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TwoGoose Ventures
Rajen Ruparell founded TwoGoose Ventures in 2023 after exits from Groupon International and Endy. The office operates from Toronto and deploys family capital...
TwoGoose Ventures
Rajen Ruparell founded TwoGoose Ventures in 2023 after exits from Groupon International and Endy. The office operates from Toronto and deploys family capital directly. TwoGoose targets direct co-investments and SPVs in technology, D2C retail, IoT, real estate, consumer health, food, and e-commerce. Holdings include the Toronto Urban Portfolio and Calgary commercial real estate. The firm maintains North American focus and works with co-investors such as Travis Kalanick and Michele Romanow. The office lists Afraj Gill as partner. It holds memberships in the Chicago Architecture Foundation, Canada-US Business Council, Techweek, and Royal Conservatory of Music. Rajen J. Ruparell Family Foundation runs separate giving in health, education, community support, and arts. TwoGoose maintains a direct-ownership model that favors control positions over diversified fund commitments.
General information
Firm type
Single Family Office
Year founded
2023
AUM
Undisclosed
Location
Region
North America
Country
Canada
City
Toronto
Corporate office
Toronto, Ontario, Canada
Principals
Rajen Ruparell
Founder
Altss tracks 1 additional named team member for this firm — including direct investment leads, IR, and operating principals not listed on the public website.
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Frequently asked questions
Who runs investment decisions at TwoGoose Ventures?
Rajen Ruparell sets direction as founder. Afraj Gill serves as partner on the operating team.
How does TwoGoose Ventures source proprietary deal flow?
The office draws on Rajen Ruparell's prior relationships from Groupon International and the Toronto tech ecosystem, including co-investors such as Travis Kalanick and Michele Romanow.
Does TwoGoose Ventures participate in fund commitments or only direct deals?
TwoGoose focuses on direct co-investments and SPVs. It does not disclose allocations to external funds.
Where does the underlying wealth come from?
Rajen Ruparell built the capital through co-founding Groupon International and the sale of Endy to Sleep Country Canada.
Does TwoGoose Ventures maintain philanthropic structures, and how are they separated?
The Rajen J. Ruparell Family Foundation operates separately with four pillars: Health, Education, Community Support, and Arts & Culture.
Profile maintained by Altss using OSINT (open-source intelligence), regulatory filings, licensed data partners, and verified direct submissions. Read the methodology. Last updated: . Continuous refresh with full update cycles at least every 30 days.
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