How This Entrepreneur Went From Being a Freelancer to an Agency Owner

[00:00:05] Jon Penland: Okay. Hey everyone. My name is Jon Penland and Reverse Engineered is brought to you by Kinsta, a premium managed hosting provider. In today’s episode, I’m speaking with Maddy Osman, Founder and SEO Content Strategist at The Blogsmith. Maddy, welcome to Reverse Engineered. 

[00:00:23] Maddy Osman: Thank you so much for having me today. 

[00:00:26] Jon Penland: So to get us started, Maddy, can you introduce yourself to our listeners? 

[00:00:28] Maddy Osman: Absolutely. So I started The Blogsmith, which is an SEO content agency. We have worked with Kinsta before. And I’m focused, I would say primarily on the B2B technology space. We love working with brands that are doing cool things with technology and just need to communicate that to, you know, their regular users and the layperson, especially as far as things like release notes and things like that. So we love, we love working with technology   brands and that’s pretty much what I’m up to these days. 

[00:01:03] Jon Penland: Okay. So I do think that lots of our listeners are going to know when we start talking about content and SEO they’ll know what we’re talking about, but I do think it’s possible that some of our listeners won’t immediately know what we’re talking about. So before we get too far into this conversation, can you give our listeners a one-minute, two-minute crash course on what it is that your agency, The Blogsmith, actually does for the B2B companies that you’re working with?

[00:01:30] Maddy Osman: Absolutely. And I want to take it a step back to just define it kind of like you were saying. I think the best way to conceptualize what content marketing is, really starts at the Genesis, as far as I can recall of one content marketing started. There’s probably, you know, even early civilizations or something that had their own forum with pictograms on the wall, things like that.

[00:01:57] But, the earliest, I think established in the market idea of content marketing is The Michelin Guide. So basically, the Michelin tire company put together this guide to the top restaurants in different metro areas, you know, big, major cities and things like that, around the world. And nowadays we know these restaurants that have been mentioned in this guide, as you know, some of the best restaurants you could go to.

[00:02:25] They have star ratings from one to, I think, three. And, you know, they’re typically more expensive than the average restaurant, but it’s because, you know, they’ve earned the right to charge the prices that they charge. And it really came back to this guide that Michelin put together. And so, you know, people might wonder, “Well, why did Michelin tires, you know, publish this restaurant guide?

[00:02:50] What, what did they get out of it?” And it’s interesting to consider kind of like the mental leaps that they must’ve made at that point in time when it really was not a thing to do content marketing, especially something that’s not, you know, about tires specifically. Right? So I think that in this case, it helped Michelin tires to sell more tires because then people, you know, wanted to go to these restaurants and drive around and do all that.

[00:03:17] And so, it’s not, in this case, it wasn’t the most direct going from point A to point B. Right? But I think the lesson that we can take away from it for today is that even in situations like that where, you know, maybe there’s a little bit of a mental leap, or maybe it’s not directly related to, to like describing what the tires do or something like that.

[00:03:40] It’s interesting that it kind of made them a thought leader in this other industry, but then it comes them and the form of people trust them essentially with their tires, because they’ve associated themselves with these big brands that, you know, big in the restaurant space, but that have a lot of respect from the restaurants, audiences.

[00:04:03] And so it’s, you know, maybe not the most exact example or something that is the easiest to understand, but it’s, it’s something worth diving into, because it then inspired a lot of other things that are like that, that are now happening here. So in terms of what The Blogsmith does for our clients, we are focused on the writing side of things.

[00:04:27] And so we are helping to create that content, making sure that it’s on brand, that it serves the right type of customer, that this brand is trying to attract, and that might be different customers at different stages in the buyer’s journey. It’s also a matter of making sure that that content is created in such a way that it can show up in relevant search for these types of customers that this brand wants to connect with.

[00:04:54] So that’s, that’s the marketing side of things. There’s like the writing side of things, which has marketing in terms of, you know, branding and communications obviously, but then the part where it pulls in people is really that SEO side of things. And for some customers, we’re also helping with social media copy and submitting them to, submitting content to places where people will share it and, you know, other aspects of distribution. But I would say, primarily we’re focused on the writing and the organic SEO side of things. 

[00:05:28] Jon Penland: Yeah. I had never, I’ve never heard of the Michelin Guide. That’s actually really fascinating to me that the… 

[00:05:35] Maddy Osman: So fascinating. 

[00:05:36] Jon Penland: …thought process, yeah. The thought process, as I think about it, so I’m imagining like somebody in marketing and Michelin going, how do we sell more tire? Like, how do we increase demand for tires?

[00:05:48] And somebody being like, “You know, what, if people took more road trips, we would sell more tires.” And so they’re like, “Well, how can we help encourage a culture of road tripping?” And they’re like, “I know, best restaurants all over the country.” Right? Like jump in your car, go check out this restaurant in Chicago, go check out a restaurant in New York.

[00:06:07] Right? Like, so it’s not directly connected to Michelin’s business, but it supports the activities that Michelin’s business relies on. And so I like bringing that back to Kinsta. If you think about, for those who are familiar with Kinsta’s blog, we publish all sorts of stuff that does not directly drive a customer to sign up for our services.

[00:06:32] Like, there’s so much that we publish that something like, you know, here are these, HTTP error codes and here’s what they mean, or here’s how you launch a successful e-commerce website. Some of that stuff does directly tie back to driving somebody to be a Kinsta customer. A lot of it just encourages sort of like self-driven WordPress-based online activity, which indirectly supports Kinsta’s business.

[00:06:57] Right? So I think our connection is closer than the Michelin Guide, but it’s the same kind of… 

[00:07:04] Maddy Osman: A little bit. 

[00:07:04] Jon Penland: …a really, that’s a really fascinating, yeah, yeah. A little bit closer, right, than publishing a restaurant guide to hope people go on road trips, but, but still similar concept is really fascinating. So something that I really want to talk to you about-

[00:07:18] Maddy Osman: I was going to say, that’s something that I remember writing for Kinsta, that people keep coming back to me about like, ’cause it just continues to rank and people continue to find value from it, is I wrote something about, it was like LinkedIn stats or something, you know, things that you need to know in order to then use the platform in an optimal way for, you know, sales and networking and things like that.

[00:07:42] And it’s like, obviously you’re not a social platform. You know, you’re not necessarily trying to get people to even use social platforms, but it’s related to that audience of somebody who is in digital marketing or who is a business owner, who’s, you know, building their website and then is thinking about the things that are tangentially related to that.

[00:08:04] And so it’s like, yeah. Maybe it wasn’t about like, you know, how to like get into the WordPress database or something like that. But obviously there’s still value to that because people keep finding it. People keep going back to Kinsta and it’s helping Kinsta to be a thought leader in the general space, in addition to the specific space. 

[00:08:24] Jon Penland: Right. Right. And we’re supporting that small business owner or that marketing strategist who a part of their portfolio of business may well be a WordPress website. So, even though this is not directly necessarily connected, right, it’s like, how do we support that individual who apart of what they do is going to be, is going to come back to the services Kinsta offers?

[00:08:47] Yeah. So one thing we were chatting about briefly before we jumped into the call is that my background is actually in content marketing before I joined, actually my first involvement with Kinsta was in content marketing. And I’m really fascinated to understand sort of your story in content marketing. How you got into it and how you got to where you are today?

[00:09:06] So that’s, that’s where I really want to kind of dive in and focus today. So, take me back to the beginning. How did you get into content marketing?

[00:09:17] Maddy Osman: Yeah. I think it honestly started when I was much younger. I think it was like, I was 11 years old and I taught myself CSS, HTML, just like basic website design stuff. It was probably at the time, ’cause I wanted to customize my Neopets profile or something like that. And, you know, you start to pick it up ’cause it’s fun and I didn’t have a goal in mind for it, but then it led actually to my first college job. I worked at a marketing and design agency at the school that I went to and that’s kind of where I picked up the marketing side of things.

[00:09:55] I saw what everybody else was doing. And I was really excited about the whole process from start to finish of working with clients and solving problems. So eventually, I think my boss noticed that, like I wasn’t the stereotypical, like quiet developer type and I had a lot to say, and he offered the opportunity for me to then contribute to the student life blog, which was really exciting to me because I really loved my college town and there was just so much to do there.

[00:10:26] And the whole point of the blog was like trying to steer kids away from drinking. So, you know, it was very just like positive, fun, like things that anybody could do. And I also got the opportunity to help with the social media side of things too, which was really exciting to me. I think, you know, that was the first time I had used it as a marketing tool or it’s like a way to communicate with an audience that wasn’t like my immediate friends and family.

[00:10:52] And so from that job, I took on a bunch of different roles after graduation, and even in college, I did some brand ambassadorships, so I learned a little bit more about sales and marketing in that way. I worked in sales at Groupon after I graduated. So I learned all about that side of things.

[00:11:36] And then my last job before I quit and decided I really want to do this full time was another sales job, but it was at a marketing company. And so kind of putting all these different things together, I thought that my freelance path would be more social media, website design stuff, but eventually, I realized it was really the blogging, that was what made, what made me excited to do that work and what I thought that I could then offer as a service to other people by creating a consistency around my processes. So that’s kind of the long convoluted way that I got from there to here. 

[00:12:11] Jon Penland: Yeah. So your first paying customer, so you did a lot of stuff where you’re working for other businesses, and it sounds like maybe you were working on gigs on the side a little bit. And I’m curious, as you started shifting into working as a freelancer, it sounds like initially, your initial freelance work wasn’t even as a writer. Is that accurate? Was your initial work doing social media, web design, that type of thing?

[00:12:39] Maddy Osman: Was definitely a mix. So I, you know, the freelancing that involved writing was things that I fell into. It wasn’t, it wasn’t necessarily job opportunities I sought out. So it really was very serendipitous for this to happen. And essentially the reason that I was able to quit my full-time job was because I had somebody that I worked with on a freelance basis who said, “I’m looking for someone to help in a bigger capacity, being kind of like a virtual assistant, focusing like mostly on content.”

[00:13:13] Social media was the big part. And then you had a couple of clients who had blogs that they needed to have written on a regular basis. And so I did all those things and none of it had to do with web design. And, and that was the catalyst for me to go out on my own because I knew I could at least pay rent with what he was going to be paying me.

[00:13:38] And then it really just developed further from there where I took on a lot of this mix of projects. And then eventually I think it was actually after the WordCamp that we both last attended before. You know, WordCamps got shut down, unfortunately, but it was, I think I had, like an aha moment there that the content was really the thing that I was good at and that I liked and that I really needed to just cut out all this other stuff and double down on that. 

[00:14:05] Jon Penland: Yeah. Yeah. So, okay. So, so you were doing a variety of things and then you had this, this moment sometime a couple of years ago where you were like, “All right, this is really the thing.” So as you start focusing on that piece of the work that you’re doing, what do you think allows you to stand out as a freelancer?

[00:14:26] There’s a lot of freelance writers. What do you think made you unique? Or what was the unique value that you brought to the table as a freelance writer?

[00:14:35] Maddy Osman: Totally. I think there’s a couple of things that helped me to get where I am today. And a lot of it just comes down to my background, but the first thing was sales savvy. I’m not afraid to ask for what I want. I’m not afraid to ask for what I’m worth. And I think that with freelance writers, like developers, it just tends to be a more introverted person.

[00:14:55] Right? And there’s nothing wrong with that, but it is harder to ask for what you want when you know, you’re, you’re an introvert basically. So I think like whenever I talk to freelance writers who are just getting started, that’s something that I say, “Maybe you should get a sales job first because essentially you’re getting paid for the training. You’ll learn a lot.” I mean, really, I think that everybody should have a full-time job before freelancing because you learn about the organization and how to work with different people, how to communicate well, how to solve problems. And you just learn from people who have already figured it out, right, like, how they handle invoicing, how they handle client issues, whatever. So get a sales job and then maybe get a marketing agency job and then freelance. And then you’re going to be, there’s going to be so much further along and you’re not going to have to do as much grunt work because you will be confident in what you’re presenting to people.

[00:16:01] I think communication is also just a big skill in general. You know, you deal with tough situations with different clients and it really is, you have to be very purposeful with how you enter into those tough conversations and how you navigate out of them. And I think a lot of it has to do with just having a plan going in and not winging it.

[00:16:26] One thing that has been really helpful to me lately is once the pandemic started, I started therapy just because it was just such an overwhelming time. And, I had never done it before for myself, but it’s even now, I stopped and then I restarted. And, what I really use therapy mostly for is like communication with other people.

[00:16:21] I use it as a tool to get another perspective on tough clients situations, tough friends situations, tough family situations. So like, that is actually a pro tip, like get a therapist and they’ll help you communicate through any of these like weird things that you’re uncomfortable with. And it’s just nice to have somebody else that you can talk to.

[00:17:18] And you could also accomplish that and like an accountability group or a mastermind or something like that, but just get out of your own head about things. And then I think like the last big thing that has helped me to stand out, at least moving forward, maybe not initially, but now, is that I have spent a lot of time cultivating a style guide for The Blogsmith that is based on AP style, news journalism, but then takes it like many steps further into formatting, into handling different types of articles.

[00:17:16] And the reason I developed it was because I knew that I wanted to scale this business. And I knew that working with a lot of different people, I was going to get that many different formatting, you know, situations when they were turning things in. And so I wanted to cut down on edits, but I also wanted to ensure that I could produce consistent, high-quality products. And so that style guide, I think it’s like 17 pages long now. It’s really ridiculous.

[00:18:22] But I’ve also used that to write a book that initially, the thought process was like, “I could share this with my team if they want additional context or examples.” But it’s something that I’m going to offer for sale after it goes through professional edits and some other things that I’m still working on.

[00:18:41] But you know, just the thing that is kind of like the elements of style, but updated for today, for people who just want to create consistent, high-quality content. 

[00:18:55] Jon Penland: Yeah. So I heard like a few different things there that you brought to the table that made you, or that made you unique and that makes you unique today. So like, one of the things is sort of this business-savvy sales marketing background. The second piece was you talked about getting out of your head, finding a way to work through communication issues where everything’s not just in your head, and then the third piece had to do with quality.

[00:19:18] Right? So like had to do, today that’s accomplished with a style guide, but I have to assume that looking backwards, quality was also a piece of that equation early on. Right? Like it’s, it’s so funny that you mentioned those things. Go ahead.

[00:19:36] Maddy Osman: I was just going to say it was in my head. Right? So I had ideas about what quality meant, but it wasn’t until I documented them that I was able to scale my business. 

[00:19:45] Jon Penland: Yeah. It’s funny that you mentioned those things because I think a lot of people, when they think about a freelance writer getting started, they would maybe say, “Well, I had this area of really deep expertise, or I was just a really great writer.” And those things do matter. I’m not saying that those things don’t matter, but the things that I would have highlighted as being things that were important when I was in that space as well were actually a lot of the same things. It was like, I try to be a professional, right? Like I try to make sure that…

[00:20:23] Maddy Osman: That’s what it is. 

[00:20:24] Jon Penland: I have professional communications with my clients. Yeah. And that I deal with them professionally and that they enjoy working with me. And then the quality piece has to be there. I, I will admit I did not have the communication thing down the way you’ve talked about. That’s a superpower I hadn’t unlocked yet. 

[00:20:34] Maddy Osman: I didn’t always have it either.

[00:20:37] Jon Penland: Yeah. Yeah. That’s awesome. Okay. So, you’re a freelancer, you’re working independently. And at some point, you made the decision that it was time to move from being an individual freelancer to building an agency. And I’m curious, what prompted you to make that change?

[00:20:57] Maddy Osman: Yeah. I don’t know what it was. I know that it was around that last WordCamp US and I dunno. I think it was like a very existential moment for me because in that same year my dad had unexpectedly passed and he’s like my greatest inspiration because he was an entrepreneur. He showed me that anything is possible.

[00:21:23] I mean, when I told my parents that I was going to quit my job and go freelance, like you would probably expect a parent to be like, “Hmm, maybe like you should keep your job. You know, like maybe don’t, or whatever.” And my parents are like, “Do it. Like we believe in you.” And so like, there was never any doubt from them that I could do it.

[00:21:46] And I think that’s what eventually led to me doing this. But yeah, that year I was just, I was just thinking a lot about existence in general and like, what is, what is the point of this all. You know, what is my purpose here? What am I, what am I supposed to do? I don’t think this is it yet.

[00:21:23] And then I thought, “This is, this aspect of what I’m doing is something that I think I can continue to improve upon.” I think that it’s something that every business needs, to some extent. I mean, even if SEO content goes away, like we still need marketing and communications, right? Like even if we don’t have computers in the future, like we still need to be able to communicate and pictographs or whatever.

[00:22:31] I mean, so yeah. There, some of it is existential crisis and some of it is just doubling down on what was working. So I think that for anybody who’s struggling with what you want to do in life, like, I don’t know, take a step back from what you’re doing every day and consider if that is what you want to do every day. And if not, like what would give you that happiness and, and where could you make a difference? ‘Cause I think that’s the other thing with me trying to develop this book that’s based on my style guide. It’s like, I don’t want it to just improve my writing if it can help other people to communicate effectively with whoever it is they’re trying to communicate. Then I want to share that with them. 

[00:23:15] Jon Penland: Hmm. So like practically speaking, you’ve kind of gone through this process where you backed up big picture and you’re like, “All right, I’m going to double down on this thing that is valuable to me.” Some personal life circumstances making you kind of take that step back. Practically speaking, what’s your first step then? Who’s the first person you hired? How did you decide, “All right. I’m going to hire a writer. I’m going to hire an editor?” Like, what’s the first step? How’d you do that?

[00:23:45] Maddy Osman: Totally. So before that point, I had hired, I think I was working with two VAs at that point, so two virtual assistants. And they helped me with various admin stuff. They helped me with research. They helped me with some aspects of prepping the writing without actually doing the writing.

[00:24:02] And then I think one of them also helped me with graphic design stuff. So I was starting the very basics of this agency that I didn’t even know I wanted, but you know, the pieces that I knew I couldn’t do as effectively, or that like, there were just going to be very time consuming and I could use some help to be effective with my tasks.

[00:24:22] And so it started with the VAs and then the VA’s kind of led to starting to hire writers who, you know, basically would subcontract or I would subcontract to them, but I would still be the editor. You know, it would still be up to me to manage the client relationship, to manage that level of quality, that was important.

[00:24:45] And to make sure that the writers were prepared with all the information that I had. So from there, once I started hiring a couple of different writers, that’s when I realized, “You know, I’m going to get stuck unless I have somebody to help me with edits, just because it was starting to become a larger quantity of content.”

[00:25:03] And so that’s when I developed the style guide kind of in tandem with hiring an editor and it started very piecemeal where it’s like, “Okay. Let’s note that. You know, like let’s make sure that we do this moving forward.” And then it developed into like the document that is today, that’s very organized. It has examples.

[00:25:20] It has justification’s for everything. So really that first editor that I hired was very critical to scaling this. The writers also were very important, but they still have a limiting factor for me in terms of me having to oversee them. And so from the editor, I hired another editor because it just, you know, it got to the point where I didn’t want it to be all on one person.

[00:25:48] And the other thing is you have to realize that as you grow, no role should have only one person in it because people take vacations or they get sick, or they don’t want to work with you anymore. That’s all normal stuff. And so I hired another editor, I think currently on the Blogsmith team, we have three editors and maybe we’ll need another one soon too, but it works great, right now. And then after getting those very critical people in place, I started to get to the point where, you know, I was still very involved in day to day admin stuff, and I still owned all the client relationships. And so it was at that point that I realized, “Okay, I need somebody who’s going to be in charge of just project management.

[00:26:32] Like, are we on deadline? You know, does the client need anything to move this forward? Do we need edits?” You know, whatever, but just being in charge of that and being in charge of notifying people on the team who might be falling behind or who just need to know about new assignments and putting new assignments into the workflow.

[00:26:51] And then I also hired somebody to help me with keyword research because I was becoming the bottleneck on that. And so it was, again, a process of, kind of examining like what I do internally and then documenting it and then being an overseer of that person until I was confident that they were handling it and understanding what I was looking for.

[00:27:12] And then really the last, like big two more people that I’ve put in place. One was an account manager. So once I had the project management stuff figured out I wanted somebody, I wanted the project manager to own the internal relationships, and the account manager to own the external relationships, and somebody who could solve problems that didn’t necessarily need me for everything but only for the biggest things.

[00:27:37] And then the last like major person I’ve put in place before now, I’m starting to think of like doubling up on more of these roles and things like that is somebody who had been writing for me for a while, who expressed an interest in making this more of her full time gig. And so now I have somebody who’s like my right-hand woman and she just helps me to oversee client relationships, oversee these different people on my team, move stuff forward, troubleshoot.

[00:28:12] So, that has been honestly so critical for growth because now I can focus on the sales side of things, which eventually I want to put somebody in place for that as well. But it’s just like one of the things that I can’t let go of yet. What was the other big thing? Process development and, and making, you know, our writing better and always being aware of, you know, the newest changes in Google and, and how we need to react to those things. 

[00:28:37] Jon Penland: Yeah. Yeah. That’s really fascinating. What I feel like I’m hearing is it was kind of this iterative process where you were aware of where you were the bottleneck in the process. So initially, you’re the bottleneck and the writing. And so you’re like, “Well, let me back up a step and edit and bring on other writers.”

[00:28:56] And then you’re like, “Now I’m the bottleneck, as the editor. Let me bring on additional editors.” And then you’re like, “All right, now I’m the bottleneck in managing stuff internally, making sure all the different wheels and cogs are turning, or we bring on a project manager? Now I’m, now I’m the bottleneck because I can only talk to so many clients. Let me bring on an account manager.”

[00:29:12] Right? So there’s kind of like this iterative process where you’re going, “Where am I the constraint on the ability of this business to handle throughput? Like where am I the bottleneck in the process?” So that’s really, that’s really fascinating. I’m curious if there were any of those things that you found particularly challenging to hand over, either because it was just difficult or because there was an emotional aspect to it where it’s like giving up something that you care a lot about? 

[00:29:42] Maddy Osman: Yeah. I mean, all of them. Right? But I think the hardest, the hardest to start with was the writing, because I was so invested in it and, and because I didn’t have the style guide in place. So quality, I hired great people. I will say I got lucky. It wasn’t skill that helped me find those people early on.

[00:30:09] It was luck. And it worked out where, you know, I had very minimal edits on what they were doing, especially after being like, “Okay, this is how I really want this.” Stuff like that. So that was initially the most difficult thing to consider giving up, even hiring the virtual assistants to help me with research, I felt like, you know, it’s like, it’s cheating the process or something, but it’s like, as a business owner, you don’t have to be involved in every single step.

[00:30:37] It’s your job to stand behind the work, obviously and to have a process that ensures that the output that you create is high quality and up to your level of standards. But you don’t have to be the one that, you know, messages the writers every day to say, “You know, here’s where we’re at. Here’s your news stuff that you should work on. And also where’s this article or whatever?” I mean, like, it doesn’t have to be me. So, that was the hardest, I think the writing. And then the next hardest thing for me is going to be the sales, just because I come from this background where, you know, I went through all this training and I have all these ideas about how it’s supposed to go.

[00:31:17] And so even, even starting to put those materials together for The Blogsmith, it’s just like, I’m overthinking every single detail, you know? And so it’s like, I’m getting in my own way to some extent on that. But, I also know like, that is not where, I mean, I add value to it now because I’m the, I’m the person on the team who has the most experience with that. But I’m not the person, like I could hire somebody and they could probably do a much better job than me. So you just have to accept you’re not the best at everything. 

[00:31:53] Jon Penland: Yeah, it’s funny that you mentioned the thing about feeling like you were cheating the process when you first hired a virtual assistant. Because when I was a writer, I can remember very distinctly, I had a conversation with a website editor for one of my clients. And I had just found out, I was, you know, a content marketing, just gotten into that, into that market or into that space.

[00:32:15] And I really didn’t realize at the time, this seems very naive looking back, but at the time I didn’t realize that some of the other people writing for that blog were just editing content that they had worked with other freelance writers to produce. And I found that out and I was talking to that editor.

[00:32:34] And I felt like it was a scandal. Right? And I was like, “Oh my goodness.” You know? And, then he was like, “Jon, I would actually be in favor of you hiring a couple of writers, the quality of the work you give me is good. And if you could produce more work than it was of the same quality, that’d be awesome.”

[00:32:48] And it was super mind-opening to me because I was like, not only am I not cheating the process by doing that but here’s a client who’s telling me, “I would actually love it if you would stop writing everything. Go find some writers and edit, so that I get the same quality and a higher volume.”

[00:33:08] But I do think that the hiring the VAs was sort of like a, I don’t know, that feels like a key takeaway for people who are in that space. That feels like an easy or a, perhaps the lowest risk way to dip your toe into the waters of working with somebody else on your team. Right?

[00:33:29] Like moving from, ‘it’s just me to it’s me plus another person or two’. That feels like a really natural and perhaps the least risky way to do that. And I’ve heard several people talk about working with VAs. So how did you get into first working with VAs? Have you, did you find that to be super helpful in making this transition?

[00:33:53] Maddy Osman: A hundred percent. Yeah. So I think I got the idea from that person that I worked with, who made me the offer to then be able to quit my full-time job. Like he had enough work for me. He was exploring this kind of VA model. I essentially was his VA, but he was also hiring people for other aspects of his business.

[00:34:14] And, and he was mentoring me at the same time, which was, you know, really appreciated. I could ask him anything I wanted about growing my business because he knew that that was going to be my goal after quitting, that I would then want to find other clients and things too. And so, he was very transparent with me about how he went about it and things that I should think about and even like questions I could ask them to determine if there was a fit.

[00:34:40] And, I mean, that gave me the permission to pursue it, that I probably would not have taken on my own. And I think one of the biggest things you can learn from it, and I would agree that it’s kind of like a great entry-level way to experiment with, growing your business or even just like, like lessening the workload of stuff that you don’t have to do.

[00:35:12] That’s not like your core competency. The lesson I learned was how to delegate. And I think that that’s a skill that a lot of people don’t have because they’re insistent that they need to do absolutely everything, where it’s like, start, start with the research, right? Even if it’s not, work-related, say, I want to plan a trip in the future. And I don’t have time to look up all the details of all these attractions and hotels that fit my guidelines or whatever. Like just experiment with that and see, you know, give them, you always want to preface an assignment with some details and some expectations, especially setting a time limit for how long you think it should take because otherwise people will take forever.

[00:35:48] But with that in mind, by giving some direction and then learning from the process, it’ll make it easier to delegate anything else in the future. 

[00:36:00] Jon Penland: Yeah, that just strikes me as like, I dunno, like a great, the term I keep thinking of is like life hack, which I don’t want to use, but like that, that just strikes me as like a great tip or whatever for a freelancer to take away as like, “I’m in this process of trying to figure out how do I build my business?”

[00:36:16] Like a VA seems like a really natural way to begin doing that in a low-risk way. So we’ve talked a bit about how you got started in content, and then we’ve talked about how you sort of began the transition of becoming an agency. And I am curious now to kind of focus full bore on your business today.

[00:36:36] One of the things that you’ve talked about a lot is this style guide. And, and I think for some of our listeners are probably not sure what that is. So can you explain what that style guide is and how that ensures quality remains high, even as you’re delegating tasks?

[00:36:51] Maddy Osman: Totally. Yeah. So a style guide is essentially just a list of rules to follow or choices to make and how to make those choices when it comes to communicating via text or visuals. There are many established style guides that exist already. So there’s AP Associated Press, which is like a Wall Street Journal, New York Times, all of them would follow that.

[00:37:20] Probably Time Magazine follows the same thing. There’s The Chicago Manual of Style, which is more like nonfiction books. There’s an MLA, which is more like research, I think academic. So there are all these established style guides. And then a lot of brands create their own style guides. I would say most brands have the visual style guide, which just shows like, ‘”This is our topography. These are our colors. This is our logo and how you can use it.” But any brand that does a large quantity of publishing likely also has a written style guide, kind of adapted from probably one of these other style guides I’ve mentioned, most likely AP just because written news use stuff follows that.

[00:38:06] And so, with The Blogsmith style guide I wanted to just make things a little bit more clear. So we have an AP style guide subscription. We always check there first, whenever we’re considering adding a new rule to the style guide. I always want to run it by AP style first to see if they have an opinion on this and what is it, and do we agree with that. So adding to our style guide is either just like clarifying that rule, maybe with a slight difference or it’s just reiterating that rule really and saying like, “This is important to us.” And then as far as developing the style guide, it really has been just responding to different things over time.

[00:38:48] You know, like I noticed that I want subheadings to be formatted with a certain case, or I want to make sure that if it’s a listicle, you know, that the number formatting and headings is this way. It’s things like word choice. And, you know, we don’t want to, for example, we don’t want our words to unintentionally alienate somebody that we’re trying to speak to.

[00:39:13] So it’s being very intentional with language. It’s things like how do we style links so that they are, so that they’re setting expectations for what’s on the other end of them and that they follow us SEO best practices in terms of using keywords in them. So, so, yeah. I mean, the style guide, I would say mostly developed just from every day and, you know, thinking different things and we continue to add to it every day.

[00:39:41] And that’s why it’s a working document. It’s never going to be done, but it continues to be a better resource because we’re always thinking about it. And we’re always thinking about how we could use it to help writers improve, to say like, “You know, we’ve noticed over the past several pieces that like, you keep doing this, but just so you know, like here’s how we discuss it in the style guide so that you have a full understanding of why we do it the way we do it.” So yeah. Hopefully that answers the question. 

[00:40:11] Jon Penland: Yeah, it does. I’m curious. Have you found it to be challenging to have your writers and editors really understand and adopt the style guide and have it guide their writing? Like, do you usually, when you put it more bluntly, the first time you work with a writer, do you usually have to come back and be like, “All right, all this stuff is not according to our style guide?” And what does that process look like? Or do you have a formal onboarding process for the style guide to train them up on how to use it?

[00:40:43] Maddy Osman: Sure. Yeah. So when I’m first introducing the style guide to a writer and it actually starts, I think, in the job description I think I have a link to it because I want them to be aware that we do have standards that we’re going to hold you to. After somebody submits an application where we’re just asking them different questions to help us determine if there’s a fit, we would offer a paid test project and we typically do two because the first round we want to keep things really simple.

[00:39:55] And we just want to see if there’s any fit. And then the second round we’re seeing if there’s a Blogsmith specific, like if they could follow the style more, if they could follow the process more, and things like that. And so, what we say during the testing phase is, “I don’t think I have been linked to the style guide, actually.”

[00:41:35] I’m like, “If you’ve seen the style guide that, yes, it’s a beast, it’s a little bit overwhelming, here’s a takeaway of typically what we see from new freelance writers that it makes the biggest impact.” And it’s like the biggest mistake that people make. And it’s, it’s honestly things like in our style guide, we tell people to limit the size of sentences and paragraphs so that they don’t ramble on forever.

[00:41:57] And so that we’re creating consistent white space and things like that to get people to keep reading. And so a lot of it is like, honestly, just about that. It’s little things that make the biggest impact. So what we tell them is, “You know, that’s, that’s what we’re judging you on. We’re not judging you on adherence to the full style guide.” But the way that it kind of works in, after we would onboard them and work with them in a greater capacity, it’s just a matter of reminding them within our project management system.

[00:42:27] So we’ll have different sections that like in the checklist that they would check off and like one of them’s image guidelines, for example. Like, “Did you suggest a feature image? Did you, or did you get one created through one of the graphic design partners that we work with? And, you know, did you make sure to add alt text?” And it’s just like reminders.

[00:42:48] So we do reminders, but then ultimately the editors are the gatekeepers of style. So they’re the ones who are kind of tracking over time. Like, “Oh, this person keeps doing this and so, you know, I’m going to share why that’s not the case.” And sometimes it involves editors going back and looking over, especially during the paid test project stage. It’s going back and looking over suggested edits.

[00:43:10] So we don’t just directly edit the document in those early stages. We do suggested edits so that they could see where it is that we made those changes visually. So, yeah. I don’t think it’s been as big of a problem as I might’ve anticipated that it would be, but it’s also because I’m not expecting them to get it, a hundred percent from the get-go. 

[00:43:35] Jon Penland: Sure. But I also feel like to a certain degree you are selecting for people who are going to be capable of following it. Well, not to a certain degree, to a huge degree. Right? And so I actually think that strikes me as a really effective way of ensuring that by the time somebody reaches the point of actually being assigned a paid article, they’ve already demonstrated in a couple of different ways that they’re capable of following at least the most critical portions of that style guide.

[00:44:05] I think that’s actually, I love that. I think that’s awesome. Okay. So, how would you describe The Blogsmith’s go to market strategy at this point? How do you attract and land new customers?

[00:44:22] Maddy Osman: Sure. Yeah. Honestly, since I started the agency side of things, it’s been pretty much all inbound. One of my friends, we were talking the other day about how service professionals don’t like to market and it’s so true. And it’s because we operate usually very well on word-of-mouth referrals and things like that.

[00:44:48] So now that I’ve gotten a lot of the pieces in place, I’m doing a little bit more to more aggressively go after things, or just more intentionally, I guess, go after things and, and pitch business that doesn’t necessarily just fall into our laps. So I mean, luckily The Blogsmith we’ve created a good reputation for quality, a lot of it having to do with the style guide and the process of just onboarding new people onto our team and getting on the same page.

[00:45:11] Now that I’ve got the systems in place and I want to grow a little bit faster than it is organically, I’m really going to be leaning back on my sales days and the things that I learned when I was going through all of that. And I think that for us specifically, it’s a lot of being successful with sort of more like the cold pitching or even just going after jobs that are posted and things like that. 

[00:46:04] Jon Penland: The thing about being a freelance writer is that your byline appears all over the place, right? Like, one of the beautiful things about being a freelance writer is that by doing the work, you’re sort of advertising yourself because your name’s getting out there. Did you find that a lot of your customers found you that way? Like, here’s a customer in the same space, we found this writer on a competitor’s website and let’s go talk to this writer?”

[00:46:17] Maddy Osman: Yeah. No, that’s a really good point that I forgot to bring up, which is that that happens all the time. Right? And so that’s why, if somebody wants ghostwriting, for example, if you’re a freelancer, you should always charge them more for that because you miss out on the marketing opportunities of having your byline in a place where other people can see it, having an author bio that they can click and go to your website. But I was going to say one of the most successful situations like that has been writing for Search Engine Journal. So I started writing for Search Engine Journal when, it was right when I started freelancing. They advertise that they were looking for, you know, another writer or something on staff. And I was shooting above my weight and that, because I was so new and I really did not have the experience. I had the gumption. And so I wrote this test piece for them.

[00:47:14] And it was all about, is posting the same blog post on something like LinkedIn and Medium and your website, is that considered duplicate content. And I just really dug into that. I looked at other people’s experiments and then I reported it back. And, they loved the article. I think they recognized that I was still way too green to be a staff writer.

[00:47:35] But they offered me the opportunity to be a contributor on a regular basis. And, I will say Search Engine Journal does not pay. I mean, I’m sure they pay their staff writers, but they don’t pay their contributors. So it’s something that I do to this day that is not paid, but so many people get in touch that say, “Oh, hey, I saw your article on whatever. And we’re looking for, you know, this or something.” So it has absolutely like I can directly correlate certain business to, to certain articles that I’ve written for Search Engine Journal. And because it’s in this space that I want to operate in SEO and content marketing and things like that, it also lends credibility to me that helped me to get my initial clients, which then led to more and more clients.

[00:48:22] So, yeah. I mean, there are so many things in freelancing that can cause this chain reaction that leads to greater things. If you take the opportunity in front of you very seriously and sort of like, you know, use it in a way that you can show people who you are on a platform that maybe isn’t yours.

[00:48:43] Jon Penland: That feels like one of the really rare exceptions where working for exposure pays off. Right? Like, because there’s that, that old tired meme about, like asking a freelancer to work for free for exposure. And that feels like one of the few exceptions where, “Okay, at Search Engine Journal, there’s a ton of volume here. This is going to help establish me in the space.” A little bit of an exception there to the normal rule of not taking on that free work.

[00:49:10] Maddy Osman: Oh, a hundred percent. Yeah. Like don’t let that me saying that then make you go out and do free guest posts on you know, anywhere that’ll have you, you got a vet. And you’ve got to, you’ve got to realize that there is a cost associated with that time or the resources that you’re putting into that content.

[00:49:36] And I would say if there is something that you’re doing, you know, more than one post for overtime, like you have to measure that and actually justify it. And there are very few, that’s probably the only outlet I would ever do anything for free for. And if I found out that they were paying other contributors, I would stop. You know? 

[00:49:54] Jon Penland: Yeah, for sure. For sure. Yeah. Speaking of money, I noticed that you published pricing on your website, which in my experience is not super common for SEO content agencies to just go ahead and splash pricing on their website. So what, what prompted you to do that? Like what’s the sort of pros and cons of taking that approach?

[00:50:18] Maddy Osman: There’s so many pros and cons. The initial prompt I would say is it was just being that sole operator, getting on sales calls, where we were not on the same ballpark at all, not in the same ballpark at all. And being like, I can’t do sales calls all day that are not going to ever turn into anything.

[00:50:37] Like I just, I don’t have time. I don’t have the energy. I mean, sales calls, even as, I think I’m an ambivert, maybe I think I present as an extrovert, but I think I’m actually an ambivert. And, it’s like sales calls just like, take so much out of you, the prep, the anticipation, doing the call, you know, having to act on it afterward.

[00:51:00] It’s just, it’s such a, I love talking to customers, but that initial sales call is, it’s something that I don’t think anybody ever like really gets over, I mean, unless, unless you don’t have to do the work after maybe like, if you’re the type of salesperson who just gets to do sales. Right? But getting back on track here, the pricing.

[00:51:24] Jon Penland: Yeah. So the pricings on the website.

[00:51:25] Maddy Osman: I published it so that I could refer to it when people booked calls with me, so that I could say, you know, I have like a little checkmark thing that says, “I acknowledge and I’ve looked at the pricing and there’s a link to it.” So that there’s no excuse not to see it. And like, you know, we’re on the same page, like booking this call means that pricing is not an issue and we’re really just talking details or other questions that you might have at this point.

[00:51:51] So I actually don’t really do sales calls anymore, unless it’s somebody who’s just like, absolutely never heard of me and I’m pitching them. But if it’s more of an inbound lead, then they have to acknowledge the pricing before I talk to them. And, so that’s really the reason. I have had clients tell me that if I hadn’t published it, and if it wasn’t the price it was, they probably wouldn’t have been as interested in working together because it’s like a signal of the quality to some extent. You know, if I had published it and it was really low, then that would be a sign that I don’t value the output that we create.

[00:52:30] And even now I should probably raise the prices and, you know, it’s something that I think about too. But, but the way that I think about it and the way that I was describing this with another group I’m in recently, is just the idea that if I’m considering a new service or tool or something, I’m a buyer and I’m looking at my options.

[00:52:53] It’s going to really deter me if I can’t find pricing easily. And if somebody else is maybe gathering that information for their boss or, you know, something like that, there’s some sort of stat that’s like 70% of a buyer’s decision is made before they then reach out to you and want to have that sales call. And that part of that is gathering information about pricing and comparing it to your budget. So I just think that the decision, I want that decision to be made before they talk to me, right? Like I don’t want to argue semantics over pricing. I want to talk about if I’m going to be a fit for your business based on what you do and what you’re hoping to achieve. Like that’s what I want the call to be about. 

[00:53:35] Jon Penland: Yeah. And I think you really hit on a key point there that the price does to a degree signal, how much time you’re going to be able to invest in building out a piece of content for a client, right? Because if you’ve quoted, if you’ve quoted a really cutthroat rate, you’re going to have to turn that out as fast as you possibly can. Whereas if you’ve quoted a rate that allows you to take the time to do your research, to get it right, it actually allows your customer to be more demanding of you too, to hold you to a different standard than simply looking for words to fill up a page. So I think that’s actually a really great point about how publishing that out there, letting folks know, like, “I’m not, I’m not the bottom of the price chain here, right? Like I’m not your cheapest option” signals to them that  you’re going to get a different experience, a different quality product than if you went with somebody who was at the very bottom of the price list. 

[00:54:23]Yeah. So if you, if you were talking to an established freelancer, but somebody who has not ventured beyond that individual freelance place yet could be, could be a writer or a completely different field, so the field doesn’t really so much matter, but they’re considering transitioning as you have from being just an individual freelancer to actually having an agency. What sort of advice would you give them? How do they get started? 

[00:55:04] Maddy Osman: The first thing is to find a mentor who’s been there, somebody who can help you with all the random questions that you’re going to have. I think that also things like industry Slack groups can help to fill any holes you might have with people in your network or people in your extended network. And I think that a lot of people are willing to mentor.

[00:55:32] I think that you have to also make it worth their time by coming to a mentor situation with good questions. And I think that the thing about mentors is like, you could never like pay them what their advice is worth to you. So you have to find another way to sort of give back to them. And I think like one of the things that I recommend to people is like, “Does your mentor have like a favorite charity or organization or cause, and maybe could you like volunteer, you know, some of your time to just show your appreciation for what they’ve done.” So, you know, mentorship, it’s transactional, but not in terms of money. It’s in terms of time. It’s terms of, in terms of care that you put into the situation. I think that in transitioning to an agency model like mine, you should be focusing now on documenting all your processes.

[00:56:20] I use this Google Chrome extension called Scribe and it’s awesome. You just hit a button and it records every activity on your screen and you can add written direction to it and also take screenshots. So that’s the easiest way to do it, but it could also be doing things like just videoing yourself doing something on your screen. It’s things like creating a style guide or creating a blog post template, but just, but yeah, anything that you can explain that you would want somebody else to do for you just getting ahead of that right now. It’s things like making sure that you’re on the right track with branding. Does that need to change?

[00:57:06] If, if your business changes, a lot of freelancers use their names as their business. And so you might have to think about like, “Well, what does this look like if I have other people involved?” And so for me, it involved redesigning my website, making it clear that it’s not just me. And it’s only about content marketing now. It’s not about website design or social media or whatever. And then finally, it’s, I think, I mean, there’s a lot of things, right? But, I think it’s also just hiring that first person as a contractor so that it’s safe to experiment and scale up and down and learn to delegate because that’s going to be a skill that will serve you well, as you keep following that path. It’s, it’s going to become more and more critical as your time dwindles, your energy dwindles so that you can only focus on, you know, the most important things.

[00:58:00] I think that those are, those are probably the best pieces of advice I could give to get started. 

[00:58:07] Jon Penland: Yeah. I love that idea of, you know, documenting your processes. ‘Cause the other, the thing that strikes me about the process of documenting how things work, how you do things, is it forces you a lot of times to stop and think about what you’re doing for the first time? And the other thing that it can force you to do is at least for me, when I stop and document something that I’ve done a hundred times, a lot of times, there’s this little piece of it that I knew could be optimized or automated or done better. 

[00:58:42] And I’ve just continued to allow that, to kind of hang out in my process. And when I stop and document it and get ready to share it, somebody else, I’m like, “Okay, I better fix this because it’s going to be embarrassing to put out there that I’m still doing this really inefficient, imperfect thing that I’ve known for six months, I should have changed.”

[00:58:59] So I actually think that process of sitting down and documenting helps you understand your business better and can help you find and fix inefficiencies and little problems, things that can be better. That’s cool. Okay. So as we, yeah, as we wrap this conversation to a close, I have two parting questions for you.

[00:59:18] So the first is, what is one resource you would recommend to our listeners that could be a blog or book, an event, newsletter, anything really? What’s one thing our listeners should definitely check out?

[00:59:30] Maddy Osman: That’s a great question. I’m going to recommend my favorite book that many of you’ve probably already read, but I would encourage a reread, which is ‘How to Win Friends and Influence People’ by Dale Carnegie. It is applicable to any job you can ever have, and it’s all about good communication and communicating in a way that benefits you.

[00:59:55] But it doesn’t like throw under, other people under the bus either. So general, but I think it could help anything. 

[01:00:04] Jon Penland: Yeah, absolutely. I’ve read that book, probably two or three times. And, and likewise, I think you’re absolutely right on there saying that the advice in that book is applicable and useful no matter what you were doing in life. So that’s awesome. Last parting question. Where can our listeners go to connect with you or to learn more about The Blogsmith?

[01:00:27] Maddy Osman: Sure. I’m going to add one more book too. So if you want to be kind of where I, where I’m heading, where I’m going, where I sort of am, another great book is ‘Scale’. And it’s about all the things that we’ve talked about today. In terms of where you can find me, I’m probably most active on Twitter @MaddyOsman.

[01:00:47] You can also catch up with what The Blogsmith’s doing at theblogsmith.com. And if you have any questions for me, I’m always willing to help, you know, just Tweet me or DM me and yeah, let me, let me see if I can help you solve your problems. 

[01:01:07] Jon Penland: That’s awesome. So @MaddyOsman on Twitter and theblogsmith.com. So, all right. Well, Maddy, thank you so much for being on Reverse Engineered.

[01:01:12] Maddy Osman: Absolutely. Thanks so much for having me. 

[01:01:17] Jon Penland: Yeah, it’s been great to have you on the show and thank you to our listeners. That’s all for today’s podcast. You can access the episode show notes at kinsta.com/podcast. That’s K I N S T A. com/podcast. If you enjoyed this episode, don’t forget to subscribe to Reverse Engineered and leave us a review on Apple Podcasts or the platform you’re listening on right now. See you next time.