James Smith

I’ve dedicated my career to the service of Canadian startups, growing up with our venture industry since 1995. In that time, I have assisted firms raise over $10B in venture capital, supported over $14B in exit transactions, and acted as the principal legal advisor from firm incorporation to Canada’s leading startups, including Wattpad, TopHat, Ada Support, Jobber and Shopify.

I have since July 2022 rededicated myself to early-stage venture work, and to supporting Canadian-based founders of high-growth enterprises.

Upside Venture Law is a solo album venture law thing, focusing on four things. First, acting for a curated group of startups from ideation to Series A, in much the way I have throughout my career. Second, providing guidance to high-net worth founders with a concierge suite of founder-focused services to support personal investment and LP strategies, personal tax planning, and, importantly, conflicts management support in equity financing and M&A transactions. Third, providing legal advice to investors in diligence-light, Canadian-based investment and portfolio activities, whether early-stage led rounds or follow-on commitments. Lastly, supporting adventurepreneurship in Canada’s resort and mountain communities, providing pay-as-you-go legal guidance for action sports athletes during their podium years, and helping with venture creation initiatives as their careers mature.

I am always open to hear about new projects, and how I might assist.