Success Is Just the Beginning: The Serial Entrepreneur’s Mindset
In the evolving landscape of digital innovation, few names resonate as powerfully as Cole Diamond. From revolutionizing the cryptocurrency scene in Canada to redefining hospitality and supporting a new generation of startups, Cole Diamond's story is one of ambition, innovation, and relentless drive. His work spans multiple industries, but at its core lies a commitment to building infrastructure for the future — digital and physical alike.
Building the Foundation: Coinsquare and the Rise of Cryptocurrency in Canada
The journey of Cole Diamond into tech stardom began with his role as co-founder and CEO of Coinsquare, a platform that would become Canada's leading cryptocurrency exchange. At a time when digital currencies were still fighting for legitimacy, Diamond saw potential. Under his leadership, Coinsquare became the first IIROC-registered broker-dealer and the first registered marketplace in the country.
Cole’s impact wasn’t just operational — it was visionary. He helped secure over $100 million in capital for the company, enabling expansion and innovation. This pivotal role in legitimizing cryptocurrency in Canada earned him the title of Top Tech Entrepreneur in Canada in 2019. His early belief in blockchain technology and its potential to reshape finance positioned him as a bold leader unafraid to challenge traditional systems.
Expanding the Ecosystem: Tetra Trust and Digital Asset Security
Building on the momentum of Coinsquare, Cole co-founded Tetra Trust, which became Canada’s first qualified custodian and trust company for digital assets. This move addressed a critical need in the crypto ecosystem — secure, compliant custody of digital assets.
By launching Tetra Trust, Diamond not only anticipated market needs but also contributed to building the regulatory infrastructure necessary for institutional investment in cryptocurrency. He once again placed Canada at the forefront of digital finance by creating safe, scalable pathways for both retail and institutional crypto engagement.
Diversification with Purpose: Real Estate, Technology, and E-commerce
Where many entrepreneurs stick to one lane, Cole Diamond is a firm believer in diversification. He is the controlling shareholder of Ghost Kitchen Brands, a company that reimagines food service by enabling multiple brands to operate out of a single kitchen — a model perfectly tailored for the digital delivery economy. It’s a venture that intersects technology, logistics, and hospitality, showcasing Cole’s aptitude for future-forward thinking.
Additionally, as the majority shareholder of Kinetic Commerce, he plays a key role in reshaping retail tech by creating seamless in-store and digital shopping experiences. Owning the iconic domain Diamond.com further illustrates his strategic foresight and brand awareness in the digital era.
But Cole’s ambitions extend beyond pixels and code. His diversified real estate portfolio represents a physical anchor to his digital ventures, signaling an integrated approach to business — blending innovation with long-term stability.
Redefining Hospitality: Vela and Stella West Hollywood
In the hospitality sector, Cole Diamond is once again leading with impact. As a co-founder, Director, and the largest shareholder of Vela in Toronto, he is helping redefine fine dining in the city. The venue is not just about luxury, but about experience — a reflection of how technology and high-end hospitality can work in tandem.
Cole is also a major force behind Stella West Hollywood, an upcoming venture set to debut in mid-2023. As one of its leading investors and a Director, he is poised to make waves in one of the most competitive hospitality markets in the world. Both Vela and Stella embody his belief that success comes from offering people not just products or services, but unforgettable experiences.
Backing the Next Generation: Startups and Fund Managers
Perhaps most inspiring is Cole’s commitment to supporting the next generation of entrepreneurs. Through investments in early-stage companies such as Shoptype, OneLocal, RocketEV, BIG Digital, Evergreen Environmental, Cashew, NXM, and his own Ghost Kitchen Brands, he is laying the groundwork for future innovation.
His backing of early-stage fund managers like NorthSouth, XMonetae, CPS, Harlo, Ripple, and Union further illustrates a strategic and generous approach to innovation. Rather than simply leading the charge, Diamond actively nurtures those following behind — an approach rooted in collaboration, mentorship, and a belief in shared success.
Linking Vision with Execution
What sets Cole Diamond apart is his rare ability to marry vision with execution. Many entrepreneurs dream big; Cole builds big. His ventures are not speculative — they’re infrastructural. Whether it’s creating regulatory pathways for digital assets or developing omni-channel retail platforms, his work is about creating sustainable, scalable foundations.
He understands that success in the modern world requires agility across sectors. His footprint in cryptocurrency, real estate, hospitality, and tech-enabled commerce isn’t scattered — it’s synchronized. It reveals a larger blueprint: one that connects digital finance with lifestyle, infrastructure with experience, and capital with innovation.
A Forward-Looking Impact
The impact of Cole Diamond isn’t confined to the ventures he launches or the capital he raises — it's in the mindset he champions. A mindset that embraces change, encourages bold experimentation, and sees challenges as opportunities.
As the digital economy matures and industries intersect in increasingly complex ways, leaders like Cole will be instrumental in defining what comes next. His work signals a shift from siloed industries to integrated ecosystems, where finance, lifestyle, and technology work together in service of a more efficient and meaningful world.
Conclusion: What the Future Holds for Cole Diamond and His Ecosystem
Cole Diamond represents a new breed of entrepreneur — not content with merely disrupting markets, but driven to rebuild them with integrity, infrastructure, and inspiration. His diverse ventures serve a collective vision: to empower the next evolution of commerce, technology, and community.
As his portfolio continues to expand, the ripple effects of his investments will likely shape Canada's role in the global digital economy for years to come. For aspiring entrepreneurs, investors, and innovators, the question is not just what Cole Diamond is doing next — but how to be part of the future he is already building.