Notes from My Blog Rebranding Strategy

February 17, 2016

rebranding strategy

This is a guest article by Maddy Osman.

Hey, I’m Maddy, the creative genius (hehe) behind Chicago Cheap Ass and The Blogsmith. I’ve actually been blogging for years, but my concept Chicago Cheap Ass is on the cusp of its very first birthday. It’s exciting and has got me all nostalgic.

Rebranding Strategy Overview

Maddy’s Rebranding Strategy: Chicago Cheap Ass

Changing My Blog’s Theme

About a month ago, I decided to change my blog’s theme design. It was this sudden and urgent feeling that I couldn’t shake. I can’t explain why it happened, but it probably had something to do with my blog’s anniversary and letting lessons from the past year really sink in.

rebranding strategy
A much improved design for!

I’m part of an amazing blogging collective in Chicago called the Windy City Blogger Collective. After being exposed to so many creative bloggers and their own concepts, I had a very particular look and feel in mind for my new blog.

I knew I wanted to showcase all of my different categories on my homepage, with previews of my posts with images. I found a carousel plugin that would achieve this look and feel, but it was hard to get it to work perfectly (or at least to my standards). Since the plugin was paid, I had some support from the developer, but ultimately had to hire a web designer to fix the remaining issues. I do basic web design, but this was a little over my head and definitely not something I had a lot of time to spend on.

A lesson I learned from this process is that if you have little web design issues that you can clearly articulate to someone (not – “the doohickey is doing something weird”), use Fiverr to get it fixed. I spent probably $50 total on a number of web changes. If I had hired a web designer, it would have been $100-200.

There are still small tweaks I need to make, but I’m very happy with the design as it stands. The articles are very Medium-like – big featured image, clean design and a timer for how long the article takes to read.

Changing My Blog’s Tagline

My blog is called Chicago Cheap Ass. Sometimes that gets in the way of attracting brands who’d like to work with me (and can pay a fair price or make a fair exchange for the work involved). My tagline used to be, “The best deals and values in Chicago.”

My initial vision for my website was just sharing deals. It’s moved towards also sharing Chicago food and events that may not be cheap, but are a good value for the price. In addition, I work with Amazon to review technology products that aren’t necessarily cheap. But I’m not full of it – I buy high priced tech when it makes sense. I pay for events even if they’re not cheap. I would never promote something on my blog that didn’t suit the lifestyle I’m always preaching about.

Honestly, I’m still trying to figure out what my tagline should be, because the other issue is that some of my posts are not just about Chicago and have a more broad audience appeal. I’m toying with something like:

“Chicago-based food and events; frugal lifestyle advice for all.”

I would love to hear your feedback and brilliance in the comments!

At the end of the day, I want to have a more broad appeal to brands who don’t think I’m going to be sending them cheap customers!

Changing My Blog’s Content

Finally, a year of blogging has encouraged me to take a more critical look at the blog posts I create and provide additional value to readers.

One thing I used to do that I will not continue to do is write a post in a format like:

[Insert Product/Event/Restaurant Here] Review

Now, I’m going to use each post to share a unique viewpoint. To give you an example, I recently went to my favorite Spanish restaurant in Chicago (which is beloved by a LOT of residents, so it’s quite familiar). My review post for them is going to be called:

“My top 5 tapas at [Restaurant]”

This will result in a much more useful piece of content for my readers.

Changing My Blog’s Logo

rebranding strategy

Right now, my blog’s logo is a crappy word art picture I made in Photoshop. I am NOT a graphic designer and I don’t have a great eye for it. I recognize my limitations, which is another important lesson learned from blogging this past year. I’m currently working with a graphic designer to make it more beautiful – stay tuned!

Changing My Blog’s Link Structure

As a result of research and need, I’m completely changing the link structure on my blog’s menu. Two pages that will be undergoing a massive makeover:

  • Press (as in, work with me for brands)
  • Write for Chicago Cheap Ass

I’m also going to be adding some Chicago “guides” that are longer form posts. I want to gear these towards Tourists, to capture that audience, but they will also be useful for residents!

I’ve also changed my categories from about 10 to just 4. Those four categories are reflected in the carousel of blog posts on my homepage!

Just when I think I’ve finally got it all figured out, I get a new idea that I can’t shake. My blog is a constant work in progress!

Hopefully you’ve learned something from my blog’s rebrand/redesign and can take something from it to help your own blog.

Behind the scenes of a blog rebranding strategy. Helpful tips!

Is there anything you’ve been dying to change? Share your thoughts in the comments!

Author Bio:

Maddy Osman is a digital marketer who has a passion for blogging. Her lifestyle blog,, shows young adults how the find the best deals and values in Chicago. If you’re more interested in learning how to be more effective with your own blog, check out her website,



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  1. Brent Jones says:    •   4 years

    Hi Maddy,

    I know we’ve been chatting a bit through Hangouts about your re-branding. Looks good! You’ve obviously put a lot of blood, sweat and tears into this. You should be proud.

    Matt, thanks for featuring this post from Maddy. Having just gone through the re-branding process myself, I think more bloggers should chronicle what they are doing.

    It’s great for the creative process for the rest of us.


    1. Maddy says:    •   4 years

      Brent – Definitely a lot of effort! But I’m in love with the result. Thanks for sharing your thoughts 🙂

      1. Brent Jones says:    •   4 years

        Fo’ shizzle.

      2. Brent Jones says:    •   4 years

        Fo’ shizzle.

    2. Matthew Loomis says:    •   4 years Author

      Hi Brent,

      I’m really happy that Maddy shared this here. Lots of readers here are in similar boats–new to blogging, or one to two years experience.

      One year in, we learn a lot, and I know myself and many others look at rebranding at that point. We know the domain needs renewing, we might as well make the most of it.

      I know many bloggers go their first year without any logo, they need to improve their design, reorganize their site…I know this post is helpful for many readers here.

      Some will be too shy to ask questions out in the open here. I know they’re reading, though.

      Maddy, I like your new logo, btw. 🙂


      1. Brent Jones says:    •   4 years

        Thanks Matt! Actually, I ended up with two new logos… BJO and Better Freelancing.

        I think the important thing to underscore too is that you can start to lay the foundation for success without the logo, the perfect color scheme, the perfect theme and plugins…

        You just need to GET STARTED and a lot of people seem to miss that part. 🙂


        PS: Sorry, I replied to Maddy’s comment above twice by accident. Feel free to delete one of them.

        1. Matthew Loomis says:    •   4 years Author

          Amen brotha! I see that all the time. People fear getting started for one reason or other, most have an excuse that isn’t really the issue.

          Fear is the issue. The good news is they can overcome their blogophobia.

          And btw, I like the new BJO logo. Where can I see the Better Freelancing logo?

          1. Brent Jones says:    •   4 years
          2. Matthew Loomis says:    •   4 years Author

            Ah, there it is. Nice! You obviously have BJO and BF close together with your branding. Why did you make them look so similar?

            Asking to help the readers with more useful info. 😉

          3. Brent Jones says:    •   4 years

            Well, good question Matt.

            Everything I’m publishing online has a similar look and feel to it. Same color palette, same fonts, same style…

            It’s all intentional as part of an overall branding effort.

            Check out my social profiles… quotes, tips of the day, cover photos, blog post featured images, blog post featured images customized for Pinterest, logos, YouTube video thumbnails…

            They all essentially follow the same format.

            I want my content to be easy to recognize and to stand out a bit from the rest of the noise in most of our timelines.

            Hopefully I accomplished just that! And hopefully that answers your question.

            For other readers, your logo / watermark / whatever doesn’t have to be complicated.

            Pick two or three dedicated brand colors, fonts, get a simple logo to start, and use those elements everywhere — social media posts, cover photos, newsletters, blog posts, etc.

            You don’t need to do this on day one, but you will want to start giving some thought to your visual branding as you begin to fine-tune your niche.

            People should instantly be able to recognize your content based on your branding, even if it didn’t have your name in the title or the domain name.


          4. Matthew Loomis says:    •   4 years Author

            All makes sense, Brent. I was unclear at first if you had started a second separate website or not. If Better Freelancing is a content campaign or something under BJO, then what you’re doing works well.

      2. Maddy says:    •   4 years


        Thanks for giving me a chance to guest post on your awesome blog!

        And it’s a pretty sweet logo for just $5, amirite? 😀

        1. Matthew Loomis says:    •   4 years Author


          Yep, you got a nice logo and that’s a good promo for Fiverr and should encourage many of the readers here.
          See that? Building a blog doesn’t have to be expensive.


  2. Adrienne says:    •   4 years

    Hey Matthew and Maddy,

    I recently went through a rebrand myself Maddy. I was SO tired of my old theme and had been trying so hard to define what it is that I do so that I didn’t go into lengthy detail trying to help explain things to people. It was a lot of work and I did do the theme myself. I haven’t really done a logo, I just have not come up with anything I’m happy with and I have hired a few people to create some for me. They just aren’t speaking to me I’m afraid.

    Sounds though like you’ve got things going in the right direction at least and I do know that these things take time. It seems like it’s taken me months to get to where I am now.

    I wish you the best moving forward and the blog looks good.


    1. Maddy says:    •   4 years


      Loving the new theme! It’s so nice to look at your blog after a major facelift, isn’t it?

      As far as logos – give Fiverr a try. It’s a low cost/high potential reward situation. It helps to go in with some idea of a concept, but the best logo designers can help you come up with it, too 🙂


  3. Matthew Loomis says:    •   4 years Author

    Hi Adrienne,

    Not sure what your budget is on a logo, but if you are interested in getting a referral from me on a logo designer, you can email me.

    At least now things are coming together for you on all other fronts. That’s great.


  4. Andrea Beltrami says:    •   4 years

    It makes my wine filled soul sing when I see people diving into the branding end of their biz. I can’t shower you with enough praise for putting in the hard work, Maddy! YOU GO GIRL!! It looks like a major piece of your rebrand is getting more clarity. THAT’S the beauty of branding, so you’re well on your way.

    Matthew is so right, a lot of peeps get through the 1st year with out much in the way of a defined brand, and I get it. There’s a ton of shit to learn in this online solo space. But the riches that come from investing in your brand will fill your treasure chest for years to come.

    Oh and can I just say I la la loooove hearing Brent speak to consistency and the strategy behind his rebrand. Makes a branding bestie beam, brotha man! And just think…you were so attached to that red button not even a year ago! 😛

    Adrienne…you’ll get there, lady! You do so damn many amazing things I can only hope to be half as cool as you someday.

    Thanks for the shoulder tap, Matthew! It kinda feels like a little happy hour hangout up in these comments. I got the next round!…

    1. Brent Jones says:    •   4 years

      Hey, that red button still has a special place in my soul…


      Honestly, a lot of my newfound courage in the branding realm came not just from what you teach, Dre, but from mimicking what you do.

      I’m not on your level just yet but I think I’ve made some pretty significant progress over the past couple months.


      1. Andrea Beltrami says:    •   4 years

        You’ve come SOOOO FAR, that’s why I feel totally at ease to give ya shit! 😉

        Seriously though, you’re so rocking the shit outta your branding and like I said, seeing you stay consistent is just f’ing EPIC!!

        You put the work in and it shows!

    2. Matthew Loomis says:    •   4 years Author

      Andrea, great to see you join this branding party! Was hoping you would drop by, because you know your branding stuff. 🙂

      I look back at my first year of freelancing (Kaboomis Copy) and it played out similar to what we just described. Now, I did start out with my logo which everyone liked, but after a year I was so ready to go to a self hosted blog instead of and so I started a new site. That site is down now, so if anyone is curious, she gone.

      You’re right Andrea, there’s a lot to learn. It’s good folks reading here get introduced to you.

      What a happy “hour” this has turned into. 😉 Who’s going to drop by next?


    3. Maddy says:    •   4 years


      I’ve spent a lot more time thinking about branding! Just read an awesome book called “How to Style Your Brand” and it helped kick my ass about focusing on creating more clarity (and a more beautiful product). I’ll be looking to your blog and emails for more branding wisdom as I work on my other brand – The Blogsmith!


  5. Andrea Beltrami says:    •   4 years

    The more the merrier….I’m putting it all on Brent’s business card so we’re gravy! 😛

    Of course I’ll stop by, any party Matthew throws has ‘epic’ written all over it. BAM!

    P.S. You don’t want to see what my first site looked like. Thank god she BE GONE too.

    1. Matthew Loomis says:    •   4 years Author

      LOL They gone. ha ha

      We’re still here though. The party is just getting started. 😉

      The party got real epic when you showed up, Andrea.

  6. Andréa says:    •   4 years

    Looks like things are coming along nicely, Maddy! Brent showed me a preview of your new logo earlier and I like it! Don’t be hard on yourself for your DIY logo. It’s great to start off with a bit of elbow grease until you get things running (aka get cash/sponsors flowing).

    You’re off to a great start! And like Dre said, you’re really honing in on the non-visual part of branding. Getting some brand clarity is KEY!

    Keep up the good work. 🙂

    1. Maddy says:    •   4 years


      Glad you like it!! The DIY logo wasn’t awful – some people even praised it. But I knew deep down it could be better and glad I took the step to make it so 🙂 I hope 2016 is a year where both of our brands grow big!!


  7. Peter says:    •   4 years

    Branding is huge for my company too and I also love Fiverr. I use them for logo design and have probably only spent about $30. The results have been so awesome!

    I’m excited to hear more about everyone’s progress!, Thanks Matt for sending me to this article from your emails! I’m a loyal opener and reader of em’


    1. Matthew Loomis says:    •   4 years Author

      Hi Peter,

      How are you? Good to see you again. Glad you liked this. 🙂


    2. Maddy says:    •   4 years


      People just don’t give Fiverr the credit it deserves! Lots of potential for getting help from skilled people… all on a budget!


  8. Jeanette Hall says:    •   4 years

    How about changing the tag-line to Chicago-style food and events; money saving advice for all.

    1. Maddy says:    •   4 years



      That’s what I ended up deciding on. We’re on the same page 😀 Thanks for your input!

  9. Cole says:    •   4 years

    I rebranded my blog last year and it is a lot of work! I ended up changing my tagline, overall look and feel, and really honed in on my niche. All of the work is worth it though! I enjoyed reading how you went about it!

    1. Maddy says:    •   4 years


      Nice to hear from someone who knows! I feel so much better after my blog’s rebrand 🙂

  10. Sherman Smith says:    •   4 years

    Hey Maddy,

    It’s great to see that you’re rebranding yourself. I’ve seen branding as a continuous process for myself. I’ve changed my message and I’m putting more laser focus on who I want to target. As time change, we adjust so you definitely have the right mindset now and it’ll be easy to adjust to the times for you in the future as well.

    Thanks for sharing Maddy! Have a great week!

    1. Maddy says:    •   4 years


      I feel the same way! My personal branding will also be evolving. I’d say even now it’s not 100% where I want it to be, but it’s a step in the right direction! Thanks for stopping by 🙂