Building, Scaling, and Selling. With Robert Nathan
In this episode, hosts Coleman and KJ sit down with Robert Nathan, a serial entrepreneur, investor, and visionary leader who has spent decades shaping the logistics, freight tech, and AI landscape.
From starting on the loading docks at 14 years old to building, scaling, and successfully exiting multi-million dollar enterprises, Robert shares the raw, unfiltered realities of the founder's journey.
He dives deep into the ultimate highs like landing on the Inc. 500 list and the brutal lows of having to downsize a company to survive an economic crash.Whether you are an aspiring founder, a logistics professional, or curious about how artificial intelligence is rewriting the rules of global supply chains, this masterclass in resilience and innovation is a must-watch.
📌 Key Takeaways From This Episode:
The "Axe" vs. The "Hatchet": Crucial leadership advice on making swift, decisive corporate changes when the market turns against you.
Building a Sellable Business: Why the best companies don't actually get sold, they get bought.
The Rise of "LaaS": Robert introduces his thesis on the future of Logistics as a Service and why AI innovation must come from inside the industry.
The Future of Freight Brokerage: Will brokers exist in 10 to 15 years? Robert breaks down the striking parallels to Wall Street and Robinhood.
Robby founded Envoy AI in 2023 after seven years at FreightWaves and TQL. The company builds autonomous agents for freight brokerages — handling quoting, carrier matching, and load coverage end‑to‑end. Envoy raised a $14M Series A from 8VC and Greycroft in 2025 and now powers desks at four of the top‑20 US brokerages.
Prefer audio? Listen here.
Timestamps
| 00:00 | Cold open — "I killed my own product and slept fine." |
| 02:40 | Why dashboards lost the brokerage |
| 09:15 | The agent stack at Envoy, walked end‑to‑end |
| 18:02 | Pricing models freight brokers will actually pay for |
| 27:34 | Hiring a 30‑person desk in 2026 vs. 2022 |
| 36:10 | What Robby's last investor meeting actually sounded like |
| 44:05 | The capacity crisis nobody is pricing in |
| 49:30 | One thing Robby would say to his 2019 self |
Pulled Quotes
"If your software needs a human to log in every morning, you didn't sell software — you sold a chore. We've been doing it backwards for a decade."
— Robby Nathan, 12:08
Links
| Mentioned in this episode | |
|---|---|
| Envoy AI | tryenvoy.ai |
| FreightWaves SONAR | sonar.freightwaves.com |
| TQL public filing, Q4 2025 | → Read the doc |
| "The end of the desk" (Robby's essay) | tryenvoy.ai/blog/end-of-desk |
Full transcript.
00:00:00.000 Yeah, and we can have an an extension of
00:00:01.920 Envoy AI down here, too. You're always
00:00:03.560 welcome to
00:00:04.584 >> [laughter]
00:00:04.880 >> Denver office.
00:00:05.840 >> Exactly. So, I think we're ready to just
00:00:07.760 get started. So, obviously very excited
00:00:11.280 to have, in my opinion, I believe KJ's
00:00:13.320 opinion, one of the leaders in the in
00:00:16.120 the
00:00:17.000 founding space within logistics and then
00:00:19.480 freight tech and now AI in in Robert
00:00:22.200 Nathan. So, thank you so much for coming
00:00:23.600 on the show today.
00:00:24.320 >> Thank you very much. Appreciate you guys
00:00:25.680 having me.
00:00:26.280 >> Yeah. Robbie, thank you for making the
00:00:27.480 trip down to our studio. I know it was
00:00:29.560 probably 45 50 minutes, so I know you're
00:00:31.480 busy, but thank you so much for coming
00:00:32.800 down.
00:00:34.080 Um your entrepreneur journey has been
00:00:36.680 across a few different things. It seems
00:00:38.560 like the thread is logistics, but where
00:00:40.600 did your entrepreneur spark start?
00:00:43.160 >> So, it's not that exciting. I started on
00:00:45.480 the loading docks when I was 14 years
00:00:47.480 old. Um during the summertime, I would
00:00:50.160 load trucks. I would count fasteners. It
00:00:53.240 was for a small distribution company
00:00:54.920 that my father had. Um we were sorting
00:00:57.280 screws, shipping them all over Chicago,
00:00:59.880 and that was how I learned about
00:01:01.880 businesses. I'd pull up at a dock,
00:01:05.360 and some would be small companies, some
00:01:07.040 would be big, and
00:01:08.680 all those companies were producing a
00:01:10.800 different product. And that was my sort
00:01:13.600 of entryway into entrepreneurial
00:01:16.240 activity and understanding that if you
00:01:19.000 have an idea, you could build a product,
00:01:21.200 sell it, distribute it, and make the
00:01:23.480 world a better place.
00:01:24.520 >> So, you worked for your dad in the
00:01:25.320 summers, is that right?
00:01:26.240 >> That I Yes, and I don't know if that
00:01:27.800 still happens these days.
00:01:29.920 By the way, I saw your daughter that's
00:01:31.480 working, you know, here and and spending
00:01:33.040 some time, which I think is great. More
00:01:34.960 people need to send their kids to work.
00:01:37.840 And you know, there's different ideas of
00:01:40.280 what type of work, and
00:01:42.160 you know, I think there's a lot of
00:01:44.600 There's just a lot of value that comes
00:01:46.280 from real work and communicating to real
00:01:48.880 people.
00:01:49.960 Everyone's talking about AI, but I think
00:01:53.000 we need to bring the kids back to back
00:01:55.200 to the office.
00:01:56.440 >> I agree totally.
00:01:57.360 >> Yeah, well, okay, so we're going to
00:01:59.280 touch on this a little bit later on as
00:02:00.560 we talk, but you've got two young boys,
00:02:01.960 I've got a daughter that's 1 and 1/2. Is
00:02:03.680 there anything that you're doing with
00:02:04.960 them to help kind of make sure that
00:02:07.040 they're getting that work ethic? Because
00:02:08.360 I would love to learn and make sure that
00:02:09.960 I'm instilling that in my kids,
00:02:11.001 [laughter] too.
00:02:11.520 >> So similar to being a CEO, everything
00:02:14.080 you do in front of your children, you're
00:02:16.120 modeling.
00:02:17.440 They're watching, they want to know what
00:02:19.440 you're doing, they're even if you think
00:02:21.240 they're not watching, they are. And the
00:02:22.560 same thing in in business, when you're a
00:02:24.040 CEO of a big company, people are
00:02:26.040 watching what you're doing, how you're
00:02:27.720 speaking, and um so I I just think the
00:02:30.440 the practice of understanding that uh
00:02:33.440 your children are not just going to do
00:02:35.360 what you say, but they're going to do
00:02:36.920 what you do.
00:02:38.440 And that's just something that I I think
00:02:41.480 is really important as as as I parent.
00:02:44.200 Um
00:02:44.800 Yeah, so what when your kids uh might
00:02:47.360 pop in a Zoom uh
00:02:48.991 >> [clears throat]
00:02:49.000 >> call or or whatnot, I think that's
00:02:51.320 great. I think people should smile about
00:02:53.080 that versus uh um not being happy about
00:02:56.080 that.
00:02:56.600 >> I mean, in the end, we're dealing with
00:02:57.720 people. Life happens, you're going to
00:02:59.200 have your kid pop in there, so I I 100%
00:03:01.080 agree. But backtracking to when you were
00:03:03.760 working over the summers, that's
00:03:05.320 obviously within the logistics space.
00:03:07.680 Was there something that when you were
00:03:10.120 doing that, you knew you wanted to go
00:03:11.720 into logistics, or you knew 100% that
00:03:14.120 you wanted to be an entrepreneur? Was
00:03:15.680 there any kind of aha moment doing that?
00:03:17.600 >> So no one wakes up and says I want to be
00:03:19.400 in logistics, [laughter] but just like
00:03:20.800 we teach, you know, our kids and model,
00:03:23.040 you have to be problem solvers. And when
00:03:25.600 you think about logistics, it's all
00:03:27.680 about solving problems. It's all about
00:03:30.519 solving problems faster, decreasing
00:03:32.160 latency, coming up with viable
00:03:33.720 solutions.
00:03:35.440 Um
00:03:36.200 So
00:03:38.320 >> Yeah.
00:03:39.840 And was there
00:03:42.200 the interesting dynamic of working with
00:03:44.400 your dad? So I had the the pleasure of
00:03:46.239 doing that, my father owns an an
00:03:47.720 architecture firm, and I was doing
00:03:48.959 similar things, just trying to help
00:03:50.800 clerical, or whatever it was, when I was
00:03:52.480 growing up. Did you like that dynamic of
00:03:54.920 working together?
00:03:56.600 >> So, I was This was back in the day
00:03:58.720 before there was Waze, before Google
00:04:00.560 Maps. So, there was only MapQuest. And
00:04:03.720 so, you'd have to print out MapQuest,
00:04:05.960 and I'd be driving around the inner city
00:04:07.560 of Chicago. And when you I'd get lost,
00:04:11.160 I'd have to call my dad.
00:04:13.200 >> Yeah.
00:04:13.720 >> And so, not only did I fail the mission
00:04:16.720 not going from point A to point B, I'd
00:04:19.120 have to And in some cases, you know, I
00:04:21.440 didn't have a cell phone at the time.
00:04:23.160 So, I'd have to get out of the car and
00:04:25.120 go into gas station and ask people and
00:04:27.480 problem-solve. And sometimes I'd have to
00:04:30.120 call my dad
00:04:31.360 and whip out the Rand McNally.
00:04:33.120 >> Well, that's something we all share in
00:04:34.040 commonality as well. I worked for my
00:04:35.480 dad. It was a linen company. So, if you
00:04:37.560 go to a nice restaurant, the chef coats,
00:04:39.080 the chef hats.
00:04:40.320 Uh it was founded in 1926. And so, my
00:04:43.120 job as a 13-year-old was to go wash the
00:04:44.680 trucks on the weekends. So, you imagine
00:04:46.400 like a UPS-sized truck. So, I'm from
00:04:48.280 Tacoma, Washington. So, it didn't matter
00:04:49.640 if it snowed, it rained, whatever it
00:04:51.560 was, I had to wash the trucks. And I
00:04:53.120 think they paid me $55 a week.
00:04:56.063 >> [laughter]
00:04:56.718 [clears throat]
00:04:56.720 >> Hey, at least you're still earning some
00:04:58.160 income.
00:04:58.400 >> asked the question about working for
00:04:59.680 your father. Maybe not my favorite
00:05:01.400 thing, cuz I felt like most of my life I
00:05:03.080 was his employee. He had four sons, so
00:05:05.919 um but definitely taught me you know,
00:05:07.120 taught me hard work.
00:05:08.160 >> Yeah. Yeah. Um I It's a similar thing
00:05:11.440 with me. It's like I think that the
00:05:13.280 experience is so phenomenal. I love my
00:05:15.360 dad to death. Him and I see things very
00:05:17.520 differently. And I by no means have the
00:05:19.800 the entrepreneurial spirit like you, but
00:05:21.280 I was always telling him like, "You
00:05:22.640 should be able to do this or do this a
00:05:24.120 little bit differently." So, I always
00:05:25.320 like to see what or I guess how that
00:05:28.000 dynamic works.
00:05:29.520 >> Now, in terms of dads, the biggest gift
00:05:32.000 that he gave me was not teaching me how
00:05:34.480 to work or letting me work for him. It
00:05:36.720 was not allowing me to work for him
00:05:38.880 after college.
00:05:40.520 And I wanted to. I thought I could make
00:05:42.320 his business so much better, and and we
00:05:44.680 could grow it. And he said, "You need to
00:05:46.919 go do your own thing. We don't believe
00:05:48.920 in nepotism in this family and go out
00:05:51.920 and make your own way." And so, at 22,
00:05:55.880 uh I had to figure it out myself.
00:05:57.800 >> I love that. And we I definitely want to
00:05:59.360 touch on that here in a second, but if
00:06:01.200 we're taking one step back, so worked
00:06:03.360 with your dad, understanding the
00:06:04.840 logistics space, driving a truck,
00:06:07.400 you decided on CU Boulder. Why did you
00:06:09.960 decide to come to school out here? Why
00:06:11.880 philosophy? Like what made you kind of
00:06:14.040 venture out?
00:06:15.480 >> Uh so,
00:06:16.920 uh
00:06:18.360 >> Were there other schools that you were
00:06:19.520 looking at besides Boulder?
00:06:21.160 >> Yes, uh my mother is still not happy
00:06:23.480 with me that I got [laughter] into many
00:06:25.280 other schools that uh might have had a
00:06:27.600 better reputation from an academic
00:06:29.680 institution uh perspective, but I wanted
00:06:32.320 to go to Boulder. I love the mountains.
00:06:34.280 I thought it'd be a great lifestyle, 300
00:06:36.200 days years of uh days of sun, and uh
00:06:40.880 that's that that was where I made the
00:06:42.400 decision. Now, why did I study
00:06:43.600 philosophy? I wanted to read, I wanted
00:06:45.680 to write, I wanted to learn about
00:06:47.720 systems, and at the time it was it was
00:06:49.760 called social policy and values, so I
00:06:51.560 was really interested in how do we make
00:06:53.760 the world a better place? Now, I didn't
00:06:55.480 know later on that making the world a
00:06:57.720 better place through logistics was
00:06:59.520 possible,
00:07:00.240 >> Yeah.
00:07:00.640 >> but I do think that the the operators
00:07:03.600 that have stayed in this industry the
00:07:05.160 longest fundamentally believe that we
00:07:07.880 are helping to make the world just a a
00:07:09.919 little better by whether it's technology
00:07:12.480 or a service or um
00:07:14.680 by bringing on great great teams.
00:07:16.919 >> Was there any type of like a specific
00:07:18.440 professor that said something profound
00:07:20.440 to you that made you change away from
00:07:22.200 philosophy and go back to business or or
00:07:24.680 is there like a theme that or there's
00:07:26.040 something you learned there that is
00:07:27.240 still sticks with you to this day?
00:07:28.560 >> So, the the theme that sticks with me
00:07:30.600 was I know that I don't know. It was the
00:07:33.720 greatest paradox it was it was a
00:07:35.720 Socratic uh Socrates used to say it,
00:07:38.240 which was I know that I don't know. And
00:07:40.919 we
00:07:41.125 >> [clears throat]
00:07:41.200 >> when we think about business, we're
00:07:43.080 testing ideas and concepts that we think
00:07:46.040 we know, but we need to actually test
00:07:48.280 them in the laboratory and see if
00:07:49.640 they're they're actually create ROI. So,
00:07:52.480 um I think that's what stuck with me.
00:07:55.000 Um why did I go into business? Well,
00:07:57.720 very hard to make money as a modern day
00:07:59.560 philosopher.
00:08:01.120 Uh I tried to when I was 22, I spent
00:08:03.480 some time overseas in China.
00:08:06.000 Uh and then when I got back to the
00:08:07.360 United States, uh
00:08:09.280 uh it was either uh philosophy, which
00:08:11.400 was not easy to generate income, or go
00:08:14.200 into the wide world of logistics. So, uh
00:08:16.720 was fortunate to get my first start at a
00:08:19.440 company called AFN,
00:08:21.440 uh and that's where I learned the
00:08:22.440 industry.
00:08:23.640 >> Interesting. And definitely want to
00:08:24.880 learn about AFN, too. But I didn't
00:08:26.160 actually know that you had the
00:08:26.880 opportunity to go abroad and go over to
00:08:28.680 China after school. What were you doing
00:08:30.560 there?
00:08:31.200 >> I'm not at liberty to say.
00:08:32.870 >> [laughter]
00:08:34.080 >> Yeah, I was in China is a is definitely
00:08:35.960 crazy place. So, AFN, how did you then
00:08:38.919 end up in AFN? And then again, going
00:08:40.599 back to what you're saying before,
00:08:41.799 couldn't work with your dad. Like, what
00:08:43.640 made you really want to get into the
00:08:45.080 logistics space? Or did it just fall
00:08:46.960 into your lap?
00:08:47.600 >> interject a quick question? Like, how
00:08:49.080 did you apply online? Or like, how did
00:08:51.320 you get Did you look at other brokerages
00:08:53.480 or other types of companies?
00:08:54.640 >> So, this is interesting. So, I remember
00:08:56.440 being 22 years old, I came I 20 I came
00:08:59.360 back from China, and I got on
00:09:01.480 CareerBuilder.
00:09:02.440 >> Yeah.
00:09:03.520 >> And no one emailed me back.
00:09:06.520 I didn't get any emails. And I didn't
00:09:09.240 know what to do.
00:09:10.520 And so, I I'd heard that there was this
00:09:12.839 thing called freight brokerage, and
00:09:14.280 there was this legend called Paul Loeb.
00:09:16.800 And Paul Loeb lived in uh a town uh just
00:09:19.800 north of of Chicago, and I happened to
00:09:22.520 grow up in that town. And so, I'd heard
00:09:24.280 about logistics. And Paul not just
00:09:27.880 created American Backhaulers, and really
00:09:29.880 is the godfather of modern day
00:09:32.680 uh freight brokerage, but he spawned
00:09:35.200 this ecosystem in the northern suburbs
00:09:38.360 of Chicago that created I'd say 20 plus
00:09:42.440 CEOs of top 200 3PLs. So, it was it was
00:09:48.280 sort of by default
00:09:49.960 maybe by where I lived that I just
00:09:51.840 gravitated towards logistics, walked on
00:09:54.360 the floor at AFN, and
00:09:57.440 2 days later had a role.
00:09:59.080 >> I love it. We were talking about this
00:10:00.720 earlier in terms and we love asking
00:10:03.240 everybody that question how you get into
00:10:04.960 logistics because I feel like it's one
00:10:06.320 of those industries you don't expect to
00:10:08.360 get into and then it kind of just keeps
00:10:09.720 you here forever where I was at DePaul
00:10:12.320 going to school and I was just working
00:10:14.040 out with a guy. He's like, "What are you
00:10:15.440 doing after school?" I'm like,
00:10:16.720 "I have no idea at this point." He ended
00:10:18.760 up getting a job at C.H. Robinson and he
00:10:20.680 said you should apply, applied, went
00:10:22.880 through a couple interviews, and then
00:10:23.960 literally just the first job that I
00:10:25.280 applied to found myself starting there
00:10:27.280 in a very similar type of situation.
00:10:29.720 >> Yeah, I got it. I played for
00:10:31.040 GlobalTrans. So, I was flipping homes
00:10:32.640 and it was like the end of '06 early
00:10:34.120 '07. And my dad's like, "I think you
00:10:36.480 need to figure out something else to
00:10:38.080 do."
00:10:38.632 >> [laughter]
00:10:39.200 >> Um and I'm not sure if you're
00:10:40.080 capitalized enough to keep going you
00:10:41.680 know as long as you want to go. And for
00:10:43.400 me I just applied online, Mike Little
00:10:45.120 called [clears throat] me. Um he didn't
00:10:46.440 like me for his role, Andrew liked me
00:10:48.839 for his role, hired me, and I've been in
00:10:51.040 logistics ever since.
00:10:52.160 >> Yeah. And so when you started with AFN,
00:10:54.560 what were you doing there?
00:10:55.920 >> I was a carrier sales rep. So, actually
00:10:58.040 this was interesting. I was not a
00:11:00.080 carrier sales rep. I wasn't even allowed
00:11:01.720 to make outbound calls. I was a phone
00:11:04.160 answer. So, I went to 4 years of school,
00:11:06.240 I read all this philosophy, I thought I
00:11:08.320 had a high IQ, and I'm sitting there
00:11:10.800 answering phone calls
00:11:13.280 and dispatching drivers.
00:11:16.040 So, I'm sitting there and this is like
00:11:17.720 my fourth day
00:11:19.440 and I'm talk- talking a hundred drivers
00:11:21.400 a day and I'm dispatching them and
00:11:23.040 remember from my MapQuest days I'm not
00:11:24.839 really that good at directions.
00:11:25.792 [laughter]
00:11:26.760 So,
00:11:27.920 I figured that I had to get out of of
00:11:30.200 dispatch as fast as possible.
00:11:32.440 >> Yeah.
00:11:33.000 >> And so I was sitting at the time next to
00:11:35.360 this guy named Mark Robbins who still
00:11:37.200 he's a 2,000 load book
00:11:40.120 a month rapid global trans still is
00:11:41.880 fantastic a brilliant carrier up.
00:11:44.360 >> Yeah.
00:11:44.720 >> And I sat next to him. And I just
00:11:47.000 watched everything he did. And then
00:11:48.880 behind me I had Mike Hammel who is is at
00:11:51.760 Highway now. He was tremendous leader
00:11:54.400 and manager
00:11:55.920 who who helped me navigate through my
00:11:57.600 first couple of months. And they built a
00:12:00.080 great ecosystem at AFN. Mike Nervick and
00:12:03.880 and Ryan Dobby who's no longer here.
00:12:06.320 They taught a lot of people. They made a
00:12:08.880 lot of people better.
00:12:11.000 And you know they sort of took what Paul
00:12:12.960 Loeb did and created a another
00:12:15.200 generation of freight operators.
00:12:17.680 >> Yeah. I think that that is one of the
00:12:19.720 things that separates a lot of the the
00:12:21.720 people in our space is are the ones that
00:12:23.920 take it upon themselves to either A find
00:12:26.280 mentors in the space to really learn
00:12:27.760 from but also just take it upon yourself
00:12:29.440 to do the job. It was a very similar
00:12:31.840 experience at least for my end where you
00:12:34.120 know for your degree and went in and
00:12:36.160 then I was doing something very similar.
00:12:37.600 I was an order taker filling out sheets
00:12:39.520 online and and just making sure that
00:12:41.200 things were moving seamlessly but I was
00:12:43.440 like how can I continue and actually
00:12:45.280 further progress my career?
00:12:47.560 So actually funny enough there's one of
00:12:49.839 my former mentors from Robinson is here.
00:12:52.440 His son just got accepted to Boulder so
00:12:53.760 I'm going to go meet up with him a
00:12:54.600 little bit later. I get to catch up with
00:12:56.360 him. But also it's just about me then
00:12:59.560 sitting there and saying I need to go
00:13:01.240 out and actively make cold calls. I need
00:13:03.080 to start building a book of business
00:13:04.920 outside of one the normal time that I'm
00:13:06.960 supposed to be working and I feel like
00:13:08.480 that's tends to lead to success in the
00:13:10.400 space.
00:13:10.880 >> Are you talking about Ray Black?
00:13:11.960 >> Yeah, Ray Black well yeah. Yep. Yeah,
00:13:13.640 he's up here. Yeah.
00:13:14.640 >> So Coleman just it's it's the people
00:13:17.440 that understand and it sounds like you
00:13:19.040 had that moment no one's coming to save
00:13:22.080 you.
00:13:22.480 >> Yep.
00:13:23.320 >> You're sitting in that desk. You're 22
00:13:25.920 you're 44 you're me you're a CEO.
00:13:27.960 >> Yeah.
00:13:28.400 >> No one's coming to save you.
00:13:29.960 >> Yep.
00:13:30.360 >> You need to work and you need to
00:13:31.680 execute.
00:13:32.520 >> Yeah. That's and it's interesting that
00:13:34.480 you say that and especially being in our
00:13:36.160 seats now when we're talking people
00:13:37.520 through their careers,
00:13:39.080 I'd say that that's a a great thing to
00:13:41.240 reiterate to everybody because
00:13:43.640 traditionally, right, you can climb the
00:13:45.000 corporate ladder and do whatever it is,
00:13:46.760 but even then, you still have to go
00:13:48.400 above and beyond and make sure that
00:13:49.800 you're getting recognized, not
00:13:50.920 necessarily just staying in your silo,
00:13:52.840 right?
00:13:52.920 >> When we talk about careers, we talk
00:13:54.560 about parenting or managing in business,
00:13:57.280 teaching your team, teaching your kids
00:13:59.960 how to advocate for themselves.
00:14:01.680 >> Yeah.
00:14:02.240 >> That is the skill. Be relentless, but
00:14:04.440 how do we advocate for ourselves? You
00:14:06.600 could be the best operator, but you're
00:14:08.000 not if you're not advocating
00:14:10.040 to your your manager, it's really hard
00:14:12.360 to achieve upward mobility.
00:14:13.920 >> Yeah.
00:14:15.040 >> So,
00:14:15.440 >> Yeah.
00:14:15.640 >> So, at AFN, like how did you continue to
00:14:17.840 advocate for yourself or maybe become an
00:14:19.680 intrapreneur?
00:14:20.840 >> So,
00:14:22.560 great, I love the word intrapreneur
00:14:24.280 because I think that there's a lot of
00:14:26.560 talented people out there that have
00:14:28.920 built [clears throat] businesses inside
00:14:30.720 of businesses. Um
00:14:32.440 and that was my first taste. Uh it was
00:14:34.160 called the CCC, critical conversion,
00:14:36.880 uh concept, which was I believed at the
00:14:39.160 time that there was this opportunity to
00:14:41.440 convert
00:14:43.680 over-the-road freight to intermodal. And
00:14:45.839 this was before people were really doing
00:14:47.360 that. Uh and I had a wonderful manager
00:14:50.280 who, Mike Hamel, who said, "Go and build
00:14:52.400 a business plan and do that and start
00:14:54.240 booking intermodal loads." So, figuring
00:14:56.440 out at the time it was just mode
00:14:58.160 diversification.
00:14:59.839 Uh so,
00:15:00.920 how that can relate to today, it's just
00:15:03.040 figuring out different avenues of
00:15:04.640 revenue generation, um
00:15:07.360 challenging that, trying to understand,
00:15:09.200 you know, where you can add value to
00:15:11.200 your customers. In this case, it was
00:15:13.520 uh finding a more cost-efficient way to
00:15:16.520 ship their freight via intermodal.
00:15:19.280 >> So, did you build out that product for
00:15:20.880 AFN then?
00:15:21.320 >> So, I built out for AFN. It was small. I
00:15:25.120 actually
00:15:26.320 brought them the thesis that we needed
00:15:27.720 to buy an IMC. This is 2005. I'm 23 and
00:15:31.840 I said, "We have to buy an IMC."
00:15:33.920 >> Yeah.
00:15:34.360 >> That's the only way to be get get big in
00:15:36.160 intermodal. And a year later actually
00:15:38.920 Coyote did buy an IMC and they moved
00:15:41.480 that direction. We never did.
00:15:44.520 AFN was a tremendous company,
00:15:45.830 [clears throat] ended up exiting to
00:15:47.400 Global Tranz years later. Um but that
00:15:51.680 was my first taste of like how do you
00:15:53.240 build something inside of a company and
00:15:56.160 how do you go from zero intermodal loads
00:15:58.360 to making it a multi-million dollar
00:16:00.440 business unit?
00:16:01.640 >> Yeah.
00:16:02.560 So, you were at AFN for what was it,
00:16:04.360 five years?
00:16:05.040 >> I was there for 30 months.
00:16:07.920 I actually never would have left
00:16:10.400 but
00:16:13.440 businesses, as you know, commission
00:16:15.320 structures change in the logistics
00:16:17.120 sector. If you're a leader, you should
00:16:19.000 definitely think before you change
00:16:20.320 commission structures.
00:16:22.320 And it's just very easy as a as a young
00:16:25.520 operator, my commission changed and I
00:16:27.520 walked out the next day and had the
00:16:30.120 opportunity to start Load Delivered
00:16:31.720 Logistics with
00:16:33.560 my former camp counselor. So, I was 7
00:16:36.400 years old, I went to this camp and had a
00:16:39.240 a tremendous
00:16:40.680 counselor named John Micklon.
00:16:42.760 His family was an owner in the Chicago
00:16:44.880 Bulls and
00:16:47.520 we started the company in 2008 and that
00:16:50.720 was how Load Delivered launched.
00:16:53.200 >> Oh, go ahead, please.
00:16:53.920 >> going to say it is wild how if you cut
00:16:55.520 commissions or change commission
00:16:56.720 structures, there's an exodus. I sold
00:16:58.839 computers at IBM. They changed it five
00:17:01.000 times in two and a half years. Everybody
00:17:02.920 left.
00:17:03.839 >> Yeah.
00:17:04.000 >> And it's like, here's the new commission
00:17:05.000 plan, right? And it's like, you're going
00:17:06.560 to make more money. It's like, okay, I
00:17:07.680 have to sell twice as much to make a
00:17:09.000 little less than before.
00:17:10.240 >> Mhm.
00:17:10.680 >> I mean, they can spin it any way they
00:17:11.800 want but you're going to leave if you're
00:17:14.160 a salesperson.
00:17:15.119 >> Well, what do you what do you think
00:17:16.439 about commission plans in in freight,
00:17:18.839 right? Especially with AI. How do How
00:17:22.480 are our operators going to think about
00:17:24.359 commission reps versus AI reps in the
00:17:27.040 future?
00:17:27.760 >> Yeah.
00:17:28.439 >> Man, that's such a a loaded question. I
00:17:30.920 think it's going to change all the time.
00:17:32.720 I think that if you're looking at an AI
00:17:35.400 rep, I don't think that there's going to
00:17:36.680 be any commission that's associated with
00:17:38.240 it. Obviously, because it's not an
00:17:39.800 actual human being doing it. I don't
00:17:41.960 think that we're necessarily either at a
00:17:43.840 point now or in the future to where
00:17:46.400 something in AI is going to be
00:17:48.200 sophisticated enough to go through an
00:17:49.840 enterprise cell. I think that you're
00:17:51.320 always going to have to have somebody
00:17:52.600 associated with it. But to your point, I
00:17:55.520 wouldn't be surprised if it there is a
00:17:57.880 lesser of a commission because AI is
00:18:00.520 involved in some way, shape, or form.
00:18:02.640 So, theoretically, sales reps can go out
00:18:04.840 and do more with it and hopefully recoup
00:18:06.800 some of that money.
00:18:07.520 >> maybe contrarily, if a person could do
00:18:09.240 25 loads a day, but now they can do
00:18:11.680 1,200 loads a day, like maybe the
00:18:13.520 commission is through the roof. And the
00:18:15.280 AI's been able to help them get there.
00:18:16.880 >> Yeah. Yeah.
00:18:18.080 >> How How do you How do you approach it?
00:18:20.160 Or how do you think the brokerage part
00:18:21.360 of it
00:18:21.480 >> So, I think Tim Barton, for instance, as
00:18:23.680 a good example, building a company that
00:18:26.440 really is built for the customer
00:18:28.120 relationship person.
00:18:29.480 >> Yeah.
00:18:29.960 >> So, if you look at at the
00:18:33.000 freight brokerages in general, um and
00:18:35.240 Tim built freightquote.com, which was
00:18:37.000 tremendously successful, sold to CH
00:18:38.560 Robinson.
00:18:39.200 >> Yeah.
00:18:39.920 >> Uh you look at Paul Loeb, you look at
00:18:41.720 Jeff Silver. They all built these
00:18:43.920 big brokerages. Um and then
00:18:47.680 you look at uh
00:18:49.480 you look at the the model that actually
00:18:51.240 works today.
00:18:52.280 >> Mhm.
00:18:53.000 >> The most profitable brokerages right now
00:18:56.320 are cradle-to-grave.
00:18:58.080 >> Really?
00:18:58.800 >> You need to be able to operate on both
00:19:01.440 sides. And so, where I see technology
00:19:03.520 coming in is it's going to empower that
00:19:05.680 person with customer relationships
00:19:08.000 >> Mhm.
00:19:08.600 >> to book freight, operate freight
00:19:10.800 autonomously
00:19:12.440 versus they used to have to depend on a
00:19:14.520 carrier up on an operations rep on a
00:19:16.800 finance person. I think that will evolve
00:19:19.440 a little bit and I think, you know, some
00:19:21.000 of your clients are ahead of that curve.
00:19:23.240 Um
00:19:24.400 we'll probably see more of of that model
00:19:26.680 in the near future.
00:19:27.920 >> Interesting. I know that was and I'm
00:19:29.120 sure you experienced this at AFN as
00:19:30.600 well. That was one of the most
00:19:31.520 frustrating part of the jobs from a
00:19:33.200 buy-sell model is I land a bunch of
00:19:35.880 freight then I have to rely on other
00:19:37.200 people that might not necessarily care
00:19:39.520 as much as I do to uh make sure that
00:19:41.440 everything moves seamlessly. So, having
00:19:42.920 the control I 100% can see the value in
00:19:44.920 that.
00:19:46.218 >> [snorts]
00:19:46.280 >> I think that's interesting.
00:19:47.440 >> Yeah.
00:19:47.760 >> Cuz you look at maybe the last large one
00:19:49.280 was maybe Access America that sold to
00:19:50.840 Coyote and then they had some challenges
00:19:53.080 to be able to convert everybody over to
00:19:54.880 a buy-sell model.
00:19:55.880 >> Yeah.
00:19:56.920 Um
00:19:58.280 backtracking actually to when you
00:19:59.320 started Load Delivered. That was a super
00:20:01.000 interesting take when you were talking
00:20:02.280 about how you wanted to start it with
00:20:03.520 the the former camp counselor. What was
00:20:04.880 his name again?
00:20:05.760 >> Uh John Micklon.
00:20:06.880 >> John Micklon. How where did that come
00:20:08.680 from? Did you just leave one day at AFN
00:20:10.680 and said, I need to call this guy up or
00:20:12.360 or what was the thought process to
00:20:13.840 actually getting it started?
00:20:14.880 >> So, well
00:20:16.600 backing up actually, John was one of the
00:20:19.080 seed founders for D&D Express which was
00:20:21.480 started by Danny Zamos.
00:20:23.760 John sold that to Paul Loeb and that was
00:20:26.080 how Paul started uh Command
00:20:28.560 Transportation which later sold for $420
00:20:31.600 million to Echo Global.
00:20:33.600 >> Mhm.
00:20:34.040 >> Uh
00:20:34.640 and so, he'd had some experience uh
00:20:37.520 early on building uh and John and I just
00:20:40.080 thought we could build something better
00:20:41.960 and and bigger and uh with a little more
00:20:43.960 technology in it.
00:20:45.840 >> Did you take any investment to start the
00:20:47.160 business or was it bootstrapped?
00:20:48.560 >> Uh John was the money behind it uh but I
00:20:51.200 consider it was pretty bootstrapped. Uh
00:20:53.440 we we did not scale with institutional
00:20:56.040 capital.
00:20:57.200 Uh and at the time we were battling
00:20:59.040 institutional capital. So, when Warburg
00:21:00.920 Pincus started to uh build out Coyote,
00:21:04.480 you know, and we go back to that model
00:21:07.040 that was not a profitable model. If you
00:21:09.200 look at Coyote, they did not make money
00:21:12.040 with the exception of $90 million in
00:21:14.240 EBITDA the year they were able to exit
00:21:16.600 for $1.8 billion to UPS. So,
00:21:19.800 that model never produced a lot of
00:21:21.320 money, which is interesting because you
00:21:22.760 have the Coyote model
00:21:24.440 and then people from Coyote got sucked
00:21:26.480 into to Convoy or to Uber Freight or
00:21:28.920 other digital models, and now they're
00:21:30.600 getting sucked into these AI companies.
00:21:32.200 So, you have people that have never made
00:21:34.200 money in freight
00:21:35.520 >> Yeah.
00:21:35.760 >> that their careers have been subsidized
00:21:37.760 by three or four different companies,
00:21:39.920 private equity or VC, and these
00:21:41.920 companies have never materialized into
00:21:44.240 profitable entities.
00:21:46.200 Um so, it's just it's interesting to see
00:21:47.760 how the freight game has evolved. Um
00:21:50.600 that said, we're really early on in this
00:21:53.160 next cycle.
00:21:54.440 >> Yeah. And we work with founders all the
00:21:56.760 time.
00:21:57.640 You're obviously [clears throat] a
00:21:58.280 multiple-time founder. What was the
00:22:00.320 first day like of just getting Load
00:22:02.640 Delivered started?
00:22:04.360 >> The silence is the most [laughter]
00:22:07.280 interesting part of a startup. And no
00:22:09.040 one talks about this.
00:22:11.040 You're You don't have any inbound
00:22:12.840 emails.
00:22:14.120 And so, just think about we all are are
00:22:15.840 in the business and we have these Slacks
00:22:17.640 coming in and emails coming in and phone
00:22:19.760 calls.
00:22:21.080 No one calls you.
00:22:22.240 >> Yeah.
00:22:22.520 >> No one emails you. And And so, that's
00:22:24.040 always interesting and a lonely moment.
00:22:26.560 But, that's when you That's part of the
00:22:29.560 the embracing is that lonely moment. I
00:22:31.600 call it the the sadness, uh the
00:22:33.560 loneliness that nobody notices.
00:22:35.920 Uh
00:22:36.720 And that's when entrepreneurs really
00:22:38.600 start to innovate.
00:22:39.960 >> Yeah.
00:22:40.920 >> I find at least.
00:22:42.120 >> Yeah.
00:22:43.080 And I would say that arguably probably
00:22:45.520 one of the worst times to start a
00:22:47.160 business, at least before 2009, just
00:22:49.400 with everything that was going on in the
00:22:50.680 economy. But, you obviously found a
00:22:52.640 large amount of success
00:22:54.760 really since you started it, especially
00:22:56.120 over that four-year period, give or
00:22:57.960 take. What was that like?
00:22:59.800 >> So, when When started, it was actually
00:23:01.080 Bear Stearns that just
00:23:03.560 uh you know, basically collapsed. The
00:23:04.880 economy was in disarray.
00:23:06.560 >> Yeah.
00:23:08.480 >> And the It's easier now because, you
00:23:11.160 know, I was young. I didn't have any
00:23:13.160 money. I didn't have a family. I wasn't
00:23:15.480 as knowledgeable about macroeconomics
00:23:17.520 situation and uh
00:23:20.360 we turned off the the
00:23:23.120 any news. There was no news allowed in
00:23:25.880 our office.
00:23:26.680 >> Wow.
00:23:27.040 >> Because it was so negative and energy
00:23:29.320 that was going on in 2008, I said if we
00:23:31.880 want to win, we need to turn off the
00:23:33.240 news and we need to focus internally. We
00:23:35.400 can only control
00:23:37.560 what goes on in this office. And we are
00:23:40.320 in an industry where uh there's a lot of
00:23:43.360 uh activity and motion. There's trucks.
00:23:46.360 Uh
00:23:47.120 we need to focus internally and that's
00:23:51.160 what we did for literally the next 11
00:23:53.120 years.
00:23:53.920 >> The first four or five years though, I
00:23:55.160 mean, it really worked turning the news
00:23:56.560 off cuz I think what was your growth
00:23:57.880 like? Over 975% or something?
00:24:00.040 >> We were in Inc. 500, which is really
00:24:01.720 exciting. Uh we were uh 11th
00:24:03.880 fastest-growing company in Chicago. Um
00:24:06.640 so, we hit that ex- sort of accelerator
00:24:09.360 button.
00:24:10.520 Uh I think it was partially good timing,
00:24:12.640 partially a fantastic team.
00:24:14.840 >> Yeah.
00:24:15.080 >> Um
00:24:16.200 and then a lot of it was just great
00:24:18.080 customer support. And we we focused on
00:24:21.040 customers. And I know that's the ethos
00:24:22.840 of of Talent Solvers, but it's all about
00:24:25.280 the customers. And I think especially
00:24:27.720 specifically in brokerage, if you can
00:24:29.080 really lean into the customer service in
00:24:31.240 that 2008 to 2012 time frame, it was a
00:24:34.480 lot easier to grow
00:24:36.280 uh
00:24:36.840 versus today when you think about
00:24:38.560 scaling, there's just a lot of different
00:24:40.880 variables that go into the ability to
00:24:43.160 scale and scale profitably.
00:24:45.560 >> So, growing that much in your late 20s,
00:24:48.520 did ego ever come into Do you have to
00:24:50.640 check your ego at the door? I mean, it
00:24:52.240 must have been pretty empowering.
00:24:54.000 >> So,
00:24:55.520 I had a lot of I had a great team, and
00:24:58.080 if you have a great team, they'll check
00:24:59.880 your ego.
00:25:00.622 >> [laughter]
00:25:01.360 >> Uh and so I think that's important,
00:25:03.000 surrounding yourself with mentors
00:25:05.840 uh that and advisors, I think is
00:25:07.720 critical. And also recognizing, you
00:25:10.720 know, going back to that philosophy, is
00:25:13.120 I know that I don't know. And so I think
00:25:15.640 that if you constantly are trying to
00:25:17.360 learn and grow,
00:25:19.040 um
00:25:19.920 you don't get sort of
00:25:22.840 pulled into uh you know, thinking that
00:25:25.160 you're you're bigger than you are.
00:25:26.560 >> Yeah. Was there ever a point in time of
00:25:29.040 running Load Deliver over those 10 years
00:25:30.680 where you ever
00:25:31.960 I might go out of business tomorrow.
00:25:33.440 >> Twice.
00:25:34.520 >> Really?
00:25:35.200 >> There was two times where essentially a
00:25:37.400 lot of brokerages run negative working
00:25:39.040 capital businesses, so
00:25:41.160 uh it's dollar in, dollar out. And when
00:25:43.320 you scale too fast and the market flips,
00:25:46.320 very hard to recover from that. So your
00:25:48.160 debt-to-equity ratio flips, the bank uh
00:25:51.040 typically are not very excited um
00:25:53.920 when you're in that situation. So there
00:25:55.880 was two times, you know,
00:25:57.640 we were a big company and you know, you
00:25:59.680 have to pay yourself zero. Um you have
00:26:01.600 to figure out how to um operate
00:26:03.760 differently, and and that's what
00:26:05.360 prepared me for this evolution. Um
00:26:08.600 you know, I had to go from 184 people
00:26:12.320 to 77.
00:26:14.160 And people don't hear about that in Inc.
00:26:16.480 magazine or in Crain's, but we had to
00:26:18.920 systematically create operational
00:26:20.960 leverage in our business because the
00:26:23.480 market compressed. And so when I talked
00:26:25.720 to operators over the past couple years,
00:26:27.600 I I understood the pain they're going
00:26:29.160 through.
00:26:30.360 Uh a lot are still in that sort of right
00:26:33.000 now in this in this market, but
00:26:34.840 hopefully in the next couple months
00:26:36.200 they'll be able to work themselves out.
00:26:38.960 >> I think that's one of the important
00:26:40.160 things to understand from an
00:26:41.360 entrepreneurial journey is that
00:26:43.080 everybody always talks about the good,
00:26:44.960 right? Yeah, exactly, making the Inc.
00:26:46.680 500 and all that. But there are
00:26:48.480 inevitably down times again when you're
00:26:50.560 having to scale or drop head count by
00:26:52.480 50%
00:26:54.120 um
00:26:54.960 but I think all of everything that you
00:26:56.440 were just talking about and especially
00:26:58.160 when the economy was rough talking about
00:27:00.360 how we can control what's in our four
00:27:02.000 walls that speaks a lot to the culture
00:27:04.400 that you had built there and again
00:27:06.760 making sure that as you're reducing head
00:27:08.680 count you're still keeping people on
00:27:10.160 board and they're still motivated.
00:27:12.800 Describe the kind of the importance of
00:27:14.400 the culture that you built there in
00:27:16.200 terms of getting to the success that you
00:27:17.960 wanted um and just kind of how you did
00:27:20.120 that.
00:27:22.560 >> That's uh
00:27:25.640 I'm not sure. I'd have to think about
00:27:27.240 that. [laughter] That's
00:27:28.000 >> there's one cool thing you did from a
00:27:29.240 culture perspective that I learned when
00:27:30.720 I first met you was that maybe on I'm
00:27:33.520 not sure if it was once a month or every
00:27:35.480 other Friday you'd have somebody come in
00:27:37.560 and maybe do nails for the ladies that
00:27:38.880 worked in the office.
00:27:40.480 >> Uh
00:27:41.120 so
00:27:41.960 >> I remember it.
00:27:43.000 >> That that was definitely [laughter]
00:27:45.120 So here was the best advice I got from a
00:27:47.480 leader who was a CFO of of five publicly
00:27:49.920 traded companies. He was the one that He
00:27:52.720 said he he's like you are going to need
00:27:54.840 to change your business model and you
00:27:57.120 could either take a hatchet
00:27:59.640 or you could take an axe.
00:28:01.760 And I'll help you do either but we're
00:28:04.240 going to have to change the dynamics of
00:28:05.880 this business. And um so during that
00:28:09.280 time when we had to decrease the amount
00:28:11.560 of people he said the people on your
00:28:13.880 team you need to continue to take care
00:28:15.880 of. You need to make sure they're paid
00:28:18.160 well. You need to make sure that
00:28:19.840 everything that you were giving them
00:28:21.280 prior to um doing some layoffs that you
00:28:23.960 can continue that. And so what we did is
00:28:26.280 we we rallied around the the best people
00:28:29.480 at the company they stepped up and in
00:28:31.560 2018 uh a lot of those leaders ended up
00:28:34.640 doing really well upon the exit.
00:28:36.640 >> Yeah.
00:28:37.040 >> Good for you. That's good advice from
00:28:38.320 your mentor.
00:28:39.080 >> Yeah. And can you elaborate on what the
00:28:42.240 difference between an axe and a hatchet
00:28:43.800 is? I'm assuming hatchet just a little
00:28:45.600 bit slower in terms of how you're
00:28:46.920 changing the business versus axe. You're
00:28:48.560 just going in and changing everything
00:28:49.880 right off the bat.
00:28:50.800 >> Yeah, so most first-time founders will
00:28:52.560 always choose the hatchet when given the
00:28:54.459 >> [laughter]
00:28:54.560 >> opportunity.
00:28:56.160 I chose the hatchet.
00:28:57.400 >> Yeah.
00:28:58.720 >> Which is was a great experience. The The
00:29:01.160 axe would be to make big decisions
00:29:03.520 quickly.
00:29:04.120 >> Mhm.
00:29:04.760 >> And move swift.
00:29:06.440 Everyone's always
00:29:07.720 careful about culture and optics and
00:29:09.960 what people think. No one cares.
00:29:12.600 >> Yeah.
00:29:13.480 >> What's important is that you have if you
00:29:16.040 have if you have fiduciary
00:29:17.560 responsibility, you are making sure that
00:29:19.400 you take care of your investors and your
00:29:21.080 team.
00:29:21.600 >> Mhm.
00:29:22.280 >> And that was always really important to
00:29:25.000 me.
00:29:25.880 >> So I'm assuming your stance changed now.
00:29:27.680 If you were to having to do something
00:29:29.360 over again from that drastic, you're
00:29:31.320 taking the axe to it.
00:29:32.720 >> Absolutely.
00:29:33.800 >> Interesting.
00:29:35.000 So started Load Delivered, obviously
00:29:37.480 extremely successful, and then I believe
00:29:38.920 it was in 2013 started and founded a
00:29:41.320 company called Logistical Labs. Where
00:29:43.440 did that come from? What was the goal
00:29:45.960 behind it in working with both of them
00:29:47.760 in tandem?
00:29:48.880 >> So Logistical Labs was created because
00:29:52.160 we just could not compete with C.H.
00:29:54.080 Robinson and Coyote. I was looking I was
00:29:56.440 actually here at Whitewave Foods, Jake
00:29:58.120 Kilgore, really good guy
00:30:00.920 see him at the Denver Transportation
00:30:02.280 Club.
00:30:02.720 >> Yeah.
00:30:03.040 >> He we were at Whitewave in Broomfield,
00:30:05.360 Colorado, and he was talking about the
00:30:07.440 RFP.
00:30:08.240 >> Mhm.
00:30:08.840 >> And I recognized that we did not have
00:30:11.160 the capabilities to
00:30:14.080 take data and do quote effectively. And
00:30:16.920 so I spent the next year of my life
00:30:18.600 researching pricing and and how we could
00:30:21.240 price better,
00:30:23.000 existing systems that worked, and there
00:30:24.960 were no systems that were out there.
00:30:26.560 >> Mhm.
00:30:27.160 >> And so I went to Lithuania.
00:30:29.560 I took, you know, whatever I had in my
00:30:31.680 401k, it was a couple hundred thousand
00:30:33.240 dollars, went to Lithuania, and we
00:30:35.440 launched Logistical Labs. The first
00:30:37.440 customer was was Load Delivered, and it
00:30:39.360 was pricing and modal optimization. How
00:30:41.600 could we price more accurately with
00:30:44.520 using algorithms, big data, different
00:30:47.440 sources, bring that in and and push out
00:30:50.200 prices fast to Fortune 500. So, it
00:30:53.040 worked. And it worked so well that over
00:30:55.440 the next couple years, we had
00:30:57.440 billion-dollar companies, Werner, CRST,
00:31:00.440 US Xpress that embraced the technology
00:31:03.480 and started to use it to grow their
00:31:05.640 brokerages from small brokerages to
00:31:07.880 billion-dollar companies.
00:31:09.360 >> Was there any concern from those
00:31:11.120 customers that Load Delivered had some
00:31:13.760 of their data?
00:31:14.560 >> So,
00:31:15.560 it's
00:31:16.640 you know, I take a lot of pride in this
00:31:19.000 and you know, starting this AI company
00:31:20.880 when we think about data and the
00:31:22.400 importance of trust.
00:31:24.320 We had 68 customers' data that was all
00:31:28.240 in Logistical Labs. We never looked at
00:31:30.360 it once.
00:31:32.000 And the thesis was eventually I wanted
00:31:35.040 to build this exchange, wanted to build
00:31:36.800 this consortium, believed that this this
00:31:39.240 group of 65 companies could do better
00:31:42.080 together.
00:31:43.640 In 2018, we we sold the both companies,
00:31:46.440 Load Delivered and Logistical Labs
00:31:47.960 before we got to that vision. Um but
00:31:51.000 absolutely people were concerned about
00:31:53.080 sharing data. They thought I was crazy.
00:31:56.040 They said, "Wait, you think you could
00:31:58.960 help us price better, but you need us to
00:32:01.920 give you your data."
00:32:04.080 Fast forward 12, 13 years later,
00:32:06.640 it's very normal to exchange data so
00:32:08.800 that people can help you price or help
00:32:11.240 you find trucks. And so,
00:32:13.080 you know, breaking down some of those
00:32:14.320 barriers early on
00:32:16.360 was difficult. I remember getting a
00:32:17.720 cease and desist
00:32:19.360 from DAT, a cease and desist from
00:32:21.200 Truckstop cuz they never had anyone hit
00:32:24.240 their hit their system that many times
00:32:26.280 for rating.
00:32:27.320 >> Yeah.
00:32:27.480 >> And this is like before real APIs even
00:32:30.040 existed. And so,
00:32:32.280 they're like, "How could you potentially
00:32:33.720 hit it that many times?" And said, "We
00:32:36.160 We need the data to be able to help sub
00:32:38.680 billion dollar brokers price.
00:32:41.040 And yeah.
00:32:42.080 >> Man, I can't even imagine running one
00:32:44.560 company. I mean, kudos to obviously you
00:32:46.480 and then you for founding your own your
00:32:48.440 own companies, but what was that like
00:32:49.960 running two at the same time?
00:32:52.120 >> So, I had a amazing Chris Richardi who's
00:32:54.760 the the COO, president, chief product
00:32:57.200 officer. Now has a big role at Capstone.
00:32:59.880 He really ran that company
00:33:02.400 and took the the vision and executed. Um
00:33:05.760 so, I'll give him all that that credit,
00:33:07.560 him him and the team over there.
00:33:08.960 >> Yeah. Well, we'll still give you some of
00:33:10.440 the credit. That's for sure. Obviously
00:33:12.280 well deserved, but I think that goes
00:33:14.240 back to some of the things that we were
00:33:15.160 talking about and the importance of team
00:33:16.440 and building the right team.
00:33:17.773 >> [gasps]
00:33:18.040 >> So, Load Delivered, Logistical Labs,
00:33:21.120 both doing extremely well and then you
00:33:23.520 alluded to it already, but in 2018 went
00:33:26.200 through an acquisition. Were you
00:33:28.000 actively seeking something? Did
00:33:29.440 something come to you? What kind of
00:33:31.240 spurred that?
00:33:32.160 >> So, in 2015, you saw
00:33:35.560 Command Transportation and Coyote hit
00:33:37.600 the bid.
00:33:38.240 >> Yep.
00:33:39.080 >> So, 2014 was the hype cycle, really good
00:33:41.560 business, and [clears throat] you saw
00:33:43.160 those leaders had a lot of experience
00:33:45.440 and they knew it was time to sell.
00:33:48.320 So, having been brought [clears throat]
00:33:50.000 up in the Chicago freight brokerage
00:33:51.480 ecosystem, I think it's important to
00:33:53.680 respect and look at what your elders are
00:33:55.640 doing.
00:33:57.200 I saw what they did and when the the
00:34:00.400 market tanked in 2016,
00:34:03.000 I knew that as soon as the market sort
00:34:05.680 of changed, we needed to be in a
00:34:07.880 position to exit. And partially it was
00:34:10.480 because of the compression that was
00:34:11.960 coming in from Uber Freight, Convoy,
00:34:14.879 some of the digital brokerages. They
00:34:16.879 were playing with institutional capital
00:34:19.520 and they were basically buying market
00:34:21.719 share at negative margin. And so, I was
00:34:24.080 running a a profitable freight
00:34:25.879 brokerage. We were doing, you know,
00:34:27.320 eight or nine million in EBITDA and I
00:34:30.080 just saw that it
00:34:31.840 was always told uh
00:34:33.639 never be in a fight with someone that is
00:34:36.520 a little irrational, and I felt that we
00:34:39.199 were uh there was just an opportunity to
00:34:42.399 uh exit, move on, and and continue to
00:34:44.879 innovate elsewhere.
00:34:46.080 >> So, like finding an acquirer for your
00:34:49.040 business, is it almost like a sales
00:34:50.840 process like
00:34:52.600 obtaining like venture capital or like
00:34:54.639 how do you go about finding suitors?
00:34:56.520 >> So, the best companies don't get sold,
00:34:58.240 they get bought.
00:35:00.040 >> Interesting.
00:35:00.760 >> And I think that was a big, you know,
00:35:03.080 big part of of my evolution. Uh we had
00:35:06.720 gone to market in 2014 or 2015
00:35:10.080 uh and just when you go and try to sell
00:35:13.000 a company, it doesn't work.
00:35:14.520 >> Interesting.
00:35:14.760 >> You need to build a great organization,
00:35:17.880 something that will last, something that
00:35:19.520 will live uh you know, for many years
00:35:22.240 beyond. Uh that was actually something I
00:35:24.720 learned from from mentors early on. It
00:35:26.640 was not just how good of a company you
00:35:28.760 can build,
00:35:29.680 >> but how many years after you leave will
00:35:32.200 it be around?
00:35:34.280 Interesting.
00:35:34.840 >> And you know, I think you know,
00:35:36.960 there's talk about legacy. I don't
00:35:38.480 really necessarily believe in legacy,
00:35:40.000 but I believe in whatever you do, it
00:35:42.320 should have a lasting positive impact.
00:35:44.560 >> Yeah.
00:35:45.000 >> And um so,
00:35:47.480 yeah.
00:35:47.920 >> I mean, fast forward today, I think I
00:35:49.280 saw a picture on LinkedIn where you had
00:35:50.680 a party with your former Load Delivered
00:35:52.240 teammates.
00:35:52.920 >> It's uh I have a big place in my heart
00:35:55.600 for for Load Delivered, for the team out
00:35:57.800 there, and uh yeah, it's it's the
00:36:00.840 relationships that you create in this
00:36:02.640 industry and in business in general are
00:36:04.880 are tremendous. Um I know, you know, KJ,
00:36:07.360 you have a lot of great industry
00:36:08.840 friends, and um
00:36:10.720 that's part of the fun.
00:36:12.080 >> It is fun. And I want to talk about af-
00:36:14.480 once that acquisition or the sell
00:36:16.400 actually happened, but I think that's
00:36:18.800 something else that's interesting from
00:36:20.040 an entrepreneurial standpoint. You were
00:36:21.440 talking about building a business and
00:36:22.880 something that is going to stay there
00:36:24.640 even when, you, you decide to depart,
00:36:26.400 whatever it is. Did you start Load
00:36:28.680 Delivered and then
00:36:30.120 potentially Logistical Labs with the
00:36:32.000 goal in mind of I know I'm going to sell
00:36:33.720 this one day, or were you going into it
00:36:35.800 as I'm just going to build a business
00:36:37.160 and then see what happens?
00:36:38.280 >> to be a billion-dollar company. I wanted
00:36:40.240 to be a top 10 freight broker. I was
00:36:42.440 convinced in my early 20s that was going
00:36:44.840 to happen. Um but I think it was also
00:36:47.800 important to, you know, recognize your
00:36:50.520 strengths, recognize where you need to
00:36:52.960 grow as an individual. Um I wanted to be
00:36:56.360 a CEO of a billion-dollar company, and I
00:36:58.920 thought the best way would be to sell
00:37:00.520 into that company.
00:37:02.000 >> Mhm.
00:37:02.440 >> Um the CEO of Capstone is tremendous. Uh
00:37:05.960 I ended up selling the company to HIG
00:37:07.720 Capital uh year after he bought Load
00:37:10.080 Delivered. Um so Capstone's doing great,
00:37:12.800 but uh that was part of it is I wanted
00:37:15.400 to learn what it was like to be an
00:37:17.280 executive at a billion-dollar company
00:37:19.760 versus a founder at a hundred-plus
00:37:21.800 million-dollar company.
00:37:23.160 >> Yeah.
00:37:24.080 Then
00:37:25.200 with that in mind, when this all
00:37:27.840 actually happened, then you got into
00:37:29.120 venture capital, correct?
00:37:30.800 >> So
00:37:31.880 as most founders do, you sell your
00:37:33.600 company, you've worked so hard, and
00:37:35.320 you're trying to figure out exactly what
00:37:37.000 the next steps were.
00:37:38.800 Uh and so investing and being an angel
00:37:41.120 investor in the sector was just a very
00:37:43.600 logical progression.
00:37:45.840 Uh and yeah, over the course of uh 7
00:37:49.240 years, we've invested in now eight uh
00:37:52.040 freight tech 25 companies, one IPO,
00:37:56.000 uh three unicorns, and uh hopefully uh
00:37:59.160 more in the near future.
00:38:00.920 >> And post-sale, you also kind of came
00:38:03.000 full circle and moved back to Colorado.
00:38:05.520 >> Yeah, I spent a lot of time in front of
00:38:07.120 the computer screen uh for for 11 years
00:38:10.000 building Load Delivered. Uh
00:38:12.200 you know, when you love your business,
00:38:14.480 you love what you do, you you can be a
00:38:16.200 little obsessive-compulsive about it.
00:38:18.280 And I thought it was important to go
00:38:20.080 from, you know, 14-15 hours a day in
00:38:21.880 front of a computer screen to get back
00:38:23.760 to my roots. Uh Um I always wanted to
00:38:25.680 build a family
00:38:27.000 in Colorado. When I graduated at CU,
00:38:29.720 there was no job opportunity. Had to
00:38:31.600 move back to Chicago. And so, uh as soon
00:38:34.480 as I had the opportunity uh to move back
00:38:36.480 here, I did. And uh
00:38:39.400 yeah, I try to spend a lot of time
00:38:41.520 outdoors and and in the nature.
00:38:43.520 >> Yeah, so that was that post 18 and going
00:38:45.480 into 19?
00:38:46.560 >> Uh so, that was I I was at Capstone for
00:38:48.840 uh 12 months and 1 day after the exit.
00:38:51.320 Uh I thought it was very important to
00:38:52.960 transition my leadership team. I wanted
00:38:55.720 all them to have a really strong role at
00:38:57.480 the new entity. Um
00:38:59.520 and yeah, so that was about 2019 before
00:39:02.520 COVID. We moved out here.
00:39:04.760 Uh and uh that's when we started to uh
00:39:07.280 build out the the venture firm.
00:39:10.320 >> Having that experience and then going
00:39:11.640 into the venture firm, how did selling
00:39:13.920 your business and then being part of
00:39:15.680 that affect how you evaluated companies
00:39:18.800 when you're investing in them?
00:39:20.520 >> So, being an operator, you can afford to
00:39:23.320 be very emotional. Being an investor,
00:39:25.200 you cannot be emotional.
00:39:26.880 >> Hm.
00:39:27.080 >> I think that's the biggest difference.
00:39:29.000 Uh and that's what I learned.
00:39:30.880 Um you know, also, people don't talk
00:39:33.120 about all the the losers that they
00:39:35.057 >> [laughter]
00:39:35.440 >> the companies that maybe didn't do as
00:39:37.120 well. Uh and and the losses. And I think
00:39:39.800 that's also
00:39:41.760 it sounds cliché, but you do learn more
00:39:43.800 from the losses sometimes than the
00:39:45.720 winners.
00:39:46.960 Uh and that's that's part of life.
00:39:49.320 >> I'm going to say along the way as well,
00:39:50.520 like
00:39:51.480 getting into deep into COVID, you
00:39:52.960 started another transportation business
00:39:54.440 or you bought one.
00:39:55.480 >> So, I we uh so, I loved out being out in
00:39:58.800 the outdoors. And the thought was we
00:40:01.440 built a company called Romeo. And we
00:40:03.400 were building camper vans. And then we
00:40:05.640 were renting camper vans out. And we
00:40:08.200 were trying to create an experience for
00:40:10.200 people during COVID where they could go
00:40:12.200 to the mountains, rent a camper van,
00:40:14.680 uh and enjoy life.
00:40:17.120 What we found during that business was
00:40:20.160 building. So, there's building
00:40:22.080 technology and then there's building
00:40:23.320 vehicles.
00:40:24.800 Uh it was a tremendous experience
00:40:26.280 building the vehicles,
00:40:27.960 uh but what I realized I don't love
00:40:32.000 I I didn't love building hard assets. I
00:40:35.320 don't love owning hard assets unless
00:40:38.280 it's real estate. And so, what we
00:40:40.120 decided to do, we built 25 vehicles, we
00:40:42.600 sold all 25 vehicles,
00:40:44.880 and we started building uh buying
00:40:47.640 industrial real estate to build and
00:40:50.400 store the vehicles, and we recognized
00:40:52.920 that that business was going to be much
00:40:54.480 more profitable industrial outdoor
00:40:56.120 storage than the van business. So, we
00:40:59.400 shut the van business down. Now, we have
00:41:01.200 an industrial outdoor storage business,
00:41:03.400 uh large property, 10 acres in uh
00:41:06.320 Dacono, Colorado, and then 12 different
00:41:08.960 facilities across the country, uh
00:41:11.240 ranging from like Alabama up to uh to
00:41:14.080 Massachusetts.
00:41:15.080 >> So, if you like scroll your LinkedIn
00:41:16.640 profile, you can see Go Romeo on there.
00:41:18.800 For me, how I got exposed to it when I
00:41:20.520 ran Global Trade Acquisition or Project
00:41:22.160 44, it was a perk for the employees
00:41:24.160 during COVID.
00:41:25.480 People would like you could set up time,
00:41:27.800 right? You could say, "I want to go and
00:41:29.160 have it for like this week, and I'm
00:41:30.440 going to go to Wyoming and work remote."
00:41:32.480 So, it was a perk for at least a year at
00:41:33.840 Project 44. That's how I got exposed to
00:41:35.400 it.
00:41:36.200 >> That's and we had great feedback. Like
00:41:37.960 people loved renting those vehicles.
00:41:40.120 They were in front of computers all the
00:41:41.640 time, and then they'd get to go in a
00:41:43.120 Romeo and and roam all over the country,
00:41:45.560 and uh
00:41:46.760 you know, I think as as AI becomes more
00:41:48.680 prevalent, we're going to see more
00:41:50.360 people want to get outside, get
00:41:52.560 outdoors, have real experiences. I think
00:41:55.600 we're seeing that in the economy
00:41:56.800 already, where people
00:41:58.680 uh
00:41:59.360 they want to they want to embrace uh
00:42:01.920 embrace nature versus just being in
00:42:03.920 front of the computer.
00:42:04.760 >> Well, all three of us live in Colorado,
00:42:06.440 raising families in Colorado. I
00:42:08.440 completely agree.
00:42:09.280 >> Oh, yeah.
00:42:09.640 >> You were ahead of the game with that.
00:42:10.760 >> Yeah. I think that there's a lot of
00:42:12.640 people that are starting to experience
00:42:13.920 that and making sure that they're
00:42:16.080 getting more than just what's outside of
00:42:18.240 the four walls at work or something like
00:42:19.840 that. I made a very similar transition
00:42:21.760 to you where we were in Chicago up until
00:42:23.520 2019, moved out here at the same time
00:42:25.400 because we knew that we wanted to have a
00:42:28.000 little bit more of that outdoors
00:42:29.600 exposure. Absolutely love Chicago. I
00:42:31.880 personally think it's the best city in
00:42:32.960 the world that I've been to, but ready
00:42:35.520 for a little bit
00:42:37.640 extra curriculars outside of just
00:42:39.320 downtown.
00:42:40.600 So, it's it's important for that. Um I
00:42:42.760 did want to circle back really quick. I
00:42:44.080 mean, I guess you were still in venture
00:42:45.880 while you were doing Go Romeo. One of
00:42:48.320 the things that I think is super
00:42:49.360 interesting and if you had to pick
00:42:50.720 between the two, if you're investing in
00:42:52.840 a company, what's more important? Is it
00:42:55.360 the jockey or the horse? And again, what
00:42:57.640 I mean by that is is it the founder or
00:42:59.480 is it the idea behind that founder?
00:43:03.400 >> The the standard commentary
00:43:05.969 [clears throat] is it's all about the
00:43:07.000 founder.
00:43:07.720 >> Yeah.
00:43:08.760 And I do agree with that.
00:43:10.880 But there's a combination of founder
00:43:15.560 and the timing in the sector that
00:43:18.440 they're in.
00:43:19.560 >> Yeah.
00:43:20.480 >> And so a combination of founder and
00:43:24.080 timing and what they're working on and
00:43:26.480 what's what what's behind that? What is
00:43:28.840 going to help be like the impetus to
00:43:30.960 take that from a normal business to
00:43:33.440 something greater. [clears throat]
00:43:35.320 Highway's a great example. So, I was one
00:43:37.000 of the first checks into Highway,
00:43:39.680 wonderful company helping to fight
00:43:41.200 freight fraud in the logistics sector
00:43:44.120 and
00:43:45.560 it was So, one is investing in founders
00:43:47.920 that are trying to like build the
00:43:49.080 future, not build for today. I think
00:43:51.080 it's is really important. Highway was
00:43:53.560 one of those situations where he was
00:43:54.880 trying to to build for the future.
00:43:57.440 Um but what they had happen, not just a
00:43:59.880 great jockey, not just a great idea,
00:44:02.280 they had something happen during that.
00:44:05.240 There was a large There was more fraud
00:44:08.160 that started to occur in the industry
00:44:11.320 and the largest competitor
00:44:12.780 [clears throat]
00:44:13.320 had some technical difficulties.
00:44:16.120 And so they they had lightning
00:44:18.675 >> [clears throat]
00:44:18.720 >> and they were able to go from zero to
00:44:20.640 1250 customers and raise a really big
00:44:23.040 round from FTV and are doing fantastic.
00:44:26.320 And so I think it's a combination of the
00:44:28.320 jockey. I think the idea is important
00:44:30.680 but I think there has to be some sort of
00:44:33.080 tailwind behind uh behind it in in this
00:44:36.240 day and age.
00:44:37.600 >> That makes sense. And so
00:44:40.880 venture started Go Romeo and I think
00:44:44.320 that that brings us to what you're doing
00:44:46.080 today, right? You wanted to get back in
00:44:48.520 the game. What made you want to start
00:44:50.200 another company?
00:44:51.920 >> Yeah, I mean that's a great question
00:44:53.000 because I mean young children, two young
00:44:55.040 boys at the time. Is it that you you
00:44:57.280 couldn't pass up the opportunity how big
00:44:58.630 [clears throat] AI is going to be? It
00:44:59.840 was you wanted the action. It was
00:45:02.360 serving customers. It was helping
00:45:04.120 brokerages. I mean there's a lot of
00:45:05.720 stuff to think through to decide to get
00:45:06.840 into an arms race really.
00:45:09.520 >> Yeah, I you know the
00:45:13.480 when you're when you
00:45:15.640 are an entrepreneur, you get pulled. You
00:45:18.320 have this pull
00:45:20.040 and it's not logical.
00:45:22.800 It doesn't always feel great but
00:45:25.000 something is just telling you that you
00:45:26.520 have to get in the game and innovate and
00:45:28.680 make a difference and an impact and
00:45:31.000 I had I know KJ you like to you do
00:45:33.560 martial arts. So I was training with a
00:45:35.880 UFC fighter. I was running up mountains.
00:45:39.240 I was trying to push my body I think
00:45:41.760 because cuz I wasn't in the the business
00:45:44.040 game at the level I wanted. And
00:45:47.160 I was actually training with my UFC
00:45:48.600 fighter. I was training for a match and
00:45:51.160 I got punched really hard.
00:45:53.651 >> [laughter]
00:45:53.960 >> And
00:45:55.240 teeth like flew out of my mouth. And I
00:45:58.280 went home to my wife and I'd been
00:46:01.320 reading a lot about AI.
00:46:03.680 And she's like, "Are you sure you don't
00:46:04.960 want to go back into business or do
00:46:07.160 something else?"
00:46:08.320 >> Yeah.
00:46:08.800 >> And
00:46:09.240 >> can keep your teeth intact.
00:46:10.480 >> keep your teeth. And so, I One is I
00:46:12.640 thought AI would be a lot safer place,
00:46:14.600 but it was that pull. It was It didn't
00:46:16.880 matter how far I ran up a mountain or
00:46:19.800 how hard I got punched. I just I wanted
00:46:22.760 to innovate in logistics.
00:46:24.800 >> Punched or choked, it's really humbling.
00:46:27.057 >> [laughter]
00:46:28.640 >> Yeah. And so, I think that that is a
00:46:31.000 testament to the the real founders and
00:46:33.400 entrepreneurs that are out there. I
00:46:35.600 think that you can find somebody that
00:46:37.400 wants to start a business, and whether
00:46:38.680 it goes well or doesn't, they're like,
00:46:40.760 "Okay, I did it once. I can just go back
00:46:43.040 into corporate America." Not that
00:46:44.200 there's anything wrong with that, but
00:46:45.920 every single founder that I've ever
00:46:47.120 talked to, a real entrepreneur, has said
00:46:48.680 that exact same thing. There's that itch
00:46:51.000 of, "Okay, I had a
00:46:53.600 success, whether it was an acquisition
00:46:55.400 or sale, but I can't just sit here and
00:46:58.160 not do anything and wait on the
00:46:59.400 sidelines."
00:47:00.240 >> It's wiring in the brain.
00:47:02.000 >> Yeah. Yeah.
00:47:03.360 Um so, you were talking about the AI
00:47:05.200 space.
00:47:06.440 Why did you decide to start Envoy? Was
00:47:09.200 it Again, you saw everything that's
00:47:10.720 going on with AI, this is the next wave,
00:47:13.360 was it just the timing of things? What
00:47:15.760 really kind of drew this out?
00:47:17.720 >> So,
00:47:18.720 part of it was I I was
00:47:20.880 getting pulled in by my friends to look
00:47:23.160 at the V1 applications, and they wanted
00:47:26.400 to
00:47:27.400 see what I thought. And I started to
00:47:29.520 look at the logistics companies that
00:47:32.320 were starting to come out in that time
00:47:34.040 frame, and I thought I could do it
00:47:35.760 better.
00:47:36.760 >> Yeah.
00:47:37.480 >> And I thought there was a different way.
00:47:39.240 And so, we started building this AI
00:47:41.320 orchestration, we started thinking about
00:47:43.080 the forward deployed engineer model, and
00:47:45.160 we just didn't believe that it was
00:47:46.800 correct. We thought it was wrong. Uh and
00:47:49.600 I mentioned this earlier, it's if you
00:47:51.440 have large contracts, if you're
00:47:52.920 Palantir, and you're innovating uh for a
00:47:55.720 large army contract that's 10 years,
00:47:58.360 yeah, 5 years, great. You can send an
00:48:00.360 NFT, you can
00:48:01.920 look at the SOP, but freight is in
00:48:04.280 constant most motion.
00:48:05.640 >> Yeah.
00:48:06.560 >> And I don't believe that that model will
00:48:09.040 compound over time. I think it's a
00:48:10.960 results outcomes based model that AI
00:48:13.800 companies are going to need to produce.
00:48:15.480 It's going to look closer to what a BPO
00:48:17.520 looks like today.
00:48:18.520 >> Mhm.
00:48:19.000 >> And that's what's interesting. It's this
00:48:20.840 blending, I'm calling it Lass. It's a
00:48:23.240 blending of logistics and services.
00:48:25.320 >> Yeah.
00:48:25.720 >> So it's not technology logistics
00:48:27.280 services and technology. It's not SaaS,
00:48:30.480 it's not a brokerage. It's going to be
00:48:32.600 Lass. And we're starting to see some V1
00:48:34.880 companies come out. I think we'll see
00:48:37.040 more in the in the next several months.
00:48:40.000 >> I would think you have a unique lens
00:48:41.480 having sold built a brokerage and a
00:48:44.840 pricing tool and then coming on the AI
00:48:47.040 side where I think some of the other
00:48:48.640 startups in the space, the version one
00:48:50.040 you're talking about, they're from
00:48:51.520 outside the industry some of them.
00:48:53.760 >> And and you know, in certain respects
00:48:55.640 that's advantage that can be an
00:48:56.880 advantage.
00:48:57.760 >> Absolutely, fresh eyes.
00:48:58.360 >> But I'm a believer experience teaches
00:49:00.520 wisdom.
00:49:01.960 And wisdom trumps wisdom creates trust.
00:49:07.400 I I think that innovation in our
00:49:09.600 industry needs to happen from inside the
00:49:11.880 industry. It's not going to happen from
00:49:14.080 outside of the industry. And so
00:49:17.280 yeah, just a different different style.
00:49:19.160 I love competing is part of the fun in
00:49:21.320 business. So I have a lot of respect for
00:49:22.880 all those companies. We talk all the
00:49:24.800 founders and
00:49:26.400 it's healthy competition.
00:49:28.600 >> Is there anything specific, and I know
00:49:30.040 we're talking about the the hatchet and
00:49:31.560 the axe before, is there anything
00:49:33.280 specific that you feel like you learned
00:49:35.080 from Load Delivered, from Logistical
00:49:36.720 Labs, from your venture time,
00:49:39.080 that you're taking into this, you know,
00:49:41.200 Envoy, of making sure that you do this
00:49:43.880 or don't do this as you continue and
00:49:45.600 scale things?
00:49:47.240 >> I think part of it is everyone
00:49:49.680 uh
00:49:51.800 trying to be the the CEO I always wanted
00:49:54.480 to be, the founder I always wanted to be
00:49:56.160 in my 20s.
00:49:57.520 Uh
00:49:58.520 a little less I think it's hard to
00:50:00.560 everyone has this idea of of how they
00:50:02.240 should operate a business.
00:50:04.720 And my goal this time around is is to do
00:50:06.720 exactly what I want and do it quickly.
00:50:09.000 >> Yeah.
00:50:11.160 >> Making decisions faster
00:50:13.280 and again just building a great team
00:50:14.760 around around myself and co-founder.
00:50:17.600 >> Yeah.
00:50:18.800 As also being somebody that's entrenched
00:50:21.320 in AI every day, I feel like you can
00:50:23.240 talk to some people and some others that
00:50:25.440 say that this is AI of the future we're
00:50:28.080 super far along with this. A lot of
00:50:29.520 other people are saying we're just
00:50:30.560 scratching the surface. Where do you
00:50:32.200 think that we're at in the AI journey of
00:50:34.760 things?
00:50:36.640 >> I think it's early. I think if you
00:50:38.200 believe that super intelligence will
00:50:40.360 happen in the next couple years then
00:50:44.280 um
00:50:45.400 we're early. You know there's this
00:50:47.600 there's this rhetoric in San Francisco
00:50:49.400 that like all white collar jobs will die
00:50:52.360 and be eradicated and you should
00:50:53.800 basically go learn how to be an HVAC an
00:50:56.680 HVAC or or do something in the services.
00:51:00.400 Let's say that's true. The same way that
00:51:03.040 driverless cars were true.
00:51:04.720 >> Yeah.
00:51:05.760 >> It's always going to take two to three
00:51:08.240 times longer than people think.
00:51:10.440 >> Mhm.
00:51:10.880 >> Um now it might be a little accelerated
00:51:13.200 in this hype cycle with AI tremendous
00:51:15.520 amount of money being poured into data
00:51:17.760 centers. Data centers will help compute.
00:51:20.680 There's going to be a lot of opportunity
00:51:22.320 for things to move fast but
00:51:24.840 um
00:51:26.360 not in logistics.
00:51:28.280 >> What is super intelligence?
00:51:30.360 >> Um
00:51:31.240 you're going to have to ask the the
00:51:32.360 folks at Stanford.
00:51:33.600 >> [laughter]
00:51:34.255 [clears throat]
00:51:34.560 >> Uh
00:51:35.400 they're working on super intelligence
00:51:37.320 which is you know essentially we're
00:51:39.920 thinking about multi-channel agents
00:51:42.440 agents talking to agents and passing
00:51:44.400 along like super intelligence is
00:51:48.040 uh
00:51:48.720 >> The next step.
00:51:49.640 >> Yeah. Whole 'nother ball game.
00:51:50.840 >> Yeah, we're going to reach a singularity
00:51:52.320 or not, but to get back to your point
00:51:54.440 about it takes longer. You know, we
00:51:56.640 heard the hype from whether it was Uber
00:51:58.120 Freight or Uber about autonomous trucks.
00:52:00.640 You know, I think last summer you and I
00:52:01.680 got in our first Waymo.
00:52:02.680 >> Yeah.
00:52:03.400 >> So, I think in logistics and
00:52:05.040 transportation, also when you're
00:52:06.200 building like assets you have to move it
00:52:07.680 does take longer. There's also like the
00:52:09.640 proof of concept of making sure like
00:52:11.000 there's not injuries or deaths or things
00:52:12.840 like that. And I think there's some
00:52:13.920 proof out there now with full service
00:52:15.720 full service driving cars like
00:52:17.840 the percentage is it's way safer to be
00:52:19.400 in them.
00:52:19.920 >> Yeah.
00:52:20.480 >> But it's um it's going to be interesting
00:52:22.440 how it plays out. So, I guess
00:52:24.760 pivot to a question.
00:52:26.360 If we're getting close to super
00:52:27.880 intelligence, you have a young daughter,
00:52:30.360 my daughter's a little bit older, you
00:52:31.400 have young boys,
00:52:32.640 you know, what is the job market or
00:52:35.240 what's going to be available in 10 or 15
00:52:37.800 years when we look at robotics and AI
00:52:39.360 coming together?
00:52:41.560 >> I mean, it's wild.
00:52:44.880 >> That's that's that's the type of uh
00:52:48.120 question that I don't think anyone
00:52:50.840 really knows the answer.
00:52:52.200 >> Yeah.
00:52:52.640 >> Yeah.
00:52:53.960 Sometimes you you want to wake up and do
00:52:56.280 you just move to the mountains deep deep
00:52:57.920 in the mountains [laughter] and
00:52:59.640 uh
00:53:00.840 I think it's more like taking a step
00:53:03.000 back and just being like what where are
00:53:04.760 we at as a society? What are we doing as
00:53:07.360 a society? And we're spending a lot of
00:53:09.400 time like this.
00:53:11.280 >> Yeah.
00:53:11.960 >> On our phone. A lot of time like this.
00:53:15.200 And
00:53:17.920 forget about what happens in 15 years.
00:53:19.720 What's going to happen when our kids see
00:53:21.480 us like all just walking around like
00:53:23.400 this on their on our phones or
00:53:24.920 communicating like this versus spending
00:53:27.160 more time sort of one-on-one with them.
00:53:29.240 And so, I think first it's like
00:53:32.000 detaching from technology.
00:53:34.360 Um
00:53:35.040 And then second, teach your kids how to
00:53:36.920 be relentless, teach them how to be a
00:53:38.640 problem solvers.
00:53:40.520 Uh I think those are are That's really
00:53:42.960 important, but we don't know if there's
00:53:46.040 you know, lawyers, I don't know,
00:53:48.000 doctors, sure we'll need doctors, but
00:53:50.600 will they have a different role?
00:53:52.440 Freight brokers definitely will have a
00:53:53.840 different role. Uh,
00:53:55.760 yeah, world's changing fast and you
00:53:57.520 know,
00:53:58.480 it's on us to navigate through it with
00:54:00.520 our children.
00:54:01.240 >> Yeah. It's funny that you said freight
00:54:03.080 brokers cuz that was one of the things
00:54:04.280 that we as we get to the tail end of the
00:54:05.880 conversation, I was very curious if you
00:54:07.520 had an opinion on Do you think freight
00:54:09.360 brokers are still going to be a thing in
00:54:10.880 10, 20 years?
00:54:15.000 >> So, when I was growing up there was
00:54:16.680 stock brokers.
00:54:18.000 >> Yeah.
00:54:18.280 >> And now there's Robinhood.
00:54:19.720 >> Yeah.
00:54:20.960 >> Stock brokers took a couple points of
00:54:23.040 every trade. Robinhood, you can trade
00:54:25.800 make as many trades as you want. And
00:54:29.480 just think about that construct and I
00:54:31.440 think there
00:54:33.520 there are some parallels to freight
00:54:36.200 brokerage. That said, stocks aren't in
00:54:39.440 motion and trucks are.
00:54:41.520 And so, it will never go Robinhood, but
00:54:45.840 uh, freight brokerage will will feel
00:54:47.920 very different in the next cycle.
00:54:49.960 >> Yeah.
00:54:51.120 >> That's a really good analogy.
00:54:52.560 >> Yeah.
00:54:53.320 >> I should be in Chicago, yeah.
00:54:54.680 >> Yep. And as we wrap things up, what we
00:54:57.560 always love to do is is give you the
00:54:59.440 mic. A 45 second minute, however long
00:55:01.680 you want to go for, talk to us about
00:55:03.480 anything that you feel like anybody
00:55:04.800 that's watching the Founders Lounge
00:55:06.200 didn't get insights to, talk about
00:55:08.680 Envoy, talk about what you're excited
00:55:10.160 about in this space, really open mic
00:55:11.880 time for you.
00:55:14.320 >> Open mic, uh,
00:55:16.000 >> If anything.
00:55:16.800 >> So,
00:55:17.613 >> [snorts]
00:55:17.880 >> you know, I used to be a rapper. And no,
00:55:20.160 I wasn't.
00:55:20.640 >> Oh, I was going to say oh man, I didn't
00:55:22.480 know you fought in the UFC, you know,
00:55:23.560 that's
00:55:23.720 >> No, but I'll give you this, this is a
00:55:25.560 random fact. So,
00:55:27.600 uh, back in the day before there was
00:55:30.480 reality TV, there was documentaries. So,
00:55:33.720 I was on one of the first reality TVs
00:55:36.320 for high school kids
00:55:38.280 uh, in Chicago, Illinois in 2000. It was
00:55:40.640 called American High. It was on Fox TV.
00:55:44.080 Didn't go so well, so we later got
00:55:45.560 booted to PBS.
00:55:47.400 But yeah, that was my entry into being
00:55:49.240 in front of the camera was I was 20
00:55:51.560 years old and
00:55:52.960 getting filmed every day in in my senior
00:55:54.880 year in high school.
00:55:56.040 >> Wow.
00:55:56.680 >> That's pretty interesting. Now, and
00:55:57.840 that's not just being filmed, but it's
00:55:59.640 also I think we were setting up you were
00:56:01.640 talking about your voice. What was it
00:56:03.640 about JB Hunt you're able to gain some
00:56:05.360 business?
00:56:06.600 >> So
00:56:07.040 >> Through we were kind of chopping it up
00:56:08.080 just for a little bit.
00:56:08.520 >> Yeah. So what made my career, I'll give
00:56:10.280 a shout out to Lori Patrick who's still
00:56:12.120 at JB Hunt today. I was 22 years old. I
00:56:15.240 wanted so badly to work with JB Hunt and
00:56:17.920 I finally on the night shift found a way
00:56:20.840 to to get access to some of their
00:56:22.880 trucks, called back the next day. They
00:56:25.200 worked with us and I was so proud of
00:56:27.960 myself for navigating, using my brain,
00:56:30.800 only to find out a month later the only
00:56:32.960 reason she let me in and started working
00:56:35.560 cuz she thought I had a nice voice.
00:56:38.760 And yeah, so that was really deflated
00:56:41.800 me.
00:56:42.760 >> But whatever gets it done, you still
00:56:43.840 have got it done in the end, which is
00:56:45.240 good.
00:56:46.680 Well, I think that we have thoroughly
00:56:48.920 enjoyed this conversation, really
00:56:50.200 getting a peek behind the scenes of
00:56:52.160 successes, failures, really
00:56:53.560 understanding you as a person and wanted
00:56:55.960 to thank you so much for taking the time
00:56:57.200 to come down here, hang out with us in
00:56:58.640 our studio and and let us grill you for
00:57:00.840 a little bit.
00:57:01.440 >> Thanks Coleman. Thanks KJ. I appreciate
00:57:03.800 all you and Talent Solvers does
00:57:06.080 for me in the logistics community.
00:57:07.640 Thanks a lot, guys. [music]
00:57:08.640 >> Thank you.
00:57:09.120 >> Right on.
00:57:14.859 >> [music]
00:58:09.800 >> Mhm.
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