Our Approach | Eliminate Fragmentation, Build Wealth | Cunningham & Associates

Every business owner or high-net-worth individual knows the feeling: your CPA, your wealth manager, your banker — each doing their job, but no one taking responsibility for your overall strategy.

This is the core problem of fragmented advice:

Your CPA optimizes for compliance; your advisor optimizes for pre-tax returns; your attorney draws static documents.

But they operate in their best interest, they don't see the bigger picture and they are not collaborating with each other to ensure the best outcomes for you.

As a result, opportunities are missed, taxes are filed but not optimized, and your macro financial picture suffers. Investments aren't informed and tax efficient , your compensation isn't structure properly, your business structure isn't optimized and estate plans suffer the consequences. Bottom line, your true wealth is quietly diminished.

Private Tax Advisory isn’t a buzz-phrase. It’s a fully integrated model built for owners and high net worth families who demand - and require - more than compliance.

Private Tax is not intangible strategy. It is a tangible, adaptive, measurable, scalable plan that evolves with you and your business and delivers accountability and measurable return on investment.

Private tax does not limit you to hours, or limit your access to our team of tax and wealth professionals and their breadth of expertise. It empowers you to make informed decisions in the near and long term by providing you with as much, or as little as you need from us - whenever you need it.

Private Tax is tax and wealth advisory the way it should be.

We don’t start with your tax return—we start with your goals, your business, your unique situation.
Our tax forward approach drives decision making across your investments, your business, your compensation, entity choice, exit timing, estate plan.
Instead of isolated reports, we deliver a consolidated Private Tax Strategy that consists of 3 core documents.
We coordinate the execution: you’ll never have a great idea die in hand-offs between advisors.
Our value-driven model aligns our incentive with yours: if we don’t deliver savings and outcomes, we don’t get paid.

Think of Private Tax Strategy as the operating system for your financial life. Here’s what it includes:

Tax Strategy – immediate and multi-year roadmap of credits, elections, depreciation, compensation, timing.
Tax-Efficient Investing – build portfolios to minimize tax drag and maximize after-tax compounding.
Compensation & Distributions – optimize W-2, K-1, dividends, retirement flows in light of business and personal goals.
Entity Structure – align your business structure today and for your exit to ensure you’re not leaving value on the table.
Valuation Drivers & Exit Readiness – prepare your business for sale with tax, structure, and timing in mind.
Estate & Succession – flexible planning built around your legacy, business, and family.

Our process: Assess → Analyze → Implement.

You’ll receive clear deliverables, timelines, checkpoints. And because we coordinate or complement your CPA, attorney, wealth manager—whatever the arrangement—the plan lives and evolves with you.

We will measure, monitor and control our relationship through 3 core documents, The Private Tax Plan, The Enterprise Scorecard, and The Relationship Scorecard.

Most business owners feel like they’re managing their advisors—chasing their CPA for updates, forwarding documents to their attorney, clarifying numbers for their wealth manager, and trying to make sure everyone’s advice aligns. That’s not how it should work.

At Cunningham & Associates, we remove that burden entirely.

We become your central advisor

We take ownership of the process—defining roles, timelines, deliverables, and accountability for every professional involved. Everyone—CPA, attorney, banker, wealth manager—is working from the same playbook: your Private Tax Plan. This living blueprint keeps every decision, meeting, and adjustment anchored to one coordinated strategy.

We build or integrate your team

If you already have trusted advisors, we collaborate and coordinate with them to elevate communication and execution. If you need a stronger bench, we can assemble a team of vetted experts—CPAs, attorneys, valuation specialists, bankers, and investment professionals—whose skills complement your needs. In either case, our role is to unify the expertise around your best interests.

We improve communication and clarity

We facilitate regular reviews and structured updates so that every party stays informed and aligned. No more fragmented advice or contradictory recommendations—just transparent progress reports showing what’s been completed, what’s next, and how it affects your wealth.

We deliver integration and results

The outcome is less friction, fewer surprises, faster implementation, and measurably better results. Every component of your financial life—tax, investing, compensation, entity structure, exit, and estate planning—works together to protect and grow your wealth with precision and purpose.

Don't Wait, Set Up A Time To Talk With Our Team Today.

Every dollar you pay in taxes is a dollar you won't be able to invest in your future. A 15 minute call could change your financial future.

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Don't Wait, Set Up A Time To Talk With Our Team Today.