How To Pick Up a New Skill and Make Money At The Same Time

My foray into starting a t-shirt business so I could get better at Adobe Illustrator.
With a step-by-step guide so you can do it, too.

Learn a new skill while making money

New skills. Wouldn’t it be great if we had endless time to learn new things? I sure do.

It seems daily I find something new I want to learn or get better at. But each of those things pull me away from my core business. You know… the one that pays my mortgage and preschool tuition.

Still, I try to do as much as I can. Inevitably, I start down the path of learning something new—usually by Googling for tutorials. I get really into it at the outset. But my efforts dwindle as the bill-paying projects begin to take priority or once I feel I’ve “cracked the case” on a new interest.

However, my curiosity never dwindles. I do wish I could learn it all.

If I really wanted to improve my skills in as short a time as possible I would dedicate a certain amount of time and take a course.

Udemy Courses

There’s no shortage of internet services you can pay for knowledge.

I don’t know about you, but my problem with learning a skill through courses is that with no end game in sight, it becomes far too easy to lose interest after the first couple of sessions. Something else always takes priority over my desire to get better at the original skill.

I thought: how I could make learning new skills more of a priority?

I noticed things that are priorities for me are those related to making money.

Is it possible to create some kind of small side hustle with a potential (even if small) for revenue and use that to improve the skills I sought?

Turns out you can!

This is the story of how I combined a bunch of things I wanted to learn into a neat little package that had a clear starting and end point.



A few months ago I knew I had some free time coming up and thought about a project I could do that would be fun and include some items from my “Learn List”– the things I wanted to get better at.

I know how to use Adobe Illustrator, but very marginally. I’ve wanted to gain mastery of Illustrator for awhile, but when you are spending most of your time on the projects that are driving revenue it’s difficult to say, “let me take a break for a couple hours and play around with Illustrator.” That’s a good way to disappear down a time-suck rabbit hole.

Part one: I  needed to figure out a side hustle that would require me to get better at Illustrator.

Another topic I’m interested in is e-commerce. For a long-time, my focus has been the B2B market. Part two: I thought it would be refreshing to work on a side project in the B2C space.

Put these two together and I came up with the idea of a launching an e-commerce store where I would sell items that I design.



Do any Google search on starting an e-commerce store and you’ll get flooded with websites and experts talking about making t-shirts as the best, easiest way to start.

Now, if I was creating a serious new business venture I would quickly realize that the design your own t-shirt business is completely flooded. You know a market is flooded when you can pay multiple “experts” $197 to teach you how to make $64,000 in 6 months with your t-shirt business.

This is normally where I would stop with forward progress on an idea and continue to mull it over and try to figure out the best angle. All the while, I’m learning nothing new and creating nothing.

With the mindset of this is an experiment and a way for me learn new skills it became much easier.

Here I was, ready to create my first online t-shirt business–but what kind of shirts should I sell??

I thought about things I’m really into that other people would potentially also be interested in.

Well, I really love pizza. And I also love my city of Philadelphia.

Easy. I’ll create Pizzadelphia.



I began sketching out a bunch of designs I thought would make for a cool t-shirt. But while furiously sketching, I let my brain slip into a dream zone where I imagined a pizza apparel empire–all of the partnerships I could create, events I could hold, and massive press I could garner from the amazing pizza exploits I was dreaming up.

Uh oh.

It’s too easy to slip down the path of grandiose ideas. This a struggle many entrepreneurs face–it’s called “shiny object syndrome”. It happens when you divert your attention and efforts to the newest, most interesting thing in front of you. A procrastinator’s dream.

I had to quickly erase all those thoughts from my head and re-focus. I’m conducting an experiment so I can learn a new set of skills.

I needed to put a clear goal in sight.

My finish line became an e-commerce store that sold Philadelphia-inspired, pizza-themed apparel. And I wanted the whole process to be automated so once the store was up I didn’t have to do anything with it. I wanted fulfillment, payment, shipping, etc. to all be automated. It would be completely passive.

Even with a clear path to completion I didn’t have a deadline. There was no rush to actually do this. That, and plus my lizard brain still tugged away wanting me to make this a real business.

I finally found the trick that allowed me to within a few weeks create and launch an e-commerce store while learning my way around Illustrator.

Go in with the mindset of learning so you can teach someone else.



About a month after I came up with the initial idea for the t-shirt business I was to start a Big Brother program. Twice a month I’d meet with my “Little”–a Philadelphia high school student. This program had an entrepreneurial focus and I thought, “what a great way to show a high school kid a business that even he can start!”

Now my focus was: I need to start and launch this t-shirt store before the Big Brother program begins so I can show it off to a 16-year old.

And that actually worked for me.

I knew the three important factors:

  • what I wanted to do
  • why I wanted to do it
  • and when I had to do it by.

And none of those decisions had making money at its core. […I think there might be a lesson here.]



The first design concept I had was for the Philly landmark LOVE statue logo covered in pizza. But I had no idea how to accomplish this.

Luckily, another thing on my Learn List was to use Fiverr to hire someone. I had yet to use Fiverr and figured this would be a great reason to try it out. I found an illustrator who did some other food-related cartoons similar to the style I was looking for. I ended spending more than $5 because I wanted to the original .AI file and the commercial license.

After I received the file, I deconstructed it to figure out how he created it and even made some tweaks to the final illustration. Doing this, combined with some YouTube videos as I went along, provided tremendous value.

Pizza Love

I learned way more by tooling around with a single design that I planned to use on a new business than if I watched a bunch of tutorials working on a design I didn’t care at all about.

From here, I dove right in trying to use Illustrator to create the other designs I had sketched out. Some were easier than others. After spending too much time trying to figure out how to create a specific design idea–a heavily-designed, text-based, neighborhood map of Philly pizza shops–I realized I needed to give up on it and move on to something more within my reach.

Remember, I was under the gun to have this store up and running in a few weeks. If I didn’t have the time constraint I likely would’ve kept hacking away at the design that wasn’t working until inevitably something else would take priority of my time and this whole project would wither away like so many others.



Once I had a few finalized designs that I liked, next step was to figure out the whole production process. After doing some research I settled on StorEnvy for the e-commerce site and Printful for the t-shirt production.

On both the e-com side and production side there are a handful of choices.

First, I needed to determine who should make my shirts. I went into this project wanting to automate the entire process. So doing any kind of local screen printing that would require carrying inventory, an up-front investment, and doing the fulfillment myself was out of the question.

The alternative was to find a company that would print-on-demand. Luckily, there are a handful of options for this service. They all use what is called DTG, or Direct-to-Garment printing. DTG is a popular alternative to traditional screen printing–hence the massive competition within the online t-shirt business.

DTG printing is not without its problems though. They are more expensive to print, and there’s no quantity discount since each shirt costs the same to produce no matter how many you buy. Also, DTG is often cited to be of lesser quality than traditional screen printing. However, when I received my first DTG printed sample I was pleasantly surprised at the quality.


The first POD company I found was Printful . I researched a few others but I didn’t want to take too much time deciding. Printful had a very easy to navigate website and a lot of integrations to e-commerce companies. Because automation for me was key this was very important. Plus, Printful sells other items like tote bags, posters, pillows, mugs, and leggings. (Yes… making pizza leggings did cross my mind.)


A cool feature of Printful (and some of the other companies) is their t-shirt mockup generator. You can easily stick your design on a mockup of the t-shirt you want to sell and use that picture in your e-com store. They even have a few mockups of models wearing your shirt design. The pics with the models I don’t think are very good, but it’s great to have a pic of someone “wearing” your shirt to showcase on your website. I’ve read studies somewhere proving that consumers are more apt to buy something when they see other people’s faces.

Printful also gives you a pretty good deal on purchasing samples of your products.

And this is where my biggest expense came from. Printful offers a large amount of choice and I wasn’t sure what quality of shirt to get. After receiving a few samples I settled on the pricier American Apparel 2001 shirt. Choosing this shirt meant I would need to charge a higher price to maintain a respectable margin. I felt comfortable doing this because the American Apparel 2001 models are the most common shirts used by online t-shirt designers. And after getting a couple samples of the different types I could see why.

Getting samples of your shirt is critical to ensure your design looks good.

While my biggest outlay was on these sample shirts the upside is I now have a bunch of reject Pizzadelphia shirts that I wear to the gym.


Before settling on Printful, I briefly considered using a new Amazon program that launched while in the middle of this project called Merch by Amazon. It was created for the developers selling games on Amazon’s platform to also sell shirts as swag for their companies.

Merch By Amazon

The upside of Amazon was the shirts cost less money, of course everything was automated, and I’d be able to use Amazon’s platform for better discovery of my shirts. I threw up one design and purchased my own shirt. I didn’t love the quality and a major problem with Amazon is all of the customer data is on their platform and unavailable to the seller.

Amazon would’ve been the easiest way to get started, but it really wasn’t I envisioned.

Once I settled on Printful the next step was to pick the e-commerce provider.


E-Commerce Shops

The field of e-commerce providers was much larger than POD providers. Here are the ones I considered:


I would’ve loved to use Shopify . When I began thinking about e-commerce I started listening to a great podcast called Shopify Masters. It’s an interview show with successful e-commerce entrepreneurs and they all use and rave about Shopify. The problem with Shopify is it costs $39/month. No way I could justify that for my experiment business that would likely not see any revenue in the beginning.

Big Cartel

Big Cartel is a very popular choice for artists and other t-shirt designers, especially if you only have a few items to sell. The big plus for Big Cartel is their freemium model, which makes the service free to use for up to five items. I knew I wanted to sell more than five shirt designs so that put the kibosh on this one.


WooCommerce was attractive because it’s core functionality is free in the form of a Plug-In for WordPress sites. The downside is you need to obviously have a WordPress site. This could be complicated for some people if you are not familiar with WordPress. I already had a few WordPress sites so I knew this wouldn’t be a major hurdle for me, but there are costs associated with WordPress. Going this route meant hosting costs and worse—I’d need to design a new website. That would take me too long and I’d waste too much time trying to design an e-commerce site that I liked. Knowing this, I didn’t even investigate WooCommerce any further. I required a done-for-you service like Shopify or Big Cartel.


And that’s when I stumbled upon StorEnvy. I liked this one probably the least but they checked all the boxes in terms of requirements and had the right price—Free. StorEnvy seems targeted as an evolution for Etsy store owners to upgrade them to a platform that provides the seller a little more ownership.

The benefits of StorEnvy is the platform is completely free, they integrate fairly seamlessly with Printful, integrate with PayPal and Stripe for payments, and gives you access to HTML/CSS code so you can customize the design.

Unlike Shopify—which provides retailers with their own e-com platform—StorEnvy is positioned more as a marketplace platform. It has a discovery element to find products. And this is how StorEnvy makes its money. When someone purchases your goods through the StorEnvy marketplace they get a 10% cut of your sale. But if you sell from the custom storefront they give you then you keep 100% of the sales. Seemed like a pretty sweet deal to me.


Setting up the custom store was fairly easy. On the Printful side, I just had to watch a short video tutorial they made on how to sync up the items between the two services.

When all was said and done the last step was to place an order through my new StorEnvy shop to make sure all of the credit card processing stuff worked and it came out on the other end. This is a crucial step. If you launch a store but don’t test that you can actually take payment for an item you can really screw yourself.

For my test purchase, I ordered a “Pizza Love” mug. Because, why not?

Pizza Love Mug

Next step was to open the store and let the world know about Pizzadelphia.



Not quite. From a business perspective, I massively failed to gain traction. Mostly because I barely told anyone about my venture. I knew going into this that without marketing and promotion on the back end, no one was going to buy my shirts.

But I was okay with that.

I didn’t go into this project with the goal of making a lot of money. I quickly realized that the time it would take to market and grow this business is time that can better be spent on growing the real business that I run during the day.

The upside is I now have a drawerful of pizza t-shirts that I wear pretty much all the time as they are probably the nicest quality t-shirts I own.

I do think there is a small market for Philly-pizza related apparel. Since I started this project at the beginning of Winter—not quite t-shirt weather—I’m thinking I might wait until Spring rolls around to see what else I can do with Pizzadelphia.

Testing Out Instagram

The one marketing tactic I did try was Instagram. I’m far from an avid Instagram user but this was another thing on my Learn List that I wanted to try out.

I knew very little about hashtags and how to actually use them effectively. That took some Googling and trial and error, but now I know that it’s smart to save your commonly used hashtags in a separate note-taking app and copy and paste them into Instagram when you want to use them.

Once I decided to start posting on Instagram I knew I wanted to post some cool videos. But I had no idea how to do that. Bundled with the Adobe Illustrator software I owned was Adobe’s After Effects motion graphic software. I thought that would be fun to learn and took off on a slight tangent.

Having never touched After Effects before in my life this one was a little more daunting than working with Adobe Illustrator. However, a few YouTube tutorials later I was able to make the below videos.



While I’m no auteur, these were super fun to make and satisfied my desire to figure out how to make Henry Rollins’ head spin round.

What’s Next?

If I wanted to spend time gaining more traction my next step would be to focus on Facebook. Figuring out how to advertise on Facebook is another thing on my Learn List so I might start testing out Facebook Ads. However, I heard Facebook Ads don’t work so well for selling goods, but are great for building your audience. I’m not sure how effective they’d be for this venture but it might be worth experimenting.

I could also send some of my high-profile friends in the pizza scene (don’t laugh—this is a real thing) t-shirts to promote on their social media feeds and see if that works.


At the end of the day, here were all my expenses for this endeavor:

• domain — $12
• Shirt samples — $57.36
• Test order (mug) — $10
• Fiverr Illustration — $31.50
• Printful account — $0
• StoreEnvy account — $0
• Illustrator — $0 (already owned, which definitely helps)
• After Effects — $0 (bundled with Illustrator)

Total Expenditure = $110.86



Absolutely. I set out to learn new skills and ended up putting out something new into the world.

From a “learn new skills” perspective, this whole experiment was a smashing success. Within a few weeks, and at a cost of a little over $100, I…

• Dramatically raised my competency in Illustrator
• Learned the ins and outs of print on demand
• Learned the basics of After Effects
• Learned how to post an animated GIF to Instagram (this was probably the hardest thing to figure out)
• Learned how to properly use hashtags on Instagram
• Actually sold a few shirts to strangers who liked my designs!

In the end, the whole experiment was well worth it because I made one kid’s size t-shirt that my 4-year old daughter proudly wears to school declaring that she loves Pizzadelphia!

Iva Pizzadelphia


Think about what’s on your Learn List (you do have one, right?). Which skills can you possibly combine and create a meaningful side hustle from? Remember, the key is to have a compelling reason to get started and a specific deadline to finish. Now go out and make something!

Check out the store at:

Pizzadelphia shirts