Integrated Tax Strategy for High-Net-Worth Individuals | Intentional LLC | Fort Mill, SC

Tax Strategy

Your tax bill is a
byproduct of your
decisions.

Most people find out what they owe in April. We think about the tax implications of every investment decision throughout the year so the number in April is one you planned for, not one that surprises you.

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Tax planning and investment management belong in the same conversation.

The problem

Your portfolio and your
tax return are the
same conversation.

Many advisors manage your investments in one conversation and send you to your CPA for another. The two rarely talk to each other. The result is a portfolio that performs well on paper but leaves significant after-tax return on the table.


I've seen this play out consistently over 17 years. Clients with competent CPAs and competent advisors who never speak. Tax decisions made in isolation from investment decisions. Investment decisions made with no awareness of their tax consequences. It's one of the most common and most avoidable sources of wealth erosion I know of.

"The return on your portfolio is what you keep, not what you earn. Tax strategy is not a year-end conversation. It belongs in every decision we make."
James Roberts, Founder, Intentional LLC

Two ways we add value

Ongoing tax strategy.
Event-driven tax planning.
Both, always.

Ongoing

Built into every investment decision

Tax-loss harvesting, asset location across account types, qualified dividend management, Roth conversion strategies, and timing of capital gains realizations. These aren't tasks we do once a year. They happen throughout the year as markets move and your situation evolves.

The goal is a financial plan that is always tax-aware, not just tax-aware when your CPA asks for documents in March.

Event-driven

Planning around the moments that matter most

Business sales, equity compensation events, large capital gains, retirement account transitions, inheritances. These are the moments where the tax decisions are biggest and the window to plan is often shorter than people realize.

We get involved before these events, not after. The earlier the conversation starts, the more we can do. Learn more about pre-transaction planning.

What we work on

The tax strategies
we use most often.

Every client situation is different. These are the tools we reach for most frequently across our client relationships.

01
Tax-loss harvesting

Systematically realizing losses to offset gains elsewhere in the portfolio. Done consistently, this is one of the most reliable sources of after-tax return available to investors. Done carelessly, it creates wash-sale violations that eliminate the benefit entirely.

02
Asset location optimization

Placing investments in the account type where they are most tax-efficient. Tax-inefficient assets like bonds and income-producing holdings belong in tax-deferred accounts. Tax-efficient assets like index funds belong in taxable accounts. Aggressive growth assets belong in Roth accounts, where that growth compounds and comes out entirely tax-free. Three distinct buckets, each with a different tax purpose. Getting all three right is one of the most consistent sources of after-tax return we build into every client portfolio.

03
Roth conversion planning

Identifying the right years and the right amounts to convert traditional IRA assets to Roth. The goal is to fill lower tax brackets strategically over time, reducing the long-term tax burden on retirement assets before RMDs force the issue.

04
Equity compensation planning

ISOs, NSOs, RSUs, and ESPP shares all carry different tax treatments and require different timing strategies. We work with clients to plan the exercise and sale of equity compensation in a way that avoids unnecessary concentration and minimizes tax exposure.

05
Charitable giving strategies

Donor Advised Funds, Charitable Remainder Trusts, and qualified charitable distributions from IRAs can significantly reduce taxable income in high-income years. We incorporate these into the broader tax plan because charitable intent and tax efficiency aren't mutually exclusive. Particularly relevant for business owners approaching a liquidity event.

06
Qualified opportunity zones

For clients with large capital gains events, qualified opportunity zone investments can provide significant deferral and potential exclusion benefits when structured correctly and held for the appropriate period. The window to act is tied to the gain event, not something to evaluate later.

How we work

We work with your CPA.
Not around them.

We don't prepare tax returns. That's your CPA's job, and a good one deserves to stay in that lane. What we do is make sure the investment and planning decisions made throughout the year are ones your CPA can work with effectively.


In our experience, the most expensive gaps in tax planning aren't mistakes made by the advisor or the CPA individually. They're the decisions that fall between the two conversations that never happened. We close that gap.

What coordination looks like

  • Proactive communication with your CPA about investment decisions before they affect your tax situation
  • Year-end planning conversations to identify harvesting and conversion opportunities before December 31
  • Estimated tax projections throughout the year so April isn't a surprise
  • Review of prior year returns to identify missed opportunities going forward
  • Coordination on major financial events before they happen, not after
  • Reporting and documentation designed to make your CPA's work easier, not more complicated

"A referral from a CPA or estate attorney is one of the relationships I take most seriously."

If you are a CPA, estate planning attorney, or M&A advisor with clients approaching a significant financial event, I am happy to be a resource. My role is to complement your work, coordinate around it, and make sure nothing important falls through when the planning crosses disciplines. I work with a small number of referral relationships intentionally. The goal is depth, not volume.

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Who this is for

If taxes are one of your
largest expenses, they deserve
serious attention.

For high-income and high-net-worth individuals, taxes are often the single largest drag on long-term wealth accumulation. A proactive tax strategy built into your financial plan, not bolted on after the fact, makes a real difference over time.

If your current advisor isn't talking to you about taxes throughout the year, that's a gap worth closing.

  • High-income earners looking for more proactive tax management throughout the year
  • Business owners with complex tax situations across personal and business entities
  • Executives with significant equity compensation requiring careful exercise and sale planning
  • Individuals approaching or in retirement navigating Roth conversions and required minimum distributions
  • Anyone who experienced a large taxable event and wants to plan more carefully going forward
  • Clients whose investment advisor and CPA don't communicate with each other

Common Questions

What people ask about
tax strategy and wealth.

The questions below cover the tax planning topics that come up most frequently with high-net-worth individuals, business owners, and executives.

  • Integrated tax strategy means that tax implications are built into every investment and financial planning decision made throughout the year, rather than addressed reactively at tax time. For high-net-worth individuals, this includes asset location optimization, tax-loss harvesting, Roth conversion planning, charitable giving strategies, and ongoing coordination with a CPA to ensure investment decisions and tax returns are aligned. The goal is a financial plan where the investment strategy and the tax strategy are the same conversation.
  • Tax preparation is the process of documenting what happened in a prior year and filing a return. Tax strategy is the process of making decisions throughout the year that affect what that return will look like before it's filed. A CPA handles tax preparation. A wealth advisor with an integrated tax approach handles the investment and planning decisions that create the tax picture the CPA then works with. The two are most valuable when they're working from the same page throughout the year, not just at filing time.
  • Tax-loss harvesting is the practice of realizing investment losses intentionally to offset capital gains elsewhere in a portfolio. When done consistently throughout the year, it is one of the most reliable sources of tax efficiency available to investors. The key is doing it in a way that maintains the intended investment exposure and avoids wash-sale violations that would eliminate the benefit entirely.
  • Asset location optimization is the practice of placing investments in the account type where they are most tax-efficient. Tax-inefficient assets such as taxable bonds, REITs, and actively managed funds generate ordinary income and belong in tax-deferred accounts like IRAs and 401(k)s. Tax-efficient assets like index funds and municipal bonds belong in taxable accounts. Most portfolios ignore this entirely, leaving meaningful after-tax return on the table every year.
  • A Roth conversion strategy involves moving assets from a traditional IRA or 401(k) into a Roth IRA, paying income tax on the converted amount now in exchange for tax-free growth and withdrawals later. The goal is to identify years when your marginal tax rate is lower than expected in the future, and convert enough to fill lower tax brackets strategically over time. This is particularly valuable for high-net-worth individuals in years with lower income, before Social Security begins, or before required minimum distributions start forcing taxable withdrawals.
  • A Donor Advised Fund (DAF) is a charitable giving account that allows you to make an irrevocable contribution of cash or appreciated securities, receive an immediate tax deduction, and then distribute grants to qualified charities over time. DAFs are particularly effective in high-income years because they allow you to front-load the tax deduction in the year you need it most while retaining flexibility about which charities ultimately benefit. Contributing appreciated securities directly to a DAF also eliminates the capital gains tax that would otherwise apply to a sale.
  • A Charitable Remainder Trust (CRT) is an irrevocable trust that allows you to contribute appreciated assets, receive an income stream for a defined period or for life, take a partial charitable deduction in the year of contribution, and ultimately transfer the remaining assets to a qualified charity. CRTs are commonly used by business owners approaching a liquidity event because they allow the trust, rather than the owner, to sell appreciated assets without triggering immediate capital gains tax, while providing income and charitable benefit. The structure must be in place before the transaction closes to be effective. Learn more about pre-transaction planning.

Start planning

Tax strategy works best
when it starts early.

The decisions that affect your tax bill are made throughout the year. The more of them we're involved in before they happen, the better the outcome. Schedule a conversation with James.

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