The Freight Show

The Freight Show

#23 How Will Hopkins (BlackBox Logistics) Got Fired Right Before His Biggest Opportunity

Will Hopkins started a brokerage after getting fired, spent a year dispatching on the carrier side, and built BlackBox Logistics to $70M. This conversation is about what it took to break through a plateau and what brokers look like from the truck cab.

The short version

Will Hopkins started at a Roadrunner agency at 19, moved in with two coworkers, and eventually decided the three of them should start their own brokerage. The plan was to quit after the holidays and keep their vacation pay. It didn't go that way. Logan quit on the spot when management asked him to move his desk. When they pressed him on who was coming with him, he said Hopkins and William. Will and William got fired.

They had non-competes to sit out, so they started a dispatching company instead, booking loads off truck stops for owner-operators with brand-new authorities. Will calls it the best thing that ever happened to his career. Working on the carrier side for a year gave him a view of what brokers look like from the truck cab, and it shaped how BlackBox approaches carrier relationships today.

By the time their non-competes expired, COVID had hit. They started the brokerage in William's living room in Birmingham with no AC. They've since built BlackBox into roughly $70 million in annual revenue as a flatbed-focused brokerage.

A lot of this conversation is about what it took to break through a plateau in the $35 to $50 million range. The answer wasn't a new sales strategy. It was building out a team system that documents tribal knowledge as institutional process, defines clear escalation paths, and creates a career path so that a high-performing seller doesn't have to keep handling data entry and track-and-trace to stay relevant. Layers of specialization freed up the senior account managers to actually focus on the part of the job that produces revenue.

Will also has a measured, specific read on the Supreme Court decision in the Montgomery-Carabay case and what it actually means for brokers his size. He's not losing sleep over it.

Key Takeaways

  • Getting fired forced the best learning of Will's career. A year on the carrier side, dispatching loads for owner-operators with new authority, gave Will a ground-level view of how brokers treat carriers. That perspective directly shaped the support infrastructure BlackBox built for the carriers in its network today.

  • The $35-50M plateau is a process problem, not a sales problem. BlackBox got stuck at that revenue level for two years before identifying that "tribal knowledge" was the blocker. Different senior reps gave different answers to the same question. Documenting that into one clear, accessible institutional process, with defined escalation paths and a visual workflow, was the structural change that let the business move forward.

  • Carrier rep productivity comes from repeat loads per carrier, not loads per rep. The metric that separates top carrier sales performers at BlackBox isn't how many loads they book overall. It's how many loads they book with the same carrier. A rep booking three loads per carrier per month rather than one is dramatically more efficient, because sourcing a known carrier takes a fraction of the time of cold-sourcing a new one for every shipment.

  • Eastern European carrier sales talent is plug-and-play. BlackBox found that Serbian and Polish carrier reps with a decade of freight experience can start booking loads on day two. Compared to the six to nine months it typically takes to get a US college graduate fully productive, that's a material difference in time-to-contribution.

  • The C.H. Robinson Supreme Court decision isn't an existential threat to mid-sized brokers. Will's read: brokers that were already doing proper carrier vetting aren't changing much. Insurance will go up, but that cost is manageable.

Notable Quotes

"We started a dispatching company, which I think was really the best thing I did for my career. It allowed us to see it from the carrier side working with a lot of owner operators, small fleets, new authority, booking loads off truck stops for these guys, trying to get their business off the ground."

Will Hopkins, Co-founder, BlackBox Logistics

"A lot of brokers get to the 50,000,000 mark. And then to get from 50 to 500, the two most common routes are: a, we have a clear path to expand load share within the customer without burning out operations — rinse and repeat — or b, you get a bunch of really good cradle to grave brokers and build out teams with entrepreneurial spirit."

Will Hopkins, Co-founder, BlackBox Logistics

"We had a lot of tribal knowledge and that tribal knowledge being different depending on who you ask. Broker Tom has an issue. He walks over, asks this guy that's been here three years, what should I do? He tells him one thing. Goes to ask somebody else. They tell him something completely different. Making it institutional knowledge, building out systems, having a place where people can access that knowledge — that was the shift."

Will Hopkins, Co-founder, BlackBox Logistics

Episode Chapters

  1. 00:00Intro: Will and Jesse have been following each other's content
  2. 01:09Will's take on the Supreme Court decision and why BlackBox isn't reacting much
  3. 02:23Why the small-to-mid-sized broker extinction narrative is overblown
  4. 05:41Freight was always a strange exception on intermediary liability
  5. 08:30What "reasonable" carrier vetting will end up meaning in practice
  6. 11:09The insurance math and why Will doesn't see this threatening BlackBox's bottom line
  7. 12:50Mega carriers, road check theater, and why announcing inspections still works
  8. 15:51The record month that meant nothing: average revenue per load doubled, but it was capacity-driven
  9. 17:02Why flatbed is tighter than van and reefer right now
  10. 18:11The data center myth: 5% of construction flatbed moves, but feels like 100%
  11. 21:25Why Will stopped predicting freight markets
  12. 22:17Picking the most useful mental frame and refusing to believe your own market story
  13. 25:55What COVID hiring taught BlackBox about discipline through the cycle
  14. 28:15Hitting the $35-50M plateau and what "what got you here won't get you there" actually meant
  15. 29:17Building the seller-level career path and the team system that broke them out
  16. 30:38Turning tribal knowledge into institutional knowledge across the floor
  17. 31:20Partner Logan's internal tooling: Slack-based load previews, data entry bots, the BlackBox Dash
  18. 32:53Why the pod model beats the pure split model on customer ownership
  19. 35:18Building support around great account managers so they don't burn out
  20. 36:31Hiring green talent vs. plug-and-play recruits and how the freight recession brought BlackBox top operators
  21. 37:29Why Eastern European carrier sales reps have been a productivity unlock
  22. 40:16Carrier ownership inside a pod system and the trade-offs BlackBox accepts
  23. 44:24The metric that separates top carrier reps: loads per carrier, not loads per rep
  24. 45:47The origin story: working at Roadrunner at 19
  25. 47:25Logan quitting on the spot, Will and William getting fired, and the non-compete that forced the dispatch detour
  26. 47:50A year dispatching for owner-operators and brand-new authorities
  27. 48:09Starting BlackBox in William's living room with no AC in Birmingham
  28. 49:15What was harder than expected: managing employees, not moving freight
  29. 51:54Three founders, three roles, and the rare stable equilibrium of a founding team
  30. 55:12What gets Will most excited: being present, investing in the process, not staring at the scoreboard

Full Transcript

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Introduction and Background

Jesse Buckingham: Welcome back to the Freight Show. I'm here with Will Hopkins, founder of BlackBox Logistics out of Birmingham, Alabama. Will, thanks for being on.

Will Hopkins: Yeah, happy to be here. Thanks for having me.

Jesse Buckingham: Let's start from the beginning. How did you get into freight?

Will Hopkins: Yeah, so I was 19, just out of high school, didn't really know what I wanted to do. A buddy of mine was working at a Roadrunner agency in Birmingham and said hey, come try this out, you can make good money. So I went in, started as an entry-level broker, learned the business from the ground up. That was probably 2013 or 2014.

Getting Fired and the Non-Compete Year

Jesse Buckingham: So walk me through how BlackBox actually started, because I know there's a story there.

Will Hopkins: Yeah, so I'm at this Roadrunner agency with two other guys, Logan and William. And we all kind of figured out around the same time that we should be doing this for ourselves. We made a plan to quit after the holidays, keep our vacation pay, do it the right way. Logan had other ideas.

Jesse Buckingham: What happened?

Will Hopkins: Management asked Logan to move his desk. He said no, quit on the spot. Then they asked him who was going with him. He said me and William. We hadn't agreed to that. So Will and I got fired for something we hadn't actually done yet.

Jesse Buckingham: That's a wild way to start a company.

Will Hopkins: Yeah. But here's the thing. We had non-competes. So we couldn't start a brokerage right away. We had to figure out something else to do for a year. And that's where it got interesting.

Dispatching for Owner-Operators: The Carrier Side Education

Jesse Buckingham: So what did you do during the non-compete?

Will Hopkins: We started a dispatching company. Just us, working out of someone's apartment, booking loads for owner-operators with brand-new authorities. You're out there at truck stops, you're working the boards, you're dealing with drivers directly. It was a completely different world from brokerage.

Jesse Buckingham: What did you learn?

Will Hopkins: Getting fired was the best thing that ever happened to me. I spent a year on the carrier side and I learned more about freight in that year than I had in the three before it. When you sit in the cab and you see how a broker treats a driver, it changes everything. We built our carrier support model around that experience. The carriers in our network today get a level of attention and communication that I think most brokers just don't provide, because they've never been on that side of it.

Starting BlackBox in a Living Room During COVID

Jesse Buckingham: So your non-compete expires. What happens next?

Will Hopkins: COVID had just hit. Perfect timing, right? We started the brokerage out of William's living room in Birmingham. No AC that first summer. Just phones and laptops and whatever carrier relationships we'd built up during the dispatching year.

Jesse Buckingham: Were you scared?

Will Hopkins: Honestly not that scared. We'd already been through the worst of it getting fired and having to pivot. And the market was weird during COVID but there was freight moving. Flatbed in particular was strong. We focused there from day one and it worked.

Breaking Through the $35-50M Plateau

Jesse Buckingham: You grew pretty quickly after that. But I know you hit a plateau. Talk me through that.

Will Hopkins: Yeah. We were stuck at $35 to $50 million for two years and we couldn't figure out why. The answer was tribal knowledge. Every senior rep had their own way of doing things and none of it was written down. You'd ask two different senior reps how to handle the same situation and you'd get two different answers. That's not scalable.

Jesse Buckingham: How did you fix it?

Will Hopkins: We spent a lot of time just documenting everything. What does a good carrier call look like? What's the escalation path when a load goes sideways? What does account management actually mean at BlackBox? We put it all in writing, built visual workflows, defined who owns what. It sounds simple but it took us probably six months to do it right.

Documenting Tribal Knowledge as Institutional Process

Jesse Buckingham: Once you had that documented, what changed?

Will Hopkins: The senior reps could actually focus on selling. Before, they were doing data entry, track and trace, customer service, all of it mixed together. Once we separated those functions and had clear process, the senior account managers got their time back. Revenue started moving again pretty quickly after that.

Jesse Buckingham: What does your team structure look like now?

Will Hopkins: We've got pods. Each pod has a senior account manager who owns the shipper relationships, carrier reps underneath them, and ops support. The senior AM isn't doing data entry anymore. They're selling and they're managing the relationships that produce revenue. The carrier reps are running on a specific metric, which is loads per carrier per month, not just total loads booked.

Jesse Buckingham: Why that metric?

Will Hopkins: A rep who's booking three loads with the same carrier versus one load is three times more efficient. The relationship is already there. The trust is there. You're not starting over every single time. Finding a new carrier for every load is the most expensive way to cover freight. We want our carrier reps building books of carriers they go back to over and over.

Eastern European Carrier Sales Talent

Jesse Buckingham: You mentioned you've been bringing on carrier reps from Eastern Europe. Tell me about that.

Will Hopkins: Yeah. We found a pipeline of Serbian and Polish reps who've been in freight for ten or fifteen years. They understand the industry, they understand carrier sales, they can work US hours. On day two they're booking loads. That's not an exaggeration. Compare that to the six to nine months it takes to get a US college graduate fully productive in a carrier rep seat and the math is pretty obvious.

Jesse Buckingham: Is there a language barrier?

Will Hopkins: Not really. Their English is fine. Carriers don't care where you're from if you're getting them loaded and paying them on time. That's the relationship. We provide that and the carrier reps handle the volume.

The C.H. Robinson Supreme Court Decision

Jesse Buckingham: Last thing I want to hit on. The Supreme Court decision in the Montgomery-Carabay case. What's your read?

Will Hopkins: My read is that brokers who were already doing proper carrier vetting aren't changing much. The liability question that case raises is real but if you've been vetting carriers the right way, using the right data, doing the due diligence, you're probably fine. Insurance costs will go up a bit. That's manageable.

Jesse Buckingham: Are you worried?

Will Hopkins: Not really. The carriers most likely to exit the market because of this are the ones who probably shouldn't have been operating anyway. Can't meet a basic safety standard, that's a bad actor leaving. More freight shifts to mega carriers over time, sure. But the brokerage value proposition doesn't go away. Shippers still need coverage. They still need someone managing that complexity. We do that.

Jesse Buckingham: Will, this was great. Thanks for coming on.

Will Hopkins: Yeah, appreciate it. Thanks for having me.

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