Toronto’s entrepreneurial landscape is bracing for the next wave of innovation from serial entrepreneur Cole Diamond Toronto with the upcoming launch of his new technology venture, Trade In, slated for early next year.1 Known for his groundbreaking work as the co-founder and former CEO of Coinsquare, Canada’s premier cryptocurrency broker-dealer, and his disruptive influence on industries ranging from digital asset custody (Tetra Trust) to food delivery (Ghost Kitchens International), Diamond’s latest endeavor promises to be another significant addition to Toronto’s thriving tech ecosystem.2
While specific details about Trade In remain largely under wraps, the very name sparks speculation about its potential focus. Given Diamond’s track record of identifying and capitalizing on market inefficiencies and evolving consumer behaviors, Trade In is anticipated to be a technology-driven solution aimed at disrupting an existing market. His investment portfolio, which includes early-stage companies like RoketEV (electric vehicle infrastructure), KEEP (digital identity), and BIG Digital (digital marketing), offers some clues to his broader interests in transformative technologies.3
The most compelling hints, however, point towards a potential reinvention of the automotive market. The term "Trade In" strongly suggests a platform or service focused on the buying, selling, or trading of vehicles. This aligns with Diamond's recent activities and the inherent opportunities for technological disruption within the automotive sector, particularly the used car market. This market is often plagued by a lack of transparency, cumbersome processes, and trust concerns – all areas ripe for the kind of innovative solutions Diamond has previously delivered.
Launching a tech venture focused on the automotive market from Toronto makes strategic sense. The city is a major urban center with a significant and diverse consumer base. Its growing embrace of digital solutions and its position as a hub for technological talent provide a fertile ground for a disruptive player to gain traction and scale.4 Diamond’s established network within Toronto’s business and tech communities would also be a valuable asset in introducing and growing Trade In.
The application of technology to the automotive market is brimming with potential. Trade In could leverage AI-powered pricing tools for fairer valuations, virtual reality for remote vehicle inspections, blockchain for secure transaction records, or a streamlined online marketplace to connect buyers and sellers more efficiently. Diamond’s experience in building secure and user-friendly digital platforms with Coinsquare would be directly applicable to creating a trustworthy and seamless experience for automotive transactions.
Furthermore, the increasing global shift towards electric vehicles and sustainable transportation could also play a role in Trade In’s vision. Diamond’s early investment in RoketEV indicates an awareness of this trend, and Trade In might aim to facilitate the transition to EVs by providing a platform that simplifies their trade-in process, addresses concerns about charging infrastructure, or offers a marketplace specifically for electric vehicles.
As Toronto eagerly awaits the full unveiling of Trade In in 2025, the city’s entrepreneurial and tech communities are optimistic about the potential impact of Cole Diamond’s latest venture. His history of building successful and disruptive companies from Toronto underscores his commitment to the city’s innovation ecosystem. Trade In promises to be another exciting chapter in his entrepreneurial journey, potentially reshaping a significant consumer market and further solidifying Toronto’s reputation as a hub for technological advancement.