The Freight Pod
The Freight Pod
Andrew Silver
Ep. #88: Tom Madine, CEO, ShipStation Global
1 hour 48 minutes Posted Aug 4, 2026 at 11:00 am.
Sponsor Open And Scale Hook
Chicago Studio Welcome And Guest
From Telecom Sales To Freight
Selling Parcel To Underserved SMBs
Franchise Consolidation And Roll-Up
Agents Franchises And Direct Channels
M&A Integration: Culture Brand Incentives
Vision Execution And Winning Belief
Leading Through COVID And A Downcycle
Multi-Mode Growth And Carrier Strategy
Octane And ShipStation Global Thesis
Private Equity Fit And CEO Truth
Risks That Matter: Carriers And Cyber
What Success Looks Like Next
Final Thoughts And Sign-Off
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1:48:34
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Show notes
From a live, in-person Chicago studio, we sit down with Tom Madine to unpack what real scale looks like in transportation, and why SMB shipping is still one of the most misunderstood corners of logistics. Tom shares his path from early sales roles into building Worldwide Express, then zooms out to the hard truth: small and midsize shippers don’t just buy rates. They buy accountability, fast fixes, and a partner who can “make it right” when the inevitable problems hit. We go deep on business ...