Tech Freelance Work With Maddy Osman
Maddy Osman discovered her deep love for all things digital back when she was doing freelance work in tech. Finding her purpose in this space, she strived to grow her skills and build her network, eventually starting her own B2B content SEO agency. In this episode, she joins Asmita Puri to share the genesis story of The Blogsmith, as well as her strategies for maintaining a collaborative team and setting the right business standards. Maddy also discusses how she mastered the art of work delegation that allowed her to step away from the daily operations that consume a huge chunk of her time.
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Tech Freelance Work With Maddy Osman
In this episode, I have the pleasure of hosting Maddy Osman, the visionary Founder of Blogsmith. She will take us on an exciting journey from her childhood days of tinkering with HTML to building her own content and SEO agency. Maddy has some incredible insights on how being curious played a massive role in her tech evolution and how taking risks led to unprecedented growth. She talks about the importance of finding the right balance between being hands-on with the latest tech and being a company leader. I think Maddy's narrative is a testament to the power of curiosity, calculated risks, and the art of delegation in building a thriving business.
She talks about the importance of setting boundaries and taking strategic breaks to maintain a sustainable work-life balance. If you are an entrepreneur, you won't want to miss out on Maddy's story, which is a vivid illustration of the constant pursuit of learning and growth that feels like success. As always, I recommend grabbing your favorite beverage and a snack for this inspiring conversation as we uncover Maddy's invaluable lessons, strategies, and wisdom. With that, here's the episode.
Story And Career Path
Maddy, welcome to the show. It is good to have you here. Before we get started, why don't you introduce yourself to the reader?
Thank you so much for having me. I love the idea behind this show. Some of the episodes that have come out far. I’m glad to join the ranks. My background is I own a B2B content SEO agency called The Blogsmith, but my journey started with website design, which I know we're going to talk about. I've written a book called Writing For Humans And Robots: The New Rules Of Content Style that is based on our approach at my agency but harkens back to those early days of getting started in the tech world.
I'm very intrigued by that book. I can't wait to learn more about it. Let's dig deeper into your journey. You mentioned it started with playing with HTML or building websites. Let's start there. How did you go from playing with HTML as a child and then running your own agency?
I'll try to keep this as concise as possible, but essentially my dad was an entrepreneur. That's where this idea of, “You could be whatever you want to be when you grow up,” came from. In some ways, it supported my early tinkering with HTML and CSS and learning things like how to do basic graphic design with Photoshop. I would go to my dad's office after school. Some of his employees there were resources for those things. I could ask as I was playing around and have a second opinion if there was something that I was stuck on. You probably remember Neopets in MySpace and you could customize your profiles there. That's probably where this desire to learn it initially came from. I am making my own websites for fun.
I went to college and was looking for a job there. There was an opportunity to work at the student life marketing and design department where I had the opportunity to work with different student organizations and other university arms, like the bookstore and things like that. Through that job, I was able to learn a lot more about website design under the mentorship of my boss. I also learned about how agencies work.
I learned in that job that I liked marketing. I knew that I wanted to be a Business major, but it wasn't until that job that I knew I wanted to be a Marketing major. I did that job pretty much the whole time I was in college. I had some other jobs to the side of that, including some freelance jobs, but they all related back to that. At that job, I was also given the opportunity to create content for the Student Life blog and social media channels. That sparked this early interest for me in creating content.
You were saying you were creating content for the school Student Life.
I had the opportunity to create content for the Student Life blog and social media properties, but it took me a while after that to realize that that was going to be my focus, it was an important point in time for figuring out where I wanted to go with my career. I graduated. I got a full-time job in sales, which at the time was not the end goal. I always thought that that was going to be like a foot-in-the-door type of thing, but it didn't result in that fast enough for my liking. I experimented with different digital marketing techniques to the side of my sales job. I started a lifestyle blog. I wanted to see, “How do I get people to visit it? Whatever I figure out if that works, is that something that I want to make my job?”
I wasn't even thinking of freelancing it, but maybe get an in-house role somewhere. I did some freelance work on the side. One of my clients said he had enough work to cover my baseline, rent, and that sort of thing. I want to look for other clients too. It was enough to be able to take that leap in order to quit my full-time job. I wasn't even necessarily thinking that I wanted to do it full-time, but it was this specific client's offer that made it a real possibility for me. The rest is history.
I made that my full-time job. I took on more clients. I was doing a lot of different things in the freelance world. I was doing website design, content, both blogs and social media content then eventually a couple of years later I think I decided that I couldn't be good at all those things or I couldn't be great at all those things. I wanted to pick one and I wanted that to be my focus. The focus was long-form content creation. After deciding that was my focus, that's when I also decided that I wanted to grow to an agency model knowing that my own inputs were limited and any creative work naturally has some burnout points. I didn't want to reach that.
My first question is, what was your first website?
I used GeoCities and I'm trying to think of the first thing that I ever created. I had a bunch of goofy stuff that I did. One thing that I remember doing, in particular, was I made a fake band website to troll one of my friends. It was a slight misspelling of a popular band. I had way too much free time on my hands. I took a picture of the band. I photoshopped in a picture of Michael Jackson or something. I want to see if she would accept this as the band's website that it sounded like, or if she would notice the slight misspelling and the Photoshop. I did stuff to suit my own whims.
Jumping Into Freelancing
To play around with things. I'm also curious, I think starting freelance work, I would imagine, or maybe this is my way of thinking because for me working for a company comes with a certain level of stability and as an immigrant, it also comes with a visa. I'm wondering what mindset or where the courage in some ways to go and start working freelance after, 1 or 1.5-year out of school. I think that takes a certain level of courage and your ability to take risks. All of that is involved here. I'm curious if you can touch on that piece a little bit. I don't think I formed a question essentially, but I'm like, “How did you do that?”
For me, it's that unique situation of my dad being an entrepreneur. He modeled the possibility for me. The other notable thing that happened in college was my boss at that foundational job where I was able to expand my web design experience and learn about different aspects of marketing. He gave me an opportunity that he couldn't take on which was a freelance project. That was the first freelance project that I ever took on. It flipped a switch in my brain, like the idea that I could do that, that I didn't have to do a W2 job or something like that. I didn't have to work for an organization, but I could create my own opportunities, set my own rules, and handle it the way that I thought it should be handled.
One thing I will say is that if I hadn't had that job and if I hadn't had my next job, my full-time job after graduating, sales and learning from systems at both of those jobs and established ways of doing things, I don't think I would've been as successful freelancing. I do think that that's an important thing. If you want to freelance, I don't know if like school's the answer necessarily. That would to me be a mechanism for networking and trying out different opportunities and things like that. School teaches you how to learn and it's not always much about the specific information, but it teaches you how to do some important things.
It depends on the industry. What I'm trying to say in a roundabout way is you have a lot of learning to do before you're going to be successful on your own. At a minimum, it means being employed by someone else first and learning from what works for them or what doesn't work for them. That's part of what gave me the courage. It was not only having almost like these safe tests of being able to do freelance but having a job but also taking the time to learn and not thinking that I knew everything. That's the thing. I still try to embody that perspective. I've learned a lot. I'm an expert on certain things, but there's a lot that I dunno and I defer to people that are smarter than me in those areas.
You have a lot of learning to do before you become successful.
Landing Into Agency
That was the third thing that stood out to me. The first one I was curious about was the website. Secondly, the courage aspect. Third, I was inspired by the confidence that you showed in saying that I don't know everything and instead of trying to do it all, I am going to do the agency model and try to bring in people who know what they're doing while I focus on what I'm good at. From the agency aspect of it, did you always know that that's what you were going to do or do you think your goal more every year or every other day?
It's more of the latter for sure. The agency thing was maybe a surprise to me like I think the freelancing was a surprise. To some extent I'm a go-with-the-flow person, like testing things, seeing what works, seeing what I like seeing, and where my energy calls me. That's how I landed on the agency thing. The other piece of that was that I've always been interested in scaling outputs, especially as a writer figuring out, first of all, it started with working with virtual assistants. How can I break up this process so that other people can help me and it's not 100% all on me all the time? I started with virtual assistants who helped me with research for the pieces that I was working on, gathering statistics, helping me to do some topic ideation, and things like that.
After I got used to that, the next step was hiring writers that I could work with who would represent me. I went from being a collaborator with the virtual assistants to being the editor for these writers and still doing some of my own writing At that point, I realized I don't want to be an editor. That's not what I got into this business to do. It's important that anything that I put out there that has my name on it is representative of me and that is high content quality or high quality content. This is not the role that I want to play in my business it was at that point that I realized I needed to create systems for that and then take on the next role.
In my case, it was hiring an editor and working with her to create the Blogsmith style guide. For those who are outside the content world or close to it, it's based on the AP style guide, which is like what news journalists use. The idea is that you're standardizing your approach to writing, how we write headings, how we use formatting, important considerations for word choice, and some of our processes for using keywords since SEO is an aspect of what we do for clients. By doing that, I was able to then hire more editors, more writers and know that my approach was the one that was going to be standardized and used with all clients so that even if I didn't personally write or edit a piece, it still represented my approach to creating content.
That was the big thing. Everything else from there was a matter of taking a deep dive into the SEOs on our team and keyword research processes. It's, “How would I approach this?” I create a standard process and then I delegate it and I train and then they learn how to train other people on how to do it or how to make it better. It's important I think to hire people who are not just order takers, but people that you can truly collaborate with who bring their own perspective to it I think. That's been the reason why this agency model is working. That's like the progression generally speaking.
Freelance Work: Hire people who are not order takers but those who has their own perspectives to offer and can collaborate with you.
Stepping Away And Taking A Break
I want to talk about the break or stepping away from your agency because that was another part of our call that stood out to me. Pivoting a little because we've been talking about your goals, but now we're talking about stepping away from what you have been able to create. During our intro call, you mentioned that you took a break for three months and there were no significant fires. How do you get to a point where you can do that? Speak to the processes. You touched on that a little bit, but the processes that you set up allow you to step away.
It's something that I've been building towards for years not intentionally, but it has culminated in a way that has worked out well for the timing of having a baby and needing to step back. Essentially, I mean it's what I talked about in terms of things like becoming good at delegation. I’m trying to flesh out every process that makes up this business, even the ones that are not as fun for me, like for example, standard approaches to bookkeeping, invoicing, and creating financial statements. That stuff doesn't come naturally to me. I spent 2023 leading up to my maternity leave doing a very deep dive on what that should look like, hiring people to help me with that, and shoring up those processes so that by the time the bookkeepers on my team are generating statements, I can look at it and I can understand like exactly what's going on.
It's things like that. It's things like getting ahead of any policies. One thing that I think is maybe more complicated than it should be, but it's the way that the business works is we have a pricing per word model, both in terms of what we charge clients, but in terms of what writers charge us. Pretty much everybody else on the team is hourly, but the writers, it's this specific pricing model and it's because it correlates to how we charge clients. My end goal is to get away from that, but it's what works right now. It's something that I wasn't going to blow up before leaving. One thing that I did was we don't usually have issues with people questioning how it works. For example, you have to add edits to a piece and it takes that piece significantly over the initially agreed-upon word count.
The question is, “Do I get to charge more for that? Does that fall in or outside of the scope of what has been quoted?” That's one example. I wanted to get very granular about what they're billing us for, what we expect for that, and what falls outside of the scope that they can bill extra for. We have an unofficial approach to it and I wanted to make it official. I wanted to be very upfront and clear so that I'm not rushing back from maternity leave to clarify some random situations that we already have an answer for. Things like that. Things like, “When are people like eligible for a raise in their rate? What are our standards for that? What specific milestone should they be hitting within a certain role, for example?”
Freelance Work: Be upfront with how you want things to be done in your business. This way, everything will run smoothly even if you go on a vacation or take a leave.
I wanted it to be so clear because I didn't want to be spending my maternity leave answering those questions or people wondering when I am going to be able to talk about that. I wanted to be clear and I wanted to give people a process that they could follow that made sense. Giving them this information with enough time that they can ask questions about it I clarify or I could redo the processes. There was a lot of stuff like that where it's like, “We're growing. We haven't officially had a process for this. We've unofficially had processes for these things. Let's make it very clear.”
I feel the need to applaud you on taking a break and taking a break. In general, whether it is your own business, your own agency, or even those working for a corporation, people have a difficult time, or at least I grew up in a culture where people had a difficult time and I know for a fact I had a difficult time taking a step back from work, although I am much better about it now. If I take a break, I take a break.
I think initially it was hard because that project is your baby and you want to make sure it goes well. I admire the fact that you are like, “I'm taking these three months off. This is all that I'm setting up. I'm setting this up so that when I'm away, I'm away. I have to applaud that. It's amazing. It sounds like you have healthy boundaries or maybe I'm wrong.
It's a process. I mean I think you said it yourself, which is you have to grow into it. You have to give yourself that permission. I think especially now that like my life has changed considerably, now that I have a little dependent, I have to take care of it.
You have an actual baby.
I have a literal baby in addition to my business baby. Whenever anything about work starts to stress me out, I have to remind myself, that it's a priority for me, but it's not the priority for me anymore. In the past, I've experimented with taking two weeks off for vacation and because of some of these processes that's worked, but I check in, and I still obsess about it and whatever. Even when I take that time off in the past like, “Am I like off? I'm still tied to it,” but now that I have a kid, I want to be present for him. I want to be present for my husband. I need to draw that clear boundary or else I'm not being a good contributor to my family. There's no greater motivation than that.
Freelance Work: Draw a clear boundary between business and family. Otherwise, you are not being a good contributor to your loved ones.
Running The Agency
I remember you mentioned that you launched this agency many years ago. Do you still get to work on marketing design and play around with the latest technology because that's what you did? That's what brought you joy as a child. Are you focused on the company? Are you a company manager, a CEO, a founder, and now far removed from the everyday little things that used to bring you joy as a kid?
It’s both. I have to do the boring stuff that nobody wants to do, but it comes hand in hand with running a business. I have to do the hard things. I have to do the boring things and the things that are outside of my sphere of genius, like the bookkeeping stuff that I mentioned. Every minute I spend on it, I'm like, “This sucks. I hate it,” but it has to be done. There's no working around it If I want to be a successful business owner. I was listening to the podcast or something the other day. I can't remember exactly what the context was, but it was something about like you need to understand how to do things, especially when it comes to financials that may or may not have been what it was about.
You don't want your lack of interest to result in something bad happening because you ignored it or you couldn't be bothered to dig into it. That's my example. I'm sure everybody has their own thing that they don't love to do. It was about marketing and things that are outside of your normal area, whether you're a marketer or business owner. If you hire somebody to do your PPC ads, you don't have to know how to do them as a best practice, but you should still understand the basics so that if they're working or not or if you're overspending your money well placed with this person you've delegated it to or this agency.
That's one thing. In terms of the things that bring me joy, the things that I'm passionate about. It's morphed a little bit. I don't do so much of the website design and tinkering anymore. Although there are times that I make like updates on our site but have mostly determined that it's better for me to delegate that thing because I get stuck in problem-solving mode and it is taking way more time than I honestly have available. That being said, one thing that brings me joy is no code and automation stuff, fiddling with it, trying to create process improvements or better workflows. That's taken the place of it in terms of solving problems within my own business, connecting disparate apps or tools using those principles, and things like that.
It's evolved. It is the best way to describe it. The other thing I was going to say in terms of writing, it's like, I don't like writing anymore and that is something that I do enjoy in writing my book. That took care of a lot of what I wanted to do with that then I'm like, “I'm good for now because that was a very involved process.” Every once in a while we have a client or even a topic or something that is close to my heart or that they specifically want me to write for and depending on the opportunity then I'll do it. For example, I was reached out to Midway by Newsweek and they wanted entrepreneur contributors. I wrote all those pieces for Newsweek that have my byline. It was cool. I was not expecting that.
Skillsets To Success
Before we jump into Rapid fire, during our conversation you've touched on a bunch of skills or characteristic traits, some personality traits that have helped you become who you are or defined your path far, but if you were to present the vast set of skills that have made it possible for you to successfully run an agency each day, it cannot be an exhaustive list because I haven't given you time to think about it. I’m wondering what are those skill sets you think that have helped you get to where you are now.
I think the biggest one that comes to mind are curiosity and a willingness to follow it because that's what got me here from tinkering with web design, trying out different marketing techniques to seeing what it would be like to start my own business and not doing a 9:00 to 5:00 job anymore and continuing to learn because I think especially in the agency world, you have to be willing to adapt constantly because you are your client's first line of defense against anything that happens, especially SEO.
It depends on what your agency does, but with SEO, things change every single day. If you're stagnant it's not going to work. Curiosity is important. You have to be discerning in terms of the way you create processes and the people that you work with. You have to be willing to let go of your own ideal system in some ways. When it comes to delegating, you can share the best practices and you should expect a baseline of how people follow them, but nobody's ever going to do it exactly the same way that you do. That's okay as long as they're still doing it to the level of quality that you would do it. I don't think that I would've gotten this far in business if I hadn't accepted that and embraced that. It took me a long time to do that.
Rapid Fire
The last one you mentioned getting rid of some of your idealism. It happens at work when I'm reviewing code or someone's reviewing my code. It’s like, “The review comment does use this instead of this for a loop.” It is something like that. Is it because it is the, “You would do it this way or is it absolutely necessary?” The other skills that you mentioned, are curiosity, growth, and mindset, and those are important. Talking to you, those come out. I can tell that you have that growth mindset where you're like, “What’s next? I need to learn this. I will do this,” but getting rid of idealism, I did not see that coming. We can jump into Rapid fire. First question that I have for you, what is the one word you would use to describe your leadership style?
I don't know if it's exactly true, but I would say hopefully servant leadership. I don't think that I know everything right and I want to help the rest of my team get their stuff done. That's what I'm going to go with.
What is the best piece of advice you've ever received?
Probably something having to do with mentorship that not only should you seek it, but if you're benefiting from it you should give it as well. It's a cycle.
What is the piece of advice you would give someone who is thinking of joining tech but then they're opposed to joining a regular 9:00 to 5:00, a large or a small corporation?
In general, start with a passion project because you might not find fulfillment in whatever job you do leading up to that, and being able to tinker around and develop skills is something that you have complete control of and then you can decide where to go from there or what might be missing or things like that. Something that everybody should do is play around with the passion project and it'll help you figure out what you want.
Play around with your passion project. It will help you figure out what you want to do in life.
You mentioned Newsweek, but if you were to call out one dream collaboration or client, who would that be?
One of my goals for this year is to write for some of the publications that I haven't been published in before that represent the type of people that I aspire to be, the other bylines are like my aspirational people. Writing for either the online or media like a print version of something like Inc., Adweek, or Entrepreneur. That would be a dream for me. I put it out into the universe.
Closing Words
Manifesting. Before we wrap up, where can people find you?
On Twitter, now X, I'm @MaddyOsman there. I always love connecting with people on LinkedIn. It's @MaddyFrench. That's my married name, but I still go by my maiden name and work because that's my identity. If you're interested, you could check out my book, Writing For Humans And Robots: The New Rules Of Content Style. It's on Amazon in both print and Kindle editions.
Thank you so much. This has been a lovely conversation.
Likewise.
