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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

00:32:36

Robert Farlow from Plato

The Hard Part with Evan McCann ·

2025/12/11

Robert Farlow is the Co-Founder and CEO of Plato.Training Environments for Browser AgentsChapters00:00 The Genesis of Browser Agents02:38 Building Universal Agents05:25 Training Models and Learning Mechanisms08:02 The Future of Browsers and Agents10:39 Trust and Error Management in Automation13:39 Synthetic Data and Edge Cases16:15 Complexity in Multi-Step Tasks18:53 Navigating the AI Landscape21:39 The Data Wars and Business Incentives24:07 The Evolution of User Interfaces26:36 Building in San

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00:35:23

Brent Lane from BigGeo

The Hard Part with Evan McCann ·

2025/11/25

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.Chapters00:00 Understanding Geospatial Data02:45 The Importance of Location-Based Context05:37 Infrastructure Challenges in Geospatial Data08:09 The Future of Spatial Analytics11:03 Monetization of Geospatial Data13:53

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00:43:26

Ignacio Tartavull from Pinkbot

The Hard Part with Evan McCann ·

2025/11/21

Ignacio Tartavull is the CEO of Pinkbot.Pinkbot builds robots that make last-mile delivery faster, cheaper and greener.Chapters00:00 Intro1:45 From Education to Neuroscience: The Journey Begins02:33 The Shift to Autonomous Driving: A New Challenge05:34 Navigating City Regulations: The Toronto Experience08:13 Logistics of Robot Deliveries: How It Works10:46 Real-World Challenges: Interacting with the Environment13:51 Financial Aspects: Cost-Effectiveness of Delivery Robots16:31 Business Model:

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00:40:52

Ben Vinegar from Modem

The Hard Part with Evan McCann ·

2025/11/10

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.Chapters00:00 Intro1:45 The Future of Developer Tools05:35 The Changing Role of Software Engineers15:04 Open Source in the Age of AI19:02 Stickiness of Developer Tools20:34 The Evolution of Developer Tools27:58 Hiring in the Modern Tech Landscape31:24 The Toronto Tech

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00:46:33

Justin Sky from Rose Rocket

The Hard Part with Evan McCann ·

2025/10/29

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.Chapters00:00 Intro1:40 Acquisitions and Strategic Fit02:18 Leveraging AI and LLMs in Business04:41 Replatforming for Future Growth07:44 The Surge of New Players in Transportation Tech10:58 Understanding the Transportation Industry13:42 The Future of Autonomous Trucks15:32 Industry Dynamics and

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00:43:40

Elan Lee from Exploding Kittens

The Hard Part with Evan McCann ·

2025/10/27

Elan Lee is the CEO of Exploding Kittens.Chapters00:00 Intro1:40 Designing Engaging Games02:49 The Importance of Player Feedback05:28 Accessibility and Player Experience08:22 The Golden Age of Tabletop Games11:25 Kickstarter Success Strategies13:54 Building and Sustaining Community16:53 Quality Control in Physical Games19:25 Expansions and Game Evolution21:38 Retail Dynamics in Tabletop Games23:26 Balancing Creativity and Business26:13 Persistence in Game Development28:20 Team Structure and Internal

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00:43:08

Ahmed Nimale from KYD Labs

The Hard Part with Evan McCann ·

2025/10/22

Ahmed Nimale is the Co-Founder and CEO of KYD Labs.Chapters00:00 Intro1:40 The Journey into Live Entertainment02:56 Understanding the Ticketing Landscape05:35 The Role of Venues and Ticketing Platforms08:20 Marketing Challenges in Live Events11:28 Financial Dynamics of Live Entertainment14:17 The Future of Ticket Pricing17:01 The Impact of Resale Markets20:13 The Role of AI and Technology in Live Events22:57 Direct Artist-Fan Relationships25:18 The Evolution of Music Financing28:24 The Future of

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00:36:40

Doug Roseborough

The Hard Part with Evan McCann ·

2025/10/21

Doug Roseborough spent his career at multiple leading technology companies including 30 plus years at Oracle.Chapters00:00 Intro1:40 Early Days at Oracle02:56 Oracle's Secret Sauce05:16 Transition to the Bay Area08:15 Rolling Out Pricing Models10:31 Cultural Insights at Oracle13:05 Leadership and Team Dynamics15:35 Operations at Oracle17:59 Effective Meetings20:38 Customer Engagement Strategies23:00 Startup Advice25:37 Navigating a Noisy Market28:11 Bay Area Mentality30:31 Career Reflections and

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00:29:43

Tamer Shahin and Jerry Chen from Hiro

The Hard Part with Evan McCann ·

2025/10/17

Tamer Shahin and Jerry Chen are the Co-Founders of Hiro.Hiro improves child health by turning physiotherapy into fun, interactive, movement-based games designed for kids of all abilities.Chapters00:00 Intro1:40 Inspiration Behind Hero02:55 Understanding Therapy for Children with Disabilities06:19 Gamifying Physiotherapy: The Solution08:25 Accessibility and Convenience in Physiotherapy11:39 Leveraging Technology for Progress Tracking14:02 Feedback from Parents and Therapists14:47 Pricing and

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00:50:26

Cameron Conn from Champlain

The Hard Part with Evan McCann ·

2025/10/14

Cameron Conn is the CEO of Champlain.Cameron previously Co-Founded OneComply (acquired by GeoComply).Chapters00:00 Intro1:40 Cameron's Journey Through Industries07:51 Transitioning to Retail and Learning the Ropes12:14 Positioning and Pricing Strategies in Apparel19:11 Navigating Wholesale and Direct-to-Consumer Channels26:25 Navigating Industry Challenges27:36 The Vancouver Apparel Scene29:53 Understanding Manufacturing Relationships33:00 Designing Collections with Purpose35:22 The Value of

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00:42:48

Robert Saunders from Ownright

The Hard Part with Evan McCann ·

2025/10/08

Robert Saunders is the Co-Founder and CEO of Ownright.Ownright simplifies real estate transactions with the perfect combination of expert legal guidance, a client-first approach, and efficient technology. Chapters00:00 Intro1:40 The Genesis of Ownright07:14 Navigating Regulatory Challenges13:14 Financial Hurdles in Real Estate Transactions17:28 Growth Strategies and Market Expansion20:50 Understanding Pricing and Unit Economics24:38 Leveraging AI for Efficiency32:11 The Future of PropTech37:23 The

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00:45:53

Brennan Spellacy from Patch

The Hard Part with Evan McCann ·

2025/10/06

Brennan Spellacy is the Co-Founder and CEO of Patch.Patch combines technology and carbon markets expertise to help companies build and execute their carbon credit strategies from end to end, channelling capital into critical climate solutions.Chapters0:00 Intro1:40 The Evolution of Sonder: From Flatbook to Hospitality Innovator06:41 Transitioning to Patch: The Journey to Founding a Climate Solution11:07 Understanding Carbon Markets: The Role of Patch in Sustainability16:09 Navigating Complexity:

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00:49:12

Francois Lafortune from Diagram Ventures

The Hard Part with Evan McCann ·

2025/10/01

Francois Lafortune is the Co-Founder and CEO of Diagram Ventures.Francois is also a Managing Partner at Sagard and Chairman of the Board at Nesto.Diagram is a venture launchpad building the next generation of global companies based in Canada. They develop and incubate our own ideas, and find exceptional entrepreneurs and technologists to build companies with us.Chapters00:00 Introduction2:00 The Genesis of Diagram: A Venture Studio's Origin05:23 Navigating the Idea Flow: From Concept to

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00:32:23

Rishard Rameez from Zown

The Hard Part with Evan McCann ·

2025/09/29

Rishard Rameez is the Co-Founder and CEO of Zown.Zown is a buyer-first real estate platform operating in both Canada and the U.S., built to reward and empower people to reach their homeownership dreams faster. Through their model, buyers receive up to $25,000 toward their home purchase — funded through the commission Zown earns. There’s no repayment, and buyers keep full ownership from day one. Chapters00:00 Podcast Introduction2:00 The Spark of Innovation: A Reddit Post04:43 Identifying the Gaps in

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00:41:25

Michael Serbinis from League

The Hard Part with Evan McCann ·

2025/09/26

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

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00:38:14

Nicholas Chepesiuk from Qualifacts

The Hard Part with Evan McCann ·

2025/09/25

Nicholas Chepesiuk is the VP of Innovation at Qualifacts.Nicholas was the Founder & CEO of OnCall Health, which was acquired by Qualifacts in 2022.Chapters00:00 Podcast Introduction2:00 Foundational Experiences in Early Roles07:21 Telehealth Surge: Impact of the Pandemic12:53 Post-Acquisition Insights and Growth Strategies18:06 Trends and Opportunities in Healthcare23:19 Building a Strong Company Culture28:21 Personal Resilience and Coping Mechanisms

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00:41:26

Derrick Emsley from tentree and veritree

The Hard Part with Evan McCann ·

2025/09/19

Derrick Emsley is the Co-Founder of tentree and veritree.Chapters00:00 Podcast Introduction2:00 The Genesis of Tentree05:04 Lessons Learned in Entrepreneurship07:36 Transitioning to Veritree09:07 Navigating the Climate Tech Landscape12:07 Project Selection and Impact14:52 Building Partnerships and Verification17:37 The Importance of Trees20:24 Consumer Behavior and Local Impact23:12 Trends in Sustainability25:52 Metrics and ROI in Sustainability28:38 Learning and Growth as a Founder31:26 Team

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00:40:15

Chloe Liang from Cocasa

The Hard Part with Evan McCann ·

2025/09/17

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.Chapters00:00 Podcast Introduction2:00 From Banking to Founding: Chloe's Journey10:31 Identifying the Problem: Cocasa's Mission21:08 Understanding the Cocasa Model35:25 Navigating Challenges as a Founder40:06 Engagement and Community Building

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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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