I Make $120K/Year With My Print On Demand T-Shirt Side Hustle

Published: October 5th, 2021
Cinquanta Cox-Smith
Cinquanta Cox-Smith
from Killeen, TX, USA
started September 2009
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Hello! Who are you and what business did you start?

Hey, y’all I’m Cinquanta Cox-Smith I hate putting myself in a box, but If I had to explain what I do: I’m a Multipreneur. (Author, Podcaster, and Entrepreneur) I’ve been helping entrepreneurs start an EASY Print On Demand side hustle from anywhere for about 3 years now. I’m originally from a small town in South Carolina called Georgetown. It’s historic in many ways, especially for the Geechee Gullah culture. I’m an Army Veteran and my Husband (Shawn) is an active-duty soldier. We have 2 kids Kyree (15) and Sharye (12). Let’s not forget about our dog ChuChu. He's most definitely the star of this show.

I’ve built my brand around the Print On Demand industry and I run multiple POD (Print On Demand) brands spread throughout at least 5-6 platforms. My main Brand Coins and Connections has my best-selling shirt which is a text-based design that says “I target audience to be other entrepreneurs who need apparel to describe their journey.”Not everyone is an extrovert so the idea was that most of the shirts would start a conversation. Our shirt “My Life Is Dope and I Do Dope Sh*t” is a really popular one along with “I Hope My Hustle Offends The Sh*T Out Of You” people love the word SH*T, and I do too! I love that our shirts help the marketing aspect easier at conferences and events and people notice what you are wearing before they notice you sometimes. So by having eye-catching apparel it’s the hook and reel to introducing your brand.







I’ve always felt like this was just a hobby, or I was just making shirts but Print On Demand is so much more than that. It’s helped me create $7,000 in one month selling POD journals on Amazon KDP, it’s helped me land a Magazine Cover with my T-Shirts for Stars & Stripes (American Military Newspaper). It’s helped me teach over 10,000 people how to create passive & residual income from home with just a computer and some wi-fi. Most importantly it’s allowed me the gift of TIME. Time to spend and travel with my family. Once we get further along into this interview. I’ll tell you about how I accidentally started in the Print On Demand industry 12 years ago.


What's your backstory and how did you come up with the idea?

Twelve years ago in September 2009, Kanye West stormed Taylor Swift on the stage at the MTV Awards, and I was deep into my Twitter journey. I had the idea to create a shirt, but I didn’t want to use a transfer pack from Walmart and an iron. So I searched google and found a site called Spreadshirt.com That’s where my journey started. At the time I had no clue it was called Print On Demand. I had no clue that a few years later 2011-2012 that I would teach myself how to drop ship products from Aliexpress to eBay. I just knew that I wanted to make money and this was working. A successful attempt to make one shirt led me on a journey to uncover so many more products and platforms that drive the Print On Demand industry.

People thought the shirts I created were unique and funny. I even created shirts for some DJs (@thedjaone and @djblord ). These shirts had their Twitter @’s on them. It solidified early on that I knew how to network and market a product. I’ve always been creative with my hands. Painting designs on shirts and jeans in High School, or just cutting my shirts up to make cool designs, and writing poetry in a binder so that’s as far as my experience goes. When we are younger our creativity has no boundaries and there are no rules. It’s how people start to perceive us as we get older that puts a halt to that creativity layer deep down inside of us. I have always tried my best to stay in my lane even when everyone else was doing the same thing.

I’ve tried so many different things in my business journey. I’ve done jewelry, sewing, writing, trying to be one of the twerk team members on YouTube, hell the Army, but creating and designing is my biggest flex. My confession. I’ve never been financially stable during my journey. I would use tax time or side hustles as a means to fund my dream. With that comes disappointment, loss of money, and frustration to want to give up. I gave up a lot, and I’ve even spent $10k in less than 2 weeks multiple times, but I always remember that extra strength that shoots through me when my back is against the wall. I’m not a millionaire in 30 days, but I’ve got longevity and that’s a success story as well.

Take us through the process of designing, prototyping, and manufacturing your first product.

I had to make sure the products that I wanted to create I would wear a lot, but it also needed to resonate with my audience. Phrases needed to be catchy and quick to read when in passing. I went to Pinterest initially when it wasn’t too hard to find some fun quotes to remix and make into your own. Once I had enough quotes I started ordering samples and packaging for my brand. I purchased poly mailers and stickers from a site called Sticker Mule.

I might have switched niches or changed the direction of my businesses, but I never quit.

When it came to trying to design embroidery patches I went back to the handy dandy Aliexpress website, and later on, I found an enamel pin manufacturer gxpins.

As far as platforms I did use Shopify and Printful initially in the beginning as well, but as the years went on I operated on both Shopify and Etsy. My Etsy store started to outperform Shopify and it felt like the right decision to close my Shopify store. I now use my Shopify on pause but I use it for some of the apps that are Print On Demand. Like Teelaunch, Printful, and Printify, and Art Of Where to name a few.


I always switch gears in my business so selling courses, tutorials and even writing books seem like another way to make additional income so I started recording my process with Print On Demand and putting them for sale on my Gumroad Site. The world of digital products is profitable, but you need to make sure people want what you are selling and that they need it. Once I learned to take my skill from writing books to creating blank journals on Amazon. I found a secondary source of income. That became my main source. That journal course has sold a lot and to think I gave it away for free at first. Now people have created entire businesses around creating journals and templates for businesses.


I must admit after it’s all said and done I didn’t make my business completely legal until I started making $10,000 in a quarter. I thought that was a lot until I started making $10,000 in a month. Making sure I had an LLC, a business bank account, and finally trademarking my brand. It’s been a long journey and I’m sure I did things backward but we all learn. Learning about payroll and paying taxes with Gusto was an adventure as well.

I’ll include early photos of my first embroidery patches and a phone screenshot of my Shopify dashboard in 2017. I was still unsure of what I was doing. I was still shipping products out to customers. It wasn’t until around 2020. That I realized I wanted my business to be 100% Print On Demand.




Describe the process of launching the business.

I started almost all of my businesses with less than $100. I started my Print On Demand business with $0. I remember joining a Facebook group around 2016 that reshaped how I looked at business. Build Brand Launch was just starting lots of valuable information was within that group that helped me on my journey. Arsha Joneswho is the owner of Capital City, and Tees in The Trap created the group. She and a guy named Lamar Tyler did this free ads course.

I remember taking notes and also implementing these things I had learned. I set up my first Shopify store, and because I had already had some success in dropshipping I was able to create a Chihuahua lovers store. I decided to sell jewelry. After 24 hours of creating a Facebook page and Shopify store. I opened it with like 3 products and ran the Facebook ad. I got my first sale within 48 hours. I heard that chi-chang and I’ve been hustling ever since.

I let the Chihuahua store go after the initial 30-day trial and then started building Coins and Connections.


The site has since changed a lot and now I run my eCommerce store on Etsy and other various Print On Demand platforms.

I’m not a millionaire in 30 days, but I’ve got longevity and that’s a success story as well.

I’ll say it again. I wasn’t always financially stable running my business. I used any income I had from my full-time job until I quit in March 2017. Since then I’ve only held one part-time job from 2018-2019 a little less than a year. Other than that I’ve been a full-time entrepreneur. I had one Shopify Capital loan and my other side hustles as a website tester helped me to keep my business afloat when I didn’t have it. Usertesting.com has been a big help funding my business. I made $490 in one month. $10 for doing website testing for 3-10 minutes of your time.


My biggest lesson learned is knowing that I can learn something and implement it and get results in 72 hours if I’m determined to succeed in business. Launches should be well thought out but implemented quickly.

Since launch, what has worked to attract and retain customers?

The best thing I ever learned was SEO when I was blogging early on. Here is a screenshot from my first blog and my blog now. When I first started blogging I was writing about everything. Clothing, reviews for products sent to me from Amazon, beauty stuff, and Dollar General penny items. I had no clue what I wanted to do or why I even had a website, but it helped me to start. I learned a lot about SEO, and Google Analytics.

Smile For Me;


Once I learned more about blogging and hosting my site along with email marketing I moved over to WordPress. Where I’ve been hosting my blog, and all things books and business about my entrepreneurial journey. My focus there is Print On Demand and the educational materials and videos I sell and share.


I’ve probably watched numerous videos on SEO, signed up for free courses, but you need to ultimately understand how search engine optimization works. Once you understand how it works then you’ll be able to teach the search engine how to find you and how you show up on google. Here’s a tip: search my name “Cinquanta Cox-Smith” and see how many pages are dedicated to me and my business. How far back do information about me and my business, + books go back. Learn this key SEO skill, and you’ll always make room for organic traffic. It’s just like Amazon. Enough people type in gifts for moms Amazon will start populating those terms and then suggest gifts for moms of toddlers and more.

Ultimately just start. It’s okay if you have to do it alone or with no money. Just begin where you are.

While we are on the subject of Amazon let’s talk about how you can find untapped niches for just about anything on the platform. Whether you want to do an MBA, FBA, or even KDP. (Merch By Amazon, Fulfilled By Amazon, Kindle Direct Publishing) You can find niches to get into. Knowing how to niche down is the most important thing. You can find a popular niche and do some digging and sometimes it’s not a lot and find a small niche inside that big one that can create additional income for you. Check out my playlist on YouTube where I do niche research for random Keywords. It's called Let’s Niche Down. Learning to do this will help you research better. One of the best techniques when it comes to business is using the platforms to do research.


How are you doing today and what does the future look like?

Today I’m in between whether I wanna start another Print On Demand business or continue to grow the profitable one I currently own. I’ve had setbacks with my main brand, but it’s been profitable from day one. It’s my top source of income. I’ve started to do more Print On Demand custom orders and it’s helped my business grow on Etsy and I’ve had repeat wholesale orders. I think that’s kind of where I am joining some wholesale sites to get more eyes on my products.

I don’t have a lot of expenses because I do Print On Demand. I’ve done ads now and then, but I don’t rely on them or an email list. My main brand has little to no social media presence and I’m okay with that. People always look at me like huh. But it’s totally what I’m going for. A ghost business where you don’t know I own it but it’s successful. When I get bad reviews I don’t take it to heart. It’s a reflection of what they may think of the printing company and not necessarily my customer service or product design. 100% of my sales come through Amazon, Etsy, and other sites like: Redbubble, Teepublic, Teespring, Spreadshirt, Cafe Press, and Society 6.

A normal day for me is making sure orders are being processed, and answering any emails about orders. I do a lot of designing, creating, recording, and editing when I do spend time in my office. I’ve already been able to expand my reach to the UK, Japan, and a few other territories by offering international shipping and just through Etsy & Amazon.

For my Print On Demand business, I just want to be able to continue to grow the brands and introduce more products. I have a goal of longevity. That may look like building brands and selling them once they become profitable or continuing to share my knowledge so others can do the same. Either way in a few years. I know I won’t be producing new content as far as videos and podcasts. I’ll be working behind the scenes with little to no social media interaction. It’s fun but it’s a distraction. If I can build a successful brand once with no social media. I can do it again. This is the goal.

Not using social media to market, and gain more exposure for my brands is very scary for a lot of people, but there are already lots of brands we don’t know what the CEO looks like. Being able to apply that to a small business that also has little to no social media presence is sort of how things used to work. They relied on word of mouth, and print marketing to get customers inside the stores and to their website if this was available. I’m a behind-the-scenes type of person so because this was able to work for me a few times. I enjoy the peace without pressure.


Etsy & Amazon KDP Dashboards: One of my Etsy POD shops and One of my Amazon KDP accounts

Through starting the business, have you learned anything particularly helpful or advantageous?

I’ve learned lots of helpful things that kind of haunt me to this day. I noticed that during the summer months business could take a tank, and I’ve lost my website domain or business emails because of not having the income. It kind of taught me to invest in yearly subscriptions or paying annually for tools I often use.

My biggest tip and takeaway is to always be authentic.

Always check your junk email. There may be an important email you are missing that can change your life. Along with your message requests on Instagram and Facebook. It might sound like trivial advice, but I know someone who missed an opportunity with The Ellen Show by not checking those inboxes after going viral on Instagram.

Now, this is a big one. Once you get the partnership or the deal. Get a lawyer to help you understand the verbiage in the contracts. Not one of your friends who aspires to be a lawyer. Also have a contract in place when you are providing services to people, NDA, non-compete disclosure for employers or contractors. Many people will take until they create a complete copy of your business. Don’t try to bootstrap it all by yourself. It’s okay to apply for grants and scholarships. It’s okay to have a Kickstarter campaign or pitch other companies, and corporations. Always have a backup plan at least 2 or 3 because things will fail, not work out, fall through, and make you want to quit your business.

What platform/tools do you use for your business?

I have so many. Wow, but my very first one is Canva. I think I’ve been using it since it came out, and it’s been instrumental in my business from creating book covers, journals, social media content, podcast graphics, and more.

Canva - If you’ve read this and you're interested in all the talk about Print On Demand and wondering what it means and how can I just design products without having inventory and not have to worry about shipping. Printful is the best place to start. It’s not the first site I used when starting my journey. But it’s the main one that I use for all of my t-shirts, journals, and mugs.

I love that I can make money on Amazon. So I enjoy using Amazon.KDP Self Publishing | Amazon Kindle Direct Publishing, Amazon Merch, and ACX for my book business needs. Their platform has so many users that it’s free traffic if you focus on your SEO.

Etsy is by far one platform that is slept on, but I left Shopify for ETSY. I used them for years, but again sending traffic to your site is a daily process and struggle. I wanted to be able to know that I can bring traffic consistently without ads. So organic traffic is how I make that happen.

I use a service that I enjoy called Book Bolt for journal creation and when I need more elements and tools I use a site called Creative Fabrica. They have just about everything there. Coloring pages, and also elements you can use in Canva.

My last two tools that have been a game-changer for video and podcast content are called Descript. It cuts down the time on editing and transcription. Best $30 bucks I’ve spent monthly. Along with podcast tools I use Headliner to turn my audio into nice audiograms or videos for my YouTube channel.


I don’t use too many different paid tools because I like to keep my expenses under $100 a month so the maintenance is low but the income is good.

What have been the most influential books, podcasts, or other resources?

Some of my favorites books have been:

Some podcasts that I enjoy are:

All of these books and podcasts continue to inspire me because as a black woman seeing others be successful, and coming from similar backgrounds as me encourages me and motivates me to continue living out my dreams. It helps me to tell the universe what I want and to stay committed to going to get it by any means necessary. Unless it’s about going to jail or losing sleep. You can count me out lol!

Advice for other entrepreneurs who want to get started or are just starting?

I’ve had to learn things hard my entire life, and most of all in business. Not sticking with one thing or finding a niche early on has had me at the beginner point numerous times over the past couple of years. It’s not wrong to chase the money, but chase it the right way the first time so it will continuously flow to you.

It’s easy to see yourself doing the same thing for the rest of your life, and have fun while doing it. So find that thing as we call it your niche. Define it, and make sure people understand what it is you do. Having clarity helps people shop with you, or spend time and money with you.

My biggest tip and takeaway is to always be authentic. I used to feel like I had to tone down my personality to fit in when my business needed the true me to stand out. So if you are the awkward, funny, corny, or nerdy person in your friend group. Keep those unique traits about yourself and share them with the world. I guarantee you there are so many others who can relate.

Ultimately just start. It’s okay if you have to do it alone or with no money. Just begin where you are.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

Cinquanta Cox-Smith, Founder of Cinquanta Cox-Smith
Pat Walls,  Founder of Starter Story
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