Integrated financial services for high-net-worth individuals and families in Chicago, IL

Three things often keep wealthy families awake at night: taxes eroding wealth from multiple income sources, rising lifestyle costs exceeding projections, and the complexity of transferring assets without losing half to estate taxes.

You need more than separate advisors working in silos. You need coordination. We ensure your financial plan includes strategic alignment across your advisors; CPAs, financial advisors, and estate attorneys. We work in service of your family’s long-term financial vision.

Personal service, national reach – We’re based in Chicago, but we support clients across the U.S.

Privacy and discretion are standard in every conversation. We understand the sensitivity of wealth-related decisions. As fiduciaries, we’re legally required to act in your best interest at all times.

Tailored tax strategy for high-net-worth individuals

Our CPAs for high-net-worth (HNWI) individuals and families specialize in year-round financial planning, not just tax prep.

The high-earner tax challenge: Once your income passes $200,000, your tax picture changes dramatically.

You’re hit with new taxes, phased-out deductions, and complex planning opportunities most preparers overlook. For high earners and wealthy families, that complexity compounds across compensation, investments, and estate strategy.

For families with substantial wealth, the stakes get even higher. Estate planning, trust structures, multi-jurisdictional compliance, and wealth transfer strategies all need to work together. A single misstep in planning can cost your family hundreds of thousands of dollars in avoidable taxes.

Learn more about our financial planning and tax services.

We have been using Pasquesi Partners for many years. Our income tax returns are really complicated due to some investments we have. We do not have the expertise to complete our returns. In addition, we get tax planning advice throughout the year to help minimize the impacts on our return. In addition, they are up-to-date on all tax changes that occur at the State and Federal levels. They provide detailed explanations on how these changes impact our returns. I wouldn’t be able to do this myself and very grateful to have an trustworthy accountant help us out every year.

– Aaron W.

HNWI accounting and tax solutions

Get clear guidance on when to act and what each decision means for your tax bill. We provide year-round insight and coordination among advisors.

Executive compensation planning

Stock options, RSUs, and performance bonuses create complex tax situations most preparers miss.

We work with you throughout the year to time stock option exercises, plan RSU sales around your other income, and structure deferred compensation to minimize lifetime tax liability.

Investment tax optimization

Investment income suffers when capital gains timing goes unmanaged. Realized gains stack on top of your salary, pushing you into higher brackets.

Strategic tax-loss harvesting, capital gains planning, and coordination with your retirement distributions keep more money in your accounts.

Retirement planning

High earners face income limits on Roth contributions and complex decisions about traditional versus Roth accounts.

We maximize your contribution windows across all available retirement plans and implement backdoor Roth IRA strategies when direct contributions aren’t allowed.

Estate planning & wealth transfer

Estate and gift taxes can take up to 40% of assets transferred to the next generation.

We work alongside your estate attorney to structure trusts, implement strategic gifting programs, and plan wealth transfers that minimize tax impact.

Philanthropic & charitable giving

Charitable giving lets you support causes you care about while reducing your tax burden, but timing and structure matter.

Strategic charitable planning reduces your tax burden while increasing your philanthropic impact.

Business succession planning

Selling too early leaves money on the table. Waiting too long creates estate tax problems and family conflicts.

We coordinate succession planning with your overall wealth strategy, evaluating entity structure changes, management transitions, and sale timing to optimize tax outcomes.

Book a confidential consultation to see how Chicago-based CPA firm can simplify your financial life.

Rob Pasquesi, Chicago CPA for HNWI, in a dark suit with a welcoming smile

Have questions about how we can support you? Book your complimentary 20-minute consultation call with Rob.

Our process brings peace of mind to complex finances. You always have a clear next step and a single point of contact.

Learn more about working with us.

How we work with HNWI clients

Proactive, responsive, clear. Since 2014, we’ve provided our high-net-worth clients with integrated financial guidance, tax strategy, and accounting expertise.

Discovery & priorities

An in-depth, private consultation. You share where you are, where you want to go, and what keeps you up at night.

Strategic planning

We develop a tailored tax and financial roadmap. You get clear recommendations with the reasoning behind each one.

Coordination & oversight

Your financial advisor knows your tax strategy. Your estate attorney understands your income timeline. Everything works together.

Ongoing advisory

We adjust your strategy as your income, investments, or goals evolve.

High-net-worth tax & accounting FAQs

How do you protect our privacy?

Privacy and discretion are foundational to our work. We operate with strict internal protocols, encrypted systems, and minimal data-sharing practices to ensure your information stays secure. More importantly, we understand the sensitivity of wealth-related decisions and treat every client interaction with the confidentiality it deserves. We’re happy to answer your questions – reach out to book a complimentary consultation to discuss any concerns.

Can you help with estate and gift tax issues?

Yes. We work closely with estate attorneys to coordinate gift strategies, trust structures, and multi-generational wealth plans. Our role is to ensure the tax side of your legacy is handled with precision, so your assets pass to the next generation efficiently, and in alignment with your long-term goals.

Is it better to use a CPA or a private accountant?

For complex financial lives, a Certified Public Accountant (CPA) offers a higher standard of expertise, ethics, and oversight. CPAs are licensed professionals held to rigorous continuing education and fiduciary standards—especially important when dealing with multi-layered tax situations, stock compensation, or estate planning. A private accountant may handle basic bookkeeping, but a CPA is trained to guide high-stakes decisions and long-term strategy. Reach out to book a complimentary call to discuss your specific needs.

How does a legacy plan work?

A legacy plan is more than just estate documents, it’s a coordinated strategy to transfer your wealth, values, and intentions to future generations. We work alongside your estate attorney to structure gifts, trusts, and entity plans that reduce tax exposure and align with your family’s goals. Our role is to ensure the financial and tax pieces support a smooth, intentional handoff of your assets.

What is the best way to leave your estate to your children?

There’s no one-size-fits-all answer but the key is thoughtful coordination. We help you explore tax-efficient ways to transfer wealth, such as strategic gifting, trust structures, and entity planning. Working with your estate attorney, we ensure your plan aligns with both your long-term intentions and current tax laws so your children receive more of your legacy, with fewer complications and surprises.

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