Middlemen: Truckers, Brokers, and the Supply Chain Swamp

Chapter 6 - Pump & Dump

“It’s not exactly the Peace Corps.

We’re freight brokers, man.”

—Kyle, Senior Sales Rep

A few weeks went by. Each day I walked in and out of Dinkum Logistics I left feeling a bit shocked, in one way or another. 

This world of Supply Chain was all very amusing to me: the antics of Dinkum employees crashing around the bullpen floor all week; the barking of managers as they flipped from motivational to threatening on a dime; the obscure locations we hauled loads from in Lithia Springs GA and Commerce CA and Billings MT and Akron OH; the ease at which we Brokers could generate $500 when we match the right load with the right trucker at the right time; the constant slurs, threats, and profanities from the surly truckers we hired; the speed and carelessness at which Broker and Trucker negotiated the terms of service: “Hi, nice to meet you… do you want this $300,000 truckload of Nikes?”, “Sure, I’ll move it for three grand.” “Okay, here’s the address. Please deliver on time.” “What was your name again?”

Or maybe it was just the fact that when people said “The Supply Chain” I didn’t really know what that meant until I became a freight broker and started ripping calls and slinging truckloads of dog food around to various Walmarts around the Southeast. Salt Lake to Decatur—that lane was a goddamn gold mine for me. 

A few weeks in, I was really starting to get a sense for what this place was all about. For better or for worse.

My alarm got me up early and I put my clothes on. Brewed a pot of coffee. It was going to be a big day, they told me. I was assigned to shadow Kyle around. All I knew about him was that he wore a Vineyard Vines vest every day and had just bought himself a new truck. Freight had been good to him. 

I stepped out my door and felt the heat drag on me. The sun hadn't even risen yet, but it was already 80 degrees and humid. It felt like walking through a toaster oven. October in Austin, baby. 

I jumped in my car and headed downtown, dodging the minefield of potholes on the way in. I passed a homeless man outside the public library waiting for it to open in an hour. He probably just wanted to hang inside the air conditioning. A jogger ran by him, checking his watch. One guy dying to get inside, one guy dying to get out. 

Then I got to the brokerage. Noah was in before me, so was Mollie. She had the aux chord this morning, so there was Bikini Kill piping in over the loudspeaker: the crashing of cymbals, an off-beat kick drum, and the lofi bitching about something or other. It was early and I felt like bitching, too. 

I checked a few emails, took a few calls, and got into it. 

Kyle noticed something I was doing wrong. I heard him go “pff”, and he swung right over to point it out. 

“Naw man, you’re doing it all wrong… look, let me show you.” Kyle said to me. He’s the Senior Sales Rep from Chicago. Tall guy, handsome, with the eyes of a maniac. If you told me he kept his ex-girlfriends in the refrigerator, I’d believe you. But he was one hell of a freight broker, and today he was showing me the ropes.

“Look man,” he said, “you’re focused on selling all the wrong things. Premium Logistics Services? Cost Certainty? Those are just buzzwords, no one cares. Keep it simple with your prospects - we move loads.” 

“We move loads, got it.” I said. “But what about building relationships? Or demonstrating value? Isn’t that what business is all about?”

Kyle looked at me funny. 

“I mean sure, man. Having a relationship with a guy, making small talk about sports, or whatever… That certainly helps, but to be honest – we’re just whores to these people. Who can move their loads cheapest?” He scoffed, then he turned back to his screens. He was studying market trends, where the trucks had moved overnight, and which markets were hot. 

Kyle was right, I was overcomplicating it. My prospect had just hung up on me, slammed the phone. It was becoming a pattern today. 

I glanced around the sales floor for a moment, looking for inspiration – it was a circus as usual. Casey was yelling at a dispatcher, something like “take the load! Just take it! $5000 IS a market rate!” Salazar slammed his phone on someone and called them an idiot beneath his breath. Then he stood up and dropped off a package below an empty desk. Noah was, as usual, quietly booking more loads than anyone at the brokerage. Moving loads, printing money. 

It was cold across the brokerage floor that morning, with bright fluorescent lights watching everything we did. 

Who are these ruthless heathens? I thought about that phone call I overheard between Hartman and the VP. It was crazy how they talked about the potential hires. Where would the next crop come from? I wondered if it’d be the run-of-the-mill pipeline of college grads, flunkie sales reps, or wanderers like me who moved to town with no connections. Hartman was trying to hire a Penn State kid and the VP wasn’t having it. It was an amusing phone call to hear: “yes… yes . . . I know he’s pedigreed, I know he’s got hedge fund experience . . . you’re saying you don’t want hedge fund experience?  . . . he won’t be a good culture fit here? Got it, sir…”

Maybe the VP was right. I’m not sure a Hedge Fund kid would be a good fit at Dinkum either. Sure, the lines of coke would make him feel right at home, but ultimately our commission checks had far fewer zeros.

I was scrolling through the internet praying for a lead. 

“Here, let me drive.” Kyle said. He grabbed my laptop and pulled up Google. “Where are you from?

“DC.” I said. “Well, Northern Virginia, actually. But I usually just tell people DC because it’s easier.”

“DC? Great… Here—check this out.”

He googled DC and switched over to the map view. Then he started scrolling around until he found the part of town with all the warehouses. 

“Here you go.” He said.

“What’s this?” I asked.

“Your leads.”

“My leads? . . . where?”

“These warehouses, bro. Call them. There’s 5o results on this google search, and I guarantee you most of them ship freight. Call every single one and ask them for freight.”

“What do I say?”

“Introduce yourself: say ‘Hi, this is Chris calling in from Dinkum Logistics, I’ve got an empty truck across the street from your warehouse ready to rock n’ roll!’ and then ask him if he’s got any loads we could move.”

“Empty truck?” I said. “But don’t we have to find the trucks first?”

Kyle smirked. 

“Trucks? Shit… no dude, nobody has an empty truck when they call out. Waste too much time. We’ll worry about finding the truck later. Just win the freakin’ loads…”

And that was that. I was off to the races. 

The goal for the day was to make 200 cold calls. That’s it – just talk to as many businesses as possible, praying they ship freight. The ones that do, harass them until they send us a load. A truckload of almonds, or potatoes, or steel, or whatever – it doesn’t really matter what. Any truckload we book is an opportunity to generate margin. And when the shipper finally caves and sends us a load? That’s when we pray the Trucking Gods reward us. If they do, we’ll find an empty truck near the warehouse who will agree to move the load for less than we’re being paid by the shipper. That’s how we generate a margin. 

But you can never be sure where the trucks are each morning until you start calling. It’s all a gamble. 

Calling around is how you get a feel for the market. Which cities are hot. Where the truckers want to go. You can also just take off your headset and listen to the chatter around the bullpen. You can see how quickly Vlad calls in when we post a Chicago to Dallas load, which is normally a very juicy lane. The phone lines were the rumor mills – you’d hear whispers of which cities were hot each morning and where the truckers were hiding. NorCal was hot yesterday. Today it’s the Midwest and Florida. Everyone was trying to get down there for some reason. 

So there I was all morning, firing off sales calls, trying out various pitches, saying whatever I could to try and win a load. God willing. I needed to focus on winning freight and showing Management I deserved my seat. It wasn’t going well. I made 40 more outbounds and there was not much traction at all. There were dial tones. From the folks who did pickup, there were lots of “I’ll get back to you”s. 

Kyle noticed I was flailing. 

“You know what?” he said, turning away from his standup desk, “I’ll show you how to win some freight.” 

He must’ve been feeling generous because he normally looked over my head whenever we spoke. It never felt condescending, he just seemed like he was preoccupied. His eyes were glazed over all the time, that’s what concerned me. I was also very concerned that Kyle was the only straight edge employee Dinkum had, the only guy who didn’t smoke, drink, or do pills. Including Management. He was clean cut, dapper, and sober – yet, somehow, he was still able to put in 14 hour days at a freight brokerage and crush his numbers. Quite the sicko.

“I could use the help… thank you Kyle, I appreciate it.” I wondered what kind of tricks he had up his sleeves. 

Kyle swung over to my desk and formally introduced himself. He was friendlier this time. He told me about how he got into freight brokering. He told me he threw his arm out in the Minor Leagues after a nice career at Northwestern. Then he flailed around a few insurance firms for two years and struggled to obtain his Series 7. To his dad’s disappointment, he was never able to bust into Wall Street – his dyslexia was the real problem. And after his family’s private equity firm went belly up in ‘08, Kyle had nowhere else to go. Luckily, some brokerages in Chicago were hiring, “anyone with a pulse,” he told me, but instead of peddling penny stocks to dentists in the Midwest, these brokerages peddled freight. There’s a million freight brokerages in Chicago, and they’re all looking for guys like Kyle. He was picked up by one and quickly learned the ropes. Within a year he was able to upgrade his apartment, his collared shirts, and his big watch. “I absolutely love this industry,” he said, “anyone can get rich.” I hoped he was right. Kyle might’ve been the only employee at Dinkum who was genuinely grateful for his seat.

We went back to the screens. 

“What am I lookin’ at here?” Kyle asked, arms crossed, squinting. 

“Just replying to an email,” I said. “I’m asking this shipper in Beaumont, Texas, if he’ll pay $1200 to move his load of steel to Houston.”

“Oh man,” he said. “Good luck making money moving steel. You’ve got to be prepared to get grimy if you want to win steel loads. These steel shippers are cheap bastards. . . Ever since China got involved, it’s all about cost per pound.”

“So the rates are cheap?” I asked.

“Bro,” He said, eyebrows raised. “Not only are they cheap - we’re going to have to get creative to win these loads. . . Luckily, there’s a couple things we can do to increase our chances.”

There’s two sides of this business – the carrier (trucker) side and the shipper (customer) side. Two totally different vibes. Today, management wanted to see firsthand which of us junior reps was cut out for customer sales. It seemed like it was mostly the jocks and the Midwesterners – all the Chris’s and Kyles’s from Chicago or St. Louis – those were the types they selected for customer sales. Management seemed to prefer guys with tidy haircuts and pastel button downs to speak with the shippers. Nobody too edge edgy. Wouldn't want to spook the customers. 

For Customer Sales, it seemed like you needed to have certain hobbies, too. The love of gulf, fantasy sports, an enthusiasm towards craft beer. These things gave our customer reps plenty of small talk when they were on video calls or on-site visits. The Customer Reps were cleancut and waspy, and they looked a lot like the LOgistics Managers and Warehouse Supervisors we were selling to.

Anyone who had “Supply Chain” in their job title, they were our target market. Having this comfortable familiarity sure seemed to help sales close more deals. I guess Hartman was right, his advice for the industry – start by calling people who look like you. 

The carrier side had a different vibe to it. Noah, Benny, and the boys, they were a little more rough around the edges. Salazar would likely be placed over there, too, if he didn’t get himself fired first. When it comes to Carrier Sales, management seemed to prefer the alternative. The dirtbags and the burnouts. The ex-bartenders, the potheads, and the tattooed. On the carrier sales team, it mattered far less what you looked like. It was a blue collar / dirty job, if offices had such a thing. The job of a carrier rep has nothing to do with shaking hands and looking pretty. Your job is to call as many truckers as you can, haggle about trucking rates, and get the loads moved. Each and every day. 

You might also spend some time tracking down the occasional MIA truck driver, so investigative skills come in handy. 

And since carrier sales is a job done almost entirely on the phone, all anyone cares about is your voice – and your ability to work long hours. They lived in the bullpen, sitting deep in their chairs, only getting up to refill on coffee or go pee. They sucked vape pens and showed up to work high, relying on alcohol to even them out. But they were nicely compensated. 

Casey told me the good carrier reps that moved a lot of freight could easily clear six figures in their first year. But you had to stomach the financial swings. Their pay swung with the booms and busts of the market. Dinkum paid a low base salary (by design) which kept the carrier reps from taking time off. They were paid 15% of the margin on any load they booked. This might only be like $50 per load, but if you booked a few dozen loads per day, you’re looking at a substantial paycheck – no matter what you look like.  

Management seemed to think I had the temperment of a customer rep. They liked the way I spoke, my clean shirts, and my college education. “Let’s see how you do in front of customers, Chris.” Hartman said to me. “I’m ready to rip some freight, sir.” 

Before they penciled me in, they wanted to see if I was resilient enough to handle the rejection of sales. I had never sold anything, except the occasional sucker at the poker table who thought I had the nuts. It was usually a reverse-tell that worked for me, showing weakness so they’d think I was faking it. But selling freight was far different than playing poker. It’s a torturing task. It’s nothing but no’s, all day, every day. 

During Proving Ground, Hartman touted a sales study that showed you’d have to make a thousand phone calls, on average, before you’d land a new customer. 1,000-t0-1, those were the odds around here. The same odds as hitting a 10-team parlay on Sunday, which I could never seem to hit. Management might’ve been right about me being a better fit on the customer side. But either way, I needed to clean up my pitch ASAP and get some money going. 

How do freight brokers pitch? It takes some mental gymnastics. We’re trying to convince shippers to give us their loads, but since we’re just middlemen, we can’t actually haul the loads ourselves. We have to find a trucker to move the loads. But how do we find a trucker before we have a load to give them? It’s a chicken or the egg situation. It was a conundrum, if I’d ever seen one. I hadn’t figured it out yet and it made me dizzy. You could hear a shakiness in my voice when I pitched.  

I took a swig of coffee. Then another. It was out, so I got up to refill and came back to the desk with Kyle.  

“I’ve got an idea.” Kyle said, interrupting my daydream.“Here, give me your phone.” He demanded.

“My cell phone?” I asked.

“Yes, your cell phone. Let me borrow your cell phone for a minute. I’m going to show you a little trick I like to use for hunting. Works every time.”

I handed Kyle my phone, having no clue what he’d do with it. This might become a regret.

“I’ve got a customer down in Woodville, Mississippi.” He said, eyes narrowing. “Total Bumfuck Egypt. Guy runs a lumber mill down there – it’s not steel, but commodities are all the same shit. He lets the loads rot away until a trucker calls in with the cheapest rate. Otherwise, he’ll just let it sit and gather cobwebs. Like I said – moving commodities is as grimy as it gets.”

Kyle punched in a number and listened to the tone. “His name is Jimbo. . . I swear to god, bro.” He whispered as the phone rang. 

Then Jimbo picked up. 

“Hahh, this is Jimbo, how may ah help yew?” He said in a muddy, twangy draw.

Kyle went right into his pitch, but oddly he was speaking in a different voice. “Howdy there sir, this is Jeff calling in from Speedy Logistics. Do you have any loads I could move for ya today?” Kyle’s voice was squeaky and high, like he was impersonating his little brother. And he introduced himself as Jeff, from Speedy Logistics. Why was Kyle disguising himself? Was he having a manic episode?

“Weeeall,” Jimbo said. “Ah’ve got uh couple uh loads ah need moved up tuh Albuquerque this week. Each one is settin’ at 48,000 pounds a pop. Yew got uh truck for me?”

Kyle waited a moment, smiling out of the corner of his mouth. He looked at me, winked, then returned to the call.“Why yes sir I do, I’ve got a truck empty now, gassed up and ready to roll! Can you do $4000?” 

“Four grand?!” Jimbo said. He was appalled by the rate. “Ah’m used tuh payin’ close tuh half that! . . . With all dew respect, whut are yew smokin’?!”

“Well, sir.” Kyle said, carrying on his abnormally squeaky voice and newfound alias. “Have you heard about the spike in diesel this week? Must be the mudslides in your area, tankers can’t get in. Also, my carrier partners are telling me it’s 20 loads per truck in Mississippi. The market flipped overnight, and unfortunately for you, sir, you’ve found yourself on the wrong side of it. Four grand is what these are going for today - if you need these loads moved, take it or leave it.” 

“Yahhh, wheel see about that!” Jimbo shouted. Then he hung up and went back to whatever he was doing. 

I was confused. The only thing about Kyle’s pitch that might’ve been true was the mudslides, and I wasn’t even sure about that. It could've been a bullshit scare tactic. The rest was pure bullshit, I knew for sure. 20 loads per truck? Mississippi rarely gets above ten since there’s barely any manufacturing down there. Just a handful of dying lumber mills and places where they assemble sedans. What was Kyle up to? I thought to myself.

“Did you hear that?!” Kyle asked, excited. “Sticker shock – that guy was repulsed when I gave him my rate! Step one is complete.” 

Kyle handed me my phone. Then he looked at his watch and seemed to count to something. He waited there, his bottom jaw slightly open. He was thrilled with himself. 

A minute passed. 

“Now check this out.” Kyle said. He picked up his phone this time and punched in Jimbo’s number. Jimbo picked up. Kyle introduced himself in his normal voice with his normal name: “Gooood morning, sir! Do you have any Albuquerque loads available?” He asked cheerfully. 

“Yeh, whatchyu got?” Jimbo asked with suspicion. 

“Well,” Kyle said, “my owner operator is down in Woodville, he just got unloaded. He’s based in Albuquerque and needs a load home for the weekend. Real desperate. We’re just lookin’ to cover his fuel on the way back . . . can you do $3000, sir?”

“$3000?! Even with the mud-slads?!” Jimbo asked.

“Yessir.” Kyle said.

“That’s thuh best rate ah’ve heard today! Lock it een buddy!” 

Jimbo sounded like a man with the winning lottery ticket in his pocket, thinking he had gotten a good deal to move his load of lumber up to Albuquerque. But it wasn’t a good deal for ole’ Jimbo. He got absolutely took. Kyle tricked him. Ran him over. He was paying $3000 bucks for a load that normally goes for $2400. I guess that’s the power of sticker shock – and market manipulation. The two thanked each other for their business, emailed the contract, and locked it in the load.  

“Alrighty sir, I’ll write up the paperwork now. Thank you.” Kyle remained calm until the moment he hung up the phone. Then the excitement burst onto his face. He had just gotten a load with $600 extra in it and he was so proud of himself, totally amped up. 

“Let’s goooo dude!” He said. I could tell he lived for these kinds of moments. 

He made a fist and turned to the carrier reps behind him and hollered: “I’ve got a Schmoker hittin’ the board!!! Mississippi to New Mexico, who wants to book a G-Rip on this flaty?!” To which someone responded “Let’s fucking go dude! Feed the beast.”

That’s how it’s done? I thought to myself, careful to keep a straight face – I didn’t want anyone to know I wasn’t with it. It felt scummy, for sure. And it felt like something I might have to do in order to survive around here. 

I looked around to see if anyone had noticed what Kyle was doing. There was a group of carrier reps hanging around the beer fridge, sipping Lone Stars. Noah was shuffling back from the bathroom taking a long drag from his pen. Mollie had given up the aux chord and there was Old Town Road playing on the speakers. 

“Ridin’ on a tractor, leanin’ on my bladder” . . . I figured it was Hartman’s favorite song because he played it every day. 

No one had noticed a thing. The freight kept on movin’.