This transcript was generated from the episode audio and may contain minor errors.
[Music]
Hello there friends, listeners, side hustle school community. Welcome back, we're gonna start a brand new week today. My name is Chris Guillebeau. This is episode 464 of the show. Starting out with a strong story as we try to do every week.
Today is all about a college student who starts an historic letter subscription service. Really, really smart project. He's doing something fun and it's actually quite scalable. Now I don't think every side hustle needs to be scalable. There are lots of episodes, lots of features we do about somebody who does something that's gonna go on to make a couple thousand dollars a month and that's great.
Or alternatively, it's gonna make a lot of money in a short period of time, but because of the nature of it, it's not going to be sustainable. Like it's not gonna go on forever. And all of that is fine and well, but it's also great when somebody creates a project that has a potential at least to not only be an initial success, but to be a recurring success, typically with recurring revenue, which we'll talk about, but also something that can grow and serve a lot of people over time. That's exactly what we've got today with this story, a student who cashes in on his love of history by mailing beautifully designed letters to monthly subscribers. Along the way, he learned some important lessons about gift items, automation, and not listening to customers when they say they want something.
Good lessons there, so stay tuned. I'll say thanks to today's sponsor and then I'll bring you this story. [Music]
Michael Sitver is a college student and self-confessed history nerd from Chicago, Illinois. He's always loved studying the great historic events and people of times gone by. While standing in his mailbox one day, an idea struck him that would change the course of his own history.
He thought about how much he would enjoy receiving a letter written by a legendary figure from the past, like Einstein, Kennedy, Gandhi, or Churchill. He wondered if others would too. So he decided to find out in the form of a project that he hoped would make money. First, he crunched a few numbers, just ballpark calculations of price, profit margin, and estimated market size. Everything added up on his spreadsheet, so he knew this was an idea worth playing around with.
He chose a name, LetterJoy, and bought the domain. Then he used a service called Strikingly to quickly build a free landing page, which helped him to visualize the business and think through what the product and pricing would look like. Michael says he does this with a lot of ideas because it's a quick and easy way to figure out whether the idea really comes together. It's also a good test to see if he still has the, "Wow, this is cool" feeling after spending two hours thinking about it. In this case, the feeling endured.
After setting up the page, he was then ready to start seeking out customers, so he turned to his favorite niche history podcast as a place to advertise. He spent $80 on a month's worth of ads and the orders began to trickle in. Within a month, he had his first eight customers and was mailing them weekly letters that he designed and printed himself. Now there was still a lot to figure out at this stage. Fulfilling more than a handful of orders each week meant sorting out a proper system for tracking, printing, and sending the letters to each subscriber.
He also realized he was undercharging based on the actual cost of creating the orders. So Michael pressed pause on LetterJoy for a couple of months while he worked on creating a database and looking into designers and printers he could work with to smooth the process. When he took the business off pause, two months later, he was raring to go. So far, he'd invested just $100 into the business and he decided to spend the next $100 on marketing following the success of the podcast ad. This time he experimented with Twitter ads targeted to history buffs, which is now one of LetterJoy's main advertising channels.
Now this business is doing really well. Pricing is something else Michael's experimented with over time. He's currently charging $13 to $16 a month. The number of subscribers increases each month and revenue has doubled every couple of months as well. How much money are we talking about?
Well, last month, LetterJoy brought in five figures in net income. That's right, five figures last month. Like all good historians, Michael has learned from the past. His experience of running a business selling physical products on subscription has taught him a few lessons. Maybe these will be helpful to some of our listeners.
First lesson is to do a test run of the product before you start selling gifts or subscriptions that lock you in. You need to be able to make changes. The second is to pause before you scale, just like he did, make enough sales of your product to get an idea of how it works and which parts are slow or difficult. Then pause so you can fix them and build for scale. I thought that was pretty interesting myself.
I'd never actually thought about pausing a subscription business and then figuring out the kinks and then getting back to it. Smart idea. The third is to choose suppliers who can scale at the same pace you do. If you set things up with a supplier that you quickly outgrow, it can cause all sorts of headaches and sleepless nights. Might come back to that in the commentary section.
And finally, keep it simple, stupid from the start. Follow the KISS principle. When thinking about your production process, ask yourself over and over, how can I make this simpler? And when customers ask for options that create added complexity, say no. That's right, when customers ask for something, turn them down.
Simplicity is a higher value. LetterJoy operates differently now compared to its early days, but Michael says that smoothing out production has been a slow, steady process. Each week's new orders create a new opportunity to learn and iterate. Also, each new process and upgrade is funded by revenue from the business itself, rather than any outside investment. This is the side hustle school way, of course.
And as Michael puts it, he's building the plane as it flies. Not good to do for real airplanes, by the way. But for letters in the mail, that works. Over time, Michael has also learned a lot about his audience. And this is interesting too.
He had assumed that they would be similar to him. 18 to 25 year old history geeks. But he quickly saw that parents of young children and retirees were LetterJoy's key demographics. He's also seen that the majority of people want to buy a LetterJoy subscription as a gift for someone else. Once he learned this, he could update his messaging and target people differently in his online advertising.
So what's next? Well, Michael will be further automating the product process so that he can focus on new development, building out the marketing even further, and all while continuing to enjoy geeking out on history's greatest stories for a few hours each week. Is LetterJoy destined for greatness to be recorded in history for all time? Well, that's hard to say. It might take a while.
But even if not, it's a most notable side hustle success. Awesome, congratulations to Michael. I love this project. I especially respect how he's focused on automation. And not just automation, but learning as he's gone along and adapting, iterating, taking the new information that he acquires, and then adjusting his process.
Very smart, I also loved how he doesn't listen to his customers when they request different features and options. It is a common mistake of new small business owners, new entrepreneurs, new side hustlers, to think that they have to give customers everything they say they want. That is not true for all sorts of reasons. One, because what people say they want and what they actually want are not always the same thing. But also, because your capacity is limited.
You have to choose what your vision's gonna be, what your focus is. And also, people's needs are different. So most likely, you're gonna be serving more than one person. Michael has hundreds of customers. He can't do custom orders for each person, or for even any particular subset of that group.
So he's got his eyes on the prize. He knows what he's trying to do overall. I think that's good. Now, in the notes, I forgot to mention a couple of his challenges. Long-time listeners know that we don't shy away from talking about what's hard, about the mistakes people make, about the failures we all make.
Those things are common. I never want to say that starting this kind of project is easy. It's not that it's easy, it's important. And you can simplify. You can figure out how to do it.
But you usually have to overcome some things along the way. So in Michael's case, he says, here is a non-exhaustive list of some of the production crises we've had. One time, our third-party fulfillment company lied about fulfilling orders, requiring us to build our own fulfillment system in a week. Another time, a bug in his code caused a number of subscribers to get duplicate letters in one week. It's like, surprise, I guess Gandhi decided to write twice.
Thanks, man. And his high-quality, high-speed printer broke down in its second week, forcing him to stay up until 3 a.m. three days in a row to get orders out. All right, so again, it's not easy. I'm not selling a dream, I'm selling reality.
This can be tough, but the question you have to ask yourself is, is it worth it? Is it worth it for you? So obviously, Michael's been able to say, yes, it's absolutely worth it for me, and so many of the other people that we talk about, and so many of our listeners as well. But ultimately, that's a question for you, because you're gonna be the one who has to face those challenges. And I share these stories as living, daily examples of people who've faced those challenges, found a way to overcome them, and maybe in some cases have gone on to make an historical success.
Or even if it's not historical, it's making their life better in a tangible, meaningful way. That is, of course, my goal for you as well. Thank you for listening today. As always, inspiration is good, but inspiration with action is better. If you'd like to learn more about letter joy and all the different resources I mentioned, just come and check out the show notes for today's episode.
Those are it, sidehustleschool.com/464. We have another episode coming up tomorrow and each day this week. Be sure you're subscribed to Napple Podcasts or wherever you listen to podcasts. I don't want you to miss something that could make a difference in your life. So I'm gonna do the best job I can in bringing that to you.
My name is Chris Guillebeau for Side Hustle School.
