Building Better: How Darren Engels is Paving a Path for Ventures to Succeed
Tailwind founder and CEO talks about Tailwind’s roots and his drive to help businesses flourish
Work hard, get money. For an entrepreneur with a big idea, it’s a story many have been told and it seems simple, right? An angel will come along and fund your venture. If you ask Darren Engels, he’ll tell you it’s a bit more complicated than that.
“I knew the competition for capital was high, but in the beginning, I didn’t realize just how high it was for early- and growth-stage companies. Less than 1% of companies are investable by institutional capital, which I think would surprise most people,” says Engels, Tailwind’s CEO. “There are a lot of smart people doing interesting things, but getting your company ready for external capital is a different skillset that most entrepreneurs don’t have.”
“So, if you’re excellent at your profession and want to grow your business, do you want to risk diluting your focus trying to put in the things that investors care about, like a proper governance structure, reporting, or marketing?” he says. “It’s going to be harder than you think, and we have to assume there are no angels, there’s no silver bullet. It can kill an entrepreneur’s spirit if they are not ready for it.”
Engels was working at a respected investment bank when an idea started to grow to build something of his own. Combining a love of early-stage companies with deep experience with capital providers and investors, something sparked to bring a unique offering to the venture capital space. After a year of reflection, tweaking, and then some more tweaking, he landed on Tailwind, based in Calgary, Alberta.
“I thought the traditional investment banking model was broken. It was super transactional and not relationship oriented—it was about the money, not about making businesses better,” Engels says. “I wanted to knit together the rigour of investment banking with other tools, like risk mitigation and a fresh approach to telling the story of a venture, to create value for our clients and capital providers. To me, it’s a responsibility. Our work helps founders build better businesses.”
Engels created a proven process, honed since Tailwind’s inception, that enables his clients to solidify their fundamentals, helping ensure they can confidently withstand the scrutiny of due diligence. The Tailwind process includes identifying vulnerabilities, mitigating risks, empowering clients to tell their story in the language of investors, and connecting them with capital providers.
“We help companies avoid a ‘no’ from capital providers. We act as a strategic partner, which frees up the CEO to focus on growing the business, while we work on strengthening it, and then articulating it to investors,” he says. “It takes a certain mindset to demonstrate a venture is worthy—it’s not as easy as convincing them. You have to do the hard work and prove value, and then you might get the money.”
Engels should know. As a start-up itself, Tailwind has grown from just him and some interns to a team of eight. Since its inception, they have helped dozens of companies through FlightPlan™️ and Check6™️, enabling 14 ventures to raise capital (with an 86% success rate), resulting in more than $370 million raised since 2022.
“We knew we were onto something when some investors asked to share our work with others on our behalf. That’s a good feeling—when someone asks to share it, it’s the best thing,” he says.
From his early idea, he has since built a collaborative and open office, usually complete with a dog or two wandering through the space. It mirrors his own style, full of flowing ideas and helping people out.
“I wanted a culture where I wanted to come to work and learn,” he says. “If I am going to spend more time with these people than my family, I needed to like working with them.”
Engels surrounded himself with a range of interesting people with broad backgrounds and experiences—not just a typical investment banker Type A personality—that pushed him to further develop a growth mindset that has helped him see what might be possible.
“I think I underestimated how good we could be. I’ve surprised myself. It’s been harder than I thought, but it might be better than I thought, too,” he says.
Now entering 2025, Tailwind isn’t slowing down. Over the next year, Engels sees more national and US-growth, a tech-enabled platform and becoming more active in the investment community.
“We have a proven process that we can confidently share to help more companies,” he says. “If I look ahead to when I’m done my tenure at Tailwind, I believe we will have been able to successfully help create 1,000,000 jobs and impact double that.”
“I want to make our community better, and if I could say that we’ve succeeded on that, it would be pretty rad.”
About the author:
Gillian Edwards is a communicator based in Calgary, with 15+ years of expertise in the higher education, business, and non-profit sectors. Her approach is grounded in good judgment, strong relationships and a sense of humour. She quit her 9-to-5 last year to start her own business, Frances & Associates, working with interesting people and projects.