$370 Million Raised in 2 Years: How People, Process, and Purpose Fueled Our Clients' Success
When ClearSky Global secured $C230 million, it wasn't just another deal for Calgary's emerging tech scene—it was validation. The CVCA H1 2024 Venture Capital Report finally confirmed what insiders had been whispering: Calgary had quietly risen to become Canada's third-largest venture market, and according to Pitchbook’s Global VC Rankings, 61st globally. Behind ClearSky's raise—celebrated as Deal of the Year at the Start Alberta Tech Awards, and standing as the largest early-stage financing for SAF, all-time, globally—lies a counterintuitive success story.
While Canadian venture capital deal value has dropped 47% year-over-year, our firm has helped clients secure C$370 million since 2022. This anomaly isn't accidental. In a landscape where only about one in 200 startups attempting to raise venture capital succeeds, our portfolio companies are raising venture capital funding at an 86% success rate and are closing rounds at a pace 44% faster than the market rate. Their secret? A framework built on three pillars that transcends traditional fundraising approaches: People, Process, and Purpose. Our founders’ success stories are not just achievements but evidence of a repeatable methodology that works counter to market trends.
People
Tailwind’s team has grown from three to eight, with people from a variety of backgrounds in addition to finance—marketing, research, tech, agriculture, academia—which brings diversity of thought and experience that enables non-traditional thinking in an increasingly uncertain landscape. Different in background, the team is united by shared values of pursuing excellence, thinking bigger and creating happiness.
As a sector-agnostic firm, this is incredibly important. Cross-sector expertise plays a key role in bridging communication gaps between founders and investors from different industries and theses, allowing us to translate sector-specific terminology into a common language that both parties can easily understand.
Our firm's distinct advantage lies in our ability to convert relationship capital into financial capital. The strength of these connections stems from reciprocal trust developed over years. This reputation creates a reinforcing cycle—our rigorous vetting process makes us a trusted deal flow source, which in turn attracts higher-quality investors and opportunities.
Process
In a market where deal count has contracted by 14% since 2023, our unique diligent preparedness framework has emerged as a decisive differentiator for clients navigating heightened investor scrutiny. Unlike standard approaches that focus primarily on financial metrics, our methodology has been engineered to anticipate and address the evolving risk sensitivities of post-2022 investors.
Check6™ is a fast, cost-effective way to help companies get investment-ready and successfully complete a founder-led raise, ensuring founders understand how capital providers will evaluate their opportunity, identifying the key blind spots in their venture that pose barriers to capital, and illuminating strategic pathways to success. Built on insights from hundreds of hours working with high-net-worth investors, family offices, VCs, and PEs, Check6™ gives early- and growth-stage companies a structured, investor-focused approach to capital raising.
FlightPlan™ ensures that the venture has the requisite discipline and competencies to earn investor trust, strengthening the fundamentals and financials, and producing a comprehensive set of materials that demonstrate to investors their ability to create impact and value.
This preparation creates a multiplier effect when ventures work with us on Launch Capital Raise, a facilitated raise process in which we selectively market them to our investor network. The trust established through our rigorous process translates to privileged attention from capital providers increasingly protective of their time and resources.
Raising capital is hard, and takes a lot of time–—time, which is the most valuable resource a founder has. A founder's skill in strategically prioritizing and managing their time plays a crucial role in determining the company's chances of success or failure.
Purpose
The $C370 million we've helped secure over two years represents more than a financial milestone—it's a catalyst for tangible economic and social transformation. Our purpose is to diligently prepare companies to scale and attract capital so that they can create impact and value. Why? Because we believe economic prosperity uplifts humanity, and that diligently prepared companies are more likely to scale, create jobs, and transform communities.
Our portfolio companies now span three continents, allowing us to support ventures with impact on a global scale.
Our engagement model fundamentally reinforces entrepreneurial capability. "Tailwind has given me growth and hope," explains Martin Molyneaux, President and CEO of Molyneaux Asset Management, after investing in our vetted portfolio companies. On the founder side, Mark Tysowski, Founder and CEO of Canadian Resource Roadways, shared that “Tailwind’s contributions were fundamental in nature” to achieving a successful raise.
Success Favours the Diligently Prepared
When Darren Engels founded our firm, he envisioned a foundationally different approach to founder support—one that combines the analytical rigor of finance with marketing expertise in a proprietary, holistic, and structured approach that we call diligent preparedness, to build a better business.
The ultimate measure of our impact won't be capital deployed but dreams realized—innovative solutions reaching markets that need them, jobs created in communities that benefit from them, and founders fulfilling potential that might otherwise have remained unrealized. For us, success means continuing to evolve our People, Process and Purpose framework into an increasingly powerful catalyst for ventures that combine commercial viability with meaningful impact