Tax Structuring Services in Chicago, IL

Choosing the right entity is the foundation of tax-efficient operations. We analyze your business model, revenue expectations, ownership structure, and growth plans to recommend the optimal entity type.

Our analysis covers:
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• Sole proprietorships and their limitations for growing businesses.
• Partnerships and multi-member LLCs with customized operating agreements.
• S corporations for self-employment tax savings and pass-through benefits.
• C corporations for retained earnings and potential qualified small business stock exclusions.
• Professional corporations and limited liability partnerships for licensed professionals.
• Hybrid structures combining multiple entity types for optimal results.

Allow us to handle formation paperwork, initial capitalization requirements, federal and state registration, and establishment of corporate governance that supports your long-term strategy.

Your business has evolved, and your structure should, too. We evaluate whether your current entity still serves your interests or whether conversion could deliver meaningful tax savings.

Common conversions include:
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• LLC to S corporation election for payroll tax savings.
• C corporation to S corporation for pass-through treatment.
• Sole proprietorship to LLC or corporation for liability protection and tax flexibility.
• Single-member LLC to multi-member structure for family income shifting.

We analyze the tax implications of conversion, including built-in gains, asset basis adjustments, and state-level considerations. Our team manages the technical requirements and timing to minimize disruption and maximize benefit.

Sophisticated operations often require multiple legal entities working together. In this case, we design holding company structures that consolidate ownership, protect assets, and create tax planning opportunities.

Benefits include:
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• Centralized cash management and intercompany financing.
• Segregation of high-risk operations from valuable assets.
• Streamlined ownership transfers and estate planning.
• Strategic allocation of income across entities for optimal tax brackets.
• Flexibility for selling individual business units while retaining others.

Our team coordinates with your legal advisors to ensure structures deliver tax advantages while still meeting operational needs.

How you take money from your business dramatically impacts your tax bill. This is why we develop compensation strategies that balance salary, distributions, benefits, and other payments to minimize overall tax liability.

Our planning addresses:
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• Reasonable compensation requirements for S corporation shareholders.
• Self-employment tax minimization through proper income classification.
• Qualified business income deduction maximization under Section 199A.
• Integration of retirement plan contributions with compensation planning.
• Timing of distributions to optimize personal tax positions.

We coordinate compensation planning with payroll services and employee benefit plan design to create comprehensive solutions.

With the $10,000 cap on state and local tax (SALT) deductions for individuals, many states have enacted workarounds allowing pass-through entities to pay state income tax at the entity level, creating federal deductions for owners.

We analyze whether PTET elections benefit your situation, calculate potential savings, file required elections and returns, and coordinate state payments with estimated tax requirements. For Illinois businesses and those operating in multiple states, these elections can deliver substantial federal tax savings.

Owning a business creates opportunities for tax-efficient wealth transfer to family members. We design structures that shift income to lower-bracket family members while maintaining control and facilitating long-term estate planning.

Strategies include:
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• Family limited partnerships for real estate and business holdings.
• Gift and sale arrangements for ownership interests.
• Trust ownership structures for asset protection and estate reduction.
• Employment of family members in appropriate roles.
• Leveraging annual exclusion gifts and lifetime exemptions.

These arrangements integrate with our estate & trust tax preparation and tax and estate planning for closely held businesses services.

If you’re buying or selling a business, the deal structure determines who pays what taxes and when. We advise on the tax implications of asset purchases versus stock sales, allocation of purchase price among asset classes, earnout arrangements and deferred payments, and Section 338 elections for deemed asset sales.

Our transaction structuring also coordinates with mergers and acquisitions (M&A) advisory to ensure your interests are protected throughout the deal process.

If your business operates across state lines, this creates additional structuring considerations. The Lewis.cpa team helps you minimize state tax exposure through strategic nexus management, apportionment planning, and entity domicile selection.

Our multi-state planning includes:
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• Analysis of nexus-creating activities in each jurisdiction.
• Recommendations for entity structure to minimize state tax filing requirements.
• Integration with state and local tax (SALT) compliance services.
• Planning around varying state treatment of passthrough entities.

Your business structure impacts how efficiently you can transition to retirement or exit through sale. We design structures that facilitate smooth transitions while minimizing tax impact.

Exit planning structures address:
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• Qualified small business stock eligibility for C corporation shareholders.
• Section 1202 exclusions for long-term capital gains.
• Installment sale arrangements for seller financing.
• Employee stock ownership plans (ESOPs) as tax-advantaged exit strategies.
• Succession planning for family business transfers.

If you want to create complete transition roadmaps, integrate these strategies with business succession planning.

For profitable businesses, S corporation status can save thousands in self-employment taxes annually by allowing owners to take reasonable salaries plus distributions. We calculate optimal salary levels, document reasonable compensation determinations, file Form 2553 for S election, and manage payroll and distribution timing.

The Section 199A deduction allows many pass-through business owners to deduct up to 20% of qualified business income. We structure operations to maximize this deduction by optimizing W-2 wages paid to owners, managing income thresholds for specified service businesses, coordinating multiple business activities, and timing income and deductions for maximum benefit.

Separating high-risk operations from valuable assets protects your business interests. We design structures that place operating activities in one entity while holding real estate, intellectual property, or equipment in separate entities. This segregation offers liability protection, enables different tax treatment for passive and active income, and facilitates future sales of individual components.

When appropriate, we structure businesses to shift income to family members in lower tax brackets through legitimate employment arrangements, ownership gifts or sales, trust beneficiary distributions, and family partnership or LLC allocations.

These arrangements need careful documentation and substantiation, which we provide to support your position.

C corporations can retain and reinvest earnings at the 21% corporate rate, which may be lower than individual rates for high-income owners. We analyze whether C corporation status benefits your situation, calculate the breakeven point for corporate versus passthrough taxation, plan dividend timing for qualified dividend treatment, and coordinate with R&D tax credit services and other corporate incentives.

For businesses with cross-border operations, we design structures that defer U.S. tax on foreign income, leverage favorable tax treaties, comply with transfer pricing requirements, and coordinate with U.S. expat tax preparation for international owners.

This planning integrates with foreign bank account reporting compliance, giving you peace of mind that you meet all international requirements.