Jennifer Tolsky advises businesses, families and individuals in complex estate planning, wealth transfer, business succession planning and taxation matters. Jennifer’s experience includes analyzing income tax and estate tax implications, and reviewing business transactions to determine the income tax implications. Her wealth and succession planning experience strikes the strategic balance between executing her client’s vision and providing tax efficient solutions.
Before joining Gould & Ratner, Jennifer was a tax associate with RSM US LLP, where she prepared complex individual, trust, partnership and gift tax returns.
Jennifer is an active member of the Chicago Bar Association, Illinois Bar Association and the Chicago Estate Planning Council (CEPC). She also frequently writes articles related to changes in tax law.
Jennifer earned her J.D. from UIC John Marshall Law School, and received her bachelor’s degree in economics from the University of Illinois at Urbana-Champaign.
Jennifer is a Certified Public Accountant and is fluent in Korean.
- University of Illinois Chicago School of Law, J.D., 2008
- DePaul University, Accounting Studies (non-degree), 2010
- University of Illinois at Urbana-Champaign, B.A., Economics, 2005
Key Cases or Transactions
- Represented a family estate in planning strategies, including the sales of interests in entities and creation of trusts beneficial for estate tax purposes.
- Represented an oil and gas company in a restructure of certain tax benefits.
- Represented a family estate in the simplification of business holdings and estate planning.
- Represented various high net worth individuals in drafting estate plans, including revocable trusts, wills and powers of attorney for property and healthcare.
- Advised one of the nation’s largest operators for barges in tax structure and tax research related to purchases and acquisitions.
- Advised various entities with respect to the BE-10 disclosure requirements.
- Represented several high net worth individuals in the creation of private foundations and charitable trusts, including ensuring they meet certain requirements under the IRS.
- Assisted a high net worth individual with navigating 1031 exchange requirements.
- Represented a Chicago-based digital healthcare agency in its sale to a global commercialization partner for the life sciences industry.
- Gould & Ratner Selects Practice Chairs, Announces New Vice Chair Role, March 13, 2023
- Five Gould & Ratner Lawyers Named Illinois Super Lawyers and Rising Stars for 2023, January 24, 2023
- Eight Gould & Ratner Lawyers Named Illinois Super Lawyers and Rising Stars for 2022, January 28, 2022
- Gould & Ratner Recently Closed the Sale of closerlook to Fishawack Health, June 9, 2021
- The Natural Segue Between Tax Compliance and Estate Planning: Jennifer Tolsky Promoted to Partner at Gould & Ratner, May 8, 2019
- Jennifer Tolsky Named Partner at Gould & Ratner, April 25, 2019
- SECURE 2.0 Act of 2022 Makes Big Changes to Retirement Plans , January 12, 2023
- IRS Issues Proposed Regulations Affecting Inherited Retirement Accounts Under the SECURE Act , April 26, 2022
- Proposed Federal Tax Changes Take Aim at Wealthy Businesses and Individuals , October 7, 2021
- IRS Notice Provides Relief for Renewable Energy Construction Projects , July 26, 2021
- Pending Changes to Illinois Tax Laws Include SALT Workaround , June 4, 2021
- New Stimulus Allows Faster Depreciation of Certain Residential Rental Property Held by Electing Real Property Trades or Businesses , January 14, 2021
- Why Taxpayers May Want to File a Protective Claim With the IRS for a Refund of ACA-Related Taxes , July 9, 2020
- Low Interest Rates May Provide Planning Opportunity , April 17, 2020
- How the SBA’s Affiliation Rules May Affect Your Loan Eligibility for COVID-19 Economic Relief , April 15, 2020
- IRS Automatically Postpones Additional Payment, Filing Deadlines to July 15 , April 14, 2020
- IRS Issues COVID-19 Tax Credit Details and Instructions , April 1, 2020
- CARES Act Provides Tax Relief to Individuals, Businesses Impacted by COVID-19 , March 30, 2020
- Some Employers Eligible for Reimbursement of Employee Paid Leave Related to COVID-19 , March 24, 2020
- Illinois Allows Easier Way For Remote Retailers to Collect Sales Tax , July 16, 2019
- New Opportunity Zones Guidance from IRS Clarifies Key Provisions of Program , June 5, 2019
- The New Limited Interest Deduction: Good For Business? , February 5, 2018