Freight Broker Training and Content Marketing Strategy with Freight 360
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In this episode, Nate Cross and Ben Kowalski, creators of the Freight Broker Basics course and the Freight 360 podcast, share their insights on content marketing, freight broker training, and balancing work with side projects. They offer valuable tips on prospecting, follow-up processes, cold-calling techniques, and how AI tools like ChatGPT can aid brokers. The two also cover challenges new brokers face, creating authentic content, effective marketing emails, and advice for managing personal branding efforts.



  • The number one reason that brokers don’t succeed in the sales side is they’re not make they’re not putting the activity in, it’s a numbers game. And if they just if you’re not making the calls, number one, it’s less opportunity to talk to people. And number two, it’s less opportunity for you to refine your skills to effectively communicate.” – Nate
  • “A lot of this was just me and him writing it out, coming up with the topics sharing it back and forth and then sending it to other people we knew in the industry to audit it for us and say, Hey, what are else? What else are we missing?” – Ben Kowolski on creating the Freight Broker Basics course.
  • “So the coffee challenge is really just to go when next time you buy coffee, you have to ask them for a discount, which no matter what it is, you just say hey, can I get 25% off this cup of coffee, which is a really awkward thing to ask.” – Ben Kowolski on practicing negotiating skills
  • “Everybody likes to teach and talk about things they know. I want to ask just enough questions to get this person I’m calling to be interested in to want to talk to me a question does that.” – Ben Kowolski on effective prospecting.
  • “I think it does help us get better at the things we’re doing. I hope there’s more of that and less of people just outsourcing it directly and going, whatever, what’s good enough, send it as big unintended consequences.” – Ben Kowolski on using AI tools to assist rather than fully automate.
  • “And I don’t know what that’s going to look like. So there’s a fear a little bit. But I’m like, Well, I’d rather move towards the fear and be on the front edge of it. Because there will be winners, and there will be losers.” – Ben Kowolski on adopting AI early.
  • “The vast majority of brokerages are smaller than that. So they don’t they’re not going to have the manpower or the the cash flow to pay somebody to be like your education person.” – Nate Krause on why most brokerages don’t have robust internal training.



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Show Transcript

See full episode transcriptTranscript is autogenerated by AI

Ben Kowalski: 0:05

I think you're going to see some tools and things in the carrier capacity and rate side, like Nate mentioned, that are going to be, I mean, exponentially better than what we have probably within one to three years from where we're at now just seeing kind of what they're working on and where some of these things are so really excited and, to be honest, like also very scared, Like I think about it a lot, because I think this is going to shift a lot of industries in a way that we just nobody knows and nobody can expect or predict.

Blythe Brumleve: 0:39

Welcome into another episode of Everything is Logistics, a podcast for the thinkers in freight. We are proudly presented by SPI Logistics and I am your host, Blythe Brumleve. Today we've got an awesome show for you. We've got two guests that are joining us from the Freight 360 podcast and also the creators of the Freight Broker Basics course, and that is Nate Cross and Ben Kowalski. So we're going to be talking all about freight broker training, content, marketing and how to fit it all into your daily jobs and managing it all within reasonable expectations. So, Nate and Ben, welcome to the show.

Nate Cross: 1:15

Thanks, Blythe, it's good to be here yeah pleasure to be here.

Blythe Brumleve: 1:20

Now, Ben, you've been on the show before Nate. This is your first time on the show and I don't typically do two guests on the show before Nate. This is your first time on the show and I don't, you know, typically do, like you know, two guests on a show at a time. But I'm hoping that I can, you know, ask all these, both of these questions, to both of you, or all of these questions to both of you, and I would like to know originally, how did you guys meet? How did you guys start working together?

Ben Kowalski: 1:41

It's actually an interesting story. Nate, you want to go?

Nate Cross: 1:44

Yeah, it is a good story. So what about 10 years ago?

Ben Kowalski: 1:49

Yeah, give or take. It was probably 2015,.

Nate Cross: 1:52

2016,. Around that time, I was working at another brokerage. I actually tried to recruit Ben to leave his brokerage and come work for mine. Didn't happen, but we stayed in touch over the years and then I had started a podcast in 2019 called the Midnight Freight Broker and I left the company I was at, went to the company I'm with now and COVID hit A lot of people started consuming content differently. Podcasts got big. Luckily, I already had one. Ben came on a couple of times, just as another expert in the industry, and I feel like it was more so Ben being like hey, let's do something with this, let's actually make it into a legit thing where we do it continuously. So we rebranded to Freight360 in 2020, right, probably summertime of 2020. Yep, and started doing the show and we've been doing it every week ever since. And it's evolved way beyond that ever since to include other types of, like you know, video content, blogs, et cetera. But that's kind of the origin story is tried to recruit Ben, stayed in touch and then we just joined forces.

Ben Kowalski: 3:06

I think what's always interesting about that right I really like that story is because, well, we teach people how to prospect, how to and again, what is prospecting? It's just calling people you've never met and just trying to connect to be able to get to know them, make friends, make acquaintances, right. Like I've always viewed it very similar to like what you do is like a politician, like that's all you're really doing Trying to connect with people, talk, get them to know, like and trust you. Right, and like that one or two conversations we had a long time ago right Goes to show how effective Nate was at that. Right, because that's what I picked up on and I still to this day remember like being on the phone with him and making a mental note like, yeah, it's not going to work now, but he hustles, he knows his shit pardon my French but like understands how to connect and how to do this quickly. And I'm like I could tell he's good at what he does, like I didn't need to really ask him many questions because he conveyed that confidence so quickly that like we just connected real quick.

Ben Kowalski: 4:01

I remember putting a note in my phone and just like keep just made a mental note like keep in touch with him at some point down the line, like there's probably going to be an opportunity to work together. And I just kept that in the back of my mind. And then, when I left the big box brokerage to kind of wait out my non-compete, I went into consulting specifically and then noticed Nate's show was going and I was like I really want to be back involved in logistics and I kind of had to wait out a little bit of timeframe. So it was a perfect opportunity to get exposure, be tied back into the market. For you know my like wait out period, if you will. And again, nate and I just kind of looked at it and saw what we could do with it and just kind of started building it and, you know, consistently moving ahead, week after week, doing the things we'll talk about in this episode content and whatnot, and all the things that go along with that.

Blythe Brumleve: 4:52

Now, do you remember sort of those early light bulb moments? Was it COVID, or was it? You know the conversations that you were having initially. That said, I need to not only start the podcast, but keep it going.

Nate Cross: 5:02

So yeah, I'll answer that. So I was doing it when I left the company I was with before I ended up just doing it by myself at home during the COVID shutdown and I would be like, all right, how much content can I get through talking by myself on a podcast once a week? And then, when Ben had reached out and was like, hey, you know what, you know, what do you think about me coming out and we'll do an episode on you know, fill in the blank, whatever it was, I was like hell, yeah, I was like somebody to join me, so I'm not just talking alone this whole time. So we did, and I was like, hey, let's do it again next week. And then eventually it was like you just want to do this whole thing together and keep it going. And as soon as we started doing it together and Ben, I think it was probably your first time podcasting Within a couple of weeks you got more comfortable finding your voice in the podcast space versus cold calling.

Nate Cross: 5:55

It's very different ways of communicating. But eventually we got really good at it. The content got really robust and good and it was much more long form. Instead of a 20-minute podcast, we'd bang out like 45, 50 minutes and you know now we've had episodes that go well over an hour if we've got a good guest and just really good content, um, or we'll do like a two or three part series on something. So I think when him and I started doing it together, the light bulb came on, like went on in my head, like definitely got to do this as a group instead of just having someone on as a guest periodically, because I think the two of us together, this synergy, it's like that whole. You know what you can do together. It was that synergy, right, what you do together is, you know, greater than the output of your individual. You know what I'm talking about, right? If you?

Ben Kowalski: 6:41

want to go far, go together. If you want to go fast, go alone, right. You know what I'm talking about, right. But like, if you want to go far, go together. If you want to go fast, go alone, right. And I also think it's the dynamic, right.

Ben Kowalski: 6:47

Like, we have very different personalities and Nate, I think, is much more detail-oriented and focuses on things in a way that I just don't have that propensity. My personality, I think, is different in that way, right. So why I think it always worked early on and got better was because we have very different perspectives on the same job. Nate primarily manages lots of agents and a lot of the clerical backend and a lot of the very procedural standard operating procedures that I follow and teach, but Nate lives in that world. I lived in the world of customer relationships, negotiating like the moving of the freight. Nate had a much different perspective on the same position, so we were able to talk through one topic from different points of view. So it wasn't we're never competing for each other, right Like four for attention because they're very different perspectives that compliment each other, which is, I think, why it worked very early on and why it's continued to work.

Blythe Brumleve: 7:48

Yeah, I agree wholeheartedly. I do a monthly show called Freight Friends with Grace Sharkey, and being able to play off of each other takes a little bit of time. But now I feel like we've hit a really good groove where I know where her strengths are and she knows where my strengths are. We kind of complement each other when it comes to the weaknesses aspect. But I I'm curious as to how, how long did it take you to sort of figure out what strengths each of you should? Because a podcast is a lot of work in addition to your full-time job. So how did you sort of balance out those initial responsibilities of who's going to take care of what?

Nate Cross: 8:26

um, I well, I mean even to this day the podcast, because remember I was running the podcast for like six or nine months before ben came on and we rebranded. So I got really really good at like very quickly being able to record, edit and release with like very minimal work.

Blythe Brumleve: 8:47

So you do all of it.

Nate Cross: 8:49

So, naturally, when Ben came on, like I just kind of kept doing that and it's extremely even to this point, like from getting it recorded, processed, edited, put out an audio and video, any kind of after effects, um thumbnail.

Nate Cross: 9:04

It's like an hour at most, so it's it's like very little amount of um additional work for me to do that and I, like I based on when we record, each week I have a I kind of work those little things in during my downtime at my regular job. Um, whereas Ben I think as far as like other stuff that we do, ben has been very good with like relationship development with folks that we get involved with, whether it's affiliate or sponsorship or just connections that can get us boosted to the next level, kind of leveraging someone else's network, uh, to try and get us more viewership and all and all that stuff. So we we've kind of just naturally gone into the areas that we, I think have our strengths in, not to say that one of us doesn't fill in for the other one either, because that always happens too, but just kind of naturally went in that direction.

Ben Kowalski: 9:55

Yeah, and I think again to just add, like, early on, I well, I listened to a lot of podcasts. So, like I really enjoy the medium, I spend probably at least I'm just guessing 15 to probably 30 hours a week, right, listening to some audio content, either a book or a podcast. So a lot of the big names that most people are familiar with, like you know Tim Ferriss, Huberman, podcast, those groups, Peter Attia, but also I don't know if anyone's like or if you've heard of like my first million, like I followed that newsletter from when it started listen to the podcast. So I tracked what was working for them and when Nate and I hooked up, I didn't want to say like I had a roadmap, but I had their roadmap and a lot of that was well, this is working. We're in a niche. We can own this niche. Let's just do what is working for other people, right?

Ben Kowalski: 10:41

So early on, he focused a lot on the audio. I did a lot of deep dives into YouTube, what was functioning, research, what works, what doesn't work, a lot of those things. And I kind of spent a lot of my time on the video side as we got that off the ground. He spent a lot of time on that side of things and that was really our first year until we were able to leverage some larger relationships with DAT and things and they came back to us for the course and then it became more narrow. I guess the focus we worked with Lean at the time and our strategy was really we want to be the educational source for the industry for every fundamental thing you need to learn in your first year to three years, because that's really what we felt was missing. Whether we're working with a new agent or somebody that's just coming into the industry, like we just see what they're running into all day. So, to create the content, it was like a flywheel right, Like I'm working with a client or Nate was working with an agent, they're running into the same problems and then Nate and I would get together like what do you run into this week? Well, everybody's having an issue with this.

Ben Kowalski: 11:44

There's our topic, because it's already top of mind, and I also felt like the best thing about this and what I like most the podcast, as well as like coaching or consulting is that, like you don't, I feel like the best way to improve in anything is to teach it right, no matter what that is so for me to have to work to articulate things better, to be better understood by different people with different learning experiences.

Ben Kowalski: 12:10

This show gave me a very good you know, repetitive every single week to practice changing the way I say things right. Like, I think, everybody, when you do something for a long time, you forget what people know and don't know and when you learned what. So we're constantly being able to be grounded back at the beginner level or intermediate and sometimes experience level, where they're running into where their issues are that's really where a lot of our content comes from is just kind of boots on the ground, experience things that we run into on a daily or weekly basis and the industry kind of works the same for the most part. So what he's running into, I'm running into, usually whether it's a tight market or a loose market, and that's really why we haven't had to spend a ton of time developing an outline for what we're going to talk about. We're really going to talk about whatever that issue is people are running into, because we're running into it as well.

Blythe Brumleve: 13:00

Are you in freight sales with a book of business looking for a new home? Or perhaps you're a freight agent in need of a better partnership? These are the kinds of conversations we're exploring in our podcast interview series called the Freight Agent Trenches, sponsored by SPI Logistics. Now I can tell you all day that SPI is one of the most successful logistics firms in North America, who helps their agents with back office operations such as admin, finance, it and sales. But I would much rather you hear it directly from SPI's freight agents themselves.

Blythe Brumleve: 13:32

And what better way to do that than by listening to the experienced freight agents tell their stories behind the how and the why they joined SPI? Hit the freight agent link in our show notes to listen to these conversations or, if you're ready to make the jump, visit spi3plcom. And so it sounds like that this is almost like market research for you guys, or your own experience as market research. Then you're conveying that through your podcast and then it's turning into additional opportunities where you can almost study yourself as an athlete, you know, study other creators, other broadcasters and how they approach it, and then use that same insight to to, to your point, ben, to to then reframe how you speak to your prospects. Is that accurate?

Ben Kowalski: 14:20

Absolutely Right. And again to the to the same point of, like COVID right to, what was happening at the same time was, like everybody goes home, and I mean I'll just speak for myself Like I spent my entire professional life in sales floors, like surrounded with that energy, that culture, like there is a difference to doing any type of sales in that environment versus in your home, right. So for me, I felt a huge absence of that when it was gone and this was a great way for him and I to stay connected with lots of people in the industry, very frequently, both, as you know, a show, but also people reaching back out to us telling us what they're running into hey, what you talked about, like we're running into this. So it was also a great way for us to kind of intentionally create as close as we could to the environment that we used to be in, even though we're no longer in it, which I thought was a huge benefit.

Nate Cross: 15:13

I'll add to that too. I think it was like Mark Cuban saying you don't get rich without a little bit of luck in there. But there was a bit of luck on the timing of all that, because you think about people that are leaving the bullpen. Right, they're leaving that sales office environment for an extended period of time. They don't get that mentorship or advisement or training or guidance that they would get from a peer or a supervisor in person. So they started relying on content on YouTube and on podcasts and all that stuff. So we just happened to be, we already had kind of the runway launched and then, as our content just kept, you know, we did more and more and more content. We just had we had people that had ears, that wanted to listen to us, because they weren't getting it anywhere else and they needed it.

Nate Cross: 15:57

So there's also this thing in the freight world where a lot of companies and I've literally seen this argued in depositions before that I've taken place and they say our training material is proprietary and it's like, how, it's like basic sales stuff.

Nate Cross: 16:12

How is it proprietary? So, anyway, everyone holds their training close to the chest in freight brokerage, saying that it's some secret sauce, and we're like well, it's not really A lot of these basic principles are all the same. So our goal was like let's just have transparent education that's accessible to everybody in our industry, and we'll continue to add content to that. The reality is, you know, for every you know thousand people that listen to your content, how many people actually take action and follow what you tell them to do? It's like probably less than 1%. So it's not like we're giving away the farm or anything, but you know, at least the timing was good and we were able to create an environment where, to this day, people use our content to train their new employees, and it's amazing to see that we've been able to get to that level.

Blythe Brumleve: 16:54

That's awesome. Let's actually dive a little bit deeper into the Freight Broker Basics course. What was, I guess, the moment that you decided, okay, this is something that we should actually tackle? Was it, you know, working with dad, or was it seeing some of the numbers from YouTube? What was that?

Nate Cross: 17:11

How did you make that that logical next step so yeah, it was actually, um, we had been in contact with DAT for a while, built a pretty good relationship, and they kind of had the idea they're like, you know, we have all these people getting into freight brokerage Cause remember, you know, the post COVID shutdowns everybody was trying to get into trucking and brokerage because there were so much freight to move in a lot of just chaos. They're like you know, we have all these people asking for education and we don't have a solution for them and they're like do you, you know, do you guys think that you could put something together and we can kind of co-spearhead this thing? And so that was kind of their idea.

Nate Cross: 17:50

And I've seen a bunch of courses that have been out there for years and the reality is they're either outdated or created and taught by someone that's either not still in the industry or never was in the industry. So the credibility is lacking. Not still in the industry or never was in the industry, so the credibility is lacking. So it's kind of a mix of there just wasn't a lot out there and DAT had a need and we had a good relationship and rapport with them that were like, yeah, let's do it, but remember, we both have full-time jobs, so it wasn't like we can just stop working for three weeks and bang out the content. It took us what like six months to get everything fully put together.

Nate Cross: 18:24

It took them very long time to do it.

Ben Kowalski: 18:26

I would say like, yeah, it was definitely six to eight months and it was very much like I can imagine what it would be like to write a book. I mean, we had to outline it. We went through every course we could find, audit it, bought every one that was available, went through every single one we could find, wrote down what they all had, what we felt were mostly missing and where we felt we could improve. So we had everything that everyone else's course and then we're like what is missing from all of them? And it was mostly sales stuff and a lot of like what you really do day to day. Like it was all like high overview, like, oh, you'll call a shipper, get a load and you book a truck, and then they're looking at each other like, if you gave this to me, I couldn't do that. That's not enough information. There's so many steps in between here.

Ben Kowalski: 19:06

So again, a lot of this was just me and him writing it out, coming up with the topics, sharing it back and forth and then sending it to other people we know in the industry to audit it for us and say, hey, what else are we missing? So DAT was a great resource A lot of other folks that we've worked with Kevin Hill and other people in the industry that have been able to lend a hand and look at it and give us their thoughts, to build this out really as robust as we could, so that, if we were going to put our name on this and spend this time, we wanted to make sure it was at least comprehensive and it did what we said it was going to do Teach you literally how to broker freight, not teach you what a freight broker does. Teach you how to do it, and those are very different things. That I think what separates our course from other courses.

Blythe Brumleve: 19:50

Oh, that's super interesting.

Blythe Brumleve: 19:51

Yeah, I would imagine for a lot of those people who are making those courses, they don't have that firsthand knowledge that you guys already have and working with industry experts, because I've actually.

Blythe Brumleve: 20:02

You know, ben, I had you on my previous podcast and we were talking about courses that were or I brought it up so I'll put my name onto that but some of them were straight up scams. There was one woman in particular that reached out to me that she took a freight broker course with the promise at the end of the course that she would be able to join as an agent under that MC and operate, and they just left her high and dry. They never offered. She paid thousands of dollars for this course that she didn't really have, hoping that it would lead to a job, and then it turns out it was just she just took some YouTube videos and watched those and that was the extent of her training. So it was one of those things where it's like, wow, how often is you know some of these scammy tactics being played out within our industry? And I think it's it's probably a fairly high number.

Nate Cross: 20:56

Yeah, yeah, I think you're right. Like I remember, when we went through to, like Ben said, we went through and audited the existing courses, cause you have to do, you have to know your competition is right. When we went through to, like Ben said, we went through and audited the existing courses. You have to know who your competition is right. So we went and figured out what's out there and I remember reading one of the lessons that this guy's course had and it was so outdated that it said that the surety bond requirement was $10,000 when it had been $75,000 for like seven years at that point. So like it was outdated by almost a decade and I didn't even bother going through the rest of the. He had like a big section on like regulations and like um governing bodies and I'm like that stuff changes like so fast um, and I think that's a pivot.

Nate Cross: 21:37

But like you know, tia right, they're a great um partner of ours as well and ben and I, along with chrisolly, we teach their new broker training now and their new broker coaching sessions. So what we did is, when Ann Ranke came in, we got to meet her very early on in her time with TIA. They had a big push on like we want this education piece to be tight knit, ironclad and like legitimate. So they had us go through and audit their existing course and then become the instructors for it. So we created with again with Chris Jolly, a new curriculum which has again since then evolved a second time to stay up with the you know, with the times and and make sure it's as robust as possible. But, um, it goes to show that you know someone is reputable, as, as TIA and DAT, they're going to want to make sure they've got relevant, good content out there where just any Joe Schmo could be like oh yeah, freight broker course, come give me $2,000 and I'll guarantee you can make six figures a year. And it's like well, no, the content is what it is, but the way that you actually teach it, present it and keep it up to date is going to be a big game changer as well.

Nate Cross: 22:50

Ben, we talk about it a lot, with people Set expectations. You can't just watch a video and expect stuff's going to happen. You've got to take the actual information there, go and apply it and, more likely than not, you probably have to consume that content upwards of 10 to 15 times over a period of a year or so for it to really sink in, and you have to put the reps in for it to become comfortable as well. So there is a lot of junk courses out there. I think ours is obviously. We created it in conjunction with DAT. I think it's great, tia's very reputable organization and we help teach that as well. But outside of that I've yet to come across a really good, stellar, commercially available training program that's not internal to a company. So a lot of scam options out there.

Blythe Brumleve: 23:38

And I'm curious why don't you think that more companies create their own internal course? I mean just thinking of it from a logistics standpoint. It would be much more efficient to create a course you know once or twice, you know once every few years and have your new employees take that versus just you know, trusting that somebody within the company is going to train them right. Is there any reason why most companies or do most companies have their own internal training around just the basics of a freight broker?

Nate Cross: 24:07

Yeah, go ahead.

Ben Kowalski: 24:08

Ben, because you worked at a big box, I was going to say, like the bigger companies definitely have a more standardized version and do have, I would say, like, kind of closest. Like you know, I worked at TQL. I've gone through theirs. Like they have a robust, and again, I went through that eight, nine years ago and it was pretty good then, right. And again, comparable to any of the courses that are just available, like theirs was much better, right, and I had a vivid memory of that when we wrote ours as to like, oh, these bigger companies are doing this a little bit differently, right, and what they focus on. And again, they need somebody to do the job, because if they put someone through the course and they can't do it, they got no benefit. They just spent a whole bunch of time for nothing. So they have an invested interest in the outcome in a way that people selling a course I don't think do.

Ben Kowalski: 24:55

And again, I've had the opportunity to work with all of the larger brokerages and go through a lot of their training and like, again, in that I would say there's a difference. And again, there's a reason why they have longer non-competes and why they protect the employees that they are training to do this. It costs a lot of money for these bigger companies to do that for sure. But when you get off of the very big, large cap brokerages, most of the small caps for sure, don't do this because it just takes a lot of time. Right Again, nate and I have jobs where I'm brokering or Nate's running a brokerage. It took us eight months to do this, two of us, right, and I remember like, like mostly 12 hour days, like eight hours at my normal job, three, four hours work on this after work. Like, there aren't a lot of managers or owners of smaller brokerages that have that additional bandwidth or time because they've got freight to move and customers to deal with.

Ben Kowalski: 25:45

Right, the middle-sized companies.

Ben Kowalski: 25:47

I think you see a little bit of it, but, again, there tends to be so many more urgent things that hit their to-do list every day that this just always ends up getting moved down.

Ben Kowalski: 25:58

And when I talk to owners that use our course for this purpose, which is another reason, that's why they get access to it and why it renews every year, because they use this to train their employees, because it's a great starting point, and I've always said look, hey, you can spend six to eight months to do this yourself, use ours and then add the other stuff that we missed, that you want your team to know, and at least you don't have to start from zero.

Ben Kowalski: 26:25

You can get the fundamentals, use something that is readily available at a pretty low cost point and then add anything you want to do on top of it, and I think that's why the mid-sized companies and smaller companies don't really often build this from the ground up and again, even when they build it, you got to update it, right, the same thing that Nate and I are saying. So, like some of the other companies I know that have done this, they did it four or five years ago and they're like, yeah, it really needs updated how we vet carriers changed All the frauds, changed things, and it's like, well, who's got the time to go do this? So then it just always again moves down the priority list until maybe they get to it, maybe they don't.

Nate Cross: 26:57

I think so. Like when I got so, I worked for a trucking company before I got into brokerage. When I got into brokerage I had to learn the 3PL side of it and I went to a company that at the time was like 40 or $50 million a year and they actually had like a corporate trainer, right, a guy whose sole job was to train new people and keep our content up to date. But even that, like himself, couldn't train everybody and keep himself up to date. There was outdated stuff.

Nate Cross: 27:28

I think the training manual that I had when I started was 10 or 12 years old and I was like, oh gosh. And they would tell me like, oh yeah, this has changed since this was written, but it just takes a lot of work and the vast majority of brokerages are smaller than that, so they're not going to have the manpower, the cash flow to pay somebody to be like your education person. So I think that that's why the majority of brokerages don't have their own internal training, because they don't have the time, they don't have the money. They're just kind of bootstrapping it and doing it that way, whereas, like Ben said, tql, ch Robinson Echoes right, they're massive, they have big standardized training curriculum and they likely have a large amount of people that are either in charge of teaching or creating, or both when it comes to their educational content, and they value that. They keep it close to the chest and they consider it proprietary.

Blythe Brumleve: 28:20

Brokering success demands a battle-ready strategy. Tye TMS equips freight brokers with the ultimate battle station for conquering a tough market. With Tai, brokers gain access to a comprehensive platform where rate intelligence and quote history converge on a single screen. It's not just a page, it's a strategic command center designed to help brokers win. Tai equips your team with all of the data they need to negotiate with confidence and allows them to communicate directly with carriers and customers from a simple control base. Revolutionize the way your brokers perform by giving them a competitive advantage with Tye TMS. For more info, go to tai-softwarecom backslash battle stations, and we also have a link for you in the show notes to sign up for a demo. And so, when you're thinking about this course and thinking about updating it throughout the year or throughout the years, what are some of those, I guess, big problems that new freight brokers are facing now? That is more up to date as far as like a training perspective, versus even just a few years ago.

Nate Cross: 29:28

Well, I mean, I think the problems tend to be somewhat similar. To give you like a specific example, we've done a lot of content lately on fraud. Right, because fraud didn't exist in the caliber that it does today if you go back 10 years, like double brokering was a thing. We talk about it in our course, but we had to create a lot of additional content afterward about identifying fraudulent, illegal brokerage activity, double brokers, identity theft, all of that stuff Cause the issues and a lot of the solutions and tools now are didn't exist five years ago. So that's a prime example.

Nate Cross: 30:01

Another one, though that was around before but has changed, is market fluctuation. So we would tend to see ebb and flow of the market, let's say, every 18 to 24 months, whereas we've seen this elongated market cycle that started over four years ago and still hasn't come full circle yet. Right, like we went from when post-pandemic, when it boomed, and like about four years ago, um, and then about two years later it dipped off. It still hasn't come back full circle. So a lot of it is um. You know, it's just we, we taught it, we. You know there's content out there about market fluctuation and how to handle it, but it's more so on a smaller level than what we're seeing now. So we've had a lot of content on hey, this elongated um market downturn. Here's how you can prospect, you know, um effectively in this market. It's not going anywhere quickly. It'll change eventually it always does but we're going to be here for a little while, so you have to adjust to make content in that arena and I think that's a really big one.

Ben Kowalski: 31:02

I'll just elaborate a little more on right Is most of the folks that came into our industry and the big wave during COVID right? If you think about it, there's always the different market cycles. I just look at it very simply right, when you have a peak of a market, it's very hard to find trucks and rates are very high. Right and the bottom of a market, trucks are easy to find and rates are low. Right. So when it's hard to find trucks, service trumps rate most of the time, because shippers still need to move things and it's important they get there, so they don't have the ability to pay any less than they want to. You got to pay what it costs because that's what a truck's going to cost and the market we're in now it's price over service, at least for the time being. Right. So what we've seen are lots of folks that came in in the peak of the market during the pandemic, which also lasted the longest peak market ever. Right, they're used to picking up a phone and any shipper that answered was like hey, we'll onboard you. If you can get us a truck, we'll work with you. That was the bar, because everybody needed trucks and a shipper that might have traditionally only worked with a handful of brokers would onboard 20 or 30 because they just couldn't get the capacity. So anybody that could, they were willing to Right. So again you end up with habits from folks that came in that, like anybody I call will do business with me. It's all great if you can find a carrier.

Ben Kowalski: 32:16

Now we're in the exact opposite of like shippers don't have a lot of urgent needs. Act opposite of like shippers don't have a lot of urgent needs. You have to find a way to add value. That isn't as obvious as I can. Find you a truck right. Maybe it's service, maybe it's how they invoice, maybe it's how you communicate, like whatever nuance is important to that shipper. You have to uncover those in this market.

Ben Kowalski: 32:37

Now that is a world of difference from the way operated when a lot of folks came into it. So a lot of our clients and a lot of people coming to us are like we were killing it. Everybody was doing great. We had 15 salespeople. Now we're down to six and nobody can seem to bring in a customer.

Ben Kowalski: 32:53

And then when we are asking more questions, we're finding they're approaching their prospects as if it's the same market with the same expectations of if I call somebody and they don't work with me, I go to the next one. Well, in this market, you've got to talk to a shipper maybe six to 12 times over two or three months before they'll give you a shot to work with their freight, as opposed to three years ago, one phone call. They're going to send you lanes, to quote. So it's a completely different environment. I look at it as the context of the sport you're playing in. Right, there's like different rules, you're playing a different sport, like that might've been like traditional NFL, and this is like arena, you know football, where, like it's a different sport because it's got a different size field and you've got to do different things to be able to succeed.

Nate Cross: 33:33

So I would say like that are larger shifts and you know it's funny too, ben, you mentioned all of that. Out of all the courses that we looked at before we created our, our outline and our curriculum, I didn't see a single one that ever talked about market fluctuation, even like the predictable stuff Like, for example, produce. Right, produce has cyclical to cyclical nature, depending on what you're moving, when you're moving in and where it's moving out of. Um hurricane season right, you guys both live in Florida like that every single year come September. Right, it's hurricane season. It's extremely predictable. The severity of it might change, but you know it's versus a cold market and then in that transitioning phase from one one side to the other. So, yeah, it's, it's crazy for sure.

Blythe Brumleve: 34:31

I was going to say, when you're teaching at, at TIA, I would imagine that you're, you're, you're teaching over. Are they live courses, or or is it?

Nate Cross: 34:39

you know the the live courses, or is it, you know, the the same course, maybe just repackaged for them, so that's live. They have like a web-based learning and then they go through coaching sessions with us. So there's, I think, what do? We have 12 total coaching sessions and we, ben and I do half of them correct.

Ben Kowalski: 34:55

So we, it's like a. It's a structured curriculum, that happened. I think we're doing trimesters now, right, nate, like we used to be quarterly. Now we're, and I think we do it like no, it's a structured curriculum. That happened. I think we're doing trimesters now, right, nate, like we used to be quarterly, now we're in, I think we do it like quarterly now Cause it's 12.

Nate Cross: 35:06

Okay, it's 12. Yeah, it used to be trimesters.

Ben Kowalski: 35:09

The class comes in. It goes for a full quarter. There's an outline curriculum that we worked with them and Chris, jolly you know, to outline what able to really operate in the industry now. So there's a set list of topics and then every week, either Chris or us. I think it's every week, right, nate, every week yeah.

Ben Kowalski: 35:28

Yeah, they're sitting in a class and it's either us or him teaching it, and then we have our topics and we get to allow them to ask questions. So it's a very engaged type of coaching, right, like I call it like the Socratic method, like, so we're asking questions to engage them, not lecturing them as if, like you need to learn this, read this. It's more like what are you experiencing and getting them to share so that we can take the lesson and articulate in a way that is relevant to where they're at in their journey. Right, which I think is also different. Right, I have a I think Nate and I both have this right Like it's like first principle understandings.

Ben Kowalski: 36:04

I think lots of companies and lots of training go like just do this because you're supposed to right Like book a load, pay the least amount of money and that's it. And Nate and I approached this more from like okay, but like why and what are the things that play into that negotiation? Right, Like the shipper rate, the weight of the load? Right, for instance, and like how those things affect what you're doing, so that people get a foundational understanding of the industry, not just a whole lot of tasks that they need to execute every day, because to me, like that's not teaching somebody how to fish, that's just getting somebody to follow directions. We want people to learn and understand, to be able to do this themselves, which I think is also very different.

Blythe Brumleve: 36:47

Do you find that it? Because, if I'm reading between the lines, it sounds like a lot of the. I guess the troubles or challenges that brokers are experiencing right now is the same whether you're new or experienced. Yes, Yep, Very much the same. And I think fluctuations affect everybody, no matter their status.

Ben Kowalski: 37:07

They're all still working the same market, right. So they're running into the same playing field. To keep the analogy right, Everybody's still playing the same field, right? I think what is different in your experience level is just the problems you face, right? If you're running a book of business and you personally got eight people on your team and you're moving 200 loads a week, like your issues are usually more like how do you create the space to prospect more right To be able to do those things? For somebody newer, it's more usually accountability and making sure they're doing enough of the right things to get them where they want to go, when they expect to get there, right. So I would say, fundamentally, they are doing the same things, but there's usually a different impediment to them being able to execute. That thing is what differentiates them.

Blythe Brumleve: 37:50

I'm curious as to what does, because I used to work at an asset-based brokerage, but that was years ago and I do wonder what does the I guess a typical day look like for a freight broker, from the moment they get into the office to when they know it's okay to leave? What does that process look like for them? Is it mostly software dominated now? Is it pounding the phones? Is it both?

Nate Cross: 38:13

I think it really depends on a couple things. Number one where are you in your journey? Are you brand new or have you been there for three years or five years? And the other part is what you know, what is your role? Are you running your own brokerage? Are you just a sales rep? Are you a cradle to grave broker that does sales and operations? Are you just a carrier rep? It really depends and it's fine.

Nate Cross: 38:33

We just did an episode on that came out like what five days ago or four days ago on what is the average like day or week of a freight broker, and we talked through it. No day is the same, but it's. There's a lot of like consistency that involves um, putting out flyers in the morning, talking with customers, um prospecting, booking trucks in the afternoon, putting out fires as they come up and setting up your stuff for the next day. That's. That's kind of like your super watered down generalization of it.

Nate Cross: 39:02

But, depending on where you are, if you're brand new you're going to spend way more time prospecting and following up and generating leads versus booking trucks putting out fires, because you don't have any fires to put out if you're brand new, whereas if you've been doing it for 10 years. You're very likely not the one putting out all the fires. You got someone else doing that. You might just be working on building relationships with existing customers, trying to find some new big whales and fish out there. It just really depends, but it's a lot of. It is repetitive and cyclical, but at the same time, no day is exactly the same, because you never know what's going to come your way.

Blythe Brumleve: 39:36

What are some of those fires look like that you're putting out every day.

Nate Cross: 39:40

Truck shows up late, truck breaks down, you get scammed on something, bad weather, ben, I mean, there's a million, I would say a lot of.

Ben Kowalski: 39:49

I think, yeah, your more common ones too, right, and Nate touched on it's like a lot of it's just covering trucks or recovering loads, right, because if your customer is very price sensitive, right, you then have less money to work with to pay the carriers. Right, you do what you can to be able to pay them as much as you can to make it work. But again, if I've got only a certain amount of money to work with and that's on the lower end for this load, there's a very high likelihood this carrier is going to find a better load before my load picks up, which increases the amount of times I've got to put another truck on the same load. So that is one of the larger fires in this type of market that everyone runs into is just rebooking the same loads. Like I was talking with a client actually right before this. They track this metric and they want it to be like closer to like eight to one and they're seeing it like five to one, meaning like for every five booked loads of the truck picks up one recovery right, and they're seeing they want that closer to eight. So those are some of the things they're trying to track because this is one of the more common fires. That one in fraud, because it takes you longer to vet a carrier now to make sure they are who they are is another one. And again, just unexpected things, meaning like you spend all of your time to be able to create the demand for yourself and your services. That's all. Prospecting is Right. And then once you're effective at it, now you've got to keep doing that thing but be able to adjust as your customer has a need, because your shippers, by definition to use a brokerage it's usually an unexpected load they need help with. Either their truck didn't show up or they got an additional shipment that they didn't expect in the middle of the day, so that email comes to you at two thirty in the afternoon.

Ben Kowalski: 41:26

Maybe you plan to prospect, but it makes no sense to not capitalize on the opportunities that take you forever to get. So you've got to be able to pivot, jump to that, be responsive and resilient to your customer, let them know you're always on top of it. And then you've got to be able to pivot right back to prospecting, because that's a big issue with most brokers is like it's not easy for any human to switch tasks constantly, like multitasking is a huge efficiency killer in most professions but inherent to the way our job functions. Like you have to be able to be good at it and you but you have to be able to switch back to right. Like you can't just be hitting at the loudest thing that is most urgent and never the most important.

Ben Kowalski: 42:13

And to your question earlier, like experienced brokers, this is where they need the most help because they're always jumping at the most urgent thing. So what they end up doing is never getting to prospect because you're never going to have somebody walk over to you or call you and yell at you and go did you make your prospecting calls? Like that's you right. So like those are the things that always get pushed down the to-do list or to tomorrow, day after day, and the more experienced brokers end up in a position they don't want to be in. They lose a big customer or something because they weren't doing that consistently Right. So, again, like it's creating that space or the habits and showing them how to improve on these things so that they can get to the thing that's most important to their business, not just what's most important to the customer, when the customer needs it Right. And I'd say like that is the big difference on like fires, between early on and like later on in your career.

Blythe Brumleve: 43:05

Are there any AI tools that have sort of entered into. You know, maybe it's a TMS, or you know just an independent tool that can be plugged into a TMS, or you know WMS or pick your software that you've seen? That looks really promising to help brokers manage some of those, I guess, sort of low value tasks.

Nate Cross: 43:26

The thing that comes to mind for me, ben, is Levity. I mean, so Levity is a company that so Tilo is the co-founder, he's been on our podcast before and I believe Freight Caviar as well, but they've been around for a handful of years and I think they're kind of taking like the hey, we're not changing the game and bringing something new. We're going to, like you just said, some of those low efficiency tasks. We're going to help you automate those so it'll read your email, be able to go run a rate through DAT or green screen or whatever, build a load in your TMS for you, things like that.

Nate Cross: 44:03

But outside of them, I feel like AI is a huge opportunity right now in our industry and I think, being that the AI boom really started what like a year and a half ago, I want to say, like when ChatGPT became like open for anybody to use, that, when I like just kind of went nuts. I haven't seen it like fully. I haven't seen anyone just come in and be like boom, here's an awesome product, it's gonna change the way we do everything. I think it's slowly starting to evolve in there. Um, like I've definitely seen with dat, some of their like predictive rates, uh, that they rolled out last year. That that's a pretty cool tool. I'm not sure if that would be considered AI or not, but I don't know. Ben, what do you got? You're like more in tune with the AI stuff than me.

Ben Kowalski: 44:48

Yeah, I think there's a lot. Levity is a really cool product that helps you really. It goes back to what we were saying earlier, like the fire, right, if I'm prospecting and my customer needs something. I need my customer to realize or to believe that I am always on top of it, right. But I also have this other thing to do. What I really liked about levity is like if you've got customers that tend to send requests like throughout the day and you want to get them a quick, quick response and almost buy yourself time to work on it, levity is great because it integrates with the TMS and your email so it can respond to your customer while you're prospecting and then you can jump on it after. So it works really well for customers that have like very consistent messages in some ways, like I just think of like lumber as an example, they'll send out load lists every day, a few times a day on lanes. They need help. Levity is a great tool because it will respond to my customer and the way I want it to, without me having to stop what I'm doing, buys me time to finish what I'm doing then to work on that, and again, there's more functionality beyond that. But that is another tool that again helps us not have to be as reactive and allows us to be a little more intentional, which I really like about it.

Ben Kowalski: 46:01

A few other products that are out there I know that they're being worked on and we're keeping an eye on. We definitely don't want to announce them, but I've seen a couple of tools that are working on negotiating, like chatbots that will negotiate rates on behalf of carrier teams. I've seen those improve a little bit. There's one company in that space that's doing pretty well with that and I think you're going to see some tools and things in the carrier capacity and rate side, like Nate mentioned, that are going to be, I mean, exponentially better than what we have, probably within one to three years from where we're at now just seeing kind of what they're working on and where some of these things are so really excited and, to be honest, like also very scared, like I think about it a lot, because I think this is going to shift a lot of industries in a way that we just nobody knows and nobody can expect or predict, and I don't know what that's going to look like. So there's a fear a little bit, but I'm like, well, I'd rather move towards the fear and be on the front edge of it, because there will be winners and there will be losers, and I, at least, want to give myself, my team and the people I work with as many of these advantages to be in the group with the highest likelihood of succeeding.

Ben Kowalski: 47:13

Because I think, just like when the internet came along 30, some 35 years ago, right Early adopters had huge wins right Over the ones that waited to get on board, and that could be the. That could be the difference between your business being around and not being around three to five years from now. So to me, like it's very important I don't think it's necessarily impacting day to day so significantly right now, but I read something I don't know if it was Elon or somebody put it out. It was a chart showing, like, the exponential improvement in AI technology and it's like a factor of 10 or 100 on top of what tech improves every year. I can't remember the ratio that tech improves every year. Like there's that number that they came out like the 60s, that it gets this much better every year.

Nate Cross: 47:58

Is it like double every year right?

Ben Kowalski: 48:01

Is it like chip?

Nate Cross: 48:02

capacity or I don't know.

Ben Kowalski: 48:03

I'm not like a tech nerd, but but anyway, ai yeah to that point is supposed to be like a factor of like 10 or a hundred compared to that and how quickly it's improving year over year. So I mean I would be surprised if it didn't have significant changes to our industry somewhere in the next three to five years.

Blythe Brumleve: 48:19

Yeah, I agree wholeheartedly and it feels, you know, with ChatGPT, just storming onto the scene and just using it. I use it now every day, every day within, and I find a new way to use it all the time. The app is fantastic. I'm using it more than Google search now and I'm, you know, it's able to give me, you know, very like uh, nuance and it you know nuance. At times, of course, it still has hallucinations, but it's able to give me a much more clearer answer and I'm able to take, you know, for example, like a podcast transcript and upload it to it and say you know, what are some of you know, the give me 10 or 15 of the most powerful quotes from this conversation and it's able to spit those out in seconds, and so a part of it is like, wow, this is really, this is really powerful. But then, on the flip side, it's one of those things where it's like is this going to be able to replace me one day, like I? You know there is that level of fear that's involved as well, but I'm, I'm right there with you, ben.

Blythe Brumleve: 49:18

I think that you have to experiment with these tools, even if they are a little scary. This is a quote that I heard recently that I fully believe is that AI won't necessarily replace your job, but a person using AI will. I think that it's had a massive impact on just my small marketing team and with the content we're able to distribute and create, and I hope that I'm not as replaceable. But I think it's an interesting sort of argument or an interesting internal debate around your own ego. Am I actually better than AI? Can I be better than AI? And I think that that's maybe a good thing to sort of pursue is to to try to be that better version of yourself.

Ben Kowalski: 50:06

For sure. Moore's law doubles every one and a half years.

Blythe Brumleve: 50:09

There it is. Oh nice, Nicely done.

Nate Cross: 50:12

So I'll add in too, on the AI piece, the like meeting assistance, like, so, the ones that plug into like your zoom meetings, your team's meetings, and they get like cause you were mentioning Blythe like the transcript, I'd be able to do stuff the ones that will like give you um, Ben, I forgot the one that you use all the time Um, there's Otter, there's Fathom, yeah, yeah.

Nate Cross: 50:42

I told us want it. It's really cool. So, with the podcast too, which is cool is we upload our. I edit the audio real quick, throw it up on Buzzsprout, and then it'll create chapters. It'll give a description. If you want help, you give a title. It's really really cool how it's gone in the content. Space Freight brokers, though, and Ben I, I'm gonna full-heartedly agree with you on this. I think the negotiation piece is going to be really interesting to see how that pans out in the coming years. I saw an instagram club the other day that claimed it was like a ai voice talking to a driver or dispatcher on the phone trying to um who was calling in about a rate or about an available load. But the capacity thing and um, you know we won't say too much about it, but I can. I'm with you.

Ben Kowalski: 51:30

One to three years, I think you're gonna see some big, big new players in that space who people have probably never even heard of right now no, and they're using that now, like again I don't know tangent, but I know they're using ai chatbots to make what we would have called robocalls back in the day. So, like telemarketers that have very structured scripts where this objection gets this response. But they're using that right now for, like fundraising things, like they record the best salespeople, all the responses, all the objections, and it literally just executes based on what it's hearing. So it's using the human voice of, like the better salespeople and it's just literally able to have this conversation because they're very repetitive, they tend to have the same patterns, so it's definitely being used in other sales industries for sure. Now I think ours is a little more nuanced and I think it's going to be a steeper hill to climb, but we'll see what the future holds for sure.

Blythe Brumleve: 52:27

Well, we just talked about what sort of the typical day looks like for a freight broker. How do you think AI impacts that at all? I'm imagining that it's going to help with a variety of those functions, but does it fundamentally change what you're doing throughout the day?

Nate Cross: 52:42

I don't think it fundamentally changes. I think a lot of the mundane tasks will be made more efficient and it'll create a lot more time and opportunity for relationship building, business development, probably to run like a leaner admin support team so you can grow without having to hire as many extra bodies. I think it'll kind of assist companies and brokers in that way. But I think fundamentally we're still going to be. You know, we're logisticians, we solve logistics problems for our customers Until the way that freight is transported changes drastically. I don't see that or massive regulation overall. I don't see the average conceptual, fundamental tasks that we do changing too much. Ben, what do you think?

Ben Kowalski: 53:27

I think it's more to what you had said earlier. Right, it's more of the person with the tool, not instead of the person. So, again, nate's example, the way I look at it, I'm like, hey, if I normally would need to hire six or eight people to cover my loads for me to sell right, and maybe I only need two or three right? Same thing in like coding. Like, again, I know that some of the tools that are out there with AI that assist code, like coders, like. I've read reports that say, like you know, a B grade coder can now operate like an A grade coder with the tool because it's helping them find their errors faster and giving them suggestions so they're learning quicker, they get feedback faster, right, I think you could probably see something similar to that as it becomes adopted within our industry. Again, whether it's negotiating, check calls or whatever the tedious manual task that normally is, to be honest, like entry-level people mostly fill these positions in our industry, right? So I think you'll probably just see a lesser need for those people. And also, those people don't tend to stay very long either, like they'll come in. They tend to turn over within a year and go somewhere else. So I don't see it as necessarily replacing people. I just see it as becoming more effective and more efficient in some ways to allow us to do more with less resources.

Ben Kowalski: 54:46

I've seen the same thing in warehouses. Right, like I read a report because a lot of this robotics and things in AI are being used in warehousing within our industries, right, whether it's stocking shelves, you know, staging a truck with pallets to get it ready before that truck arrives. There was a really good article or it was a good podcast. Someone who was being interviewed that owns a large portfolio of warehouse and he goes listen, we have 100% turnover in our warehouses. He's like not like hyperbole, not like almost 100, meaning every year. He's like I've been in this industry for 20 years. He goes we don't have one employee in five of our warehouses that has been there longer than a year.

Ben Kowalski: 55:23

Nobody wants the job. People take it until they don't need it anymore. They can find something better and they leave. So we have huge costs of training people for jobs that nobody really wants anyway. He's like you know everyone's yelling at me saying I want robotics to replace people, but like if I could get people, I wouldn't have wanted the robotics. He's like I'm trying to solve a problem that is created from the fact that nobody really wants this job to begin with. Now, I think that could be a slippery slope, and who knows where that leads to. But at the very least I think early on that's what it's likely to play out. But who knows?

Blythe Brumleve: 55:56

Yeah, it's one of those.

Blythe Brumleve: 56:06

I think it's something you know.

Blythe Brumleve: 56:07

There's a lot of fuss that that's made about warehouse robotics and how it's replacing jobs, um, but in also, you know, with autonomous trucks as well, and I think for a lot of folks, they they've slowly come to the realization that you were worried about the wrong careers that were going to be replaced very soon, because it's very challenging to replace those those.

Blythe Brumleve: 56:18

You know the, the almost the blue collar workforce. It's more of the white collar workforce that is going to be impacted much more quickly than the in-house workers. And even then, to your point about warehouse robotics, it's something like more than 90% of all the warehouses across the country use no form of robotics whatsoever, and there's a real issue like Amazon is actually really genuinely worried that they are going to run out of people to hire for their warehouses because they have so much churn, and so it's just a fascinating just sort of debate around. You know AI and how you define AI of you, especially for small business owners or small teams being able to these tools feel like a great equalizer versus some of the bigger companies that have the budget for, you know, a 20 person marketing team or 20 person, 50 person sales team where you can use some of these tools and really almost put your workforce on steroids. Oh, go ahead, put your workforce on steroids.

Ben Kowalski: 57:21

Oh, go ahead. I was going to say to that point, right to like, circle back on something we had said either in the green room or early on, right? How are we using these tools now to create more time or space? Right, and again, I think we're all on the same page. At least I know we've talked about this offline. It's like we're not using AI to create our content by any means. Right, I think there's a whole. We could talk for an hour on what's happening to the environment and the SEO with just content that's generated through.

Nate Cross: 57:49

AI tools.

Ben Kowalski: 57:51

They're just regurgitating other things. That's all it does, right. So like it's not expanding, it's not creating novel thoughts, it's just regurgitating things and again like whole other side topic. But what we use this for right is like I think it's incredibly regurgitating things and again like whole other side topic. But what we use this for right Is like I think it's incredibly valuable for me to kind of get started when I'm by myself, sometimes Right, like you're kind of at the space where it's like they call it writer's block.

Ben Kowalski: 58:12

We were like I got a couple ideas I don't really know how to get the momentum, and I'll just be like hey, suggest an intro.

Ben Kowalski: 58:19

Or like write me a script on this and I'll look at it. I'm like, yeah, like that doesn't feel right, but I'm like this little piece right here seems like a good starting point and then you can just start writing. And again, like it's not to replace at least I don't view it as a way to replace what I'm doing I'm like this just is a person that I can use when I need to, that can help me also spell check, they can help me look at my grammar, that I'll sometimes throw a whole script in for YouTube or whatever, and go like edit this and suggest another format and I'll see what it takes out, and go, oh yeah, like this didn't really make a lot of sense there. That was like a tangent. We can move that, so I think it does help us get better at the things we're doing. I hope there's more of that and less of people just outsourcing it directly and going whatever looks good enough, send it.

Nate Cross: 59:04

Because I think that has big unintended consequences.

Nate Cross: 59:08

AI is definitely at a place right now, too, where you can spot if something was purely written by AI. And the images too. Like you know that's an AI generated image. So like, for example, I have never in my life ever used the word delve and if you ever ask chat gpt to write something, it's gonna say let's delve into. And I'm like I would never talk like that, right and but I've gotten newsletters and I've seen emails where I'm like that's 100 chat gpt, it's not even like gpt4, it's 3.5 the free one, because they won't even pay 20 bucks a month. They're sending this crap out. So but as stuff evolves down the road, it's probably gonna be hard to identify what's what.

Nate Cross: 59:50

And I do think, like, for these people that just write mass email, email blast to shippers, like it could get to a point where you could say like, hey, write me 100 unique emails that cover these 10 bullet points and make it. But anyway, maybe something like that could help somebody create an email campaign on a marketing side. But I don't know. I'm curious to see where it goes. I think that the human being there's a thirst for human connection and I think that true business uh, tracked the word delve and the massive amount of increase of that word being used, uh is directly correlated thing.

Blythe Brumleve: 1:00:48

Right, it's like a GPT, like the correlation with like when GPT launched, versus that word being used. It's like up and dramatically to the right. Uh, so to to, to y'all's point, it really is. It's one of those things where you have to. It's still a human is required during most of the marketing process. I am curious because we have talked about prospecting a lot during this conversation, and if you were to advise a new freight broker on balancing the skills that they need to learn with some of these AI tools, what would be some of those suggestions that you would take when it comes to prospecting?

Ben Kowalski: 1:01:31

On the tools, to what aspect of prospecting? I guess like lead generation or like in general.

Blythe Brumleve: 1:01:39

I guess maybe I'll pose the question this way how would you, if you were to hire a new freight broker right now, what would be the most important aspects of prospecting that you would teach them?

Nate Cross: 1:01:50

I would say that Ben and I, we have a pretty consistent message on this, and it's number one is to break up lead generation, which is identifying who these leads are, and then prospecting, which is the actual act of reaching out, whether it's call, email, in-person, visit your follow-ups. But I would say it would be to really hone in on those two things Find a very efficient way to get a lot of leads quickly with very little work and then make a lot of phone calls. The reality is, you know if somebody is brand new and has never made a cold call, they're going to suck at it at first. You know, way more likely than not, and it takes I would say it probably takes two to 300 calls before you even like find your own voice and feel comfortable doing it, cause every time you, every time before then you're like this feels so awkward, I just can't wait to get off the phone. The person on the other end of the phone, you know they hate me, they just they, they're so mad that I'm calling them.

Nate Cross: 1:02:50

It's like no, that's not the reality of it. Like make a hundred calls or 200 calls and you'll rise it Like it's really not that bad 90% of the time, but I would say it's yeah. So to recap that, efficiently get a ton of leads easily, with minimal effort, and then just go through repetitions of reaching out, figuring out what your opening is, how you're going to run through your questions of prospecting, identifying the right questions to ask at the right time and what to say in response to a certain objection. Those are probably your biggest ones. I think that the number one reason that brokers don't succeed in the sales side is they're not putting the activity in. It's a numbers game and if you're not making the calls, number one, it's less opportunity to talk to people and number two, it's less opportunity for you to refine your skills to effectively communicate. So that would that would be my answer on that one.

Blythe Brumleve: 1:03:42

If most of the I guess that the people that they're calling aren't picking up the phone, how are they getting better at at cold calling?

Nate Cross: 1:03:50

So I would say that if someone doesn't answer the phone, there's another way to get ahold of them, cause you might have the wrong number, it might be a phone tree, it might be you have their voicemail. There's crafty ways to get yourself to the right person, and I've. You know I'm not going to endorse any one of them, but I'll tell you ways that people will do. That is, they'll be like all right, I'm going to call the accounting team or the accounting department and ask to be rerouted this person because I had the wrong extension. Or I'm going to call the sales team, become buddy-buddy with them and then ask to be transferred. Or I'm going to call their boss and who doesn't have time for me, and the boss is going to say, hey, call this person back.

Nate Cross: 1:04:26

There's all kinds of ways to do it, but I did a cold calling blitz about two months ago with one of the guys in our brokerage and we went through. I I want to say it was like 50 phone calls in one hour and I think we had six. We actually talked to like six or seven people and out of those six or seven people, only one or two of them was actually a, you know, shipping manager or in the freight department that would act like a traffic manager, that would actually tender loads out. The other ones were like operators or you know someone that's just screening phone, like your gatekeeper, stuff like that. But the vast majority no one answered. It's just that simple. So that's why we say 100 calls a day. You're going to spend two to three hours, 100 calls a day and you're going to have a very, very few amount of good conversations. But it's a numbers game. Ben, what was your stat? Like over 1,000 phone calls before you got your first customer? Something like that.

Ben Kowalski: 1:05:18

It was like 2200, something like that.

Ben Kowalski: 1:05:19

2200 yeah I was in a market similar to this, like whatever 2016, and again, like the other thing, too is it's anecdotal but I've never seen anybody put in exactly what nate said consistent effort, making the calls and doing in a way where they're hitting a consistent number, even if it's 60 or 80, right, and maybe not hitting that 100. I've never seen anybody do that day in and day out for a period of at least five or six months and not end up with customers and succeed in the industry. Every single person I've ever seen not make it didn't make it for one reason. And like we always had a joke in management and this is true in like all sales Like if you were looking at your underperformers and results by money, you could almost always directly correlate it back with the activity on their phone. The guy making the least or the gal making the least made the least amount of calls. The person making the most always makes the most calls.

Ben Kowalski: 1:06:09

Right, and yeah, there's nuance and subjectivity to how and what they're saying, what we work on in coaching and things, but the reality is is like if that's not true, the rest doesn't matter. Right, like I could teach you to be the best basketball shooter in the world. But if you don't take shots, that doesn't do you any good either. Right, like if you're not going to put yourself in the place where you're everybody's uncomfortable, you're picking up the phone and calling somebody that didn't expect your phone call. Like you're taught your entire life to avoid being rude and that like that isn't, that isn't acceptable and it frustrates you when people do it. So to make somebody do this intentionally is emotional. That hurdle is the hardest thing to get them through. But if you can get them through it and do it consistently, that's by far the biggest fail or win fork in the road, if you will.

Blythe Brumleve: 1:06:58

And so once you because I am curious, like once you get the person on the phone, what is your advice to keeping them on the phone and listening to you?

Ben Kowalski: 1:07:08

Here's the way I kind of break down that approach is that, like, whatever you should say, it needs to get to very quickly what's in it for the person you're calling, not what's in it for you. Most people call and announce who they are and why they're calling and what they can do. The person you just called and interrupted doesn't care about any of that. They don't even care who you are. Yet they want to know if it was important enough for them to pay attention to, because they're still doing whatever it was they were when you called them, right. So you need to get very quickly to what's in it for them, whether it's you ship to a location close to them. You've got other trucks that deliver in their area, you've got customers that are in the same niche. Whatever that is of value that you're leading with, better be concise and matter to that person enough that they at least stop doing what they're doing right and then pay attention to you. That's one first step, right, and then from there, right, like you can pivot in a different ways based on what you say, but also right, like right. After that you're going to expect an objection Like hey, we're good, we don't need any help, thanks for calling. So then the next step is I usually call it like going for no, and it's you literally do that. I would say like hey, look, you know, to be honest, like I wasn't expecting to work together. In fact, hell, I don't even know if would be a fit to work together If you had a load. I was calling because I thought it might make sense to have a quick chat Again. This is why I called and then go into it, right, because whatever that is, they're never paying attention to you anyway until you at least get that thing first, right, and then, if you've got that, then you can at least move towards either a personal thing like hey, it's Monday, how was your weekend, how's your day shaping up? Getting them to just get into the flow of a conversation it's at the end of the week, maybe I'm going to go to personal. Like hey, thursday, one more and out the door, how's your week shaping up? Got any plans for the weekend? Right, I'm trying to talk to them the same way I would anybody that would be a friend or a colleague you would see in person, right, and it's just getting people to understand, like, if you get somebody to talk to you.

Ben Kowalski: 1:09:07

Actually an effective prospecting call is like no statements. There's a statement or two at the beginning of what's in it for you. The rest is me just asking you enough questions to keep you talking about what you care about. That's how I get you to like and trust me. Is that people? It's like what is everybody? The sweetest sound to everybody is their own name and everybody likes to teach and talk about things they know. I want to ask just enough questions to get this person I'm calling to be interested and to want to talk to me. A question does that. So it's really the questions, far more than the statements or anything you do, that gets that person to connect with you.

Nate Cross: 1:09:40

I want to add into and we talk about this a lot in our content is I'm like anti-script. I know some people are very like here's a script, read off of it, and that's great. If you're brand new and you don't know what else to say, I get it. But I've always gone I've done this myself and I still do this myself is if there's something new that you're trying to sell on or call on, have some sort of bullet points to give you an idea of the things you want to hit on, but don't have it literally written out verbatim and then have a list of prospecting questions to ask that you can kind of plug in as they're appropriate. Prospecting questions to ask that you can kind of plug in as they're appropriate, and also bullet points on objections, like Ben you just mentioned. You know the conversation should sound. It should be easy, right? You ask the question, they gave you an answer and then you ask the next question. But if you use a script, your next statement might be extremely way off from what their response was. When you know, when you um from whatever you had asked before.

Nate Cross: 1:10:40

I always think about a prospecting call is like the goosebumps books If you guys ever read those when you're younger was like all right, if you want to open this door, skip to page 47, right, like you should have a bunch of options in front of you. So instead of a script, when I was early on I had, um, like an Excel sheet or printed out on a word document just the big items that I wanted to hit on, and eventually you don't need it anymore, it's all up here in your head and you just can naturally open up a conversation. And like you, ben, I always try to open a conversation by just immediately releasing any tension in there. Whether it's a joke, I like I always you know football season I'll make a joke about how my bills sucked on sunday or whatever it was.

Nate Cross: 1:11:24

Um, or you know, in buffalo, it's june. Of course we have a blizzard right now. You know, you say something just to relieve the tension and pressure because you might get a little chuckle out of them. And now you're you know you're less nervous or intimidated on the phone. So break the ice, ask questions, build rapport, and I like to keep them short and sweet and have a reason to follow back up.

Ben Kowalski: 1:11:47

I would add, like one more thing to this too, and it was, I think, Noah Kagan was. This was in his recent book. He talked about this and you've probably heard this at some point. Right, have you ever heard of the coffee challenge that they've ever. They've ever heard that.

Ben Kowalski: 1:12:00

So, basically, right, the initial part of a phone call is really just the this little dance that all people do when they meet anybody anywhere to determine does this person have the same values as me? Right, you run into somebody at the grocery store, the cashier, wherever? Right, that's why you have these tedious conversations about like weather or whatever. Right, You're just trying to gauge this person's feeling and whether or not you proceed. Right, that's all this really is.

Ben Kowalski: 1:12:26

And one of my favorite things to do with newer salespeople, or even brokers, right, is like I'll ask them to do this and practice this in their day-to-day lives because it helps them with this muscle.

Ben Kowalski: 1:12:38

Right, it's one of the reasons why I think, like bartenders and servers tend to be very good in sales because they're just doing this all day, connecting with new people, making small talk and getting there very quickly. So the coffee challenge is really just to go. When next time you buy coffee. You have to ask them for a discount, which no matter what it is. You just hey, can I get 25% off this cup of coffee, which is a really awkward thing to ask and they're going to feel awkward, but it puts you intentionally in the space you're in and prospecting. That allows you to practice this in another setting, and it's literally the same thing you do on the phone, but you have more information because you can see the person. You can read them here with their body language or see what their body language is telling you. So I think those are other great ways to improve on this very specific skill set of connecting with people you've never talked to before.

Blythe Brumleve: 1:13:26

And then what does the I guess the the follow-up process look like, which I know can be super intensive, but just you know sort of a quick overview of what that process looks like. You've done the hard work of getting the leads, calling them, getting them on the phone, have a conversation with them. Does email play a role? Does LinkedIn play a role? Or maybe a combination of all of those things?

Nate Cross: 1:13:47

I would say all of the above. I think it depends on how the conversation goes, but I am personally a huge fan of communicating across multiple different platforms, but, more importantly, communicate the way that your prospect wants to be communicated with. So, by all means, throw a LinkedIn request, send a thank you email or a follow-up email. If they're open to give you your cell phone number or their cell phone number. I love that because then you can shoot a text like hey, you got a quick second, I got a question for you, right.

Nate Cross: 1:14:17

But I think that the takeaway is, when you're following up, have a reason to follow up. Don't don't call and just say I just wanted to touch base, right, like that's the dumbest follow up because you just you're wasting their time. But a good reason is hey, you mentioned this to me on the phone last week, jim. I looked into it and well, you know, blah, blah, blah, you know, like that you've got an actual reason to follow up. That's adding value to them. Like Ben said a bit ago, was you want to quickly get to a point where there's something in it for them, not for you, and that's a good follow-up is going to have something in it for them.

Ben Kowalski: 1:14:53

Yeah, for sure. And I think as you get better at this, you tend to leave the last conversation in a way that you can pick up the follow-up, in a way that they're not going to remember most of your last conversation, right? They're going to remember how they felt when they talked to you, right? Did they want to avoid you or do they want to engage? And then it's mostly like Nate said have something prepared.

Ben Kowalski: 1:15:13

Do not ever call and be like, hey, just following up, do you got any freight for me? Like, nobody wants that call. It doesn't add any value to anybody's life, so you would need a specific reason and you have to work to craft these on, like some calls. So that's why your notes in your CRM are incredibly important, because all of the money is in the follow-up. You're not going to get any business unless you can follow up with them at least a half a dozen times or more, and your ability to connect with them in the future is related to how you left the last one right, and what you're going to ask them when you connect back with them again, for sure.

Blythe Brumleve: 1:15:47

All right, I know we got to wrap up, so you know what. One quick question, just to sort of you know, round out the entire conversation. You guys are, you're experienced agents, brokers, you know creators within the freight industry. What advice would you give to other folks within the industry on how to balance marketing yourself, your personal brand, in addition to managing a full time job?

Nate Cross: 1:16:13

Oh, that's a tricky one, I think for some people they because marketing is such a broad term I would just I would say, if you're trying to do like marketing as far as like on like a social platform or website, I would say like create, just start creating content, whether it's blogs or posts. It kind of just shows up like kind of highlights who you are as a person and gives a little bit of like the human touch versus like, for example, linkedin right, some people all they do is share articles on there. But then there's a handful of more than a handful now people in my feed that like they tell personal stories and it's like I want to read this stuff and if I ever needed X, y and Z, I'm going to that dude because I feel like I kind of know him and I've never spoken to him. So I would say, like, have some kind of like authenticity in how you're sharing information or posting things. But you know, I don't have a good answer for you.

Ben Kowalski: 1:17:13

No, and I think that's really. I think what you touched on right is like one is it should be authentic to you Because, like we were talking about, with any of the LLMs or chat, gpts or whatever, right Like they all kind of sound the same, which means, even if it is an effective email or post, right Like there's no way for the person reading it to know anything about you other than the information, so it's nothing to do with you, so there's a very low likelihood you connect with them. So I think authentic content is valuable. And I think other marketing right, we're talking like emails and just whatever that is the message when I'm crafting them. Like is, if I had their job, would I be irritated? Someone who sent this or would I appreciate it? And if I would appreciate it, then I know I've got a closer message Right.

Ben Kowalski: 1:17:58

And the only thing I would add is like, with marketing emails specifically, is less is more. People put like these diatribes and these like long essays and I'm like I'll ask anybody. I have a client. I'm like open your email. I'm like how far into this email would you read before you clicked out of it If it wasn't somebody you knew? Right, and like, oh, a sentence or two, right. So again, how it's even like spaced and how short it is, I think matters a lot as well as your subject lines. Like it needs to hit home, be short, to the point and valuable. If it hits those three things, you're adding value and you're helping them connect with you in a way that builds a stronger relationship, because that's the goal at the end of the day.

Ben Kowalski: 1:18:41

Right, it's not being everything to everybody and just posting everywhere that you can do anything that anybody needs, because nobody wants a generalist and anybody they hire. Like, if you hire an attorney, you want somebody that is really good at the thing you're hiring them for. If you're hiring a doctor, you want to know the doctor that's really good at what's wrong with you, not the one that can do everything. Same thing in our industry. Right, like, stick to your strong suits. Try to be specific in a way that shows you can help this person or this industry or this type of shipper with this thing, not that you can do everything they've ever needed. Everybody tells them that that doesn't differentiate you. So those are the I guess the like, I don't know like kind of first principle things. I think, like the content that I either send to shippers, put on LinkedIn or even YouTube content, for that matter, right Like, if it's not hitting those things, it's just noise.

Blythe Brumleve: 1:19:34

Well, that is a perfect place to wrap this conversation. Tons of insight, tons of great advice and tips for folks out there, especially who are working in the freight broker role and beyond, just in general, of learning how to market yourself and create content and balance it all. I think we're all trying to figure out how to get a little bit more balance between all of those different things. So, Nate and Ben, where can folks follow you? Follow more of your work, you know. Get a copy of the Freight Broker Basics course.

Nate Cross: 1:20:02

Yeah, easiest way is our website, You'll see, right on the homepage you can sign up for our twice a week newsletter, which has free content and industry news. It's got our course link on there. You can see the curriculum. You can even see the first lesson for free just to kind of preview what it's all about and how it's taught, essentially how it's put out there. And you'll also find there all of our blogs, videos, podcasts. It's out there. We're on YouTube, if you just look Freight360 up. We're on Spotify, apple Podcasts, you name it. Our podcast is out there, just Google freight 360. You'll find us.

Blythe Brumleve: 1:20:43

Awesome and I will make sure to put links to all of those things in the show notes just to make it easy for folks. Um, but Nate and Ben really appreciate your time and and and your insight and perspective on this episode. I hope folks will will find a lot. I think they will. I I know that they'll find a lot of value in this episode. So thank you again. Thanks, blythe, thanks for having us.

Blythe Brumleve: 1:21:09

I hope you enjoyed this episode of Everything is Logistics, a podcast for the thinkers in freight, telling the stories behind how your favorite stuff and people get from point A to B. Subscribe to the show, sign up for our newsletter and follow our socials over at everythingislogisticscom. And, in addition to the podcast, I also wanted to let y'all know about another company I operate and that's Digital Dispatch, where we help you build a better website. Now, a lot of the times, we hand this task of building a new website or refreshing a current one off to a co-worker's child, a neighbor down the street or a stranger around the world, where you probably spend more time explaining the freight industry than it takes to actually build the dang website. Well, that doesn't happen at Digital Dispatch. We've been building online since 2009, but we're also early adopters of AI automation and other website tactics that help your company to be a central place to pull in all of your social media posts, recruit new employees and give potential customers a glimpse into how you operate your business.

Blythe Brumleve: 1:22:06

Our new website builds start as low as $1,500, along with ongoing website management, maintenance and updates starting at $90 a month, plus some bonus freight, marketing and sales content similar to what you hear on the podcast. You can watch a quick explainer video over on digitaldispatchio. Just check out the pricing page once you arrive and you can see how we can build your digital ecosystem on a strong foundation. Until then, I hope you enjoyed this episode. I'll see you all real soon and go Jags.

About the Author

Blythe Brumleve
Blythe Brumleve
Creative entrepreneur in freight. Founder of Digital Dispatch and host of Everything is Logistics. Co-Founder at Jax Podcasters Unite. Board member of Transportation Marketing and Sales Association. Freightwaves on-air personality. Annoying Jaguars fan. test

To read more about Blythe, check out her full bio here.