downturn can hit your income and savings at the same time. We help you see your true exposure, including unvested awards, and decide how much concentration you're willing to keep, why, and for how long.
Should I sell my company stock all at once or over time?
It depends on your taxes, your trading windows, your cash needs, and how much risk you can afford to carry, so there's no universal answer. Selling everything at once removes concentration risk quickly but can concentrate the tax bill in one year, while selling in stages spreads out taxes and timing but leaves you exposed longer. Many executives use a written schedule or a 10b5-1 plan so the decision is made deliberately rather than in reaction to headlines or the share price. We model the options side by side, with your CPA, before you act.
What if I sell my company stock and it keeps going up?
That fear is real, and it's one of the most common reasons executives stay overconcentrated longer than they intended. No one can reliably predict a single stock's next move, so the goal is a plan you can live with whether the price rises or falls, not a perfectly timed sale. Diversifying in steps, and deciding in advance how much you'll keep, can reduce regret on both sides of the trade.
Can you help with RSUs, ISOs, NSOs, and ESPP shares?
Yes. Equity compensation is the core of our work: deciding when to exercise, hold, sell, or gift RSUs, incentive stock options (ISOs), non-qualified stock options (NSOs), and employee stock purchase plan (ESPP) shares. Each type is taxed differently. For example, RSUs are generally taxed as ordinary income when they vest, while exercising ISOs can trigger the alternative minimum tax (AMT). We bring each grant into your broader financial plan and coordinate the tax analysis with your CPA.
Are there ways to diversify concentrated stock without a large tax bill?
There are several approaches to consider, though none eliminates taxes entirely and not all of them fit every situation. Examples include selling in stages across tax years, selling specific high-cost-basis shares first, gifting appreciated shares to charity or a donor-advised fund, and net unrealized appreciation (NUA) treatment for company stock held in a 401(k). Some strategies are limited by company policy or eligibility rules. We evaluate the trade-offs with you and your CPA before anything is implemented.
What is a 10b5-1 plan, and do I need one?
A Rule 10b5-1 plan is a written, pre-arranged trading plan that lets company insiders buy or sell shares on a set schedule, which can help when blackout periods and inside information make it hard to trade. Under current SEC rules, officers and directors face a cooling-off period before trades can begin, along with other conditions. Whether you need one depends on your role, your company's insider-trading policy, and your diversification goals. We help you think through the schedule and its place in your plan, working alongside your company's legal or compliance team.
03
Taxes
Why do I owe more tax on my RSUs than was withheld?
Employers usually withhold federal tax on vesting RSUs at a flat supplemental rate, which is often lower than a senior executive's actual tax bracket. Add state taxes, other income, and large vesting events, and the gap can show up as a surprise bill in April. Planning ahead lets you set aside cash, adjust estimated payments, or time other decisions so the tax doesn't catch you off guard. We coordinate those projections with your CPA.
Do you prepare taxes or give tax advice?
No. Eight Oaks does not prepare tax returns or provide standalone tax or legal advice. We build tax-aware financial plans and investment strategies and coordinate them with your CPA and attorney. We encourage you to review major decisions with your CPA or attorney before acting. If you don't have a CPA who works with equity compensation, we can talk about how to find one.
04
Retirement & California-to-Tennessee moves
How do I know when work can become optional?
Work becomes optional when your assets, benefits, and future income can support the life you want without the paycheck. We connect your spending, unvested and vested equity, deferred compensation, Social Security timing, healthcare costs before Medicare, and taxes into a retirement cash-flow projection so you can see an estimated timeline based on your plan. We then build a tax-aware income plan to replace your salary once you stop working. Projections are estimates and will change as markets and your life change, which is why the plan is updated over time.
What should I decide about deferred compensation and company stock in my 401(k) before I leave?
Make these decisions before your last day, because some deferred-compensation elections and 401(k) options are hard or impossible to change afterward. Nonqualified deferred-compensation payouts are often set by elections you made years ago and can stack on top of other income in your first years of retirement. If your 401(k) holds highly appreciated company stock, net unrealized appreciation (NUA) treatment may be worth analyzing before you roll anything over. We review your plan documents with you and your CPA well ahead of your separation date.
If I move from California to Tennessee, will California still tax my stock compensation?
Possibly, yes. California generally taxes the portion of RSU and stock-option income that relates to the time you worked in California, even if the shares vest or the options are exercised after you've moved (see California FTB Publication 1004). Moving also requires a genuine change of domicile, and California looks at many factors to decide whether you've truly left (FTB Publication 1031). We help you map out timing, vesting schedules, and sale decisions around a move and coordinate the analysis with your CPA.
What else should I plan for when moving from California to Tennessee?
Tennessee doesn't have a broad personal income tax on wages or investment income, but the move affects more than taxes. Common planning items include the timing of a large sale, bonus, or deferred-compensation payout relative to your move date; the sale of a California home; updating estate documents, insurance, and account registrations for your new state; and documenting your change of residency. Eight Oaks has ties to both Orange County and Middle Tennessee, so we can help you sequence these decisions with your CPA and attorney.
05
How we work: fees, fiduciary duty & conflicts
How are Eight Oaks' fees calculated?
Most Eight Oaks clients work with the firm on a fee basis, with a tiered annual advisory fee that declines as managed assets increase. Each rate applies only to the assets within that tier, not to your entire balance; the published schedule starts at 1.25% on the first $500,000 and steps down from there (see our Fees & Minimums page). Financial planning may be included at no additional charge for clients who meet the advisory relationship minimums. Account-level expenses, investment-manager fees, and product expenses are explained before any agreement is signed.
Do you offer planning-only engagements?
Yes, in some cases Eight Oaks offers financial planning as a separate engagement without ongoing investment management. The scope and fee are discussed and agreed on before any work begins. Planning-only can make sense if you want a coordinated plan for an equity-comp or retirement decision but prefer to manage your own investments for now. Please note, though, that these engagements are rare. The majority of our client relationships revolve around Eight Oaks managing client assets for a fee, with planning included in the asset-based fee schedule.
Is Eight Oaks Financial a fiduciary?
Yes, for advisory clients. The majority of our clients work with us through fee-based advisory accounts, where we are held to a fiduciary standard, which means we must put your interests first. If any account is handled as a brokerage account instead, a different standard (Regulation Best Interest) applies, and we'll tell you which applies to each account before you open it.
Will you try to sell me products, and what conflicts of interest should I know about?
Our work starts with a financial plan, not a product, and the planning process comes before any recommendation. Most clients pay a fee based on the assets we manage rather than commissions, which keeps our pay tied to the relationship instead of to transactions. Like any advisor, we do have conflicts of interest. For example, an asset-based fee means we're paid more when more assets are managed, and some brokerage or insurance products pay commissions. These conflicts are disclosed in writing in LPL's Form CRS and advisory brochure, which we'll walk through with you before you engage.
What is Eight Oaks Financial's relationship with LPL Financial?
Andy Chatham is a registered representative and investment adviser representative of LPL Financial, which serves as the broker-dealer and registered investment advisor through which securities and advisory services are offered. LPL, a Member FINRA/SIPC, provides custody, trading, technology, and compliance oversight. Eight Oaks Financial LLC and LPL Financial are separate entities.
Who will I work with, and how often will we meet?
Your relationship is led by Andy Chatham, who has worked in financial services since 1994, with support from Tom Snyder, CFA, Eight Oaks' Director of Investment Strategies, and the rest of our team. During the first year, we generally meet quarterly while we complete your plan and put agreed actions in place. After that, most clients meet semiannually, with extra conversations when important decisions come up. After every meeting we update a shared "mind map" of your financial life so you and the team are always working from the same picture.
06
Getting started
How hard is it to switch from my current advisor?
Switching is usually less work than people expect, because the new firm handles most of the paperwork and many accounts can be transferred "in kind" without selling your investments. Before anything moves, we review what you own, what selling or transferring could cost in taxes or fees, and which positions may be better left in place for now. There's no need to speak to your current advisor before making a change.
What happens after I fill out the "See if we're a fit" questionnaire?
The See if we're a fit questionnaire asks a few short questions about what prompted you to reach out, where you are in your career or retirement, and the general range you have to invest. You won't be asked for account numbers or other sensitive information. Eight Oaks normally responds within one business day, and if it looks like a fit, we'll schedule a complimentary first conversation, generally 20 to 60 minutes by Zoom or phone, usually with Andy. Neither the questionnaire nor the conversation commits you to anything.
How can I check Andy Chatham's background and credentials?
You can review the registrations, employment history, and any disclosures for Andy Chatham (listed as Andrew Chatham) on FINRA BrokerCheck (CRD #2701265). His history includes Northwestern Mutual and MassMutual before he joined LPL Financial in 2016. We encourage every prospective client to check the background of any advisor they're considering.
Have a question about your situation?
A conversation can help you decide whether Eight Oaks is the right fit.
