What It's About
A chance encounter leads to a new side hustle opportunity—and eventually, a full-time business.
Business Model
Skills Required
Complexity
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!
MENTIONED IN THIS EPISODE:
- 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
- Wine Enthusiast | How to Taste Wine: Learn how to taste and evaluate a glass of wine like an expert by following our wine tasting tips. First step? Find out the right environment for tasting
- Stressed-Out Mom Gives Up TV to Launch Her Hustle: How a San Diego accountant coping with the struggles of new motherhood launched her own private label wine hustle for stressed out parents like herself
- Busy Marketing Professional Fills Niche with Biking Wine Tours: A marketing executive sees an opportunity to fulfill a niche tourism need in an up-and-coming wine region
Download Episodes By Months: Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC | Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC | 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 |
Resources
GET $625 IN FREE TRAVEL
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! ✈️
CREATE YOUR ONLINE STORE
Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.
Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today!
Learn More
Quote of the Day
Sponsors & Gratitude
Create a Stunning Website With Wordpress
Today’s episode of Side Hustle School is brought to you by Wordpress.com! Whether you’re looking to create a personal blog, business site, or both—you’ll make a big impact, when you build your website on WordPress.com. 💻
Get 15% off when you build your website with Wordpress.com—use promo code PODCAST when you check out.
Get Started 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.
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,
