A New Wave of Entrepreneurship

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.

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.

Join us for a captivating conversation with visionary entrepreneur Drayton Mulindabigwi. This episode delves into Drayton's unique journey from Rwanda to Canada, inspired by the resilience of his parents, genocide survivors, and how it shaped his ambitions and approach to overcoming adversity. Drayton shares invaluable insights on combating imposter syndrome, fostering creativity, and the significance of resilience, networking, and strategic risk-taking in entrepreneurship.

This episode is jam-packed with advice for young entrepreneurs eager to make their mark without years of experience, emphasizing the power of dreaming big and leveraging one's unique background to create change.

Dive into the raw and inspiring story of Martin Basiri, Co-Founder of ApplyBoard and CEO of Passage, in this compelling episode. From his humble beginnings in Iran to founding one of Canada's tech success stories, Martin opens up about the rollercoaster of entrepreneurship. He discusses the grit, vision, and perseverance needed to transform personal adversity into a globally recognized educational platform.

Through tales of overcoming cultural barriers, mastering new skills, and navigating the complexities of the tech startup ecosystem, Martin's story is a testament to the power of relentless ambition and innovation.

Whether you're an aspiring entrepreneur or simply interested in the stories behind tech innovators, this episode offers a candid look into the highs and lows of building something from the ground up.

Join us on a captivating journey with Abi Coman-Walker , from her dynamic career transition from the financial sector to the forefront of biotechnology. This episode delves into Abi's remarkable career path, which spans from being an executive at HSBC, one of the world's leading international banks, to becoming the Chief Operating Officer at one of Canada's pioneering therapeutics companies. Abi shares her insights on building flexibility in one's career as interests evolve over time, reflecting on her own experiences and the pivotal role she played in the delivery of COVID-19 vaccines.

Learn about the importance of adaptability, the value of diverse experiences, and how embracing change can lead to unexpected and rewarding career trajectories. Whether you're navigating your own career path or interested in the intersection of finance and biotechnology, this episode offers valuable lessons on growth, resilience, and the impact of embracing new opportunities.

Meet Reuven Ashtar, CEO of Never Napping. This episode delves into Reuven’s diverse career, transitioning from law to becoming a key player in the YouTube and influencer sphere. Gain insider insights into what it takes to be a successful talent manager in the ever-evolving landscape of social media. Learn about the challenges and triumphs of managing top YouTubers and influencers, understanding their unique needs, and crafting strategies that resonate with a digital-first audience. Reuven shares invaluable tips for aspiring influencers and content creators on how to build a compelling online presence, make impactful content, and harness the power of digital platforms.

Whether you’re a budding YouTuber, an aspiring influencer, or simply fascinated by the mechanics of digital fame, this episode is a treasure trove of practical wisdom and industry secrets.

Embark on a journey of leadership with Tamara Vrooman, CEO of Vancouver International Airport (YVR). This conversation takes flight into the essence of curiosity-driven leadership, illustrating how Tamara's inquisitive nature has fueled her rise across varied sectors, culminating in her role at YVR. We explore how her curiosity not only elevates her management style but also shapes the future of aviation at one of Canada's busiest airports. Get ready for a deep dive into the power of curiosity in leadership, far beyond the runways of YVR.

Dive into the world of serial entrepreneurship with Lourdes Juan, a mastermind behind several successful businesses. In this episode, Lourdes reveals her secrets to juggling multiple ventures, from urban planning to technology. Learn how she prioritizes tasks, manages time, and selects the right team for each unique project. Discover her approach to problem-solving and innovation, and how these skills are crucial in different sectors. Lourdes also shares personal insights on maintaining mental health amidst the chaos of entrepreneurship and the significance of rituals in her daily routine. Whether you're a budding entrepreneur or looking to expand your business portfolio, this episode is packed with actionable strategies and personal anecdotes to guide you in managing multiple ventures effectively.

Join Karen Greve Young, CEO of Futurpreneur Canada, in a deep dive into the world of inclusive leadership. Karen brings her wealth of experience in fostering economic and social inclusivity to the forefront, offering key insights into assembling diverse and effective leadership teams. In this episode, she highlights the balance of lived experiences with professional expertise essential for transformative leadership. Karen addresses the critical importance of genuine representation in the workplace, navigates the challenges of tokenism, and shares practical tactics for building fair and dynamic organizational cultures.

Meet Stewart Beck, a distinguished diplomat with a rich history of fostering international relations and promoting Canadian interests abroad. With a career spanning pivotal roles in places like Taiwan, Silicon Valley, and as the President of the Asia Pacific Foundation of Canada, Beck brings a wealth of experience in understanding global dynamics and their impact on entrepreneurship. In this conversation, we explore Beck's insights on how Canada can cultivate a culture of entrepreneurship, drawing from global best practices and his unique experiences. Beck discusses the need for embracing risk, the importance of failure in entrepreneurial journeys, and the impact of immigration on Canada's entrepreneurial landscape. This episode offers valuable perspectives for anyone interested in the intersection of diplomacy, global economics, and entrepreneurship.

Meet Ian Brooks, CEO of HelloFresh Canada, a pioneer in the meal kit industry. Embarking on an unconventional career path, Ian transitioned from environmental sciences to revolutionize the way we approach meal preparation. His journey includes diverse experiences in environmental consulting, technology project management, and strategic roles at Johnson & Johnson and McKinsey & Company. At HelloFresh, Ian has been instrumental in transforming meal preparation through innovative, eco-friendly meal kits, significantly reducing food waste and carbon footprint compared to traditional grocery shopping. He discusses the challenges and triumphs of introducing HelloFresh to Canada, emphasizing the brand's commitment to sustainability and healthy eating. This episode is a deep dive into the evolving landscape of the meal kit industry, offering valuable insights for entrepreneurs, environmental enthusiasts, and anyone interested in the intersection of food, technology, and sustainability.

Meet Geoff Smith, the Chair of EllisDon, a major player in Canada's construction industry with an impressive $5 billion in annual revenue and 4,000 employees. Geoff, who previously served as CEO for nearly 25 years, shares his experience in evolving EllisDon from a conventional general contracting firm to a diversified leader in construction. He discusses the challenges and strategies involved in this transformation, highlighting the importance of adopting innovative approaches, fostering a culture of trust, and integrating digital solutions. This episode provides valuable insights into driving change in a traditional industry, making it essential listening for leaders, entrepreneurs, and anyone interested in the dynamics of business adaptation and industry leadership.

Explore the art of scaling social innovation with AJ Tibando, Co-Founder and Chief Strategy Officer at Palette Skills. In this episode, AJ navigates the journey of transforming big ideas into impactful realities. She delves into Palette's approach to tackling societal issues, employing innovative funding models and a strategic non-profit mindset. AJ discusses the importance of thorough research and deep customer understanding in developing sustainable and socially conscious business models. Ideal for social entrepreneurs, policymakers, and change-makers, this episode offers a practical look into creating lasting change in the tech and education sectors. It’s a must-listen for those eager to make a difference in the world of social entrepreneurship, providing actionable insights and valuable perspectives.

In this inspiring episode, join award-winning social entrepreneur Jenn Harper, CEO and Founder of Cheekbone Beauty Cosmetics INC, as she discusses the transformative power of vulnerability in leadership. Delve into the journey of embracing one’s own vulnerabilities to emerge as a more effective and empathetic leader. This episode offers a profound look at personal growth, emotional intelligence, and the strength that comes from vulnerability, making it a must-listen for leaders, managers, and anyone looking to foster a more authentic leadership style.

Join Kevin Kliman, CEO and co-founder of Humi, as he unveils the secrets of building a successful team in a high-growth tech environment. From his early days as a dentist and aspiring hockey player to leading Humi, Canada's top employment solution, Kevin shares his unique journey and insights. Explore the challenges and triumphs of team building, reinvesting in the community, and nurturing tech talent in Canada. This episode is perfect for entrepreneurs, tech enthusiasts, and leaders looking to scale their teams effectively in the fast-paced tech world.

Join us in an insightful conversation with John Montalbano, former CEO of RBC Global Asset Management. With a career that culminated in managing $370 billion in assets, John offers a rare glimpse into the strategies that propel a company into the top tiers of global asset management. Serving as a Director and Audit Chair for organizations such as the Canada Pension Plan Investment Board and AbCellera Inc., he brings a wealth of knowledge in corporate governance and financial strategy. This episode isn't just about John's career journey; it's a guide for aspiring finance professionals, corporate leaders, and entrepreneurs seeking mentorship and leadership insights. We discuss the essence of impactful mentorship in the world of finance, and how these lessons can be applied across industries for those aiming to leave a mark in their fields.

Join us for an insightful episode featuring Hamza Khan, best-selling author, award-winning entrepreneur, and globally-renowned keynote speaker. As a trusted voice in leadership, Hamza's TEDx talk, "Stop Managing, Start Leading," has resonated with over two million viewers. In this episode, Hamza Khan shares his expertise on shifting from management to true leadership. Discover actionable strategies and real-world examples to empower you and your team to excel in today's dynamic business landscape. Whether you're an aspiring leader or a seasoned professional, Hamza's wisdom will inspire you to lead with purpose and resilience.

Join us in an engaging conversation with Jonathan Hackett, Co-Head of BMO’s Energy Transition Group and a leader in Sustainable Finance. With a career from quantum physics research to advising on low-carbon economy transitions, Mr. Hackett brings a unique perspective on driving sustainable innovation. This episode delves into his journey from his doctoral research in Quantum Gravity and Topology to leading BMO's $250MM impact investment fund. Discover how he's shaping the future of finance by guiding clients through ESG challenges and developing innovative, sustainable financing structures. This episode is an invaluable resource for entrepreneurs, investors, and anyone eager to contribute to a more sustainable and resilient economy, providing key insights into the sectors of sustainable finance and energy transition.

The Right Honourable David Johnston was Canada’s 28th governor general. During his mandate, he established the Rideau Hall Foundation (RHF), a registered charity that supports and amplifies the Office of the Governor General in its work to connect, honour and inspire Canadians.

Prior to his installation as governor general, Mr. Johnston was a professor of law for 45 years, and served as President of the University of Waterloo for two terms, Principal of McGill University for 3 terms. 

He holds degrees from Harvard, Cambridge and Queen’s and has received more than three dozen honorary degrees or fellowships. He has authored or co-authored more than 30 books. He was named Companion of the Order of Canada in 1997. He has chaired or served on many provincial and federal task forces and committees, and has served on the boards of more than a dozen public companies. 

In this episode, we discuss the challenges and opportunities to make Canada more innovative.

Kayla Isabelle is the Chief Executive Officer at Startup Canada, the gateway to Canada’s entrepreneurial ecosystem. Startup Canada’s mission is to connect Canada’s entrepreneurs with the tools, community, and support they need to start and build their businesses. Kayla has dedicated her career to supporting entrepreneurs, both in Canada and internationally. An award-winning leader, strategic communications consultant, and change management facilitator, she is passionate about leveraging the power of storytelling in the entrepreneurial community. Kayla sits down with Scott to discuss the state of entrepreneurship in Canada.

Bruce Sellery is the CEO of Credit Canada, the country’s oldest non-profit credit counseling agency. He comes to the role after two decades as a business journalist, personal finance expert, and financial literacy consultant. He was an anchor for BNN Bloomberg in Toronto and New York City, a contributor on CBC TV’s The Exchange, and the host of Million Dollar Neighbourhood on the Oprah Winfrey Network. Bruce is the Money Columnist for CBC Radio And he hosts a national weekly radio show for SiriusXM. Bruce sits down with Scott to talk about fostering financial resilience in entrepreneurs.

Gururaj “Desh” Deshpande is President and Chairman, Sparta Group LLC Dr. Deshpande founded Cascade Communications and Sycamore Networks and has chaired and funded several other companies. Deshpande is a life member of the MIT Corporation. The Deshpande Foundation supports Social entrepreneurship and provided the founding grant for NSF Innovation Corps (I-CorpsTM) and Deshpande Center at MIT. Desh sits down with Scott to discuss what it takes to be an innovative and successful entrepreneur.

Ronald Richardson is a corporate director and private investor with active roles and investment interests in the technology, energy, space, and not-for-profit sectors. As a private investor, Ronald manages an investment portfolio of over 40 companies, is a member of the Capital Angel Network, an advisor to L-Spark, SheBoot, and the Next36 program cohorts. Ronald sits down with Scott to discuss the importance of board governance.

John Baird is a Senior Advisor at Bennett Jones LLP and a former Senior Cabinet Minister in the Government of Canada. An instrumental figure in bilateral trade and investment relationships, Mr. Baird has played a leading role in the Canada-China dialogue and worked to build ties with ASEAN countries. In addition, Mr. Baird has worked closely with international leaders to strengthen security and economic ties with the United States and Middle Eastern countries. Before entering federal politics, Mr. Baird spent ten years in the Ontario Legislature where he served as Minister of Community and Social Services, Minister of Energy, and Government House Leader. John sits down with Scott to discuss how to manage geopolitical risks.

Stephen is the former Governor of The Bank of Canada and a widely recognized economist with nearly 40 years of experience in financial markets, forecasting, and economic policy, including 35 years in the public sector. Stephen is also the author of “The Next Age of Uncertainty: How the World Can Adapt to a Riskier Future,” which maps out the powerful economic forces that are shaping our future and the ideas that will allow us to master them. Stephen Poloz sits down with Scott to discuss how to navigate uncertainty. 

Irfhan Rawji is the Founder & CEO of MobSquad, an innovative Canadian start-up that ensures high-caliber software engineers with U.S. work visa challenges remain working with their current company but is near-shored from Canada. Irfhan is also a Managing Partner with Relay Ventures, an early-stage venture capital firm with US$600MM of assets under management. Irfhan sits down with Scott to offer his perspectives on what makes Canada an attractive place to work, the immigrant wage gap, and the role of MobSquad.

John Ruffolo is the Founder and Managing Partner of Maverix Private Equity, a private equity firm focused on technology-enabled growth and disruption investment strategies. As an active board member in the profit and not-for-profit sectors, John works with many leading innovative organizations including AI Partnerships Corp., engineering.com, Ether Capital, OneEleven, the David Suzuki Foundation, the CIBC Foundation, and the Royal Ontario Museum. 

Throughout his career, John continues to be recognized for his unparalleled contributions to the growth of the technology sector and expansive vision of Canada’s economy. For instance, in 2014, John was recognized as Canada’s #1 of the 100 Most Powerful Business People by Canadian Business Magazine (#3 in 2015) and was selected as one of Toronto’s 50 Most Influential People by Toronto Life (#16 in 2015, #40 in 2016, #26 in 2017). In 2018, John was honored with the Order of Merit of the Italian Republic, making him a fifth Class Knight. 

John sits down with Scott to offer his perspectives on fostering self-discipline.

Chad Lubelsky is currently the Vice President, of Strategy, Impact, and Development at Volunteer Canada, where he leads strategy, development, and implementation of new models and pathways for volunteering and civic participation by centering belonging and inclusion. Chad has 20+ years of working in social change. He started his career as a journalist before pivoting to nonprofits. Since then he has worked in International Development, youth engagement, human rights, Internet policy, education, communications, food security, social inclusion, philanthropy, and more. Chad sits down with Scott to offer his perspectives on the role of post-secondary institutions.

Jason Della Rocca is a game industry entrepreneur, funding advisor, and cluster expert. He specializes in business/partnership development, pitching/funding, and ecosystem/cluster development. As the co-founder of Executions Labs, he was a hands-on early-stage investor in over 20 independent game studios from North America and Europe. He sits down with Scott to discuss how to build a successful video game company.

Senator Colin Deacon brings a unique perspective to Canada’s Upper Chamber. Prior to joining The Senate of Canada, he spent much of his career turning ideas into organizations, products, and services that improve lives. Senator Deacon sits down with Scott to discuss how to build an entrepreneurial government. 

Janet is a Partner at Real Ventures, a leading source of capital for entrepreneurs who are building the next generation of leading tech companies. Janet has led investments in over a dozen companies and works actively with founders to help them build large, industry-defining companies. In 2004, Janet launched Kijiji.ca and grew it to become one of the most visited websites in Canada. Subsequently, she led the Kijiji Global business, launching the site in new countries and accelerating growth in North America, Europe, and Asia. Janet also spent four years at eBay in Silicon Valley where she helped transform eBay from a Collectibles to a mainstream marketplace. Janet sits down with Scott to discuss learning how to make difficult decisions.

Jay Reid offers people tools to activate their adaptability with minimal fuss and maximal joy. He does this through The Making-Box, a company he co-founded in 2013. Since then, Jay has led adaptability training and team-development programs at organizations across the globe including Shopify, Google, RBC, Loblaws, Danube University Krems, and hundreds of others. He sits down with Scott to talk about how to become more adaptable.

Sara Wilshaw is the Chief Trade Commissioner at Global Affairs Canada. She leads a global team that helps Canadian businesses explore international markets, find new customers and partners, and promote exports. She sits down with Scott to discuss fostering Canadian trade around the world.

Christian Lassonde is the Founder and Managing Partner of Impression Ventures, a VC firm focused on investing in Seed and Series A deals in the financial technology sector. He has also taught high-growth technology entrepreneurship at The Next 36. Christian sits down with Scott to provide actionable advice on how entrepreneurs should interact with venture capitalists.

Sam Duboc is president and CEO of Elkland Capital Inc., a family-owned investment firm with a current portfolio covering a wide range of industries, including, but not limited to health sciences, clean energy, marketing services, and technology. He is the former Executive Chair of MindBeacon, Chair of The Business Development Bank of Canada, Co-Founder & COO of LoyaltyOne, Director of Porter Airlines, and Co-Founder & Founder of LEAP | Pecaut Centre for Social Impact. Sam sits down with Scott to talk about his mental health journey and how to reduce the stigma around mental health.

Darian Kovacs is an Indigenous founder of Vancouver-based Jelly Digital Marketing & PR, and a digital marketing school, Jelly Academy. He’s the host of the Marketing News Canada podcast, a contributing writer for the Globe & Mail, Forbes, Entrepreneur, Canadian Business Quarterly, and Future Economy, and is on the board of NPower Canada. Darian joins Scott to offer his perspective on how to become a successful marketer.

Goldy Hyder is the President and CEO of the Business Council of Canada, a non-partisan association composed of chief executives and entrepreneurs of Canada's leading enterprises. He sits down with Scott to discuss how to increase Canada’s labour productivity and overall economic competitiveness.

Sukhinder Singh Cassidy is a leading technology executive and entrepreneur, board member, and investor with experience at companies such as Google and Amazon. As of February 2023, she is the CEO Designate of Xero, a cloud-based accounting software platform for small businesses with over three million subscribers globally. Sukhinder sits down with Scott to discuss how to choose possibilities and take smart risks.

Benjamin Bergen and Dana O’Born are respectively the President and Vice President of the Council of Canadian Innovators, a national business council representing over 150 of Canada’s fastest-growing technology-intensive companies. CCI is dedicated to helping high-growth Canadian-based technology firms scale up globally by advancing public policy strategies that increase access to talent, capital, and customers for domestic innovation firms. Benjamin and Dana sit down with Scott to discuss how to grow the intangible economy and foster a more prosperous and globally competitive Canada.

Tim Jackson is the President & CEO of Shad Canada, an annual Canadian summer enrichment program for high-achieving high school students. Shad Valley started in Aurora, Ontario in 1989 and has grown into Shad Canada which offers a widespread STEAM and entrepreneurship program for over a thousand students in partnership with top Canadian universities each year.

Tim sits down with Scott to discuss how the not-for-profit and for-profit sectors can learn from each other.

Mike Wessinger is Co-Founder and Executive Chair of the Board of Directors at

PointClickCare, the #1 cloud-based healthcare software provider helping long-term and post-acute care (LTPAC) providers. As of July 2022, PointClickCare generates more than US$ 500 million in annual revenue and has been growing by about 20 percent a year. Mike sits down with Scott to discuss how to build a work culture that encourages people to stay and grow.

Michael Garrity, Founder, and CEO of Financeit, has disrupted the financial technology industry for over two decades by bringing innovative technologies to traditional markets. Tune in to his conversation with Scott as they discuss how to cultivate a culture of feedback within an organization.

Kirstine Stewart is an internationally award-winning leader with deep expertise working at the intersection of media and technology, and a reputation for turning around revenue performance and driving new market expansion on a global scale. She sits down with Scott to discuss how to cultivate self-awareness, bring value to others, and how to find the right company that fits your values.

Annette Verschuren is Chair and CEO of NRStor Inc, an energy storage development company. Formerly the president of The Home Depot Canada and Asia, she oversaw the growth of the company’s Canadian operations from 19 stores to 179 stores nationally. She sits down with Scott to discuss how to trust your instincts when making decisions, how to foster a strong work ethic, and how to influence others.

Martin Picard is the co-founder of Sonder, which provides hotel amenities without the formality and manages over 6,300 units in over 35 cities in 10 countries and has served over 1 million guests. He sits down with Scott to discuss how shifting consumer preferences are transforming the hospitality industry and how he built Sonder.

Eva Lau is a well-respected entrepreneur-turned-investor and one of the few women leading a venture fund in Canada. She is the Founding Partner of Two Small Fish Ventures. She sits down with Scott Stirrett to talk about building your inner resilience. The most important takeaways were about understanding that time heals all wounds, love yourself, and her story on staying resilient while building Wattpad.

Fahd Al-Hattab is the Founder & Leadership Development Speaker at Unicorn Labs, a company that coaches managers into leaders and creates high-performing teams that scale. He sits down with Scott Stirrett to discuss the many ways managers can either fail or set up their teams for success. Building psychological safety amongst your teams, and how to be an effective coach as a manager.