The Hard Part with Evan McCann

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

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: Strategies for Chief Sustainability Officers20:43 Crafting Effective Sustainability Strategies: Insights from Patch24:21 Strategic Procurement in Carbon Credits27:49 Navigating Global Projects and Technology Risks31:28 Understanding the Global Carbon Market Landscape35:14 Pricing Dynamics and Industry-Specific Strategies38:58 Future Trends in Carbon Markets and Technology43:40 Resilience in Entrepreneurship45:44 Engagement and Community Building

Francois Lafortune, Co-founder and CEO of Diagram Ventures, shares his entrepreneurial journey, inspired by his work with Wealthsimple. He discusses how Diagram sources and validates ideas through a problem-first approach and outlines criteria for startups' success, including market timing and competition analysis. Francois emphasizes the importance of building strong founding teams and explains their strategy for maintaining a founder-friendly investment model. He also highlights emerging trends beyond AI, such as stablecoins and digital payments, providing insight into the future of business.

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 Real Estate Services11:16 Transforming Home Buying: The Financial Impact13:23 Overcoming Traditional Barriers in Real Estate14:46 Expanding Horizons: Geographic Growth and Market Dynamics16:25 Understanding the Real Estate Commission Structure20:30 Leveraging Technology for Scalability23:12 Marketing Strategies in a Noisy Market25:51 Navigating Market Dynamics and Economic Factors30:23 Finding Purpose in Hard Times