Brick by Brick with Joe DiLeo

We've got one of the new themes kind of emerging this year in the show is we have a lot of relationships in Nashville that have sprung out of the Bitfreighter Golf Tournament , led by Brad Perling and his team , josh Lyles with Sales Dash , the CRM and a handful of other folks , and it makes life wonderful when you get to travel to cities like Nashville and you

run into a bunch of people that you know and friends that you haven't seen for a while . So we're going to add one more Nashville founder to the fold this week with Joe Dilio , who's the founder and CEO of Chariot Logistics . Good morning , joe . How are you today ?

They're like oh , nashville's Freight Alley too . I don't know if that's the truth or not , but you know , I think what makes it is Nashville's an attractive city and what we do in freight brokerage it's .

You know we got a lot of new grads that come out to get into it and people like to move to Nashville because they want to go party on Broadway and you know , I think that that kind of equates to why we have good freight brokerage talent here .

I think we have a good talent pool and we're seeing more and more brokerages pop up , you know , and there's some other bigger shops that have opened up , you know branches and stuff here . But I think it's a good city .

I think that you know it's a fun city , I think , which equates to a lot of it , because you know people , quite frankly , they want to move to Nashville . They probably came here on a vacation and they're like , oh , I'd like to move there . So you know which we like .

You know , come on , nashville's growing and growing and growing , and so are the freight brokerages . So we need good people .

I went to UT , got a , got a at that point it was a logistics degree . Now they're called supply chain degrees and um , my first job was at a place called Calvary Logistics and um , kind of go in the door and I was like they didn't teach me anything about this in college . I did . This was this was not like logistics , uh , so learned that .

And I was like man , these guys are making so much money and this is not hard . I could do this on my own . And then I had this great idea that I'm going to start a freight brokerage and I did . I was 25 . And at that time the barriers to entry were not anywhere near they are now . This is before the MAP-21 and the 75K broker bond .

And you know you just had to put up a 10K bond and pretty much you could hit the ground running . So I did . You know , I was living in the city with some roommates Me and Brad actually lived together at that point because we were working at Calvary together and I was like man , I'm going to start a freight brokerage and move back in with my dad .

So I moved back in with my dad because I I was like I'm gonna need all the money I need .

So that was a humbling experience and just started from from the ground up and it was me , a computer , a DAT login and I guess what , what at the time would have been called a CRM , but now would probably just be called a , you know , an obsolete piece of technology but and just kind of hit the ground running like didn't have any customers to bring with me ,

didn't have any , you know , like pre-existing relationships where I was getting freight . So you know , I was , I was 25 years old and it was May of 2012 , was when we first started . I was 25 years old and it was May of 2012 was when we first started .

And for those first , I think it took me three months to get my first load and move it and it was just grinding out , just hammering calls and hammering and hammering and hammering , and it was a lot of hard work . But I'll never forget when I got my first load .

It was a load of bricks from Nashville , tennessee , to Charlotte , north Carolina , and I was such a new broker and this was before all this like fraud , double brokering , everything like that . But I had a new MC number . My MC number is 782830 .

And now that's like that's an old MC number , but back in the day I'd tell them that they I'll never forget I would call people and they'd be be like what's your mc number ? They'd be like I'm like seven , eight . They'd be oh , that's a brand new mc number , I don't know . I don't know if we can work with you guys .

So you know , we would get freight and or I would get freight and then it would . And then that's when , like , the battle began of like trying to find carriers who would be like , oh , this guy's not gonna like scam me , or this guy's not going to like scam me , or this guy's not going to pay me , kind of thing .

And you know , I spent a lot , I've spent lots of times on the phone with you know , carriers , finance departments and factoring companies and just being like I promise I'll pay you , or you know I'm brand new , but I , you know I'll pay you .

You know having to pay people , like money in advance and stuff like that and um , really kind of just like went through that for like a year .

And then we started , then I started really gaining traction , um , and then , uh , you know , I was by myself for two years , it was just me , um , and I got it and I was probably booking , I don't know , maybe maybe 20 loads a week .

If we're being honest , my first year , um , and you know , a funny thing about it is I had a , a buddy of mine who was actually a carrier that I used to do a lot of work with at when I was working at Calvary , and he , the carrier , he was like a load planning dispatch service , so that's like what he did , and he , he , like I , kind of was like you

know , I'm going to try and do that too . So I , so I was kind of working both sides a little bit to where I was .

I had some owner operators that I developed some relationships with and I actually got them to like I was like , hey , man , I , you know , if you need help getting loads of load boards , like I'll help you and I would like call and like I would help these carriers .

But the whole goal was I was like I'm going to put them on my freight , I'm going to , I want to put these carriers on my freight . And that just turned into something that never worked out because it was just one person doing it .

But I'm very fond of my load plan dispatching years and it was about two years because it's really kind of what kept the lights on and paid the bills in Chariot because , you know , these guys were paying me like $300 a month to like I would find them loads every day , which was interesting . I learned a lot about it .

There was , you know , there's a funny story where I was , I picked up a load , or I we picked up a load , and it was an older driver and I had to .

He shows up at a Walmart and it's a driver assist of a load of mulch and they didn't tell us that and it was about 30 miles North of Nashville and my driver's there and he's like hey man , I'm here , they're telling me that I got to unload this product myself and this guy's like 70 years old and couldn't work it out with the broker and I had to get .

I got in my car and drove up to Bowling Green , kentucky , to this Walmart and driver assisted this load of mulch out of the back of this trailer . And I'll tell you what , if you don't talk about some hard work in a 99 degree Tennessee heat with 44,000 pounds of mulch , that was it .

But you know , really grassroots approach to like brokerage in the beginning and did what it took to , you know , to keep the doors open , to keep you know , to keep freight coming through and never , never , ever , thought that it wasn't going to work .

And it was a lot of hard work for the first two years and , you know , I finally got to the point to where , you know , I was like , all right , getting some traction , we got some freight . So then I hired my first employee in like 2014 .

Um , then hired my second employee that same year , and then , you know , hired my third employee , like the same years , and then , and then , at that point , I had to give up the low plan dispatch , which was hard to me , cause I had , like , really , really , um , gotten to know these drivers , uh , but at that point it was like I can't spend all my time ,

you know , helping you guys find loads . I got my own loads , I got books , so , which was good , which was always the plan .

But it's a kind of a humble origin story , but you know , it's rooted in just hard work , you know , and I was willing to kind of , you know , take that chance when I was young , because I was thinking .

I was like , if I'm going to do this , I need to do it now because I'm not married , don't have any kids , I didn't , you know , barely had any bills moved back in with my dad , kind of thing , and , um , it was like now's the time to do it . Um , now's the time to do it . And I did and never looked back .

Um , when I , when I started , I thought I knew everything about logistics and transportation , very quickly into it I realized that you do not know what you're doing . So you know , kind of had to fake it until I made it . You know that was the same for us Fake it till you make it , fake it till you make it .

And we did , and you know it's just grown organically , got a lot of good people . And then , you know , and I got to the point like I would say , like 2015, .

You know , we've been in business for like three years and we were , you know , being profitable at that point , making good money and , you know , moving a good amount of freight , and then started bringing on some people from some other brokerages .

We were like , hey , you know , came in from some other brokers , this is how you need to do it , this is how we're going to go land customers . I was never on . Everything I knew about sales . I had to self-teach myself because I was a carrier sales rep at Calvary . I was never on the sales side .

I learned that just through hammering the phones and getting my teeth kicked in . I brought some guys in who helped with corporate selling and , you know , landed our first , you know . You know , top 100 accounts started moving . You know TMS , managed freight . So that was really in 2015 , was really when we started .

I would say that we really kind of became like more of a sophisticated broker , started interacting with people like via EDI and , you know , got our first like accounts that we had like managed trans , who like the big , like TMS , you know systems and stuff like that .

So you know , in 15 , that was when it really started to take off , because before that it was more of like . You know , we were , you know , chasing your , you know your mid-market shippers . Your guys are sending out load lists and not to say that we don't still do business with them , because those are accounts that you have to do business with .

But that was when we first kind of broke into that more of that corporate logistics , which we do a lot of that too . So we're , you know , we're doing both these days . I'm very thankful for that . But you know it is a . You know 15 was kind of when we started , but you know it is a . You know 15 was kind of when we started .

You know , doing it a little differently . And then we had a sales team and an ops team and kind of segmented the brokerage to where we had people concentrating on care relationships , people concentrating on customers , and then we just continue to add to that fire . And here we are . You know that would be what nine years later .

We just celebrated our 12-year anniversary . Congratulations , yeah , thank you . And you know we're not the biggest broker . I've seen some brokers pop up that are newer than us , that are bigger than us , but I equate us to like an oak tree .

Like the oak tree is the tree that grows the slowest but it's the strongest and has the deepest roots , is the tree that grows the slowest but it's the strongest and has the deepest roots and we've been able to , you know , retain this organic brokerage , which allows us to do things that other brokers don't do , allows us to , you know , invest in our people more

. I don't have to report to a board of directors that are finance people that aren't freight people , you know , to a board of directors that are finance people that aren't freight people .

You know , I , I report to you know , myself , I guess , and uh , um , you know , and we , we're very proud of that and you know , from our perspective , it's the goal is not to be the biggest , it's to be chariot and um , you know , we've , I've struggled with that a lot and especially in like you know , with like the , the keeping up with the Joneses culture

of like social media and stuff these days . You know , and you know the old saying , like comparisons , the thief of joy , like you know it is , it's the truth . And uh , you know , especially as a bootstrapper , you gotta , gotta realize who you are . Now I was talking to like a recruiter not too long ago .

You know we were talking about different brokerages and then , you know , and talking about just like people and talent and stuff like that , and he said to me he was like he was , you know , talking to comparing to somebody's other brokers and he was like man , you're bootstrapped , you're built different and I'm like you know I am , I am like we're and we're able

to add and flow with the markets and , you know , we're able to get lean if we need to . And you know we got a really solid foundation , got a very solid team , really have core people who've been with us for a long time , and you know we've built something very special . And our motto here is carrying people to a better place .

It's not like , you know , get more freight . You know , make more money . It's like carrying people to a better place and obviously an easy way to do that is to , you know , pay people money . It's like carrying people to a better place and obviously an easy way to do that is to , you know , pay people money , because money is what make the world go round .

But there's other things , like you know , work-life balance , like actually enjoying and liking your job .

You know , having a boss that is going to like invest and care about you , and those are things that we , you know , really take pride in at Chariot and I've seen , like my , my , really take pride in a chariot and I've seen , like my , my employees and people who've worked with us for a long time , like where they came in at because none of these people had

any experience with our coming in and like where they're at now . It's like these are like transportation professions , like you know they , they're , you know they are , you know they are sophisticated , educated . You know experts in freight brokerage , and that's something very proud of .

And I've seen these guys achieve life goals , get married , buy houses , go on their dream vacations . You know , whatever , whatever their goals are and you know I feel , like you know I've been a part of that and that's really what gets you going is your people . You know Henry Ford said it .

He was like you can take everything away from me , but leave me my people and I'll rebuild it better and that's just kind of the philosophy that we've always had here . You know it's it's it's about our people , it's about doing .

You know it's about , you know , trying to empower them and being loyal to them and then they'll be loyal to you and we're able to do that because it's not all about the bottom line and I'm not saying like we don't have to make money because we do and that's that's the focus , but it's it's not the only thing that matters and it's not what drives every

decision . So you know , that's when I you know , if I think back to 2012 when I started it , that was always in me was like , cause I to 2012 ?

When I started it , that was always in me was like because I saw how , like a corporate brokerage kind of did things and kind of , you know , ran through some people and kind of burned some people out and I was like you know , this can be done different . And you know it's like I want to start a freight brokerage and do it different .

And I feel like we have and , yeah , might not be as big as the guys down the street , but we're solid and we're proud of that and we have customers that love us . We have carriers that love us , we got employees that love us and we're growing every day . And you know it's the , you know sky's the limit is the goal here .

It's like the goal is not to like get big and sell or get big and flip it . It's just like let's just keep doing what we're doing and keep carrying people to a better place . Because the way that I view it is like Chariot is how we help people , like it's how we help people , like we help our customers by moving their freight .

We help our carriers by providing them with loads . We help our employees by giving them a you know , a great job that they enjoy going to , where they're not just a number , they're a person . And for us that's very important , especially with our motto of carrying people to a better place , because people are your number one asset , especially in freight brokerage .

I mean , this is a relationship business .

Nobody outside of maybe your immediate family knew that every day you chalked up a zero on the board , and to show up and do that 70 , 80 , 90 days in a row with nobody else seeing it that kind of hustle and commitment is not something that we talk about or celebrate very often .

We like the shiny objects and things that go viral , and so to go from that place to you know , freight brokerage is not complicated . At its core , it's a relationship business . You got two sides to a transaction .

You have a bunch of administrative stuff that happens in between , but it can still be so it doesn't have to be AI drones and you know space travel to be a successful business , and to do that quietly and steadily every day over a long period of time doesn't get enough attention , and so that's our whole goal here is let's put some of the attention there ,

because , while we need innovators and companies that are venture-backed , that take really big risks and change the industry in massive ways , what we need more of , in my opinion , is folks that just show up and do the work every day , don't seek status or attention and just want to add value and do it in a way that's consistent with their values .

So well done on the on the first 12 years , I think , and especially those first two , that that , that part of your story just really really resonates with me .

And then football back in early 2000s , gallatin , tennessee , is a little different than football nowadays and it was , you know , three a day practices and , and you know , mandatory summertime workouts and you know , year round which I still think they do the year round but that kind of I would say that kind of gave me the like we're not going to give up , we're

not going to quit , kind of kind of mentality .

Um , my dad's an entrepreneur , he's a , he's a , uh , a pretty successful builder , um , and he , uh , he , he instilled some of those values in me too , cause I , you know , growing up he wasn't always super successful and um saw him kind of go up and down but never really gave up and really , you know , has done well for himself .

So I think maybe I was I don't know maybe born to be an entrepreneur . I don't know . People say that entrepreneurs aren't born , they're made , and I do agree with that .

But you know , it started at an early age and I wanted to . The biggest thing about it was I wanted to control my own destiny . I very quickly learned from getting out of college and like working for people . I was like man , I don't want to work for anybody , I want to work for myself and I want to control my own destiny .

And I was like I'm good at this freight brokerage thing , cause . I was , I was you know , you know one of the top brokers there and I was like I'm going to try this . And then it was like if this doesn't work , I'm going to try something else . But I just like , stuck with it . It's working so , and I'm glad that it is .

And now I'm like now I'm a freight guy , but you know , I think that that was . I think that when you look at really successful people that you have to make a decision , that failure is not an option . It's like we're not going to fail , because even if you do fail , you learn something .

And you didn't fail , because it's not always about the success your highs are never as high and your lows are never as low . There's a poem that I read a lot by Rudyard Kipling called If , and one of the lines in there that I love is is if you can treat triumph and disaster or no .

It says triumph and disaster are both imposters and need to be treated the same , and it's like there are victories and wins in the highs and the lows . Right , like as a businessman , you prove your salt and your worst . Like not . When times are good , like when they're bad right , it's like that . That's like when , like you know , push comes to shove .

Like you know , it's easy to be a like . It's easy to be a like , a king , in peacetime .

It's hard to be a king in war , or , you know , I'm not for sure , but , um , you know , and it's , it's a mentality that you have to have of of you know , I'm not going to fail and even if I do fail , I didn't fail because worst case scenario is I have faith in myself and I know that joe is going to be successful in anything that he does .

Because I'm going to work hard , because working hard outdoes everything . Like , a lot of people don't want to work hard , they want to work smart . It's like work , don't work hard , work smart . It's like do both works , we're hard , but work smart too , and then you take over the world and just show up every day . It's showing up every day .

I mean , showing up every day is 90% of the battle .

And I mean , you know , and I look back to like our early days , it was like just me , Like I remember I was getting this freight from Anderson , South Carolina , to Athens , Tennessee , and it was like one of my first like repeat lanes that I would get and it was like I'm not going to book these loads unless I'm in the office at 5 am catching these early

trucks that fly off the board so fast and I would just be there and be like man , this sucks , but it's like I got to get up and do it or I'm not going to book these loads and I need these loads and I just remember that , just coming to the office just that early specifically just to book those loads , and it's like you have to be willing to do like

the hard work on the front end so you sound .

You know , if you got money in a bank account , you should put it to work Right and you know that's kind of always been the philosophy here is we're going to , we're going to take our success and we're going to continue to invest in it , because investing in yourself is the best investment .

Financial planners will tell you that they'll be like hey , you know , if you have a business that you can , that you're running and you're making money , you know investing in that , but you gotta be smart about it .

You don't want to over invest , which we saw a lot of that during the pandemic but you know , continuing to invest in what you're operating and never being satisfied , like never being like I've made it . You know like like the day that I made it is probably the day that I die . Is is is how it is . Um , you know it's .

You know never , never , just thinking that you've made it and I've learned that the hard way .

Cause you know we've we way , because we've had some highs and we've had some lows , and it's like you have to always go back to like it's about what you're going to do daily and it doesn't matter what that role is , whether you're a broker on the broker floor or the CEO founder , it's about what you're willing to do every day .

It's like that , saying success is never earned , it's rented every . You know it's about what you're willing to do every day . You know it's like that . Saying , like success is never like earned , it's rented every day and the rents due , or something like that , and I can't remember how exact same is , but and that goes .

I mean , you know , even if you were a billion dollar a year . Brokerage . Like you know , you got to , like you got to earn it every day , especially in what we do . You're rebidding your freight and stuff every year . Just because you did $80 million one year , you're not guaranteed to do it the next year . You've got to go get that freight every day .

You've got to move those loads every day . In what we do , it's not like set it and forget it , it's like no , we get these loads and we have to book them every single day . Now , as you get bigger , it gets easier , and as you get to scale , it gets easier . But it doesn't mean you still don't have to do it .

It just gets different , and I don't even like to use the term easier . It just gets different and you can do it more efficiently .

You know that idea of you know unitalitarianism is , you have the benefit of all outweighs the benefit of one , and that's always tough , especially in the kind of business that we are , with everybody being , you know , so close , you know us , you know caring about our people We've had to do that in the past and that's never , never , never easy .

You know managing the cash flow is always tough . Being an organic business and collecting your freight , those are always stressful things , dealing with freight claims , but I'm sure that any guy that's run a freight brokerage would say those things , especially in this market now .

But when you , when you have to make calls to protect everybody that's going to negatively affect you know one or two people , that's when it's the toughest because you know we do care about other people . But you know , sometimes you know things happen and it's out of your control , um , and you have to . You have to be smart and you have to .

You know live to fight another day , um , and you know we have . We've experienced that in our 12 years .

I'm not going to be , I'm not going to , uh , you know , not be transparent about that and I think any successful uh business has been a business for , you know , 12 years , has has gone through those ups and downs and those are tough calls to make and but it's like you know , the right thing is always the hardest thing to do and you know you have to

remember that , um , and you have to , you know you have to kind of channel that , because if you don't do those things then everyone's going to be affected . You know , if you've got like toxic top performers that are affecting your culture , like you can't hold onto those people .

I believe I've tried , I've tried , you know , and , and you can't , and the thing I've learned is like you can influence people but you can't change . You know you can , you can . You know you can pour into them , you can influence them , you can train them , but at the end of the day , people are who they choose to be .

And I've met other big brokers at conferences and stuff like that , even Bob King , who is now at a brokerage here in town that he started . He was the guy who started Calvary and I worked for him . I mean those guys , I've watched them and I've seen what they've done . Those guys are all very smart , very successful and very impressive .

Do I have personal relationships with those guys ? No , not at all . Maybe , bob , a little bit . But the people that you look up to , just as we know each other , are , yeah . But I mean , you know a lot of mentors in my life have been people not in the freight industry . You know some other .

You know successful business guys that I've seen that are in different industries , whether it's restaurants here in Nashville or concrete here in Nashville and stuff like that .

Some people that I look up to and obviously it's starting like I did and not rising through the ranks of a brokerage but just being a broker who's just like one day I'm going to the ranks of a brokerage , but kind of just being like a broker who's just like one day it's like I'm going to start my own freight brokerage , like get up and do it Like .

I've kind of like been all of them you know not on my own or anything like that , but it's . You know , I didn't have that opportunity to really work under a lot of people to get mentored . And that's something , and really that drives me to try to be a mentor , because I'm like man , I didn't have that whole ideology of like .

You know , people that didn't grow up with a father figure like want to be a good father . You know it's like . Now I want to be a mentor to people . I want to like help people , I want to pour into people and you know it's it's . It's something that obviously is . You know , everybody needs to have a mentor . I would agree with that .

Maybe that's something that I've lacked a little bit , but again it's made me want to be a mentor . So I think that that's a win . Again , back to that thing that there's no such thing as failure . In Joe DiLeo's eyes , it's just opportunities and learning .

It's my favorite and it's not a hot chicken joint . It's like a steakhouse and it's like a . It's like a fancier steakhouse , but they have it on the menu . It's a hot chicken sandwich and it is . In my opinion , it's the best one .

That again doesn't get a lot of attention and in part , we want to change that just by spreading awareness of a different way of approaching work and a different definition of success than making hundreds of millions of dollars .

Learn a lot of learn , learn a lot of stuff , and I tend to have to learn things the hard way so they stick . So I'm gonna keep on learning so well we , we'll follow up with you in 2036 .

too .

Be sure to like , follow or subscribe to the podcast to get the latest updates . To learn more about the show and connect with the growing community of entrepreneurs , visit logisticsfounderscom . And , of course , thank you to all the founders who trust us to share their stories .