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Side Hustle School

Ep. 3270 - Weekend Workshop: From Rock Bottom to Business Empire

Side Hustle School

Chris Guillebeau / Onward Project

Business, Careers, Entrepreneurship

4.8 โ€ข 3.3K Ratings

๐Ÿ—“๏ธ 14 December 2025

โฑ๏ธ 7 minutes

๐Ÿงพ๏ธ Download transcript

Summary

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: a British woman goes from living in a shelter to running a million-dollar business.

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

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. ๐Ÿ˜Ž ๐Ÿ™๐Ÿผ 



See omnystudio.com/listener for privacy information.

Transcript

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0:00.0

Lemonada.

0:02.7

What if being a teenage mother living in a homeless shelter could actually become the foundation for a multi-million dollar business?

0:18.6

That is exactly what Naomi Dunford from the UK accomplished when she

0:22.4

transformed her desperate circumstances into the motivation for creating itty biz.

0:27.4

Welcome back to Saitosyl School. My name is Chris Gillibow, your host. This is a segment known as

0:32.0

Weekend Workshop. We're going to title this one from Rock Bottom to Business Empire.

0:36.6

The segment is all about helping you learn the key steps to a new hustle, one step,

0:40.7

or concept per week.

0:42.6

It includes activities, examples, and more.

0:45.2

We're using the book side hustle from idea to income in 27 days, which is available

0:49.9

wherever books are sold.

0:51.7

And for the first half of the year, we went through the 27 steps in the book.

0:55.5

Now, in the second half, we're looking at more detailed case studies so you can hear and

0:59.7

understand how people apply the framework. So I like to give you these little inspirational stories

1:04.0

as we do and give you some practical steps, maybe some grounding for your first or your next

1:08.8

side hustle idea. So let's talk about Naomi.

1:11.6

Naomi's actually a friend of mine. I haven't talked for many, many years, but long ago, I used to

1:15.5

know her. She was one of the original bloggers in the cohort that I kind of came up with, 2008,

1:21.9

2009, 10, et cetera. And her story, as I noted, actually began in a homeless shelter. She was a teenage mom, a high school

1:29.6

dropout. Facing a future with seemingly no viable options. So the statistics were stacked against

1:35.8

her, but Naomi had hidden advantages. Her dad had built several businesses. Her mom worked in

1:41.4

marketing and her grandfather had been in advertising. So she had this

...

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