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Groshek_Jeff

Jeff Groshek

PartnerBoston

With over 25 years of experience at both law and accounting firms, Jeff’s practice focuses on all areas of federal and state taxation, with an emphasis on domestic and international tax structuring, contractual matters, planning, corporate transactions – mergers and acquisitions, real estate, and partnership formations. He has a broad background in federal income tax law and provides tax advice in Internal Revenue Service and state tax controversy matters, drawing on his experience as an IRS District Counsel.

Jeff represents clients on both the buy-side and sell-side in several hundred taxable and tax-free transactions ranging from $5 million to $6 billion. Within the real estate industry, his experience includes joint ventures, fund formation, like kind exchanges (e.g., forward, reverse, build to suit, drop and swaps, swap and drops, ground leases, and tenancy in common) and similar tax planning vehicles, supporting multiple property types including hospitality, retail, homebuilders, military, and multi-housing.

Work Experience

  • Hinckley Allen
    • Partner (2019-Present)
    • Associate (2003-2005)
  • Gesmer Updegrove
    • Partner (2011-2015, 2016-2019)
  • EY
    • Tax Transaction Adviser (2015-2016)
  • Greenberg Traurig
    • Associate (2005-2011)

Honors & Awards

  • Boston Magazine, Top Lawyers (2023-2025)
    • Tax Law
  • Massachusetts Lawyers Weekly, Go-To Lawyer, Taxation (2022)

Certifications

  • Former Certified Public Accountant (CPA)
    • Massachusetts
    • Wisconsin

Professional Affiliations

  • American Bar Association
  • Boston Bar Association
  • Massachusetts Society of Certified Public Accountants
  • Wisconsin Institute of Certified Public Accountants

Bar Memberships

  • Massachusetts
  • Wisconsin
  • United States District Court for the Eastern District of Wisconsin
  • United States Tax Court, Massachusetts
Publication

Key Tax Implications of the One Big Beautiful Bill Act

On July 4, 2025, the federal government enacted H. R. 1, “An Act to provide for reconciliation” which is popularly known as the One Big Beautiful Bill Act (“OBBBA”). OBBBA’s 870 pages included significant tax changes, making some provisions of the…

Publication

Qualified Small Business Stock: Pre-Acquisition Planning for Tax Savings Upon Exit

Issuing qualified small business stock (“QSBS”) is a valuable tool that can provide significant tax savings to searchers and independent sponsors alike upon the eventual sale of one or more of their portfolio companies. Taxpayers who hold QSBS for more…

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Firm News

Boston Magazine Recognizes 26 Hinckley Allen Attorneys in 2025 Top Lawyers List

Hinckley Allen is proud to announce that 26 of its attorneys have been named to Boston Magazine’s 2025 Top Lawyers list, representing a broad range of its practice groups. This year, six Hinckley Allen attorneys are newly recognized among the pu…

Firm News

Twenty Hinckley Allen Attorneys Honored Among Boston Magazine’s Top Lawyers

At Hinckley Allen, our attorneys are consistently recognized by their peers and respected industry groups for their exceptional skill, dedication to their clients, and leadership within the legal profession. We are proud to announce that several of our att…

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Case Study

Hinckley Allen Guides Complex ESOP for Family-Owned Construction Firm

Hinckley Allen represented Rifenburg Holdings, Inc. (“Rifenburg”) in the sale of 100% ownership interests to the organization’s newly formed Employee Stock Ownership Plan (ESOP). Rifenburg, one of Upstate New York’s oldest and largest family-owned …

Case Study

Hinckley Allen Facilitates Brinker Capital Merger in Significant Moment for Financial Services Industry

Hinckley Allen represented its long-time client, Brinker Capital, a registered investment adviser, and its affiliated broker-dealer, in their sale to new investment partnership controlled by funds affiliated with Genstar Capital Partners, a California-base…

Past Event

Guide to Opportunity Zones in Massachusetts

June 19, 2019

Jeff Groshek and Leah C. Rubega will discuss "Opportunity Zones: How they work and what will be the winning process in Massachusetts? " at the Realtors Commercial Alliance of MA June Meeting. Commercial real estate professionals will be provided with an upd…

Past Event

The Land of Oz (Opportunity Zones)

March 22, 2019

John H. Sokul, Jr. and Jeff Groshek join the Arnett Development Group's (ADG) and New Hampshire Commercial Investment Board of Realtors (NHCIBOR) panel on "The Land of Oz (Opportunity Zones) to help attendees to understand the Qualified Opportunity Zone pr…