
Private Client Tax Strategy
Stop reacting to taxes.
Start planning for them.
Written, multi-year tax strategy for executives with equity compensation, business owners, and anyone facing a liquidity event.
Strategy is led by Matthew McClintock, J.D., LL.M., a former IRS Criminal Investigation Special Agent. We plan before the vest, the sale, or the year end, work alongside your CPA, and support the positions we report on qualifying returns.
Tax results depend on your facts, eligibility, implementation, documentation, and applicable law. No particular tax result is guaranteed.
How it works
Four stages, in this order.
OSA designs the tax strategy, coordinates implementation, offers preparation and optimization, and provides defined support for the positions it puts on qualifying returns. Clients can retain their existing CPA, purchase broader audit support when appropriate, and engage separately for matters outside the agreed scope.
Most high earners have a CPA who reports last year and nobody who plans next year. The sequence below is what we own.
- 01
Diagnose
Review income, existing returns, ownership, transactions, and planning goals.
- 02
Design
Model the tax consequences and build a strategy with defined actions and assumptions.
- 03
Coordinate
Establish implementation priorities, responsibilities, and documentation with your professional team.
- 04
Prepare and support
Add preparation and optimization, then receive the defined post-filing support included for qualifying returns.
- Diagnostic first
- Before anything is recommended
- Written scope
- Services agreed before work begins
- Your CPA stays
- Unless you decide otherwise
- Nationwide
- Remote-first practice
Where the work happens
Save. Protect. Grow.
Three planning questions, addressed in sequence. Each starts with your circumstances rather than a predetermined product.

Reduce Current Tax Exposure
Identify and model opportunities to reduce tax exposure through eligible deductions, credits, depreciation, timing, and business tax planning. The strategy starts with your circumstances, not a predetermined product.
Explore Tax Strategies
Asset Protection & Tax Planning
OSA connects asset protection objectives with proactive tax planning. We evaluate the tax implications of ownership arrangements, entity structures, business succession, and wealth-transfer decisions, then coordinate a planning roadmap with your existing professional team.
Build My Asset Protection & Tax Plan
Business Growth & Exit Tax Planning
Understand the tax consequences of expansion, acquisitions, equity compensation, liquidity events, and a future business sale. Plan the tax decisions before the transaction is complete.
Plan My Next Business MoveNo asset protection or tax outcome is guaranteed. Legal services are separate, require a separate engagement, and are not included in OSA services.
Deliverables
A tax strategy you can put to work.
Your engagement translates planning into defined deliverables, assigned actions, and coordinated follow-through.
- Tax Strategy Blueprint
- A written roadmap identifying the strategies to evaluate, implementation steps, assumptions, timing, and coordination points.
- Client-specific modeling
- Federal and state tax analysis of the proposed plan, including relevant limits and alternative scenarios.
- Strategy interaction review
- Consider how deductions, credits, depreciation, losses, participation, ownership, and timing interact before implementation.
- Asset protection and tax planning
- Tax analysis and coordination around ownership, entities, succession, and wealth-transfer objectives.
- Implementation calendar
- A practical schedule of actions, required documentation, professional responsibilities, and deadlines.
- Periodic and year-end reviews
- Scheduled updates to reflect income changes, completed steps, and approaching planning deadlines.
- Return-preparer package
- An organized strategy summary, calculations, and implementation records for the professional preparing the covered returns.
Service structure
Five services. Here is how each is sold.
Strategy is the core. Preparation and broader audit support are optional. Your written proposal sets out services, fees, and coverage before anything begins.
Private Tax Advisory
Strategy, modeling, asset protection and tax-planning coordination, implementation roadmap, agreed reviews, and CPA coordination.
Read moreOptional preparation scopePreparation & Optimization
Only the taxpayers, returns, jurisdictions, and tax years identified in the preparation engagement.
Read moreIncluded for qualifying OSA-prepared returnsPosition Defense
Defined support for Covered Positions during the agreed protection period and within stated limits.
Read moreOptional broader service planAudit Protection
Covered notice and examination work beyond the included Position Defense scope.
Read moreSeparate engagementTax Controversy
Existing disputes, Appeals, collection matters, and other accepted issues outside the protection plan.
Read moreYour written engagement identifies included services, fees, limits, and exclusions. Preparation and broader audit services are included only when expressly selected or specified. Purchasing tax advisory services does not require a separate investment purchase or enrollment in a future investment-management service.
Your existing team
Keep Your CPA. Add a Tax Strategy Team.
You do not have to change tax preparers to work with OSA. We can develop the strategy, coordinate implementation, and provide the analysis and records your existing CPA needs to evaluate the reporting.
OSA Strategy + Your Existing CPA
OSA handles the agreed strategy and coordination work. Your preparer evaluates, prepares, and files the returns within that professional's engagement.
OSA Strategy + OSA Preparation
One coordinated process from planning through preparation, filing, and the defined Position Defense benefit for qualifying returns.
Strategy documentation and CPA coordination are part of the agreed advisory scope. Position Defense for OSA-prepared returns does not automatically extend to a return prepared by another professional. Any additional review, notice response, or representation is separately identified in writing.
Who we serve
For Clients Whose Tax Planning Needs More Than a Filing Appointment.
OSA works with business owners and founders; executives with significant compensation or equity events; real estate owners; and families planning major transactions, charitable contributions, business succession, or other complex tax decisions.
The relationship begins with a review of your circumstances, planning objectives, service needs, and fit for the engagement.
Discuss My Tax SituationInsights
What we are reading, and what it means.
Field notes on structure, sequence, and timing.
Alternative Minimum Tax and the Cost of a Good Year
The Vesting Calendar You Did Not Set
On the Order of Operations

Leadership
Tax strategy built around the whole picture.
OSA brings strategy design, tax modeling, implementation coordination, and preparation support into a connected advisory relationship, with responsibilities assigned to the professionals engaged for each service.
Matthew C. McClintock, J.D., LL.M.
Principal, Tax Strategy & Structure
LL.M. in Taxation, University of Alabama · J.D., Loyola University New Orleans · Admitted, United States Tax Court
Dr. Bryan Dutson
Principal, Client Strategy
Hundreds of tax-advantaged investments analyzed · Personal plan design for high-income earners, equity holders, and business owners
- Taxpayers assisted
- 52K+
- IRS audits resolved successfully
- 95.28%
Figures reported by McClintock Tax Law LLC, Matthew McClintock's separate and independent practice, across its prior matters. They are not results of Odyssey Strategic Advisors and do not predict the outcome of any future matter.
Begin
Speak with a principal.
A confidential conversation about your income, entities, and timing. No pitch, no junior staff, and no obligation.
Engagements typically begin at $2M+ of annual income, or a comparable taxable event.
Investment Services
Coming SoonTax-aware investment management. Coming soon.
OSA is developing a future investment-management offering intended to coordinate portfolio decisions with tax planning. This is separate from the tax-advisory services available today. Investment-management services are not currently available through this website.
Coming Soon. Future investment-advisory and investment-management services would be provided through an appropriately registered investment adviser under separate agreements and fees. Availability and timing are subject to provider arrangements, applicable registration requirements, and operational readiness. These services are not included in the current OSA tax-advisory subscription.
Notify Me When Available