4.8 • 3.3K Ratings
🗓️ 27 July 2025
⏱️ 7 minutes
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This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: from doing to teaching.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.
Show notes: SideHustleSchool.com
Email: [email protected]
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com
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0:00.0 | Lemonada. |
0:02.7 | What if the key to scaling your expertise wasn't doing more work, but teaching others to do the work themselves? |
0:17.5 | That's exactly what Shannon Madden discovered when she transformed her web design hustle from |
0:22.0 | trading time for money into a scalable teaching business that reached thousands of students. |
0:27.8 | Hey friends, welcome to Sautil School. Chris Gillivow here, your host. This is our weekend workshop |
0:32.9 | segment. It's all about helping you learn the key steps to a new hustle in 2025, one step or concept per week. |
0:39.2 | It includes activities, examples, and more. And of course, it's all free. For the first half of the year, |
0:44.1 | we went through the 27 steps in the book Side Hustle, from idea to income in 27 days. Now in the second |
0:50.2 | half, we're looking at more detailed case studies so you can understand how people apply |
0:54.4 | this framework. So let's talk about Shannon, Shannon Madden. Shannon Madden worked a full-time |
1:00.5 | IT job, but it developed strong WordPress skills on the side. WordPress is a platform you can use to |
1:06.7 | make websites. And she initially monetized this knowledge by taking on freelance web design |
1:11.6 | projects for small businesses. And that was fine, steady work, well-paying, but Shannon quickly |
1:17.5 | ran into the classic service provider problem, which is that her income was directly tied to |
1:22.7 | her available time. To earn more, she had to work more hours. There was no way to scale |
1:27.3 | beyond those time |
1:28.4 | limitations. She also noticed something interesting about her clients. Many were frustrated by their |
1:33.4 | dependence on web designers for every small update. They wanted to learn how to manage their own |
1:38.3 | websites, but felt overwhelmed by WordPress's complexity. WordPress is the kind of platform that can be |
1:43.8 | simple or it can be |
1:44.7 | complex. There's a lot you can do with it, but sometimes beginners or newbies struggle to adapt. |
1:50.8 | And this frustration represented an opportunity. Shannon didn't recognize it first, but then she |
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