How Do You Solve a Problem Like Bad Carriers? With Cassandra Gaines, Founder and CEO of Carrier Assure

Freight Nation: A Trucking Podcast

In this episode of Freight Nation: A Trucking Podcast, host Brent Hutto is joined by Cassandra Gaines, Founder and CEO of Carrier Assure. Tune in to hear Cassandra’s story, how she suddenly found herself in the world of trucking law, and how her years in multiple businesses led to her devising the software system Carrier Assure that would change the face of trucking in America forever.

Cassandra is a world-class trucking lawyer who’s worked with the likes of Lewis Brisbois, Echo Global Logistics, and Schneider National. You may know her as the host of “MadGaines”, the live trucking show launched from her MadGaines podcast that made transportation law exciting!

Episode Highlights:

[02:17] - Cassandra shares her journey on the road to becoming a Trucking Lawyer, from early days fresh-out-of-college, working in sales, and how the threat of losing her job pushed her to move to law school. Cassandra shares how law school retrained her brain and helped her on the path to becoming a full-fledged trucking lawyer, working under Jeffrey Simmons on a range of trucking-related cases.

[11:23] - Cassandra tells us about the differences between being a lawyer at a law firm, being a lawyer in-house, and working for her own business. She explains that learning how to balance business concerns, and understanding the practicalities of everything, is a fun experience to go through. We hear a story about her past role at GlobalTranz, how she made a mistake with the compliance team, and how she learned from that experience. From there, the conversation turns to her own experience of running her own business, and the process of learning to delegate and how to hire the right people.

[20:32] - In 2018, Cassandra received many messages from companies asking for legal advice. After realizing money was an issue for these people, Cassandra grabbed her phone and started making online content to help answer their questions. After a couple years of this, the pandemic hit. Cassandra, then, started doing live Q&As online to help the trucking industry. That is when everything changed.

[30:30] - Cassandra tells us how shockingly difficult the lack of an industry standard for carrier vetting was, and how RMIS helped her and her team save loads of time. But how do you know who’s good and who’s bad after that initial vetting? Cassandra brought in software developers to produce Carrier Assure: a complimentary system to RMIS that would help organize and grade existing carriers.

[36:38] - Cassandra tells us about the flood of messages she started receiving from truckers who had been given bad grades on Carrier Assure. It was a big mountain to get over, and she explains how she is working to introduce processes to help drivers improve - but it wasn’t the easiest road at all.

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