TCC Podcast #145: Trusting Yourself with Jay Pitkanen - The Copywriter Club
TCC Podcast #145: Trusting Yourself with Jay Pitkanen

Copywriter Jay Pitkanen is our guest for the 145th  episode of The Copywriter Club Podcast. Jay has an interesting background, having worked as a taxi driver and relationship coach which has prepared him well for the work he does as a copywriter. Kira and Rob asked Jay about:
•  how he went from poker player to blogger to copywriter to coach
•  what his business looks like today and what he writes
•  why we need to be “cool with being vulnerable”
•  what the typical conversation with his coaching clients looks like
•  what it takes to shift someone’s mindset and why it works
•  improving the offer to create a better connection with the audience
•  the value of personality in attracting the right clients
•  why trusting yourself leads to more opportunity—don’t wait for permission
•  the power of controversy and the effect on his business
•  the mistakes copywriters make that hold them back

We also asked Jay about the lessons he learned as a taxi driver—his #1 takeaway from that experience is don’t show fear… and maybe that’s a good lesson for copywriters as well.

To hear this one, click the play button below, download the episode to your favorite podcast app, or scroll down for a full transcript.


The people and stuff we mentioned on the show:

John Morrow
Luke Sullivan
Jay’s website
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
The Copywriter Underground
Intro: Content (for now)
Outro: Gravity


Full Transcript:

Rob:   This podcast is sponsored by The Copywriter Underground.

Kira:   It’s our new membership designed for you to help you attract more clients and hit 10K a month consistently.

Rob:   For more information or to sign up, go to

What if you could hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes and their habits then steal an idea or two to inspire your own work? That’s what Kira and I do every week at The Copywriter Club Podcast.

Kira:   You’re invited to join the club for episode 145 as we can chat with copywriter and relationship coach, Jay Pitkanen about marketing his business, what copywriting and relationship coaching have in common, owning your voice and viewpoints, and the business lessons he learned while driving a taxi.

Kira:   Welcome, Jay.

Rob:   Hey, hey. Glad to have you here.

Jay:    Hi guys. Thanks for having me.

Kira:   Yeah, great to have you here, Jay. I know we were just mentioning before we started recording that we had connected a couple of years ago, maybe three or four years ago. I’m not even sure how long ago now and so it’s great to catch up with you now and hear about how your business has changed. So why don’t we start with just how you got started as a copywriter and where you are today?

Jay:    Oh, sure. So the thing is, I’ve always been interested in how people’s minds work and how I can influence that. It’s been like a curiosity of mine ever since … as long as I can remember. I used to be a poker player for a while and then that got a bit too stressful to do as a living thing, but that always … The reason I was interested in that was because I loved to see what’s going on in people’s minds, or at least I thought I could do that and that was so fascinating to me and ever since then, it’s been expressing myself in a way to get other people interested in stuff and just hearing how people think and ways to get to influence that.

That’s always been such a huge fascination of mine and I wonder when the first time I really got into copywriting though was. It must’ve been like five or six years ago, when I started one of my first blogs and really got into writing.

Kira:   Yeah, just when you got started with copywriting and then how that’s changed too. Are you a copywriter today or has that morphed into something else over the last few years?

Jay:    Out of my blog … First there was I wanted to monetize my blogs. I wanted to be a blogger right? This was a whole huge thing four years ago. Everyone wanted to be a blogger and I’m like ‘Hey, I can make money with this, so yeah, I’m going to be a blogger.’ Whatever that means, I went to John Morrow and did his class and started building my blog, but I realized that more than the blog writing, I was interested in the marketing stuff, so then through that, I got a job at this software company, Thryv Scenes, which some of you may have heard of. I think that was actually the place when I really, really dived into copywriting as it is, as a sales tool, as a sales mechanism.

So we worked together for a couple years but then I realized I really got to do my own thing, so I started … We went our separate ways and I started building my own business and I figured since I liked writing and I liked the marketing stuff work so copywriting must be my thing and the interesting thing was as a new business owner, I started looking for gigs and I started hanging out with other copywriters.

I realized that most of my time was spent coaching other writers to do better with their work, coaching on confidence, coaching on marketing strategy, coaching on everything which is not me doing copywriting and that’s when I started to think ‘Hang on. Maybe I’m not a copywriter as such. Maybe I should just be a marketing strategist and let the writers do the copywriting, right?

That’s where I am today. I’m more doing the marketing strategy for copywriters and of course do my own copywriting on the side, but I’m more focused on the strategy consulting and coaching.

Rob:   It’s cool, so tell us a little bit more about that, what you’re doing today, the marketing and the coaching side of it and how you’re using copy to magnify what you’re doing there.

Jay:    Right, right. As I’ve been working with freelancers who want to grow their own business and copywriters and writers, the creative sort of people, the people with creative minds and the sensitive people, I realize that there’s a huge demand for a product, for confidence and for that not caring so much about other people’s opinions mindset. I started building a product on that and then I realized that ‘Hang on. I’m expressing my own skillset, my own talent and I’m basically writing the sales stuff for my own stuff and the sales content, the landing pages, the sales pages for my own product’ and there I realized that ‘Okay, actually I have the copywriting skills to express my own product benefits’ and the stuff like that, so that’s what I’m thinking about now, is this huge sales base that I just wrote for myself.

It felt more my thing, because I’m basically … not writing copy as such, not writing copy as a service, but I’m more … Through copywriting, I’m serving my coaching clients.

Kira:   So today, most of your work is around different coaching programs. Is that right?

Jay:    It’s kind of right and I think you mentioned the picture I took in the local town square. I had this sign that says ‘Pre-dating advice’ and that’s … It’s one of the things I do. This was actually quite a random idea, but the main thing in my coaching is confidence and communication. As you notice, I’m a great communicator and I never make any mistakes on that, but it’s all about … That’s what I teach people, is to be cool with being vulnerable and making mistakes and it leads to all these side projects, like the dating and relationship coaching which always requires vulnerability and good communication and freelancers who want up their own business, that also requires a connection with your own vulnerable side and knowing what you actually want from the business.

Kira:   Yeah, I love that concept of being cool with … cool with being vulnerable. I think that’s such a good way of putting it, so it sounds like right now, you have maybe two different types of clients. You have copywriters potentially and other creatives and then you have maybe another bucket of people who are in the dating world and just trying to hook up, so is that accurate?

Jay:    Well, kind of. I don’t have many dating clients per se, but it’s more like I have a couple of clients who are men, men who are trying to learn how to be better men. Maybe not better is probably not the word, but grow into the man they always wanted to be. That’s the kind of client I have, but I also have the marketing strategy clients and this is the really interesting thing because I keep … I can look back at a couple of … the past decade basically and I’ve been flipping around between teaching people and marketing.

It’s been two distinct buckets and just in the past few days, I’ve been wondering is there a connection there because what I’ve always … and both of these skillsets require teaching and explaining and helping people understand stuff, so that’s … I think there is my skillset, really, is hanging out with people and listening to what they want and what kind of goals they have and helping them get to that place, or at least show them a direction to get there.

Kira:   Right. Yeah. I can see where there’s an overlap and it might be interesting to talk about the overlap between the two spaces you work in. Could you give us just an example of a couple action steps you would give to one of your clients? Let’s start with the dating space. Maybe one of the men you’ve worked with who wants to be more vulnerable and cool and become the person they want to become, what would you ask them to do typically?

Jay:    Typically, it always starts with ‘Forget about the girls or guys’. Forget about the type of person you’re attracted to. Just forget about trying to get that and they’re like ‘What? But that’s the point!’ But it’s absolutely not the point. It’s the opposite of the point. Where we always begin and where we always should begin is sitting down, listening to yourself and listening to all the thoughts and feelings that come up, meditation, and learning to accept those things.

That’s the first step and this is what I start with all my … It’s basically what I do with my marketing class as well. We get together and we figure out their culture and their values and what they want their business to look like to the outside. This is what we do with the dating clients and it really only takes I would say a couple of hours of meditation for these guys to go from ‘Ooh. I want the date’ to ‘Oh, look at this beautiful world and all the beautiful people in it’ and once you make that even slight shift in mindset, suddenly people want to hang around with you. People are much more interested in being in your orbit as in you become more attractive. Does that make sense?

Rob:   Yeah, it definitely makes sense. So tell us why that works. What’s the reason that that shift works and I think I can see a copy lesson in this as well, but I’m really curious to know how a shift that simple can be so effective.

Jay:    So attraction … We can’t be attracted to everyone. I’m not even going to try to say that because that’s just not true, but with some people, we feel attracted to and they feel attracted to us because we’re different sort of people with different sort of values and different sort of energy, if you want to use that word.

I’ll use it very carefully as well, but the whole problem with most people, at least most people today is that they are completely disconnected from who they actually are because society wants us to be … wants us to conform to a perfect standard, wants us to be good enough, wants us to have … look attractive, look beautiful, wear the right sets of clothes, do the right sets of things, speak in a perfect way.

We create these standards for ourselves and living in a place like that, either consciously or subconsciously, you push your real self deep down so nobody would see it, but the problem is, that’s where the interesting stuff really lies and once you start meditating, once you start accepting those parts of you which are imperfect, which are ugly, which are nasty, which don’t conform to societal standards of being good, then suddenly first of all, you become interesting.

But, also what makes you really attractive after that is the fact that you accept yourself and you have this glow of accepting the world and having this love for yourself and acceptance for yourself. It immediately becomes acceptance for other people as well, because you no longer … You don’t judge yourself so you have no reason to judge other people in those things either and people can see that. People can sense that from a mile away.

You’ve seen people who are smiling and glowing and radiating, even in a place like New York and people stand out if they’re positive like that.

Rob:   No doubt about it. So let me see if I can draw a copywriting lesson from what you’re saying because it’s related to some things that (Luke) Sullivan shared on our podcast a few weeks ago, when you talk about being interesting as a person makes you a better copywriter, but it seems to me that part of what you’re saying here is to take a step back and think about the offer before you even are thinking about who the customer is or who I’m trying to attract.

You’re improving the offer. You’re trying to figure out what it is that you have to offer the world or that be interesting thing and a lot of copywriters start writing with ‘Oh, we need … We have a particular thing that we’re doing’. Maybe it’s a course. Maybe it’s something that you’re selling, or some kind of service that you’re working on and we immediately accept that’s what it is. There’s no changes there and we jump into who is the customer and how do we sell it and maybe there’s a step back that we should even be taking where we say ‘The offer isn’t good enough. What we’re offering here isn’t going to sell to the audience that we want to sell to and we need to take some time to figure that out before we put it out into the world’. Does that seem like a good lesson to draw from the relationship that you’ve talked about?

Jay:    I think so and that’s the way I run my agency basically. I’m not sure if everyone agrees with that, but it makes sense to me and it’s a natural place for me to start up the marketing process and I’m going to call it marketing process because what you’re talking about is copywriting process but I think they’re one and the same, really, or at least on many levels, the same thing.

So what you basically said is ‘Is the product even worth writing about to this audience?’ And I think that’s a great question because well … so my marketing process, like I said it starts from figuring out the values, figuring out the culture, figuring out what type of message, what type of value the company wants to bring to the world and how they want to communicate to their audience and what they want to … how they want to help their audience.

And if the product doesn’t communicate that, then it’s … at least in my opinion, it’s very, very difficult if not impossible to make a good copy, make good sales copy for that product. It’s going to sound fake because it’s not going to reflect the company’s message and while it may connect with the audience, they’re going to feel some sort of disconnect.

I wish I had some factual numbers to put on this, but this is just my gut reaction to whole thing and this is how I like to do it, so if instead, the message the company wants to send is completely congruent with the product they’re giving out, then I would say the copy almost writes itself. Of course then again, then it can do interviews and you can do the whole copywriting, the work process, but it’s much, much easier to write when there’s … What’s that thing? There’s a good term for that thing, when there’s a congruency going through the whole sales process.

Kira:   Parallel? It’s …

Jay:    The con.

Kira:   We know..I think congruent’s pretty good. I can’t top that.

Rob:   Maybe congruent is the right word.

Jay:    Yeah, yeah. Let’s go with that because yeah … so there’s a congruency coming from the company’s message to the product, then it’s so much easier to write a copy, to deliver that message to the customer.

Kira:   Different copywriters we’ve worked with in some of our programs and when they’re working on their website and they’re updating their website copy, of course we all get stuck and just freeze, but it seems like it’s tough when you’re thinking about your audience and your potential clients and you’re trying to speak to them and capture their voice, but you just leave yourself out of it completely. At least that’s what I’m taking away from what you’re saying. Maybe you do have to start with your own brand, your own viewpoints, your own values and start with you, with your own brand before you even start connecting to the audience because if you’re not clear about who you are and what you stand for, then it’s really hard to make that connection.

And I think as copywriters, we’re trained to focus on the prospect in conversion copy, which is correct, but when it comes to our own brand, it could be the opposite. Or at least for me, when I worked on my website, I didn’t think about clients. I just thought about myself. I was really selfish with the process and I was like ‘What do I want to say? What do I want to feel like? What do I want to share?’, and it ended up attracting the right people, but again, it’s just different, depending on if you’re working on conversion copy versus your own brand and sharing your brand values, so I think that’s where some of us get tripped up, at least where I’ve gotten tripped up in the past.

Jay:    Yeah, but Kira, you’re one of the few people in the copywriting world whose website I remember. The reason for that is you put your whole personality into it and that’s part of what I try to teach with my coaching is that the value that people want to see is it’s hiding deep within you and you have to access that and you have to be vulnerable enough to show it on your copywriting sales page.

Of course, this works great when you’re working on your own brand because I think your own brand needs to show off how crazy you are and how perfect you are in your own little weird world because people are going to resonate with that more than the message, more than the words you write on the page and once you get into contact with that, then the message just takes care of itself.

The best copy, the best articles ever written are the ones where you just sit down and let the creative process flow through you instead of trying to carefully pick each word, to make convert one person more.

Kira:   Hey, we’re just jumping into the show today to tell you a little bit more about The Copywriter Underground. Rob, what do you like best about this membership?

Rob:   So, this membership community is full of copywriters that are investing in their businesses and taking what they do seriously. Everything is focused around three ideas: copywriting and getting better at the craft that we all do, marketing and getting in front of the right customers so that you can charge more and earn more and also mindsets so that you can get out of your head and focus on the things that will help you be successful at what we do.

There’s a private Facebook group for the members of the community and we also send out a monthly newsletter that’s full of advice again, on those three areas: copywriting, marketing, and mindset, things that you can markup and tear out. Put them in your file. Save them for whatever and it’s not going to get lost in your email inbox. Kira, what do you like about The Copywriter Underground?

Kira:   I love the monthly hot seat calls where our members have a chance to sit in the hot seat and ask a big question or get ideas, or talk through a challenge in their business, because we all learn from those situations, and then I also feel like the templates we include in the membership are valuable because who wants to reinvent the wheel and Rob and I end up sharing a lot of the templates and resources we use in our own businesses so I would definitely want to grab those.

Rob:   So if you were interested in joining a community of copywriters that are investing in their business and in themselves, trying to do more, get more clients, earn more money consistently, go to to learn more. Now, back to the program.

Kira:   So do you have any questions or a step by step process for someone who’s listening, who knows they’re struggling with this and they agree that this is important, but they aren’t necessarily working with someone, or coach. Maybe they’re not able to hire a coach yet. What could they do on their own just to get some of these answers and figure out these core elements of who they are, whether they’re trying to market their business, or they’re trying to step into the dating world, again, it’s so similar.

What are one or two questions they should ask about their own life and business?

Jay:    I’m not so sure about questions because that’s always … If I ask questions, that’s me leading them to an answer but the fact is, people always know the answer. You know what to write. That’s a fact, but to pull that answer from within you … and I sound so woo woo saying these things, but I really don’t mean it that way, because your brain works in a certain way so you know how to express things. You just have to trust that voice, but to pull this information out of yourself, well I always recommend meditation because that’s what you should do every day is to sit by yourself and listen to your thinking and process that crap going on in your brain and let that smoothen out, but for writing, the most important tool is journaling.

By journaling, I mean … You can do the morning pages thing, but the thing I do is I just open up a Word document or a Google Docs document and I start writing non-stop. I start putting words onto the page and if I get stuck, then I just keep repeating the same word and the most important part of that is it keeps your fingers moving, keep your thoughts coming out because that’s a way to unclog the garden hose. Kyle [inaudible 00:23:43] calls it … You turn on the garden hose and at first, it’s sputtering and all the muddy water that’s been accumulating, it comes out, but then after a while, everything becomes clear and it’s a smooth flow, so that’s what happens with your writing and your thoughts as well once you get into that space where you’re not constantly filtering, constantly editing yourself.

Then the real good stuff starts coming out and once you get into that place, then you can just start writing your copy because again, you know all the answers, but I wanted to add to that because this is very good advice if you’re building your own brand, but if you’re writing copy for someone else, that’s a slightly different animal because you’re also meant to speak with the company’s voice, so in that case, first of all, I would recommend only taking clients with whom you resonate on a personal level so you understand their product and you feel it’s a good product on some level, at least, because only then I feel it’s worth writing about, but even then, the same principles apply because then you put your own style into whatever you want to say about their product and again, if you stuck, you know how to do this.

That may sound like a cop out again, by the way, when I say that you know how to do this, so if you’re a completely new copywriter, of course it’s a good idea to get the fundamentals down, get the … What are these acronyms for a good sales copy? Read a couple of those so you understand what a good structure might be and then once your brain starts to get accumulated to … acclimated? What’s that word? Once your brain starts to get acclimated with how the sales process works, then it can just pour your creativity into that structure, into that template.

Rob:   So Jay, I’m curious if there are other lessons that you’ve learned in marketing or as you’ve been building your own coaching business that apply directly to copywriting in the way that we communicate what’s important or the offer that we have for our clients. Maybe that’s a terrible question, but what other things have you learned as you’ve built that business that might apply to a copy?

Kira:   I wasn’t laughing at you. I was laughing with you, by the way.

Rob:   Yeah, I’m definitely laughing with me too.

Jay:    Maybe I’m repeating myself, but I think the only thing … the biggest thing is to trust yourself and this is reminding me of … in the last few days, I’ve done a lot of meditating and reflecting on my couple of … basically the last decade of mine and wondering why I keep flipping between marketing strategy and coaching and it’s always been a case of not trusting myself enough to just go with the flow and by the flow, I mean there’s been times when life has clearly handed me an opportunity to do something but I’ve been too scared to take the opportunity or I’ve thought that ‘Okay, that opportunity’s a bit silly. I’ll do this thing which is the proper thing to do which is what people expect me to do, so I’m going to go that way’ and then because I’m not that person, I’m the person who wants to do the opportunity, then something inside me keeps pulling me that way and I was looking back and I realized I’ve been trying to do these proper things but in the meantime I was helping a couple friends with their marketing, doing these marketing strategy projects on the side without even realizing that that might be a good profession, good source of income.

So I was … I’m not going to say wasting my time, but I was needlessly distracted by trying to be something which I am not, so I’m not really sure if that’s even close to answering your question, but I think … it’s always … You know what to do and you get these senses of what you would like to do and you have to trust that feeling, even though it sounds crazy and it sounds scary and maybe no one else is doing it, but if it feels right to you, you have to go that direction.

Kira:   Maybe even obvious, trusting yourself, but I think it’s so important because so many copywriters are just waiting for permission to do something and I’ve been there too and we wrapped up our Mastermind retreat last week … two weeks ago and we had all these hot seat coaching sessions, right, so everyone’s asking a question to the group and we’re giving feedback and advice and what we noticed is that a lot of the people, the copywriters in the hot seat were asking for permission.

They already knew exactly what to do and they wanted permission and some feedback from the group which is totally normal and it was great that we could do that for that person, but I think it’s starting to really resonate with me too, just that you’re right. We can take the copywriting courses, get the basics, continue to learn. We’re not saying to stop, but don’t freeze because you don’t trust yourself to move forward and to veer off and get like … and take a framework and make it your own and do something a little bit different or crazy.

That’s where it gets interesting and like you said, that’s where you start to figure out ‘Okay, this is how I can show up and this is what I can do’ and that’s what you’re doing in your business now. Can you give us any examples, really specific examples of some of these changes you’ve made? Like you said you were trying the right thing, or you’re trying to do what you were supposed to do, but it wasn’t working, can you just get more specific there with your examples?

Jay:    Yeah. You mentioned permission. That’s a huge thing because I’m just thinking about all the times I felt personally that ‘Okay, I should be working. I should be working right now. I’m wasting my time. I’m not doing what I should be doing. I should be pitching. I should be doing this’ and every time you get that feeling that you should be doing something because it feels … otherwise they feel guilty or lazy or whatever word you want to put to it, that’s usually something that is coming from an external source because to be more specific in the whole ‘trust yourself’ thing because again, that sounds like a huge cop out. Everyone says trust … It’s like in the dating world. ‘Dad, how do you get a date?’ ‘Well, just be yourself, son.’ That doesn’t help me!

Rob:   Yeah, being myself has gotten me the date so far, right, so I need to be something else.

Kira:   It got you married, Rob. It got you married!

Rob:   That’s true.

Jay:    Yeah, but the fact is become your best self and that’s where we can start building on that, but anyway. On the ‘trust yourself’ thing, how can you trust yourself if you have no idea who you are and that’s where we start getting in to the more action steps things and it really is a matter of meditation. I really like meditation, so it’s a good thing and I would say exercise and eating healthy, doing all these things, but the main way you start to trust yourself and the main way you start to learn who you are is to listen to these urges.

If you feel like ‘Okay, today I should write six pages of this thing. Today I should pitch this client. Today I should build an email automation’, whatever. If it feels like you should do it, then it’s probably not the thing you want to be doing. Sometimes I feel like I want to watch six episodes of some series on Netflix, so then I do that and even though there’s a little voice in me that says ‘You should feel guilty about this.’, first of all, I accept that voice and I love it because it’s part of my past story that’s trying to tell me that ‘Please don’t succeed and go to the next level’ because by doing that, by being lazy and by being something my parents for example would give me a whole lot of feedback about, it might lead to a new idea.

It might lead to a brilliant piece of copy I might write in the next hour or it might lead to a new article. It might lead to something. It might even lead to a new client if … let’s say you watch six hours of … What do the kids watch these days and then the next day, you’re in a coffee shop and someone comes over and they just watched the same series and suddenly, you have the same topic to talk about and maybe they become your new client and you never know where it’s going to lead when you just listen to that deep intuition, that … when that voice inside you says ‘Nope. Today we’re going to just sit around and do nothing and not feel guilty about it.’

That’s one of the examples where you just have to trust that thing, however crazy it sounds. I’ve had more than once in the past couple of years … I’ve felt like ‘Okay, I’ve got to take a break from Facebook because it makes me crazy.’ I always post silly stuff and get into silly arguments with silly people. It’s no use to anyone. It doesn’t … I would much rather be spreading good feelings to the world and for the first time in years … What was it, four months ago, I decided ‘Okay. I’ll just stop using Facebook for a while’, whatever that means and then just following basically that same line of thought, I bought a ticket to Germany because it felt like a good idea. Then in Germany, in Munich, I got … My rental car was upgraded to a wonderful Beemer which was nice and then just following the same line of thinking of following that weird little voice inside you that feels good, that led eventually to negotiations with a certain luxury car manufacturer in Munich about some sort of co-creation opportunities.

We haven’t done it yet, but the guy is wonderful and I love the brand and there’s no reason we can’t work together, so that deal might eventually be worth six figures, seven figures, I don’t know. If I would’ve stayed here and just hit my head against the wall trying to put content on Facebook, I don’t think that would’ve led anywhere. Maybe I would’ve felt horrible and depressed and … Is this practical enough? Should we go deeper?

Kira:   Yeah, get off Facebook and you get a Beemer. I think it’s a really practical…I’ll take it.

Jay:    Sure. Well, flights don’t cost that much. The reason I flew there is because currently, I live in a small country and we don’t really have anything here, but if you live in any size city, you can just go down to your local whatever shop which interests you and say hello because that’s what humans do. We like to connect and feel connected with people who are interested in the same things we are, and the reason I mentioned the BMW is because I had rented just a basic car, just to get around Munich and the guy at the rental as they often do, he tried to upsell me on the car and I’m like ‘No, no, no. I’ll just take the Volkswagen. I don’t really care.’ Then he’s like ‘Okay, dude. I’ll just give you the BMW for the same price as the Volkswagen.’ I’m like ‘Why would you do that?’ That’s the thing. It could be just a coincidence, but I think there’s …

Kira:   You must’ve seemed like a responsible person.

Jay:    Yeah, I think that’s part of it, because there’s always this sort of … Once you start following that weird little voice inside you, once you start doing that, and people start reacting to you in different ways. People realize that ‘Hang on. This person’s actually in charge. They’re in control of their own life and they’re on a path of creating something and it seems really cool’, because people want to be that. People want to also express themselves in their own unique way and people, I think, sense this on some level.

It’s not the first time I’ve heard that people start getting free stuff when they start following their little weird voice inside.

Rob:   So Jay, let’s change the conversation just a little bit. You mentioned some of the discussions that you’ve had on Facebook and one of the things that I’ve noticed about you over the years is that some of your comments might be a little strong. Some people might think that they’re controversial or would disagree with you and yet you own them and stand … share what you believe and stand up for those kinds of things. Have you found that that impacts your business at all and talk a little bit about just the importance of owning your voice and your viewpoints.

Jay:    It’s something I’m acutely aware of. I have a tendency to say too much, but also I do stand by what I say because I mean well and especially in copywriting groups, what really ticks me off is the guy or the girl who comes to that group and they post something just to get … For example, they’re complaining about not getting clients because blah-dee-blah-dee-blah and they want to get validation for their lack of success because they don’t want to do the work.

It’s so easy to see through that. It’s like ‘Okay, have you done the work?’ and they clearly haven’t so then I call it out and people … That’s uncomfortable. It’s uncomfortable facing that fact. ‘Okay. I didn’t do this. I should’ve done all the work before coming here and playing the victim card.’ That’s something I’ve seen a few times and that’s something I’ve commented on, but it’s not to be an ass. It’s because I believe someone’s going to read that and go ‘Yeah. I shouldn’t complain. I should just sit down and try again.’

And over the years, I’ve tried to become a bit more diplomatic and try to come more from a place of love rather than pick fights, but I suppose there’s a part of me that likes to argue and debate and that’s also something I always look for, is not a fight, but a good debate opponent and I’ve made some good friends that way, so I guess it works out.

But I do feel that if it’s not on Facebook, but let’s say in real life because Facebook is all these things a weird filter and weird color and weird atmosphere. If it’s in real life and you feel like saying something, I do feel you must say it because every time you say something, that comes from the heart and you are not trying to insult someone or bring someone down. If it’s just a thing you feel like saying, then you must say it because that is a signal to your body …

That’s a signal from you to your body, not to make a duelist thing out of this, but it’s a signal to yourself that it’s safe to be yourself and it’s a signal to yourself that you can trust yourself. You can express yourself and good things will come out of it and I do believe good things will come out of it because if the people around you are not going to let you be yourself, then those are not your people and eventually you will find your people and hang out with those people more and that’s going to be beneficial to you.

Maybe I should underline that all of this needs to come from a place of love and co-creation, because this may sound like a license to just be an asshole and be horrible to everyone, but then that’s totally not what I’m saying.

Kira:   Yeah, no we get it. I think it connects back to what you were saying before about trusting your gut and trusting yourself and making those choices in your business and that feeds into your opinions and viewpoints too, trusting yourself that you feel a certain way for a certain reason and not holding back and sharing that, but yeah. I agree with you. It’s got to come from a good place, not from especially online, just trying to stir up controversy for the sake of stirring it up. That drives me crazy, but I get that’s not what you’re saying at all.

So I’m just curious. What other … Because you’ve worked with other copywriters and marketers really intimately with your coaching, what other mistakes do you see copywriters making that hold them back today, that you want to call out and share?

Jay:    This is actually a trap I fell into many, many, many times is trying to follow the expert. I think following the expert is a good idea because … It’s fundamentally a good idea, because you can learn what they’ve done and follow their thought process, but every time I’ve tried to follow the expert very literally and do everything exactly like they say, it sounds like a good idea, right? Just follow the expert. Just do what they did and you’ll get success, right, but more often than not, people don’t succeed with these methods. Online courses for example, they’re hugely successful these days.

Everyone is buying online courses all the time, but the rate of finishing an online course … I mean, it’s like 1% or less. What’s the reason for that? I think following the expert’s thought process is a good idea, but you have to do it your own way and that’s my big lesson I’ve learned in the past few years and I think that’s where many people get stuck is that they can’t follow the expert’s advice to the T, to the precisely, but … because they’re not that expert. They’re a completely different person so they have to make it their own and they have to process this whatever method it is or just forget the method in the first place and just accept that ‘Okay, this method, it doesn’t really work for me. I’ll try something else.’ and then do it their own way because people always talk about that shiny object syndrome, but I’m building a new business every week and that’s …

I say that, but it’s always rooted in the same place. They’re always rooted in the teaching and coaching and the consulting. That’s my core skillset, so I have to try these new methods because they feel right in the moment, and even though that method may not by itself lead to something, a brilliant success, I might get one little tidbit, one little bit out of that method that’s like ‘Okay, hey. This actually works for my thing.’, and at the end of the day, I’ve tried all these different methods and I’m starting to build my thing and my unique thing and that’s my method that’s going to bring me success.

I think that’s what copywriters should embrace more because people speak bad about the shiny object syndrome but I think just embrace the thing which brings you value, personally, which feels like the right thing to do, which feels like the inspiring thing to do, but that comes with a slight caveat.

It means you also have to trust yourself to not do it out of fear. If you’re avoiding doing the work which is putting yourself out there and being vulnerable and being embarrassed and getting haters and getting people who don’t like your comments, you have to be able to do that because that’s the way you build your own journey essentially.

Rob:   So Jay, I’m not sure if I read this right or not, but you used to be a taxi driver, is that right?

Jay:    Yes.

Rob:   What kind of life lessons or even marketing lessons did you learn from that experience?

Jay:    That was an interesting time in my life. I had my own demons to sort out so I went to … I escaped life to just drive a dark luxury car in the middle of the night, which ironically, now I’m approaching luxury brands and cars so there’s always a connection in that thing, and back then, it’s customer service.

You have to read the customer to know if they’re dangerous or not. You have to guide the conversation to keep them happy and give you a good tip, so it’s … there’s all these skills which are kind of similar to marketing and you have to … This is not anything glamorous like driving a taxi in New York City or anything. It’s just Helsinki. In Helsinki, we have the newest Mercedes taxi and you’re basically driving people to the airport and back. There’s nothing hugely exciting about that, but it was a very interesting time in my life, I would say.

Kira:   I know. I have so many questions about that. I know we have a couple minutes left, so did you get anybody dangerous? I think you were doing it for a couple years, right? Did you have anyone you had to kick out, where you just read the situation immediately and knew it was not safe?

Jay:    Oh, yeah. Oh, yeah. It’s always … this is an especially good tip for copywriters, when you’re looking for … when you’re pitching new clients and while you’re talking with people and you get this feeling, this deep grumble in your stomach like ‘This guy is not good company. Just get rid of them.’ Even though they look perfectly fine, but there’s something off. Something is really weird going on and occasionally this would happen and I started to … Most of the time, I trusted that. I’m like ‘Okay. I’m just not taking that. I can’t deal with this right now’ so I didn’t take that client. Sometimes I did and it was … It always ended up in some weird argument and I always ended up kicking them out and it’s … then it’s …

It leads in this place where you’re just feeling negative for a while and it’s never a good idea and this is actually a really interesting point because you can see these guys from a mile away and if you just learn to trust that, if you feel like a client is bad, don’t take it. Whatever money they offer you, don’t take it because it’s always going to bite you in the bum.

And … Oh, oh, oh. There’s an opposite example of that. I took this one guy from a train station, took this one guy who looked really scruffy and I’m like ‘Oh. It’s normal northern Helsinki type.’ He looked completely harmless. I didn’t get any of that dangerous vibe from him, so we started driving home and he was drunk as Finnish people usually are and in the middle of that trip, he takes a knife out, a knife which is not like a kitchen knife.

This is a fricken meat cleaver. He takes it out and he says ‘Give me all your money.’ But because I knew there was nothing dangerous about this guy, I’m like ‘Are you serious? Okay. I’m just going to leave you here. This is not cool, man.’ That may sound a bit psychotic now, looking back, but there was nothing dangerous about this guy and that’s also a lesson that keeps coming back.

If on the surface they seem weird, or if on the surface, something doesn’t add up but you get a good feeling, I’m going to say trust the good feeling because it’s like we’ve been talking about. It usually leads to good things.

Kira:   Wait, but he had a knife, right?

Jay:    Sure, but yeah. If we’re speaking more in a practical way, I’m driving a car. I need to stay calm. He has a knife. He’s drunk. He doesn’t know what he’s talking about, so I have to show only good feelings toward him, but also not show any fear, because that’s what really gets them riled up so this is also my thought process. I’m not completely insane here, but there’s also that sense that you get when someone who’s really, really dangerous, like really … If you’re on some sort of drug trip, then you’re not thinking clearly, but you’re also completely irrational, this person was not that sort.

Kira:   Yeah, it’s a good lesson, just with clients, not to show fear if they show you a knife of some sort in the project. Don’t show fear.

Jay:    Yeah, they don’t have to show you a knife, but it’s also a … fear can … If we’re talking about copywriting projects, they’re not going to show you a knife, I hope. This is in the industry, why not? If you get that feeling of a lack in self worth for example, that is fear and they’re going to see that. They’re going to notice that immediately.

Rob:   So Jay, if … We’ve come to the end of the hour. If people want to connect with you online or in person, where can they go to find you?

Jay:    In person, that might be a bit of a challenge, but if you want to message me directly, I’m, or you can just visit my website, and I love talking with people and if anyone has a question about this whole confidence thing and feeling like they don’t really know which direction they want to take their business or their life, I’m glad to … I’m happy to listen to that. I don’t have all the answers, but I have some good questions.

Kira:   All right. Thank you so much, Jay. It was great to catch up with you and hear about how your business has changed and I like that we have a theme for this podcast about trusting yourself. I think that’s a great lesson to take away from this conversation, so thank you so much.

Jay:    Hey, thanks so much guys. This was so much fun.

Rob:   Yeah, thanks, Jay.

You’ve been listening to The Copywriter Club Podcast with Kira Hug and Rob Marsh. Music from the show is a clip from Gravity by Whitest Boy Alive, available at iTunes. If you like what you’ve heard, you can help us spread the word by subscribing at iTunes and by leaving a review. For show notes, a full transcript and links to our free Facebook community, visit We’ll see you next episode.



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