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Cole Schafer

Copywriting is hard. Which is why we always appreciate great copy when we see it. It’s usually simple, clear, and tickles your brain if written well.

Copywriting and Cold Emails
Copywriting and Cold Emails

Copywriting and Cold Emails

Ep
142
Jul
14
With
Cole Schafer
Or Listen On:

Live fast, write often.

Copywriting is hard. Which is why we always appreciate great copy when we see it. It’s usually  simple, clear, and tickles your brain if written well.

Cole Schafer is a creative writer. By day he runs a small advertising business called *Honey Copy*. By night, he writes and publishes poetry under the alias, January Black.

He’s got a lot to say and he does it without mincing words. But in a way that will make you smirk.

In this episode, Cole and Chris talk about the nuance and challenges of language and how to wield it with grace. We’ll hear about how he found writing, why he left a well-paying agency job for manual labor, and how to name a $15 cookie so that people will happily buy it.

Hosted By
special guest
produced by
edited by
music by
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Episode Transcript

Cole:

You sort of have to set your ego and pride aside and you have to start cold emailing anyone you can get your hands on, and I sent out hundreds of cold emails every single week, and the way that filtered down was 100 cold emails would end up getting about 10 people to agree to jump on a call. Three would kind of be like, "Eh, let's give it a try." And then one would end up being a client. I mean, it felt like if I send 100, one could end up giving me a chance.

Greg:

Welcome to The Futur Podcast, a show that explores the interesting overlap between design, marketing, and business. I'm Greg Gunn. I don't know about you, but when it comes to copywriting I start sweating and forget how to use the English language. Maybe it's a lack of vocabulary, but my words taste like plain oatmeal. There's nothing wrong with them, they're just really boring, which is why I always appreciate great copy. It's simple, it's clear, and it tickles your brain if done right.


Today's guest is a creative writer. By day, he runs a small advertising business called Honey Copy, but by night he writes and publishes poetry under the alias January Black. So yeah, he's got lots to say, and he does it without mincing words, but in a way that will kind of make you smirk too. In this episode, he and Chris talk about the nuance and challenges of language, and how to wield it with grace. We'll hear about how he found writing, why he left a well-paying agency job for manual labor, and how to name a $15 cookie so that people will happily pay for it. Please enjoy our conversation with Cole Schafer.

Chris:

Cole, excited to talk to you. I saw your tweet and it's nice to know that you're also aware of what we're doing here. So, for people who don't know who you are, can you introduce yourself, please?

Cole:

Absolutely. My name is Cole Schafer. I am a creative writer over at a small advertising shop called Honey Copy where I write advertising that hopefully doesn't sound like advertising for brands of all shapes and sizes. When I'm not doing that, I am writing poetry under the alias January Black on Instagram, where I have a couple books of poetry and prose out, and I have a third one coming out very, very soon.

Chris:

There's a bunch of things already just in that introduction I need to talk to you about. I know you do these interviews, but for people who don't know I'm just going to dig into some of your history and your kind of what makes you unique, if that's okay with you.

Cole:

Absolutely.

Chris:

Okay. So, I was on your site, Honey Copy, and just looking at the way that you write, it does sound very different. Tell me a little bit about your style of writing and how you developed it.

Cole:

So, I think the reason I write differently than probably most copywriters is probably because I don't have any sort of formal education in writing, and I haven't read a ton of the sort of OG advertising books. I'm aware of the Gary Halberts and the Joe Sugarmans and all that, but they were never sort of my teachers. My teachers were Hemingway, and Steinbeck, and some really stunning writers in fiction, and those were always the people that I really admired. I try to, even though I understand that copywriting is about selling things, I try to do that with pretty words, not just in car salesman, sort of leaving people feeling uncomfortable and stuff.

Chris:

Mm-hmm (affirmative). I get a very conversational tone in the way that you write. There is a certain self-confidence and a swagger to it, the way you write, especially on your website. So, did this feel like it was the right thing to do or did this develop over time?

Cole:

So, it's never been a super intentional choice. I think that something I like to warn people about is when I'm Honey Copy, right? And I'm writing under Honey Copy, I'm a very different person than if you were to of out and have coffee with me, or have a beer, or hang out. I am not arrogant in person. I never try to make people feel uncomfortable or anything like that, but with writing I think that there's sort of an alter ego that comes into play with some of that stuff, and I try to definitely shoot people straight when I'm writing, but it has never been an intentional choice. I think more so it's the tone, it's just developed as I've written and it's felt very, very natural for me.

Chris:

Mm-hmm (affirmative). Okay. I'm trying to read some of the things that you're really known for because you ... A writer writes, that's what I'm reading. I'm like wow, okay, this is pretty cool. So, you have a very successful newsletter. You're talking about how people really show up and want to hear your thoughts on this thing. You talk about this guide of copywriting that you've written. I think you have a course or maybe courses.

Cole:

Mm-hmm (affirmative).

Chris:

I think I've heard that too. Then you're also a hired gun. In terms of your business as Honey Copy, how does it all break up? What does your Honey Copy writing empire look like in terms of the different things that you're doing?

Cole:

Sure. So, about 50% of my income comes strictly through being a hired gun, a freelancer for various brands. I've always believed that you should be super niche about the services that you offer but you shouldn't necessarily be niche about the clients that you're working with. So, the clients I work with are in a number of different industries, whether it's cannabis, or some type of SaaS startup, or even Bowflex. They're in a number of different industries. So, that makes up about 50% of my take at the end of the year, and then the other 50% is through my courses, which is a copywriting course, a freelance course, and then also my books of poetry as well.

Chris:

And you were describing something like there's what you do ... Did you use the words like what you do by day, your day job is the writing part, and then your night job is all these other fun cool stuff that you're doing, including the poetry and going under the name of January Black. Is that the mix right there?

Cole:

Yeah, that's the mix. I mean, the courses are obviously under Honey Copy and under myself, but the poetry, that's me moonlighting. At night, I love to write poetry, and I'm using a lot of the stuff I'm learning in advertising to market that poetry, and I've sort of created this alter ego, January Black, where maybe some of the things that I'm writing in poetry are a little bit more provocative than what I'm writing on Honey Copy, and I can create that separation a little bit, and really stamping in the ground, it's like this is art, it's not advertising. So, there should be some distance between me and what I'm creating there.

Chris:

Mm-hmm (affirmative). When you create this alter ego, this is really interesting to me, you create an alter ego. Does it allow you to become someone else?

Cole:

Sure, sure. So, I'm actually in the middle of releasing my third book now, and with it I'm releasing the alter ego. So, nobody even knows the name right now, but for that alter ego we've done videos where I have black mascara on, and I'm in a black suit, and I have my fingernails painted black, and I'm a completely different person, and that's been very intentional because there's something strange about writing. You have to be careful what you write because people can easily begin to associate that almost too much with you as a person. So, I think sometimes when you can create that alter ego, it creates that distance. But yeah, it has allowed me to write in a different what than what I maybe write for Honey Copy.

Chris:

So, who do you feel more alike? Like who you are or your alter ego, or is it neither or both?

Cole:

So, I kind of joke that January Black is everything that I wish I could be, right? So he doesn't have to worry about losing his hair, probably does much better with women, is much more sweet talking and more swagger. He has no insecurities, probably has a bigger dick than me. I mean, probably makes more money than me. I mean, so there's aspects of him that are me, but he's not me, you know? And I could pretend to be him at night when I sit down at the typewriter, you know?

Chris:

Yeah. Are there rituals or a ceremony that you go through, like step into character? Do you go full Christian Bale on this or is it just once your finger touches the keyboard you're that person?

Cole:

Yeah, I'd say it really comes out when I'm writing the poetry, that this is January, this isn't as much Cole anymore.

Chris:

Mm-hmm (affirmative). People who know of you as both people, do they think like, "Hey man, you can't say that"?

Cole:

Mm-hmm (affirmative).

Chris:

And how is that going to affect you as Cole, as the copywriter who is a hired gun?

Cole:

Mm-hmm (affirmative), mm-hmm (affirmative). Sure. So I've fortunately never ... A lot of my clients will follow me on, follow both writings. So, I've never had any major issue there. I'm sure it will eventually come, but the main thing is there's places I'm willing to go and push the boundaries, and be provocative, and then there's other places I'm not like I don't ever want to push the boundaries on race, or politics, or anything in that realm, but I am okay with talking about sex, and alcohol, and more of maybe the wild sides of being in your 20s and that exploration. So, I think it's choosing where you want to go, but I think with that it's never being afraid or above apologizing.


I've had to apologize a few times where maybe I crossed a line. Like a good example. So, my dad's half Japanese and my mother is half Syrian, and so I consider myself pretty well-cultured, but growing up a common sort of schoolyard taunt that people would use if you gave them something and they didn't give you it back was don't be an Indian giver, which has become a very derogatory term. But anyways, in my newsletter that goes out to almost 15,000 people now I accidentally used the term, and I didn't mean to hurt anyone. I didn't mean to step on anyone's toes, and having grown up being called some derogatory terms towards Asian people, I knew like oh man, that probably hurt some people. So, I just publicly apologized. So, I think it's being willing to push the boundaries, but when you push it too far and you're hurting people then I think you just take a step back and say, "Hey, I'm learning and I'm sorry." And being genuine in that apology too.

Chris:

Did you grow up in America?

Cole:

I did, I did. I grew up in Southern Indiana, but my grandmother was full Japanese. So, I'd spend half of every week at her house, and that was just stepping into Japan. She'd speak to me in Japanese, even though I couldn't understand it, and she made sure that I was very, very aware of that side of my heritage.

Chris:

Okay, this is really interesting. I didn't intend the conversation to go here, but I can relate to what you're saying. I came to America when I was three years old, and there were some issues about race I didn't fully understand. So, that term that you said, Indian giver, I think it's part of maybe the way that we grew up in America where the popular culture says this and it seems to be normal, until you start to understand how offensive it can be. We're seeing that still happen with people, like the Washington Redskins finally saying, "Okay, these are people." That it's not a mascot and you can't just do that, because it's not actually honoring Native Americans.

Cole:

Absolutely.

Chris:

And so we're starting to discover all that stuff. So, I can see how even for me growing up I would use terms like that's racist against me. What am I saying? Why would I even say that?

Cole:

Yeah, yeah. Yeah.

Chris:

Right?

Cole:

Yeah.

Chris:

So, this goes out, and then you hear the feedback, and then like a man you adjust, and you apologize, and you learn, and you move on, right?

Cole:

Absolutely. I think it's so important for writers to recognize that language changes, and what's appropriate today might not be appropriate tomorrow. Even though I don't think anyone should have really ever been using the term Indian giver, as someone who is Japanese there was a point in time where the word, I'm not going to say it, but J-A-P was you could say it, it wasn't a big deal, but nowadays if I hear someone say it I have this very visceral reaction where I'm like, "Ooh." It's a cringe, and I very politely just let them know hey, that to some people can be a little bit offensive. Would you mind not using that? But I think that's also really important for people to recognize, whether you're a writer or not, is just have grace with people because everyone has grown up in different parts of the world, and I think that it has to be we have to approach those situations from a place of understanding and education rather than being verbally violent towards them because they said something that they don't totally recognize was wrong in that moment.

Chris:

Right. I think you're using the velvet glove versus the cast iron glove to respond to that saying you may or may not be aware, and now you're aware, and the decisions you make from this day forward, that's kind of on you and not on me at this point, right?

Cole:

Sure, absolutely.

Chris:

Yeah. Okay, I love that. I'm always fascinated by people who work in the creative space because it's not, I don't think, part of the natural way that we kind of wake up one day when we're a kid thinking, "Oh, I'm going to be a copywriter, I'm going to make a course on copywriting and how to freelance." I'm curious, if you can retrace your steps back to maybe like you're pre-aware of it even that writing may be your jam. Do you know where you are and what you're doing, and then it becomes sort of clear at that moment?

Cole:

Sure. So, I think that the reason, and this is a theory, but I think the reason for creatives why finding that vocation is such a big experience is because it's this, in my opinion, this journey into adulthood in a lot of ways, where previously defining that creative pursuit, we are children, and I think it's important to remember that you can be an adolescent until you're 35, if you don't grow up. For most of my childhood it was basketball. In Indiana basketball is religion. I mean, the high school gyms are five, six, 7,000 people. I worked really hard at that and eventually played some college ball at Bellarmine University in Louisville, Kentucky.


My grandmother, who I had just mentioned, one day I got a call from my dad late at night and said she was not, something really bad happened. Later my grandfather would tell me was that they were at her house, and they're in her kitchen, and they're flirting like they were 18 again, they've been together since they were 20, and he goes, "We went and got some ice cream out of the freezer and I made her a bowl, and then I made myself a bowl." And they went into separate rooms because he loves watching sports and she loved watching Korean dramas. It was real common in like Japanese culture, and hear a crash and a scream, and she dropped dead from an aneurism. That was really, really tough because it was one, like losing someone who is your best friend, but in addition to that it was like my first look at this idea of mortality, right?


I remember spending much of the remaining year falling out of love with basketball. The party was over. I mean, she watched 950 out of the 1,000 games I played growing up. So, for me it was like if we're all going to die, why am I shooting this ball through the hoop? And I mourned her loss in this beautiful cathedral that sits high above Bellarmine's campus. I mean, it's gorgeous, and it has these windows that run from floor to ceiling, and they're as big as invisible giants, and you can just look out at them at Louisville. I mean, it's gorgeous. There was a piano in there, and I didn't know how to play piano at the time, but I would just sit down and play with the keys, and I began writing lines to the music I was playing. That was sort of this catalyst moment I think where I realized that writing could not just be this thing that you had to do in school, but it could be this thing that could get you through, whatever it was you were experiencing.


From that point on I'm not going to say that I knew I wanted to write advertising or I knew I wanted to be a writer, but it was this transition where I think I not only started falling in love with writing in that moment, but I also recognized that we're all killing off our youth for something, and did not want it to be basketball anymore, so I quit basketball. I've since decided that that sacrifice is writing.

Chris:

Wow. That's powerful. Well, thank you for sharing that with me. I wonder if your grandmother didn't pass away in that moment, would you still be a writer today, or would you be playing basketball, or doing something different?

Cole:

I wonder that sometimes too. I truly, and I don't have an answer. I hope I'd find writing.

Chris:

Yeah. Eventually it finds you or you find it, right?

Cole:

Right.

Chris:

But it sounded to me like in that moment with your closeness, your relationship with your grandmother and her passing, you found writing as a way to process what you're going through, your pain and maybe to be able to heal yourself, and then you recognized it. Maybe that was just the beginning. As you said, it wasn't like that moment forward I'm going to be a copywriter and work in advertising. So, where else does it pop up in the timeline where you're like, "Okay this is something I can't ignore. There's something here"?

Cole:

Sure. So three years later I graduate from the University of Southern Indiana, because I transferred after basketball didn't work out and I decided to walk away. I did what most college grads do, I went to work for a company. I got about a month or two months into this company. It was actually a small town kind of agency, but I wasn't writing there. I wasn't doing any sort of writing. My boss was great. The employees there were great. The agency did good work, but I hated it. I think that something that's really important to recognize in yourself is are you a good employee or not.


There's a really famous Chuck Daly story who was the infamous coach of the Detroit Pistons, who coached Dennis Rodman for a long time, where Dennis Rodman was mouthing off in practice and one of the assistants was really getting into him, and Chuck Daly called him over and he said, "Leave Rodman alone. You can't put a saddle on a mustang." And I think that that story resonates with a lot of entrepreneurs, and freelancers, and creatives, where they kind of do feel a little bit like that mustang that society is wanting to throw a saddle on them, and it resonated with me a lot.


So anyways, I'm working in this agency and I'm hating my job. I am talking about wanting to be a writer, I'm talking about making a living in writing, but I'm not making that jump. One day I stand up from my desk and I walk out, which I don't recommend doing, I regret doing that, and I emailed my boss and the next day we left on really, really good terms, and I started working for this construction company. The reason I did that is I could work from 7:00 AM to 3:00 PM every day, and then once I got off work I could write, and write, and write and work on my craft.


The first day of that construction company my boss hands me car keys, he hands me a utility knife, duct tape, and an address on a slip of paper. So, I remember thinking this feels like I'm a hit man now, or like I'm going to go murder someone. So, I get in this beat up van and all summer long I'm going into these old apartment buildings and tearing out carpet. How that works is you're driving a knife through the carpet, you're ripping, you're rolling it up, you're wrapping duct tape around it, throwing it over your shoulder, and it's just nasty, nasty work.


Irony would have it, that my agency decides to get a renovation done on their building. My boss has no idea I work there. They hire my construction company to do the renovation. So, I am back in my agency with my ex employees, I'm tearing out carpet. No one is looking down on me, but they are kind of having this look like, what the heck has gotten into Cole? He kind of had a great job, now he's carrying out carpet. I remember that moment was a very, very intense moment, because I felt lower than low, but I also recognized that I would rather, if for the rest of my life I have to work manual labor to pay the bills while I pursue this dream of writing at night, that hurts a hell of a lot less than sitting in a cubicle working a job that I don't like. For me, that was rock bottom, and I haven't looked back since.

Chris:

I think I might have missed that detail when you said you stood up at your desk and then something happened, but then you called your boss. Did you literally walk out on the job? Did you stand up on your desk and say something?

Cole:

No, no, I wasn't rude.

Chris:

Okay.

Cole:

I just literally ... She wasn't in the office at the time. I just stood up.

Chris:

I see.

Cole:

And walked out of the building and went home. That's definitely not something I'm proud of. I think that it's like the equivalent to ghosting someone, but fortunately I emailed her and said, "Hey, I'd love to come in tomorrow and really have a good conversation about what's going on." And we left on really good terms, so.

Chris:

That's good, okay. So, this moment. Okay, you're doing heavy, dirty physical labor. I know what it's like. When you move a carpet it's like dust, and dust mites, and it's okay, but you're doing this, but that's the price you pay to work on your dream, the thing that fulfills you, right?

Cole:

Mm-hmm (affirmative).

Chris:

And I can imagine, like it's ironic. I have to go back there and I'm doing this lower manual labor job, and that must have felt pretty horrible, but you were pretty resolved in your mind at this point. I'd rather do this and feel this way because I get to be more of who I am.

Cole:

Sure. You're spot on.

Chris:

Okay, wonderful. Okay. So, let's track forward, then when you feel like you got your first big break in copywriting, getting paid. I guess everybody would be a writer, not everybody can be a good writer, and fewer writers get paid to make a living, right? The theme of a lot of the things that I talk about is how to help people make a living, that's the important part, doing what they love. So, where is that point when you're like, "I've arrived. I am now Cole the writer."

Cole:

So, I think I became the writer when I decided to walk away from that job because I was, to use sort of a story that Pressfield has used before, burning your ships at shore, right? Where I walked away from the cushy job, or what felt cushy, and I went all in on this dream. So, I think as soon as you do that, you're turning pro in a way, and Pressfield has said that so many times, but that was the first day I felt like okay, even though I'm taking $15 an hour cash tearing out carpet, I feel more professional than these other people who say they want to be writers but aren't doing anything about it writer. Let me not even compare it to other people, let me compare it to me, the day before, when I was saying I wanted to be a writer.


But how I started getting my first clients, and this is more a tactical, you sort of have to set your ego and pride aside and you have to start cold emailing anyone you can get your hands on, and that's what I was doing. I was researching cool startups, and I chose startups versus more established brands because they have younger people running them, they're more open to risk. I think it felt like they'd be more open to giving some kid a chance, and I was right.


I sent out hundreds of cold emails every single week. The way that filtered down was 100 cold emails would end up getting about 10 people to agree to jump on a call. Three would kind of be like, "Eh, let's give it a try." And then one would end up being a client. I mean, it felt like if I send 100, one could end up giving me a chance and I did that for a year, and I eventually got to a place where I was making more money writing than I was tearing out carpet, and it made sense to no longer tear out carpet.

Chris:

That's really cool. So, when you're sending out these emails, I guess you figured out what works obviously, because otherwise we would not be talking today because you'd still be slinging carpet and writing poetry, or writing stories at night. What have you found out in terms of all these emails you must have sent out that works, that gets people to hey, there's a lot of noise, you got to do something to fight that noise. So, what did you discover?

Cole:

Sure. So, when I first started out I was very spammy, right? And I think that sometimes you're that way when you're desperate and you're like, "I need to find someone to work with me." And with that I would write really long emails, but now I'm on the other side of it where I'm kind of the person receiving the cold emails and I can't tell you how many times I get a note from a aspiring writer, and it's four or five paragraph, like a four or five paragraph email. When you have dozens, and dozens, and dozens of emails hitting your inbox every day, for me to read that and for me to turn around and respond thoughtfully, that could be a 30 minute to 45 minute long process.


So, when you're sending someone that long of an email, and especially if you're doing it so cold, you're not just asking them to respond, you're really asking them for money, because if you value your hour at 200, 300, $400, if I'm going to respond thoughtfully to this person's email and I'm spending 30 minutes on it, that might cost me 250, $300 to do that. So, I think you have to be incredibly respectful of the people you're reaching out to and recognize they're very busy. So, write two to three lines in that email, and always at the end of that email ask for exactly what it is you want.


I always show new freelancers tough love, where they'll send me a super long email and I'll get to the bottom of it and this is when I've half read them, and there's no call to action, right? That's copywriting 101. By the end of it I have to know what you want me to do, and I'll respond and I'll say, "Write me again. Do it with 25% of the words and just ask me exactly what you want me to do for you and I'll see if I can help." And the people who take the time to do that, I try to always help them, but I learned that more on the other side of it, where I'm like you're reaching out to busy creative directors and CMOs, and entrepreneurs, and you think that they have the time to read a 400 word email? They just don't. So, keep it super short. Be honest, be human, and always ask exactly what it is you want by the end of that email.

Chris:

A couple of thoughts on that, which is could you give us an example of what you think is a good call to action at the end of an email?

Cole:

Sure. So, let's say I'm reaching out to Bowflex to write copy for Bowflex. Most people might approach that and say, "I'm going to reach out to Bowflex's creative director and to see if they need a copywriter." And they might say like, "Can I write copy for Bowflex?" The better approach is to take a specific product Bowflex is selling and get really, really focused on that one product. So, for example Bowflex has a bike, it's called the C6. That is a competitor to Peloton. So, being that Peloton is the behemoth in the market, if you're wanting to try to write copy for Bowflex, I think you're better off if you're going to cold email them saying, "Hey, I noticed that you all recently launched the C6 bike. I imagine there's a lot of copy you're needing for that. Would you by chance be interested in looking at some of my work?"
There's a good chance they won't respond to that email, so then you email them again three, four, five days later and you say, "Hey, I know you're super busy. I've done some work in the fitness industry and I just wanted to send you something I did for this small startup in LA that sells hydropowered dumbbells." Or something, and send them a link to that. Then if they don't respond again, send them a third email, and it might be, "Hey, I saw this email that Peloton sent out. I feel like there's an opportunity for us to do a cool guerrilla marketing tactic on this. Are you interested? Here's the idea." So, I think you have to get really specific versus taking more broad strokes.
Something I always encourage people to do is if you're not getting responses, instead of applying and asking, just do it. So, Nora Ephron, who was arguable one of the most culturally impactful writers of the past 50 years, she directed and wrote When Harry Met Sally, and Julie & Julia, and this fabulous book called Heartburn about her divorce with Bernstein, who did the Watergate investigations and stuff. When she was first starting out, her dream was to write for the New York Post, for whatever reason. So, she was 22. The New York Post gets shut down because all the writers there go on strike. So, what Nora Ephron does is she writers a parody to the New York Post, and editors get their hands on it and they're up in arms, and they're offended, and they're all upset, but the publisher of the New York Post reads the parody and she says, "If this woman can write a parody of the New York Post, she can write for the New York Post. Give her a job." So, they gave her a one week trial.


They gave her this story on the New York Zoo, where there were two hooded seals that got brought into the zoo to mate with one another because their population was super endangered, but the seals weren't having sex. So, it was really awkward because these seals weren't mating, and their species depended on it. So, she wrote this story on it, and it ended up being a breakout success. New Yorkers found it hilarious, and then she had a job at the New York Post.


So, all that to say, if people aren't responding to your cold emails, do it without their permission. Send it to them and see what they say, versus just going strictly the cold email route. So, don't apply, do.

Chris:

Nice. So, when you were giving examples of what the emails might sound like, it didn't sound like advertising, it just sounded like one person reaching out to another person. Is that part of the secret?

Cole:

Yeah, I think so. Yeah, I think so. I think good advertising writing is viewing the brand as an individual and viewing the writing that you're doing to another individual, not a "target market."

Chris:

Right. Are there any things that you do to try to understand that individual better so that you can more authentically speak and connect to them?

Cole:

So, generally when I'm doing like a voice guide for a brand, I'm having this conversation with the brand and saying if ... Actually, I'll give you an example. So, I got hired on to write copy for a cookie brand in LA called Last Crumb. Their cookies sell for like 15 bucks a cookie, it's absurd, and they sell out. They hired me on and they said, "Just push the voices as far as you want." And a lot of the development I've done was kind of like saying okay, who is the brand if the brand was a person? So, we were able to come up with these really awesome product descriptions that weren't at all like oh, this chocolate chip cookie is ooey-gooey, like a normal product description. It was actually going into narratives, because basically what we had discussed and decided was if Last Crumb was our best friend, it would be someone who is charismatic, he's funny, but he's also a deep thinker, he's a storyteller. He's probably not always politically correct, and the descriptions are pretty spot on with what we had written with that.

Chris:

Can you read some of them? Is it okay?

Cole:

Yeah, absolutely.

Chris:

I'd like to hear it, yeah, because a $15 cookie.

Cole:

Yeah, yeah.

Chris:

What? It better be a really good cookie.

Cole:

Yeah. Let me find a ... Find one real quick.

Chris:

Okay. And is this the brand bible examples of how the brand should speak or is this literally like part of the messaging they send out?

Cole:

Yeah. So, this is actually these are the cookies and the product. So, I named all the products. So, for example, instead of doing a chocolate chip cookie I named it The Better Than Sex Cookie. This cookie is a peanut butter cookie, I named it the Madonna, because Madonna is a huge fan of peanut butter. There's a secret society of peanut butter lovers, so we called it the Madonna. Then the lemon cookie is when life gives you lemons. I think this is actually a really good example of a description.
So, this one's called When Life Gives You Lemons, and this is the description that I wrote. This cookie is as lemony as Snicket. It'll make your sucker pucker. God damn, that last bit was just wildly inappropriate. Anyway, while most lemon bars are as underwhelming as a week old party balloon, our lemon bar cookie actually tastes like lemons are at the party, not like a bunch of lemons are chilling on their phones in the other room, caring more about showing the virtual world of Instagram they're at the party, versus actually being present in the physical world at the party with their friends, who actually care about them. Which is like a much larger question of, can we truly experience anything physically if we aren't present, both mentally and emotionally? But now we're just rambling. We'll shut the hell up and just tell you about the ingredients, and then we dive into the ingredients.


So, it's like these vignettes, right? Where they don't feel like product descriptions, but people are loving them, and it's weird, and it's worked so far, so.

Chris:

Do you think there is this marriage of taste and what you're getting in your mouth, and them reading the narrative and it completes the experience for a person?

Cole:

Yeah, I think so. I think that so much of copy and design is creating this placebo effect. Seth Godin talks about that a lot, where it's less about the ... I think part of a product being great is also creating that magic around it, and I think that that's what design and copy can do.

Chris:

Mm-hmm (affirmative). It's like the we're complicit in the lie that is being told to us, and then we buy in. So the cookie tastes better because we want it to taste better, and the wine is bolder because it's already in our mind that way, right?

Cole:

Yeah.

Chris:

So, you are making it a little easy for them to like this is a story I want to tell myself when I eat this cookie.

Cole:

Exactly. I think so. I think it's important as writers and designers, and marketers, right? To be very aware when you're a character in that story. When I got flew out to Minsk, Belarus to write copy for some startups out there, and before I left I was like, "I need a really good pair of boots because it's freezing there." And so I go to the Red Wing store here in Nashville, Tennessee, and I walk in and this guy is there and he goes, "Have you ever bought a pair of Red Wings?" And I go, "No." And the way he walks me through the Red Wing experience was unbelievable.


He sat me down, he slips the boot on, and he's kind of squeezing my ankles as he's bringing on this book and he goes, and once I had it on and he had tied it up he kind of stopped me and he goes, "Now I want you to know that by the time you're done wearing these boots for the first couple days you're going to want to cut off your feet, they're going to hurt so bad. You have to earn this kind of Red Wings, you have to earn them. Your ankles are going to bleed a little bit, they're going to hurt, but you get through that week, they're going to be the best boots you ever wear." That moment I was sold. I was sold. I was like, "I have to earn these, I'm down. I want them." And I walked away with 300 pair of Red Wing boots that made by ankles bleed all the way throughout Belarus, and as I'm wearing them I'm like, "No, I'm earning these." And I still have those boots, right? But imagine if he wouldn't have said that.


Imagine if he would've just given those to me and I'm in Minsk and my heels and my ankles are rubbed raw, and I'm like, "This was the worst purchasing decision I've ever made." But since he told me that story, all of a sudden it becomes this magical experience, it becomes a part of me in a lot of ways.

Chris:

Yeah. I think he did a little neurolinguistic programming on you there for you to recode the pain, your ankles bleeding, and thinking these freaking stiff boots are tearing my feet apart.

Cole:

Yeah.

Chris:

But now it becomes like a badge of honor to survive that, to say, "I'm tougher than the boot and I'm tougher than you pansies who are not going to go through this." Right?

Cole:

Absolutely. I think it wasn't the first kid he had sold boots to, that's for sure.

Chris:

Right. Was the pain worth it?

Cole:

Oh yeah. I still have them. I mean, it's been three years and they're the best shoes, boots, anything I've ever earned, and that might just be the placebo, right? But I love them.

Chris:

You were complacent in that story.

Cole:

Yeah, yeah. I've fallen for them.

Greg:

Time for a quick break, but we'll be right back with more from Cole.

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Greg:

Welcome back to our conversation with Cole Schafer.

Chris:

This ties into something that I firmly believe and that we need meaning in our life, and when things don't make sense we will form our own narrative, and oftentimes if you don't give someone a good story, they make up a story that is not beneficial to you and your brand. So, give them the story and help them fill in the gaps.
So, this cookie, I'm not going to ... I don't know if you're a cookie connoisseur, but how much of the actual taste of the cookie is the thing that drives the story, or are you just the kind of guy who is like, "Let me look at that cookie, I got it. I'm going to do my thing." How does that work for you on a creative level?

Cole:

Sure. So, one thing I will say is the cookies are the best cookies I've ever had in my life, and they sent me a box of 12 and I was just dumbfounded, they're that good. But something that David Ogilvy would always do is he believed that as an ad man you had to be your client's best client. So, he used all of his client's products. Early on in your freelancing career when you are dirt poor, you can't afford to use all of your client's products, right? It's just not possible. Something that I am trying to do more of, and I don't do it all the time, but I'm trying to do this more, is when I write copy for a product, I'm trying to use it. If I'm going to do it on an ongoing basis, I try to become my client's best client.


So, when I was writing for Bowflex I remember being in a bar one night and they were talking about the Peloton bike, and I was like, "No, no, no. You have to check out the C6 bike. You got to check out the C6 bike." And I think I might have sold someone on that bike that night, but I think that's important. I think you have to have that level of conviction in the brands you're working with because I do think it separates you from everybody else who is just doing it to get paid, right? I think you have to have that kind of conviction in the brands that you're writing for, because the reader and the customer, and the prospect, they can sense that. They can sense if you don't believe in the product. So, I try to only write for the brands that I truly believe in. I mean, I try to use the products, and I'm trying to do more of that.

Chris:

Okay. We've mentioned this before in terms of your newsletter. Getting someone's email address, that's kind of a big deal, because you can try to yell at them from all over social media, but to this day I think email conversions are very high relative to all other forms. So, what does somebody need to know in terms of effectively building out people who want to subscribe to your newsletter? What do you have to do? You have some tips for us?

Cole:

Sure. So, my newsletters have been one of the best business decisions I've ever made, and I run three of them. I run one called Sticky Notes, which is my largest kind of flagship newsletter. Then I run a second one called Stranger Than Fiction, and that's specifically about it's the pitch is batshit crazy marketing ideas that have made brands a lot of money. Then the third one is a paid newsletter, and it's called Chasing Hemingway, and it's really about my journey as a writer, hopefully trying to go from a competent and maybe good to hopefully one day great, and I try to create these metaphors constantly in that newsletter between writing and life and how those two exist in a really magical way together, because there are so many metaphors between writing and living. But I think if you're going to start a newsletter it helps to be really specific.


With Sticky Notes, I think it's a bit of an anomaly just because it's not super specific. I write about just about everything in that newsletter, and it's done really well, but Stranger Than Fiction, where the promise is very focused, and that's I look on the web for really cool marketing ideas that have made brands money, and I write about that each week. That newsletter grew really, really fast because it was so specific. I think with podcasting, if a podcaster is wanting to run a newsletter instead of saying, "Yeah, I write about podcasting." Why not say, "Every single morning I'm going to send you the one podcast episode you have to listen to for that day." Right? Because everyone, I'm a podcast junkie, I experience it all the time, it's like Netflix. You get into Netflix, you're scrolling, and scrolling, and scrolling, and everything kind of looks good and you don't know what to watch. It happens all the time with podcasts. So, if you're wanting to start a newsletter I would just say get very specific with the promise and don't view it as a newsletter, view it as a product, right?


So, Sticky Notes, and Stranger Than Fiction, and Chasing Hemingway, those to me are all products that I'm giving away for free each week. Chasing Hemingway is paid, but those other two, I legitimately feel like they are each one is worth someone paying 10 bucks, but I'm not asking them to do that. So, when you approach this like I'm creating this product, I think that you take the process a lot more seriously. That's not me just talking out my butt, I think if you were to subscribe to Sticky Notes you would see those three newsletters take up about 15 to 20 hours a week for me. They're just that important to my business, and I just care a lot about them.

Chris:

Wow, that's not just like hey, let me spam your inbox, this is like you're working on this now. If you're spending half your work week writing these newsletters. So, these go out once a week. Is that the cadence?

Cole:

Yeah, they go out once a week, and the reason they've been so big is I can ... So, I view my marketing strategy, and I think this can be effective for anyone who is freelancing or an agency, but it's like this funnel where at the top there's this article. So each week I'm putting out three to five articles, right? And they're going to LinkedIn, and Twitter, and Instagram, and then once people read those articles then I'm hitting them with this call to action, join one of my email lists. Then you get further down the funnel and now you have 20,000 email subscribers across three different newsletters. Then you're trying to, one, build that trust with this free product you're giving them, but you're also trying to get them to buy the $97 guide. Oh, you don't have the three, four, $5,000 to hire me as a writer? Spend the 97 bucks and learn copywriting in house. You're not into copywriting? Well, buy one of my poetry books. You don't like any of this but you love my newsletters? Just buy me a Moscow mule on Gumroad. It's 15 bucks. So, then it's filtering people into these buckets where oh, this bucket makes sense for me. That product really resonates with me.
So, the reason I spend so much time on my newsletters is because it honestly has allowed me not to have to cold email anymore, right? I never have to cold email anyone, and it brings me a lot of joy too.

Chris:

If a person is just starting out, and they're like, "Cole, I love this. I want to do that. I want to get to 15,000 people on my email list." What do they have to do to get started in terms of building up someone who is going to look out for the email list? Is it doing some of the things you already mentioned?

Cole:

Yeah. I would say the first race is to just get to 100, right? And I think you do that by creating a really solid opt-in page where you have a little email lander and you can check those out on my site, but mine converted 80%, 70%, and I think Hemingway is much lower because it's paid, but then it's all about just moving traffic to that page, just get people on that page. But I think your race is to 100 and you can just go through your phone and if you were legitimately taking it seriously, just write some of your friends, your best friends, just say, "Hey, I'm starting this thing. I'd love for you to subscribe to it." And get to 100 people, and at the end of every newsletter you send out, just say, "Hey. I would love for you to send this or forward it to someone that you think would enjoy it."


So, start small, and then I think by having 100, 200 people on your email list, then you sort of have that audience that can kind of keep you going as you make that next jump to 1,000. But to get to a 1,000 I think you have to really be taking it seriously, and you have to either have this, like a podcast, you have to have a regular article writing schedule where you're publishing a lot. You'd have to have like a Twitter where you have a large enough following where you're tweeting things out where people are actually reading them. You do have to be putting in the work to get to that larger kind of audience.

Chris:

For you, do you write the newsletter as in real time each week or do you write, are you several weeks ahead so that you don't have to feel that pressure?

Cole:

It's all real time for me.

Chris:

Okay.

Cole:

So, because I think that that's one thing that has differentiated me a little bit as a writer, is my marketing and my advertising and my writing is very real time. So, I don't have this crazy overarching strategy. It's more so like it's more intuitive, and as I go I kind of create and do cool things. One example is for the release of my third book, After Her, I was like, "What could I do for a prerelease that could be really cool?" So, I decided to burn the book. So, me and my videographer, it's like 10 o'clock at night, I get this wild idea. I'm like, "You know what? I'm going burn the cover in the back." So, we go to Kroger and we get lighter fluid and a match and we light this thing on fire, and we start taking pictures of the book, and I post it to Instagram. The goal was people are going to be curious what the actual cover looks like, because I burnt this cover, that they'll buy the book and it'll be a surprise once it comes official launch day.


People wrote me and they were like, "That's the coolest book cover I've ever seen." And so I'm now kind of panicking thinking okay, I spent a $1,000 getting this designed perfectly and people are liking the charred version more. Now is this going to be some big upset when the real version comes out? So, I had to kind of pivot last minute. So, this is what the burnt cover looks like, right? I mean, it's-

Chris:

Look at that.

Cole:

It's really badly burnt up. But anyways, when that happened I started to kind of freak out and then I thought, "Well, this might be even a cooler marketing strategy." So, my next step was for each book I might buy a blowtorch and just lightly burn every book, because who's received a charred book in the mail? Or if that doesn't work, I might buy a bunch of vintage match boxes and then add a note in there that just says burn after reading, so building that into the marketing strategy for the book. But I think sometimes as marketers we're so caught up in this idea of you have to have a strategy, you have to have a strategy, that we miss out on the small magical moments that can happen along the way. So, I think you have to kind of create space for yourself to have this stupid burn the book idea that turns into the really cool marketing concept of everyone gets a really cool 1960s matchbox, or everyone gets a slightly charred book, you know?

Chris:

Yeah. Wow. That's pretty fascinating because something that you did as part of a publicity marketing campaign turned into wait a minute, there's something really cool about this and I'm going to change my game plan. Then the story of the process of the book cover becomes a part of the narrative of the book itself.

Cole:

Mm-hmm (affirmative).

Chris:

I think that's really cool. Really clever. So, I guess the advantage of doing something in real time is you get to be very topical. It's like you're passionate about it right now, but then you don't also then know the arc of how it all works out.

Cole:

Right.

Chris:

So you're just going week by week, and so that's I guess a preference, because I forget which late night show comedians would do this, where I think it was Letterman who would record two or three shows together so it had a certain energy, because it's more efficient, and then maybe Leno who did it every single night like a standup.

Cole:

Yeah.

Chris:

So, his cadence was different. I might have mixed that up, but that's you. You're like I'm going to be here, it's Tuesday, it's Thursday, I'm going to write what I feel and get it ready for next week, but there's pressure to do that.

Cole:

Yeah, there's a ton of pressure. And I'll also say, you have ... I checked out your agency, right? And it's not just you, you have a team. I don't think that works for a team, right? If you have a bunch of people just saying you're going to go rogue and do whatever you want, I just don't think that works. So, if you're a solo creator I think you have a little bit more room to create in real time, if that makes sense. Like with your podcast, I know a lot of podcasters will batch podcasts where they'll record a bunch of them in one day. I totally can see where that makes sense with how energy intensive that is, and for creatives you have to have that deep work where you can take three, four hours to really dive into a sales page, or dive into writing a book or a blog. If you're recording every single day, you probably have like 30 minutes to prep before, you have the hour and a half long interview, then you have 30 minutes to just get back and focus afterwards. So, I totally understand batching. Just for me, I've been able to keep things a lot more exciting by kind of creating in real time.

Chris:

Yeah. I don't know how people do that, I really don't. I don't know how people do six or ... I can't even do, I don't think I could do two of these a day because for me as an introvert there's recovery time.

Cole:

Yeah, yeah.

Chris:

I'm really focused on our conversation, and I'm going to go lay down. I'll probably have a cookie, I don't know why, after our call, and then just like okay, I need to recuperate and charge the batteries, if you will. So, it's a different thing.

Cole:

Yeah, yeah. I think just everyone's a little different.

Chris:

Yeah. Okay, so tell us a little bit. I'm just cognizant of time here. Maybe I have one or two more questions for you, but tell us a little bit more about ... Your business model fascinates me, and I like to share stories of success where people can have an alternative way of working and living. So there's, we already talked about it, the service part that you do by day, a hired gun to write copy for different marketing campaigns and for different companies, and then there's the passive income stuff that you do. I think you said you had two courses, one on copywriting and one on ... What is it?

Cole:

Freelancing.

Chris:

Freelancing, I'm sorry.

Cole:

Yeah.

Chris:

Copywriting and freelancing, and then there's your poetry at night. Then there's this thing, this paid Slack community. What is that?

Cole:

Yeah. So, that's called the A Team. I wanted to sort of compile this group of really awesome creatives and people in advertising, and entrepreneurs, and writers, because something like I've recognized is I've been lucky to garner like a pretty decent size audience, not every freelancer has that luxury. They might go their entire career where they don't have a list of thousands of people that they can email, right? So, for a lot of freelancers you can make really good money by having great connections, right? Where you might be a freelance graphic designer who is friends with a bunch of other freelance graphic designers, and if they get too busy they can pass you off work.
So, what I wanted to do with the A Team was kind of create this town where, this online environment where people can learn from one another, but they can also pass off leads to one another. So, I'm in a position now where I'm really lucky to be able to turn the projects that don't make sense for me down, whether I don't agree with the product, or it just doesn't resonate with me, or the budget is so low that I can't do my best work for the budget. So, the A Team is this place where if something like that happens, I can just drop the lead in there, drop the email address in there, and now freelancers who maybe charge less who still do solid work have this opportunity to reach out to these brands. On top of that, you're getting this cool environment where people seem to be pretty supportive of one another and open to learn, and I think we have a few agency owners in there who are further along in their career who also want to kind of help people up too. So, as an introvert, it's been a little bit of a weird place to operate, but I run it with my brother too. So, he helps manage the whole community, which takes a lot of the pressure off of me.

Chris:

So, it's a place where people can meet other people from different disciplines but also to hire one another and also to get leads. Is that the main?

Cole:

Yeah. So, the main kind of I think if we were to say there's the three benefits. One is being able to get direct feedback on all your work, right? So, we'll have graphic designers in there who drop a website they just designed and they're asking for feedback. So, feedback is huge. I think the next thing is leads and sort of partnerships that haven't been happening, that don't happen as much outside of a community like that. I think a huge thing for all graphic designers and copywriters is to find another person who they really respect in the opposing field and then just partner up with them and say hey, there are so many times I start writing copy and I need a web designer, be top of mind for that person. So, leads and partnerships is kind of the second major benefit.


Then I think the third is just that community. We do monthly meetups where just online we'll do these speed dating rounds where everyone gets in and you have five minutes to talk to someone face-to-face, then it switches and you do it with the next person. So, I think the community aspect is a huge selling point just because we haven't really gotten that this past year and a half with COVID and stuff.

Chris:

Yeah. We definitely need that. We're feeling the hunger for social connection and to be along, to belong to part of a community. What is the price for that?

Cole:

Yeah. So, we tested out various pricing. Right now it's at $100 a month. Something we really want to do with it is just keep it small. So, 250 people, and that price point forces people to, one, I think it filters out those who aren't serious about it, but when you're paying 100 bucks a month, you're taking it more seriously too, and you want to get your money's worth. So, it's been good to price it higher. There might be a day where we adjust it some, but the 50 to $100 range is where we've kind of been testing.

Chris:

That sounds pretty reasonable, especially if you're able to get those three things. Getting feedback, I mean, what would somebody pay for feedback? And if it's good feedback, it's going to help you grow. The whole idea about leads and being able to put money back in your own pocket, that's a good hook.

Cole:

Mm-hmm (affirmative), for sure.

Chris:

Yeah. Awesome. Okay, so if people want to find more about your writing, your poetry, and everything else that you do, where is the best place to send them?

Cole:

So, for the poetry just Instagram. My handle is @cole_schafer. Then if they want to connect with me more in advertising and the article, long-form writing side of things, I'm just at just honeycopy.com and I have a bunch of newsletters there where they can subscribe and I'll be in touch in a week. Yeah.

Chris:

So, the website honeycopy.com is where they can find everything, right?

Cole:

Everything, yeah. Everything.

Chris:

In terms of different newsletters, okay. Fantastic. You are available for contract work, right?

Cole:

Yeah, yeah, absolutely.

Chris:

So, people want to find out, they just go to your website and hire you. Is that the way it works?

Cole:

Yeah, it works that way, or a lot of them just respond to my newsletter, or they'll reach out on Instagram, which is funny to me because that's all poetry, it's not really about advertising, but they'll say, "We'd love to hire you for this." And so yeah. It's mainly just through the newsletter that people reach out and Instagram some.

Chris:

It was a real pleasure talking to you, Cole. Thank you.

Cole:

Yeah, man. This was a lot of fun. My name is Cole Schafer and you are listening to The Futur.

Greg:

Thanks for joining us this time. If you haven't already, subscribe to our show on your favorite podcasting app and get a new insightful episode from us every week. The Futur podcast is hosted by Chris Do and produced by me, Greg Gunn. Thank you to Anthony Barro for editing and mixing this episode, and thank you to Adam Sanborne for our intro music.


If you enjoyed this episode, then do us a favor by rating and reviewing our show on Apple Podcasts. It'll help us grow the show and make future episodes that much better. Have a question for Chris or me? Head over to thefutur.com/heychris and ask away. We read every submission and we just might answer yours in a later episode. If you'd like to support this show and invest in yourself while you're at it, visit thefutur.com to find video courses, digital products, and a bunch of helpful resources about design and creative business. Thanks again for listening and we'll see you next time.

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