The Hard Part with Evan McCann

Josh Domingues is the Founder & Executive Chairman of Flashfood.Flashfood is on a mission to feed families, not landfills. Their app connects shoppers with fresh produce, meat and other groceries at up to 50% off. By partnering with retailers across North America, they offer nutritious staples at affordable prices and reduce the amount of food going to landfills. Takeaways- Josh's Connection to Food Waste- Understanding Food Waste and Its Impact- Early Product Validation- Building Consumer Demand- Navigating Grocery Store Partnerships- The Journey of Raising Capital and Scaling- Scaling Effectively by Simplifying Processes for Retailers- The Reality of Scaling in the US- Building an Effective Executive Team- The State of Canadian TechChapters00:00 The Genesis of Flashfood04:31 Understanding Food Waste and Its Impact11:01 Building Consumer Demand14:33 Navigating Grocery Store Partnerships18:11 The Journey of Raising Capital and Scaling23:41 The Reality of Scaling in the U.S.27:39 Building an Effective Executive Team37:30 The State of Canadian Tech43:58 Personal and Professional Growth StrategiesKeywordsFlashfood, food waste, grocery app, sustainability, startup journey, consumer demand, fundraising, grocery partnerships, environmental impact, food industry, scaling, U.S. market, executive team, Canadian tech, entrepreneurship, growth mindset, leadership, building businesses, Flashfood, innovation

Michael Buhr, the Executive Director of C100, is a veteran with over 30 years in Silicon Valley, dedicated to connecting Canadian tech entrepreneurs with global resources. In this engaging discussion, he highlights the mission of C100 in fostering mentorship and collaboration among the Canadian expat community in the Bay Area. Buhr dives into the changing entrepreneurial landscape, the challenges faced by growing companies, and the importance of in-person connections. He also emphasizes a unique Canadian mindset that encourages support and ambition in the tech sector.

Meti Basiri is the Co-Founder and CEO of ApplyBoard.ApplyBoard's mission is to empower students worldwide to unlock opportunities for the best education. With their innovative platform and expert team, they simplify the journey—from exploration and application to enrollment—helping thousands of students achieve their dreams of studying abroad.Takeaways- ApplyBoard's First Round of Investment.- Mission-Driven Culture and Creating Impact.- Scaling Challenges and Strategies- Adapting to Recent Policy Changes- ApplyBoard's Newest Venture - Capio- Maintaining Startup Mentality During Growth- Navigating Startup Culture and Growth Challenges- The Balance of Internal Promotions vs. External Hires- Co-Founder Dynamics: Family and Business- International Expansion: Cultural Adaptation and ChallengesChapters00:00 The Founding Story of ApplyBoard06:23 Navigating Early Investments09:11 Mission-Driven Culture and Impact13:58 Scaling Challenges and Strategies17:07 Adapting to Policy Changes21:09 Innovating with New Ventures24:05 Maintaining Startup Mentality During Growth26:29 Navigating Startup Culture and Growth Challenges29:13 The Balance of Internal Promotions vs. External Hires35:57 Co-Founder Dynamics: Family and Business39:30 International Expansion: Cultural Adaptation and Challenges43:27 Personal Growth and Resilience in Business47:37 Finding Balance: Hobbies and Positive MindsetKeywordsApplyBoard, entrepreneurship, international students, education, startup culture, investment, scaling, mission-driven, policy changes, innovation, startup culture, hiring practices, co-founder relationships, international expansion, personal growth, resilience, business challenges, company values, team dynamics, leadership

Stephen Seibel is the Founder and COO of Clutch.Clutch is Canada’s largest online used car retailer, delivering a seamless, hassle-free car buying and financing experience to drivers everywhere. Takeaways- Stephen's move from investment banking to starting Clutch.- Why he booked a one-way ticket to Halifax to launch the business.- Navigating regulartory hurdles.- Clutch's business model began with a consignment approach.- Early fundraising for a capital-intensive business like Clutch was particularly challenging in Canada.- Dive deep into the car sales industry in Canada and the US.- Why Canada is the ideal place to build Clutch.- Why they source cars directly from consumers.- Clutch has purchased over 27,000 cars from Canadians.- Clutch utilizes machine learning to optimize car offers and inventory management.- Clutch is designed to be a managed two-sided marketplace, differentiating it from competitors.- The logistics of delivering cars across Canada.- Their 100K sqft facility in Mississauga and how they do everything in-house.- Building trust, ads, marketing, partnership with the Raptors.- Building a national brand an industry that is traditional local or regional.- The nuances with financing.- Building for over 9 years and loving the grind.- Bringing Dan Park onboard to be CEO and their strong relationship.Chapters00:00 From Banking to Entrepreneurship: The Journey Begins05:03 Overcoming Regulatory Hurdles: The Halifax Move12:01 The Drive to Succeed: Motivation Behind Clutch14:55 Disrupting the Auto Industry: Clutch's Unique Model20:58 Data-Driven Decisions: Sourcing Quality Cars25:43 Automating Car Purchases: A Data-Driven Approach26:47 Navigating Complex Logistics in the Automotive Industry30:39 Financing Challenges in Used Car Sales35:21 Building a Trustworthy Brand in Used Car Sales39:12 Leadership Dynamics: The Role of a CEO43:07 Personal and Professional Aspirations: Looking AheadKeywordsEvan McCann, Stephen Seibel, Clutch, entrepreneurship, investment banking, auto industry, regulatory challenges, car buying experience, data-driven business, Canadian market, automotive logistics, used car financing, brand trust, leadership, data-driven decisions

Rishi Nayyar is the Co-Founder and CEO of PocketHealth.PocketHealth is on a mission to empower every patient with instant access, control and understanding of their health records while streamlining medical image sharing for healthcare providers. Takeaways- Current Landscape of Medical Imaging- Building a Patient-Centric Platform- Prioritizing Security and Privacy- Navigating Different User Experiences- Understanding Market Differences: US vs Canada- Filling Gaps in Patient Care- The Role of AI in Healthcare- Team Dynamics and R&D Focus- Sales Strategies in Healthcare- Trends in Healthcare Technology- Empowering Patients Through Visibility- Lessons Learned Over a DecadeChapters00:00 The Genesis of Pocket Health02:48 Current Landscape of Medical Imaging05:50 Building a Patient-Centric Platform11:13 Prioritizing Security and Privacy14:17 Navigating Different User Experiences16:17 Understanding Market Differences: US vs Canada19:09 Filling Gaps in Patient Care21:50 The Role of AI in Healthcare24:28 Team Dynamics and R&D Focus26:29 Sales Strategies in Healthcare28:24 Trends in Healthcare Technology31:12 Empowering Patients Through Visibility34:13 Lessons Learned Over a Decade37:22 Cultural Shifts in Patient Engagement39:13 Quickfire Round: Insights and InspirationsKeywordshealth tech, patient engagement, medical imaging, AI in healthcare, startup journey, security and privacy, healthcare innovation, Pocket Health, US vs Canada healthcare, patient empowerment

Mark Goad is the GM of Canada at Alan.The health partner who prevents, insures, and cares daily - Alan's mission is a healthier humanity.Alan is partnered with 30,000 companies, has more than 700,000 members, is at +€470m ARR with 600 employees in France, Spain, Belgium and now Canada.Takeaways- Choosing to pursue business over a CFA.- His move and time in venture.- Career decision-making.- His role as Board Chair of CAMH Engage.- How the Alan opportunity came about.- Why he wanted to join a French company entering the Canadian market.- Working with regulators. - Working for a global organization but also localizing the offering and product for Canada.- Understanding the Canadian market's nuances is key.- Innovation in healthcare.- Direct billing.- Their launch customer segment and why that focus.- Community engagement and building awareness.- Unique traits of Alan's culture, operations and day-to-day.- Hiring strategies.- Transforming insurance and the purchasing experience.Chapters00:00 The Entrepreneurial Spirit: Early Beginnings06:01 Navigating Career Decisions: Embracing Risk12:04 Joining Alan: A Unique Opportunity in Healthcare18:03 Localizing Healthcare: Adapting to the Canadian Market25:27 Building a Strong Community Presence31:27 Transforming Insurance Purchasing Experience37:16 Engaging with Startups EffectivelyKeywordsentrepreneurship, venture capital, career decisions, mental health, healthcare innovation, regulatory challenges, Canadian market, startup culture, risk management, insurance industry, insurance, direct billing, customer experience, startup culture, healthcare, community engagement, hiring strategies, technology integration, market entry, mental health

Simon De Baene is the Co-Founder and CEO of Workleap.Workleap is for HR teams that need to solve HR challenges. They help you make your people happier and more productive with the easiest employee experience technology to launch, manage and love. Takeaways- Why the name Gsoft was inspired by G-Unit.- Starting Gsoft (now Workleap) at 20 years old right out of school- Transitioning from a service company to a product company.- Building products allows for more control over destiny.- The decision to shut down the service side to focus on products.- Raising the first external capital from CDPQ after 19+ years.- Maintaining passion for close to 20 years.- Working half his life on Workleap.- Achieving $150M in revenue.- Major rebrand to WorkLeap and how to do that well.- The impacts of AI in the HR space.- Building company culture.- Why you can't be everything to everyone.- The importance of embracing change and letting go of nostalgia.- Building and staying in Montreal.- His one regret in building Workleap, not surrounding himself with advisors and mentors earlier.Chapters00:00 The Genesis of Gsoft: A Young Entrepreneur's Journey05:09 Transitioning from Service to Product: The Birth of Sharegate13:22 Navigating Growth: The Dual Product Strategy16:18 Capital Efficiency and the Decision to Raise Funds22:21 Maintaining Passion: A Lifelong Commitment to Workleap26:44 Rebranding: From Gsoft to Workleap27:18 The Evolution of Branding and Identity29:57 Navigating Workplace Changes and AI Integration34:53 Building and Scaling Company Culture40:00 Leadership Lessons and Personal Growth43:52 Proudly Building in Montreal49:01 Personal and Professional AspirationsKeywordsGsoft, Workleap, entrepreneurship, product development, service company, Sharegate, OfficeVibe, capital efficiency, rebranding, workplace tools, branding, workplace changes, AI, company culture, leadership, Montreal, entrepreneurship, personal growth, remote work, product development

Great to dive into Build Canada with Daniel Debow!Build Canada is a platform of bold ideas for growth, innovation, and prosperity. Every policy is proposed by successful Canadian entrepreneurs with deep knowledge from building in the relevant areas. They are supported by policy experts with experience in government. Their singular focus is a Canada where people build again.Takeaways- What is Build Canada? Why did it start? Why now?- How did the team actually get Build Canada out of the group chat?- Fostering economic growth in Canada.- Why memos? Why that format?- The team of volunteers driving Build Canada.- Diversity in voices is crucial for comprehensive policy discussions.- Criticism of the initiative.- Creating positivity and actionable change.- Encouraging builders to speak up.- Courage is essential for public discourse and change.- Direct communication versus traditional media.- Diving into the product and systems behind Build Canada.- Why a bipartisan approach?- Building a community around shared values.- A love for one's country can inspire action and change.Chapters00:00 Introduction to Build Canada02:51 The Format and Purpose of Policy Memos06:08 Diversity of Voices in Policy Memos08:48 Team Dynamics and Volunteer Commitment12:06 Addressing Criticism and Misconceptions14:59 Creating Positivity and Actionable Change18:02 Encouraging Builders to Speak Up21:07 Courage to Speak Up22:37 The Power of Direct Communication23:41 Building Canada: A Digital Revolution25:14 Bipartisan Approach to Policy29:19 Engaging with Government and Public Policy35:21 Personal Motivations Behind Build Canada38:33 Looking Ahead: Future Projects and PassionsKeywordsBuild Canada, public policy, entrepreneurship, policy memos, Canadian growth, volunteer organization, builders, economic change, policy ideas, community engagement, Canada, public policy, entrepreneurship, Build Canada, digital communication, government engagement, bipartisan, courage, personal motivation, community

Kat Garcia is the Co-Founder and Co-CEO of Ground.Uncover untapped revenue, with zero effort. Ground is an AI revenue driver growing the next generation of consumer companies, for Founders, Agencies, and Go-to-Market Teams.Takeaways- Kat's time at BCG Digital Ventures.- Understanding customer psychology.- Retention strategies and how Ground helps.- Growth teams face unprecedented challenges currently.- Integrating with existing tools.- AI models leveraging product, customer, and browsing data.- Ground helps businesses drive revenue without changing teams.- Insights from AI can inform better product decisions.- Personalization is now achievable due to AI.- New York's tech scene.KeywordsAI, entrepreneurship, growth marketing, BCG Digital Ventures, revenue generation, retention strategies, tech founder, e-commerce, product development, market trends, AI, customer journey, e-commerce, personalization, marketing, technology, consumer behavior, retention, insights, business growth

Anson Yu and Hudhayfa (HudZah) Nazoordeen, co-hosts of Socratica, discuss their unique initiative fostering interdisciplinary collaboration among creatives. They share how Socratica was born as a countercultural response to post-COVID isolation, emphasizing community ownership and personal agency. The duo explains the concept of 'permission' that allows members to explore diverse interests freely. They outline the structured sessions and emerging community nodes, highlighting the critical role of alumni and the evolving symposium in maintaining vibrant connections.