Charley Dehoney | Vice President of ZEBOX America, Sales Expert, Investor, & Former Division I Football Player Talks Overcoming Adversity, Getting Started in Technology, Startups, and Angel Investing

Greg Spillane: 0:05

So how's Omaha man?

Charley Dehoney: 0:08

Omaha's? Great this time of year, we have a sunny, sunny 55 degree weather blue skies. You never know when the last sunny day is so definitely going to get out and grab a run this afternoon, because it might snow over the weekend. You just don't know this time of year. Yeah. So obviously we've known each other forever. In Southern California guy like myself. Were you? Are you born and raised in San Diego? Were you born in here? Or did you you move to Southern California somewhere else? Right? Yeah, that's right. I was born in Idaho and lived there till I was like seven or eight, moved around a bunch of places and like western US, landed in Southern California when I was about 10 and then moved to San Diego at 12. So I always had this context that California is beautiful as it is and how much opportunity there is that there's always like life outside of California. Yeah. So how has that been? You know, I mean, coming out of California, you've been in the tech scene. You know, you're in Omaha, amazing place to live. I've seen some pretty successful people, Warren Buffett being one that's that's done pretty well out there. How is that transition done? It's been great, you know, it's the perfect time of life. For me, I think, to move to a place like this, my wife of 17 years now, she and I met each other at Rancho Bernardo High School where I met you. And, you know, it was an awesome journey and a great place to grow up. But as we put our children into school, and I continue to build my career as an entrepreneur, there was a lot of reasons why we felt like getting out of California getting the middle the country made sense. And there's a couple things about living in Omaha that I just cherish every single day is the quality of life, you know, the education, the values, the Midwestern culture, like this is a perfect place to have my family and my children at this stage of life. And then secondly, there's this like, undercover entrepreneurial scene in Omaha, and like massive companies here that have made millionaires that, you know, many of these entrepreneurs and these, these corporate executives give back and whether they're, it's their time or their money. And so, I found just a really great tribe of mix of, you know, sort of big time executives and startup folks alike, to really just kind of like, build my network. And it's, it's been almost three years now. And not once have I regretted the move,

Greg Spillane: 2:28

you know, it, it's the COVID thing, especially, I think accelerated this, but but I think it's so good for the startup world in general. I mean, and you know, we're similar age, and I'm a couple years ahead of you. But we grew up in a world where, you know, the Silicon Valley was the mecca of the tech scene. And, and it still is, in many ways, and you know, that that may not change for a while. But with this advent of just more people being remote, you know, you're seeing all these different cities pop up that, you know, have been around for a while, but you know, like Salt Lake City, and you know, Austin and even Phoenix is starting to get a little bit and you know, Southern California and Omaha, it's, I think it's really great. I think that just gives more opportunity for people to be creative to feel like they can go out there and raise money to create disruptive companies, there's talent pools, and it doesn't all have to concentrate out that, you know, San Francisco, San Jose area.

Charley Dehoney: 3:21

Yeah, look at him as a as near and dear as the Silicon Valley is to my heart. And then, you know, growing up in California, feeling that sun on your skin, when you get off the plane, it just never gets old. But you get outside of California, and you realize that talent is everywhere. And opportunity historically hasn't been. So I think like spreading that out and seeing the movement like you're seeing in Miami right now, where a couple of VCs just show up and say, Hey, let's make this the next Silicon Valley. And then you see, you know, the mayor and the governor kind of saying, like, Hey, let us know how we can help. It's really just inspirational to see, you know, folks, finding their way finding happiness, and really not letting location be an obstacle to their success. Right. That's, that's the key to it all.

Greg Spillane: 4:04

So take it a step back. I've had a couple of guests on the show people that I've known for, you know, a long time 20 plus years, you know, some ex college teammates, etc. But we actually go back farther than that. Hmm. I mean, you know, you're I think you're the first guy that you know, goes back to high school, possibly even maybe middle school and they started you know, playing sports against each other.

Charley Dehoney: 4:25

Yeah, that's right. Um, so I mean, I definitely remember you know, during football camp freshman year, my first time like walking on a ranch mera High School and number 65. You know, this, this blue chip tackle, leading the team and so certainly like going to all the games and watching you guys on Friday nights, there's a certain sense of like idolization around when you're a freshman and you see the guys on varsity and certainly being an offensive lineman and you were the top dog you know, on offensive line, which is saying a lot because there's a lot of talent on that offensive line right with with Mitch white and there's you weren't the only one out there, but certainly you were the one that right out of high school, you know, got the best opportunity and went to San Diego State. So in all my recruiting trips down there, and you know, always, always senior around, down there at San Diego State, it was always great to like have that sort of like person to look up to, you know, I remember seeing seeing you when I was in first period, you walked by my math class and that always like the school, this guy says hi to me, and then think we played some basketball against each other in the rec league through high school and stuff. So it was just cool to always know you and look up to you. And then when we reconnected like, professionally, you know, that was awesome.

Greg Spillane: 5:35

Yeah, no, it really was. Thank you for that, by the way. You know, I guess that's the power of being the the upperclassmen and in high school, right, but you obviously had a fantastic career in high school, you you had an opportunity to play at the collegiate level. Sounds like you know, it didn't go exactly right, right out of high school. But you know, you persevered and obviously ended up at San Jose State. So maybe tell talk a little bit about that experience.

Charley Dehoney: 6:06

Yeah, I would say that, you know, really, my, my kind of college journey started when I was like four or five. I remember asking my dad like, Dad, where am I going to go to college, and my mother and father didn't go to school. And we grew up in some pretty adverse situations, you know, especially financially, at times, there's, there was five of us, I was the middle of five kids. And I remember asking my dad, where he thought I should go to college, and he kind of laughed at me and said, You better get a college scholarship, if you're gonna go, you know, he walked me through them after putting five kids through school. And, you know, we already knew that there wasn't enough to go around. So I just had it in my mind that I was going to find a way to get to school. And so out of high school, I had one offer, and it was Idaho State and Pocatello, Idaho playing in the big sky. You know, I went up there sort of expecting it to be everything that I had hoped. And you know, that first year wasn't easy. I blew up my shoulder had a surgery, our entire coaching staff got fired. And then I came home for Christmas break and my mother passed away. And so like being dealt all those blows, in the first semester, it was really sort of a time in my life where I felt like I needed to change direction to do something else. But I didn't have anything else lined up. And so fortunately, the new coach from Idaho State, a guy named Larry Lewis, who was not like the most love guy in the world, but I always found that the hardest coaches to deal with are the ones that I remember and think about the most. And, and I never had a bad, you know, relationship, Larry, but he flew to my mom's funeral and basically challenged my logic. And so Charlie, if you stay here, you know, what are you going to do? How are you going to help your little brother and sister you know, like, they're in high school, like, you need to get your degree, that's what your mom wanted. So fortunately, Coach Lewis like, you know, kind of drugged me back up to campus and Pocatello and, and I went back up there and, you know, finish out my redshirt year. And then I got the opportunity to start a bunch of games played all five positions. In my second year, I was an offensive lineman like you. So I played center right guard, left guard, right tackle left tackle, and really got the experience the on field experience gave me the confidence in knowing that look like I love these guys I'm playing with up here. I like certain parts about living in Pocatello. But by that time, my high school girlfriend had become a very serious part of my life. And fortunately, I stuck with her. She stuck with me, I should say, because we built a wonderful life together. Now it says my wife, but in those days, she was going to UC Davis and I really wanted to get back to California. So really, without much of a plan. I packed up my 84 Honda Accord, I drove all the way down the 15 to Rancho Bernardo from Idaho, and kind of spent that summer getting my getting my stuff together and working to save a little bit of money. And then that's when the coaches from Palomar, you know, they found out from our common coach, Damon Baldwin, he had plugged them in and I was back in town. And, you know, he really thought that there would probably be an opportunity for maybe him to recruit me if I kind of went to Palomar. And so fortunately, Coach B hooked it up and let those guys know, I was in town and they weren't gonna let me not play on the team.

Greg Spillane: 9:01

It's amazing. It's amazing how, you know, how big of an impact coaches make in people's lives? Right? I mean, just that experience of a coach, you know, coming to fly in, you know, during, you know, arguably probably one of the most difficult times in your entire life and, you know, really, you know, probably and yeah, maybe a little bit because they want you back and this that the other but at the end of the day, it's because they care about you as a man and they want the best thing for you as a man. So I love hearing stories about that, you know, the junior college level is it's brutal, right? I mean, and what I mean by that is, it's like a pack of, you know, I don't wanna say why dogs but like, it's a bunch of people coming in and they all have this dream to get to the next level. And in many cases, they're willing to do whatever it takes, they are there to step on anybody's throat, they will they will go to any lengths to get to that next level. And you know, the people who are able to get Get in there and be successful and get to that next level, like, you got to compete, right? You got to persevere. Like, it's, it's not easy. And if you're weak or you know, you're you're not willing to put it in, like, they'll run you out there. I mean, I think that's the one thing about sports, in general is just the meritocracy nature of it. And you know, and I think that that's what, you know, apply so well to the entrepreneurial world. But, you know, what was that experience? Like? Or what was your mindset in when you when you got there, and you just had this, like, now I'm going to be, I'm going to be one of the guys that makes it?

Charley Dehoney: 10:31

Well, I would say, you know, having the perspective of going off to play at a four year school, you know, I remember being in the dorms my freshman year, and we would, we would all tell these jokes about our buddy who stayed home to, you know, take the semester off, or go to junior college. And, you know, the next thing, you know, this guy's 18, he's got a truck payment and a tattoo on his arm that he financed, and he's got to go work with the mill, because he can't really take his education seriously. So I had a couple things sort of like, to really keep front of mind, when I was going into junior college, one, I was back at home, like right in front of my dad, my little brother and sister, and, you know, my mom had passed away and things weren't going like super well at home. And there was a lot of challenges that were presented as a byproduct of that. But I always looked at like happiness as a choice. And the closer I got to adulthood, the more sort of influence I was gonna have on personal happiness. And I knew that playing college football and seeing myself on television was a goal that I set when I was a young kid, and then I was gonna execute that goal. And that year, I spent a lot of time you know, you play your game in junior college in the morning. And a lot of times, you know, the guys would go out after the game, and not that I missed any parties. But a lot of times, I would really cherish these moments where I get to go home after the game and watch a couple games with my dad. And so we're watching guys play on TV, and I'm just going, I could do this, I know I could be there, I know I can do this, I just have to keep working. And despite all the distractions, all the things that can pop up at junior college, you know, I was able to put my studies in front of me, I knew exactly what I needed to do to bounce back and transfer back to a division one school because I mean, remember, this is before the transfer portal, right? Like this is before kids could just, you know, get upset with the coach and go find a new school like it took some real grit and resolve to actually like transfer from one institution to another and within the NCAA, and you start seeing all the light changes now and you like get a little like, little kind of like, upset sometimes thinking like, why did they make it so hard on kids, it's great to see that things are going in a better way for the players and the kids. Don't get me wrong. But I also think back to that second year that I was in Idaho State, and how hard it was to really just grind through that. But it really gave me this sort of appreciation and understanding of being back at Palomar and I'm back in San Diego. And I'm playing with guys that I saw them on PrEP kits or prep pigskin review on the Friday nights and, and I remember these guys winning championships and Oceanside high school and playing against these guys of Vista High School. And now we're together. Plus, we've got some guys from Orange County some guys bounce back from the Marines. You just have this ragtag motley crew of dudes. And I'll never forget my first practice going out there and it's in the summertime. So you're thinking like, you know, there's no pads, you're just kind of shorts and shirts. And Coach Kraft who went on to coach at San Diego State and just like, probably the craziest offensive mind that I ever met and just so effective as a coach. He lined us up and we get out there and our first practice and I lined up against Tony sale, got to wrestle, he's passed away now. But this is junior sales, little brother, he was fresh out of prison. He actually went in prison spent prison spend maybe 10 years in prison, maybe more for a fight broke out in high school when he was a freshman. And that person ended up dying in the course of action there. So I'm lined up against Tony, he was not a guy that you really want to run into in a dark alley. And we got no pads on and we're going one on one, I'm center, he's nose guard. And it was an absolute battle. And when I saw how hard he was going and how physical he was playing, that sort of heightened my competitive arousal. Next thing you know, like, we're both shirts are ripped off chests are bleeding. His fingernails are about this long at the time. And and I just knew, right that it was gonna be a knife fight every single week, if you wanted to play junior college football, you literally were standing in the way of somebody else's dream on the other side of the ball from you, and they're gonna play harder than they were going to play in any other level in football. So while I had this experience playing at the division one level up at Idaho State, I was able to bounce back and take a lot of the learnings and coaches out there. I really like that around this group of guys that and it's as close to again, I think, as I'll ever be in my life, but I look back on some of these guys whether they were Hispanic black, you know, Polynesian, white, like, we were all there just ragging on each other, pushing each other, partying together, won a bunch of games. It was just such a great experience and it was not exactly what I expected it to be, to be honest with you.

Greg Spillane: 14:58

And then you get to Santa Jose State. Was the experience any different there? Or was it similar?

Charley Dehoney: 15:04

No, it was, I mean, San Jose State was amazing. So going back to, this would have been the 2000 season when I was playing a junior college. One of those games I was telling you that I was watching with my dad that year was number nine TCU led by Hola, Danny and Thomas and rolls into Spartan Stadium on a Friday night. And San Jose State put it to them. And they tore down the goalposts and they stormed the field and watch that TV Go, man. It's amazing dad, like that's a great place like this program was up and coming. And this coach, the guy was coaching the team there was named Dave Baldwin. And I kind of took note on that team earlier that year, because they played USC all the way to fourth quarter that already beaten Stanford. And when they knocked off TCU, I was like, Man, I want to go there. So they automatically got high on my list plus with 100 miles away from Davis, where my wife Katie was a student at the time. And so it just seemed like a good natural fit. Now, throughout the course of the season, I got a ton of attention from some really great schools, a lot of schools that I knew that if I went and played there, I already had the context of seeing these programs that junior college guys sometimes come in and just a number. They're just kind of like a spot on the depth chart. And I really wanted to stay away from like holding a bag and practice or running scout team like I really wanted to go two more years left, I wanted to play. And I was I knew that I could play at that level. But right at the end of the year, Coach Baldwin and his whole staff got fired. And so that really took a lot of wind out of my sails because I'd already been through the disappointment of the like, unproductive recruiting process coming out of high school and a story for another day is how I ended up getting connected at Idaho State because it all goes back to actually guys that coach Baldwin knew that were gas' with him at San Diego State guy named Joe Green and a guy named John Ely really kind of like connected to get me into Idaho State. But I just didn't want to squander my my last two years of playing college football. So I started exploring all these other opportunities. And then I got a call one day on my mobile phone. It was like my, my first Nokia mobile phone ever had. And I was going to Bob Conley, who was the offensive line coach at sales at some of the state he had been recruiting me and he got rehired. So that was like a huge turn of events it till had just come in as a head coach. He was the head coach and waiting in Arkansas and the assistant head coach there and he came in abroad south Arkansas folks, and luckily Bob got the job. So he brought me up that weekend, had a great recruiting trip. The previous weekend, my tight end, and one of my best friends from Palomar had been up on a trip. So I'll never forget that Sunday when they kind of marched you in. And you talked to the head coach after you've kind of been out partying for two nights and meeting all the guys and getting to know the city. I was in love with San Jose. It was the heart of the Silicon Valley. We went out downtown got to know like the whole scene and I thought, Man, this is a place I could go great guys. And then Coach Hill brought me and he said, Charlie, we'd like to have your scholarship, we'd like you to come back up. And we need you here next week because classes are starting because this middle of January. Like to coach you know, my only concern is I don't know where I live. I don't know what a roommate I'd have and stuff. And I know my friend, set day Oh, my my pal martide. And he was up here last weekend. You know, I know you offered him a scholarship and he's kind of waiting for another offer. But you know if if Seth could come up here, I know it really made me help my transition make me a lot more comfortable. And Coach, I'll never forget this. He looks at me. He goes, son, if I was going to go into a foxhole with you, and I said Charlie, would you like to come into my foxhole. And then you said I'll come in your foxhole of Seth can come into the foxhole. I'd really start to question whether or not I needed you in my foxhole or not. Like you're a coach. I'm good. I'll see you Monday. And that was a Sunday morning. I flew home that afternoon. I packed two suitcases. I flew back up on Monday started classes on Wednesday had nowhere to live. Another teammate Patrick battle Castle Park guy, let me stay on this floor. That lasted for about two weeks until one night his snake got out of the cage and curled up on my back while I was sleeping on the floor just to stay warm. And then after that, I moved back into the dorms. But I mean, it was kind of a weird winding path to like, probably the most influential stage in my life as those two years I spent at San Jose State.

Greg Spillane: 19:11

That I love that story. First of all, I love because I've known you for as long as I have and I've known you professionally and you know, I know you're you're you're in the CEO and now really in the investor world. But you know, you cut your teeth, in many ways is a really successful VP of sales. So So I love that the little sales pitch that you had to throw in there early on. It's just amazing that you had offered a scholarship and it's like yeah, but let's talk a little bit about what what else we can do here like what else can you throw in? Yeah.

Charley Dehoney: 19:41

Yeah, what it's what it's silly move. But you know what, those two years at San Jose State like being in the heart of the Silicon Valley and really like one thing about playing football San Jose State is like you have to work hard to earn the attention because there's so much going on inside of that world where like, you know, kind of mid major college football program isn't that like highest priority on everybody's mind. So, you know, it gave me the opportunity to really kind of see a group of guys on my team and I met just a ton of people through the ecosystem, that just really, I found that like, that place hustle, like the Silicon Valley is all about hustle. And you know, you definitely, as a kid that doesn't, you know, come from a lot of privilege, you definitely see how the, you know, the guys up in Palo Alto, you know, had an easier path. And it kind of gives you that chip on your shoulder, the haves versus the have nots. So I really attribute you know, my, my sort of ability and I don't want to say success as an entrepreneur, because like your whole job as an entrepreneur is just to like not die and have to like, go get a real job. And so the fact that I've been able to kind of like in the stay and stay in the startup world, be a founder, co founder, and just kind of like exist now as a, as an aspiring investor, I attribute a lot of it to just like, finding happiness outside of like your immediate day job. So San Jose State wasn't a great program. While I was there, there was plenty of challenges on the field. And there was always, you know, somebody dividing something on the team, or somebody taking issue with something and, you know, really it like, I figured out like my superpower at San Jose State was like, I could go on and make everybody laugh just by like keeping a smile on my face showing up with some energy. You know, if somebody was having a bad day, or they're irritated about this, I could kind of point out Well, guys, like at least it's not raining today. So yeah, we got to go practice, but like, look how beautiful the weather is in the South Bay. And, of course, like a lot of probably less appropriate things and ways of getting people to laugh. But I felt like that's where I kind of discovered my ability to be a unifier and a motivator and a leader. And I was able to do that, and work on the side. So I could afford a car and have a cell phone and a girlfriend. So like Silicon Valley, and San Jose, it really is like a place that I'll never forget, because it just opened my eyes how big the world was, and how much opportunity was out there. And then 90% of it was your mindset, and your attitude.

Greg Spillane: 21:58

So yeah, I mean, you know, I can say that, having worked with you, and following your career and kind of go in and out of our lives professionally, you know, you're in self proclaimed like a SAS startup tech, like, geek, like you're a student of the game. Like I've learned a ton from you in my career. I mean, you you follow the industry, you know, what's going on, you know, the trends, you know, where the ball is moving. You overlay that with your, you know, I guess probably started your career in the logistics space and supply chain, and you've really carved out a an amazing niche for yourself. But the question I have is, you know, I mean, as you're going through, you know, the the ranks and college football and kind of doing that battle. I mean, you know, the misnomer is that your student athletes, if you really athlete students, I mean, it's people don't want to hear that, but that's just the fact of life. Is that when that love or that passion for technology developed? Or is that something that happened, you know, after your career start?

Charley Dehoney: 22:57

Well, I would say that, you know, I'm from this like, kind of strange generation where not a millennial, not a full millennial, but you know, certainly was an early adopter of technology. You know, like the got the video games when I was like five years old, six years old, got into mobile phones in high school and, and PCs, and really, like flirted with my wife via American online instant messenger. And so like, had enough exposure to the digital side. And plus, I had a little brother and sister who are squarely in that millennial generation. So it's kind of on that cusp. And then, certainly going to school in San Jose, like we were very gifted and had the opportunity to, like get exposed to technology through school and probably more of a digital experience by going to school in the early 2000s. And most kids had, but I was always interested in, in technology. And frankly, part of going to San Jose State was the.com boom was like in full effect and it tanked while I was there, like in 2000 2001. And so seeing that whole kind of downtown area shrivel and see things change. It was kind of a depressing time. Still got exposed to a lot of technology, a lot of entrepreneurship. But like when I got out of school, there wasn't these $100,000 A year software sales, sales jobs that like my buddies had gotten a couple of years before. So that was a little bit depressing. And like I really want to be an entrepreneur, but I had no money and no skills. And so the next best thing for me it was I was reading the Forbes 400 And I saw that a lot of these guys, the most successful guys, it started off in b2b sales. A lot of them sold copiers. So I thought like I needed to get into copier sales. And that led me on this journey of applying with, you know, 50 6070 companies with the 40 plus first interviews went on a bunch of field rides and my criteria was like very clear, like I want somewhere with super aggressive training in a business that I can grow within so I wanted a bigger company and the company I started with wasn't that big then they've gone on to become a multi billion dollar your company but I started off like going door to door selling overnight shipping with a company called worldwide Express. And it was a franchise based company. That was the first guy hired in the Sacramento office. So it had this startup feel my manager Ryan venturing. Awesome, dude. He had played college football at University of Minnesota, we completely bonded on the first interview, and I'm like, This guy can teach me some things. He was driving a Lincoln wearing a suit every day. And he wasn't that much older than me. So I was like, Okay, if this guy could do it, I can do it. But really, what that instilled was this, like framework of success, like the basic sales training, there was so intense, it was a full suit organization, I found out that if you could win, if you could win the kind of prize for the best role play at the end of the week, you'd get a Montblanc pen and they give you 1000 bucks. So my dumbass goes out, takes my wife's credit card, and I, she's my girlfriend then. And I go to Nordstrom, I buy myself a really nice suit, I bought myself some really nice shoes. The total was just under 1000 bucks. And I felt like well, I'm going to kind of use this to finance, you know, my success. And then I'll win the pen. I got second, I lost. But I at least made an impression on people that like, I was there to take this seriously. And I was going to take my career seriously. So whirlwind expresses the perfect organization to kind of get in into early on some of my mentors, there are still mentors and dear friends today and people that like relationships I cherish. And I learned a ton, but the real, I think opportunity inside of that. And the thing that I never could have picked like, was that getting into logistics in 2003 is eBay and Amazon were just becoming household names. It was kind of I could connect that God I could see like, Okay, well, like I started using eBay in high school. My parents don't trust these online marketplaces and putting their credit cards online, but like, eventually everybody will and through college I use those services a lot more. So I can see that okay, maybe this parcel shipping thing is going to grow at what I didn't expect was like how ecommerce and this whole entire kind of like intersection of transportation and technology was just going to become like, such a focal point and curiosity center for me. So in right out of like school, as I was doing sales, I would always look at these, you'd go door to door and like literally walk into a shipping dock and just say, hey, I want to introduce myself to the owner, you know, we're in a full suit like a complete douche. And I would see these big piles of packages and these ecommerce companies, I would think to myself, like, how do I get that. And then I quickly figured out that, to get that you had to automate the process, and you had to live in the checkout? Well, my company worldwide Express didn't have that ability. But we were a reseller for everyone Express and eventually DHL. And their systems could do that. So I taught myself SQL and like 23 years old to figure out how to integrate these databases did a horrible job. I can't believe some of these people even like let me come to their warehouse at night after I was work done working and integrate these systems. But like, I figured it out. There was no YouTube at that time. So it was all kind of like sequel for Dummies calling in favors and remoting in developers via go to my PC, I had my own subscription. And, you know, really just kind of like, stay curious and like watch the industry evolve. And then, you know, had some great success at worldwide couple small exits in my 20s. And I got off on my own and in my late 20s With back to Rancho Bernardo or hometown and started a couple of logistics companies and, and as E commerce really kind of took hold, I started seeing opportunities popping up to digitize certain parts of the supply chain and transportation, didn't know how to do it didn't know what to do. But in 2012, I was in San Francisco for a business event, there was a huge crowd of people waiting for cabs. I was waiting in line, I couldn't get a cab my standard, you know method is to stand in front of everybody and be bigger and hold up my arm and that wasn't working. So as I'm waiting for the cab, I see this guy go like, pulls out his phone, you know, iPhones are brand new back then two years old, he pulls out his phone. Next, you know, a black car pulls up and picks him up like five minutes later. I'm like, Holy shit, man, like, how did you do that? He's like, he's getting in the car. It's like, it's the Uber download the Uber. So I did. And then like, the next day, I took a town car. And that like just changed my life. I like knew that that was gonna change supply chain logistics, and I wanted to be a part of that. And so I spent the next kind of year and a half trying to figure out like, what's what do I do? What's my path? How do you raise venture capital? Like, who's working on interesting things? And that was kind of a real big turning point for me.

Greg Spillane: 29:31

Yeah, it's amazing. Um, and and then you joined cargo Matic right as the head of sales there. Yeah,

Charley Dehoney: 29:37

that's exactly right. Yeah. Real early on. That was just like, Yeah, but it was just staying in touch. It was networking. So this was a friend of mine who I'd gotten to know, in my logistics company, he had warehouse in LA and, you know, he knew I had this background of scaling sales teams and stuff and kept trying to get in touch with me and we missed each other a bunch and he finally told me what he's working on. He was like, you know, have you heard of Uber? I said, I love over omega. For trucking, he's like, Well, we just need an app. We don't know what to do with it. We want to get you involved. And so I drove to La the next day from San Diego. He showed me the app, it was him and his co founder, Jonathan Kessler, this guy's name's Brent Parker showed it to me in an apartment on the west side of LA. And I just fell in love. And I said, like, how do I get involved? So, you know, that led to you know, a couple of discussions became employee number one wrote an angel check into the business and spent about a year and a half really like learning how to raise venture capital, how to build, you know, a team, how to give product feedback, and like that was my first time working with like, Harvard people, and like, really, really high level intellectual people and working shoulder to shoulder with them, and having them look at me and go, like, oh, my gosh, you know so much about this industry. And I'm thinking like, oh, my gosh, you know so much about everything else. So it was just like a perfect fit for me and my natural curiosity. And it was also a good time, right? Because like, when I was running my two companies, their lifestyle businesses, I was coaching high school football at Rancho Bernardo, like really enjoying like storehouses spending my time, but in the back of my mind, also wondering, like, you know, am I falling behind, like, you know, that was a great time for me to like, focus on my family build something that was meaningful, like, be close to my wife, who became my business partner. You know, she gave birth to our two children, our two oldest children, and like, we would bring them to our office. And so it was a great time in my personal life and my family, but professionally, I started seeing all this innovation, you know, the venture capital was coming back around, although people weren't investing in supply chain yet. And it just seemed like, a great time for me to kind of like refocus, reinvigorate, reengage, and then yeah, cargo Matic led to my experience, my involvement with ship hawk and early stage team was able to help them kind of that's where I learned a lot about SAS sales, and we pivoted that company from a digital freight marketplace to a software product and an API first company and then, and then, you know, after after ship Hawk, you know, a guy that I knew tweeted out that they were looking for a VP of sales at a little startup in San Diego called events.com. And, and then you and I got to spend about a year and a half working together, which was a an incredible time,

Greg Spillane: 32:13

there was that was, and it was a great year and a half. Now, it's a fantastic story with

Charley Dehoney: 32:18

a great year and a half in some ways, but I think there was also a lot of learnings and stuff in terms of like, well, we were tangling, we're untangling some really, really, really challenging problems there. And, but it gave us a chance, I think, to to sharpen up. Yeah, yeah. Would you agree with that?

Greg Spillane: 32:34

I would agree with that. I mean, it definitely started this, you know, from my personal story, it started this weird niche that maybe I found where I became this like turnaround guy where I got pulled into these, you know, kind of messes, right? I mean, they're these startups, they had raised capital, they had investors, they had boards, little attraction, an opportunity existed, but they just were, you know, I mean, just kind of spinning around in circles. And a obviously, things could have gone a lot of different ways. And in most cases, they're going in the wrong way. And, you know, they bring in and you sort of got this, this pile of clay that you you got to work with, and you got to figure out how to turn this thing around and make a successful business. And, you know, there was, there was some strange legacy there. And we were dealing with a lot of things with that company. But you know, I'm really proud of what we were able to accomplish there. And I mean, that company still to this day, it's, you know, it's around, it's doing well, and it's, it's a platform that people use, and, you know, there's people whose livelihood is, you know, still to this day, based on on a lot of the work that we put in there. I mean, that that platform that was built, like we we hadn't even written one line of that code until till I, you know, I got there, I was part of that. And you came in, and you helped legitimize the sales team and build out the sales process. And I mean, you know, in retrospect, we did really well there. I mean, we scaled out things to many, many millions of dollars in revenue in a very short period of time on a on a true SaaS based platform. So yeah, it's, that was, that was quite the journey, man. And I remember that process, too. And I remember when you you reached out to me, and, you know, I'd remembered you and those types of things. But, you know, I don't think we had known each other professionally. And you don't remember through that interview process, you know, you you really just wowed everybody with with sort of your strategic thought process. It wasn't just what you done. It was, you know, your approach to how you wanted to do things. And, you know, I know that that, you know, Greg Peries, our CEO at the time was, was really impressed and I think you came in and you lived up to the billing. Actually a question I have for you, because I think a lot of people get can get pigeonholed into the sales world, right? And you're a really gregarious guy and just a gifted talented sales guy. And I think that to your point, you're really good at building teams and really good at managing people and good motivating people, which agio a great VP of sales, but you've moved on, and you've been a CEO, and you know, now you're you're in, you know, really almost the VC world, if anything, how was that transition? Because that's not an easy transition, a lot of people have a hard time breaking out of that sales world and get getting into the operational the executive

Charley Dehoney: 35:18

world. Yes, I think there's a few elements of it. You know, first off, I'm a fourth generation salesperson. So I think, you know, the gift of gab is with the Irish people call it and I was fortunate to be able to speak in public without being nervous, and these other things that I realized, and also, you know, have a dad, that was a very gifted people person. And really, I've got like an older sister who's like, very eloquently spoken, and has built a big business of her own. And so like growing up with that confidence, and knowing that, like, hey, I can talk my way out of this is like a blessing and a curse. But I would also say that, when my dad would tell me, you're going to be a salesman, when you grow up, I would always have this chip on my shoulder, like, I will see, like, I'm gonna own that, that company. And that's what I want to do. And, and so I just committed early in my life, that I want to be an entrepreneur at some point. And I knew that that was going to require a more well rounded skill set, and you have to be, you know, versed in all the disciplines. And so I think that was, you know, sort of, like where I started sales from was that I was like, sort of going to be a stepping stone for me, or, you know, I needed that training. And I'm certainly glad that that's where I started. But I also worked my way into general management, like very early in my career. So I had p&l ownership, which forces you to understand finance and operations, really like logistics and supply chain, like sales and operations are closely closely intertwined. Because if you're not, it's such a transactional, executional business that you can sell all you want. But if you can't fulfill like the relationship ends and the conversations over so I think just the kind of like, customer service nature, and the customer retention nature of building a residual business, like like Logistics is, has been critical in my path as well. And then I think, as far as you know, jumping into business ownership, and really, using my own capital, and I never raise external capital for the companies that I own on my own, and probably wouldn't now knowing what I know now, but back then you don't know what you don't know. And so I think it really just forced me to understand how a company or a model makes their money. And then if you if you understand that sales is merely one function in the business, but you're committed to that function, because it's a primary function, and one of the most important that I think it just like, always helped me keep in context, that there's a bigger picture, the world doesn't stop and start with sales, but we have to be very good at sales. So I knew that that early in my career that like, there was going to be a natural progression from sales to sales leadership, and I spent a bunch of time you know, in GM roles, and then as I got into these venture back things, it was very clear that if you don't sell you die, and it gave me the opportunity working in great teams, it gave me the opportunity to wholly focus on sales. And like, the cool thing is, there's no original thought and more, all the answers are out there, somebody has run this playbook before you got to find the playbook that works the best. And then you got to be able to run it at least as good as data, but you should be able to run it better, because now you have the perspective. So I, everyday I sell, all I do is sell, selling myself selling a vision selling a relationship, you know, potential. And so I think in my in my current role in kind of working in corporate innovation and an investment, like understanding that these large organizations have their own way of being sold to, and oftentimes, startups don't understand that language, I'm seeing that this is a fascinating sort of problem to be working on. And I'm having fun doing this project, because the language of sales is not universal, and like organizational size, structure, culture, all of these things will impact what those sales protocols look like. And organizations really need to be built to sell. And then large organizations aren't always really built to buy very well, if you don't understand their kind of language. So it all comes back to you know, money going from one one pocket to the other. And, and kind of the release of that comes down to communication, which is sales.

Greg Spillane: 39:28

Yeah, I think you make an amazing point there. And something that's so true. I mean, I've you know, been in situations in my career where you know, I'm essentially a salesperson, my business development person. And you know, now you know, having moved beyond that and supportive you know, executive leadership management, those types of things, you know, I get asked all the time, you know, about that sales background, and I have to explain to people I sell way more as a CEO of a company that I ever sold when I was a salesperson, and and I know that sounds kind of counterproductive but it's but you know, like you're selling your vision You're selling yourself, you're selling your company, you're selling your product, right? Your employees have to believe in you, they have to believe in the vision that you're set your your investors, they need to believe in you, they need to believe in your company and where you're going, right? You need to be able to sell partners as what you're doing on a day in day out basis. So it really does prepare you well, especially if you have some some of those other backgrounds. So, you know, we talked a little bit about your ability to build teams, you know, I think that that's something that you pride yourself on, it's something that I've experienced firsthand. You know, when you when you look at recruiting people, when you look at building a team of people, what are what are, you know, sort of the qualities that that, that you try to find in somebody that you want to bring on board that you think is going to be successful working with you and for you.

Charley Dehoney: 40:46

So I think I'm gonna answer that in a couple of phases, like I always do, too long, probably. But I think first off, you have to always hire for passion, then somebody you know, in the logistics technology world and a lot of business I've been involved with, I think you either had to have passion in logistics, you have to have passion in technology. And in the early days of supply chain tech kind of expansion over the last 10 years, you had to hire for one side or the other. And as long as there was some passion there, you could teach the other technical parts. And the further I go in my career, the more I realize this is a very big world, and everybody was born to do something. And the absolute best thing you could do as a leader and a team builder is find the human that was born to do the behavior of the work that you have available for them, and stop what you're doing. When you meet that person, stop everything, hire that person, put all of your energy into getting them on board and getting them up to speed, take great care of them, get them the package they need. If you have to pay a little bit more, it's fine, cut it out of the next hire. But the person born to do that job is the only person you want to work with. And at this point in my life, I don't want to work on projects where I have enough time to let these underdeveloped talents develop into their role. Now that's I mean, this doesn't go for like entry level roles, like right, like most of the time and executive level positions over the last five years, I've been spending my time hiring the executives that are going to really steer the business. And what I found, especially in those executive level roles, if you can find somebody born to do what you need them to do, stop what you're doing, hire them and get out of their way. Give them everything they need, listen to them regularly, break down the obstacles and the roadblocks but just let them do their job. And then when you get the right person in the right role, it's like poetry in motion. And as the leader you feel weightless and you feel almost like there's going to be an hour or two every day where you're kind of bored. And you're gonna have to fight the temptation to go up the floor and metal and turn screws. Because really, you know, I found this out of the business we moved out here to acquire here in Omaha man instruct brokerage. You know, I got in and I had to make some kind of radical changes right off the bat, you know, move some people around, install some technology and everything. But once we got that, past that first five, six months, I looked around, I realized, like we have the best human beings in the world running this operation. And the only thing I can do to make this better is to go hire the best sales team out here to support them. Because anything else I do is just going to be disruptive and meddling to the business. And so I'm always going to be grateful for the guy chatting bristled at random business over there. Tina rhymer, and, and Chris Newby and these, you know, some of the people I hired Blaine Neufeld, Sam Blount, you know, we were able to kind of take this amazing machine, and then put a world class sales team on top of it, because we were so good at executing, when I would show the operation to these heavy hitter salespeople. They're like, yeah, that's it, that's all I need right there. That group right there can make me successful. So you got to put the right people in the right seats. And what I found is that most of the time organizations are full of all the right people in the wrong roles. So it's not always easy to shift. But if you can get people to believe that you have their best interests in mind, and the best interest of the company in mind, which shouldn't be difficult, right? If you can just be humble and communicate, honestly. And you just get the right people in the right roles and get out of their way. And that's when life becomes fun, in my opinion. So

Greg Spillane: 44:16

your CEO days, obviously not done. I'm sure you have many more startups in your future as an operator, as a founder. But you're now as we talked about, sort of an investor, right? You're working a little bit more in the VC world and you know, nosey boxes and our accelerator. I'm sure you're involved in, you know, the selection of these different companies helping incubate these companies. You're making your own personal investments. I'm sure you're making recommendations to others. When you see a startup, what what are you looking for? Is it the idea? Is it the team I know it's a combination of both but help me you know, get in your head a little bit with with your thought process when you see it Companies are like, Yeah, this is a winner like, these guys,

Charley Dehoney: 45:02

I'm not putting my money here. So I guess, you know, a lot of the, you know, Scott, my investment journey was born in these operational endeavors like joining the team early at cargo Matic and ship hawk and airspace. And for me, it was a very validating, feeling to know that like, hey, Charlie's not a wealthy guy, he's putting a little bit of money into this thing. He's rolling up his sleeves, he's taken a full time role in this. He's changing his LinkedIn, he's going all in, he's at the conventions, and he's here to help us, you know, drive this business forward. And what I found was that conviction and being steeped in the operation, and everything else, gave me this view of like, the common problems inside of startups and the common pitfalls. And then, you know, when I took the role at Manning's, and I kind of got things like, normalized here, I had the opportunity to start kind of networking and meeting some early stage startups and founders were approaching me, I was had, by that time raised venture capital and three different businesses. So I had a decent network of VCs, from the supply chain and logistics space that were always interested in kind of networking and staying in touch on different opportunities. So, you know, I took that opportunity, while I was in the CEO role at a larger company was to like start giving back and mentoring a little bit. And then advisory roles, presented themselves. And what I found is I was helping companies solve the same problems. And I was doing it in a fraction of the time that I had done them in when I was previously operating the business because I realized there was a few things that I'm super good at, in the startup kind of in the startup context, and everything else sucks so bad, and there's somebody else that's so good at doing these things. So it's like the perfect time in life, I think, for me to share what I've learned, you know, I've always believed that advice should be free. And if somebody like values, your advice, and they want to kind of like solidify or formalize that relationship, for the last few years, I've been in a situation to do that. So in about two and a half years, I've, I've deployed about 350k of my own money, built a portfolio of about 30 Plus logistics technology focused early stage startups. And really my kind of goal in doing that was, I wanted to align myself with some great founders obviously, take the opportunity to try to make some money, personally. But more importantly, you know, through the performance of the companies that had been involved with it, and cargo Matic and ship dock and airspace, we were outperforming most venture funds, you know, and the money I put into those businesses have done much better than dollar for dollar than most VC funds are doing. So I thought, if I could do that on a larger scale, maybe there's a fun to be raised someday. So happily running, you know, a company post the sale of Mannings. Last year, I took a role running another private equity backed company, as a CEO, and was having a great time building a team in the US and doing some fun things. But this opportunity was Xbox came along. And, and there was a few things about it that just made it extremely attractive to me in terms of where I'm at today. So, you know, part of the reason why I've been able to, you know, participate in as many investments that have in two half years is because, you know, I try to be like, even though I'm a low tech size investor, I try to be a high leverage investor, you know, in these startups. And so, I've been able to kind of like, help them with corporate partnerships and help them find their product market fit, help them get their first hire for my network, or whatever the case is, maybe it's just like, telling them every like, you know, once a month, I Hey, buddy, you're doing great, don't quit, you know, but for whatever reason, you know, my contributions have been valued with these founders. And then they introduced me more founders, and it's just kind of grown organically from there. When I set out originally, I didn't expect to like deploy this much money. I'm not a wealthy guy, but this was important to me. And fortunately, my wife supported me on it that star but really, the opportunity was Xbox was, you know, it was founded about three years ago by Rudolph Sangay, who's this billionaire shipping magnate. He's the chairman of CMA CGM, the third largest steamship line in the world. He's the son of the founder and CMA CGM has been transformative. And in developing containerized, shipping, you know, the boxes that are all stuck out the port's right now, they own those vessels in those boxes. And they, they've revolutionized that industry over the last 40 years, and wrote off notice about, you know, many years ago that the innovation slowing down in the organization, the bigger they got, the harder it was to innovate. You were actually the first person to tell me about the book Innovators Dilemma, but this is the email dead dilemma inherent in large organizations is the doers are doing and there's no room or oxygen for innovation or for creative thought, and so rapidly that you needed to separate that. And that there was an opportunity to sort of cooperate amongst other stakeholders in the supply chain and curate a base of corporate partners instead of having one internal accelerator. This is a multi corporate accelerator, and we're currently supported by about 10. Not all of them are public yet but we'll be announcing like, throughout the fourth quarter of this year, the remainder of the corporate partners that companies like see CMA CGM, third largest Steamship Line, their, their freight forwarding division, see the logistics top five Global Freight Forwarder largest rail, one of the largest railroads in the US, one of the largest ports in the US, one of the largest software companies in logistics, supply chain visibility, all of these companies have come together, and they're paying fees annually to support the the operations of Xbox. And so you know, my role and the team that I'm buildings role here in the US is to work with these corporate partners to identify opportunities for innovation inside their business, help coach them on developing the proper framework for innovation and kind of create some entry points and gateways into their org for an innovation program. And then also define some common problem statements that can be addressed through innovative technology and the introduction of some startups into these large corporate partners. So once we have a common understanding, it's an aligned timelines around when we'd like to solve these problems by then we'll be sourcing startups to go out and solve these problems. And then on the startup side, the common problem that I've seen in my career, and the thing I'm seeing here is the boxes that every startup founder wants to punch above their weight class, and they want to get their product in front of the kind of titans of industry as early as they can. And I'm seeing now as I see founders continuously pitching to startups, or to to corporate executives, is that these corporate executives are brilliant people like they're Ivy League educated, they're super, super knowledgeable about their slice of the universe, you start getting into Silicon Valley buzzwords, and you start pitching a big customer, like you're pitching a VC, like you're having the wrong message for the wrong audience. And basically, the it's like inside of these big corporations, especially in supply chain logistics, were just so executional focus, the operation, you know, the moving of the boats, the moving of the trains, the moving of the freight, the operation of the warehouse, that's the central nervous system and the heartbeat of the organization. All of the people are like an immune system. And startups feel like germs when they first get introduced. So really, like these organizations are structured to filter out new ideas, because everybody, you know, has conviction around the way they're doing things today. So at Xbox, you know, we're hiring entrepreneurs, residents, and really great staff, to coach these startups help them develop their messaging. And oftentimes, these startups are just an idea, it's a concept so we can help them, you know, get from zero to one and match them up with folks that can help develop their prototype, help them find a founding team, and really help them incubate their concept until they're ready to go, what we're seeing probably the most traction and so far, in the first couple months of my journey here is what I'm considering more like Mac acceleration, like startups that are already like the Series A, maybe Series B, you know, range where they develop their product, they have some product market fit, maybe supply chain is a new vertical they're trying to go into or maybe they only have a couple of marquee customers in the supply chain space, but they're going to be able to address and solve the problems of our corporate partners, like we're able to kind of reach into those networks and connect those dots, and really facilitate some healthy dialogues. And so it's cool to work with these big companies and be welcomed in there with open arms. And I'm the guy like wearing a t shirt and jeans, in the boardroom at the whiteboard. But really, it's it's fun to kind of like play this translation layer right now. And also learning a ton about big company and big companies around the world, which is not sort of my domain expertise to this point

Greg Spillane: 53:38

was this the most fun you've had professionally.

Charley Dehoney: 53:42

You know, it's hard to say because like, it's like, everything I do is so fun. But I'll tell you, I've traveled nine out of 10 weeks, this my first week, in Omaha, I've gotten more work done in my co working space here in Omaha, because I can sit here and mow through and execute, there's no distractions. But when I get like, there's certain part about traveling with children is you know, and young children leaving the wife behind and putting all that work on her. That like gives you a little anxiety, you know, like the, like the Sunday lose a little bit. But man when I get on the plane, and I start heading to the next city, and like I'm going to, you know, map something out with a big company, or I'm sitting there watching a founder, present his project to a large corporate partner, and I can see the nods across the Zoom meeting. Like that is awesome. Because like that's the lightning, that's where these businesses can go from, you know, meaningful to valuable. And to be a part of that. Like, I mean, I have goosebumps right now thinking about it because it's like so when I first got offered this job, I told my wife like I think I have to take this and she's like, but you love what you're doing. And I was like yeah, but you know if they would have hired if they would have paid me to lift weights and chase girls in high school. I would have taken that job too. So this is probably as close to that as I'll get like coaching founders and talking logistics tackle You know,

Greg Spillane: 55:01

couple last questions. If you could go back and give 18 year old Charlie, one piece of advice, what would it be?

Charley Dehoney: 55:12

18 year old Charlie, one piece of advice, I would say, start earlier. You know, get going. I don't regret playing college football one bit. But, you know, if I wanted to be playing on TV, maybe not go to Idaho State, if I wanted to be closer to my girlfriend at the time, maybe don't let her you know, get away and maybe like, take these things more seriously. Certainly from a family planning perspective. You know, having three kids, I came from five, Katie came from six, we thought we had a dozen kids. But together, we started at 30. Because we really thoroughly enjoyed our 20s and being together and traveling. I wouldn't mind you know, having a couple more children. Now the ship sailed on that one. So, you know, I think for me, it's like, it took me going to college. And it took me like starting my career world Express and like, cutting my teeth there and climbing the ladder to really get the confidence. But like, I wasn't any better prepared to start my own journey and start my first company than I probably would have been and, and now that I'm working with so many founders and so many, just like super, super captivating people, they're half my age and twice as smart. I just see in their eyes, it's like, Dude, you don't even know what you don't know. And that's the beauty of this whole equation is like you're unjaded, you're unbridled. Like, you're gonna find some oxygen here, and you found me, which tells me that you're out there like clicking around at night looking for somebody that can help you. And, you know, it's a different world, we can all kind of like, you know, draw the differences between today's world, you know, you and I didn't meet on Twitter until there was a reconnect again, on Twitter until there was a Twitter right. But the point is, I think, you know, if success is meant to be yours, put yourself out there in the universe. Get going, open your mind, talk to people smarter than you listen more than you speak and just just go find it. Just go find the happiness.

Greg Spillane: 57:09

You're gonna let your kids your sons play football.

Charley Dehoney: 57:13

So we're in transition right now they've been we've been a flag only family, I've tried to keep my kids distracted by playing competitive sports in every capacity. You know, I had, like, you had many friends who ended up in tough situations based on you know, the concussion situation, including, you know, a guy that went to Poway that we both knew drew Walras, who played a Colorado and then for the Rams, who unfortunately committed suicide, you know, like Junior saao shot themselves in the stomach to preserve the brain. So, you know, in my internet work, there's always been this like, worry that like, my kids would want to play football and I'd have to be in the situation and my wife and I have always been anti and I've always told her that if it comes down to my son, playing football or smoking pot behind the bleachers, because he's rebelling because I won't let him play football like that's going to be an easy choice for me. And then I moved here to Nebraska and I kid you not for the first flag football practice. I took my son to I was an assistant coach, we had more dads on the field and children which is incredible. Do the math on that. So football is the the big deal here in Nebraska obviously. So they start playing tackle at seventh grade, how we played flag football in middle school, seventh grade, they play tackle here. So my sixth going on seventh grader is committed that he's going to be on that seventh grade team next year. His little brother Luke has never let him do something without him. So so Luke's in a in a long debate with his mother right now about what we're doing next year. So for me you know, I think I'm going to put in a request to Santa to get a helmet and shoulder pads and maybe get these guys done up in the basement this winter and see if we can't get them prepared to do it in a safe in a safe and fun way.

Greg Spillane: 58:57

Appreciate you coming on man it's been it's been a pleasure knowing you for all these years and you've been someone who I've like I said I think I've learned a ton from you know just just by person. Yeah, so it's been great man I wish you all the all the best in the future and look forward to more opportunities to work together on stuff.

Charley Dehoney: 59:20

You as well man until Erica and the girls I said hello and look forward to to stay in touch. loving, loving your podcast so far. Listen to the JR episode. Running his mouth is always miss that guy. But really, really appreciate you putting this out there man. Great content, and looking forward to staying in touch with your podcasts. Keep going man

Greg Spillane: 59:39

cheers buddy.