Think Like a Lawyer: An Underground School For Lifelong Learning

This transcript was generated from the episode audio and may contain minor errors.

Are you a lifelong learner? What are you learning? Since you're listening to Cytosville School, I'm going to assume you're interested in starting a money-making project of some kind. That's probably not all you're interested in. So, what else are you learning? What are you studying?

What are you trying to master? Or maybe just dip your toes into... Over here, I recently went to a yoga retreat for the first time ever. It was in Arizona for a few days, and I really enjoyed it. I've been doing yoga for a few years, but I've never actually gone to a yoga retreat.

So, that was fun. And I also got a running coach who, in two short sessions, has shown me a lot that I had no idea about. Which is kind of ridiculous, because I used to think, like, running, you just go out and do it. Like, why do you need to be taught how to run? But apparently, you actually do need to be taught, at least if you want to improve, if you want to prevent injury, you know, take care of yourself, all that kind of stuff.

So, those are a couple things for me. And one thing that's really great about the internet is the access that we all have to so many learning resources. You can learn all kinds of stuff through podcasts, of course. But not only that, of course, there are many, many other resources as well. And it's not just the online world.

Non-traditional and far less expensive schools and continuing education programs are flourishing. When I say far less expensive, I'm comparing that to traditional colleges and universities. So, in today's story, because there is a segue, there was a point, in today's story, you'll hear about a lawyer who opens an underground school for lifelong learning. This school grows from one class that he teaches in a small community center all the way to 75 classes with 900 students. He actually goes on to sell this project, which I'll tell you about.

So, we're calling it Think Like a Lawyer, an Underground School for Lifelong Learning. That story is coming right up. Stay tuned. Douglas Soi is passionate about learning. After finishing college, he went on to law school.

After graduating and entering the workforce, a longtime Portland, Oregon resident noticed something. Opportunities for learning new and interesting things were few and far between, at least the way that he envisioned and the way that he learned best. As he looked around, he felt an undeniable sense that this was affecting people. Most of us go through school, maybe earning a degree on the way to full-time employment, and then sometimes we stagnate, we fall into a life of repetition, but we don't learn that much. When Douglas was positive, this wasn't a natural way for humans to behave.

He believed the desire to learn is lifelong, and that picking up a new skill or interest, particularly at the same time other people are doing it, is a great way to improve your well-being. So, after pondering for a while, he put two and two together, and in 2014 made a move to open his own school. Now, how do you go about opening your own school? Douglas was no Professor X from the X-Men. He didn't have the funds, real estate, or superpowers to open a traditional college or university, and he also didn't want to.

Douglas was just a regular guy, but even a regular guy or woman can do something amazing by starting small and having conviction. Maybe they can even change the world. Every great change starts with a small step, and Douglas was about to take his. To begin, he'd teach only one class. The topic for that class was criminal law, how to think like a lawyer.

Law was what Douglas knew, so compiling the subject matter into something easily digestible was simple. It took him a month to prepare the course. To drum up interest, he turned to Facebook and presented the idea of his course to his network and a few Portland-based groups. Next, he needed a place to host the class, somewhere that didn't cost a lot of money. He turned to his local community center to rent out a space.

Many cities have something like this. They can often be a cheap way to have a party, arrange a meeting, or, in Douglas's case, start a school. Now that he had a classroom and enough students to fill it, class was in session, and that first course went well. And it was over students and instructor all went out for drinks to celebrate. This became a tradition that would continue for all his classes over the next year.

Also, after that first course, he had the courage to put a little more effort into the project. He decided to officially name it, which it didn't have a name before he did the first course, and launch a website. He called it Portland Underground Grad School, or PUGS for short. During that first year, Douglas continued to teach the same course every month, and then he added more courses. He'd rent rooms in different community centers around the city to keep the cost down so that he didn't need a permanent space.

Over the next four years, the volume of courses grew to eight per month. And, of course, he couldn't teach all the different courses himself, so he eventually found other instructors. He has a unique set of criteria for coming up with what to offer through PUGS. First, he looks at his personal experience. What would he find interesting and beneficial?

Second, what's popular at the moment? For example, after the 2016 election, the college offered social justice courses that proved very popular. Third, and perhaps most importantly, are the instructors themselves. Do they have an audience already? Are they the right person to teach the topic?

And how effective will they be at promoting a course? By looking around the community, Douglas was able to find suitable people to teach classes on topics like self-improvement, creativity, and culture. Naturally, some were more popular than others, so every now and then the timetable was switched out to make way for something new. Now, speaking of new and unique, here's something that's pretty cool. Douglas didn't want the price to be a limiting factor to anyone.

He felt like anyone who wanted to learn should be able to enter his class, so he chose a scaling pricing model based on a person's hourly wage. Those with a higher income paid more than those who earned less. This model proved extremely popular. Its uniqueness was a big factor in growth. All this brings us to 2018, where PUGS was running hot.

Douglas had built the school up to 75 different courses with 900 students. He was also earning $5,000 a month. And again, remember, this is a side hustle. Those figures caught the attention of a buyer through his network, and he was able to sell for a tidy profit. While starting the school and then growing the business for a sale was never the intention when he was starting out, it was a nice byproduct.

What he's most excited about is it gives him a financial cushion for other projects. And that's exactly what he's doing. Throughout Douglas' time with PUGS, he learned to love working on a small business. On top of that, he loved the financial freedom it gave him and the ability to be flexible with his life choices. He also loved teaching, sharing his knowledge with others so that they could go out and then make their way in the world a little more equipped.

So Douglas has combined all these things into his next hustle. It's called the School of Financial Freedom. This new school aims to help people take control of their finances, live the life they want. He plans to teach good financial habits and the power of making your money work for you instead of the other way around. Launching PUGS was the ultimate learning experience, hopes he never stops learning, teaching and building.

Well, I love the name Portland Underground Brad School. It has this subversiveness to it. It almost just, you know, right from the title you hear underground. It's like something that is again subversive or just deliberately non-traditional. So you get a little bit of a concept right away.

And of course, he then did a wonderful job of marketing it, building up, developing courses, you know, recruiting other instructors, you know, all those kinds of things. So what if you out there want to sell your side hustle or build your side hustle to the point where you can sell it? Well, you have to kind of do something like heat it, which is not build a brand on himself, take the time to think about structure, to create some process that can easily be followed by somebody else so it's not all dependent on you or any one particular person. And last but not least, you need to build up that monthly recurring income so that it is pretty consistent and not just consistent but also growing. That is the path to selling your business at a good multiple.

And the valuation is going to be based to a large degree on that monthly income number. But of course, you don't have to grow your side hustle to sell it. You can just grow it because it's important to you. And that is totally valid and wonderful too. Now, speaking of good things and non-traditional education, I want to give a shout out to my friend Michelle Jones from the Wayfinding Academy, another non-traditional school in Portland, Oregon.

She recently gave a TEDx talk that she has been preparing for several months for. Michelle is really passionate about non-traditional education and she started this whole college called the Wayfinding Academy a couple of years ago. Her talk is called "How to Do College Better." It's available now for free online. And of course, I will link that up in the show notes. Speaking of show notes, those notes are at sidehustleschool.com/802.

In addition to that talk, we'll link up pugs, anything else that I talked about through the episode, and perhaps any other fun resources. Who knows? There could be something fun there. I'm just saying. So wherever you are, I hope you are a lifelong learner as well.

Ask yourself, you know, I'm busy, I don't have a lot of time, but is there something I can learn? Is there something else that I'm not learning right now? It's interesting to me. Because learning can make our lives better, even if we don't have a grand purpose to it. I really believe that.

I think it's okay to go and take a couple of language classes, even if you're not sure you want to, you know, ultimately become fluent in that language and move abroad with the State Department. You could learn to knit, even if you never want to make a quilt. You know, just learning for its own sake is a good thing. So I encourage you to do some learning today. I'm going to go out and do that myself.

I'll report back on my next yoga retreat or whatever I end up doing. And yeah, so much more is on the way. Do come back tomorrow for another episode. My name is Chris Guillebeau, and this is Side Hustle School. from The Onward Project.