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Stuart F. Bollefer

Partner* Admitted to the Ontario Bar: 1982
*Practising as a professional corporation
People > Stuart F. Bollefer

With over 30 years of experience in tax law and estate planning, Stuart has earned recognition for bringing technical expertise to bear along with a keen awareness of the human dynamics of his clients’ situations. Stuart is a natural problem solver, and has the ability to find innovative resolutions to his clients’ tax issues. With exceptional communications skills, he breaks down complex domestic and multijurisdictional issues into a meaningful context for his clients.

Stuart is a member of the firm's Tax group and Chair of the Tax & Succession Planning Group. He has extensive experience providing domestic and international tax advice with respect to mergers and acquisitions, structuring shareholder agreements, inbound and outbound investment and business expansion, and estate and wealth preservation planning.

Awards & Recognition

  • Trust and Estate Practitioner designation (TEP)
  • Recognized in The Canadian Legal Lexpert Directory as a leading lawyer in Estate & Personal Tax Planning

Professional Involvement

Memberships

  • Canadian Tax Foundation
  • Canadian Bar Association
  • Ontario Bar Association
  • International Fiscal Association (Canadian Branch)
  • Society of Trust and Estate Practitioners (STEP Canada)

Teaching Engagements

  • Former instructor, Taxation, Bar Admission Course, Law Society of Upper Canada

Selected Speaking Engagements

CONFERENCES AND PRESENTATIONS

“TOSI Workshop,” Edward Village Hotel North York, 4 December 2018

“Tax Law Essentials for Private, Owner-Managed and Family Businesses,” Aird & Berlis LLP Webinar, 20 November 2018

“Tax On Split Income,” Canadian Tax Foundation 2018 Ontario Tax Conference & Live Webcast, 22 October 2018

“Tax On Split Income – How Not to Get Trapped in the TOSI Rabbit Hole” Norton McMullen LLP, Markham, ON, 27 September 2018

“Income Splitting: How Will Proposed Amendments Affect You?” RBC Wealth Management Services National Conference, 20 April 2018

“Income Splitting: How Will Proposed Amendments Affect You?” TD Wealth Advisory Services, 9 April 2018

“Income Splitting: How Will Proposed Amendments Affect You?” Aird & Berlis LLP Webinar, 7 February 2018

“Case Study: Income Tax Issues in Estate Administration,” Cidel Provence Conference 2017, Nice, France, September 13-16, 2017

“Taxation of Private Corporations: How Will Proposed Amendments Affect You?” Aird & Berlis LLP Webinar, 27 July 2017

“Shareholder Agreements – Disability and Tax Implications to Keep in Mind,” North York District Chartered Professional Accountants Association, 7 March 2016

“Shareholder Agreements - Some Selected Tax Issues,” Wolters Kluwer, 20 January 2016

“Shareholder Agreements - Some Selected Tax Issues,” Collins Barrow 2015 National Tax Conference, 1 June 2015

“Dealing with the 21 Year Deemed Disposition,” Cidel Provence Conference 2014, Nice, France, September 2014

"Post Mortem Planning – Dealing with Double Tax on Death," Ontario Bar Association, Taxation Law/Trusts and Estates Law Program, 29 May 2014

"Shareholder Agreements: Legal and Tax Issues," AJAG, 17 January 2013

"Post Mortem Planning Dealing with Double Tax on Death," Ontario Bar Association, 24 October 2012

“Living with Canada’s Proposed Non-Resident Trust Rules,” STEP Cayman Islands Branch, 31 May 2012

“Post Mortem and Testamentary Trust Planning,” Wealth Advisor Conference, CIBC Private Wealth Management, 19 January 2012

“Shareholders’ Agreements,” CCH Webinar, 19 October 2011

“Tax Planning Update,” Norton McMullen & Co. LLP, 19 May 2011
“Structuring Your Company for Transition,” CIBC Wood Gundy, 20 January 2011

"Shareholders' Agreements: Structuring a Client Corporation's Ownership and Transition," STEP Canada 12th National Conference, 7 June 2010

"Structuring Your Company for Transition," CIBC Wood Gundy, 18 May 2010

"Tax Planning for the Owner-Manager and Professional," Dundee Securities Corporation, 28 April 2010 and 3 May 2010

"Buy-outs on Death," Aird & Berlis LLP Shareholders' Agreement Conference, 18 February 2010

"Structuring Your Company for Transition," CIBC Wood Gundy, 27 January 2010

"Shareholders' Agreements," Shimmerman Penn LLP, 21 January 2010

"Shareholder Agreements," STEP Seminar, 15 December 2009

"Structuring Your Company for Transition," Family Firm Institute Best Practice Seminar, 2 December 2009

"Business Succession Planning: Tax Issues to Consider Now, for Future Exit Strategies," Goodman Private Wealth Management, 18 November 2009

"From Recession to Succession: Discovering Opportunities in Today's Economic Climate," BMO Business Succession Seminar, 16 June 2009

"Passing On Your Business with Confidence," RBC Business Succession Seminar, 13 May 2009

"Post-Mortem Tax Planning - The Double Tax Problem," Tax for Succession Planning, Trusts and Estates Practitioners Program, Ontario Bar Association, 3 March 2009

"Moving Forward From Your Business: Tax Issues to Consider Now, for Future Exit Strategies," A&B Technology Law Seminar: What Every Business Should Know, 25 February 2009

"Planning Points for the New or Existing Client," Norton McMullen & Co. LLP, 27 November 2008

"Domestic and International Planning Points," RBC Dominion Securities, 22 October 2008

"Business Succession Planning - A Case Study," RBC Private Bankers, 9 October 2007

"Case Study: The New Client," Osgoode Hall Law School Graduate Program, LLM Tax Specialist Program, 22 July 2006

"What is Succession Planning?" TD Private Client Services, 19 May 2006

"Case Study: The New Client," RBC Webcast Presentation, 13 & 17 April 2006

"Shareholder Agreements / Life Insurance Funded Buy-Sell on Death," Ontario Tax Conference, 17 & 18 October 2005

"Buy-outs on Death," Aird & Berlis LLP Shareholders' Agreement Conference, 21 February 2005

"Estate Planning Presentation," FundEX, 1 October 2004

"Holding Companies," Barakett & Associates, The Briars, August 2004

"Case Study: The New Client," 2004

"Creative Uses of Trusts," CG&B, 11 September 2001

"Double Tax on Death Employment Benefit and Other Plans," CG&B, July 2001

"Tax Issues in Cross-border Real Estate Investments - US Investment in Canadian Real Estate," Counsel for International Tax Education, 18 October 2000

AIRD & BERLIS LLP TAX BREAKFAST CLUB PRESENTATIONS

“Post Mortem Planning,” November 2011

"Shareholders' Agreements," November 2009

"Part II International Tax Planning for the Owner-Manager," December 2007

"International Tax Planning for the Owner-Manager," October 2007

"Business Succession Planning: A Case Study," November 2006

"Taxation of Foreign Source Income/ Foreign Business Structure Case Study," October 2005

"Tax Implications of Shareholders Agreement," October 2004

"Taxation of Dividends," May 2004

"Corporate Divorce - Spin-Offs and Transfers - Business Divorce in Joint Ventures; Butterfly Transactions and Alternatives; Protecting Corporate Surplus; Real Estate Break-Ups; Section 55: When a Tax Free Dividend Becomes a Capital Gain," September 2003

"Interest Deductibility; GAAR Update; Recent CCRA Administrative Positions and Proposed Non-Resident Trusts Legislation," December 2002

"Non Resident Trust Update," December 2002

"GAAR: Update on Recent CCRA GAAR Activity," December 2002

"FIE Decision Tree," November 2002

"Taxation of Investment Income, Update on Proposed FIE Rules and Review of FAPI," November 2002 (with Jack Bernstein and Kay Leung)

"Case Study: The New Client," September 2002

"Post Mortem Planning," May 2002

"Life Insurance Funded Shareholder Agreements," Fall 2001

"Revised Foreign Investment Entities Proposals," September 2001

"Life Insurance Funded Shareholder Agreements," June 2001

Selected Publications

“Tax On Split Income – A Detailed Analysis (Or How Not to Get Trapped in the TOSI Rabbit Hole),” Canadian Tax Foundation 2018 Ontario Tax Conference & Live Webcast, October 2018 (Co-authored with David Malach)

"Buy-Sell Provisions and their Effect on Canadian Control of Private Corporations: Part 2,” Tax Profile, Wolters Kluwer, January 2018 and in part reproduced in TaxLine, Aird & Berlis LLP, February 2018 (Co-authored with Jack Bernstein and Saam Nainifard)

"Buy-Sell Provisions and their Effect on Canadian Control of Private Corporations: Part 1,” Tax Profile, Wolters Kluwer, December 2017 and in part reproduced in TaxLine, Aird & Berlis LLP, January 2018 (Co-authored with Jack Bernstein and Saam Nainifard)

"Buy-Sell Provisions and Their Effect on Canadian Control of Private Corporations,” Tax Notes International, June 2017 (Co-authored with Jack Bernstein and Saam Nainifard)

"Residency of Trusts Particularly in the Context of Estates," Tax Profile, CCH Canada Limited, April 2012

“Post-Mortem Planning – Double Taxation on Death,” Tax Profile, CCH Canadian Limited, February 2012 and TaxLine, CCH Canadian Limited, March 2012

“Summary of Canada Revenue Agency Round Table Held at the 13th National STEP Canada Conference,” Tax Profile, CCH Canadian Limited, June 2011, TaxLine, CCH Canadian Limited, July 2011 and The Estate Planner, CCH Canadian Limited, August 2011

"Shareholders' Agreements – A Survey of Income Tax Issues,” Tax Profile, CCH Canadian Limited, January 2010 and TaxLine, CCH Canadian Limited, February 2010

Editor in Chief and Contributing Author, "Shareholders' Agreements: A Tax and Legal Guide," third edition, CCH Canadian Limited, June 2009

"The Business in Transition: Making the Succession Plan Work - Business Owner's Edition," LexisNexis, 2009 (Co-authored with David Malach)

"The Business in Transition: Making the Succession Plan Work," LexisNexis, 2008 (Co-authored with David Malach)

"International Tax Planning For The Owner/Manager - Part IV: Holdings, Sales and Reorganizations of Foreign Affiliates, and the Distribution of Surplus Accounts," Tax Profile, CCH Canadian Limited, July 2008 and TaxLine, CCH Canadian Limited, August 2008

"International Tax Planning For The Owner/Manager - Part III: Using Foreign Affiliates in Offshore Operations," Tax Profile, CCH Canadian Limited, June 2008 and TaxLine, CCH Canadian Limited, July 2008

"International Tax Planning For The Owner/Manager - Part II: Determining Active Business Status and Avoiding FAPI," Tax Profile, CCH Canadian Limited, April 2008 and TaxLine, CCH Canadian Limited, May 2008

"International Tax Planning For The Owner/Manager - Part I," Tax Profile, CCH Canadian Limited, March 2008 and TaxLine, CCH Canadian Limited, April 2008

"Foreign Investment Entities in Canada," HNW Journal, January/February 2008

"Foreign Source Income: Outbound Structures and Foreign Tax Credit Planning - Part II," Tax Profile, CCH Canadian Limited, February 2006 and TaxLine, CCH Canadian Limited, March 2006 (Co-authored with Robert Martini)

"Foreign Source Income: Outbound Structures and Foreign Tax Credit Planning - Part I," Tax Profile, CCH Canadian Limited, January 2006

"Structuring Foreign Investments," Tax Profile, CCH Canadian Limited, May 2005 and TaxLine, CCH Canadian Limited, June 2005

Contributor and Editor, "Shareholders' Agreements: A Tax and Legal Guide," second edition, CCH Canadian Limited, 2005

"Taxation of Dividends: A Survey In The Context of Private Corporation and Their Shareholders - Part II," Tax Profile, CCH Canadian Limited, December 2004 and TaxLine, CCH Canadian Limited, January 2005

"Taxation of Dividends: A Survey In The Context of Private Corporation and Their Shareholders - Part I," Tax Profile, CCH Canadian Limited, October 2004 and TaxLine, CCH Canadian Limited, November 2004

"Review of Tax Implications of Corporate-Owned Life Insurance Buy-Sell Agreements," Tax Profile, CCH Canadian Limited, September 2004 and TaxLine, CCH Canadian Limited October 2004 (Co-authored with Jack Bernstein and Henry Chong)

"Shareholders' Agreements: A Tax and Legal Guide," second edition, CCH Canadian Limited, 2004 (Co-author with Steve Kelman, Jack Bernstein and Dennis Miller)

"Effecting and Estate Freeze," Strategies, CIBC Private Wealth Management: 2004

"Split Up of Corporate Business Partnerships," Tax Profile, CCH Canadian Limited, October 2003

"Memorandum: Revised Foreign Investment Entities Proposals," Tax Profile, CCH Canadian Limited, March 2003 (Co-author with Jack Bernstein and Henry Chong)

"A Review of Canada's Revised Foreign Investment Entities Proposals," Tax Notes, Tax Notes International, March 2003 (Co-author with Jack Bernstein)

"Case Study: The New Client," Tax Profile, CCH Canadian Limited, February 2003 (Co-author with Robert Martini)

"Non-Resident Trust Update," Tax Notes, Tax Notes International, January 2003 and Tax Profile, CCH Canadian Limited, January 2003 (Co-author with Jack Bernstein)

"Update on Current CCRA GAAR Activity," Tax Profile, CCH Canadian Limited, December 2002 (Co-author with Jack Bernstein)

"Update on CCRA's Administrative Positions on Interest Deductibility and Other Matters," Tax Profile, CCH Canadian Limited, November 2002 (Co-author with Jack Bernstein and Kay Leung)

"Non-Resident Trust Update," Canadian Tax Highlights, CCH Canadian Limited, November 2002 (Co-author with Jack Bernstein)

"Revised Foreign Investment Equities Proposals," Tax Profile, CCH Canadian Limited, September 2001 (Co-author with Jack Bernstein and Henry Chong)

"Canadian Foreign Investment Entities: An Analysis of Recent Draft Legislation," Tax Notes, Tax Notes International, September 2001 (Co-author with Jack Bernstein and Henry Chong)

"Double Tax Issues On Section 85 Rollover," Tax Profile, CCH Canadian Limited, June 2001

"Planning For Double Tax on Death," Canadian Tax Highlights, CCH Canadian Limited, June 2001 (Co-author with Jack Bernstein)

"Canada Customs and Revenue Agency Comment on Technical Positions and Cases of Recent Interest," Tax Profile, CCH Canadian Limited, November 2000

Insights

Publications Article Nov 21, 2018 An Update on Multiple Wills
Publications Article Feb 27, 2018 Highlights of the 2018 Federal Budget

Education

  • LLB, University of Toronto, 1980
  • BA, Wilfrid Laurier University, 1977

Expertise