9 min 42 sec

Minnesotan Earns $70,000/Year Teaching Wine Classes

When a lawyer demands tasting lessons from a wine store employee, the employee realizes there’s a demand for his knowledge. He eventually leaves his job to educate people about wine full-time.
Classes Education Service Wine

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What It's About

A chance encounter leads to a new side hustle opportunity—and eventually, a full-time business.

Business Model
Skills Required
Wine Knowledge & Communication
Profit Potential

Words of Wisdom

Going from $1,000 to $5,000 is not 5x as hard—it's more like 2x because you already have something that’s working. You have a proven model, so you don’t have to reinvent an all-new model. What you have to do is exactly what Jason did: reach more people, segment your audience so you have different options at different prices, become more efficient with the right tools and resources, and create extensions—like the wine tour, or then the wine tour referral extension, and now the training extension for wholesalers.

Fun Fact

Before Jason started offering wine classes, he was going to school to become a high school history and geography teacher. But after some time in the classroom, he became disenchanted with the idea. When he ended up teaching adults about the history of wine instead of kids about geography he still ended up using his teaching skills.

Notes from Chris

Episode 297

Today’s hustler is Jason Kallsen from Minnesota, whose side hustle came directly from his day job, though in a very unexpected way. Back in 1997, Jason was working for a wine shop when a guy came running in, saying that he was in a huge hurry but needed lots of wine to share with a bunch of fellow lawyers for a party he was hosting at his house. He pointed to his cart and said “Fill it up!” So Jason filled up the cart.

He thought nothing of it until a week later when he saw the same BMW raced into the parking lot, and the same lawyer running into the store again. Jason thought he hated the wine, so he actively hid in the store. The guy eventually found Jason and pointed at him accusingly while asking, “You picked out all those wines, right?! They were incredible but so obscure nobody knew what they were. So fill my cart up again with the same wines and come to my house next week and teach us about them! My friends really want to hear from you!” That was Jason’s lightbulb moment.

He filled up that guy’s cart again, went to his house, did the wine tasting, presented maps, talked about history and geography, and got paid for it. While that first time he only charged $50, most of which went towards pizza on the way home, it was the start of something.

The very next week he began a side hustle educating people about wine under the name Twin Cities Wine. Before long, he found so much success with this new side hustle and the projects that sprang from it, he ended up leaving his wine selling position in 2015.

At this point, Jason estimates that he’s taught over 10,000 people in his Intro to Wine class alone. Thinking about how many people he’s taught helps prevent the inevitable burnout of being a full-time entrepreneur, as do regular breaks from both wine and teaching. As he shared, “I constantly think about how lucky I am. I drink some of the best wines in the world for a living and get to teach people about them. It’s far more work than most would think, but I love my life.” Cheers to that!


  • Twin Cities Wine: Did you know that the shape of the glass you use to drink wine has a strong effect on how the wine presents itself both on the nose and on the palate? Check out Jason's website to learn more!
  • MailChimp: The email service Jason uses to send out his newsletter
  • Eventbrite: The event sales platform that Jason used to schedule and ticket his events

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

Yours in the revolution,


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Quote of the Day
"If you want to start a side hustle, set a target goal every month of something you want to buy or pay off with the money you earn. If you can pay your car or student loans off with a Side Hustle then you feel the value far more than just buying pizza and video games. That will keep you motivated to keep hustling."
—Jason Kallsen #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau