What makes a good newsletter? How about “unfiltered stories and what we learn from them?” For this episode of The Copywriter Club Podcast, I interviewed business strategist Kristin Kenzy, the writer and strategist behind the Drunk Business Advice newsletter. Kristin’s formula for figuring out what makes a good story for sharing in email or newsletters is gold. As is her “accordion pitch” process. Don’t miss this one. Click the play button below, or scroll down for a full transcript.
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Stuff to check out:
Kristin’s NewsletterThe Copywriter Club Facebook Group
The Copywriter Underground
Full Transcript:
Rob Marsh: Okay before we get into our interview… long time listeners are probably wondering, what’s up with the new music? For the past five-ish years, we’ve been using a bit of music composed for us by Addison Rice. But after so many years, it just felt like it was time for a change. So the music is different for the new year and we’ll see if we can’t go another five years or so with this new mix.
On top of that, you’ve probably noticed that I’ve been hosting the podcast for the past six months without my one-time co-host Kira Hug. Enough people have asked what’s up with that, that it’s probably time to let you all know what’s up. I mentioned this briefly on one of our throwback episodes, but to make sure you don’t miss it…
I wish there was a juicy story here, or a controversy, a messy falling out worthy of the pages of People magazine, but there’s not. Last year Kira told me that after seven years working on The Copywriter Club, that this project just didn’t light her up like it used to, and she was ready for a different kind of challenge. So we worked to slowly move her out of her daily role at The Copywriter Club. Kira’s still officiallly—legally—a partner behind the scenes, but is no longer working on Copywriter Club projects. We’re still friends. There was no drama… just time for a change.
At the time I considered ending the podcast, but whenever I mentioned ending the podcast to someone I trusted, they all said, “no, you can’t do that… this podcast is too important for writers who want a look into how other people are running their businesses.” And on top of that I really enjoy talking with copywriters and other marketing experts about this thing we all do. It’s still lighting me up and I’ve got some great guests coming in the next few weeks, so hopefully you’ll all stay tuned to see what’s coming next. I’m still committed to our original promise of sharing strategies and ideas you can steal and use in your own business.
Speaking of great guests… my guest today is business strategist and story teller Kristin Kenzy. Kristin writes one of my favorite newsletters, Drunk Business Advice. In it, she combines interesting marketing take-aways with fantastic storytelling that makes me (and thousands of other readers) look forward to it each week. I wanted to talk with Kristin about her approach to finding and writing the stories she shares. The formula she uses to figure out if a story is worth telling is excellent and she walked me through during our interview. We also talked about why writers need to stop journaling and a better way to pitch prospects in person… something Kristin calls “accordian pitching”. It’s good stuff, so stay tuned to hear what she had to share.
Before we jump into this interview, we’ve got some really great guest trainings lined up in The Copywriter Underground this month… one on building connections with prospects and clients without burning out on social media. If you’re like me and struggle to show up on social media consistently, this one will change your approach entirely. And a second training on landing a “real” in-house job—either part time or full time—if you are looking for something a little more stable than freelancing is. Ironicallly, copywriters are bad at telling our own career stories and this workshop will show you what to do if you want to land one of these so-called “real” jobs. Both of these workshops are exclusively available for members of The Copywriter Underground. If you want access to them plus more than 30 templates, 70 other workshops and trainings, and monthly coaching from me, you can learn more at thecopywriterclub.com/tcu. If you’ve been thinking about trying out The Underground, this month is the month to do it. Go to thecopywriterclub.com/tcu for more information.
And now, let’s go to our interview with Kristin Kenzy.
Rob Marsh: Welcome to The Copywriter Club Podcast. We always start with your story, but I’ve got to say, I’m hesitating to ask that because you’ve had so many experiences that I’ve read about in your newsletter. We could talk about your story for the entire podcast. So your version of how you got to where you are today, running your own newsletter and the businesses that you’ve been starting.
Kristin Kenzy: Of course. Well, thank you, Rob, for having me. It’s really an honor to jump in here in the week between Christmas and New Year’s, where none of us know what day it is or what’s going on outside or where anything is in the world, to actually be a little centered and talk about writing and talk about business.
So I’ll answer your question by just looking at the last couple of years, because the last couple of years is when I’ve become a writer. And I have a definition of a writer, right? A writer is someone that actually gets paid to write. So lots of people write. I have written throughout my entire life. A lot of us have written, have published, have done self-exploratory work through writing. But I only became a writer really in the last 18 months. And that is a result of having had 20 years of entrepreneurship experience. So as you mentioned, we can talk a lot about all of those different ventures that I’ve been a part of, but how that switched from being an entrepreneur to being really a writer or an entrepreneurial writer is getting hired by Trends by the Hustle. Trends was the premium subscription of the Hustle newsletter for about five years, and it was an entrepreneurship analytics publication. And they had had many editors, many writers, many analysts over the years, and they needed someone to take it over who actually wasn’t a writer. They wanted someone who viewed the world through the lens of entrepreneurship.
So with zero editorial background, zero professional writing experience, I stepped into that role simply because they thought that I knew how to talk to that audience. And again, I looked at it as an exercise in clarity, an exercise in taking actual experiences, actual advice, actual data, and communicating it as effectively as possible to an audience that is really looking to be entertained while they’re reading it, but also they need to get something out of it. So that started my entire sort of writing journey, and I was the managing editor there for about a year. Decided to part ways with them just because The hustle and trends had been acquired by HubSpot, which is a big software conglomerate. And journalism and media and corporate America don’t blend super well. And I thought that there was just some cultural nuance there that wasn’t really jiving for me. But in that time, I had just fallen in love with editorial. I had met the coolest people that I’ve ever known before in my entire life, in my entire career, who were our writers and our analysts. The most incredible entrepreneurs who were part of our readership and part of our community. And I just said, this is what I want to do. And I felt that after having 20 years of business experience, I had earned the right to stop doing it and start talking about it and start teaching it. And so I made that big shift. I was, you know, a huge part of my career was in real estate development. And I like to say I retired my hard hat and adopted a laptop as my main business tool and made that shift into editorial. But again, I don’t look at any of this as a writer. I look at it as a person who has had experiences that I think can help others. and or entertain others, hopefully both. And that’s really the platform by which I’ve built my newsletter and all of the other editorial and community aspects of what I’m working on right now.
Rob Marsh: So before we jump into a lot of that stuff, what’s really interesting with what you’ve shared so far is the fact that you weren’t a writer before you became a writer. And there are a lot of people who listen to this podcast who are starting writing businesses or have been writing for a little while. They’re looking for clients. that the challenge of how do I communicate now that I can do this thing, this writing thing. And you obviously did it. I mean, it’s almost counterintuitive where you say, well, I, you know, you, you managed, you know, skating rinks and you’ve like, you mentioned your real estate development stuff that you’ve done and you’ve worked on a cruise ship and all of like these amazing experiences. But it wasn’t writing. And so what was the thing that made you think or even made the hustle think that you were the right person for that job?
Kristin Kenzy: There’s, there’s two things. So what the hustle thought and what I thought, two different things. Um, so I think the hustle really did want someone who could manage the business of their trends publication. I think they were thinking about that because trends was a business within a business. When the hustle was purchased by HubSpot, they relinquished their advertising business. They were, you know, that was how they made money before. And they became a platform for which HubSpot could promote its products and services. Whereas Trends uniquely was not that. Trends was a premium subscription. So they needed to look at Trends as a business plus editorial. So I was responsible for both of those elements, right? I was the managing editor, not the editor-in-chief who was in charge of both the hustle and trends. I was really looking at how can we maximize this business? Who are our readers? What interests them most? And when I say who are our readers, what stage in development are they? Are they people who are questioning going into entrepreneurship, questioning taking that leap and quitting their 9 to 5? Are they experienced entrepreneurs who are looking for operational tactics? Are they investors who are looking to keep their finger on the pulse of what’s happening in the startup world, right? Like, you know, delineating between all of those different user groups and then creating product services, programming, and of course, strong editorial that resonated with them. So I think that that’s really what they were looking at me for. I think that they thought, okay, our writers are strong enough that if our managing editor isn’t the best editor in the world, the business will still thrive as a result of that. So I think that that’s where they were coming from. I don’t think they expected me to step into the editorial side. And I know I didn’t expect myself to step into the editorial side as competently as I ended up doing. That was a huge surprise to everybody. And the thing that I thought I would find most interesting about taking on that role was building relationships with that audience. So I had been a subscriber and member of Trends since its inception, and I was an active part of that community. That’s how they knew me. I actually ran their blockchain subchapter as a volunteer, because at the time I was the COO of a blockchain startup. And so I wanted to like, you know, make sure that we were exploiting all the resources that Trends had to offer in that industry and making sure that we were constantly discovering things and sharing it with the community. So I was very actively involved and I had met some of the coolest people ever. And I was just like, if I could be in a position of authority and looked up to by this incredible community of entrepreneurs and business leaders, That can’t be bad for me at all. There’s no downside to that. And so I was really in it more for the community, the relationships, the connections, and looking at it as a stepping stone to what my next venture might be. And I think that they really wanted someone who could streamline their business operations and make sure that they were maximizing all of their programming and all of the products within the trend suite, not just the editorial.
Rob Marsh: Okay, that all makes sense. So you left there and maybe there was a step in between, but you have started your own newsletter, Drunk Business Advice, which before we started recording, I told you I love it. I think it really stands out in the newsletter space in some really unique ways. Tell us about that. Why start a newsletter and what is your approach?
Kristin Kenzy: So this all happened while I was still with Trends. It’s funny. I had wanted to either start a newsletter or a podcast or both. And it was because I had suddenly been exposed to the world of media. And like I had mentioned, I had just met so many great people. And conversely to the world of tech and the world of real estate that I had come up through, I felt like there was an openness to the relationships I was building. I met, for the first time in my career, really incredible women who wanted to uplift other women. And in a lot of more male-dominated industries, even the women in them kind of want to push women down. And I had experienced a lot of that sort of thing. And so I kind of, not to be too kumbaya about it, was like, Oh, this is just like a fantastic space to be in. And this is how I want my world to look. And so, um, I had started, my initial idea was to start a podcast and a newsletter called business and benevolence. And this was from a, uh, panel that I hosted while I was with trends with people who were really strong business leaders and entrepreneurs, but also either ran nonprofits on the side or had, um, certain like, uh, social or economic missions that were really just benevolent within their businesses. And it was this idea that you can be both and you can be successful at both, right? You don’t have to be, you know, looking just at shareholder management. You can look at stakeholder management and manage both and make the world a better place while also running a super successful and profitable business. And I wanted to explore that a little bit more greatly. And so that was kind of the first idea that I played around with. And then I’ll tell you how drunk business advice, which is so much more suitable to me, by the way, than the benevolence thing, came about. I had been at an event here in New York City that a friend of mine was hosting for entrepreneurs. And she’s someone that I support and I try to go to as many of her events as possible. And I was talking to someone there about his fundraising strategy. He was trying to raise venture capital, but also looking at smaller angel and even like some private equity. And I was talking to him about the strategy and we were having wine and then we were talking about the strategy and then we were having more wine. And then we were talking about the strategy and having even more wine. And I came up with an idea to kind of flip his fundraising strategy on its head by segmenting all of his business units and making them investable assets as individuals rather than the whole company. Not to get into too many details about it, but it was like this whole like completely rethinking how he was going to go out and raise money. And he went and did it. And the next morning I had an editorial meeting with Trends, with all of our writers, and I was like, oh my God, last night this guy took my drunk business advice. And it was the most, like, I can’t believe that he took this advice. And they were like, that needs to be your newsletter. Drunk business advice. And so it started with a name first, and I didn’t really know what I wanted to write about. But as I was workshopping the idea, I initially wanted to look at sort of the key aspects of business operations that get ignored. So I had three tests, the toilet test, the tell me test, and oh my gosh, there was one more. Now I feel like a presidential candidate in a debate for getting the third thing of a policy. So I’ll talk about the first two first and then the third will come back to me. So the toilet test was what’s the toilet of your business, right? What is the thing that if you don’t keep it maintained and running well, the shit will hit the fan, literally. But it’s not a sexy thing to look at. How do you identify that and keep that running? The tell me test was all about communication. And that is, how are you communicating your mission, your values, your structure, your tactics, your policies, not just to your staff, but to your audience? Because there’s usually a strong disconnect between what you want to do and how that’s actually landing on your team and on your audience. And now the third one is still like, leaving me, which is good. It’s good that this has happened because obviously that was not the right structure for drunk business advice. I recorded four podcast episodes initially of drunk business advice, focusing on those topics, and it just didn’t work. There’s a bunch of reasons why it didn’t work. Number one, I suck at podcasts. I—full disclosure—don’t really listen to podcasts. It’s not how I consume media. I’m a reader. And what you’re doing is incredibly difficult. Interviewing people live, editing them, promoting them, all of that stuff I was just not good at. But also, I felt like I was too structured by having these tests, these cutesy little tests. And that’s also my biggest flaw in copywriting is that I tend to be a little too cute with copy and try to find things that are a little too fun and adding structure where structure doesn’t need to be. And so I took a big step back for like probably four or five months to rethink it. And I realized that the essence of drunk business advice is just unfiltered stories and what we learn when we are actually talking to people we care about with a drink in our hand and reliving those experiences and having those experiences reflected back onto us by our friends and the people who are hearing them. And so that’s the direction that I ended up going. It’s far less structured and so far has been working a lot better than trying to be cutesy and offer all these different operational advice elements.
Rob Marsh: I think it’s the stories that resonate so much, at least why I love the newsletter so much. There’s a ton of variety. One of the first newsletters that really resonated with me, I think you were doing a critique of managed care facilities because you were putting, I think, a relative in a managed care facility, which I’ve had a mom go through that and, you know, passed away in a facility and like the criticisms that you were offering through that all hit home, but you were telling it in a way that was so compelling and almost, I mean, the experience is kind of over the top, but it was almost over the top ridiculously bad. But then the next week’s episode may be about your experience managing an ice rink or an experience on a cruise ship. The stories are so different, but they’re always compelling. So let’s talk a little bit about storytelling. And I know you even got, I think, a program where you’re helping business leaders tell their own stories. But how do you approach stories? As you’re thinking about this, oh, this would be a good story, or this is not a good story for the newsletter. What do I need to do to make this story acceptable for the newsletter? Let’s talk about that process a little.
Kristin Kenzy: Sure. So for the first probably 20 to 25 issues, I had no process. I was just publishing. And this is, I guess, one of those unique aspects of coming at this as a non-writer, right? I don’t have any experience in being taught how to write, in storytelling formulas, in any of this stuff. And it’s actually been through working with other people who have that background to provide me with clarity on what it is I’m actually doing so that I can repeat it moving forward. Because that was my biggest problem is when I first started writing drug business advice, people would ask me that question and my answer was, I have no idea. I just write it. It’s like when I was a figure skater, I didn’t know how I did a double axel. I couldn’t break it down for you because it was almost like muscle memory and I would just do it. And that’s how I was initially writing it. But since I’ve started working with actual writers and people who have been giving me feedback on what it is that I’m putting out there, I’ve been able to put a lot more structure around my process. And that’s one of the things that I’m going to be working on with my new Rebel Scribes cohort, the business leaders that are going to be joining me here in January to work on their own storytelling. So, there’s a few things. The first thing that I do, or the big structure, is something that I never knew of, but apparently is pretty common in storytelling, and that’s the, and then, because, and therefore structure. Do you know what I’m talking about when I say that, or should I?
Rob Marsh: Well, I mean, let’s elaborate on it a little bit, just in case somebody listening doesn’t. There’s a few different versions of this framework for, like, how does the story work?
Kristin Kenzy: Absolutely. And so I start with the and then. Most people tell stories this way, just, you know, when they’re talking to their friends or communicating with people on social media. And it’s this sort of anecdotal stream of consciousness way of telling a story. It’s one event happens, then another event happens, then another event happens. It’s not a story, but is a series of events. And so like, as an example, this might be, My boss dismissed my idea in a meeting. And then I started not caring about my job. And then I got called into a performance review. And then I decided I was unhappy, and then I quit. That’s a series of events. And I start with that because that’s how most of us, like, remember things. Remember this event happened, and that event happened, and that event happened. Or in the cases where I’m interviewing subjects for drunk business advice, that’s how they usually relay things to me as well, right? Like, this is the story of what happened. The next step is the because, right? Looking at the why behind that. So after I get the and thens out, and I don’t self-edit myself while I’m trying to do that. I don’t try to self-edit and go, and then, oh, what was the because here? I just get it all down. Then I try to add the becauses. So what this might look like in the previous example is my boss dismissed my idea in a meeting because he was always adamant about appearing to be the smartest guy in the room. Because I realized that I was never going to feel valued at work, I began disconnecting my self-worth with my job performance. Because I was then underperforming, I was called in for a performance review. And during that performance review, it became clear that because my boss was never going to provide me with the validation and the upward mobility I needed, that it was time for me to resign. So now that’s more of a story. And we’re getting through to the why behind the and thens. And then the final thing is the therefore. So that’s the last thing that I do, and that’s typically the drunk business advice. And for those of you who may have read it, I always kind of start, there’s this bubble at the top that has the drunk business advice, and they’re just a few bullet points to kind of entice you into what’s going to come. But the final thing is the therefore. So the therefore in this example might be, You know, therefore, while it’s healthy to find self-worth in other places other than work, work consumes so much of our time and energy that it’s important to recognize the signs of a toxic workplace and make changes before that toxic environment impacts our mental health, our reputation, our career. And that’s like, that’s the final therefore. And then you have something that is worth reading because not only does it take the reader on a journey that they can emotionally relate to, there’s advice there, right? There’s something about a piece of value that they could take away. So I start with my and thens and I just get the anecdote on paper. Then I try to look behind that, come up with the becauses. And then I finally come up with the therefore. What are the main takeaways from this? The things that really matter and that I want them to remember after reading the story.
Rob Marsh: Copywriters will recognize the advice part as the transformation or the result or the thing that we’re driving to that’s going to create that sale or whatever the activity that we need somebody to take. And so it makes sense, not just from a storytelling, situation, but when we’re writing any kind of content, any kind of copy that’s trying to move somebody from where they are now to where they want to be at some point in the future. And I think one of the wonderful things about your newsletter is it’s not always something that we’re aware of that movement because of how it’s coming from your life and your experience. But again, we’re along for the journey the whole time. And when we get there, it’s really satisfying to read.
Kristin Kenzy: That’s really nice of you to say. And I’m glad that that’s coming through. But it is hard. And you had asked how I determine what stories are worthwhile. And it really is that bridge between the and then and the because. Because if there is a because behind the story, and it’s not just a fun anecdote, I started writing one the other day, a story that I have told a million times before about a horrible experience I had at Disney World. And there’s actually a lot of business lessons in it. from a Disney perspective because they just dropped the ball on, they were definitely not the happiest place on earth. And there are just some crazy anecdotes and things that happened there. But as I was putting the story together, I just couldn’t find enough because and therefore in it. It was just to me a series of ridiculous anecdotes. And I might be able to take some of those anecdotes and use some of those for like social media posts or other things. But drunk business advice, as you mentioned, it’s long form narrative. And I need to have really strong becauses and really strong therefores. And I wrote half of it and went, there’s just not enough here. And again, this is a story that I’ve told at dinner parties for years, thinking it’s one of the best stories I have in my back pocket. And it’s really not. It’s just like an outrageous thing that happened in a series of events. but there’s nothing to really draw from it.
Rob Marsh: Yeah, there’s a big, I mean, there are all kinds of different stories, varying lengths or whatever. But when you need a story that fits a purpose, you know, if you’re trying to communicate something specific, like you said, advice or some kind of transformation, there has to be a change. There has to be that thing. You’re right. And so, yeah, there’s a place in the world for anecdotes and funny stories, you know, the give a laugh at the bar or whatever. But for a serious or a weekly newsletter, it’s nice to have a little bit more.
Kristin Kenzy: Absolutely.
Rob Marsh: Okay, so we’ve talked just a little bit about your storytelling approach. One of the things you mentioned to me that got me thinking before we started recording, you sent an email with a couple of ideas of some things we could talk about. One of them was stop journaling. And one of the things that experts have said is if you want stories to tell, you need to be writing them down in the journal and you’ve got to keep this list of your potential stories and you’ve got to be thinking about it. So I’m curious about, your approach. I know you’re not saying don’t write things down or don’t keep a journal, but what do you mean by that idea of stop journaling?
Kristin Kenzy: So I would say there’s a difference between a journal and a second brain. And I am a really strong advocate for keeping a second brain, recording your thoughts, making sure that you have notes written down every time an idea comes to you, every time you remember something, witness something, have a conversation that inspires you. Yes, 100% write that stuff down. So when I say journaling, I say like, OK, it’s like that dear diary at the end of the day. Here’s all the stuff that I did today. possibly here’s how it made me feel. The reason I think people should stop doing that and start writing for an audience is because when you’re writing for an audience, it forces you to find value in your experience that is going to be, you know, value for the audience. I like to say that my favorite quote is from one of my best professional mentors, Frank Sipovitz. He was in charge of the Super Bowl during the blackout. And he was in charge of the Super Bowl for 10 years. Prior to that, he was in charge of the NHL events. And prior to that, he was in charge of Radio City Music Hall. So this guy has been in some of the most crisis, dire situations you could ever imagine. And my favorite quote from him is, learning isn’t linear. You don’t have an experience and immediately learn from it and take those learnings and apply them to your life or whatever it is you’re doing, your profession. Our brains don’t work like that. We don’t look backwards like that. Some of the lessons kind of seep into our subconscious and become like intuitive and things like that. But like intellectually, we typically don’t look at our experiences as lessons. You know, we’re not an after school special, right? Where it’s like, oh, this experience happens and here’s what we learned from it, boys and girls. That’s not how our brains work. But we can trick our brains into doing that if we start writing those experiences down for an audience. and forcing ourselves to extract the lessons because now not only are, you know, they hopefully learning something and we’re providing value to an audience, but now we’ve intellectualized this and brought it up into the forefront of our minds so that we can now use those lessons as we move forward through our lives. And so I would argue that anyone who journals right now or likes to write down their experiences, their thoughts, their feelings, I would encourage them to start doing that for an audience. Whether it’s you’re posting on LinkedIn or any sort of other social media you happen to be on, starting a newsletter, even if you only have 20 subscribers and they’re your friends and family and cousins, right? Even if you have that small of an audience, it’s worth doing just because it’s going to force you to reflect back on your life and extract value from your experiences. So it’s a little bit of a life hack. And I also think that writing for an audience opens up enormous opportunities. Because even if you start small and gain a little bit of traction, staying top of mind for people and constantly bringing people value means that people are going to start reaching out to you for all kinds of things. I mean, I just got a text message this morning from a former colleague who I’ve remained top of mind for and wants to know if I’m interested in a job. Answers probably no on that one, but how many people get text messages like that when you’re not actively putting yourself out there? So I think it’s super valuable for a number of reasons.
Rob Marsh: I think also using writing to an audience, which is a little bit, you know, using writing as a thinking tool to figure out what you’re saying or what you’re thinking in the moment. But there’s a filtering effect that happens there too. You know, there are some regular email writers when their email shows up in my inbox where I think, that story maybe wasn’t that valuable for me as an audience, right? you know, wasn’t what I was expecting from that particular writer, whereas if they were thinking, oh, my writer includes this persona, this kind of person, and so they’re interested in, you know, this topic, or my lessons about, you know, this experience, it feels like that filtering effect could improve a lot of email writers work.
Kristin Kenzy: Oh, completely. Because you are, you’re thinking about who that person is that’s reading it. And it’s also possible to kind of segment that, right? So sending, if you have an audience and you know a little bit about that audience, you can choose to send them different versions of the same lesson in ways that will resonate with them. Or you can just choose to only send them things that you believe are really going to be impactful so that you get that click and you get that open. every time rather than them starting to become disinterested and then just not opening your email when it does contain a little nugget of gold for them. And I think that that’s something that not enough newsletter operators are actually doing right now. I asked this question to a group of newsletter operators the other night, how many segments do you send the same email to? And the answer is usually one. I have my audience segmented based on acquisition method, based on how they’ve responded to various surveys and things that I put out. For instance, entrepreneurs versus nine to fivers with a side hustle versus retirees versus C-suite. I have this information about my audience. Why not segment it? And if I want to in the future, create customized content for those segments. So I do think that that’s something that people should start thinking about at the very top, even before they have a large audience, is how to find out the most you can about them and then segment them. And sometimes you’ll just send the same blast out to everyone, and that might be the case, you know, 90% of the time. But having that information about your audience so that you can customize the message is really important as well.
Rob Marsh: Yeah, I remember you sent a subscriber survey to me that I filled out. In fact, that was probably our first email exchange.
Kristin Kenzy: Can we tell people what you told me?
Rob Marsh: Sure. Well, I mean, you’ll have to talk about what was on your survey.
Kristin Kenzy: I just want Rob’s audience to know that he told me to f*** off in that.
Rob Marsh: Sort of, sort of.
Kristin Kenzy: No, it was perfect. It was the best response I ever got from that survey.
Rob Marsh: We have to be clear, the survey itself categorizes each person, so I had to select a couple of things. One of them was my age, and I think The age for millennials said you were in the prime of your game or something. And then the one for my age group, which is just slightly older than millennial, was something about being past, not past the prime of my life, but being at the stage of my life where I could tell people to F off, basically. And so, yeah, I responded back with, I was trying to be funny, I think.
Kristin Kenzy: It was the best response I’ve ever gotten. I love that. And it showed that you actually like paid attention to the content and were engaged with it. And I love seeing stuff like that. And I’m never offended when people use that language with me because I use that language with them.
Rob Marsh: I think this points out to an interesting bit of micro copy as well, where it’s not just about the big long form newsletter. But it’s about all of the other ways that you communicate and a survey can be fun. And so especially if you’re asking people to divulge information about themselves, you ought to make it fun or at least enticing for them in some way so that they’re willing to share. And your survey did that, at least for me.
Kristin Kenzy: Thank you. Thank you. I think it’s important to bring authenticity and personality to every type of communication you have with your audience. And whether it’s a survey, whether it’s a social media post, whether it’s just an email exchange, you know, I get a lot of responses to the newsletters that I send out. And when I respond, I try to be the same person that they expect, right? I try to be fun and, you know, engaging and authentic. And I never set up If I scale to a certain level, I might have to do this, but I usually don’t set up any sort of auto replies, nor do I have at this point an assistant or anyone responding on my behalf, which I know a lot of the bigger publications have to do. I really do try to individually respond to every single thing people send me, because they’ve taken time out of their day to say hello to me, and they deserve an authentic response from me.
Rob Marsh: So when we’re talking about segmenting, have you done this with Drunk Business Advice yet, where you’re sending a different message to certain segments that I may be not seeing, or is this the plan for the future?
Kristin Kenzy: It’s more of a plan for the future. My audience, first of all, isn’t big enough yet, I think, to send those segments, but I guess the point behind this was that start collecting that data early so that you can begin segmenting once your audience gets to that point. The only difference that I have right now in emails that I’ve sent have been to promote Rebel Scribes, my writing cohort. based on people who have either shown engagement, responded to surveys, versus people who might read the newsletter and open the newsletter but are a little bit more passive. And that’s mainly just to reward those who are more engaged with special offers and pre-launches and things like that. It’s not been a like, hey, this is the segment of C-suite, so I’m going to speak to you differently than the segment who are entrepreneurs. I haven’t experimented with that yet, but I plan to in the future.
Rob Marsh: You did do that when you were with Trends, though. I mean, that publication was pretty intense in the way they used data and thought about data.
Kristin Kenzy: We actually did not. The whole time I was there, we definitely didn’t mix our editorial. Our editorial was the same message to everyone. It was a premium subscription. People paid for that. Everyone got the same thing. On the marketing side of things, we did. We segmented our list and did email marketing to try to target the most, what we thought were the best types of Trends members, which were people who were actually operating and actually doing. We found that even though people who were thinking about diving into entrepreneurship were really engaged at the beginning, they typically didn’t renew their subscription. Whereas people who were operators, you know, because if they go a year and they don’t start a business, why are they, you know, and so we were really looking more for operators, people who actually had quite a bit of experience and were looking to either pivot their business, start a new business, open up different operational aspects to their business, and they were looking for different insights. we found them to be far more engaging. And so we did segment our list based on that to try to make sure that we were targeting the right members for more sustainability and less churn overall. But editorially, no, we just sent the same email out to everyone. We probably should have thought more about that actually. But I was new at this back then. So I didn’t even think to like, these are all lessons again, learning’s not linear. And these are all lessons that I’ve learned throughout that process.
Rob Marsh: Yeah. One of the things that you mentioned that we should definitely talk about is related to this, that’s humanizing data. The fact that there is a difference between talking about numbers and knowing numbers or the way that we talk about numbers. And this is a huge problem online, you know, especially in marketing where people are willing to share like top line numbers, but they don’t talk about all of them. you know, the stuff that happens underneath, you know, when we’re talking things like income or revenue or costs and value and all of that stuff. I’m assuming you’ve got maybe a related take on that. What do you think about this whole way that we talk about data?
Kristin Kenzy: I mean, everything is spun. So to answer your question about like sometimes people are gonna like share whatever numbers make them look the best. And if that’s top line revenue and not profitability, then that’s what they’re gonna share. So I don’t know that I have a judgment to make on that because I mean, that’s more their own kind of moral dilemma. When I talk about humanizing data, I’m talking about how when you are either pitching an idea or telling someone about your business and there’s data involved. The quote that I use is like, everyone wants to know your numbers, but no one wants to listen to you talk about your numbers because it’s boring as hell, right? You want to express numbers in a way that makes people able to relate to them. So to give you a couple of examples, and I’m going to credit Carmine Gallo with this as well. He was another mentor of mine. He’s published I think 10 books now, several bestsellers. His latest is The Bezos Blueprint, where he analyzed all of Jeff Bezos’ shareholder letters over the course of the decade or so that he was chairman of Amazon and writing shareholder letters. He talked about Jeff Bezos’ storytelling ability, his ability to simplify complex situations and concepts. And most importantly, his ability to humanize data. So this is a concept that I got from Carmine Gallo in this book. And to give you an example, we might say, by the year 2050, there will be over 850 million tons of plastic in the ocean. What does that mean? It means nothing.
Rob Marsh: It means there’s a lot of plastic in the ocean.
Kristin Kenzy: It means there’s a lot of plastic in the ocean. But what if we rephrase that and we said, by 2050, the weight of all the plastic in the ocean will be greater than the weight of all the fish? That humanizes it. It conceptualizes it. And you can think, well, there’s a lot of fish in the ocean. There’s actually, I think it’s 890 million tons of fish in the ocean. And it’s going to be greater than that of all the fish. Or if we have, I have a few really good ones here. Amazon stores over 3 billion gigabytes of data.
Rob Marsh: I have no idea what a gigabyte is.
Kristin Kenzy: Amazon stores so much data that if you burned it all onto DVDs, the stack would reach the International Space Station twice. So these are examples of how you can take any time you’re writing and I try to do this. My example is figure skating, right? So when I talk about how I injured myself as a figure skater, when a figure skater falls on a jump, it’s eight times their body weight. So what I did is I was like, well, when I was a figure skater, I weighed about 100 pounds. What weighs 800 pounds? And I went through this process of trying to figure out things that weigh 800 pounds, and I figured out that a grand piano weighs about 800 pounds. I’m like, what a visual is that? So now when I talk about that, I say that when I fell on that jump, the force of it was equivalent to a grand piano crashing onto a frozen sidewalk. And that just helps. You can hear the wood splintering, right? You can feel the impact. And you can now understand what an incredible injury I had as a result of that particular fall, right? So I always try to look for ways to take a number and then humanize it or contextualize it in a way that people can understand. And I still don’t know really how many gigabytes of data all these DVDs stacked up to the International Space Station might be, but it instilled a feeling in me of like, that’s an astronomically large number. That’s an incomprehensibly large number. And Amazon stores all of that data. That’s incredible. That’s what I mean when I say humanized data, and I think it’s a really strong exercise that we can all do when we write. Every time a number comes up, just stop yourself. Well, write because you shouldn’t stop yourself while you’re writing. Write everything down. But when you’re going through that because and therefore process in your self-editing, think about more creative ways that you can tell those stories. I’ll tell you what, AI is a fantastic tool for this. Because you can put that number into ChatGPT or Cloud or whatever you use and say, give me 20 examples of this. And then you want to verify and make sure, of course, that those examples are not hallucinated and that those numbers all stack up. But it can definitely help the process when you’re trying to think of creative ways to humanize your data.
Rob Marsh: This is another huge copywriting lesson, and it’s not just numbers and data that we need to contextualize, it’s experiences, right? So, this is just off the top of my head, but if you are writing for, say, a knee supplement, because your knees hurt and you want to sell this and you’re selling it to maybe someone in their 50s or 60s, You can’t just say it stops knee pain. You have to contextualize what that knee pain is, right? Like it’s keeping you from playing tennis or being able to go running or maybe playing with your grandkids or whatever those things are. We have to contextualize this stuff in order to tell a better story and in order to get readers to relate to the stuff that we’re doing. This is key to connecting emotionally with our readers.
Kristin Kenzy: Absolutely. And it’s honestly something that I struggle with in copywriting because while I do think I’m strong editorially and with long form narrative, I lean into the cute with copy and I forget about the emotion behind it. I forget about the why. And luckily I have people in my life that are constantly banging me over the head, reminding me that I need to focus on that whenever I’m writing copy because I think it’s hard. I think it’s really hard.
Rob Marsh: Yeah. One other thing that you mentioned that we should touch on that’s a totally different subject, I think, but it’s accordion pitching. And part of this, again, copywriters, content writers, we’re always pitching for work. Oftentimes we’re pitching for other opportunities. But you said that we need to sort of shut up a little bit and take maybe a different approach.
Kristin Kenzy: Well, I mean, it’s all accordion pitching is, and this is a skill that I learned from a screenwriter friend of mine. And so it’s actually a screenwriting concept, and I’ve never heard of this being applied in business. But an accordion pitch is where you just give a little nugget of information at the top, and then you look for a positive signal to proceed. And then you give a little bit more. And I think what founders specifically, I’m not quite sure about freelancers or copywriters, usually folks are pretty good at nailing their one-liner, right? If somebody asks, what do you do? Or what does your company do? We practice this, we rehearse it. There’s a lot of people that’ll say that your one-liner is, my company solves X for Y using this secret sauce. There’s all kinds of formulas for doing this. And that’s great. What happens when they say, interesting, tell me more. Word vomit. I would say that even in this conversation, I have been guilty of that because I’ve been answering, I think, far too monologuish and not turning this into a conversation. You’re okay with that because you’re a podcast host, but if we were meeting at a dinner party, you’d be like, oh my God, I want this girl to shut up. When is she going to let me show interest or ask a question? And so what an accordion pitch basically does is, and I have, I know that people can’t see, but I have a visual aid for this, which is when somebody asks, what do you do? You open up the accordion just a little bit and you say something like, oh, I write a newsletter called Drunk Business Advice. wow, like, okay, that’s, and then I stop there, right? I write a newsletter called Drunk Business Advice, and if they’re like, yeah, okay, and they change the subject, then I know that they’re not interested in learning more about drunk business advice, and that’s okay, because I’ve given them that opportunity to say no, but if they’re like, oh, wow, what’s drunk business advice? I’ll expand the accordion a little bit more, and I’ll say, well, you know, learning isn’t linear, Our lives are not like afterschool specials. We don’t immediately learn our lessons right after we have our experiences. And what drug business advice does is it dives into those experiences in an unfiltered way to provide valuable lessons in an entertaining way. interesting, tell me more, or they might change the subject at that point or ask a question. But if they say interesting, tell me more, then I open the accordion a little bit more and I say, well, I send it every Thursday. I also have writing workshop and I can go on and on. Right. But the idea is that you will have, you know, three to five to six layers of your story. to be able to communicate in a conversational setting that occurs when people are giving you positive signals that they want to learn more. And also giving them an out and therefore respecting their time. Because nobody wants to be that person at the cocktail party who’s just blabbering on about themselves for an hour, not giving anyone else the opportunity to interject or change the subject. And so that’s accordion pitching.
Rob Marsh: I love this idea because everybody has that first answer, but almost nobody has thought through, okay, if I keep opening the kimono just a little bit more, revealing a little bit more, oftentimes we haven’t thought through like, what are those second, third, fourth level answers? And not just like, what would I say, but how do I make it so intriguing that the next response is tell me more. Every time is to tell me more. And that takes work. Again, copywriters, content writers should be able to figure that out. That’s what we’re supposed to do for our clients. But when we sit down to do it for ourselves, it’s oftentimes a harder task and it takes a lot of thinking through to get that right.
Kristin Kenzy: Totally. You hit such a fantastic point. I can give this advice all day long, but even I am bad at doing it. We all know what we should be doing, but trying to do it for yourself is really challenging. As you’re going through this process, don’t be too hard on yourself because even the people who are touting this as being the best process ever still have a hard time doing it in execution.
Rob Marsh: Well, this is one of the things that we’ve always taught in our programs. It’s oftentimes really good to have somebody that you can reflect this with. It’s like, this is what I wrote. How would you change it? This is what you wrote. This is how I respond to it. So having a business buddy, a writing partner, however you want to call it, somebody that you can reflect that is really helpful.
Kristin Kenzy: It takes practice. You can’t really do this necessarily in front of a mirror. It’s great to have a buddy who’s doing this. And this is one of the things we’re doing in my upcoming cohort is everyone’s going to craft their own accordion pitch and they’re going to have an accountability partner who they’re going to practice the hell out of it with. Because you need to be in that situation when someone’s either showing interest or maybe not showing interest or kind of showing interest. And you need to run through those scenarios and role play it so that when you get to that situation where you’re in front of someone who it matters for, then you operate like it’s by rote, like you don’t even have to think about it.
Rob Marsh: While we’re talking about this idea of having people to work through things, I know you’re interested in learning. You’ve done courses at Harvard. You’re in masterminds. Talk just a little bit about why you’re so invested in those kinds of experiences as opposed to only just reading books or only reading newsletters or what other learning opportunities that we all have.
Kristin Kenzy: And well, we all learn from books. Books are great. Teachers are great. Practice is amazing. But we learn the most by surrounding ourselves with people who care about our goals as much as we do. I mean, it just 10Xs everything. So for instance, I have a mastermind. called Stealth, Stealth Mastermind. And I was launching a landing page for a new product the other day. And I went to my mastermind and I said, shred this. And within 10 minutes, from people that I trust and love and respect, had feedback that completely reshaped that landing page. And, you know, of course you can hire someone to build a landing page for you and you can like go through and watch YouTube videos and read, you know, newsletters and listen to podcasts about all this stuff, but I mean they just within five minutes I had a completely different approach to what I was doing. And having, I think, a relationship with people who you love and trust also motivates you to do more. It’s really difficult when you’re a business owner, especially if you’re a solopreneur or someone who’s really just starting out, to have that accountability and feel like there’s someone looking at you saying, what are you doing today? How far have you gotten? And so I think the communities are really important. And for instance, when I went to Harvard, that was probably my biggest revelation. I was thrilled, obviously, to be going to executive grad school at Harvard. It was the biggest achievement and joy of my life. And I went in thinking, oh, I’m going to get the best education ever. Why wouldn’t I? The education was fine. I mean, it was good. The education was fine. The real value was derived from the relationships that I built with my classmates. And that compounds just every single day. I’m in touch with them, honestly, almost every single day. I’m either texting or on a phone call with one of them. And they make me better people. One last anecdote on this point. I received a response to my last Drunk Business Advice newsletter that was about friendships from a reader who’s really fantastic. And he talked about a Simon Sinek concept, which I had not heard about before, but was something about how friends are not people who are there for you when you’re down. They’re really people who are truly happy for you when you succeed. And when you surround yourself with people who are just as happy about your success as you are, it compounds as well. And I had never thought of it that way. I had always thought people who are the best friends are the ones that are there to rescue you. And that’s true. And you can have those friends. But the ones that celebrate your successes very meaningfully and truthfully are probably the best friends.
Rob Marsh: Yeah, that’s a really good way to look at masterminds and cohorts as those friends who are there. And I’ve seen that reflected as well. It seems to be the people who are most engaged and most caring are most excited about everybody else’s success, even when they’re not seeing it, or the same level of success.
Kristin Kenzy: Exactly. And they don’t want to tear you down to their level, right? They want to pump you up.
Rob Marsh: Yeah, exactly. Okay, Kristin, if you could go back to Kristin just starting out in the business world and give her some advice that might help her make progress faster or might help her make more sense of the whole journey in some way, what would you tell her?
Kristin Kenzy: Honestly, what we had just talked about the value of relationships. I was bullied horribly in high school. And so I thought that I could have success or friends, but not both. That was, I sincerely thought that because my friends in high school, anytime I did well, you know, exceeded, whether it was academically or in any of the extracurriculars I did, they weren’t my friends anymore, right? And they would try to bully me and beat me down. And so I sincerely had starting out in my career, this idea that like, well, I can’t make friends with anyone because they are going to inhibit my success. And that couldn’t be further from the truth. And as a result, I threw a wall up. for like 20 years and did not allow myself to have vulnerable and authentic relationships. I did not open myself up to mentorship. I did not open myself up to mentor. I really felt like this was my journey and everyone else was out to get me. And that couldn’t have been further from the truth because looking back, I had many opportunities to build incredibly meaningful relationships with people who I kept at a distance. And so that would be the advice that I give to myself is that life is not high school. Those crazy mean girls in high school are not the same people that you’re going to interact with. Keep your wits about you. Don’t let yourself be taken advantage of, of course, but allow yourself to be in vulnerable relationships because I feel like that would have just not just given me more success, but made life more enjoyable. It would have given me more joy. And I do regret that I didn’t experience a ton of joy early in my career. It was a lot of work and no play. It could have been a lot more play and a lot more fun.
Rob Marsh: Yeah. Interesting. Okay. And great advice because everybody needs more play, more joy. Yeah. So if people have been listening, and I hope everybody who’s listened is thinking, I definitely want to subscribe to Drunk Business Advice. I got to see what Kristin’s sharing with the world. Where should they go?
Kristin Kenzy: Drunkbusinessadvice.com.
Rob Marsh: And let Kristin know you heard about it on the podcast so she can segment you properly because someday who knows if there’ll be a podcast segment.
Kristin Kenzy: Absolutely. And shoot me an email. Once you get my first welcome letter, definitely shoot me an email. I will respond and I’m really excited to meet you.
Rob Marsh: Amazing. Thank you, Kristin, for sharing such great advice. I’m excited to share this with everybody who listens and yeah, let’s keep in touch.
Kristin Kenzy: Thank you, Rob. This has been so much fun. I really appreciate you having me on.
Rob Marsh: Thanks to Kristin Kenzy for taking some time to sit down with me. You should definitely check out her newsletter at drunkbusinessadvice.com. If you join her list, you’re gonna see the survey that I responded to. We talked about that earlier when Kristin mentioned that I told her to F off and you’ll see the context of why I said that to her. And you’ll have a shot at possibly giving her an even better response than I did. I’m not kidding when I say that her newsletter is a favorite and you should definitely check it out.
Let me make one last plug for The Copywriter Underground before we wrap. You heard Kristin and me talking about the power of masterminds and connections for growing your business and how they lead to all kinds of opportunities that you just don’t get working on your own. If you’re not ready for an expensive mastermind, but you want that kind of support and connection, you need to check out The Copywriter Underground now at thecopyrighterclub.com/tcu. I mentioned all the stuff that includes at the top of the show, so that’s enough. But just trust me, this is the month to join if you want to try it out.
