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Episode 13: How Do You Solve a Problem Like Bad Carriers? With Cassandra Gaines, Founder and CEO of Carrier Assure

Intro – 00:00:00:

Welcome to Freight Nation: A Trucking Podcast where we explore the fascinating world of trucking and freight management. We dive deep into the freight industry and uncover why the trucking industry is more crucial to our country now than ever before. Stay tuned to uncover the driving forces behind successful trucking businesses and hear from the hardworking truckers and leaders who keep the world moving. Let’s hit the road.

Brent – 00:00:26:

All right. Well, welcome back to Freight Nation, a podcast by truckstop.com. We appreciate you being here today, listening along or watching along. It means a lot that you would give us your time and listen to great stories about logistics and trucking. And man, we got another great one today. One of my good friends on today, one of the most interesting people in all of freight logistics, Miss Cassandra Gaines. That’s right. You’ve probably seen her all over the place. She went from being just a college athlete to law in logistics to a media maven to a tech maven. So she’s done it all from top to bottom. And we’re going to hear her whole story today. And we’re so excited that she’s joined us on Freight Nation. Cassandra, thank you so much, my friend, for being a part of this.

Cassandra – 00:01:10:

Thank you for having me. I’m very excited. This has been a wonderful podcast. I’ve been following you.

Brent – 00:01:16:

Well, thank you. Well, I hope I’m doing you proud because I model a lot of my sort of enthusiasm around the shows and the media that you’ve produced. You’ve done an excellent job with that. So thank you so much. So I got to meet Cassandra at a TIA show in 2014 in Tucson, Arizona. We crossed each other in the hall and I was like, hey, I got to meet this person. So I got introduced to one of the most dynamic and enthusiastic and people in the marketplace that, by the way, also speaks her mind no matter where she is. And so we became fast friends and have been super friends since 2014, which is a lot like logistics, right? I mean, Cassandra, I know that it really is a lot like logistics, but I know you didn’t start out born in the trucking industry. You started out very differently. So start us out with like, okay, so young Cassandra, when she was in college and saw kind of where you were and then what drew you to law and then what brought you a little bit kind of on the logistics side? Tell our listeners and watchers. Where it all started.

Cassandra – 00:02:17:

I love that because everybody has like this great story because none of us really started out thinking, I’m going to be in trucking. We all have this crazy journey on the way there. But young Cassandra, even before college, I was all about sports. I did so many sports and I loved school. And I’ve always been like a very self-driven person like your kid. Sometimes I can be a perfectionist. So in school, I definitely did not have the dream that I’m going to be in trucking. I didn’t even know I was going to be a lawyer. And after college, I went into sales and operations for like five years in New York City. And I had a great time. And then the economy started to take a dive in 2008. And I had a relative that was like, you need to go to Law School. And here are the reasons why you’re going to love it. You have a personality for it. Yeah, just he kept pushing me. And I was about to be laid off anyway, along with all my colleagues. So I applied and I got into various schools and I just took the plunge. I really. I wanted a new adventure and I wanted a new skill set as well. And it was the best decision I ever made. Law School is so hard, but they really retrain your brain in the way you think. But I definitely didn’t go into Law School thinking I’m going to be a trucking lawyer. And in fact, when it came out, I knew I was going to be a litigator, which means you go to court. And I knew I was not going to do criminal law. I hate criminal law. I hate our criminal justice system. I love civil. So I knew at least what. I wanted to go. And so when I first joined the first law firm, which was based in Phoenix, although I’m a New Yorker, I was open to moving anywhere is, you know, how it is, you know, for the best job, but it doesn’t matter where it is. You’re going to take the plunge. And I was at the law firm and they make you do rotation in different areas of law to get used to it and figure out what you like. And I. This law firm didn’t like they had a lot of partners. Some of the partners just were not all that great, not very smart. Some of them were really smart. But the one that I love the most, his name is Jeffrey Simmons, and he was the COO at Global trends. And he was the best partner at this law firm by far. He’s an amazing guy. Anybody who meets him, they will know exactly what we’re talking about. And so all I did was, I’m sure you would have done the same thing, which is like I memorized his schedule. I was there before he showed up. And I was like, what assignments do you have for me today? And I can do that. Oh, sure. I know. I know trucking law, whatever. And then I would go randomly like research and stay up all night writing his briefs because he was the best at it. And I wanted to be the best too. And so years went by and suddenly I was like, I’m a trucking lawyer. That’s all I’ve been doing. I didn’t care what kind of law it was. I liked him and I liked this. And so that’s when I started going to TIA, TLA, a bunch of associations. And I met you. And I realized that in the area of law that Jeff was in, A, didn’t have any females. And B, looked like it was a really great niche. Being trucking is so dynamic. It is so difficult. And the law is the same way. It’s a very difficult area of law.

Brent – 00:05:28:

I wanna ask you a quick question about this. This just jumped to my mind. You said something that I’ve said many times to people about going to Law School. And it applies to like any additional education that you can help yourself. You said it helped you think differently. Man, could you just discuss that just a little bit? Because I want to continue with the story, but I don’t want to miss this. Because this helps people when you can train your brain to think differently. Talk a little bit about that.

Cassandra – 00:05:53:

Yeah, that’s important. Not a lot of people actually ask me that. It’s funny you ask, because my husband and I were just talking about, we’re telling a relative at Thanksgiving why we went to Law School. We both said the same thing at the same time. I was like… But it does retrain the way you think. It retrains the way you write, the way you speak, and the way you analyze situations. So I think when I went into Law School, my brain was pretty black and white. I was like one or the other, one or the other. And Law School brings you to not be black and white at all and to take in the entire situation and look for angles that no one would ever see, no one would ever consider. And then the other thing it does for you is you consume a significant amount of information. You have to distill it really fast, apply principles, and be able to spit it back out. And they train you to do that. And so they spend three years retraining you as a person, how you think, how you act, how you speak. And it takes you years. They actually don’t teach you how to be a lawyer at all because it takes that long to retrain you as a person. Isn’t that crazy? And they scared the heck out of you too. So all three years, scare the crap out of you. And I was always like the fear of failure. And the fear is really high because they give you so much information and then they give you one test at the end of the year. And if you fail it, you’re done. And it’s the same thing for every year. You don’t get homework or projects or anything. It’s just one test. And people fail it all the time. And then that’s the same way passing the bar. They just give you, so you take in a lot of information and you have to distill it, analyze it, and spit it back out and take a certain breed of people.

Brent – 00:07:33:

Wow, that’s super cool. So you’ve retrained, and I wanted you to say that because I’ve talked to many people that have been in the law field and they say the same thing. It’s really about changing your mindset and how you approach problems, how you approach situations. And that’s why having a good lawyer inside a business is super, super advantage to you. All right, so you became a trucking lawyer. You became a trucking attorney, and that was your whole goal. Just kidding. It was what you found was really compelling. And here’s something else I want you to talk about the value of this. Because I think this is, and I’m so glad you brought up Jeff. Talk about for a second about the value of working with somebody that you respect and that you admire and that can teach you. Talk a little bit about that because it sounds like you fell into a great situation that matched your desire for pursuing excellence.

Cassandra – 00:08:23:

I think you learn this when you’re an athlete, as you are as well, because we look for who the best coach is and who’s going to make, who’s the best. I want to be trained by the best, but they can’t be jerks either. They have to actually take the time to teach you and care about you as a person as well, as to be a two-way street. And so that to me has always been my path of how I can become excellent is surrounding myself with excellent people who care, who are good, wholesome people too. And so I would say along my way, every place I’ve been, every place I’ve been successful has been because of other people helping me along the way. And that has been very, very essential to how I perform. And I think that’s been a game changer for me. Like when I was working with Jeff Simmons and I made sure that he was my go-to person, even though sometimes at that law firm and Jeff will tell you the same, they would threaten me. They would be like, you have to work with other partners. You have to work with us. And I’m like, he’s a drug. And he’s not good at what he does. I know Jeff is excellent. I’m staying with Jeff. And they would come in and say, you will be fired, Cassandra. And I was like, this is my life. This is my career, my life. I’m staying with them. And I mean, I was younger, so I was a little bit sharper than I should have done. And I thought that as years go on. But I had no problem. Jeff Simmons will tell you at that law firm, I had no problem being like, no, you can fire me. I’m okay with that.

Brent – 00:09:53:

Well, I’m not surprised that you took that act at all from the person I met. Well, pretty much Cassandra. That’s awesome. But you know what? That can benefit you in a lot of most situations, and sometimes it doesn’t. But in most situations, when you’re sure of yourself, that benefits you. So that’s fantastic that you’re having that person that you can learn from. It’s so key. It’s just so key. So you became a trucking attorney, and you didn’t just work for Global Trans. You had several other really high-profile companies you worked with. Could you talk a little bit about working in the greater scope of the trucking industry and logistics? You met some fun people.

Cassandra – 00:10:30:

Yeah, I transitioned to Global trends, then I went to ECHO, then I went to Schneider, and then I went out on my own and started working for other brokerages and trucking companies. But I will tell those who are planning, thinking about going to Law School, they are a lawyer. Being a lawyer at a law firm is completely different than being a lawyer when you’re in-house. And that transition is just a whole other ballgame. And that was a big learning curve for me to learn to balance business. I mean, you have a great in-house counsel. I’ve met a couple of years at Trucks, and they do a good job of balancing those business concerns, watching out for the business, also understanding the practicality of everything, and not being so adherent to the law and scaring the crap out of everybody, if that makes sense too. It’s a fun experience and a way to change yourself as a lawyer as well.

Brent – 00:11:23:

So you worked for ECHO and then you worked for Schneider.

Cassandra – 00:11:29:

Covault first, and then ECHO, and then Schneider.

Brent – 00:11:33:

Can you share a couple stories that you kind of did? You were like, oh my gosh, I can’t believe that happened. Just a couple. You got…

Cassandra – 00:11:39:

Yeah, I have tons of them, but I will give you a couple of them. I tell this one publicly because everyone who’s been in this position laughs, but I got into Global Trans. It was the first time in-house counsel, really excited. And the compliance team reported it to me. That’s the team that vet carriers and they decide, is this carrier going to be active? Are they going to perform? Are they going to run our shipments? And I looked over the shipper contracts and they all said these carriers have to have commercial general insurance, general commercial policy. And then I’m looking through our compliance process and I’m like, we’re not making sure that these carriers have general liability. Oh my God, that is so much risk with that. We could be sued for all these things. This is crazy. And so told my company, every carrier that comes in the door, we got to require general insurance and we got to change this. Everybody’s got to have general insurance. I’d say within three hours, I had three leaders in my office being like, what are you doing? You are slowing up our everything. You are ruining everything. They were screaming, we were yelling. I was like, who the fuck are you doing this? Da, da, da, it’s great. But then, you know, talk free and I get excited. And those who have been in-house, they know how it feels when you have different readers coming at you. It does bring out curse words in you. But they were right. And it’s a great learning lesson for me. So in the industry, these brokers require carriers to have on the spot market, require carriers to have this general commercial liability policy, even though the shipper contracts do, even though your carrier contracts do. And it’s because these carriers, these small carriers do not have that coverage, period. You can require it for like some of the dedicated carriers, larger carriers will have it, but these small spot carriers, they don’t have it. And that was like my first in-house, I failed. I went home that night and I was like, Why didn’t I consult with leadership before I made some kind of decision like that? So I wasn’t a good teammate. I didn’t do enough research. It was the lawyer in me coming out that was like scared, right? So a lot of those types of decisions I really had to learn from and learn to work as a team too. And you lose that team environment a little bit at a law firm. That always cracks me up when I think about that.

Brent – 00:13:50:

So thank you for that story and being so transparent about that. That’s a big deal. Yeah. As we get older, we realize we all make mistakes, you know, and you’re kind of much more comfortable saying, yep, messed that one up. How do I pivot from it and move forward? So that’s super cool. So you worked in-house in some places and then decided to go out on your own and do some legal consulting for other businesses as well. How did your private practice go for you? How’d that work as far as like what you learned?

Cassandra – 00:14:17:

That was another really big learning curve at Schneider, Schneider was like the coolest job I ever had. They literally threw me in. They’re like, here, run our insurance department where all the accidents happen, all the lawsuits, all of the country. It was so, so fun. So after getting that experience and the ECHO and the law firm already that I’ve worked for and Global Trans, I knew I had so much to offer other companies. And I wanted to give it a shot being on my own as a business owner. And being able to work with so many different entities and learn more. The biggest challenge I would tell anybody who’s thinking of stepping out on your own and go from working 10 years for companies, large, to stepping out on your own, and you’re the leader, and you’re the one, all the business pressure comes down. The thing I learned is you are the only reason why things fail and when things don’t go right. You cannot blame it on this person over here, this bureaucracy, or da-da-da-da, or not enough budget. Nope. Every day, it’s you in the mirror, and when things aren’t going right in your own company, and not going in the right direction, there’s no one to blame. So you have to reassess yourself as a leader and reevaluate, what can I do to make this company successful? And I would say that is the biggest learning change. So you have your highs and your lows in your own business. And in my lows, I learned valuable lessons like that, which helped me be very successful. And I had a great time running my own law firm. It was so fun.

Brent – 00:15:46:

I’ve been there too, ran my own business, and it all rises and falls on whether or not you show up every day. In running your own practice, and by the way, I want to talk for a couple minutes about this because a tremendous amount of the logistics industry is small businesses. And they’re sometimes single operators or sometimes maybe two or three people in an office, but it’s always a very tight, short, a few amount of people that run the business. And so I want to talk a little bit more about, if you wouldn’t mind, about just things that you… Maybe something you might’ve done differently or something that you said, oh gosh, that worked out well for me. I made that decision. You’re running your own business because I’d love for the listeners and watchers to like hear from your experience because not only are you trying to run a business, you also have that, remember that lens of law around you going, oh gosh, I gotta look around all the corners all the time with everything. So talk a little bit about being a business owner and then seeing it through that lens.

Cassandra – 00:16:38:

I love that question, which also means that you’ve been a business owner and you know where I’m coming from because you asked that great question. And it was more of like a leading question because you knew. I would say that the biggest experience in failing is more when you go from a leader. When you start off, you are the only person. You are the treadmill operator is what some people call it. There’s podcasts about it and different things. You go from an individual contributor where you’re just running the show and you’re do to do until a point where the business gets so much that you become the problem and why your company can’t grow. And I would say that in the experience as well as running my own law firm, my own company, there was a pivot point where I was getting too much business and handle enough of it and And not learning how to delegate because I’m so scared. And who to hire or how to hire. And I hired and managed hundreds of people in my career. And but when it’s your own business and your own money, very different. And so I think that was like one of the biggest learning lessons from a failure to success when I was running that law firm. And I think for anybody who’s like, yeah, I feel like that. I feel like every day the business, like there’s a point where if the business doesn’t run without you, like you can’t take a four day vacation, the business doesn’t run just down. You are still like a sole operator of a business. And you’re going to get to a point where you’ve got to learn how to be a real business and delegate as employees and all and know how to grow and not too fast. And getting to that point is a very hard experience and to go learn for anybody who interested to hear more, you know, there’s a podcaster called Dave Ramsey. He’s been around forever. You probably have heard of him. And he used to have a radio. I used to listen to him on the radio and then he moved into podcasts, of course. So I always recommend that people listen to him every day. You should listen to him. I mean, there are others too. He’s not the entrepreneur on fires, another one. There’s a couple other ones to really make sure that you’re in that mindset of how to become a leader and be excellent at what you do. I like to steal what you tell your kids. Be excellent at what you do. I love that. So I’m probably going to repeat that now.

Brent – 00:18:42:

It’s all from somebody else. It’s just moving it forward, but you’re welcome to use it. Anything I say is probably from somebody else, but I follow along the same thing. And I’ve been listening to Dave Ramsey since, gosh, I think since the early 90s. And just the idea of working towards being personally debt-free because of the freedom that it gives you and those sort of things. Be able to make decisions in the right context without a tremendous amount of pressure on you. So that’s super cool that you give that advice. The guy in trucking that I call the small carrier Dave Ramsey is a guy named Kevin Rutherford who has Let’s Trucks. He talks along the same principles, and I’m always kidding him like he’s Dave Ramsey for trucking. So that’s super cool. So you started out with just like, as you said in the beginning, trucking. Many of us just, we don’t go, well, I’m going to be in trucking. And then you get into trucking and you go, this is the coolest industry in the world. I love it. I love what it does. I love how it helps them, the American public. And more important, I like the people that are in trucking because they’re just good salt of the earth. I want to produce a good product. I want to help people out, type of people that they’d like to be around. So I’m with you. I felt the same way. Boy, am I glad I ended up here. So amen to that. So you started your own thing. And then I remember when you did this, because I was like, why is Cassandra doing that? You started this crazy podcast. I’m not sure if you called it MadGaines. Did you call it MadGaines in the beginning or did it become that?

Cassandra – 00:20:08:

Not in the beginning. It became MadGaines. Yeah, it became that.

Brent – 00:20:11:

Yeah, it became that. So I was following along with it. I’m like, oh my gosh. And the thing is that I learned from you is that you took the gift that you were born with. Which is a gift of communication and personality and leveraged it for your business success. But you had a lot of fun doing it. So tell me about what day did you wake up on and went, I’m gonna start a podcast.

Cassandra – 00:20:35:

It was, I know exactly the day. This is how I’m going to do it. I didn’t even know what the heck a podcast was. It was 2018 and I had my own business and people were emailing me or messaging me or calling me and they were like, we have problems with this or what do I do about this and they couldn’t afford to hire me. Really, to get my advice, I would have to like let us out. I’d have to listen to you. I have to understand the facts and I give you advice. It’s going to cost you a couple grand, even if it’s something easy. And some of these business owners who like have a couple grand to spend on a lawyer, So what I did was I went on, I made videos with my phone. And you can see if you guys go to, you can Google Cassandra Gaines on YouTube. That was really, really old. And I made these videos. I literally put my phone up. I made the videos. Didn’t really know what I was doing. The horrible quality, horrible videos. But what I thought to myself was, and what you and I were talking about earlier, is don’t be perfect. The goal is to help people who can’t afford to hire a lawyer. And there are people out there who have common questions. And you, with transportation law, you can’t just Google this stuff. You can’t open up a book and learn it. There are very, very few lawyers who know it. And very little, probably like 100 of us in the country that truly know and understand transportation law in all aspects. I’m overestimating. So they’re hard to find and they’re expensive, etc. So what I did was I’m like, just to give back. And be helpful and not feel like a jerk to these people who can’t afford me. I’m just gonna make these videos. It doesn’t matter how ghetto or horrible they look because they’re getting free advice. They won’t care. And so I made videos. I was like, here’s how you do this in a contract. Here’s what it means when you do this. If you have a carrier or if you are a carrier that has this problem, you can see they’re really old on YouTube. They’re embarrassing. I hate like even looking at them because they’re so embarrassing. But I did that. I did that for two years. I just threw it up on the YouTube.

Brent – 00:22:25:

What do you hate most about them?

Cassandra – 00:22:27:

The bad quality. The bad quality. Literally, I’m like messing with the phone. And the phone’s wiggling. And like, I’m like showing my screen on the computer. And you can see the like the weird screen in the computer. It just walks back. Sounds bad. One of them I did in a coffee shop. And you can hear the coffee shop noise. But the worst thing about being a lawyer, by the way, is every hour you are not billing someone, you’re not making money. So that’s why I was like, I didn’t want to spend too much time in these videos because I wasn’t making money on these videos. And anybody watching these videos, they’re not going to hire me. They’re people who can’t afford a lawyer. So the YouTube channel started to snowball a little bit. And I never noticed until maybe a year went by and I looked at it. I’m like, oh, wow, a lot of people watch this. And it started to snowball and snowball. And then 2020 hit with COVID. And our industry, as you know, was crazy. There were points in time where truck drivers didn’t even know that they could get into the state of California. There were situations where truck drivers were not allowed into certain sections of New York City. The regulations were changing like that. Things were just all over the place for trucking. Truckers and brokers were fighting. So I learned how to go live, and I had no idea what I was doing, Brent. I Google and searched. I stayed up nights after nights learning how to go live. It’s not as easy as it was. It is now. Now it’s done. Good, good. But it was not that. It took a long time, and it was difficult. So I was like, I’m going to go live. I’ll do like a one-hour live session every Friday or something. People can ask me any legal question they want, and I’ll offer free advice to help people. And so I did. I went live. I didn’t know what I was doing. Some of those are also… At first, I think I did it on ZOOM and Vimeo, and then I did some more on YouTube. But some of those you can find on YouTube, too. And it was funny because people call in, and it was like Dave Ramsey live, and I would help them through problems. But then at one point, I looked down, and there were 3,000 people watching and listening. And I was like… Why? I’m a lawyer. We’re talking about legal stuff. Like, why? And I realized if people didn’t really care about the law thing, they were looking for community because people scare. And there’s so much going on in our industry and everybody’s at home. And so that is really what took off. And I kept doing, and then I just started doing live shows. And then I moved into, we’re not going to talk about law. We’re going to talk about all this other crazy stuff going on in our industry. We’re going to have interviews and turn them into a podcast. I didn’t even know what a podcast was. It just happened.

Brent – 00:25:00:

Yeah, but Cassandra, you are entertaining.

Cassandra – 00:25:03:

That’s because I have fun with it.

Brent – 00:25:04:

Well, that’s right. You have fun with it and you bring it back down to a base level where everybody can begin to understand it. I remember the first time I saw a trucking economist that I didn’t think was boring that I thought was really fun to listen to. I remember I was at the NASTRAC conference down in Orlando and I saw this guy named John Larkin on stage. I’m going, oh, he’s a pretty fun guy to listen to. I like him a lot. And then I understood it as well. So I remember watching your programs and when somebody bring in any topic and you’d answer the question and you’d make it personal always with them. And so that sort of connection with people is an incredible way for you to, A, number one, show you care, but B, extend the effect of your brand and your ability to reach a marketplace. So super, super innovative.

Cassandra – 00:25:47:

Yeah, isn’t that cool? Isn’t it crazy where life can bring us?

Brent – 00:25:50:

Yeah. So MadGaines didn’t just sit around in a podcast. You got approached by somebody or maybe you approached somebody. I don’t know exactly how this one worked out. So I’d love to hear how you ended up on the biggest platform in the marketplace. So tell a little bit about how that happened.

Cassandra – 00:26:06:

Oh, I should have mentioned, FreightWaves has been involved, I would say, 2019. I got introduced to FreightWaves, and I started appearing on their podcasts. And they were also just learning how to do lives, things. And they’re such good people. Such good people. And they were really fun. And Dooner is the one who he was like, you should do your own show. And he even told me, call it MadGaines. Because you’re always so crazy and wild. It was his idea. Yeah. It was his idea, which makes sense. He’s always the brilliant one with podcasting. And he helped me along the way. And so it was natural that the platform would just go over to Freeway sooner or later. At first, they were like, I will at first tooth be sold. And they’ll agree to this. I’m not disclosing anything. But they were like, your show is a bit crazy. We were going to bring you over to Freeway, but your show’s a bit crazy. It was crazy. There was a time where the show was… Crazy. Like there were tens of thousands of people watching it. And I mean, we had people cursing,

Brent – 00:27:07:

we had people screaming at each other. It was like the WWE. I know I watched some of it.

Cassandra – 00:27:14:

It was nuts. It was like Joe Rogan on steroids for our industry. And you know, one time I remember someone was a guest or something and they were smoking weed.

Brent – 00:27:24:

No way.

Cassandra – 00:27:25:

Yeah, I’m like, come on. Us hanging around drinking wine or something and cursing, that’s fine, whatever, but I’m like, I’m not judging anybody who drinks once a week to each their own, whatever anybody wants to do. No judgment. On the show, people. Come on up. And so that’s how wild it got. So, you know, it was natural to get to FreightWaves. And it did until I think they dropped all of their podcasters about a year ago. And so that’s where things kind of went their direction.

Brent – 00:27:53:

Right. Where does the MadGaines show sit today?

Cassandra – 00:27:56:

So good question. So my marketing team and I are working on a new plan and we’re going to announce it soon. So stay tuned. We are going to do a little bit of a spin and a reinvention on it.

Brent – 00:28:07:

Okay. Well, that’s good. Reinventing is awesome. That’s what you do in marketing. Yeah. Well, I mean, the talent is on my podcast right now. The talent, what made bad gains? Successful and great is the talent that’s on it, which was you, your personality driving it forward. And so that’s why I encourage, you said something earlier about the brand that you have and that you need to protect that all the time. You mentioned that when you had started your own business about everything rises and falls on you. And it’s so true. And if I learned anything in my 26 years of trucking marketing and marketing before that, is that the only brand you own at the end of the day is the brand of you. And how are you going to either increase the value of that brand or decrease the value of that brand every single day? And so that’s all you truly control. You don’t control anybody else’s actions. You can’t. But your responsibility is the brand of Cassandra or I have the brand of Brent. And so that’s pretty cool. So it’s good to hear you’re going to be relaunching it and bring it back out because I think the audience likes to hear from it. So that’s super cool. So Cassandra. If that wasn’t enough. Miss Gaines. That wasn’t enough. You’re like, hmm, what’s next for Casanova? What’s a problem that needs to be solved? And I remember talking to you when you first brought it out, and I was like, it kind of came out of nowhere. You go, no, it didn’t. You said, I’ve been thinking about this for a long time, about this being a problem. So you launched Carrier Assure two and a half years ago?

Cassandra – 00:29:33:

2000 to mid-2022. Yeah, yeah.

Brent – 00:29:36:


Cassandra – 00:29:37:

It’s been a year and a half long.

Brent – 00:29:38:

All right, you’re a thinker and an innovator. What spun it up? And then what made you take action on it? And then talk about how you’ve built it out. Because this is super cool. Because you had an opportunity in law, you had an opportunity in media, and now you’ve got an opportunity in building a product for the industry on the tech side. But my point, though, is that you’ve continued to iterate your business and moving it forward. So that’s super cool. That’s another lesson everybody needs to learn. You have to iterate your business. So talk about where to boil up, when did you make the decision, and then where have you taken it?

Cassandra – 00:30:11:

I think that it’s so funny. I love this. I love the passion you have and the energy you bring to this. It’s so fun. You’re doing what you’re born to do. You have been doing what you’re born to do, but you’re doing again what you’re born to do.

Brent – 00:30:23:

Me and Lady Gaga, we’re born that way, so we’re good.

Cassandra – 00:30:26:

Yes! So when I was working at all of these logistics companies, and even when I was at Schneider, it was confusing to me why everyone had the different way of vetting and onboarding a full truckload carrier. And many people do it wrong. Many people don’t understand the data. They don’t have the right data. They’re all, it’s weird. There’s no industry standard. So if you’re Wallart and you wanna hire a carrier, You may look at a carrier completely different than if you’re Target hiring a carrier. You’re ECHO hiring a carrier, and it’s an art and a science. And it drove me nuts. All of it drove me nuts. The inability to scale on this business when you have 15 people, but 1.15 people were reporting to me. They’re all sitting there typing in, looking at carriers, individual carriers. Such a waste of time when I need those 15 people to be looking at all this stuff over here. And so, and we’ll tell you that RMIS had come around and you guys bought RMIS, which changed the industry because it allowed, I don’t know, for some reason, not a lot of people used RMIS. And then when you guys brought it to light, it just, I feel like everybody was getting RMIS and it sped everything up and made it so much easier. I remember when my team had RMIS and I was like, where has this been for so long? The industry standard piece. And for those of you who don’t know, RMIS, because you’re coming here for a truck stop, RMIS does all that onboarding work for them and literally acts like a filter for these carriers. And it’s essential to your business as a logistics provider and as a shipper. What drove me even more nuts, there’s no industry standard. For how carriers should perform, a whole truckload of carriers. That drives me bananas. It is so hard, Brent, even if you know the data and you know everything, and you’ve got all of RMIS’s powerful data right in front of you, Unless you are really, really, really, really, really good. It’s very hard to know, is this carrier going to do a good job, full truckload of TVs running all the way across the country? Or can I give them full truckload of water bottles instead and see how they do? Should I give them something that is overhaul, flatbed, difficult, refrigerated? There’s no way to rack and stack and different things like that. No quick way. So what I did was, it’s been driving me nuts for years. So I took some of my revenue from GainBlocker. And I did something very risky and dangerous. And I talked to my husband about it before I did it because it was a big chunk of money. And I went and hired a developer, a couple of developers, and I had them create a prototype.

Brent – 00:32:55:

That’s putting your money where your mouth is there. There you go.

Cassandra – 00:32:58:

Yes. And my husband was like, I support you. You’ve got to live your dream. We’re both like this. You met Colin. We’re both like, you’ve got to live your dream. You’ve got to live your dream. That’s why we’re put on here on Plant4. And I’m like, well, this is my dream, Colin. This industry needs this. And so I created a prototype for what I felt was pretty way the data is, how it works, because there’s hundreds of algorithms that I had to literally sit there and type out perfectly for developer to do. And then there’s data science involved too. And you know a lot of how this stuff works. And so I created the prototype and then I rolled it out to a couple big companies. I’m like, it’s ugly, but tell me what you think, how’s it working for you? And it was working. And I was like, holy crap, I can’t believe this. And so I happened to mention it, Doug Wagner at ECHO. And I was like, I’ve been working on this. I had a prototype. You’re like the most savvy person I know when it comes to investments and technology. It’s his passion. And Doug was my mentor and has been to this day through everything. He was like, you amazing guy. And he’s like, you’ve got, you should investors. Here’s how you should do it. And blow this thing up, Cassandra. And I think that gave me courage to see someone else. Again, a mentor.

Brent – 00:34:10:

Another person investing in you, giving you, yeah, that’s incredible.

Cassandra – 00:34:14:

And these people, I never forget them. They have forever my loyalty. And there’s many of them, including yourself, that I will never forget. But he’s been coaching me all along. So this is cool, you guys. Because I never imagined a lawyer Just go and be a tech leader. And at night, I’d be like, what am I doing? And I don’t know this. No, screw that. I can learn it. So the other voice was like, screw that. I can learn it. Just build off your passion and how you want to change the industry. How I want to change the industry. Is I want good carriers, good truckload carriers. They know their business. They know their vehicles. They know their DOT performance. They know how to preach their plan. I want them to be illuminated. And I want all these bottom feeders, who maybe shouldn’t even be in our industry, to be pushed out a little bit. Not saying all of them are bottom feeders, but you know, and all of us listening agree, there’s a big chunk of carriers who should never be in this business. And they’re still running around, getting drug violations, drinking and driving, causing big accidents. They gotta go. Stealing things. So yeah, I took that passion and that’s what gave me the courage to start Carrier Assure. And so we took the prototype, rebuilt the whole thing, made it beautiful. And then that took about eight months. And then we launched in June of 2022, utterly terrified. But we went beta and then launched. I can’t remember which one, but beta for a while. But it was really cool to see all these companies using your platform.

Brent – 00:35:37:

That’s when you and I sat down at the Arkansas F3. We met the day before and you were talking all about your product and you were so excited about it.

Cassandra – 00:35:47:

Yes, we did. We talked for a while about it.

Brent – 00:35:50:

We did. We sat there almost 45 minutes talking about it.

Cassandra – 00:35:54:

And you were like, is it an onboarding platform? I’m like, it’s not. I’m not competition with our mass. It’s complimentary. And I kept telling you, it’s complimentary. But until you see it, people think, oh, onboarding. No, no, no, no. It’s not for coin to be onboarding. They’re not going to go in that direction.

Brent – 00:36:09:

And I was impressed by you because you kept asking me questions like, how should I go about doing this? What’s your thought about going into this? And I was honored that you would ask me my opinion on something.

Cassandra – 00:36:20:

You have been with Truck Stop, who is a huge brand in our industry, who started out. You were with Truck Stop from the very beginning, all the way to becoming a big, huge brand. So those people who haven’t known Truck Stop’s history. And of course, I’m going to ask you, of course.

Brent – 00:36:35:

Well, thank you. Thank you. I appreciate that. So you got into the beta in June 2022 and you’re bringing it out to the marketplace. And then, all right, then what was the next big mountain that you were like, oh gosh, I got to climb that now. What do I do?

Cassandra – 00:36:52:

I’ll tell you because you’ll never see this one coming. Or maybe you’re actually way smarter than me. I saw this coming a mile away. There was one mountain that hit me all at once. We grade the carriers as you know. A to F. I kept it very simple. There was no confusion. And it doesn’t mean you’re going to get in an accident. It means you need more vetting. Just put on short hauls. Do additional da-da-da-da. It’s like a way to guide somebody. Like a credit score. If we’re rewilling the money, check their credit score. If it’s bad, find things to do. So what I didn’t see is the product became popular way faster than I expected. And as you said, when I launched it, I kept telling people… We got a big problem coming toward us with this stuff and problems. I got lucky and I saw it a mile away. And so I did hit right at perfect timing.

Brent – 00:37:38:

It was almost perfect.

Cassandra – 00:37:40:

It was good timing. And so carriers, I didn’t expect the response from carriers, poor scores with a D or an F it was like a flood coming at me, I had death threats. I had a carrier who said they were literally like, I’m driving to your house right now to kill you and your kids. And I was like, well, I had a kid, so. Yeah, a bit dramatic on that. Yeah, very dramatic. But these people, it’s their livelihood. And you guys also know that when you blow up somebody’s spot and they have been maybe doing something they shouldn’t be doing, of course they’re going to react strongly. That was a big mountain to get over. And to remember… Also, that you can’t just disregard these people’s businesses because they have these bad. You’ve got to partner with them and give them avenues to improve their scores and things like that. And we’re still working on that, giving them as much feedback and being as responsive as possible. That was one big piece that I didn’t see coming as fast as it came.

Brent – 00:38:38:

The Whiplash of that you didn’t see coming. Yeah, that’s…

Cassandra – 00:38:42:

At one point in time, Brent, in the same week, I had three large carriers call me and scream at me for their scores. And then I had a person who threatened to kill me and then file a bar complaint against me, which was weird. And it was a bunch of that stuff. And I remember I literally sat down and cried because I was like the industry lightning rod right now. I’m just a lightning rod. And the next day, like athletes do, you pick yourself up and you’re like, I believe in what I’m doing. And I believe the difference I’m going to be making. And it’ll keep going.

Brent – 00:39:14:

Well, it’s good, no doubt. No matter what, my dad said the only time you’re ever going to lose if you get knocked down and you decide to stay down, you just got to get back up and get back in the game no matter what. So that’s super cool. So I know that Carrier Assure has created a lot of success in the market. Good to hear that you’re always trying to improve the process and continue to help carriers work their way into the best scores possible for themselves inside of it. I think your story is so compelling, Cassandra, because who would have ever thought this aspiring soccer player would become a tech giant inside of transportation? You know, somebody who’s creating technical advances inside of transportation. Only inside of our industry can that happen. And so it’s just a wonderful story.

Cassandra – 00:39:58:

It’s a good American dream, right?

Brent – 00:39:59:

It totally is. It’s a good American dream that took 10 plus years. People think it’s overnight. It’s never overnight. It’s a decade or longer, sometimes 20 years for it to happen.

Cassandra – 00:40:08:

And people are like, Cassandra launched this business and look how fast she’s gotten. Like, we’re at 8,600 users now and dah, dah, dah. And they’re like, look how fast she did it. I can do it that fast too. And I’m like, that was actually 10 years of building up relationships and knowledge and dah, dah, dah, dah to be able to launch it like that. But I will tell you that being a partner with, and for those of you who don’t know, Carrier Assure is an exclusive partner with RMIS and being able to stand next to a company who has also changed our industry and has excellent relationships with our carriers and excellent load board and obviously has always had an excellent product. But to be able to stand next to that company and be involved with them every day and work with your company too and all your great people, that is a freaking honor. Utter honor. And also inspiring.

Brent – 00:40:54:

Well, yeah, well, thank you. We feel the same way, Carrier Assure. We wouldn’t have pursued the partnership. So my goal today was for others to see your ingenuity, to see your innovation, to see your grit. And to be inspired by it, using their experience, by using their talent, and by using their never give upness, that desire, that persistence, that persistence to stay at it, that you can find success if you’ll just stay after it. And so I see you in that light, Cassandra, where you’re somebody who’s taken every piece of their talent and tried to create something that can benefit others. And that’s a really admiring thing. And so I just appreciate you being on Freight Nation today. It’s just an honor to hear the rest of the story. I’ve heard a lot of it. It’s good to hear some other parts of it. So I really appreciate you being on today.

Cassandra – 00:41:38:

Thank you for having me. I really appreciate it. What a good time.

Brent – 00:41:42:

Well, it’s a great time. So Cassandra, again, thank you. And Freight Nation, that’s a wrap on another episode at Freight Nation, a podcast by truckstop.com. I appreciate you watching and listening today. Y’all feel the same way? Y’all ready to go? Yeah, it’s good stuff. It’s so fun doing these things because I love to hear the story and I hope that you do too. Catch us next time on Freight Nation. We appreciate you listening and watching. Don’t forget to work hard, be kind, and stay humble. All right, thanks. Join us next time for Freight Nation. Talk to you soon.

Outro – 00:42:15:

On behalf of the Truck Stop team, thanks for listening to this episode of Freight Nation. To find out more about the show, head to truckstop.com/podcast. If you enjoyed this episode, make sure you hit subscribe so you don’t miss any future episodes. Until then, keep on trucking and exploring the open roads with Freight Nation: A Trucking Podcast.

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