The Hard Part with Evan McCann

Evan McCann
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  • BUSINESS
  • UPDATED WEEKLY

The Hard Part, hosted by Evan McCann, uncovers the stories, strategies, and playbooks of Canada’s most influential founders, investors, and leaders. While Canadian innovators often fly under the radar compared to their American peers, The Hard Part shines a spotlight on their impact, redefining Canada’s role in global entrepreneurship.

  1. 23H AGO

    Michael Serbinis from League

    Michael Serbinis is the Founder and CEO of League. Founded in 2014, League is the leading healthcare consumer experience platform, reaching more than 40 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. Chapters 00:00 Podcast Introduction 2:00 Getting Shit Done: The Core Philosophy 07:02 Healthcare Challenges: Access and Understanding 13:20 The Agentic Era: AI in Healthcare 19:30 Learning and Adapting: The Key to Success 22:23 Partnerships: Transforming Healthcare Together 26:18 League's Platform Approach: A New Era in Healthcare 31:49 Balancing Family and Business: A Personal Journey 36:18 Perseverance in Hard Times: Lessons Learned

    41 min

  2. 1D AGO

    Nicholas Chepesiuk from Qualifacts

    Nicholas Chepesiuk is the VP of Innovation at Qualifacts. Nicholas was the Founder & CEO of OnCall Health, which was acquired by Qualifacts in 2022. Chapters 00:00 Podcast Introduction 2:00 Foundational Experiences in Early Roles 07:21 Telehealth Surge: Impact of the Pandemic 12:53 Post-Acquisition Insights and Growth Strategies 18:06 Trends and Opportunities in Healthcare 23:19 Building a Strong Company Culture 28:21 Personal Resilience and Coping Mechanisms

    38 min

  3. SEP 19

    Derrick Emsley from tentree and veritree

    Derrick Emsley is the Co-Founder of tentree and veritree. Chapters 00:00 Podcast Introduction 2:00 The Genesis of Tentree 05:04 Lessons Learned in Entrepreneurship 07:36 Transitioning to Veritree 09:07 Navigating the Climate Tech Landscape 12:07 Project Selection and Impact 14:52 Building Partnerships and Verification 17:37 The Importance of Trees 20:24 Consumer Behavior and Local Impact 23:12 Trends in Sustainability 25:52 Metrics and ROI in Sustainability 28:38 Learning and Growth as a Founder 31:26 Team Dynamics and Culture 34:09 The Role of Impact in Business 37:01 Technology in Tracking Projects 39:52 Overcoming Challenges in Entrepreneurship

    41 min

  4. SEP 17

    Chloe Liang from Cocasa

    Chloe Liang is the Co-Founder of Cocasa. Cocasa is revolutionizing travel and property ownership by allowing members to buy equity in luxurious holiday homes from €39,000/10% share. Chapters 00:00 Podcast Introduction 2:00 From Banking to Founding: Chloe's Journey 10:31 Identifying the Problem: Cocasa's Mission 21:08 Understanding the Cocasa Model 35:25 Navigating Challenges as a Founder 40:06 Engagement and Community Building

    40 min

  5. SEP 15

    Kyle Norton from Owner

    Kyle Norton is the Chief Revenue Officer at Owner. Chapters 0:00 Podcast Intro 2:00 Evaluating Companies: The Key Factors 07:38 Building a Revenue Team: Initial Steps and Strategies 11:39 Quality Over Quantity: The Importance of Revenue Quality 15:49 AI in Sales: Internal and External Impacts 20:42 Navigating the Changing Landscape of Outbound Sales 26:58 Hiring for Success: Qualities in Sales Roles 33:15 The Hybrid Work Debate: In-Person vs Remote 38:47 Geographic Strategy: Where to Position Sales Reps 44:09 Continuous Learning: The Benefits of Advisory Roles 47:20 Resilience in Sales: Maintaining Drive Through Challenges 52:31 Introduction to the Hard Part Podcast 52:31 Engagement and Community Building

    53 min

  6. SEP 10

    Benjamin Bergen from Council of Canadian Innovators

    Benjamin Bergen is the President at Council of Canadian Innovators (CCI). CCI is a member-based organization reshaping how governments across Canada think about innovation policy and supporting homegrown scale-ups to drive prosperity. Chapters 00:00 Podcast Introduction 2:45 Reflecting on a Decade of CCI's Impact 05:32 Understanding the Shifts in Innovation Policy 08:10 The Importance of Effective Government Policies 11:16 Building Stronger Industry-Government Relationships 13:37 Navigating National Sovereignty in a Global Economy 16:44 The Role of Government Procurement in Innovation 25:10 Navigating Government Contracts and Policy Advocacy 29:23 Capital Investment and Government's Role 32:24 Tax Competitiveness and Brain Drain 34:25 CCI's Mandate to Innovate 36:02 Navigating Federal and Provincial Regulations 38:29 Intellectual Property in the Innovation Economy 42:08 Engagement Between Government and Industry 44:07 Finding Purpose in Challenging Times

    48 min

  7. SEP 8

    Nicole LeBlanc from Woven Capital

    Nicole LeBlanc is a Partner at Woven Capital. Woven Capital is the $800M investment arm of Toyota Motor Corporation. Their aim is to broaden the group’s global reach and accelerate innovation by investing in exceptional growth-stage ventures. Chapters 00:00 Podcast Introduction 2:45 Introduction to Woven Capital 05:38 Investment Strategy and Structure 08:13 Exciting Technologies and Market Trends 11:18 Post-Investment Support and Value Addition 14:16 Global Investment Focus and Cultural Insights 16:53 Diverse Applications of Toyota's Expertise 19:44 Robotics and Future Trends 22:38 Corporate Venture Capital Landscape in Canada 25:16 Learning as an Investor 28:07 Fund Structure and Investment Strategy 31:08 Cultural Differences in Business Practices 33:42 Deep Tech and Hardware Investments 36:27 AI Applications and Industry Trends 39:23 Resilience and Optimism in Challenging Times

    41 min

  8. SEP 5

    Anthony Azrak and Jai Mansukhani from OpenSesame

    Anthony Azrak and Jai Mansukhani are the Co-Founders of OpenSesame. OpenSesame is building Cell, an embedded AI agent layer that lets users explore, understand, and take action inside any SaaS product using natural language. Chapters 0:00 Introduction 2:45 Introduction to Speedrun and OpenSesame's Experience 05:30 Identifying the AI Gap and OpenSesame's Focus 08:20 Customer Use Cases and Product Iteration 11:08 Target Market and Software Company Dynamics 13:58 The Future of AI Interaction and User Experience 16:49 Navigating the AI Landscape and Customer Education 19:33 Feature Development and Revenue Opportunities 22:34 Customer Discovery and Feedback Mechanisms 25:05 The Future of Work with Natural Language Interfaces 28:30 Raising Capital and the SF Ecosystem 32:25 The Language User Interface Revolution 37:21 Team Dynamics and Hiring in the AI Era 40:37 The Advantages of Being in Silicon Valley 42:49 Navigating Challenges as a Founder

    46 min
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About

The Hard Part, hosted by Evan McCann, uncovers the stories, strategies, and playbooks of Canada’s most influential founders, investors, and leaders. While Canadian innovators often fly under the radar compared to their American peers, The Hard Part shines a spotlight on their impact, redefining Canada’s role in global entrepreneurship.

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