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Johnny Cupcakes: A T-Shirt Mogul and Multimillionaire

Johnny Cupcakes rolls a fresh oneA few weeks ago I was in Cape Cod – I was doing research for a Lonely Planet guide to New England – and after I’d wrapped up my research in the area, I decided to take a weekend off in Boston. I’d only been to Boston once before, but that was way back in the late summer of 1997, and I wasn’t even in the city for a full 24 hours. I only remember walking through Chinatown, and then spending part of the evening in Cambridge, near Harvard Square. So in other words, I didn’t really see the city at all.

Unfortunately, my Big Plans for the weekend ended up falling through. I was supposed to get together with a freelance writer friend from Pittsburgh who had relocated to Boston about a year ago for work. But I got blown-off, big time, and in a really embarrassing sort of way. I’m not spilling any of the nasty details, though, so please don’t ask. (If you do want nasty details, however, you’ll find those en masse on the pages of the Marriage Without Monogamy column I write for Tango.) 

After the weekend in Boston was over, I drove back to Philly, even though I still had a week’s worth of research to take care of in Connecticut. Somehow, I’d picked up a nasty case of strep throat during my time on the Cape, and all I could think about was how bad I wanted to spend the next two or three days in bed, with C feeding me chicken soup and popping her mystery prescription pills into my gaping maw. And probably because I have a tendency to be nearly as masochistic as I am sadistic, I sent an email to the freelance writer friend in Boston. And while I didn’t exactly come out and ask her what had happened, I hinted at it, in a sort of passive-aggressive (but still technically polite) sort of way.

The result? Nothing whatsoever. One more blow-off. And probably, one more friend who has pemanently taken me off her proverbial Christmas card list.

Seriously: This has been happening to me a lot lately. To wit: Things will be trotting along just fine and dandy with a particular friend or acquaintance, and then seemingly out of nowhere, the emails stop being replied to, the voicemails stop being returned… and eventually it occurs to me that this person – once a good friend who may have even shared a good number of personal and private secrets with me, but now someone who just wishes I would go away – is probably trying to send a great big obvious hint.  

I’ve been asking myself why this has been happening with so much regularity lately, and I was talking with C about it the other day as well, and we came to the conclusion that this is just one of the unfortunate effects of growing older. I’m not sure I even believe that conclusion entirely, but then again, it is true that childhood and adolescence, to some degree, are all about friendships, whereas most stages of adulthood are not. Probably none, now that I think of it.

What I mean is that up until a certain life stage – high school graduation for some of us, and university graduation for others – our friendships, and to a slightly lesser degree our romantic relationships, make up the collective center of our universe. We do so many things with our friends during those life stages – as opposed to doing things alone, I mean – and sometimes we do so many things with big groups of friends. I remember quite often hanging out with large groups of people during my college days, and I suffer from Generalized anxiety disorder, so that’s saying something!

On the opposite end of the spectrum, it’s been ten years since I graduated from college – I’m almost 35 years old, and I’m a self-employed journalist who works out of a home office – and I can honestly say that aside from family gatherings and work-related events, I don’t even remember the last time I hung out with more than two other people at the same time. 

A certified Young Pioneer, de-stressingI was lucky enough to have parents who paid my way through college, so even though Real Life and all its attendant lessons didn’t begin for me until the day I was handed my university diploma, I did at least get to enjoy an extra four years of adolescence. And while a large part of me now regrets how irresponsibily I treated those bonus years, another part of me remembers how much unabashed fun I had – just straight-up, no-strings-attached fun. (Thanks Mom & Dad!) But life just isn’t like that anymore, and of course, that’s because I wasn’t living in the Real World during those days. But I’ll tell you what: I’m sure as hell living in the Real World now. 

= =

Anyway, enough of the depressing stuff. Friends come and friends go, right? At any rate, if you happened to see the title of this post and you’re still reading, I’m gonna guess that you’re either very interested in my personal life, or you’re not familiar with Johnny Cupcakes. (That’s him in the photo directly above, meditating inside a circle of birthday cupcakes. That’s also Johnny in the photo at the very top of this post. He appears to be rolling dough in a kitchen, but take a closer look – he’s actually rolling a Johnny Cupcakes T-shirt.)  

I had never heard anything at all about Johnny Cupcakes until my recent weekend in Boston – I hadn’t even heard the name. But during my last night in town, even though I was feeling absolutely miserable because the strep throat was at its worst, and because I still wasn’t on antibiotics, I forced myself to get out of the hotel and to do a little exploring. I nearly hopped on the subway, because I had a long list of bookstores I was dying to check out in Cambridge. But my hotel just happened to be on the other side of the Boston Common from Newbury Street, which I’d been wanting to visit for eons, ever since I first started seeing advertisements in independent and underground magazines for Newbury Comics. So I crossed the park, and by the end of the night I had walked from one end of Newbury Street to the other, and then back again.

If you’ve never had the pleasure of window shopping along Newbury yourself, it’s easy enough to imagine: Think of a wide, tree-lined, perfectly straight boulevard that stretches on for eight very long blocks – two miles long, in fact. It’s packed on both sides with pricey retails shops, trendy boutiques, cafes, bookstores, upscale eateries, and the occasional office space and apartment building. From what I could gather, the retail value seems to drop along Newbury Street as you get further and further from the Boston Common, which is where Marc Jacobs and Chanel and other boutiques like those are located.

But if you keep on walking in the direction away from the park, you’ll start to find businesses of a much more interesting sort. Trident Booksellers & Cafe (338 Newbury Street) was one I stumbled upon. (Try the breakfast burrito.) According to Trident’s Website, it’s “the last remaining independent bookstore in Boston proper.” I find it almost impossible to believe that Boston, of all places, has just one non-chain bookstore, although when you consider all the bookshops located right across the river in Cambridge, I suppose it’s not quite as bad as it sounds. But still.

Anyway, I was maybe three-quarters of the way up the street when my stomach started growling, and that’s probably why I noticed a small shop across the road with black awnings. This was Johnny Cupcakes. The store’s logo was a cupcake with crossbones underneath, clearly a play on the skull-and-crossbones design. I’m well aware of the relatively new cupcake cafe trend, and so when I saw the Johnny Cupcakes logo, my initial thought was that I had just stumbled upon the first ever hipster-owned, punk rock cupcake boutique. My mind was fairly blown at the thought, and even though I am not at all the type of person who would pay $4.00 for a cupcake, I more or less resigned myself right then and there to making a purchase. I was hungry, for one thing. And I was just absolutely floored by the business idea. It’s got to take a pretty heavy set of balls to open a punk-rock cupcake shop down the street from Banana Republic and Ralph Lauren, after all. 

So I ran up the stairs and into the cafe, and the first thing I noticed was the huge amount of unusual merchandise for sale. Really cool designer T-shirts; one-inch buttons – stuff like that. It wasn’t until I had literally checked out the merch lining all four walls, however, that I realized I hadn’t found the cupcakes yet. There were authentic bakery racks lined up in front of a brick wall, but they were all being used to store and display more T-shirts. Even the glass display case next to the cash register held no baked goods – just more T-shirts. That was when I noticed a big sign hanging on the wall. It was filled with text, and once I began reading it, I realized it was a brief history of the Johnny Cupcakes empire itself. The first line was printed in oversized type. It said, “I started this company as a joke.”

I won’t bother explaining the entire story here, but if you’re interested in learning about one of the most unusual T-shirt and merchandise companies in the country, you can read about it yourself by clicking here. And if you live on the west coast, mark your calendar: A new Johnny Cupcakes location is opening soon at 7959 Melrose Avenue in Los Angeles. According to the clerk I spoke with at the Newbury Street store, the L.A. shop is going to be full of surprises that won’t be fully revealed until the grand opening on Saturday, August 2, 2008. There’s a slight chance I might fly out for the opening, and there’s also a chance I might be writing about Johnny and his brilliant business for an upcoming issue of Paste magazine, so check this space on August 2 or 3 for photos and updates. (And click here to read my first article for Paste, a brief profile of Heartschallenger, the world’s most creative ice-cream truck company.)

UPDATE: The Johnny Cupcakes Los Angeles shop is now open for business, and what an incredible place it is. It’s destination retail in the extreme. To check out a professionally-produced video of the new store, click here.

And in other news: I unfortunately never did manage to sell my Johnny Cupcakes pitch to Paste magazine, but I did recently get a chance to personally meet and interview Johnny, just the same. As I’ve mentioned before on these pages, my fiance and I are currently in the process of launching a professionally-designed, newsstand quality magazine about creative and alternative entrepreneurs.

Young Pioneers is the title of the magazine, and Johnny Cupcakes graciously agreed to be our very first cover star. My plan was to check out one of Johnny’s very popular college lectures about creative entrepreneurship, and to then interview him at his company headquarters the following day, where we had also scheduled a photoshoot with the incredibly talented Dave Green, a very friendly Boston-based freelance photographer. So in early February 2008, I spent nearly an entire day driving from Philly to Boston in a terrifying snowstorm. I managed to find my way to the gorgeous campus of Bentley University, which was absolutely drowning in snow, just minutes before Johnny took to the stage in a large lecture room there, and started sharing the story of how his business came to be. (For proof of just how harsh the weather was that day, take a look at the photo of the official Johnny Cupcakes van, below, parked outside the company’s headquarters in Weymouth, Mass.)  


Johnny’s talks about alternative entrepreneurship and the history of his company have become so popular, in fact, that colleges and universities all across the country are now booking the guy like crazy. Johnny does manage to keep a fairly well-updated schedule of his lecture circuit on his MySpace page, and he also occasionally gives advance notice of those appearances on his very popular blog, so check out both of those sites if you’re interested in seeing Johnny when (and if) he comes to your part of the country.

  1. September 9, 2010 at 5:55 PM

    Wow, great read and feel lucky I ran across this blog

  2. June 5, 2010 at 12:01 PM

    Your web is awesome..pls dont’t forget to visit & enjoy my web too 🙂

  3. June 12, 2008 at 9:22 PM

    I thoroughly enjoyed reading this. Thanks for all the good hype.

    Johnny’s Mom

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