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Oct 29, 2025 46 min

Justin Sky from Rose Rocket

from The Hard Part with Evan McCann Hosted by 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. Chapters 00:00 Intro 1:40 Acquisitions and Strategic Fit 02:18 Leveraging AI and LLMs in Business 04:41 Replatforming for Future Growth 07:44 The Surge of New Players in Transportation Tech 10:58 Understanding the Transportation Industry 13:42 The Future of Autonomous Trucks 15:32 Industry Dynamics and Consolidation Trends 17:59 Advice for Founders in Traditional Industries 21:23 Hiring for Culture and Values 24:39 The Evolution of Y Combinator 27:14 Refilling the Founder’s Tank 30:42 Navigating the Toronto Ecosystem 33:02 Strategic Fundraising Insights 35:03 Building a Diverse and Effective Board 37:16 The Toronto Tech Scene: Growth and Challenges 40:15 Lessons from the Journey of Entrepreneurship

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Justin Sky from Rose Rocket

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