Auto-transcribed via Deepgram nova-3. Speaker labels are approximate; light cleanup applied. "Jesse Buckingham" labels in this transcript refer to the show host Jesse Buckingham, co-founder of Vooma. "Speaker 2" is Jesse Buckingham in host segments.
[00:00]
Jesse Buckingham: This is a big reason why I was an advocate for natural language processing ten years ago. So ten years ago in 2016, I started a company called Freight AI. And the biggest reason was that using humans natural language. Drivers don't care if they get you, the broker, on the phone at 3AM. They care that they get the problem solved quickly and efficiently within their workflow at 3AM, which is the promise of AI, right? Here's the thing, as a freight broker, your goal as a freight broker is to get zero inbound phone calls. Every time you get an inbound phone call, it means something it's a bad sign.
Host: Welcome to the Freight Show podcast. Today, we're joined by Ryan Schreiber, chief growth officer at Metaphora and one of the most outspoken voices in freight tech. Ryan's spent the last decade at the intersection of logistics, software, and strategy, helping brokers, carriers, and shippers modernize their operations. He breaks down what's really broken in freight, why most tech projects fail before they start, and how AI can reshape workflows when applied to the right problems, not just shiny ones. Ryan also dives into the concept of orchestration, explaining how technology, process, and people must harmonize like an orchestra to truly transform a logistics business. Alright, let's dive in. This episode is brought to you by Voomah, the back office automation platform for freight brokerages and 3PLs. From AI powered document handling to streamlined workflows, VOMA helps logistics teams scale smarter. Learn more at voma.com.
[02:00]
Speaker 2: Okay. Welcome everyone to the freight show. We have my good friend and how would you describe your role? Because obviously you're a chief growth officer at metaphor, but I feel like you're a, like an industry pundit as well. Maybe.
Jesse Buckingham: Man, you know, our old head of marketing, who's one of my wife's best friends, her name's Teresa, Ron Kio. She's great. She one time, referred to me as Fred Astadel. Freud Estaddle. Okay. I like that. Like that. Like, that's on my, like, LinkedIn headline is is Freud Estaddle. One of our one of our customers one time called me Freight Jesus. Although I feel like both of those are names you can't, like, can't call yourself an influencer. If you refer to yourself as an influencer, you're a douchebag. Other people can refer to you as an influencer. But you can refer to yourself as Freight Jesus, though. Well, no. I I don't think you can. I that is my point. So, like, those are things you can't call yourself, but other people have called me those things. Think that I would describe myself as somebody who is in the middle of for the last ten years, I've really been in the middle of freight tech. I've started freight tech companies, I advise for freight tech companies, I'm a consultant now for brokers, carriers, shippers, private equity firms, freight tech companies directly. So I'm sort of in the middle of this, and I consider myself a bit of an advocate for the future. One of the things we were talking about before you turned this on was this idea that progress will happen and things will change. Stagnation is never you're always moving, you're either moving forward or you're moving backwards, but you're always moving. And so like I sort of am the, I consider myself a bit of an advocate of the future. All of those are a bit unspecific, and to your point, it's really hard. I mean, it's hard to be specific about what I do because
[04:04]
Jesse Buckingham: I'm just a person who knows people and connects. I like to think of myself as a connector. I connect ideas, I connect people, I connect people to ideas, I connect ideas to each other, I connect people to people. And that's a bit of like where I sit and what I do to kind of like just help make the industry less broken. It's really broken, and it breaks people. You know, when we were raising money for my last company, that was one of my talkie tracks about why we did this. I was like, it's broken, and it breaks people. It breaks dispatchers and drivers and brokers and shipping managers, and it's just so fundamentally broken.
Speaker 2: What do you think is broken about it?
Jesse Buckingham: So I think what's broken about it is that it's not so much about that it is opaque. That is certainly part of it. Like a lot of human stress comes from uncertainty, right? Like when you know what's going to happen, no matter how bad it is, in general, you have a way to deal with it. There are so many variables that go into the successful movements of goods, the successful storage of goods, things that are in supply chain, right? Like sourcing materials, where you source materials, where you manufacture, how you get things, what your trade lanes are,
[06:08]
Jesse Buckingham: you know, how you de risk those things, what's going to happen. Those are all things that are just like, that are really difficult, and they're like factorial problems, right? They are multiples of multiples problems. But I think that at the end of the day, like one of the reasons it's broken is that there's so much blocking and tackling that is tied up in this concept of service and relationship that doesn't need to be or have to be. This is a big reason why I was an advocate for natural language processing ten years ago. So ten years ago in 2016, I started a company called Freight AI, and we started around when Convoy and Uber started, and their thesis was an app, and our thesis was chat and other applications of natural language processing, right? And the biggest reason was that for me, is that humans communicate using natural language, right? Like that is our most natural, that is our most, what's the word I'm looking for? Like, it's primal. Our most primal user interface. Because language is a user interface, right?
[08:09]
Jesse Buckingham: Like they meow at humans because that is how it's an interface that they have with humans that gets them what they want. Right? Like, language isn't language is an abstraction. Communication language is an abstraction. And it's our most natural user interface. And that just was a concept that I thought about how all of this was siloed information. Right? So like my TMS is over here and my phone's over here. So like if it's 3AM and a driver needs a delivery number, the only way for him to get that is to reach out to somebody. And yeah, he could go into an app, but an app requires process learning in a way that natural language doesn't.
[10:15]
Jesse Buckingham: And to get to that it's not a problem is the same twenty first steps as it is to it is a problem. That constant pressure, have, like the ability to manage the workflow is impossible. You can't triage the level of work that you have and that pressure on the system. You know, we used to quote C. H. Robinson's 10 ks when we were fundraising for freight.ai, and it would talk about, you know, they would say that their number one risk is scaling humans to meet demand seasonally, right? And so, you know, it's a massive challenge because it adds that pressure to the system.
Speaker 2: I see all the time is that the it's like the demand, the demand from the system of human labor to deal with issues is not uniform, but you have to staff it in a uniform way. And so the way that you do that is that you're almost like necessarily either like bubbling out of your mind and stress because it's too much to do, or you're like kind of underutilized. Which is kinda interesting. That's right, yeah. Yeah, I think about it a lot like the problem of cloud computing.
[12:15]
Jesse Buckingham: This ties into how I think about orchestration, which we can talk about.
[14:17]
Jesse Buckingham: Think about what an orchestra does. It brings together a bunch of resources, and then the maestro, orchestrates the orchestra. And sometimes you need a little bit more trumpet, and sometimes you need a little bit more flute. And it's bringing together disparate resources and making them harmonize. There's a reason that the word harmonize means a thing. It means working, right, in harmony. For me, all of this is derivative from user experience. And so orchestration is bringing together resources and then effectively deploying those resources. So again, I think about a lot like cloud computing. So cloud computing, going back to legacy, before cloud computing, the only way to add more compute power, more servers. And so this is why Amazon came up with cloud computing in the first place. Amazon was like, we got this problem. During peak season, we need an F ton of these servers. And then nine months a year, we have nothing to do with these servers and they sit there and they just cost us money. We overclock, you know, to just take some like technology kind of concepts, right? We overclock the processor, which is the person. We overclock the processor 99% of the time. And so that processor gets really hot and then becomes less effective, right?
[18:21]
Jesse Buckingham: I actually I think the problem one of the problems that we have is not so much is is is how we frame the problem actually, Jess. Like, someone does actually have to deal with that problem. That person is the driver, unfortunately. And so it all anchors back to that driver's experience. What's the experience we want the driver to have? And I want the driver to have as little friction in that experience as possible. That's also what the driver wants. Drivers don't care if they get you, the broker, on the phone at three a. m, they care that they get the problem solved quickly and efficiently within their workflow at three a. m, which is the promise of AI, right? And again, not having to download some random app, and then click 16 different places, and why conversation, again, is the most natural primitive user interface.
[20:23]
Jesse Buckingham: The foundation of what I'm saying is the problems that we face in the industry right now are largely operational problems, and a lot of the problems that we face with technology and technology companies face, and that brokers and carriers and shippers face with getting the value out of technology aren't technology problems, they're operational problems. And they stem from a fundamental lack of understanding of the problem in and of itself. It's like if you go to the doctor, and you go to a doctor, it's like you've got a broken arm, and so instead of going to an orthopedic surgeon, you go to an allergist, technically an MD, but the guy's like, oh, okay, great. We got a rash. Let's take that's why your arm hurts because you got a rash. So if we treat the rash, your arm will be better. And then it's like, okay, well, the rash is gone, but my arm's still broken and it still hurts. It's a fundamental misunderstanding what the actual problem is. I'll give you a really on the nose example as it relates to AI. I was with a top five broker a couple, like a month or so ago, two months ago, and they had done a voice AI, they piloted with a bunch of different companies, and they did a voice AI pilot with one of them, and I asked how it was going, and they said, Not well. And I said, Why not? That's surprising. And they said, Well, our pilot was answering inbound carrier phone calls because we saw that we had this problem of like a bunch of our calls go unanswered. And so we saw it if we answered all of the calls, then, you know, like that'll solve the problem.
[22:28]
Jesse Buckingham: Our conversion rate on those calls has gone down dramatically. So now we're actually just paying double because the bottleneck is no longer answering the calls. The bottleneck is still our people. I still have to pay all of these people, and I'm answering all of the calls. Here's the thing. As a freight broker, you're solving the wrong problem. Your goal as a freight broker is to get zero inbound phone calls, and there's gonna be some brokers listening to this going, what do you mean? That's absurd. No, no. Every time you get an inbound phone call, it means something, it's a bad sign. How could it possibly be a bad sign, Ryan? What if it's a shipper calling me to give me a load? Well, it means you weren't on the phone with that shipper getting the load. You weren't following up on the quote appropriately, you weren't there, you know, right? Like, you didn't know that this shipper ideally, you know, the shipper gives out the loads at 9AM, you call them at 08:45, and you're like, here are all the open quotes, what am I winning? Every inbound phone call is actually a bad signal. So you solved the wrong problem. That's why you weren't getting value out of the initiative. It's an operational problem. You solved the wrong you applied technology to the wrong problem. You didn't fundamentally understand the problem is that you needed to solve.
[27:05]
Jesse Buckingham: The actual problem that you have in your capacity organization by the way, whether you're buy, sell, or cradle to grave, capacity is a capability. Procurement is capability if you're a freight broker. The problem that you have in procurement is creating the space in the context of the rest of the work to effectively source capacity. That's the right framing of the problem. When we talk about orchestration, orchestration also means that. That's the white space I think people miss.
[29:10]
Jesse Buckingham: So you have to cohort. You have to kind of, like, understand the metric. So the way that most capacity organizations operate today is actually more what I would derisively call cradle to grave two point zero. And not derisive towards cradle to grave, because I actually think cradle to grave with the right technology, can be an incredibly effective model. But you gotta kinda understand that today, there are really three discrete sourcing events that happen, and should look a little bit like a funnel. The first is what we would call strategic sourcing, which is long term procurement. That's long term stable capacity. That's where you're looking for private fleets or you're looking for traditional backhaul carriers. You're looking for carriers that have regular capacity or looking for help with their backhauls, that book their trucks 72-48 out because they have frequency and regularity. And those are harder to find. They're harder to sell, and it looks a lot more like enterprise shipper sales. It's longer sales cycle. It's more relationship driven. It's less transaction driven.
[33:18]
Jesse Buckingham: I call it Cradle to Grave two point o because right now, we're asking one rep typically to do all three of those, or at least we're asking one rep to do two of those. We might ask them to do coverage and strategic sourcing. We might break out strategic sourcing and ask them to do coverage and advanced booking. But it fundamentally misunderstands the buying habits and behaviors of the service providers with whom you want to engage.
[37:23]
Jesse Buckingham: You want the carriers who want your freight, not the carriers who will take your freight. And you have to have the right measures in place to understand, do you have that? I've been in a lot of these businesses, and I will tell you, and I've done the analysis myself, and our team has done the analysis, very rarely, even at the biggest shops, very rarely does a material number of the carriers want their freight versus will take their freight. It goes down to network fit. What are the problems this carrier is trying to solve? What are the services they offer? If they move a regular route over the road freight, they are never to be a carrier that wants your freight. They will always be a carrier that will take your freight. May appreciate the business, but that doesn't solve a network problem for them.
[41:27]
Jesse Buckingham: Orchestration is really important in that in those micro decisionings. One of the reasons that this is hard to execute against is in the context of what's on the board today and tomorrow. What quotes I have open right now versus in the future that I have to follow-up on. You know, creating the time and the space, as you said it earlier, to invest in some of these initiatives. And then presenting the user and the people in the business with the information that makes it easy enough for them to actually understand where they should make that investment, and how they should make that investment, and when's the time to do that. Like, you know what? Right now, just post that load to the load board, because we've got way too much freight to cover. And so those are all things that it's an operational problem, not a technology problem.
[43:30]
Jesse Buckingham: I don't know who needs to hear this, but AI is both harder and easier than you're making it.
Speaker 2: Okay. I like it. Let's keep it kind of vague, and I don't wanna even know what that means. I just wanna let the audience kind of sit with that.
Jesse Buckingham: That's why I love it. That's why I posted that one. Yeah. It's like, it's supposed to be a little hot takey, you know? So it's also to poke fun at myself, because I think that it's really funny when people post. I don't know who needs to hear this, it's always the most self serving statement of all time.
Speaker 2: Right. And we could go for a lot longer and we probably will again at some stage, but it was, thank you very much for coming on the show. Really enjoyed the conversation.
Jesse Buckingham: Thanks for asking me, bro. I appreciate it. Thanks so much. Until next time. Always fun.