240. From $100K in Debt to a $25M Print on Demand Empire

0:00Chris Heckman:The morning his first store launch, Chris woke up early, rushed to his dashboard, and saw zeros across the board, with money already drained from his ad account. He was carrying nearly$100 ,000 in credit card debt, he had no backup plan, and he had just watched his big break produce absolutely nothing. Most people quit that morning. Chris Heckman almost did it too. Instead, he learned how to treat failure like data and over the next eight years, built a print-on-demand business that would generate$25 million in sales. I'm Ryan Atkinson and you're listening to the Outflip Podcast, where we interview entrepreneurs to hear their advice on how you can start a business too.

0:40Chris Heckman:I am so excited to welcome Chris to the podcast today to talk about print-on-demand, his origin story, and all that comes with it. So Chris, thank you so much for being here today. What's going on, Ryan? Happy to be here. Thanks for having me. We got a fellow Austinite on the pod. I'm always excited when we can do that. But for someone that doesn't know what print on demand is, give us a little high level of what do you do? What does Chris do? Yeah, so print on demand is simply the way that we fulfill orders. So if you're a customer and you come to my site, if you place an order, instead of me having all the inventory, like in our e-commerce brand catalog, which is thousands of products, instead of me having to have a warehouse, I just simply route the order over to a partner that then prints it packs it and ships it directly to you So it's a really lightweight business model that honestly My favorite part about it is it just lets you work from your laptop wherever you want without being tied down That is like the dream business for a lot of people.

1:34Chris Heckman:What did you do in revenue? I kind of gave it on the intro but the last 12 months how big of a business is this? Yeah, so i've been doing this for almost a decade started in 2016 which is, you can see the t-shirt shaped bags under my eyes. In the past year on our brand Sloth Hiking Club, we've done a little bit over 1.1 million. Oh man, incredible. We're going to talk about how you got there, but let's go back to college because you graduated college, really no job lined up. Ended up at Amazon just to like pay the bills here, but quite within about, I think, three months here, if I have it right.

2:03Chris Heckman:Tell us what was going through your mind that day when you were quitting Amazon and like, hey, I'm going to go try and start something myself. south? Yeah, honestly, it started a little bit before that. I had like a, not even a quarter life crisis, an existential 18, 19 year old crisis, if that's even a thing. When I was an intern at a company over the summer and great company, it's a recognizable name. And as I was there, I learned a lot from this walk a mile program where you go around and talk to people and learn about their roles. Super interesting and learned a lot about their different fields.

2:34But the thing that really stood out to me was hearing people, the way they kind of spoke about their job, it almost seemed like it was a foregone conclusion in their minds that that was going to be the rest of their life. Obviously, like everybody has different situations and, you know, kids and family to support. So I'm not knocking anybody by any means. But as an 18 or 19 year old, I was like, that doesn't seem exciting.

2:56Chris Heckman:I don't want to be able to predict what the next 40, 50, 60 years looks like. I haven't, I can't even drink yet. Like, that seems crazy. And so that was kind of like the raw, unfiltered thought process. And then when I graduated, still had that, no idea what to do with it. So I sat down, basically just started Googling how to start a business. Parents and reality came knocking about six months into that. They're like, you know, you still, it's great. The little bubble you put yourself in trying to figure this out, you have bills to pay. So I ended up taking the job at Amazon, as you said. And then fortunately, that was really the fire that sparked, I think, me stepping into a real role, realizing this could be the next 20, 30 years if I don't change something fast, that it really got me to buckle down, think a little bit more pragmatically about my business.

3:40I was far from smooth sailing from that point forward. But yeah, it was about three months later that I left that and went all in.

3:46Chris Heckman:What gave you the confidence to go all in? Obviously, you go to Amazon. You are like, OK, I'm going to actually focus on my business as well. What gave you the confidence to go all in after just three months? Honestly, I don't know, to be honest. I was stubborn. I probably, my ego, if I'm being really honest, like all those things, all that I do know is that at the back of my mind, I had what some people call like a burn the boats mentality, meaning I literally told my parents this at one point to their dismay. I said, I will live in a cardboard box under a bridge before I go back to another nine to five.

4:19Like I'm going to make this work or that's the alternative. There is no in between. and honestly, I think I got lucky with that because if I didn't have that, there would have been so many times where the logical thing to do was quit or go back to a job and that kept me pushing through.

4:35Chris Heckman:Yeah. What were you doing in revenue? Because I'm asking this because when I quit my job to go all in on my own business, it's so funny what we were doing in revenue. We were literally doing like$2 ,500, like$3 ,000 a month and looking back on it, it's like I cannot believe I quit my job to do that full time. I'm curious about what were you doing in revenue then? We were, and this wasn't even a e-com brand yet. I was doing like agency stuff for e-commerce sellers, kind of getting my feet wet. And we were doing about, it sounds like a lot more than it actually was, but it was about 15 to$20 ,000 per month.

5:09But the big caveat on that was we had only shown that kind of revenue for about a month before I was like, that's it. Like I've solved the equation, not realizing like, hey, maybe you should let this go for like three, six months, make sure it's actually stable. Long story short, it was not stable.

5:27Chris Heckman:But that's how much we were doing at the time. I love it. Well, I love the comments that speaks to like entrepreneur mindset of just like diving into it. Speaking of diving into it. So a friend invites you into his house with like 12 other people. Tell us about like this situation. What was the opportunity? And like, how did this set you up for success? Yeah. So it was the afternoon that I got back after I just quit the job at Amazon. I'm clean slate, wipe my hands of it, looking forward to the future. Fortunately, out of the blue, I got a call from a friend of mine who I hadn't spoken to in years, college friend, and he didn't have the house yet.

5:58He really just had the idea of, I saw you post in a Facebook group, which was ClickFunnels. A lot of people know it from back in the day. And basically we linked up, saw that we were running businesses together and he pulled together, it was 12 of us, like a ragtag team of people, recent college graduates to people who had been out for a year or two. The common factor was everybody was wanting to grow businesses. Everybody was specifically in e-commerce. A lot of us were coming into it with like next to no experience, very, very little money, if any, to our name. And we kind of, it started off as like this really fun thing, but the benefits started compounding pretty quickly in terms of like the incubator effects.

6:40Now, to be clear, I was like 22, 23 at the time. I was not that mature. I just thought this big house, like everyone around shop, cool. But in hindsight, there was a lot of benefits that came from it.

6:50Chris Heckman:Yeah, what were like some of the benefits? I'm always so jealous of that. Like, cause there's been times like where I just want to like get some of my friends and be like, let's go to like Puerto Rico for like a month and like just like all work out there. What were some of the benefits? I'm going to start telling people, hey, Chris told me we should do it. So let's do it. But say, what were some of the benefits? The main one is one that I don't think, at least for me, I would have been able to recreate any other way besides living there, which is, and you probably heard this before, the best way to learn a language is to go immerse yourself in the country.

7:17You're going to learn it so much faster that way. Exact same thing applied here. And then at the same time, that was compounded by the fact that not only were we all immersed in it, but we were all learning so rapidly, not because any one of us were super geniuses, but it was because Chris would go over here and he'd make this little mistake on like conversion rate optimization then he'd come back and share with the whole house and then you know john would figure this out on ads and he shared that so like the collective knowledge of the group it was like the tide that raises all ships and so an example of what that looked like was you would come down to the kitchen table at eight in the morning to check your ads and there already be six other guys down there like sharing their metrics talking about what they're doing and again at the time we just thought it was a lot of fun, but you learn rapidly because before that I was by myself.

8:04I was in a little apartment in the middle of New Jersey. I would come home, lock my whiteboard on the wall with my goals and action items. You learn very differently than in that kind of environment.

8:16Chris Heckman:Yeah, I like it. Well, let's fast forward into print on demand. So before we dive into the whole business model, all the actionable tips people can take away, how did you fall into print on demand then? Long story short, we tested a ton of different products. We were very product agnostic. The only thing that was a constant in our business and our approach was we used Shopify, which it doesn't even have to be Shopify. It's just a site that you own, not a marketplace. That was our take on it. And we drove traffic with Facebook ads and email marketing. So it was like three prongs. And then the optional fourth or the variable we were always testing was different products.

8:49So we went through like 3PL. We've had eight different brands over the years, 18 if you count the 10 failures, but they were everything from 3PL, socks, yoga mats, jewelry, home decor. And almost every one of those was what I mentioned at the beginning, where if you come to my site and order it, I'm able to go into my warehouse and then ship it out to you. That was how we did it for 90 % of the time while we were living together. That was traditional. That's what made sense. So that's where we ended up first. The downside of that is all of your cashflow, depending on how you run your business and how close you're monitoring your financials, all of your cashflow goes back into inventory.

9:27And so how we stumbled into print-on-demand was it was on one of our stores that was in like kind of a feminine niche where it was jewelry, home decor. Then one of the things we had on there was apparel. And apparel was all fulfilled by print-on-demand. The t-shirt started taking off. And then we were like, looked at, you know, the ABC analysis of how much we're selling on the other stuff. We're like 80-20 to a T. It was 20 % of our products, 80 % of revenue. We're like, why don't we just drop everything else and just do print on demand? That's what we did.

9:57Chris Heckman:Are you working a nine to five, but dream of entrepreneurial freedom? Look no further than the UFLIP Academy, the number one entrepreneurial platform with 20 plus step-by-step courses taught by active business owners, live workshops, hands-on skill training, a business idea database, and a thriving entrepreneur community to keep you accountable. Click the link in the description below to join the Uplup Academy today and make this the year you stopped dreaming and started building your business without guesswork. So how did you, for print on demand for someone that doesn't know, you just kind of gave it there, but I just want to make it crystal clear.

10:35Chris Heckman:What does like print on demand mean for someone that's listening for like the first time? the simplest analogy is like if you've ever walked into a store and or if you ever been like on a boardwalk and they have like one of those printing press things where you take the t-shirt you choose the design and then they make it on demand they print it and then they hand it to you that's print on demand that's all that it is the only difference is that obviously you're not physically walking into the store it's a website and rather than me having thousands of printers i just have a partner And so the way the economics work out, if anybody's interested, is we charge roughly$30 for a shirt.

11:12So you would pay us$30 and then plus shipping called$35. So you pay us$35. And then our cost on that, depending on the quality you go with, is about$14 to$15. So we're left over with$20 a margin that we're making in between.

11:28Chris Heckman:I want to ask this question. How do you determine what to design on a t-shirt? So someone's like, okay, that sounds really cool. I feel like I could come with a few ideas, but like for what you know now, like how do you decide like what the best ideas are? How do you know one has like potential? Yeah, step one, I completely throw out anything that I think is going to sell well. We have a running joke that anything I think is going to perform well, normally tanks. And anything that I expect to tank normally skyrockets. One of our coaches actually had the craziest story of this. He had, we use a Trello board for tracking designers and the pipeline.

12:04There was a design on there and it's normal. You go through and purge stuff. There's just crap building up. A design that he was about to purge, take out back and just bury it so nobody ever sees it. He ended up letting it go through. That design went on to sell, I forget the exact number, but it was tens of thousands of units of one design. Yeah, so that was very humbling because you realize I know nothing. And the direct answer to your question is just meet the market where they are. Find out what your people want and then get obsessed with the fact that you can't know upfront, but you can find the answer.

12:40And the way you find the answer is by launching as many products as you can. We aim for 100. And then you run ads. You basically open up the doors to your shop and then you watch. Just like if you were a shop owner, you have all your products on the shelves, you open the doors, where do people go on the shelves? And a lot of people, when they open up their first store, they open up the doors and then they're like, all right, they just stare at the cash register. It's like nothing is happening at the cash register. All the good stuff is happening in the aisles.

13:07Chris Heckman:That's where you got to be looking. Yeah, that's a really nice analogy. But how do I know like what to design on a t-shirt? Like I could think of like a few ideas that I could put on like a t-shirt, but like where do you get like the design inspiration from? Talk to us about that as well. Yeah. So forget about the design, which sounds counterintuitive. It was to me too. Designs isn't what actually sells. It's the concept. It's the messaging. Because people are not buying it for wall art. It's not going to be a beautiful sunset watercolor. That's a different market. Designing for a t-shirt, somebody is making a statement about who they are when they wear that six inches beneath their chest for 12 hours out of the day.

13:43When you're walking down the street here in Austin and you see me, you're going to see that shirt and you're going to make assumptions about me, positive or negative. That's what people are buying based on. And so the design is really distant second to what it actually says. So straightforward way to approach it. Start with one niche. One niche being what's something you're interested in. It could be coffee. People overthink this. Just start with something you like and then come up with niche related jokes or humor that only you would or somebody in your niche would find funny. The sweet spot for this is if you're in your niche, say that you're really into, I don't know, water polo.

14:18If you see a shirt and I'm in the water polo niche, my shirt, when I sell it, it should make total sense to you. But anybody who does not understand water polo, they look at that like, I don't really get it. That is the sweet spot. And that scares a lot of sellers because it requires you to say no to 80, 90 % of the market in order to really stand out to the remaining 10 to 20%.

14:40Chris Heckman:That is really good. So is there a concept? Should you only stick with one niche? Because the question I'm going to ask here is like, a lot of times someone says, okay, have like a broad niche here, like shoes, and then have another broad niche, like coffee, and then combine them to like gather to make it like more niche. Does that also work in dropshipping? Yeah. So you start with one parent niche. So the stores that we've been in yoga, it was a great one. We had nature and outdoors. We did tie dye, which doesn't quite count as a niche. Like that's more product specific. And then our current one sloth hiking club, each one of them, like we had crossovers, which is what you're describing.

15:16So we would have like sloth hiking and then with a cup of coffee. So like totally applies as long as you maintain like the vertical that you're in. The reason that that's important, people hear like you got to stay on niche. Like why does it actually matter? Because if you're a customer and you see my ad and I'm broadcasting to the world, we're a water polo store. And you're like, okay, these people get me. You click on the ad, you land on a site that has there's the water polo thing but then it's next to croquet and then next to ping pong it's like immediately waters down the effect opposed to they land they click on the water polo design they see nothing but water polo and they're like these people get me and then they

15:55Chris Heckman:start shopping what are some of the best niches you've experienced in this space is it the yoga what are if someone's just getting started what are some good niches to consider obviously they should consider what their own interests are but like what are some good niches yeah so that first piece is really important like a fantastic niche is like flowers and this was one that i did on a demo store yeah because it's so visual and like there there's so many crossovers and like you can do mindfulness positivity all of that great niche i started it as a demo store about three weeks into running it i was like if i have to stare at another dandelion and upload another ad like i'm gonna go get the 95 this is not for me so it really does need to be something that is sustainable something where you sit down and you actually have some level of enjoyment the sweet spot that if i'm starting a new niche i want there to be a really big element of humor and this is kind of specific to me but dark humor or sarcasm like something in the water polo space that is like anybody who's in the niche they get it and they're like oh yeah i'm so tired of that i'm so sick of that another example is on our other brand history tees this is the perfect example to sum it up the top selling design was a picture of Lincoln.

17:07And it said, it said just a terrible image. And it said Ford's theater, one out of five stars would not recommend, which that's about as dark as the humor gets. But that's the sweet spot because you have to know something about history to get the reference. And then two, the humor is so provocative that it gets a ton of comments, which then sparks the algorithm. And that's really what leads to going like quote unquote viral, like a lot of people chase.

17:32Chris Heckman:What I love about one thing that you said is when you wear like a t-shirt, it truly is like a statement of like who they are as like a person. I was just thinking, I saw someone the other day wearing a t-shirt that said like, pray on it. In an instance, like I kind of get like a sense of like who they are. So I think people should like really take home of that. I'm sure you have a lot more instances when it comes to mind like that as well. Like it truly is a statement of who the person is. Yeah, a hundred percent. And I think for anybody who's watching this, considering getting into print on demand or already in it, do not like attach your ego to any one of the designs that you're making because your job is to make educated guesses about what other people want.

18:09Your job is not to impose what you want on your customers and pretend that you know better than them. And it takes a little bit of humbling, especially I find if it's somebody who's coming from a graphic or like creative background, because that's their skill set. Like they have, and it's true, you have great taste, but nobody cares about your taste. They care about theirs.

18:31Chris Heckman:Okay, so someone says, okay, I got a good design. It's got some sarcasm in it. It's got some dark humor. It's a niche. Chris, how the heck do I go market this thing? Do I just go pour a bunch of money into ads? Do I just go post a bunch on TikTok? What you know now, what's the best way to get like those first 10 to 50 customers, let's call it. Yeah, paid ads, hands down, on Meta. I used to beat around the bush with this and say, you can go organic if you want to save money. No, just set aside$50 a weekend for paid ads. If you want to do organic, it can work. You're going to be waiting years. Have there been people that do it?

19:06Sure. It's outliers. You need$50 per weekend,$12.50 per day. Run your ads Thursday to Sunday. And then in the beginning, don't watch for conversions. Watch for the cost per click. So we want it to be in the 50 to 75 range. When you're in that range, it shows that you have something there. And we start with one design. Great. Good start. You need 100. You need 100 shots in the dark. And then you launch them into ads. And basically, Meta is telling you people like these five to 10. They hate the rest. And very normal success rate is like one to 2%, if that, on the first hundred. And when I see somebody has even one design out of their first hundred that's taking off that's incredible because that's all you need that's a thread you pull on like if it was lincoln five star the perfect example is when we launched history tees it was a bunch of different stuff from like women's history to american history to all these different things i personally like these like blueprint maps of like sherman tanks i thought that was cool nobody agreed with me that's okay because we had one design in there that was the lincoln five star review so as soon as we launched that, that was getting, it was like 20 cent cost per clicks.

20:19And as soon as we saw that, we're like, okay, got it. Take down all this stuff. No ego attached to it. We're just going to lean into the humor and the sarcasm. And then we just went from like that very simple iteration process, just list out historical figures in this case. And then like, what was something sarcastic or a joke we can make about it. And even there, after we had that thread, it was like a 20 to 30 % hit rate at most. But that's the whole game. Launch with 100, find the one winner, and then you keep

20:47Chris Heckman:doubling down. So cool. I want to clarify this. So you could really start with this like$50 just on an ad budget,$12.50 a day or so for three days? Yeah. So 50 bucks per weekend. So it comes out to 200 bucks per month. And you should be getting at least a handful of purchases towards the, we call them testing cycles. Like you run one weekend and then you look at your data and And normally there's not much there. That's okay. You just find the nuggets. And then Monday to Wednesday, you make another 25 designs. So you make 100 and you go to 125. You run another weekend test. And you're basically just stepwise increasing until eventually you find a set of designs that are able to carry the account.

21:28And you're getting consistent cheap traffic. And then you start tweaking the site and get people actually converting.