Cole Diamond is a serial entrepreneur best known as the co-founder and former CEO of Coinsquare, Canada’s premier cryptocurrency broker-dealer. He is also the co-founder of Tetra Trust, Canada’s first digital asset custodian, and was the steadying force behind Ghost Kitchens International, which has reshaped the food delivery industry. He has backed numerous notable early-stage startups, including RoketEV, KEEP, and BIG Digital. Diamond is preparing to launch his new company, Trade In, early next year.
Q: How would you say your time at Coinsquare has shaped your subsequent career?
Cole Diamond: My time at Coinsquare gave me a great understanding of the disruptive power of innovation. I had a front-row seat as cryptocurrency was upending traditional financial markets, despite the best efforts of some of the more entrenched legacy players. Leading Coinsquare also reinforced the importance of resilience and adaptability in all avenues of business, which are lessons that I’ve carried with me into every venture I’m involved in. It was a wild ride; an MBA on the road… and now I’m ready for anything.
Q: How do you balance the risks and rewards of investing in radically different industries, such as hospitality, real estate, and technology?
Cole Diamond: I try to recognize the potential in people/teams and ideas, regardless of the sector. Every industry has its own rhythm. I focus on the people first. I’m comfortable with risk when I’m comfortable with the people I’m taking the risk with. Then come fundamentals of the business, etc etc. But if I look back on my winners and losers, it’s primarily because of the people I invested with.
Q: There is significant buzz about your new company, Trade In. Is there anything you can tell us about it in advance of its announced debut next year?
Cole Diamond: We’re closing in on some key investments, and we’re at a pivotal moment. I can’t tell you much about it, except that we are reinventing the way that people sell their cars. I’m excited to run a company again. It’s built around an idea that I have a lot of confidence in. Everybody involved is really excited about it and fully committed to delivering something innovative that will connect with a wide audience. Automotive is the largest consumer market, and we have an opportunity to be a major player.
Q: Is there anything you would have done differently in your entrepreneurial career?
Cole Diamond: Like any early-stage investor and/or entrepreneur, I’ve made moves I wish I could take back. But as far as my approach, I can’t say I would have fundamentally done things differently. I’ve had a lot of successes, and I’ve learned from the missteps. Overall, I’ve learned a lot from being ultra aggressive and I am proud of the outcomes that came from it.
Q: What advice would you offer to young entrepreneurs facing an uncertain business landscape?
Cole Diamond: There will always be uncertainty in business. If you try to wait around for the perfect time, you’ll miss out on opportunities. I will say this – if you try to trod the well-known paths, you’re not going to distinguish yourself, especially as an entrepreneur. Don’t be afraid of the unknown. It’s the trailblazers who end up accomplishing the most, both in business and in life. Man plans, God laughs. Godspeed.
