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The Entrepreneurial Mindset of the Pop-Punk Lifestyle with Sam Dean - Honest Ecommerce Ep. 154

On the tail end of some major life changes, in 2006, at the age of 23, Sam Dean took every penny he and his wife had (and some they didn't) and bet it all on selling body jewelry to strangers on the internet. 

Fresh off the memories of the "dot com bubble" and unknowingly walking towards the '08 Financial Crisis, Sam was continuously warned by family and friends that the internet and body jewelry are fads and won't be around forever. 

15 years later it seems wild that anyone ever doubted the Ecommerce future, but Sam saw the writing on the wall. 

With hundreds of thousands of customers, Plug Your Holes now ships 8-12k orders per month and employs over 2 dozen people in their Kansas City headquarters. 

Sam is now looking to the future of PYH, his family and his other endeavors. 

In This Conversation We Discuss: 

  • [00:00] Intro
  • [00:59] Sam’s journey to Ecom
  • [02:33] The idea of selling body jewelry
  • [03:38] The genre and aesthetics are misaligned
  • [04:34] Inherent go-to-market strategy from bands
  • [06:14] The Vans Warped Tour Experience
  • [08:13] How the Tour helped Plug Your Holes
  • [09:39] 2000’s Ecom vs now
  • [11:47] Sponsor: Electric Eye electriceye.io
  • [12:07] Sponsor: Mesa apps.shopify.com/mesa
  • [12:58] Sponsor: Gorgias gorgias.grsm.io/honest
  • [14:18] Sponsor: Rewind rewind.io/honest
  • [14:51] Sponsor: Klaviyo klaviyo.com/honest
  • [15:38] Social media approach to awareness
  • [18:19] Mistakes Sam wants you to avoid
  • [20:26] What you start with doesn’t really matter
  • [21:10] Determining what you are really doing
  • [22:01] Concert goers and body jewelry customers
  • [23:19] Culture, acceptance, and employment crisis
  • [24:34] Take the first step
  • [25:25] Pushing your minimum viable product


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Sam Dean  

I think the number one thing that I see out of wantrepreneurs is inability to take the first step. Get out there and put out a shitty product and learn while you're running.

Chase Clymer  

Welcome to Honest Ecommerce, a podcast dedicated to cutting through the BS and finding actionable advice for online store owners. I'm your host, Chase Clymer. And I believe running a direct-to-consumer brand does not have to be complicated or a guessing game. 

On this podcast, we interview founders and experts who are putting in the work and creating real results. 

I also share my own insights from running our top Shopify consultancy, Electric Eye. We cut the fluff in favor of facts to help you grow your Ecommerce business.

Let's get on with the show.

Alright, everybody, welcome back to another episode of Honest Ecommerce. It's not often that my life goes full circle and I get to have a guest on the podcast from my previous adventures. 

But it's gonna be a really fun conversation today. Welcome to the show, Sam Dean from Plug Your Holes. Welcome to the show, Sam. 

Sam Dean  

Howdy. Howdy. 

Chase Clymer  

Aw, this is going to be very fun. So I don't want to give away how our paths might have crossed back then. I'm sure we've met in passing. But it's been so long now. 

But just take me back to 2006. And where did you get the idea to just dive all in on trying to sell people jewelry on the internet?

Sam Dean  

Well, in the life prior to that one and the chapters prior, I was touring in bands as a musician. And that ended. I'd gone from band to band and then just didn't have that next one to go to. 

So I started selling advertisements for a local Yellow Pages competitor and I was really bad at it. And I took... 

We had to go into an off-season for printing before distribution and I promised myself I wouldn't go back to it. So I said this internet thing looks promising. And people thought I was crazy. 

But I sold a whole bunch of PS3s, Nintendo Wiis, and 10th anniversary Tickle Me Elmos on eBay to start up, to get a little bit of capital, and started a website and about that... 

Plug Your Holes is probably about the 40th name we came up with and it was the only one I remembered the next day. So I figured that was probably a good sign. 

And we started to Plug Your Holes on September 27 2006. And by Christmas of that year, it was enough to be my full-time job and saved that phone book company from me having to come back and desperately try to sell advertisements that nobody wanted.

Chase Clymer  

Absolutely. So what was it... How did the idea... Because I know there's a lot of entrepreneurs out there that want to get into Ecommerce. How did the idea come to you to sell body jewelry specifically?

Sam Dean  

Yeah. Body jewelry. So it wasn't just a body jewelry space, it was more plugs for stretched ears. 

Chase Clymer  


Sam Dean  

And there were a couple companies out there that did it. I felt that the aesthetic that was being presented was that of a tattoo shop or... I felt very strangely out of touch. 

Logos that had barbed wire and things like that. And it was kind of hokey. 

The prices were astronomical. So I knew that there could [definitely be] some room for competition there. And I had been a piercer... And actually that's how I would supplement my income with touring: I would do piercing. 

So I had some wholesale connections for the supplies I already used to be able to start with a relatively modest selection of body jewelry. 

And it was just really... I felt we could do better. I could do better with the aesthetics and become more competitive with pricing. And it worked.

Chase Clymer  

I can... I agree with you. I actually used to have gauged ears up until 6 years ago. I had surgery to get them closed up. A little inside scoop there.

Sam Dean  


Chase Clymer  

But I do remember that it was very (laughs)... It was very  "alternative biker"... There was this whole aesthetic along with pierced ears, especially like gauged ears. And I was like "Half of this music scene are wimps. We like pop punk music. It's not that hardcore." (laughs) But... 

Sam Dean  


Chase Clymer  

...some of the alternatives to get, the accessories that you need for your lifestyle, I guess, weren't marketed to everybody. They are marketed to like the super nichey subcultures I guess.

Sam Dean  

Yeah, exactly. And it's... When the rest of us were listening to Taking Back Sunday and Dashboard Confessional, the aesthetic definitely didn't line up. 

So... And then as time has gone on... So just as the background of being a musician and stuff, I didn't have any formal marketing experience. 

I had worked a few sales jobs and was relatively competent at anything that wasn't a phone book. But when it came to... When it comes to being in a band, there's only... 

There's really just a couple couple things you do and one of those is you hit the road, and you go on tour, and another is you have good merch because you want people to buy your shit. So that's what keeps you out there other than the guarantees every night. 

So I had the same idea and focused on getting a really great looking logo from a good designer and rolled with all that. And the logos definitely evolved and changed over the years. And some of the motivations for those changes changed with time as well but... 

And then we went on tour. So I didn't know how to buy ads and even back then there were pretty horseshit ads unless it was Google search. And even then it was highly competitive and not a lot of customer retention. But yeah, we emailed... 

I had Kevin Lyman's email address from one of the bands I was in and hit him up. And I said "Hey, I'd like to come do the Vans Warped Tour. I just started this business, what do I need to do?" 

And he just basically replied with a thumbs up and forwarded me over to somebody in production. And I had 6 months to get ready to do something that was dramatically unprepared to do, but we did it. 

And then we did it again and again and again all the way till the end. We did 13 Warped Tours along with a lot of other festivals.

Chase Clymer  

Aw, you transitioned so beautifully. I didn't have to ask the question. 

So the go-to-market strategy was "I'm just gonna do what bands do, I'm going to go on the road, I'm going to basically do events," Right? "I'm going to go out there..."

Sam Dean  


Chase Clymer  

"...everyday, I'm going to sweat and I'm going to hustle." What was... For a listener out there that isn't used to what Warped Tour was, what was that experience? What is that level of dedication, duty... What was that experience like? Let's just start there.

Sam Dean  

For anybody who doesn't know, everybody on the tour, even first heard of punk rock summer camp. So it is very much that. It's a whole bunch of... 

There's 80 or so bands, there's 1000 people on the tour as part of the touring apparatus of production and staging and everything else. 100-ish vehicles, I guess... It is roughly 2 months of chaos and sweat and rain but a lot of fun. A lot of camaraderie. 

Everybody walks away from that tour every year, very close. I still have a lot of very close friends that we met up there. And it's a really good experience to also interact in a one-on-one manner with the fans of the company. 

We built a lot of very loyal followers. because we just had a really good chat about Futurama and San Antonio. It's like, you don't really... 

Especially in the Ecommerce space, you don't get a lot of opportunities to see your customers or your fans, depending on how you refer to them. And we got to... We really got to build up those relationships and a lot of them were great.

Chase Clymer  

Yeah, that's fantastic. There's one thing you forgot to mention there that I kinda want to... It's dirty and sweaty and stinky at times (laughs).

Sam Dean  

Yeah. I've been in sand storms, hurricanes... We've had tornadoes touched down nearby. I've seen more rain than you could possibly imagine. Lightning striking bridges that are directly above the staging. Yeah. 

When it comes to weather and the environment that you put yourself in on a Warped Tour... It gives you a lot. It gives you a pretty broad spectrum of options. 

And you got to figure out how to get shit down and all of it. So whether it's heatstroke weather or torrential downpour.

Chase Clymer  

Yeah. What else... It also gives you thousands and thousands of potential customers. So how did doing this touring, summer touring schedule, impact the business? 

What did that do?

Sam Dean  

I would definitely say early on, it had a lot more bang. Not so much that it wasn't good later on, it was just the proportion of online sales to in-person sales definitely changed over the years. 

I think those first couple years, we would do nearly half of our yearly revenue on the tour. And then as time went on, we grew and grew and grew online. 

And the amount... You're kind of capped at making out there. We hit a ceiling with that. 

But yeah, it's great to see 300,000 people over the course of a summer. And a lot of them did come back to the website, became lifelong customers and didn't just wait for us to come to their town. But also this is relatively early in the E commerce world. 

A lot of these people would wait for us to come back to town. They weren't comfortable shopping online. It hasn't become part of, you know, everyday behavior yet. 

So, we did everything we could, but some people just wait for us to come to their town next year.

Chase Clymer  

I've definitely bought stuff from the tent. And if we looked it up, I may be in the customer database. That'd be a really fun thing to do. 

Sam Dean  

Oh, I can look it up. 

Chase Clymer  

But... So the Internet of 2006 and selling online was... That's 15 years ago. That's...

Sam Dean  


Chase Clymer  

It's so much different than today. So how has the business of selling online changed within your business model? I'm assuming that there's just a lot of stuff that's come and gone throughout the years...

Sam Dean  

I would definitely say payment processors... Payment processing has gotten a lot easier. Just even getting somebody to have... We started off on the card system osCommerce. And that's entirely server side. You host everything. And that was great for a while. 

I think we were [there] maybe 3 or 4 years, before we switched to Shopify. But they're just... 

You had to bring in a developer,or you had to know coding to be able to get it to look the way you want. 

And all these MySpace kids have at least a little bit of HTML background. But I'm not the kind of guy who can build your website from scratch. So you're waiting... 

Anybody who's worked with developers, freelance developers, knows that they work on their own schedule. So if you want something done by Black Friday, you probably need to start in July. Yeah. 

A lot of growing pains in the beginning. Inventory management was horseshit. Just little things. But then we switched to something like Shopify and... I don't remember the exact year but it's been at least 10 years, maybe 11 years that we've been on it. And it's 

Chase Clymer  

Early adopters.

Sam Dean  

Oh yeah. Yeah, yeah. Very early. They're damn near a household name now. You can go... They're a publicly traded multi gajillion dollar company. 

So when we first got on that I was really intrigued with their apps and their themes and the ability to put something together that is just as aesthetically and functionally professional as any of the big players. 

And I think that gave us a little bit of edge. We actually saw a really big spike in sales when we switched to Shopify. That was... I can only really attribute the fact that it just looked better. The organization, the nav, everything was better. 

But when it comes to the things that I've [noticed], I guess, really changed, honestly, [is the] adoption of Ecommerce tendencies. People... And even before COVID, it was such a... 

So many people had switched over but now since COVID it's been stratospheric.

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Chase Clymer  

So let's talk... Let's transition now to more of what's going on now. Obviously, Vans Warped Tour no longer exists sadly. Huge part of my childhood. A huge part of a lot of people's lives. 

So obviously, that's not driving a lot of new customer acquisition. What are you guys doing today? How is driving awareness for Plug Your Holes?

Sam Dean  

Yeah, we still do some of the fest stuff even if it's not Warped Tour, because... Even outside of Warped Tour, we were doing Soundwave in Australia and we were doing Bamboozle, Skate and Surf or whatever you want to call it, and Riot Fest and a bunch of these. 

We don't do a ton of them. We pick and choose especially based on the location and "is the juice worth the squeeze" kind of thing. 

But we just did our first fest back in Birmingham, Alabama, of all places. A fest called Furnace Fest, which they did on their 21 year anniversary of that Fest... 

And not that they did all the fest in the middle. And it was more like a midlife crisis fest where you're getting a ton of bands that haven't played a show in 15 or 20 years.  

Everybody's bald or gray haired, they're bringing their damn kids, at this point, so I knew I had to be part of that in some way, shape, or form. 

So we sponsored the stage for all the old guys on it. And it was a blast. We had a really great time. Chad Johnson and Mike Ziemer put on one hell of a fest. We're probably doing So What Fest in May in Dallas. 

But other than that, I imagine a lot of what we do is pretty conventional, or at least... I mean, it's just conventional to me. I don't know. 

Influencer marketing, Facebook and Instagram ad campaigns, Pinterest, TikTok, Google... We're not super aggressive with Google, we just kind of want to own certain words. 

Once again, I've just never had the best luck with lifetime customer value at Google and also customer retention. They go hand in hand. But that's always been an interesting area. 

We do text message marketing for retargeting. I'm sure there's more. YouTube... 

Yeah, we do it all and that we've always been very social media centric, because when I... When we started, the other thing that we had going for us was we didn't have any money. 

And so we were fortunate enough that the bands that I was in prior, had given me some connections with other larger bands. And so it helps. 

A Day To Remember was posting about us on their MySpace and things like that. 

So, though we don't get as much of that sort of grassroots stuff anymore just due to saturation and algorithms, we're very, very social media centric in our approach. And then pulling people into the fold.

Chase Clymer  

Absolutely. Now, if there's a magic time machine, you can go back in time, you can tell yourself not to do something, is there any mistake that comes to mind that you want to help people avoid?

Sam Dean  

Yep. Yeah. There's a few. But one that pops into my mind is... 

I'll preface it with this. I'm not somebody who really lives in the past. I try to [ignore the] past and focus on the future. 

So I don't really spend a lot of time thinking about what I could have done differently. I think about what I will do differently next time. But if I had to avoid one really shitty moment in my life, it was the year we opened up a brick and mortar. 

We opened a store called Bangarang. And it taught me a lot of what not to do. 

We sold collectibles and body jewelry. In the beginning it was relatively popular. We definitely had some ordeals with our landlords, not fixing the HVAC and things like that. 

And then it really taught me the importance of vocation. And understanding the demand for the product. It's right about the time Funko Pops and Kidrobot characters started really popping off and we were selling a lot of the rare stuff. 

And we probably couldn't really get out of the store for less than $100 because it was pretty rare stuff. And unless it was like the holidays, we would carry like Frozen Pops just because some dude's kid is gonna come in and want an Olaf or something, so... 

But when it came to the challenges that we faced there, we quickly realized that the margins are dramatically different when you have that overhead. 

And the greatest thing about the internet is you have a nearly infinite pool of customers that all can fit in the store at the same time, who don't care what street address you have. That just doesn't apply to brick and mortar. 

And so you realize your limitations very quickly. And, eventually we shuttered the doors because it was becoming not just its own time suck and liability, but it was also becoming a burden on Plug Your Holes itself. 

So I was putting so much time trying to save this thing that was letting other things fall by the wayside that were causing damage to the golden goose, so to speak.

Chase Clymer  

Absolutely. That's actually a great thing to dive into. There's a lot of brands that I think start on one side of it and try the other. 

And I know brands that have started brick and mortar, launched Ecommerce, and then got rid of their brick and mortar stores just because that... Yeah, so it's...

Sam Dean  

Oh yeah. 

Chase Clymer  

...something worth considering. But also, you'll see there's like a lot of the direct-to-consumer, like big VC backed, funded brands... 

You'll see that they started direct-to-consumer, and they got a crazy reach, and then started to build out in-store experiences for more brand awareness. So, there's no right way to do it. 

Sam Dean  


Chase Clymer  

That's what I'm pointing out here.

Sam Dean  

Yeah. Yeah, I definitely agree with that. I think you just have to know what you're getting into and ask yourself also, "Is this something that I'm doing as an extension of the brand as a brand building exercise? Or is this something I'm doing as another revenue stream?" 

And you have to ask yourself, "Is the juice worth the squeeze?" We've talked about doing pop-ups. Obviously, doing a tour is sort of like an activation that you'd see at a larger downtown or something like that. But we've considered it. 

We've considered opening brick-and-mortar mall locations, before, it was clear that the death of malls was imminent. We go back and forth. 

We talk about this stuff and we kind of take a survey of the landscape that's out there right now. And we'll talk about it once every year, but we're not necessarily... 

We might never do anything like that. 

Chase Clymer  


Sam Dean  

We might pull the trigger on something in 6 months. I have no idea. You know, it really just comes down to the opportunities available and whatnot, so...

Chase Clymer  

Oh, absolutely. But I think that... Especially for your product,  the Rock and Roll concert audience just overlaps so well with the audience that would be interested in body jewelry.

Sam Dean  

Yeah. And the one thing I will say about that, though, is that that has changed a lot over the 15 years. I joke around that I started a company to sell circles to angry teenagers. 

And I guess that's probably what a lot of people did because CD or vinyl is a circle. They probably sell to an angry teenager as well. But more so I would say that, as our audience has... 

Chase Clymer  


Sam Dean  

..aged up, they haven't necessarily aged out. And so whereas you got your ears sewn shut 6 years ago... We have plenty of customers who are in their 30s, have professions, they are in the nursing world, or they're in accounting, or... 

You could just tell by scrolling past a few of the emails in the backend that these people have a work email, but they're using a college email because they're a professor or maybe they're a student. So there's a lot more diversity to it. 

And I think a lot of people...

Chase Clymer  


Sam Dean  

It's gone from subculture to culture. And it's... When most of the major corporations in America have some sort of policy regarding how big your stretch ears can be, you're probably gonna be fine.

Chase Clymer  

It's the same thing with just the general acceptance of tattoos. I think it's gone hand-in-hand. The subcultures now... There's just so many of us. 

And especially with a labor shortage, you gotta have to stop caring what I look like and understand I'm smart. 

Sam Dean  

Oh yeah. Even just like some of the things we're talking about. We were seeing companies hire, hire back drug offenders that they'd let go of, because of pissing dirty. 

And now they're like, "You know what, fuck it. We don't even care. Just come on back. You were a good employee. And it was stupid of us, for us to care." 

I tell my employees all the time. I, we have an arrangement, I have bought X amount of your work and time in exchange for a fair salary. And what you do outside of that is none of my fucking business. 

So, I want them to... I don't own their lives. And so... And you know what, going back to what you're saying about the amount of companies that can't really be picky anymore. 

I think it's going to open up a lot of possibilities for people who have criminal records, who have body modifications, who maybe don't... They just don't look the part culturally. 

People have a tendency to pick and choose when they can but desperation... Desperation is a motherfucker. So, yeah. And we're seeing it. We're seeing it in real time. And I think it's a good thing.

Chase Clymer  

Yeah, absolutely. Now, is there anything that I forgot to ask you about today that you think might resonate with our audience?

Sam Dean  

I don't think there's anything necessarily that... I just do my absolute best to try to encourage people to take the first step. Don't worry about getting all your ducks in a row necessarily. 

It's a hell of a lot easier to learn how to swim once you're in the water. And I think the number one thing that I see out of wantrepreneurs is that inability to take the first step. 

Get out there, put out a shitty product and learn while you're running because otherwise, you're just going to put it off indefinitely. 

And it will always be a "I had a great idea once." Well take that idea, go do something. Prove it.

Chase Clymer  

Sam, thank you so much for that. That's my... That's my whole goal with this is [to] just... Let's tell the truth. Just get started and you'll figure it out along the way. 

It's a long journey. It's a marathon, not a sprint.

Sam Dean  

Yeah absolutely. There's a... I think the book is called MVP. But there's a really good book about that. And MVP stands for minimum viable product. And just get something in front of someone's face, and then let them tell you what sucks about it and make adjustments. 

But yeah, that's awesome. And I'm definitely a supporter of your cause as I am regularly trying to encourage people to go out and go on their own. 

And there's nothing... And then you're going to have sleepless nights. And yeah. It takes a lot more guts than brains sometimes but yeah. 

Most of the time, it's the best thing you'll ever do. The worst day here is better than the best day working for someone else. 

Chase Clymer  

Oh yeah, dude. Entrepreneurship is fun. Sam, thank you so much for coming on the show today. 

Sam Dean  

Yeah, absolutely. Thank you for... Thank you for having me. 

Chase Clymer  

Alright. I can't thank our guests enough for coming on the show and sharing their knowledge and journey with us. 

We've got a lot to think about and potentially add into our own business. You can find all the links in the show notes. 

Make sure you head over to honestecommerce.co to check out all the other amazing content that we have. Make sure you subscribe, leave a review. And obviously if you're thinking about growing your business, check out our agency at electriceye.io. Until next time.