Lawyer Profile -
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Published on: 8/27/2009
Last Visited: 8/27/2009
Jay Shepherd
Originally trained as a tax lawyer with one of Toronto's major law firms, Jay has parlayed his unusual, "out-of-the-box" way of looking at things into reputations both in tax planning, and as a high-tech lawyer.
On the tax side, Jay's planning work is characterized by creativity.
More than anything else, Jay excels at providing unexpected solutions to seemingly intractable problems.
On the corporate side, his clients - mainly small and medium-sized companies with technology-driven businesses - also value that same ability to look at problems from a different perspective, and find solutions where none are obvious.
They also value his strong practical experience, and his ability to cut through the legal "stuff" and solve their business problems, rather than just giving the legal answer.
Jay is perhaps best known for doing "deals".
In his twenty-plus years of practice, he has completed more than four hundred business deals - debt and equity financings, complex tax restructurings, purchases and sales of assets and shares, strategic alliances, distributorship and other licensing deals, reorganizations, etc.
He is known as a "closer", meaning that when he takes a deal on, there is a high probability that he will find a way to bring it to a successful closing, despite roadblocks along the way.
But Jay doesn't just show up for the deals.
His clients know that he's around, day in and day out, to help them solve the ongoing problems and issues that face any entrepreneurial enterprise.
This means that Jay is usually a key outside advisor to the CEO, has often sat on the boards of directors or advisory boards of small companies, and always takes an active role in helping those companies succeed.
All of this flows out of a career that has been more than a bit unusual.
A radical student in the sixties (editor of his school's scandalous newspaper, local newspaper columnist, published fiction writer), Jay abruptly dropped out of high school, cut his hair (which took a while), and started work as a bank trainee.
Then, after seven successful years as a banker, Jay woke up one day and decided to go to law school.
He graduated first out of three hundred lawyers from Osgoode Hall Law School, garnering a lengthy list of prizes and awards, then went on to get a Masters of Law at University of Toronto, to teach part-time at Osgoode for eleven years, and to publish extensively in areas spanning a broad range from fiduciaries, to tax policy, to financing techniques, to renewable energy, to racial bias in the legal system.
In private practice, Jay spent his first decade as a tax and corporate lawyer in a major downtown firm, then his next decade as the senior partner of a boutique corporate law firm.
At that point, after being recruited by a client, he left the practice of law to join a high-tech company, and spent two turbulent years sitting in the CEO chair himself.
In 2002 he returned to private practice with Shibley Righton LLP.
Jay is active in community activities, and in particular has for many years been a well-known figure in Canada's renewable energy sector - as a financier, owner, counsel, organizer, and national spokesperson.
In 1995 he was awarded the Hedley Palmer Award for his longstanding contributions to the independent power industry in Canada.
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