Maddy Osman, The Blogsmith
Maddy Osman draws on past experiences as she manages her SEO content agency, The Blogsmith. Growing up with an entrepreneur dad, she understands that owning a business requires intentional boundaries. Her previous job in the Groupon sales department taught her that rejection isn’t personal. Freelance writing for a Chicago lifestyle blog sharpened her SEO skills. Maddy uses these lessons learned to improve — both herself and her business.
Episode 41 – Maddy Osman, The Blogsmith
[00:00:54] Sanjay Parekh: Maddy Osman started The Blogsmith, an SEO content agency for B2B tech companies, in 2015. But before that, Maddy had several jobs in the Chicago and Denver area, where she gained skills in Wordpress website design, social media management, and content creation. Here today to share more about her business, how she builds efficient processes, and her book… is Maddy Osman. Maddy, welcome to the show.
[00:01:17] Maddy Osman: Thank you so much for having me.
[00:01:20] Sanjay Parekh: So, I'm excited, interested to talk to you, because I'm hoping that at the end of this we can, pull out some tips and tricks for our listeners about how to do SEO better. But before we get there, give us a little bit about your background and kind of what got you to the point that you're at now.
[00:01:36] Maddy Osman: Totally. So, from Chicago suburbs. Originally live in Denver. Now I've been to Iowa, studied abroad in Spain for a little bit. Just never sit still. But I taught myself web design at age 11. That's what led me to my college job, where I got to really learn a lot more about it from professional. I worked in a student run marketing and design agency, and that's where I also discovered a love for content. And so really from. I graduated, I did a couple sales jobs, I did a couple, I did freelancing on the side of all my full-time jobs. And basically I just decided that I was going to take those freelance jobs, make those into a full-time job for myself. And then that's what eventually led to me starting my agency, taking that freelance work full-time.
[00:02:30] Sanjay Parekh: So, was this the first time you've done something entrepreneurial like this? Did you, like you started learning web design when you were 11. Were you like doing it for other people then and, like on the side? What was going on?
[00:02:42] Maddy Osman: Sure. Yeah. So, I would say that the whole idea of entrepreneurialism really originates with my dad. There's maybe like two really impactful figures. It was him, and then it was my boss at that college job because he's the one who gave me my first freelance gig, or kind of connected me to it and made me think that it was possible to do my own job outside of, you know, the structure of a company that's, you know, making all the rules and all that good stuff. But my dad, he started a company called Independent Systems many years ago, and then, has since sold it to a company called Avalara to fund his retirement. And I used to work with my dad. I would go in and clean his office to, to pay for my horseback riding lessons, and then I would go in just, you know, to either just like help or just like make a little bit spare cash to spend, answering phones, doing data entries. So, I mean, that was really like my first brush with entrepreneurialism and being able to see my dad and, you know, like, here's his office, here's his staff, here's the product that they're selling. I also saw the flip side of that, which was, you know, he would always be working on vacations. And you know, he had all this technology that I was really interested in in terms of like, you know, super old laptops and like super old hotspots. And I just thought that was so cool. And I know he thought, you know, it's just like a thorn in my side to have to do all this work, you know, outside of typical hours. But there's something about the whole package, you know, that was of interest to.
[00:04:26] Sanjay Parekh: Yeah, it's interesting you touch on that and that's like the blessing and the curse of being a founder, right? Is that you're never on vacation, but you can also take vacation almost anytime that you want. Because you're the boss. And you can figure it out. And if you can balance all of those things, it can work for you. Yeah. So, let's talk a little bit then about, how you started the business itself. So, you said you took all these kinds of freelance things, but what was that initial spark of why you wanted it? Like, you knew that you could do it and you'd seen, you know, your dad that had done it. Why did you want to do it?
[00:05:11] Maddy Osman: I think for me, I always saw myself as being traditionally employed, at least in terms of like my main job. I've always been a person who likes to explore my hobbies and my interests. Like web design for me for a long time was just that it was a hobby. I didn't see it as like a means to an end in terms of a job or employment or anything like that. But for me, at least when I graduated, doing these projects to the side of my full-time job was really like it was me. I'll back up to say that when I got my sales job at Groupon, to me that was a foot in the door. I didn't want to do sales, but I learned a ton doing sales, so I don't regret that I spent as much time as I did in sales in general. But I never saw myself as a salesperson or that would be my identity or my full-time job forever.
[00:06:06] Maddy Osman: It was, I really wanted a marketing job. And so, by doing these projects to the side of the sales job and then the one that came after it, which was also a sales job, for me, it was a way to test the waters, I guess, and to build skills that I wasn't being paid necessarily to spend my time on at work. So, I kind of had to bring it outside of work. And I guess like another related thing that was really foundational to what I do now is not a job, but a project. I built a hobby blog. It was about living in Chicago, you know, being a young professional on a budget. How can I enjoy the city to the fullest? And that's when I tried a lot of different marketing tactics to see how I could get traffic to the blog. And SEO was one of them that I knew nothing about, but that I got the chance to really experiment with and then see what could happen when it works well, and so, you know, it wasn't just the jobs, it was all the projects to the side of my full-time job that led me to where I am today.
[00:07:09] Sanjay Parekh: Yeah. So, I’ve got to imagine that the sales job, now like in retrospect has served you well because that's like the number one job as a founder, as an entrepreneur. Are there any lessons that you had, I can't even imagine what it's like to be a salesperson for group on, like, what, are there any lessons that you, that still have stuck with you since then?
[00:07:32] Maddy Osman: Yeah, I think one of the big ones is just, rejection isn't personal, right? Like it helps to get that out of my system for somebody else's company before trying to do sales for mine. That's a huge one. And then just, I think the lesson in general is if you have the opportunity before you build a business where you're going to have to be constantly selling your products and services, even just you as the person to execute on them. Get a sales job. I say it to any like freelancer that comes up to me asking for help. I say, if possible, do a couple of months. It's probably going to suck, but you're going to learn so much, and you can take that into any job you have because sales is so fundamental to a lot of the things we do. Winning budget for a project. I mean, I'm sure you're familiar with Daniel Pink. He's this author who writes all these super awesome books. One of the ones that has stuck with me is to sell as human because it really is.
[00:08:38] Sanjay Parekh: Yeah, I’ve got to say, it's unfortunate that, door to door sales is not a thing anymore because when I was growing up.
[00:08:45] Maddy Osman: Is it?
[00:08:45] Sanjay Parekh: I don't know, I've not had anybody come to my door in a very long time. This is not an invitation, by the way, people. But I did door-to-door sales of custom imprinted holiday cards when I was a kid. And that, it teaches you a lot when you're ringing somebody's doorbell. They're not expecting you. And you have to sell them and close a deal right there on their porch. Yeah. I think that sets you up for the ability to accept rejection much later. Yes. let's talk a little bit about stress because this whole thing can be very stressful. Oh, yes. You know, there's deals that you're hoping to get, they don't happen, or there's a deadline and you know, you're behind or whatever it is. How do you manage and deal with the stress of being a founder?
[00:09:36] Maddy Osman: Yeah, it's hard and I think it's a daily battle. Just as soon as I feel like I have it conquered, you know, something comes out of left field. So, yeah, I mean, so part of it is just being realistic and like being kind to yourself, you know, just stuff happens. I'm a very process-oriented person, so I try to over plan literally everything in my life. But, you know, I can't plan for every single potential thing that could happen because we as humans, we're unpredictable. That's just like, that's just facts. So, I think what's important is to create routines in your life and stick to them, like having time for exercise or just getting out in the sun, you know, with your dog on a walk for 30 minutes a day, or going to sleep at, you know, a semi-regular time every night. I don't know that the specific routines are important, but just that you figure out what's important to you. For me it might be things like, I like to do a little bit of art, not for anyone but myself, just the act of creating and sitting down and making time for myself. Or another thing is like, I like to try to get in at least like a half hour of reading a book a day. And so, it's like no matter how stressed I am, whatever those routines are, as long as I still prioritize those, I feel a lot better at the end of the day than the days when I let the stress completely control me.
[00:11:09] Sanjay Parekh: Yeah. Let's, talking about that, let's talk about setting boundaries. You mentioned like your dad and going on vacation, and he'd still be working and all that. Has that impacted you and how do you think about setting those boundaries and then, you know, family time or friend time or vacation time? Like how do you separate these things?
[00:11:29] Maddy Osman: Totally. Yeah. No, my dad for all the things he did well, there were things that like I definitely wanted to improve upon his process, and I will say, he was good at enjoying the vacation. Like he would try to get it all done in the morning, you know, he would wake up early, which is like not my idea of a good vacation, but to each their own. My dad in his retirement would also wake up at like 5:00 or 6:00 AM to feed the dog. So, like, that's totally just him. But, yeah, in terms of creating boundaries, I think for me it's like when my business was more side hustle than full-time. I was grinding and I think it was easy to do because I didn't have that many responsibilities. I didn't have a kid, I was living in like a studio apartment, so not like a whole lot of expenses, not a lot of responsibilities. And so, it was okay maybe to not have those boundaries back when I first started because I just needed to put in the work. And I think there is like a time and a place in business where it's. You just need to grind. I feel the same way about when I wrote my book. It was a lot of nights and weekends and things like that because I just needed to, I just needed to get through it, you know? And now I can, like, now I can take those back and I do, like most days I don't work weekends anymore. I still work nights sometimes. But the thing for me is that I don't get a lot done during the day. Like I take calls and things like that. I just work better at night when, you know, nobody's online. Nobody's expecting an answer from me, and so I take, you know, I do my exercise during the day, or I'll run an errand, or I'll take a nap or whatever. Like, it's fine because I'll work on it later. But I would say weekends have been a good boundary that I've added in my life where it's like, if there's a project that I'm like super excited about, it doesn't really feel like work, but if it's like the weekly checklist of things that I have to do, like that's not a good weekend project. So that's, that's some of it. I think, you know, the other thing is like what everybody says, which is like, don't set a precedent with clients that you're going to be answering immediately when they send you an email. You know, it's okay if you want to answer it right then and there but schedule it for business hours to send and set that precedent for them, for you. I think for me that's most of what it is. I mean, the last thing that I'll say on that is just like trying to set expectations really early in that relationship. We have a couple of like documents, like a, like an intro packet we'll send out that's like, here's our hours, here's what you can expect for communications and getting a response.
[00:14:11] Maddy Osman: You know, here's, what our project management workflow looks like. So, whatever you can do to kind of get ahead. Whatever problems you're noticing now, I guess with clients, start to create a system to handle those so that you can always refer back and say, hey, wait a second. Like, this is what, this is how we started the relationship. Your expectation is not in line with what we've already agreed to if it becomes a problem.
[00:14:37] Sanjay Parekh: Yeah. Yeah. Let's, switch gears a little bit and talk about, an area that I think is an issue for a lot of people that are wanting to be entrepreneurs or wanting to start a side hustle, is being fearful of what might happen. What were you fearful of when you were embarking on all of this and are there fears that you still have now and kind of what are they?
[00:15:01] Maddy Osman: Yeah, I think the biggest fear is failure, right? I mean, and I think that,
[00:15:07] Sanjay Parekh: And what are you fearful of about failure? Right? Like, what do you think is going to happen if you?
[00:15:13] Maddy Osman: It's a scary situation to play out, I think, for anybody. And it's like, for me, a big thing that I worry about is reputation, you know? And so, I could be doing everything right, but maybe somebody that I've hired will execute differently than what I would do, regardless of all the systems and processes and whatever that I've put into place.
[00:15:37] Maddy Osman: So, so part of it is just reputation and the impact of failure on that and how does that affect my future prospects? You know, like, will people still want to work with me if some failure happens, you know? Will I have to get a full-time job again? That's the biggest fear. If I can't hack it on my own will, I have to, for lack of better phrasing, be like under somebody else's control in my work life. I think fear of failure is like being out of control. Of my own life and my own future, and I'm so unemployable at this point. I don't know if that should go in the final or not, but I just like, I'm so used to doing things my way now and being on my schedule and, you know, like building things the way I want to build them in my timeline with my processes. So, I think the biggest fear for me is losing that.
[00:16:40] Sanjay Parekh: Yeah. So, do you think, so is that what keeps you going then and overrides the fear? Like how do you manage the fear?
[00:16:49] Maddy Osman: Yeah. It's like, how do you balance like the fear versus like the want or something?
[00:16:55] Sanjay Parekh: Right? Do you think about that? Or do you just barrel through it and you're like, I'm not even going to think about it?
[00:17:03] Maddy Osman: I think there are some days that it becomes debilitating and maybe not the fear so much, it's just like something came out of left field that I didn't anticipate, you know, that my processes like are not built to handle in the current state of affairs and I think when that happens, I try to get back to like routines and stuff. If I'm sitting at my computer and I'm just like staring at the screen, I need to go outside. You know, I need to like get some fresh air. I need to like re-get my perspective back. I just need to get away from the problem for a short amount of time. And I felt the same way when I worked at Groupon, and I was dealing with rejection over and over and over again. It's like, take a walk, then let's attack this again. So, I think. My motivation or my driving force is to be able to like reset, to be able to like to identify the issue and reset it. I don't know if that answers the question.
[00:17:58] Sanjay Parekh: No, no, I think it's great because I think that is one of the challenges with a lot of people because they're worried about, having to deal with things that they don't know how to deal with. And that’s, I think that just defines entrepreneurship, right?
[00:18:11] Maddy Osman: Like yeah, it's basically what you're doing as a job.
[00:18:14] Sanjay Parekh: You're just having to deal with things that you've never dealt with before and you just kind of have to figure it out, right? And I think a lot of us figure out as we go, that. Nothing is that like killer really at the end of it, right? Like if you do it wrong, it's not a mortal flaw. Like you're not going to die.
[00:18:33] Maddy Osman: Totally. And even if client's mad about something, it's like they might be blowing it, or you might be taking it worse than it's even meant to be coming across. And so, I mean, and I think sometimes if you're having like a really terrible day, then you just call it and you say, I'm going to work twice as hard tomorrow and I'm just going to like take a mental health break. So, I think that's the thing too, is to just like, don't keep pushing when it's not going to work. Take care of yourself and then come back stronger than ever ready to like face this.
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[00:19:28] Sanjay Parekh: Let's talk about your processes you've kind of iterated on this, you've learned stuff kind of as you're building this. Like how have you figured out how to build efficient processes? How have you designed it? I mean like, do you start somewhere or you know, like, how do you work yourself through that process?
[00:19:52] Maddy Osman: Totally, yeah. I guess I'll start by saying I wish this was like a class in business school, business process improvement or management. Maybe it's like an MBA class, but it definitely wasn't, you know, general business school gen eds. Yeah, so part of it I think is finding like the resources to even think about that for somebody who. Put themselves directly in that position in the past. And so, one thing I did was just like, look up like different, like textbooks, you know, and what is process, you know, creation and stuff like that. But I would say that really came from zeroing in on a tool that I wanted to be, like the central point of my business operations, a process management tool versus a project management tool.
[00:20:43] Maddy Osman: I had, you know, played around with a bunch of different things and kind of transitioning from me as a freelance writer, to me, having a team that I needed to collaborate with is just like a whole different beast. You know, like I used Todoist in my daily life for just about everything, and I did use that at the beginning, and it was nice light wave. It did the job for a good chunk of time, but as the operation grew more sophisticated, we really needed something that could be customized. And so, what I did was I built out our process on a tool called Process Street. It's like a no-code tool that you can really get granular, you're not boxed in. It has a lot of integrations to other tools. And so now from here on out, all my processes are built on process.
[00:21:34] Sanjay Parekh: Okay. That's a great tip. Let's talk about the process that you had though, in writing your first book here. You've never written a book before. How did you figure that out? Like, how did you do that process of figuring out how, like, I need to write it, I need to edit it? All the things that you need to do and when you're starting, like you don't know all the things you need to do and as you uncover them, so how did you figure out that process and how did that work for you?
[00:22:03] Maddy Osman: Totally. Yeah. So, it definitely helped that I had helped other authors launch their books and helped with some of the marketing that happened in like the months leading up. And then day of, a couple authors who had also done Amazon launches. So, that's part of it. So, I kind of reverse engineered their processes by having been a part of these launch teams, I had basically helped them with their organic content. And then I worked with a friend who did a lot of paid things like on Amazon and otherwise on Facebook, etcetera, paid ads. And so that really helped. And then as far as like the writing of it really grew from my own need. And so, we have at The Blog Smith, the style guide that's currently about 35 pages long. It's a little bit intense, but it goes through like everything you need to know to write for The Blog Smith, how we do headings, how we do visuals, how we do links, the rules, how we choose words, you know, for clients in our industry, how we come across as expert without coming across too jargony. And so, the book I decided that I wanted to add context to the style guide, add examples, add explanations for the stated rules. Show, you know, you should do this versus don't do this. Like actual things we've found in writing and improved. And so yeah, the book really started from my own need, and it started from having this background of working with these other authors and seeing a little bit of their ideation process, but definitely their publishing process and their marketing process. And yeah, I just kind of like split it up into different steps. Another tool that came in handy for both that project and working in my agency in general is Airtable, because you can just input data, you can organize it a lot of different ways, and so planning the launch of my book and the marketing that had to happen and even like the podcasts that I wanted to be on and things like that, it was all kind of contained with an air table with different dates and different tabs of different types of media I was going after. And kind of a fun thing is that both of these no-code tools across the street and Airtable, I use them in my personal life too. Like this past weekend, this is super nerdy, but I built out, if you've ever seen, oh God, I'm going to forget the name. Not Clueless. Yes. Clueless. Where she has that, wardrobe, you know, where she can kind of see like everything that's in it. Yeah. So, I built my own, like clueless. Wardrobe interface and I haven't added everything to it. I made a little photo studio in my house so I can take a picture of all my wardrobe items, but, so I'm building out like an, like a database where I could see, okay, what does this shirt look like with these pants or whatever, and so I just, I like, I love these tools because there's so many different ways you could use them, personal or professional.
[00:25:08] Sanjay Parekh: Yeah, or you could just be like me and just grab two random, items of clothing and hope they go together. And if they don't, you know that somebody in the house is going to tell you that. My process is relying on other people telling them I'm goofing up. It's not a great process, but it is a process. For our listeners that might be thinking about taking the leap like you did, of launching a side hustle or taking their side hustle into a full-time business, what advice would you have for them?
[00:25:47] Maddy Osman: Sure. I'll start by saying like, the straw that broke the camel's back, or whatever you want to call it for me, it was, I had been working with this freelance client to the side of my full-time job, and he was like, hey, I'm looking for kind of like a virtual assistant content manager who would help me execute on social and some blog posts for like several of my clients. and he, was like, you know, I know you have a full-time job. Like what would it take for you to go freelance full-time and help me, this wouldn't be your full thing, like you'd still want to get other clients, but what would you need to feel like secure in making that leap? And so basically, you know, we came up with a number that made sense for the work, and it was enough to like cover my basic bills. So, for me that's what it took was a big enough client. that I knew I still had to get other clients and I was ready for the hustle, and I was, you know, fresh off these sales jobs. I had a couple of other freelance clients, so I didn't feel overwhelmed in that. What I would say to others who are contemplating this is like, yeah, definitely if you have a big client like that, that's great. It's probably better to build up several clients and sort of start small with them and find a place where you can scale up or, you know, you've, one thing that's really important, I think, is to validate your idea or your service before you quit your full-time job. So, if you can validate that, and then you have either sort of like a waiting list or agreements with, say for example you have freelance clients or something like that, that you could scale up at a certain date. Like that would be the ideal situation is that you've built something. You have business coming in, people are happy with it. You know, there's more demand than your current supply. That's the ideal situation. The only other thing that I would say for sure is to build up like an emergency fund and be ready, because cash flow is going to be irregular for the first several months, if not for like your whole life as a freelancer. So, you want to be a little bit ahead, you're probably going to have to. Like what I did when I went full-time freelance, you know, tighten the belt on. Maybe you don't get Netflix for a year. You know, like it's sad, but like, you have to kind of, you have to kind of let go of some of the fun stuff while you do the early hustle and then you build it back in eventually.
[00:28:16] Sanjay Parekh: Yeah, okay. So, last question for you, for our listeners. What are those couple of tips in terms of SEO or content writing or whatever that you've seen people do poorly, that you can quickly give our listeners some tips and tricks on how to do better with what they do?
[00:28:37] Maddy Osman: Hmm. Mistakes. I think, the biggest mistake is to not consider your audience, right? To write something because you think it sounds cool or because somebody else told you, you should do it, but you never actually never think of it from the perspective of the person that you know you're trying to get to buy from you, for example, or who is otherwise interacting with your content to learn something. And so, the reader experience, like for us at The Blog Smith, that is the most important thing. That's why our style guide is so long. That's why I wrote this book. And I think it's neglected. And one thing that's really, I think, interesting about my background as a website designer is like, it really made me think a lot about the user experience. And so, it came from the perspective of design, but now it totally applies to everything I do with the writing of content and the visuals and just the full thing. This is, I don't know if this is something that people do wrong, although probably a lot of people just don't do this at all. But it's also like once you know what keyword you want to go after or when you're in the discovery process, type it into Google and see what actually comes up and sort of analyze the results. Like are you proposing something that's like what's already out there? What are you going do to make it different? Or are you trying to like also fit like a round peg in the square hole because what you maybe already wrote or are in the process of writing doesn't really match the answers that Google is putting out for that keyword. I'll give you an example, a personal one. So, when I was learning about SEO with this lifestyle blog, I wrote this piece called Free Lollapalooza Tickets. Because Chicago just has, you know, the funniest music festivals and that's one of my favorites. And I used to volunteer at Lollapalooza and that's how I got in for free. I would put in a couple hours, filling people's water bottles, and then I got to enjoy the rest of the day. And so. I wrote a blog about it with kind of a click baby title. It wasn't untrue. Because you can still get a free Lollapalooza ticket. You just have to work. That's the other end of it anyway, to me, I think about that example. When I think about fitting a round peg in a square hole or whatever, because it's like I was kind of forcing an idea that wasn't compatible with the keyword. Because if I typed in free Lollapalooza tickets, probably like the intent of that search is people looking for giveaways or something.
[00:31:20] Sanjay Parekh: Right, right.
[00:31:22] Maddy Osman: Like it maybe still works, but it's also like I'm being a little mischievous about it, you know? And so, yeah, that's all I'm saying is like, are you being mischievous about it or like, does it actually match like the real intent?
[00:31:35] Sanjay Parekh: Right. And if you are, then is it actually serving your goal in terms of what we were trying to accomplish?
[00:31:40] Maddy Osman: Exactly.
[00:31:41] Sanjay Parekh: Otherwise, you're just wasting your time?
[00:31:43] Maddy Osman: And that's what it comes down to, right? Because if people have an idea of what they're going to get and they click on it and then it's nothing like their idea, then they're just going to leave. Right?
[00:31:53] Sanjay Parekh: Right. And that was a waste and click for you anyways at that point, so. That is actually a fascinating idea and something for us to think about and I'm glad we're ending on that. Maddy, where can our listeners find and connect with you?
[00:32:07] Maddy Osman: Sure. Depending on the state of Twitter in a couple weeks, you could find me there @MaddyOsman. And then you could check out our work on theblogsmith.com and if you like what I'm saying about the reader experience, then I would encourage you to check out my book, which is Writing for Humans and Robots, the New Rules of Content Style, and get it on Kindle or Print on Amazon.
[00:32:34] Sanjay Parekh: Awesome. Thanks for being on the show.
[00:32:37] Maddy Osman: Thank you so much for having me.
[00:32:43] Sanjay Parekh: Thank you for listening to this week's episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. And if you have a story you want to hear on this podcast, please visit www.hiscox.com/shareyourstory. I'm your host Sanjay Parekh. You can find me on Twitter @sanjay or on my website at www.sanjayparekh.com