About
Smycorp Investments Inc. is the principal investment vehicle of Craig Smith. We own, reposition and partner in commercial real estate across the city, and structure vehicles that bring our partners into those investments alongside us.
OUR STORY
Smycorp began with a salesperson who couldn't stop thinking like an owner. Years of working on commercial real estate deals gave Craig a building-by-building knowledge of downtown Toronto: who owned what, what each property could become, and why it hadn't yet. In 1997, he set up Smycorp to invest in the buildings and neighbourhoods he knew best, this time as an owner.
Smycorp ran alongside Craig’s sales and advisory career until October 2025, when it became his full focus. Today we work from the Gooderham Building, Toronto’s Flatiron, built in 1892, as both investor and tenant.
TEAM
Craig Smith
Principal
Craig is a Toronto real estate investor and entrepreneur with more than 30 years of experience across brokerage, investment and venture building in commercial real estate. He founded Ashlar Urban Realty in 1999 and built it into one of Toronto's most respected downtown commercial firms; following its acquisition by Cushman & Wakefield in 2017, he was Head of Eastern Canada for the firm's Equity, Debt and Structured Finance group until October 2025. Over his career he has negotiated thousands of transactions worth billions of dollars across urban Toronto. Craig co-founded CHC Realty Investments, which grew into a publicly traded student housing platform across Ontario and Quebec, and Skye Trillium, a CMBS debt fund. He serves as Principal Advisor to Aura Partners Inc., Brokerage, has served on the board of Pinewood Studios and as President of both NAIOP's Greater Toronto Chapter and the National Club, and holds a degree from Western University, where he was student body president.
Stuart Sylvester
Saira leads finance, governance and controls across Smycorp and its affiliated entities. She brings more than two decades of senior leadership across financial services, healthcare and high-growth companies, specializing in building institutional-grade financial infrastructure that positions organizations for capital investment and disciplined growth. Saira spent more than a decade at TD, most recently as AVP, Corporate Projects, Governance & Controls, and since 2018 has advised founders and boards as a fractional CFO and governance consultant. She is also an active angel investor and growth advisor to Canadian entrepreneurs.
Senior Advisor, Investment
Ariana leads strategy, planning and communications across Smycorp and its affiliated ventures, from investor materials and positioning to the planning context behind new opportunities. An urban planner with fifteen years in the real estate and development sectors, she was previously Director, Engagement at TAS, where she led stakeholder engagement and communications across an $800M+ mixed-use, commercial and urban industrial portfolio, working alongside development, investment and asset management teams. Ariana holds a Master of Planning from Toronto Metropolitan University and a BA from Western University.
Saira Somani, CPA, CMA
Saira leads finance, governance and controls across Smycorp and its affiliated entities. She brings more than two decades of senior leadership across financial services, healthcare and high-growth companies, specializing in building institutional-grade financial infrastructure that positions organizations for capital investment and disciplined growth. Saira spent more than a decade at TD, most recently as AVP, Corporate Projects, Governance & Controls, and since 2018 has advised founders and boards as a fractional CFO and governance consultant. She is also an active angel investor and growth advisor to Canadian entrepreneurs.
VP, Finance
Ariana Holt
VP, Strategy, Planning & Communications
IN GOOD COMPANY
Everything we do, we do with partners: capital partners, operators, advisors and specialists who know their markets as well as we know ours. Here are some of the groups we work with.
.png)
