The Hard Part with Evan McCann

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 Building a Unified Data Platform16:42 The Role of AI in Geospatial Data19:29 Navigating Sovereign Data and Cloud Solutions22:14 Team Dynamics in a Tech-Driven World25:02 Finding Balance in Business and Life

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: Partnering with Restaurants19:23 The Future of Autonomous Vehicles: A Long Road Ahead22:13 The Future of Delivery Platforms23:34 Weather Challenges in Delivery24:39 Enterprise Partnerships and Their Impact27:26 Insights from Being a Courier32:19 The Future of Delivery Beyond Food34:01 Regulatory Considerations for Delivery Robots35:38 Urban vs. Suburban Delivery Dynamics38:06 Building a Robotics Company40:26 Designing for the Future of Transportation41:20 Overcoming Challenges in Business

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 Scene vs. San Francisco38:20 Resilience in Entrepreneurship

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 Consolidation Trends17:59 Advice for Founders in Traditional Industries21:23 Hiring for Culture and Values24:39 The Evolution of Y Combinator27:14 Refilling the Founder’s Tank30:42 Navigating the Toronto Ecosystem33:02 Strategic Fundraising Insights35:03 Building a Diverse and Effective Board37:16 The Toronto Tech Scene: Growth and Challenges40:15 Lessons from the Journey of Entrepreneurship

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 Operations28:47 Understanding Customer Needs31:12 Designing for Social Interaction32:21 Innovation vs. Remakes in Gaming34:21 The Testing and Refinement Process37:19 Balancing Rigour with Timelines38:59 Recognizing Joy in Gameplay39:55 Coping with Hard Times

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 Live Event Production31:17 The Intersection of Crypto and Live Events34:03 Artist Engagement and Fan Loyalty37:01 Navigating the Music Industry's Financial Landscape39:48 Finding Balance as a Founder

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 AI Impact33:06 Dealing with Hard Times

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 Accessibility Considerations15:58 Market Size and Potential17:39 Product Development and Iteration22:25 Engaging with Families for Feedback26:14 Addressing Therapist Shortages27:31 Government Partnerships and Support28:06 Overcoming Challenges as Founders

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 Collaborations39:42 Complexity in Apparel Collections43:55 The Investment Landscape in Apparel48:30 Overcoming Hard Times

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 Rebranding Journey41:36 Finding Balance in Entrepreneurship