Justin Sky from Rose Rocket

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The Hard Part with Evan McCann

Evan McCann

360 episodes

23 hours ago

The Hard Part, hosted by Evan McCann, uncovers the stories, strategies, and playbooks of Canada’s most influential founders, investors, and leaders. While Canadian innovators often fly under the radar compared to their American peers, The Hard Part shines a spotlight on their impact, redefining Canada’s role in global entrepreneurship.

Business

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Business

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Justin Sky from Rose Rocket

The Hard Part with Evan McCann

46 minutes 33 seconds

6 days ago

Justin Sky from Rose Rocket

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