Jake Kacynski is a Member of the firm’s Business Law and Transactions, Taxation and Business Planning, Private Equity, Venture Capital and Emerging Companies, and Banking and Finance practice groups. He advises clients operating across a diverse array of industries, including manufacturing, construction, hospitality, utilities, retail, health care, telecommunications, alternative energy, emerging technologies, financial institutions, investment funds, and private equity. He counsels publicly traded and closely held corporate and flow-through clients on complex tax issues.

Jake carries out engineering and strategic tax planning objectives to optimize client-specific tax opportunities through structuring dissociated buy and sell side merger and acquisition transactions, acquisitive reorganizations, enterprise restructurings, stock redemptions, liquidations, corporate divisions, and specialty asset purchases while navigating intricate international, federal, state, and local tax frameworks. Jake has significant experience with non-transactional matters, such as providing tax controversy and audit defense representation, filing state bad debt refund claims, preparing and claiming federal tax credits, conducting reverse tax audits, and resolving reporting and filing obligation noncompliance across international, federal, state, and local tax regimes.

PROFESSIONAL BACKGROUND

After earning his Master of Laws in Taxation, Jake began employment as a tax associate at Caterpillar Financial Services Corporation. In 2020, he worked at Deloitte as a tax senior until 2022. From 2022 to 2026, he was a tax attorney at Howard & Howard Attorneys PLLC. Jake joined Aronberg Goldgehn in 2026.

SPEECHES AND PUBLICATIONS

• Co-host, North Shore General Counsel Association Meeting, 2023

• Author, Tax Credits & Incentives Employment Retention Credit, 2023

• Author, The IRS Resumes Employee Retention Credit Claim Processing and Reopens the Employee Retention Credit Voluntary Disclosure Program, 2024

• Author, ERC Claim Processing Restart is a Boon for Cash-Poor Business, Bloomberg Tax, 2024

• Interviewee, Don’t Fall for Bad Tax Advice on Social Media, Chicago Sun-Times, 2025

REPRESENTATIVE MATTERS

• Tax structuring lead on specialty asset acquisition involving private business aircrafts, addressing entity formation and transaction structuring, SALT exposure (sales, use, personal property, and excise), and deductibility considerations under assorted leasing arrangements contemplated in the purchase agreement.
    

• Following trust litigation, as Principal Tax Advisor, structured a non-liquidating distribution via redemption of C-Corp stock held in trust, implementing a tax-optimized alternative to liquidation for a disqualified investment corporation; drafted redemption structure and finalized tax provisions in governing agreements.

• Engaged as Principal Tax Advisor to audit a prior cross-border transaction in connection with the wind-down of domestic operations under court-ordered receivership; identified prior CPA firm’s misclassification of a $131.8M equity sale (CAD/USD spot rate 0.79) as an asset sale between a Canadian entity and U.S. affiliate. Recommended corrective measures to address improper asset basis step-up and ensure accurate tax treatment and amended reporting.

•  Lead Tax Counsel to the same cannabis-sector client under court-ordered receivership during subsequent domestic asset sale; managed tax diligence, drafted asset purchase agreement provisions, and strategically structured transactions to qualify for SALT occasional sale exemption—resulting in $3M in sales tax savings on tangible personal property.

•  Lead U.S. Tax Counsel to U.K.-based investment firm in sale of substantial European real estate asset holdings via U.K. REIT to U.S. private equity firm; conducted U.S. tax compliance due diligence and exposure analysis.

•  Served as Tax Structuring Lead and principal architect of a multistate, tax-deferred internal restructuring involving 14 entities across 8 jurisdictions for a high-growth home healthcare company; designed and executed successive F and D Reorganizations to enhance federal tax reporting efficiency, preserve historical tax attributes, and limit inter-entity liability. Oversaw QSub election and LLC conversion timing, resolved SALT implications, implemented asset segregation via holding entities, drafted plans of reorganization and tax provisions in corporate documents.

•  Served as Personal Tax Advisor to a one-third equity partner in connection with the sale of his business to a private equity investor; reviewed transaction documents and advised on personal and business tax implications of the transaction, including tax-deferred partial equity rollover, sale of remaining equity, gain recognition, basis adjustments, SALT exposure, multi-tiered partnership structure, Net Investment Income Tax, and Section 754 election strategy.

•  Identified and developed a new firmwide service offering centered on the Employee Retention Credit (ERC); assessed taxpayer eligibility, built intake and tax return amendment frameworks, drafted opinion letters, audited third-party claims, and provided IRS audit defense and tax controversy representation—securing multimillion-dollar federal refunds across multiple clients. Nationally published on the subject by Bloomberg Tax.

•  Served as Principal Tax Counsel to startup board on SALT implications of intangible asset classification, advising on characterization as business versus nonbusiness income and corresponding apportionment versus allocation treatment across jurisdictions.

•  Authored SALT opinion letter addressing subsequent $380M disposition of intangible assets as non-apportionable business income in select jurisdictions lacking nexus; informed taxpayer’s filing position prepared in anticipation of potential SALT controversy representation.

• Advised a major software service provider on the applicability of the Chicago Cloud Tax, including treatment of IRC §501(c)(3) tax-exempt customers, and facilitated entry into a voluntary disclosure agreement to mitigate prior noncompliance exposure.

•  Serve as lead U.S. Tax Advisor to offshore flow-through fund trading futures and ETFs on U.S. exchanges; oversee U.S. tax compliance for the fund and its subsidiaries across complex foreign investment structures.

•  U.S. Tax Advisor to Dutch Private Equity Firm on U.S. tax structuring for acquisition vehicle; formed U.S.-based LLC taxed as a partnership to acquire multiple U.S. entities, achieving income tax deferral until distribution, tax-efficient growth, flexible allocation of income, losses, and credits, and optimized loss utilization across partners.

•  Advise foreign and U.S. nonprofit organizations on structuring to enable U.S. donors to claim charitable contribution deductions for funds used in foreign charitable operations; including formation of “Friends Of” entities, guiding regulatory compliance for outbound grants, and addressing the use of Donor Advised Funds to support international giving.

•  Advised franchisors on federal and state tax exposure related to classifying franchisees as independent contractors; recommended best practices and remedial measures to substantiate classification and mitigate potential compliance challenges.

•  Represented clients in appeals of SBA denials of Paycheck Protection Program loan forgiveness, leveraging additional pandemic-related relief programs to optimize financial outcomes; secured full forgiveness of $6M+ in aggregate loan amounts across multiple affiliates by successfully challenging and overturning the SBA’s agency-wide interpretation of “common parent” used to cap borrower eligibility.

•  Lead Tax Counsel to business owner in workforce reclassification matters, transitioning historically misclassified independent contractors to W-2 employees; facilitated entry into the IRS Voluntary Classification Settlement Program (VCSP) to cap audit risk exposure and resolved parallel state agency compliance considerations.

•  Represented CPA firm in regulatory proceedings before the PCAOB related to alleged noncompliance under the Sarbanes–Oxley Act; negotiated and secured settlement agreement to resolve enforcement action.

RELATED NEWS

• Aronberg Goldgehn Welcomes Member Jake Kacynski