Creating Success on Repeat: Inside the Serial Entrepreneur’s World
In the dynamic intersection of finance, technology, real estate, and hospitality, few names carry as much cross-industry influence as Cole Diamond. A serial entrepreneur with a sharp eye for innovation and a bold appetite for calculated risk, Diamond’s career is a testament to how vision, tenacity, and timing can converge to create transformative ventures. From co-founding Canada’s top cryptocurrency companies to redefining the culinary experience and empowering early-stage startups, Cole Diamond’s impact is expansive, strategic, and undeniably future-forward.
The Crypto Pioneer: Redefining Digital Finance in Canada
Cole Diamond is best known as the co-founder and former CEO of Coinsquare, Canada’s leading cryptocurrency exchange. When the crypto world was still emerging from the fringes of finance, Diamond positioned Coinsquare at the forefront of legitimacy and regulatory compliance.
In 2018, Coinsquare became Canada’s number one crypto exchange under Diamond’s leadership. But that wasn’t the only milestone—Cole was instrumental in making Coinsquare the first IIROC-registered broker-dealer and marketplace for digital assets in Canada, setting a national precedent in digital asset regulation. His leadership also led to the company raising over $100 million in capital, a testament to investor confidence and strategic growth.
In 2019, this groundbreaking work earned Diamond the Top Tech Entrepreneur in Canada award, solidifying his reputation as one of the most influential figures in the country’s tech landscape.
Expanding the Digital Ecosystem: Tetra Trust and Custody Innovation
Never one to rest on laurels, Cole Diamond continued pushing boundaries with the founding of Tetra Trust—Canada’s first qualified custodian and trust company for digital assets. While Coinsquare gave Canadians a platform to trade crypto, Tetra Trust addressed the equally critical need for secure and regulated storage of those assets.
Tetra Trust represented the next logical step in building a robust digital finance ecosystem in Canada. By offering institutional-grade custody solutions, Diamond not only solved a market need but also supported the broader adoption of cryptocurrency among banks, fintechs, and asset managers.
This end-to-end approach—exchange and custody—shows how Cole isn’t just chasing trends. He’s building infrastructure.
Diversification and Strategic Investments: From Ghost Kitchens to Digital Retail
While some entrepreneurs stick to one vertical, Cole Diamond thrives across industries. Today, he’s the controlling shareholder of Ghost Kitchen Brands, a revolutionary food delivery platform leveraging existing restaurant infrastructure to deliver food from multiple brands under one roof.
Ghost Kitchen Brands has capitalized on the post-pandemic food delivery surge, utilizing tech-first logistics to maximize efficiency and minimize overhead. As delivery becomes a mainstay in urban life, Diamond’s foresight places him at the core of this evolution.
He's also a majority shareholder in Kinetic Commerce, a company bridging the digital and physical retail experience through connected technologies. In an era where e-commerce and brick-and-mortar are converging, this investment aligns perfectly with global retail trends.
Moreover, Diamond owns Diamond.com, an ultra-premium domain asset that reflects both branding genius and long-term digital strategy.
Real Estate: Building Legacy Through Tangibility
Real estate is often considered a classic choice for diversification, but Cole Diamond doesn’t just dabble—he builds a portfolio that balances stability with innovation. Whether through strategic property acquisition or investment in emerging neighborhoods, his approach demonstrates a long-term vision grounded in market awareness.
What sets his real estate interests apart is how they align with his other ventures—creating cross-industry synergies. For example, his involvement in hospitality spaces like Vela and Stella isn’t just about owning buildings; it’s about owning experiences.
Hospitality Ventures: Elevating Taste and Experience
In the heart of Toronto, Cole Diamond is the co-founder and largest shareholder of Vela, a fine dining establishment that merges culinary excellence with immersive ambiance. Beyond the food, it’s a space that embodies creativity, luxury, and community.
Diamond is also a leading investor and Director of Stella West Hollywood, a highly anticipated hospitality destination slated for opening in mid-2023. With Stella, Diamond is entering the global stage—proof that his vision isn't confined to Canadian borders.
What’s remarkable here is how he blends passion with business acumen. These aren’t vanity projects; they’re curated investments driven by high-growth potential and cultural relevance.
Empowering the Next Generation: Investments in Startups and Funds
Not all of Cole Diamond’s successes are his own—many are built through his mentorship and funding of early-stage entrepreneurs. His portfolio includes diverse startups like Shoptype, OneLocal, RocketEV, BIG Digital, Cashew, and Amino. These startups range across marketing automation, electric vehicles, digital out-of-home advertising, fintech, and health tech.
Diamond isn’t just writing checks—he’s actively supporting the visionaries who are shaping tomorrow. Whether through strategic guidance, board roles, or operational advice, he brings value beyond capital.
In parallel, he supports emerging fund managers such as NorthSouth, XMonetae, CPS, Harlo, Ripple, and Union, helping deploy smart capital into untapped opportunities. This dual strategy of direct and fund-based investing shows how Diamond is creating a sustainable ecosystem of innovation.
What Makes Cole Diamond Different?
At the core of Cole Diamond’s success is his ability to see what others don’t—then build what others can’t. He identifies nascent trends, scales fast, and brings regulatory and institutional credibility to unstructured industries.
He is not just a founder or investor—he’s a system builder.
His ventures aren’t isolated; they often complement one another. His ability to connect fintech with regulation, digital retail with real estate, or hospitality with brand strategy reflects an uncommon fluency across disciplines.
Equally important is his commitment to Canadian innovation. By laying the groundwork for cryptocurrency infrastructure and supporting local startups, Diamond has made a lasting imprint on Canada’s economic future.
Conclusion: The Blueprint for a 21st Century Entrepreneur
In a world where many chase quick wins, Cole Diamond is playing a longer, more meaningful game. He doesn’t just invest—he builds. He doesn’t just innovate—he institutionalizes. Whether it's transforming Canada's crypto landscape, redefining hospitality, or empowering a new wave of startups, Diamond's approach is holistic, strategic, and rooted in vision.
As technology, culture, and finance continue to evolve, entrepreneurs like Cole Diamond will define what leadership looks like in the 21st century. He is a rare example of someone who not only rides the wave of disruption—but architects it.
The question isn’t what Cole Diamond will do next—it’s how the industries he touches will evolve because of it.