FAQs

Yes. Oak Street Advisors is a fee-only, SEC-registered investment advisor and acts as a fiduciary, legally required to act in clients' best interest at all times.

Oak Street Advisors generally works with individuals and families who have $500,000 or more in directly investable assets.

No. Oak Street Advisors focuses on ongoing relationships that combine financial planning, tax planning, and investment management rather than single, standalone planning engagements.

Our financial plans typically run 40 to 75 pages and cover every area of your financial life in one coordinated document: retirement income planning, tax strategy, investment management, Social Security optimization, insurance review, estate planning coordination, and employer benefits. Nothing is treated in isolation. The way you save, invest, withdraw, and transfer wealth all affect each other, and the plan reflects that. Every plan is written specifically for your situation, not generated from a template.

Our fees vary based on the complexity of your situation and the amount of assets you need help managing. For clients who need both financial planning and ongoing investment management, the financial planning work is typically included in our asset management fee rather than billed separately. Our full fee schedule is disclosed in our ADV Part 2, which is available on request or at adviserinfo.sec.gov. The best way to get a clear picture of what working with us would cost is to schedule an intro call.

We work with individuals and families who have $500,000 or more in directly investable assets. Most of our clients are either approaching retirement and want a clear picture of what the next chapter will look like financially, or they are high earners and business owners who feel their tax bill is too high and their savings strategy has never been fully organized. What they tend to have in common is a financial life complex enough that a generic approach won't cut it.

It starts with a no-cost intro call where we get a sense of your situation, and you get a sense of how we work. If it's a good fit, we move into a planning engagement that begins with a thorough review of your finances: income, investments, accounts, tax situation, insurance, estate documents, and goals. From there, we build a comprehensive financial plan and walk through it with you in detail. For ongoing clients, the plan is a living document we revisit and update as your life changes.

 A fee-only advisor is paid directly by you and only you. No commissions, no payments from fund companies, no revenue from any product you buy. A fee-based advisor may charge fees but can also earn commissions from products they recommend, which creates potential conflicts of interest even when the advisor means well. The reason we chose to be fee-only is simple: we want to offer you the best solution without you ever having to wonder whether the recommendation is in your interest or ours.

The CFP designation is the most widely recognized credential in financial planning. Earning it requires completing a rigorous education program, passing a comprehensive board exam, accumulating thousands of hours of real planning experience, and committing to ongoing continuing education. CFP professionals are also held to an ethical standard that requires them to act in the client's best interest when providing financial planning services. It means you are working with someone who has put in the time to understand this work at a serious level, not just someone with a license to sell financial products.

That depends on where you are starting from, but in our experience, the areas where clients see the most meaningful improvement are tax savings, retirement income clarity, and investment structure. Some clients come in overpaying on taxes by tens of thousands of dollars a year because nobody has ever looked at their full picture. Others have never had a clear answer to when they can actually retire and what they can spend. A good financial plan won't promise a specific investment return, but it should give you a specific, defensible strategy and the confidence that your money is working as hard as it can for you.

Our investment management is not a standalone service. It is built into your financial plan from the start. That means every portfolio we manage is constructed around your retirement timeline, your income needs, your tax situation, and your capacity for risk. We develop an Investment Policy Statement specific to your situation, implement and monitor your portfolio on a discretionary basis, rebalance when allocations drift, and coordinate investment decisions with your tax strategy throughout. You also receive straightforward reporting without jargon.

Our fees are based on assets under management and are disclosed in full in our ADV Part 2A, which is available on request or at adviserinfo.sec.gov. The financial planning work is included in the investment management relationship rather than being billed separately. The best way to get a clear picture of what working with us would cost is to schedule an intro call.

We work with individuals, couples, trusts, estates, and business retirement plans with $500,000 or more in directly investable assets. Most of our clients either have a complex financial picture that a generic brokerage account is not built to handle, or they have accumulated significant assets over the years and want someone to manage them with a deliberate strategy behind every decision. We do not offer stand-alone investment management without a financial plan.

We start with a comprehensive financial plan before we manage a single dollar. Once we understand your goals, timeline, tax situation, and income needs, we develop an Investment Policy Statement that defines your target allocation, risk tolerance, and investment guidelines. From there, we implement your portfolio and manage it on an ongoing basis, rebalancing when needed and adjusting as your circumstances change. The plan and the portfolio are reviewed together, not separately.

Most clients hold a combination of our three core strategies depending on their situation. Our Core ETF strategy uses low-cost, tax-efficient exchange-traded funds for broad diversification. Our Dividend Income strategy is built for clients who need reliable cash flow, typically retirees or people approaching retirement. Our Growth strategy targets clients with a longer time horizon who are focused on building wealth rather than drawing income. We also take a flexible approach to asset allocation, which means we do not treat target allocations as permanent fixtures when market or personal circumstances change. And we factor asset location into every portfolio from the start, matching specific investments to the account types where they will be taxed most favorably.

Both, depending on the situation. For most clients, the core equity exposure is built around low-cost ETFs, which is closer to a passive approach. But we do not believe in setting an allocation and walking away from it. We monitor portfolios actively, rebalance deliberately, harvest losses when appropriate, and adjust positioning when conditions or client circumstances warrant it. The goal is not to beat a benchmark every quarter. It is to serve your financial plan over the long term.

We will not promise a specific return, and you should be skeptical of any advisor who does. What we can tell you is that clients who work with us typically see improvement in three areas: their tax drag goes down because we are managing asset location and harvesting losses systematically, their investment costs go down because we use low-cost vehicles and earn nothing from product sales, and their overall strategy gets more coherent because the portfolio is built around a financial plan rather than assembled piece by piece over the years. Those are the results that compound over time.

It depends on your income, whether you have employees, and how aggressively you want to reduce taxable income. A Solo 401(k) is often the most flexible option for sole proprietors. A Safe-Harbor 401(k) works well for small businesses with employees. A Cash Balance Plan can allow far higher contributions for high earners who want to maximize tax deferral. We model all available options against your specific situation.

In most cases, yes. Self-employed individuals can generally deduct 100% of health insurance premiums for themselves and their families, reducing adjusted gross income. How this interacts with an S-Corp structure, a marketplace plan, or a group plan depends on your specific setup.

The Qualified Business Income (QBI) deduction under Section 199A allows eligible self-employed individuals and pass-through business owners to deduct up to 20% of qualified business income from their taxable income. Eligibility and the size of the deduction depend on your income level, the type of business you operate, and how you structure your compensation. It is one of the most valuable deductions available to business owners and one of the more complex to maximize correctly.

A Cash Balance Plan is a type of defined benefit retirement plan that allows significantly higher annual contributions than a 401(k) or SEP IRA alone. It works well for high-earning business owners, typically in their late 40s or 50s, who want to shelter a large amount of income from taxes annually. The trade-off is higher administrative complexity and a commitment to fund the plan each year.

An S-Corp election can reduce self-employment taxes by allowing a portion of business income to be taken as a distribution rather than a salary. Whether it makes sense depends on your net income, your compensation needs, and the administrative costs involved. The benefit tends to be meaningful above a certain income level and negligible below it. We model the specific numbers for your situation before making a recommendation.

No, and having two separate plans that don't reference each other is often the problem. Your business compensation strategy, your retirement plan, your tax exposure, and your personal financial goals are all connected. A plan that treats them as separate tends to leave opportunities on the table. We build one integrated plan that covers both.

Tax preparation is the process of filing an accurate return based on decisions you have already made. Tax planning is the work you do before those decisions, building a strategy to reduce your tax bill in the current year and over your lifetime.

Yes. We are not CPAs, and we do not prepare returns. We work alongside your CPA. We bring a forward-looking perspective on investment and financial planning that complements what your CPA does.

A Roth conversion moves money from a traditional, tax-deferred retirement account into a tax-free Roth account. You pay income tax on the amount converted in the year you do it. Whether it makes sense depends on your current tax bracket, your projected future bracket, and a number of other factors. We model this in detail for every client.

IRMAA (Income-Related Monthly Adjustment Amount) is a Medicare premium surcharge that kicks in once your income crosses certain thresholds. If your income goes above those thresholds, your Medicare Part B and Part D premiums can jump significantly. Smart tax planning, including Roth conversions and careful income sequencing, can help you avoid or reduce IRMAA exposure.

Asset location means putting specific investments in the account types where they will be taxed most favorably. For example, investments that generate ordinary income may be better held in a tax-deferred account, while investments expected to grow significantly over time may be better in a Roth. Over decades, good asset location can meaningfully improve your after-tax returns.

The best time is before you feel like you need it. The strategies that have the biggest impact, Roth conversions, account structuring, and asset location, require time to work. Clients who start planning in their 40s and 50s have far more options than those who come to us at 65 wishing they had started sooner.

Yes. Roth IRA contributions and Roth conversions are separate strategies, and you may be able to use both in the same year. However, contribution limits and income rules apply to direct Roth IRA contributions, while converted amounts are generally taxable in the year of conversion.

Yes. A Roth conversion doesn't have to involve your entire traditional IRA. Converting a portion of the account can allow you to manage the amount of taxable income created by the conversion and revisit the strategy in future years.

A large Roth conversion can increase your modified adjusted gross income, which may affect Medicare Part B and Part D premiums through the Income-Related Monthly Adjustment Amount (IRMAA). Because Medicare generally looks at income from two years earlier, it's important to consider this potential effect before completing a large conversion.

It can. A Roth conversion generally increases your taxable income for the year, which can affect the calculation used to determine whether a portion of your Social Security benefits is taxable. This is one reason to consider a conversion as part of your broader tax plan rather than looking only at the immediate tax bill.

When possible, paying the conversion tax with money outside the retirement account can allow the full converted amount to remain invested in the Roth IRA. Using retirement funds to pay the tax reduces the amount ultimately transferred to the Roth and may have additional tax consequences, particularly if you're under age 59½.

Roth conversion planning can be useful several years before you actually retire. Reviewing your expected income, retirement account balances, Social Security timing, Medicare, and future RMDs can help identify years when a conversion may be more attractive.

Consider your current and expected future tax rates, the amount you want to convert, how you'll pay the resulting taxes, Medicare premiums, Social Security taxation, state income taxes, future RMDs, and your overall retirement and estate-planning goals.

A fee-only financial advisor is paid directly by the client for advice. We receive no commissions or other payments from third parties, which means there's nothing clouding our judgment or creating a conflict of interest between us and you.

Maybe. If your advisor is a registered investment adviser under the Investment Advisers Act of 1940, they're legally bound to act as a fiduciary. If they work for a broker-dealer, they're held to a suitability standard instead, which is a lower bar. Insurance agents generally aren't fiduciaries either.

Fees vary by firm and by the complexity of your situation. Some advisors charge hourly, some charge a flat planning fee, and some include planning as part of an asset management fee. Our fees are fully disclosed in our Form ADV Part 2, and we're happy to walk through them on an intro call.

A comprehensive financial plan looks at every part of your financial life — taxes, income protection, education and retirement expenses, estate planning, and more — and maps out the steps to reach your goals. It's a customized document built around your life, not a template.

We have offices in Myrtle Beach and Mt. Pleasant (Charleston), South Carolina, and work with clients throughout the coastal Carolinas.