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

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