Navigating the Startup Systems

The fast-paced world of entrepreneurship, where innovation and ambition collide, can often be fraught with perils. But University of Calgary graduates Keara Gillis and Sarah Mateshaytis are doing their best to help people find success with grace, understanding and empathy. 

Their journey, intertwined with the genesis of their own social enterprise, Collectively Tangled, sheds light on the often-overlooked mental health challenges facing startups and entrepreneurs. Entrepreneurs often face an uphill battle of uncertainty, stress and constant pressure to succeed. The pursuit of perfection and the blurred boundaries between work and personal life further compound these challenges, leaving many entrepreneurs vulnerable to burnout, anxiety and depression.

For Gillis and Mateshaytis, both MSW’20, the decision to start Collectively Tangled wasn't just a professional endeavour; it was born from a deeply personal understanding of the toll the startup journey can exact on mental well-being.

As young entrepreneurs themselves, they feel a genuine connection to the clients they serve. This understanding of how founders grapple with isolation, financial strain and the constant fear of failure allows the pair of former classmates to speak to their clients, having dealt with much of the same pitfalls. 

Against this backdrop, and coming out of a tumultuous, COVID-19 pandemic-impacted 2020 and 2021, Collectively Tangled emerged offering support and resources to address the unique mental health needs of the startup community. By acknowledging and destigmatizing these challenges, Gillis and Mateshaytis aim to empower entrepreneurs to prioritize their well-being and build organizations that prioritize it.

Graduate Studies Collision

Gillis embarked on a career of purpose and impact from her days as an undergraduate student at Western University in Ontario where she pursued a degree in psychology. After graduating, she delved into the realm of youth engagement, landing a role with Mind Your Mind, an organization at the forefront of online mental health resources for young people. Her work involved creating virtual tools and co-creating resources with youth, bridging the gap between experts and the end-users of mental health services.

From there, she transitioned to roles with the Mood Disorders Association of Ontario, the Ontario Centre of Excellence for Child and Youth Mental Health, and Team UnBreakable, focusing on peer support and youth suicide-prevention programs. Her passion for empowering young people and enhancing mental health education led her into classrooms, where she worked closely with teachers and social workers to provide holistic support.

Throughout her journey, Gillis remained committed to amplifying the voices of marginalized communities and addressing systemic barriers to mental health care. This drive for systemic change ultimately led her to pursue a Master of Social Work at UCalgary. Drawn to the program's emphasis on clinical skills and its potential for broader systems-level impact, she saw an opportunity to deepen her understanding of social dynamics and intervention strategies.

For Mateshaytis, her path towards founding Collectively Tangled was shaped by a diverse range of experiences, spanning continents and disciplines, yet all converging on a shared passion for social impact and systemic change. She completed her undergraduate studies in journalism and philosophy in Halifax and later taught English in Taiwan. This sparked an interest in social services and community development. Upon returning to Canada, she found herself drawn to the field of social work, recognizing it as a powerful vehicle for effecting positive change. 

In 2018, Mateshaytis also started her MSW at UCalgary, specializing in clinical counselling, igniting a desire to pursue more macro-level interventions. She and Gillis delved into the intricacies of systemic change, recognizing the untapped potential for integrating mental health support into the startup and innovation sector. Their shared vision crystallized as they explored opportunities within Calgary's innovation ecosystem, leveraging their combined expertise to forge connections and lay the groundwork for what would become Collectively Tangled. With a firm belief in the transformative power of collective action and community-driven solutions, they set out to revolutionize mental health support for entrepreneurs and startups, but always with empathy, innovation and a commitment to social impact. 

“We did our master's degrees and we were both working in these in clinical counselling roles, and we loved the work,” says Gillis. “But it felt important for both of us to do more macro work, so really approaching and targeting things at more of a systems level and less of that surface level.”

How does a startup social enterprise find a way to scale its social impact? 

For Collectively Tangled, the answer came in the winter of 2023 when Mateshaytis and Gillis were accepted as fellows in the Research 2 Social Innovation (R2SI) incubator program, an Innovate Calgary program with close connections to UCalgary academia and research, offering a valuable opportunity for researchers, faculty members and more. The program provides coaching, expert advising, skills-based workshops, student support and a supportive community of like-minded innovators, all aiming to support moving research into impact. This support network and resources helped Mateshaytis and Gillis further develop and advance their social enterprise, while also developing strong connections within the Calgary innovation ecosystem. 

Enter Collectively Tangled

“Based on research, entrepreneurs experience mental health challenges at greater rates than the general population,” says Mateshaytis. “We're talking about very motivated, driven individuals who are typically under a lot of stress and a lot of pressure. It's hard and it's challenging and it attracts a certain type of person; it’s not for everybody.”

Mateshaytis remains grounded in her belief that true change begins at the intersection of individual empowerment and systemic reform — an ethos that continues to guide her work with Gillis. Both were driven by a shared curiosity about the intricate interplay between individual well-being and broader community dynamics, rooted in their exploration of systems theory. Their backgrounds in clinical social work provided them with insights into the complexities of human experience, but they couldn't shake the idea that traditional therapeutic approaches were merely surface-level solutions to deeper systemic issues.

The growth of Collectively Tangled was accelerated by the realization that mental health challenges within the startup and innovation sector were not isolated incidents, but symptomatic of larger structural issues. Drawing upon radical systems theory, which emphasizes the interconnectedness of individual experiences and broader societal structures, they recognized the need for a paradigm shift in how mental health support was conceptualized and delivered. R2SI provided the many of the resources needed for Collectively Tangled to transform its academic research and expertise on mental health into actionable social impact. 

“It’s very interesting because, obviously, we have the mental health expertise, but in this journey that we've been on for the past couple years, we now are very much having the experiences of the entrepreneurs and people that we're supporting,” says Mateshaytis. “It’s a unique perspective to have because we also recognize how hard it is. It’s not an easy thing that these folks are trying to build and grow businesses — and we know that first-hand.”

Both she and Gillis envision a future where mental health support is not only accessible, but deeply ingrained and normalized within the fabric of the startup and innovation sector. It’s a vision they can clearly see as startup entrepreneurs themselves. 

“We say, because we offer specialized services to entrepreneurs, that it’s offered by mental health professionals who are founders, too,” says Gillis. “We walk the walk and are able to tailor content, speak the language, and understand the specific stressors and challenges because we also are living it.” 

Friendship First, Partnership Second.

Gillis says she and Mateshaytis are very similar in many ways their approach to this issue. “At the core of our work and approach, our values are deeply aligned,” she says. “However, as individuals, we have distinct styles and tendencies. I tend to move quickly, while Sarah is more deliberate and cautious. This balance between our approaches is incredibly valuable, plus her dedication and work ethic are truly admirable, she’s one of the hardest workers I've ever had the privilege of knowing."

Adds Mateshaytis: “I truly admire Keara's ability to grasp big-picture concepts and effectively distil them into manageable components. I always call her the ‘Question Queen.’ She has a remarkable talent for asking insightful and probing questions and, whether in conversation or any context, her innate curiosity shines through. She always seeks deeper understanding and clarity."

Gillis and Mateshaytis' move from classmates to co-founders exemplifies the power of shared vision, resilience and collaboration. They continue to strive to fill the systemic gaps in mental health support within the startup and innovation sector. As Collectively Tangled continues to evolve, they remain steadfast in their dedication to creating a future where mental health is not just prioritized, but an integral part of every organization, with hopes of expanding outside of Canada. But, like many system-wide social problems, their focus has now shifted from awareness and theory to solutions and, most importantly, action.

“In the end, it comes back to something that we at Collectively Tangled are really passionate about and that’s how are we bridging the talk to action,” says Mateshaytis. “What are we doing about it? It's amazing that we're talking more about it. We love that and will gladly be a part of any and every conversation, but what are the next steps?”