Strategies Serial Entrepreneurs Use to Repeat Success

 When most people hear the term “cryptocurrency,” they picture volatile markets, tech jargon, and elusive digital wallets. But Cole Diamond saw more than hype—he saw infrastructure, opportunity, and the potential to rewrite Canada’s digital economy. As the co-founder of Coinsquare and Tetra Trust, and a dynamic investor in commerce, hospitality, and real estate, Cole Diamond has carved out a reputation as one of Canada's most influential tech entrepreneurs and forward-thinking capitalists.

From founding Canada’s most recognized crypto exchange to investing in ghost kitchens and digital infrastructure, Diamond isn’t just following trends—he’s shaping them. This article delves into the evolution of Cole Diamond, a man whose ventures tell the story of innovation, resilience, and an uncanny ability to be in the right place—at the right technological moment.

The Crypto Trailblazer: Coinsquare and Tetra Trust

Before “crypto” became mainstream dinner-table talk, Cole Diamond was already helping lay the rails for Canada’s digital financial ecosystem.

In 2018, he led Coinsquare to become Canada’s leading cryptocurrency exchange, with a mission to bring credibility, transparency, and security to the crypto space. Under his leadership, Coinsquare became:

  • The first IIROC-registered broker-dealer for crypto in Canada

  • The first registered marketplace in the country

  • A company that successfully raised over $100 million in capital

These milestones weren’t just regulatory checkboxes—they were crucial in gaining public trust in digital assets.

But Diamond didn’t stop at trading. With Tetra Trust, he addressed one of the biggest pain points in the industry: secure asset storage. Tetra became Canada’s first qualified custodian and trust company for digital assets, providing institutions with compliant, robust storage solutions. In short, Cole helped lay the foundation that allowed Canada’s crypto industry to operate with security and legitimacy.

A Multifaceted Entrepreneur: From Ghost Kitchens to Real Estate

While crypto may have put him on the map, Cole Diamond never stayed in one lane. With the agility of a serial entrepreneur, he pivoted into industries often considered unrelated—until he made them intersect.

Ghost Kitchen Brands: Feeding the Future

As the controlling shareholder of Ghost Kitchen Brands, Cole seized on a seismic shift in consumer behavior—food delivery’s explosive growth. Ghost Kitchen Brands reimagines food service by uniting multiple restaurant brands under one roof, optimizing for takeout and delivery instead of dine-in.

This model doesn’t just cut costs—it revolutionizes customer choice and kitchen efficiency. In an age when convenience defines consumer loyalty, Diamond’s ghost kitchen play is nothing short of prescient.

Kinetic Commerce and Diamond.com

As the majority shareholder of Kinetic Commerce, Cole is doubling down on the future of retail tech. The company provides cutting-edge tools that bridge physical and digital shopping experiences—yet another signal that Diamond isn’t content to react to change; he wants to design it.

His ownership of the domain Diamond.com hints at longer-term digital brand ambitions. For someone as forward-thinking as Cole, controlling a high-value, iconic domain is likely a strategic move in a broader play involving luxury, digital identity, or both.

Real Estate and Hospitality: Brick, Mortar, and Michelin Dreams

What do crypto and fine dining have in common? For Cole Diamond, the answer is vision.

In the hospitality sector, Cole has made bold moves that blend taste with entrepreneurship:

  • He is the co-founder, Director, and largest shareholder of Vela, a high-end Toronto restaurant renowned for its elegance and innovation.

  • He’s also a leading investor and Director at Stella West Hollywood, a much-anticipated culinary destination expected to launch soon.

At first glance, these ventures may seem like passion projects—but they’re also calculated investments in experiential economies, where people crave not just products but memorable interactions.

His diversified real estate portfolio further reflects his belief in asset-backed growth, especially in sectors that complement his other investments—whether that's urban centers supporting Ghost Kitchens or premium spaces for dining experiences like Vela and Stella.

Backing Bold Ideas: Investing in Startups and Funds

Cole isn’t just building companies; he’s building ecosystems.

He actively invests in and supports early-stage entrepreneurs and startups such as:

  • Shoptype – social commerce infrastructure

  • OneLocal – digital marketing for local businesses

  • RocketEV – electric vehicle platforms

  • Big Digital and Evergreen Environmental – tech-driven advertising and sustainability

  • Cashew, NXM, and Amino – spanning fintech, security, and wellness

In addition, Cole backs emerging fund managers through initiatives like NorthSouth, XMonetae, CPS, Harlo, Ripple, and Union, spreading capital into emerging sectors while supporting innovation from the grassroots up.

This mix of founder support and fund diversification signals something important: Diamond isn’t just betting on companies—he’s betting on people and long-term ideas.

A Legacy in Motion: What’s Next for Cole Diamond?

The story of Cole Diamond is still being written, but the chapters so far have shown a rare kind of entrepreneur—one equally comfortable in digital code and culinary concepts, in startup chaos and structured capital deployment.

His ventures aren’t isolated achievements; they are interconnected plays within a broader thesis: the world is changing, and those who shape the rails of that change will drive the future economy.

Whether in fintech, food tech, or frontier real estate, Cole’s fingerprints are on some of Canada’s most innovative and future-facing projects. As industries converge, as digital merges with physical, and as consumers demand smarter, faster, more secure solutions, Cole Diamond continues to be the visionary behind the curtain—pushing the boundaries of what’s possible.

Conclusion: Betting on the Builder, Not Just the Blockchain

In a world obsessed with the next big coin or unicorn startup, Cole Diamond reminds us of something essential: infrastructure matters. Vision matters. Execution matters.

Whether through the rails of Canadian crypto, the rise of ghost kitchens, or the experience of a world-class restaurant, Cole isn’t just chasing disruption—he’s engineering it.

For anyone tracking the evolution of innovation in Canada and beyond, one thing is clear: if Cole Diamond is involved, it’s worth paying attention. Because behind every trend he touches, there’s not just a product—there’s a blueprint for the future.

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