TCC Podcast 33: Taking Uncomfortable Action with Ry Schwartz - The Copywriter Club
TCC Podcast 33: Taking Uncomfortable Action with Ry Schwartz

Our first guest to make an encore appearance on the club podcast is Canadian copywriter, Ry Schwartz, who just flew in from Costa Rica in time to talk with Rob and Kira about:
• the new “product” Ry is launching soon with his girlfriend
• using masterminds to meet potential clients
• how he deals with “freak out”
• how he vets clients (sometimes he asks them to sing with him)
• how he conducts his R&D (and what client work has to do with it)
• what he does to get people to take “uncomfortable action”
• how he invoices for “giving a damn”
• what he would do today if he had to start over from scratch

There’s so much good stuff in this episode that we’ve already listened to it three times before we released it. Don’t miss all the great advice Ry has to share. Click the play button below, or scroll down for a full transcript.

The people and stuff we mentioned on the show:

Sponsor: AirStory Copy School
Joanna Wiebe
Marc Angelo Capalla
Superhero Academy
The Wonder Twins
The Babysitters Club
High Existence
The other Ry Schwartz podcast
Marian Schembari
Carpool Karoke
Sam Woods
Amy Porterfield
Tarzan Kay
Gabby Bernstein
Jeff Walker
Ryan Levesque
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity

Full Transcript:

The Copywriter Club Podcast is sponsored by Airstory, the writing platform for professional writers who want to get more done in half the time. Learn more at

Rob: 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 33 as we chat with copywriter Ry Schwartz about what he would do if he had to start over from scratch, how he thinks through email sequences, how to focus when you’re freaking out, and vetting new clients.

Joins conversation in progress…

Kira: Well, maybe we can start there. We’re not doing an official intro, I don’t think. I want to hear more about your travels and where you’ve been and why you’ve been traveling and what you’ve been doing off the radar.

Ry: Yes. Yes, so I’ve been really on the road since mid-February. I’ve been location-independent for three or four years right now. I never really took advantage. I get very romantic about the idea of travel, but in practical terms, I can’t leave my house without packing for Cliff Bars, just because I have this intense fear of starvation. It really took a lot to pull the trigger on that, but it’s something that my girlfriend, Sue, and I were talking about for two years, just even considering relocating to Costa Rica for the winter, because who wants to be in Montreal in the winter? Then yeah, I finally pulled the trigger. I surprised her with this three-week trip, part of it at this mastermind. A few of the things are already taken care of for us and we don’t have to pack too many Cliff Bars.

Yeah, we ventured down there in mid-February. It was initially supposed to be on the backend, at the end of the launch I was doing with the Copy Hackers. We were going to launch Copy School. I was going to create my new program within in, and then we were just going to celebrate with this three-week cathartic release in the jungle. As luck would have it, our launch dates got pushed back. I was actually in the jungle trying to get any kind of Wi-Fi possible in any location possible in order to write emails for the launch and just work with that pivot. God bless Joanna for being patient with that. I’m like, “I literally am in the middle of the jungle. There is no Wi-Fi present. The only Wi-Fi providers are three hours away and they really don’t give a crap about my product launch right now.”

Yeah, that was part of the adventure was working on that and getting things lined up while also enjoying and submitting to the jungle experience and being present to that. That was super wild. To make matters even crazier, and this is where the story really takes some interesting turns, is our first live webinars to launch our new program were literally scheduled for the day we were getting back from Costa Rica, so all the work was there. Three days before we are scheduled to come back, my girlfriend starts not feeling so well. She’s going to hit me when listens to this.

Kira: Oh, boy.

Ry: I’m so getting in trouble, but … Okay. Maybe she won’t listen to this. I’ll just make sure she doesn’t listen to it. This is super, super intimate information here, but yeah, she starts throwing up wildly, not your typical I ate too much at that buffet kind of throwing up, like the nasty stuff. Yeah, I was like, “I don’t know, maybe she caught some foreign jungle virus and she’ll be fine because immune systems are awesome and we’ll be okay,” but it just kept persisting.

At this point, I got to add to the story, we actually left the jungle. The later part of our trip was actually meeting, this was a terrible idea on my end, but it was to move from the craziness of the jungle and this festival we were at in the last few days where people are just doing all sorts of crazy things and staying up until 3 a.m., listening to crazy music. Moving from that setting to Laguna Beach where we were actually meeting up with my parents and my sister for three days of family time.

It was during this family time that Sue really was having this weird post-jungle virus which intuitively I was like, “Yeah, I don’t know, this might not just be a jungle virus.” I Ubered to a CVS, bought a pregnancy test. We had no reason to think that a pregnancy test would be needed. We were reverse trying. We were un-trying to get pregnant, and then, yeah, it was like, “Pee on the stick and see what happens,” just put that aside easier, and it came back positive. Of course, I’m like-

Kira: Oh.

Ry: Yeah, I know, gasp. Then like…

Rob: Wait, are you announcing to the world on our podcast?

Ry: I think this is the official world announcement.

Rob: Wow.

Kira: This was unexpected.

Ry: There was total denial, complete denial, because once again, we were reverse trying. There was no reason to expect this, so take the same Uber back to the same CVS and get eight more brands of pregnancy test, pretty much.

Kira: Oh, my goodness. That sounds about right.

Ry: Just like, “Drink a lot of water because we’re going to be doing this all afternoon.” Yeah, one by one, they all started coming back positive. There’s this total freak-out. The immediate feeling is we felt like rebellious 17-year-olds that just screwed out their lives and can’t go to college anymore. Yeah, that was like just this moment of complete shock and overwhelm, and then in two days, we’re launching this new course. I’m giving birth to something. My girlfriend is eventually going to give birth to something. So much freaking birth happening right now and we were still stuck in Laguna Beach.

We raced back to Montreal, still in denial about the pregnancy, so we go to the hospital, a walk-in clinic there, and I’m literally preparing for tomorrow’s launch webinar in the waiting room trying to see what my fate holds, because I still don’t believe all nine pregnancy tests, because those things are totally unreliable.

Rob: Because, yeah, why? Yeah.

Ry: Yeah. Yeah, and it turns out … You need someone in a lab coat to say you’re pregnant before you finally believe it, but we get that confirmation. My world totally flips, total overwhelm, come home, somehow try to process that while processing our big launch the next day, yeah, get on that webinar, I think, on two hours sleep, and it all somehow worked out.

What I learned out of that process is that, after all these years, I still have the capacity to freak-out. I am not this unbreakable thing. I’m like, “Whoa, this is that stress thing people talk about all the time, like, ‘Oh, that’s where it lands.” It was just super heavy, but we did it. Yeah, fast-forward, three weeks later, she is definitely confirmed pregnant.

Kira: Oh, my goodness.

Ry: It’s awesome, and I’m feeling really good about that. The launch went really well.

Rob: Wow.

Ry: We have a bunch of amazing students in the program and just having a blast doing that. Yes, total crazy post-Costa Rican turmoil. Yeah, the jungle does crazy things to you, apparently, like pregnancy.

Rob: I am so staying away from the jungle.

Kira: I’m not going to the jungle.

Ry: Yes, stay away from the jungle.

Kira: I will not be going to the jungle anytime soon.

Ry: Yeah, finally, here we are, I’m finally able to take a deep breath and be like, “That was unexpected,” but it worked out. Yes, that is what I’ve been up to. My life is pretty boring.

Kira: Whoa.

Ry: Yeah.

Rob: That’s crazy. I have 15 questions that I want to ask, and they now all feel really small and insignificant. I mean, we should just end it here. Call it the birth announcement podcast, and we’re done.

Ry: Let’s call it a day. Yeah, put it in like the bonus material. You know what? I’m so ready for small and insignificant in life. I’m like, “Stop giving me the big tsunami waves. Give me something manageable that I could actually stay on my surfboard.” I’m good with small and insignificant. I like small and insignificant.

Rob: Let’s do it then. You went to Costa Rica as part of a mastermind.

Ry: Yes.

Rob: Tell us about that. We’ve talked about masterminding on the podcast several times with different guests. Tell us, what do you get out of a mastermind and why did you go? I know a lot of times, masterminds are secretive. You’re not allowed to share the stuff that’s going on in them, but the extent that you can, and you’re being open today, tell us about it.

Ry: Yeah, that’s a great question. It was organized by one of my friends, Marc Angelo Coppola, and he is actually a local Montrealer. He and I go way-ish back. I met him about two or three… Yeah, three-ish years ago right when I was making that pivot from nine-to-five copywriter, making 30k a year to really transitioning into owning my own business around it. He was my first coach that I really hired before I could even afford a coach or a mentor.

I remember, when I hired him, I had literally just quit my gig from the stroke ward, and I was two days out of the hospital, and yeah, had no idea what I was going to do. I just really needed someone to believe in these ambitions and really help guide them and stir them and just bring me back to that place of possibility frequently, because there’s so much doubt in those early days, literally, those early hours post-safety net, post-whatever you’re coming from.

He was my first coach actually, and he has grown a ton also in that time, and we’ve really kept in touch. Yeah, he assembled his first big mastermind. It was called The Superhero Academy something Summit. I don’t know. I don’t even remember. It’s Costa Rica. It’s in the jungle. The Superhero Academy Mastermind, and-

Rob: Which superhero are you, Ry?

Ry: They asked that on day one, and I had to be the lame kid who said that I never watched any superhero stuff. I was too busy… Literally, when I was a kid, I was reading The Baby-Sitters Club. I don’t know if anybody even remembers this.

Kira: I did too.

Ry: That’s what I was doing. I had the life of a…

Rob: You know one of the Wonder Twins then?

Ry: Well, I had a twin sister, and she was a little more persuasive in getting the things she wanted. I pretty much had to deal with her toys and books, yeah.

Kira: That was a good book series though. It’s not so bad.

Ry: It was amazing. It was inspiring. I think it was pretty transformative in life, actually. Yeah, we were at that mastermind, and it was not a copywriter-specific one. It was really a lot of entrepreneurs doing some amazing transformative stuff, a lot of big initiatives. We had people from the blog, Futurism and HighExistence, and just these big media companies. I mean, change-makers gets overused, but these are legitimately people who can say they’re changing the world and mean it.

It’s pretty awesome to just get that exposure to the types of companies I could really help and partner with. It wasn’t like… I’ve done a lot of business conferences before where it was just like the same old conversations, but this one really seemed to just push me in new ways, new ways of seeing where these bigger companies with a lot of potential are still stuck and still bottlenecked in their copy and just have conversations around that.

Yeah, that was cool, but yeah, I mean, my initial motivation, if Marc is listening to this, I am so happy I went there, and it was an amazing experience, but my initial motivation was really to finally take that plunge and go to Costa Rica with Sue and feel like a lot of the logistics were already taken care of, and whatever I got out of the mastermind would be amazing and awesome and extra, but it ended up just being a totally amazing transformative experience in itself.

Kira: Okay, I want to say congratulations because I realize I did not say congratulations on having a baby. You mentioned freaking out. It sounds like it surprised you that you could still freak-out. I want to know more about what does freaking out look like to you and how do you cope with it when it is happening, especially since it happened so recently to you, because I do freak-out a lot, and could use some coping mechanisms if you can recommend any.

Ry: What did freak-out feel like? freak-out felt like this sense of no-way-outness, and that this would inevitably end in disaster in every possible way, helplessness around it, literally feeling like I was facing a task that despite any courage I can muster up, it would be futile in comparison to what was about to hit me. That’s how freak-out announced itself. There’s no romantic happy ending of resolving the freak-out.

I think what I learnt there is that even amazing results and outcomes can be bred out freak-out if you … I actually learnt that overcoming freak-out wasn’t really the goal, just doing what I had to do despite it really seemed to be what I needed to do. I was still showing up. I was still writing the emails I had to write, preparing the webinar that I had to prepare. Getting the call even if I felt less than ideal that just trusting that you have so much to lean on within your experience, within your skillset, within your resources that you never acknowledge you have, and that even if you are feeling less than optimal, less than amazing, less than bulletproofed and optimized, to put it in entrepreneurial terms, you could still totally kick ass.

That was an important lesson for me. The goal became less about trying to feel optimal all the time and overcome all these hurdles and freak-outs and stressors and all that, and just really trusting that. Yeah, I’ve spent these last few years of really building this capacity to express in useful ways and perform in ways that even if I’m not in a perfect place at that very moment, I could still do really, really great stuff. That was it. The freak-out dissolved post that. I didn’t resolve the freak-out as I was going through it. The freak-out ended really after I was able to succeed in those situations despite it.

Kira: No, that’s really helpful. I mean, even just before jumping into this conversation, I was dealing my own freak-out of childcare issues, but that’s really well-put. It’s like you can lean on your experience and how you show up in the world and just show … I think that’s the key is showing up, right? Showing up to the phone call. Showing up to the interview. Even when everything else fells like it’s falling apart at times, just to continue to show up.

Ry: Yeah, for sure. I think I was lucky enough to be in a place where I literally had no choice but to show up. Those webinars were booked. Those calls were booked. Everything was already there. If I was left to my own devices, I probably would’ve hid in my closet and said, “Screw you world.” Yeah, I think putting ourselves in these places where we literally have no choice but to show up is just super important. That’s really how I started my copywriting career. We spoke about it on the last podcasts.

It’s like I got that gig without knowing what copywriting was, and I show up on day one and have this huge office and don’t even know what the role is that I was hired to do. Freak-out there, but, I mean, you’re already in it. You’re already taking some punches. The best you could do is just throw some back as best as you can. Yeah, I think we tend to underestimate the resources we do have to lean on and our ability to really perform even when we feel totally backed in that corner.

Kira: I was going to ask also about the impact of you travel on your writing and your creativity and just your business growth as well, because I feel the same way where I am not traveling as much as I would like right now, and I do wonder at times if maybe that’s … Maybe I would be such a better writer if I was traveling and just integrating all these new cultures and ideas into my work. Can you just speak to that?

Ry: I felt exactly how you felt. I felt like I was just limiting myself by not getting this crazy exposure to different cultures and traveling around. What I found really is the feeling I get being in different cities and different countries is really the same feeling I get just being in a different neighborhood 15 minutes away from where I am now and seeing different people in a different coffee shop. There’s so much carryover there. It’s not necessarily different cultural experiences that inspire my writing. It’s just a sense of possibility and wonder.

I feel like that could be achieved 10,000 miles away or 10 miles away with conversations with people you wouldn’t normally have conversations with. That’s what I found. I do tend to get this elevated state of possibility when I travel. I get really great writing done in new coffee shops and new places, in backseats of Ubers, talking to people that I’d never speak to in a million years, but I feel like that possibility and that resourcefulness is available without crazy travel. I think it’s just the state of receptivity it puts you in and being receptive to ideas and insights that are coming through you.

Rob: Ry, while we’re talking about freaking out. I think a lot of us freak … When we freak-out, it’s because of our clients. We’re put in a situation, dealing with a difficult client or a project that’s maybe gone south and it doesn’t do what we want it to do. How do you decide which clients you want to work with? What’s your vetting process, and how do you make sure that when you’re working with clients, you’re not put in situations where you are freaking-out all the time? I don’t imagine you freaking out very often, I have to say.

Ry: I mean, when I do, it’s pretty funny, actually. I will literally jump up and down. That’s how I actually release it. I look like an angry kid who didn’t get his Oreos. I mean, the first step right there is to acknowledge that in the kind of work we do, problems are going to arise. Projects will take on lives of their own and do some crazy stuff. Really, that’s why the first step in my vetting process is to make sure that I can build a relationship with this person where we could approach these challenges with excitement and resourcefulness instead of finger-pointing and blame and lack of communication.

Obviously, yes, we are trying to build processes as we go that limit the potential for blowups and freak-out. Really, on the most fundamental level, is I need to ask myself, “Is this the kind of person that I’d want to solve a problem with?” That’s really served me well. All my clients right now, everyone I work with on any level are people that I have no problem having a call-out 11 o’clock at night if something goes south and we need to solve it together, because I just trust in their emotional maturity and their ability and their resourcefulness and their poise to work with me to get it done. That’s really the first thing to key in on.

How I filter or vet for that is not a proven science. It’s really just like in those initial conversations. Right from the bat, I will be my weird self without reservation. I will invite them to be their weird self without reservation. I think one thing, I put on that thread where Marian was asking about my vetting process is it’s totally spontaneous. One call I had in the summer, I was watching … I was watching. I was binging Carpool Karaoke, because I had just discovered it. I had avoided for months, and now I have this backlog of 12 episodes to watch.

Rob: That’s a vortex. It’s very easy to get sucked into.

Ry: Right, it’s amazing.

Rob: That’s happened to me.

Ry: Yeah? Okay, I don’t feel so ashamed of it anymore. Yeah, I was watching the Adele one and the Red Hot Chili Peppers one, and I’m like, “This is amazing.” Then I get this email popup. I have the Gmail tab open, so you see the number go up, and of course, our ADD brains, “I need to see what that email is right now.” It was a client, a potential client who got referred and wanted to talk about writing this funnel. Yeah, at that point, I was still happy to entertain the idea of taking new clients, so I suggested just getting on the line.

I don’t tend to be that person who needs to overplan and book things far in advance. I’m like, “Here is my number, call me right now.” We’re talking, and he’s like, “How’s your day going?” I’m like, “I’m actually watching Carpool Karaoke right now. Do you want to sing the Red Hot Chili Peppers with me?” It was just like dead silence. It was worse than dead silence actually. I think there was silence on the other end, except there was … I think it’s the sound of a cleaning crew or someone vacuuming in the background on the other end.

It was like even the more awkward silence because you have vacuuming and silence, which is worse than tumbleweed which is at least more discrete. Yeah, it was awkward. Yeah, I think you get a sense very quickly. Is this someone that I could really see myself getting to know on a very deep level? As we spoke the last time, that’s part of my process, is really getting to know some intimate details of their lives and really having multiple conversations to extract that.

That openness on someone, that openness is actually a very important quality on the part of my client. How willing are they to open up? Is this going to be like pulling teeth to just get some information from them that I feel is going to make their funnel perform better, their emails perform better? Are they already in the state of, yeah, being totally ready to embrace process no matter how weird that process might seem on the surface? Yeah, just little things like that, just spontaneous ways that I could just try to engage people on the levels I feel they need to be engaged on in order for me to get good results or them and be able to solve problems with them with less freak-out.

Kira: Can you share what happened after the uncomfortable vacuum cleaner in the back? How did you play that off? Were just like, “Hey, this probably isn’t a good fit?” Like, “Have a good life.”

Ry: That probably would’ve been the best way to do it. I’ve always been bad at breakups ever since I was … I was going to say 16, and then I’m like, “I didn’t have girlfriends at 16. Yeah, don’t flatter yourself Ryan.” Yeah, no, I mean, I probably could’ve ended it there, and I probably should’ve, but no, I heard out the rest of the brief and just really listened to it.

Yeah, I think, once I had that all out, I just said, “I’ll think about it,” like what you do when you know you’re not going to buy something anyway. I think I had to breakup via email. Yeah, it’s like a area where I’m not great that. I’m not great at saying no. I still have that people pleasing part of me that just wants to serve everybody and do everything, and that tends to kick in. Nothing smooth about it.

Kira: What does your business look like today? Maybe it’s changed or maybe it hasn’t changed from last conversation, but do you have a set number of clients, and then you have wiggle room here and there to take on these potential clients. We know you’re established and you are sought after, so do you have room to grow at this stage?

Ry: Since our last call, so I did create a program called 10x Launches, which is really all about taking all this email copy knowledge, all this sales page knowledge and actually showing people how to write within the context of product launches and course launches and these sequences that we’re seeing right now. That is one thing I launched in February with Copy Hackers. That’s been fun.

That’s actually been really fulfilling to start leveraging some of these things I’m doing and actually teaching other people how to do it, so that I could actually not have to have so many one-on-one conversations about it anymore. That’s been awesome. I think, as far as the one-on-one stuff goes, I really don’t see myself ever ditching it, not because I absolutely love doing non-scalable activities, but because I totally see that as my lab, as my paid R&D.

Kira: Yeah.

Ry: Where else am I going to get the insights to share? Where else am I going to test the strategies that I could teach later? Most big companies have to invest thousands if not millions in R&D. Here, we get paid thousands to do our R&D, if you’re framing it that way, if you’re in the position where you do know you want to teach or consult or just do things where you further leverage those strategies you developed within the trenches.

No, I haven’t closed the door to one-on-one. In very real terms, I’ve taken on one new client this year, and their mission really, really spoke to me. It seemed like something that I could definitely sink my teeth into and enjoy. I’m obviously not doing anything I don’t believe in. I haven’t been doing that for a while, but yeah, I do absolutely make sure there is some availability to entertain those conversations to do one-on-one work.

Rob: I know you covered this stuff in the 10x Launches, 10x Email, but walk us through that process of deciding how many emails go into a sequence, what the sequence looks like, when does it start, does it go beyond the actual launch and doing some follow-up stuff? Brain dump on us here and help us understand that whole process, because this is something that I struggle with. Is five emails enough? Do I need 13? Do I need something in between? I don’t always get it, and so tell me your process.

Ry: The best entry point into that is really what inspires the process and where I’m borrowing from. One thing that’s always really intrigued me and sparked my curiosity is why one-on-one sales and enrollment conversations will close at 20 to 50%, whereas online marketing and email marketing will close at 2 to 3%. There’s that 10x gap there, literally, that 10x gap, and I was always curious, so I’m like, “How do we do that at scale?” That was really the question that’s always driving my curiosity and driving the content I’m creating and driving the type of marketing I do for my clients.

Part of my education this year has been not just rereading the same books copywriters are supposed to reread once a year, but actually speaking to enrollment specialists, speaking to coaches, interviewing them, talking to them about, how do they engineer that aha moment where it tilts and a prospect starts becoming a client? How do we actually engineer that context of yes? I interviewed a bunch of people who typically will get those amazing close rates, and then started just noticing some similarities and saying, “This we could do at scale. This we could do at scale. This we could do at scale.” That’s really been the basis of how I’ve planned sequences.

I mean, one thing is the frequency. Whenever we are in launch mode, making sure that you do remain present and top-of-mind during that intensive period is super vital. A good coach or a good enrollment specialist closes that many people because they coach decisiveness at the end of it. A good coach won’t let you off the hook until you get a stance and say, “Yes, this is for me. No, it’s not for me.” Giving people opportunities to make a decision and actually take ownership of a decision usually does warrant multiple emails.

That is why I have no reservation in sending an email a day between your cart open and your cart close, because people do need to come to that decision, and I challenge them to come to that decision, which is something that great coaches do. They will challenge you where you need to be challenged, and they won’t be timid about that. Yeah, I am not a timid marketer. I am not worried appearing in the inbox too frequently or being too challenging, because that is usually what it takes for people to take uncomfortable action.

As long as you believe that, that uncomfortable action is in service of what they’ve said they want to do, and to me, when they opt-in to a funnel, into a webinar for a lead magnet, they are saying they want to do something. They are saying they are committed to an outcome. My job is really to reflect that back to them, add meaning behind that click, and then coach them towards whatever decisions they need to make to really amplify it and take it to the next level. Yes, as far as frequency goes, that does mean for the duration of the launch, yes, being in their inbox daily. It means not letting them off the hook to the best of your ability until they’ve made that decision one way or another.

I mean, the amount of emails will also rely on the data you get throughout it, if they’ve attended your webinar versus not attended your webinar. That gives you a data point to pivot the conversation. That’s what great enrollment conversations do. There are many paths towards that finish line. Obviously, it’s a lot more dynamic in a one-on-one conversation and you could pivot a lot more, but you could pivot multiple times in a launch sequence based on what they’re doing or not doing, based on whether they’re opening or not opening, based on which videos they watched and how much of that video they watch versus how much they didn’t based on how they even entered and what they told you about it at the beginning and what their intent and desired outcome is.

Usually, for a launch, I will be present as often as needed in the inbox, but I will also have, typically, 30 to 40 emails just because of those different paths it might take. Does that kind of answer the question? A lot of emails and very frequent?

Rob: Yeah, I mean, definitely, it answers it. When you say 30 to 40, my head explodes. I’m imagining all of the different branches and the sequence and trying to think through that. Did your client as you to do all of that work for you? Are you working with your client to step through what that process is? If they don’t open this one, you’re suggesting that they do something else. Is the client thinking that through? My gut things it’s you that’s doing all this work, but that’s a ton of work.

Ry: Yes, so at this point, it is me. I really have noticed these patterns of where those pivots need to take place. Obviously, you can’t track every behavior and pivot based on every behavior, because that would probably bring us to those 100 or 200 emails and you have email bots at that point that pretty much just do it for you. That would be amazing, but knowing where to pivot definitely helps.

I’m not saying that like all 30 or 40 emails are totally unique, some of them are just small tweaks or keeping the same frame, but in describing the outcomes, we’re going to be hyper-specific to what we know about them. If they opted-in on the front-end and you have some segmentation that tells you a little bit more about where they’re at, whether it’s on a skill level, beginner, intermediate, advanced, or whether it’s what their main motivation is.

I mean, for example, if you have people confirm to join a webinar, and on the Thank You page you just asked them what they’re most excited to learn, what outcome are they most excited to produce, and there were four options, then that gives you a data point to use in your follow-up messaging. You know what they were most excited about. Knowing very strategically what pivots I’m looking to make and not making it an overwhelming thing has helped a lot. Sometimes, it just comes down to the same email but different testimonials that better reflect that client and their part of the journey. It sounds overwhelming at first, but there’s definitely a way to do it in a sane, manageable way.

Kira: Okay, I think everyone who is launching should listen to this show, because this is just pure gold. When you say uncomfortable action and not letting them off the hook, what does that mean exactly and how are you doing that?

Ry: Obviously, you can’t hold a gun to anyone’s head. You’re not present in the room with them, but if you were trying to sell me on being your copy cub. I love that term. I keep seeing it pop up, and it’s so cute.

Kira: Wait, I will be your copy cub, Ry.

Ry: No, I will be your copy cup.

Rob: We are your copycats. That’s why we’re doing this Ry, is to learn from you.

Kira: We’re your cubs. We’re your little cubs.

Rob: This is school for us.

Ry: I want to be a cub again. That’s all I want. I mean, I’m going to mention Sam Woods here. I want to be his cub.

Rob: Yes. Yeah.

Ry: I feel that’s cub daddy in the world, so yeah.

Rob: He’s a good cub daddy.

Ry: Good cub daddy. I have a very simple way of doing it. I have three decision points I make people take. I just hold them to the decisions they have made. In the prelaunch, they’ve already opted-in, but before we really ramp things up with the webinar or the prelaunch video series or whatever we’re doing, I’ll send out a final email before that kicks in and just say, “This is what we’re going to be up to. These are the outcomes you can expect. If you’re really down for this journey, nothing to do right now,” but I give them an out. I’m like, “If this is something that you’re not ready for at all, here is your escape plan.”

I’m getting implied affirmation to continue the conversation, which is what great coaches and enrollment specialists do. I’ll do that into prelaunch. I’ll do that right before we open cart. If we’re opening cart at 9 a.m. the next day, I’ll send a late night message or an early evening message the day before and just give that calm before the storm warning, like, “I’m going to open this up. There’s going to be some awesome bonuses and a great opportunity for you here. If you love all the free value you’ve gotten up to now and feel like that’s enough and you really don’t want to enter the conversation anymore, here’s your chance to leave.”

I give people that out, and it just gives them that choice. I want to coach people into making choices multiple times for the ultimate choice, choice momentum, if you will. Get people in the habit of making choices, whether it’s a firm action of actually clicking something or the implied choice and just not bailing. That is still a choice. Then, finally, in the closing sequence, on the last day, the closing emails I send are usually … At that point, they are already product-aware, solution-aware, promo-aware. They’re already aware of everything. They’re probably self-aware and probably have actualized themselves on levels they haven’t done before.

They’re aware on every single level. At that point, you don’t need to make them more aware of any of those things. You just really need to coach decisiveness. That’s really been the biggest game changer. If there’s one thing that has made me close more sales, it’s knowing that’s all I’m doing at the end. I am coaching decisiveness, and there will be that email where I just ask them, like, “Make a decision.” I’ll give them a link to say, “No, I don’t want this.” It’s just too much too soon or whatever that looks like in that context, but just getting people to take that stand for themselves and holding them to that standard of not just letting a stupid pixelized countdown timer hit zero and then shrugging their shoulders and saying, “Oh, well, I guess I missed it.”

Hedge against the possibility you don’t want, position against the possibility that doesn’t serve you or the person reading it. If they want to take that action and say, “I don’t want this,” I’d rather them do that than just go out in a whimper of inaction, coaching action, coaching decisiveness, coaching choice, and their ability to choose, that’s really what I’m trying to do in those final phases of any sequence.

Kira: My follow-up question is just, you are building out these funnels. You understand the psychology behind them and the structure, and you’re laying out this plan for your clients, how do you build that service into your pricing, because this is where I’ve struggled with recently as I’ve done more of this. Are you just building it into the amount you charge per email knowing that you’re going to do all this extra work ahead of time, or is it a separate service pre-writing portion?

Ry: Yes, I was actually exploring this myself and ready to write an article, but I could like the article on the fly right now. Pretty much, the only line item that I would put on an invoice … I put the project name on an invoice, and that is really it. I don’t list all of the deliverables. I don’t list all the asset. I just list the project name, one single line item, that if I was being totally honest to myself, what that line item is isn’t the name of the project. It is literally giving a damn.

That is all it is, being in total service of the success of a project. That is what people are paying me for. The stuff I’m writing within that, the strategic insight I’m bringing to that, that is all in service of giving a damn about the outcome. Yeah, that’s really kind of my short answer. I don’t have separate pricing for separate aspects of it. That would just overwhelm me. Some people are probably a lot more organized than I am, and they feel totally comfortable pricing that out. I suggest they do. I suggest every copywriter get to the point where they are charging for strategy or building that in, because I feel like that’s where you’ve really taken that next level, where you could take that leadership and instruct your client on what they need instead of waiting for their orders.

That’s just a place I wish everyone listening to this would bring themselves to be and do what it takes to get to that place to feel confident enough to do that, whether that’s taking the courses you’ve been holding off on or getting that mentorship and Sam Woods’ copy cup or whatever you need to do. To me, that’s just the level everyone needs to get to. From there, whether it’s a single line item called giving a damn or listing it out one by one. That is totally a personality thing.

Rob: I want some clarity on this then. When you’re talking with a client and you send that initial invoice, have you already spec’d out what that assignment is going to involve so that you know already that you’re going to be writing 25 emails and a landing page, or is it more like I know I’m going to spend a month caring about your project, so I’m going to estimate for a month’s worth of time?

Ry: That’s an awesome question. Yes, I will spec out the amount of emails, if there’s a sales pitch, yeah, I will spec it out. I will have my ballpark values of all those items, and I will also recognize that a big project … At this point, I’m not taking more than one per month, if that, maybe even one per quarter, so yeah, it is really also the cost to lockdown my time for two or three or four weeks, but really, I start from the place of spec’ing it out and having a ballpark value for all those assets.

Rob: Okay, you’ve got such great expertise. You’ve got such great contacts with very high level internet entrepreneurs, people watch your courses all the time, but if all of that went away, you were just Ry Schwartz who doesn’t know what copywriting is again, how would you start over? What would you do to get yourself back to where you are, and could you do it faster than what it took to do it the first time?

Ry: Oh, yeah, I would actually almost love that challenge, to be anonymous and have to start all over again and do it from scratch. I dream about that. I’m like, “What would I tell copy cup Ry right now?” What I would do right now is, I mean, we touched upon it a bit before, but it’s so worth reinforcing right now, is that we work in an industry where the demand is much bigger than the supply. When I talk about the supply, I’m not talking about the amount of people who are hanging a shingle and calling themselves a copywriter.

I’m talking about copywriters who are able and confident enough to take a leadership stance with their clients, almost more of a consultant practitioner role and lead that process and make them feel taken care of and deliver on time. There is a shortage of that, of people that a client feels totally comfortable surrendering that part of their business to. I would really hone in on that skill, how to deliver that amazing experience and that value where they feel totally at ease with that, and the results are there.

How I would get myself to that place to feel confident enough to be that person is really simple. I would’ve taken those courses and gotten a mentor much sooner. I feel the only thing that held me back was my own confidence in my abilities. That’s the number one reason people don’t raise their rates, is because they don’t yet think they could deliver that much value. Sometimes that’s totally BS and they already are there and it’s total impostor syndrome. I think the first time I raised my rates was the weekend after reading all three Copy Hackers guides. I’m like, “Okay, I probably know more about this than 90% of the people I’m going to talk to.” That felt good. That was a confidence boost.

It’s partly that. In the first three months of my career, I would definitely steep myself in whatever I needed to steep myself in to feel like I got this, because I know from that place of knowing I got this, I could have those conversations with more ease. I could take that leadership stance more clearly instead of being a waiter at TGI Friday’s, wondering what the client is going to order. I want to tell the client based on their situation what they need and how I would approach it. I want them to see me as more than the copywriter who is going to wait for what they want and tell them what they need instead.

Part of that involves both a skillset in copywriting, which I think everyone is actively developing, as well as a skillset in the marketing methods and strategies that your industry is using. I wasn’t just learning copywriting. I was a big student of all these launch methods that were top of mind to my client. I mean, that’s basic customer research. What are your clients looking at reading? What are they exposed to? If you can meet them on that level and give them confidence that you get their world, you get their competitors, you get their industry because you’re a part of it, that just allowed me to break through that much quicker and built their confidence and trust in me.

They shouldn’t need to onboard you on their industry. You should be able to add value to them about your insights to your industry. That doesn’t necessarily take years to develop. That just takes conscious exposure, reading those blogs, going to those events. That would’ve also been an enormous speed past. It took me years to break out of my shell and get on a plane and start meeting people face to face, but it’s a crazy shortcut. It’s a crazy shortcut. I was totally introverted. I didn’t even want to talk to other copywriters for years because I just felt that they’d be better. They are the competition. I wanted to dig my head in the sand and not be exposed to that at all, even though, intuitively, I totally believed in cooperation over competition, which has totally been true.

Just to give you an example of that, two weeks ago, I was in San Diego, and just to show you how connected this world is, when I’m having coffee with Amy and we’re just sitting there chatting. I get this email from Tarzan, who is in this group. She did an episode with you guys, and she was talking about … She sent an email to her list talking about her affiliate launch for B-School, and how she won this award that got her name put next to people like Amy Porterfield and Gabby Bernstein and a few other people.

I’m reading that as Amy is getting her coffee. I showed that to Amy, and Amy is like, “What? I’m that famous? No way.” Then two seconds later, we’re recording a video sending it to Tarzan, and I introduced them, and Tarzan might be helping Amy on her podcast marketing now. It’s just forming those connections and just letting people know what you’re awesome at and what you’re confident at. All those conversations are happening. That’s how I would accelerate my career. Tarzan didn’t need to send a cold email to Amy. She just had to make it very clear what she was awesome at and confident doing and foster those connections with other copywriters. That’s all that it took to form that connection. Kira, your name also came up in that same conversation. People talk. It blows my mind.

Kira: Wait. Wait. What did you say?

Ry: I didn’t say anything.

Kira: Oh.

Ry: Amy asked me if I knew you because you kept coming up, because, yeah, I guess, the people you work with know Amy. It’s just all so super connected. Yeah, to just sum it up, the things I would do, I would take those first three months of my career to really steep myself in, both copywriting education, the speed past to that. I would not take nine months reading every book.

I would take whatever course or mentorship is available to me right now to get up to speed right away on the specific things within copywriting I want to do, whether it’s sales pages, whether it’s emails, whether it’s Facebook ads. Whatever it is, you could achieve mastery much quicker if you double-down on one thing that you know a lot of clients want, versus everything, and then I would also take some of that time, that education time to expose myself to the marketing strategies that my market is already exposed to.

So many people just felt totally at ease three years ago, and, yeah, I could be like, “Okay, so you want to do a Jeff Walker style launch. You want to do the Ryan Levesque style launch. You want to do an Evergreen webinar system.” They didn’t have to explain to me what those were. Instead, I was able to add value based on my understanding of those things. That would be part two, and part three is just getting out of your shell earlier even if it’s uncomfortable.

That’s why I love the group you guys put together because of all those conversations and people just putting themselves out there. I know who does what, at least the people who are vocal about it. It just makes it so much easier to recommend people, first of all, but also, I think one thing that your group provides that a lot of people will only realize in retrospect is how much they’re learning my osmosis, just how much they’re learning by being there, by participating in the conversations, by feeling like a copywriter.

You’re not just some random person in a barn house anymore. You’re a part of this group of people on the rise and doing awesome things with that skillset. Yeah, all those things, super important that I just don’t see a reason why it needs to take more than six to twelve months to really have a great career as a freelance copywriter or a business owner in that space.

Kira: Ry, we’re out of time and I feel like … I love these conversations with you, and then I also, I feel like it also lights a fire underneath me and maybe listeners can relate, because you challenge all of us too to really up our game. You really remind me of the things I should still work on, and even areas where I can improve. I think it’s a good thing. I think we should be challenging each other to improve and become better at our craft, so thank you, and thank you for sharing your baby announcement with us too in an unexpected way. We did not expect that at all. Congratulations to you and Sue.

Rob: Yes, definitely.

Kira: At this point, where can people find out more about you? Is your new website up? Has it remained the same?

Ry: It would be really embarrassing if I said it wasn’t live yet, because, I think, when we did the podcast last, I announced the website. I said it’ll be up in a few weeks. It is live, and it’s embarrassing because I haven’t driven any traffic to it because it’s ready. I’m still getting little tweaks done here and there, but somehow, I went into my email account the other day and I already have 30 subscribers and I think it all came from the show. It’s super embarrassing because I didn’t event send a confirmation email. I’m like, “Oh, you signed up on that ugly form?” Like, “What’s wrong with you?” Super embarrassing, but yeah, it is active. It is live, and it is I just haven’t formally launched it yet.

Rob: You’re in the Facebook group. You hang out a little bit with us there, quietly, until people call you out, but not a good place to find you.

Ry: Oh, my God. I mean, here is my admission. In a group with copywriters, people are just so smart and witty, and I freeze-

Kira: I know, obnoxious, isn’t it?

Ry: It’s so much pressure, I’m like, “How do I sound cool in this reply and not lame?”

Kira: You always sound cool. I actually get angry sometimes because you always sound cool. You always are so good and on point with your copy, even in comments, even in comments.

Ry: Oh my God, it does not always come naturally. Sometimes I will get writer’s block replying to a comment in that group because I can’t disappoint these amazing writers. Yes, even I feel insecure a bit, trying to look good inside the Copywriters Club. Yeah.

Kira: You never disappoint.

Ry: Thank you.

Kira: You never disappoint.

Ry: Good to know. I mean, you guys are always on point with it too. It’s tough, and you guys are just prolific with it. You have 20 amazing posts per day. Yeah, it’s not easy, but I’m doing my best.

Rob: We appreciate it, Ry. Thank you very much and thanks for joining us for a second interview. I can already envision a third and a fourth, so more to look forward to.

Ry: Oh my God, I can’t wait.

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

  • Fred Becker

    Thank you both for another great interview from another top writer with several professionals tips and ideas to utilize.

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