The Supply Chain Rockstars with Bill Driegert

This episode's Rockstar is someone whose fingerprints are all over modern freight transportation. Long before digital freight matching, AI-powered pricing, and real-time visibility became industry staples, Bill Driegert was helping build the foundation that made much of it possible.

Bill has helped transform how freight capacity is discovered, priced, and moved across North America. Few people have witnessed—and influenced—the evolution of trucking markets the way Bill has.

We're excited to dive into his entrepreneurial journey, his perspective on today's freight market, and what he sees coming next as technology and transportation continue to converge.

Transcript

SPEAKER_02 0:00

Bart, man, I've missed you so much. How you been?

SPEAKER_05 0:03

I've been great, Will. How about yourself? What you been up to?

SPEAKER_02 0:06

Man, I've been good. I you know, I I got to go over to Barcelona. I know you've done that a bunch uh for the Gartner Symposium. Um, but I've seen a bunch of music in the past month since we've done an episode, so can't wait to tell you all about that. Um, but before we even get into that, man, I want to hear about your trip to London, right? You were in London with your brother? Is that correct?

SPEAKER_05 0:28

I was in London, my brother turned 60, so went to Belgium quickly, then went with the train from Belgium to London. It's always a great experience going under that channel. Uh, I did three concerts there, I should say three musical events. We went to a guy called Glenn Hansart at the roundhouse in London.

SPEAKER_02 0:47

Uh that's the guy, that's the movie.

SPEAKER_05 0:49

Yeah, he's amazing. Yeah, from the commitments. You're absolutely right. Yeah. Then we went on Sunday to David Bowie's exhibition, You're Not Alone, at the Lightroom.

SPEAKER_02 0:58

Fantastic.

SPEAKER_05 0:59

That was incredible. I mean, I got goosebumps. And then I went on Monday on my brother's birthday. We went to the world-famous Ronnie Scott's jazz club, and we saw Simon Phillips' band, Protocol. And you know, Simon Phillips, he's um he was the drummer for Toto for 20 years. Before that, the drummer of of the Who, and I'll show you talking about Toto. I got this thing when I met the guys from Toto Toto. I got do you see that? The drum skin.

SPEAKER_02 1:28

Yeah, dude.

SPEAKER_05 1:29

So it's signed by all the guys. So I saw the guy with his jazz band at the world famous Ronnie Scott's. It was incredible. But tell me about you have you bought some guitars, you you went to concerts, you got some new music. Tell me about that.

SPEAKER_02 1:46

Man, all kinds of cool stuff. I saw the black keys here. I think I talked to you about it like right for a minute, but I saw the black keys at the tabernacle, which is if you've never been to the tabernacle, anybody's listening. I mean, it's just one of the best places in the world to see music. And I had tickets like right on the side stage. So you're basically like behind the stage. So it was just amazing to see those guys in a in a place, you know, they for whatever reason they're playing theaters. We don't have to get into why, but I love it. For us, it's great that they're playing theaters because it's wonderful to see them so up close, but tremendous, tremendous. And you know, I went to uh Ole Miss and celebrated all of that uh hill country music, and they still play that music. And so for me, it's like it's like kind of like going home. So I love that. And uh I went to see a bluegrass show uh with some friends of mine in town, and the band that was playing invited Dan Teminsky up, and then he ended up being the lead singer. And if you don't remember who Dan Teminsky, you know his voice because you know, brother, where out thou, where art thou? He was Clooney's voice in the in the movie. He was the one singing uh Man of Casasara.

SPEAKER_04 2:53

Yeah, and I was like on the bill, just showed up.

SPEAKER_02 2:56

It was so cool. Um, and then one of the really cool things, Bart, you know, when we go to these conferences, a lot of the times it's pretty lame what they put on as the event, you know what I mean? And um and Gartner tries really hard. And in Orlando, they they actually had a Yacht Rock band this year that I that I enjoyed. I love Yacht Rock, so that was great. Speaking of Toto, Yacht Rock, and uh and this year uh I went to Barcelona, as I was saying, they had this band called the Ziggurat Band, and we're gonna put it in our uh on our site so that people can see it. Uh of the video I took. I mean, especially like a circus band. It was really unbelievable. Like they're they're throwing stuff in the air, these guys are moving the whole time. They look, they got they look like circus freaks, and they're just ripping these songs. It was so funny.

SPEAKER_05 3:39

I think I saw that little movie you posted on LinkedIn. It was pretty cool, very colorful.

SPEAKER_02 3:44

Yeah, that was colorful. It was cool. But uh yeah, man, I picked up this this here resonator back here, this uh light blue resonator. I picked that up last week just because uh it's one of those when you walk into the store. This has happened to me a couple times, and you walk into the store and you look at it, and you're like, that is so pretty. If that can play worth a damn, I'm taking it home, and that's wow. So here it is.

SPEAKER_05 4:05

So yeah, when I was in London, we we went to go and eat in Denmark Street. I'm not sure if you're familiar with Denmark Street, but it's like the equivalent of Tin Pen Alley.

SPEAKER_02 4:14

It's actually where what part of town is that in?

SPEAKER_05 4:16

That's actually in Soho. And then and so um that's actually also the street and a bar, and we ate in the bar that's now a restaurant that evening where David Bowie met his first original band that he he got together with. Oh, badly. But yeah, but now all of these, a lot of these um storefronts, they're music and instrument stores. And you look at the window and you see all these beautiful guitars, and us as music lovers and guitar lovers, I mean, you see your guitars, see mine. You just start drooling, just looking at them, uh dreaming. But there's a lot of musicians that that come out there.

SPEAKER_02 4:53

Yeah, man. Well, Ronnie Scouts, I'm I'm jealous. Uh, that's that on my next trip to London. I'm gonna make sure and do that. Yeah, um, well, I know that based on that trip, that you have got a really good song of the day for us, Bart. Uh so that's right. You start us off.

SPEAKER_05 5:09

What is your let's just start and welcome everyone to the show?

SPEAKER_02 5:14

Yeah, we should probably do that. We should probably let them know what we're doing here. Welcome to Supply Chain Rock Stars, guys. We're so happy you're here. Thanks for sticking with us. And uh we've uh you know, it's we've had a fun little transition here. Everybody seems to really like the show, and as we said, please write in if you want to be on it. We'd we'd love to get your take wherever you are on supply chain. We've got a great guest today, and uh one of the things we like to do is is share the music we've been listening to and share our favorite songs. So uh we're gonna let Bart kick it off today. Supply chain rock stars episode.

SPEAKER_05 5:49

Thanks, Will. Yeah, so my song of the day, obviously, I said I went to London. I got inspired by seeing that David Bowie show, uh, that immersive exhibition at the Lightroom scroll You're Not Alone. And so, for that, my song for this episode is David Bowie Changes. And why changes? I think it's a rock and roll song, but it's connected to supply chain, uh, right? Because it's kind of like how do you bring that gap between kind of when we talk about things like strategy and supply chain and pure, what I call pure rock star energy. He gave me goosebumps when I saw it on the screen. But really, if you look at it, right, the whole message of the song, it's embracing that inevitable disruptive transformation, what he calls that that change, right? And that's what we're seeing in supply chain, what's a lot of us are facing um in the market today, um, because we know it's no longer the stable environment that we had decades ago, but we have all this geopolitical, socioeconomic friction. And as Bowie famously sings, changes turn and face the strain. We're all in the supply chain facing the strain. So companies need to face that strain, and they need to do it obviously by building better supply chains and using more technology. But the other part, it's it's also about people. It talks a little bit about changing the people and the guard and shifting models, which was obviously happening in the late 60s and 70s. There's this sentence in there, and these children that you spit on as they try to change their worlds are immune to your consultations. They're quite aware of what they're going through. And that again is the perfect representation of what we're seeing friction between kind of the old school of thinking and the new mindset that we see in supply chains. So, how about you, Will? What do you got for us for today? What's your song for the episode?

SPEAKER_02 8:02

My song is I'm a Ram by Chris Stapleton. Now, it's not actually by Chris Stapleton, it's an Al Green cover, but I know we all love Chris Stapleton, and I felt like he'd be a good representation. And he recorded a couple years ago, and he just has such great taste. The more successful he gets, the better his taste gets, which I just love. But the reason I chose this would really, I mean, I love Stapleton, but is that I'm reading this book called Soul Survivor. Uh, and it's about Al Green. And Al Green, you know, I'm from Memphis, Tennessee area. Al Green is from Memphis Tennessee area, but not only that, he his church and his house is in my neighborhood, Shelby Forest, where I grew up. Um and you know, when I first heard this song, I'm a Ram, it was actually played by this band in Memphis. The very first favorite band that I had, I have a lot of favorite bands. But my first favorite band is this band called Big Ass Truck. Okay, Big Ass Truck. And I was hooked, like I saw it in the paper, and I was like, okay, they're playing at the I'm Indy Daisy, I'm going to see and I 16. Incredible. But they played this song, and I thought it was their song, which I always love when that happens, right? Because then you find out it's not his song, it's Al Green's song, and you're like, oh, my parents love Al Green. Let me go start listening to some Al Green, and it takes you down this whole rabbit hole, and it's a beautiful thing. Um, but you know, uh just for anybody, if you now that I've gone down and read this book, it's taken me down this huge rabbit hole of Al Green and High High Music, which is the studio that he recorded in in Memphis. But trust me, take this, take this trip if you want to. But uh from a supply chain perspective, I know we try to we want to have a link. The very first lyric is drive on till I get there. I got to drive on until I get there. I'm a ram. Yes, I am, and I know just what to do. And it makes me think about, you know, the American truck driver, and uh, you know, now they're dealing, they're constantly dealing with something, constantly, right? Now they're dealing with these crazy diesel prices, and they're doing everything they can to like save on fuel. Like I read the other day in the journal how they are starting to uh go slower, like uphills, like they are really, really thinking through the data to show them like how can we squeeze every ounce of this five-dollar diesel fuel. And it's cool that our guest today is, you know, he's he's uh really ingrained in a lot of this stuff. So I can't wait to talk to him about that. But uh, but that's my song. And uh I want you guys to enjoy the great Chris Stapleton. He's on tour this year. I'm gonna take him, my wife to see him on her birthday. He's playing here in Atlanta on his All-American Roadshow tour. Highly recommend y'all see that. So we'll listen to that for a second.

SPEAKER_01 10:52

Until the gift day.

SPEAKER_05 11:00

That's great. Well, and as as you already said, I'm sure our guest for today is gonna love that that big ass truck, right? Because he's a rock star. Yeah, he's a rock star that has his fingerprints not just on the fret of our guitars, but all over modern freight transportation. And and long before what we call digital freight matching, AI-powered pricing, and what we call real-time visibility, all of those things, right? Before those were these big industry staples, Bill Driegert was helping building the foundation of a lot of that. And he's really helped transform how freight capacity is discovered, how it's priced, and how freight is moved across North America. And I mean, I'm really interested to deep dive into his entrepreneurial journey, his kind of road, uh, you know, kind of in transportation and his perspective on today's freight market with a lot of the things that you're talking about as well, and also what he sees coming next as technology and transportation as we continue to converge those two lanes together. So we are going to welcome Bill to the supply chain rock stars.

SPEAKER_02 12:21

We are so happy to welcome today's rock star, Bill Driegert, someone whose fingerprints are all over modern freight transportation. Bill, how are you doing, man?

SPEAKER_05 12:32

Doing great. Glad to be here. Good seeing you, Bill.

SPEAKER_02 12:37

Yeah, and not only that, man, we can see behind you. Bill is a drummer. We love drummers on supply chain rock stars. I love drummers in general. So can't wait to hear about your journey as a drummer and the heartbeat of the band, the heartbeat of the supply chain, the drums. Love it.

SPEAKER_05 12:54

Bill, you're our first drummer on the show. We mentioned that in the opening. We've had guitar players, keyboard players, first drummer. And like I said, you know, I was just at Ronnie Scottsy and Simon Phillips, one of the big big drummers, uh, solo, but also with the Who, and then 20 Years with Total, which is my favorite band. So, or one of them.

SPEAKER_00 13:14

Drummers are often the like the odd person out of the band. So that's not.

SPEAKER_02 13:18

Well, you know, Bill, you know, Bill, I just I just saw the Black Keys, right? And what's cool about the Black Keys is that they have Patrick Kearney like right up front, you know what I mean? Which is cool. It's it's great. They've got uh, you know, he he's just right up front leading the band, and they actually have the the the rhythm section behind him, which is uh they may be the only only ones that do that, but if they put him front and center, like uh with the drummer saying, like a Phil Collins style, too, where they rhythm drummer really is like the front man of the band.

SPEAKER_00 13:47

It's pretty rare, but there's a few notable examples.

SPEAKER_02 13:49

Um the band.

SPEAKER_05 13:54

A lot of guys, and they sing and they yeah, they drive that whole band.

SPEAKER_02 14:02

Well, we could talk about drones all day, and I know that we will, but Bill, uh, we'd love to hear about, you know, your background, how you got, how did you get into this? We all sort of stumble into supply chain, I think, in some some shape, form, or fashion. And so I'd love to hear about how you got your first, you can go back as far as you want, you know, take it back to high school, take it back to college, take it back to the first truck you drove, whatever you want to say.

SPEAKER_00 14:25

Yeah, I I did not have a plan to get into supply chain logistics. It was I kind of took two steps into freight and brokerage away from where I originally intended to do, which was mechanical engineering. So way back in high school when I graduated, I went to Georgia Tech specifically because I want to do mechanical engineering. I was a car guy. I've always been a car guy. So I was like, I want to build race cars. That sounds cool. And so I went to Georgia Tech, I joined the Formula SAE team, and then I actually hooked up with a uh race car shop, a guy that had been like supporting some cars for rally racing up in Vermont. And I did a race, a rally car race, and then we started talking to him about well, could we do something bigger with this whole race uh support thing? And and I quit school and moved up, uh, built a new business with him where we were doing uh race car fabrication as well as part sales and uh race support, and did that for like two and a half years. And so that's what I thought I was gonna do originally when I got out of school. But it's very hard to make money in racing, and this was right around the dot-com bust. So I did this between 90, well, really, because I I the business itself was like 99 through 2002. So and we saw, we definitely saw a post-war bubble pop, a like a significant drop in entries. Like the one of the races we we did was main summer rally, and one year there's 110 entries. The very next year there were like 42 entries uh in the same same race. So all of a sudden a bunch of people left. So it was just clearly wasn't gonna work at the time. I so I moved back to Dallas where I'm from originally, went to school, decided to finish school at SMU locally. There also were not a lot of jobs available, so I started looking for internships. And one internship that was available was at Frito-Lay, uh, where eventually I met Bart originally. But uh, uh internship at Frito Lay-yeah, up in the Frisco area. Uh was fortunate to get it, and then effectively moved to then I shifted to full-time and was there for six and a half years. And that pulled me into supply chain. Initially I was building production, I got to go to all the Frito-Lay production facilities. So I was building production planning uh software in terms of how to optimize labor for producing Doritos and uh lays and Frito. But then so to carry that through to Freight. So at Frito, while I was there, I applied to a master's program at MIT. And my uh boss at the time said, Well, we don't want to lose you. Can like can we work something out? So we worked something out where I did some, I continued to do work and helped fist it helped pay for the masters as I went through the the program. And I did my master's thesis on on uh a free to lay problem and then went back to Frido. But while I was there, I met uh Jeff Silver, who had a key executive at American Backcallers, and it sold American Backcallers to uh C. Robinson. Then he had gone to work for CH for a bit. He had quit and he had a five-year non-compute agreement, and he was sitting that out and getting master's degrees. He got his MBA at at Michigan, and then he did this program at MIT. But he already had in mind that he was gonna start Coyote, obviously not Coyote at the time, but something. And so 2003 he said, hey, 2006, three years later, I'm gonna my non-compute runs out, give me a call. Uh we'd love to have you on board. And that that happened. So April 2006, I picked up the phone, I called him, and he said, Yep, I'm starting something, gonna build uh brokerage software. And I remember my boss at uh Pepsi being like, You want to go into trucking? You really want to go into trucking? And so that was the leap into freight brokerage, and then I came on. Um, there were three other employees at the time at Coyote, they were all engineers. We were gonna build just software. That was the original vision. And I came on as a fourth employee and uh onwards and upwards from there. Coyote obviously did well, but changed. We became a broker within four months. We said, Hey, we're just gonna be a broker, and then built it up from there.

SPEAKER_02 18:39

From racing to trucking, love it.

SPEAKER_05 18:41

Yeah, very cool. Yeah, I was uh just recently I was in uh Chicago for uh for a customer event and a customer advisory board. It was in the Willis Tower, right around the corner for from where we met in the old AT building right there. Um in the I55 Monroe, if I remember. Yeah, the ATC. Absolutely right. Yep, yeah. It's uh it was a great time, right? This was about I started at at PepsiCo 2005, had moved from the UK to the US, was traveling a whole bunch, and then like I gotta find something where I don't have to travel so much. Uh joined PepsiCo, and then I was every other week in Chicago. So I spent uh part of my time on on the one-up team, right? The SAP team, and then the rest of the time on all the other projects. But Chicago's evolved as well, right?

SPEAKER_00 19:26

Yeah, that's kind of a crazy experience, too. So uh when I got out of my team, I went back to Pepsi and then almost immediately got put on this project, Project One Up in Chicago. Yeah, even though technically I was still living in Dallas. During that period, I actually moved to Philadelphia because my wife would depend for nursing school, and I was commuting every week into Chicago, and then one month I had to stay um back for tax purposes. But it was just kind of a crazy deal where they're flying everybody in just during the week, staying at President's Towers downtown Chicago and flying out on Thursday.

SPEAKER_05 20:00

I know, and then then a lot of these people came back when we started going from Quaker Tropic Anagator, AQTG, as we used to call it, right? That release, and then we brought it over to Friedelay, and then all those people from Fritale went back to Texas, and then we brought a whole bunch of people that were based in Chicago and they moved over um to the Texas area. Now, I think after um Coyote, I think did you go from there? Was it you went to Amazon first? Then so tell us a little bit about that. And I know you did Amazon, I think you started Uber Freight, right? Or Lior, and then uh from there, I think Flexboard, now DAT. How did that go? Because that's a lot of really the big names in transportation and companies really had a big impact, whether very successfully, but at least there was a lot of innovation, a lot of change, right? And and like you said, you talked about the whole dot com. I was part of a a company called Transportation Zone, and our investor was Ross Perot. And unfortunately, we didn't make it, we didn't come out of the bubble. Uh, we basically the bubble busted and we went bust in 2001. But it's not because something isn't successful that it wasn't, you know, completely changing the way people thought. My wife, when I met her in 2000, she was working for a company called Cosmo.com. I don't know if you remember that. It's the these organizations at the time or for retail, where like on Amazon, but back in 2000, you could order something, would be delivered uh by a courier to your door within the hour and cheaper for what it was in the store. Now we say, oh, delivery within the hour. I think Walmart just announced they're going to deliver within 30 minutes. But they were doing that in 2000. Um, obviously they couldn't make money off out of it and went bust. But tell us a little bit about that story you went and how you kind of yourself kind of went through all these, I'd say, big innovations and trying to change from the old way of doing brokerage and transportation to kind of the new vision and to where it is today.

unknown 21:59

Yeah.

SPEAKER_00 22:00

Yeah. I think this like throughout my career, it I've always chased things that seem the most interesting, even if it may not initially look the most lucrative. But just from uh like putting like you know, you get often you get presented opportunities and I think people have their own ways of gauging each opportunity. But for me it was more like, is this the most interesting next thing to do? And Amazon, when I went to Amazon at the time, it was um certainly going through pretty dramatic transformation. And Amazon, when I joined, I joined the team that was uh that whose mandate was to build out the final mile uh capability. So the domestic delivery market. So the opportunity there was we're potentially going to build another UPS or FedEx, and this is a rare opportunity. So that seemed fascinating. When I got there, we had one delivery station in LA. We had built started, we had built out a pretty successful delivery network in the UK at the time. That was actually the first place that Amazon built out its final aisle network. We had started to pilot stuff in India and we were looking at Japan, but we quickly doubled down on building out the U.S. But we took it from one delivery station to 27 delivery stations. But yeah, that was um like that was just a very interesting. Amazon was a fascinating place to be at that point in time because we were making such crazy investments and and building out the infrastructure, which really they I mean, they continue to make crazy investments, but uh it's like the scale coming into that was just like wow, you just you could do so much, move so fast, but it was also this crazy grinder where you're kind of in the middle of this machine. Um we and two the Cosmo example is interesting because one of the projects I worked on was uh the launch of Prime Now. And the budget for Prime Now initially was basically like a billion dollars. We're willing to spend a billion dollars building out this um instant final mile, and we're willing to make a lot of mistakes as well, which is I think also fascinating with how they operate over there. It's like throw a lot of stuff against the wall, see what sticks, double down on what's working. We try like continue to turn over what's not working, but don't give up. Just like we we accept there's gonna be mistakes and we're gonna keep pushing. But yeah, two years at Amazon. I definitely I it was fascinating. I would recommend it to anybody just from a culture and learning how to operate an operation. But I also got to the point where I really wanted to get back into something where I could make a bigger, you know, take a bigger stake, make a bigger uh impact and uh build something from zero. And I wanted to get to the Bay Area. So, because I wanted to I wanted to like meet the VCs and plug into the startup community out here. And I knew uh, you know, being local would be provide its own sort of advantages, which ultimately it did. So I took a a job as a COO at a company called Pillow Home, it was a totally different space. Actually, to the supply chain piece, I actually wanted to try something outside of supply chain and maybe get into a different career, try something else. And so short-term property management. It was Airbnb was bumping, it was really a supplemental service to Airbnb. The company ended up getting acquired um by Expedia, uh, it was called Pillow Homes, but was only there for a very brief period of time because I got introduced to the team at Auto, which was the autonomous trucking company. And um, of course, they got acquired by Uber and in the process of that had the opportunity to pitch to Travis, hey, we should build an Uber for Freight. They had started thinking about that. I had come in and been advising them on that and also helping them uh source talent and brought a few notable people in to, hey, talk to them, maybe they can run this thing. But then when the deal came through, they said, hey, you know, you should run it, go build it in the corner. And uh we built Uber Freight. But that was um we kind of I was put in a corner and it was part of the autonomy team. But of course, in terms of like chasing your interest, it was going to auto, and there's uh there's a new wave of AV and like all these physical AI companies that are just exploding now in San Francisco. And if you go into these offices, it's like it's just the coolest thing. It feels like being in a toy shop where it's you've got these uh you know, all sorts of machine tools, like all sorts of fabrication happening, you know, robots. And it was similar when first showed up at Auto. There were all these like somebody had an old Dodge charger in there. Um, and then somebody had a Skyline GTR they were working on on the weekend because I came in, I think, on a Sunday, and they had all these like uh you know, water jet cutters, lens fabrication machines, all this crazy machine equipment. It's like, okay, this is just a cool place to be, right? Just a fascinating place to be. Yeah, and building a brokerage within that environment seemed like a unique challenge. And so um came on board, and yeah, I like I said, it was part of the autonomy team for the first uh four going on five years, where we were supposed to be like we were uh going to be the platform ultimately to which the autonomy deployed on the trucking side. Um, but it it took on a life of its own, of course. And the idea of an Uber freight was such a strong idea that gained a lot of momentum. And then we acquired Transplace. Became a very different company post-transplace acquisition. And I think you've seen the like the revenue results. It got it kind of slowed down a bit of momentum. It basically culturally, all of a sudden you it was about absorbing this whole new, much larger company and bringing them together. I think ultimately that did stabilize Uber Freight and made sure that it survived because of course the biggest competitor was not. And part of that, as part of my story as well, was giving that a second wind. I ended up leaving Uber Freight. I got an inbound from Dave Clark, who, when I was at Amazon, I'd reported through Dave Clark's organization. He um, you know, he built quite a reputation as a preeminent operator at Amazon. Came into Flexport as CEO. Um, that was a bit of a rocky transition. I think just Flexport was at a different moment in time and um had gone through, you know, the market was was adjusting. And so he did not stay very long at at um Flexport. But when Ryan came back in, within a few months of that, we had the opportunity to acquire the the assets of convoy. And um having built Uber Frey, the convoy story was very compelling. And so we were able to pick that up cheap and um relaunch it and then sell it to DAT. And I think that to me, the unifying thread through that, maybe back all the way back to like 2012 at uh Coyote was I've been very focused on trying to automate freight and the the belief that ultimately this execution layer of like transactional execution layer should just be API to API, execute a fra execute a load, uh carrier logs in, hits the button, books a load, broker posts a load, it magically disappears. Like that sort of capability, bringing that to the market at scale, has been really a journey since even at Coyote, we were working on projects in that direction. And then, of course, Amazon with their relay app and a lot of the work. We went in when we launched the freight brokerage there. Similar thinking went in there. And then, of course, we were freight. That was the whole idea is how do we automate this whole brokerage piece? And then with Convoy, it's been how do I take that tech now? Because these these concepts work. It works in practice. So how do we take that and give it to the whole market so that every carrier, every broker can use it, and then integrate it into the DAT platform? So it's just how that marketplace operates, moving it from a Craigslist world to a Amazon world, right? Where all the execution happens or can happen on platform. And then of course, oh while that, well, I've been trying to push that journey. AI has come in on top, which has uh been a rapid accelerator on a lot of that and uh changed the market. So anyway, that's the that's the long version of the whole of the story.

SPEAKER_05 29:36

Very interesting story will bring us back to the music part.

SPEAKER_02 29:40

Well, hold on. I gotta know. So so Bill, they're doing the convoy deal. Were you like the you were like the sweetener, like they put in the pot, like we can't do it. And they're like, all right, we'll give you Bill. And then you're like, okay, okay, deal's done.

SPEAKER_00 29:52

No, it was more um I offered that up. So, you know, I'd come to Flexport originally to be trucking capabilities, and part of the mandate had been to build something like a convoy or an Uber freight. And I thought post-deal, like one, that there's no better place to execute this than DAT, and I want to be a part of that. Interesting for me, as having been pushing this for decades now, I want to see the end of that journey. And DAT is a, I mean, it's a great company. It's 47 years old. Uh, it's got an incredible product, everybody uses it. Like there's it's an incredible platform to build within. So it was just it was a cool, again, chasing my interest. My interest was how do how do we take this and like scale it within DAT and make this part of the infrastructure of how freight executes and transactional freight executes.

SPEAKER_02 30:41

So that's kind of where our stories intersected there, Bill, when during that whole convoy thing, which was cool because that goes back to my background. Like when we started lead coverage, it was literally during the advent of digital freight brokerage, right? And convoy, like I remember to the day we were working for Cargo Chief, I remember to the day that Convoy was announced, and we're like, oh shit. Because it felt up until then, we're you know, they had Andreessen and the whole thing.

SPEAKER_00 31:08

Yeah, yeah, yeah. Uh he was very very good at raising capital. Yes. They had a gold-plated uh cap table. It was quite I mean, that's yeah. Dan is um, I mean, he's he's an amazing guy. And you like given how many companies entered that space, how well the fact that because it was easier at Uber Freight, of um like to be honest, because Uber with the Uber name behind you, that automatically you have the credibility. So and we didn't have to spend as much time out there in the fundraising environment. To be able to go just from scratch to market, to be able to bring this gold-plated investor list, like that is a uh rare skill if you and then if you compare it versus all the other companies that entered the space. Now it may not have ultimately like worked out, but um it was um it was I mean quite impressive as we were going through the process. And it was a unique moment in time, too, where you needed, I think, a unique set of skills. And you're dealing when capital is free, you like the game is you've you've got to raise if you're gonna compete and you've got to be able to play at you know, you've got to quickly position yourself to be one of those one players. And um Convoy did that quite well.

SPEAKER_05 32:16

Um although Convoy in the end wasn't a financial success, I will say Dan in my book, he's a rock star as well, and great guy.

SPEAKER_00 32:24

Yeah, and he's he was super like also it wouldn't exist, it wouldn't have exist it wouldn't exist today if he didn't like believe in it and was super gracious through the process and thoughtful and like he wanted to see this have another life. So yeah, he's um yeah, big fan.

SPEAKER_02 32:42

So I'll be so so Bill, you're you're back at let's take back to tech, right? You're you're you're Georgia Tech, you're living on the flats. Uh well actually, where did you live when you were going to Tech?

SPEAKER_00 32:56

Uh Smith Hall. Smith Hall. So like the um, I mean, basically, like I could look out my window at diversity, if you know, like right there.

SPEAKER_02 33:03

Of course. Yeah, that's where our office is. We're we're like right on the campus. But so did you go down at like were you were you playing drums back then? Did you go down to Smith's old bar?

SPEAKER_00 33:13

Like, what was the No, yeah, it was an interesting transition. So uh the music backstory, like I I probably peaked in high school with my musical career because I was in a I was in like the band for high school, and it was a punk band, and there weren't many punk bands in in Dallas, and we played uh we would probably play I don't know, three, four nights a week because any club downtown that had a punk band come through would be like, Hey, you guys want to play? It was like probably us and there maybe were other like three other bands that they would rotate, but within Dallas? We were on the rotation to open for any acts where they didn't have like a local opener.

SPEAKER_05 33:48

What was the name of the band, the original band? Family values. Family values is the name of the band.

SPEAKER_00 33:52

Oh you go to Spotify. Yeah, you can find it on Spotify, but it's like the ninth listing of Family Values, so you gotta think a little bit. And there's even a little you could, I think there's a picture of me in the listing on Spotify if you mostly that's gonna be in our Spotify.

SPEAKER_02 34:08

We do a Spotify playlist for every episode. That's 100% gonna be on there, my man.

SPEAKER_00 34:14

Yeah, it was um it was like California style pop punk. Like the bands we idolized were um Bad Religion, No Effects, Wagon, those bands. So that was the sound we were going for. And it was, I mean, it was such an interesting transition too, because I was uh you had to stay fit. Like when you get a band, every every song is like you know, it's very fast. Like I can't play a lot of those songs today, they're just too they're too fast. Um, or I definitely couldn't do it for like an hour, like back then. And so I was probably you know burning like a thousand calories every time we did a show or doubt about it. Yeah, and so I like I went to college and immediately gained weight because I wasn't playing drums, like just I wasn't having that level of activity. But yeah, that uh we we toured during the summer and um we went, we would go, we'd play all sorts of regional shows. Uh we got signed on a label, we put out a little seven-inch, we're supposed to put out a whole album. But when it came down to it, I uh the rest of the band wanted to go to LA and try to make a day. And they did. The whole band moved to LA, and I was like, you know what? I'm gonna go to college. And um like I like it's just so hard. The other thing you learn as in as a musician, if you've been in it a while and played in bands, is just how many fantastic bands just never really break through and how hard that is. And so I think at the time I was just like, I love this, but at the same time, like and also in punk, it wasn't like that was a real moneymaker at the time, although it was just at that point where we're green day and we start like we're starting to break through. Um, but I said, you know what, I'm gonna like I'm gonna go to college. They went, they they gave a run of it. So like a few of the guys still play music, one of them still publishes music today. Um, so they had a run of it. But I go into to Georgia Chapter, all of a sudden it's like, okay, well, I I'm in the freshman dorm. Where do I like? I don't can't bring my drums along. I I would you and then at that point too, like once people are like, oh, you're a drummer, you want to play my band. Well, there's also like once you've done it at a certain level and you feel like, you know, even if it was semi-professional, then they'd be like, I just got a guitar, you know, six months ago. Do you want or you know, you don't play? It's it's just like, uh, I you know, I I don't know. Um so take and like it was hard to find that community when I was there too, because I didn't stay that long. But later, I eventually when I came back to Dallas, I started playing in more bands again and have played in a few bands since then and had a few that were published, but um never quite to the intensity of where because in high school it was what we did. It was like the I'd come home and like the band was already there, and we're just hanging out and playing, and we had a little set up a little recording studio, and we'd have other bands come over all the time. That's just what we did. It's like every day there'd be we'd be playing, another band would be there, we'd be going to a show, we'd be playing a show. It was just like that was it.

SPEAKER_05 37:01

So Billy that you say mainly listen to to punk, or do you listen to a variety of music and then my musical tastes have matured, yeah.

SPEAKER_00 37:09

Certainly I listened to right, but I still, as a drummer, you like to play the heavy stuff because you want to play like you know, it's just more energetic. Um, but yeah, no, I've I have a pretty broad spectrum of but we were at um actually we just went to um Bottle Rock, uh which is a big music festival out here, and um I saw uh Bush played and then Foo Fighters played. Oh, cool. Yeah, and Gavin Rosdale is in the dude's 60 years old, and he still has so much energy. I'm like, man, I I had never seen them before, and now I was like, I wish I had seen them in their prime because it was such a good show. And like, man, it's still at it. And uh you know, Dave Grohl's 57 and still got it and going at it. And it's like there aren't that many. Um, there's not like a next, I mean, there's definitely younger rock bands, but not the same scale of like that last wave.

SPEAKER_02 38:05

But um yeah, I still yeah, people been trying to kill rock for 60 years, you know. It's still out there, it's amazing, man.

SPEAKER_05 38:15

Like I said, it went to Simon Phillips. I think he went pro when he was 17. He's 72 now. But when you see him in the drums, you'd think he's still a 30-year-old kid, you know, because he's like he's got all that energy and he's going at a full blast, double bass drum. Huge, huge kit. It's amazing. So, out of all the music, because we always ask the guests to to bring their favorite song or the song they they picked for the episode, what what song did you pick, Bill? And and give us a little bit of background, why why particularly that one?

SPEAKER_00 38:45

Yeah, so Ocean by John Butler, which is uh I play this, it's probably been on my playlist for I don't know, four or five years now, continually, because it's one of those songs. It it it's a guitar solo. So it's a it's a long one. 11 almost 12-minute guitar solo. And my kids are like, not the dad, they call they think of it as like dad music. Um, but it's just it's one of the songs that kind of takes you on a journey, and it's uh it's just a beautiful piece of music, too, if you got to listen to it. Um, but I think it's just it's just a vibe. It's one of the songs also, you know, you you want songs that you can put on at work and they just like put you in a good mood, or you can just like and you don't have to think about it too hard, right? And it's not like uh chaotic or it just kind of puts you in that nice state of mind. So that's my song. That's like, I don't know if I'll ever not have that song on playlist, or there's times where I'll just want to like hit the button. I have a fondness for like small bands, like two, three pieces as well. White stripes being very famous. But the other I there was another song that I considered on this, which was Death, Death from Above, and they're a little heavier, but it's just a bassist and a drummer, and then the drummer sings, and that's it. And their sound is so full, it's like they're they're able to just like bring so much energy with with just a two-piece. And that always amazes me, too, when you've got like a because it like that stage presence again, the live show, like how much energy can you bring? How much of like that force do you do you have behind you uh makes all the difference?

unknown 40:30

Yeah.

SPEAKER_00 40:32

Yeah, no doubt about it.

SPEAKER_05 40:34

Question I had for you, Bill, and I know for drummers, right? You talk a lot about drum breaks, right? It's where pretty much everyone stops playing, and it's the drummer does his thing. What would you say in your career? And it sounds like you had many, but what would you say was like one of your your career, like your your top breaks, big breaks in the industry, where you kind of go like, that was a moment that was really vital for me looking back where you are today, that you said that was vital. And and where, and and part of the goal is not what was that event in time? But I know a lot of people in supply chain are sometimes looking at it as like, where do I go to with this career? How do I go there? But give us a little bit of insight, what you saw as a big break that you said that's a turn I made or a direction I went into that really got me on my way to to do what I wanted to do.

SPEAKER_00 41:24

Yeah, I'll there were a few. So when I decided to leave Amazon, like I said, I I went to I took a chance because I I just wanted to get to San Francisco, which sounds a little crazy. It was more about the destination, but it was more I had seen there was a wave of investment happening. It seemed like there was a lot of activity, and it just I just felt like if I got local, I could start to plug into the like communities and networking, and which which I did. And then I got introduced to the team at auto, and that was a I mean so it like that leap deciding to get down here because what happened is the in retrospect, it makes perfect sense, but at the time I wasn't thinking of it this way. But San Francisco, there are no operators in San Francisco, it's all product people, and product people love operators because operators can actually get their ideas done. And for a lot of the like more operations-driven types of companies, and Uber being the exception, Uber brought a lot of operators in here. But historically, like let's say you're a product manager at a Google and you're starting a new company and you're not really um, I'd say highly operational. And so people that have operational backgrounds, like there are not, there are very few freight people. So if there's any autonomous trucking companies or AI startups and freight, I tend to get introduced or know them just be from proximity. And that's the kind of bet that I don't think I totally thought through, but I also knew that proximity would drive connections and there'd be value to that. Um, the other big swing, like going to Amazon, was a bit of a swing because I'd Coyote was doing well. I'd had such a long career there, and that was like really my first um, I'd say big bet on a start. I mean, that was a swing too. So I feel like I could break each out, but each time made a big career change, it was usually a pretty fair amount of risk associated with that. Um, rarely was it like a clean, oh yeah, this makes a lot of sense, and I'm just gonna make a lot more money, or that sort of thing. It was more like oftentimes I took a step back in in comp, particularly when you're going to a startup where you're getting you know equity and nothing's liquid. Um, so yeah. My advice is like, yeah, just follow what's interesting. Like uh I think people uh it you know, the default is to be a bit more conservative or think about okay, well, I've got the and the other thing is I also several times took a step back in title because I don't think people understand that like a always that something like an Amazon, like I went from a C level title at Coyote to a director title uh at Amazon, and um it from equivalence, people don't always understand that different companies have very different maps. And so I think people get caught into that. Oh, I've got to go from a director to senior director to a VP to a, you know, like I've got to move up the ladder or chain very traditional way, or I've got, you know, I got to make the X more comp with the next role I go to. Um, which it's really when you're building a career, it's more about like, are you learning? Are you expanding your network? Are you expanding your frontier? Are you taking risk? Like, are you I also think it's important to kind of reset and get back, get your hands back into it periodically, because otherwise you don't want to lose grounding.

SPEAKER_02 44:28

Um I love that. That's really good advice. Like, get in and get in and do the work sometimes. I love that. I mean, we do that at league coverage all the time, actually. So I get that. It's really fun to get in there and make stuff happen.

SPEAKER_00 44:40

Which is absolutely critical if you're going into like startup environments or you know, trying to get into that space. You're gonna have to.

SPEAKER_02 44:50

Well, great. Bill, this has been tremendous, man. Uh, love your your history, and certainly I I did not know that about you being a punk rocker. So uh that's fantastic. I can't wait to talk more about that next time I've got to do it.

SPEAKER_00 45:02

Yeah, I've got uh smack of seven inches. Actually, I need to I need to give away. So it's just at some point or else they're gonna die with me. It's like I need to build seven inches. So I just start getting out of that.

SPEAKER_02 45:14

Yeah, so just have that as the giveaway at like whatever, like at manifest or something. Just have just have your seven.

SPEAKER_00 45:20

It's very me though. Like it wouldn't make sense for DAT to have it as a as a giveaway.

SPEAKER_02 45:24

We'll just put DAT on it. It'll be fun. It'll be fun.

SPEAKER_05 45:31

That is pretty cool. Now, before we we do the outro, I was wanted to always talk or ask a couple of questions, right? Kind of looking forward and and obviously 2026, there's so many things going on, right? We just had the Supreme Court case, we see all these things happening with high diesel fuel prices. So, what from your perspective and having that kind of first of all, rich history in the whole freight world, but also understanding it really. What is kind of one your advice of what companies should be looking into in 2026? And maybe what are things that people currently aren't really focused on that they really should?

SPEAKER_00 46:10

Yeah, I think my advice has been pretty consistent, which is one, uh, because there's all this this wave of automation and AI capabilities in the market, you should be getting your opex in order and you should be obsessive about making sure that you've got competitive op ex. Because on the other side, there's gonna be a lot of opportunities. So in breaking it down by segment. If I'm a shipper, I know that I'm going to like my carriers are gonna be coming back to market. So I want to have effective procurement, I want to be running probably faster procurement cycles. But the more automation I have via API and other tools and mini-bids and other capabilities, the faster I'm gonna be able to act. If I'm a broker, similarly, you want to have automation because you're gonna have to be able to, you want to be able to take those bets and you wanna be able to go after that spot freight, and you want to be able to price 100% of quotes that hit hit your desk. And because shippers are going to be having uh a lot of rejections, you want to be at the table and you want to have those conversations. Like volatility creates a lot of opportunity for broker. And uh upmarket is bad for a shipper, it's good for carriers, it's good for uh um brokers. For brokers, it's more if it's going up or it's going down, you have opportunity. It's when it's flat you have less opportunity because the less stuff hits the kind of rolls over, uh, hits the spot board or creates new opportunities. For a shipper, these are probably the more it's more most difficult for a shipper because we're in uh a compressing or you know, uh tighten market. And for best for carriers, because and and we see that um within our own data, right? Because so more and more carriers are more and more owner operators entering the space. It we've kind of reversed the revocation versus registration trend uh because rates are going back up. And again, same on the carrier side, there's so much automation. You want to you want to chase those opportunities. You want to get plugged in, right? You want as much surface area. Like when things are volatile, like you want to maximize your surface area. You want to spend less time on the back office task and more time in the front meeting with your partners and finding those opportunities, chasing spot bids. Uh so that's like the high-level advice. It's just there is a lot more opportunity when things are shifting quickly than when things are last several years. It's just been so difficult because it's not even been volatile, it's just been flat, flat, flat, low, low, low. You know, care every carriers and brokers are struggling. Shippers, it's easy from a budgeting perspective. Go back to the pandemic, shippers started, they started using API pricing a lot more. They started shortening their bid cycles last several years. So, like, hey, you know, it's easy. Don't have to necessarily do that. We can just retain the rates. And now all of a sudden the world is changing. Everybody's got to be reactive. The more automated you are, the more reactive you can be as well, right? Because it's all just friction. Otherwise, you want to take friction out of the system. And when the market's moving, if you're the first to react, you're in front of it. If you're faster, if you're more automated, you got less lag, less momentum behind how you react to the market, then you're just you're gonna win.

SPEAKER_05 49:02

Yeah, and of course, uh very true, right? I was was reading an article um just recently, it's Accenture, and and their prognosis is within 10 years, within supply chain, we're gonna have a gap of 1.1 million employees in supply chain. So, although a lot there's a lot of talk in AI about how we automate, how we can get rid of people, we're actually not gonna have enough people because workforce is aging, um, and and we're gonna have a lot of work that needs to be done still by people, right? Whether it's augmented task or certain part or subtask or being automated. So, what's kind of your advice for people when they either when they start their education or where they're going in their career, of how can they really kind of upskill themselves to be like at a DAT, what would people need to do to be that talent of the future? Because it's not enough to just have our analytical skills and maybe some freight experience, because we know tomorrow the skills, the brain skills that we need to have is different. What's your view on that? And and for a company like DAT, where do you think the people part is going to go?

SPEAKER_00 50:08

Totally. I think that the bias is shifting to more like high agency, high motivation, like high, highly proactive employees. And really, more than anything, what I'm saying with AI is that it's it's um you don't have to have as deep technical skills, but you absolutely have to have good ideas, right? And you have to have good intuition and you have to know the right questions to ask, and you have to be proactive and you have to be curious. Like these sorts of core capabilities become more and more important. And you see it. And I've seen this described several times of like, it's not going to be like AI versus people, right? It's gonna be people with AI versus people without AI, right? And so it's like people that use the tools that learn that kind of progress forward, that understand where and how and when and how do I be more productive. Because the other side of this too is uh when people are more productive, you hire more people because your company is more successful. Like it's like doesn't these tend to correlate. And and as long as the world has existed, if things get cheaper, you buy more of it, right? It's things get meaning. So if intelligence is cheaper, you're gonna use more of it, you can do more, you're gonna accomplish more. Um, there's going to be jobs available, but you want to be on the right side of that curve, right? In terms of adoption, curiosity, learning. And I think more than anything, and I the other way I heard this described, right, is that people that people that use AI to be better or learn or move faster, and then people that use AI to not have to do the work, right? And so you want to be on the other side of that as well, right? You want to be the person that's using these new tools to learn, to move faster, to get more done, to uh improve your own capabilities and capabilities of your business, not so that you can just automate and walk away. Like that's not the that's not the opportunity here. The opportunity is to just move faster. Move faster, get more business, grow, hire more people, right? Um keep building.

SPEAKER_02 51:57

Well, I know we like Bart. We like to ask for uh uh an outro song for sure. So we don't mean to surprise you. I know you gave us a bunch of songs, but in the in the context of what we've been talking about today, like we like to have we like to play play out the episode. So is there something that comes to mind, a song that comes to mind that will roll just think about while the credits are rolling?

SPEAKER_00 52:19

The reason I love this song is like I grew up in Texas, and it's something about the vibe. He he also has a so he did this with Cronbian, and they also have a song called Crongabin.

SPEAKER_02 52:28

Yeah, Texas Sun.

SPEAKER_00 52:30

And they also have a song called Texas Sun, but this one to me feels more Texas. It feels like the kind of like I can imagine just like and we have this old Dodge truck, and every time I'm driving that truck, I'm like just imagining listening to the song, just driving through West Texas, and uh it's just like that is the vibe of that song to me. And it's uh so so much so that we named our truck Mariella. So that's the the lore there.