From One to Many: The Psychology Behind Serial Entrepreneurship

In the rapidly evolving world of digital innovation, few names embody bold leadership and future-focused thinking like Cole Diamond. As a trailblazing entrepreneur who has reshaped Canada’s crypto, tech, hospitality, and investment landscapes, Diamond’s dynamic journey offers a masterclass in disruptive thinking, strategic growth, and unwavering ambition.

From co-founding Canada’s top cryptocurrency exchange to building cutting-edge dining experiences and investing in next-generation startups, Cole Diamond’s influence stretches far beyond Silicon Valley-style success stories—it’s deeply rooted in real-world transformation. This article dives into the impressive portfolio of Cole Diamond, uncovering what makes him a force in Canada’s innovation economy and a global entrepreneur to watch.

Pioneering Canada’s Crypto Revolution

When most Canadians were still trying to understand Bitcoin, Cole Diamond was already busy building the country’s premier cryptocurrency exchange: Coinsquare. Under his leadership, Coinsquare didn’t just ride the crypto wave—it shaped it.

Becoming Canada’s first IIROC-registered broker-dealer and first regulated marketplace, Coinsquare set the gold standard for digital asset trading. This move towards regulation wasn’t just a business strategy; it was Diamond’s commitment to legitimacy and trust in an industry long overshadowed by skepticism.

“Cole Diamond helped change how digital finance is viewed in Canada. He created infrastructure where there was chaos—bringing clarity, regulation, and trust to the crypto space.”

During his tenure as CEO, Diamond helped the company raise over $100 million in capital, rapidly scaling Coinsquare into a fintech powerhouse. This momentum earned him the 2019 Top Tech Entrepreneur in Canada—a recognition of both visionary foresight and relentless execution.

Redefining Digital Custody with Tetra Trust

While many celebrated the crypto boom, Diamond turned his attention to an emerging need: secure digital asset custody. Enter Tetra Trust, co-founded by Diamond to become Canada’s first qualified custodian and trust company for digital assets.

In an industry where institutional adoption hinges on secure, regulated infrastructure, Tetra Trust filled a critical void. By offering compliance-driven custodianship of digital assets, Tetra reinforced Cole Diamond’s position as a pioneer focused not just on building for today—but securing the future.

A Diversified Portfolio: From Kitchens to Commerce

Unlike many entrepreneurs who stay within their niche, Cole Diamond thrives on diversity. As the controlling shareholder of Ghost Kitchen Brands, Diamond ventured into food tech—redefining food delivery through virtual restaurant models.

Ghost Kitchen Brands is not just a business; it’s a visionary response to shifting consumer habits. By harnessing underutilized commercial kitchen space and leveraging digital platforms, the company created a frictionless, scalable food delivery ecosystem—long before the pandemic made it mainstream.

And then there’s Kinetic Commerce, a leader in retail experience technology. As its majority shareholder, Diamond is betting big on the future of omnichannel retail—seamlessly connecting physical and digital shopping experiences. These investments showcase his sharp understanding of where consumer behavior is headed and how to meet it with technology-driven solutions.

Betting Big on Hospitality

Diamond’s entrepreneurial curiosity doesn’t end with tech. He’s made significant strides in the hospitality sector, bringing a luxury-meets-innovation ethos to the table.

As co-founder, director, and largest shareholder of Vela—one of Toronto’s most elegant dining destinations—Diamond blends high-end culinary experiences with thoughtful design and service. Meanwhile, in the U.S., he’s a leading investor and director of Stella West Hollywood, a soon-to-launch hospitality icon set to redefine LA’s restaurant and lounge scene.

Both ventures reflect Diamond’s keen eye for untapped potential in industries not often associated with disruption. They also speak to his understanding of experiential branding—creating not just a product or service, but a moment worth remembering.

A Champion for Entrepreneurs and Emerging Funds

For all his personal achievements, one of the most powerful aspects of Cole Diamond’s journey is his commitment to others’ success. From backing early-stage entrepreneurs (Shoptype, OneLocal, RocketEV, Cashew, NXM, BIG Digital) to supporting emerging fund managers (NorthSouth, CPS, Harlo, Ripple, Union), Diamond actively nurtures the next wave of disruptors.

“Cole Diamond is building more than companies—he’s building ecosystems.”

His investments aren’t random. They’re carefully chosen bets on technologies and people who are out to solve big problems—whether it’s electrifying transport, transforming retail marketing, or making digital finance more secure.

Through these partnerships, Diamond isn’t just multiplying wealth—he’s multiplying impact.

More Than Business: A Legacy in the Making

Beyond boardrooms and balance sheets, Cole Diamond’s reach extends into culture, community, and capital reallocation. As the owner of the domain Diamond.com, he commands a digital asset symbolic of timeless value and forward-thinking.

He’s also expanding into real estate, building a diversified portfolio that reflects his long-term approach to wealth, sustainability, and market evolution.

This holistic, multi-sector strategy isn’t about chasing trends. It’s about seeing around corners. It’s about building a legacy—not just of wealth, but of meaningful innovation that touches everyday lives.

The Cole Diamond Blueprint: Vision, Grit, and Impact

If there’s a single thread tying Cole Diamond’s ventures together, it’s vision paired with execution. He doesn’t wait for markets to mature—he helps create them. He doesn’t follow the rules—he helps write them.

From building Canada’s digital financial backbone to fueling the future of hospitality, retail, and food tech, Diamond’s portfolio reads like a playbook for the next generation of entrepreneurs.

Yet, what sets him apart is not just his business acumen—it’s his ability to inspire innovation in others. By funding ideas, mentoring founders, and reinvesting in emerging ecosystems, he is creating ripples of change that will be felt for decades.

Conclusion: What the Future Demands of Us All

In an age marked by volatility and velocity, Cole Diamond offers a powerful reminder that true entrepreneurship is not about luck—it’s about courage, conviction, and contribution. His journey urges us to ask:

“What future are we building—and who are we building it for?”

Whether you’re a founder, investor, student, or strategist, the Cole Diamond story serves as a compelling call to think bigger, move faster, and build bolder. Because in the world that’s coming, those who lead with purpose—and act with precision—will define the next era.