Auto-transcribed via Deepgram nova-3. Speaker labels are approximate; light cleanup applied.
[00:00]
Jesse Buckingham: Gonna be entering a world where the job of a freight broker will look quite different to how it looks today. I think when you're, like, building businesses, you've gotta, like, take every advantage that you can because your default is that you have no right to exist in the world. Right? Sometimes it'll be some, like, really interesting, complex, maybe, like, technical work. Or sometimes it's like bashing down a door to get, like, the right conversation with the right IT person at the right company to, like, actually turn the thing on. You know? Welcome to the Freight Show podcast.
Speaker 2: Today, we're joined by Mike and Jesse, cofounders of Vuma. What started as a chance introduction between a builder and a strategist turned into one of Freight's most exciting automation platforms. They share their early experiments. Yes, even wild ideas like training crows for last mile delivery, why killing the wrong projects mattered, and how they landed on solving one of logistics' biggest bottlenecks, unstructured data. We'll also dive into the origin of the Vuma name, their decision to build in person in San Francisco, and the values that drive their culture: hands on execution, long term games, and intellectual honesty. Finally, Mike and Jesse paint a vision of the future, AI coworkers handling the repetitive grind, so freight pros can focus on strategy, problem solving, and growth. Alright. Let's dive in. This episode is brought to you by Voomah, the back office automation platform for freight brokerages and three p l's. From AI powered document handling to streamlined workflows, Voomah helps logistics teams scale smarter. Learn more at voomah.com.
Speaker 3: What was your first impression of each other when you met? And where was your headspace in terms of the problems you were thinking about? What were you looking into?
Jesse Buckingham: Intolerable South African.
Mike Carter: No. I was gonna go in a similar direction. Because I feel like almost every Australian person I know is, a bit crazy. And you I think you actually kind of want that in a co founder. You know? It's like, is it kind of a crazy thing to do to start a company. So I was like, okay, this guy's gonna be willing to do what it whatever it takes. What what gave you that impression? His you know, mostly his voice, but no, we had a we had a really, like, warm introduction by Alex Avery who connected us. And we had, we had both left, like, the businesses that we were in before, and we were looking to start a company, both of us, in the, like, space of automation and logistics. And so I caught up with Alex second, and I think, Jesse, you'd you'd been, keeping up with him. And and, Alex basically told me, he was like, this is like deja vu, someone who I this starting basically the same company as you, so you guys should get together. And that's, that's when we met up.
Jesse Buckingham: Yeah. And it was I think it was both of, like, time where we're both looking at starting ideas in the logistics industry. And I was actually, like, co founder dating with somebody who was looking at an idea in self driving. So part of Avery's recommendation was to chat to Mike to get his perspective on it. And I remember just chatting, like chatting to Mike and I was like struck by how his, like, clarity of thought and intelligence was just like much, much higher than the individual that I was talking about. So I was like, maybe we should work together. And Mike was, you know, it was, it was pretty clear, like from the beginning that there was like an opportunity for like a very complimentary partnership to come together because, Mike was clearly like very gifted technically and could build really any like anything, and had, you know, in his past, like built some very, very challenging systems and things. And I'd, you know, had a ton of experience on the, like, commercial side, like, understanding, like, how to validate and sell. And,
[04:05]
and I actually think, like, the best, like, cofounder partnerships are are the ones where people bring very different things to the table because I think from the the very beginning of our partnership, it was clear that we were, like, better together. Each of us, like, pursuing things individually, like, you know, and that that became, like, very clear once we started working together. Mike was actually working on a really crazy idea. Well, I thought, which one are you talking about? Well, Mike's Mike's worked on some very crazy ideas, including trying to train.
Mike Carter: You get this wrong every time. Trying to train
Jesse Buckingham: pigeons. Nope. Crows. I guess you know. Okay. You got it. I always gonna be trying to train crows to like using robots to train crows to collect trash. Yep. That's the that's, yeah, really crazy. And yet to be built into a multibillion dollar business, but maybe one day. One day. Maybe that will be like I think the real robots will probably beat the crows to it, but it's a Yeah. It was an interesting one. But Mike yeah. I mean, Mike, you can you can share the, original, like, idea that you were looking at and how we started working on it together. Yeah. I was looking actually at the final mile space. And,
Mike Carter: for lack of better words, I was basically stalking delivery drivers and and, like, doing time studies on how they spent their time. And if you actually go follow a route, which I I was doing, you know, basically driving behind them and and using a little, like, app that I built to, like, measure, okay, how long are they in the back of the the truck for? How long are they looking for the package? How long are they walking to the the door? All that. And you see that there's actually quite a lot of time spent in that sort of sort and search part of the route. And so I was I was looking at robots actually that you could use and, like, have in the back of the van to to cut that time out and have the package ready when you get to the the place that needs to be delivered. And it's, like, very real sort of, like, time cost opportunity.
[06:08]
Not as easy of a sort of, like, commercial case. There's a lot sort of there's a lot that goes into Final Mile, and especially the sort of, like, that physical part of the Final Mile, the the the route and the delivery. Working with Jesse, like, all of a sudden where I had done a lot of those sort of, like, you know, bottoms up research on what the operation looks like, what the technology could look like, we were all of a sudden in conversations with, like, everyone who you would wanna be talking to if you were validating, like, can we sell this thing? And I think Jesse and I were were both looking for people who had, like, complementary skill sets. I was looking for somebody who was, like, a world class commercial brain. And so we all of a sudden were in these conversations, actually seeing, like, what people's sort of willingness to engage on it would would look like. And to cut a long story short, realized that, like, that wasn't gonna sell very well. And so we ended up, like, killing that idea, moving on from it, and, and, like, you know, a few more twists in the in the journey, but found our our way to, like, the the the the work that we're doing now.
Jesse Buckingham: Yeah. And part of the even the Mike was, like, looking at two names for the business initially. And I think one of them was like,
Mike Carter: like cargo arm or like cargo trucks. And then the other was like, like literal names too. Yeah. It was like, yeah, you don't have to guess too much, but it, it, it would have made it a lot harder to change what we were working on. Was a rough. Yeah.
Jesse Buckingham: And I actually went back recently and looked at the original, like we had a slide deck because we, we got like far with this idea. We're actually talking to like UPS's innovation team, and they were like, hey, we can't find out anything about you guys online. Like, what's the deal? And it's because we, like, you know, made the slide deck there, like, night before. But we but we ran with, like, Voomer, as the, like, original name. And, Mike, you can share a little bit about like where the where the name comes from. Yeah. So Vuma is
Mike Carter: like a bit of a butchered pronunciation of Vuma, which is like the the the the real word. It's a South African slang word, and it basically means like energy,
[08:12]
speed. The the closest analogy that I've come to is if you know the word Andale, it's like, you know, let's go kind of. So so that's, that's where it came from. I'm I'm South African, and sometimes you can hear it in my voice. And the you know, at that stage, we were not, like, very strongly committed to any particular idea, but we knew the sort of thematics that we were interested in and the sort of, like, efficiency, you know, resilience, optimization of logistics workflows, all of those that sort of, like, concept, applied pretty well to. So that's why we chose to go into that UPS meeting.
Speaker 3: Nice. I'm sure, you know, across the the time there's been kind of a graveyard of ideas and products. But how did you know when you were onto something, you were solving the right problem with Mhmm. Boomer or eventually became Boomer.
Jesse Buckingham: Yeah. We I mean, there was this at the very, like, highest level, I've been working in and selling into freight brokers and trucking companies in my former life. Just looking at like, it it's such a massive industry that still take, you know, even at that point just took so many, like, bodies to be able to move freight. And there'd been a lot of investment in technology in the ten years prior. You know, digital freight matching platforms, various attempts at marketplaces, there were visibility tools that were coming in. But when you actually kind of, like, peeled the onion and looked at how freight was actually getting moved, it was still the case that everything required a ton of work. Even these things that were driving a lot of automation were, like, actually having, you know, like, a pretty marginal impact. Even in situations where you're getting automated tracking, you still had, you know, large teams of people, like, calling on, turning on ELDs, trying to figure out where trucks were. And so it was quite clear that, like, we the problem was not actually getting solved. And this was a point in time where we were very
[10:18]
early to seeing some of the, like, generative AI that was coming out. This was pre chat GBT, and we were, you know, experimenting. And Mike had had experience with, you know, some of the very early versions of language models and, and started, like, testing out various ideas. And it was just very clear to us very early that a lot of the problems that were previously very hard to solve in logistics suddenly had this moment where they became tractable problems to solve. And so the original vision for Voomer was to build a universal concierge, to sit next to brokers and dispatches at trucking companies to be able to sit in the inbox and pass through emails, identify opportunities, respond to them, be able to provide coaching, be able to go out and perform check calls on their behalf, figure out in the TMS who a good carrier might be and actually go out and reach out to that carrier. And we started talking to folks about this idea, and this was this was before everything that we've now seen in AI where that idea doesn't actually seem so crazy. In fact, we're, like, pretty close to being able to build that future. But at the time, it was a lot of like, oh, shit. I mean, that sounds amazing, but, like, that sounds impossible. And a lot of product surface area at the time. And so a lot of the early, you know, versions of Voomer was figuring out what the right entry point is Yeah. Was to actually building that. And one of the problems that we'd seen in talking to both trucking companies and and brokerages was, just how much, like, unstructured data came through emails, PDFs, spreadsheets that even in small businesses would have multiple people whose entire job it was to just sit there and, like, key data from one system into the other. And that was in the small end. And then we started talking to and showing prototypes of our order entry product to some of the biggest brokerages in the space. And they were like, hang on. This is a huge issue for us. And so it was sort of this moment where we realized, like, that this, like, unstructured
[12:28]
data for email is actually a really acute problem all across the industry. And there was an opportunity to, like, solve that with production scale systems at the time. So, we started there as with this view that that would be the first skill that we developed towards this, broader platform over time.
Speaker 3: Yeah. It sounds like, it kind of started with this grandiose vision, shrunk down to serve the the current need, and now we're kind of actually Yeah. As new, moving back into that. So looking ahead at, like and I think part of that's due to where the technology is at and how far it's progressed. If we're to, fast forward, say, even three or five years into the future, like, what do you think, first, from a technology standpoint with AI, what what what does the world look like? But specifically within logistics, how how does the world you know what what is what do freight brokers look like in five years from now?
Jesse Buckingham: Yeah. I'm happy to start. You wanna start on it? Yeah.
Mike Carter: I think in
Jesse Buckingham: five years, we're gonna be entering a world where the job of a freight broker will look quite different to how it looks today. If you look at a, you know, a broker on the floor today, there's parts of their job where they're a strategic consultant to their customers, helping to, like, resolve their supply chain issues. There's part of their role, which is, you know, being the person that like, when a truck falls off at 3PM on a Friday, they figure out how to get that freight moved, whatever it takes. Those roles I think will persist. I think those are really important. And I think that that is this, like, critical thing that a logistics service provider offers to a shipper. But there's also a lot of that job, which is responding to quote requests that come into the inbox, clicking through nineteen eighties portals, entering a bunch of reference numbers to look at available times, to kind of figure out which appointment to schedule,
[14:34]
you know, answering potentially hundreds or thousands of calls, you know, per day from a carrier to kinda figure out who who you can actually work with and who's the right fit for for your load. These are these are things that actually do not add that much value. They are critical parts of the job that don't need to not need to be done. And so we sort of envisage this future where the role of a logistics operator is an elevated one where they are supported by teams of AI coworkers, that they can collaborate with, that takes care of all the the rote and the, like, menial stuff. And their role is very, very much focused on the, like, complex problem solving, the judgment layers, and being a better strategic partner, to their to their customer. And we think that that's a pretty pretty exciting future actually because, the job becomes much more meaningful and engaging. It's challenging today to retain people in logistics often because it's just such a hard job. You know, you're it's not twelve hours a day. It's fourteen hours a day. You're expected to be on your could be a Friday night and you're, like, trying to enjoy yourselves with your friends and, you know, something goes wrong, like you need to be on it. And if we can like start to make that job a little bit easier by like handling a lot of, those pieces on behalf of of the operator, then I think it, I think it creates for like a more more meaningful job for them. Yeah.
Mike Carter: Yeah. And and and I think that so if you think about, like, the next couple of years, I think that sort of transformation happens and a lot more of the blocking and tackling is done by AI. It also means that the amount of blocking and tackling can go up. Right? So we start to see opportunities where you're you're you're not just sort of settling for the offer that you have in hand. You're actually able to see a lot more of the market and get a better sense for, like, what what the options are if you're looking for a carrier or if you're a shipper looking for for options to move for your move your freight. And so you start to like, you kind of graduate from the level of, like, okay. We're rate limited by the number of humans that can be doing calls and emails and and and, you know, work between systems into a less constrained ecosystem there.
[16:44]
And we get everybody sort of lit up. If you think about the logistics or logistics industries as, like, nodes in the network that are interacting with each other, a lot of them are under digitized, and so you you start to bring those all online. And so there's gonna be a next wave of opportunities where you can be optimizing the sort of, like, the the system as a whole. All of the players will be easier to you know, they'll have an easier time interacting with one another and opportunities to, like, actually clear the market in in more efficient ways than it's cleared today. So we're I you know, step one is building the the agents and and, like, bringing that whole sort of first phase to life, and then there's a lot that can be built on top of that. Mhmm.
Speaker 3: Shifting gears a little bit into kind of Vuma culture and just, I guess, Vuma values too. Before I do that, I'd be curious to learn. I just think it's always interesting. Like, tell us about a time, I'm sure there's been many, where you guys completely disagreed with each other. And how did you resolve that? What's the process? I'm sure that's kind of like, you know, like any marriage, getting to know each other, that's the first. Oh, this is a
Mike Carter: Trying to think what the best example of this is.
Jesse Buckingham: Trying to think of some of the early ones. I think they had, like, less disagreements, but more, like, areas where it was clear that we needed to, like, get to an alignment and, like, explore the explore the problem. We have one, like, some early on, like, making the decision about that we were gonna build an in person company in SF. That wasn't initially clear to us. Yep. That's true.
Speaker 3: Yeah. Why why why why did you come to that conclusion?
Jesse Buckingham: We, you know, ultimately, there there's trade offs. Right? And so each of us, like, understood the, like, pros and cons. You know, a lot of it is, like, over your career, you build a network of really amazing people when they're all distributed across the world, and there's there are amazing people everywhere. And so it was there was a real trade off,
[18:55]
in saying, hey, we're gonna we're gonna restrict our hiring pool to, like, a specific geography. And this was a time during the middle of co like, or back end of COVID really, where that wasn't it wasn't sort of immediately clear that SF was gonna like have this resurgence. But I think for us, we ultimately landed on it because it's our belief that if you wanna build a world changing and enduring business, that your probability of doing that is much, much higher when you have everyone in the same room creating energy, solving problems quickly, moving faster, and just creating like a like a feedback energy where one person's, ambition and aggression feeds off on the other, and everything just kinda moves faster. And it's not to say that it's impossible to do it remote. It's just much harder. And, you know, I think when you're, like, building businesses, you've gotta, like, take every advantage that you can because your default is that you have no right to exist in the world. Right? Mhmm.
Speaker 3: Yeah. I guess somewhat related to that, I mean, that falls into, what are kind of the the mission or the operational values and what when you have kind of because you guys have been pretty intentional about that just in terms of from the early days. Like, what were the things you keyed on and why? Then take me to the main Yeah. That really stuck out.
Mike Carter: I mean so, I mean, we could walk through them, but the the ones that, at least for for me, are, like, super important. And the ones that, like, jump into my mind when I think about our values are, like, everyone gets their hands dirty. Long term games with long term people. And, forget exactly how we phrase it, but the the one about intellectual honesty, more or less. So the those three like, everyone gets their hands dirty. Startups are so messy. And, like, if anyone is,
[20:59]
is, like, not willing to dive into the trenches, it's super easy to just basically not not get anywhere. The things that actually move the needle at the end of the day, like sometimes it'll be some like really interesting, complex, maybe like technical work, or sometimes it's like bashing down a door to get like the right conversation with the right IT person at the right company to, like, actually turn the thing on. You know? And, like, all of those things, whether sexy or not sexy, like, are absolutely critical for success. And and so, like, I think that's one that that for me is is really important. The long term games with long term people, It's a I think it's like a commitment. It's a commitment to, like, the people that we work with, both, like, within the company and to our customers as well. That, like, we're here thinking about, like, how this looks over the course of time, and we're not trying to sort of, like, you know, find any, like, quick wins at somebody's expense. It also comes into, like, how we work with one another that if you're if you're thinking about something as, like, a relationship that you're developing over time, you know, you asked the question about disagreements. Part of the reason why I think we stay aligned really well, Jesse and I, but I think across the team, is we we we, like, lean into those moments where that disagreement might be starting to form. And and we, like, actually force ourselves to say, like, what what's going on here? How do we work together better? Do How we understand each other better? How do we understand the sort of the problem better? Because it's usually the case that if you have people who are disagreeing, there's, like, a third thing. Right? There's it's it's usually there's, like, one person's perspective, the other person's perspective, and then there's a third thing that you've gotta find in the conversation, which is usually better than either of the two perspectives to begin with, because it has more nuance or more surveillance to it. And then the intellectual honesty piece, I mean, dovetails fairly well from what what I I I just mentioned, but you don't get anywhere in startups sort of deceiving yourself. And from sort of the the the very earliest times that Jesse and I were working together, we were, like, very intentional to, like, look at the data in front of us and
[23:02]
focus on the things that were, like, real signal. You know, there there there there are a lot of things that are sort of vanity signal or, like, you really want to believe, but they're, you know, not not true. And if you sort of open your eyes and and focus on the things that really matter, the the metrics that that signal that, like, value is being delivered to an end user, and, like, the the sort of, like, real merits of the arguments that you have in front of you, I think you end up going somewhere where whereas, like, you know, the the game of startup is hard enough, and and and if you and if you're lying to yourself through it, it's it's just a lot harder.
Jesse Buckingham: I don't know if there are any others that you, I think the only other one that I would add is, like, one of our values is like run with the ball. And I think the the types of people that we look for and are in the team are ones that are like entrepreneurs and owners in their their own right. Like everyone, when we think about whether or not to bring them onto the team, it's thinking about, like, if we gave this person a big, hairy, ambiguous problem, are they gonna, like, really get their hands around it and and, like, run with it and take it down the pitch? Because, you know, we sort of think about, you know, a lot of, like, our capacity to, like, execute. We have, like, big and ambitious plans. And the only way that we get there is by having a, like, complete team of individuals where you could really tap almost anyone on the shoulder to take on any challenge, and they're gonna they're gonna run with it and, like, drive it through to completion. And so I think that makes it, like, a pretty pretty fun place to work as a result because I think everyone kinda feels like they're, you know, they're, they're really like part of it and owning something very like big and meaningful. And they've got real accountability and responsibility.
Mike Carter: Oh, we should mention the float like a butterfly.
Jesse Buckingham: Sting like a bee. Yeah. I feel like it.
Mike Carter: I I actually really like it because it it is like similar to, well,
[25:03]
like, you do go through ups and downs in startups and and, like, part of what makes it, like, a a journey that you wanna reinvest in is, like, the people around you and what it's actually just like being in the trenches with them. And, like, Jesse's funny as hell. We've probably all, like, you know, been in stitches laughing at things that he's said and done. And, like, it it it it actually matters, you know, like, bringing bringing yourself to work and and bringing the, like, the sort of love of the game to work as well. Mhmm.
Speaker 3: One one of the things I personally enjoy going through the interview process was the deep dive interview. Yeah. So I was hoping maybe you could provide some context on a, what that is, b, how that came to be, and c, probably there's a lot of things here and take take what you want. Like, what what what does it help you identify? Why why is it there?
Jesse Buckingham: You know I said? Yeah. Yeah. Yeah. We do the deep dive with people for a few reasons. One of them is what you've described. It's an opportunity for us to really get to know someone. And traditionally, like, you know, an interview process, you're kind of like, zeroing in on specific stories, and it's very hard to kinda piece together the full arc of someone's life and experience. And even when you start to work with people professionally, you don't really ever take that time to sort of understand, like, fully where they came from. But it's really rich. It's rich for the candidate because, you know, they get to share their full story and not in in a way that feels very, like, organic and authentic. But it's also really rich for us because people's past is, like, littered with all of this evidence of, like, who they are and how they, like, make decisions and what were the values that actually, you know, drove the choices that they make and who influenced them along the way, and what are the reflections and learnings that they've had, about their experience. And so it's just very, very rich in, like, helping to develop a full profile of a person and an amazing opportunity for someone. Like, people feel seen because they've had the opportunity to,
[27:06]
to share their full full story. And so it's one of, like, my favorite parts of the interview process and one of the ones that, you know, I think is is is one of the richest as well in terms of signal. Yeah. Cool.
Speaker 3: Couple questions left here. What book has influenced you the most? I know it's not a big book, it could be a podcast, whatever, however you wanna take it, whatever piece of if we're doing a podcast here or a community review or what one piece of media is. So please.
Mike Carter: Individually or, like, as a partnership company? Individually? Well, mean, yeah, take it as you will. That's a lot. Yeah. I think I I have two. One is pretty tactical, and the other one is more, like, philosophical. The the tactical one is the mom test. I think, like, anyone is who's who's read it and, like, done customer discovery or, like, user discovery. It's just sort of, like, chock full of the the things that you kind of need to have in your brain and the the very, like, tactical approaches to, like, getting real signal from customers or, like, prospective buyers and things like that. And so that that's that's mine for the tactical side. The philosophical side, I love Atlas Shrugged, which I know is, like, a little bit contra controversial. But it's just about, like, people taking on, like, just insane, like, ambitious goals and, like, fighting through a world that is, like, you know, determined to take them down and, like, achieving on the other side. Now, like, the the the story is not all about that, and there's definitely some, like, interesting sort of, like, extreme perspectives in there. But I love like, when I sort of wanna get pumped up about, like, being an entrepreneur and being, like, resilient and things like that, that's that's probably my go to.
[29:10]
Jesse Buckingham: The one that always comes to mind for me is this is a long time ago, but I think reading Daniel Kahneman's thinking fast and slow was maybe one of the most impactful at that time in that. I think for me, was like the first opportunity where I started to understand more about how my brain actually worked. And I think that taking that step then allows you to create a lot of separation between how things impact you and then how you choose to respond to them. So I think it was probably the beginning of of that journey for me, which I think is actually a really important thing that you need to be very good at when you're in the world of company building and startups, especially because they are just such a roller coaster ride that you need a level some amount of levelness, so that you can, like, react and have good judgment and respond well to all of the the ups and downs.
Speaker 3: So this last question, I I think is one of the more important ones. So yeah. Well, I guess we'll just dive right into it. So would you rather fight one horse sized duck? How do you like duck sized horses?
Jesse Buckingham: One horse sized duck or a 100 give me the 100 horse sized horses. Taking them all down. Just kidding. Strong. So you reframe the question. Yeah. Yeah. Yeah. Or neither. That's how you would agree with Yeah. Have you seen the, the people that are using AI to like reenact it? No, I haven't. Cause they do, they do like donkey, like, it's like, it's like a gorilla taking on 100, the 100 horses. That's pretty good. The gorilla wins in all of us. Really? Yeah.
Speaker 3: Yeah. Gorillas are like, I
Jesse Buckingham: would go the one, like the one big horse sized duck. Just one. Yeah.
Mike Carter: I've you think so? Yeah. Yeah. One horse sized duck. What would the, what's the other option? A 100 horse sized duck
[31:16]
Jesse Buckingham: sized horses.
Mike Carter: I think I'm going a 100 horse sized duck sized horses.
Jesse Buckingham: Yeah. Actually, can I change my hands? You stomp them. Their legs will break, you know? Yeah. Nothing's gonna even happen. You wouldn't even have to deal with them. You just keep living I your
Mike Carter: think I'd rather fight a 100 duck size horses more than I'd like to fight a 100 duck sized ducks. Do you know what I mean? I feel like ducks are mean. Horses, they're probably not even gonna fight you. So they just
Speaker 3: kinda run around you. Then you have a 100 ducks. Yeah. Horse sized ducks now. Like, you could probably, like, sell that into, like, some sort of, like, exhibit or something. I don't know. There's a lot of opportunity. Anyway, so so that's that. Thank you so much for the interview, the snippets, the the the wisdom. And yeah.