A New Wave of Entrepreneurship Venture for Canada

Join us for an engaging episode with Cyrus Symoom, Co-CEO of Clariti, a software company for state and local governments, to delve deep into the world of entrepreneurship through acquisition (ETA).

Cyrus shares his incredible journey of purchasing Clariti through a self-funded search at just 26 years old, highlighting the challenges and triumphs of acquiring and scaling a tech company in the Canadian landscape.

Cyrus also explains how he approached his six month search process and raised eight-figure equity financing, the strategic and cultural shifts made to transform a 20-person company into a 120-employee leader in its field, the importance of low ego and high humility in leading an organization through significant changes, and why more Canadians should consider ETA as a career path.

Whether you're an aspiring entrepreneur, a seasoned investor, or simply curious about ETA, this episode offers practical advice, personal anecdotes, and strategic insights into building a thriving business.

In this enlightening episode, we sit down with Juanita Lee-Garcia, the executive director of the Upside Foundation and a pivotal figure in Canadian philanthropy.

Juanita shares her insights into the evolving landscape of philanthropy in Canada, discussing the challenges and transformations she envisions for the sector over the next decade. From her early experiences as a beneficiary of philanthropic efforts to her influential role in shaping venture philanthropy,

Juanita provides a deep dive into how philanthropy is intertwined with systemic change, the ideological shifts within the sector, and the innovative approaches to philanthropic engagement.

This episode is a must-listen for anyone interested in understanding the complexities and potential of philanthropy to effect significant social change.

In this insightful episode, we sit down with Glen Silvestri, Managing Partner of Sage Capital, to explore the nuanced world of search funds and entrepreneurship through acquisition (ETA) in Canada.

Glen shares his journey from the early days at Ontario Teachers to becoming a pivotal figure in the Canadian search fund landscape, highlighting the growth and opportunities within this unique investment space. Listeners will gain a deep understanding of what search funds are, the typical profiles of searchers, and the strategic thinking involved in investing in and growing small businesses through this model.

Glen discusses the challenges of balancing investor expectations with entrepreneurial visions and how Sage Capital supports its portfolio companies from acquisition to successful exit strategies.

This episode is a must-listen for anyone curious about alternative paths to entrepreneurship and investment, offering a blend of practical advice, industry insights, and personal anecdotes that illuminate the path to successful investments in the search fund ecosystem.

Join us for an engaging discussion with Sean Speer, editor at large at The Hub. Sean shares insights into the pioneering media model of The Hub, a news and commentary website that's reshaping the Canadian media landscape by providing a platform for conservative and center-right perspectives.

The Hub isn’t just another news outlet; it's a startup in the media industry that bridges intellectual discussions with public engagement.

Throughout the episode, Sean reflects on the initial challenges and triumphs of establishing The Hub, from conceptualization to realization, and delves into the importance of civil, respectful, and pragmatic public discourse in today's rapidly changing media environment.

Whether you're intrigued by the dynamics of new media models or interested in the intersections of politics and media, this episode offers a deep dive into the evolution of media with one of its innovative leaders.

Discover the power of resilience within you.

Hosted by Jennie Wedd, Venture for Canada's Senior Lead of Strategic Relations & Marketing, this compilation episode dives deep into the heart of resilience.

Join Jennie and guests Danièle Henkel, President at Les Entreprises Danièle Henkel; Sukhinder Singh Cassidy, CEO at Xero; and John Ruffolo, Founder and Managing Partner at Maverix Private Equity as they recount their journeys of resilience, joy, and strength. From heartfelt stories to actionable advice, discover how to view adversity as an ally and embrace fear as a friend.

Whether you're facing personal or professional obstacles, this episode equips you with practical strategies, mindset shifts, and the inspiration needed to transform your greatest challenges into opportunities.

In this episode, you'll learn how to:


Find strength and joy, even in the toughest times.
Embrace challenges as a chance for growth and reflection.
Take micro-risks to help overcome your limiting beliefs.
View fear not as a barrier but as a motivator for change.
Align your actions with your core values for a more authentic life.

Reflection questions:


What values are non-negotiable in my life?
When have I felt most authentically myself, and what activities was I engaged in?
How often do I speak to myself with criticism instead of compassion?
What lessons have I learned from my greatest setbacks?
What is this feeling of fear trying to tell me?

Links to the original episodes:


Danièle Henkel: Resilience and trusting oneself with Danièle Henkel
Sukhinder Singh Cassidy: Sukhinder Singh Cassidy: Becoming a Risk Taker
John Ruffolo: John Ruffolo: Fostering Self-Discipline

Meet Jessica Bosman & Bryn Davis Williams, the co-founders of DOUBL. This startup isn’t just changing how we think about clothing; it's pioneering a future where apparel, starting with bras, is made to measure and ordered from the palm of your hand.

In this episode, discover how Jessica and Bryn leverage advanced technology to address long-standing issues in retail. The founders share their journey from a business school project to tackling the static retail landscape, driven by the desire to innovate a stagnant industry. They discuss the challenges of custom manufacturing, the ethics of sourcing, and their vision for a sizeless, sustainable fashion world.

Get ready for a deep dive into the intricacies of building a brand, the importance of focus, and how DOUBL is set to disrupt traditional retail models, making personalized, ethical apparel the norm.