The Copywriting Rules You WISH They'd Taught You with Lately's Cofounder and CEO, Kate Chernis

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Alrighty, I'm going to kick it off. Welcome everybody to Saster Scale. I'm Lindsey Leggett and I'm part of the Saastr team and it is an honor to be part of today's session with Kate. I'm just going to go over a few housekeeping items and then I'm going to pass it over to Kate and we're going to have a great conversation for the next 30 minutes. Kate, if you don't mind just passing to the next slide for a few housekeeping reminders.

You betcha.

Excellent. So, as you all know, hopefully this is an interactive session. It is a roundtable. We are trying to create an opportunity for everybody to discuss and interact with one another. So we really do encourage you to take advantage of this unique format. You will see that most of your cameras are on and we love that as well as your audio. You're able to unmute yourself and join the conversation. So we really do encourage you to do so. Kate has a great presentation that she'll be sharing with us, but the goal is also to make this interactive for all of you. So feel free to just join by unmuting yourself, raising your hand in the reactions, dropping a comment in the chat. There's a lot of different ways to interact with this group and we're really excited about that. This session is being recorded and you will receive the link following this event to hear it again if you'd like or share it with your peers. And last but not least, you know, half of our goal for these events is to create a moment and an opportunity to network with others. So you'll see. I'll drop in the chat link to join our one to one networking that will be live this entire week. We really encourage you to do that. So I will send that via chat and please take advantage of that. So without further ado, it is an honor to introduce Kate Bradley Chernis. She's the CEO and co founder of Lately and her topic today is Steven, stop killing your sales with bad writing. Kate, I'm going to pass it over to you. Thanks for joining us today.

Awesome. Thanks, Lindsey. Hey everybody. How are you? Don't be shy. I love knowing the most boring things like where are you? So I saw Israel, India, Michigan, Long story. I'm dying to know. Toronto, Ottawa. And I love knowing about the weather. It's sunny here. It's like 31 degrees, so it kind of feels like winter. But we're still praying that it'll be warm enough to eat outside with friends around A fire. Because hey, this is some weird ass stuff happening right now. But so thanks to everybody. Love to hear from you. We're going to start out with just a quick explanation. So first of all, who am I? Why should you be listening to me today? So first of all, I used to be a rock and roll DJ. My last gig was actually broadcasting to 20 million listeners a day for XM Satellite Radio. I'm old enough to like know what radio is and I love it actually. Amazingly, the tricks I used in radio to activate those 20 million listeners and turn them into not just listeners but fans are the same tricks. I used to get Walmart 130% ROI year over year for three years when I owned a marketing agency. How I got from being a DJ to an agency owner is like fun other story for when we can have a beer. But segue to today. Those are the same tricks we also use with the AI from lately, which is the tech startup that I run now, which we can talk about later. The most important thing here is. What up, Ben? 4:00am yeah. That's crazy. Oh my God, Sydney. The most important thing is why are you listening today? And the reason is because being bad at writing is super costly. And it's not just about sales and marketing, but it's also internally, right? So the way you communicate with your engineers or HR or accounting can also be challenging as well as how you communicate with your customers or your future customers. It's costing companies 400 billion with a B dollars a year, which is like totally insane. And then Companies are spending 3.1 billion on remedial writing training. Like that just sounds terrible, like someone just spanked you, right? You don't want to be in remedial writing land. So this is an important thing to get right, which is why we're going to talk about it today. Totally ask any questions. I love faces too. So if you want to pop on and like, welcome to my my home office. This has been my home office for years, so I'm not just quarantining in it. But that's my Pac man poster back there. Original from the 80s. It's velour. No kidding. So I like to see your faces too. All right, so we're going to start with this. I've got like dozens of rules. I just chose like a few top 10 for you guys. This one's my favorite. Raise your hand or in the chat or wherever. If you are a start owner or founder, these rules in this slide apply to also your pitches, right? So confidence is really Everything. It's so often. Yes. Awesome. Angie. So often. Not what you're saying, but how you're saying it. Right? There's words that you need to 86 from your vocabulary. I was just totally giving Ben, one of my sales teams members, some. Some elbowing this morning for this exact same thing. So the words need think. I just wanted to say hi. Right? Or probably, maybe, possibly. Those are weak words. They undercut you. Women especially. Right. You have to be strong and powerful because it's boys club central. Right? So you don't want to set yourself up for the doubt that is already prevalent. Right. I mean, it's just part of the deal. So you want to be strong in those words. And this includes certainly in sales. Not lately can help you increase your engagement by 12,000%. Lately helps you increase your engagement. Right. Help is even a weak word to some end, believe it or not. But you guys get the idea there, right? Okay, cool. Yeah. Own the caps. Exactly. Right. I love. By the way, we're going to talk about this in a little bit here, but I like to write how I talk. Remember, I was a rock and roll DJ for a long time, so I'm really interested in hearing what I say and how you hear it as well. All right, so we're going to jump onto this one. Hopefully a lot of people are going to be blushing right now. What's up, child of cute person? So cute. So checkout is like the worst. Stop saying it, okay? Check out my blog. Check out my panel at Sester. It doesn't mean anything. No one ever, ever, ever in the history of writing checkout. Checked out your thing. It just doesn't happen. Right? Because there's no value there. There's nothing for somebody to understand of what's coming, coming behind. Right? The word checkout alone undercuts trust. Remember we talked about confidence earlier? We're going to be talking about confidence and trust a lot here today. Check out. Because it doesn't give me an idea of what's coming behind. It makes me think you're fake or spammy. Right? And there are so many more beautiful, lovely verbs to use in the English language in any lang. Right? So I want you guys to think about those. Learn more. Get ready to have your mind blown, you know, jump up and down like a hot banana, pepper, whatever it is. Like you want to activate those verbs and think about, like, how you can use them. I love a thesaurus, folks. But I'm going to show you my favorite book in the world right now. It's called I read books, like actual books that you can hold and write in. This one's called L is for lollygag. Quirky words for a clever tongue. And the reason I love it so much is it inspires me to think differently and think about words other than checkout. So this is like lily livered Lindsey Woolsey crinoline houndstooth. Right? It's just a list of, like, really funky words which can help jog ideas and help you stand out in other ways. Yeah. Cool. I love it, Lauren. Good job. All right, so we're going to go to the next one again. Jump in if you guys have any. Have any questions. Thanks, Chris. Nice to see you too. Read what you write out loud. So I touched on this before, so if it feels awkward saying it, it feels awkward reading it. This one is so easy for you to apply always. Right? So whether it's an email or a Slack message or a social media post, if you read it out loud and you trip over the words or they feel funky coming out of your mouth, you know something is wrong. Right? Again, we talked about radio, so I'll share you guys a little secret that I learned. The neuroscience of music says that when you listen to a song, your brain has to index every other song you've ever heard in order to place that new song inside your memory banks. Right? Which means when you listen to music, nostalgia kicks in automatically. It's why it's so powerful, why we feel so much emotion when we hear music. Right. And so nostalgia is about something familiar and then targeting, tucking that new in the familiar so they can both connect. Right, A trust, trust there. Right? So your voice is a note. It's a frequency. All voices have a frequency similarly. Right. And when you read copy on the Internet, you actually read it out loud in your mind, you hear that voice again, so the same ideas are happening. So it's my job as a broadcaster, whether through writing or through a screen or through the microphone, to get you to trust me and to think about how you're hearing, literally hearing what I say. So that's why talking out loud when you write is so super duper powerful. All right, cool. Awesome. So is it sporty? Is that how I say your name? We are fans of writing out loud. That's great. And thanks, Laura, for throwing the book up there. Yeah, that's the. Didn't mean to cut you there, but that's the way. Oh, you're the best. I love you. Who are you? You're working for me. Awesome. Cool. So passive language is an Easy one to think about. You probably heard this in school. If you didn't, shame on your English teacher. But you want to avoid passive language. Again, it's for a lot of reasons. Number one, it feels awkward. The boots that are green, the dog that you walked. Right. Caitley's writing rules. My team calls me Kately. Kately from lately. So you can see the difference here. Of is a key signifier. Visually. Like, usually the word of signifies that you've got some passive writing going on there. You can pull out the characters. You make it more human. I'm going to talk a lot about the humanity of communication today. I think you guys already are feeling this. But humans, you trust them. You like them. Familiar things. Familiar things help you receive new things. This is about sales and marketing. You can only sell me something if you trust and like me. Right? That's. That's all what this is all tied to. That's an easy one to apply. How's everybody doing? Good. Good. Awesome. Okay, cool. So this one, I think, is really interesting, and it's awesome, Andy. Thanks. It's kind of complicated, and there's a little psychology to it, right? So. And by the way, all marketing, messaging, sales messaging, or any messaging, even to your husband is sneaky, right? You're. You want something, you do whatever it is. You want them to take out the trash, you want them to buy your things. And so you have to think about the manipulation, which is what it is. It's psychological manipulation to get people to do what you want them to do. Why is great tool in that way? Because, number one, you expect to hear because after why. And so when you don't resolve it, when you. When you ask a why and you don't give the because, it forces people to think of the because in their mind, right? So it's why you see people ask one question online. You know, why does. Why does my hair, you know, get all frizzy every morning? I don't know. Whatever it is. So if people start to be compelled to answer that. So it can be very tricksy if you answer it yourself, you can take the air out of the ball, right? Do you guys know that metaphor from I played soccer? Right. So when you kick the ball down the field, if the ball comes to you, you don't stop the ball throw and turn around and push it towards the goal. You literally just pick up the ball and keep it moving. You want to keep that energy flowing. So why is very sneaky like that. And then. But. But I'm going to. Then contradict myself and tell you about using because at the same time. So when you do use because, guess what? It does. It makes you trustworthy because you resolved the why, right? So there has been studies on email pitches, by the way, where someone would present a pitch or a problem. You know, hey, so and so do you know why your company is wasting $400 billion a year on bad writing? Because, blah, blah, blah, right? So the emails that had a because to resolve A why got 60 or 70% greater reply, right? Which is so interesting. So there was some sort of recognition that because is very trustworthy. It gives you the resolve, the resonance. And then I'm going to read some of these. So I'm just going to read these out loud. I know this is abnormal to have a slides with so much text, but you guys can get these slides and take them afterwards, which is why I wrote them out. Okay. So you can hear me say, I was wondering how your free trial is going because I'm here to save you time in your evaluation. Right? That's the first one. The second one, I was wondering how your free trial is going. I'm here to save you time in your evaluation. So that's without. Because you can see that the second one feels less human, feels less conversational, right? So it already makes you feel like it's pre written by a robot or an automation and not targeted to you. I'm also using because in the beginning of the sentence, right? Whatever rules somebody taught you in school, most of them you can throw away. You get to use poetic license in all your writing. Remember we talked about confidence? It's not so much what you say or what you write, it's how you do it, right? So you can break any rules you want as long as you do it with confidence. Because gives you that pause there. We've got a question. So it's a question mark. Also, there's a lot of visual cues happening here too. I'm also capitalizing awesome in the top one. We talked about all caps earlier. Try lately because it is awesome. Hear what I'm doing. I'm thinking out loud, right? You guys are hearing the same things as I'm writing it, right? I also didn't contract the word. It is there and that's here, right? Just want to show you. Because you can contract stuff a lot to have a personal voice, Persona or natural human, all the conversational things. But once in a while you don't. It lets the paragraph stand out. Try lately because it is awesome, right? So that you hear how that Is right. There's more staccato to it. There's. I'm hearing it in music. Yeah. Yeah. Okay. How you guys doing? I'm going to breathe, everybody. Good? Is this fun? I think this is fun. You're reading out loud. Okay, cool. Awesome. This one's my favorite. So back to. Thanks, Laura. Back to the psychology of the things. So people are easy. We're all so easy. We all just want to be told that we're wonderful and awesome and beautiful and smart and tall and all the things, right? So let me personally just stop here for a sec and say, you guys rule. I mean, seriously, you're still here. We're 10 minutes into this. You're taking the time to read all this with me because your time is valuable to me. So I sure hope this is helpful for you. So thank you. And if you have any comments or suggestions, don't be shy. Just shoot them away at Caitley. AI, thanks again. Okay, so you heard me read that, and I did it on purpose. And I hope you guys can see how I wrote it as I said it. You could hear, right? You could hear my voice. I love you, Andy. So I want you guys. People have a hard time getting their voice across. They think that's the biggest challenge. And it's really so easy. Read out loud, right? So again, this is a psychological manipulation. I'm using the ellipsis first, right. In the sentence. And I'm doing that as a reason. Let me just stop here for a second. Say you rule. Right? So you can hear the rule. I've also bolded that line at first because I want to draw your eye there. I'm using things like sec. I say sec. I say second instead of second. Right? You get the gist here. And then I'm using some conversational stuff. I mean, like, you might say like, or. So I mean, seriously, you're still here. I'm asking a question. Right? Putting that question mark is a visual thing because you see the. Because there. Thank you again. And I'm telling you, you're awesome. And I'm also giving you a call to action. If you have any comments or suggestions, don't be shy. Just shoot them my way. So and is important you can start sentences with and if you want, I contradicted myself. I use the word just. Just shoot in my way. It's okay in that. In that scenario, I feel like. Because again, I'm trying to make myself very accessible for you. Yeah. There are four dot ellipses. And it's because it should Be that. So that's a typo, actually. And I'll tell you why. Because I use. I cheat. I use voice activated software. I don't type at all with my hands. I only write with my voice because I have a partial permanent disability and I can't type without pain. And so the computer dragon, naturally speaking, thinks that the word you should have been capitalized there, which technically it should have, right? So that would have been a full stop sentence in the beginning, which is how you would normally do ellipses, and then the next sentence would be capitalized. So good catch. You can work for me, Philippe. Yeah. So you guys get that, right? Like, hopefully you smiled. I was like, you guys rule. This is a sales sneaky, sneaky sales trick we've used a million times over in emails and DMs just being like. Someone's like, oh, hey, so and so I saw you at Sastor. I want to do your demo of your product. Oh, my God, Laura, you are awesome. Thanks so much for coming today. Right? Like, it's just so. It's so easy and it works. All right, cool. So let's keep going to this one is the golden rule, which I love so much. And I love this for so many reasons, because now, now, global pandemic of craziness where people are literally starving outside your door. Like, now is the good time to remember that the golden rule applies everywhere in your life all the time. Right? I just donated 100 bucks to the food bank actually today, here, because my mom reminded me that people were starving and I was like, oh, right, that's bad. But I think have that compassion around even your own employees and your peers is super important as well. Remembering that the person on the other end of the microphone or the screen. Hi. This is why I want to see your faces. This is why I want to know, are you in India? Toronto? Palm Springs? Where are you? So I can start to have that sympathy, empathy, that human connection. I can trust you? You can trust me. This is a little bit getting into. Right on. Siesta keys. I'm so jealous, John, of like, you know, future of work and how you work with each other. But I found that if you take the time to think about what's happening for your audience, who your audience is that you're writing for again, Text, Slack sales and marketing. It doesn't matter. And you know who they are and you can write to them, then you're going to get a better. A better response. I'll give you an example. The time zones, it's an easy one. Right. So I learned this in radio. Right on, Rob. So it's 6pm There. You're pretty far ahead of us. Hopefully you're having a cocktail. But in radio, we were broadcasting to the entire world, but we were told to focus on our country. And so I always had to be like 9am East, 12pm west for every show that we talked about. Right. This. I found my. My team. I have team members sometimes in Malaysia, Canada, you know, west coast, now in South Africa, all over the place. And so time zones are a crucial way for us to, you know, work and operate and our customers as well. Right. So we're constantly asking what the time zones are. This will eliminate so much back and forth. So obvious. Right? Like, just think about the person. I'm dumb. I was an English major, fiction writing major. I can't do math. Like, just do the math for me. Right? Get me 3/4 of the way there. So that the conversation we need to have is about the one quarter that only our human brains can need to be together. Right. That makes sense. Okay, cool. By the way, this is a pro tip. Reading aloud can write can prevent you from sounding like a jerk. So I suffer from this acutely. I'm a woman. That's part of it. I sound like a bitch most of the time, so I have to use a lot of smiley faces and you are awesome and emojis and things like that. But I catch myself when I'm doing it because I can hear how I sound out loud. It's why my husband will often say to me, can I have the nice voice? Right. So just think about, like, what, what? Your nice voice is awesome. Hey, Mark, how's it going? Welcome from Auckland. So another. How we doing on time, Lindsay? We doing okay here?

Somebody tell me we've got about six minutes left.

Okay, I'm gonna go fast. Awesome. So don't bury the lead. This is the one thing I see all the time. In school, they taught you to write an intro to a paper to warm people up. Stop doing that. We're too impatient. You don't have time for it. Most of what you write vomited out on the page. This is a really good method. Vomited out. And then edit, edit, edit. Should be 4 times 4 to 1 ratio of editing to actually getting it on the page. Almost always your first sentence is a waste of time. Get rid of it. And that includes social media messages especially. Even my own team does this all the time. Just get right to the point. Right. There's so many reasons time it's also back to trust. The more you have to justify something without just getting to it, the more I'm like, yeah, you're full of it, right? So I just want you guys to be more merciless. We talked about the eyeballs and how people or the ears and how people sound. But this is also like a meal, right? Visual experience. With writing, you have to think about how everything looks. People forget you guys. We have this magical thing right in front of us. It's called a keyboard, right? There are ellipses and stars and parentheses and italics and em dashes and en dashes and numbers and question marks and all these things. Use them. They're there to help you stand out, which is our problem, right? As people, we have to cut through the noise out there. And the last thing we touched on this a little before is thinking about what your objective is, right? Your objective is to get me to do something for you, always. Whether it's to get me to fill out my time card or to get my husband to take out the trash or to get someone to buy my product. By the way, in social media messaging or even sales of general sales and marketing messaging, there's only two objectives. They are click or share. Right? Click or share. It's very, very simple. The smaller you are, it's going to be share. Because the click, it's just harder. You haven't really earned that trust yet. Except for how to content. There's a little hint for you, but if you guys can pare it down and just think of those two objectives and always ask, is what I'm writing focused on that objective or not? Right. You guys are so awesome. So that's it for me. If we have 60 seconds for questions, I'm happ take them. If not, you can always just grab me online. I'm everywhere. Cool. Everybody good? Yes.

Hey, real quick question. Do you like any of these sort of copywriting frameworks? Like there's like storybrand, Some of these are frameworks people have come up with. Do you like any of those or think about any of those?

So give me more of an example. Like, what about the frameworks specifically?

Well, like storybrand tells you how to, like how to think about your messaging, how to write your copy, you know, so on and so forth. There's a whole book series of seminars, blah, blah, blah. And so I don't, I mean, maybe you haven't used any of those. And don't worry about those. I was just curious if you've, you know, encountered those or like any of them.

I haven't. I mean, here's what we know is there's. This is more art than science. There's no magical one way, just. Same way there's not writing a pitch deck, right? To do anything except for, I mean.