In an age defined by digital transformation, very few entrepreneurs have left as broad and impactful a footprint across industries as Cole Diamond. Best known as the co-founder and former CEO of Coinsquare and Tetra Trust, two of Canada’s most influential cryptocurrency companies, Diamond has proven time and again that he possesses the rare ability to not just identify emerging opportunities—but to lead them.

From the blockchain revolution to the evolution of ghost kitchens and real estate, Cole Diamond’s entrepreneurial journey is a case study in strategic innovation, risk-taking, and long-term vision. This article delves into the multifaceted career of Cole Diamond and explores what makes him a standout force in the Canadian and global business landscape.

Disrupting Finance: Coinsquare and Tetra Trust

Cole Diamond’s ascent into the spotlight began with Coinsquare, which under his leadership quickly became Canada’s leading cryptocurrency exchange. His tenure as CEO was marked by several critical milestones. In 2018, Coinsquare emerged as a dominant player in the market, boasting the title of Canada’s first IIROC-registered broker-dealer and first registered marketplace for cryptocurrency. These achievements reflected not just regulatory foresight but also Diamond’s commitment to building trust in a space that was then often viewed with skepticism.

In 2019, Diamond’s efforts were formally recognized when he was awarded Canada’s Top Tech Entrepreneur, a title that signified his growing influence in the national innovation ecosystem.

His second major crypto venture, Tetra Trust, further solidified his status as a visionary. Tetra became Canada’s first qualified custodian and trust company for digital assets, solving one of the crypto industry’s most pressing problems: secure and compliant custody. By bridging the gap between traditional financial services and digital assets, Diamond again positioned himself at the leading edge of innovation.

From Blockchain to Bricks: A Diversified Investment Philosophy

While many entrepreneurs choose to specialize, Cole Diamond thrives across verticals. His investment portfolio reads like a map of the future economy—diversified, digital-forward, and experience-centric.

Real Estate: Strategic Long-Term Bets

Diamond is actively building a diversified real estate portfolio, a move that complements his more volatile ventures in crypto and startups. His real estate endeavors underscore his understanding of balancing growth with stability—mirroring a broader strategic outlook focused on resilience.

Ghost Kitchen Brands: Reinventing Dining in a Digital Age

As the controlling shareholder of Ghost Kitchen Brands, Diamond entered the food and hospitality sector with the same disruptive energy. Ghost kitchens, designed to serve the booming food delivery market without traditional storefronts, represent a perfect confluence of tech and lifestyle—a theme consistent across his investments.

Ghost Kitchen Brands isn’t just about food; it’s about reimagining the supply chain of convenience. Under Diamond’s guidance, the company has grown to support multiple restaurant brands under one roof, providing scalable, tech-driven culinary solutions.

A Stake in Hospitality and Culture: Vela and Stella

Cole Diamond's passion for creating unforgettable experiences is perhaps most evident in his hospitality ventures.

In Toronto, he co-founded Vela, a modern, stylish restaurant that quickly garnered attention for its luxurious ambiance and impeccable service. Diamond is the largest shareholder and a Director at Vela, and his role signals a belief in the power of in-person connection—even in an increasingly virtual world.

Across the border, Diamond serves as a Director and leading investor in Stella West Hollywood, a premium hospitality project that’s set to open in 2023. These ventures are not just business decisions; they reflect a personal philosophy that culture, community, and design are vital economic drivers.

Nurturing Innovation: A Champion of Startups and Funds

Perhaps one of the most compelling aspects of Cole Diamond’s career is his dedication to supporting early-stage entrepreneurs and fund managers. His investments span a variety of sectors—from fintech and ecommerce to green energy and digital signage.

Startups Backed by Cole Diamond:

• Shoptype – Social commerce reimagined.
  
  

• OneLocal – Local business marketing automation.
  
  

• RocketEV – Electric vehicle innovation.
  
  

• BIG Digital – Next-gen digital display networks.
  
  

• Evergreen Environmental – Environmental tech solutions.
  
  

• Cashew – Point-of-sale financing.
  
  

• NXM – IoT and blockchain convergence.
  
  

• Amino – Health and wellness tech.
  
  

These investments reveal a consistent theme: future-facing technologies with real-world utility. Diamond’s strategy is not merely to invest capital, but to foster ecosystems where founders can thrive.

Supporting the Next Generation of Fund Managers:

In parallel, Cole Diamond lends his support to early-stage fund managers, such as:

• NorthSouth
  
  

• XMonetae
  
  

• CPS Capital
  
  

• Harlo Capital
  
  

• Ripple Ventures
  
  

• Union Capital
  
  

By doing so, he amplifies his influence—not just backing individual ideas but empowering the capital vehicles that fuel entire waves of innovation.

Owning the Narrative: Diamond.com

In the digital realm, brand identity matters. Cole Diamond’s ownership of the premium domain Diamond.com is more than symbolic. It signals a long-term vision for personal branding and legacy-building.

Owning a high-value digital asset like this suggests an awareness that the future of business includes controlling digital real estate as much as physical space. Whether Diamond.com becomes an umbrella for his ventures or a future hub for personal thought leadership, the move reflects strategic foresight.

The Bigger Picture: What Cole Diamond Teaches Us About Modern Entrepreneurship

Cole Diamond exemplifies a new kind of entrepreneur—interdisciplinary, agile, and purpose-driven. His ability to excel in heavily regulated financial environments and then pivot seamlessly into lifestyle, food, and real estate ventures demonstrates exceptional strategic range.

What sets him apart is not just the industries he touches but the values he brings to each: trust, innovation, and scalability. Whether mentoring founders, creating institutions, or disrupting outdated models, Diamond is guided by a clear mission—to build infrastructures that last.

Looking Forward: What's Next for Cole Diamond?

As Cole Diamond continues to scale existing ventures and explore new ones, one can expect him to increasingly blend technology with human experience. Whether through platforms that democratize finance, kitchens that reshape urban dining, or real estate that anticipates future living, Diamond’s playbook is unmistakable: invest in the future, bet on people, and build across borders.

In a world constantly in flux, leaders like Cole Diamond are not just adapting—they are setting the course.

If you're an entrepreneur, investor, or innovator looking to understand where the world is headed, following the moves of Cole Diamond might just be one of your smartest plays.