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Trailfund Inc. is a Toronto-based, AI-powered commercial mortgage origination company. According to Cision Canada's news-release listing, it was founded in 2024 by Steve (Steven) Treger and Judah Cooper and has been acquired by KingSett Capital. Trailfund built a platform aimed at the commercial real estate lending market; per the company's own site and third-party business directories, it is designed to help commercial real estate firms originate, underwrite, and close deals faster, positioning itself as a system purpose-built for CRE with features including a deal pipeline/CRM and automated extraction of metrics from financial models. Steven Treger is listed as co-founder and CEO and Judah Cooper as co-founder; both are based in Toronto, and the company is a small startup (roughly 11–50 employees, per ZoomInfo). KingSett Capital is described in its own releases as Canada's leading private equity real estate investment firm, with a substantial real estate lending arm, and is led by CEO Rob Kumer. The acquisition gives KingSett an in-house AI origination/underwriting capability for its commercial mortgage lending business.
Parties
Company
KingSett Capital
Company
Trailfund Inc.
Deal Type
Merger & AcquisitionIndustry
Tech/Computer/ITTransaction
Undisclosed/ConfidentialDeal Status
ClosedClosing Date
21 May 2026