Swigcasso – My Main Side Hustle


It all started with a casual stroll up 94 floors in Downtown Chicago…

When I worked in Illinois, I worked for a sports nutrition company that sponsored an event called “The Hustle up the Hancock”. It consisted of running/walking up The Hancock  94 floors, 1,632 steps of pure torture. You can learn more about the Hustle here .. Every year, the company would send out an email asking if anyone wants to run the event and I was always game. We’d train for months in order to build up the endurance even though every year you fight the urge to vomit and you’re convinced your lungs are bleeding. And you get to the top and they hand you a banana when that’s the last thing you want, but you get the most beautiful view of Chicago at the top. The company who sponsored us covered our entrance fee, but always asked that we raise money for the Respiratory Health Association. And let me tell you, it wasn’t easy to raise that money.

So I thought, “hey, I should give people an incentive to donate to this charity”. The week before I had painted a wine glass as a surprise gift for a friend of mine that consisted of two cats, Harriet Tubman, and bowl of mushroom risotto. She actually chose those subjects (with a little trickery). I had to surprise her so I asked her to fill out a “Mad Libs” style text message in order for me to choose what to paint.

I was not a painter by any means. I’ve always been able to draw well, but painting was not my jam. I had no idea what I was doing. So naturally I thought, “I should paint for people as a ‘thank you’ for their donation”. And that’s what I did. I sent out a Facebook post asking for donations and offering up a “painted wine glass with the subject of their choice”.

I instantly started getting SO MANY DONATIONS. And then the requests started rolling in. “Nicolas Cage” was one of the first requests and I thought, “dear God what did I get myself into?!?”. I painted that and I think I did ok. Not great by any means, but for me being so new at painting, I thought it wasn’t the worst. Then I received requests for “Predator”, Ron Swanson, Dwayne “The Rock” Johnson, someone’s dog, 3 Star Wars characters surrounded by wine grapes, and so many more. I painted all those too. They were getting a little better each time.

Then I invested in a few good quality brushes and started trying out all the different acrylic paints that Michaels had to offer to find the best ones, and my paintings got better and better. A few more donations later and it was finally time for the big event, The Hustle. I found out just minutes before I started running up the stairs that I was the #1 fundraiser from our company and I even had a big-wig at the Respiratory Health Association come up to me and personally shake my hand and congratulate me on my fundraising success. I felt like a total boss.

The Hustle came and went and I was no longer collecting donations for the RHA. And therefore, I wasn’t painting. So I decided to start an Etsy business to keep developing my talents, and to make some money for myself while I wasn’t raising money for the RHA.  But I needed a business name…

I saw this video on YouTube about a pig that learned how to paint and his name was “Pigcasso”. I liked that pig and figured “I’m basically that pig but I’m painting wine glasses”….and “Swigcasso” was born!

I had a store name, designed a really quick logo on Canva, and my store was up and running! I would listen to the “Side Hustle School” podcast for tips on starting my side hustle business and I made sure to see other “wine glass painting Etsy shops” and really look into their Instagram and Shop pages for inspiration. The more successful shops had excellent photos of their products. So I made sure to buy a wooden board and a piece of burlap from Walmart to be my base and background, and then I threw in my favorite bottle of wine and two corks for additional design elements in my photos. My only listings on my page were for custom glasses – so the customer could ask me to paint anything they wanted.

My Etsy Site – Swigcasso!

My biggest success for sales was actually just advertising my business on my cubicle at work. My coworkers loved having someone nearby able to create custom gifts for birthdays, weddings, anniversaries, etc. I probably have sold 50+ glasses to date, but only a handful actually went through Etsy. It was much easier for me to handle the local jobs in-person and get paid with cash.

If you go look at my store today, there are only 2 pre-painted cups up for sale. Every Christmas season I take so many orders and I end up getting burnt out on painting by the time the holiday comes up. I usually take a break every January and jump back into painting by February.

As far as a side hustle goes, opening an Etsy shop has been amazing for me and I would suggest it to anyone. Listing fees are only $0.20 per listing, Etsy doesn’t take a cut of your sales, and the shipping costs through Etsy are much cheaper than if you go to the post office yourself. I saved enough money to go to London, Paris and Bordeaux with that money so I can’t complain. The only thing is that I can’t make that much more money each month with this particular hustle. It isn’t passive, by any means. Each glass sold can take me 1-4 hours to paint depending on the subject. So I can only paint so many glasses a month. I’m currently exploring a few options to make more money in less time, and I’ll definitely keep you all posted on that progress as it develops! Until then, I’ll still be painting and selling on Swigcasso!

So you might be reading this and thinking “I can’t paint to save my life, how am I supposed to start a painting side hustle?”. Don’t worry, you don’t have to. The message here is to do something, anything, to make a little extra money to put towards the principle balance on those loans. The best advice given to me when I started was to “start right away”. Start sooner than you’re ready. Because you’re never going to feel 100% ready and you’re always going to want to hold back until it is “perfect”. The best part of this side hustle was learning as I kept going. And I was able to take those creative problem solving skills and apply them to my other side hustles as well.

And it’s funny that I give that advice at this particular point in my life and my debt journey because the fear of failure has been holding me back from starting a new side hustle. I kept giving excuses as to why I haven’t started. Who am I to give great advice that I’m not using myself? My promise to both you and myself is to forge ahead with the new side hustle ventures and stop letting fear keep me from achieving those dreams. You’ll be seeing some new stuff come from me that definitely won’t be polished or ready, but it’ll be up and we’ll embrace the successes and failures together.

4 comments on “Swigcasso – My Main Side Hustle”

      1. Too funny! Thank you for the sweet compliment. I enjoy your blog as well – so close to home. Keep in touch and I’ll do the same 🙂


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s