Taxes are not an annual event. They're a multi-decade conversation.
For business owners and high-income professionals, federal income tax, state tax, self-employment tax, and the net investment income tax can combine to push the marginal rate well above 50%. A disciplined planning process, run year-round and coordinated across investments, entities, and estate structures, can reclaim a meaningful share of that.
Are you planning your taxes, or just filing them?
Take the 16-question Tax Planning Readiness Diagnostic. Score yourself across four areas and find your highest-leverage next move.
50%+
Combined marginal rate many founders and executives face after federal, state, self-employment, and NII tax.
3
Distinct time horizons we plan against: this year, this lifetime, and the generations that follow.
12
Months a year we are reviewing positions, conversion windows, gifting opportunities, and entity choices.
Filing is a formality. The decisions happen earlier.
Most people think about taxes once a year, when they sit down to file. By that point, nearly every opportunity to reduce the bill has already passed. Proactive tax planning flips the sequence: you make strategic decisions throughout the year so that filing becomes a non-event, not a surprise.
At Whitwell & Co. we coordinate directly with your CPA and attorney so investment decisions, business-entity choices, and estate structures all work together toward one goal: keeping more of what you earn.
Four dimensions. One coordinated plan.
Each dimension works a different lever of the tax code. Together, they create a strategy that compounds over decades.
Current-Year Taxes
Reducing the tax bill you owe this April.
Key Strategies
- Maximizing deductions
- Tax-loss harvesting
- Retirement-account contributions
- Qualified Business Income deduction
Tax-Free Income
Building income streams that are never taxed.
Key Strategies
- Roth conversions
- Insurance-based strategies
- Qualified Small Business Stock (Section 1202)
Strategic Deferrals
Deferring income by design, not from a reflex to avoid tax.
Key Strategies
- Growth annuities for tax-deferred, timing-controlled income
- Max-funded defined benefit plans that feed the Roth bucket
- Recognizing income when your rate is lowest, not just later
Estate Tax Reduction
Transferring wealth with minimal estate and gift taxes.
Key Strategies
- Irrevocable trusts
- Grantor-retained annuity trusts (GRATs)
- Charitable-remainder trusts
- Annual gifting strategies
How effective is your current tax plan?
If the answer to most of these is "no" or "I am not sure," there is likely meaningful money on the table.
- Has your advisor discussed Roth conversion windows in the last twelve months?
- Do you know whether your stock could qualify for the Section 1202 exclusion?
- Has a charitable-remainder trust ever been modeled for your situation?
- Is your tax-loss harvesting coordinated with your portfolio rebalances?
- Is your CPA looped into investment and entity decisions before they happen?
- Has anyone modeled whether deferring income now helps or hurts you if future tax rates rise?
The short version.
For Business Owners
For Individuals
A 30-minute conversation. No obligation.
We offer a complimentary tax-position review that benchmarks your current situation against the strategies available to someone in your bracket. The review takes about thirty minutes and can reveal opportunities worth tens of thousands of dollars per year.
If we can help, we will explain exactly how. If your current plan is already well-optimized, we will tell you that too.
Schedule your complimentary tax-position review.
Find out how much you could save with proactive, multi-dimensional tax planning. We do not believe in pressure or hard pitches. We believe in the right relationship with the right people at the right time.
Schedule the ReviewEducational content based on Whitwell & Co.'s tax-planning framework, authored by Stefan Whitwell, CFA®, CIPM. Not individualized tax, legal, or investment advice. Coordinate with your CPA and attorney on specific decisions.