Auto-transcribed via Deepgram nova-3. Speaker labels are approximate; light cleanup applied. Note: speaker attribution in the source file is inverted — "Jesse Buckingham" labels carry Ryan Keepman's responses throughout.
[00:00] Introduction
I'm excited to share this conversation with all of you with Ryan Keepman. Ryan has been running Evans Transportation for the last seven years after taking over the family business. Evans was started in 1986 right at the turn of deregulation and is probably one of the few businesses started at that time that remains family owned. There's a lot of other brokerages that started at that point that have since been acquired or folded. And Evans and Ryan have a very interesting and refreshing take, and it built a really interesting business by leaning into a lot of the more complex freight and they're doing some really cool stuff. And so it was a great conversation hearing about the thinking behind and the strategy behind diversification of different service offerings, how to actually land the plane on that because it can be really difficult when and how you should do that. And also just around generally, like, culture, Evans has built a really interesting and special culture, and so it's cool to kinda hear from Ryan how they brought that into the world. I hope you enjoy this conversation with Ryan Keepman from Evans Transportation. Well, welcome everyone to another episode of the the Freight Show. Very excited to have Ryan Keepman on today. Ryan, it's great to see you.
Ryan Keepman: I appreciate the opportunity. I'm excited for the conversation today and look forward to talking about all the great things Vooma's doing for Evans and anything you wanna ask me. I'm an open book probably to a fault.
[02:05] Founding Evans in 1986
Jesse Buckingham: Well, no, I've been really looking forward to this because we've chatted a little bit, but I've had the great fortune of working with your team for a number of years now, but have been excited to kinda hear more about the Evans story and the Evans journey, and maybe take it back to the beginning. I think 1985 ish, maybe it was the year the business was formed, but tell me a little bit about the story from the beginning and the big milestones along the way.
Ryan Keepman: Well, this is one of those, like, three and a half hour Joe Rogan podcast. Right? So it's a forty year history. You asked me a question. No. Yeah. It's a really unique story, especially being blood related to the founder being my father and knowing what he did with two kids at that time was what I call probably crazy. But he came from nothing. He learned the industry from his father-in-law, my mom's father, who was pretty innovative in the state of Wisconsin where we're still based today or headquartered in the transportation space and also kinda came from nothing. And, you know, he had started just to it is important to tell you a little bit about my grandfather. He had started the first piggybacking rail company that I think eventually was absorbed by Hub Group. He still has the original Ryder leasing location that's outside of the Milwaukee Zoo. For a lot of people, know it's a huge location that he started and sold to Ryder, but that was in a regulated environment. So he still had a full time job selling transportation, but was an entrepreneur at heart. And my dad married my mom. Quick story is he — you know, my grandfather was kinda like the madman era, martini lunches, and then kinda probably going back to the local tavern. It is Wisconsin. And so he was already pretty checked out by the time my dad was in the space and learning the business from his father-in-law. And he'd asked him if he would start a freight brokerage because Reagan had just deregulated transportation. So the idea came from knocking out a bunch of doors, and most companies were out of business that he was told to go call on during the cold wars of early eighties and decided to start something.
Jesse Buckingham: Like, you mean, these are some shippers that he was calling on? What was impacting those businesses?
Ryan Keepman: Back then, I think just the manufacturing environment in the Milwaukee area was quite depressed. And it was just a slower time in our economy, both globally and in The United States. And there was just a lot of uncertainty at that time. I'm no historian, but from what I do know is he had he tells a story where he was given 10 business cards and addresses to go call on in his Rolodex each day, and eight out of 10 would be shut down. And so he had no he had the vision that there had to be a better way to do transportation. And so my grandfather said there's no way we'll start a brokerage. So he said, okay. I'm gonna start one on my own, and that was when he went out, and I think he had a couple of different stints in trying to start something. And eventually, he found his way with a partner at the time, Marty Johnson, and he didn't tell my mother. He leveraged three credit cards and the house that he had, his first house he had purchased, and started Evans, and I was, like, four years old. My sister was one. I said, that's crazy. How did you do that? And he said, oh, I had no other choice in my mind, and I wanted to work for myself. And so I did it.
[06:11] Buying out the original partner
Jesse Buckingham: I love these gutsy stories. I started Vooma when my first kid was born, like, basically at the same time. But we also raised venture money, and I've always got so much respect for these entrepreneurs that, you know, load up on the credit card debt and put, like, you know, real finances on the line. It takes a lot of guts.
Ryan Keepman: Oh, yeah. I do too because I like to think of myself as high risk, but then when I start to hear those actual stories of people with their families and their kids. You see, I see a lot of people when you got these little, like, the little guys, you sort of realize you're like, fuck. I actually need to make sure I deliver here. Exactly. So he's always had such a passion for people and relationships. The two of them really started the whole business emphasis on the relationship side of the business. Built a moderate, you know, brokerage. I think one of the first couple 100 MC numbers out of what there's been 40,000. And the quick evolution of the business from 1985 forward was they were a small broker for the first five to seven years and then purchased a couple different trucking companies. So they know the local cartage company, Jeff's Fast Freight out of Milwaukee area for those Milwaukee listeners. And then a company out of Perrysburg, Ohio that was a medical delivery emergency deliveries, I think it's called EMD. And then they also invested in a few warehouses. So they did get into assets for a period of time. Help them really understand the entire scope of transportation from all levels. And in 1996, they had a client come to them and said, you guys do a really nice job. Customer service is great. We want you to do everything for us. And it was a food ingredient manufacturer. So that client gave them the ability to start to create their own before the I think name even existed at TMS. So they created what was known to be mother. That was the name of it — mother was our TMS until, I wanna say, like, 2010. So for the first fourteen years. That really helped them grow the business. They were able to be way ahead of the times.
Ryan Keepman: And then if you fast forward to 2018, my dad and I bought his partner out who had 50% of the stock through a long process. Again, being young entrepreneurs, there was no buy sell agreement. They each bought in to the business for a thousand bucks and figured we'll just figure it out from here, and maybe one day we'll sell it. And at that point in time, I was working for the company. I had personally fallen into transportation, really had no interest in working in the family business. My dad wanted to do other things. He's since adopted three siblings from Ethiopia that he adopted in his mid fifties and my mom in her early fifties, which is amazing. And just wanted to have it, you know, do some different things in life. Felt he was extremely blessed to be where he was coming from where he did and said, here you go.
[10:25] Building the truckload division as defense
Ryan Keepman: And during that process of buying out our previous partner, I had put a team together that I thought were some of the best in the space who I'd come across at the different industry events, some outside of the space. And in 2018, we recognized how bad we were at truckload, and we were losing a lot of clients. We were truly at that point doing about 70,000,000 a year in freight. Not doing so well. We're losing money from 2016 to 2018. And knew we needed to diversify and add some areas. And when one side of the business might be down, the other side could lift it up. And started a truckload division up in Minneapolis. And that division kinda took off and did real well for us. And then added since then to sum it up, we basically added a Mexico division, a specialized solutions division. So a group that does, you know, heavy haul that requires permitting and escorts, the whole gamut of services, engineers even on staff now to help drop those loads so they can move legally and provide a lot of consultation for our clients. We've also started a parcel solutions division and most recently started a government services division as well. So we are approved through the DOD on not all of the criteria that you need to have certifications for, but many of them. And so our business has really grown and extremely fortunate to buck the trend in the industry right now because it is very tough in that van freight brokerage market.
[14:28] The 3.5PL model explained
Jesse Buckingham: I was so curious to understand more about the decision to diversify. What was your framework for that?
Ryan Keepman: I would say that we started the truckload brokerage first. We like to call it truckload procurement because it's not a true brokerage with inside sellers pounding the phones, building relationships to move freight. We actually started as more of a coverage group that's specialized on carrier procurement. And I would say it was more of a defense mechanism to shield off brokerages who had morphed into managed trans and LTL operators and TMS providers so that we wouldn't lose clients because we had lost, gosh, we lost three of our top 10 clients from 2016 to 2018.
Jesse Buckingham: What was the competitive dynamic there? Because those brokers were starting to do managed trans and then they had this sort of value prop of, hey, we've got a brokerage, we also do managed trans.
Ryan Keepman: Price. We didn't buy well. They exposed a weakness. There was no question at that time.
Ryan Keepman: What's transformed in the market is that that three and a half PL, if you will. I don't know how many of these PLs we can have. But if you think about it, you sit as basically a four PL and you can blind bid as a three PL the shipments that come into your system from your customer. Yet you have other brokerages that the customer wants to have a part of the mix for each shipment that comes across, and you have the system worked out so that our team doesn't have visibility to undercut another three PL and win a load by $5 or something like that. It allows us to truly operate with no visibility on one side of the house. And that's how we've been able to achieve it quite successfully. I'd say that's probably the fastest growing area of our managed transportation.
[18:33] Managed transportation adoption and CFO sales cycles
Jesse Buckingham: When you're selling managed trans, how often are you replacing an incumbent vendor versus convincing somebody to outsource the management of their transportation?
Ryan Keepman: Yeah. That's changed a lot. I think we're up over 70%, right, of shippers — 75% of shippers in that range are using a three PL already today. We are most regularly now replacing. I don't have an exact number, but I know it's rare that we run into a shipper managing everything in house. My guess would be somewhere one to two out of 10. And so strategy and where we typically start our sales cycle is with a CFO of a mid market manufacturing company or a larger, whether Fortune 500 or larger manufacturer shipper with, like, a VP of supply chain. So it's really a strategic decision. And it's their responsibility to roll it out and make it successful. That's been a lot more effective for us in rolling out these managed transportation solutions.
[22:51] Diversification as a moat
Ryan Keepman: The parcel division was added truly to create a greater moat for us with our clients and continue to add value to their supply chains. And if we can help a customer, you know, move anything, we joke and say from envelopes to excavators, we truly can. And it's not an initiative to be the jack of all trades and master of none. You hired true experts who, excuse me, done it on their own or done it with a company, and they bring that actual, you know, subject matter expert knowledge with them and their ability to deploy it. We're also looking to bring in a warehouse product as well.
Jesse Buckingham: Very cool. How does that fit into the mix? What scenarios is that useful?
Ryan Keepman: The verticals that we're in right now have a lot to do with energy, AI, or data centers. People need space right now, whether that's indoor, outdoor. They need yards. They need somebody to facilitate the loading and unloading of their product so it can be there, be ready because these are such time critical. We hired a team to operate the facilities. The person that we've hired has stood up two other operations and was the president of their warehousing divisions for two different companies for both over ten years. It's more about the network and being able to support specific locations in his geographical areas that he supported in the past.
[26:57] Which shippers want a full-suite partner
Jesse Buckingham: Are there specific segments or types of shippers for whom the value proposition of we can help you solve a bunch of problems is more compelling?
Ryan Keepman: Scaling industries or verticals where people are growing so fast that their value prop to their end customer is far greater than them spending the time internally to create that full solution. And their business requires an outsourced solution to support it and people versus doing it in house. Given the speed of technology, and if you can build that trust, it equates to deals quite quickly. It's allowed us to really tap into some of the fastest growing verticals in The US right now. We've been very intentional about not selling price. We are not looking for what we call broker poker freight where people are shopping dozens of brokers and spending a lot of time on the nickels and dimes. We're looking to add much more value both upstream and downstream for our clients.
[31:09] Saying no to 10 of 13 moves
Ryan Keepman: We've said no to multiple clients in warehousing, almost knowing what you're not good at first is maybe more important. I do think a lot of freight brokers try to truly be that jack of all trades. And you fail in one area, you lose trust in the other areas, and you expose yourself. So we've been very, very intentional about only supporting complex problems where we are truly experts. And one area, we had a customer come to us that's a very large customer now a couple of years ago. And they said, we have these what are called MEB loads that require perimeter trailers or just crazy type equipment types. And they said, you cannot screw this up. Here are 13 moves and it equated to, like, great revenue — honestly, it's like $20,000,000 in revenue, but they're very high cost per move. And we went back to him and said, we're only gonna do three. And they said, no. We want you to do all 13. We said, we'll fail. But we'll do really well at these first three so we can get started on the right foot. And that has built a tremendous amount of credibility and trust with them. We leaned in where we knew we could cover them on the lanes where we had coverage. And we said, hey, we'll even offer up some competitors that you might wanna test out. We wanna help you, but we also don't wanna fail you. And so we've grown slowly with that client over time as we built more trust.
Jesse Buckingham: What is the bottleneck? Like, when you say you will fail, where's the bottleneck?
Ryan Keepman: In this specific instance it's capacity. There's only so many of these trailers available in the marketplace, and the government has access to a significant percentage of them. So having those carrier relationships, which is so critical so we can rely on them, those bottlenecks are truly just a result of a lack of manufacturing for this product — or the product being the trailer — that nobody knew would be so heavily required until all of a sudden it was. There's only a couple of manufacturers. A current production cycle is six months.
[35:15] Lessons from launching new service lines
Jesse Buckingham: Are there any lessons that you've learned about how to successfully get into a new service line?
Ryan Keepman: Yeah. I think everything against what I'm saying probably right now, but it's slowing down and hitting pause maybe more frequently. Doesn't mean you can't go fast still, but slowing down for periods of time to relevel set and have the teams on the same page because everybody we hire runs hard and is quite relentless in nature and competitive. So they wanna prove whatever it is they're bringing to the table and add value to the company immediately. And sometimes that can get lost in translation and frustration can build. But one thing we do really well at Evans, we spend a lot of time together. And I think maybe that's the lesson that has been learned is really getting these teams together, meaning face to face. There is no better recipe for challenging conversations to happen than in person. So really bringing people together, and we call it doing life together.
[39:26] Evans culture
Jesse Buckingham: How would you describe the Evans culture to someone that doesn't work in the business?
Ryan Keepman: We call it the Evans family for a reason. We're still family owned, and we love to bring that type of environment into the workplace. Look. We spend more time with the people that we're at work with than we do with our actual families. So the culture is quite dynamic. I would say the offices are a little bit different just based on the people and the interests of those offices. But overall and in general, we try to just create a culture that people can be open. We're open to hearing ideas. We are here to do much greater things than just move freight. We're here to build legacies all individually, but collectively as a team as well. We spend a lot of time with one another when we do our executive retreats or our leadership retreats or our sales retreats. You don't get a bunch of hotel rooms in a big city. We stay in a VRBO together. Grill out and we do activities that take us into that ten percent that you just keep closed up. We'd like to get into that 10% and get to know one another so that every day we go out to battle together, we got each other's backs.
Ryan Keepman: And one thing I do when trying to find out who somebody is from their core inside out — I live in the Panhandle of Florida. I've taken to the fishing hobby quite a bit. So bringing people out on the boat and not just for a couple hours, but spending eight hours together with them. Just kinda putting people in unique environments and seeing who they are when they just have to be them. Get comfortable being uncomfortable because we're constantly changing. We're constantly growing and not just growing to grow, but listening to our customers and what it is. And so I need to have people on our team that listen really well and also challenge too. They're not afraid to tell a customer or a carrier you're wrong and here's why I believe you're wrong.
[43:28] Managing a distributed leadership team
Jesse Buckingham: Your leadership team is in different parts of the US. How do you manage that?
Ryan Keepman: I guess I don't really know any difference. My goal has always been to go get the best people, and we'll figure out the location part later. We have two of our leadership or executive members in Delafield, Wisconsin outside of Milwaukee, and we have one up in Minneapolis, one in Atlanta, one in Chattanooga, and myself down here. So we do, to actually answer your question, quarterly in person meetings at usually one of the office locations so we can spend time with our team. And then our leadership team as well is also remote. So bringing them together on a quarterly basis, all of our teams and their managers or directors or VPs are required to bring the teams together quarterly. Whether it's our key account management team, our sales team, our tech team, everybody's getting together regularly. And we always do experiences. For example, our last executive retreat, we showed up to a cliff and one of John Conrad's buddies was standing there with rappelling ropes. Our CFO says right away, he goes, you know, this is probably a bad idea from a risk perspective. But some of us did it. And those type of experiences, they just glue you together.
[47:43] Leadership evolution
Jesse Buckingham: What are some of the big ways in which you have shifted your leadership over the last ten, twenty years?
Ryan Keepman: I think something I can be vulnerable about — I struggled with being direct with people, you know, and wanting to tell them something they wanted to hear. What I've learned through not telling people what they should hear — telling people what they wanna hear but should be telling them something else — is it creates a lot more of an issue down the road versus just being direct up front with somebody. So from job role or responsibility, the extreme on one end to a simple, no. You're wrong about this decision, and here's why. Not just letting it pass because you have so many of those opportunities as a leader. It doesn't get people better. And one of the greatest rewards in leadership is seeing true transformation in people. Not just from a performance in work, which is super important, but also seeing their lives get enhanced and making a dramatic impact on their family they never made before. I also read a book recently — Strength to Strength. It talks about how, as leaders, we do have to continue to change. And it's kinda when you hit that 40-43 age bracket, kinda like the Michael Jordans or the Brett Favres of the world, who just can't give it up. What got them to that pinnacle requires change. And so you can't play hoops the rest of your life. You've gotta make an intentional change as a person. So I bought that book for my entire leadership team. I wanna see people continue to grow, mature, and be the best people they were designed to be.
[53:47] How AI gave Evans brokers their relationship time back
Ryan Keepman: Being around people. I just love to be around people. I can be alone, but I noticed that my energy feeds off of others quite a bit. And one of my friends always says, good people attract good people. When I'm around those people, I'm my best self, and I'm my best energy. My kids — every car ride that I have my daughter on that's 14, shutting her phone off so I can get her attention. And I have a 16 year old boy as well. He brings his buddies up to the farm and we hunt and do things like that. Once you get north of I-10, all the phones come into the console of the car. By the time we're on our way home, these 16 year old boys are singing. They're acting like kids again, and you can't get the smiles off their face. It's kinda going back to that interpersonal side that is being lost by technology.
Ryan Keepman: And we are so grateful for Vooma. Where you think AI could kinda take away that interpersonal ability to have a business transaction with somebody, for us, it's enhanced it. We had one of our brokers the other day tell us that with some of the bots that you've created for us or the answering services, he used to receive so many calls in a day. Obviously, couldn't answer them all from the load boards. Carriers calling in. He said the other day, he only received 10 calls and it allowed him to call all of his favorite carriers and say Merry Christmas. Tell him how appreciative he was and ended up booking a few loads because of it. But it's allowed us to focus more on the relationship side of the business, which is what we value.