8 min 37 sec

Host a Birthday Party, Drink Wine, Make $2,000

A birthday “paint and sip” celebration becomes an accidental side hustle, providing a sustainable income for an artist in between day jobs.
Arts & Crafts Events Service Unique Ideas

Subscribe Now For A Free Five Step Tutorial

What It's About

A birthday “paint and sip” celebration combined with a Facebook post becomes an accidental side hustle.

Business Model
Arts & Crafts
Skills Required
Creativity & Trend Spotting
Profit Potential

Words of Wisdom

Here we have the right balance in art as a social activity, and one that removes inhibitions through the wine and casual nature of it. Add the clever name like “Proof in Painting” and it’s a low-risk commitment for someone to sign up for one of these events. The people who sign up are different than those who take art classes—and this is key to Chelsea’s success.

Fun Fact

A month after arriving in Oregon, Chelsea was talking to someone who asked the very common question: "what were you doing before you moved here?" She listed her endeavors and included the painting.

He said "I work at the country club and we had a meeting 3 days ago that we want to start offering these. Could you do them for us?" And just like that, she had a monthly gig!

Notes from Chris

Episode 467
Chelsea Gittle was trying to do something nice for her mother’s birthday. The former environmental consultant and life-long painter wanted to throw an artistic birthday celebration. She rounded up a few of her mom’s friends and invited them over for what she called a “paint and sip” party. They drank wine, ate food, and Chelsea led the group through an interactive painting experience. Much to her delight, everyone loved it!

When she got home, Chelsea uploaded a few pictures of the event to Facebook as a way to mark the occasion. But when she looked back a few hours later, she found lots of her friends were interested in the experience as well. So, she set up an event for the next week, and all of her friends loved it as well!

Over the next few months, Chelsea ran a couple more of these paint and sip parties for her friends, but never really thought of them as a business opportunity. It wasn’t until one whole year later, when her dog injured its knee and needed surgery, that she saw the potential as a moneymaking venture.

Instead of starting a GoFundMe page to raise the money for her dog’s surgery, she decided she would generate the income herself. She felt she didn’t want to take people’s charity if she had the skills to earn money on her own. So, she created an event called “Paint Party for Good Paws” and posted about it on Facebook.

A few people came along and helped her earn a good chunk of the money for the surgery. While she was hosting the event, a few of the attendees asked if she would host a monthly event for them and their colleagues. Chelsea agreed and set the price per event at $35 per person. This was enough to cover all of the supplies, from the wine through to the paints, and give her some profit to put towards the rest of the surgery. Which, after a few months, she was able to pay off in full.

With the surgery paid for, Chelsea felt she would keep the project going to cover her income while she was between jobs. To give the business a professional feel, she gave it the name Proof in Painting.

Chelsea spends between four and forty hours a month on her side hustle and earns up to $2,000 a month, depending on the demand.

She’s currently looking for a full-time job. She wants to keep Proof in Painting as her side hustle and continue to host events. But the stability of a full-time job would be refreshing and allow her to keep a more stable income. It just goes to show you that it is possible to paint and sip your way to a sustainable second income.


  • Proof in Painting: Art in front of others is always better with a glass of wine (or two)—learn more about Chelsea's sip and painting project over on her website!
  • Wix: The online website building platform that Chelsea used to set up her website for Proof in Painting

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


Download Episodes By Months:

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |



Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️

Learn More


Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for my past 5 websites. It's cheap, flexible, and you can get support 24 hours a day.

Get your own hosting plan for just $2.49 a month!

Learn More

Quote of the Day
"Sometimes you get such a great idea that you have to just go for it. Don't get caught up in the details or bogged down with overhead costs—there are always alternatives!"
—Chelsea Gittle #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

Today’s episode of Side Hustle School is brought to you by ShipStation, the #1 choice of online sellers. 📦

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.

Get it Here

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau