Streamlined Solopreneur: Tips to Help Busy Business Owners Save Time

When you write content, who are you writing for? It’s an important question to consider— you need to have someone in mind when you write. But there’s another audience you should have the robots. Specifically, search engines. If you’re not writing for both, you could be missing out on traffic, signups, and sales. Luckily, Maddy Osman and her new book, Writing for Humans and Robots, is here to help.
Top Takeaways:
  • When writing for humans, you need to appeal to the people you’re writing for. This is where stories, empathy, and consistency come on.
  • When you write for robots, you need to consider what your content is optimized for: keywords, good headlines, and spoiler alert: What humans what to know.
  • The right headline can satisfy both humans and robots. Write something that gets people to click and search engines will recommend your content to more people.
Show Notes:
Sponsored by: Nexcess | TextExpander | LearnDash
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What is Streamlined Solopreneur: Tips to Help Busy Business Owners Save Time?

What if you could save 12+ hours per week in your business? Being a solopreneur sometimes focuses too much on the “solo” part: doing all the jobs, figuring things out yourself, and spending too much time in your business. But we didn’t start out own solo business to spend all of our time at our desk.

We did it because we want freedom: to travel; to spend time with our family; to watch a movie in the middle of a week day. That’s why Streamlined Solopreneur exists.

Each week, host Joe Casabona talks about how you can build a better business through smarter systems and automated processes. He does this by bringing on expert guests, and sharing his own experience from years as a busy solopreneur parent — so that being a solopreneur feels…less solo.

With every episode, you'll get insights, great stories, and 1-3 actions you can take today to improve your business processes and spend your time the way you want.

Joe Casabona: When you write your content, who are you writing for? It’s an important question to answer. You need to have someone in mind when you write. But there’s another audience you should have: the robots, specifically search engines. If you’re not writing for both, you could be missing out on traffic, signups, and sales. Luckily, Maddy Osman and her new book, Writing for Humans and Robots, is here to help.

This is Episode 272. You can find all of the links including a link to Maddy’s book over at howibuilt.it/272. Thanks to today’s sponsors. They are Nexcess, LearnDash, and TextExpander. You’ll hear about them more later on in the show. But for now, let’s get on to the intro, and then the interview.

[00:00:54]

Intro: Hey everybody, and welcome to How I Built It, the podcast that helps small business owners create engaging content that drives sales. Each week I talk about how you can build good content faster to increase revenue and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

[00:01:17]

Joe Casabona: All right, I am here with Maddy Osman, founder of the Blogsmith and author of the upcoming book, Writing for Humans and Robots: The New Rules of Content Style. Maddy is a good friend of mine. We were in a Mastermind group for a while and she’s been on the show before talking about getting gigs on Fiverr. This is much more in her wheelhouse though. So I feel like that last episode, I’ll link in the show notes, but that was like a favor to me. This is repaying that favor. Maddy, how are you today?

Maddy Osman: I’m doing great. Thank you so much for reaching out and giving me this opportunity to chat about something I’ve been spending a lot of time on.

Joe Casabona: So you started writing this a couple of… Was this a NaNoWriMo production, right? This is like a couple of NaNoWriMos ago?

Maddy Osman: It was, yeah. I think it was NaNoWriMo of November 2020. It kind of sat around for a bit because I was in limbo about my pandemic wedding. And then that kind of became a thing again when I planned the reception. And I just figured, you know, I’m not going to have the brainpower to finish this until I just get that done.

Joe Casabona: Now, I’ve tried and failed many NaNoWriMo before. That’s not to say like… I’m multiple… Multiple? Multiply published author. Self-published once, half-assed. And I’ll probably self-publish again. So it’s not that I don’t have the capacity to write a book, but I feel like if I’m left to my own devices, right, which is like, oh, NaNoWriMo, I have to show up every day myself, it’s pretty easy to get busy. And with three kids… Well, I guess it was just two kids at that point.

Maddy Osman: Definitely.

Joe Casabona: I did start writing a book in the last NaNoWriMo. What kind of discipline did you need for writing for NaNoWriMo? And does their support system help? Because maybe that was my problem. I just didn’t take advantage of their own support.

Maddy Osman: I think normally, pre-pandemic, NaNoWriMo typically has city hubs, like groups where you could actually physically, go in, do your writing, go to like a library or something.

Joe Casabona: Cool.

Maddy Osman: And obviously, that wasn’t the case in 2020. They have a forum type thing through their website and then I think they also have a Discord channel. So you can kind of just pop in and be like, you know, “This is me kind of checking in. Here’s what I’m working on today.” And that’s the camaraderie of just existing in that virtual space together.

I didn’t end up interacting much with their forum or chats or anything like that. They also have like… there’s a Reddit, a sub-Reddit for NaNoWriMo. Kind of the same thing. But what I did was more using Twitter and using the NaNoWriMo hashtag, you know, kind of following along with other people’s projects, while also sharing my progress.

So I think what it comes down to is that everybody gets that accountability different. Like one of those things isn’t gonna work for everyone, but there are many different communities. So you just have to find the one that you’re most excited about or that you’re most willing to participate in. So that kept me going. To kind of like announce my intent and then to share what I was doing every day, that convinced me I think to just keep doing it and keep sharing.

Joe Casabona: That’s awesome. And finding value in Twitter too. I know that in our Mastermind group we discussed my massive disdain for Twitter. But I’ve been using it more effective lately. More effectively. That’s too many adverbs. Anyway, I’ve been doing better work.

Maddy Osman: It could work.

Joe Casabona: It could work, yeah, right? I’ve been doing better at it lately. A couple of weeks ago, as people are hearing this, I interviewed Jay Clouse talking about #Tweet100, which was kind of the thing that made me use Twitter more effectively because that legitimately did gain me a lot of followers. Well, relative to the number I usually gain. So I’ve backpedaled a little bit. I heavily filter Twitter. But finding the right communities, and especially because they have that community tab now, Twitter can be super effective.

Maddy Osman: Yeah, you have some good rules in place to make it manageable.

Joe Casabona: I sure do. I’m always afraid to share… I accidentally shared my Twitter mute terms before in a live stream, and I was like, Oh, man.” Because I just feel like I’m gonna get yelled at. Like, How could you mute this thing that I care about?

Maddy Osman: Right, right. It’s personal.

Joe Casabona: You should know, listeners, it’s not a single cause or anything. It’s just things I’m sick of hearing about on Twitter. I think that’s the important part. I don’t care about people’s hot takes about whatever. I want actual experts talking about it so that I’m informed and not just like what this person thought at three in the morning. Anyway, that’s not what we’re here to talk about. We’re here to talk about your book.

The other thing I wanted to talk to you about or mention about NaNoWriMo is it feels like it’s mostly geared towards fiction. Is that…?

Maddy Osman: Yes.

Joe Casabona: Okay. Because in your book is nonfiction, my book was nonfiction. All of my books are nonfiction, I guess. Did it make it harder to use their resources because of that?

Maddy Osman: I mean, it’s definitely different. Like, it’s going a little bit against the grain of what their sort of like online logging tool is meant for, kind of what the community stands for.

Joe Casabona: Right. Because they have like, “Who’s your main character, or whatever?” And I’m like, “The reader, I guess, I don’t know.”

Maddy Osman: A business owner.

Joe Casabona: Right, cool. Maybe that’s an interesting exercise to try, though. Maybe that’ll be one of my YouTube videos. It’ll be like, I’m going to try to fit this nonfiction book into a fiction box or whatever. Awesome.

So let’s dive into the book. We’re gonna dive specifically into one chapter in a minute, and then you can really, listeners, get to see the kind of value you’re gonna get. But I want to talk more generally about how you came up with this idea first.

Maddy Osman: Totally. So the initial initial idea came from the fact that I knew I wanted to write a book. And then during the pandemic, you know, we all had some extra time, I think, that it’s usually spent outside of our houses. So we had to find ways to keep ourselves entertained in our houses. So I was like, “Okay, I have this time, I know I want to do something, what exactly do I want to do?”

And it was, I think, around the same time I had developed a style guide for the Blogsmith for our writers and for editors. It was at a time where the team was starting to expand beyond me and maybe like one or two other writers. It was growing. So I needed some sort of tool to be able to consistently grow my team without sacrificing quality, without creating a lot of edits. Because as you grow, if you have problems, those problems just become larger if you don’t have a plan for how to deal with them.

So, you know, I’m thinking about this style guide, I’m thinking… It’s already pretty long. It’s like 20 pages long. It’s no small thing. But I thought that what it was missing was some helpful contexts and examples and not just like sharing a rule of style, like, “You should write headings this way,” but to give the context of like, “Don’t do this. Here’s why. Do this. Here’s why.” Just to make it something that somebody could actually apply to their writing versus like, What does that mean?

Joe Casabona: It’s almost like how in the brand guidelines they’ll show like, “Proper use of a logo,” and then they’ll have like, “Poor use of a logo” with like an x over it.

Maddy Osman: Exactly. I mean, it’s hard to come up with those examples if you don’t have prior experience, or if you’re new to the team, or if you’re new to writing for a certain client or something like that. So I think I went into NaNoWriMo thinking, “I’m just gonna expand this style guide and kind of see where that goes.” So at the end of the… what is it? 30 days? Is it 31 days in November?

Joe Casabona: 30 days take…

Maddy Osman: 30 days has September and November.

Joe Casabona: November, April, June, and November.

Maddy Osman: Yeah, right. We got to figure this out.

Joe Casabona: We got there. It’s 30 days.

Maddy Osman: So every NaNoWriMo, there’s 30 days to write 50,000 words, we’ve established.

Joe Casabona: Perfect.

Maddy Osman: So at the end of those 30 days, I had however many chapters. Some of them I spent multiple days on, some of them it was one day, or maybe there were days where I did two chapters at a time because they were short. It didn’t have a coherent structure, yet, it was kind of still like just a bunch of related things. But it wasn’t until I did a round of professional edits. I also had my mom proofread to add sort of like the industry outsider perspective. And like, do these words make sense?

Joe Casabona: Your mom teaches English or-

Maddy Osman: She did.

Joe Casabona: She did. Okay.

Maddy Osman: She was she was an English teacher for many years. She like ruthlessly corrects my grammar as we speak. She was a great person to nitpick the details. But yeah, it wasn’t until I completed, honestly, a few rounds of edits that I was like, “Okay, these things go together, these things go together. And that’s then where the sort of like Writing for Humans and Robots came together for me. Because it was like, This stuff, that’s just for the human. This stuff it’s kind of about both of them.

[00:12:11]

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[00:13:08]

Joe Casabona: So it sounds like the story kind of came after you had this skeleton of a style guide.

Maddy Osman: Right.

Joe Casabona: Did you outline at all? Maybe I overcomplicate my process, but I will like mind map, especially with my HTML book, because HTML and CSS is such a-

Maddy Osman: You have to.

Joe Casabona: It’s such a vast thing that I’m like, “Okay, I’m writing a book for people who have never written HTML and CSS before. What do I cover? What don’t I?

Maddy Osman: You have to cover certain things.

Joe Casabona: Yeah, right. Did you do something similar? I guess what was your brainstorming process? I don’t want to put you in a mind box.

Maddy Osman: My maps are great. And I would say, however you outline, it’s going to be similar to that. Just kind of throwing ideas onto the screen, trying to make connections, figuring out what the end goal is, obviously. So I think what I did was I really just took that style guide that I had and kind of broke it down into like, “Okay, so these concepts kind of go together. Like that’s a chapter. You know, maybe I’ll talk about this, maybe this is too much information, or maybe that’s not relevant to a book or maybe that’s just Blogsmith specific. So let’s ax that.”

So the outlining stage was just kind of translating the style guide into like sections, and then essentially taking those and then expanding them during the draft. It was pretty easy because I already had that at least foundation. And I would say that if I were to do NaNoWriMo again, I would absolutely need an outline because I think it’s hard to show up every day if you don’t know what you’re going to work on, or if you don’t even have options. Because there were some chapters where I’m just like, “This is just gonna be hard to explain.” It’s like one of those… I’m sure you get it all the time with like the HTML and CSS. It’s just like there’s some things you’re like, “I get it. It’s hard to explain though,” you know?

Joe Casabona: Right. Right. Especially depending on who you’re writing for. Like, “Is it for a beginner? How much context do I need to provide?”

Maddy Osman: Right. Exactly.

Joe Casabona: “Is it someone advanced?”

Maddy Osman: Just like thinking through that.

Joe Casabona: Yeah. It’s hard. And teaching is hard.

Maddy Osman: It really is. Some days it’s like my brain doesn’t have the capacity to write about x technical subject, but maybe I could work on the chapter about images, which is kind of fun.

Joe Casabona: Yeah, that’s so funny. Because I have to write my books linearly, or my courses.

Maddy Osman: Make sense.

Joe Casabona: I don’t write courses or books out of order because I feel like… And I know, people who do. Like your approach is probably a good one, especially if you have writer’s block. And maybe I’ve done it before, because I’ve had chapters where it was like kind of like discrete topics that were kind of set apart from everything else.

Maddy Osman: Sure.

Joe Casabona: If I reference something, I want to make sure it’s already written. And I want to like say, “In chapter seven…”

Maddy Osman: That’s part of it.

Joe Casabona: Yeah, right. I guess that’s where the proofreaders come in and stuff like that. But depending on the process, they’re like proofing chapters separately. They’re not reading the whole book through once, most likely.

Maddy Osman: Yeah, typically, especially if it’s not in that final order. But I will say that when I had my team go through and do edits, which actually that was probably the edit that most shaped the book was one of the people who use Blogsmith style every day actually went in and clarified things or added context or challenged things, that’s definitely where it became the best. But I’m trying to think of what I was trying to say.

Joe Casabona: Referencing-

Maddy Osman: Oh, continuity. Yes. So we did an edit at the very end, throughout, but then again at the end, just to be like, “Is this the first mention of a concept? Have we defined it? Doesn’t make sense in this order?” Because we changed the order after the initial edits. So yeah, it was totally possible that some things did not make sense in the new order. I think that’s an important edit to go through no matter what, but especially if you’re going to be rearranging things after the fact, because it’s very likely that you miss something.

Joe Casabona: And I should make clear that I actually don’t know how my book was proofread. We’ll talk about this in Build Something More. But this is a self-published book that Maddy has written. I have self-published once, but my self-published was basically like a bunch of articles put together. So we’ll talk the differences in process there.

If you want to get an ad-free extended version of this conversation, head over to the show notes, howibuilt.it/272. You’ll see a sign-up there, you’ll also see a link to Maddy’s book, which you can preorder now, and you’ll hear kind of Maddy’s approach to self-publishing and going through all of the edits herself versus my experience, which was through a book publisher who had a team put in place. So again, that’s howibuilt.it/272.

But yeah, I don’t really know. I know that my book had like four or five editors. I had one point of contact who would read the chapter as I handed it to him. And then he’d send it to a technical editor to make sure everything was code correct. And this guy must have had the HTML spec memorized, because he’d be like, “Well, that’s not right.” And I’m like, “I don’t know. I’m self-taught.” So I’m grateful for-

Maddy Osman: “It’s right for me.”

Joe Casabona: Yeah, right. Yeah. But then I suspect as the book actually came together, the other editors would read it more in order to make sure like if I had an acronym, like you said, I spelled it out first, and then use the acronym or whatever. The biggest continuity for me.

Maddy Osman: I was just gonna say I think that technical aspect is really important for a nonfiction book. Like in my book, obviously, I’m talking about some things about SEO. So it’s like I don’t want to make a claim that I don’t believe or that is something that’s easy for somebody to disprove. And it’s hard because there are so many… What’s the opposite of absolute? Relative? There’s some-

Joe Casabona: Yeah. Like subject of use.

Maddy Osman: So you know, it’s like anytime I made a claim like have to have a citation. I over cited everything.

Joe Casabona: I did the same thing. And then my editor was like, “This is not an academic paper. You’re the expert.” But the thing that informed that was my very first book that I published was called like Building WordPress Themes from Scratch, and I mentioned a technique that was persona non grata by the time the book came out. And the people were like, “How could you tell people to…”

I was using query posts or something like that. It was something that early on we decided you’re not supposed to do and it was in the book. And I was like, “Man, never again…” Like, I will always make sure now that I’m doing the right thing. It’s scary, right, when you’re putting something in a page? You can’t just update the page of a book that’s been printed. Like you can have the [erotus?] section, but-

Maddy Osman: Right. It’s not like a blog, which is what I’m more used to. So it’s definitely an adjustment.

Joe Casabona: Awesome. So the book came together. We’ll talk about the self-publishing process in Build Something More. Why don’t we go through an outline so people can kind of get an idea of everything that’s around the main chapter we’ll talk about. This is broken down into two sections, right? Writing for humans-

Maddy Osman: Technically three. But yeah, it’s like two main ones.

Joe Casabona: So we’re writing for humans, we’re writing for robots, and then I guess we’re kind of combining it.

Maddy Osman: Putting it all together.

Joe Casabona: I mean, I have the book up here. I got an advanced copy, which makes me feel really good as a podcaster, and hashtag influencer.

Maddy Osman: Hashtag.

Joe Casabona: Hashtag. But I mean, there’s like 22 chapters in this. It’s a weighty book.

Maddy Osman: Yeah. I have the proof. Not like for reals for reals. But it’s good meat.

Joe Casabona: Look at that. That’s nice. This is another thing. My publisher is always like, “You need to write more words.” And I’m like, “I don’t think I need more words. I’m writing the minimum number of words to communicate the concept.” And they’re like, “But we need this to be a certain amount of pages to sell it at the price we want to sell it at.” I’m like, “Fine.” Just a really funny insight into that.

Okay, so part one writing for humans. Give us like a 10,000-foot overview of this section. What is writing for humans?

Maddy Osman: I think writing for humans is just appealing to the person that could actually like make a purchase. You know, the person who stands to either benefit from your content or for you to benefit from them reading your content. So it’s all about things like being thoughtful with word choice, so that you’re not unintentionally alienating them.

It’s about things like how to use numbers in a consistent way. Because without having rules around how you use them, it’s really easy to get like 10 different things. And then, you know, if you’re, for example, writing for a specific client, and you have multiple writers writing for that client and the stuff doesn’t look the same, then it doesn’t make you look good.

It’s about things like formatting, using lists, how you… I don’t know if this is in the humans or the robots chapter, but how to use links, you know, like the anchor text. Even things like being careful about extra stuff at the end of the link, like UTM tags, or whatever. They may not be necessary because you probably have a different campaign than the person who originally shared that link.

And then yeah, the last big thing in that section, I think, is visuals. Because there’s some crossover with how a robot would process that visual, but ultimately it’s for that human reader and to engage them and keep them interested in reading what you put together.

Joe Casabona: That’s really cool. I like that you explicitly mentioned numbers because this is always something I struggle with. The rule of thumb that I learned was like I think up to six or seven, you’re supposed to write the number out, like in letters.

Maddy Osman: It’s something like under 10, I think.

Joe Casabona: Okay, is it under 10? I wasn’t sure. But up to a certain number.

Maddy Osman: I think that’s AP style specifically. It could be different with Chicago, for example.

Joe Casabona: Oh, gotcha. That’s always interesting to me. I’m like, “I wonder why.” But then like, I guess in certain context, if you’re talking about math, you’re not gonna write like T-E-N plus 7, like one seven. I just think it’s really interesting that you… Grammarly always corrects me with that. I paid for Grammarly for a quarter.

Maddy Osman: That chapter was probably one of the more boring ones to write, but also like one of the more necessary for my team. Because it’s also like talking about things like using symbols. Like some brands that I’ve worked with want to use the percent sign, some of them want to spell it out. And it’s like, you know, in order to be consistent with that so that they’re not constantly telling me like, “Hey, Maddy, why did you do it this way? We already told you we want it this way.” That’s why it’s important to have a style guide and to define those rules. It just helps you look like more of a professional and it saves your clients time on making those silly edits.

[00:26:09]

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[00:27:07]

Joe Casabona: So let’s go on a quick side quest here. Do you have a different style guide for each client? Or do you have your base style guide when you make adjustments based on the client’s preferences?

Maddy Osman: That’s more important it is. Some clients are very specific. So if they have a detailed style guide, we’re probably just gonna go with that. And then the writers know Blogsmith’s style for whatever it isn’t explicitly defined. But for the most part, it’s just making adjustments and kind of saying, like, “Here’s where that rule differs from ours.”

Joe Casabona: Nice. What’s interesting about this in that book, is you mentioned that was a boring chapter to write. Again, just like in my last book, you know, kind of the, whatever, how to use an FTP program is like not… I mean, HTML is not like a page-turner, right? It’s like I wrote a textbook. But this could really serve as a resource, not only for content creators like myself and the listeners but for agencies who might need to put together their own style guide. Right?

Maddy Osman: Yeah. I mean, I think that’s the hope ultimately is that people will use this to create their own rules. They don’t have to look exactly like mine, but as long as you’re defining them and sharing them with whoever’s involved in that process, the goal is ultimately to save everybody time and effort.

Joe Casabona: That’s awesome. So the writing for robots section, by robots you basically mean “I won’t explicitly name any search engine,” but search engines, right?

Maddy Osman: Yes, exactly. So any sort of robotic entity that would be indexing, and then serving up your content to that end user. And mostly search engine spiders. But what’s kind of interesting too is now we have all these AI tools, especially in the world of writing. So it’s just interesting to maybe put yourself in the perspective of how these robots quote-unquote think, how they process information, and even how much more sophisticated they’re getting as search engines refine their algorithms.

Joe Casabona: That’s another kind of interesting thing to think about. Have you used any AI tools to write any content for yourself, we’ll say? I don’t want to put your agency on blast here, but have you tried any?

Maddy Osman: We’ve definitely tried them, I would say more for like components of the creation process, whether that’s headline generation idea, or even like an initial outline. We use two AI or maybe they’re more machine learning or maybe it’s a combo tools right now for the briefing process and then kind of for the final content optimization process.

I think you’re familiar with them. Clearscope is one and then Phrase is another. The way that those work is more kind of just like scraping Google data, and then presenting it to you in a way that you can act on it versus like creating an outline or something like that. But it’s the idea that it’s saving us doing all that research, giving us an early win kind of.

Joe Casabona: That’s really interesting. I’ve always been kind of suspect of them. I tried Anyword. Full disclosure, Anyword paid me for a review on my YouTube channel. And I gave it a try, and I was actually surprised. I mean, the main content was like whatever. But the headlines, right, I think it was like ideas for how to make money with your podcast. There were a couple that I didn’t think of or didn’t think of immediately, like selling merch or whatever. And I thought that that was really impressive. If nothing else, it did. It gave me like an outline to work from, which I thought was pretty cool.

Maddy Osman: I think that’s the main use case of them right now. It’s to sort of assist you. It shouldn’t replace your own human ingenuity or your won human emotions, whatever it is about you that connects with other people. But it’s interesting.

Before this, I was on Twitter, and I saw that somebody had done like an experiment where they had published like 30,000 AI-written articles. And he said like only a very small percentage of them ever got indexed. They hit their peak rank, but now are going downhill. And he’s like, you know, “If I want to improve that, I’m gonna have to totally rewrite these articles.” So at this point, Google has come out and said that any AI-generated content is not something that, if they know that that’s what it is, they’re gonna rank. So something to think about.

Joe Casabona: And some of these tools, like are basically lifting paragraphs. Well, from what I understand. From what people have told me, these tools can sometimes lift straight paragraphs from other blog posts, right?

Maddy Osman: Right.

Joe Casabona: Plus, AI can’t tell a story from your personal life. I just wrote a blog post today about how the eye doctor, my optometrist got an extra 40 bucks out of me, and I happily paid it because I didn’t want to get dilated because that’s like four to six hours out of my workday that I lose, right?

And they’re like, “Well, for $39 we can just do a photo of the back of your eye and that doesn’t affect your vision at all.” And I’m like, “Yeah, perfect. Done.” And then I related that back to like, if you understand your customers and their problems, you can also come up with these little add-on offers.

Maddy Osman: 100%.

Joe Casabona: AI is not going to the doctor, you know.

Maddy Osman: And I think what’s really interesting too is it would be hard for I think, either of us, even though we are content creators, to like look at two sentences side by side and be able to identify which one was which. But if it came down to like, in the wild, you know, looking at those two things and one of those influencing a purchase decision, I think the one that does that would be the human-written one because it would be written from a point of empathy or sympathy or whatever, you know, just to whatever extent. Versus the robot one can’t do that yet. Maybe it can do whatever.

Joe Casabona: Right, right. That’s something that Shawn Hesketh of WP101 videos just talked about. Like, when we were making videos together, he would talk about this attention to detail and syncing up the background music so that when you do something like the crescendo of the background music matches that, or when you say click like then the click happens. Because people might not be able to verbalize why something seems off, but they’ll know. It’ll be kind of instinct. Like, “This doesn’t right.” So those little attentions to details. I can’t do that yet. Hopefully never. Right? I’m a technologist, but I don’t want that.

Awesome. So writing for humans, appealing to the person, the empathy, being thoughtful in your word choice and things like that, writing for robots, appealing to search engines, and maybe some of these AI tools. Then you put it all together. How do you write content that works for both humans and robots? I assume is what that is.

Maddy Osman: Yeah. A lot of it is kind of like building out your own style guide. Like taking some of these lessons and some of these thoughts and like, how can you then apply it to your own brand? It’s also kind of tangentially related to like social media style, and how does that differ from long-form content. You know, what things are the same, what things are different? And then I share a couple examples of both social media and written brand style guides that people can also consult, again, just as like a reference to build their own.

Joe Casabona: Nice. So with that, let’s talk a little bit about… You know, I looked through the book. I didn’t read it cover to cover yet, but it is on my Kindle ready to go. But chapter 11 is the one that really stood out for me. That’s in part two writing for robots. Though, I suspect there’s good advice for—I mean, I know there is for humans and robots here—how to write compelling SEO titles and page titles.

My favorite part of this chapter was kind of headline formulas, right? A keen observer of howibuilt.it might have noticed that, any of my episodes from like 2018 and before were formatted like, Episode 132, you know, guests name and company name. But recently I created a spreadsheet of all of those, I came up with new titles, and my VA went in and updated all of those titles.

Maddy Osman: That’s awesome.

Joe Casabona: Because episode whatever, name and whatever is like not a compelling headline. Whereas like, how to deal with negative reviews on your product with Jason Coleman, that is a compelling headline.

Maddy Osman: Totally.

Joe Casabona: So what’s your advice for writing a good headline, I guess, from the robot perspective and from the human perspective?

Maddy Osman: Totally. Okay, let’s start with the human one. There’s a stat, a fact and example, whatever you want to call it, that has stuck with me pretty much since I read about it. And it’s an example from Buffer. And so what they do is, whenever they’re trying to determine what the best headline for an article, the article title should be, they’ll tweet different versions of it. So they’ll use that as the tweet copy. And then they just dig into the analytics on that, you know, what got the most impressions, click-throughs, whatever. And then that ends up becoming the title of their article.

So I think that’s so great, because it ultimately doesn’t matter how good you think the title is, right? You might think that you have such a Witter, just like perfect, whatever, but obviously, if nobody ever clicks through and reads what it corresponds to, the title did not do its job.

Joe Casabona: Right. Right.

Maddy Osman: So I think their tip is just great, because it then involves the end reader and it’s real data. It’s sharing it with your audience and seeing what performs. So that’s my favorite human example. I think-

Joe Casabona: So real quick on that, they’ll tweet the headline I assume with a link, right? Because I feel just the headline feels like a non-sequitur.

Maddy Osman: Right. Right. Right.

Joe Casabona: Like, “20 ways to increase engagement. What are they?” Cool.

Maddy Osman: Exactly. So they kind of like AB testing headline. So they must pick one, right? And then they kind of AB test on Twitter. That’s cool.

Maddy Osman: Exactly. And then as far as robots, again, it really comes down to eventually how it influences the human. But I think a good way to judge how the robots are processing your content is to definitely if you don’t already have Google Search Console installed on your website and have it gathering data. And then they have this search results report where you can see the clicks and impressions associated with the different keywords that you’re ranking for. I guess it’s not so much about titles but more so just what is ranking, like what you are effectively ranking for, and the words that people are using to find you. So I think that that’s an important insight from the robot side, but to apply to the end reader.

Joe Casabona: And that’s really interesting, right? Because you said it really still comes down to how it influences the human. Because I mean, Google specifically, right, they are… Part of their PageRank is what people are clicking on and recommending, right?

Maddy Osman: Exactly.

Joe Casabona: So you can have the most factually correct article, but if it’s just called like whatever-

Maddy Osman: Boring.

Joe Casabona: Yeah. Like a treaty on headlines or whatever, no one’s gonna click on that.

Maddy Osman: Right.

Joe Casabona: You also in this chapter mentioned… Well, actually, you mentioned Google Search Console. Are there any other… I’ve been on a quest for a good keyword research tool lately. Full disclosure, Ahrefs was a sponsor of this show and I use their free thing, but they don’t accept American Express as I record this, and that’s where I run all of my business expenses through. I get unreasonably mad when somebody doesn’t accept that.

Maddy Osman: There’s a lot of people that don’t, for sure. I have one for personal credit card and I always feel bad when I bring it to like a small business and like, “I guess I’ll use my other card.” But if it’s like Dunkin Donuts, or whatever, I’m like, “You guys could take the hit.”

Joe Casabona: In my opinion, if you have an enterprise-level plan, you should probably accept AmEx. Again, full disclosure, that’s not like a knock on the tool or anything. I try to keep my books as clean and run all of my expenses through AmEx. What are you using these days for keyword research?

Maddy Osman: I will say mostly Ahrefs. But there are some really awesome free tools that work within the search engine results page of whatever keywords you want more information about. Keywords Everywhere, great Chrome extension. I believe they have a Firefox extension as well. And it just kind of adds data on the sidebar of whatever SERP you’re searching for.

Then on a similar note, Keyword Surfer, which is Surfer SEOs, I think they just call themselves Surfer now, same sort of idea. And then I think they have some additional insights that you wouldn’t get just from Keywords Everywhere. They’ve kind of opened their tool up a bit, kind of like Ahrefs has where they have some free versions or free features. And I do talk about both of those in the book. I’m trying to remember which chapter that was. It’s got to be… I’m trying to remember. It’s definitely in this humans and robots section, I would say.

Joe Casabona: Nice, nice. You know, this reminds me of the index process. Your book doesn’t have an index probably because you’re self-published. I asked my editor, I’m like, “How do you automate creating the index?” and they’re like, “We don’t.”

Maddy Osman: “We don’t.”

Joe Casabona: Someone reads the book and then decides what the important words to include in the index. I’m like, “What? That sounds like the worst job in the world to me.”

Maddy Osman: I thought about it, but I was like, I don’t know… there could definitely be a benefit to that. But I feel like maybe the book is not long enough for… Kind of already has. It’s kind of organized in a way where you should find it where you expect it.

Joe Casabona: Right. I mean, especially today, if you get the digital copy, You don’t need the index. You just search for a word.

Maddy Osman: That is true.

Joe Casabona: I just thought that was really interesting. Cool. So thanks for those recommendations. I’ll probably just like stop being a turd and use a different card for Ahrefs because it is a really good tool.

Maddy Osman: I will say I don’t know if they’re still doing this, but they had an offer where if you donated to a cause that’s helping the situation in Ukraine, they had like a certain list but they offered to match whatever you spent on that. So the Blogsmith are… Not April. What’s before April? March. I’m already getting lost in this.

Joe Casabona: One of these months.

Maddy Osman: One of the months that happened this year already, our Blogsmith donation recipient was United Help Ukraine. And then like two days later, they’re like, “Oh, we’re doing this thing.” And I think it’s because a lot of people who work at Ahrefs are based in Ukraine. So they may still be doing that.

[00:45:15]

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[00:46:21]

Joe Casabona: And then I’ll just throw one more tool in the ring here. It’s YouTube specific but it’s been hugely helpful for me on planning this series on YouTube, which hopefully is out by the time this episode comes out. But it is TubeBuddy. It’s a Chrome extension. It kind of works right alongside YouTube, right?

So you go to a video, it gives you all the stats and the keyword ranking. But there’s also a keyword research tool built into it. That was really helpful. Like I would search like Stream Deck and it wouldn’t really… They’re like, “This is okay.” But then I’m like Stream Deck pedal, and they’re like, “Yeah, make content on that.” Awesome.

So we have the human and head and robot aspect of headlines. What’s your approach to writing a headline? I’ve heard like, write 25 headlines and then see which ones you like best? Is that good advice? Do you do research first? Do you AB test?

Maddy Osman: I think for me I like to think about headlines after the articles written. And I don’t know if that’s right or ideal or whatever, but it’s hard for me to conceptualize what the title should be without having the content. As far as like help coming up with options, because I do think that there is merit to coming up with, say, 10 examples and then narrowing that list, a couple of things that I mentioned in the book, beyond those headline generation tools are some like headline analysis tools.

So you could take those formulas and do five or ten headlines or something like that, and then run them through these analysis tools, which take them from different perspectives. Like one of them is from sort of like the emotional analysis, which, you know, ultimately that’s kind of that human reader you’re trying to reach. They’re definitely thinking with their emotions, when they’re reacting to what content they want to read, based on the headline.

Also, CoSchedule has a really great analysis tool that probably has the most highest level of detail in terms of like, you know, you’re using emotional words, or this is the breakdown of common versus uncommon words, which you want to think about because you want to appeal to your target audience. You know, are they very sophisticated in the way that they talk? Or is it closer to the average eighth-grade level of reading. And then Sharethrough has another tool that’s very similar to the CoSchedule one that, again, just helps break it down by different, different aspects. And then what I like about them is they give some really specific suggestions for what to think about to tweak it.

Joe Casabona: That’s awesome. The CoSchedule… Gosh, I forgot the CoSchedule tool exists, but I use that for a lot, especially after Nate Ellering was with the company and came on the show a long time ago. I think he mentioned it and I was like, “Yes, I’m gonna use this all the time.” And I did and then I stopped. But that’s really interesting. There’s a lot of really good resources here.

Now, we’re coming up on time. This has been such a great conversation. If people want to buy your book, like I said, as this episode comes out, it’s available for pre-order. When does it come out? And where can they order it?

Maddy Osman: Sure. So it’ll be on Amazon for at least the first 90 days. Taken advantage of that… Kindle Selects, what everything they do.

Joe Casabona: Nice.

Maddy Osman: It comes out July 18. So right now it’s available for preorder as a Kindle, and then on July 18th, the print version will be available. I did not know that before starting this process. That if you do their publishing for the print book, you can’t do pre-orders for it.

Joe Casabona: Oh, that’s really interesting. It’s probably because the order comes in and then a robot sends it to the printing press, and the printer prints it and then it gets shipped out all automatically. If you preorder it, it’ll just be like that conveyor belt that gets backed up. It’s like bunch of books with nowhere to go. That is really interesting. I didn’t realize that either.

Maddy Osman: It’s so weird.

Joe Casabona: Cool. Well, my advice would be folks to preorder the Kindle version. And then if you really want the print version, buy it on July 18th.

Maddy Osman: There you go.

Joe Casabona: Awesome. Maddy, I mean, I like to ask, do you have any trade secrets for us? Do you have any trade secrets for us?

Maddy Osman: Should I focus it on publishing or writing for humans and robots?

Joe Casabona: Dealer’s choice.

Maddy Osman: Dealer’s choice.

Joe Casabona: Pick your favorite one. I maybe will focus it on publishing just because it’s so top of mind. But I think it’s important to realize that if you do want to self-publish, it is an incredible amount of work. It’s worth it because you get creative control, and you can really make it what you want. You can put in the level of effort that you have.

The other important thing I think to know is the writing, the publishing, the formatting, the book cover, all those details is like half of it. And then the promotion is the other half of it. So don’t think that you’re done just because the book is done. That’s about 50% of the process.

Joe Casabona: I’ll just echo like that is also the same for publishers. Like they want to know how you’re gonna promote the book, too. So that’s not just a self-publishing thing. If you want to write a book, you got to be willing to promote it. What a great trade secret!

And it’s a perfect trade secret, because we’re going to talk more about that in Build Something More, which is only available to members of the Creator Crew. You can sign up over at howibuilt.it/272. It’s 50 bucks a year. That’s less than five bucks a month. I’m certain that’s less than the coffee I’m drinking. Maddy, is it less than the beverage that you’re currently drinking? I feel like you got that from somewhere. Oh, that’s just your own water cup.

Maddy Osman: Well, but it’s Macha from my Machabar, which is not inexpensive, but it probably is just a teeny bit less expensive than going to Starbucks.

Joe Casabona: See that.

Maddy Osman: Just love them.

Joe Casabona: My coffee from Starbucks was like six bucks the other day. So 50 bucks a year over at howibuilt.it/272. Maddy, thanks so much for joining us today. I really appreciate it.

Maddy Osman: Thanks so much for having me.

Joe Casabona: And thank you to everybody listening. I appreciate it. Thanks to our sponsors for this episode, StellarWP, actually LearnDash by StellarWP, TextExpander, and Nexcess. Until next time, get out there and build something!