Convoy (with CEO Dan Lewis)

Coming to you live from the University of Washington, Ben and David are joined by hundreds of awesome Seattle listeners (and a few non-Seattle listeners!) to cover the meteoric rise of trucking industry disruptor and hometown hero Convoy. How did Dan and Convoy go from nervously conducting market research at truck stops on I-5 to one of the largest logistics companies and fastest-growing startups in the world in just four short years, raising over $650m (not a typo) along the way? Tune in to find out! Special thank you to the Paul Allen School of Computer Science and Engineering at the University of Washington and to Pioneer Square Labs for generously sponsoring the show venue. Sponsors: Vanta: https://bit.ly/acquiredvantaServiceNow: https://bit.ly/acquiredservicenow26Legora: https://bit.ly/acquiredlegoraStatsig: https://bit.ly/acquiredstatsig26 More Acquired! Get email updates https://www.acquired.fm/email with hints on next episode and follow-ups from recent episodesJoin the Slack http://acquired.fm/slackSubscribe to ACQ2 https://pod.link/acquiredlpMerch Store https://www.acquired.fm/store! © Copyright 2015-2026 ACQ, LLC Carveouts: Mystery: https://mystery.sh https://mystery.sh/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ben Gilbert?

  All right, I just checked and the waveform does spike and clip when I scream like that, so we'll try not to do that anymore, for the sake of everyone at home.

• 0:19Ben Gilbert?

  Welcome to Season 5, Episode 9. The home stretch. Of Acquired, the podcast about great technology companies and the stories behind them. We are coming to you live today from the University of Washington. Audience, can we hear ya?

• 0:45Ben Gilbert?

  I'm Ben Gilbert.

• 0:46David Rosenthal?

  I'm David Rosenthal.

• 0:48Ben Gilbert?

  And we are your hosts. Let's talk about trucks. 18-wheelers, semis, the long-haul guys. One out of every four of these that you see on the road is completely empty. Truckers finish a job and then pick up the phone to find their next load, which could be a state or more away. You might think, they should be able to just have their boss or coworker figure it out across multiple trucks and coordinate. But get this, 90% of trucking companies have six or fewer trucks. And 97% have fewer than 20 trucks. There are over a million independent trucking companies, or carriers, as we'll call them

• 1:31Ben Gilbert?

  tonight, in the United States alone. So, enter Convoy. Today, we are going to talk about this company, which has only existed unbelievably for four and a half years, and their ambitious plans to make it easy for any truck driver to find a nearby load, transparently see what they'll get paid, and do it all, as you would expect, right on their smartphone.

• 1:51David Rosenthal?

  We've existed for four and a half years, too. We're almost as big as Convoy.

• 1:56Ben Gilbert?

  Yeah, this was like a sick dose of perspective. When we were doing the research, David and I realized that Convoy was started between the time that we had lunch and talked about doing the show, and when we actually started the show. It's freaky to see, you know, close to a thousand-person company at Acquired well on its way.

• 2:18Ben Gilbert?

  All right, listeners. Now is a great time to tell you about a longtime friend of the show, Vanta. AI has scrambled the whole security picture. It used to be that you prove that you were secure once a year on audit or a static PDF, then everyone would nod and you're done. But in an AI-first world, that doesn't hold up anymore.

• 2:37David Rosenthal?

  Yep. Your risk surface changes every week now. A vendor turns on an AI feature, or someone writes in a new model without telling IT, and your posture is different than it was last week, let alone at your last audit. Vanta's own research found that around 70% of companies have this quote-unquote "shadow AI" running with no security review at all.

• 2:58Ben Gilbert?

  Right. And that's where Vanta comes in. They're the leading agentic trust platform, meaning they've built the thing that closes the gap. And the way that they close that gap is Vanta Agent. Think of it as a GRC engineer, that's Governance, Risk and Compliance, except that it's software and it doesn't sleep. It finds the issues, drafts the fixes, and cuts the time that you'd spend on vendor assessments in half.

• 3:20David Rosenthal?

  In half! Which is exactly why more than 16,000 companies today run on Vanta. Companies like Ramp, Cursor, and Snowflake all stay audit-ready and catch the risks that crop up between audits across every vendor, every AI tool, the whole environment.

• 3:38Ben Gilbert?

  And that's the real value. Trust has to be continuous now, which is why Vanta automates your security, your compliance, and the work to earn and prove trust. We're huge fans of Vanta over here, and literally hundreds of Acquired listeners have become Vanta customers at their companies over the years. So you can get $1,000 off Vanta at vanta.com/acquired. That's V-A-N-T-A dot com slash acquired for $1,000 off, and just tell them that Ben and David sent you. Now, listeners, if you want to go deeper on company-building topics, or you just want to support the show, you should become an Acquired Limited Partner. We have a second show where we get into the nitty-gritty with expert operators and investors, like the CEO of Webflow and partners at Benchmark, Emergence, and other great venture firms.

• 4:23Ben Gilbert?

  You can become an LP by going to glow.fm slash acquired, or by clicking the link in the show notes, and all new listeners get a seven-day free trial. Of course, there are tons of ways to be involved with the show. You can join the Slack, available at acquired.fm, rate us on iTunes, and we always appreciate any shout-outs anybody wants to give on Twitter or the social media platform of your choice.

• 4:45David Rosenthal?

  Or in person.

• 4:46Ben Gilbert?

  Or in person.

• 4:50Ben Gilbert?

  This is like really crazy doing the show and like looking up and seeing people and like you're gonna hear all the parts where we say "um," which we always cut. You're gonna hear like, you know, when I look at David, I'm like, "That didn't make any sense. Can we delete that in post?" And anyway, with all that, on to Convoy.

• 5:09David Rosenthal?

  Woo, on to Convoy. Hang on, Dan.

• 5:13David Rosenthal?

  So, when Ben and I started thinking about doing this crazy thing and planning for our first independent live show here in Seattle, this is actually our second live show. Our first was thanks to our friends at Geekwire. There was only one company and one entrepreneur that we wanted on the show, and that was Convoy and its founder and co-founder and CEO, Dan Lewis. Not only because, as Min mentioned, it is, I think as we speak, the highest valued startup in the Pacific Northwest, having raised a whopping $668 million in total capital, but more so because I think its story illustrates a really important new theme in tech that we haven't talked as much yet about on the show, but I think

• 5:56David Rosenthal?

  it's gonna shape many of the next generation of great technology companies. And that's taking all the lessons in tech from previous generation companies like Amazon, where Dan worked, Airbnb, Uber, DoorDash, all of them that were focused on consumer-driven businesses and using that same tech to disrupt super-large, super-old-school B2B industries. So, obviously, Convoy is at the vanguard of this, but they're not alone. There's Flexport out there, which folks might have heard of, RigUp in oil and gas, even our own portfolio company at Wave, Quotapro, which does this in the scrap metal industry. And I think we're gonna see a lot more of this in the coming years. So, we are super, super excited to have Dan Lewis, co-founder and CEO of Convoy, up to join us. Come on up, Dan.

• 6:48Speaker 02

  Hello. Hi, I'm on. Perfect.

• 6:52David Rosenthal?

  Before we dive into the typical acquired history and facts and go back to 10 years before your birth and all that,

• 7:00David Rosenthal?

  I want to ask first-

• 7:02Speaker 02

  You guys can tell me about that.

• 7:05David Rosenthal?

  We'll actually start 100 years before your birth, but can you give us a quick, high-level overview to just set the stage for our audience of there are many companies in the trucking space. What exactly does Convoy do? You connect existing truckers, not autonomous truckers, people who are driving rigs today with people that want to ship stuff.

• 7:24Speaker 02

  That's right. So Convoy's a digital freight network. And if you think about how trucking works, as we mentioned earlier, it's extremely fragmented. The average trucking company has three trucks. So you have a bunch of mom and pop trucking companies on one side, and a bunch of companies that want to ship freight on the other side. The mom and pop companies don't have a way to go source that business directly. They don't have a sales and marketing team and operations team. So they work through middlemen, typically brokers or large asset-based carriers that also run a brokerage on the side. That's extremely fragmented. The participants in the middle are trying to, as individuals, maintain relationships with truck drivers and shippers and connect the dots. So any individual person only sees a miniscule piece of the pie, can't really identify all the opportunities, optimize

• 8:09Speaker 02

  the system, and figure out what's going on. So what Convoy does is we're replacing the traditional brokerage model. We're aggregating that long tail, and we're getting them all onto the same platform, all onto the same technology stack, so that we can learn about them, know where they are, and then optimize their routes, keep them efficient, keep them productive, fewer empty miles, reduces a ton of waste in the system, helps shippers get trucks more flexibly and faster, helps truck drivers get jobs that are more convenient to where they're located, what they want to do, and effectively like just creates a more productive trucking system. So to your point about, you know, not just building software, kind of replacing the system, that's what we're doing with technology.

• 8:49David Rosenthal?

  So, okay, to rewind. You grew up here in Seattle, birthplace of Amazon.

• 8:55David Rosenthal?

  Long before Amazon was built. What was your family like? You know, what was your journey that ended up in this?

• 9:03Speaker 02

  David, we are going deep. Yeah, here we go. All right. Yeah, so my family is born and raised in this area. My dad went to UW. We, I grew, I lived, actually, when we were building a house in Northgate. I lived in Ravenna for like a year as a kid. So I was very local. My grandfather started a mom and pop kind of office supply distribution company out of his garage in Ravenna. My dad and uncle worked with that for a while, still doing that kind of stuff today. So kind of small business family, but not really a tech family. I have relatives in Seattle that, you know, did biology for the Washington, for Washington State. I have other ones that work for the ferry department. A cousin of mine, you know, manages one of the fire stations in Seattle. You know, a lot of kind of different local jobs, but not so much directly in the tech industry growing up.

• 9:47Speaker 02

  I just happened to grow up at a time when it, it was flourishing and Microsoft was coming on the stage and it kind of got me interested in tech early on.

• 9:54David Rosenthal?

  Yeah, so you went to Yale. You were a liberal arts major at Yale. And then importantly for the story, you join a consulting firm after graduation. What were some of the like projects you worked on? You were at Oliver Wyman, right?

• 10:08Speaker 02

  Yeah, I was at Oliver Wyman.

• 10:10David Rosenthal?

  And Oliver Wyman does a lot of work with logistics-based industries, airlines and the like, like, you know, what did you learn there? Both in terms of exposure to some industries that would come in helpful later for Convoy, but also just skills that you learned?

• 10:24Speaker 02

  Yeah, so I did learn a lot about supply chain logistics when I was working there. I worked for the Panama Canal for a little while. I lived in Spain and I worked for Welling Airlines. And we did a bunch of other projects with airlines, some projects with Boeing, actually. So there were a lot of different logistics problems that we were working on. In terms of skills, I think the thing that was the most impactful for me in consulting, and it's something that kind of bugged me for a long time in my life, to be honest. I remember even in high school and junior high, like I did a lot of different things. I was always the kid that did like seven different activities, you know, sports, student government, tried this hobby, tried that hobby, wanted to learn this thing. And I never really went deep. And I remember thinking at one point, kind of jealous of the person that found that one thing that they really love and they're like super deep in it.

• 11:08Speaker 02

  And I kind of was wondering, maybe I could just pick something. And I never was able to just settle on one thing. So consulting really fit me. I did 26 projects, probably over, you know, four years or so. And but I kept wondering, when am I going to figure out that thing that I really love? And I bounced around. I did lots of different things, marketing, product management, engineering-related work. And it wasn't until I started a company that I realized the thing that I was actually really good at and that I had trained myself to do over and over was to very rapidly understand new spaces and be able to start things and kick things off and like very quickly get something off the ground. And that was a skill, I think, that I came from consulting initially.

• 11:46Ben Gilbert?

  Dan, did you find that you were great at that, but not as operational as you would like? Like, the knock on people that started consulting or spent too much time in consulting is always like, oh, yeah, they're the smartest person in the room. Like, they can definitely tell you how to solve your problem. But like, when it comes to doing it, it doesn't work. Like, was that your experience or?

• 12:03Speaker 02

  Yeah, it's a really, really good question. When I first started, I don't think I recognized, but that that actually was the case in consulting. Like, I thought that I understood things and then I realized I was just doing the strategy portion.

• 12:12David Rosenthal?

  Because you went right from consulting to a startup, right?

• 12:14Speaker 02

  Well, the latter half of consulting, though, was all operations. So actually, like, when I was in Spain, I was I was running a procurement project for seven months. And it was end-to-end designing all of the specs for how we're going to do maintenance for aircraft engines, APUs, working with 30 different vendors on a six-month procurement process and getting in all the details of finance and operations and logistics. So that's when I realized that I was learning that for the first time and a lot of the other stuff was strategies. I feel like I had the benefit towards the latter part of my consulting career of really getting into the weeds and working on some really meat and potatoes kind of projects, operationally minded. I then went pretty far away from that, though, to be honest, after consulting into tech, and I didn't do that again for a while.

• 12:57David Rosenthal?

  After four years of this, you come back to Seattle, which is now... What year are we in now when you joined Skydeck?

• 13:04Speaker 02

  When I joined Skydeck, 2007.

• 13:08David Rosenthal?

  Seven, okay, so. Tech is a thing, you know, Convoy hasn't been started yet, but so the Seattle startup market isn't quite what it is today. What prompted you, other than perhaps wanting to come home to, you know, you're working in logistics at airports, I'm gonna go back into the tech world and join a, join a crazy new startup?

• 13:28Ben Gilbert?

  Yeah, and to, for people who aren't from Seattle, the way to think about this is Amazon is in one building at this point.

• 13:33David Rosenthal?

  Yeah.

• 13:34Speaker 02

  Yeah. So, Skydeck was in the Bay Area. I actually didn't leave right away. What I, what I did, and this is something about how I just got into startups, I always wanted to do something in tech. Like, when I was 10, my dad worked for US West, or, you know, the phone, the local phone company. He brought home like an IBM XT, I remember, you know, really kind of, you know, DOS 3.0, and I just, I just kind of learned how to use it. It became, I taught myself a bunch of things on there. I started with basic and just taught myself a bunch of really simple things. You know, wanted to figure out how to optimize the computer so I could play more video games. And got online, you know, very early on through like the library system and started teaching myself how all that stuff worked. So I kind of was really interested in tech early on. Got away from it a while, but that's how I made money in college. Like, I made money building websites for the athletics department.

• 14:18Speaker 02

  I did a lot of IT support and helped people, back then, to make, you know, 10, 15 bucks an hour, just to have some money in college. So it was sort of something I developed early. And then when I was consulting, I was like, I want to go back into tech. I kind of had this bug. And I didn't know how to quite get back in there, because most tech companies and startups look at consultants, you know, and aren't that interested. At least, back then. I mean, especially in Silicon Valley, a lot of the early-stage ones were looking for folks with more technology experience.

• 14:44David Rosenthal?

  So I think it really was part of, you know, in a lot of ways, you guys today at Convoy share a lot of heritage with Uber. And I think it was, it was them that really were like, oh yeah, no, we're gonna hire a bunch of people from Goldman, we're gonna hire a bunch of people from McKinsey, and bring that operational, you know, know-how into, into the startup world. But yeah, back then, that was, that was like, not cool.

• 15:05Speaker 02

  It was definitely not normal. And I hustled. Like, I, I remember taking vacation from Oliver Wyman for like, a week and a half, and all I did was network. I just wrote a list of everyone I wanted to meet, and then found ways to meet them, and then would ask them who Who else they knew in the space and I started working on a startup ideas. I would just take time off to work on startup ideas. And I had this idea for location based services like data research company and surveys company. So I started diving really far into that, wrote a whole business plan, met maybe 40 or 50 people. And never decided to do it, but I realized really quickly the power of networking and information. I would have lists of people that I would write down and all my notes in my meetings with them.

• 15:45Speaker 02

  And then I realized after 10 or 20 meetings, every meeting I went into, I knew more about the space and the person I was talking to. And I could introduce them to all these new companies. So it became like this information broker role. I finally networked my way into Skydeck.

• 15:59David Rosenthal?

  You should have been an associate at a venture capital firm.

• 16:01Speaker 02

  I guess so. But yeah, I tried early and that didn't work out. But that's how I met found Skydeck. So I actually like networked my way in while trying to start my own thing. Met this group. They had founded a company in New York called Vindigo, which was the early like mobile app developer for brew handsets running on Verizon. Had some had some success doing that, moved out to Silicon Valley to build this new company. I was compelled and like basically somehow convinced them to hire me. Like they were all engineers and they're like, why would we hire you? You're this, you're this consultant.

• 16:35David Rosenthal?

  Was Skydeck also focused on like brew handsets?

• 16:38Speaker 02

  No, not at that time. It was pre iOS. iOS came out right in 2007. I started this company in May 2007. So they were thinking about how do we, you know, social networks and the social graph was the big thing back then. And mobile, like location based services, things kind of very early. So they were thinking, hey, you have all this data in the phone bill. It's like someone's social graph. Can we let you unlock that and combine that with like your email and contacts? Text message records. All your text messages and phone records and start to to and combine your contacts. So all of a sudden you can see your real social graph. And is there a way to monetize that or to plug that into other systems that are being built at that time?

• 17:18David Rosenthal?

  And the big reveal is this company ends up becoming Haya, right?

• 17:22Speaker 02

  I mean, it went through a whole bunch of...

• 17:26David Rosenthal?

  Not directly.

• 17:26Speaker 02

  They didn't end up there.

• 17:27David Rosenthal?

  Yeah. Which is a spam call blocking service now.

• 17:31Speaker 02

  Yeah, and they actually did that. So they had a call system specifically designed to help you identify if someone was calling that you didn't want to pick up. They built it, they had a, they got it pretty far actually, and they had a partnership with Google. And then Google kind of shut it down and built it. They basically said, "You can't do this anymore on Android, you can't get access to the phone records." So we shut that down, and then they had something similar come out.

• 17:53David Rosenthal?

  You have this startup experience, these crazy pivots. You end up coming back to Seattle, then our fault for not realizing it was with Skydeck, but coming back to Microsoft. So your first journey now, you've gone from consulting, startup, big tech company. What did you learn at Microsoft?

• 18:11Speaker 02

  And I was very lucky to get a job at Microsoft at the time. It was 2008. I got back to Seattle, I left my job in the summer of 2008, went on a round the world trip.

• 18:22David Rosenthal?

  Wow, good timing.

• 18:23Speaker 02

  Came back in October 2008. While I was gone, Washington Mutual went out of business, so my bank went out of business. I had left a bunch of stock, you know, most of my money in stock at the time, or stocks, and I wasn't really paying very close attention to it. So most of that was gone. I didn't have a job because I had quit my job. I thought I was going to start working with some of the partners from the management consulting firm I'd been at as a contractor, but to get my feet under me when I got back to Seattle, that was no longer available when I got back. So I remember meeting a friend of mine at Black Bottle in Belltown, a guy named Fritz Landman.

• 18:54David Rosenthal?

  Yeah.

• 18:55Speaker 02

  Who I'd gone to college with. And he was at Microsoft at the time, and I was like, "Hey, what should I do? Like, it's kind of, it looks pretty bad out there." And he's like, "I don't know." And he like had a text message from somebody pretty high up at Microsoft saying, "We are hiring no more consultants, like, starting next month." So I was like, "I guess that's not going to be an option." I just did the thing I did back when I was looking at Skydeck. I just hustled again and did a meeting every, you know, five or six meetings a day. Networked, created my list, tried to find a job, got no interviews, couldn't get an interview from Amazon, couldn't interview from anybody at the time. Because the market was in such a rocky state. And fortunately, I knew some people at Microsoft through Fritz.

• 19:33Speaker 02

  Who gave me a shot at an interview and I got a product manager job there. So

• 19:36David Rosenthal?

  Man, and you hadn't been a product manager at Skydeck, right?

• 19:38Speaker 02

  I had not been a product manager at Skydeck, but I basically was because we were so early. I just thought like one, so I was able to get through the interview. I want to give that context because like that was a point where you imagine, you know, I grew up in Seattle. You know, went to a more local school, somehow like ended up at Yale. There's a story around that, worked really hard for five years, was really frugal, saved. And then in 2008, like made that one decision, was kind of offline for a few months and came back to Seattle. Basically with nothing, no job, no money and didn't place to live. So like I have seen that side of it and you know, I didn't panic.

• 20:19Speaker 02

  I just knew I could work hard and find a job, but I think I have a lot of respect going through seeing 2000. I graduated in 2003, so I went through the 2001. There were very few jobs when I was graduating. Again, really struggled to get that first job. Worked really hard, a lot of friends of mine took a long time to get those jobs. 2008, so I feel like I've been through a couple of these really hard periods, which I think made me really value the opportunities that I've had. And so when I got that job at Microsoft, I was like very proud of it and very excited about the company. I grew up in Seattle, you know, looking at Seattle times, reading about Microsoft. I remember looking at their stock price when it was like printed in the newspaper, like so intrigued by this growing company as a kid. So it was like a dream for me to get a job there.

• 21:00Ben Gilbert?

  Which this is a unique Seattle thing, so I didn't grow up here and like nowhere in the US has reverence for Microsoft like Seattle does. I mean, if you grow up here, it is like there's so much giving back to the community. It created so much wealth for the community. It puts Seattle on the map in a lot of ways and like in Ohio, you know, I was like, oh, well, yeah, those are the bad computers. Like

• 21:26Speaker 02

  Yeah, I didn't

• 21:26David Rosenthal?

  Of course, you ended up working for Microsoft for many years, so you know, hey.

• 21:32Speaker 02

  Yeah. You're right, that was that was kind of the foray into Seattle for me. And so I was, you know, I I didn't take anything for granted because I realized there we're in a world of plenty right now. We were just talking about how much capital is available. Convoy has been able to raise a lot of money. You know, everyone that's graduated in the last 10 years has only lived in an environment where everything's up and to the right effectively. And I've lived through two other cycles now. And one, I was again, you know, just out of college and was later. But I think that's just, it's made me never take for granted anything we're doing. And I I don't rest and feel like we're there. Like, I'm just like, we gotta build a really healthy, sustainable business and hurry. And we're taking a big swing. So the more money

• 22:13Speaker 02

  you raise, and the bigger the opportunity you go after, the more challenges you're you face in terms of getting there.

• 22:21David Rosenthal?

  So, Microsoft, then you're like, I'm gonna go back, do the startup thing again. Wavy. Another startup, we were investors when I was at Madrona. Great product idea, didn't end up realizing its vision, gets acquired by Google.

• 22:34Ben Gilbert?

  And Dan, you were head of product there, is that right?

• 22:37Speaker 02

  Yeah, I was I was head of product. I mean, it was a pretty small. So I did a lot of I did a lot of stuff, like marketing, products, planning, like a bunch of different things, sort of jack of all trades, I think, in that experience.

• 22:47David Rosenthal?

  So how long did you stay at Google? And then and then was it the because the team, Adrian moved down to Mountain View, right?

• 22:54Speaker 02

  Yes.

• 22:54David Rosenthal?

  And then did you stay in Seattle? And is that how you ended up at Amazon?

• 22:57Speaker 02

  That's right. So the company was acquired in 2011, if I remember correctly, or 2010, 2011. And ultimately, the entire team moved down to the Bay Area to join the Machine Intelligence Group. And I learned I learned an incredible amount at Wavy. I decided I wanted to move to the Bay Area. And so I was working remotely for Google for a while. I was looking at several options in Seattle to join some of the teams here. And I just decided I didn't want to be part of a remote office at that time. I think Google's actually scaled pretty significantly since then. But I remember going down to the Bay Area once to meet some of the leadership of the team that I may have been joining. There were two or three options in Seattle. And I distinctly remember sitting down with them. And I won't

• 23:40Speaker 02

  say the person's name. But I remember they were like, you know, we just have a love hate relationship with our remote offices. I was like, oh.

• 23:47Ben Gilbert?

  What's the hate part?

• 23:49Speaker 02

  Okay, he's like, yeah, you know, we like to keep a lot of the planning and a lot of the figuring things out down here. And then we have some satellite teams up there that kind of execute on specific pieces. I was like, That sounds fine if you're in maybe engineering. What I wanted to do was very different than that. So that was actually the thing that caused me to not stay at Google. I was like, I don't really want to have that experience where I'm kind of supporting a remote office. I want to be in the thick of it. I looked at several different companies at that time. Someone I had networked with early on, when I was doing Wavy, I reconnected with them. They were at Amazon. And was really inspired by the team they built, the organization they're building. So I went, that's why I went to Amazon.

• 24:26Ben Gilbert?

  Dan, have you ever had a job that you applied for? That you like, you apply and then you're like, I hope they get back to me without like having a relationship with someone there?

• 24:34Speaker 02

  Have I ever gotten a job or applied a job?

• 24:36Ben Gilbert?

  Have any of the jobs that you've ever held ever been from like a job portal?

• 24:41Speaker 02

  I think so. There were two, actually. My freshman year internship, the internship I had after freshman year. I think I applied to an online posting. I joined a company called PR.com in Seattle. Which was acquired by Wagner Edstrom. And so very 1999 name, PR.com. We did PR for tech companies.

• 25:04Speaker 02

  I didn't even really know how to be an intern. I think I just like went on vacation once for a week and they were like, you're supposed to tell us. I was like, oh, okay. Like I was, I was kind of, um, and then the other time was I applied to some, not a job board, but companies came to Yale looking for candidates. And there was like, you know, some companies on campus recruiting. So I went that channel. But after that, no. After that, it's always been through the relationships that I've built. And I very often hire, if, you know, I reach out to a lot of people and I do a lot of personal sourcing. And that's always been a big part of my, my thinking.

• 25:38Ben Gilbert?

  That's great.

• 25:38Speaker 02

  I have sent out a lot of applications where I didn't get anything.

• 25:41Ben Gilbert?

  Oh, yeah. You and me both.

• 25:42Speaker 02

  I was trained, like, I got that job I mentioned out of, out of, out of Yale. I think I got that in the spring. I sent a lot of resumes out and applied to a lot of places. I had taken my junior year off and went to Chile. So I became fluent in Spanish and the summer before and after I worked for my family's delivery business. So I didn't have like the post sophomore, post junior year, strong

• 26:03Ben Gilbert?

  Internships.

• 26:04Speaker 02

  Internships. And coming out in 2003, again, tight job market. I didn't have like, I could do it, but I didn't have the story. So the traditional channel didn't really work for me. And then back again in 2000 and, you know, overtime applied to different roles. And again, 2008, when I was applying, like, I just didn't work at all. So I think when I've mostly been looking for roles, I've been in situations where that just didn't work. And that's why I've kind of trained myself to not really go down that path.

• 26:30Ben Gilbert?

  All right, listeners. Now is a great time to thank our longtime friend of the show, ServiceNow. If you are running a large enterprise, AI agents are likely spread across every team and deploying them is no longer the hard part.

• 26:44David Rosenthal?

  Yeah. The hard part is knowing what permissions they have, what employees are using them for, or what decisions AI is making. AI security for an enterprise at scale is not a small concern. Like, the risks are real.

• 26:58Ben Gilbert?

  Exactly. And the challenge with AI is governing it, securing it, measuring it, and making sure that it actually delivers value. That is why ServiceNow built the AI Control Tower.

• 27:08David Rosenthal?

  Yep. AI Control Tower gives enterprises a single place to see, manage, govern, and optimize AI across the entire business. And it works with any AI, not just theirs. Every device on your network, every permission across every system, every AI agent, visible and secure in one place.

• 27:25Ben Gilbert?

  And ServiceNow can do this because they've spent more than 20 years building the operational backbone of the enterprise. The workflows, governance, approvals, security controls, and institutional knowledge that power how work actually gets done across IT, HR, customer service, finance, and security.

• 27:42David Rosenthal?

  ServiceNow already runs more than 100 billion workflows annually and trillions of transactions for more than 85% of the Fortune 500. So when companies need a place to govern AI at enterprise scale, they're building on a platform at the center of how their business already operates.

• 27:58Ben Gilbert?

  And in a future that isn't going to be one AI, it's going to be thousands of AI agents working across every function of the company. But the question is, who's managing them all?

• 28:07David Rosenthal?

  So if you're trying to turn AI ambition into real business outcomes and make it work safely, securely, at scale, go check out servicenow.com/acquired and tell them that Ben and David sent you.

• 28:18Ben Gilbert?

  All right, so Wavy happens, you end up at Amazon. I want to ask one question on Amazon before moving on to the founding of, well, you founding companies, and then we'll get to Convoy. Recently, Amazon has sort of been dubbed the CEO factory. And we've seen data of all these great CEOs at big, fast-growing companies that have come out of Amazon. What is it in your mind that creates that?

• 28:40Speaker 02

  There are a lot of other companies, too, that I think that do a good job of spawning CEOs. I think one thing that Amazon does is that it expects a lot of ownership from the people that are in the role. And it kind of has a culture of assigning, you know, a single-threaded leader or a person who's ultimately responsible for the outcome of the thing, at least in my experience. And that design puts you in a position where you feel responsibility across multiple functions, even if you don't own all those functions. And I think that that sort of cross-functional leadership at many levels of the company and strong push towards ownership is really important.

• 29:23Speaker 02

  And I think you see that both on the business side and on the technology side. When I was at Wavy, we tended to bias towards hiring a lot of engineers from Amazon. And of course, there's great engineers at every company, but the experience we had was that they had been expected to own more of the end-to-end aspect of their system versus just one piece. And I think I saw the same thing on the product and business side as well. I think that probably attracts people to want that and then trains people in how to think that way.

• 29:51Ben Gilbert?

  Yeah.

• 29:52Speaker 02

  So then, you know, you can slot into those opportunities.

• 29:55Ben Gilbert?

  Is there a proactivity and a hustle that doesn't exist at other, bigger companies? Is that part of it, or is that sort of overly mythologized?

• 30:03Speaker 02

  You know, I have only worked at several, and I didn't spend as much time at Google. But I have been at Microsoft and others, and I think that's definitely, there is a distinction that's true on that. And so I'll give you the example. When I got to Amazon... And this is not maybe the typical role, but I didn't have a team. They just said, look, you're a person who's going to build a team. Go do some research in this general scope of the world. Figure out what Amazon should be doing and why. And I wrote five, six pagers in my first two and a half months. I pitched them to the leadership.

• 30:33David Rosenthal?

  Six pages, of course, being the canonical Amazon.

• 30:35Speaker 02

  The canonical Amazon document.

• 30:36David Rosenthal?

  No PowerPoint.

• 30:37Speaker 02

  Yeah, straight, write a doc. So I wrote five or six, you know, four or five docs, actually, that were each different business ideas. And I pitched them and I got funding for three of them. And then over the next, you know, two or three months, I went out and hired the teams.

• 30:51David Rosenthal?

  Who were you reporting to at the time?

• 30:53Speaker 02

  A guy named Michael Doertie and then his skip level was Sebastian Gunningham, who was actually on the, um, that list as well, the CEO factory list for, because he's now the co-CEO of WeWork, which is a whole different entry strategy. Pause, pause, backpedal.

• 31:08Speaker 02

  Whole different thing. But, uh, but he was creating this area for this to happen. So that was really, the fact that that can exist in a company is pretty inspiring. And then what I realized after I'd been there for a while was the planning process encourages people to come up with new ideas and pitch those ideas. And if they get the pitch, if they're able to build consensus and a storyline around it and demonstrate some early value, they can go build a team around it and data wins. So if you're, if you want, I remember there's an example that buy, you know, ask a question, get an answer on Amazon. That's a feature that exists on Amazon. You can ask a question on a product page and other people, other customers or manufacturers will answer that. That product was developed by someone else in the same organization that I was part of.

• 31:51Speaker 02

  And I kind of was, uh, worked on that a little bit, but it wasn't, you know, I didn't directly develop that. That was originally given the thumbs down by leadership. But the team said, okay, fine, we're going to figure it out. And they went and emailed a bunch of customers, asked them questions and came back and said, actually, if you email customers and you ask them questions, they will answer them at this rate. And then the, the person who had said, no, it's like, oh, I thought they wouldn't. Turns out they will go do it, right? So someone just said, I don't agree with you. I'm going to go show you the data and I got it. They got a team out of it and they built it. And so that, that's sort of internal culture of funding, good ideas. And if people do the research and put the hustle into figure it out, funding that. Has created, obviously, a very broad range of businesses and products that Amazon has created, and a culture of kind of starting new things.

• 32:36Speaker 02

  So I think that's probably unique, actually, the range of things they're doing.

• 32:39Ben Gilbert?

  So you leave Amazon to start a company. Are you writing six-pagers? And was Convoy originally a six-pager? Was that the format in which you thought about new businesses?

• 32:49Speaker 02

  I didn't do it that way. And Convoy is a combination of influence from many different companies, actually. I wouldn't say just Amazon. There are a couple of things we took from Amazon that we thought were really important, but we've taken from a lot of experiences we've had. Convoy, the original experience coming out of Amazon was a lot of research. I wrote a document, but I didn't think about it. I wrote like different forms of documents to capture and structure my thoughts. But it was, again, I need to talk to a lot of people. Like, let's find the problem. And I didn't really know exactly where the problem was going to be. I was like, logistics seems really interesting. And one of the things was, you know, I kind of had this moment at Amazon where I was like, it looks like the supply chain just won. And the feeling was, okay, when online shopping, and I told this story maybe once before,

• 33:32Speaker 02

  but not very often, when online shopping started, you had to decide, am I going to go to the store and buy it last minute? Which means I get to procrastinate, which people love to procrastinate, or I have to buy it online five to seven days in advance before I need it? Which means I can be lazy, but I can't procrastinate. So you have to be lazy or procrastinate. And that's like two really strong human conditions that people really want to do. And this goes back to my cognitive science yell. This is like our TikTok episode. People want those things, right? And you had to decide. And then Amazon Prime comes out, and all of a sudden, it's two days. So all of a sudden, I can order it online, be lazy, and I can procrastinate in order at the last minute. And so what happened was, people changed their behavior.

• 34:15Speaker 02

  You started waiting to order it two days in advance if you were a Prime customer because you could. And once you waited till two or three days left, where else are you going to buy it? No one else delivers in that timeframe. So the secret was being faster than everyone else and creating that rhythm. It wasn't about the exact two days. It's two days was faster than everybody, so you'd wait, and then you'd order because everybody procrastinates. So you always wait. So we would wait till the last minute. Once that kicked in, massive shift of business to Amazon, especially for a Prime customer, effectively a monopoly over like the purchasing in that timeframe. When I saw the data and kind of understood the impact of that, I was like, wow, the supply chain just dominated. Like, that is why people are shifting their behavior. They can't see it, they can't touch it. It's not about the location of the store, the parking. It's about

• 34:58Speaker 02

  two-day delivery, making me procrastinate and buy online from Amazon, right? Super powerful. All these other businesses started reacting to that. And I was like, okay, I gotta figure out something in supply chain. I talked to other investors in Seattle. Hadi Portovi was somebody I spent some time with early on, who wanted me to kind of look into trucking specifically in supply chain. I was looking at several parts of supply chain. I then took directions, started diving into the trucking aspect a lot more. And there are three or four interesting businesses in trucking I uncovered. But that was just through talking to people.

• 35:27David Rosenthal?

  Yeah.

• 35:27Speaker 02

  You know, just hustling and getting out there to truck stops and...

• 35:31David Rosenthal?

  Well, this way, so I think all of these threads of your background kind of come together here with Convoy. So even before you land on, you know, you talked to Hadi and you land on trucking within logistics and then the specific marketplace idea within trucking, one thing you guys did that I never see any other companies do is you recruited your team before you had the company. So you and Grant, Grant Goodell, your co-founder, did you guys meet at Amazon?

• 35:57Speaker 02

  Grant was on my team at Amazon, yeah.

• 35:58David Rosenthal?

  But you had five engineers that were part of your team even before you had landed on the idea for Convoy, right? Talk us through how you thought about that.

• 36:08Speaker 02

  I learned about this back when I was trying to get the job at Skydeck. I wasn't, and I have a strong technical background, and I know a lot about developing software now, but I'm not a software engineer. And so I realized, at least in my perspective, and some of the investors in here can decide if this is right or wrong, but as a, trying to get seed funding, what I learned and felt early on was, you kind of have to check three boxes. You have to have, you have to have an idea that they can at least understand and believe is compelling and believe it has the right dynamics that could return on the, you could return on the investment, right? Can be that kind of an idea. The second is, you have to be a personality, an individual, that is compelling to them. Because, and I think a big part of that is, A, they want to believe that you're going to do the work,

• 36:53Speaker 02

  you're going to hustle, you're going to commit to it, you're going to get it done, you're going to be smart and thoughtful about your approach, and you have to convince hundreds of other people over the next few years that what you're doing is worth it.

• 37:02David Rosenthal?

  Yeah.

• 37:02Speaker 02

  So you'd be really persuasive.

• 37:03David Rosenthal?

  Cool. I've heard you talk about this before. Many entrepreneurs can check boxes one and two.

• 37:08Speaker 02

  Exactly. I couldn't checkbox three of build it.

• 37:11David Rosenthal?

  Yeah.

• 37:12Speaker 02

  I couldn't build it myself. And I didn't believe that I could go outsource that to like a contractor to build my idea. I knew enough about the ecosystem that I wasn't going to be able to track the investors that I wanted and the supporters if I was, that was my strategy for development. So like, I need to get the best engineers around the table. Otherwise, I might not be able to raise seed funding. And as much risk as I wanted to take and as you take doing a startup, I actually wanted to minimize my risk in getting this thing going. And so I, what I did is I, I had a sense of some of the ideas that I wanted. I knew I needed a strong technical co-founder who knew how to build a startup. So I spent time trying to find that person. And then that was Grant, right? So Grant and I decided to do this. Then I went back to the team I'd worked with at Wavy,

• 37:58Speaker 02

  some of the people there, and some people I had worked with at Amazon, who are, who, some of them were there and some of them weren't there anymore. And I started just planting the seeds and the ideas. And I got a few of them to say, I'll do it. And actually, a few of them said, I'll do it independently of the idea. Like, there's two or three ideas, whichever one, let's do it. That's incredible. And so then I was like, okay, now I'm pretty confident. And that was what I needed. Then I put together the pitch deck and said, there were, and we started kind of building it on the side. We started setting up kind of the development environment, getting, deciding what we were going to build, kind of building some of the, the building blocks of actually getting an app developed, things like that, getting some of these things structured and organized, and started doing a bunch of research. And then that brought some of the engineers in. U Dub actually was where we started the company.

• 38:42David Rosenthal?

  Ah, the table. I've heard you talk about the table. Was the table here at U Dub?

• 38:46Speaker 02

  The table was here at U Dub.

• 38:46David Rosenthal?

  Wow.

• 38:47Speaker 02

  So Techstars has their office here at U Dub, in the old law school library. And, or, you know, that's where, that's where it was. So Chris DeVore let us sit at one of the tables. Actually, to go all the way back, so we started there, I guess I should say. Like, that's where we actually kind of like, once we knew we were going to do this, we went there. Before that, to be totally Seattle, to give all the context, like, Maverick reached out to me and said, hey, we heard you're going to do this. We want to give you an office to work out of. And so I went down and worked at a Mavron for a while and I knew some of the Mavron partners and they were really, they kind of gave me that access and let me kind of get my feet on the ground, give me a place to start working in some infrastructure. So I did all my research there. And then I went to them and said, I'm sorry, I'm doing a B to B idea. Because they only invest in consumer. And they were like, oh, okay. And I was like, so I'm gonna

• 39:32David Rosenthal?

  You're out.

• 39:35Speaker 02

  I should probably leave. But they were, they were great. They were really supportive. And so then I, and then Chris was like, well, you guys can just use one of our tables, because we're not using our tables, we're between classes. So we sat at the table in that, in that library and was, it was so perfect. Because what ended up happening is we were in this fun, dynamic environment, a lot of energy in that room, a lot of people were, you know, were coming in and out, and had this great feeling, it had a startup feeling before we started. So I had three of the five at that point, that wanted to do it. And what we did is we, we just invited other people to come work with us. Because we had

• 40:11David Rosenthal?

  This is such a great, like, starting your company hack.

• 40:13Speaker 02

  There was on my team at Amazon had quit, and he's like, I'm gonna start my own, like, gaming related thing. And it was great. No, I mean, yeah, he was funny. If he was here, he would laugh about that. Because I was like, great idea. Come work on it sitting next to us at this table. So he just started hanging out there. And then we just started adding people to this table. And then we would kind of get to know them and then, and then ultimately, they, we got some little attraction like, oh, this is interesting. So we kind of recruited the other two folks from there. Not everyone joined, you know, some people decided not to, and a lot of people weren't interested at the time. But that was kind of how we got it going. And, and that was the beginning. And then once we got funding, then we went and got our own spot. So Seattle, I would just say, just to be really clear, like, the ecosystem in Seattle helped. Like, we didn't have funding in those first two locations,

• 40:58Speaker 02

  and they gave us a chance to kind of get our feet on the ground in a great environment, which was compelling.

• 41:02Ben Gilbert?

  That's awesome. Did, did it, did the thought occur to you that like, yeah, it's gonna help us raise money, like, yeah, it's gonna help me feel more confident about this enterprise I'm starting, but like, holy crap, we're, we're hiring five engineers and we don't yet know, like, we, not, not pre-product market fit, like, we haven't gotten any signal from customers that we're building anything remotely right.

• 41:23Speaker 02

  That's true.

• 41:26David Rosenthal?

  Well, when you put it that way.

• 41:29Speaker 02

  Partially because I didn't know, so I had, as I mentioned, I went out and talked to a lot of other brokers. I went and talked to a lot of shippers. Yeah, you notoriously hung out at truck stops. A lot of truck stops. I did all that stuff. And those were fun. I remember I told this story, but,

• 41:43Speaker 02

  you know, the first shipper I walked into, I walked in, panicked, asked where the bathroom was because they like gave me a warehouse. I went to the bathroom, the warehouse and left. Like, I didn't know what to say. I was like, okay, that didn't work. So I went back to my car.

• 41:56David Rosenthal?

  Maybe you're just not CEO material.

• 41:59Speaker 02

  The first truck stop I went into, same kind of thing. I went in there and I looked at all the people sitting at their, you know, having lunch individually at each table by themselves. Everyone turns and looks at me when I walk in. I'm dressed not like a truck driver. And went back to my car and thought about it again. So I, you know, my clipboard and Starbucks gift cards were effective, but not in that moment. But I, but I learned a lot. And some of the companies along the way, what I found was most ideas I'd ever had in my life, including the location-based services, like Data Research One and maybe 10 others. I had some really bad ideas. Bluetooth-enabled diapers? Really bad ideas. All sorts of stuff. You know, this one, actually, every time I shared it with somebody from the industry, they were excited about it and felt like it was necessary.

• 42:41Speaker 02

  So I got really strong, positive feedback from the industry that I had never experienced before and I'd ever thought about something else. So I didn't know, but I knew there was a problem. Like, I was really sure there was a problem. People were hungry for something to be better. I didn't know how to solve it. And so that was where we kind of started and we brought in those folks. The best part is we did all this without ever incorporating. So we were just, we like, we knew that was important, but we were very much, let's avoid the trappings of a startup. Let's just start building it. So we had the, kind of, maybe there's some legal reasons not to do that, probably. But we had, we were like working out of these different offices. We were kind of getting people to sign up to work with us. We built our, you know,

• 43:21Speaker 02

  we built our pitch deck. We were out pitching investors. You know, we were working on the code with, with folks part-time at that, at that time. And then we started the company once someone told us they wanted to fund. And then we needed a bank account. So we were like, oh, we have to have a bank account that you can fund because I can't just give them my, I used my phone number, my home address when we were first starting, which was a bad idea. Really bad idea.

• 43:44Ben Gilbert?

  Do you still get a lot of mail like for?

• 43:46Speaker 02

  I get a lot of phone calls too. I need to change the phone number. I do a lot of customer support when I pick up for truck drivers. Or if they're looking, someone's like, I didn't get paid yet. I'm like, okay, I'm working on it. But yeah, so that was like, that was the origin. But it was really funny. So Drew Houston from Dropbox, I think I've ever told him this, was the first one, like everybody, we were gonna close and it was like over a day and he was like, oh, we gotta, we gotta close. And I think that we, we, our first bank account was Silicon Valley Bank. We realized we had to incorporate. So we got, you know, we actually, I remember it was like a Monday.

• 44:20Ben Gilbert?

  Drew wanted to invest? That was the?

• 44:22Speaker 02

  He was gonna invest. He was, well, he was ready to wire like before everybody else. Like, can I wire? I was like, oh, hold on, like, we have some bank issues. Let me get back to you. And I remember, sorry, I didn't mean to throw you under the bus on that one.

• 44:34Ben Gilbert?

  The issue being we haven't reached out to them yet.

• 44:36Speaker 02

  Yeah, the air cover. The issue being we haven't set up the account. But what we did is we, we reached out to an attorney. I won't mention who it was. It was like on a Monday. And they were like, great, we'll do it. And it was, I had an attorney that I knew pretty well, but my co-founder had reached out. And he was taking care of that. So I didn't even thought about it. We were running so fast that week. And, and I was like, oh, who'd you reach out to? And he told me, he's like, okay, sounds good. Let's get this started and set up. And then the person just didn't call us back for like, they were just quiet for like two days. And we called them like, oh yeah, I'm on it, I'm on it. You know, like, no, you said you'd do it tomorrow. Okay, we're done. Like, two day contract, we're not working anymore. I called someone I'd worked with actually at Wavy and Nick from Oric, who was the only attorney I'd ever worked with in this context, who I really liked.

• 45:20Speaker 02

  And he got it turned around like 24 hours. And then we opened a banking account and got our money. I think the learning from that is like, don't worry about getting all the trappings of the startup, I would say, like all the things that kind of on paper designate that there's the startup. Just spend all your energy on, is this the right business? Right? Because none of that stuff really matters unless you have the right business.

• 45:42Ben Gilbert?

  Right. The startup isn't the legal entity in the payroll system and the IP assignment. Like it's having a thing that exists in the world that didn't exist before that customers want.

• 45:50Speaker 02

  That someone's interested in or that someone's willing to fund to figure out if people will be interested in it. Yeah.

• 45:54David Rosenthal?

  This business that you're triangulating on, that becomes convoy of a marketplace of

• 46:00David Rosenthal?

  Truckers and shippers. How did you get the initial liquidity for this to happen? Because it's one thing to say, "Oh, hey, join my marketplace as a shipper. You can ship stuff and it'll be great. And I promise to get there on time." And you've got one trucker that's like 100 miles away. How did you bootstrap this?

• 46:21Speaker 02

  Yeah. And I think there are a few people in the audience that have more long-term first-hand knowledge of this than I do. So the way we originally bootstrapped it was, well, we made a mistake. We thought truck drivers would be compelled by our amazing vision. You know, we thought the great design of our app and the vision of our ability to help them would compel them to download and use our app. We worked really fast. So we raised money in May and then we raised again in July, our seed round. And then we launched at the end of August. How much did you raise in May and July? I think it was like a million in May, like a million and a half in July, something like that. We built the app just for Android initially, a web experience and a pricing model and

• 47:06Speaker 02

  matching model. And then we went to market. So it's the basic bare bones of an experience. And we took this app, we went and showed a bunch of truck drivers. I remember going back to the truck stops and completely safe about this. But everybody in the company, when they saw a truck, would take a picture of the side of the truck and put it on a Slack channel. So we had this Slack channel, the side of trucks, because everybody has their MC number and DOT number.

• 47:28David Rosenthal?

  You can go look up those trucks.

• 47:29Speaker 02

  Look up who are these local truck drivers, all these small... Because we didn't even know where to find them, even though there are online directories we discovered later. And there's lots of... There are way more efficient ways to do this. Like, driving down the road, taking pictures of trucks you're driving by and then posting to Slack is not safe. But we felt like it was important. So we just went to warehouses and just took pictures of trucks coming in and out, or truck stops. And we were just talking to people. And so we developed this local network of maybe, you know... Some trucks to call and then we just went trucks to ask them and nobody was interested. We completely bombed and I remember-

• 48:05David Rosenthal?

  And this was a big part of the, I meant to cover earlier, but a huge part of the thesis that I imagine as you're building up this business plan-

• 48:11Speaker 02

  The truck drivers would use it?

• 48:12David Rosenthal?

  Well, the truck drivers use it, but truck drivers have smartphones now. Like, these are the days when, you know, this is 2015. Everybody has a smartphone. Truck drivers, they were never gonna touch software. They were never gonna install a desktop in their trucks. Like, but now they have a smartphone. They have a computer.

• 48:26Speaker 02

  They were just getting smartphones then.

• 48:28David Rosenthal?

  Yeah.

• 48:28Speaker 02

  Right then. They're thinking about, which completely rightfully so, I wanna get some work. We were realizing brokers are not love-hate relationship. I also heard that from truck drivers about brokers, right? There are a lot of, kinda shady fly-by-night brokers. There are a lot of very respectable, great ones, but people, like, here's the thing that'll happen. This is, you know, will happen. Someone will create a brokerage. They will go to a shipper and say, "Hey, I'm a broker. I can do your work for you." The shipper says, "Great. Here are these 25 loads to do."

• 48:56Ben Gilbert?

  And is it hard to get a broker's license? Like, is this, is this a big hurdle?

• 49:00Speaker 02

  It's not that hard to get a broker's license.

• 49:01Ben Gilbert?

  Any single person. This is why there's a million.

• 49:03Speaker 02

  Well, there's brokers. There's 15, 18,000 brokers in the US, yeah. So you can go get a broker's license and they're, you know, most brokers are totally legitimate, do a great job. But sometimes a broker will do this. They'll go get work from a shipper. Maybe the shipper pays, is gonna pay them for 20 loads, right? 20 grand in total revenue. They go get trucks to do the job. The trucks complete the job. The shipper pays the broker. The broker disappears. Right? Never pays the truck drivers. That, that happens. And, or they don't pay them what they're deserved. So the, the whole idea of this middleman that kind of controls payments on both sides. And it's kind of, it's a zero-sum game where they're trying to pay the carrier as little as possible to make the maximum profit on every job. The truck drivers don't always love that, right? So coming in as a new broker-

• 49:44David Rosenthal?

  Well, and that's the, that's the worst-case scenario, but even in a good scenario, you're an individual broker. You're a human, right? You're thinking, "How many trucks do I know? How many shippers do I know?" You're trying to coordinate those trucks and then you've got the payment issue, right? Like, you're getting paid by the shippers, but you're not getting that money right away. And then the truck driver, like, he or she is driving the load, right? And then they're like, "Well, I just worked. Like, I need my money. I need to get paid." And the broker's like, "Well, I haven't gotten paid yet."

• 50:10Speaker 02

  Exactly. That also happens. So there's a lot of discrepancies around how much, how much you actually wanna pay them. It's complicated. So basically, that's a situation where the truck driver doesn't always trust the broker. A brand-new broker on the scene that says they have this app that's magically gonna give you freight when you open it is not fully believable by someone who- Who is used to load boards, which are effectively Craigslist and brokers say, I have a load. The broker doesn't actually have the load. They just post it. So truck drivers will call them and say, yeah, I want the load. Oh, great. How much are you willing to do it for? Eight hundred bucks. Oh, great. Hold on. Let me just double check to make sure it's still available. Hey, shipper, I can do it for 950. Right? Like, because they don't have the load yet. So they're kind of playing both sides. This is, this, this happens. And so then truck drivers don't always assume that when they see a load posted on these traditional load boards, that it's a real load. Could be a phantom load, right?

• 50:55Speaker 02

  So that's the environment you're walking into. You're, we're discovering this. We realize that truck drivers don't fully trust this notion. We're brand new. Our MC number, our official like motor carrier numbers of brokers, a day old. So like, who are you? So it was hard to get them on. So what happened was nobody would go on. And then we said, okay, we realized that tactics, the flywheel will not start spinning if we start with supply. So we went to the

• 51:16David Rosenthal?

  And the orthodoxy is you're building a marketplace, you've got to start with supply.

• 51:18Speaker 02

  That's right. Exactly. That's what we thought. So, and we're like, you got the supply ready for the demand. Because Uber's model was they had to have a car ready because you're going to need the car in five minutes, right? What we realized was we could get a freight from the shipper and it doesn't pick up for 24 to 48 hours. Maybe 72 hours. So the, what we actually figured out was the best way to build the flywheel was not to go start with supply. It was to get demand, take each individual shipment, go to the supply and say, I have a shipment for you. Do you want it? Yes, real shipment. I'm in. Great. It's waiting for you in the app. So then you go from a 0% conversion to like 95% conversion, where if the truck driver wants that job, they're going to download the app to get it, right? And so that ended up flipping it and making it go fast.

• 52:03Speaker 02

  So then what the secret sauce, the success factor for Convoy was about how rapidly we could onboard and, and evaluate a new carrier. So it was about speed of carrier onboarding became the most important thing. Because effectively the clock's ticking. Once you take the job from the shipper, you, we had to go get a new carrier into our platform. Sign them up, train them to use the app, get them to download it, do the paperwork. You know, get them to sign our agreement and do the job in 24 to 48 hours. That became the like secret sauce for building the brokerage. And that's how we got the flywheel going.

• 52:32David Rosenthal?

  Well, I think that's what's so cool about you guys in these B2B marketplaces is, again, you think about the consumer-driven companies, it's about how can I satisfy the product need of the consumer as quickly as possible. In these B2B marketplaces, it's about money. It's like, I have money. Like, I have a job, and I will get you the money as soon as possible. Like, that can drive it. And so the other thing that you guys did, it was pretty early on, right, is you institute, we will pay you within a day of delivering the load, right?

• 52:58Speaker 02

  That's right.

• 52:59David Rosenthal?

  How did you make that happen?

• 53:01Speaker 02

  So that idea came out of, again, the flywheel works in our world, not only do you need the driver to do the job, they need to download the app and use the app. And so a lot of work has gone into make that app as simple as possible. But we need them to use it. And one of the best ways to get them to use it was to say, if you use it throughout the job, and you upload the paperwork to the app, then we can pay you really fast. And so it created an incentive for them to use the technology, which then reduced our costs and gave us the data we needed to run our business. So effectively, if I could pay the carrier 30 days before they're used to getting paid, the cost for me to finance that is a lot less than the benefit that I get from a carrier

• 53:46Speaker 02

  using my technology platform, from the data that I collect, the operational efficiencies that come from that, the visibility, and the network that I build. And so that was effectively a cost of growing the network faster.

• 53:58Ben Gilbert?

  There's this interesting, sort of famous venture capital question, that is, why now? People have tried this business before, and people specifically have tried building a digital freight brokerage before. And so, why now? And it is such a clear and present answer of, of course, smartphones came out in 2007, but like, the broad adoption by everyone who drives a truck wasn't until the 2014, 2015 era. And once that happened, not only could you get them to upload this stuff, but like, you could passively collect location data and just know, like, hey, where are the loads? Like, I don't have to, we don't have to have people calling and saying, like, has it gotten there yet? Like, you just know.

• 54:35Speaker 02

  That's right. Yeah. And that's why it's important that they use the app.

• 54:37David Rosenthal?

  And I think that's what's cool. But that, it's not enough. You're just like, oh, all the pieces are there. There are companies out there that are like, basically installing smartphone guts on trailers at this point, right? Like, you can sell software and try and be like, oh, yeah, like, it's better. Like, the industry should do this. Or you could, you could... You know, create incentives like you guys did to make it economically better for participants in the ecosystem to do that. And the way you do that is you actually create a full stack company, right?

• 55:03Speaker 02

  That's right. Yeah, exactly. That was the, you could build software and we could have built this software and sold it to brokerages. We kind of thought about that. There were two big reasons we didn't do that. One is we really wanted to do something transformative. And it's very hard to change an industry by selling a software product to the person running the industry. Maybe that will drive their behavior, but it's probably not going to really drive massive behavior change. And they're going to dictate what they want from you. So you'll kind of build to their expectations and needs. They ultimately own it.

• 55:34Ben Gilbert?

  The analogy is those flywheel apps in taxis.

• 55:38Speaker 02

  Yeah.

• 55:38Ben Gilbert?

  You know, like that, that wasn't what took over the world.

• 55:40Speaker 02

  Yeah, that's right. And we wanted to be in that position. We wanted to be the principal in the transaction. We wanted to have the relationship with both sides. So we could not only improve the efficiency of the marketplace, we could go upstream into each of their businesses and solve their problems. Because ultimately, that leads to a bigger total business opportunity. And we don't think this ends with truckload freight, right? We're, we're thinking now about it. We've already built a transportation management system, a TMS software solution for medium, medium shippers to use that they can run all of their freight on. So they can actually book their loads on Convoy and book their loads on any other trucking company via Convoy's platform. And that starts to give us a bunch of other benefits. We do the same thing on the other side. So you can build out and out by owning that relationship.

• 56:22Ben Gilbert?

  And that's free, right? That trucking management system software?

• 56:25Speaker 02

  Yeah, it's free for medium ship and for medium and small shippers.

• 56:28Ben Gilbert?

  So that serves as your top of funnel for the, the shipper side where, hey, you may not be using Convoy today in the traditional way that everyone else uses it. Here's some free software, you know, it'll provide all these benefits to you. Is that how you think about that?

• 56:41Speaker 02

  Yes, it's, it's, it's still early, but there are a lot of actually larger companies using it too. We have companies, you know, doing 15, 20,000 loads a year that are using it.

• 56:49David Rosenthal?

  Is the right analogy here, Amazon Marketplace?

• 56:52Speaker 02

  This is, it could move in that direction at some point. That would be effectively really creating like a marketplace for other brokers as well. Today, we're not doing that. When a company is using that, that TMS, it's a shipper.

• 57:06David Rosenthal?

  It's a shipper.

• 57:07Speaker 02

  It's a company that's shipping freight, right? The company that's actually purchasing the shipping service.

• 57:11Ben Gilbert?

  All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, Logora, the agentic operating system that is redefining how the world's best legal teams work.

• 57:24David Rosenthal?

  Yep, it's sort of obvious that AI is going to completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Logora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 57:41Ben Gilbert?

  So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm for months. They sat with the lawyers just watching how the work really gets done.

• 57:56David Rosenthal?

  And that's how you get features that customers love, like Tabular Review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Logora's bet here is interesting. Since it lets each lawyer handle more complexity, any given person can increase the quality of their work and do higher value work. And this means that the pie can grow even as each individual task takes less time.

• 58:20Ben Gilbert?

  And they recently launched Logora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.

• 58:39David Rosenthal?

  And Logora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Logora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Logora now has over 100,000 lawyers on the platform from 1,200 legal teams in 50 countries. And crazily, they went from 1 million to 100 million in ARR in about 18 months.

• 59:09Ben Gilbert?

  Truly insane numbers, and that is the real test. Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time, or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in-house at a company, you can learn more at lagora.com/acquired and just tell them that Ben and David sent you. All right, so Dan, I want to take us in a little bit of a different direction and kind of not catch us up all the way to today, but talk about some of these milestones in the company. Convoy has grown absurdly fast, like in revenue, in fundraising, in headcount, in every observable metric, like it is outpacing the traditional startup. I mean, what you're four and a half years in.

• 59:54Ben Gilbert?

  So can you talk about some of the points where you made the decision to put the foot on the gas? And sorry for the, anyway. How you made those decisions, the trade-offs involved in making those decisions? It just fascinates me that it is so aggressive.

• 1:00:11Speaker 02

  You know, I think from the very beginning of the company, we believed that speed was a feature of a company. Like there's a, we thought a lot about our values, who we want to be as a company, you know, how do you create foundational values that lead to the experience you want to have as a business? And speed was always one of them. We believe that, as you said, 2014, 2015 was when truck drivers started getting smartphones. And prior to that, this isn't possible because you can't mail a truck driver a piece of hardware that they're going to install in their cab four states away when the job picks up in a day or two, right? It's just not a feasible thing. When we felt like the window opened, we realized it was a really good idea. There were other people looking at the space and we wanted to move really quickly.

• 1:00:55Speaker 02

  So we did decide early on that this was going to be a feature of the company and we were going to try to push ourselves. So in year one, I mean, I'll just walk you through the year one timeframe, which was very fast. We, you know, started hacking on it in March, incorporated the company April 1st, not on purpose, but like it's been fun. There's a couple of things that we've now built around that. We, again, you know, raised, raised the money in kind of April is timeframe and kind of July, I think a little bit. And then, so I guess it would have been April when we incorporated, we raised money. And then we built it, like I said, launched it in August in a private kind of beta environment with 20 or 30 customers, announced to the world in October, and then raised our Series A in November. And close in December. So it was a very fast first year.

• 1:01:39David Rosenthal?

  And that Series A was a $16 million round from Greylock.

• 1:01:42Speaker 02

  That's correct.

• 1:01:43David Rosenthal?

  Which now you're like, oh, $16 million Series A seems reasonable. That was like,

• 1:01:46Speaker 02

  That was very, very large.

• 1:01:47David Rosenthal?

  And very fast.

• 1:01:48Speaker 02

  Yeah, it was a very large. And again, that came back to the theory of we're going to try to go fast.

• 1:01:53Speaker 02

  We need to align around the capital that will allow us to go fast because we've felt like we've seen so many of these markets. And this was also in the earlier days of many of these shared economy and like, and like other sort of ride sharing type services where people saw how speed mattered and the first mover was able to get in a very advantageous position. It's not exactly the same in B2B and in this, in hindsight, but at the time we're like, no, we don't, we're not sure, but we need to go fast. We don't want to find out too late that this, that speed was really important. So we built that, we built it quickly and we determined that was going to be a big factor.

• 1:02:25Ben Gilbert?

  And is that because you thought, okay, competitors are going to see this too?

• 1:02:27Speaker 02

  Competitors, yeah. We thought people were going to get into it and we felt like we, it was, yeah, these opportunities don't come along very often. A technology changed that unlocked the potential to build this business. And drivers adopted that at this time. So there really, it was, it was an open window for this massive business to be disrupted. There have been a lot of companies. Coyote Logistics is a very innovative company that came along in 2006-ish. Several others have attempted to do innovative things as well. They just didn't have the smartphone. And it turns out with a transportation service and location where location is so critical, you couldn't completely disrupt it without that. And so that was why we're like, hey, speed's going to matter. So we really worked really hard and made it, one of our values is always have a sense of urgency.

• 1:03:12Speaker 02

  We made a bunch of decisions along the way to do that, even in the code. If one of our engineers was going to build something and was going to do it in a relatively hacky, unsustainable way, but it was for speed early, they would comment it out with CTFU, which was catch the F up, which was, which was the way we thought about it. Like we're, we just said, we're behind. We don't know who we're behind right now, but we're, we assume we're behind. Let's go fast. We, we wanted to do that. And in hindsight, I think it was the right call. We were able to kind of help design the industry in the category. We're of the independent startups, I would say the most notable brand. We were able to have more options when it came to fundraising because there weren't others that were ahead of us that had already raised from these investors.

• 1:03:55Speaker 02

  And we were able to build a strong brand and relationship with shippers, carriers, ecosystem partners, the industry, et cetera. Or right now, I still think we're a long ways away from, you know, from success. But we have the opportunity now to be the company that really disrupts this. And we wouldn't have had that if we would have gone slower. Now we need to like, now it's really important. You can't keep the same mindset forever. You have to shift and evolve based on the conditions of the business and the environment you're in. But that was the right mindset for the environment we were in, the business we were going after for those first four years.

• 1:04:29Ben Gilbert?

  I love that, that first few milestones. Give us some more along the lifetime of the company, whatever you're willing to share, whether it's employees or customers or revenue or whatever. But like, help us understand sort of the exponential nature of those next few years.

• 1:04:42Speaker 02

  For the first, like, I think eight quarters or so, we were doubling volume every, or every quarter approximately.

• 1:04:48Ben Gilbert?

  And that's like GMV, like the amount of-

• 1:04:49Speaker 02

  Yeah, the number of shipments we were doing. We looked at it as shipments.

• 1:04:51Ben Gilbert?

  Shipments.

• 1:04:52Speaker 02

  Number of loads. That was probably not exactly that, but it was, we doubled for quite a while. We're not doubling, we're not doing that right now. It's sort of, we reached the size where that's very, that'd be very, very difficult. You know, but we've grown, we've more than doubled over the last couple of years, each year. And so that has been very aggressive and it's challenging because as you're, if you're trying to grow your business at that scale and you're trying to maintain your culture and your identity and you're trying to hire efficiently and maintain the same kind of bar, it's very difficult to do it that, at that speed. And I've just said this before, but I, you know, it feels like we're a four-year-old that looks like an eight-year-old. Because the outside world often looks at us and people that join from other companies is like, well, you're this company that has a pretty notable name now.

• 1:05:35Speaker 02

  You've raised a lot of money, you've grown to be pretty significant, you have a national presence, you have all these big customers relying on you. You know, we're the biggest trucking company for several name brand, you know, Fortune 100 companies now in the, in the country. So we've really gone to be way beyond niche. But internally, we're four years old. And so to build this in four years and the infrastructure and the systems, they're just not all there. And sometimes we, I think we hold ourselves to an unreasonable bar in that respect. And I actually encourage our team sometimes to, to not, not even push us to get there. Like you actually want to be sometimes a little bit less developed because you can move faster and be more flexible. You don't want to look like a 10-year-old company when you're four years old. You want to be four years old. And so that's, that's something that's really important.

• 1:06:18David Rosenthal?

  There's two, I think, really important strategic decisions in this that feed into this mindset of grow and scale fast that I want to ask you about. The first one is, back in the early days, in the seed round, leading up to the Series A, you were operating only in one corridor, right? One product, one type of trucking in one corridor in the Pacific Northwest, right? More or less.

• 1:06:42Speaker 02

  Whatever trucking we could get.

• 1:06:44David Rosenthal?

  Yeah, exactly.

• 1:06:45Speaker 02

  We weren't sure exactly which category to just, we were taking several different.

• 1:06:49David Rosenthal?

  Because there are a bunch of categories in trucking of different types of loads, and then there's also geography. And then you guys had to make a decision about scaling. It was kind of like, you know, if you use the analogy of like a consumer marketplace, like a Yelp or an Uber, you had like one city that was working. And then there's the canonical question of like, well, what do you do next? Do you expand nationwide? Do you go to one other city? Do you do another? And like, for you guys, I think the question was, do we expand to other types of products of trucking, or do we expand nationwide? And you eventually made the decision to expand nationwide, right? Pretty, pretty early. How did you think through that? Because it wasn't obvious, right? You could say like, expand nationwide, but that means we need to have supply nationwide of all these trucks, and we can need to serve our shippers really, really well. How did you do that so quickly?

• 1:07:35Speaker 02

  So, it's, it's, the marketplace works on a lane level. So a lane is either a metro, we call a lane in our world is either a metro, it's like the greater Seattle area, where a shipment would pick up and drop off in the same location, the driver's home that night, or it's a point-to-point, Seattle to Sacramento, Sacramento to Phoenix, for example. And so the marketplace develops at that level. And one of the challenges we encountered early on was, we kind of had to decide, are we going to be super local-focused? And there's a category factor of it's very local. They actually don't drive more than a couple hundred miles in one direction because they want to get home every night.

• 1:08:08David Rosenthal?

  They sleep at home every night.

• 1:08:09Speaker 02

  Sleep at home every night. And so we could have focused specifically on local. And we did that for a while. Then we started realizing that, you know, most of the dollars, most of the companies that are really in need of help. Have more complicated supply chains than just shipping locally. So some of the shippers that we were working with locally are like, this is helpful. But what's really painful for me are these shipments I have that go between different geographies. And I need your help there. And we started talking to some bigger companies and they're like, well, I really need your help in this part of the country or on these lanes. Right? And so it was important to be very disciplined about what we did and didn't do early on. But we kind of let the customer lead us a little bit early to understand what the opportunity was. And as soon as you start thinking about, we're going to support this lane.

• 1:08:54Speaker 02

  Now you need a truck driver that's willing to drive a little bit further outside of that local area. And when the truck driver is in that next location, if you want to think about how you keep them engaged with your platform, well, you might need another job for them. Otherwise they're going to exit your platform and getting them back's hard.

• 1:09:08David Rosenthal?

  They're going to get to St. Louis and they're like, all right, I'm going to go back to my traditional broker.

• 1:09:11Speaker 02

  San Francisco or Oakland or something from Seattle. And so, you know, we did local for a while, but we started to have opportunities outside of that. And we realized we, we had to kind of have a controlled slide. So we couldn't just go national at first, but we had to really think about corridors and parts of the country where we could develop that flywheel.

• 1:09:30David Rosenthal?

  But you had, once you went beyond local, you had a national network effect, right? Because these truckers, once you went beyond local, they were the carriers. They, they operate nationally, right? So like you winning a bunch of carriers helps you with shippers in St. Louis and helps you with shippers in Boston and helps you with shippers in.

• 1:09:48Ben Gilbert?

  Big carriers operate locally, but if you're bringing on these three to five truck carriers, do they operate, I'm sorry, nationally like that?

• 1:09:56Speaker 02

  Uh, there's, all of them do all of those things. There's, there's ratios, but like all of them do all those things. So there's regional carriers too. Maybe they're out for a week, right? And so you can kind of start focusing on that. So you're right, what we had to do was say, we're not going to have no, like we're going to have some leakage. Like a carrier will come into our network and maybe they'll leave the I five corridor. And that's okay, we're not going to chase them, we're not going to go develop those other markets. Enough of them will stay there. We can't do supply and demand nationally at the same time. So we, we focused on the Northwest. And then we actually went kind of some West Coast. And then we went to Texas. There's a story on that where Unilever reached out and said, hey, we're doing this pilot with some of the new companies. And you guys just announced yourselves, we were about to start with these other two, do you guys want to try it too?

• 1:10:42Speaker 02

  And I remember

• 1:10:43David Rosenthal?

  There's only one right answer to that question.

• 1:10:44Speaker 02

  That's an amazing thing for a startup to get. Yes, I was, I was really confused as to why they called us. Cause we were doing very local, like hyper Seattle shipments, kind of up in, just in that area at the time. And I remember

• 1:10:55David Rosenthal?

  I remember you guys announcing this deal.

• 1:10:56Speaker 02

  Yeah, I was sitting across from this guy named Lauren Siks, who's been at Convoy from the beginning. I remember just literally doing a Hail Mary pass in the room. I was like, okay, here we go. And I was like, I'm going to say it. And so I didn't know what to say to the, to Unilever. Cause I was like, well, I think I said something like, we would be willing to work with you guys, but we need all your freight on the West Coast.

• 1:11:15David Rosenthal?

  Whoa.

• 1:11:16Speaker 02

  Just because I was like, I don't know, I'm going to, they offer.

• 1:11:19David Rosenthal?

  You got nothing to lose.

• 1:11:20Speaker 02

  Like, let's pilot that. Um, and I, and the person thought like, I think I was probably half serious, but they like, could not even rationally believe I may have been serious. So they just laughed and thought it was funny. Um, and then I was like, ah, ha, ha, ha, like, yeah, that's where, where do you guys want us?

• 1:11:35David Rosenthal?

  But like, really?

• 1:11:36Speaker 02

  But, but, okay. Um, and so I was still learning at that point. Um, and they said, okay, we'll just, we'll get back to a location, but maybe it'll be California, maybe it'll be Texas. And they ultimately asked us to start off in Texas. And I'm like, okay, this is interesting. Texas is a very heavy local freight market. So it kind of fit our MO a little bit. And we went down there and we started with them in Texas. Cause they ship from city in Texas to other cities in Texas. And we told them, we're only going to do local. So one of the hard things we had to do, and this is very important again for a startup, know who you want to be in your, and how to sequence. And so we, we said, we're only going to do drive in. At the time it was only flatbed and drive in, but we really were only doing drive in. So for them, we're only going to do drive in shipments. We're only going to do local drive in shipments.

• 1:12:20Speaker 02

  And we're only going to do shipments that are not like, that are within this timeframe. Like you have to give us this much notice. And we kind of said, if you want to work with us, we're not going to extend ourselves into something we don't know how to do yet. And we're building this network and the way we thought about our network, someone very, you know, wise early on said, built, when you're building a marketplace or network, you want every single piece of demand that comes in that marketplace to apply to all of your supply. Like the ideal world is that every demand opportunity could be serviced by all of your supply. That is the least fragmented marketplace. So you will, in the most quick, the fastest manner possible, reach liquidity in that marketplace. So we looked at it and said, what are all the dimensions that split supply? And because you have carriers that are local, regional, and long haul. Those are different. There's some bleed over between regional and local and regional and long haul,

• 1:13:05Speaker 02

  but effectively those are different carrier segments.

• 1:13:07Ben Gilbert?

  Yeah.

• 1:13:08Speaker 02

  And because you have different equipment types, because we think, so we said to Unilever and others, we're only going to operate in this bucket. You draw the buckets up there, we're only going to do this, and we can't break that because if we do, we won't be able to give you the experience you're looking for. And every other broker in the country goes to them and says, "I can handle you nationwide tomorrow." Because what they're doing is picking up the phone and calling a bunch of trucking companies and not requiring them to use technology, not having to build a network, just saying, "Well, you do the job." Whereas we required, we had to get the driver to use the tech and to build this flywheel and try to have this automated matching. So we had to really concentrate early on. That was a very important lesson in not going too broad.

• 1:13:44Ben Gilbert?

  All right. So one more scale question that I have for you, or scaling question, then I promise I'm done. So we're in this interesting time in startups in the capital ecosystem where people are starting to favor unit economics over growth. And I'm curious your perspective on that general transition. But as it applies to Convoy, I'm curious about, over the last four years, what are the ways that, what are the ways in which you've said, "Okay, this is a good time to give on unit economics so that we can grow," and what levers did you use to do that?

• 1:14:16Speaker 02

  So the two probably prominent reasons why we've done that is we have a customer. That customer wants to ramp in a timeframe that we could not reasonably do with the support services that we have today. And therefore, we have to, we have to expand the team, like all dimensions of the team. Could be building capacity with truck drivers, could be providing customer service, could be account management. We have to scale those faster and ahead of the growth and train, and get the people into the company and ensure that we offer like an A-plus level of service. We're a tech broker from Seattle with a very little, very short track record. If someone's going to make a bet on us, they're looking for us to fail on the non-technical aspects like service and support,

• 1:15:00Speaker 02

  and really making sure it works and ten, and providing that account management, the support, right? So we need to be great at that because they're going to assume that's going to be our weak spot. So one was over-investing, I would say, or investing heavily in that at different periods. And when things started to, like, like crack, we might grow too fast in rows. We're not doing that. Slow it down and then reinvest in that. So that was one. The second is...

• 1:15:22Speaker 02

  Developing the flywheel and the way freight works is there's no such thing as the price of the there's no known price of the truck. So for a job from Seattle to Portland, you might have one truck that's willing to do that job tomorrow for $400 and one truck that's willing to do it for $900. You know, maybe, maybe even less and more for very different reasons. One really doesn't want to do it. One really wants to do it. So the market's kind of made every day. If I take five shipments today and I have five trucks in my network already, I can probably service all those shipments with the right economics and pretty efficiently because I already have the trucks in my network. But if I want to grow my network, I'm going to say to the shipper, give me 10.

• 1:16:03Speaker 02

  I only have five trucks. I need to go get five more trucks that are less conveniently located that I don't know yet. And I'm probably going to have to pay more to get them on my platform. But that's the way to get them on the platform. And so in order to drive density into our lanes and build the marketplace, we would bring on more demand than we had supplied to cover and then use that demand to bring in more supply in a in each of those jobs.

• 1:16:26David Rosenthal?

  It's getting to the reverse of the traditional marketplace. Like, oh, you're going to invest like let's onboard a bunch of supply. And then when the demand, you know, we'll run adwords for the demand. For you guys, you're like, let's use sales to onboard a bunch of demand and then that'll attract the supply.

• 1:16:38Speaker 02

  That's right. And there's, you know, there's different balances as the, the market shifts back and forth. But so we, in those shipments, for example, we would not have great unit economics. But it's actually the number. It's ironic. It's like not, you don't get a bulk discount in trucking. You get like a bulk surplus because the more jobs you take, any broker, the more jobs they take on a given lane on a given day spends more per average to cover them. Because you're buying a variable cost product that goes up with the amount you use. If you have 10 trucks, those trucks are going to be, imagine those trucks in order from cheapest to most expensive.

• 1:17:10David Rosenthal?

  Yeah.

• 1:17:11Speaker 02

  You're going to try to get the cheapest truck first. So if I take one job and I get the cheapest truck in my network for that job, I have covered it at the maximum spread, but every additional job I take, the next best truck would be less efficient for that job.

• 1:17:23Ben Gilbert?

  It's effectively a worse and worse product market fit for that individual job.

• 1:17:27Speaker 02

  For the individual truck driver in that moment, for that shipment. But that's how you build supply, and then once you get enough, then you have a healthy ecosystem where you have a lot of trucks, you get the data to where they are, you can then start to efficiently match a job to a truck better than the traditional industry player can who's just calling around. And so that's the investment you make in building this.

• 1:17:43Ben Gilbert?

  Right.

• 1:17:44Speaker 02

  There's a dozen other things, but that's one of the investments we made.

• 1:17:46Ben Gilbert?

  So you could, you could sacrifice unit economics for a long time to make sure you have like tons and tons of carriers, truckers that are constantly using the app, tons and tons of shippers that trust you all the time, so that at some point in the near future, you're like, look, the spread between that one truck and that one shipment that has amazing unit economics for us, and finding that place where it's really expensive for us and we don't make much of a margin, if anything at all, it just keeps pushing that further and further out because there's much more liquidity on the platform.

• 1:18:16Speaker 02

  Exactly.

• 1:18:17Ben Gilbert?

  Is that like, that's like the long-term thesis?

• 1:18:19Speaker 02

  And there's a lot of, obviously there's a lot of nuance behind that, but that's effectively how it works. And, you know, we're making a bunch of other investments. We have a big product data science engineering team. We have all these other functions that we're building to kind of build a brand and the technology and the infrastructure in parallel with the business. And those are all upfront investments where you kind of, they give you, they can help in terms of your growth. But fundamentally, that's, those are the primary drivers. Making sure you do a great job for your customer, it's worth investing early on when you're building your reputation and your brand in a traditional industry as an outsider, screwing that up early, it means you don't have a chance in the future. And then being able to grow your flywheel quickly and, and, and building density on

• 1:19:00Speaker 02

  your lanes is very important for, and we have all the data now that shows when you do that, here's what happens. Like, the world looks better, so we can justify those, those investments.

• 1:19:11Ben Gilbert?

  Thank you. David, do you want to move right into tech themes? Do we want to like catch us up to today in some capacity?

• 1:19:18David Rosenthal?

  Well, so today, where would you say you guys rank in terms of brokerages within the industry? Obviously you're a tech-enabled brokerage, but give us a sense of scale for where you're at within the industry and how penetrated you guys think you are thus far?

• 1:19:37Speaker 02

  We're still a fraction of the total trucking market. The truckload market is about $600 billion a year in the US. And that includes private fleets and for higher, but we can compete with all that. The largest broker in the country, largest truckload freight brokerage is doing about $10 billion a year in truckload freight. And then there's another five to 10 that are between 2, 3 and $10 billion. So that's the ecosystem of pure brokers. There's a lot of large carriers that also run brokerages. We would probably be in about the top 20, top maybe 15.

• 1:20:12David Rosenthal?

  Wow.

• 1:20:12Speaker 02

  So we're pretty significant in the brokerage.

• 1:20:15David Rosenthal?

  That's pretty incredible. And all these other companies are decades old.

• 1:20:18Speaker 02

  Yeah.

• 1:20:20David Rosenthal?

  Yeah. Cool.

• 1:20:22Ben Gilbert?

  For folks who are new to the show, we do a section after this history and facts called "What Would Have Happened Otherwise?", where if this is a traditional acquired episode and we're talking about a transaction that happened, it's usually what if that transaction didn't happen? What if big co didn't buy little co? I think it's interesting here to dive in a little bit of like, what if you guys grew at a normal startup pace? And where you would be today? What if that risk didn't pay off? You told us a lot about it, but the way that I would describe it is like, number one, there's numerous people who could have beat you to the punch on having a whole bunch of supply and a whole bunch of demand, truckers and shippers. I'm curious if there's a data mote here beyond just the marketplace liquidity?

• 1:21:03Ben Gilbert?

  Have you, by rushing into this and being an early player, what other things has it allowed you to do that otherwise, if you were, say, 300 people today or something, and able to service the amount of volume on your platform that that amount would give you, then what would you be giving up?

• 1:21:23Speaker 02

  Let's say that we had grown slower. We hadn't really gone national. We wouldn't have a chance to write the story about what's going to happen. And the reason is that you can't really, we wouldn't be able to define the future unless the major players in the industry. viewed us very credibly and we're using our service. So the largest shippers in the country, many of them are now using Convoy. A lot of the biggest ecosystem partners, the events and sort of influencers within the industry are looking to Convoy for what's the future? And we're, we're kind of defining it. Like we're, we're creating a category, digital freight network. We're describing what that is, we're telling that story. And I think that like you had to make a bet to be in a position where you, you were at scale,

• 1:22:08Speaker 02

  you mattered in the industry and you were one of the first to do that. If you're not one of the first, no one's gonna look to you for the story about what's happening. And so it's, it's, it's a lot harder for the folks that are a few below to influence what's going on.

• 1:22:23Ben Gilbert?

  And in a big way, these sales, they're, you know, you're making sales on both sides. You're, you're selling the shippers on your platform and you're selling the, the truckers on, you know, being a part of it, on taking the loads. Like there's an immense amount of trust there. Like you, you're convincing them ahead of actually demonstrating value. So it's sort of like you need to, you need to have, you need to be buzzy in this particular instance because you need them to, to be very receptive to working with you.

• 1:22:49Speaker 02

  That's right. And we were, again, you know, when we first started, I remember going to a dinner with a bunch of traditional industry trucking companies. And I have a lot of respect for the companies that do this. It's a very, very difficult industry. It's a hard job, being a truck driver is hard, running a trucking business is hard. It's a thin margin, complicated business. And it's hard to differentiate and do it as a, as a traditional broker carrier. But there was definitely a sense early on of, yeah, Convoy's doing this, but it's not really different and no one's gonna really take it that seriously. And I remember early on, on being told by our customers and by analysts in the industry that our competitors were basically saying, you know, Convoy just gets the freight that nobody else wants.

• 1:23:28Ben Gilbert?

  I remember those narratives.

• 1:23:29Speaker 02

  Yeah, Convoy's kind of picking up some of the scraps out there. And, you know, I remember hearing, you know, sitting and listening in and people didn't necessarily know I was there.

• 1:23:36Ben Gilbert?

  Convoy, who are those guys?

• 1:23:37Speaker 02

  Computers don't match freight, you know, people match freight.

• 1:23:40Ben Gilbert?

  Right.

• 1:23:40Speaker 02

  It just doesn't happen. And.

• 1:23:43Ben Gilbert?

  Ironically, computers matching freight is like an amazing use of computers.

• 1:23:46Speaker 02

  It's a very good use of computers. And again, I don't, I, I don't think that they didn't recognize that it was coming, but it's, it's sort of what you want to say because it's the right thing and they don't have it yet. And there are some just really big challenges for them to get there. So I think, you know, being in the position when we were, gave us a chance to. To kind of write the rules a little bit and be the first to come up with some of the models, like the free quick pay model, the guaranteed detention model, the idea of providing data and insights back to your customer. So collecting data about what's happening, every time a truck shows up at a location, when did they show up, how long did they wait, how long did it take to get loaded? How did they rate the facility? What was their experience? That particular shipment, how was it tendered to us?

• 1:24:29Speaker 02

  We can correlate data across all these experiences and go back to our customers and say, you know, this particular facility is underperforming other facilities in the region from your competitors that are competing for trucks. And this facility in this city is doing better during this shift than that one. Right? And you should be changing your tendering practices because when you tender in the morning, the trucks are more expensive. And like

• 1:24:49Ben Gilbert?

  They've never had data like this before.

• 1:24:50Speaker 02

  No one's done that. And so we kind of started that. And we've started a lot of things. And the idea of an instant price, you can instantly get a price that is committed to and you can see what capacity it's through an API.

• 1:25:01Ben Gilbert?

  Right. It's not going to get haggled on the phone like this is the price.

• 1:25:03Speaker 02

  So sort of, you know, you start to get to say, this is what the future should look like. And that's one of the advantages of being early. And, you know, others can quickly mimic that. And we haven't invented all of the things, but actually we have been very inventive. We've been the leader in new design. And I think it gives us a chance that, you know, our shippers and folks that are making kind of the calls in the industry and influence matters, like perception is reality in a lot of these things where if you're at a conference and the conference organizers or a famous freight analyst or, you know, a transaction analyst from a big bank gets up and says, you know, we really think digital freight works for the future for this reason. That starts to make it kind of a reality, right? It becomes a self fulfilling prophecy because then all the shippers are like, oh, well, then we should probably start buying into this.

• 1:25:47Speaker 02

  You need that perception momentum early on. And if you don't go fast and you don't get there quickly, you don't really get to contribute to that as much.

• 1:25:54Ben Gilbert?

  Yeah. And David, we're full blown in playbook now, but this is like totally one of mine is like in startups, in a lot of ways, perception is reality with the market, with your customers. I think I've said this on the show before, but one of the best definitions of a startup is from one of my colleagues at Pioneer Square Labs, Mike Galgong. He pointed out to me that a startup is very frequently just like Getting and scrapping and biting something that it doesn't yet deserve, whether it's a hire, whether it's a customer, revenue. Like, you're not there yet, but like, you're really trying to create the perception that you're there. And it's this interesting self fulfilling prophecy flywheel of like, once you actually do get that resource and that person joins your team, that customer commits to you, then like, you kind of are there. And then you can leverage that to the next rung.

• 1:26:38Ben Gilbert?

  And I mean, it sounds like you guys have codified this in the convoy flywheel, but like, that is the business for you guys.

• 1:26:44Speaker 02

  And it is every decision you make. So, early on, you're talking to somebody about a job, and like, "Well, I don't know if it's gonna work. Should I join?" I'm like, "I don't know. Like, if you join, you're half the company. So like, it'll be up to you." It's not like you're joining a thing that has a-

• 1:26:59David Rosenthal?

  That's some good jujitsu.

• 1:27:00Speaker 02

  Has like a potential, right? I mean, and it was hard to hire early on. Like, convincing someone to leave a job.

• 1:27:08Ben Gilbert?

  Except for the five people that followed you independent of whatever your idea was.

• 1:27:11Speaker 02

  That's right. I mean, that was, well, no, I mean, you know, we talked about some of the scope, but you're right. We had some, but that's also, that was hard. That was trust built up over years.

• 1:27:19Ben Gilbert?

  Totally.

• 1:27:20Speaker 02

  Right? I remember trying to convince a lot of people to join Convoy. And it was interesting, we had used the, in any tactic, in the tactic of like, "Well, you get to build this" and all these different things. But the economy has been doing really well. So, a lot of big companies have also had very strong stock value appreciation over the last 10 years. And so oftentimes, the pitch that the startup has is like, you know, that we're gonna have, we'll have faster appreciation. But when Amazon is doubling, you know, every year, then it's like, that's a pretty strong thing as well.

• 1:27:49David Rosenthal?

  Your stock price has to appreciate faster than Amazon's stock price.

• 1:27:52Speaker 02

  And it has. It definitely has, but that's cooled off too. So like, but during certain phases, it gets harder and easier, based on how well like, the alternative is growing. And I remember talking to somebody that I was trying to convince to join. I try to remember who this person was exactly. But I remember, I was like, "Well, here's how much we think your convoy stock would be worth." And they were like, "Well, I'm doing the math, and I think Amazon will be worth $8 trillion in three years." And I was like Seattle problems. Why? They're like, well, if you look at the last couple of years of like their stock price appreciation, or whatever it was, the timeframe they were using, it was like the exact right time. At some point, you have to start working back from GDP. Yeah, I know. But I was kind of like, I was like, I just, I felt so compelled to convince this person.

• 1:28:34Speaker 02

  That's sort of physically impossible. And you can't apply like a growth rate to a company that scale that's like that. It happened for, like, that rate happened for maybe the last year.

• 1:28:42David Rosenthal?

  Did you convince the person? Did you make the hire?

• 1:28:44Speaker 02

  This is a while ago. I'm trying to remember if that person, if that exact conversation turns into the hire. I believe they did. Awesome. But that was, I need a better answer for that. But that was, um, Cut it. But I just remember, I remember the conversation so vividly, and it was over the phone. So it wasn't like an easy, like, one to land. But I was like, no, no, you can't. Please don't do this. Please don't make this decision believing this will be an eight trillion dollar company. Like, that's not a thing.

• 1:29:05David Rosenthal?

  Yeah.

• 1:29:06Speaker 02

  And so, and so, but it was hard. And that just emblemized, like, um, the, the issue of that perception, right? So, so what I did early on was, there were a lot of tactics we used to try to convince them to do it. But early on, before that was a thing, I remember drawing, what I would do is I would take a piece of paper, and I would, and the X-axis was someone's career. And I'd be like, year zero. And I was like, how many years do you think you want to work? And like, no one really knows. They just say something like 30, 40, whatever. Could be more, could be less. And, and I'm like, okay, great. So, and here's your earnings. That's like the Y-axis. And I'm going to draw a curve that shows how much money you'll be making every year, and like your total wealth accumulation from your salary, or like what you expect to make here.

• 1:29:48Speaker 02

  And, you know, beginning, you're making about this much. It'll probably go up pretty steeply at some point. It'll kind of flatten off a little bit. It's generally like a, you know, salary curve. And if you add up that 30, the, the area under the curve is your, is your earnings in your life. And I'm like, I'm asking you to do it.

• 1:30:02David Rosenthal?

  You're sounding really like a former consultant here.

• 1:30:03Speaker 02

  I know, I know. It's like, if you integrate your salary, you will get. Exactly. But it worked. And I was like, look, I was like, just, this one year, it's going to come down a little bit. And then it'll go back up if we don't, like, if it doesn't work out, and you're, you leave after a year because this didn't, didn't work for you, like, then that's the area of your total.

• 1:30:21David Rosenthal?

  We were talking to your co-founder Grant this morning in preparation, and he was like, your reward for working at a failed startup in this environment is you get a better job.

• 1:30:29Speaker 02

  Yeah, probably get a better job.

• 1:30:30David Rosenthal?

  Yeah.

• 1:30:30Speaker 02

  Yeah. So that was exactly right. So if you take that little dip, you either get like the bump from Convoy working. Or you have this really interesting compelling experience and you get then your line goes up a little bit.

• 1:30:41David Rosenthal?

  Yeah, you get a higher level at Amazon when you go back.

• 1:30:43Speaker 02

  And so, yeah, I mean, it was a lot of, it's, I mean, hiring is hard. We've had success, but man, it is, everybody knows it's hard to hire effectively.

• 1:30:51Ben Gilbert?

  Yep. All right, David, anything else for the playbook?

• 1:30:53David Rosenthal?

  Yeah, well, real quick, my playbook, what I'd love to do, I mean, we'll work on this in future episodes, but because of this B2B marketplace is so different and new and you guys are at the Vanguard, I tried to codify like, what are some principles? I'm curious if you're like, nod, say yes if you agree or no, but to drive success in a B2B marketplace.

• 1:31:11Ben Gilbert?

  This is fun. We get to great David.

• 1:31:12David Rosenthal?

  Is demand drives supply. If you're bringing the money, you can create, you can align incentives in a market and get people to adopt a new technology that otherwise would be really hard. Like a G-Wiz feature isn't going to compel a trucker to download an app. That's one. Two, timing is super important. Like I think what you guys did with getting truckers paid to use the app within a day, like that's game changing for the industry. And so if you can change cash flow timing, and we're seeing this in other companies, that can be a huge driver of growth. So that's two. Three, I really like what you said about those early days when people were haters were talking about convoy and they were like, you guys only take the jobs that nobody wants.

• 1:31:52David Rosenthal?

  Well, it's like, if you take those jobs that nobody wants, you can, you can take the scraps from the industry, but because you're building a technology company in a holistic marketplace, you can then aggregate the supply out of that. And then get to a point where really, really quickly, you have a better cost structure for the jobs that everybody wants, right?

• 1:32:12Speaker 02

  And the, and the companies will take you seriously.

• 1:32:13David Rosenthal?

  Yeah.

• 1:32:13Speaker 02

  Operating at scale on the lanes that they care about. So you can use, you can use whatever you get to kind of get the carrier base going and then translate that into a virtual network. And because we plug all the trucks into our technology platform, as we scale, we effectively have this, this, you know, partnerships that lead to this virtual fleet, which we have visibility into and a direct connection with, which gives us capabilities that feel like, like it's a, it's a more like first party network for the shipper.

• 1:32:42David Rosenthal?

  Yeah.

• 1:32:42Speaker 02

  And so that's a really powerful combination.

• 1:32:44David Rosenthal?

  Yeah. And then the last one, which we didn't have time to get into today, but I also find it really interesting in these markets is you're saying like, price is not. Set. It's not, these are not efficient markets. And so ultimately, like, your big goal is like, if you guys can be efficiently setting price in a way that nobody else can, well, then you've just like completely aggregated the industry. So that's my, that's my last one.

• 1:33:07Ben Gilbert?

  That's a really good transition into grading. So again, on a traditional acquired episode, we would grade if big co-buying little co was like the right use of capital. And in some cases, you've got Instagram and oh my God, you couldn't have parked capital anywhere better. And in other cases, you know, lots of other great options to, to invest that capital. In these ones where either it's a near-term acquisition or like, there's no transaction that's happened with Convoy, you know, going public or, or selling or anything like that. The, the way that I think we're going to do this is grade what the A-plus sort of future scenario is for the company. Like, what are the things that have to be true in order for Convoy to create and capture

• 1:33:51Ben Gilbert?

  a ton of value in the world? And what's the scenario where it's a lower grade? You know, I think David put in here, what's the scenario where it could be a C minus? Where those things don't come true? And what are the factors there? Dan, you homed in on something earlier that was this, this concept that I really didn't understand before about every single, in an inefficient marketplace with low demand and low supply on it, there really is only like maybe one truck and one shipper for which you can be profitable on a transaction. Or maybe, and then like you grow to two or three or four. And if you have all the trucks and everyone who's shipping freight on your platform, then like, my gosh, you can handle a ton of volume and be profitable on, on those transactions.

• 1:34:36Ben Gilbert?

  And for me to get to an A+, I think, only after like reading a bunch about your business for the last, you know, month and then talking to you today, I think it's going to be, can you widen that gap faster than your company consumes capital? It's basically like, can you create enough slots, enough matches between trucker and freight where each one of those transactions is above some certain bar of how profitable they need to be and do all the volume before some, you know, run out, run out of money? Like the end game for every startup. Am I, am I capturing it well? Like, do you, is that how you think about it? And is that how you think about like, here's the spread of scenarios in our future?

• 1:35:18Speaker 02

  Yeah. And so a big part of it is getting all the trucks on board. And it's really about making those truck drivers more productive. That's actually what this comes down to. So it's the empty miles we talked about. So convoy can significantly reduce empty miles.

• 1:35:32David Rosenthal?

  Yeah. Well, and that's why price is hard, right? Because it's worth different, same job is worth different things to different people.

• 1:35:38Speaker 02

  We just took, we launched something this year called batching. You can take two or three jobs together. Our system will identify these jobs and look at all the possible combinations and automatically stitch together multiple jobs. And then offer it to carriers with ideal locations to maybe a triangle or a round trip. With the ideal appointment times. And we found that carriers will take that job for a significantly lower price than they would have taken each of the jobs in combination if you add them up as individual. And that's because we're creating efficiencies and making that carrier more productive. So that's the kind of stuff we have to figure out. And when we do that, and we actually saw the carriers that do that. Run empty about 19% of the time. That are, you know, if they're really plugged into convoy doing the batching system today with our current density of batching.

• 1:36:20Speaker 02

  The ones that don't run empty about 35, 36% of the time.

• 1:36:24David Rosenthal?

  Wow.

• 1:36:24Speaker 02

  And so just when you look at like the impact on the environment. You're reducing emissions from using batches by about 45%. Like you're reducing empty mile emissions about 45%, which is massive. That directly also translate into lower cost for the truck. The actual small trucking company spends less money to do the jobs because they're driving fewer empty miles. You know, trying to reduce wait times, all these things. So we view it as let's knock down the waste. Let's go after empty miles, unnecessary wait times, you know, loading and unloading times and just find ways to reduce those. And if we can do that quickly. Plus add more volume into that, like lower the waste and add more volume. Then we're creating a better cost structure. And then we're in an advantageous position and we have options.

• 1:37:09Speaker 02

  And getting that in place at scale with the capital we have is the key.

• 1:37:15Ben Gilbert?

  Awesome. David, anything else, Dad?

• 1:37:17David Rosenthal?

  I think that's right. All right, listeners. Now is a great time to talk about one of our favorite companies, Statsig.

• 1:37:25Ben Gilbert?

  Yes, there is a reason why the best product teams rely on Statsig, whether they are iterating on their core product features or shipping AI-powered experiences at scale.

• 1:37:36David Rosenthal?

  Yep. In the crazy speed of today's AI world, shipping fast is just table stakes now. It's basically trivial to build and deploy your app constantly. The real advantage is how quickly you learn what changes actually created value for customers and how fast you can use that signal to guide what you ship next.

• 1:37:56Ben Gilbert?

  This is where Statsig comes in. It brings experimentation, feature flags, and product analytics into one unified system so teams can ship safely, test rigorously, and directly link what they changed to how users actually behaved.

• 1:38:09David Rosenthal?

  So if you want to make learning your competitive advantage, whether you're building new AI experiences or just evolving your existing core product, go to statsig.com/acquired to get started.

• 1:38:20Ben Gilbert?

  Wow. Listeners, thank you for going on this journey with us. For folks who listen to a lot of episodes, I think you'll be like, oh, yeah, it's about how long it usually takes. For folks who came tonight expecting a commute-to-work podcast, it's been longer than that.

• 1:38:33David Rosenthal?

  Thank you for bearing with us.

• 1:38:34Ben Gilbert?

  Yeah. Do you want to do carve-outs? I have one I want to do.

• 1:38:38David Rosenthal?

  Okay, go for it.

• 1:38:40Ben Gilbert?

  And we haven't done carve-outs in a bunch of episodes because we've been jammed for time. And mine is a very cool app that is based here in Seattle that David and I used last night for the Acquired Annual Holiday Party that is former Convoy alum. So Vincent Shane from Mystery have created something incredibly cool. I think it's mystery.sh for anyone who wants to try it out. And you basically can... Set a time, say some of your preferences of the things you like to do and the things you might want to do that day or night, and then random things happen to you. And like, lists show up and they take you places and you get fed and then like you don't know how the night's gonna go.

• 1:39:18David Rosenthal?

  With people that you choose the people you do it. They don't like send random people to you.

• 1:39:21Ben Gilbert?

  Correct.

• 1:39:22David Rosenthal?

  So we chose to do this with each other.

• 1:39:23Ben Gilbert?

  Correct. Yes. So Dave and I like went fencing last night. Who would have thought we'd go fencing?

• 1:39:28David Rosenthal?

  It was super awesome.

• 1:39:29Ben Gilbert?

  But we went fencing and it was amazing. So if you're looking for like new things to do in your life, I highly recommend mystery.

• 1:39:35David Rosenthal?

  Likewise, it was a blast.

• 1:39:37Ben Gilbert?

  Awesome. All right. Listeners, thank you so much. We hope you you enjoyed the episode. If you haven't subscribed, you can at acquired.fm or in the podcast player of your choice. If you'd like to become an acquired limited partner, that is glow.fm/acquired. Thank you so much to Dan.

• 1:39:55David Rosenthal?

  And all of you here live with us. This has been such a new and awesome experience for us, so thank you.