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PODCAST

The Hard Part with Evan McCann

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.

business

All Episodes

00:52:40

Kyle Norton from Owner

The Hard Part with Evan McCann ·

2025/09/15

Kyle Norton is the Chief Revenue Officer at Owner.Chapters0:00 Podcast Intro2:00 Evaluating Companies: The Key Factors07:38 Building a Revenue Team: Initial Steps and Strategies11:39 Quality Over Quantity: The Importance of Revenue Quality15:49 AI in Sales: Internal and External Impacts20:42 Navigating the Changing Landscape of Outbound Sales26:58 Hiring for Success: Qualities in Sales Roles33:15 The Hybrid Work Debate: In-Person vs Remote38:47 Geographic Strategy: Where to Position Sales Reps44:09

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00:47:34

Benjamin Bergen from Council of Canadian Innovators

The Hard Part with Evan McCann ·

2025/09/10

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.Chapters00:00 Podcast Introduction2:45 Reflecting on a Decade of CCI's Impact05:32 Understanding the Shifts in Innovation Policy08:10 The Importance of Effective Government Policies11:16 Building Stronger Industry-Government Relationships13:37 Navigating National

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00:41:16

Nicole LeBlanc from Woven Capital

The Hard Part with Evan McCann ·

2025/09/08

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. Chapters00:00 Podcast Introduction 2:45 Introduction to Woven Capital05:38 Investment Strategy and Structure08:13 Exciting Technologies and Market Trends11:18 Post-Investment Support and Value Addition14:16 Global Investment Focus and Cultural Insights16:53

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00:45:30

Anthony Azrak and Jai Mansukhani from OpenSesame

The Hard Part with Evan McCann ·

2025/09/05

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.Chapters0:00 Introduction2:45 Introduction to Speedrun and OpenSesame's Experience05:30 Identifying the AI Gap and OpenSesame's Focus08:20 Customer Use Cases and Product Iteration11:08 Target Market and Software Company Dynamics13:58 The Future of AI Interaction and User

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00:43:13

Derek Bullen from S.i. Systems

The Hard Part with Evan McCann ·

2025/09/03

Derek Bullen is the Founder and Board Director of S.i. Systems.S.i. Systems is one of the largest Canadian IT staffing and consulting firms that connects organizations with skilled technology professionals. They specialize in providing contract, permanent, and project-based talent across areas like software development, business analysis, project management, and IT infrastructure.Chapters0:00 Introduction2:45 Founding Principles and Evolution of SI Systems11:02 Shifts in the Contractor

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00:43:07

Emily Luk from Wealthsimple

The Hard Part with Evan McCann ·

2025/09/02

Emily Luk is a member of the Product team at Wealthsimple.She previously Co-Founded Plenty, which was acquired by Wealthsimple.Chapters00:00 Emily's Journey: From Venture, Stripe and Even.05:44 Cultural Insights from Stripe and Even08:27 The Birth of Plenty: Identifying Gaps in FinTech11:17 Navigating FinTech Challenges and Infrastructure14:17 Unlocking Multi-User Experiences in FinTech17:11 The Evolution of Consumer FinTech19:56 Wealthsimple Acquisition: A Seamless Transition23:01 Building a

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00:40:59

Matthew Lombardi from The Icebreaker

The Hard Part with Evan McCann ·

2025/08/29

Matthew Lombardi co-founded The Icebreaker with Jeff Waite and Michael Edwards.The Icebreaker is Canada's defence innovation network, trusted by founders and funders, operators and professionals at DND and the CAF, defence primes, IDEaS, NATO DIANA, and everywhere decisions are made to defend the nation.Their mission: to make Canada a net exporter of defence technology by 2030.The Icebreak LinksThe Icebreaker Hackathon on September 20.Hundreds of Canadian companies making ‘dual use’ products

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00:37:47

Carter Li from SWTCH

The Hard Part with Evan McCann ·

2025/08/27

Carter Li is the CEO of SWTCH.SWTCH - https://swtchenergy.com/Chapters00:00 Genesis of SWTCH: A Personal Journey05:35 Challenges of EV Charging in Existing Infrastructure08:06 Designing Charging Solutions Based on Dwell Time11:05 Technological Advances in EV Charging13:49 The Value of EV Infrastructure in Real Estate16:33 Shifts in the EV Charging Landscape19:32 Vertical Integration in Charging Solutions22:27 Innovative Solutions for Grid Overload25:29 Monetization Strategies in Charging

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00:47:20

Simon Hørup Eskildsen from turbopuffer

The Hard Part with Evan McCann ·

2025/08/25

Simon Hørup Eskildsen is the Co-Founder and CEO of turbopuffer.turbopuffer is a fast search engine that combines vector and full-text search using object storage, making all your data easily searchable.Chapters00:00 Introduction to turbopuffer06:46 Revolutionizing Search with TurboPuffer11:45 Technical Innovations Behind TurboPuffer15:55 Caching Mechanisms and Performance19:27 Scaling Challenges and Solutions23:09 Navigating Industry Shifts and Market Dynamics30:08 Sales Strategies and Founder-Led

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00:47:08

Stewart Lyons from Bird

The Hard Part with Evan McCann ·

2025/08/22

Stewart Lyons is the CEO of Bird.Bird is on a mission to provide eco-friendly transportation for everyone. Chapters00:00 Stewart Lyons: A Journey Through Entrepreneurship05:29 Navigating Regulatory Challenges in Canada08:04 Turning Around Bird Global: Strategies and Insights11:07 Operating a Global Business from Canada13:15 Building Trust with Regulators and City Partners15:52 Operational Complexity: Making Bird Profitable18:37 Innovations in Scooter Technology21:11 Seasonal Operations: Adapting to

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00:40:09

Christian Weedbrook from Xanadu

The Hard Part with Evan McCann ·

2025/08/20

Christian Weedbrook is the Founder and CEO of Xanadu.Xanadu is a Canadian quantum technology company and one of the world's leading photonic quantum hardware providers. Chapters00:00 Understanding Quantum Computing05:51 Infrastructure and Capital Needs for Quantum08:40 Raising Capital in Quantum Tech11:58 Government Support and Quantum14:16 Photonics vs. Other Quantum Approaches15:55 Talent Acquisition in Quantum17:45 Global Operations and Foundry Partnerships19:27 Staying Canadian in a Global

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00:38:17

Dennis Pilarinos from Unblocked

The Hard Part with Evan McCann ·

2025/08/19

Dennis Pilarinos is the Founder and CEO of Unblocked.Unblocked brings all the context about your codebase together, so your team gets expert-level answers, no matter where they’re working.Chapters00:00 The Journey of Dennis09:48 Building Developer Tools: Challenges and Insights16:59 The Importance of User Experience in Development24:45 AI's Role in Modern Development29:58 Attracting Top Talent in Tech34:19 The Evolution of Vancouver Tech Ecosystem

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00:45:35

Mark Doble from Alexi

The Hard Part with Evan McCann ·

2025/08/18

Mark Doble is the CEO of Alexi.Alexi is the flexible AI platform trusted by leading law firms to develop proprietary insights, orchestrate high-quality work, and deliver stronger results — in a fully private, firm-controlled environment.Chapters00:00 Exploring the Gaps in Legal Tech05:26 The Evolution of Legal Research Automation08:00 Understanding AI Hallucinations in Legal Contexts12:20 The Role of Human Lawyers in an AI-Driven World15:38 Building a Platform for Law Firms20:12 Navigating the

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00:47:25

Stu Szabo from Beacon

The Hard Part with Evan McCann ·

2025/08/15

Stu Szabo is the Co-Founder and CEO of Beacon.Beacon is a new solution built to facilitate smooth transitions for immigrants relocating to Canada. Their Super App simplifies the financial and informational hurdles that newcomers face, offering everything from banking solutions to essential resources, all designed to ease the transition into Canadian life.Chapters00:00 The Inspiration Behind MyBeacon07:14 Transitioning from Investor to CEO12:36 Rethinking Financial Services16:28 The Immigrant

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00:52:37

Andrew Ostro from PolicyMe

The Hard Part with Evan McCann ·

2025/08/14

Andrew Ostro is the Co-Founder and CEO of PolicyMe.PolicyMe's mission is to reinvent insurance for Canadians by merging smart technology with unwavering humanity–driving down costs, simplifying protection, and prioritizing your needs at every step.Chapters00:00 The Birth of PolicyMe05:25 Understanding Life Insurance08:37 The Buying Process of Life Insurance11:36 Streamlining Insurance Pricing14:40 Innovations in Underwriting17:17 AI and Operational Efficiency21:18 Types of Life Insurance25:03

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00:49:18

Kylan Gibbs from Inworld

The Hard Part with Evan McCann ·

2025/08/13

Kylan Gibbs is the Co-Founder and CEO of Inworld.Inworld develops AI products for builders of consumer applications, enabling scaled applications that grow into user needs and organically evolve through experience.Chapters00:00 Founding Story of Inworld05:29 Consumer vs. Enterprise AI Applications08:33 Bridging the Gap: Prototypes to Production11:34 Runtime: Scaling Consumer AI Applications14:20 Experimentation and User Engagement17:18 The Complexity of AI in Consumer Products20:11 Personalization

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00:40:02

Mike Peasgood from ENVGO

The Hard Part with Evan McCann ·

2025/08/11

Mike Peasgood is the Co-Founder and CEO of ENVGO.ENVGO is a technology company bringing cleantech solutions to the boating industry. At ENVGO, they are making high performance boating clean, efficient, and low maintenance. They are building a future where hydrofoiling electric watercraft are powered by clean energy, and offer an experience of flight over the water. Chapters00:00 Founding Aeryon Labs (acquired by FLIR Systems)05:32 Building Aerial Robotics: Key Differentiators08:13 The Birth of

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00:43:22

Daniel Wigdor from AXL

The Hard Part with Evan McCann ·

2025/08/08

Daniel Wigdor is the Co-Founder and CEO of AXL.AXL is a Canadian venture studio transforming world-class research into high-growth companies that shape the future of applied AI. Led by seasoned tech entrepreneurs and applied AI experts, AXL’s mission is to ensure Canada’s top breakthroughs are built and scaled at home. By connecting academia with real market demand and full-stack venture creation, AXL helps Canada move from invention to impact, anchoring talent, intellectual property, and long-term

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00:39:25

Zane Hengsperger from Nox Metals

The Hard Part with Evan McCann ·

2025/08/06

Zane Hengsperger is the Founder and CEO of Nox Metals.Nox Metals is the modern factory for fast, low-cost metals.Chapters00:00 Inspiration Behind Metal Fabrication05:42 Current Landscape of Metal Processing08:20 Sourcing and Quoting in Metal Fabrication11:08 Geographical Considerations in Metal Supply13:47 Venture Capital and Manufacturing16:42 Navigating the Re-Industrialization Movement19:06 Automation and Operational Efficiency22:03 Building a Diverse Team for Manufacturing24:52 Scaling Physical

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00:40:36

Andrew McLeod from Certn

The Hard Part with Evan McCann ·

2025/07/30

Andrew McLeod is the Co-Founder and CEO of Certn.Certn isn’t a background check provider with a tech department; it’s a tech-first leader innovating every part of the background screening process. Certn is changing background screening globally by offering the easiest-to-use platform, checks in 200+ countries and territories, free 24/7 customer support, and fast and compliant results. Trusted by 10,000+ clients, Certn helps businesses manage risk, stay compliant, and hire faster—all while delivering

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367 results

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