Chris Cochran, Founder & CEO of FreightWise

Real Leadership

Chris Cochran didn’t set out to disrupt one of the most entrenched industries in the U.S. — he just knew there had to be a better way. Now, as founder and CEO of FreightWise, he’s led one of the fastest-growing logistics tech companies in the country—proving that innovation doesn’t have to come from Silicon Valley to change everything.

In this episode of Real Leadership, Chris shares the story behind FreightWise’s rise, the lessons he’s learned from building in one of the most complex sectors, and why the AI revolution is less about hype—and more about what’s possible when leaders stay focused on value.

In this episode, we cover:

• Why small and mid-size businesses are the future of supply chain innovation
• The hard truth about AI adoption—and why most projects fail
• The freight tech shift that could redefine warehouse productivity
• What makes a great client relationship (and what can break it)
• How EBITDA became a mindset—and a mission

Time Stamps

02:17 - Understanding FreightWise and Its Market

13:25 - The Future of AI in Logistics

23:15 - Career Guidance in an AI-Driven World

29:14 - Lessons from Entrepreneurial Journey

36:01 - The Value of EBITDA in Business Growth

Show Notes

• Chris’s LinkedIn: https://www.linkedin.com/in/chrisrwcochran/
• FreightWise: https://www.linkedin.com/company/freightwise-llc/
• Freightwise LinkedIn: https://www.linkedin.com/company/freightwise-llc/
• Jim’s LinkedIn: linkedin.com/in/jim-weaver-36457418
• Real Leadership Podcast: realleadership.oningroup.com
• Real Leadership LinkedIn:https://www.linkedin.com/company/104897916/
• The Ōnin Group: oningroup.com/clients