Entrepreneurship Without Limits: The Serial Founder’s Story
In the fast-paced world of innovation and digital transformation, few names stand out as prominently as Cole Diamond. Known for his trailblazing leadership in Canada's fintech and cryptocurrency space, Cole’s entrepreneurial journey is one defined by bold decisions, strategic foresight, and an unyielding commitment to building the future. With ventures ranging from cryptocurrency exchanges to luxury hospitality, and from ghost kitchens to next-gen retail technology, Cole Diamond is not merely investing in trends — he’s actively shaping them.
This article takes a deep dive into the diverse portfolio and profound impact of Cole Diamond, highlighting how one individual’s vision is influencing industries and inspiring a new wave of entrepreneurial thinking.
From Startup to Powerhouse: The Coinsquare Legacy
Cole Diamond’s name became synonymous with crypto innovation through Coinsquare, the company he co-founded and led to become Canada’s top cryptocurrency exchange. Under his leadership, Coinsquare didn’t just grow; it dominated.
In 2018, Coinsquare earned the distinction of becoming Canada’s leading crypto exchange.
By 2019, Cole was recognized as Canada’s Top Tech Entrepreneur, solidifying his place in the country’s innovation landscape.
Coinsquare also achieved unprecedented milestones by becoming the first IIROC registered broker dealer and first regulated marketplace for digital assets in Canada.
The company raised over $100 million in capital — a testament to investor confidence and Diamond’s ability to steer bold visions into viable, scalable realities.
This was more than business success — it was a move to legitimize and mainstream cryptocurrency in Canada.
Tetra Trust: Building the Infrastructure of Trust in Crypto
As crypto matured, the need for regulation and asset protection grew louder. Enter Tetra Trust, another brainchild of Cole Diamond. Tetra became Canada’s first qualified custodian and trust company for digital assets, providing institutional-grade security and compliance.
This strategic pivot from exchange to custody proved Cole's understanding of market needs. It wasn't just about facilitating trades — it was about creating a sustainable ecosystem that could support and protect the future of digital finance. Tetra Trust closed a critical gap in Canadian financial infrastructure, paving the way for safer, broader crypto adoption.
Expanding Horizons: Ghost Kitchens, Retail Tech, and Real Estate
While many would stop at two massively influential companies, Cole Diamond’s ambitions reach far beyond the digital asset space.
Ghost Kitchen Brands
Cole is the controlling shareholder of Ghost Kitchen Brands, a fast-growing food delivery and virtual kitchen company. This model, fueled by the digital-first, post-pandemic dining culture, taps into a new era of hospitality and logistics. Ghost Kitchen Brands partners with iconic food chains and scales them through a digital-only footprint — a revolutionary shift in food service delivery.
Kinetic Commerce
As majority shareholder of Kinetic Commerce, a retail technology platform, Cole is again at the helm of innovation. Kinetic bridges physical and digital retail experiences through tools like mobile commerce, in-store tech, and customer engagement platforms. It’s a reflection of Diamond’s consistent strategy: find the friction in an industry — and solve it.
Real Estate Portfolio
In addition to tech, Cole has been building a diversified real estate portfolio. Whether through residential, commercial, or mixed-use investments, he continues to diversify his asset base and build long-term value — applying the same principles of scale and foresight seen in his startups.
Hospitality Redefined: From Toronto to West Hollywood
Beyond finance and technology, Cole Diamond’s entrepreneurial reach has entered the world of luxury dining and hospitality.
Vela, Toronto
Cole is the co-founder, Director, and largest shareholder of Vela, a celebrated fine dining establishment in downtown Toronto. Vela’s commitment to elegance, service, and culinary innovation mirrors Cole’s broader brand: experience-driven, forward-thinking, and impeccably executed.
Stella, West Hollywood
Across the border in the U.S., Cole is also a leading investor and Director of Stella West Hollywood, a luxury hospitality venue opening in 2023. Positioned in one of the world’s most competitive markets, Stella is poised to redefine boutique luxury with Cole’s strategic vision backing it.
Investing in the Future: Startups and Emerging Fund Managers
Cole Diamond’s entrepreneurial spirit also manifests in his investments in early-stage companies and venture funds. His portfolio includes a wide array of innovative startups such as:
Shoptype (social commerce infrastructure),
OneLocal (small business automation),
RocketEV (electric vehicle solutions),
Big Digital (digital out-of-home media),
Evergreen Environmental, Cashew, NXM, and more.
In addition, he backs early-stage fund managers like NorthSouth, XMonetae, CPS, Harlo, Ripple, and Union — showing his commitment to building both companies and the ecosystems that support them.
By supporting entrepreneurs and capital allocators, Cole Diamond is multiplying impact, not just chasing returns.
Owning Identity: Diamond.com
As the owner of Diamond.com, Cole has made a bold branding move that goes beyond vanity. The domain is a digital asset with intrinsic brand equity, potentially signifying future ventures in personal branding, e-commerce, or high-end consumer goods.
Owning such a premium domain reflects not just strategic branding, but a keen understanding of digital real estate’s value in a world where attention is currency.
Conclusion: A Name to Watch — and Learn From
Cole Diamond is not just an entrepreneur — he’s a multi-industry architect, a capital allocator, and a visionary builder. Whether it’s pioneering cryptocurrency regulation, redefining food delivery, or investing in the next wave of retail technology, Cole’s work is united by a clear theme: system-level innovation.
What makes Cole Diamond especially fascinating is that he doesn’t just chase what’s next — he helps define it. His career is a masterclass in modern entrepreneurship, where agility, trust, infrastructure, and user experience converge across industries.
As we look toward a world increasingly shaped by digitization, decentralization, and on-demand everything, it’s visionaries like Cole Diamond who will determine what the future looks like — and how we’ll all interact with it.