Noob School - Jack Sterling on Data, Veterans, and Building Purpose After Service | #NoobSchoolPodcast

Episode Date: October 24, 2025

My son Jack Sterling returns to Noob School for his fourth appearance — officially becoming the most frequent guest on the show. This one dives deep into what Jack’s been up to lately — from his growing business, Cloud Hound, to his work with Upstate Warrior Solution helping veterans transition into entrepreneurship. We start off trading thoughts on our favorite podcasts and how shows like Lions Led by Donkeys and My First Million have influenced the way Jack thinks about leadership, learning, and risk-taking. Jack shares how fantasy football and analytics sparked his fascination with data — eventually leading him to pursue a master’s degree in data analytics at Clemson. But the heart of the episode is about purpose — how veterans can rediscover team, mission, and structure through entrepreneurship. Jack breaks down how his program at the Rupert Hughes Veteran Center supports veterans, first responders, and their families across the Upstate by helping them navigate healthcare, education, and business ownership. He shares inspiring success stories from entrepreneurs who’ve come through the program — from a veteran-run medical training company using human remains for realistic field instruction, to another launching Upstate South Carolina’s first paddle tennis facility. We also dig into the lessons he’s learned running Cloud Hound — from ditching international business to focusing on “cyber and fiber” solutions for local clients, and why most security breaches start with people, not technology. Jack explains his live training on social engineering, phishing, and why emotional manipulation is hackers’ easiest path in. To wrap it up, he shares the book that’s had the biggest impact on him — “Tribe” by Sebastian Junger — and why it reframed his entire view of community, fulfillment, and the difference between the military and civilian worlds. If you’ve ever wondered how to find purpose after leaving a structured environment, or how to turn your skills into impact, this one’s for you. Get your sales in rhythm with The Sterling Method: https://SterlingSales.co I'm going to be sharing my secrets on all my social channels, but if you want them all at your fingertips, start with my book, Sales for Noobs: https://amzn.to/3tiaxsL Subscribe to our newsletter today: https://bit.ly/3Ned5kL #SalesTraining #B2BSales #SalesExcellence #SalesStrategy #BusinessGrowth #SalesLeadership #SalesSuccess #SalesCoaching #SalesSkills #SalesInnovation #SalesTips #SalesPerformance #SalesTransformation #SalesTeamDevelopment #SalesMotivation #SalesEnablement #SalesGoals #SalesExpertise #SalesInsights #SalesTrends#salestrends

Back here, I believe this is podcast four, one, two, three, four. Returning guest number four. Yeah, so this will be your fourth podcast, my son, Jack, Sterling, and that puts you number one, sir. All-time most frequent guest? I think Mr. Michael Pace is number two, or maybe Marty. Is this the first show back from overseas? Yeah. So I'm back on, first on the list when we get back overseas.

That feels pretty, pretty. pretty special. Thanks for having me. Well, thank you. I hope I don't, you know, my accent hasn't changed at all. Hopefully all of our preparation and hard work getting ready for this show is going to pay off. Yeah. Unfortunately, all these notes, none of them are about you.

That's just a blank piece of paper. Yeah. So it's just, we're going to have to just, you know, let me talk about what we already know. We're going to fall back on our existing rapport, I think. Right. Right. Right. So podcast number, Chris, 150.

156, I believe. 156. Wow. Podcasts 156. I don't think Rogan has that many. I think he does. Does he? We want more. Okay. Probably in the thousands. I've been doing it for a while. Well, that's a good point. You know, if you think about, you know, Rogan now we look at him and he's so successful, he certainly wasn't when he was at 156. No one even knew he was doing a podcast.

I mean, I think he had a pretty good because he was the ring announcer for UFC because he'd done the Fear Factor thing. Yeah. He had a brand. People knew who he was. And so he might not have been. And I think he was making more money at 156 than you are on your podcast. I think you're right about that. But, I mean, as I recall, they were in, like, his garage or something. Oh, for sure. Yeah, it was definitely more grungy than it is now.

Nobody was paying him $100 million for a podcast. Just to talk about ancient aliens and peyote. Well, I kind of like that. I love that. I'm not saying anything negative about it. It's just too much to listen to sometimes. Four hours a day or three hours a day. It's a lot.

It's a lot. Lent itself to clips. Yeah, clips are good. Yeah. I watch him sometimes just to learn. And one of the things I like about it is he's just so, he's like him a lot in every opinion, but he's just so relaxed about the whole damn thing. He's genuine.

Yeah. And people like that versus, hello, this is John here with you. They don't want that. True. What's your favorite podcast? Well, I'd say there's really two categories of podcasts that I listen to primarily. there's a military history podcast called Lions Led by Donkeys. The podcast hosts.

Lions what? Led by donkeys. Okay. All right. That would be bad military leadership? Basically. Okay. So it's taking stuff.

Sometimes it's little, you know, things that happen in military history you might not have heard about. Or it's things you definitely heard about, but not from the perspective that they're telling it from, which is typically the lived experience of the people fighting the fight, right? We read in history books, you know, we invaded here. and this happened, kind of the big picture's strategic peace perspective. This is much more, you know, the Joe on the ground in the trench who's got dysentery and body lice and is trying to just survive the day, right?

It's funny. It's kind of a dark humor. They kind of talk about this stuff, you know. Like, for example, they cover Napoleon's march into Russia. Just disaster, right? They went in with 500,000. They weren't really even trying to start a fight. They were just trying to stunt on this young Russian prince or czar.

didn't go that way. They ended up getting into a fight in the middle of the Russian winter, and about 9-tenths of them died. The ones that came back, straggled back into Eastern Europe looking like a literal army of zombies right there. This is Poland going into Russia? This is Napoleon. Oh, Napoleon?

His grand army was all nations that he had subjugated. All these different... They didn't speak the same language. They didn't have a common uniform. They had no plan. A lot of them didn't have shoes. They just walked in, got completely wrecked. And I think that's...

where the modern conception of zombies comes from. Zombies. It looked like it. They were taking bites out of each other because they were starving to death and they were all freezing and covered in frostbites. If I bite to your shoulder, you don't even get to notice. So this is what emerged back out of Russia

in Eastern Europe and they're like, well, zombies. So that's one podcast. It's line filled by donkeys. Hold on. Let's talk about something. What is the, what, which episode do you think that you like the best? Well, then, Napoleon's Grand Army

marching into Russia was one of the ones that I found most, just fascinating because of fact that they weren't trying to start a fight. They were the most powerful force on the planet, but they didn't plan to go fight, so they were not ready. They had ancient cannons. What were they going there for? Napoleon and the Tsar, the Tsar Nicholas, I want to say, were kind of buddies. And then once he became the czar, he kind of got a little bit like,

I got to be, you know, true to my own countryman. I can't be doing whatever you want, Napoleon. And Napoleon's like, I don't really like that. I'm like other people having influence every you. So I'm going to march this big-ass army that I hastily assembled Napoleon's Grand Army, marches it into your backyard just to kind of do a drive-by, right?

Show a force. I'm not going to shoot. We're just going to come through and show you how big and powerful we are. So you'll remember that we're good friends and you want to listen to me when I talk. Yeah. shoes were gone, all the horses were gone and eaten, the cannons were all broken, they were, everyone was diseased, everyone had, you know, a frozen diarrhea sickle coming out of their backside. Like, it was one of the most hellacious lived experiences you can imagine.

And I think with a lot of times history, we think about the numbers and the kind of geopolitics of it, but 500,000 people marching into the Russian winter and then just getting chewed up like hamburger meat and then coming back. The lions led by donkeys. That's a podcast on Spotify? iTunes. iTunes. Yeah, iTunes podcast or Apple Podcast or whatever it is.

Okay. That's where I get it. What's the other one? So the other one, I put a bucket because there's a few different content creators that I follow in the space, but fantasy football is my number one hobby obsession, a combination of data analytics and beating my friends at stuff. It's kind of like what makes me stay on that stuff. But the various content creators that use a data-driven.

an analytical approach to understand the game of football, which is a small sample size, high variance environment. It's really was kind of my first, like, gateway drug into, like, math and why you would be interested in analyzing numbers and data, right? So I, you know, grew up telling myself the story that I didn't really like math. I wasn't very good at it, like history and reading and writing. And so it wasn't really until kind of preparing for business school and then just consuming a bunch of fantasy, because I sucked it.

When I started, I was getting beat constantly, having to do the losers' punishment and stuff. So I was like, how do I not suck so much at this? Looking for something, that lens of data in a field that's really driven by a lot of kind of like archaic thought, you know, kind of the old school football mentality. We're just going to grind it out. How big is his stone? Yeah, like, oh, he looks real good. It looks real smooth. He's very subjective analysis.

And they had like for like length of arms for the office of linemen. Yeah. There's something there, some signal, but not to the extent that it's. may not to be. But yeah, the data analytics, you know, ended up going to Clemson for data analytics masters. And so it really kind of was my gateway drug to looking at anything football or otherwise through the lens of data and what can the data tell us, right?

So that was, those are really the two that I spend, if I'm listening to a podcast, it's one of those two types. In Noob School, of course. Newb school, of course. That's more of a YouTube thing. That's true. You do have a podcast, but. Yeah.

You just get the clips. Just the clips. Yeah. That's a good way to do it. We don't have enough time to watch all the good podcasts. There's so many good ones. And that's what I listen, listening to me, even on Sunday on game day, for the most part, I'm putting on Red Zone and I put my headphones in.

And I'm not watching the game. I'm just listening to Chris Hanson or Scott Hanson Red Sox the Catcher Predator guy. Scott Hanson. You're watching two things too much. Yeah, two separate shows. Two Hansons, very different tenor to those shows. But yeah, he's talking, you know, just covering all the games. all the time, no commercials.

The great thing about watching to Chris Hansen, the catch a predator, is we know what's going to happen. Every time. They're going to catch the guy. Oh, God. Yeah. I'd much rather do Scott Hanson's job. Yeah, true, true.

Well, that's cool. That's cool. I think my first million is a great business when I listened to. Is that Guy Raz? That's how I built this. No, that's how I built it. I like that, too.

I don't listen to it much because I don't, it doesn't, like show up on my stuff so I don't go find it. But my first millions to guys that both became successful entrepreneurs. And not, you know, not crazy successful like in the newsletter business and nothing, nothing bizarrely crazy, but just successful at a relatively young age. And they said, we're going to do a podcast called My First Million just about how people got to that first, you know, first base of being wealthy. You know, my first business, how it did well. and everyone they tell these just remarkable stories. You're like, wow.

Because like you said about head tracks, a lot of people think, well, first they got to do this, this, this, and then I can do this, and these people are like, no, you can just do it this way. You can just do it, yeah. So I like that one. And then what's the one with the four guys from Silicon Valley? It's not my first million.

All in podcast. All in, okay, yeah. I enjoy that. I listen to that a few times too. Yeah, it's not all, it's certainly not all group think. at least one to two of them and the other two are giving you both perspectives on things

whichever way you believe and they're just smart I mean they're the kind of people who've made hundreds of millions of dollars or more and getting their perspective on what they think about doing things certain ways is I think really interesting

Yeah definitely You know One guy said something interesting. Chimoth is his name. He was the first, really the first sales manager at Facebook. Okay. That would be a good job.

Yeah. But he happens to be really smart. And he's the one who helped figure out how to monetize the millions of users they'd gotten. How do we monetize this into all the different ways they sell ads and things like that? And so, you know, one thing leads to another and they go public. And his stock's worth, you know, billion dollars. And I don't know what the age was, but, you know, relatively young age, probably mid to late 30s, he got out.

He's like, you know, I don't need any more money. And this is, you know, imagine how hard you're working if you're the head of sales for Facebook. Yeah. And so he got out. And someone asked him, you said, you know, if you just would have stayed. or not sold your stock, that would be like $50 billion. Yeah. He goes, do you regret that?

And he goes, not a bit. Yeah. And it was an interesting reason for people, if you're thinking about your life, he's like, it's worth not having all that money to have all that freedom I've had. Yeah. You know, to be my own man, to invest my money where I want to to start my own businesses and not be straddled as a employee. Right.

You know. And that's a lot of money. to leave him on the table, but of course, at the point he made the decision, you don't know if that billion is going down to nothing either. That's right. Yeah. I mean, and what's, and functionally, I understand there's, you can, you know, if you're spending billionaire money, but like for me and you, functionally, what's the difference between one and $50 billion? None. Not really. I mean, some, obviously. Probably more trouble. Probably more trouble. You know, you can get into more trouble. You can take a bigger bite and get way out of your skis where...

Somebody told me, not told me, but I've read about this, this guy has been exposed to lots and lots of super rich people. He says in his experimentation or his study, $250 million is the Mendoza line. He goes under that, people are kind of under the radar. They're happiest clams, of course, and they're, you know,

you've got latitude to do whatever they want. And once you start pushing north and you're half a bill, Bill, those people are just miserable. Yeah. It's just, you know, the Gulf Stream's not working again. Yeah.

You know, we've got to get to use the other Gulf Stream The old one. And you start to get that kind of attitude. Well, so-and-so got a 260-foot yacht. Mine's only 240 feet. Right. Trade it in. I only have one helicopter pad.

Right. And also, you're so rich, everyone wants that money that all, you're kind of becoming this bubble of people who just praise you like you're the king. Yeah. And so you can't be normal anymore. We had freshman year at Rhodes. We had a, actually sophomore year, so he was a freshman. And freshman coming in and the incoming class was a Rockefeller.

And it was like he couldn't be friends with anybody because everybody knew, based on his last name, that he was, you know, a billionaire. And, you know, you try to – we were kind of recruited him into our fraternity, right? And I was, I was tasked with fraternity, this guy particularly. And it was like, I'm going to give him kind of the slow play. Like, kind of I don't really care. Like, whatever you're a rock fella. What a big deal? And I was just like, hey, man, what are you up to this weekend?

Like, we're doing a little off-campus party thing. You want to come over. We're going to get a keg and stuff. It would be funny. He goes, yeah, that sounds fun. Beer pong, bag toss, all that stuff. I can't. What are you doing?

It's like, I'm going to Texas to drive my family's Formula One car. I'm like, cool. We're just different planes of existence, you know? Whatever. Yeah, so it didn't bother me in the least. Like you said, though, it puts him in a place where he can't be like one of the dudes. You've got to be someone like him to be on his level, you know, to not think this person's only here for my money, right? Or whether they're, whatever they're asking for, what their angle is, you've got to think.

It's like a very big imbalance between lifestyles. Yeah. Right. Well, so when we get the $250 million, just stop it right there. I just, you won't know about it. I'll just disappear off the face of the earth. Oh, we're going to hang. No, we and you will stay hang.

I'm saying the general people, the we out there. Right. That's the, I think. And help others. Quietly. Anonymity, right? Yes. Right.

You know, we don't need to heap praise or focus. just help people quietly, right? Well, speaking of Helping, let's talk about, you got a few things to talk about, but let's talk about what you do with the Veterans Center here in town, the Rupert Murdoch. Rupert Hughes, veteran center,

R-HVC, aka the Roop, the Roop. The Rooke's not on fire. It is. So Rupert Hughes Veteran Center here in Greenville. Upstate Warrior Solutions. Upstate Warrior Solutions. Yes. Okay.

So let's just paint the picture for a second. So here I am happily self-employed three and a half years ago doing my business with Cloudhound, you know, trying to sell cyber and fiber. Charlie Hall, president of upstate warriors solution. Marine, I think he's a lieutenant colonel now, but in the reserves. I met Charlie, great guy. I knew up upstate warriors, but I didn't really have any connection to them beyond that. And so he kind of just called me out of the blue one day. And it was like, we've got, we're moving into this new building in a few months,

we've got this capacity to add an entrepreneur program. We have employment covered. You know, upstate warriors mantra is duplicate nothing and partner with everybody, right? So we want to start adding entrepreneurship to our line card. We can help people who are entrepreneurial, not just looking for a job. And so wasn't looking for it, wasn't thinking about doing something like that. It never crossed my mind. But once the opportunity popped up,

it really kind of formed a yen to my existing yang. So I have this self-employment, no team, no office, unlimited ability to make commissions, but also zero benefits or, you know, don't do anything on that making money. So it was missing that team element was the biggest part. I am solopreneur, you know, grew up playing on team sports during the Navy because I missed being on a team, wanted to be on the SEAL teams. And so that noticing team aspect was a big. You know, the tradeoff was they got to be with my kids every day and do the family stuff first and foremost.

And so adding the upstate warriors to the equation pulled me away from that a little bit, put me with my cloudhound work a significant amount. But I said, hey, I've never been in an entrepreneur program. I've never started one. Let alone never run one. But I think that's in keeping with the entrepreneurial spirit, right? We're going to do stuff that we've never done before and just do it anyway. So we agreed to those terms.

and so now I do that part-time. It ends up being a little more than part-time just because of the nature of having the team and the demands there. But yeah, anybody, so we serve the seven counties of the upstate. Seven counties. Seven counties.

We serve veterans in the military, law enforcement, firefighter, first responder, EMS, all that jazz. Any veterans in military or first responders. And their families. And their families. Right? So they get the spouse of a veteran,

son of a veteran, et cetera. They can come to us, and we serve the whole person. in one place, right? So you can come to us, everything from health care, housing, education, employment, entrepreneurship. Meaning you have people that will help them figure all that. Correct. We're not going to be your doctor. We'll help you navigate the health system. We're not going to be your teacher. We're going to help you navigate the education system, right? So for me, it's, I'm not the world's greatest entrepreneur. I don't pretend to be. I've

got the experience that I have working for myself, but I've never hired or fired somebody or, you know, really managed a payroll or have a brick-of-mortar or anything like that. So there's plenty of stuff in business that I have not done yet. more of a sounding board, accountability partner, ally advocate, and, you know, someone to go to bat for you. And that's really, you know, not to my own horn, but that is impactful, right? When you come from the military, if you're on this high team, high accountability, high structure environment, and you leave, whether you retire, whether you get out at, you know, nine years or four years or whatever, you're leaving that. I was fully aware of what I was getting out of and knowing I was going under the woods alone without a map, right? and you get to your destination, you're there,

and you're just like, I feel like I can't do anything, right? Because I'm used to having this high capacity to do stuff because I've got this big support structure underneath me. Yeah. But now I'm just a dude, and I don't have any support structure, right? I mean, maybe a dude, but like, not from a professional standpoint and not like the military provides, right? I use the analogy of Lance Armstrong, right?

The dude could get on a bike and pedal, could not build a bicycle to save his life, right? So you kind of get out, you have to be the navigator, the bike builder, the engineer, the nutrition, You do all the stuff. You don't know where to start. You don't even know. That's why, you know, when we look at the psychological profiling we do on people, the Colby test, generally speaking, that most of the entrepreneurs, successful entrepreneurs, have a very balanced profile.

You have a very balanced profile. Yeah. Yeah, not extreme in any one category. It just means that you can handle selling, marketing. You're okay with doing numbers, you know. And there's some people like me, you know, it's just like mostly selling, you know, not so good. on the numbers. Yeah, because of the extreme subject matter expert versus kind of the generalist,

jack of all trades. That's a good point. If you do have someone that's really deep into one area, they probably need a good partner. A partner, excuse me, a partner, or in some cases, might not be a good idea. Yeah. You know, I talked to a guy or young man two days, a couple days ago, and he wants to do his own thing, and I said, well, you need to take this test, and we did the test, and he's got,

on scale, on one to ten, almost. almost no propensity to be a risk taker. So it's like, I want to be a risk taker. Okay, well, you know, something right to check. How am I going to, is it at risk? Yeah. No, and that self-knowledge is huge. And I think that's, you know, one of the things that I think I help people with when we sit

down to talk is, is like they're in their own bubble now, right? They get out and there's no one telling them, yes, no, good, bad, anything. They're just like, they don't know what, you can have no feedback, right? They're not getting any pushback or friction on anything they're doing. It's just like, I'm just doing stuff in a vacuum. And so when they say stuff to me, I'm not going to ever be the dream killer. I don't pretend to be the shark tank that says, hey, this is a great idea, invest or no. So it's more just to be a sounding board and reflect back what they're saying to me.

It's like, make sure I'm hearing this right. You're going to do X, Y, and C. And they're like, well, when you say it like that, maybe that's not the best idea. I'm not going to quit my job three months before retirement and start a self-practice, you know. You're going to come up for $350,000. Yeah. Yeah. You need a million dollars for the mixed martial arts dojo.

Like, great. But let's talk about. Build a studio. We're going to. And sometimes you get really good ideas that come through, too, and someone's actually done a lot of the work. And I think that's, you know, we're not in the business of picking winners and losers. We're there to help everybody on their journey, right?

So if the guy that needs to make money right now to pay his bills next month, we're going to help that guy, right? He probably needs a job, first and foremost. Well, you know, if you're trying to start a business because you've got to make the bills paid this week, it's like, that's not to do it. It's got to be fun, though, because you know, I both like talking about ideas. But when I was finally ready to go to work, and I thought I would start, you know, have an entrepreneurial idea.

So knowing nothing, like age 23, knowing zero and having no experience, I said, well, I'm going to start two businesses, because I can't decide which one's going to be better. They're both so good. I hear that one a lot. I hear people that are like, here's my business. And okay, cool. And the next thing I'm going to do,

another thing I'm doing, like, okay, let's just, I like a lot of analogies. To me, analogists have always helped make sense. So the analogy that I use in that case is, you ever try to start a fire with a magnifying glass? You know how hard it is? It must be. Very difficult, right? You got to get the sun just right.

You got to hold it just right. The conditions have to be dry. You've got to be consistent and keep that thing precisely on the same spot. Otherwise, it's not going to light. Well, what they're trying to do, trying to start two fires at the same time with the magnifying glass, just jumping back and forth and you might get too warm spots. Over here. Over here. You're warming up two spots, but you're never going to ignite, right?

And really, if you want to have something, you've got to get that thing. ignited, burning, and stable. It's not going to go out in a minute or two before you take a little bit of those coals out and start something else, right? Because it's very difficult to start something that doesn't exist. I think, you know, when I study Richard Branson,

he's the model that I use. He's like, he's the starter, man. He loves to start it. So he has enough money where he can, like, try something. And if it works at all, he could just leave someone behind an ops person to deal with it, you know, and try to grow it. Yep. He says, I'm on to the next thing.

But when he started, he probably wasn't doing that. He was like, I got to, this is the one thing. He knew everything. The one thing has to be everything. Yes, one thing. He knew everything. And as soon as it's ready, either you close it down or you put someone in charge and you move on. That's got to be a pretty interesting point when you have that one singular vision for however many years it takes to get it to reality.

And then one day you're like, man, I don't even need to be in the driver's seat anymore. Right. Probably better for me not to be in the driver's seat. Yeah. And I can expand my scope and look at other stuff. And really at that point, almost isn't entrepreneurship anymore, right? It's like you're kind of like your investor or yourself, your self-backer kind of thing. Right, right.

You move into the owner's box. And yeah, it's just then someone's got to have the team meeting every day and look at the numbers and make sure you collect the money. and all those ops kind of things. And entrepreneur doesn't like all this stuff. No, I'm keenly aware of that. It seems it has a sniff of kind of corporatism. Like, we've got to put a little bit of corporate governance structure on this thing. I'm like, best of luck.

Yeah. I'm going to move on to the next thing. Yeah. So, yeah, I must say I was joking about Rupert Murdoch, but Rupert, you know, we've had Charlie on the podcast, and he's just done a remarkable job. I mean, imagine, because he's dealing with mostly nonprofit organizations that are trying. And the government.

And the government. Imagine getting up all to agree to move under one roof. Watching him from an arm's distance with the amount of people that he knows, the amount of organizational entities, acronyms, initiatives that he's tracking, he goes up to Washington every so often to kind of lobby for veterans. I mean, he's one of the most masterful networkers I've ever been around. the number of people that he connects with and the repository of information he has on everybody just on top of his head seemingly it will.

I'm sure he does more work behind the scenes to make that true, but he's also super humble. He doesn't have an office in the room. He's got a cubicle just behind mine, right? Because he's never at his desk. He's always out doing stuff and meeting people. And he's also, I've never heard him describe himself as the president or the founder of upstate warrior solutions.

He's always told people I'm a coworker. I work with Jack. I work with Jack. I thought people he was one of our interns. It's funny. Poor guy. I mean, I wouldn't do it if he didn't think it was funny, but he, he's just very humble. And, you know, he's not better than anybody.

He doesn't, he doesn't perceive himself over and time. Well, probably, you know, an ideal Army officer. Didn't he go to West Point? Marine Corp, no. He didn't. And Apple. He didn't. And Apple.

He went to Apple and apples. Okay. Well, either one, I'm sure. But just that thing about duty and leadership and, you know, said leaders eat last. You know, that kind of thing. Yeah, that's great. That's great.

Well, so do you have a success story yet from somebody you've helped? Yeah. Well, one thing I'll say is the number one ask of the clients that we've worked with in the three years and change we've been running this program has been help with financing and funding the startup. It makes sense. Nobody in the military or a first responder world has ever been asked to go pay for their deployment, right?

Hey, you're going to Afghanistan. You've got to come up with $102 million dollars to go. Afghanistan, like, not, that exists, right? The taxpayers are already doing that. And there's some functionary at this, you know, Department of Defense War now that's doing the budgeting stuff, right? So not in our thought process. We're going to do a thing. So number one ask is funding. A couple of years ago, we were approached by a local nonprofit called Abundance Capital. It's a venture philanthropy outfit, which is a new concept to me. Essentially, we solicit, Charlie mostly, solicits charitable contributions, donations to our fund that abundance capital manages. And then we have

established a review panel, which is a bunch of local, probably 50-50 veterans and non, but all the local successful business people, venture capitalist type people that meet, hear the pitches of our applicants. So my job is to, is not to be a voting member on the panel, but it's to help get the pitching entities, people seeking funds ready, right? Approve them, vet them, get them pitched up, ready to go and then put them in front of the panel and let them go. And so the panel hears their pitch, asking their questions, and then makes a decision or do we're going to give them what they're asking for, something modified, or we're going to decline and give them a recourse for coming back in 90 days, meet quarterly. So it's taken a couple of years to get up and running to get

some funds. And we've got some funding from the Greenville County, the local, regional development corporation, Truest Bank. We've got some great financial partners. We've got two loans out. We've helps two local businesses. One is a, it's a team of a Marine veteran and an Army veteran that came from North American Rescue with this idea. They quit their job. It's basically this idea to start a medical training business using human remains, which is a pretty touchy kind of weird business, if you ask me, a lot of people are kind of like cadavers, huh? So, you know, when your number one cost in your business is human remains, that kind of like, you don't hear that every day, right? So they were, I think they made a quarter million dollars in revenue in their first year, totally organically.

It's not their hustling. They were debt-free, and they couldn't get a bank or anybody to lend them any money so they could scale faster, grow faster, lower their overhead costs and make their margins bigger. Couldn't get anybody. So it did make sense, and the refrain over and over again was you just haven't been around long enough. You know, 12 to 18 months old. That's just not a good bet for most lenders. So they were our first. And they came and they pitched and they didn't get the money at the first try.

We gave them a list of things to work on. And they came back and pitched 90 days later and they got $40,000 from our venture fund. So they've got that right now. They're making payments which go back into the fund for the next people to come along to ask for money. So it's kind of evergreen pays for itself. And then just last week we had another, this is a West Point grad, got named Dan Fitzgerald. He came to us a year and a half ago. And it was one of those ideas where I thought, that's great, man.

That's a cool idea, but like, that's a pie in the sky out there thing. He wanted to bring paddle tennis to the upstate. And I've never heard of paddle tennis. You met Dan. You met Dan. You met him to him to him. Yeah, yeah, yeah. So Dan wanted to bring paddle tennis.

And I don't know, paddle tennis is big in Latin America and Europe. It's like a combination of tennis and squash. Got the plexiglass walls. You can play it off the wall. So it's just a very dynamic sport. You can go out of the fence. You can go out of the fence. See, everyone's seen that clip.

It's very, it's like, you know, we've seen the pickleball crail. Yeah. Paddles different, but similar. Yeah. Racquet sport only doubles. Played with a smaller tennis ball with less air, so it's kind of squishy. But anyway, he's been grinding for the last year and a half. You know, found a business partner.

He's found it some investors. And so he's cooking with gas. And he didn't necessarily, one of our, one of the defining features of our fund is that it's not the only source of funding for people. We don't want it to be, you come to us and you get all the money you need and you don't have to go to outside funding. We want it to be a gap. or a bridge to real kind of established capital. And so he's got investors coming down the pipe in the next, let's say, two months that he feels pretty good about. But in the meantime, he's already got invoices for gravel, and he's putting these pop-up courts up.

And so he's got expenses. And so we're helping him. So he's got his spot. We got him 25K to basically bridge from here until those investors hit. Where is the spot? The Malden? I think it's in Malden. I can't remember he's definitely where he's putting it down.

I should know that. I talked to a lady investor at the startup level, but probably beyond this seed money. But she would talk to someone and said, okay, I'll invest $500,000 for this amount. But here's how I'm going to give it to you. $100 when you hit these milestones. Another $150 when you hit.

hit these milestones and $2.50 when you hit these. Yep. And after that, if you need more money, we'd go somewhere else. So she was kind of right in that spot between, you know, they're up and running and going for the big money. Yeah. That's a, you know, I think there's a, you know, the institutional investors that kind of have those thresholds.

And, like, once you've been around for a couple of years, you've got a decent base of business, then you can kind of start talking to them. Yeah. From almost everybody that I'm talking to, they're pre that. They're pre-revenue. Yeah. Just getting started in the last year. you know, looking for growth.

And then one of the other big trends that we see with these veteran clients is we, I say we as veterans, we pride ourselves on being hard workers, right? We're elite worker bees. Best way to describe it. But you need structure and guidance to be an elite worker bee, right? You need someone telling you what to do and what works needs done and where and how and all that stuff. And so a lot of veterans get out and they start a business.

They don't really want to work for the man. They want to work for themselves. I get it. But they aren't working on the business at all, right? They're a solo handyman or a landscaper, and they're doing all the landscaping and all the handyman stuff, but it's just a treadmill that never stops. Not sales and marketing or... They've got to do sales just enough to get the pipeline filled, but the minute they take a day off, they don't get paid, right? And the problem, they'll say two things like, simultaneously, I've got more work than I know what to do. I can't meet all the demand that I have out there. I also can't afford to hire someone to meet.

the additional demand. That's tough. And to me, that's the quintessential way where we can come in and help and say, you've got the drive, you've got the know-how. You need to intentionally take time to work on your business regularly to the point where you're not the doer in your business.

Right. If you own a McDonald's franchise and you were in there flipping burgers and dropping fries every night, that's a problem. You've made a mistake, right? You don't own that franchise so you can be a, you know, a fry cook.

Definitely the best, the best businesses or best business people I see have made that jump where they're not running, they're not operating anything. That's right. They have people operating the stuff and they're there to facilitate them, help them have everything they need to do the best job they can. Yep. And in some cases, I've seen people make piles of money when they back away and they're just

an owner and nobody even knows who they are. Yeah. And then they can really look big picture. Then they're strategic. They're growing in the business. And that's, well, the analogy, this is a Mike Ungerism, hey, we, restless. There's a dog. Restless puppy.

You know, the three eyes of the entrepreneur, right? What are the three eyes you need to be aware of? There's, you know, using that McDonald's franchise again. The burger flipper, right? The workery. There's the manager, store manager. And then there's the owner, right? And a lot of people, when you start a business, you're all of the above.

Right. You're flipping burgers. You're putting out customer fires. You're, you know, you're making sure that everyone's on staff and showing up and they're wearing their uniforms and then you're also doing the work. And oh, yeah, and you're also kind of talking to talk to the bank about the loan to get a second location opened up. And it's just like, you know, you know the lotto machines with the little ping pong balls bouncing

around. Like that's what your brain looks like when you're doing everything. You've got all these million priorities and they're floating around and you're like, how do I figure out which one to grab and work on right now? Yeah. It's hard. So we primarily are trying to get folks to work on their business periodically. So we do, you know, meetups.

We'll do entrepreneur nights. Just take an hour a week, take an hour a month, come work on your business. And that little bit sometimes is enough to get them thinking that way. I like that. When we were building, you know, we built one business for 20 years. And there was a whole lot of burger flipping. You show up early every day. You work all damn day.

I mean, it was a grind. But we got to the point where once a quarter, four times a year, we'd go away for a three-day weekend, the leadership team, and think about what could we become, how we'd. would we do that and just kind of brainstormed that gap between where we are now, where we want to be. And, you know, every single big thing I could point to that got us from where we started to where we ended up came from one of those weekends. It's intentional.

Things don't happen by accident usually, right? If you don't write it down, I tell people I've never done anything worthwhile that I didn't write down at some point. So I think that's the, so many, me included, we'll just jump into a business and just start doing it. We'll just start working and operating in the business. and it feels good. You know, if you're in the military,

if you're a firefighter, law enforcement, whatever, doing your job is very rewarding, right? You get paid for it, but the job itself is also very rewarding. You can see the impact of what you're doing, and you don't have to seek recognition for what you're doing. You kind of just naturally, the people that matter recognize you for what you're doing, right?

Most of the general public doesn't even know. And that's not always true in business for yourself, right? You've got to seek recognition of what you're doing. Otherwise, you know, trees fall in the woods and no one's there to see it kind of thing. And it might not be rewarding to just be constantly working. You might be kind of like burning yourself out because it's just like. Yeah.

Well, working on the business is where you want to be. But I'm so glad you're doing it. I mean, you're learning a ton, helping lots of people. You're finding, you found me some good people that you've met over there that you sent to me that I work with now. Two of them I work with every day. Well, that's really cool to hear. And I love when a good introduction works out, right?

You know, never want to have the opposite happen. But that's one of the cool things about being in the Roupe is that there's such, so when upstate warriors, before we moved into the Rube, right, the RUPS have 30,000 square foot former bank headquarters. So it's very nice, well-provision, very beautiful building. Yeah. We made it into our home, so it feels very much like you're going into someone's home where you're familiar and know people.

Before that, we had a tenth of that, we had 3,000 square feet of shared office space. There's no room for activities. We had a little cramped conference room. It was always double-booked. It smelled like the last people's lunch. Where was it? Caled on court on Pelham. Okay.

I remember that. Cross from PTG. Yeah, I remember that. So, you know, there was no room for activities. And we had all these community partners that we did stuff with. And then we were, you know, constantly referring back and forth to. But there was no space for them to be in our home, right? But now that we have all this space, all these different.

I mean, like we said, we partnered with everybody and duplicate nothing. So there's all these different community partners that are doing things with us. And they're coming through the doors and it's happening in the building. And, you know, you walk in and those be, you know, 30 sheriffs with their, you know, their police working dogs. And they're all just checking the building out and doing for a tour. Or we do a monthly radio show with Bill Friedi and comes in and he'll interview different programs or veterans. Or we get, we get one veteran entrepreneur on there per month to kind of showcase and spotlight what they're doing. I walked in a couple months ago.

And it was the, it was during the Highland Games. And the Royal Scottish Frusial leaders have a partnership with Upstate Warrior Solutions. where they come over every year for the Highland Games, and it was 20 Scotsmen in their full dress, kilt regalia and bagpipes just walking around the building, talking to people. It's very cool place to be because there's so many network nodes

that cross through those doors on a daily basis. And you have a great Christmas party every year. Yeah, you get dressed up like the Grinch. You have it for the veterans and their children, and you get staff to dress up as, like, like different Christmas characters. The first time I went, one of the guys dressed up like the Grinch.

They looked pretty cool. Well, the first little girl that walked in started screaming and he cried. So I guess live and learn. Yeah, last year's Christmas party, there was the Grinch and Santa and everything. There was also a bunch of Star Wars character for some reason.

Yeah. Like Kylo Ren just hanging out in the Christmas party. I was like, hmm, cool. Well, let's talk for just a minute. Give us a summary. I know you started Cloudhound. Gosh. How many years ago?

It would have been, I think, January 1st, 2018, with the official conception. It seems like yesterday, but I do the math. That's like seven years ago. Almost eight, yeah. We're closing it on eight, yeah. And so that was a business to be a distributor or a reseller or agent for the ScanSource, telcom and cybersecurity line, right? Correct.

Okay. Yeah, so we started selling everything that ScanSource offered to everybody on the planet, which, you know. And anywhere on the planet. Anywhere. We decided. I was coaching Jack up like, we were to stick around in Greenville, okay? We stay where we know people.

And then within a week, I said, I got a hot lead for you. I've had a friend named Stanley who lives in South California. His business is mostly Taiwanese. Taiwanese. So you're having to deal with China Telecom. We try. I mean, I've, it's a lot of top secrets of security clearance in the Navy, right? So I'm very well aware of the level of espionage that goes on in the world.

And no joke, genuinely, that deal was espionage. Really? We were trying to, the customer wanted to circumvent the great firewall of China. They had production in Taiwan, and they wanted to communicate internet traffic from Taiwan to Southern California without the snooping eyes of the Communist Party of China, right? So clearly the Chinese Communist Party wants to intercept that traffic and doesn't want that to happen. And so this is probably a six-month deal somewhere along the line. And the company hired an IT manager named, let's just call him Robert from China, right? Chinese National.

And he came to Southern California. I never actually met him in person. But he was really not very involved in any of the planning. He was just there and kind of taking notes on stuff. And once we delivered a solution, a proposal for what we would do, he just went back to China and we never heard from him again. And it was just like, oh, this is just very mundane corporate espionage. Like, okay, cool.

That was one of those decision points where we need to get out of the internet. international business and just focus on. Yeah, I mean, I think, think about the levels of complexity and the levels of difficulty, it's hard enough to run a good, strong local business for Cloudhound, but you bring in another language, you bring in, you know, what, 12,000 miles? Tried to help a hospital, it was like the hospital system in Costa Rica. It was like four major hospitals and about 60 outpatient clinics in dental practices. And they wanted to upfit all of those buildings with improved internet, right?

It's like, this is a big opportunity. You know, it's like working with like Prisma or something, you know, quite that big, but for Costa Rica is big. Well, the, you get to the, okay, we now got to go to the Costa Rican board of like commerce page and there's like a kind of a state sanctioned bribe you have to pay, like in the thousands of dollars to be able to do business in Costa Rica. I'm just like, this isn't worth it. This is not worth the squeeze, especially if you're not necessarily going to win that deal,

might do all that for nothing. Echo, fooby. So it really was. you know, and I, again, analogies are how I kind of perceive the world. So Cloudhound, when we started, was just a nondescript block of wood sitting there, right? And we've over time whittled away parts of it. So international business, for example. Telephony, right? I had, my first real breakthrough was going to PTG and they're realizing that they were just calling the carriers like everybody else for their customer. So you guys can just call me instead. And so they started

funneling me business. Their customers needed a phone service. I would go find them a phone provider. I go down. Well, what happened was they were sending me all their little squeaky wheel phone customers that made all the noise. And so this person spends, this business spends $70 a month on internet service or phone service. I get 17% commission on that monthly.

So we're talking to $8 to $12 a month. I got to spend 20 to 30 hours a month on the phone with these people putting out fires. That math doesn't work out for me very well. It was like, it was like I was getting, you know, making license plates in prison type money. And so ditch telephony, ditch the international business, really focused on the upstate. You know, today we are, I use cyber and fiber is the best way to describe what we deliver.

So internet services on the fiber side, we can do everything from fiber, broadband, 4G, 5G, satellite, you know, Starlink is an option. So helping people find their right solutions for connectivity regardless of carrier, right? And then on the cyber side, anything from proactive training on the cybersecurity awareness to putting kind of big beefy systems in place to prevent intrusion. You don't want to get ransomware if you're a manufacturer. So helping avoid that ransomware outcome, putting a plan in place for if you do get ransomwareed, what are you going to do about it? Right? Most people don't have a plan until something happens and they're reacting, trying to make it up on April. and then incident response, right?

So something does happen. We can bring in the cavalry to kind of get you back to up and running and operating smoothly. Yeah, and don't you do some in-person stuff too where you actually train people? Yeah, so most of what we do is a scan source, you know,

leaning on that scan source vendor network to provide these services. The one exception to that is a couple years ago I had a customer asked me for in-person training on social engineering. They were having a big problem with their people clicking on fishing emails and they were doing regular online

security awareness training. I think that I did once a year to kind of check the box. But then the union, this is a steel manufacturer, the steelworkers union, it's like you can't fire people if they've only had online training. They have to have in-person training. They want to fire them for this cause.

And so they're like, hey, can you come in and do in-person training on social engineering and fishing emails? And I was like, sure. So I created a course called Social Engineering Self-Defense 101. So it's very entry-level. It's non-technical. It's for everybody at the company, from the CEO down to the janitor. anybody with access to internet or IT spaces or anything like that.

And it's really talking about, you know, divide cyber crime into two different buckets, right? There's the technical stuff where people are using software and hacking expertise to break through your system, right? That's what hacking, what you think of it when you think about hacking. Most of what's happening isn't that, though. Most of it is just, it's the tail's oldest time. It's someone tricking you, duping you, using psychological tactics. emotional levers to do something

that you wouldn't normally do. It's not the real, it's not the Russian hacker. It could be. And the thing is the Russian hacker, they have technical exploits and very, you know, very good ones.

But part of that is like the easy button, it's like water. Water's always going to find the path of least resistance and so are the hackers. And most of the time, the path of least resistance is not through your technology.

It's through your people. People are, are gullible. We're trickable. We have emotions that are manipulatable. And so, you know, I tell everybody, If you think you're invulnerable to hacking, that makes you more at risk

because you don't think that you're capable of being hacked. I guarantee you, give me an hour with anybody. And I'll tell you what your levers are, what your levers are, right? Do you have kids? Okay, you just got an email from your kids middle school. There's been a school shooting. Here's the PDF for the roster and the recall information and figure out which kids went to the hospital.

Here's the casualty report. Like, you're not thinking with your higher faculties anymore. Your lizard brain is taken over and you're worried about the safety of your children. you're not thinking about this could be a hacker, I shouldn't click on this, you don't trust the domain or anything like that. You're complete shambles. Same thing.

I mean, I got popped a couple years ago because one of my prospects, the CEO of a company that I've been calling on for a couple years, Jim, what's the company's name? Whatever. New South Construction Supply. So I got an email from his actual email.

So, you know, Jim, CEO. at New South Construction.com. Say, hey, Jack, here's an RFP. Request for a proposal for your perusal. Attachment. Great. Jim finally came around to give me a shot at some business.

It's great. I never won this business with Jim. Clicked on it. It was a blank PDF. And immediately, I was like, I didn't think about it. There's a couple of key red flags there. One, I wasn't expecting it.

There was no prior conversation with Jim about an RFP. Two, this is a small privately owned company that doesn't do RFPs, right? Right. I've bid on stuff. I've never done an RIP with them. They've never talked about an RFP. And three, Jim's a good old boy from South Carolina. He's never used the word of perusal in his life. Right. You know, it was not a common language based on what I knew about Jim. And so his email actually had been hacked. That was the case where, you know, he got hacked and the attacker was using his email to send out fishing emails, which is a little more of an enhanced attack than a random spray and prey. But nonetheless, my salesperson greed got the better of me, right? Yeah.

So everyone's got that little bit of life. It's not even brief. Sometimes I think it's just, you just want to check something off the list. So, you know, just trying to. One of the most interesting things, and this is close the loop on the fishing thing here, but for a long time, we would sell a hook security. So a fishing awareness training as a service. And they're putting fake fishing emails in your inbox every month,

and they can track what you do with that email on a granular level. And so we'd get the report every month from our clients individually. So if they've got 65 email users, Here's every user and what they did with this email. And the typical failure looked like. Most, you know, 90% of people get the email. Click it, delete it. Click it, report it, whatever.

They're not opening the attachment. They're not failing. But the people that are failing almost always look the same way. They would open it on their work laptop. Sit there for two minutes. Look at it. Move on to something else. And you come back to it a couple hours later.

Look at it for a couple minutes. And then move on something else. Do that three or four times. And then go home that night and on their iPhone, they'd open it up again. and then click on it. Like, it was never just a one and open click. They were thinking about it.

You're a fisherman, right? You know how fish bite, right? You don't just get a hit on the first cast usually. You got there, and you're just teasing them. And they're coming up and they're looking, and they're swimming away. And they're looking again, maybe take a little nibble and swim away, and they come back and bite later, right? So it's this space where people don't know what to do. Like, I'm not sure what to make of this lure.

I think it's fishy. It's clearly not food, but it could be. I'll just file this away for later, kind of procrastinated a little bit. If it says RFP or $100 free Amazon gift card, you're like, well, let's check it real quick. Yeah. What's the harm, right? Employee of the month. That sounds like me.

Yeah. It should be. It's my turn. Yeah. About damn time they recognize my greatness. I need a braise, too. So, well, to that business is six years old now, seven years old. Pushing eight, yeah.

Yeah. I think you've done great with it. You've really helped some great local customers, nothing in China or Costa Rica. but I think it's good. Like, I've watched you with the local customers because you can go meet them. You can go check them out on the weekend if you have to take care of them.

You know, it's a, it's not just to sell them and walk away. No. Have a long-term relationship. And that's really the, I think, one of the big values, and it only happens with time, is that, you know,

the average tenure of a direct salesperson when any tech company is 18 months, right? They're there, they make their number, either they're doing great and they get hired to go somewhere else, or they get promoted internally, or they aren't doing great and they get fired. Right. Right. So if you've got a salesperson you like from, say, AT&T or from your cyber security vendor of choice,

they're not going to be there in two years. Right. And so you kind of got to find a new relationship and is this even the vendor. And this guy works for AT&T. So he's not going to tell me anything besides buy AT&T, right? Even if he's a great guy. And so with CloudHound, you know, I'm not leaving. even Greenville anytime soon, right? We keep doing this. And so if we met eight years ago,

did some stuff to help you or even just met and didn't do anything, you know, there's that consistency over time, whereas I'm going to outlast all those direct salespeople. Sure. Ten times out of ten. And so it's also like I'm independent and I'm not driven by any agenda or quota or particular product or service that I got to sell this month. So I'm here to help you. Yeah. Period. Right. There's really nothing else to it. So I've got people that have kind of learned that value over time. And it's not something that happens overnight. You don't just gain trust with someone on a first meeting. So there's folks that, you know, got some good trust and rapport with now and doing some good

stuff. Okay. Well, let me ask you a couple of quick hitters, and then we can wrap her up for this, for this episode. Till next time. Till next time. So give me your favorite, favorite all-time book. I'm going to say Tribe by Sebastian Junger.

Oh, tribe, yeah. It's one of the most impactful books that I've read, and it's one of the ones that recommend, I don't really recommend books to people that often, but the tribe is one that it's a war correspondent named Sebastian Junger. He spent 18 months with it embedded, embedded with a Marine unit in Afghanistan, just got one of the worst, I mean, 18, I think 50% casualty rate over 18 months. These dudes got real messed up in Afghanistan, came back to the United States and just matriculated back into society as they got out. And so he kept up with them and just kind of collected all of his thoughts and reflections on that experience.

and it takes the idea that the veteran coming back from combat is broken and needs us to help them assimilated into society and flips it on its head. It says that society is broken. We're living these individualistic, materialistic lifestyles that are not really connected to any other humans that deeply. And that's really the opposite of how our species has lived most of its existence, right? Most of human history, we lived in these small, interdependent, flat tribes

where the existence of the tribe and the group and the survival of the group was it. There was no sense of self. There was an individual component to that. Interestingly, he points to the proliferation of mirrors as something that kind of destroyed that. We see ourselves in the mirror and we kind of become self-obsessed.

And before that, it was just there is only the tribe, right? And so the military, especially in a small combat unit, you know, seal team, Ranger, Green Beret, whatever, Marine platoon, like, that's it. That's the nature of business. You are meaningless, you're worthless without your team, right? your priority it's like, you know, team, team gear,

personal gear self, right? Your gear is more important than you. So you come out and it's like everybody you see is like running up the scoreboard just trying to make their bank account bigger and that's almost that is antithetical to team. I mean, there's a pejorative in the SEAL team. I got mine.

Like if you come back from a training mission or overseas operation and you go take a shower and get dinner while everyone else is still clean all the team gear, you're a turd. I got mine, Jack, you over there, getting yours. like, that's a negative thing in the civilian world.

And everybody else is like, that's what you do, right? And so Tribe really flips it and says that you're not the broken, you know, combat fatigued veteran that needs help from everybody. It's like you know something that most people don't. It's that there's this way of living where you're living for others and it feels so much better than just showing up every day and trying to make your own bank account go, right? Well, everyone should read that book. Yep.

If you want a second one, for whom the bell tolls. Ooh, it's an old one. Great book. I read that recently at the book club that I'm in. And it's, um, if you're, if, you know, for every, for every young man, every little boy that kind of dreamed of going to war, um, it's kind of a very romantic version of, you know, he walks into the jungle of South America with a backpack full of explosives and a machine gun. He goes to look for the, for the rebels to link up and sow some mayhem. It's just a, just a fun read. Good.

Okay. Well, thank you for, uh, for coming back today. You are in the lead. I think Marty is gunning for you because he likes to come by. Bring it on, Marty. Bring it on. Maybe we have a panel. Ooh.

A star panel. A pot off. A pot off. But you're doing great with the work with the veterans. It's wonderful. I'm sure that's a fulfilling thing, you know. It's not just the work or the paycheck for sure. It's fulfilling.

And then you've got your own business. And it's nice of your continuing to get back. to others. Can't help it. You must have been raised well. We've raised very well, I think. Contribute to his parents for sure. Congratulations.

Thank you. See you next time. Echo, be ready? See how? Okay.