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Introducing: The First Annual “Wipe Your Buns With $30,000” Challenge! (Haha, I’m Not Even Kidding.)

In: Starting an Online Business

I know. I KNOW. I bring such an air of sophistication to everything I do. (See also: The Middle Finger Project, our Unf*ckwithable line of classes, and the sweet, sweet letterboard in my living room that reads, “My Name is Inigo Montoya.”) But let’s be honest: “The $30,000 Money Challenge” just doesn’t have the same ring, does it? You know when I’m in your inbox. And you also know when I show up to teach you something, it’s going to be GOOD.

Which brings me to today! And the title of this racy little post! Because—surprise—I really am kicking off an all-new challenge called, “The First Annual ‘Wipe Your Buns With $30,000’ Money Challenge.” It’s you + me, for the next thirty days, where I’m going to walk you step-by-step through how I went from making $30,000 a year, to making my first $30,000 in a weekend—all by using one little (terribly underutilized) business strategy.

I should back up.

Etttttt! Etttttt! Ettttttt! Etttttt! That’s the sound of me hitting reverse in one of those giant construction trucks, wearing a hard hat and looking like a baller. Or one of the inmates from “Orange is the New Black.”

Once upon a time, in a galaxy far, far away, I was a twenty-something creative writer who still believed that sausage didn’t really come encased in an animal’s stomach lining 🤢 and that bobby pins were supposed to be worn with the longer side down (NOT! TRUE!). I also believed that if I worked really hard, little fairies would fly down from the sky and grant me all of my wishes and probably make me a millionaire. Or something like that.

Turns out? Freelancing is hard and money is WEIRD. I spent all of my time, back then, working from dusk until dawn, hunched over a computer in some kind of inescapable matrix fueled by buffalo dip and the fruit sweat of my loins. Every day meant some sort new version of tortuously long to-do list, and just when I thought I was getting ahead, I’d end up being drowned by Some Other Freaking Thing I Had To Do, so it always felt like I was spinning my wheels and never actually getting ahead (or having a life or this thing called “freedom” everyone was talking about). In effect, I had hand made my own prison. (Orange is the New Black reference wasn’t too far off!)

This is a common thing among freelancers + entrepreneurs. Bunch of over-achieving loons, we are. We want freedom from the rigidity and monotony of the standard 9-5, and so we strike it out on our own with our skills and talents and knowledge, but then we end up creating a self-perpetuating trap for ourselves because instead of working eight hours a day, now we’re working twenty-four. Or damn near close.

And this is not the point.

I didn’t want to have to decline invitations to Sunday brunch because I had to work. I didn’t want to have to stay inside the hotel while the rest of the fam vacationed because I had to work. I didn’t want to have a desperate lack of boundaries between my personal life and my work life. I didn’t want to have to sacrifice my quality of life, for a quantity of money. But once you’re in this thing, you wake up feeling like if you don’t? Every day is another day you could be fired. The constant threat of total and utter self-destruction! So, you soldier on. You figure that eventually you’ll work it out and get a “system” into place. You figure that one day soon you’ll be one of those people with color-coded day planners, and you’ll learn how to say no, and you will be A Person Who Is On Top Of It.

Until the next client calls and sends you into yet another cycle of overwhelm and despair.

This was my life ten+ years ago when I first started freelancing in Philadelphia, unsure of what the hell I was doing. And it probably would have kept going that way, were it not for one surprising little business model tweak I accidentally stumbled upon that changed everythinnnngggggg, and even made me skinnier. (Kidding, nothing makes me skinnier. Nothing, I tell you!) Bottom line: I went from making $30,000 a year, to making $30,000 in a weekend. Which, is like, UNHEARD OF FOR A GIRL WHO GREW UP IN A TRAILER PARK, Y’ALL. Thirty thousand dollars might as well have been a million. But because I trusted myself enough to try something different?

I learned how to make money like the big boys.

I’ll give you a hint: it has nothing to do with the type of work you do, and everything to do with the kind of container you place it in. I know that doesn’t make sense to you at all yet, BUT IT WILL. That’s what we’re going to be talking about for the rest of the month: how to make real money as an independent. Not the kind of money where you’re barely scraping by, always waiting for the next client invoice to be paid, but to make the kind of money where, if you really wanted to, you could say, “I’ll wipe my a** with $30,000 and still be JUST FINE.”

Hence, the name of this delightful initiative. Except I changed “ass” to “buns” because #advertisingrules.

Tomorrow, we begin! If you want in, join our mailing list anywhere on the page. 🙂 I can’t wait to share what I know. Maybe if we all start making $30,000 in a weekend, we’ll overturn the patriarchy a whole hell of a lot faster and, you know, buy really nice shoes. The important things in life.


Xoxoxox from Costa Rica (and soon Philly, and then London, to speak at Magic Maker Live in October. Are you coming?!?! I can’t wait to see yo’ face and have a cocktail with you!)

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Introducing: The First Annual “Wipe Your Buns With $30,000” Challenge! (Haha, I’m Not Even Kidding.)

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I know. I KNOW. I bring such an air of sophistication to everything I do. (See also: The Middle Finger Project, our Unf*ckwithable line of classes, and the sweet, sweet letterboard in my living room that reads, “My Name is Inigo Montoya.”) But let’s be honest: “The $30,000 Money Challenge” just doesn’t have the same […]

In: Starting an Online Business


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Confess. You’re reading this because the title made you think of male genitalia. (…And now you’re thinking about how weird the word “genitalia” sounds.) I know, I know. I tried to avoid it, but really, I can’t. Because today’s tip is about packaging your service or product offerings, so why be modest? I’m not even […]

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You discover things you never knew about yourself. For example, you know how sometimes people play that annoying game and ask you what you’d do if you only had 24 hours to live? And so you sit there and scratch your ass, and then say something poetic like, “I’d go to the beach and let […]

In: Starting an Online Business


I'm a Bad Influence on Women

Hey, I’m Ash! Twenty years ago I was a small town girl growing up in a trailer park in rural Pennsylvania. Fifteen years ago, I lost my family and everything I knew right as I became the first to graduate college. Fourteen years ago, I found myself leaving everything behind for a new life in the city where I could be “normal.” Ten years ago I realized normal was the most disappointing thing that ever happened to me. Nine years ago I quit my job in advertising and pursued my dreams as a creative writer. Eight years ago, I built a 6-figure business doing what I love using nothing more than the Internet and my voice. And now, today, I’m the founder of The Middle Finger Project, an irreverent media co. that helps other women find their voice and teaches them to use it to build whatever the f*ck they want to. With a book coming out with Penguin Random House in February 2020 (YASSS, WE’RE A PRODUCT IN TARGET!) I’m proud to be a bad influence on women and guide them into doing something disobediently brave with their life and their career.

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