The Fire Never Goes Out: Why Serial Entrepreneurs Keep Building
In an era where innovation is currency and entrepreneurship is a catalyst for global change, Cole Diamond stands as one of Canada's most dynamic and diversified business leaders. Best known for co-founding Coinsquare and Tetra Trust, Cole’s entrepreneurial journey spans across finance, digital assets, real estate, hospitality, and tech venture investing. His relentless drive, strategic foresight, and commitment to building transformative companies have not only reshaped Canada’s cryptocurrency ecosystem but are now influencing several other sectors on a global scale.
From Coinsquare to Tetra Trust: Pioneering Canada’s Crypto Infrastructure
Cole Diamond’s rise to prominence began with the launch of Coinsquare, a platform that quickly became Canada’s leading cryptocurrency exchange by 2018. Under Cole’s leadership as CEO, Coinsquare achieved several industry milestones. It became the first IIROC-registered broker-dealer and registered marketplace for digital assets in Canada—monumental steps in legitimizing crypto trading in a highly regulated environment.
Beyond regulatory breakthroughs, Coinsquare was instrumental in raising over $100 million in capital, setting a gold standard for investor confidence and operational transparency. In recognition of his leadership and innovation, Cole was named Top Tech Entrepreneur in Canada in 2019—an award that cemented his place among North America’s elite tech visionaries.
Recognizing that cryptocurrency needed not just exchanges but secure custodianship, Cole co-founded Tetra Trust, Canada’s first qualified custodian and trust company for digital assets. Tetra Trust offered a secure bridge between traditional finance and digital assets, enabling institutional participation in crypto with regulatory confidence and financial-grade safeguards.
Expanding the Portfolio: Ghost Kitchens, Commerce Tech, and Real Estate
Having revolutionized one industry, Cole Diamond wasted no time venturing into others. As the controlling shareholder of Ghost Kitchen Brands, he entered the booming food delivery and virtual restaurant market with visionary timing. Ghost Kitchen Brands, which develops and licenses restaurant concepts that operate without dine-in services, proved prescient during the pandemic and continues to scale rapidly, leveraging data and tech to deliver convenience-first food solutions.
His commercial instincts extended further with investments in Kinetic Commerce, a retail technology company focused on enhancing digital and in-store experiences. As majority shareholder, Cole supports Kinetic’s mission to reimagine the future of commerce through interactive retail platforms that blend the online and physical worlds.
Meanwhile, Cole has been quietly assembling a diversified real estate portfolio. While details are kept under wraps, the move signals a strategic effort to build long-term asset value and stability across both commercial and residential sectors—once again demonstrating his ability to operate with both vision and precision.
Building Culture: High-End Hospitality Ventures
In a world where brand experience matters as much as product, Cole’s ventures into hospitality reflect his passion for design, luxury, and cultural impact. He is the co-founder, Director, and largest shareholder of Vela, a high-end Toronto restaurant that has earned acclaim for its modern elegance and elevated dining experience. Vela isn't just a restaurant—it’s a statement of Cole’s refined taste and commitment to creating venues that marry ambiance with innovation.
But Cole's ambitions in hospitality don’t stop at Toronto. He is also one of the leading investors and Directors of Stella West Hollywood, a high-profile project expected to launch in mid-2023. Stella is poised to become a cultural and lifestyle landmark in Los Angeles, combining premium real estate with luxury hospitality for a new era of urban elegance.
Championing Startups and Fund Managers: A Ripple Effect of Innovation
Cole Diamond isn’t just building companies—he’s fueling ecosystems. His personal investment strategy reveals a deep commitment to early-stage innovation and venture capital development. Among the startups Cole supports are:
Shoptype: A social commerce platform transforming how creators and consumers engage with brands.
RocketEV: Pioneering sustainable and electric mobility solutions.
OneLocal and Cashew: Empowering small businesses with marketing and payment tech.
Evergreen Environmental: Tackling climate issues through tech-enabled sustainability.
His portfolio includes disruptive firms like NXM, BIG Digital, and of course, Ghost Kitchen Brands, where he’s played both strategic and financial roles. Cole’s hands-on involvement helps young founders move from concept to execution faster and with more resilience.
Moreover, he backs early-stage fund managers such as NorthSouth, XMonetae, CPS Capital, Ripple Ventures, Harlo Capital, and Union Capital. By empowering fund managers at the ground floor, Cole ensures a ripple effect—capital flows to bold ideas, and innovation scales at speed.
Digital Legacy: The Owner of Diamond.com
As a nod to both branding acumen and digital foresight, Cole Diamond owns the premium domain Diamond.com. This acquisition is more than symbolic—it positions Cole to eventually launch or license a world-class digital brand under one of the most recognizable and marketable domain names in the world. In today’s digital-first economy, this asset holds massive latent potential across luxury, e-commerce, or fintech verticals.
What Sets Cole Diamond Apart?
Many entrepreneurs ride trends. Few build the infrastructure that sustains them. Cole Diamond does both. Whether it's launching Canada’s first regulated crypto exchange, investing in eco-startups, reshaping food delivery, or pioneering immersive retail, Cole’s moves are grounded in long-term value creation. His portfolio is a testament to horizontal diversification with vertical expertise—he doesn’t just touch industries; he transforms them.
Additionally, Cole embodies a rare balance of risk tolerance and regulatory respect, ensuring that even his boldest ventures operate within frameworks that attract institutional and public trust. He builds platforms, not just products, and supports people, not just profits—a hallmark of leaders who build legacies.
Looking Ahead: The Next Chapter in Cole Diamond’s Journey
As the digital economy evolves, one can expect Cole Diamond to remain at the forefront—bridging innovation with regulation, blending tech with experience, and building platforms that scale across borders and sectors. With a portfolio that spans cryptocurrency, fintech, hospitality, real estate, and venture investing, Cole is not just following trends—he is writing the blueprint for the future of entrepreneurship.
The question now is not what Cole Diamond will build next, but how far his influence will reach. In a time when industries are being redefined daily, leaders like Cole are the architects of the future.
If there’s one takeaway, it’s this: Cole Diamond isn’t just a name in Canadian business. He’s a force across global industries. Whether you’re a founder, investor, policymaker, or future entrepreneur, paying attention to his next move might just give you a front-row seat to the next wave of transformative innovation.