
In this high-energy episode, Charles sits down with Kris Dehnert—founder of Dehnert Media Group and the driving force behind Dugout Mugs—to unpack how creativity, resilience, and systems thinking can turn simple ideas into multi-million-dollar...
Loading summary
A
Welcome to the proven podcast, where it doesn't matter what you think, only what you can prove. On this episode, Chris shares how he bought his business back from bankruptcy, turning into $55 million a year with only five employees. This one's unforgiving, unrelenting, and he's just trying to help. The show starts now. All right, everybody, welcome back to the show. Chris, I'm excited to have you on.
B
Thanks for having me, man.
A
So for the few people don't know who you are and the success you've had, let's give a little bit of debrief who you are, what you've done.
B
My name's Chris Dennert, and I sell cups. No, I'm just kidding. So I do sell cups. Right, but you do. That's. That's usually the story I tell people I don't want to talk to, because that ends a conversation pretty quick. But when you dig in, we did some really fun. We turned baseball bats barrels into mugs. Probably one of the coolest mugs on the planet. And we started with an idea. It started in a kitchen that went to a shed that went to a garage that went to $55 million in sales and national international distribution. Every stadium, every state, hundreds of athletes and celebrities and players, and we just make cool stuff, man. We make really cool, high quality, premium, made in North America giftable stuff, and baseball fans love it, but it's actually transcended that. It went into corporate gifting and wedding gifting, and the list just. It keeps getting more and more broad, which is amazing to be at the helm of that ship, man.
A
Yeah. There's two things you've done. One, you're selling a product I don't need, but I want, which is challenging as hell to do it. You've also done it on a shoestring group of people. Like, you don't have a big staff that's doing this, which has been really amazing. And it's funny because you sent me one of the mugs, which, again, thank you for one of the mugs. I haven't physically touched it yet because my team won't let me near it. They're running around with this, and they're not even freaking sports fans. But you engrave the logo, and they're running around with this thing, and now all of a sudden, it's become this mascot of my org that they're. They're taking it and they're going out to eat with it. I'm like, what the hell is happening with this mug? So everybody loves It. But this isn't your first business. You. You've created multiple businesses before. This wasn't an accident. What are some of the other successes you've had?
B
I think you learn more from the failures, and you know what I mean, Right? Like, I've had some. But, yeah, I did really well in the apparel space. And I think there was a direct correlation between that and this, because the dugout mug, to me was just another canvas. The world of print on demand. You know, there was that big, like, boom of print on demand T shirts. One of the companies at the, you know, at the center, that was a company called Teespring. And I was one of the first guys on Teespring, and I kind of brought it to the social media world because I had massive audiences. I had a bunch of fan pages probably, I don't know, 6 or 7 million fans, probably closer to 7. So it was just push button, make money and talk to the fan base. Hey, what do you guys want? Oh, we want Christian shirts. It's like, all right, there you go. And. And it really allowed. And we were doing that whole business with, like, three people, and we did over $20 million in sales of T shirts with, I think, at our highest point, we had six people, and three of them were designers because they're just cranking stuff out. One of them was an ads guy, and then it was. One was customer service, and one was me. Right. So that was a win if you go into, like, real life. I. I think I won at the gym business. I started off at Gold's Gym. I was selling membership. You know, I figured out a way to leverage social media. This new website called Facebook that came out and how to drive just massive amounts of people, connect with people before they knew that it was kind of like gonna be the new norm. That was back in 2003, you know, I guess 5, 6, 7, 8. Somewhere in there. So, yeah, I did. I did really well in the gym business. But, you know, you hit that ceiling pretty quick when you realize you're working for somebody else. And it's like, okay, so what am I good at? You know, And I talk a lot about reflection. I'll probably mention a few more times, but what am I good at? What am I bad? And one of the things I'm really, really good at is sales, promotion, marketing, networking, things like that. So it's like, okay, well, I can do that one to many. And that just. What a. What a domino effect that's had in my life. Learning how to leverage technology. I'm not technical, but I know how to leverage technology, right? And that was really cool. And just we have one thing after another. And, you know, here I am selling again. I sell mugs, right? And having a lot of fun doing it.
A
So, you know, we talked about this, right? In the beginning. You said, you know, you learn from more from your failures than you will for your success. And, and we talk about this all the time. You will never succeed your way to success. You will fail your way to success. And most people don't get that. And I'm like, well, look at your kid. When your kid first started walking, it fell and it fell again, and it fell and it fell and it fell. And you didn't sit there after the 50th time, go, screw it. I'm gonna put it in a wheelchair. You just kept pushing. But we take that out of our kids in our world in school. Let's talk about some of those failures. So what are some of the failures that you learned the most, and what were the lessons you learned from them?
B
Well, I think to your point, what people do is they take away the pain. And pain and pleasure, those are the two things that really drive people. And when you fall, shit hurts. And you fall again and again, you're like, that is it. I am tired of hurting. I'm just gonna walk, right? And I, I think that's. That's what the pain is. The first time I screwed up, I didn't dial in my contracts and somebody got me for like, quarter million bucks. That shit hurt. Yeah, I didn't have a quarter million bucks to lose at the time. And, you know, you learn, okay, now I'm not going to do that again. Dialing in my contracts on the front side. With partnerships and deals and collaborations and joint ventures, the restaurant industry, we made a bunch of money selling T shirts and me and a few friends. And thank God in this deal, I was the least. I was the smallest equity holder. But we lost seven figures doing a restaurant. You know the, the old saying, the best way to make a million bucks in, in restaurants is with two, or start with two and open a restaurant. That's the best way to make a million bucks. But, yeah, like, it, it. That's a really funky industry. And I had no business being in it. I just had money. So we were just throwing at the wall and see what sticks. And it's like, I don't know about that. So again, from an investment standpoint, I. I lost a lot. Learned a lot. And I believe you're winning or learning like Those are your options. And whenever we're losing, we're learning, okay, don't do that again or do that. Do it again, but different, Right? So the restaurant industry got me. The cannabis industry got me. The crypto industry got me.
A
Yeah.
B
Now I still hold a very aggressive portfolio with crypto, but I learned what not to do. And again. So again, winning or learning, you learn to stop. The pain made you stop or the pain made you change. And then when you start doing things right, like dugout, you know, there's been pain in this company, you know, but the pleasure of it far outweighed it. So this is one of those things that the pleasure is what's driving me. You know, a year and a half ago, when my partner and I decided he was ready to be done, ready to retire. Awesome dude. He's like, you know what? I'm done. Had, just had a kid, just got married, just built a house, all the things, and it wasn't part of his path anymore. And it's like, okay, we could sell it and walk away, but I'm like, I'm having a lot of fun and it's kind of broken and I really kind of want to fix it and really drive it fast again. And. And that was my driver there. So I think you learn as much from pain. You, you learn more about yourself in pain, and then you really learn like, what's your. What you want with like the pleasure push. You know what I mean? I think is a. Okay way to say that.
A
Yeah, I think I agree 1000%. I remember when I, my first company I ever had was an IT company. We were closing like 90 something percent of our sales and I exploded. I was like, what are you doing? I go, if we're closing that high of a level, then we're not risking enough. We don't have enough pain. So I made everything go up and then we radically increased the company. When you talk about having partners, it's challenging because, you know, I want to get to the idea that you're building these empires, these new nine figure companies with a shoestring, there's just nobody there. How are you doing this with five people? We'll get to that. Because that's, that's the important part that I think that's really sexy. But when you talk about partnerships, what are the pain lessons that you've learned there? Because again, we've all done it. We've all gotten in bed with people who we just shouldn't have gotten to bed with or we've turned friendships into Partnerships. And it ruined the friendship. What are some of the struggles you've run into with that?
B
Well, the struggles I've run into again, I'd rephrase it. What are the lessons I've learned? Right. I think it's a better way of saying it. And I think reflection again on the front side. You know, partnerships and deals are one at the beginning. You know, asking better questions at the beginning, understanding what someone's blueprint looks like at the beginning. Look at a marriage. I want three kids. I want none. Hey, that shit ain't gonna work. Right. Somebody's gonna be pissed sooner than later. You know, in business, I wanna do this forever. Oh, I'm only on a four year plan. Right. I'm 22 and full of piss and vinegar. It's like, bitch, I'm 45 and I'm ready to start slowing down. Like, you have to look at these BluePR. And I don't think enough people do that. They get blinded by cash. And cash is only a singular currency. There's so many other currencies out there, in my opinion. Time, experience, fulfillment, family. There's other currencies that are involved. And if you're only basing your decision making off cash and money, I mean, in fairness, that's one of the most common currencies out. We just print that shit. It's not even attached to anything. Right. Here's more. Right. And to ever make that your North Star is foolish in my opinion. So I think there's not enough reflection on the front side with partnerships. And I got blinded by that. Like, I got in business with a family member and it went super sideways. And at the end I just like, here, take my half of the shit. I'm out. I can't do this no more with, I mean, other partnerships. Yeah. I mean, trust your gut. I don't think people do that enough. How cliche is that? Right? But, but really, some friends and I, we always laugh like, I only want to do business with people I'd go on vacation with. It's like, okay, because, you know, you got to realize if you're spending this much time with folks, you know, I, I say it all the time. A good day with bad people can still suck. And a bad day with good people can still be really awesome. Right. What you're shooting for is a good day with good people and then like, you know, pour the champagne. But the, the people in the deal are more important than the deal in most cases. At least in my world.
A
Right. 100.
B
I don't just do things transactionally. Like, this is my life, you know, I don't honestly believe in work. Life balance, right?
A
It doesn't exist.
B
Sometimes you're working, sometimes you're golfing, sometimes you're parenting, sometimes you're crying. Like it's life, you know? So I try to do life with people I like and. And with people I want to be around, right?
A
So it's funny because every time we've talked within probably four or five sentences, you talk about your kids, it just comes out. You talk about. You're like, listen, my family run first. Like the rest of this. I'm sorry. This is more important to me than anything else. Every time we've spoken. When you're starting to build the systems, and there's a difference between systems and processes. Processes involve people, systems don't. That's just. People need to understand that really quickly. You've built empires, a ton of cash, you know, amazing businesses with very few people. Because there's so many times where even I've gone into businesses and they're like, oh, I've got 30 staff. I was like, cool. How much are you making? Like a million a year. It's like, what the are you doing? What do you. What do you. What do you. This is broken. This is an ineffective model. When you go into that and you're starting to scale, how have you done it? What are the things that you do every single time? So, okay, I need this. I can outsource that because they're different conversations.
B
I think understanding what people's core competency, you know, what is their superpower kind of thing. Don't ask a fish to climb a tree. You know, the whole adage, right? I always laugh and say, there's a reason I'm not jumping hurdles. I'm old and little fat and I got bad knees. I'm not. I'm not going to do very well, right? So I think what you do is you identify the pillars in the. In the company that need attention and need to be managed by a person. And then that person has a particular skill set. So you, like, hire the person, teach them the job, right? You hire. You know, I'll give George, our guy at the front. Like, this guy is meticulous, and I hope he watches this because he's epic, right? He's meticulous, OCD kind of guy. Dude doesn't miss anything. So he's in charge of logistics, right? We got Eric, who was. You ran commercial kitchens. You want to talk about processes and boom, boom, boom, boom, boom. Okay, that's your dude, right again. Like, you just find people and you. And you. You lean into them like people. Oh, God, I've heard it so many times, and I hate it. You know, partners of mine said it, and I hated it. It's like, oh, if you don't know something, you should go learn it. It's like, fuck that. If I don't know something, best case scenario, I'm going to be mediocre. If I go spend time, energy, effort, and resources to figure this shit out, best bet is to get somebody else. I don't mow my own yard. My pool guy was here earlier. He's cleaning the pool. He's gonna do it better than me. I'm up here chatting with you, though. Your lawn guys are about to be here in a minute. It's just like, we do it in so many other areas of our life. My point, back to your question is, I find people, I find out what they do best, and then I try to inspire them to go for the vision that we have collectively put together. And if people feel ownership in vision that's been created, buddy, they're going to be behind it and behind you all the way. And. And I like to step away. You probably heard me say it in the past, but, like, give direction, not directions. That was a funny way of us explaining it internally. That really kind of stuck with me. And it was, you're really good at this, Jared, and you're really good at this, George and Nate and Brian and Eric and Tony and Tina and Milagros. Like, y' all are good at what you do. Can we all agree that this is where we're driving all. All in our own little car, our own little lane, and we're like, yeah. I'm like, all right, I'm out. They just drive there because they have ownership in what we're doing. You know, they. They believe what we believe. They see what we see. So I think asking better questions, empowering people to think freely and operate freely, the micromanagement world blows. I don't think it's a good model. People hate it, and they're hating it more. And the group of kids that are coming up and group of workers that come up, they hate it even more. But. But you got to have. That's where the systems. That's where the technology and some of this other stuff comes into play. You put up these roadblocks so they're not jumping you off a cliff. You know, that's kind of. It's kind of a hybrid.
A
It's interesting. We always talk about this. I don't care about the how. The house, irrelevant to me. You're going to figure that out. If I've hired well enough, you're going to figure it out. I'm going to let you go through this environment. I'm going to put basic bumpers in you. It's like, hey, if you get too far off track here or there. But I would rather you ask for forg and permission going after like this is where we're going. I really don't care how we get there. I don't care for on a simple, very watered down version of this. I don't care if you're on a Mac or you're on a PC. I don't care. Just go. I don't care if you work at night or if you work in the day. Just, just go. Just let him go.
B
Writing a damn letter. Get the message out 100%.
A
And like we had this literally in my org recently. Someone was putting together an email and they reached out and say, hey, I don't know if this email's right. I'm like, does it have all the key things? They're like, yes. I'm like, I don't care what the email sounds like. Go. They're like, well, can I use ChatGPT? I'm like, I have hired the wrong person. So we're already in the process of replacing that person. Because I'm like, listen, if you don't, if you're that person who needs to be guided on that level, you can't make systemized, streamlined teams. So one of the fears that people have when they build teams is like, okay, I need to have coverage. You know, I've hired Susie. Suzie is in charge of sales. What happens if Susie wins the lottery, gets eaten by a purple dragon? Whatever else it is, how do you offset that? Because Susie one day may win the lottery or get hit by a bus or whatever it is, how do you offset that fear?
B
I don't have a solid answer for that. I think what it really comes down to is having documented processes and systems. I mean with AI and we touched on it, but with AI, buddy, especially with what I do. And I think it's unique, right? I think people's journey is unique. Their businesses are unique. They have a lot of the same components. I'm not foolish, I know that. But. But I think how those components work and interact and also the person running and managing it has a lot to do with it. Like I'm a big hands off guy. So yeah, we're leaning into A.I. you know, we just replace customer service with A.I. it's not that the girl was bad, she wasn't great, but she wasn't bad. But it's like, so AI is going to work 24 7. It's infinitely scalable. Midnight, 2, 3, 4, 5 in the morning, all the way through Christmas when we normally have to double or triple our team. I'm like, yeah, okay, we're going to do that. You know, it just makes sense. Design. I make these designs for the mugs. Well, AI is doing a really good job ripping these things out. Okay, right. So then that, and then with the API and integration with, with E Com in particular and with my. That's why I stay so lean. You know, we're really lean. The only thing we're physically doing is engraving, cleaning, packing the mugs. That's it. We went from a 12,500 square foot facility. We're in the process. In the next 90 days we're gonna be down to 8,000 square. We cut a third of our, of our space. By becoming more efficient, we identified what do we need, what do we not need? Again, ask better questions. We don't need this 4, 500 square feet over here full of additional overhead and seven extra people. We could just put that on this other side. You know that again, it's just, it's understanding what you're doing. And then it's like, you know, the back in the day, the index cards on the table and moving around. Like how does it work? It sounds basic, but like that works. I mean you got to understand the moving pieces of the company. And it's like, well, the 8020 rule. I mean pick your, you know, pick your cliche. Well, 80% of our stuff's coming from over here. Why the hell we got 80% of our people working on the 20? Well, what. How can we be more efficient? So there's a couple opportunities I'm looking to roll up right now because they'll fit perfectly into the systems that we have. They'll fit perfectly into this new streamlined system at the 8,000 square foot place. And, and the in strengths here and the strengths here, like they click like it just if your plates more clear. By not getting in the weeds, I feel like you can put better things together. And, and, and that's where I try to focus. So I have to be hands off.
A
So when you talk about asking better questions because you know there's. Everyone talks in platitudes all the time. What are the what are the tactical. These are the questions that have always had the best ROI for me. Like, these are the questions I ask every single time on any single project when we get stuck or if we're going to expand or anything else. What are the ones that you're like, these are the questions I ask.
B
Where are we, you know, what's going right, what's going wrong? What do we need to do different? I mean, I've, I've said that hundreds of times. If we understand what we're doing wrong, like right now, I'll tell you what we're doing wrong. We're not as forward facing on social media as we once were. You know, we got two and a half million people on TikTok. I got a hundred thousand on, you know, 120,000 on Facebook. I got another 100,000 on Instagram. Like, we got a lot of people. We're access to a lot of people. Our email list is like 800,000. Our SMS is a couple hundred thousand. Like, this is a stack of people, right? Not doing a good enough job communicating with them as we once did. So. And I know, like, this is my style. I love it, bro. I love sticky notes. They stay right next to me because I know. And I can only put like three things at a time on them. So I'm like, check, check, check. Throw that over there. So, like, for me, I, I know one of the things we're doing the worst right now was forward facing. So I started hopping on more podcasts. I was like, all right, well, I can certainly tell my story a little bit more and talk about the company a little bit more. So I committed to that. I'm doing that. And again, it's just, that's what I ask, you know, what are we doing wrong? Our conversion rate sucks. Okay? You, you're only focusing on conversion rate right now. And then what are we doing right? And we just kind of put that on ice. Right now we're manufacturing mugs. We're doing a really good job. Our fulfillment's on point. We don't need to, you know, where could we, where could we shave? And we're like, well, with AI in particular, it's like, well, we can shave design and we could shave customer service. That saves us like $5,000 a month. That's $60,000. Your bottom line. That's not massive numbers, but those that matter, right?
A
I think it's the conversation people talk about all the time, like how do, how to become wealthy. You're not hitting grand slams. It's These signals, singles. Get on base, you know, for, you know, the idea of dugout. Just get on base as quickly and as intensely as you can.
B
So figure it out later. Like, yeah, ready, fire, aim. Like, make a move, measure the move and be ready to adjust. I mean, these people that just get on the bus and ride it until the damn wheels fall off, I mean, you can do that. I don't suggest it. Randall and I made a great move whenever Covid came around. It's like, we could have kept pushing what always worked, but we decided not to do that. We decided to change our marketing from people at ball games and tailgating to backyard barbecues and living rooms, right? Because we're marketing to people where we were. If we would have stuck to this other thing, you know, that's the. You know, that's the blockbusters, that's the circuit cities, that's the Kmarts. Like, if you try to do the same thing, it's, you know, the wheel to. The wheels fall off. You're asking. The wheels are going to fall off. So I think being fluid is really, really, really important.
A
When. So when you have a small team, they see your growth, right? They're in there, they're with you, they bleed with you. And that's how it's important to work with people you actually like. But also, one of the catches here is they're going to see your profits as well. How do you work with that compensation thing where, like, hey, guys, you did a great job. We made an extra $10 million this year. How do you deal with compensation on that level? Do you incentivize them? How integrated are they in that success?
B
I've had very open conversations with those who can wrap their head around the content of the conversation. Probably a third of my team will meet. So we do Monday meetings. We're always. We Link up Monday, 10am what's going right? What's going wrong? What do we need to change? What do we all need to know about who's leaving, who's coming, who's going? What's. You know, is there a fire? We need to collectively put out, right? So everybody's kind of just got this. This team atmosphere. It's easier to manage when it's smaller. As far as the profits, I explained in a way that they understand what I'm saying. Vanity metrics are not. Not, you know, worth even looking at. Oh, we did $10 million. It's like, yeah, but if we only made a million and we had 600,000 in overhead, that means there's only four. Right. So it's. It. I, I don't mind guiding people and talking to them and being transparent. I think transparency, I mean, people aren't stupid either. You know, I think more now than ever, access to information is everywhere. So you don't want to treat. And I don't want stupid people around me anyway. But you don't want to treat people, you know, assume they're ignorant. So I'm actually more about being transparent with them. And, and they're well paid. Actually. When I first bought my, you know, when I stepped in, I took over the company we were in. Not a great place. Like seven figures in debt. Seven figures over here for the buyout and fucking a half a million. It was ugly. And I was like, okay, well, I know I can't do it without these people, so let's talk to the people. Half the team got a raise on the first day.
A
Nice.
B
And it was about me committing to that. And they knew. It's like, hey, not a good spot, but you're getting a raise because I need you for this. Don't drop the ball. Here's the ball. Go. Right. And I. And some of the response to that has just been tremendous when you have faith in the people like that. So I've been really transparent about.
A
Now.
B
There are times where they see thousands and thousands and thousands of mugs going on. They just like, oh, this guy's just getting fat and happy over here. And we do, you know, we do bonuses and we do incentive stuff. I've, I've looked into some employee stock options kind of thing and, you know, ownership. Right. Like, I don't, I don't need it. I'm actually really basic, you know, I'm flops and T shirts and hats pretty much every day. So as long as my bills are paid, my kids are happy. Happy. And I'm living the lifestyle I want. Like, I don't mind sharing the wealth. These are the people making it happen. And that's just the mentality I have.
A
Right.
B
You mentioned other currencies, man.
A
Absolutely. And I think, I don't think people understand that. I really don't think that if you're, if you think money is going to make you happy, it's not. It's. It's never going to happen. It makes life easier. It's a great tool. I love being able to use it and, you know, be in first class, be in business class. It's a great tool, but it's not going to make you happy. It's just, it isn't A lot of people talk about AI and the integration with it and you've optimized it. What are some of the AI tools that you're using now to make your life easier?
B
Basic. I mean I use Claude, I like that one. My, my CEO Jared, he's, he uses Chat GPT and I think he got like the upgraded one. And then obviously Grok is, is doing some interesting stuff. Anything Elon's touching is interesting. So that's pretty much it. Now we use our, our CRM, we use Gorgeous and it has a, an AI component in there which is been really impressive. So the teams got on and, and integrated that with our customer service. And I mean it's, I'm getting emails back from me, you know, it's like, hey, check this out, don't forget to click here.
A
But.
B
And it just walks you right through it and responding and I'm reading some of the responses. It's like, dude, that's like, like 95% on point. And then the more you teach it, the better it's getting. So I'm like, okay, we're doing, that's what, we're doing it right now, Q3, because when Q4 hits, this thing's going to be on point and infinitely scalable. So that, that's probably the one we've used the most I've seen. There's some other guys, Mike Weiss, shout out to Mike and I know Glenn Dietzel's doing some stuff too where Voice AI, some of the stuff that's going on there is because I'm in a Mastermind board of advice. So I meet with these guys every quarter and listening to some of the stuff they're talking about. Dude, it's wild. Like the Voice AI, the outbound infinite calling Voice AI setting up stuff and lead gen and just dropping them right onto a calendar. There's some pretty cool stuff happening.
A
Gotcha. So the one that you're using where you, you know, replace customer service, that's gorgeous.
B
Yeah. So we were using gorgias in the past and we were manually doing it. It's kind of just like a hub where social and email and all blah, blah, blah and, and they launched their AI piece a while back and it took us forever to get to it and it's like, let's take a look at that. And Jared, he's, you know, he's my right hand man and dugout, he's like, dude, I'll figure it out. I said, okay, dude, figure it out. Let me know what you come up with. He Jumped in. Boom, boom, boom. And. And yeah, bro, it's rocking. It's rocking.
A
So normally when we go through these and we break things down step by step by step, if someone wanted to come in and do this and say, what has been proven to work more than anything else outside of hiring? Right. You know, keeping it lean, asking the very specific questions, what is working? What is not working? You know, what do we need to fix right now? What are some of the other things that you've run into that are like, hey, this. If I took everything away right now and I had to start over, what are the proven things that you've done that have created radical success?
B
I think success is a unique experience. I think it's unique to each person. So what I would do is I would go back to a place of peace and balance and try to understand what I really want, right? So for me, you know, when my daughter was born 10 years ago, you know, I got super sick, almost died. Like, that really sucked. Best thing that ever happened to me, honestly. But I came out the other side of that, and I was like, okay, what's important to me? And it's like, well, I don't really want to be away from my house anymore. You know, I've been working from home since before it was cool, right? And, you know, so it's about really understanding where you're trying to end up and. And then understanding who around. Like, I only take advice from people where. Who are where I wish to be. So it's like understanding who your core support group and community is. That's why I'm in the mastermind, right? And so that's not, like, a tactical answer, but I think how to do stuff is not nearly as difficult as people make it out, especially when we're in the age of technology and learning, right? I think it's understanding what success looks like, feels like, sounds like. And then, you know, then everything that lands on your plate, it's like, it is or isn't black and white. It is or isn't in the direction of where you want to go. Like, this is where I want to go. This is what I want to be. I want to make $10,000 a month with that, with working 10 hours a week. And I want to be able to go to every single dance and. And softball game and baseball game with little Billy, and I want to take my wife on a date night every week, and I want to have some investments so that when my kids, you know, like that, bro, the understanding what that looks like, I Think is really what it's about, not the, not the tactical measures to do it. I also think, now if you do need that advice, I would say I'm a huge fan of create a system you're not a component of. Because my goal is to be irrelevant in the system. I want to be the beneficiary, of course, but I want, if I'm always in the weeds, I can't, you know, be over here where I want to be. So I would tell people, create a system you're not a component of. I would tell them to really do due diligence on anybody else who's going to be a decision maker in the venture. I would say identify, like, make sure you're. It's fun. And I know that sounds weird, right? Because to me fun's a major currency. But, but there has to be a release at some point in what you're doing because it's not always easy, it's not always going to work. And I think having fun along the way will allow you a lot more resilience and durability so you can last a little longer because you're constantly getting a release along the way. I think those things are what I tell people.
A
Yeah, I think it's rare to have someone show up with the honesty and the vulnerability you have, which is start with the filter, which is I don't want to be involved. I want to be at my kids baseball games, balleray ballot. That's, that's my filter. So if I got offered a job making a bazillion dollars, but I'm never going to be home, it doesn't work for me. So put your filters and where do you want to go first? I talk about this all the time. If you're going to shoot an arrow, you don't fire the arrow. And then think, where do I want it to go? You identify your target first and then you filter out from there. So most people don't do that. The second step is having the confidence enough in yourself to know I'm not important. I'm irrelevant to the process. So I need to fire me from the beginning. If it relies on me, then I've just made a prison, not a business. And most people don't have that conversation. Most people are coming and going, hey, I'm special. This is what I know how to do. I'm amazing. I, you know, my grandmother made great cookies, therefore hence I have to make great cookies. My hallucination is, you did not grow up wanting to sell fucking mugs that Just wasn't your ball game. You're like, hey, I'm gonna make mugs.
B
It wasn't a line on career day, dude, but I'm kind of glad where I landed. Now if I look at what my core competency is, Sales, networking, promotion, like, put me on tv, I'm in. Right?
A
Right.
B
I can do it. So I, I understand the prison sentiment you made a minute ago. A minute ago you didn't make a business. Created a, like a prison cell. And I'm currently in the process of this now. All this shit's a daily practice. Okay.
A
Yeah, absolutely.
B
Oh, I got it. No, it's a daily practice. You know, just like taking a shower, bro, you're dirty. Take a shower. This is constant repetition. It's the mother of all learning. Right? So for me, I'm currently trying to build out a sales team because that is what I do best. I've been able to stay in my power, my power zone in this business, my superpower in this business almost the entire eight years. And that's why we've seen some of the success that we've had. The majority of it, I would say, is because of my ability to just push and drive and connect and make happen. Right. But I also realized that it is starting to be heavily reliant on me to bring those sales in on the front side. So now we're putting the people in place. Right? What, what really sucks is if you get stuck in a corner that you just don't know how to clean, you know, or, or you don't know how to handle. Like, that's, that is brutal.
A
But you were talking earlier.
B
I got stuck in my, my power zone. But even that, even that, I'm in the process of trying to remove myself.
A
You talk about post it notes that you have. I literally have a post it note. It's the only one that I keep on my computer that says, fire yourself. Like it sits above it, like, fire yourself. If I'm mission critical to the process, I have failed. I have created a prison. I have not created a business. It's a different conversation. The stuff that makes me the most money, I'm not involved in. So I'm constantly working every day. And I love that you said, it's like going to the gym. You gotta keep doing it over and over and over. And it's an everyday practice to sit there and fire yourself out because yesterday's.
B
Success isn't going to ask yourself again. You're asking better questions. If I was an employee, would I fire me a Lot of people don't ask themselves that. And you're like, well, I'm kind of show up late every day, leave early every day. I have a beer at noon. You know, I don't know if I would let me hang around.
A
I'm not supposed to do that. Wait, I'm not that. That's not normal.
B
Well, hey, if you would fire you, maybe you're the prop, right?
A
See, my goal is to make it. Yeah, that's my biggest thing. My goal is that I am not mission critical, that I don't matter, and that to speed that process up as fast as possible. Now, you mentioned earlier you're running through some struggles, which is, hey, you know, we. We've dropped the ball and we haven't been social enough. And I'm doing the podcast and you're doing all that. When you're asking better questions there. What are some of the ways that you're like, hey, why did you decide podcasts versus about a million other different ideas that as many as you said that I was like, well, shit, I've got this laundry list that I would go do. Why did you decide this was the best path and allocation of time?
B
I had a lot of people, it was easy. I had a lot of people asking. They're like, dude, you got to share your story with me. Can you hop on? Can you hop on? I'm like, nah, I don't have time for that. I don't have time for that. I don't. But it's like, you know what I mean? Really? I did a podcast one time and I shared the story when I got sick and a guy reached out to me. He was in another country. He reached out to me and he said, hey, dude, I listened to that podcast the other day and it saved my life. Because a week later, this and this and this happened. I want to share his business, but this, this, this happened. And I remembered what you said. I immediately did. Went to the hospital and they said, about to wait another hour, I'd be dead. I was like, that's crazy. So you never know what kind of ripples you're putting out there and impact of those. They could turn into a tsunami, right? And of good somewhere else. And I. I think I owe that to people. I'm speaking tomorrow morning at a. At a high school for emerging leaders. There's a charity called R2Cares that I work with here locally, and it's my alma mater. I graduated 25 years ago from there, and I'm gonna go speak the inaugural speaker at this like a auditorium full of people talk about emerging leadership and leadership and, and all this. So it's like, I feel like that's, that's part of success for me. I'm not, I'm. Dude, I'm not that guy that's like all stoked about leaving a legacy. Like, that's fine as long as the people that matter care about me and remember.
A
That's right.
B
I did my job. But, but I feel like putting the good out there is part of your responsibility as, as a, an influential person. And I like that. And it was, and it was, it was a lay down. I'm fine on camera. I got plenty of. To talk about what I think is cool, fun and sexy and you know, people buy it. Like at this point, like the corporate gifting side of what we're doing is really interesting. So I, I mentioned here, like, we're making mugs for Coors and Miller and Coke and Pepsi and Yamabon, Hard Rock and Celsius and T Mobile, Capital One, like crazy. So a lot of business people have been buying our mugs. You know, 36 here, 75 there, 100 here. And they're gifting them out just like you said your team, right. Like they're gifting them out because these things kill and, and you know, the podcast is a great way to do that. Podcast hosts give them out to guests and it's just a lot of, a lot of cool stuff. And it only took an hour here, an hour there. I can do it on the fly. I could do it if I'm in, you know, traveling. It's not the only thing we're doing right. Like, I'm also doing a lot of pr. Like a few days ago we were on Good Morning America, launched our Savannah Bananas line with our MLB line. And we did okay. You know, we did pretty good. So mainstream media, pr, I'm doing this kind of fit right into that. I've been. There's a couple mag magazines that just did a write up. I was in Valiant, CEO Business Wealth, Fast 50 Business Journals, Forbes, entrepreneur.com. like, there's a lot of features. And again, it's just, I'm building a personal brand, you know, this isn't my first rodeo with Dugout. I've had nine other companies before this. So my personal brand is going to outlive this company. So I'm just constantly doing things and taking little steps in the right direction. You can have two broken legs, dude, but if you're moving, like, you're still moving, you're still Moving feet are just moving. And. And. And until some of these other things shake out, like the paid ads and the traffic and the algorithms that are adjustments that are happening and all this kind of stuff, I think just keep moving, you know, Keep it moving.
A
So why do you think in the. In the print, on demand, which was a very saturated market, what. What made you stand out? How did you succeed and win where others didn't?
B
Speed to market principle, and the fact I took that shit serious. So speed to market was I didn't sit around and wait. I saw an opportunity, and I jumped in. And I jumped in with both feet. You know, I didn't just trickle my toe in the water. It's like, all right, dude, we're going to do this. We're going to do this. We're going to fail. Fastball, forward. We lose, bro. We're going to lose now, and we're going to be on to the next thing. And this. That's why I actually got out of pod. So we jumped in, and I treated it like a business. We had business meetings every week. We had the designers. Here's five things I'm thinking about. What do we want to try? Hey, this just happened. So our company was called Chasing trends, and that's what we did. It's like this happened on this reality show. Everybody's losing their mind over it. On social. I need five concepts around that, Right? And then we ran it like a business, not like a hobby or you're moonlighting doing something. We took a shit serious, and we won. And also, we were in the market fast. And then we were. We were fluid enough to identify when things started, like, changing. So whenever the. You know, I ended up being the piece. So I helped Teespring kind of write their affiliate program because I identify. It's like, okay, well, this market's getting saturated, so everybody's going to want. They wrote an article about me, like, you know, guy makes a million bucks on Teespring or something. And so I started getting a lot of people reaching out. I was like, all right. So I put an affiliate program in place where I made 50 cents a shirt in perpetuity. Very special word, that, perpetuity. And on anybody I bring to the platform. So then it's like, hey, I'm going to launch a digital mastermind. So then they paid me for me to show them what to do. Then I referred them to here, and then I'm making residuals over here. We sold, like, 3 million T shirts through that program. I made a million and a half dollars 50 cents at a time on shit I never sold, touched nothing. And so, again, like, you have to be fluid and not be scared of changing. And sometimes that can really land in your favor. People are scared to change, but the only thing that is consistent is change. And, you know, and. And I think that is why we won. We went in hard, we knew when to move, we treated it like a business. And. And anything. You should just treat it like it'll be as serious as you are. Right. I think.
A
And if you don't take it serious, it's not going to work. That's just the reality. You either go all in or you don't. So what is next for you? You know, I know Dugout's growing and you're expanding it, and the mugs are just. You've infected my entire team, you bastard. I have to buy mugs for them. Yes. I have to buy more mugs from you. So. But what is next for y' all and what y' all are doing?
B
Synergy. Identifying synergy. There's, you know, a digital company that's out there that's very much in line with what we're doing. There is some wood working stuff that fits very well with what we're doing. There's another company that's out there that is. Their systems are not as clean as mine. So there's. I could roll up a company that's making X dollars and literally double the revenue. Double the bottom line just by bringing it in house and, you know, and plugging it into my efficient systems. So trying to find ways to grow by acquisition versus just grow by additional sales. Because when you force that, you can really lose your ass because you're blowing ad dollars just burnt. Might as well light it on fire, right? So I'm trying to grow by acquisition and continue to groom the people within my company to replace me so that I'm more of a consultative, like, role. I think that's what the next two to three years looks like. And now that the company's all mine, honestly, I'm not really in a hurry. The. The events I get to go to and the things I get to do and the people I get to hang out with. I own a golf company as well. Big golf. So I have a cigar line, you know, So I have beer and baseball and golf and cigars and breweries and fun stuff. Yeah. It's like, what else am I going to do?
A
Yeah, it's the stuff. As a teenager, you'd be like, this is gonna be great. So when you Talk about your systems are more efficient. Walk me through that. What do you mean by your systems are better than others? And then how did you develop those? Because I'm a systems guy, if you want to talk. There's very few things in the world that get me more excited than systems.
B
You know, it's where. Where I. I just walk in there. And so my daughter, my 10 year old goes up there with me, you know, in busier times. I'm like, hey, baby, we're going to work today. She's like, all right, dugout mug, shirt on, hat on, let's go. And she's just taping boxes, slapping stickers, you know, doing everything. Just loves working with dad, you know, which is one of my favorite things too. But I walk around and it's like, that's a step I didn't need to take. Why. Why are we doing that? Oh, that's how we've done it. It's like, noted. I. I go in the. Just yesterday I went in there and there's a whole table, like 200 mugs in the back. It's all teams and custom and, oh, shit's everywhere. And one big table. It's like a brick of mugs on top of this massive 8, 10 foot table. I'm like, what's this? And they're like, oh, those are the ones that either had a little dent in it, or the thing was a little crooked or this and that. So, like, y' all just set it here and walked away like. Yeah. I was like, all right. Okay, now we just blow these out, turn mugs back into money. One of my favorites recently was we had. We had. The mugs are on a rotary device like this, dude. And this laser's hot. Sometimes I just freak out and zap a hole right through this thing. So they're just throwing this whole thing away. So I walked. I was up there. Let me see. I know I got one here sitting here. I know I do. Let me see if I can find it. I had. I just had a. I annihilated some stuff this morning. Oh, here. It's literally right in front of my face. So you're gonna love this. So this thing, we would just throw this away. Instead, I take. I cut off the bottom starting right here, because all this is solid wood. So then we started making batter slices turned into ornament. No ornaments.
A
And ornaments. There you go.
B
Now you want a Phillies keychain or Yankees keychain? So this was trash. And we're just throwing them out, dude. Because what are you gonna do with it? Right? So now I can turn it into six keychains that sell for 20 bucks a piece or 15 bucks a piece. That's $90. I turned trash into $90. Right, right. That was an efficiency. I, I walked up there and I just, you know, again, I just put my. I, I put myself out of the situation and I just. Look, we had two big ass shipping containers. I'm like, why do we got these? And they're like, oh, a few years ago, I was like, stop right there.
A
Yeah, right.
B
And I said, what's in them? And they said, well, we got golf balls in this one and it's about half full. And we got some other random in this one and it's half full. I was like, so what you're saying is we can make one of them all the way full and one of them can leave? And they're like, yeah. I was like, okay, well guess what we're doing today? And Everybody shifted over one to this. Filled one up, sold it for like 1100 bucks. It's only 1100 bucks, but dude, I'll take 11. You want to give it out? And I think to me it's just a common sense. And I know it's not common, right? I know how I think is unique. I walk in there and I'm like, why do we have these boxes only stacked four high? Well, because the roof's only eight feet, nine feet. I'm like, okay, so if we had a 12 foot roof, we wouldn't need as much floor space and we could just stack up and all these dudes just stack here until we pull them down and engrave. They're like, yeah. I said, okay, so the new facility, guess what? 15 foot ceilings.
A
There you go. And it's these little details that change.
B
How many times, count how many times you come down these stairs a day. 30 or 40. Okay, so what you're saying is if we took down upstairs and we set it down next to downstairs, I'm gonna save time. We could just go in a circle. And they're like, yeah. I was like, well, guess who this new place is. 4,000, 4,000. Side by side, holes in the middle, holes in the sides. It's like hard, but I think constantly looking for holes or improvements and, and never take your eyes off of that. So when people bring deals, and I have a lot of deals landing on my desk, right, the first thing I do is I poke holes. Because I know when I can't poke a hole in it, that's a winner, right? So that's what I do with my business. I walk around and I'm like, why do we have two versions of a Red Sox mug in the system? It's the same damn mug. This one says Red Sox on the tag, and this one's a Red Sox logo, but it's the same mug, but it's just printed up different with the SKUs. Like, I don't know. Well, guess what? You're going through the system today and you're going to wipe out every duplicate that's in there. And we're going to simplify it. It's just stuff like that, man. It's really not complicated. It just.
A
It really isn't.
B
Find the problems, find the holes, and fix one at a time.
A
I think it also starts again, you know, you got that filter first. The first filter is, I'm not going to go pull 40 hours a week. It's not going to happen. I'm going to be with my daughter, I'm going to be with my family. That's the thing. So how can I make sure that it's efficient if. If someone's starting through this and they're struggle busing and they're like, hey, man, Chris is amazing. I'm not going to be at this high school reunion thing, but I want to get a hold of him. I want to be part of this. I want to get to this process. How do people get a hold of you? How do they reach out to you? What's the best way to do that?
B
The only social I have that's public is LinkedIn. I find there's more serious people over there. My Instagram is friends and family. Sure. I could grow it and get a whole bunch of likes. And those are the vanity metrics that don't matter.
A
They don't.
B
So I pretty much just. You made everything private other than LinkedIn. I still do consulting. It's. It's not as common that I do that, but I'll do 90 day sprints with people like, hey, I got a product. Hey, I got a company. Hey, I got an idea. I help them get dressed, get ready for the party, go to the party, connect the dots. I'm out. Right. I still do some of that, but again, it has to check the boxes, right? Can I play with my friends? Can I leverage my network? Would my kids be proud of me? Is it going to be fun? Does the other person suck? Like, these are real check boxes, man.
A
Yeah, they're real.
B
And if you check all those boxes like, okay, this is a deal. I'D probably play around with, you're buying my time. You're doing it for three months. At the end of that, we can have a conversation. Do I continue as from an equity standpoint? Because we really got something humming here and it's not going to really work without me. Then I have that. So that's how I got into Dugout, is I got 40% equity in the company on the front side for no money down because of my involvement and what I was able to do. And then my golf company, I own 60% of that company for no money down. And it was a brand that had over half a million dollars in golf ball sales right off the bat. So it's like it. Does it fit my lifestyle? Can I play with my friends? Can I have fun? This is, you know, all these questions. So I still do my consulting. That's why I leave LinkedIn. And I'm really pretty responsive over there, But I would say that. And then obviously, Dugout mugs and big golf. I mean, check out what we're doing. What we're doing is awesome, period.
A
Yeah. So we. Yeah, absolutely. When we get sent stuff, because we had sent all the time, it normally lands flat. Your stupid mug. I'm actually a little pissed, but they love this thing. My entire team won't let me touch it at this point. They're running around with it, and so they're amazing. So where. If people want one of the mugs, where do they go? How do they get access to it?
B
Dugoutmugs.com that's the place to get it. Now if you want to do some custom stuff or get, like, some corporate mugs or something, just shoot us a message. There's Right on the site. Right on the site. Just pop it in there. Hey, saw Chris on a podcast. Wanted to chat about doing some custom stuff. And we're officially licensed with Major League Baseball, the Savannah Bananas. Like, we got it all. So you can do, like, Yankees mugs on one side from your friends at XYZ Corp on the back. We can do all that good stuff. So, yeah, pretty much. And if you want to come up with something awesome, let me know.
A
And what I loved about it was how fast it was. Literally, it was. It was like within two days it was there. It was like, what just happened? It was sick.
B
These guys are dialed in. They only do what they do best, and they don't do anything else. I don't walk up there and say, hey, Eric, looks like you're really managing shit well, can you go clean this thing? No. Or hey, Tina, you're really just on top of getting everything out the door. Can you go run the lasers like. And that's what people do. And I've seen it. I'm guilty of it. That's why I know it screws stuff up, is you find what somebody's doing and then you have them go do something else. I do it at my ma. I'll tell you a little story and we can wrap because I know you got a roll. I was at my mastermind the other day, and this guy, his name was Phil, actually, he just. Just put in an order this morning for. For mugs. So shout out, Phil. But he's like, all right, write in cursive with your dominant hand. Write your name. And everybody did. He had like 10 seconds to do it, because who remembers cursive? He said, now write it with your left hand in the same amount of time. And gave you 20 seconds. Right. More time. And it looked like trash.
A
Horrible.
B
Okay? But what he said is like, this is an example of what's happening in your business. So people are more focused and they take twice the time to do a shittier job because what you ask them to do is so far outside of their comfort zone.
A
Right?
B
Like, what a. What a great example.
A
What a great example. Good job, Phil.
B
To execute, it's like you can do a okay job if you know what you're doing. Then you can do a half ass job in twice the time if it's not your lane. But all the time, people are applying unnecessary pressure on employees by asking them to do what they're not best at. And I thought. And that really landed right.
A
Yeah, that was a really good. That's huge. So, man, I appreciate. There's so many different insights and things, and I've got to talk to you about mugs. But Chris, man, thank you so much for coming on the show. I really appreciate it.
B
Yeah, I'm always down to jump on, man. If you ever want to rap about something else, let me know. I'm around.
A
Sounds good, man. I appreciate it.
B
See it.
A
All right, that wraps up our episode. Chris is one of those few entrepreneurs who just gets in your face. He only buys what he loves. He only does what he loves. We jokingly talked about it after the call where he's like, dude, my entire life is sports, booze, and cigars. I get to do that every day and then go back to my family. What other life could you want? Talk about the proof of real entrepreneurship right there. I hope you guys enjoyed it. I'll see you in the next one.
Episode Title: $55 Million with only 5 employees – Kris Dehnert
Podcast: Proven Podcast
Host: Charles Schwartz
Guest: Kris Dehnert
Air Date: September 24, 2025
In this episode, Charles Schwartz interviews Kris Dehnert, creator of Dugout Mugs, who reinvented his business after bankruptcy and scaled it to $55 million in annual sales—with only five employees. The conversation dives into Kris’s entrepreneurial journey, the grit behind failure and recovery, the radical efficiency of lean teams, leveraging AI and systems, and the operating philosophies that underpin enduring success. Dehnert is candid, high-energy, occasionally irreverent, and deeply reflective, offering listeners actionable wisdom on building impactful and enjoyable businesses.
On Pain and Growth:
“When you fall, shit hurts. And you fall again and again, you're like, that is it. I am tired of hurting. I'm just gonna walk, right?”
—Kris ([04:46])
On Partnerships:
“A good day with bad people can still suck. And a bad day with good people can still be really awesome. What you're shooting for is a good day with good people and then, like, pour the champagne.”
—Kris ([08:15-10:31])
On Lean Teams:
“If I don't know something, best case scenario, I'm going to be mediocre... best bet is to get somebody else.”
—Kris ([11:42])
On Empowerment:
“Give direction, not directions.”
—Kris ([14:46])
On adapting in crisis:
“Ready, fire, aim. Make a move, measure the move and be ready to adjust.”
—Kris ([20:56])
On Compensation:
“Half the team got a raise on the first day. And it was about me committing to that... Don't drop the ball. Here's the ball. Go.”
—Kris ([23:54])
On Building for Personal Freedom:
“If I'm mission critical to the process, I have failed. I have created a prison. I have not created a business.”
—Host Charles Schwartz ([33:55])
On New Opportunities:
“Now I can turn [a defective mug] into six keychains that sell for 20 bucks a piece… I turned trash into $90.”
—Kris ([44:59])
On Misusing Talent:
“People are more focused and they take twice the time to do a shittier job because what you ask them to do is so far outside of their comfort zone.”
—Kris ([52:22])
[This summary omits ad reads, intros, outros, and non-content sections as requested.]