This transcript was generated from the episode audio and may contain minor errors.
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Side hustle school friends, listeners, and community, welcome back. My name is Chris Guillebeau. I've got a great story for you today. We're actually gonna talk about an important principle that we haven't really touched on very much yet. This principle is that going from $1,000 a month to $5,000 a month is not five times as hard as getting to $1,000 a month in the first place.
Did you follow me there? In other words, it's not nearly as hard to make more money from something that's already working as it is to get that thing up and running in the first place. So in this example, going from $1,000 a month to $5,000 a month is not five times as hard. It's more like twice as hard. So there's an advantage of scale and efficiency as you get better at doing this.
Now we'll talk about that lesson in the context of a story. It's from a guy in Minnesota who earns $70,000 a year teaching wine classes. He actually does this full-time now, but as you might imagine, he didn't set out to do it full-time. It all started when he had a job and first decided to start a side hustle. I'll bring you a story in just a moment.
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Today's featured hustler is Jason Carlson from Minnesota, whose side hustle came directly from his day job, but in a very unexpected way. 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 little of it until a week later when he saw the same BMW race into the parking lot and the same lawyer running into the store again. Jason thought that guy must have hated the wine, so he actually hid in the store and hoped that somebody else would help him.
But the guy eventually found Jason and said, "You're the one who picked out all those wines, right?" They were incredible, but so obscure, nobody knew what they were. So fill my cart up again with those 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 light bulb moment. He filled up that guy's cart again, went to his house and did the wine tasting.
As part of the tasting, he presented maps, talked about history and geography, and of course he got paid for it. Now he didn't get paid much. That first time he only charged $50, most of which went toward the purchase of a large pizza on the way home, but still, it was the start of something big. The very next week he began a side hustle educating people about wine. Now at the time he was running another side business in wedding photography, so he knew about the process of logistics.
He filled out a form with the state of Minnesota, he paid a couple fees, opened a bank account, and was officially in business as a wine educator. From there, Jason bought a domain name for $80. Remember, this was 1997. Domain names have come way down in price since then and created a website using HTML. Now this meant that unlike websites today, he couldn't just go and add a new blog post.
He had to rewrite the code every time he wanted to update the website. But even though the website, in his own words, looked like hell, people still found him. Twin Cities Wine Education was officially out there. Jason wanted to be careful about how he presented himself, since he worked in a wine shop and didn't want his boss to think he was trying to steal his customers. So he only brought up his wine education classes when a customer asked, and he was also transparent with his boss.
Since Jason was a dedicated employee, it didn't take his boss long to realize that the side hustle was actually a benefit to the shop's end goal of selling more wine. Initially, Jason's only objective was to bring in some extra income, and for a number of years, he did just that. He would put in enough effort to make a few hundred dollars a month, teaching only a couple classes would make enough to cover his car payment and give his budget a little extra room. It wasn't until 10 years later that Jason realized he could really ramp up this project without putting in a ton more effort. He first gave himself the goal of getting to $1,000 a month, which he very easily hit through a combination of raising his rates a bit and offering more classes.
A couple years later, he read a book called "The Art of Nonconformity," crazy title, and a particular line jumped out at him. That line was taking $1,000 a month business and turning it into a $5,000 a month business is not five times as hard, it's twice as hard. Reading that sentence, along with starting a job with a new company that turned out to be the wrong fit for him, was the spark he needed to go toward full-time self-employment. Keep in mind, he'd been doing this for a while, and he'd seen a lot of success. He just needed to make more money with it.
So to start off, he focused on streamlining. He rebuilt the website using WordPress this time, so it was much easier to use and looked more up-to-date. He also started sending out newsletters more consistently using Mailchimp. He used Eventbrite to schedule and ticket his events, which made it easier to track his sales and attendees. With Eventbrite, he also had the added advantage of bringing in new customers that find his classes directly on that platform.
With some better business tools in place, Jason focused on expanding his class offerings. He has an ultimate intro to wine class at an affordable price point, just $40. But then he also started scheduling mid- to high-end classes for customers who have graduated or already have some familiarity. These courses run more like $100 to $125 a person, and Jason treats them more like an experience than a class. Through his combined efforts working on both the backend and the front end of the business, he was able to quit his job in 2015 and focus solely on Twin Cities wine.
Jason now makes about $70,000 a year teaching people about wine, and he works hard for it. In fact, he says I'll sometimes choose to work every available hour in a week, but I have the freedom of my own schedule, a major benefit. His side hustle turned full-time hustle has now spawned side hustles of its own. Say that three times fast. Jason and his wife started another project called The Flying Grape, where they would take small groups of people to wine regions around the world.
They took a group to Portugal in 2016, had a great time, but they also realized it was gonna be a real challenge to make consistent money from leading these tours. So then they tweaked that project to be a wine travel advice site that will lead people to specific tour operators. And from those tour operators, they'll get a referral fee. In other words, they're doing less work while still generating some income. Jason has also launched Vine Thinking, a consulting and training program for wholesalers and importers.
At this point, Jason estimates that he's taught over 10,000 people in his intro to wine class alone. He says, "I constantly think about how lucky I am, "I drink some of the best wines in the world for a living, "and I get to teach people about them. "It's a lot more work than most people think, "but I love my life." Let's raise a glass to that. [Music]
All right, I too often think about how lucky I am, how fortunate I am that I get to do something I enjoy, to write, to travel, to produce this show for you. So I totally identify with Jason's comments there at the end.
I work all the time, but I love my life. If you can get to something that you enjoy doing, you look forward to doing, you're not really gonna worry too much about how much time you spend on it. So let's talk about this idea of going from $1,000 to $5,000 a month, and why it's not five times as hard. It's because in that situation, 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. That's what he did with the different classes. Become more efficient with the right tools and resources, like he did with Eventbrite, WordPress, Mailchimp, and create product and service extensions, like the Wine Tour, then the Wine Tour referral extension, and then the training program for wholesalers. All of these things are like a collection of income sources around a focused topic.
So he's still teaching people about wine, but since he has a proven model, he simply expands the model. That's why it's not exponentially harder to grow a little business like this. In fact, it's usually much easier than starting something new. This is also why I think it's so important to get to your first side hustle income as quickly as possible. That's why I have this $500 a month figure that I use.
If you're not familiar with that, every episode of side hustle school, the person is making at least $500 a month from their project. And often, as you know, they're making much more than that. But $500 is the minimum. And my goal for everyone who reads the side hustle book and applies it is that they'll make at least that much too. And I wanna get you there quickly so that you then have the opportunity to do what Jason has done, to go from 500 to 1,000, and then eventually 1,000 to 5,000, or whatever the numbers are for you.
We'll talk about that a bit more as we go on, because as I said, I believe it's important. But for now, I'm gonna close it out. As always, inspiration is good, but inspiration combined with action is better. Don't just be inspired. Think about how you can apply this to your life.
Today's show notes are at sidehustleschool.com/297. Links to everything I mentioned in the episode. Let me know what you think. You can write in from the site, or you can send a quick note to the podcast at sidehustleschool.com. Or there's also that new thing called social media.
Have you heard of it? Thank you for listening. I'm Chris Guillebeau for Side Hustle School. [Music]
