Jeff Dennis


Jeff Dennis is a lawyer, serial entrepreneur, best-selling author and public speaker. He works with fast growth entrepreneurial companies assisting them with commercialization strategy and finance.

He has worked with hundreds of companies in a wide range of industries, including real estate, film and television production, natural resources, financial services, franchising and cosmetics. He has worked with all types of tech companies – cleantech, medtech, proptech, fintech, blockchain and cryptocurrency, AI and machine learning, to name a few.

Prior to being Fasken Law’s Entrepreneur in Residence, Jeff was a founder and partner in an investment dealer. Along with his partners, he raised over $2 billion for various investment opportunities.

Jeff co-founded the Toronto Chapter of the Young Entrepreneurs Organization, now called the Entrepreneurs Organization (EO). Through his association with EO and the Ewing Marion Kauffman Foundation, he co-authored his international best-selling book, Lessons from the Edge, in which entrepreneurs share their biggest mistakes in business and the lessons they learned.

Jeff is a sought-after public speaker by entrepreneurial groups around the world. His most exotic destination was a presentation to the EO chapter in Kathmandu, Nepal.


  • Certified Director (ICD.D), Directors’ Education Program, Institute of Corporate Directors
    and the Rotman School of Business, University of Toronto
  • Birthing of Giants Executive Education Program, Massachusetts Institute of Technology, EO and INC Magazine
  • Bachelor of Law (LL.B.), University of Western Ontario
  • Bachelor of Arts (BA), Brown University, Major in Economics
  • Upper Canada College


Trusted Advisor

a. Strategic Planning
b. Restructuring Advisor
c. Negotiation Coach
d. Pitch Coach


M&A and Corporate Finance Advisory

Public Venture Capital Advisory

Learn more about Jeff’s services


I cannot say enough nice things about Jeff. As a client of Jeff, he provides the kind of “tough love” advice that most “polite” people won’t tell you, but that you absolutely need to have. He makes himself available on tight timelines to guide you through your many “emergencies” as an entrepreneur and is always optimistic but realistic. While he has strong opinions, he always opens with the question “what do you want to do?” and then guides accordingly. Finally, he opens his network to you and is ever willing to help with referrals and connections.

Rob Hong, Founder, Sapling Financial

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