Rajen Ruparell

Rajen Ruparell is a Canadian-born entrepreneur and investor based in Toronto. He graduated from Imperial College Business School in 2007 with an MSc Management after undergraduate studies in economics and politics. In an Imperial alumni profile, he said he chose business school for its entrepreneurship focus, global reputation, and the chance to live in London.

Ruparell co-founded CityDeal in 2010, a Europe-based daily-deals company that was acquired by Groupon. After the acquisition, he became a co-founder of Groupon International and worked at Groupon for roughly five years. Public bios say he helped take Groupon public, led international growth, founded and built Groupon Goods, led the global deals team, and served as SVP of global partnerships / “Chief Dealmaker” before stepping down in 2015 while remaining an advisor.

After Groupon, Ruparell became an active entrepreneur-investor. BrainStation reported in March 2015 that he planned to “aggressively explore” building and investing in Canadian e-commerce ventures like Endy. Endy launched in 2015 as a made-in-Canada online mattress brand co-founded by Ruparell and Mike Gettis; Sleep Country Canada announced in November 2018 that it would acquire Endy for up to C$88.7 million, with Ruparell identified as co-founder, chairman, and majority shareholder.

Ruparell is now Founder and Chairman of TwoGoose, described on its website as his private family office. He also founded the Rajen J. Ruparell Family Foundation and serves as co-chair of its grant committee. His board and advisory service has included the Chicago Architecture Foundation, the Canada-US Business Council, Techweek, and The Royal Conservatory of Music board.

• TwoGoose describes its operating principle as: “We work on things we like with people we like.”
• TwoGoose says its primary focus is acquiring major stakes in consumer-focused companies it is passionate about, then using its experience, skillset, and capital to create value and drive growth.
• Ruparell has publicly emphasized e-commerce models that remove intermediaries, sell at volume, and offer transparency to customers.
• He has shown a preference for companies with direct consumer pull, authentic customer love, and large-category disruption: Endy’s model focused on a simple online buying experience, Canadian-made product, and word-of-mouth rather than paid celebrity endorsement.
• His public portfolio and firm materials point to a broad but operator-led focus across consumer technology, health/wellness, retail, IoT, e-commerce, food, and related technology platforms.
• Public sources do not verify a standard check size.