Freight 360 · 2026-06-30 · 14 min
Key moments - from our scoring
Substance score
60 / 100
Five dimensions, 20 points each
This listener-driven episode tackles practical entry and operational questions in freight brokerage. The host addresses the timing for starting a brokerage business in 2026, noting improved market conditions with capacity exits creating better margins, though he emphasizes that inexperienced 1099 contractors typically need to start with an established brokerage rather than striking out independently - similar to how real estate agents must apprentice under brokers. For sales reps in Chicago-style brokerages without carrier relationships, the guidance centers on using a "corporate we" mentality and leveraging carrier intelligence tools like gen logs and Highway to identify where carriers operate, ensuring you can speak confidently about your company's capacity even without personal relationships. The final discussion covers damage liability: when shippers damage carrier equipment (forklifts through trailers, dock doors) or carriers damage shipper property, responsibility falls on the liable party's insurance, not the broker - though brokers can facilitate documentation and claims. The emphasis throughout is on proper documentation, police reports when appropriate, and detailed TMS notes to support future insurance claims or dispute resolution.
No - most established brokerages require at least one year of brokerage experience and existing customer relationships to bring you on as a 1099 agent. Instead, start by working for a brokerage that will hire you as an employee or contractor to learn the business, similar to how real estate agents must apprentice before going independent.
Use the "corporate we" mentality - refer to carrier relationships and capacity as belonging to your company rather than yourself, and leverage carrier intelligence tools like gen logs and Highway to identify where your company's carriers operate and validate your sales conversations.
The shipper is responsible, and their liability insurance covers the claim. As a broker, you are not involved in the settlement, but you can facilitate by collecting photos, documentation, and directing all materials to the responsible party for claims processing.
The carrier's liability insurance covers the damage. Document everything with photos, consider filing a police report for serious incidents, and send all documentation to the carrier's insurance company to support the claim.
Critical - document everything in your TMS even before incidents occur, then add details immediately when damage happens. Without explicit records of what happened, when, where, and why, insurance companies are unlikely to pay claims and disputes become difficult to resolve.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode provides practical, actionable advice on entering freight brokerage, handling damage claims, and sales techniques, but much of it consists of fairly straightforward industry knowledge (e.g., 1099 vs. W-2 hiring, documentation practices) that experienced operators would already know. There are some useful specifics (gen logs, Highway ELD data, the 'corporate we' sales technique), but substantial portions repeat common sense rather than novel insights.
There's more meat on the bone in 2026 than there was two years ago
if you can't convince somebody to hire you, you're probably not gonna do too well in sales because everything sales
The episode relies heavily on conventional wisdom and industry standards (starting as 1099 agents, the real estate broker comparison, insurance claim procedures). The 'corporate we' sales framing is somewhat useful but not particularly novel. The damage claim discussion follows standard liability and documentation practices with no contrarian or first-principles thinking.
they're gonna want that in return as a as kind of a trade-off
Similar to how real estate agents start working under established brokers before going independent
The two hosts appear to be experienced freight brokers/operators with genuine field experience - one runs an agent program at Pierce and has managed carrier relationships and damage claims, while the other has similar operational depth. However, this is a co-hosted Q&A format rather than an external guest interview, so caliber is contextual. Both demonstrate legitimate practitioner credibility based on specific anecdotes.
I've done four forklift through the side of the truck is like the most common one that I've seen
I run an agent program at Pierce
The episode includes some concrete examples (forklift through trailer, $4,000 dock door damage, gen logs and Highway as tools, the $500 cash settlement scenario) but lacks quantified market data, timelines, or systematic evidence. Claims about 2026 market conditions are asserted without citing data. The damage claim examples are illustrative but anecdotal rather than systematically evidenced.
forklift through the side of the of the trailer
driver damaged uh dock door um backing into it. So there's like four grand in damage
The hosts demonstrate basic follow-up capability and are willing to expand on examples, but there is limited genuine push-back or probing questions. The Q&A format constrains natural dialogue, and the hosts tend to validate and expand on questions rather than challenge underlying assumptions. No meaningful disagreement or skepticism is expressed.
What you know, how would you respond to that question there?
You ever had had any instances like that where like uh I've done four forklift through the side of the truck
Computed from the transcript - who did the talking, and the words that came up most.
Nate Cross & Ben Kowalski answer your freight brokering questions and discuss: Starting a freight brokerage without experience in 2026 Cold calling without direct carrier relationships Handling forklift damage to your box truck Support Our Sponsors: Togo: Click Here OperFi: Click Here QuikSkope - Get a Free Trial: Click Here DAT One - Brokers & Carriers: Click Here to get 10% off your first year! DAT Outgo Factoring for Carriers: Click Here AscendTMS: Click Here and use promo code RA-freight360! to get AscendTMS FREE for 90 days! Recommended Products: Click Here Freight Broker Basics Course: Click Here
Transcribed and scored by The B2B Podcast Index.
Welcome back for another edition of the Final Mile. This is our listener QA only session. So we're only talking about questions that you guys have. These all came from a mix of our YouTube comments and our Facebook group today.
So for those of you getting involved in the Facebook community, we are up to let's see what the total uh count is currently. We're at 118,000 members. So it's massive. That's a big group.
Kind of feels like a you know, never thought I'd have a Facebook group with, you know, that many people in it. But appreciate all you guys in there. Um, so uh yeah, if you guys have a question, make sure to submit it to us either from the website or as a comment or in the Facebook group and uh check out the sponsors, help support this channel. All right, let's get into this first question here.
Do you think it's worth it to start a freight brokerage business in 2026? If so, how can I start as a 1099 contractor without experience? Um, well, if you were to ask me this question like two years ago or a year ago, I'd probably have a different answer about what the freight landscape looks like. There's always an opportunity.
Uh, it's just gonna be different challenges. I think the the market is very, very opportune right now to get into um seeing a lot of folks that are um getting into brokerage. Um and this this person asked about being a 1099 contractor, seeing a lot of people looking to go the agent route and try to maximize their earnings. Um, I would say as far as the timing of 2026, uh, yeah, I think we're in a we're in a good spot.
We've seen a lot of the excess capacity exit the market. So we're seeing um pretty good amount of business and and good rates that are out there. So as a margin-based entity in the transaction, um to use the uh the old how much meat on the bone is there, um, there's more meat on the bone in 2026 than there was two years ago. So you can definitely do well in brokerage.
Your competition um is still gonna be there, um, but you're gonna find that it is potentially maybe more difficult to find capacity, but ultimately with rates being higher, that can yield some some positive gains for you. Now, as far as being a 1099 without experience, um, it's very unlikely that a larger agent-based company is going to uh bring you in if you're not experienced as a broker. Most of them are gonna have a requirement that you've at least done the job for a year.
And most of the time they're gonna want they're gonna want you to already have customers to to bring with you to get started. Um, because the agent model pays a higher commission percentage, they're gonna want that in return as a as kind of a trade-off. Um, that being said, back to our Facebook group. I oftentimes send people there that, you know, if they come to me and they're like, hey, Nate, I know you you run an agent program at Pierce.
How do I want to get started? I love Freight 360. And I'm like, that's great. Glad you guys, you know, glad you love the show and love our content.
Um, but you know, we we don't take on new folks at my company. You've got to have experience. But I'll say I'll oftentimes send them, hey, check out the Facebook group. There's people in there all the time looking to, you know, bring in new folks, train them up and take a take a chance on them.
Um, that's probably gonna be one of your best bets is to go work for somebody that isn't running a strictly 1099 model, um, but someone who runs a brokerage and is willing to take a chance on you. So, and that is uh if you can't sell yourself into getting hired by somebody, um, you might struggle to be able to sell yourself as a freight broker to a customer. So what are your thoughts on that with like the you know, someone that wants to get started as a 1099? I I love the idea of like, hey, instead of me going and start my own thing, let me go work for somebody else, but I want to do it as a contractor.
What are your thoughts on that? I I I personally am a fan of it if they can find the right fit. Yeah, I think that's a really good way to start. I don't see why you wouldn't be able to do it.
I think it is exactly it hinges on the last thing you said, which is if you can't convince somebody to hire you, you're probably not gonna do too well in sales because everything sales. Yeah. And you need to learn the industry anyway. So, like if I were gonna do that and I didn't know anything about it, I would call in brokerages and try to get a job with an agent to learn to cover loads and to just pay me on my performance.
Like, I think that's totally doable. That's ultimately, I mean, you think about the the 1099, the agent world of other industries too. Like it's very often like real estate is one I use a lot. Like if someone, if someone is 20 years in the business and runs a great real estate um company and they're you know, they're doing all kinds of you know buys and sells of houses for folks, um, they had to start somewhere.
And they very likely started by working underneath somebody else as a real estate agent, right? And um, oftentimes when you come in and you're brand new and like we don't have to get a license to be an a freight agent like you do to sell real estate as an agent. Um, but when you're brand new and you've never sold a house before, they're gonna pay you a way lesser split um to work under that company, right? And you're probably gonna find the same thing as a freight agent if you're gonna go work for uh a brokerage or a broker or an established agency um and they're gonna show you the ropes and kind of um guide you and train you, they're not gonna pay you top dollar the way that um you know a company that will bring you in as a fully experienced agent is gonna pay you.
So just kind of keep that in mind. You gotta earn your kind of earn your uh way up the ladder there. So I like it. 1099, you're gonna basically go uh strike out on your own, right?
That's really you're gonna go up to bat and you either hit one out of the park or you go home with nothing. So a lot less risk for a brokerage to bring you on 1099 versus hire you W-2 and pay you a salary. All right. Um, this next one was a comment.
It was a cold calling one that you did, and you had you had talked about like the uh the cradle to grave model where you know you've got carrier relationships, and maybe you have carriers that are in a certain area, um, and you can kind of use that as part of your sales technique. But someone asked, what about when you work for a big brokerage that runs the Chicago style brokerage? Meaning, maybe I'm only a sales rep. I don't, I don't, I don't do care the carrier side of things.
They said, What you know, when one does not have direct relationships with carriers, how would you go about handling selling in that regard? So it was your video. I'm kind of curious, and you came from the Carol to Grave model. Um, what would you, you know, how would you respond to that question there?
I would use, have you ever heard the term the corporate we, which basically you refer to we, meaning we is anybody that works in that company is basically you or your team. Basically, instead of saying, like, you know, hey, I I have uh I have these carriers that you know oftentimes operate in this area, uh, we as a company have these carriers that operate in that area. And I'll tell you this too. Like if you're if you are a um, if you're in that model and you're a sales rep, there are so many tools now that you can use to get intelligence on where carriers operate, that I would highly encourage um, you know, to be able to have access to a lot of those tools.
Like things like gen logs is like amazing when it comes to seeing where carriers are running. And even um like highway's done a pretty good job at it too, with a lot of their ELD data and inspection data and um and whatnot. So uh having access to see where carriers are operating again, and then then you kind of mirror that with the whole we mentality that you mentioned. Um, I think that's really it.
And um, you can't succeed in brokerage if you only have one side of the equation, right? If you only have customers that want to deal with you, but not carriers that want to haul for you, you're not gonna succeed. And if you only have carriers that want to haul with you, but not customers to load those trucks, you're not gonna succeed. So that's where the Chicago model, you need to have very, very good communication between those different entities.
So all right. Our last question here is uh this kind of we did an uh episode on claims on our most recent full-length podcast, and this is a sort of a nuanced question. There is who do I contact if a shipper's driver damages my box truck with their forklift? So um, I've seen this happen um when I worked at a trucking company, and we owned our own trailers, but we oftentimes would use brokers to bring in third-party carriers' trailers to load them for um you know long-haul stuff that didn't fit in our LTL network very well.
And sometimes we'd have a company forklift operator poke a hole in the side of the uh the carrier's trailer. And in this case, it's the same situation. The shipper um damages the forklift, or with the forklift damages the trailer, or vice versa, if a um if the uh driver damages property at the shipper or receiver. Like I've seen them, you know, hit low power lines or hit a um you know one of those concrete poles or something, right?
They they put they do damage to it. Um it is usually between those two parties to figure out how they want to handle it. And oftentimes, if it's serious damage, um, you'll have insurance that covers uh any kind of liability to things of that nature. So, like a moat, if a motor carrier um damages property of a shipper or receiver, usually their uh liability policy is going to cover damages if if there's an incident like that.
But if it's the shipper andor receiver damaging the carrier's equipment, like in my case, the forklift through the side of the of the trailer, um as the if you're a broker, you have no involvement in that whatsoever, but you can you know try to help facilitate the conversation, but it's it's ultimately gonna be on whoever's property and responsibility it was that damaged it is gonna have to um pay. And I've I've seen them just pay cash, like, oh yeah, I you know, I scrape the side of your trailer, and then you're like, you know, give them 500 bucks or like literally write them a check for 500 bucks.
Um, but for more serious damage, if it's worth filing a uh insurance claim on whatever policy covers that, I've seen them go that that route as well. But yeah, it's it's not the broker's not involved, it's not on that standard like cargo policy. Obviously, in this case, it's the shippers um fault that did it. Um, but yeah.
You ever had had any instances like that where like uh I've done four forklift through the side of the truck is like the most common one that I've seen. And it's I've handled all the operator. Yeah, all the above, and I facilitate almost all of them the same way, which is just like it's my customer carrier. I had a month or two ago uh driver damaged uh dock door um backing into it.
So there's like four grand in damage. I get the shipper's pictures, send it to the carrier's insurance, help them with the claim. Had the other thing too, where like the forklift a few times. I've had ones on flatbeds that were damaged, loading coils.
Um pretty common. I mean, and you really just kind of handle them the same way. Like just get all the documents, find out who's responsible, and then you just send them all to the one person, whoever that party is, right? If it's like you said, if it's the carrier that gets damaged, like hey, send me all the pictures, tell me what happened, document it, you send it to your customer.
If the building gets damaged, hey, send me all the pictures. A lot of times when the buildings are damaged, I've had police reports. Um, I don't know that that's required, but like I've seen that a few times. I would always say a rule of thumb is when in doubt, get a police report for for like a lot of different instances.
Like I've had them when if you have a driver that's being crazy um and you wanna like you want proof or some documentation of what happened if they threaten you, um, yeah, you can get a police report. So you got an irate employee, right? Yeah. I've talked with you about this in the past, right?
Police report. We've dealt with yeah, like at this point, I'm like, kind of makes me feel old because I'm like, yeah. I'm like, as you were saying all those things in my head, I just saw all of these memories of every single one of those. I'm like, employees?
Yep. Yep. Drop, yep. I'm like, handguns, yep.
I'm like damaged equipment, damaged buildings, damaged other vehicles, damaged. I'm like, yeah, at this point, like all the above. And documentation is your friend, right? Like you said, yep.
Call the police, that's what it's for. Then you've got a paper trail. Now you don't have people back. The worst is like when you've got to like work through a dispute and everyone just points fingers at each other.
Like, that's why you documentation is so helpful, which is why we also stress this all the time. Put in your notes in the TMS, document things even when they don't go wrong, because you don't know when they'll go wrong. And if you've got no notes, you have no idea what happened. It's very hard to get an insurance company to pay for anything if you can't explicitly say this happened at this time and this location for this reason.
Yep. Exactly. All right, good questions. Keep sending them our way.
We'll keep answering them. Final thoughts then. Whether you believe you can or believe you can't, you're right. And until next time, go bills.
How Freight Brokers Find Customers | Episode 34885 / 100Freight Claims Explained | Episode 34766 / 100The Pipe Stake Hustle That Won A Customer | Final Mile 14676 / 100Your SOPs Only Work When You Enforce Them | Episode 34668 / 100Real-World Crisis Calls In Freight Brokerage | Final Mile 14581 / 100