Ash Ambirge wants you to give your imposter syndrome the middle finger (and you will after this interview)

Joining me is a woman who I didn’t know much about even in preparation for this interview.

Ash Ambirge is the author of a website and now a new book with the same title. It’s called, “The Middle Finger Project: Trash Your Imposter Syndrome and Live the Unf*ckwithable Life You Deserve”

I want to find out how she built her business even though she is banned from advertising on social platforms because of the name of her business. You’re going to love this interview.

Ash Ambirge is the creator of the Middle Finger Project, which helps women figure out how to take an idea and sell it.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy where I interview entrepreneurs about how they built their businesses. Joining me is a woman who I didn’t know much about even in preparation for this interview. I did a bunch of research. I couldn’t find the stuff she was selling. I said, “Where’s your money coming from?” I heard she made money. Where’s it coming from? I know that she used to live in a trailer park. That’s kind of interesting that she started from there and that she’s doing, I don’t know, millions of dollars in revenue, I guess, or over a million.

Where’s the revenue coming from? I had no idea. And then we kind of chatted a little bit before the interview started and I said, “Okay. This is intriguing. We’ve got to talk about this.” Her name is Ash Ambirge. She is the author of a website and now a new book with the same title. It’s called, “The Middle Finger Project.” We’re going to talk about what “The Middle Finger Project” is about. I feel like you should give the subtitle. I was going to read it but I don’t think I’m going to do it justice. What’s the subtitle of the book?

Ash: Well, I mean the subtitle is, “Trash Your Imposter Syndrome and Live the Unf*ckwithable Life You Deserve.” And I don’t blame you one bit because that word is hard.

Andrew: I didn’t mean to say that this will probably have some cursing in it. Not a whole lot but we should be clear about that. I got to say that ahead of time. I think it’s because I’ve got kids who are just five and three and I tell them just about everything just about. So I forget that, yeah, you do have a kid in the car and they’re going to repeat whatever they hear. And all right, it’s not everyone thinking that . . .

Ash: There’s literally a reader advisory warning on the inside flap of this book.

Andrew: And I should say it’s the publisher you told me that came up with that subtitle.

Ash: True.

Andrew: Weird. All right.

Ash: Yes. In fact, they told me that, “Listen, Ash, if you argue against us and you don’t want to name your book, “The Middle Finger Project” with this subtitle, we’re going to fight you on it because it is so perfect for what this book is about.”

Andrew: All right. We’re going to find out where the money comes from. It’s not coming from the book yet because the book just came out. And we’re going to do it thanks for two phenomenal sponsors. The first, if you want to get into the content space, the way that Ash did, you should get a website. And I highly recommend you sign up with HostGator to get it. And if you go to, you get the lowest price possible and you’ll throw me a bone because then they’ll know that my ad worked.

And second, if you need to hire a developer, go to where you get the best of the best developers but I’ll talk about those later. Ash, the money, the highest revenue year for you is what?

Ash: A little under a million, so far.

Andrew: This was what year?

Ash: This was before I started writing a book and locked myself in a way in a room. So where are we? This was would have been 2017.

Andrew: Okay. All right. And then so does that mean that at this point, last year you did roughly the same amount, am I right?

Ash: No, last year we took a huge hit for 500,000.

Andrew: 500,000. Does this mean at this point you’ve got half a million in the bank? Can we say that?

Ash: No, because I spent it all.

Andrew: On what?

Ash: We’ve done a couple of things. I’ve done a lot of growth. I’ve done a lot of litigating. That was fun. And I’ve done some investing. I’m the now property owner in the grand city of Philadelphia.

Andrew: With a down payment is that? Is that what you put up in? This went to down payment or you bought the whole thing?

Ash: Pretty good down payment.

Andrew: Pretty good down payment. How much? What percentage? Let’s talk numbers.

Ash: 50.

Andrew: 50%.

Ash: Yeah.

Andrew: Got it. Why’d you go 50?

Ash: Because I’m a badass and I don’t want that bill.

Andrew: Got it. Wow. It’s got to feel good. And where’s the money coming from?

Ash: So this is what was interesting. We started talking about this. Most people asked me the same question, whether you are someone who has known me in high school or whether you are someone who actually is active as an entrepreneur in this space. A lot of people don’t get it. But every single thing that we sell and every single dollar we make actually happens completely invisibly on the backend via email marketing. One of the reasons for that is because of the name, “The Middle Finger Project.” A lot of social platforms, for example, ban us from actually advertising. So I had to find creative ways starting from day one to figure out how to grow a business and make it happen without ads.

Andrew: So it’s people subscribing to your email list and then they get an ad or an email selling what? What are you specifically selling?

Ash: So, so far it’s dependent on what we are selling at the time. This is one of the things that I’m hoping to get better at this year is systems. But previously it’s just been, okay, what are we into this year? What feels right? What are we making? What are we creating? What’s our schedule? Some of it is affiliate marketing, some of it it’s our products and different programs that we’ve created on our end. Some of it still might contain a one-on-one component but all of the common thread is helping in general women figure out how to take an idea and sell it.

Andrew: Like, you’ve created a course. Give me the highest revenue-generating course for you. How much money did it bring in and what did it teach?

Ash: I think the highest number we’ve done is around 400,000 in one go. And that was for a $500 product. And that would have been one of our signature courses for, okay, let’s figure out how to take your idea and turn it into a business. So sometimes that’s been under different names. We’ve done a lot of testing and experimenting with it. But some of the other things that we sell are supplemental for that. We have different kits for contract templates. We have different script templates for handling, you know, all sorts of different client interactions, whatever it is.

Andrew: Fair to say an info-marketer.

Ash: Fair to say but I would never use that term.

Andrew: I know. It used to be a thing that you could say, but you don’t want to be connected with that. Especially when you’ve got like your attitude. You don’t want to compare it to some of the direct marketers that are operating online. But I get a sense of what you’re doing. I get a sense of where you are in life. I’m curious about where you were. Trailer park, what was that like growing up in a trailer park?

Ash: Yeah, rural Pennsylvania. Single mom, complete social anxiety. Didn’t leave the house. Grew up not really seeing work being modeled for me. So I became very curious.

Andrew: She didn’t work at all?

Ash: No, she didn’t.

Andrew: A check came from the government?

Ash: Social Security disability. Yes.

Andrew: How much money are we talking about did you live on?

Ash: $558 a month?

Andrew: You could do that.

Ash: Yeah, we did that.

Andrew: A family of two?

Ash: We had $200 a month from my dad’s like child support payment until I was 18 but then that expired. But yeah, we did. And I remember borrowing money for toilet paper for sure.

Andrew: Really. And did you feel any sense of shame or any sense of loss for that? Or was it just, “This is my life. This is the way it is”?

Ash: Oh, I was mortified. I would make my mother cry. I would sneak out the back door of the trailer, walk the long way around the block and show up to the bus stop from the complete other direction. So the other kids maybe wouldn’t guess. I mean it worked for like five minutes.

Andrew: They knew where you were coming from. So I grew up in New York, I’ve talked about this a lot. Where there’s a sense of structure, of hierarchy of whether you’re the richest and most powerful person or you’re a nobody. The thing is that the middle sucks but if you are like the trash, there’s a certain glamour that the movies have made that be so cool that people aspire to have that kind of difficulty almost. Were you at that point where people said, “I wish I was like . . . Were you Ash or Ashley back then?

Ash: Definitely, Ash forever.

Andrew: Did they say, “Ash is the badass cool person that we want to be like”? In retrospect, did you see that or no?

Ash: You know, I’ve had people tell me now from high school say, “Listen, you have no idea how much I looked up to you.” Because I was, for all intents and purposes, like the perfect straight-A student, captain of my volleyball team, I was student council president. I did everything I could to overcompensate for what I felt that we lacked. And you know, really I did everything I could to be normal. So a lot of people did admire me and I don’t . . .

Andrew: Did you have the look that you have right now?

Ash: No.

Andrew: Did you have a look? High school I feel like is about whether you have a look, whether you can talk. Did you have a look?

Ash: I was very sweet and innocent. I never drank booze. So college, like I was a good girl. I would go to work at the ice cream stand after volleyball practice, make my $5 an hour and then go home, do my homework and go to bed.

Andrew: Who’s this dairy farmer you were dating as a kid?

Ash: His name was Bradford. Good name, right?

Andrew: Bradford. Cute little relationship, that type of thing?

Ash: Yup. Cute little relationship. Like you know that’s . . .

Andrew: Like Judy Blume’s books. Did you read Judy Blume’s books? I used to love them.

Ash: Yes. Of course, I did.

Andrew: Oh, they’re so good. They don’t hold up though. I went back as an adult to read them to like reconnect with my girly childhood, like dreams of the world. It doesn’t hold up. It’s pretty thin.

Ash: You know what, I mean, literally I would get up at 3:00 in the morning and help this guy go milk the cows.

Andrew: Literally?

Ash: That’s how I love with him I was.

Andrew: And you loved that you were in a shared activity together?

Ash: Yeah. I loved everything about him. He was wonderful. And then, you know, college happened. I actually got a scholarship to college from the founder of You know that company?

Andrew: Just how? You applied for a scholarship that he offered?

Ash: No, he’s actually from a rural community in Pennsylvania. Super poor. When he made it big, he came back and found the poorest county in PA, came to our school, offered this full ride to college for anyone who exhibited a) financial need and b) entrepreneurial spirit. And I won.

Andrew: And you had that as a kid?

Ash: Yes.

Andrew: How?

Ash: So I ended up getting mentored by Andy McKelvey, who was the chairman and founder of He’s long since gone but that was the thing that kind of pulled me out of the trailer park. And really, Andrew, I didn’t know what entrepreneurial was at the time. I had to look up the word. So I bullshitted my way through it, but I think he saw that I had the heart.

Andrew: How did he know that you had the potential for him to pay attention to even?

Ash: Oh, I had a ridiculous scheme that I pulled off. We had to go to Penn State. Everyone had to bring a tangible object that personified their entrepreneurial spirit. And we got kids in there with oboes. Somebody brought like their pet dog. I don’t know what they were doing with that. And me, the ever-present nerd that I was brought this series of octagon-shaped boxes. They all fold inside one another, they get smaller. I had taken all of, you know, the stupid awards that I had won.

Every single good girl thing that I had did put it into a scanner, shrunk it down, paste it onto the side of this octagon, went through, explained all of these, kept going. It was a little long-winded and finally, at the end I said to them, “But everything that I just told you means absolutely nothing. None of those are the reason why I’m the candidate and why I’m the entrepreneur. This is the real reason.” Then I pulled out the very small box and it had this little stuffed animal heart and at the time I was doing it, and I definitely felt cheesy but it worked.

Andrew: That’s what he went for.

Ash: And then I left crying because Andy McKelvey sat in the back of that room in the dark shadows, didn’t say a word. I was being interviewed upfront by a woman named Carol. And at the end, he asked me one question. It was, “If we don’t give you this scholarship, will you still go to college?” And I had to say yes. And then I thought I blew it. I left in tears and everyone knew me as the girl that cried and then I won.

Andrew: Wow. So what did he teach you?

Ash: So it started with a very embarrassing retreat that we had in Western Pennsylvania on my 18th birthday. I was there. He wanted us to understand the value of contributing whatever you can contribute to your community. That’s kind of where his aim was. He wanted us to go back to where we came from and contribute and build the world.

Andrew: To create good citizens.

Ash: Yeah. I mean, really entrepreneurship. He had done a lot with that and he believed in building things. And yeah, that was my first example of someone who was doing work that I admired.

Andrew: I knew that the company was called TMP and I didn’t know what TMP Worldwide meant. Like as I’m talking to you, I’m looking it up. It’s Telephone Marketing Programs. He founded this ad agency to allow businesses to advertise in Yellow Page ads. It was a basically Yellow Page ad agency. He then turned that into this online thing called Monster Worldwide. The firm had 5,000 employees in 36 countries and reach revenue of $1.35 billion by 2007 according to Wikipedia. And he became a big philanthropist. Wow. So through that you changed, you became more entrepreneurial and then at some point you got yourself a job making $42,000 a year. What type of job?

Ash: No, darling. My first job was for $32,000.

Andrew: 32.

Ash: Well, I negotiated up from 28.

Andrew: Doing what? This is as a college graduate?

Ash: Yes. This is a college grad situation. I went off to Philadelphia, I was determined to figure out, you know, what it looked like to do good work and live a life you were proud of. I went to an interview at what was effectively a headhunting agency in Philadelphia for a completely different position at a media company down the road. Big media company doing some bullshit like data transcription. And the interview went so well that at the end, the girl said to me, “You know what, don’t take this the wrong way but would you be interested in working for us because we’re looking for someone to spearhead some of our marketing efforts? We don’t have a huge budget, but you seem great, and I think you’d be great for the role.”

And so I had to decide whether or not I wanted that check on my resume with a big media company or I wanted a little bit more personal agency within my career, and I chose the small company. Best decision I ever made. My boss gave me full reign to do whatever I wanted, and I learned through trial and error.

Andrew: What did you do? What’s an example of something you did?

Ash: Marketing. So this was back number like direct mail marketing.

Andrew: Really?

Ash: Oh, yeah. I got my start there. He hired a consultant, brought that guy in, worked with me exclusively one-on-one to help me figure out what to do, how to run it all. The engine for me was my ideas. That guy told me how to apply them and I just came up with creative idea, creative idea, creative idea.

Andrew: Like what? Name some you’re especially proud of?

Ash: Oh gosh. Well, one of the ones that I talk about in my book that I think is a hoot is when I went to Home Depot and got this like a roll of roofing shingles. And I came back to my desk and I cut out each one and then I wrote on the back and some kind of like paint. “You plus me equals sales through the roof.” And I attached my business card and then had them like, you know, sent to these prospects in the local area because you know, they’re not going to call you from a postcard. Nobody does.

Andrew: And did it work?

Ash: And it worked. Every single person with the exception of one called me. I got all the meetings. Next thing I know the phone’s ringing off the hook. We don’t have a salesperson to go out and handle the calls. So I volunteered and I kept working my way up the ladder.

Andrew: So you’d made it. And still, I keep seeing in things that you’ve written online, in your book, in notes from my producer’s conversation with you. You say, “I did fake it to get the job.” What is it a faking thing? You’re faking as a kid, you’re faking as an adult. What do you mean by faking? It feels like you’re genuinely being interested, got a job that you genuinely cared about, aiming for a life that mattered.

Ash: Oh, I was. Enthusiasm by far was then, and still to this day is the best sales strategy I’ve ever had. But I will say that very much of that was trying to fit in with these very wealthy folks. I was in the Philadelphia’s Main Line. It’s a really ritzy section. I never saw a BMW. I never even saw a Starbuck before I got there. So everything did feel like I was faking it. I had no idea how to dress.

Andrew: But you just didn’t feel like you fit in?

Ash: No. I mean, I was studying these people in these bars at lunch who were ordering $15 cocktails. And like, you know, had froofy hair and calling each other Babs and eating lemon pepper chicken. And I mean, I’m just like, “God, you are so rich. Should we get you some kidnap insurance? Because like I can’t even fathom everything that’s happening right now.” So I tried to play that role and it wasn’t until Corporate America became I mean, just so oppressive. And I had to lean more into my creativity to make things happen that I started getting rewarded for it. And I started realizing that normal was really the most disappointing thing that ever happened to me.

Andrew: And so when you were faking it and trying to fit yourself in, what’s a goofy thing that you did that you kind of look back on and go, “This is not me” and it’s disgusting almost?

Ash: Well, a couple of things come to mind. The fake Claire’s glasses when I was like 23. Definitely I didn’t need glasses but I was wearing them thinking they make me look more sophisticated. But better is that when I went to that first interview with that head-hunting agency, I decided to try on a new last name. I don’t know what kind of a creep does this but my name is Ambirge. I went into that interview and I introduced myself as Ash Ambirgey.

Andrew: Wow, yeah.

Ash: I’m actually the last person in the whole wide world with that last name. No one else exists. So I took a little liberty and then when she offered me the job I was like, “Oh shit, I can’t tell my new boss that. I just lied to her in the interview.”

Andrew: And so you stuck with it?

Ash: So I stuck with it, yes. That’s really embarrassing example but kind of funny.

Andrew: Let me take them home and talk about my first sponsor. It’s a company called Toptal. If you’re out there and you’re hiring developers, I mean really the best of the best developers, you’re going to probably spend days, weeks, months, trying to find them, do it. Our mutual friend Gavin from Acuity Scheduling. He’s someone who you did some creative work for. He went to Toptal to hire people from there because it was fast and he hired people who can change his business. If you’re looking to hire developers, go to Top . . . Are you closing your eyes because you’re like meditating while I’m doing this ad?

Ash: No, I’m just trying not to creepily gaze into them.

Andrew: No. All I do is like look at people’s eyes to get a sense of whether like what I’m saying is landing or not. And when you look down I go, “Maybe this is not working.”

Ash: Oh, no. I know this is for the others listening.

Andrew: No. You know what, David Heinemeier Hansson has been saying, “I want to advertise in email newsletters but they can’t be email newsletters with a pixel that tracks because I’m against tracking.” I go, “But don’t you want to know like if people are opening it and who’s opening it or what?” All I do is look like as I’m talking, I’m checking does this work for you? Is this making sense? I try not to do it to the point where it’s like insecurity but I do care. What is this going too boring? Am I going too fast? And you know, having the video helps me do that. Having a pixel in my email. Yeah, people who subscribe to my email newsletter, there’s a pixel that tells me whether you like the email or not, so I know whether I should continue or not.

Anyway, so I do that with my guests. I will say this to you, Ash, and to everyone else who’s listening, go to When you do, you’ll get the best developers out there. You know what, that’s not how you would say it. How would you think about doing this ad?

Ash: Oh man. I mean, if it’s for developers, I would definitely make some kind of joke about all of the stress that we go through. I’m one of them right now, sitting here going, “God, I really need a developer.” And all the things that happen when your website breaks. The other day, my SSL security certificate expired. Didn’t know. I was like, “Ugh, why, why? Someone should be on that. Why aren’t they?”

Andrew: And that’s embarrassing in this space, right? Well, yeah, you get flagged as being an unsafe site.

Ash: No, I am an unsafe person but yes.

Andrew: I hired, Neville Medhora, the copywriter. I said, “Just help me write better ads for these interviews.” And he did. One of his ideas that I haven’t been able to work into the Toptal ad was he said, “You know, when you’re hiring, it’s usually because you don’t have enough like, people there and too much work. And then you have to go hire someone, which means you’re giving yourself another job, which you don’t have anyone else to help you with. It’s like you need this role.” I can’t express how he said it but he had the magic that I’m trying to figure out a way to express it.

Anyway, that’s too much inside baseball. I’m going to close this ad up by saying if you need to hire developers, go to You’ll get 80 hours of Toptal developer credit when you pay for your first 80 hours in addition to a no-risk trial period. That’s top isn’t top of your head. Tal as in talent. T-O-P-T-A-L dot com slash M-I X -E-R-G-Y,

Ash: Good to know. I will holler at them. Honestly, one of the things that I try very hard to do when I hire anyone is communicate the expectation that, “I’m not going to give you tasks. I can’t manage you. I need you to go in and figure out what you need to be doing and then just do it.”

Andrew: Right. Here’s the thing, here’s the problem. Go solve it for me.

Ash: Find the problems, go solve them.

Andrew: You at some point ended up meeting some mystery man. Who is this mystery man?

Ash: I did. He was Latino. We met salsa dancing and it was now this effort. I think a lot of us can relate once you’re in Corporate America for so long and all of a sudden everything you know, becomes jaded about that. I still was on this grand mission to figure out what it was to do work that mattered to me and live the life I was proud of. And I wasn’t finding that there. It was a very big disappointment for someone who spent a quarter of her life thinking that that’s what I was supposed to be doing and that the pot of gold was at the end of the rainbow.

So what I did was, I enrolled in grad school, as every idiot does when they’re 26 years old. They take out $80,000 in loans, go to grad school. I entered in through linguistics. And when I was studying linguistics, the thought occurred to me that maybe if human beings had figured out how to communicate with one another in hundreds of different ways, maybe they had also figured out hundreds of different ways to be happy. So I started looking in subcultures in Philadelphia, started doing language exchanges with different people, all sorts of restaurants, all sorts of classes and dancing and whatever. I meet this guy as a result. He made $10 an hour delivering frozen food or something.

He seems like the most content person on the planet and I was very curious about him. So I looked at him as almost like an anthropology experiment. We started dating and I wanted to know, how is it that you don’t have this same drive that I do and you’re so happy with it? So that’s what happened. I moved in with the guy. I committed. I was a participant researcher of the highest degree.

Andrew: You did it because you fell in love with him or you did it because you really were trying to understand?

Ash: No, there was a couple of things that happened all at the same time. I mean, you know, I had since quit my job, I decided I was going to become a freelance writer. I was going to follow my passion as they say and ride it into the sunset. I decided to shun money because money had gotten me nowhere. That was my goal. I was making it and I was like, “What? I can put products in my cart at Target, that’s it.” And so when I did that, I ran out because eventually when you don’t prioritize money, you run out of it. And so moving in with him is part practicality and part I mean, curiosity. I felt very woke as the young kids say these days.

Andrew: So you got to a place, I wonder about this sometimes too. Especially lately I’ve been thinking like maybe people have heard me in past interviews say, “I want more money. I want more of whatever you got. I want more money, more sex, whatever you got. If I want it, I want a lot of it. I’m not looking to do like the one-mile run. I want 26 miles, if not more.” But I’ve been thinking lately, maybe that’s not the answer. Maybe I’m just chasing things too much instead of just chilling out a little bit and letting things come to me and allowing the things that I am into . . . See, I saw your eyes do something as I said that. It was like . . .

Ash: No. It’s probably because I turned off the AC. I’m in Costa Rica right now, so I’m starting to sweat.

Andrew: I didn’t know. So what you’re saying though is you went in that direction and you discovered, yeah, you were happy but you had no money, which led to no happiness, which led you to get back on the business track but in a different way. Am I right?

Ash: Yeah, that’s right. I mean, things happened but chaotically it wasn’t expected. It was a very short-lived experiment. Things went downhill very quickly. I discovered that the guy that I had decided to very nobly move in with had 20 different identifications in a drawer, all with the same name, all with different photographs. And so he was a fraud. He was not who he said he was. The name he gave me was not who he said he was. Now I found myself in a very big pickle because I don’t have any savings. I don’t have any more credit on my credit cards. I’ve got $26 to my name and I don’t have any family members that I can turn to and be like,” Ah, you know, let me sleep in your basement.” So that was the predicament. What do you do when you hit rock bottom and you don’t know where to go?

Andrew: And what did you end up doing?

Ash: Well, I decided that I had more dignity going and sleeping in a Kmart parking lot that night than I did kind of staying in that situation.

Andrew: Literally in your car in Kmart parking lot.

Ash: Literally it was a two-door Scion TC at the time. And I was there in South Philadelphia in a very scary Kmart parking lot around 9:00 at night. And I had no idea what to do. And I was crying and I was hitting the steering wheel. I felt like I finally blew it.

Andrew: And I got to ask you something because I know it’s kind of out of order here but you tell that story really well. You’ve told it several times before, right? How can you feel comfortable repeating that story when I have guests who may be told a story one time, like 20 years ago, and I asked them to come back and tell me the origin story of how they did something and they just can’t. You feel natural and comfortable and in the moment as you’re telling that story, this is not an insult. This is something I really want to pick up on and I think is worth highlighting for people. We have an origin story. If we don’t share it well with pride, we’re robbing people with this thing that they’re trying to understand, which is where the hell did you come from? How do you get to the place where you could do that?

Ash: Well, one of the things that I teach is this idea that you have to believe that you are good enough to be received and actually that people will be thrilled to hear from you. I mean with the origin story, yeah, it’s a little bit more fresh for me because it’s been written about in my new book. I’ve been talking about it quite a bit. You know, of course, I’ve sat down and I’ve made points and I’ve made a point of memorizing how I want this flow to go.

Andrew: But as you told me, you didn’t say, “Like I said before, like I said in my book or you probably already know.” There’s some people who almost feel like, “I don’t want to bother you with this. I’ve already said it. You’ve probably read it already.” Without remembering the person listening to us has never heard of me, and they want to know where I come from.” Where does that come from?

Ash: This is just another form of a sale, isn’t it? I mean, it’s a nice sale but really I’m still selling something right now. I’m selling you the next minute of your time. And so with that, a lot of the things that I do also teach has to deal with like this idea that selling is never bothering someone. It’s just a form of helping. Like this is the most generous act anyone can be doing right now is sitting here and taking the time to share. You know, what experiences have you had? What does that mean for the rest of us? How does that contribute to the greater conversation? That’s so important.

Andrew: So when I go into this stuff, I realized when I get interviewed there are times when I do that too. When I think people already know about the greeting card company, people already know where Mixergy came from. I kind of blow past it and shift away. I never know what point do I acknowledge that some people listening had heard it before and I shouldn’t repeat it. What point do I say, “No, I’ve got to be in the moment and tell the story as if it’s for the first time”?

Ash: I think you should have two versions, the long and the short, just like you would a sales page and adjust accordingly.

Andrew: All right. I was also looking at your eyes. I said that and I realized, dammit, I saw that I derailed you in some way and you were trying to judge whether I was, I don’t know, being a [inaudible 00:27:18] or not.

Ash: No way. Seriously. I’m probably just sweating down my ass right now. I swear.

Andrew: I see.

Ash: We’re cool. We can talk about whatever you want to talk about.

Andrew: What are you doing in Costa Rica?

Ash: I’ve had a house here for the last eight years. I live here part-time.

Andrew: All right. So you get down to no money and at some point you say, I got to get on track.

Ash: Yeah, that night.

Andrew: That night.

Ash: When you’re like, “Oh shit, I’m sleeping in my car. I cannot do this. I’m not going to let this happen to me.” So you know what happened, Andrew, was kind of serendipitous. But I heard an ad on the radio. Speaking of ads.

Andrew: This is no bullshit. No, this is no BS. Sorry kids. No BS origin story thing. You just literally heard that night an ad on the radio.

Ash: Yeah. I mean, I’m sitting there in my car and I really didn’t know what to do. Most people when they’re in a bind they sell something of value that they have. Maybe some family jewels, maybe some bonds. I couldn’t even sell my car because it was upside down and the dealership wanted me to pay them $2,000 to take it off my hands. So most people would think about, you know, “What do I have of value to exchange for compensation?” And I didn’t have anything. But when I heard this guy’s radio announcer come on the radio, all he was doing was talking about Rihanna’s new album. It was no big deal. It was nothing profound. But he said it was available for preorder.

And the word preorder, all of a sudden it clicked in my head because I realized that a CD album was a form of art and it was a form of ideas and that art was worth paying for. And that art did not need to be finished yet in order to exchange it for future value. And that was when I realized I didn’t have to have the thing done. I didn’t have to have this service created. The sales page created, nothing. All I had to do was be willing to make the world an offer. And that’s what I did that night. And within 24 hours had my first $2,000.

Andrew: Because you had 2,500 blog readers at the time?

Ash: I did.

Andrew: What was on your blog?

Ash: So this was the beginning of “The Middle Finger Project.” I started it in 2009. I just started writing about the different experiences I was having working in Corporate America and looking for a better solution.

Andrew: And trying to find the thing. “The Middle Finger Project” came from where? What does the name mean?

Ash: The name comes from a meeting I had with my very last client. I was working in advertising sales right before I quit to do the freelance thing. And it was the last straw moment. His name was Terry. He was a very busy man. He had me meet him in a bar instead of his office. I took it as a challenge. I was determined to get this contract signed. I brought two contracts, one for the standard amounts that the company always hoped to get and one for double the money. And I went there to that bar. I should have known it was a red flag the moment he said to the waitress. “We’ll take two of the regular.” Which were long Island ice teas?

It was about 2:00 or 3:00 in the afternoon. But I’m from Scranton, Pennsylvania. So I’m like, okay, I can hang. I grew up in a trailer park. I know what a long Island ice tea is. Fine. We do it. He starts saying very inappropriate things across the table. He’s mansplaining. I mean, he’s doing all sorts of weird things. And finally, I get my moment to shine and I start talking about our magazine. And this magazine did kill it. We were killing it for our clients. I wanted him to advertise with us. And as soon as I started talking about that, he removed a Polaroid camera from his satchel. I don’t know why this man was carrying a Polaroid camera.

He had one and he started snapping pictures of me across the table. So I did what any woman would do in this situation and I stood up and I slid myself in the bench seat next to him and I said, “Terry, I’m going to make a deal with you. You’re going to sign this contract.” And I gave him the one for double the money. “And I’m going to take this camera.” And I kind of like, took it out of his hands. “And I’m going to go in the bathroom and I’m going to take a very special picture for you. Do we have a deal?” He said yes. I went to the bathroom, came back out. He handed me my contract. I handed him his picture. I walked away. When I was in the parking lot, I heard him groan because he was not expecting a picture of my middle finger. And that’s where the name comes from.

Andrew: And the middle finger beyond him it’s, “I’m giving the middle finger to . . . ”

Ash: At the time it was society. It definitely was corporate. You know, it was basically like, how can we do this better? And I was struggling because the people that I knew in my real life rolled their eyes at me. Everyone said, “Welcome to the real world. Suck it up. You know, this is just what work is. Work is supposed to be hard. That’s why we call it work.” And I was determined to have conversations that actually mattered, and I found those people online. The people on the internet who started reading my writing back in 2009 to this day, some of them know me better than anybody whoever has in real life.

Andrew: You were writing these long blog posts back before people understood that Google is looking for long blog posts and with no like SEO methodology behind it.

Ash: Zero.

Andrew: This is back . . .

Ash: Humans.

Andrew: There’s one. I should do a word count on this. A really long article here called “Meaningless Sex and Lifestyle Design.” “Sorry, cutie. Last night didn’t really matter.”

Ash: I was probably traveling by then. Yeah, I think I had turned some things around.

Andrew: What do you mean traveling? This is back in the days where there’s like a link to StumbleUpon, a link to add this to Digg and Delicious and all these different things. I’m looking at, I guess 2009 version of your site.

Ash: Yeah, that was when people still left blog comments. You know, all the activities happening on site. And the biggest thing that I did was really consistency. I blogged three times a week, come hell or high water and I started showing up for people.

Andrew: And this was where you said, “I’m going to write a book about . . . ”

Ash: So this is when I’m in my car and I figured that, “Okay, I have two options. I can either make the world and offer to help them in some way or I can not.” And I decided that people were already giving me their attention. And so that was a sale. And so I had 2,500 subscribers. They were all very highly engaged. I had 60% open rates. To this day, I got 50% open rates, I can’t even believe it. And so they were engaged and I said, “You know what? Here’s what we’re going to do.” And I put together a very basic email and I said, “Hey, here’s what I’m scheming up over here. I’m going to put together a book of all of the ideas that we’ve been talking about online and all the ideas that we having in these forums and my own ideas about work. And you know what our options are and drawing from my background in sales and marketing and how we can then use that to figure out how to sell ourselves.

So that was it. That was 11 bucks. We were talking earlier about something I sold for super cheap. That was 12 dollars.

Andrew: Can I tell you something else that I saw when I looked back?

Ash: Yeah.

Andrew: Aha, with my iPad? Who is on the about page right there? Can you read that from my iPad?

Ash: Yes, there it is. Oh. In 2002 I received a full scholarship to college. There it is. Wow.

Andrew: I’m pointing to the name, that is Ashley.

Ash: That is Ashley. Ew, I was . . .

Andrew: Ashley is also wearing pearls.

Ash: I know, Ashley sometimes does that.

Andrew: Some people can’t see it. She was using that name. This was you like sprucing it up a bit.

Ash: I mean, listen, I had my friend take me into the woods and take a couple of pictures of me. That was it.

Andrew: I see it. You know what, which frankly we’re talking about 10 years ago. The fact that you had professional photos instead of just like some random thing from Flickr is showing a sense of care and concern for the site that most people weren’t aware of.

Ash: I mean, if it’s useful to talk about, I mean I learned how to do like WordPress HTML on my own. I didn’t have a designer, I didn’t have a design so I just stuck to black and white, kept it as simple as possible so it was less obvious and I had no idea what I was doing and put some nice photos up and it worked.

Andrew: Look at this. I see links in the . . . What was it called? where people used to trade links on their site or link out to the sites that they like. Steve Pavlina got a link from you, “The Art of Non-Conformity” by Chris Guillebeau. Zen Habits.

Ash: Chris is now my unofficial book advisor. He’s also a Penguin portfolio.

Andrew: I just got his latest book, “The Money Tree.” He just sent it in the mail to me. I said, “Why? What are you going to do about it?” “No, no, no, I just like it.” “Can I send it over to you?” I said, “Sure, I’ll read it.” But I liked that he wasn’t pushing for anything. It wasn’t like, I don’t know.

All right. Let me take a moment, talk about my second sponsor, then come back in and I want to know now that you sold the first thing, what’s the next thing that you sold. This is very commerce-y for you? I’m talking to you specifically, Ash. Is this a lot of commerce? Like I’m asking you all about the money . . .

Ash: No, I love this.

Andrew: . . . and about this feeling and the internal.

Ash: This is what I expected. I love this stuff. I can talk business all day long.

Andrew: By the way, what do you think of my new design? I used to have my laptop or my desktop computer actually right in front of me and you could only see my head. Now you can see my hands. I’ve been told by past guests that showing hands makes people trust you. The cameras . . .

Ash: I think that’s true.

Andrew: Does it help?

Ash: Psychologically I think that’s true. Yes.

Andrew: But I also wonder if it makes it feel more confrontational. Like if you just see my face, fine. But if you see my hands constantly, it feels a little bit like, I don’t know.

Ash: No, I mean, I don’t . . .

Andrew: You just feel more intimidating.

Ash: You’re a wonderful interviewer.

Andrew: Thank you.

Ash: And if someone can’t answer your questions, then I think, you know, it’s not because of you.

Andrew: I’m genuinely caring but I also have found that people want me to just be aggressive with the questions and I can’t. Like, I almost am losing my manners a little bit instead of just letting you tell your story. I have to interrupt and say, “But do you repeat it so much. How do you not sound so repetitive?” I should be a little . . .

Ash: I appreciate that if someone is being interviewed. The worst is when someone just says, “Okay, for an hour just talk.”

Andrew: Yeah, I guess that’s true too but I never want to get to the place where you know the thing that got you there is the thing that could also take you down that if you go too much. Like if this aggressive style is what people like, I could go so deeply into this aggressive style that I end up turning everyone off and then forget that the aggressive style was just like to get at something that I was genuinely curious about. You know.

Ash: As long as you’re still a nice guy behind all that aggression.

Andrew: I never was a nice guy honestly behind any of the aggression. It was more honesty than nicety. Second sponsor is a company called HostGator. Let me ask you this. You built your business, your reputation, your sales on building a WordPress site on content. Do you believe that somebody can go to, let’s say HostGator my sponsor or another platform, sign up for a WordPress site and create the kind of brand recognition kind of affinity with their audience that you did? Can this happen today?

Ash: I actually don’t think people have a choice. I think this is your modern-day resume and I think it’s more critically [inaudible 00:38:10] than ever.

Andrew: Why not Instagram? Why not YouTube? Why not Twitter? Why does it have to be a website?

Ash: A couple of reasons. Instagram, we all know, I mean social media platforms never build a business on that. Number two though, Instagram bothers me for a lot of reasons and one of them is that I think ideas are such a great equalizer. And you can’t tell from behind the screen of someone’s writing for example, if they are in a trailer park, if they are, you know, in the middle of a really tough situation. But Instagram forces us to now put on these shows and these filters. And it takes the value of your ideas and it steals the spotlight. I don’t like it for that reason but yes, I think you absolutely need to be building a website. It is your modern-day resume, your body of work, what you care about, the things you are enthusiastic about, and really what specifically you shine at.

I encourage clients all the time to be like, hey, be straight up about the fact that, “Listen, these are the things I’m not good at. I’m not your girl if you want X, Y, or Z. But if you want this, I’m the best in the world at it and this is where you can find it.” And you find. I mean, I built a creative writing agency because my writing was creative and that was the sales pitch right there.

Andrew: I do think as a modern-day business card, as a modern-day Yellow Pages page, whatever it is, it’s an easy no-brainer win. You put up a website, people trust what you’ve said on the website or you’re a speaker, sure. They’re not going to trust that you’re the world’s greatest speaker ever. But if you decide, “Hey, I’m going to start a speaking business, put a webpage up, here’s what I’m offering.” And then even send it down to the local university or local meetup meeting people are going to take you seriously. I also find as a researcher that there’s longevity to content that’s on your own website. It is nice for me to go back and see what your website, Ash. I was going to say Ashley because that’s what I’m asking. But it’s nice to see what your site was like back then.

I’ll tell you that I’ve done interviews from years ago that will then get resurfaced on my site because people will go back and find the person who suddenly becomes important. Like, I discovered if a company gets bought out, if a company’s founder starts a new business, suddenly old articles, old interviews that I’ve done about the person will then become really big. And you don’t see old tweets go big that way. You know, this work that I’m putting into my interviews and publishing on my site get rediscovered because they’re on my site. And yes, I’m on iTunes but you know what, podcast app from Apple. They don’t go back more than 300 episodes. If you do, it chokes. There’s nothing like your site for creating this asset, this longevity.

All right. If you’re listening to me, if you’re listening to Ash and you’re listening to my other guests and you say, “All right, I’m ready. I’m going to go create a site.” Go to to do it. Would you? number one, if you go there because you’re attaching that slash Mixergy at the end, they’re going to give you the lowest price possible. Number two, it’s going to get tagged as being a customer that came through me, which means that we’re always there and we’ve got your back. And number three, they got other bonuses that I don’t have the time to tell you about. Go over there and see the list of features. They’re just going to give you a great price and a great service. And then just focus on your writing.

Ash: I love that. And you know what, honestly, because when you put your body of work on HostGator, I will say that people really do trust you to show up for them because you did such a good job of showing up for yourself and people can see that.

Andrew: Right. Don’t give me the cobbler’s kids wear broken shoes. I don’t know if that’s true. If you’re telling people something, let me see how you do it. All right. What’s the next thing that you sold? You sold the book. Now what? How do you build this business?

Ash: Services.

Andrew: Services, people talk to you?

Ash: I did the most generic thing you could ever do. I sold a service but I think it’s one of the best things you can do. Great. You know, you don’t have overhead. You don’t have any product startup costs. You can sell your knowledge in this warm of one-on-one service. And that’s exactly what I did but it was for writing. I had people asking me in my inbox. I was declining them at first because they didn’t know what to charge. Oh my God. And they wanted me to write for them because they had found my writing and they liked it. A guy by the name of Dan Todd, he used to run a company called GlobalMojo.

GlobalMojo doesn’t exist anymore. It’s now transformed into something else. But he was one of the first people to send me an email and be like, “Ash, I just found your website. Like, I’m not even in your target market but I like your style. Can you Ashify our website for us? We need to hit this younger market.” And all of a sudden, I have lots. I had this new marketing director for a company called Winston Rods, fly fishing rods reaching out to me because historically their products catered to an older demographic. And they needed to start hitting a younger demographic because, you know, their customers were going to die. So like all of these people started reaching out. I wasn’t even selling myself as a copywriter. They just saw my work.

Andrew: They would just find you from your site and say, “Wait, can I hire you to do this?”

Ash: Yes.

Andrew: How did you meet Gavin form Acuity Scheduling?

Ash: So Gavin came about later when I started, I then officially set up a creative content agency. Gavin reached out to me every single . . . In fact, this is interesting. Every single sale I’ve ever made has been inbound marketing. I’ve never done any outbound ever.

Andrew: Inbound marketing meaning, you put up an offer, people give you their email address, you follow up over time and you sell? That’s the way the Dharmesh Shah, the creator of Inbound talks about it. Is that what you mean?

Ash: Yeah. Or just the content on the site, it’s just evergreen.

Andrew: They just find the content and they say, “I want to sign up and work with you”?

Ash: Whatever it is. I mean, I’ve never reached out to a company and pitched myself, which I think has bananas. But when that happened, Gavin was looking for someone. He was very new with Acuity. Acuity was a baby. He had just started it because, you know, he made it for his mom.

Andrew: For his mom’s massage. No, was it a massage company?

Ash: Yes.

Andrew: Well, she needed a way to have people book times with her but not double book and have it automatically go to her calendar or something. That’s what he created. And he reached out to you because he saw your writing, saw that you had an agency to do this and he wanted you to do what for him?

Ash: And he wanted me to do the exact same thing that Dan Todd did. “Hey, we need personality.” That’s what people kept coming to me for. And especially this was at a time when the internet was getting more and more crowded. So you know, a sales strategy is absolutely creativity.

Andrew: For like he wanted ad? Is that what he came to you for?

Ash: Oh, no. I took over all his copy.

Andrew: So the copy on the site.

Ash: I did all of it. Yeah, I did all the original Acuity website. Everything that showed up.

Andrew: Explaining what Acuity Scheduling is, that whole thing.

Ash: Oh, yeah. All the sales copy. I didn’t all the . . .

Andrew: What did you charge for that?

Ash: Oh, man. I think Gavin was on retainer. Forgive me, Gavin, if I disclose this. But I think the last time we engaged it was for 5,000 a month.

Andrew: Oh, that’s a great price for like for attitude, for details. Wow.

Ash: It was cheaper at first too.

Andrew: Is that how you got to $100,000 a year? Where I’ve heard that was the next big step for you. No?

Ash: I mean yes and no. Yes. Like my first $103,000 happened in the 8 months that happened after that Kmart parking lot. I started selling my services and I sold, you know, preorders for this book that I wanted to write. I just wanted to create it.

Andrew: What year was this?

Ash: 2011.

Andrew: And is this the book that just came out now?

Ash: God forbid. No. Oh no, no, no. A lot of people are under the assumption that the book that came out now is like some kind of conglomeration of blog posts. It’s not, it’s a separate thing entirely. This is a real book. But it started with services. That was it.

Andrew: But in the previous book that you sold was what? The presale book.

Ash: It was called ” Guts.” I mean, it was really philosophical in nature, just discussed ideas and people really loved it. It was interesting. People really just wanted to feel seen and like, someone else got them. So that has never been for sale ever again since the beginning of time. Gavin and I work together very closely on everything. All of his . . .

Andrew: You don’t need a job, you need guts.

Ash: Yup. That’s it.

Andrew: That was the book. “Red, Hot, Fiery Passion, Soul Shaking, Good Work That Matters. Potential Power Persistence, Pizzazz and Money, Baby Money.” That was the subtitle for that book. And that’s a self-published book?

Ash: Oh God. Yeah.

Andrew: Wow.

Ash: I mean, come on, it was 2009 too. It was like a PDF version and I worked very hard on it mind you. I remember sending an email to . . .

Andrew: 128 pages. This is not like the typical tiny PDF and Clara loved it on Goodreads. You got good ratings on Goodreads.

Ash: That’s still on Goodreads? Oh no.

Andrew: It is, except for one person. Sue said this book has a lot of typos. Very distracting. You did not get an editor, it looks like.

Ash: Yeah, no. I mean, 2009 no. But literally that was for sale for like six months and then taken down.

Andrew: You know what, I’ve got to tell you people have reviewed it even as recent as a couple of years ago or last year even, Louise Stigell rated it five stars last year.

Ash: Wow. Unbelievable.

Andrew: All right. What’s the first product that you created beyond that?

Ash: Gosh. 2000, it was a copywriting workshop, a creative copywriter workshop from Santiago, Chile. It was an accident. I didn’t know I was going to be doing this, but people kept asking me then kind of like, you know, the next question, “Oh, you know, you’re writing for all these cool companies. How can I do that to you?” Kind of a thing. Or, “I like your writing.” And so I put together a very basic six-week college-level style class. It wasn’t pre-produced, it was just like, “Hey, let’s get on for a couple of hours every week for six weeks and we’re going to talk about how to inject personality into your words and your writing.” And I made my first $30,000 that way, and I was so baffled. I’m like, “Oh my God, this is outrageous, right.” Like for someone who’s just starting.

Andrew: It sounds great.

Ash: Yup. And so it became kind of an addiction because I didn’t realize the power of scale.

Andrew: Because you could do this not one-on-one for people like Gavin but in bulk. You know what, this is where my attitude is sometimes a problem. I would see it and go, “Oh, it’s not enough. It’s only 30.” I did something where we were selling like 75 no, it was 115,000. And like the first go and I go, “Oh this is not great. I don’t know how I failed so badly.”

Ash: Well, today I might think similarly.

Andrew: I think I should be a little bit more appreciative and less like demanding of more at some point, you know?

Ash: Well, I mean at this point, if I do anything under $100,000, it is sort of categorized under failure category. What can we tweak? What did we do wrong? What’s up?

Andrew: When you do tweak, what’s a thing that you had to tweak that you didn’t do right that now you’re doing better?

Ash: I got lazy.

Andrew: About?

Ash: I started assuming that all of these, you know, blog subscribers that I had were like die-hard loyalists. And I got lazy about really explaining to them why they needed to buy a thing. Because I’m like, “It’s me. You trust me. Like, you know me.” I rode my own coattails a little bit too much and I saw sales start to dip. I really had to keep going with the copy. Copy has to be strong.

Andrew: And where do you sit down and write, how do you get the copy? What’s your process?

Ash: The number one thing that has made the difference for me, no matter what it is that I’m selling is always, it always comes down to one thing and that is mystery. So bullet points. Every single time I change bullet points, my conversions go up like a lot. And so sometimes . . .

Andrew: Mystery in like the title and the first couple of paragraphs, bullet points throughout. Is that what we’re talking about?

Ash: Making people think that you know something they don’t know has to be the focus of everything that you’re writing and doing. In a way where, gosh, yes, they read through. “What’s inside this thing? What are you going to teach me? What am I going to get from this? I don’t care what it is. If it’s an app or a class or whatever, why do I care about this?” And so often we are very descriptive in nature and we describe, you know, features. But it really has to be very benefits-focused and writing those with this air of mystery but also fun. You’re going to have fun when you buy this. This is a great thing to sign up for. I’m enthusiastic about it.

Andrew: Damn, Ash. You know what, you lost me there for a second. It’s because the fricking photos throughout the years, I was going to say, you know, I happened to have had a tab open with that early version of your website and the photos on the about page look really like damn impressive. And I said, “I don’t know, maybe if you say that to a woman it feels like it’s inappropriate.” And then I come back to your main page, just look for an example of how you create mystery and look at this. This is a great shot of you on the home page, right?

Ash: That was a wig.

Andrew: I think I’ve seen a couple of wigs on you in some of the photos. I don’t give a rat’s ass. What I care about is, is there an emotional impact in the photo? Does it feel more elevated than the standard picture that people take on their phones? And because iPhone is so good, we could live with it. Is it better than that? And it is and a lot of even photos do that. Like the one of you drinking some white wine with a straw. Every bit of that is cared for. It’s a different look than you have right now as you and I are talking but they all are cared for.

Ash: Thank you. That was a professional photo shoot. I highly recommend them. If you’re looking for an example of the bullet points though, go to There’s dashes in between those but, you know, that’s a sales page we just put together to do some testing on something that I thought would be useful for my audience. Right now I’ve just come out with a book. I have a lot of questions about it. “How did you publish it? How did you do it? I want to write a book too.” So guess what? I’m going to take my knowledge and put it in a container and I’m going to sell it to you.

Andrew: By the way, I didn’t put the dashes in and the 404 page says, “Oh my God.” And then underneath it, “This page has been eaten by Alec Baldwin.” I like the little touches you mentioned earlier. Do you remember the first year that you made $1 million?

Ash: Yeah, I had to because we were in litigation and I had no choice but to ante up.

Andrew: To earn that money so that you could protect yourself from the lawsuit.

Ash: Yup. Keep going with it. Lawyers are expensive.

Andrew: Oh look at this. I do have the various, it takes me to the equity Is that thing?

Ash: Yeah. That’s in transition. Ignore that part. Scroll down to the bullet points and you’ll see what I’m talking about.

Andrew: It’s a nice layout on that. Let’s go into the lawsuit then. What happened?

Ash: That’s something that I think a lot of us have to face when we are creating things with other people. So maybe it’s your podcast or maybe you’re doing some kind of retreat with someone. Maybe it’s a JV partnership. One of the things I learned, because I used to do a lot of that with different people. I would bring in all sorts of different experts into my business and we would co-create a piece of intellectual property together that then we would, you know, sell. And it was a wonderful way of doing it. One of those creations though ended up going sour and it was simply because of poorly managed expectations.

Andrew: What do you mean? I’ve got the lawsuit here. You told me you didn’t want to give me the name of the person. I said, “Okay, I’m going to go look it up for myself because I know how to find lawsuits.” I’ve done that for past guests. I don’t know if I’ll reveal the name or who I think it is. But it seems like what you did was, somebody had to create an eBook along with instructional videos, audio lessons, and services. Was that on you to create it under their brand?

Ash: No. It was a JV that we had separately branded from both of us and she brought her knowledge and I brought my creativity and writing to the table.

Andrew: Your strategic copywriting advice and brand development services. All right, and so the two of you partnered up. Where did it not work out? What happened?

Ash: Now, this is just what happens when money is involved and things go well and you do an account . . .

Andrew: You sold it? You actually brought in money from this?

Ash: Oh yeah. I mean, our first day we did like 100 grand. I mean, it was really profitable as well. I don’t think she expected that. And then it became kind of like, “Oh well, I want to take this farther and do different things with it.” And we had different visions for it. And that’s a problem when you don’t have it outlined what’s going to happen next. And so . . .

Andrew: Oh. And then they got a trademark on the name. But you also wanted the trademark on this new entity that you created, right?

Ash: Yeah. I’m not going to be a liability to go into the details on it.

Andrew: Okay. All right. And so the whole thing fell apart because you weren’t clear about who gets what?

Ash: Yeah. And you know what, ego. Ego gets involved and she was an attorney.

Andrew: Yes. Wow.

Ash: I had to hire an attorney to figure it out and ego gets involved.

Andrew: Her whole thing is she’s an attorney from what I can see.

Ash: Yeah. It was an unfortunate situation. But you know what happens . . .

Andrew: And a well-known attorney. I see. Oh, I don’t want to get to it. I’m not going to say too much. But I am curious about what was the deal here? You were going to have to pay back the money or pay more? What’s the danger that got you to work so hard that you had to ante up, I think you said to earn over a million dollars?

Ash: For me, it was a matter of principle and I needed to fight for what I believed was right.

Andrew: Which was what? Ownership of the name or keeping half the money?

Ash: Not going to comment. Listen, so intellectual property no matter what you’re creating is a federal matter of law. So that automatically bumps you up to federal courts where you are now dealing with judges who are actually seeing cases for, you know, they’re trialing terrorists. And here we are with our little eBook and I’m walking in with a company called The Middle Finger Project and it’s just like, it’s terrifying. I did what I thought was right at the time and I’m sure she did what she thought was right at the time, which put us at odds. And so in order for me to continue doing what I thought was right, I was going to have to spend a lot of money.

I didn’t have the luxury of having a law degree to be able to defend myself or you know, pursue any legal remedies. So I had to pay for it. And let me tell you what, that quickly added up to about $30,000 a month in expenses, in just legal fees. If you have to hustle for that kind of stuff. I would never do that again if I were put in a position. It wasn’t worth it.

Andrew: Do you think you could have just had a conversation with her and cleared this up?

Ash: Yeah, sure. We tried that. We tried that a lot.

Andrew: It didn’t work because?

Ash: I don’t know why it didn’t work, Andrew. I think we just had different perceptions of what was fair and what was not fair. We couldn’t come to mutual agreement.

Andrew: The lawsuit seems like you were supposed to get 100% of the sales for the first year. 75% of the gross sales for in . . . Oh, 100% of the sales for the first two years and then 75% gross sales for the third. And I don’t know, it just keeps going. Price third and final year of license.

Ash: Sorry.

Andrew: You’re not going to go into details on it. I respect that.

Ash: Out of respect for the parties, I mean, I’m not going to comment any further on it.

Andrew: Did you freak out? Did you feel like, “I’m going to lose it all”? It doesn’t seem like it. It feels like you felt like, “I am not going to back down because I’m not going to be slapped down just because I am at a disadvantage here.”

Ash: Yeah, I mean I think it’s important to fight for what you do believe but I think that at some point you have to cut your losses and just be done with it. I would never do that again. It was four years of that taking me away from my business, away from things that matter to me to prove a point. And never again.

Andrew: And it weighed you down. Yeah, that’s what it is. All right.

Ash: Yup. Wouldn’t do it again.

Andrew: Did you freak out? Did you sleep well?

Ash: Actually I did have a lot of trouble sleeping but overall when I’m under pressure I perform better. So I did a lot of things very well in those few years.

Andrew: Like what?

Ash: Like making offers that I might not have made, like charging more money than I might not have charged. Like having the guts to just take a risk, not have it finished, not have it perfect. Just you know, put it up for sale, see what happens, try different stuff, experiment. You know.

Andrew: And then last year it was down because? So all that helped you increase revenue and profit.

Ash: Yes.

Andrew: Last year what happened?

Ash: Well, the last couple of years really it’s because my business depends so much on me as the personal brand. So this has been a real big bottleneck for us and trying to figure out ways to systematize. So I had to take time off to go write this book. I’ve been writing this book with Penguin, which signed two years ago. So it’s been two years and then some because I was working on it for a year before that with my literary agency. So that was a lot of time-consuming stuff that I wasn’t necessarily getting paid for it. Yes, you get an advance. I don’t know if you know how book advances work. My advance was for the sum of $150,000 plus a $50,000 bonus. If you earn out that advance within year one.

So you’d think that that money comes to you in advance. It doesn’t. It’s broken up into four payments over time, four years. So you need a business, you have to have a business backing you in order to do these kinds of things.

Andrew: All right. Let’s sell it then. “The Middle Finger Project.” By the way, one of the things that I like about you is I have an issue where if I get a guest on has a book, I need to read the whole book. I didn’t realize that you had a book. I was introduced to you through someone. So I said, let’s just talk to her. You sent out a Google doc telling me what’s in the book and you must have sent it to other people because I saw other people in the Google doc. I feel like every podcast guest should do something like this. For me, it helped because I didn’t have the book. I think a lot of podcasts’ hosts, they’re either lazy or overwhelmed or unsure of themselves and they need a little direction.

And if you could tell them, “Here are the 20 questions that you should be asking.” You’d give them a lifeline and if you give them a little bit more, you sometimes can direct the interview to where you want. That’s just a smart tip for anybody who’s doing a podcast.

Ash: Oh, yeah. I mean, Penguin came out with their own press kit but it was a very standard, official press kit and I wanted to do something fun. So I actually sent that Google doc to my entire email list. “Hey, you know, who do I got? Who wants to do a podcast? I don’t care if you only have your Facebook friends, will you help me the day this book comes out, post something about it. Here’s the fun doc. You know, let’s get into it. Here’s what we’re doing.” Gave people a sample. You know, it’s helpful for people to feel like they’re involved.

Andrew: And I think you said something like, “If you’re religious you’re not going to like this book.” And then I guess my assistant sent something nice.

Ash: She was amazing. She was so graceful. I mean, in that doc it’s like, who’s this book is for and then who’s this book is certainly not for. And it goes into all these, you know, no conservative people, Christian people, my ex-boyfriend named Christian, all sorts of people. And so she wrote back and she said, “This is so fresh. I love it. You know the church lady approves.” And I’m like, “Oh, no.”

Andrew: Yeah, I was going to say she is more of a conservative person and I only wonder what she would say if she got something like this. All right. So then what are we doing with this book?

Ash: This is a book that was written for anybody who currently hates their job but doesn’t know what else to do. This is the big conundrum that most people are facing. This is based on 10 years of experience of working with people from all over the globe who know the mechanics. They kind of know what they need to do if they want to strike it out on their own, do something different. But what they’re missing is the mental piece, the emotional, the confidence. They feel like imposters. They’re kind of like, “Well, who am I to blank?” So this book addresses that and it’s based in narrative and it’s based in a lot of lessons I’ve learned in 11 years of doing creative business on the internet.

Andrew: I love narratives. I hate how-to books that are just, “Here’s what you need to do.” I want to know really your story. I could get there. Here’s what you need to do from just reading the chapter titles. What I want to know is like, why do you say this? Where do you come off saying it? What happened to other people who’ve done this? Give me that.

Ash: I mean, for anyone writing a book or anyone creating anything, the question I kept at the forefront of my mind the whole time was, “Why does this matter for anybody else? Why do any of us care? What do my own experiences mean for the rest of us? How can this help us? How can this be useful information?” And I use that to guide the entire thing.

Andrew: All right. I was going to start reading the first chapter. I don’t feel like this is for me. I’m going to leave it for you.

Ash: He’s blushing. I just made Andrew Warner blush.

Andrew: You know what, I don’t have like big limits but I do feel like there’s some that I don’t feel comfortable with for some reason. I don’t know why.

Ash: You probably shouldn’t read the one with penis in it.

Andrew: No, I’m totally in to that. I just talked to the founder of Thompson Hotels. I’m looking up your homepage, you called it a landing page. You said that you’ve got like nothing really up. There’s a naked lady diving into a pool here. Like, full-on naked. But I dig your style and then instead of talking about the naked lady, I just had to figure out like, “How does he get to the style to make that look good and represent his whole brand in two images.” And we got it. I feel like he understood where I was going and he could dive into it with me, thankfully.

Ash: And now we’re all Googling madly.

Andrew: Oh, we should, I can’t wait to go see his hotels. I feel like this guy, I’ve known his hotels, a Thompson Hotel in downtown New York. I’ve known for years. This dude right down to his unkept-kept beard always has a look. I think he spent time telling me about the fricking lamp at one of his hotels and how that opens up the experience for people. I love that he cares about this stuff to that detail. And for me, I’m just curious about where that comes from, how you get to it. I’m curious about like, you know, the photos that you take on your website, the way that you communicate, the way that you use the word unfuckwithable. You know, like, that’s stuff that comes with. I didn’t . . .

Ash: You said it.

Andrew: I don’t have a problem cursing. I have a problem with being able . . .

Ash: No, that word.

Andrew: Why is that such a hard thing to say? It’s not like . . .

Ash: I don’t know. Everyone stumbles on it though. Everyone. You’re not alone. So pleasure is the short answer to that. When you’re writing, when you’re doing anything focus on creating pleasure for people. When you’re selling something, focus on a pleasurable experience. It feels good for you, it feels good for them. And it leads to these kinds of details, you know, kind of actively thinking. “Well, how could I make this fun?” Great question to ask.

Andrew: For yourself or for other people? Are you thinking for other people only?

Ash: Well, both. Sometimes when you’re approaching tasks you don’t want to be doing like your bookkeeping, for example. How can I make this fun? What can I do? You know, if you want to send out a sales email, you don’t feel like writing. How can I make this fun? Leads to way more creative solutions.

Andrew: All right. The book is called, “The Middle Finger Project.” It’s also the website. Why is it You don’t have

Ash: Well, originally I didn’t because it was parked in 2009 and then some generous reader several years ago who took one of my classes actually bought me So now we have it but it’s both. We have all of them.

Andrew: It’s a well-designed site and a well-designed book cover. But I hadn’t read the book yet and I think the first word just caught me off guard for some reason. All right. I’m not looking to leave an open loop. I think most people are then going to go, “What? Andrew, this is nothing. What are you freaking out at?” I’m not freaking out. I’m just like, all right. Listen, there’s the book. Thank you so much for being here and being so open with me. Ash, I appreciate you doing this.

Ash: Andrew, you’re the best.

Andrew: Thanks.

Ash: Thank you so much. I can’t wait. I’m going to write home, I’m going to tell all my friends, “Look for me on, baby.

Andrew: Right, baby.

Ash: Yeah, baby.

Andrew: And I lived up to like the whole hype of being an asshole before the interview starts and during.

Ash: You are phenomenal. Don’t let anyone tell you a different.

Andrew: I won’t. Thank you. Thank you all for listening. Thank you, Mixergy sponsors, HostGator and Toptal. Bye, everyone.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.