Joshua E. Gewolb

Joshua E. Gewolb

Partner

jgewolb@hselaw.com

tel: 585.231.1151

fax: 585.232.2152

Josh Gewolb brings a personal and practical approach to his representation of for-profit and nonprofit clients. He began his career as a traditional federal tax lawyer at Debevoise & Plimpton, LLP, but in over a decade at Harter Secrest & Emery, his broad technical knowledge and experience and his pragmatic focus have resulted in the expansion of his practice areas. In his diverse practice, he provides a wide range of legal advice to a spectrum of clients, from individuals to small local enterprises to large publicly-traded corporations and nonprofit entities.

Nonprofit Organizations
Josh advises myriad nonprofit organizations, including small start-ups and large national foundations, on complex nonprofit and tax law issues. He often works at the nexus of tax and nonprofit law, providing valuable counsel on the unique issues presented by mergers, acquisitions, and strategic affiliations involving nonprofit organizations. Josh has a special expertise in the area of private foundations and serves corporate and family foundations nationwide. He develops close relationships with his nonprofit clients and many think of him as not just a lawyer, but as a member of the team helping to enhance their mission and effectuate their vision.

Tax Matters
Josh combines the intellectual approach associated with a large traditional tax practice with the practical problem-solving approach required for smaller entities, including helping clients resolve audits/controversies as quickly and efficiently as possible. Josh also looks at tax through the lens of state tax planning and guides clients through the unique issues presented by state tax law.

Corporations, Individuals, and Professionals
Josh provides general corporate counsel to a wide range of clients, including emerging companies and design and other professionals. Josh’s practice frequently intersects with the trusts and estates practice, particularly as that practice relates to individuals associated with the organizations he counsels.

Thought Leadership
Josh’s comments on the historic 2017 tax reform were featured in The New York Times, the Wall Street Journal and Bloomberg Tax Daily Tax Report. He authors a column on tax matters, a blog on exempt organizations, and participates frequently in bar association reports. He is deeply engaged in current events in the law and has presented at the American Bar Association, the New York State Bar Association, and at numerous local events.

Professional & Civic Affiliations

• Member, New York State Bar Association Tax Section Executive Committee
• Co-Chair, New York State Bar Association Committee on New York State Taxes
• Secretary, Board of Directors, Pathstone Development Corporation
• Member, Board of Directors, Main Street Arts
• Member, Board of Directors, Jewish Senior Life
• Member, Board of Directors, Greater Rochester Summer Learning Association
• Member, New York State Bar Association Not-for-Profit Corporations Law Committee
• Member, Impact Investing Legal Working Group (IILWG) 2019 Conference  Planning Committee
• Former Chair, Monroe County Bar Association Tax Section

Honors & Awards

• Named as Best Lawyers^® 2021 Tax Law “Lawyer of the Year” in Rochester, NY
• Named as Best Lawyers^® 2018 Tax Law “Lawyer of the Year” in Rochester, NY
• Selected by his peers for inclusion in The Best Lawyers in America^© in the field of Tax Law
• Selected to the 2017 Upstate New York Super Lawyers Rising Stars list 

Publications

Contributor to American Bar Association and New York State Bar Association Tax Sections Reports
(Please see the first footnote on each report for description of contribution.)

• American Bar Association, “Comments on Internal Revenue Code Section 512(a)(6) Special Rule for Organizations With More Than One Unrelated Trade or Business," June 23, 2020
• Tax Section Report 1413, "Comments on 2019-2020 New York State Executive Budget," March 4, 2019
• Tax Section Report 1396, "Report on Provisions of the New Tax Law Affecting Tax-Exempt Organizations," June 7, 2018
• Tax Section Report 1391, "Comments on 2018-2019 New York State Executive Budget," March 9, 2018
• Tax Section Report 1380, "Report on Recommended Amendments to the New York State's Driver's License Suspension Program," November 3, 2017
• Tax Section Report 1379, "Report on NYS Department of Taxation and Finance Draft Regulations Regarding Computation of the Prior Net Operating Loss Conversion Subtraction," August 31, 2017
• Tax Section Report 1369, "Report on Draft Business Apportionment Factor Regulations," May 26, 2017
• Tax Section Report 1344, "Report on New York State's Driver's License Suspension Program," May 5, 2016
• Tax Section Report 1343, "Report on New York Draft Combined Return Regulations," April 27, 2016
• Tax Section Report 1319, "Comments on 2015-2016 New York State Executive Budget," March 6, 2015
• Tax Section Report 1312, "Guidance Under the New York State Corporate Tax Reform Provisions," November 20, 2014
• Tax Section Report 1301, "Comments Regarding Corporate Income Tax Reform," March 13, 2014

General

• Co-author, “Leveraging Gifts in a Low Interest Rate Environment to Save on Estate Taxes,” LegalNews.com, July 14, 2020
• Co-Author, "New Fund Review Issue for Foundation Investments under Partnership Audit Rules," Family Foundation Advisor, Volume 18, Number 06, September/October 2019

• Author of updates regarding Non-Profit Revitalization Act in White New York Business Entities, Fourteenth Edition (Matthew Bender 2014) (Part IV, Not for Profit Corporation Law, VV. 6 & 7)

• "In Complying with the New Non-Profit Law, Don’t Forget the Tax Rules," Confero Magazine, Issue No. 8, October 2014

• "New York Enacts Not-for-Profit Corporation Law Reform," LexisNexis® Emerging Issues Analysis, January 2014
• "New York Limits Executive Compensation and Administrative Expenses at State-Funded Service Providers," LexisNexis® Emerging Issues Analysis, July 2013
• "In Online Partnerships, Legal Compliance Is Key," The Chronicle of Higher Education, June 17, 2013
• "Benefit Corporations Now Authorized in New York—The Formalization of Corporate Social Responsibility," LexisNexis® Emerging Issues Analysis, March 2012
• "Benefit Corporations," White’s New York Business Entities (with Joseph G. Casion)

Rochester Business Journal Taxing Matters Column

• "Leveraging gifts in a low interest rate environment to save estate taxes," Rochester Business Journal, July 6, 2020
• "IRS issues final regulations on opportunity zones," Rochester Business Journal, March 6, 2020
• "New proposals would change estate planning for retirement accounts," Rochester Business Journal, November 18, 2019
• "IRS develops new offshore voluntary compliance protocol," Rochester Business Journal, August 2, 2019
• "New opportunity zone regulations from IRS introduce flexibility," Rochester Business Journal, May 24, 2019
• "Joining trend, New York State proposes marketplace tax system," Rochester Business Journal, March 29, 2019
• "IRS issues new guidance on worker parking tax on nonprofits," Rochester Business Journal, January 25, 2019
• "IRS issues 184 pages of guidance on passthrough deduction," Rochester Business Journal, September 28, 2018
• "States win in Supreme Court ruling on taxing internet sales," Rochester Business Journal, July 27, 2018
• "New York passes work arounds to limits on SALT deduction," Rochester Business Journal, June 1, 2018
• "Tax reform’s impact on exempt organization," Rochester Business Journal, March 23, 2018
• "New tax law revolutionizes international tax for U.S. companies," Rochester Business Journal, February 23, 2018
• "Corporate tax changes under the Tax Cuts and Jobs Act," Rochester Business Journal, February 16, 2018
• "Parsing the passthrough deductions under the Tax Cuts and Jobs Act," Rochester Business Journal, February 9, 2018
• "Individual income tax reform: The impact on Rochester residents," Rochester Business Journal, February 2, 2018
• "Tax bill would make major changes for exempt organizations," Rochester Business Journal, November 17, 2017
• "IRS cracking down on abuses of microcaptive insurance," Rochester Business Journal, September 22, 2017
• "Suspending driver’s license for failure to pay tax unfair to poor," Rochester Business Journal, August 4, 2017
• "Executive order does little to change nonprofits’ lobbying situation," Rochester Business Journal, May 26, 2017
• "Tax code offers export incentives-but don’t push too far," Rochester Business Journal, March 24, 2017
• "Prepare for total reworking of business taxes under GOP proposal," Rochester Business Journal, February 2, 2017
• "New case challenges Supreme Court precedent on remote sales," Rochester Business Journal, November 18, 2016
• "Anti-inversion regulations may impact common business transactions," Rochester Business Journal, September 23, 2016
• "New IRS audit rules for partnerships will have a big impact," Rochester Business Journal, July 22, 2016
• "Partners cannot be employees, although many will try," Rochester Business Journal, May 20, 2016
• "New rules shorten wait for S corporation asset sales," Rochester Business Journal, March 18, 2016
• "IRS issues new guidance on charitable investments by foundations," Rochester Business Journal, January 22, 2016
• "Sprint lawsuit is the first ruling on amended False Claims Act," Rochester Business Journal, November 27, 2015 
• "IRS rules target common deferral arrangement," Rochester Business Journal, August 25, 2015
• "Stage is set for possible challenge to N.Y. investment income laws," Rochester Business Journal, July 24, 2015

• "Take a lesson on tax exemption from the National Football League," Rochester Business Journal, May 29, 2015

• "Cuomo's proposal would wring taxes from out-of-state sellers," Rochester Business Journal, April 3, 2015
• "IRS still gives little guidance on self-employment tax for LLC members," Rochester Business Journal, January 30, 2015
• "Businesses of all sizes can use Buffett's Duracell Strategy," Rochester Business Journal, November 21, 2014
• "Personal goodwill can work in the right situation,” Rochester Business Journal, September 19, 2014
• "New rules eliminate need for IRS disclaimer, attendant confusion," Rochester Business Journal, July 25, 2014
• "State changes law on sourcing and taxing corporate income," Rochester Business Journal, May 30, 2014
• "Rules create a minefield for non-profits’ related-party deals," Rochester Business Journal, March 21, 2014
• "IRS guidance offers safe harbor in devising tax credit deals," Rochester Business Journal, January 14, 2014
• "Rule expands favorable tax treatment for sale of business," Rochester Business Journal, November 15, 2013
• "Income tax marriage penalty now hits same-sex spouses too," Rochester Business Journal, September 20, 2013
• "New tax-free zones offer great promise for our area," Rochester Business Journal, July 26, 2013
• "Non-profits face IRS scrutiny of unrelated business income," Rochester Business Journal, May 24, 2013
• "State law gives whistleblowers a rich incentive in tax cases," Rochester Business Journal, March 22, 2013
• "For sticky tax issues, you might need to seek tax agencies’ guidance," Rochester Business Journal, January 18, 2013
• "Don’t be unnerved if taxes rise on dividends, capital gains," Rochester Business Journal, November 23, 2012
• "If you move from New York, its income tax may tag along," Rochester Business Journal, September 28, 2012
• "Nationwide sales tax reform will inevitably be burdensome," Rochester Business Journal, July 27, 2012
• "Romney’s tax planning contains lessons for the 99 percent," Rochester Business Journal, May 11, 2012
• "Strategy can cut payroll taxes for small-business owners," Rochester Business Journal, March 9, 2012
• "IRS offers relief on employees misclassified as contractors," Rochester Business Journal, January 12, 2012
• "Hurry, small-business owners with assets to sell; this offer ends soon," Rochester Business Journal, November 11, 2011
• "Unfair sales tax enforcement victimizes partners in LLCs," Rochester Business Journal, September 16, 2011
• "Why New York sees taxable software sales everywhere," Rochester Business Journal, July 8, 2011
• "Super Saver Special: Tax-free sales of small-business stock," Rochester Business Journal, May 20, 2011

News

• "New York Quickly Drops U.S. Virus Relief on Tax Write-Offs," Bloomberg BNA Daily, April 9, 2020
• "State of Wayfair: Marketplace Bill Sent to West Virginia Governor," Bloomberg BNA, March 12, 2019
• "A New Bid to Break the Cycle of Poverty," Rochester Beacon, February 14, 2019
• "Few N.Y. Businesses Sign Up for State Program to Bypass Trump Tax Limits," The Wall Street Journal, December 2, 2018
• "New tax laws suggest changes to your accounting strategy," Rochester Business Journal, October 5, 2018
• "Tax Law Changes to Make Divorce Settlements Tougher," The Daily Record, September 10, 2018
• "New York Clarifies How to Report Repatriated Income," Bloomberg BNA, August 7, 2018
• "Will Tax Changes Drive New Yorkers to the Polls? Probably Not," The New York Times, June 10, 2018
• "Verizon Wireless Denied $19M New York Sales Tax Refund," Bloomberg BNA, April 24, 2018
• "Tax Incentives: Amazon Headquarters Bids Get Tweaks Thanks to Federal Tax Act," Bloomberg BNA, April 16, 2018
• "Federal Tax Law Could Be Stumbling Block for State Incentives," Bloomberg BNA, January 24, 2018
• "Tax Pros Brace For 2nd Wave of Tax Upheaval, From States," Law360, January 23, 2018

Presentations

• Panelist, "Opportunity Zone Summit," Rochester Institute of Technology, October 8, 2019
• "Opportunities for Impact: How Grantmakers Can Leverage Opportunity Zones," 2019 NY Funders Alliance Conference, Albany, NY, September 10, 2019
• Guest Lecturer, "The Law of Higher Education," Cornell Law School, March 21, 2019
• "Get in the Zone: Leveraging Mutual Business Opportunity through Opportunity Fund Investments," Greater Rochester Chamber of Commerce, January 30, 2019
• "Current Complex Investment Issues," ABA Tax Section 2019 Midyear Tax Meeting, January 18, 2019
• "Hot Topics for Exempt Organizations: 2018 in Review," 2018 Not-for-Profit Educational Seminar presented by The Bonadio Group, Tarrytown, NY, December 12, 2018
• "Hot Topics for Exempt Organizations: 2018 in Review," 2018 Not-for-Profit Educational Seminar presented by The Bonadio Group, Albany, NY, December 5, 2018
• "Hot Topics for Exempt Organizations: 2018 in Review," 2018 Not-for-Profit Educational Seminar presented by The Bonadio Group, Rochester, NY, December 3, 2018
• "Local Opportunities for Opportunity Zones," presented by NAIOP: Commercial Real Estate Development Association Upstate New York Chapter, November 30, 2018
• "Not-for-Profit Legal Update: What policies does my organizations really need to adopt?" The Buffalo Club, November 28, 2018
• "Entity Selection and Qualified Business Income Deduction After the TCJA," Monroe County Bar Association’s 53rd Annual Tax Institute, November 16, 2018
• "Healthcare Financial Management Association (HFMA)Tax Reform for Exempt Organizations: 10 Things You Need to Know" webinar, June 20, 2018 and September 25, 2018
• "Tax Reform for Exempt Organizations: 10 Things You Need to Know" webinar, June 14, 2018
• "Tax Reforms Impact of Higher Education," Albany College & University Spring Educational Breakfast Series presented by The Bonadio Group, June 11, 2018
• "Tax Reforms Impact of Higher Education," Central New York Higher Education Symposium presented by The Bonadio Group, June 4, 2018
• "Tax Reforms Impact of Higher Education," Rochester College & University Spring Educational Breakfast Series, presented by The Bonadio Group and the Upstate New York College Collaborative, May 21, 2018
• "Tax Law Update," Monroe County Bar Association, February 28, 2018
• "Tax Reform: What You Need to Know Seminar," HSE, Rochester, New York, February 13, 2018
• "Tax Reform: What You Need to Know Seminar," Buffalo Club, Buffalo, New York, January 30, 2018
• "The Effects of Pending Federal Tax Legislation on State and Local Taxation," New York State Bar Association Tax Section Meeting, January 23, 2018
• "From Basics to Hot Topics," New York State Bar Association’s New York Not-for-Profit Organizations Practice Symposium, November 30, 2017
• "Non-Profit Unrelated Business Income Tax," Monroe County Bar Association’s 52nd Annual Tax Institute, November 17, 2017
• Panelist, "Enough About Tax Reform: What Else Is Going on in New York" New York State Bar Association Tax Section Summer Meeting, July 22, 2017
• "2016 Amendments to the Not-for-Profit Corporation Law," New York State Bar Association 2017 Annual Meeting, January 2017
• "Tax Considerations in Choosing an Entity," Monroe County Bar Association, January 2017
• "At Risk Rules and Passive Activity Losses (PAL)," Monroe County Bar Association’s 51st Annual Tax Institute, November 2016
• "Steps to Avoid an Audit," Eyes on the Future, Greater Rochester Enterprise, September 2016
• "Recent Amendments to Non-Profit Revitalization Act (NPRA)," New York State Bar Association, Business Law Section Spring Meeting, May 2016
• Workshop on Taxes for Small Businesses, Volunteer Legal Services Project, December 2015
• "Ensuring Compliance with the Terms of Tax Exempt Status and Putting Vital Policies in Place (Part VI)," National Business Institute Seminar: Form 990: What the IRS is Looking For,” November 2015
• "Partnership Accounting Concepts for Business Lawyers," Monroe County Bar Association, May 2015
• "Foreign Reporting Rules," 48th Annual Tax Institute, Monroe County Bar Association, November 2014
• "Choice of Entity," Business Law Topics Relevant to Pro Bono Matters, Monroe County Bar Association, September 2014
• "Introduction to New York’s Not-For-Profit Law," Business Law Section Fall Meeting, New York State Bar Association, September 2014
• "Establishing Tax-Exempt Status within the IRS" and "Unrelated Business Taxable Income (UBTI)," National Business Institute Seminar: Tax Exempt Organizations from Start to Finish, June 2014
• "Pay for Success: Social Impact Bonds and Other Vehicles," Grantmakers Forum of New York, May 2014
• "New York's Nonprofit Revitalization Act of 2013," NYSBA’s Business Law Section, Committee on Continuing Legal Education, March 2014
• "The Nonprofit Revitalization Act of 2013,” Monroe County Bar Association, February 2014
• "A Tempest in a Teapot? Lessons for Tax Exempt Organizations from the IRS ‘Tea Party’," 48th Annual Tax Institute, Monroe County Bar Association, November 2013
• "Overview of Major Corporate Transactions" and "Charitable Planning (Unique Asset Considerations)," Advising and Operating the NY Not-for-Profit Organization, New York State Bar Association, November 2013
• "Tax Considerations in Mergers and Acquisitions," Mergers & Acquisitions Seminar, Monroe County Bar Association, June 2013
• "Proposed Revisions to the New York Not-for-Profit Law," Spring Meeting of the NYSBA’s Business Law Section, Corporations Law Committee, May 2013
• "Restructuring and Terminating Exempt Organizations: Procedures and Pitfalls," National Business Institute, December 2012
• "Everything You Always Wanted to Know But Were Afraid to Ask About Circular 230," 47th Annual Tax Institute, Monroe County Bar Association, November 2012
• "Tax Considerations in Choosing an Entity," Business Law Nuts & Bolts - Formations, Monroe County Bar Association, October 2012
• "Ten Things Your Internet Business Needs to Know About New York Sales Tax," HSE Webinars, June 2012
• "Federal Tax Update," 46th Annual Tax Institute, Monroe County Bar Association, November 2011
• "Particular Types of Not-for-Profit Organizations," Operating the NY Not-for-Profit Organization, New York State Bar Association, November 2011
• "Hot Topics in New York State Sales Tax," Monroe County Bar Association, June 2011
• "Business Law: Choosing an Entity & Formations," Monroe County Bar Association, December 2010
• "Safe Harbor Partnership Agreements: Dissecting the Boilerplate," 45th Annual Tax Institute, Monroe County Bar Association, November 2010
• "At Risk Rules," 44th Annual Tax Institute, Monroe County Bar Association, November 2009

Admissions

• New York

Education

• University of Michigan Law School, J.D., magna cum laude
• Harvard University, B.A., cum laude