Episode 55

Entrepreneur and prankster Johnny Cupcakes on what it takes to build and sustain a booming personal brand

Self-made entrepreneur and prankster, Johnny Earle, joins us on Overtime to chat about the making of the widely popular Johnny Cupcakes brand. Johnny takes us way back and explains how it all got started—from what inspired him to become an entrepreneur at a very young age, to the struggles of managing and sustaining a growing business, and all of the lessons he’s learned in between.

I don't have it all figured out. I never studied business, I never studied design. I make mistakes every day, but I don't care about making mistakes. I look at every mistake as an experiment, and experimenting is how you grow. I'm just a little guy who's not afraid to fail. So if I can do this with something as weird as cupcakes on T-shirts, every single person can come up with a cool idea.

Johnny also shares an incredibly hilarious April Fools’ prank his team played on customers at their retail store location you won’t want to miss! It’s just one of the many examples Johnny mentions in relation to the importance of creating a community of customers and spreading good vibes.

This episode is brought to you by .ME. Make it easy for your clients to recognize your awesomeness by featuring your best work in one place—a place you own and control. Start building your online home with .ME, the most personal Internet domain.

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Dan Cederholm: Yeah. Welcome to the show Johnny Cupcakes.

Johnny Earle: Thank you, sir. Thank you. Thank you.

Dan Cederholm: Yeah, thanks for being here. I’m a giant fan and have been for a long time actually. Fellow New Englander and that’s awesome too, and I think your story is super inspiring. I just, I’m excited to share that with listeners because I think that the story is interesting, the brand is awesome, and we’re super excited to have you here. So thank you.

Johnny Earle: Yeah, you got it. I appreciate it.

Dan Cederholm: There’s a quote, I think it’s from your about page on, but it says, “I had 16 different businesses before I was 16.” I guess entrepreneurism and creating things has always been with you?

Johnny Earle: Yes. It’s always been with me. I grew up outside of Boston in a town called Hull, Massachusetts or Nantasket Beach. It’s a very small peninsula and really fun town in the summertime, where once winter comes you have to get very creative if you want to have fun. Some people choose to do hardcore drugs, some people choose to move away, and other people use their imagination and build tree forts and play capture the flag, or in some cases start a business. I think the claim to fame that we have is the guy who started Napster was from Hull. He was living in Hull at the time. I remember my friend Cherisse delivered a pizza to his house when my friend was working for Papa Gino’s. He got a $20 tip, and a Napster T-shirt, and we couldn’t believe it at the time.

Dan Cederholm: That’s amazing. Is that John Fanning, is that his name?

Johnny Earle: Yeah, and I think someone else. He was, or maybe his uncle lives in Hull too.

Dan Cederholm: Wow. Geez, that’s amazing.

Johnny Earle: Yeah, anyhow I grew up seeing my parents commute to work, and do that hustle and that inspired me to figure out a way to spend more time with the people that I love. So I wanted to be an entrepreneur. I didn’t even know that word at the time, I just wanted to make things or find a way to make my own money, so that someday I could possibly maybe spend some more time with the people that I love. So I started with lemonade stands. I graduated to having yard sales when my family was not home. That got me in some trouble, that was my 24 hour business because I was just selling things that were in the basement or in the junk drawer. I didn’t know they were still being used. I sold drinks along Nantasket Beach.

My bony adolescent limbs, I’d drag a cooler up and down the beach. I realized at a young age I could get a 12 or 24 pack of Coca Cola for a significantly discounted price. Winter came around and I needed a new job, and I shoveled snow. I’d charge people $20 a driveway and I could barely push that shovel, but it worked out to my advantage because people felt bad for me. So they would give me extra money and for tips. My friends, they’d be sledding legally in Hingham, Massachusetts at the South Shore Country Club, but as much as I love doing that, I wanted to make some of my own money and maybe buy a better sled, or buy my own Garbage Pail Kids cards, or X-Men Trading Cards. Yeah, I had all these other businesses. I sold glow sticks at one point around 4th of July as a firework alternative. I would approach people’s parents along the beach and say, “Hey, if you don’t want your kids playing with fireworks, you could buy a glow stick.” I sold a bunch of those. I was introduced at an early age to wholesale. I used to buy so many pranks from this one joke shop in Weymouth. There was a mall called the Harborlight mall, rest in peace, but the small-

Dan Cederholm: Yeah, that’s where I was born. Weymouth.

Johnny Earle: It was. So you know Harborlight mall. So Harborlight mall, I’ve got so many stories about that mall, but the first one I’ll tell you is that there’s one store where you’d go buy your candy, but they also sold pranks. It was by the main entrance of the mall. I would buy so many pranks that this guy introduced me to wholesale, and I had no idea what it was. He said, “Hey kid, I appreciate your business, but how would you like it if I told you, you could get 144 whoopee cushions for the price of four retail whoopee cushions.” I was like, “Whoa, that’s a lot of whoopee cushions. I don’t know, but that’s a really good deal. I just have to sell four of them at a retail price to make my money back, and the rest would be profit.” So that day I left with the Bible to entrepreneurship, the Oriental Trading Company catalog. I was like, “Whoa, you can get a billion pieces of candy for $60, and if you sell them for a dollar a piece, you could make $1 billion.” At least that’s what I thought.

So I ordered my whoopee cushions and I got them the next week in the mail, and I began reselling them. This was tough. No one was buying them, but I did sell a few and I made my money back and more. Instead of people giving me money, most people would give me the middle finger when I was pranking them in the middle of class. You don’t want to play tricks on your customers, which is something I’m still trying to learn because I trick hungry people for a living. The whoopee cushions, I had so many leftover. What do you do when you have leftover inventory? For the next couple of years, everyone in my family, they got a whoopee cushion for their birthday, for Saint Patrick’s Day, for Valentine’s Day, for Christmas. I was giving these out left and right, and then I came up with a cool idea. Finally at lunchtime I decided to trade my leftover whoopee cushions with other people for candy, for their snacks or for whatever they were eating. I would take their snacks and I would resell them to other people. All of a sudden I was getting rid of old products, getting new money, new products, and putting it right back into the business. I think that’s one of the bigger lessons I learned at a younger age, is how important it is to reinvest your money back into your brand, into your ideas, whether it be products, or business cards, or events. That’s what I was doing. I was reinvesting my money back into itching powder, fart spray, stink bomb, switchblade combs, everything I shouldn’t have been selling in school, I was selling in school. Someone got an allergic reaction to itching powder and had to get rushed to the emergency room, and I almost got expelled from schools, but I got suspended. When I went back to school I had to come up with something else to sell.

Since most of my friends were selling drugs at the time, I decided to sell candy. Now that I’m introduced to the world of wholesale, I know that I could buy anything in the world at inexpensive prices as long as I take that initial risk up front. There was a school store, but I had all the good stuff. I had M&M’S, Sour Patch Kids, Sour Patch Watermelons, which are the next best thing to Blue Raspberry Gushers. These were going left and right, even my drug dealer friends were very impressed and they were like, “Dude, how much money did you make?” I was like, “Guys, you’re actually my number one customer because you have the munchies every day.” They were like, “Yeah, okay, okay.” So I stayed clear of drugs and I stayed out of trouble even though I hung out with a lot of funny people, but yeah, those are some of the hustles.

I went to a charter school, I had a hard time learning. Never was put on any drugs for it. Instead, my parents put me into a startup charter school, the South Shore Charter School. It’s now called the South Shore Public Charter School, but this school changed my life. I got to go to smaller classrooms, which helped me focus. I got to learn hands on, instead of learning about marine biology in a book, we would go on whale watches and visit different aquariums and interview people. I think that really helped me retain a lot of information. Then I also was in this school with kids that were much older than me, kids that were younger than me, people from different towns, different cities. So it was good. We even had a diversity class and we were learning about to go to a school in a small town, and learn about things beyond a typical small town mentality was really new and refreshing at that age.

Dan Cederholm: Yeah, I bet.

Johnny Earle: Those are some of the hustles. I think the hustle that gave me my biggest profit margins was while my friends were hanging out with cute girls at parties, I was hanging out with cute old ladies at Jo-Ann Fabrics and I had a new business idea. I would go up and down the fleece fabric isles of Jo-Ann Fabrics and I would buy a yard of fleece fabric that was on sale for $3. I would cut it in three strips with a pizza cutter. If you cut fleece fabric the right way, it does not fray. So if you can cut pizza, you can cut this fabric and I would resell these scarves for 30 bucks a piece. I was making $90 anytime I spent $3, so an $87 profit. I had them sold at different craft fairs. I was selling them at some stores around New England, and I was realizing how valuable my time was at a young age.

So to this day, I’ve never tried any drugs, even though I know a lot of words to gangster rap music. I’ve never had a sip of beer. I’ve never been drunk before. I’ve purchased alcohol just because of the cool topography and inspirational packaging, but I’ve never had a sip of alcohol. I’ve never had the desire to be drunk. I think it’s partially from growing up with a lot of trouble makers. My dad drank a bunch when I was younger, and I think that was one of the big things that turned me off. I was afraid that I would be addicted, and as a person who collects things, I know that if I tried marijuana, if I tried it, I know that I would want to try every possible strain of marijuana. If I drank, yeah I’d want to try it all and I’d want to collect it. I just, I don’t know and I have fun anyways. I just don’t need it right now.

Anyhow, at a young age, I was saving so much money. Not only was I saving money from not partying, but I was saving a tremendous amount of time by not going out on Thursdays, Fridays, Saturdays and recouping Sundays and half of Mondays. I was saving, I had five days a week where I had a bit more time and money and energy and focus than a lot of the kids that I went to school with, and it allowed me to focus. It allowed me to experiment and that’s what you have to do to find out what you’re passionate about. Yeah, it was a lot of adventure.

Dan Cederholm: That’s wild. So I mean early on you had that focus and drive.

Johnny Earle: The focus, yeah and the curiosity too. I sold Tupperware too. That was a bizarre adventure. Speaking of Weymouth, and other Weymouth connection I was at Stop & Shop in Weymouth. This cute old lady came up to me and she said, “How would you like to win a free minivan?” I said, “Sure, I’d love to win one. Tell me what I got to do.” She said, “You just got to sell Tupperware.” I said, “All right, I can do that.” So I started selling Tupperware when I was a teenager. I would go to these meetings in which it felt like a eyes wide shut with Tom Cruise, that movie. It was definitely a little creepy at first, but I was the only guy there. I was the only person my age, and it was incredible. I learned two big things. One I learned about French onion dip that day, which completely changed my life. Two, I learned about these orange peelers. These plastic orange peelers that you would give out as an incentive to anybody that signed up for a Tupperware party, or that purchase extra Tupperware. So at a young age, I realized how valuable it was and how important it was to thank your customers and your clients, and to give them something unordinary. Anyhow, that happened in Weymouth I remembered. One of my first jobs was in Weymouth at the Harborlight mall, at building 19. I worked in the greeting card section.

Dan Cederholm: Yeah, building 19. I remember that.

Johnny Earle: I don’t think I was legally allowed to work there because I think I was 14 at the time, but for my Christmas bonus, they gave me this little bruised Turkey. I was so proud to take that partially deformed Turkey home to my parents, and have this Thanksgiving dinner or Christmas dinner.

Dan Cederholm: The bonus was actually a turkey.

Johnny Earle: It was a turkey, a very small bruised turkey.

Dan Cederholm: Bruised turkey. That’s incredible. Along with all that entrepreneurial spirit, was also branding and design, was that conscious in your mind at the same time or did that come later with-

Johnny Earle: I collected a lot of He-Man action figures from that packaging. Little things like that. Like Cracker Jacks with the prize inside, that feeling of getting not only a prize with something, but a surprise. Something you don’t even know what’s inside of it, those things stuck with me. Getting a Hologram gambit card with a pack of X-Men Trading Card. When you’re a kid, it’s the Christmas eve feeling. It’s the first date feeling. It’s the tingles that you don’t often get from buying a product nowadays. I mean, I remember when you would buy Coca Cola Dr Pepper and you had a chance of winning. It would straight up tell you on the cap, and then at some point you had to type in a 30 digit case sensitive series of numbers and letters online, and now they’re making money off of advertising to you, while you go check out if you won or not?

Dan Cederholm: Those were contests, those were great.

Johnny Earle: They were the best.

Dan Cederholm: The very crudely printed code on the underneath the cap.

Johnny Earle: Yeah, you might be drinking half of the code if you shook up your drink before you had it. I think those stuck with me consciously and subconsciously. I just, I remember when I was hustling my pranks in school, at one point I made this prankster pack way before time when I was a teenager at the Charter School. I had all of this inventory, I would package them up and I would sell these like prank boxes. So you would get some surprises in there. I remember I called it the Johnny Mac Prankster Pack. I hand wrote it on there. I had some fancy tape and I would reuse sneaker boxes for these. I remember giving one to my friend Rick Barton at the time for his birthday over the summer, and he was elated and really excited. Yeah, those things stuck out. When I started making T-shirts later on, anytime someone bought a shirt I would make sure to give them a small token of appreciation, whether that be a Vintage Ninja Turtles, or New Kids On The Block Trading Card, or a sticker, or some candy that you don’t normally see at the store. Just something to get them talking and to make them feel good, and it wasn’t so much of a marketing idea as it was just the way my parents raised me to be thankful and thank people.

Dan Cederholm: Wow and that’s so valuable for a brand. All those things you’re talking about, I remember them and they’re so critical.

Johnny Earle: They are, I mean looking back, any cereal that I purchased was solely based on what prize was inside of the box.

Dan Cederholm: Exactly.

Johnny Earle: Yeah. Losing your teeth, you’d be so excited as a kid for the tooth fairy to come to get that little surprise, and to get that feeling of I don’t know, that magic. I think everybody can incorporate that sense of wonderment in whatever, whether you’re providing a service or selling a product. If you are at all interacting with any other human, you can for sure make them feel better beyond sending them an invoice. I mean there’s 101 ways to do it. Right now I am getting carpal tunnel syndrome. I made a deal with myself that, and I told myself that this year I’ve got all these LinkedIn connections, which LinkedIn is the most valuable thing that I’ve ever utilized for the longest time. I wouldn’t go on it because I thought it was for old people, and then I became old and I love it. It’s for young people too. It’s for everybody. When I was younger and it first came out, I was like, maybe it’s because I got so much spam for LinkedIn that I just decided to write it off, but I told myself this year I’ve got all these LinkedIn connections, what do I do with them? I’m going to write handwritten letters, postcards, typed messages, I’m going to send them physical mail. Even if it’s more than 6,000 people, I’m going to do it. So just the other day, I wrote I think 73 postcards. I didn’t just say, “Hey, let’s work together.” I made it personalized, and I’m not sending them to everyone I’m connected with. I’m sending them to the people that I want to do business with. I don’t know, I think-

Dan Cederholm: Has that always been something you’ve done for your brand, reaching out with physical things or just going the extra mile there?

Johnny Earle: It has been because again, I know that feeling. If you can make someone feel that, even if you don’t have a business, write a note to your wife or your child, or your colleague, or an old teacher who taught you something that completely changed your life, or helped you get through school. It really doesn’t take much to make someone’s day, make their year. It can go beyond an email and a text message. Again, that human element is so important. I see brands, I see people starting brands left and right, which is great, but sometimes people will get stuck on social media, which is a very important tool, but it could be so damaging and it could be the biggest time suck. If you’re not marrying your digital presence with creating real life relationships through networking events, and parties, and going to different, I don’t know, workshops or festivals, it could be very damaging to your personal growth, and your professional growth and your circle of a context if you really want to grow that. If I met someone in person and I got an email from them a few weeks later, I would certainly reply to that email. If I got a cold email from somebody, there’s a chance I could reply to it, but it all depends on what I’m doing that day, and it’s probably not going to be the first thing on the top of my mind.

Dan Cederholm: So true. It’s so true. I feel like that’s even more important today where so much of our communication is digital. At the end of the day, I’ve always found it’s those relationships that matter the most anyway.

Johnny Earle: Yeah, no, it is. I even went as far as, I was getting my teeth cleaned or maybe I was getting a cavity checked out in the city in Boston. For some reason, I got out of that chair and I wanted to buy a typewriter. I looked online, and I found a typewriter shot called Cambridge Typewriter right in Arlington, Massachusetts. I went there and I bought a typewriter from the 1930s, and I started typing notes to my customers, to some of my clients, to family members. I don’t know, not being on my computer felt so therapeutic. People receiving real mail, they celebrated it. I don’t know, I could talk for years about the importance of that, and the different ways to do that.

Dan Cederholm: The idea of surprise and thanking your customers, that was ingrained in you early on. Obviously with Johnny Cupcakes, I feel like the whole brand is that. It’s almost like you are practicing for the main event, you know right? I visited the store, your flagship store there on Newbury Street in Boston and I think it’s an amazing experience because you walk in, and it looks like a bakery. There’s vintage ovens and all the shirts are in bakery cases. I guess it’d be cool to dig into the origin of that, because it sounds like the brand maybe started a little accidentally if my research is right, but you can correct me if I’m wrong there. Then at the same time, how you’ve evolved it and grown it. It sounds like you had been practicing for much of your life.

Johnny Earle: Yeah, I’ve been waiting for this accident to happen so to speaks. Yeah. So I was in a hardcore metal band called On Broken Wings. I played samples in the band, I put in samples from horror movies in between heavy metal riffs and breakdowns.

Dan Cederholm: Awesome. Is that the name On Broken Wings from the song?

Johnny Earle: Well we didn’t take it from the song, but yeah it’s the same-

Dan Cederholm: Yeah, yeah, love it. Great, great.

Johnny Earle: As the band was starting, I was working at Ben and Jerry’s. I had a job there in Hingham Massachusetts, there used to be a Ben and Jerry’s at Crow Point in Hingham. I’d be scooping ice cream and chiseling off ice cream skim off and my arm hair every night, peeling it off like it was Elmer’s glue. At some point I was in a couple bands. When I was a teenager, I was in a rap band called Sweeps. Speaking of packaging, I got us a show at CBGBs when we were like 14, 15 years old. Too young to even drive to New York City, but I had a hunch that whoever chooses to book bands receives a lot of demo tapes. If I’m going to send one, I’m going to send it in the most wild packaging with a personal note, and we got a gig there. It was on a Wednesday night in front of like three people that midnight, but we played there and it was pretty sweet. We brought a stranger with us to drive us, which was pretty wild but we made it. See, I got into another band On Broken Wings, and while I was in the band, I also had a full time job. I was working at Newbury Comics in Braintree, Massachusetts. If you’re not from New England, Newbury Comics is a record shop, kind of like Amoeba Records on the west coast, but they sell a lot of cool tchotchkes. While I was working there, I received a tremendous amount of nicknames from my goofy coworkers. They’d call me Johnny Appleseed. If I was late for work, they’d call me Johnny Come-Lately. Johnny Cupcakes came out of nowhere, and I thought Johnny Cupcakes was so funny. It sounded like a mobster name, or a pee-wee Herman mobster name or something. I just, I don’t know, I thought it would be funny to put on a T-shirt as a joke to advertise a bakery that didn’t even sell anything. I decided to do that while I was getting T-shirts made for the hardcore metal band I was in.

Now when I was at the Charter School, one of the requirements to graduate was to get an internship. That was the most valuable thing navigating my passion in school, was having to get an internship. I don’t think you’re ever too old, or too young to intern, or to volunteer, or to job shadow because it helps you find out much quicker what you want to do for the rest of your life and more importantly, what you do not want to do for the rest of your life. So I had an internship at a silk screen shop in Weymouth, Massachusetts called Rainbow Screen. They did a lot of stuff for like Lacrosse teams, and I was right on route 3A. I would get T-shirts made for my band later on in life, and I’d always get a good deal. I always get to see the shirts before they got printed and while they were getting printed if I want it to, and I’d save money by picking up the shirts.

So at that time I was able to print stuff way more locally. We still do some stuff locally, but this was almost in my backyard. I wore one of those shirts. I wore one of those Johnny Cupcakes shirts to work, and all of these slightly miserable customers that never made eye contact with me, they started laughing, and smiling and saying, “What is Johnny Cupcakes? Is that a bakery?” I think someone once asked me if it was an adult movie store. I was like, “No, no, no, no, no, no, no, no. This is just a T-shirt. It’s just a funny nickname someone gave me.” People were like, “I have a friend named Johnny, and I love to bake, or my friend loves to bake. Where can I get one of these Johnny Cupcakes T- shirts?” So enough people asked me that I decided to make more of these T-shirts that were once made as just a random social experiment. I knew I wanted to make a clothing line at some point in my life during my adventures of being entrepreneur that that did stick out, but I didn’t know it was going to be then. I thought it would spin off from the fleece scarves that I was making. The scarf business failed because summertime came around and nobody wanted to buy these warm scarves anymore. Anyhow, the Johnny Cupcakes thing picked up. Before I knew it, I was poking fun at pop culture, replacing pop icons of cupcakes, whether it’s the statue of Liberty holding a cupcake instead of a torch, or a fighter plane dropping cupcakes instead of bombs.

Dan Cederholm: Yes, I remember that one. Yes, I loved it. I loved it.

Johnny Earle: There was some tough guys that would go into the record shop, Newbury Comics wearing these skull and crossbones shirts. I was like, “You know what? I’m going to put a cupcake there instead.” Guys thought it was funny and girls thought it was cute. Everyone thought it was random and unique, and it caused curiosity and conversation amongst complete strangers. So I just kept making more of these shirts. Anytime I’d sell 12 tee shirts, I’d take that money. I’d make 24 shirts. I would not spend money on drinking on the weekends and instead, invested into this brand. It helped me pick up a bit more traction. Strangers started coming in saying, “Are you that cupcake guy? Where can I get one of those shirts?” I’m like, “What do you need? I’ll meet you in the back parking lot at 8:00. That’s when my shifts over.” I’d sell them out of my crusty beat up 89, gray silver Toyota Camry. Anytime I’d sell a shirt, I would try to give them something special again, like some Vintage Trading Cards, or some candy, or a thank you note. I would also ask for their email address, and I would stuff it into my glove box until my glove box was barfing out scrap paper and napkins that I wrote all these little notes on for my customers. I would email people when a new shirt would come out. Since I didn’t have a store and I couldn’t always sell stuff in the parking lot of where I worked, I would meet them at the South Shore Plaza, in the food court and just make it work. I kept growing and growing, and at one point I started making more money than I made with my paycheck, and I decided to leave the record shop, leave Newbury Comics. I loved it. They were great, great company to work for.

Then when I was in my hardcore metal band touring, I would sell these out of my suitcase. They were wrinkled up. They smelled like gas and fast food, but anytime I wore a shirt, another band would ask about it and they’d either buy a shirt or I’d hook him up with a T-shirt, but then that band would tour around the world. Then they’d get photographed in magazines. Before I knew it, I was getting 30, $40,000 full page advertisements for free because someone thought my shirt was funny, or cute, or I gave out a couple of T-shirts here and there. This community of collectors started popping up. People wanted every design. I designed my first T-shirts on Microsoft Paint, the best that I could. Some of my other ones I did on Illustrator, but I soon realized that I was a much better idea person and a concept person. I have a hard time sitting still. That’s why I went to the Charter School, so to sit at a computer for a really long time and create something was a very difficult task for me. So as my brand grew, I would take my drawings, or my concepts, or my wild ideas, and I’d work with other designers. A lot of freelancers, just to mix things up. I think if you’re going to start a brand, it’s really tough to let go and to ask for help because you want to do everything.

Dan Cederholm: Absolutely. I was just going to ask about that, because you’ve grown it so large since those early days, was it difficult to let go, or how did you do it?

Johnny Earle: So the brand kept growing. From Newbury comics, I eventually left the band that I was in. I didn’t want to have half both things. I wanted to focus on either Johnny Cupcakes or being in a hardcore metal band. I chose the T-shirts because it was mysterious, and scary, and I knew nothing about it and that made me very curious. So when we were touring, I’d get up early and I’d go to other stores, and I’d asked to meet with the buyer of the stores. I got my shirt sold in a few stores, but most people told me to go to these different trade shows. I didn’t know what a trade show was. I looked it up and it was a few thousand dollars to get a small table for the weekend, and in a very expensive hotel but I knew I had to do it. So I left the band to the trade show, spent all the money I had and didn’t have.

I started getting my T-shirts sold in stores in Italy, Japan, Australia, all over the U.S. It was great. It was all I ever wanted. I wanted to introduce my brand and make strangers smile. I wanted to trick people and also make them feel good. I eventually stopped getting paid on time and at some instances, I didn’t get paid at all and that really hurt me emotionally, and as of operating small business, it really hurt me. So at an early age, I decided to not wholesale anymore and to go direct to my customers because when you sell to a store, which is like you said, do you ever ask for help? That is a helpful thing in a sense, but when you sell to a store, you’re no longer in control of the customer experience. You’re no longer in control of how your product’s displayed if it goes on sale. Then if you’re too busy or if you’re too trusting, there’s some cases where you might not get paid on time or at all, and it could really hurt your operating cash flow. So I stopped wholesaling the stores. I said I’m going to go to more events and concerts, and rent out tables at flea markets, and farmer’s markets, and craft fairs and someday I’m going to open up my own store. A store became available in Hull, Massachusetts. It was an old built garage and my dad and I converted it to a retail store. It was great. 700 bucks a month for rent, but at some point I realized you get what you pay for and not many people were walking by when you’re a gas station in a seasonal town. We did utilize that space as an office, a shipping facility. We turned it into an art gallery and featured artists from around the U.S. or from around Massachusetts every so often. It was cool, but I eventually opened on Newbury Street, and that was the turning point of my brand. This was probably 12 and a half years ago from this interview, and that was scary. I went from spending 700 bucks a month on rent to spending more than seven, eight thousand a month on rent, plus the build out, plus the employees, plus the product to be there, plus the insurance.

Dan Cederholm: That’s a big leap. That’s the most expensive retail real estate probably in the state.

Johnny Earle: It is. Yeah, it is. It is, but I sat on those steps and I counted people walking by and I realized even if I never changed my T-shirt designs, which would never happen, but even if I didn’t, the people are changing. You’ve got, I don’t know the exact number, but what feels like about a million students around New England, are moving in and out of the area every year for school. When they leave, if they happen to purchase something from you, they’re bringing your brand back to where they’re from. Then there was the convention center across the street and all this stuff lined up, and I was like, you know what? I got to take this risk. So I did it and that opening day, we made around three months rent. It was unbelievable. I hired my mom shortly after-

Dan Cederholm: In one day?

Johnny Earle: In one day, yeah. I hired my mom to be the CFO of my brand. Shortly after she was able to quit her job in the city, and that’s all I ever wanted to do, was to spend more time with my family. That’s what inspired me to be an entrepreneur at a young age. So it was this very, very sweet moment. That was the success to me was just finding a way to have time with my family.

That store when we built it out, we set it up like a bakery. Displayed T-shirts, culinary theme T-shirts inside of industrial refrigerators. We packaged them in food containers. So when you buy a Johnny Cupcake’s T-shirt, it comes in a pastry box, had vanilla scented car fresheners, I hide them in the heater vents of the store, so you smell frosting when you walk into the shop. My friend Boris, actually was like, “Johnny, how did you do that?” I was like, “It’s easy, man. You mix vanilla frosting with white paint.” He said, “Really?” I said, “Yeah, if you lick the wall right here, you can taste it.” He said, “Really?” I said, “Yeah.” He said, “Really?” I said, “Yeah, no one’s been in the store yet. It’s still new. So the walls not dirty, and you can lick it and taste it a little bit.” So he went over, he licked the wall. He’s like, “I smell it still, but I don’t taste it.” I said, “Well, I’m just kidding man. It’s actually on this wall over here.” He went over to the other wall, he licked it and then I ended up telling him, but we trick hungry people all the time.

Now I’ve had a few stores. I had a store in Los Angeles for eight years. I had a shop in London for four years. I’ve done over 500 pop-up shops around the world, which I love everything about pop-up shops. After having some retail stores, you have a lot of costs and a lot of things that just take up brain space from an operational standpoint, but when you have a pop-up shop, I’ve done again over 500 pop-up shops around the world. 99% of them I have not paid for rent. We’ll collaborate with other people, and turn it into a collaborative event. People are excited to host the brand, but in return, we’re bringing hundreds of new people to their place of business. If they want, we’ll put their business cards in every order, we’ll bring someone to do photos, we’ll hire someone to do video. If it’s an area where we don’t bring much value, maybe we’ll donate a percentage to a local charity, or we’ll let someone do a pop-up shop at our place and we’ll kind of swap spaces. I’ve done pop-up shops in people’s backyards at barbecues, in front of like 15 people. I’ve done pop-up shops at Facebook’s headquarters. I’ve done at real bakeries, at art galleries, but I love the more bizarre places where you can have these funny stories and connections, and sometimes free food.

Through that journey, yes, I’ve definitely had to ask for help and wholesale wasn’t for me. So I stopped doing that earlier on. We work with different freelancers here and there. I have a few, a couple of full time freelancers, Dale Malott, or he goes by dillustration. And Corey Reifinger. They both have been great. I do some stuff with, for doing a collaboration with a company, sometimes they have artwork in their archives that you have to abide by and go by. So we have a set book of rules that you can’t let bugs bunny’s whiskers go in this direction or that direction. Sometimes we use other people’s artwork if it’s a licensing deal or collaboration. I do a few things with my buddy Travis Price over in Australia and yeah, every now and then we’ll mix it up with some different designers here and there. Those guys are with me a lot and we have a lot of stuff in our archives too. Like I think when a brand has a logo, it’s important to always have a handful of those shirts in stock. People want the classic logo, so we’ll put different polka dots or stripes, different bits in there.

At one point I did have a lot more employees, and I had a much bigger office and it was great. Before I knew it, I kept giving people raises and bonuses, but at the same time, my rent kept going up and the cost of shipping and printing kept going up. Then you have an independent brand and you make a few mistakes around the same time, you have to untangle that mess and come up with a new solution. So we’ve definitely figured out a way to adapt, and it was heart wrenching.

I had to let go of I think seven people in my office of 12. It was a big cry fest. It was emotional. I have people with me for a long time, but I was never much of a numbers person. I just wanted to make fun things. I was like Tom Hanks and big, and I just wanted to do all this fun stuff and you got to pay attention. You got to hold people accountable. You can’t just, I don’t know, but yeah, I had to make some big transitions. Within 24 hours, we started getting so much work done, more than we ever have with twice as less people. I think there was just a lot of things that could have been different. Like we had these meetings that never went anywhere, but we wanted to do them because I don’t know, it just felt good having a meeting and doing a little show and tell what everyone’s working on, but it took up a lot of time. I signed a lease for an office that was so big and it was like $130,000 a year for this space, plus all of the problems that came with it. It was tough, but the biggest thing I learned is that you can do a lot with less and within 24 hours of making that tough transition, we started being 10 times as productive. We started having releases twice a week instead of a couple times a month. I also learned how valuable it was to work with freelancers. So definitely, I had my guy, Corey Reifinger come down from Connecticut and he moved here, and with this family and it broke my heart to have to make this transition with my brand, but we kept him on as a full time freelancer pretty much in trying to go with the flow. Every business has it. I don’t know. Have you had any moments in your time with the brand, where you’ve had to make those tough decisions?

Dan Cederholm: Yeah. Yeah, yeah. Certainly, especially early on, we didn’t know what we were doing at all. A lot of the things you’re saying resonate with me in terms of wanting to make things, and that was the most fun of it for me. The rest of it is just as important, but it took a while. I think I had a co founder, Rich Thornett. So that made it a little easier and that we had complimentary skills, but after years of trying to learn on the job, we realized, wow, we really need some help. That was the letting go part. Like where it’s hard to let go off something you’ve created from scratch. That was really difficult. It still is difficult to be honest. I think once you get to a better place, then you realize it’s worth it.

Johnny Earle: It is. It is and for me, I think my wake up call is when I married. My wife is an auditor, so completely different type of person, but she’s asked me a lot of difficult questions. She turns down most of my ideas and tells me they’re not going to work. At first, it made me really sad. I was like, now this person doesn’t even care about me. 24 hours would go by and I’d be like, “Oh my God, this person really cares about me.” She’s right, she’s always right. She would ask me difficult questions, like what does that person really do and how do you hold them accountable, and how do you know they’re really doing that? I didn’t want to stand over an employee and I thought they were all like, we were this big group of friends and I just had this, I don’t know, I was young and I wanted to have this club house of friends more than anything. So I didn’t feel comfortable standing behind someone and holding them accountable. I would rather just give everybody the benefit of the doubt because I’m a very trusting person, and I like to think everyone is a good person, but I own the company, and I am cutting the checks so there could definitely be some resentment if someone works with you. Nobody really, people want to be independent, but at the same time, they will take comfort being with somebody else, being with another brand. So I should have made that decision to let people go. I was advised to make that decision three years prior, but I didn’t have the heart to do it. So I kept making up, maybe this collaboration with G-Shock or the Simpsons will be the big thing. We almost started dabbling in wholesale again, which is something I never ever, ever wanted to do.

I think that was a wake up call for me, because I started to sacrifice my brand beliefs to pay for people that I essentially didn’t need. I don’t say I didn’t need like they were useless, they were all useful, and they helped the brand grow tremendously, but it got to a point where I grew way more internally before externally with our sales, and events, and all that stuff. So definitely, love everyone and thank everybody that’s been a part of the journey. We wouldn’t be here without them, but now it’s great. I’m learning to have a balance. I’m making time to be more present in my personal life, picking up old hobbies, loving working with a smaller team. There’s just a lot more clarity and a lot less noise, but freelance is great. Through Dribbble, I’ve definitely found quite a few people over the years where I’ve had to get help on a couple of one off projects.

Dan Cederholm: All right. Right on, that’s great.

Johnny Earle: At first, I’m like how many Bs do I have to type in? Is it three? Is it four? I try to think of a basketball and how many bounces you do. I was like, I don’t remember seeing an address. I think it was Salem, Massachusetts, was it?

Dan Cederholm: Yeah.

Johnny Earle: It’s like these guys are in Massachusetts. This is so wild, but yeah, the brand, it’s a really wild story. It’s something that you can’t really explain to someone in a minute or two.

Dan Cederholm: That’s true. I mean, right. There’s still an aspect of mystery to it, which I think is fantastic. Just wanting to know what the story is, and you’re in a better place now with the business and everything. Where do you want to take it next?

Johnny Earle: Yeah. There’s been so many different parts of the business, like when I was building out my Los Angeles shop, I worked with a company that builds Jeff Koons’ balloon animal sculptures. I had a $60,000 budget, and I spent over $600,000 to make ovens that don’t cook anything. I didn’t have this magical bag of money, and I didn’t want any investors. So I gambled my house to get money to make ovens that don’t really cook food, because that’s how much I was willing to give blood to make this Willy Wonka experience of a retail store. I knew in my heart that there has to be some value from it. So they built ovens that open and close, shoots steam out at random times, the giant entrance to the shop is a 13 foot tall oven that secretly opens. You check out over a stove top with fake fire.

So we made it impossible to not talk about, and received millions of dollars worth of free advertisement, free press features on TV, Los Angeles Times. As my lease was up and as I was experimenting with so many pop-up shops in how the flexibility, the less headaches and the finances are so much more flexible and fun and easy, I just decided to do more pop-ups in Los Angeles and not renew the lease. When I opened up that store, I did not negotiate. I was in my early 20s and I just wanted to move in and it was in 2008 right before the recession. I went in at almost $10 a square foot where everybody around me, a couple months later are paying a dollar a square foot. We still made it work and we still made a profit and built a community, but it wasn’t as flexible and profitable as a pop-up shop. I learned that through experience. Over time, each year we make a few million dollars in sales. Some more than other years depending on what risks we want to take, and what big collaborations we have coming out, but that is where we try to maintain the brand because it allows me to employ my mom, and my sister, and Kelly and Mary and John and the people who’ve been with me for a really long time. It allows us to experiment with different projects, to have our office and that’s-

Dan Cederholm: That’s awesome.

Johnny Earle: Yeah, and we’ve got some great features on different spots, different magazines, television shows. Where do I want it to go? I think the past couple of years have been a great time for clarity. I want to make time to be healthy. I want to make time to do more talks with lovely podcasts like yours. I do a lot of speaking engagements, which I fell in love with. Just help. I wish I went to a talk when I was starting my brand, because I could have saved millions of dollars worth of mistakes. If I had just listened to what other people are screwing up on, or succeeding at. So I want to be more present. Work is great. I love every part of it and I love the team that we have. It’s a well oiled machine. We have new releases twice a week and when we sell out of a product, we usually never make it again. So it becomes a collectible.

We have a customer in Belgium on Maze. She owns over 1,000 Johnny Cupcakes T-shirts. We have a lot of people that own more than 100 Johnny Cupcake shirts. I’ve met more than 2,000 people with Johnny Cupcakes Tattoos. 2,000 people I’ve seen neck tattoos, face tattoos, back tattoos. I saw a tattoo on someone’s tooth. I don’t know how they did it, but I like to call it a tattooth. I’ve seen tattoos in places I wish I didn’t see, but everyone’s been inspired and motivated to start their own business, or live a healthier lifestyle. Then I started being invited to do some creative consulting for some different brands. One big one was Gillette. We brought back their mascot from the 1950s, and we did a campaign for Father’s day a few years back. Have a potential project with Mondelēz. Right now they own Sour Patch Kids, Oreos, Nutter Butter, Trident. That’s where I get a lot of fulfillment is going into someone else’s space, someone else’s company and giving the owners or the team a bunch of ideas. Then it’s like I could get my inability to sit still works out to my advantage when I can go into another person’s environment. So for the future, yeah we want to do more consulting, more creative consulting, more speaking engagements. I’m working on a book right now.

Dan Cederholm: Fantastic.

Johnny Earle: The brand I love … Thank you. I love what the brand just keeping it the way it is. I don’t want to be in a million stores. I don’t want to sell out. I don’t want to get any investors. Maybe this will change someday in the future, but I’ve been going strong for, we’re coming up on our 18th year of being in business and very proud of everything that the team has accomplished. Yeah, I mean I think one day I want to open a haunted house, that would be pretty sweet. I’d like to write children’s books. I want to be a dad too, that’s my big thing too. I want to be a present dad. So right now I’m trying to put a lot of things in place so that I can be a really cool dad, and that’s really my number one goal.

Dan Cederholm: You probably already have a children’s line.

Johnny Earle: We do make sure it’s for kids, yeah. I think that’s going to expand doing more kid stuff. We did some shirts for dogs recently. We even made our own poo poo bags so you could pick up your poo in style.

Dan Cederholm: Yeah, I need some of those.

Johnny Earle: It’s our crappiest product yet but if we’re digging it, and I don’t know.

Dan Cederholm: You’re having so much fun.

Johnny Earle: I am. I am having fun. I had a couple of bumps in the road, but every bump is a learning experience. I screw up every day. Today I woke up to a call that my summer shop on Martha’s Vineyard flooded. There’s a foot or two feet of water in the store, and last week our heat broke in Boston when it was zero degrees. Obviously we sent our employees home and we had to pay, which is totally fine. We offered to pay everyone’s shifts while they were home, but we weren’t able to conduct business. The first 10 things we tried getting the heater fixed, it didn’t work. Every day it’s something, but you have to have a sense of humor if you’re going to be a business owner, or you’re going to be a very sad business owner. I think the biggest thing entrepreneurship teaches you is the ability to adapt, to roll with the punches. If you can have a team of people who approach problems with solutions rather than panic, then you can accomplish some pretty cool things. If you’re not afraid to ask for help and to switch things up when you’re not having fun anymore, you can never lose focus on why you started doing what you do. It’s a great reminder when you listen to cool podcasts like this, or when you go to a business seminar, or a networking event and you got to make time to talk to other people. It’s like therapy talking to other people that own businesses.

Dan Cederholm: It really is.

Johnny Earle: It’s also okay to work for someone else too. There’s definitely been times where I’ve said, “You know what? That would be kind of cool to shut things off at 5:00, 6:00 and not think about anything for the rest of the night,” but I do. We have a lot of bad reviews on all the food websites out there, because people get upset that we don’t sell real food.

Dan Cederholm: Have you ever sold cupcakes?

Johnny Earle: We did. We did sell cupcakes on April fool’s day, and we hid all of our T-shirts. We had customers that drove down from New York City, New Hampshire. We said, “Why would we sell T-shirts, we sell cupcakes. This is Johnny Cupcakes.” We videotaped everyone’s reactions, and you can view the video on YouTube if you type in Johnny Cupcakes April fool’s Day.

Dan Cederholm: We’re going to link that up in the show.

Johnny Earle: If you go to my YouTube channel, you’ll be able to see a lot of these things that I’m talking about. One more thing I’d love some of the listeners to hear about, just to give you an idea, a better idea of the brand. Around Halloween, we released Halloween theme shirts. I always thought it would be fun to release scary shirts at nighttime. So the only time you could buy them is if you go out in the dark to get your scary shirt. We even went as far as making movie titles for movies that don’t exist, like Count Spatula, and Rise of the Two-Headed Zombie Chefs, and we put the titles on the shirts. We made movie trailers on YouTube for movies that don’t exist. These were like, you would think there’s a real movie coming out. We worked with real actors, special effects people that have worked on popular movies.

Then to make it even more exciting, we showed movies in the windows. We had a costume contest at the shop, on my flagship shop on 279 Newbury Street in Boston. People came out from all over the place. Even people that didn’t want to buy something, came out for the chance to win. So we were able to create a community of customers. We rented a popcorn machine, our employees dressed up like zombies, like movie theater attendance, and we packaged the T-shirts inside VHS tapes. So you get your movie theme shirt inside of VHS tape that you can collect, and they all had different graphics on them. What else can you do to like, where do you go from there? I was like, let’s rent out a hearse and a coffin from a creepy guy on Craigslist for $220. So I did, and I got personally delivered inside of a real hearse in a real coffin when we opened the doors to this T-shirt release. It was definitely scary being in that coffin.

Dan Cederholm: How long were you in the coffin?

Johnny Earle: Longer than you think because I wanted to build up excitement and hype, and drive around the block quite a few times. So it was quiet in there. I think I found a piece of hair on me that was not my hair. I think that really got me, but you know what? That small investment got people talking about this for life, and we had a line of customers across the street that was as big as the line of customers on our side of the street, filled with people trying to figure out what the heck was going on. Every one of our customers acted as a brand ambassador and shared the story, and it was great. So I’ve rented out ice cream trucks in different cities, where we’ve sold ice cream theme shirts, and ice cream theme packaging out of ice cream trucks with real ice cream that we gave out with each purchase.We’ve done collaborations with Ninja Turtles, with Hello Kitty, with Looney Tunes, with Power Rangers, with Marilyn Monroe’s Estate. We’re working on a really big project this year, prior biggest project yet, so it’ll be a fun surprise. So yeah, I mean keeping people surprised, keeping the mystery, making people feel good, and always thanking customers, always coming out with new fun packaging. We work with hundreds of charities every year. We don’t always announce it, but every day we have requests coming in and we put together gift baskets for auctions, for charity events. So if anyone listening has a charity that’s near and dear to their heart, feel free to reach out to us.

Dan Cederholm: Well it’s fantastic.

Johnny Earle: Another thing that puts your company and your work life balance into play is health. Sometimes it takes a near death experience to realize how valuable your time, and your happiness is.

Dan Cederholm: Absolutely, yeah.

Johnny Earle: I got in an accident and once with my band, and we were supposed to be dead. We flipped over three and a half times on Route 85 in North Carolina. That put things into perspective. My mom was in Barbados in October, and she was walking on a cross walk and her and her friend got struck by a vehicle. Someone stopped but another car rushed around that vehicle, and it killed my mom’s friend on the scene. My mom was not, we didn’t think she was going to make it. We had to get her med flighted back here. She’s on her road to recovery. Actually tomorrow she gets to go back home. She’s learning to eat again, learning to walk again. It’s been a very unpredictable, and a very difficult few months or year for me. These are all just reminders to slow down, and to make more time.

Even though you build a company for freedom, but easily that company can turn into a time suck, or your own prison if you don’t learn to say no, and if you don’t build different processes, and hire the right team. So yeah, my goal is to family number one. Family, family number one, always has been but even more so now, I would rather make less sales and be at my store or office less. It’s nice to maintain a few million dollars a year each year, but as long as I could keep my employees and have a little room to play with, to make the brand magical and to have just in case a store explodes or a water pipe breaks, I could get by.

Dan Cederholm: You started by saying you got into this to spend more time with your family, and we kind of came full circle there.

Johnny Earle: Yeah, and I do spend time with them because I work with my mom every day, and I worked with my sister every day. I see them every day and it’s great. I want to make more time for my cousins, and my cousin’s kids and my future family.

Dan Cederholm: Well that’s super inspiring. It really is. Thank you for your time today.

Johnny Earle: Yeah, anytime, anytime.

Dan Cederholm: It’s been really inspiring in a lot of levels, and just hearing the stories from you is just so cool. People obviously can find you if they’re in Boston, Newbury Street in Boston, but

Johnny Earle: Yeah, @johnnycupcakes on Instagram, Twitter, YouTube, Facebook. I could tell you so many stories, but if you don’t live near Boston, there’s a chance you could still be a part of a Johnny Cupcakes experience. A year, two years ago, I started a program called the cake dealer program.

Dan Cederholm: Cake dealer?

Johnny Earle: Yeah. So we teach entrepreneurship to Johnny Cupcakes customers in different states. We teach them how to run successful pop-up shops, how to be an event planner, how to utilize social media. We give them 30% of whatever they make, and then they can also earn extra bonuses every month. So as I’m speaking with you now, there are people doing Johnny Cupcakes pop-up shops in different states, or planning them and it’s giving me more time to be with my family and it’s giving them, and we get to share this entrepreneurial journey with other people by giving them the keys to the brand. There are a lot of cities that we don’t have cake dealers in yet. So if there are any creatives that are listening, that want to have a little side hustle, feel free to hit us up. On our website, there’s more information about that.

Dan Cederholm: What a brilliant idea. It’s almost like a franchise in a way.

Johnny Earle: I got to go back to my Tupperware roots a little bit, but yeah, it’s a very personalized franchise. We don’t let anybody do it. It’s a very strict interview process.

Dan Cederholm: You’re teaching them some invaluable lessons.

Johnny Earle: Yeah. Teaching them as much as we can, and sometimes we learn from them too. I don’t have it all figured out. I never studied business, I never studied design. I make mistakes every day, but I don’t care about making mistakes. I look at every mistake as an experiment, and experimenting is how you grow. I’m just a little guy who’s not afraid to fail. So if I can do this with something as weird as cupcakes on T-shirts, every single person can come up with a cool idea. You just have to roll with the punches, have fun, be able to ask for help. Make time to learn and if something doesn’t work out, I started 16 businesses before this one. So other doors will open for you if you stay open minded, and stay positive. Everything’s valuable that you learn the mistakes more than the success, because it keeps you on your toes and you never forget those experiences. So keep your head up everybody. You got this.

Dan Cederholm: I love it. There, it’s such great advice. It’s amazing. Thank you so much, Johnny, for being here.

Johnny Earle: You got it. The listeners can come to the shop sometime where you and I are going to do a live Q&A at some point at the Johnny Cupcake shop.

Dan Cederholm: Yes, we have to make it happen.

Johnny Earle: Do a special edition Dribbble T-shirt too.

Dan Cederholm: Oh my gosh. Okay, now that would be incredible. Yeah, so actually stay tuned for that. We’ll keep everybody updated. Thanks again, Johnny Cupcakes.

Johnny Earle: Anytime. Thank you guys for listening.