Special Release: Training on the Basics with #TheFreightCoach
Freight 360
November 20, 2025
Want a freight sales edge that actually works? We break down how repeatable habits, niche focus, and real conversations turn new brokers into confident closers—no fluff, just a proven playbook built on consistent activity, early call reps, and mentorship that sharpens judgment. In a world of automation, the human moat still wins: real tone, real trust, real momentum. If this hits, subscribe and share with someone who needs the push to pick up the phone.
Support Our Sponsors:
Freight Collection Solutions – Click Here
QuikSkope – Get a Free Trial: Click Here
Levity: Click Here
DAT Freight & Analytics – Get 10% off your first year!
DAT One – Brokers & Carriers: Click Here
Recommended Products: Click Here
Freight Broker Basics Course: Click Here
Join Our Facebook Group: Click Here
Check out all of our content online: Click Here
See full episode transcriptTranscript is autogenerated by AI
What is up, ladies and gentlemen? We are back. We are live. This is the Freight Coach Podcast, the top podcast in transportation coming to you guys every single weekday. 8 30 a.m. Pacific, 10:30 Central to break down some industry headlines. But most importantly, you guys, provide some actual insight into what you can do with all of this information. If this is your first time tuning in, welcome. This is the real side of freight, ladies and gentlemen. And I say that before every single show. And what I mean by that is I only speak with transportation professionals because at the end of the day, I want to talk to the right individuals who have done what you're looking to do or who are currently doing what you're trying to achieve. So you can take that information, apply it, utilize it, and see a meaningful difference in your business and your life. Happy Thursday, everybody. I got a couple of very special guests for you guys here today. We're going to be talking about something we're all very passionate about, and that's training and development. We are uh we work with the uh the new broker success program with the TIA, and we're gonna be talking about that continuous development. So I got my man Ben Kowalski and Nate Cross back on the show to break it down. Fellas, thank you so much for taking the time to join me today. Good to be back with you, man. Yeah, pleasure. Dude, anytime the Bills Mafia gets on the show, I I like I just had um gosh dang it, I'm drawing a blank. Hold on, two seconds. Greg Finnerty on the show. I don't know if you're familiar with it.
SPEAKER_00: 1:33Oh, yeah, yeah. He I ran into him at a golf tournament over the summer. He's like, hey, Nate, you're Nate, right? And like he just knew me from Freight 360, and he's literally like right here in my backyard in Buffalo. So got to got to chat with him for a few minutes. Yeah.
SPEAKER_01: 1:46Dude, I I love having Greg on. Like he is the epitome of the Bills fan, everything. And I just told him, I'm like, dude, I just want to go to a game just to like experience it, right? Because like I've noticed it, it's kind of like everybody's welcome there, right? It doesn't matter if you're an opposing fan, like you guys just want to party and see the Bills win, and it doesn't matter who's there.
SPEAKER_00: 2:08Yeah, it can be a good team or bad team, and like, yeah, there's gonna be some shit talking for sure, but like, yeah, it's always a good time.
SPEAKER_01: 2:16No, I love it. So, dude, what's what's going on out there? How is you know, because we're coming up on we're in the middle of the the fourth group of new brokers that we've worked with this year, and you know, I I always love I training and development to me is it's like a passion because I like seeing it like click for people, right? And we're actually in the process, we just had somebody start with us here this week, and you know, she's coming in for your business development purposes and everything. And I love bringing that, like kind of like crossing those hurdles of going from not understanding the industry and having all those questions to like the actual deployment and seeing it kind of go out there. So, what's it been like? What like what are you guys seeing out there from like a training perspective? What are some of those things that you think people are still missing to this day?
SPEAKER_00: 3:05Well, I'll tell you, this is the timing of this is great because Ben and I just did a we did a session yesterday with the the current cohort. And like we this guy, one of the guys in the class, like he right before we got on, he just he emailed us and was like, Hey, just wanted to let you know. Like, I just dispatched my first truck to my pick up my first shipment. And we had talked to him, I had talked to him in like in between sessions and over the last couple of weeks, trying to kind of talk him through um pricing and you know, different things he could do. And but the big takeaway is like we and we said it then yesterday was like, so this can be done, right? Like if you follow the things that we teach, regardless of the type of market that we're in, um, you put in the effort and the reps, like the results will come. It just, you know, there's a bit of um randomness, right? And and luck, I would say, but the persistence and putting in the activity in is what is what really helps. Um, I will tell you, I think the people that have struggled, there's they're you know, a lot of the people we talk to, they're they're where they're at in their journey is like they're like, I'm brand new, haven't done anything yet, right? And we do like a prospecting or a lead gen uh session, and like you come back the next week and they haven't they still haven't done anything. So I think it's I think it's just taking action, Ben. I don't know what what your perspective would be, but that's kind of what we see every every time we do one of these courses.
SPEAKER_02: 4:27I definitely agree. And it's funny because like I always picture there's a line. Do you remember this movie? It's probably like 10 years ago, War Dogs. Do you guys remember the movie? And there's a line where they're both sitting at that like a hot dog stand, and one of them's pitching, I think it's Jonah Hill's characters, pitching the other guy on like why they should go into the business of like working with the government and selling arms, right? It doesn't really matter what it was, right? But the one guy goes, Wait a minute, you think two guys are gonna compete with these huge companies for trillions of dollars in this industry that like he's like, I don't know anything about. And then Jonah Hill's response is like, dude, do you know how big that pie is? That pie is so big, like we don't need the whole pie. We don't need half of it. We don't even need a slice. We need like a crumb. And he's like, if we can get a crumb, we can build a business. And I saw that right when I was starting around in this industry, give or take. And I just remember I'm like, that is the same thing as our industry, right? Like, it's roughly 800 billion to a trillion dollars a year gets spent moving things around the country. And a one-person brokerage has every bit of the same advantages as a big one in some cases. And sometimes, in some cases, even more, right? And it's like whether the market's going up or down, if you put the activity in and more importantly, put it in consistently. I've genuinely never come across anybody that hasn't found success in the industry if they do the things that we all three of us talk about for years in that class and on our shows.
SPEAKER_00: 5:58We had we had a guy, Ben, you and I, that we had talked with years ago when he was debating first starting off. And um we did some coaching and mentorship with him over the years, and eventually kind of, you know, he he'll check in from time to time, but he went from absolutely no experience to building a$20 million a year brokerage just from knowing the the people, right? Knowing the people that he could ask the questions to and um putting in the putting in the activity. Like that was it. So um I I think that you know, that's kind of like the two parts that you need is you know, anybody, anybody that's you know, not afraid to pick up the phone can put the activity in. But if they don't know what they don't know and they don't have someone to ask questions or bounce ideas off of, you know, they're they're just kind of going into it blind. So I think that's where I love the concept of coaching and and consulting, whether it's through like TIA or if it's a one-on-one. Um, you know, I even to this day, like Ben, you and I, like we have people that we go to for you know outside perspective and advice. We obviously have each other, which is great, but still like there's people that I go to all the time, and I'm like, hey, he's been doing this longer than me. I'm gonna ask him this question because I don't know everything, right? And he doesn't either, but he knows more than I do.
SPEAKER_01: 7:09I I think like it you be a fool to not network with people that are further along down the road. Like one of one of my best friends out there, I mean, he's he's uh Chris Brewer, he's founder of River City Logistics. Like, I talk to him a lot because like he's his company, he's built it, right? Like he's been there. And I always want to find out like, hey man, what what can I do better? Like when you're at where when you were at where I am right now, what would you do differently now? Looking back, because it's like that perspective is invaluable. And if that can save you time, I mean, or and money and mistakes, like, dude, it it's just something that I think a lot of people overlook. And, you know, when it comes down to training and development, for for example, like I will always focus on the fundamentals because that's all I've ever been able to do. That's like gained results, right? Like I think that people want to sidestep doing the actual work that's required. And, you know, for me, it's like I think people go too much too soon and then they they burn themselves out too quick. Where for me, it's like I like repeatable, scalable tasks, right? Like that's why I always talk about just add five initiative for cold calling, right? If you've never cold called in your life before, start with just making 20 calls in a day and then build up from there. It's more important that you hit those daily numbers repeatedly throughout time than it is to just do 100 in a day and then stop for three days and then try and do it again because you got to show up and put in the work and it takes a lot longer than you want. But eventually, if you're actually putting in the reps, you're gonna get better. You're gonna get that feedback, you're gonna understand how to navigate through those conversations. You'll never get there by thinking about starting. You just gotta go find a number that you can hit every day, no matter what. Cause like I don't want to do shit every single day. But I've been doing this for so long now. I know that me showing up and putting it in no matter what is way better than thinking I need to take a day to reset. That's way more detrimental to my long-term progress than just fighting through. And you know what? You might not hit 50 calls that day, but you got 20 in, right? That's better than nothing. And I think most people are have that all or nothing mentality. And sometimes, man, just that effort, that's all that matters to keep you going to reset. And then that next day you're gonna come out, you know, guns blazing.
SPEAKER_00: 9:28Yeah, you know, one of the things that we like Ben and I personally have always leaned in on when it comes to the cold calling early on, is like those first, we'll just give it, well, I'll just say like the first 500 or 1,000 calls you make, right? Like, it's not about you trying to land a customer in those calls as much as it's about you being able to figure out the best way for you to make those calls, right? You find your voice, you feel you kind of get a feel for what you're comfortable, most comfortable with as far as opening and like the questions to ask, and you start to hear the common objections and you start to realize who's on the other line of the phone, like who's the one picking up the phone when I make these calls? So it's really about putting, you know, like you said, if you do only 20 calls, that's 20 more reps you've got in that skill set versus if you do absolutely zero, right? You get people that they'll spend months like, yeah, I just gotta find the best leads, and then I'll make the calls. And it's like, you can find the greatest leads in the world, but you make that first phone, that first cold call, like you're gonna suck at it because you have no idea, no experience, right? You just gotta put those reps in, and over time it will, you will eventually get very comfortable. It's like, you know, people that do that podcast, right? The first time you ever do a podcast, you probably are super nervous and like you have no idea. You go through and you do it like Chris, you do it like every single day, right? It's second nature to you now. The same concept applies with cold calling shippers. It's that simple.
SPEAKER_02: 10:48Well, and it's funny, right? Because I think everything you just both of you just said, I agree with, right? And the thing I also want to add, and you both alluded to this, right? But like I think is almost as if not more important is when you do it every day, right? You build the habit and it doesn't seem like work, right? And it's funny because in the Tim Ferris episode this week, he was using this to talk about exercise. And he goes, People always go, I don't have enough time to start, or I gotta find the perfect routine. And he used an example. I forget who the person was, but he's like, Can you do one push-up before you go to bed? And the guy's basically like, well, yeah, I can do that. He's like, just start there. Just do one a day. Don't even think about doing more at any point in time, just do one before you go to bed. He's like, that guy six months later was doing 50 push-ups before you went to sleep, and then also started like running in the morning, right? The thing you've got to do is if you eliminate the emotional stress of, I'm so worried, I don't want to do this, I'll do it tomorrow. Just to your point, Chris, like I'll even say this sometimes. I'm like, if you haven't made any, make one today. Just make one. If you can make one, do that for a week. And then next week, see if you can make two. Just set the bar low enough that you absolutely are tripping over it, but you're getting into the routine and getting used to doing that every day. And honestly, most people just start naturally, oh, that wasn't that bad. I'll just do another one. Oh, that wasn't that bad. I'll just do another one. Because even for me, and I've made countless cold calls over my life, like when there were periods where I did it every day for years and then didn't do it for a few months because I was either doing coaching or whatever. When I went back to go get it, I'm like, I can feel it being like emotionally difficult to get back into it. I'm like, I literally talk to people every day on what to say, how to say, and what they're doing. But when I went to go do it again, I'm like, oh, this muscle is atrophied. Like, I'm just not used to it. It's like starting to run after you haven't run for a few months because you were just doing some other thing, right? It's way harder to stop and start than to just keep moving gradually towards that.
SPEAKER_01: 12:43It's a perishable skill. And I think that's what a lot of people overlook, right? And I think like the longer you do something, the um the more you think like, oh, I can just pick this back up whenever I want. And, you know, for me, it's like I I think that also when you're going out there on your own for the first time, and you know, Nate, you've been on the, you know, and Ben, even you, you've been an agent before, you've been on that side. I think a lot of people uh have a hard time accepting that the book of business they have at their original employer, they didn't actually build. It was through attrition they attained it, and they're working with it. And they they might be an account manager, right? And again, not here to knock anybody. Account managers are extremely valuable, but it's a different mentality when you have to go out there and hunt for your dinner. And I think that that's one of those things that again, that's why I'm always about you got to start somewhere, right? And it's one of those things, like, you know, Nate, you brought up the podcast here. Like we've done over 1,300 episodes. I leave them all up there because I want people to hear episode number one. I want them to hear how shitty it sounds. Well, some people might think I still sound shitty, but that's irrelevant. Um, it but like how bad it sounds compared to like where it is now, right? It's a system, and then you know, one thing people bring up to me quite often is as I don't see how you do this every single day. I don't see how you don't do this every single day. The hard work done. I have the system, I have the process, I have everything in. Like I have all of December booked out. We're already booking into January at this point, right? Like when you have that ability and that skill set through time. Again, this didn't happen year one or year three. This was like a year four thing where we actually started to build up that momentum. And then now it's like, dude, it's like second nature. Now it's not work, just like cold calling for my brokerage. It's not work to me. Like, I would be lying if I didn't say I felt that little tinge of anxiety from time to time because you just never know who's gonna pick up the phone. But I love the thrill of that.
SPEAKER_02: 15:32Yeah, and it's hold on, I would have had one thing too, because Nate and I talk about this. And when people were asking me, like, how much time do you put into prepping for a show? I'm like, 30 seconds sometimes. I'm like, Nate and I will literally yesterday we'll literally text each other, like, what do you want to talk about? We'll start, and he's like, Oh, this thought comes to mind, and then you can just do it.
SPEAKER_00: 15:51And it's like we actually our yeah, our episode yesterday was about training and development for new people.
SPEAKER_02: 15:57And it's funny, is to your point, Chris, like when he's traveling or we don't do it together for whatever reason, because like of what's just going on, like I miss doing it. I'm like, I'll text Nate and I'm like, oh dude, I'm like, can't wait for you to be back on the show again because I'm like, it's not even work, like it just becomes part of what you do and you look forward to it. And when you have the excitement, like when you're cold calling to bring the analogy back, like that little bit of fear is what makes it interesting. Like, if it wasn't there, it would just be digging a proverbial hole all day, right? You're just shoveling in and shoveling it out, right?
SPEAKER_01: 16:30Yeah, I I look at it, you know, and again, I you know, in in today's environment, I also look at like when when there's so much competition that's out there, because it is, right? No matter what. Like you look at it as, yeah, there's 25,000 brokers. I'm just pulling a number out of out of the thin air, but I think it's like 25,000 brokers that are out there, but now you have independent agents that are out there as well. So it's like, how many independent agents are out there on top of the W-2 employees for these companies? Then you'll again. So it's like there's a lot of competition, and that's just on the brokerage side. That's not talking about the trucking side of things. And I look at it is it's like when you're in a saturated industry, every industry is saturated. I don't care what anybody freight's not fucking unique. Where we're the most over every industry has it. How are you gonna stand out in a crowd? Right. And and I found, and this is somebody who sold pre-COVID and post-COVID now, the best way to stand out for me, and this is just what we built our business on, is having the exact same conversations, calling the exact same prospects and building up that niche. Like, I don't say this that we can't do drive-in and refrigerated. I could, I've done it extensively. I don't want to, like, because I found that one trick pony approach has been the most effective way for me to build my business. This isn't theory. This is what I've done to actually build my brokerage over the last 36 months. And if you're out there on social media and paying attention, it's the worst freight market of all time. There's no opportunities, nobody's added. That's all bullshit. People are adding you if you know how to actually hold a conversation and you and like you have a reason for calling them. And I think you have a lot of sales managers now who haven't called in a while, and but like they're training people to do a job that, yeah, they're right. That's how it used to be, but that's just not how it is today, where you can just call somebody, hey, we're a broker, we can save you some money, we can do everything. That used to work, but it doesn't anymore. So you got to shift, you got to train your people up, you got to get them up with the times.
SPEAKER_00: 18:37Yeah, I had a guy that started um started working with us last Friday. I put him through training on Monday. He he had worked previously, he waited out of non-compete. So he was out of the game for like a year, right? Sideline. Um, got him revamped up on Monday. His first load delivered this week, like today. Like he just put in the calls and like like it this does work. Like, obviously, you know, he he had the background and the experience, but he knew this is what worked before and it's going to work again now. So he he got right into it, made the calls, and boom, got his first customer set up, got the first load uh posted and booked, and boom, delivered. Like this, this is not like you said, it's not theory. This is like the actual real world here.
SPEAKER_01: 19:21So I think what you see more times than not, you guys, and I'd love to get your take on it, is I think it's just a lot of people who aren't actually doing the work and they've formulated a reason why they can't, you know, and and I know I did that for the majority of my life, right? Like I had a bunch of fucking excuses out there, like, oh, it's not gonna work, it's this and that, it's everything under the sun. What are your guys' thoughts on that? Do you just think it just boils down to two camps of people? It's the one who are actually doing it and the ones who are just not, and they're refusing, and they have every excuse in the world.
SPEAKER_00: 19:52Yeah, I think there's like a spectrum, right? Because there's the people that are just afraid to pick up the phone. Like Ben and I got a solicitation email this morning from a broker. Like it it was so badly written, and I just forwarded to him. I was like, I just can't believe people are actually thinking this stuff works. Like, yeah, um, so I think there's the the people like that that just refuse to pick up the phone and make the phone calls um versus the people that will do it, right? But then I think there's a spectrum of like just the skill of having like an interpersonal tact, like being able to hold a conversation because they're like I've had people that um I've worked with that are just super socially awkward, and they're like one or two only customers are just other socially awkward shipping managers, right? Like, yeah. Whereas like if you're super talkative and very just you know open and will have a conversation with anybody, you have that kind of that chameleon personality. I think they have a they have a better shot at um building a book of business um easier than someone who you know doesn't have those strong points in just being able to communicate effectively and with anybody. I think there's definitely a spectrum of those people that are trying, but yeah, there is the other camp of like they just won't. They don't, they're for whatever reason, they just won't pick up the phone and make the calls.
SPEAKER_02: 21:06I think it's human nature too, Chris. I think both of what you said is true. And I think there's it's it doesn't stay that way for everybody forever. Some people grow out of it, some people grow out of it and go back into it and they're stressed and they want to blame everything. I think human nature is your ego trying to protect itself when things aren't going well, and it does that by going, well, it's not your fault, it's the market. It's not your fault, you don't have the right tech. It's not your fault, you don't have the right this. You don't have this, it's their fault, it's the market, it's the economy, it's whatever, right? But at the end of the day, right, if you can direct that energy and fear and use it to push you forward to make the next phone call, all that stuff becomes an advantage. And it just hinges on are you going to blame anyone else or are you going to take responsibility? Because every time you blame something else, it makes you feel better right now, but you also lose the ability to change it. Because if it actually is the economy and I'm right, I can't do anything about it anyway. So then what do I do? Right. So even at the very least, if it is my fault, I have the ability to change what I'm doing to see if I can improve on it, right?
SPEAKER_00: 22:08The other thing I'll add to that too, because Chris, you brought this up earlier. Like there's 25 some thousand um licensed brokerages, and and then you add in like how many employees or agents are within there. Like it's a it's a big, big pool of internal competition, if you want to call it that. Ben and I have always said, like, dude, you just have to be like slightly better than half, like above the average, right? To be that difference maker, right? And that and that could come down to just making more calls than the average broker, right? Or, you know, it's it's it's that simple. All you gotta do is be just one percent above average, and you already got half the competition in your rear view mirror.
SPEAKER_02: 22:46It reminds me of like the story of the guy in the woods. There's three guys running from a bear and they're running as fast as they can, and the one guy realizes I don't have to outrun the bear, I just have to outrun the other two guys next to me, right? Like, you don't gotta be better than it and then everything. You just gotta be a little better than your competition.
SPEAKER_01: 23:03No, I I agree with that. And and I don't think it's you know, could Nate to your point earlier about you guys got a solicitation email. Like, I get them too, right? Like people are like it's so easy to win out there, you guys, because people are looking for the they're it's just copy and paste. They're trying to send it out, they're trying to automate it all. And to me, it's like you can just make a your ability to have a basic conversation with somebody is going to be the greatest skill set over the next five years as AI automation becomes your ability to actually communicate with somebody in person, the phone, everything else will be the greatest separator. And I think that, you know, again, as much as people are pushing that, you almost got to revert back to this the Stone Age ways of doing things because it's all about reading the room, right? Like when I'm interviewing somebody on this show, for example, um, it's my job to get them talking. And but like uh the adverse skill set to that is is when I'm cold calling somebody, I have to be able to read that person. If they don't want to talk, I don't want to push it because I will do way more damage than ending the call. And then that's the way that I approach it. So again, it's a but again, you'll never know that unless you're doing the reps. And that's why it's like again, you just gotta do it, right? And here's one thing I will say, and and again, this just comes from somebody who actually cold calls every single day. People are way friendly, more friendly than you think. Like they might they're cordial, they're not gonna be your best friend, but they're cordial, right? Like those horror stories that you hear are in the minority of the outreach that you will actually put in.
SPEAKER_02: 24:38Yeah, I couldn't agree with everything you said more, right? At the end of the day, like you can't learn that stuff through reading a book. It's the difference between knowledge and wisdom. You can read about this all day long, but you're not gonna get better at it unless you do the thing, which is wisdom through experience. And you don't do that unless you're putting the calls in, right? Understanding, building the intuition on where to judge someone, how they feel, where to talk, where to ask questions, and where to go.
SPEAKER_00: 25:04Yeah, I agree. Go ahead, Dave. I want to hit on the AI thing really quick here, too. Like you mentioned, like people do business with those that they know, like, and trust. And I I don't know about you guys, but every time I've talked to Chat GPT, I don't feel like I know, like, and trust Chat GPT. Like, I know how to use it to get certain answers. But like I had a guy that came to me and he's like, hey, I'd like I'm trying to grow from this level to this level. What do you think I should do? I found this, I can pay this company and they're gonna do all this AI stuff for me to get me all these warm conversations. And I was like, hell no. I was like, I don't want my name and reputation like affiliated whatsoever with a a startup AI voice company, because then like you might they might tarnish your relationship with a a potentially great shipper down the road. So um, yeah, I I 100% back up your opinion on that with your ability to have a conversation is gonna be your your best separator in the next five years. That's that's huge.
SPEAKER_01: 26:02No, I I appreciate it, guys. And you know, I appreciate your time. This flew by as I knew it. I was I'm not gonna let it go this long now before you guys are on the show next. I got to get you guys back on sooner because you know I know you guys are as passionate about training and development as I am, and it's uh, you know, it's one of those things it's always good having you guys back on. How does anybody reach out to you guys, though, to find out more about what you guys got going on?
SPEAKER_00: 26:23Freight360.net. That's our website. You can email us. There's a contact form right in there, and we're all over YouTube, LinkedIn, whatever. Just look us up. We should all find us.
SPEAKER_01: 26:33Ben, Nate, thank you so much. If you guys can't find them out there at all, hit me up. I will gladly put you guys in contact with them. I highly recommend you guys check out their podcast as well. You guys, they put out a lot of great content. And again, they're actually in the industry doing the job that they're talking about, right? There's no theory with any of their stuff. But that is going to be it, ladies and gentlemen. As always, if you got value in what you heard and you're not subscribed, subscribe to the show, you guys. And if you're feeling ambitious, rank it on iTunes and Spotify because if you see value, your network's gonna see it as well. I appreciate you guys. I love you guys, and we'll be talking to you soon.
