Cole Diamond is a serial entrepreneur and early-stage business investor based in Toronto. He is best known in the business world for being the co-founder and CEO of Coinsquare, Canada’s top cryptocurrency exchange, and co-founding Tetra Trust, the country’s first qualified digital asset custodian. Under his leadership, Coinsquare raised over $100M and became Canada’s first crypto-focused broker-dealer and marketplace, achieving registration with the Investment Industry Regulatory Organization of Canada (IIROC) and the Ontario Securities Commission (OSC). In recognition of his work in the field, in 2019, Cole was named Canada’s top Tech Entrepreneur by the Digital Finance Institute, a think tank that deals in matters of tech, financial innovation, and regulation.
In addition to his ventures in the crypto space, Cole Diamond has expanded into several other industries. He is the controlling shareholder of Ghost Kitchens International, a company revolutionizing the food delivery market through its innovative online order fulfillment model. Within the hospitality sector, Cole co-founded Vela, a top-rated fine-dining restaurant in downtown Toronto, and serves as the largest shareholder. He is also an investor and board member at Stella, an upscale Italian restaurant in West Hollywood, Los Angeles.
As an investor, Cole is passionate about supporting startups and innovative new ventures. He has backed companies like Big Digital, KEEP, and RoketEV. His investment portfolio extends to real estate, where he has strategically assembled a diverse range of properties in promising markets.
Cole’s career is defined by his ability to take on big challenges and big risks, disrupting industries ranging from cryptocurrency to food service and retail. His latest project, Trade In, is a tech company set to launch in 2025.
We were fortunate enough to catch up with Cole Diamond and ask him a few questions about his career journey, his philosophy on entrepreneurship, and his plans for any exciting new projects.
Q: As an entrepreneur many times over, what lessons have you learned from co-founding successful ventures like Coinsquare and Tetra Trust that you can share with our readership?
Cole Diamond: A lot of the conventional wisdom surrounding entrepreneurship is actually quite true. You have to be tenacious and adaptable. You also need to have a vision for what you want to accomplish and an inherent need to succeed against all odds. An optimistic outlook also helps things along, without question. And it goes without saying that you need to have a product or service that the public wants to buy. I realize that these are generalities, but they happen to be true and critical.
Q: You co-founded Coinsquare in 2016, which means you were a pretty early adopter in cryptocurrency terms. What inspired you to enter into that relatively unknown and unestablished industry at that point?
Cole Diamond: Put simply, I saw the potential for cryptocurrency to change the world. In the lead-up to launching Coinsquare, I also saw that Canada was lagging a bit behind in the crypto sphere, and consequently, there was space for me to fill a critical gap in the market. After realizing all this, I acted fast, and within a shorter amount of time than anticipated, the company was rocketing its way to success. It was very good timing.
Q: You’re also an investor known for supporting several startups, which is a notoriously risky thing to do. Do you have any special criteria you use when deciding where to invest your capital?
Cole Diamond: Most of my criteria for investment is based around two things: one, the idea. The idea has to be sound, well-thought-out, and above all else, innovative. I don’t have a great deal of interest in backing a rehashed version of an old idea. The second criterion I use is my impression of the entrepreneur in question. Most of my decision comes down to instinct. Is this person a go-getter? Do they truly believe in themselves and their abilities? Do they inspire confidence? Can they sell their idea well? All of these are factors I consider.
Q: What advice would you give to novice or would-be entrepreneurs interested in entering the rapidly changing tech industry?
Cole Diamond: The best piece of advice I can relay is that you absolutely, positively must stay up to date on all the latest developments—there’s just no way around it. Without mincing words, the tech space is a cutthroat environment, meaning that if you don’t continuously refine and optimize your processes, procedures, and equipment, you will inevitably fall behind your competitors. It’s not an industry that rewards complacency; quite the opposite. You have to be nimble, open-minded, and always thinking about your next move. And you need to be fast to adjust your product or service once you get to market and your customers start giving you feedback.
Q: Looking ahead, what can you share about your upcoming tech project, Trade In, and what makes it unique in the market?
Cole Diamond: At this point in Trade In’s development, there’s not too much I can share with the press. Suffice it to say, the company operates in the tech space and even now we’re looking into doing some things that will make a big splash within the auto industry. I will say this: stay tuned for the grand debut in 2025. It’s going to be big.
