What You Need Before Starting Your Second Startup

What You Need Before Starting Your Second Startup

In the world of innovation, few names resonate with the same authority and impact as Cole Diamond. An entrepreneur, investor, and builder of multi-sector empires, Cole has left an indelible mark on Canada’s financial technology space and is now making waves across real estate, hospitality, and venture investment. From founding Coinsquare, one of Canada’s foremost cryptocurrency exchanges, to spearheading the creation of Tetra Trust, the first qualified custodian for digital assets in the nation, Cole’s journey illustrates what happens when vision meets execution.

This article explores the entrepreneurial path of Cole Diamond, examining his key ventures, investment philosophy, and influence across industries—and why his story is a masterclass in modern leadership and future-forward thinking.

Pioneering the Crypto Revolution: Coinsquare and Tetra Trust

Coinsquare: Building Canada’s Crypto Foundation

Cole Diamond’s rise to prominence began with Coinsquare, a platform he co-founded and led as CEO. Under his leadership, Coinsquare didn’t just become popular—it became Canada’s leading cryptocurrency exchange. By 2018, it had solidified its reputation as the country’s most trusted name in digital asset trading. What set Coinsquare apart was not only its tech but also its regulatory innovation. It became the first IIROC-registered broker-dealer and first registered marketplace in Canada for crypto assets.

These achievements weren’t accidental. Cole guided the company through raising over $100 million in capital, gaining institutional credibility, and driving widespread adoption. In 2019, he was recognized as Canada’s top Tech Entrepreneur, an acknowledgment of his role in transforming how Canadians perceive and interact with digital finance.

Tetra Trust: Redefining Custody for Digital Assets

While many were still wrapping their heads around cryptocurrencies, Cole had already anticipated the next big need: custody. In response, he co-founded Tetra Trust, which became Canada’s first qualified custodian and trust company for digital assets. Tetra filled a crucial gap in the ecosystem by offering secure storage for digital assets—a key concern for institutions and individual investors alike.

Together, Coinsquare and Tetra Trust represent Cole’s deep understanding of financial infrastructure and his ability to not just build companies, but build ecosystems.

Strategic Diversification: From Blockchain to Kitchens

Ghost Kitchen Brands: Disrupting the Food Industry

Cole Diamond’s entrepreneurial reach extends far beyond finance. As the controlling shareholder of Ghost Kitchen Brands, Cole is betting big on the future of food. Ghost kitchens, or delivery-only restaurants, have surged in popularity post-pandemic, and Cole has been at the forefront of this disruption.

Ghost Kitchen Brands is not just any player in this space—it’s a leader in North America, providing a scalable model for food brands to expand without the overhead of traditional restaurants. This move signals Cole’s keen eye for market trends and his commitment to building platforms that anticipate consumer behavior.

Kinetic Commerce: Blending Retail and Technology

Cole is also the majority shareholder of Kinetic Commerce, a company reshaping how physical retail stores interact with digital technologies. Through mobile apps, omnichannel experiences, and retail solutions, Kinetic helps brands deliver seamless shopping journeys. This investment shows Cole’s dedication to bridging physical and digital realms, a consistent theme in his portfolio.

Real Estate and Hospitality: Creating Destinations, Not Just Spaces

While many tech entrepreneurs limit their focus to digital ventures, Cole has taken a diversified approach by building a growing real estate portfolio. In a market often considered traditional, he brings a modern investor’s agility and vision.

In the hospitality sector, Cole co-founded and serves as a Director at Vela in Toronto, a high-end dining destination already making waves in the city. He is also a leading investor and Director at Stella West Hollywood, set to open in mid-2023. These ventures demonstrate Cole’s ability to apply his entrepreneurial expertise to customer experience-driven sectors, reinforcing his multi-dimensional approach to business.

Investing in the Future: Supporting Entrepreneurs and Fund Managers

Cole Diamond doesn’t just build companies—he nurtures ecosystems. His investments span an impressive range of startups and funds, including:

• Shoptype
  
  

• OneLocal
  
  

• RocketEV
  
  

• Evergreen Environmental
  
  

• Cashew
  
  

• NXM
  
  

• Amino
  
  

• BIG Digital
  
  

In addition, he supports emerging fund managers such as NorthSouth, XMonetae, CPS, Harlo, Ripple, and Union. His investment strategy is based on early conviction and long-term partnership, showing that he values both ideas and the people behind them.

By backing these ventures, Cole is playing a vital role in shaping Canada’s next generation of founders and fund managers, ensuring that innovation continues to thrive across sectors.

A Digital Footprint That Reflects a Visionary Mind

Cole’s ownership of the premium domain Diamond.com may seem like a vanity play at first glance, but in the context of his career, it symbolizes branding acumen and long-term digital foresight. This asset mirrors the strength of his name in the business world—rare, valuable, and enduring.

Lessons from Cole Diamond’s Playbook

What sets Cole Diamond apart isn’t just his ability to launch successful companies—it’s the strategic coherence with which he operates across vastly different domains. Whether it’s blockchain, retail, food delivery, or luxury hospitality, Cole:

1. Identifies infrastructure gaps (Coinsquare, Tetra Trust)
   
   

2. Leverages market shifts (Ghost Kitchen Brands)
   
   

3. Blends innovation with tradition (real estate and hospitality)
   
   

4. Invests in people as much as in products
   
   

His career is a blueprint for future-ready entrepreneurship, where adaptability, vision, and ecosystem-building are essential to sustainable success.

Conclusion: Looking Ahead with Cole Diamond

In an era of rapid change and blurred industry boundaries, Cole Diamond is a compelling example of what a 21st-century entrepreneur should look like. He builds with foresight, invests with purpose, and operates with a clarity of mission that has made him a central figure in Canada’s innovation economy.

As digital assets mature, retail continues to evolve, and hospitality redefines itself, Cole is likely to remain at the nexus of these transformations. His journey invites aspiring entrepreneurs, investors, and business leaders to ask themselves: How can we build not just companies, but entire ecosystems? How can we make our ventures resilient across industries and relevant across time?

For those looking to understand the future of innovation, following the story of Cole Diamond is not just inspiring—it’s essential.