Lightning like Steve McQueen I'm in a fast lane when the light turns green and I built up find nothing but grit Cause I made rugged blood sweat and spit yeah, like a horse I fly for a bumpy ride I like to play hard but I work harder and I weather the storm Because I'm built stronger.
What is up, ladies and gentlemen? We are back. We are live. It is the Freight Coach podcast, the top podcast in transportation coming to you guys every single weekday, 8:30am Pacific, 10:30 Central, to break down some industry headlines. But most importantly, you guys provide some actual insight into what you can do with all of this information. If this is your first time tuning in, welcome. This is the real side of freight, ladies and gentlemen. And I say that before every single show. And what I mean by that is I only speak with transportation professionals because at the end of the day, you guys, I want to talk to the right individuals who have done what you're looking to do or who are currently doing what you're trying to achieve.
So you can take that information, apply it, utilize it, and see a meaningful difference in your business and your life. I'm going to save the rest of everything else. You guys know what to do because I got a very special guest for you guys that I'm going to bring on up here. And you know, I literally talked to him for the first time like two and a half weeks ago. And it's going to be an action packed conversation. You guys founding, you know, businesses, investing in freight in, you know, freight tech, selling a business in freight tech, and then all that is going to come full circle. So with that being said, I have freight tech aficionado, Mr. Brad Hollister on the show, ladies and gentlemen. So Brad, thank you so much for joining me.
Thanks, jolly. Thanks for having me.
No, man, absolutely. And you know, I, I just love the Wisconsin backdrop, man. It's like it kind of makes me miss home a little bit. Until you guys are getting snow. Then I'm like, I'm glad I live in Arizona now.
Yeah, you know, I got out this morning early in the woods and it was know winter is upon us here up in the Northwood. So Wisconsin is going to get snow soon, dude.
Absolutely, man. So Brad, like what, How'd you get your start in freight, man? Like what brought you into this industry?
You know, everyone has an interesting story and I think it's always by accident. You know, everybody seems to have gotten in here by accident. And then once you're in logistics or freight, some people can claw their way out For a short amount of time. But our industry always has a way of pulling you back, which is, you know, we all joke about, but, you know, I think it's for a lot of reasons. One, I mean, you build so many friendships and so many relationships that, you know, when you excel in one thing, or frankly, if you're a good person, you know, you're gonna build a following that people then people like you, and you're gonna find another seat somewhere else. But for me, I was a longtime high school and college wrestler, and.
And I ran into a friend of mine that was doing some. In the early days, do you remember when people would, like, negotiate parcel contracts?
Yeah. Yeah.
So, like in the mid 2000, like, you know, between like 2000 and 2010, it was like the birth of that industry and like the wild west. Like, you could charge. You know, there wasn't that many companies doing it. The message wasn't saturated. You could charge a ton of money, like 50% gain share for three years on a contract. And I started working with a friend of mine selling that, and we did really well. So that was kind of my first go into it. And then we moved into freight, and then I went and worked at sia. SIA was just rolling out their national network. And I'll tell you, it was a time to learn LTL from the, you know, boots on the ground, because there was no, like, fuel surcharges back then. There was like, no reweighs, no os, and D hardly.
I mean, SIA was a mess because they were putting together like six companies. So it was an awesome time to learn the LTL business. So that was really kind of what left. And then after, you know, oil and gas got up to 4 bucks a gallon, which is almost like, you know, we're used to now. But for the first time in 2008 with George W. Bush, and everyone panicked. You know, Saya went through a massive layoff, and I was the. I was the new person. I'd only been there two years. And so they went through a massive layoff. And so I went to the freight brokerage industry for a small freight broker in Wisconsin that's not around anymore and kind of learned the business that way. So it was kind of a.
I accidentally, you know, saw the business from many different sides, from parcel to LTL to truckload. I really don't have a lot of experience in ocean. But domestic. I mean, that's a whole nother mix, right? You get with an ocean person, they're speaking totally different language, but you Know, they could say the same thing about ltl for sure.
Yeah, I agree wholeheartedly with you, man, and that. But like, I think getting that kind of unique experience really helps you. I think it helps you realize the importance of focusing one thing and doing it better than literally everybody else. Because I think that, you know, and it takes going through multiple things to actually understand, like, hey, this is the area I want to focus in on. This is what I really want to niche down on. Because, you know, otherwise it's very hard to delineate your service offering or what you do differently than your competition if you're kind of doing the spray and pray methodology behind it. And I think, like, that's one thing that I'm very glad that I adopted inside of my business very early on was, is, hey, full truckload. That's all that we're going to do.
Yeah, we tried to dabble here and there, but I just came to realize, like, it's just not in our cards. Like, if we're going to do something that we can build and scale out, we have to do the exact same thing every single day. Like, we have to master the monotonous and everybody wants to chase the sexy next thing that's out there where it's like, no, I want to master the monotonous and I want to provide a service that is so much better and more efficient than everybody else out there that people are inclined to want to work with us.
Well, that's a great point. So in that, you know, unpacking what you just said, I mean, if you go to good clients, right? Good companies, solid companies that have, you know, weathered a lot of financial recessions over the years, they are pursuing the expert in that category. For example, like, you know, it would make sense that they would roll out a TMS that did, you know, everything. But when you start to look at like leading companies, they run a parcel tms, they run LTL differently, they run truckload, completely separate, and they run even returns differently. So thankfully, we're in an era that people have been able to take some pieces of AI and plug in to kind of start to make these data silos talk to each other.
But I can understand going back why leading companies, Fortune 500s would pick different technologies to do different tasks within their supply chain.
So speaking of freight tech, I mean, that's kind of like what you know, because you built up, you know, a tech company and you know, you've since exited that. And you know, what was that like? You know, kind of. Because you've been in the industry for a while, right? So you kind of saw the pre tech adoption to a little bit of tech hesitancy to now People are like, we need to automate everything inside of our day to day. And I mean, obviously there's still some resistance that's out there. But like, what was that like building that company up in kind of like. I don't want to call it the heyday of freight tech, but like, you know, with what you did, there was kind of like the beginning wave of like a lot of new technology coming into our space.
Well, it was. I have a famous quote. I was interviewed by Inc. And they asked what it's like running Swan Leap. And I said I was joking. I don't, I didn't think were recording or whatever during the interview. And I said it's kind of like looking through a kaleidoscope on LSD like every day because you just don't know what's coming at you every day. Like literally didn't know what was coming at me. Like every day was something new. And it's like, you know, I was almost worried like when everything was calm and going well, you know, like it was just chaos. And I think anybody running any kind of startup understands that, you know, it's. It was, it was honestly hell. And I had a friend of mine that just raised like $500 million outside of freight tech.
And I asked him, he's seven years in. I'm like, how's it going? You having fun? And he's like, yeah, it's awesome. I'm like, I said, bullshit. You're seven years in. I mean, you could tell your investors that, you could tell your employees that, you could tell your wife that, you know, but at the end of the day, I know like what you're going through, man. It's because, you know, even the people that have, you know, a tireless work ethic, you know, can't run at that pace forever. And I realized that in hindsight. So that, yeah, that's kind of what like led to, you know, I never built the company with an exit in mind. I don't think most entrepreneurs do because you can't go through that hard of a thing. Like 95% committed. It just will not work out in your favor.
Right.
Like, David Goggins doesn't run his races, you know, pretty sure he's going to finish.
No, I think that's a great point there, Brad, that I think is overlooked by kind of the Entrepreneur gurus on social media right now is it's like, if you're. I think if your intention is to go in and then build a company and just sell it within five years, I think that you're going to be met with massive resistance that's out there because, like, ultimately your only intent is for you to make money and nobody else is really going to gain any value from it, right? Where it's like, I think, like. And everybody goes through it, right? I don't know anybody who starts a business that's like, oh, hey, I'm hoping to come in it and then get more poor throughout this, right? Like, of course making money and building something cool is. Is on the agenda.
But I think that, you know, it's like what you have to go through. I mean, because, like, dude, I'm four years into this, right? Like, I'm not a guru or an expert. I just know what I know and what I've been through, and I'm way too fucking committed at this point to even think twice about it. But, like, the reality is this is literally the hardest thing I've ever done. And it continues to be that way. But it's not the work that's hard. It's all the other stuff that you have to deal with that you never. You're insulated from as an employee. You know, like, were talking before we started recording, you know, like, dealing with banks, dealing with lawyers, dealing with all of that stuff.
It's necessary, but it's like, man, it's so draining because, like, if you want to raise money, for example, or if you want to go get a line of credit from the bank, they can pull all that shit away at any given moment, right?
Like, when you need it. Yeah, when you need it.
Yeah. So it's like, it's all of that stuff that you have to go through and you know. Cause it's not just, oh, hey, I started an llc, now I'm a millionaire. Like, it is such a challenge.
The other problem, though is like. Like, I felt when going through it, like, I didn't there when Covid hit, right? I asked my leadership team, can you guys. I don't know what this thing's going to look like. I need to get a 1025 and a 50% cut plan for your budget. Like, I don't know what this is gonna do, right? I mean, they're. They're talking, remember, you guys remember, like, they're talking like, truckloads of bodies and stuff.
Yeah, dude.
Like, remember, like, when it first came out, it's like, oh, my God. So I. I'm like, I don't know what we're gonna do. Like, I want 10, 25, and 50% cut plan for your budget. Like, what are we gonna do if we're like, we have to base? Almost like, survive.
Yeah.
And. And you know, I had 1. My VP of Tech, not. Not the CFO or CTO, but our VP of Tech resigned because he said, you guys are going out of business. I'm like, what are you talking about? I'm doing everything I can just to stay in business. And that was, you know, what we. You know, what we did during that time. We didn't have a lot of E commerce exposure. The ones that did, like, blew up during COVID Like. Right. They did so well. We did a lot in the oil and gas space. So our revenue was down quite a bit during COVID But I was going to ask, you know, like, to everyone listening, like, there's a million, like, executive groups out there. I've heard a lot of people get value out of ypo. I couldn't make YPO work for me.
Young Presence Organization, I think it stands for. There's other CEO groups that I think have value. The problem that I had with them is I couldn't find any CEO groups that were strictly founder groups.
So I actually, I'm very like, I. I'm involved with the group and I know that there's not. It's not just founders that are in this group, but it's like the overwhelming majority is, and it's called the Arete Syndicate. And that. That has brought a ton of value in just being inside of that realm of people. Right. And it's like, I think for me, it's more of, like, being around people and knowing who to go to when, like, you're. You're faced with something that you've never known, like, been through. And then they're like, oh, dude, I've been through that 20 years ago. This is exactly how you handle it. That's the stuff that invaluable that. That's that you as a founder, I think you need to surround yourself with. And I actually just put a post out there this morning about this.
Brad, like, the best thing that I've ever, like, the most effective decision that I've ever made was is I stopped taking advice from people that aren't actually ahead of me. And that has cleared up so much stuff. Right. And again, I use it for, like, my weight. Like, I stopped taking fitness advice from people who are overweight. You know, like, I stopped taking financial advice from people who are riddled in debt because it's also it to me, it's like, it's one of those things where it's like, otherwise it's just theory, it's just an opinion. Because if it really worked, you'd be doing it.
I mean, that is so true. I mean, I kind of feel the same way with motivational speakers. I feel the same way about so many things. SEO in your business, when you're getting pitched by SEO company, it's like, if you're really good at this, why would you waste your time with selling this service? Why wouldn't you just get to the top of Google on all these wonderful things? But that's a great point because it really helps you to block the noise, right? To focus. So I, Andrew Silver or Matt Silver just posted something I thought was like a great post for this year that I hadn't seen, like one of the more powerful ones. And Matt Silver said, stop taking appointments with people as a founder. And like, I don't remember what else he said. You could probably look it up.
But like, holy shit. Like that is so important as a founder to like know going in, you know, what, you know what your objective is and everything. And also managing those expectations with, hey, here's what I want to accomplish today, you know, like, because, you know, you really don't have time to spin your tires at all. You have to be effective.
So, dude, that's another very good point though, right? Is it's like you have to do that. You have to control your calendar. And I, and again, I learned this from the entrepreneur group that I'm involved in where it's like a first meeting with somebody, unless it is a direct introduction from somebody who I know and trust. If this is kind of like a cold introduction, it's like no more than a 15 minute. If you can't get that out. And again, I'm not trying to be disrespectful, but like my time is the only value that I have, right? Like, that's the only non, like it's the only thing that I can't get more of. So it's like I have to be very mindful of that.
And then because like, I've also noticed, you know, as an early founder, because I think what a lot of that breeds though, Brad, is it's like you go from like, anybody pay attention to me, please, anybody give me the time of day. And then you get A little bit of that. And then you start to realize, like, do people just take meetings for the sake of taking meetings? Like, what are we. What are we doing here?
You know what? You know, who does? Employees.
Yeah. No, it's.
That's the truth.
It's true, man.
And that's, you know, not necessarily all employees, but it's just the mentality of somebody that is, like, busy being busy or busy producing and executing.
So, yeah, I'm right there with you on that, man. And so what was it like? You know, you're some, like, what was it like exiting a company? What was it like being acquired? What was that like? What did that feel like the next morning when it was all said and done?
Well, I hated Covid, right? Like, I hated what it did to my company. I hated what it did to my culture. You know, Like, I was, like, literally fighting with all my development team that could find all kinds of excuses because we're more productive at home. Come on. Bullshit. You are. Come on. I'm not a fool, right? But I couldn't get anybody to come back for safety and everything, so I lost that battle. And I hated it because especially back in maybe five years ago, there was constantly Silicon Valley recruiters picking off my Midwestern developers for, you know, they were making a hundred grand, 120 grand, you know, and paying. You know, the Silicon Valley recruiters are thinking, these guys are half price or less. And when I heard, like, the first Silicon Valley programmer getting, like 400 grand, I couldn't believe it.
Now it's 600 grand, I hear. You know, it's just nuts. But, I mean, that was a hard thing, is like, retention and culture and, you know, I feel like my growth really slowed down and stopped because not only was our client base slowing down, but also, like, we really couldn't visit clients anymore. You know, it was just tough to, you know, for us to win new business under the way that we are winning business. So that was tough. And then, so I couldn't, like, I'd never emotionally could get past this because the business was like a member of our family, you know, like, there was a time went to Disney and, like, I was having just a complete fire, right? I'm in the parking lot. My kids were, I don't know, maybe 14, nine and four.
I mean, and they sat in the parking lot. If I would have known it was going to be like, all morning, like, dealing with this issue, I would have just sent them in. But it was like, 10 more minutes. 10 more minutes. 10 more minutes, 10 more minutes, and it was hours. And my kids sat in the parking lot at Disney for half the day. And that's just. That's the other thing. Like, when you're in this, right? I mean, you have to have everyone else around you aligned, like your family and your spouse, and you have to. Because they have to understand that you could be in the. You could have a family vacation that gets canceled. And it's not for the faint of heart. But. So were.
We decided during COVID to go to Puerto Rico for two months because, you know, I didn't want to sit in Wisconsin and freeze. And there was no sense. And weren't, you know, able to go out. So it was a pretty nice setup. We were just sitting, you know, on the balcony, working all day. And my kids were in school, so they were sitting at the table outside with me. So I was doing calls, they were doing school. It was great. And we had seven inbound inquiries to acquire us in January. And, you know, I also wasn't prepared for that. It was like, we got a lot of, like, inbound, like, you know, inquiries, but I didn't know how real they were. And you always, as a founder kind of, like, posture, like, well, yeah, I'm not for sale, you know.
Cause I'm so cool, right? But it's. But deep down, I think. I think it was like, in hindsight, I was scared. I didn't know how to have a conversation, and I was scared. I didn't want to fuck it up. The thing about this time that was a little different was I knew all the inbound people. They were all strategic. It made it a little easier. Then Jason Swanson, my co founder, cto, said to me, brad, we're starting to develop some legacy code. And I. He hit me at, like, just a time that I was just having a hard time with some of the programmers, you know, trying to, you know, execute and get stuff out. And. And. And he said, what if we just rebuild the whole system? Like, he's like, we could do it for like a million bucks.
Like, just four guys could do it, and we could do it in probably four to six months. We know exactly what to do now. And, you know, blah, blah. We'd be like, get rid of legacy code. Get real rid of all these whining bitches that we have on our payroll, and let's just go and start over. And I'm just sell it. Take a. Take some chips off the table and keep going. I'm like, yeah, let's do it. Well, clearly that can't happen during an acquisition. Like, you know, that's, they want some non compete, they want some assurances, et cetera. But that helped me get over mentally to see my life beyond what I was doing, that I couldn't see my life beyond it. So that helped a lot.
And then from there, we thought that NTG in Atlanta would be the best place for the technology to really make a difference. And so part of it was like sending a kid off to college, right? Because like, I had to like send the tech off and put it in their hands and see what they could do with it. But I mean, you know, NTG is a leader in the industry and you know, they had great people there. And you know, I thought it was a nice fit. So it was great.
So I was going to say in true founder fashion that we'll fast forward today because you were out and then now you're just like, I like. And I'm saying this, Brad, because like I, you know, I can never, like, I cannot sit here with a straight face and ever say that I could retire. Like, I would be bored, My wife would probably, I would probably be dropped off in the desert somewhere. My wife would want to kill me if I had nothing to do. Because like, I'm just, that's just the way that I'm wired. I love the build, right? Like, I have come to the conclusion. I love going from a laptop in my bedroom to where I am. Like, I love the build aspect of it. So what is it now that. What do you got going on?
Because this is kind of a pretty exciting thing. And I'm, and I'm truly honored that you and Charlie came to me to be like, to kind of put this out there to break the news.
Okay? So imagine like we, you know, we close, we get a bunch of money wired to us. And my biggest fear in going through everything was like, how am I gonna produce income, right? Like having a bunch of money was an illogical fear that it would window dwindle down. And so for me it was like, I need to produce. So I went and built a pretty big real estate company that my wife runs. And it's pretty big, you know, has a lot of doors and she manages the managers and stuff. And, you know, we deployed the capital. I also got with a lot of, you know, kind of the seed. The seed kind of little rounds. I started seeing a lot of investment decks and made a handful of investments into some companies that I thought were, you know, pretty cool.
And I was doing this, I was living in Puerto Rico and you know, didn't have really too much more money to deploy other than, you know, safety net and stuff. And now I'm like kind of living off the rental income. And for me, Chris, it was more like losing. I was really like losing a sense of purpose, honestly. Like, I mean my best friend was, you know, this like 75 year old lady that I lived close by. We would go and have drinks together and stuff and it's just like I missed kind of all the conference, the action, you know, kind of like, you know how you kind of like put pieces together of connections or you know, solve problems, you know, business problems.
And I was missing that and I, Charlie Dahoney came to me, we had done some co investing in some other startups already and he's like, you know, we sat for hours and really laid out this idea of accounts receivable platform because when he was owning or when he owned the brokerage and his trucking company now, you know, they were having problems with getting paid and you know, the imagine receivables going 30, 45 days but things you could do yourself to fix that or using technology to fix that. And so he laid this all out for me and I had a lot of questions. It's not an area of the business that I truly understood at first. And, and so I told him like, let's do it, I'll write a check. And I wrote the check.
I was the first investor in Upwell and I'm really excited about that. So since then it's been really interesting to see how many more people he's been able to evangelize and get involved on his cap table from like the Mount Rushmore freight is on his cap table. It's, it's amazing company. And so we got back, sent one kid off to college, got back to Wisconsin and I told him, I said look, my, you know, we're going to homeschool my two children so I can make some calls with you and I can listen in on some calls. And when I started hearing the conviction and one call on, you know, in his voice, but also, you know, the customers on the other side, you know, literally like one call closes to get brokers and carriers to like automate their receivables.
I mean, holy cow, it was really powerful. And then to see how fast they've grown in just a few months, I told Charlie, I'm like, look, I'll come on board like I'll. I'll just volunteer. Like, I'll work there, you know, And. And he's like, well, I'm not gonna have you do that. And I'm like, yeah, but like, let. Forget the money, let's just build it. Let's build this thing. Now he's got a co founder. I'm not. I'm not putting my. My fingerprint on the co founder title. But yeah, he's got wonderful people over there that had a really good head start for about nine months. And so it's been really cool to sit and watch and be on calls. And then when I started kind of like taking this and thinking about it and tapping into my network, it was awesome.
When Charlie's got a huge network, I got a huge network, and there's some that don't overlap, which is great. So it's been really cool to see this kind of come together. And we are coming on your show to announce that my title as head of growth at Upwell and I'm going to run with Upwell full time for the foreseeable future. So I'm really excited to be here and help to automate receivables for trucking companies and three PLs.
Dude, I love that. I'm very, very much a fan of Charlie and anything that he does. And you know, I know with you being fully on board like this as well and running with it, I think that it's. It's definitely something that any business owner out there and it's not just a freight brokerage or a trucking company thing. When it comes down to receivables, that's the, like the capital I. You know, and then financial literacy, like, that's why we do the monthly show with denim, right? About like teaching financial literacy inside of business is a completely different ballgame than your personal finances and getting paid and making sure that you're doing that properly to manage your receivables.
I mean, I think it's a pretty common stat that's out there that most small businesses are 30 days away from being out of business every single month because of capital restraints.
Well, I'll tell you something I've learned that's really cool in just the month or so that I've been there. When you look at successful freight brokerages and we can all think in our mind five or six that we know pretty well, you think of the CEO, I mean, they're almost always a salesperson. You know, when it comes down to it, face of the company, you think of the carrier sales division that, you know, there's somebody in the carrier sales that are doing great things. You think about the tech guy, right? That's the person or woman that are running the tech strategy.
But it's not common to think about the finance group at your freight brokerage, especially the men and women that work in the receivable side that are like, that know the intricate details of like this customer needs to be billed this way in order for us to continue to receive the payment and stay in business. And so that's what's really cool is like there's been so many like really smart people that go very underappreciated in their accounts receivable department because they do things that no one sees to keep the business moving. And it's, and it's. I think a lot of us, well, especially me, has taken that for granted. No question.
Yeah, I mean, I, and I think, you know, another really big point is, you know, every customer out there that you work with, any shipping customer, they all have different billing preferences. They all have different requirements, processes and everything else. That's the one thing that you can't have happen. Right. Like, in all honesty, I think your service is obvious. Service communication is in one bucket of number two or number one, but like with and then number two. And this is a very close second with a lot of shippers. Are you invoicing them properly? Are you following their process? Because if you become a thorn in their side to get paid, you're going to be out like, I think like you'd be out faster than anything.
Yeah, I mean, not only that, but, you know, the, some people, some brokers have suggested they think the shippers add complications to slow down their payment. I don't know about that, but I will say this, that, you know, thankfully there's a person in your company that knows how to build that company or, you know, build that customer. The problem is what we found is if it is this scenario where someone's very difficult to build, then they typically will like bill them on Wednesdays or Thursday afternoons. Is the, is the, this customer billing, for example.
And the problem in that is that, you know, the broker is sitting on that money for, you know, or that ability to collect that money for a few days before they even, you know, submit the bill, which maybe it missed the payment by one day and now is going to go a whole nother payment cycle. So the, in this space, hours to process invoices could equate to a very long receivables period. So it's not, you know, inconceivable to pick up four days with automation in your receivables, which is, you know, tons of money. If you start to take some of these major mega billion dollar brokerages, you're talking, you know, 50, $60 million in value from having that money faster, dude.
Amen to that. And Brad, we're gonna have to continue with that. Like I told you that this was going to go by quick, man, and it did. And dude, I, I'm very, I appreciate you joining me. I appreciate you guys letting this be the show that announces you getting back in and joining up. Well and I'm very much a big fan of what you guys got going on over there. How does anybody reach out to you guys though, to find out more?
Upwell.com is great. I mean, my email is brad.hollisterupwell. I'm happy to, you know, get some information to somebody or see if there's anything we do to help them. But yeah, it's been a really fun ride and the story is just being written now.
So dude, I love it. And if you guys can't find Brad or up, well, hit me up. I will put you guys in direct contact with them. But that is going to be it for today. We will be back tomorrow. We got another guest coming on tomorrow, you guys. And as always, if you guys got value in what you heard, subscribe to the show. You guys share it out there. Dear network. Because if you see value, your network's going to see value as well. I appreciate you guys. I love you guys and we'll be talking to you soon. And now we just kind of have.