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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 thecopywriterunderground.com.

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,