Brilliant Ideas

#26: Break the Starving Artist Narrative Through Authentic Storytelling with Kendall Cherry

• Alyssa Bellisario • Season 1 • Episode 26

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Kendall Cherry, ghostwriter for multi-million dollar startups, shares transformative insights on overcoming the fear of selling through authentic storytelling, addressing the guilt that keeps many entrepreneurs from effectively marketing their services.

• Identifying the "starving artist narrative" that reinforces guilt around making money from creative endeavors
• Taking "sales field trips" to observe how businesses naturally incorporate selling without being pushy
• Using specific storytelling techniques that connect with potential clients without feeling vulnerable
• Speaking directly to your audience with "you" language instead of distancing with "we"
• Creating a "future casting" narrative that helps clients envision positive outcomes
• Building a content ecosystem that qualifies and nurtures leads without requiring constant sales calls
• Collecting and analyzing "walking testimonials" to identify patterns in client language
• Repurposing high-performing content strategically to save time while maintaining consistency

Connect with Kendall through her newsletter at wallflowerfridays.com or explore her LinkedIn content for practical examples of authentic selling through storytelling.

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Kendall:

A bookstore is there to sell you books. No one is going into a bookstore and thinking that you're being too salesy.

Alyssa:

Welcome to Brilliant Ideas, the podcast that takes you behind the scenes of some of the most inspiring digital products created by solopreneurs just like you. I'm your host, alyssa, a digital product strategist who helps subject matter experts grow their business with online courses, memberships, coaching programs and ebooks. If you're a solopreneur with dreams of packaging your expertise into a profitable digital product, then this is the podcast for you. Expect honest conversations of how they started, the obstacles they overcame, lessons learned the hard way and who faced the same fears, doubts and challenges you're experiencing, from unexpected surprises to breakthrough moments and everything in between. Tune in, get inspired and let's spark your next big, brilliant idea. Hey everyone, welcome back to the Brilliant Ideas Podcast.

Alyssa:

Today, I'm excited to introduce you to Kendall Cherry, the visionary behind the Candid Collective, where she's written for multi-million dollar startups and built email empires with 750,000 subscribers. In this episode, we're going to dive into a topic that hits home for so many of us overcoming that nagging voice in your head that says it's bad to sell. If you've ever struggled with self-doubt about selling or telling your story, you're in for a treat. Let's jump right in and get candid with Kendall. Welcome to the show, kendall.

Alyssa:

Thanks for coming on today. Hi, thank you for having me. It's great to have you, and you know this is a topic that people feel a little bit uneasy about, because, as a business owner, we sell things, but not everybody thinks that selling comes easy to them, because there is this unspoken fear that by telling people that they sell things, people will think that they're just in it for the money. And I've gathered lots and lots of notes from my clients and you know, talking about their offers every day is a struggle. I think that there's this deep-rooted fear coming off, that they're afraid of coming off as like annoying, or that there's like a little bit of guilt around it and feeling like, when they do talk about their offer, that it comes off as unnatural and feeling super forced. And so I'm curious in your view, can you share a moment where you pushed past the guilt or fear of selling, and what changed your perspective around it?

Kendall:

Yeah. So for me, a couple things to keep in mind. So I'm a ghost writer. I write content for clients all day, every day. So I'm basically somebody that was always probably destined to be a writer type.

Kendall:

I just happen to do it in a more commercial way, where I'm writing on behalf of businesses and it's a B2B service and something that I see a lot that I think plagues writers in particular, but I think it translates over to any form of service provider or, to be honest, any kind of business is this idea of what I write about a lot called the starving artist narrative. So for me as a writer, it shows up in most of the movies. You see, if it's writers, it's the penniless writer, it's the business owner that can't keep the lights on, and we're just shown these images in the media. This is super, super common, and so we, I think, as a collective, we've kind of internalized this. Like you say, the guilt, the shame, the like you can't actually be successful if you own your own business. If you do and you make a lot of money, it's super shady, you're doing something wrong or unethical. So we kind of have this like collective narrative that we all believe, you know, deeply ingrained in us.

Kendall:

I was that person for a really long time, especially as a writer, like I grew up hearing, you know, writing's a great hobby but you're never going to make any money for that, so it's kind of the most extreme use case, I think, coming from that background. And then I started getting curious about sales and, like you know, I need to make money, like I need to pay my bills, I need to pay my rent and all of the things. So if I wanted to do that as a writer, I started taking myself and the thing that really changed it for me I, in Austin, texas, where I live, I started taking myself on what I call sales field trips. So I would just go to like these little local shops that I really loved. For me, naturally, it was a bookstore, a very local indie bookstore, but I would just take myself on these little field trips and I would kind of take pages from the notes and books of these small businesses and I would look at, okay, especially at a bookstore, right, a bookstore is there to sell you books. No one is going into a bookstore and thinking that you're being too salesy.

Kendall:

And so I started noticing like what were these moments inside the store. Opportunities, to you know, increase the price of the transaction, sell more books. How is it happening? In this very cozy ecosystem Again, where no one's flagging book, people's trying to sell too many books. That is the purpose of why someone walks into that store.

Kendall:

And so what I noticed is, if you ever go to a bookstore, they have these little cards where it'll say Mindy likes this book, because that's not just to give you a recommendation, that's also so you'll sell and buy the book. And same thing with booksellers and like things at the cash register et cetera. And so I started looking not just at bookstores, but primarily coffee shops, bookstores, boutiques and clothing places. I started looking at these other places where, if someone, a customer, has a need, they walk in expecting to buy something to you know, to that type of store that they're walking into. And when I started, kind of unearthing that that helps me understand like, oh, these, these smaller shops are doing this, it's safe to sell in that way. So how could I incorporate that into my own work and how I kind of work around and sell in my own business?

Alyssa:

As I was saying, I totally agree with you what you were saying about the starving artist narrative and I also share with my clients that selling isn't about manipulation or feeling or trying to bully people or do those FOMO tactics that people use in their marketing.

Alyssa:

I do think that there is a subpopulation like that who typically use that whole guilting people into selling what they do, and I just feel like that is just selling using fear tactics is just not the vibe for me. But I also think it's important that they prioritize those micro problems that their customers can relate to. Um, I was recently interviewing um reed homes he's also like a sales and marketing expert just recently on the podcast and he was talking about this thing where the best way to kind of relate to your customers is to identify problems that already exist within your audience that are easily relatable. And so this leads me to my next question for you, because you are an authentic storyteller and you show people how to sell using stories, so can you share like a simple technique on how you use stories to make selling kind of less awkward?

Kendall:

use stories to make selling kind of less awkward. Yeah, one thing I love I love that you you brought up there's kind of a subpopulation or types of of people who'd sometimes can sell. Uh, that is based in fear tactics. What I will say is a lot of the clients that I write for are 95% either woman, person of color, lgbtq, and of the other 5%, the white guys, are veterans. So a lot of my sales tactics that I tend to teach people are meant for more minority populations that are actually really looking to sell in a way that's ethical, that is not just here to make money, but you genuinely, if you're going to make money, you want to feel good as you're selling but then as your customer is buying. So that's kind of my whole train of thought and that kind of authenticity and also the integrity of selling in a way that feels good For me.

Kendall:

I think storytelling is the easiest way to connect, not just your own personal experience, similar to what you said those micro problems. We as service providers, we get so much insight into selling and solving very, very specific problems. These are the things that naturally emerge over time that you and I know. This has been my story, like the things that I'm the best at are not something that on day one I flagged and was like this is going to be my whole thing, like it's something that kind of emerged naturally. And so storytelling one one tactic that I really love is very similar to like sharing pain points, but you do it a little bit more future oriented. So first, first tactical thing, I'll say I think a lot of people, when you know we write content we've sent, tend to say you know my clients or I know that we and we talked to this like big collective group of people, instead of talking directly whether it's content that you're writing, whether it's on a podcast and you're speaking, you know, maybe it's an email newsletter, whatever it is people tend to go broader because they feel weird talking directly to the person. So the thing I can say is like, even if you go back and look through like maybe the last three posts you've written or emails you sent or whatever, try to notice if you're saying the word we instead of using the word you, if you're if you and this is kind of the thing I scrubbed for all the time like your content should be saying I know that sometimes you feel like I know, I know that you know X, y, z. Whatever the problem is, it should always be pointing back to you.

Kendall:

And then, as far as like a specific story example, I really like this idea of what's called future casting. It's basically the idea where you take someone's pain point and you paint a vision of what it could look like in the future. But you use examples and again that kind of you experience. So one example I would use for my clients maybe would be the idea that you know, I know that you desire, you know, a life where you can write content or have content published for you. That you know takes less time, it makes more money and allows you to sign clients with ease. You'll notice if you were to write out that sentence, there's probably the word you in there at least four times.

Kendall:

But kind of using those pain points or the future you know story and painting that picture of what someone would desire their life to actually look like, but using the word you to kind of anchor that into an experience. I think sometimes people need permission to whether it's to dream or to brainstorm or get ideas for what that future state could look like. Sometimes, when you're deeply in the thick of things it's really tough to be like, oh yeah that you know my reality could look like that because you're so deep in it and it's so far from where you currently are. But if you can use storytelling as a way to kind of again future cast and cast a vision of what that could look like, and using the word you as the anchor, I think that is one of the best ways to show people also that you understand what motivates them, even if maybe their current state doesn't quite look like that, yet I love that technique.

Alyssa:

I'm just making some notes here.

Kendall:

It's one of those things that when I think I don't know what it is, it's like one of those kind of light bulb moments where people don't really even realize they're doing that, especially if you're writing your own content. It's like you use we and you think it's fine. And then you go back and you look and you're like, oh my gosh, I actually did that like way more times than I wanted to and it's it's the quickest fix. It's literally one word. It's not like you've got to go rewrite a bunch of content, but it's like the quickest little tweak that I that's. That's kind of the first thing I tell people is like just just scan for we versus you first and then see how far that gets you.

Alyssa:

No, that makes sense. But so I just want to backtrack a little bit to storytelling. Um, you mentioned these personal experiences that can easily, can help to easily relate to your customers. Now, now for someone like okay, so for example, for someone like me, I have a very, I would say like mundane, like I have a very like big, like, not generic, but I have a routine that I do every day. Like I don't I wouldn't say I have these like wild experiences, adventures, and I go to all these places and I, you know, I travel once in a while, but you know, I don't have it's hard for me to talk. I think for me even it's hard for me to talk about personal experiences when my day is pretty generally the same, you know, every single day. So it's like what do I talk about in my content? That would make it seem interesting.

Kendall:

Yeah. So the thing that I think the internet gets wrong a lot of times about storytelling and this is like the perfect framing. Everyone thinks that that means you have to be hashtag vulnerable. You've got to like, share some you know big traumatic experience. You've got to go on some like crazy you know million dollar vacation and then talk about what it taught you about B2B sales and it's like that's not the thing, that's not the actual solution.

Kendall:

I think what I would say is for personal experiences, people want to know what's going on behind closed doors and what kind of conversations are you having with your clients. So what questions are they asking you? I love that you came to this podcast with where you said, like you know, I went around and asked people. Those are the kinds of things that people want to know and hear the story of, because not only is it letting you show off your process and your expertise, it's giving someone that behind the scenes look of. This is how you would solve my problem once you get your hands on it, and there's going to be a million different ways that you know, based on the nature of what you do. Like the way that Alyssa solves something is going to be different than the way that Kendall solves something versus you know the other 20 million people that. Do you know the other 20 million people that? Do you know? Maybe something similar? So, allowing people to see and understand, like I have this client come with this problem or you know we how I solved a certain issue or recurring issue or a big question frequently asked questions are a really great place to anchor that in as well, but I don't actually think it means you need to have some like again big, vulnerable, traumatic story.

Kendall:

I'm actually pro like having very specific boundaries of like what I will and won't talk about. Um, cause I'm a business, not a personal. I am a personal brand. But like you don't need to know about what I talked with my therapist about this week, like that's, that's not what I'm here to do. But I think those conversations with with what you talk about with your clients how you would approach a problem, structure a project you know, tackle something with a team or you know whoever else like I think those are the things that people, when it comes to B2B world especially, it's one of those things where you don't really know what the experience is going to be like until you're in it and you've paid someone and so you kind of want to let someone know like, hey, here's what it's going to be like, here's how I would approach it, because then that would give you know the person that's reading your content.

Kendall:

They could actually assess for themselves if your approach is better than the person you know, your competitor or whoever else. So I really like that approach to storytelling, whether it's again how you would solve a problem, how you had a specific outcome, maybe certain values that you have as a part of your process, maybe you structure the way you approach things or you're onboarding in a certain way, because it highlights certain things. I think that's a way better way to set something up and it feels more authentic and genuine and it allows you to shine and show that more technical expertise without being super dry or losing people if you're an expert.

Alyssa:

I like all of it and I liked what you said about the sales conversations or just having conversations with your clients, not necessarily sales-based, but many of my clients also have trouble with sales conversations. I think there is an angle there that I think could be improved. And I know everybody, even if you think that you're in, oh, I'm great with sales conversations I think there's always something to improve there. And I know when I do sales conversations I know like everyone says I'm like crazy, but I do cold outreach and it's not for everybody.

Alyssa:

But I do it on purpose because I'm trying to figure out on my sales conversations with these complete strangers who are in my niche, like what do they need help with? Not necessarily thinking that I'm going to sell to them on that call, but to think like, okay, they are struggling with this challenge and so that could be something that I could talk about in my content. So pulling on those sales conversations can help me kind of figure out what story, what kind of stories I can share and questions that people have and things like that, what you were mentioning. Now for them, for people who struggle with sales conversations or they have maybe like a fear or a doubt of how to I guess not just to close, but just to like the structure of the sales call and just being able to sell on the call without feeling like salesy. What would you say like? What kind of mindset shifts do you suggest to overcome that self-doubt that creeps in when they're having those things, when those have those conversations?

Kendall:

Yeah. So what I will say is I'm coming from probably a pretty different perspective than you know your situation and maybe the people listening. But I was very similar to where I was, like I don't love sales conversations, I don't love the scripted. You know, I'd had a couple of coaches trying to map these scripts for me and I was like this doesn't feel authentic to me at all. Like and I and I'm also the type of person where I can tell very quickly when it comes to sales content, whether it's a one-off project or content recurring I can tell pretty quickly in about 10 seconds after reading an inquiry form where someone's gaps are and if I can help fill them. And so I'm not this person that's just trying to close anybody. I'm not trying to create a bunch of upsells. I really only sell people what they're ready to be sold for or sold to, especially when it comes to specific scope. So I operate from that mindset in general and what I will say is I don't have very many sales calls at all. I would say maybe one a month, maybe two, and I'm closing. I'm closing without a sales call and the way this is happening and I think if you're somebody that doesn't want to be doing sales. You can sell people through your content and get someone 90% to 95% of the way through the buyer's journey through a specific ecosystem to where the lead is already qualified. They know exactly what you do, your unique value proposition, your differentiators, the entire ecosystem can be set up in a way your services page on your website, your weekly email newsletter, which is basically a pipeline, nurturer the LinkedIn content, whatever it is that basically reinforces and nurtures people. So your hardest job is pretty much lead gen and then just consistently cranking out the content in a way where it works. But that is, for me, the way I see it. If you struggle with sales conversations, I personally do it because I'm a writer and I just don't like having a bunch of calls on my calendar because for me it's like I'm deep in the dock and then if I have to jump, jump in and jump out, like I'm a big deep work person, so I try to eliminate, you know, sales calls as much as I can.

Kendall:

Um, and so I just started figuring out okay, if I write the content in a specific way, you know how could I do this. Where it's, it's basically bottling up the same FAQs that I'm going to have in a sales conversation, the same talking about my services, etc. My process. How can I bottle up my best answers to what I would have to one person in a sales call and scale it so it can go to my 4,000 people on LinkedIn or my 1,500 email subscribers? How can I take that and bottle up that energy? So my best sales energy is the content that is constantly being, you know, put out into the world. And then wouldn't it be cool if that would just eliminate the need to have to be on a bunch of calls or do any sort of like manual intervention, manual selling. So that's how my business drives sales.

Kendall:

You know, we have pretty consistent sales as far as, like inquiries that come through and for me it's inquiry comes through. It is very rare at this point that I have to turn anyone away and it's pretty much a quick like here's the proposal, here's the scope, here's the payment terms, let me know if you're in, send it, move on. So all of that is like that's my, you know, quote, unquote sales process and if I do ever get on this, you know what some people may call a sales call. It's usually more of a scope check. The person's already sold. They just need to figure out you know which option or you know what which direction they want to go first. But people are basically sold before they get on a phone call or before they send the inquiry form. So it's a little bit different.

Alyssa:

I love that and I also like when you say what you said about sales energy, like protect your energy because your calendar is going to be full of sales calls, and then where does that leave you at?

Kendall:

the end of all of that like that.

Alyssa:

I mean it does. It's exhausting, um, I mean the sales calls that I have, like when I'm doing outreach or more market research. So I feel like those are a little bit different than having sales conversations where, like, if I'm doing a sales conversation, I don't, um, I don't expect a closing, I just for me, it's mostly like I need some market research, I need to see, see if my offers are landing or not, and just kind of see where my content is and things like that. So, but for an actual sales conversation or hopping on sales calls, you can absolutely do that with content Like that makes so much sense. So, yeah, no, I love that. And so we've come to our next segment here, which is called the brilliant bite of the week, and this is where you can share an actionable tip, a strategy, a mantra that will get my listeners to leave this episode and go do the thing. So what would you? Can you share something that's tangible, something that practical that they can walk away and they can use?

Kendall:

Yes, I want you to go through the last six months of content, uh, in the form of like emails, email responses from clients, testimonial forums, comments on your LinkedIn posts, um, you know, replies to your email newsletter, whatever it is. I want you to go back and create one Google Doc of your best. We'll call them walking testimonials. They could be from a formal form or I love taking a look at LinkedIn comments, dms, whatever, basically any feedback questions that people have asked you, and I want you to scrub and kind of notice what people are consistently asking for and see how you can incorporate more of that what I call like the word on the street, like how someone's actually describing their pain point in their words, and see how you can fuse that a little bit. Service providers and business owners tend to just get so caught up in the day to day that we, like, are well intentioned that we're. You know, we're going to send the testimonial form or we're going to follow up with feedback and then it just never happens. Or what happens to my clients? Because I write a lot of client case studies and testimonial kind of stories. They're like, oh my gosh, I collected the testimonial and I actually haven't looked at it since they submitted it and you're like whoa, or the content gets submitted and it doesn't really do anything other than it becomes, you know, maybe a photo of someone in a copy paste testimonial from the forum. But what I find is even more so than market research and sales calls or whatever else like your best stories and best sales angles are things that your clients and customers are already telling you about what it is that you're offering and the value you deliver. It's just we don't know what to do with that content and that qualitative data, because it's a little bit different than seeing numbers or whatever else, and so I find those are kind of the were the best gems of stories come from.

Kendall:

One of the best, best pieces that I got from a client that became this like I'll call it like this kind of cult, classic piece of content that has helped me sell a lot of services, is this it was a message, a DM, that one of my clients sent me. That was like girl, we just beat or we just confused my mom. She thought that this email newsletter you wrote as me was what, or wrote as me was me, and we tricked her. And then she was like and my best friend said the same thing, and so then it birthed this idea of like like can your content pass the best friend test? Which I could have never come up with that myself. Like I wish I was that creative. But that that concept got, you know, into my brain because it was something that a client had told me and I had it just sitting on in the photo roll on my phone because I'd screenshotted it. And then when I went back and looked I was like actually that's kind of genius for a ghostwriter. Like can we trick your best friend or your mother? Like that is so fun.

Kendall:

But those kinds of moments I think everyone tries to force, like what makes me so different? And the truth is your clients and customers are already telling you you just gotta go back and read through and see what they've said. So go go back, scrub six months, put it, put it in one Google doc, moving forward, and then from there let let that be kind of your parking lot for for content that comes back. But there's a million story, ideas and concepts that can come from their, their data and things you can repurpose too right. That can come from their data and things you can repurpose too right, completely. Yeah, all of my Spoiler alert, all of my LinkedIn content is in an 83-page doc that we cycle through every six months.

Kendall:

I never write LinkedIn content anymore. If it's quality and caliber, you can leverage a lot of that. Again, it's basically an asset. You can leverage a lot of that and just write's basically an asset. You can leverage a lot of that and just write. I write maybe one post fresh because I'm writing a book right now. So I'll write one post a week that's fresh, about the book. That's on storytelling and sales. But literally my other LinkedIn content is in an 83 page doc. My assistant schedules it for me and I know it sells it, you know, nurtures the pipeline and we call it a day. So, yeah, yeah, content on. Uh, I won't go. It's like expert mode, but it's like stealth mode, ninja mode Like, and so then all of that time saved, I'm like I'll just go write for clients, or you know, again, I'm writing a book in the background. It's kind of what I'm doing my free time. But content is high leverage if it's written in a way that's strategically telling stories and selling.

Alyssa:

Yes, that's true and like it. I mean, with all that time you could write a new piece of content and then just add it to your bank, like you're. You don't have that pressure behind you.

Kendall:

Yeah, or the one thing I noticed too is like some people will write content like you can tell it's written in the moment. It's like I saw the this is the worst example, but this is actually true life. Someone took a photo of their dog in the snow with power prints in the snow and they were like what my dog taught me about B2B sales in this snowstorm and I'm like that is not the vibe, that is not it. Like if we're, if we're doing that, you might be better off just not writing it that day. Like I don't know what to tell you, but this content, when it gets written in the moment, it doesn't age very well. Like you can have content that is really high quality that ages well and nurtures your pipeline today and also six months from now and six months after that, like some of my best performing content. I mean it's the internet has seen it probably eight or nine times and no one's no one's keeping tabs on that one piece of content that you posted, cause we're all mindlessly scrolling.

Alyssa:

So, it's.

Kendall:

It's interesting how, the more my audience grows, like I just see the engagement go up for each post, I'm like this is not the first time it's been out here, but yeah, it's one of those things. It's a different kind of mindset when it comes to content and it's not creating it live and in the moment.

Alyssa:

It's so true. It's also like the ones that I have the least amount of effort in, like when I do like B-roll content, for example, like it'll do really well, but the ones that I really spend a lot of time on it just doesn't seem to reach as much. But it just because you know. I mean, if it is just in the moment like it could be great too.

Kendall:

But, um yeah, like the paw prints in the snow, I don't know I wish I could say I was kidding, I saw and I just was like mouth hanging open. What is this? People posting, like the photos of their breakfast. I'm like this is not instagram in the 2010s. Like this is we're trying to sell things. People like so basic. Yeah, it's it.

Alyssa:

Yeah, yeah, well thanks so much, kendall, for you know, coming on the show today and sharing so many golden nuggets with us today, I'm just like pages and pages of content here, um, anyway. So I just wanted to say, um, I also want to also mention how can my listeners connect with you.

Kendall:

Yeah, so I have a newsletter that I write every week called Wallflower Fridays.

Kendall:

It's a lot of what we've talked about today, where I share either stories and different types of media or really and truly like a lot of it is based on questions that people ask me, similar to what we've talked about today questions about selling, questions about storytelling and how you can be more authentic and of integrity as you sell services or whatever it is that your business does so that you can sign up for at wallflower Fridayscom.

Kendall:

And then I would also recommend I tell people if you want to see kind of what's inside my LinkedIn content bank. I get a lot of people at this point who will DM me and tell me that they've either made popcorn or a cocktail and just started reading through my LinkedIn archive either my comments or the posts that I write. So you can find me on LinkedIn. I'd love to connect, but if you're curious about what any of that kind of content could look like, you know my best stuff is out in the open, so it's all being published, but I'd highly recommend just checking that out as well If you're looking for actual, tangible examples of just some different frameworks and things that I found work over the years. You can find me on LinkedIn.

Alyssa:

Awesome. Well, thanks so much, kendall, and I'll make sure that all of your links they're in the show notes of this episode, so make sure to check all of them out. And I just want to thank you for listening today and for hanging out with us, and I hope you found this episode as helpful as I did, and I'll catch you next time on another brilliant idea. I did and I'll catch you next time on another brilliant idea. Thanks for tuning into this episode of brilliant ideas. If you love the show, be sure to leave a review and follow me on Instagram for even more insider tips and inspiration. Ready to bring your next big, brilliant idea to life? Visit AlyssaVelsercom for resources, guidance and everything you need to start creating something amazing.