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
