The Hard Part with Evan McCann

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 Diverse Applications of Toyota's Expertise19:44 Robotics and Future Trends22:38 Corporate Venture Capital Landscape in Canada25:16 Learning as an Investor28:07 Fund Structure and Investment Strategy31:08 Cultural Differences in Business Practices33:42 Deep Tech and Hardware Investments36:27 AI Applications and Industry Trends39:23 Resilience and Optimism in Challenging Times

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 Experience16:49 Navigating the AI Landscape and Customer Education19:33 Feature Development and Revenue Opportunities22:34 Customer Discovery and Feedback Mechanisms25:05 The Future of Work with Natural Language Interfaces28:30 Raising Capital and the SF Ecosystem32:25 The Language User Interface Revolution37:21 Team Dynamics and Hiring in the AI Era40:37 The Advantages of Being in Silicon Valley42:49 Navigating Challenges as a Founder

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 Landscape13:29 The Art of Matching Talent with Opportunity18:10 Scaling the Business: Lessons Learned25:28 Building Relationships and Client Trust29:02 Leadership Transition and Executive Roles33:22 Personal Growth and Life After Leadership39:54 Navigating Hard Times and Resilience

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 Comprehensive Product Suite at Wealthsimple26:00 The Importance of Multi-User Financial Management28:35 Growth Through Multi-User Engagement31:41 Resilience in the Face of Challenges

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 useful for defence, survey finds - The Globe and MailChapters00:00 The Genesis of The Icebreaker and Canadian Defence Tech05:35 Urgency for Change in Defence Strategy08:09 Cultural Shifts in Defence Innovation10:54 The Role of Technology in Defence and Civilian Life13:32 Building a Community in Defence Tech16:27 Spotlighting Canadian Innovators19:09 Infrastructure Needs for Defence Innovation21:52 Procurement and the Future of Defence24:28 The Arctic: A New Frontier for National Security27:25 National Pride and the Defence Tech Movement30:12 Opportunities for New Talent in Defence Tech

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 Infrastructure27:15 The Future of Urban Living and EV Charging29:55 Scaling Hardware in EV Charging32:57 The Impact of Autonomous Vehicles on Charging35:44 Finding Balance in the Entrepreneurial Journey

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 Growth35:43 Pricing Models and Customer Relationships41:25 Staying in Canada vs. Moving to the US44:59 Coping with Challenges in Entrepreneurship

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 Market Conditions24:17 Seasonal Workforce and Scalability25:10 Exploring Diverse Transportation Modes27:02 Franchising and Business Replication29:53 Safety Measures in Micro-Mobility33:46 User Experience and Software Integration35:24 Subscription Model for Repeat Users37:25 Micro-Mobility as Last Mile Solution39:18 Insights on Acquisitions40:54 Balancing Growth and Profitability43:24 Motivation and Resilience in Business

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 Market21:02 Maintaining Passion and Energy22:12 Commercialization of Technology25:09 Interplay Between Quantum and AI27:06 Future of Quantum Hardware28:34 Software Development in Quantum31:18 Building Partnerships and Use Cases33:10 Quantum Computing for Battery Development34:31 Applications Across Industries36:11 Future Predictions for Quantum Computing37:21 Misconceptions About Quantum38:46 Coping with Challenges in Business

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