The Hard Part with Evan McCann

Evan McCann
  • 4.9 (29)
  • 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. MAR 30

    Alison Kaizer and Andrew D'Souza

    This episode explores how AI is transforming hiring practices, emphasizing real-time testing, new roles, and the importance of human intuition in recruitment. Guests Ali and Andrew share insights on leveraging AI for better matchmaking, feedback loops, and building effective, nimble teams. Alison is the Partner, Talent at Golden VenturesAndrew is the Founder of Boardy Chapters 00:00 Introduction and Focus on Broken Hiring Practices 01:11 Traditional Success Metrics in Hiring Are Changing 01:57 Real-Time Testing and Practical Skills Over Past Experience 02:44 Shift from Filling Roles to Strategic Matchmaking 03:55 New Roles Emerge: AI Adoption Experts and Prompt Engineers 05:48 The Evolving Role of People Management in AI Era 07:20 The Value of Curiosity and Openness to Change 08:50 Technical Skills and Building with Latest Tools 10:22 Accessing Talent Beyond Traditional Platforms 12:02 Deep Conversations and Motivations in Hiring 14:04 Using AI for Better Candidate Matchmaking 17:01 The Power of Personal Connections and Fit 17:23 Feedback Loops and Continuous Improvement in Hiring 21:20 AI as a Central Team Member and Meeting Facilitator 23:48 Scaling Talent Acquisition with AI and Data 29:45 Building Long-Term Relationships and Trust with AI 33:18 The Human Element in AI-Driven Conversations 37:07 Future of Audio and Speech in AI Interactions 42:44 Trust, Accountability, and Outcomes in AI Recruitment 47:37 Balancing AI and Human Judgment in Hiring 52:17 Personal Relationships and Work Dynamics 54:13 Closing Remarks and Key Takeaways

    55 min

  2. JAN 21

    Max Cunningham from Sesh

    Max Cunningham is the Founder and CEO of Sesh Products. Sesh Products provides modern nicotine alternatives that aim to support in reducing and controlling cravings. Chapters 00:00 The Journey Begins: From Vaping to Sesh 02:46 Cultural Insights: The Swedish Influence on Nicotine Products 05:42 Navigating Regulations: Launching in Canada vs. the U.S. 08:08 Market Dynamics: The Shift from Smoking to Pouches 11:02 Branding and Positioning: Creating a Modern Nicotine Experience 13:42 Investment Insights: Partnering with 8VC 16:33 Consumer Feedback: Iterating in a Regulated Market 19:10 The Rise of Pouches: Trends and Accessibility 22:02 Health Perspectives: The Benefits of Nicotine Pouches 24:18 Building Trust: Ethics and Responsibility in Marketing 26:58 Future Outlook: Scaling and Global Expansion

    29 min

  3. JAN 14

    Ian MacKinnon from Stingray Security

    Ian MacKinnon is the Co-Founder of Stingray Security. Real-time protection from online scams, phishing, and fake websites. Ian previously Co-Founded Later.com Chapters 00:00 The Evolution of AI-Driven Phishing 03:57 Consumer and Corporate Perspectives on Phishing 08:17 The Role of Technology in Phishing Attacks 11:58 Identifying and Preventing Scams 16:28 The Future of Phishing and AI Tools 21:27 Building Trust in a Digital World 27:03 Mobile Vulnerabilities and Phishing Risks 29:37 Deepfakes and Voice Cloning in Phishing 34:34 The Ongoing Battle Against Phishing

    38 min

  4. 2025-12-11

    Robert Farlow from Plato

    Robert Farlow is the Co-Founder and CEO of Plato. Training Environments for Browser Agents Chapters 00:00 The Genesis of Browser Agents 02:38 Building Universal Agents 05:25 Training Models and Learning Mechanisms 08:02 The Future of Browsers and Agents 10:39 Trust and Error Management in Automation 13:39 Synthetic Data and Edge Cases 16:15 Complexity in Multi-Step Tasks 18:53 Navigating the AI Landscape 21:39 The Data Wars and Business Incentives 24:07 The Evolution of User Interfaces 26:36 Building in San Francisco 28:57 The Role of AI in Team Dynamics 31:45 Resilience in Entrepreneurship

    33 min

  5. 2025-11-25

    Brent Lane from BigGeo

    Brent Lane is the CEO of BigGeo. BigGeo is transforming how the world works with geospatial data. With innovative technology and industry-leading speed, they empower organizations to visualize, interact with, and unlock the full potential of location-based insights—at any scale. Chapters 00:00 Understanding Geospatial Data 02:45 The Importance of Location-Based Context 05:37 Infrastructure Challenges in Geospatial Data 08:09 The Future of Spatial Analytics 11:03 Monetization of Geospatial Data 13:53 Building a Unified Data Platform 16:42 The Role of AI in Geospatial Data 19:29 Navigating Sovereign Data and Cloud Solutions 22:14 Team Dynamics in a Tech-Driven World 25:02 Finding Balance in Business and Life

    35 min

  6. 2025-11-21

    Ignacio Tartavull from Pinkbot

    Ignacio Tartavull is the CEO of Pinkbot. Pinkbot builds robots that make last-mile delivery faster, cheaper and greener. Chapters 00:00 Intro 1:45 From Education to Neuroscience: The Journey Begins 02:33 The Shift to Autonomous Driving: A New Challenge 05:34 Navigating City Regulations: The Toronto Experience 08:13 Logistics of Robot Deliveries: How It Works 10:46 Real-World Challenges: Interacting with the Environment 13:51 Financial Aspects: Cost-Effectiveness of Delivery Robots 16:31 Business Model: Partnering with Restaurants 19:23 The Future of Autonomous Vehicles: A Long Road Ahead 22:13 The Future of Delivery Platforms 23:34 Weather Challenges in Delivery 24:39 Enterprise Partnerships and Their Impact 27:26 Insights from Being a Courier 32:19 The Future of Delivery Beyond Food 34:01 Regulatory Considerations for Delivery Robots 35:38 Urban vs. Suburban Delivery Dynamics 38:06 Building a Robotics Company 40:26 Designing for the Future of Transportation 41:20 Overcoming Challenges in Business

    43 min

  7. 2025-11-10

    Ben Vinegar from Modem

    Ben Vinegar is the Co-Founder of Modem. Modem is your auto-triage Product Manager. Modem turns scattered feedback – from users, teammates, and software – into actionable, living issues. Save time, reduce bottlenecks, and ship faster. Chapters 00:00 Intro 1:45 The Future of Developer Tools 05:35 The Changing Role of Software Engineers 15:04 Open Source in the Age of AI 19:02 Stickiness of Developer Tools 20:34 The Evolution of Developer Tools 27:58 Hiring in the Modern Tech Landscape 31:24 The Toronto Tech Scene vs. San Francisco 38:20 Resilience in Entrepreneurship

    41 min

  8. 2025-10-29

    Justin Sky from Rose Rocket

    Justin Sky is the CEO and Co-Founder of Rose Rocket. Rose Rocket is a SaaS-based Transportation Management System (TMS) specializing in workflow automation for Enterprise and SMB transport companies. Chapters 00:00 Intro 1:40 Acquisitions and Strategic Fit 02:18 Leveraging AI and LLMs in Business 04:41 Replatforming for Future Growth 07:44 The Surge of New Players in Transportation Tech 10:58 Understanding the Transportation Industry 13:42 The Future of Autonomous Trucks 15:32 Industry Dynamics and Consolidation Trends 17:59 Advice for Founders in Traditional Industries 21:23 Hiring for Culture and Values 24:39 The Evolution of Y Combinator 27:14 Refilling the Founder’s Tank 30:42 Navigating the Toronto Ecosystem 33:02 Strategic Fundraising Insights 35:03 Building a Diverse and Effective Board 37:16 The Toronto Tech Scene: Growth and Challenges 40:15 Lessons from the Journey of Entrepreneurship

    47 min
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4.9
out of 5
29 Ratings

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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