10 min 49 sec

Think Like a Lawyer: An Underground School For Lifelong Learning

An unconventional attorney starts a non-traditional adult education school that grows to more than 900 courses.
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What It's About

A lawyer objects traditional higher education seeking to make it more affordable and accessible.

Business Model
Skills Required
Organization & Coordination
Profit Potential

Words of Wisdom

Take small steps and have a theory to test. Validate the theory, yes or no. If you're wrong, that's great to know quickly and cheaply. What's next? What's your next theory? Ask yourself how can you validate it quickly and cheaply.

Fun Fact

In the USA the cost of grad school can be anywhere from $5000 to $50,000 per year. This is an astronomical cost that saddles many students with debt for the majority of their lives. Instead, more people could move to smaller schools and online courses to obtain the skills they need.

Notes from Chris

Episode 802

Douglas Tsoi is passionate about learning. After finishing college, he went on to law school. But, after graduating and entering the workforce, the 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.

As he looked around he felt an undeniable sense that this was affecting people. Most people go through school, maybe getting a degree on the way to full-time employment. Then, they stagnate and fall into a life of repetition where they don’t learn much.

So after pondering for a while, he put two and two together. He believed if people had an easy, affordable way to learn new things, they’d jump at the chance. He decided to do something about it, and, in 2014, made a move to open his own school.

Every great change starts with that small step, and Douglas was about to take his. To begin, he’d teach only one class. The topic for that course 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 decided to turn to the local community center to rent out a space. Most cities have something like this and they can 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 registrants to fill it, class was in session. The first course went well. Douglas got a thrill out of teaching, and his students equally enjoyed learning what he had to offer.

When it was over, students and instructor all went out for drinks to celebrate. This was a tradition that would continue for all his classes over the next year.

After the first course, Douglas had the courage to put a little more effort into his project. He decided to officially name it and launch a website. He called it Portland Underground Grad School, or PUGS for short. For the site, he paid $300 for the setup. With that, his little school was official.

During the first year, Douglas continued to teach that same course every month, and then he added more. He’d rent rooms in community centers around the city to keep the costs down so he didn’t need a permanent space. Over the next four years the volume of courses grew to eight per month, or two every week. Of course, Douglas couldn’t teach all the different courses himself, so he eventually found instructors to teach them.

He has a unique 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 they offered social justice courses that proved very popular. Third, and perhaps most importantly, are the instructors themselves. Do they have an audience already—and how effective will they be at promoting a course to their own networks?

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. So, he landed on a scaling pricing model based on a person’s hourly work rate. So, those with a higher income paid more than those who earned less. This model proved extremely popular and its uniqueness was a big factor in growth. This brings us to 2018, where PUGS was running hot. Douglas had built the school up to 75 different courses, with 900 students and, and he was earning $5,000 a month from his little side hustle. Those figures caught the attention of a buyer through his network, and he was able to sell PUGS for a tidy profit.

While 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 that gives him a financial cushion to start more side hustles and build other businesses. And that’s exactly what he’s done.

Throughout Douglas’s 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 they could go off and make their way in the world a little more equipped.

So, Douglas has combined all those things into his next side hustle: it’s called the School Of Financial Freedom. Douglas’s new school that aims to help people take control of their finances, and live the life they want.

He plans to teach people good financial habits and the power of making your money work for you. Launching PUGS was the ultimate learning experience. He hopes he never stops learning, teaching, and building.



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
"When you're getting started, start with a theory and then take small steps until you validate it. Because, if you're wrong, that's great to know quickly and cheaply."
—Douglas Tsoi #SideHustleSchool

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Chris Guillebeau