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Side Hustle School

A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.

Weekly hand curated podcast episodes for learning

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The best episodes ranked using user listens.

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#666 - Weekly Recap: Don’t Sit On Your Ideas

In our forty-third recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

12mins

28 Oct 2018

Rank #1

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#709 - Stay At Home Mom Delivers Fresh Side Income

After relocating to Tennessee from Canada, a restless homemaker creates an online farmers market, delivering produce to more than 200 homes a week. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

10mins

10 Dec 2018

Rank #2

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#598 - Crafty Mompreneur Brings in $12,000 in Eight Weeks

A mom in search of a new side hustle creates a profitable after-school enrichment class.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

11mins

21 Aug 2018

Rank #3

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#732 - PE Teacher Resells Concert Tickets, Earns $12,000/Month

After selling a few tickets to concerts he couldn’t attend, this teacher found himself with a lucrative side hustle that changed his life. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

10mins

2 Jan 2019

Rank #4

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#1108 - CLASSROOM: Four Ways to Identify Moneymaking Ideas

Where do moneymaking ideas come from? From the idea fairy, of course! (Not really. In this episode, you’ll learn four easy ways to generate valuable ideas.) 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. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

12mins

13 Jan 2020

Rank #5

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#893 - Millennial Invests Side Income For Passive Profits

A man on a mission goes from unemployed to day job, then from side hustler to millionaire in five years. Putting 80% of his income into investments for an early retirement made total cents.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

10mins

12 Jun 2019

Rank #6

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#670 - Financial Blog Sprouts into $35,000/Month Money Tree

A registered nurse and financial manager start a blog for millennials. After a rough beginning, they figure out their audience and go on to earn tens of thousands of dollars a month. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

9mins

1 Nov 2018

Rank #7

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#874 - Teacher Hustles to Pay Off $100,000 in Student Loans

A young teacher uses tutoring and babysitting to pay off more than $100,000 in student loan debt in just three years.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

11mins

24 May 2019

Rank #8

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#834 - WEEKLY RECAP: How to Calculate the Value of Your Time

In our fifteenth recap of Season III, we'll highlight the lessons learned in this week. Also: an audio update from a previous case study!Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

16mins

14 Apr 2019

Rank #9

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#1098 - Q&A: What kind of business can I start with $300?

If you only have a small amount of money, what’s the best side hustle to pursue?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. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

8mins

3 Jan 2020

Rank #10

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#731 - Season III Begins! Make 2019 Your Best Year Yet

We’re back for the third year in a row with more stories! Here’s what it’s all about and what you can expect as we level-up for our awesome listeners.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.com Learn more about your ad choices. Visit podcastchoices.com/adchoices

6mins

1 Jan 2019

Rank #11

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#1164 - CLASSROOM: The MVP of Minimum Viable Products

Let’s break it down: what do you REALLY need to launch your product or service in the next 30-90 days?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. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

12mins

9 Mar 2020

Rank #12

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#880 - Second Grade Teacher Earns Second Income

After getting married, this full-time teacher draws on her organizational skills to start her own wedding planning business.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

9mins

30 May 2019

Rank #13

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#632 - Sound Engineer Makes $80,000/Year Handing Out Free Maps

A former sound engineer in Texas maps out a successful career by providing free information guides for hotel guests. The guides are underwritten by advertisers, who pay for their business to get in front of out-of-town guests.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

9mins

24 Sep 2018

Rank #14

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#1210 - Q&A: Should I quit my job and go full time with my hustle?

It’s a great place to be: your side hustle is earning as much money as your job does. But what comes next … and how do you navigate this choice?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. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

8mins

24 Apr 2020

Rank #15

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#622 - When the Rubber Hits the Road, This Mom of Three Earns $5,000/Month

After making a simple change to the color of her custom-image rubber ink stamps, this interior designer and mother-of-three from Texas began earning $5,000 a month.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

9mins

14 Sep 2018

Rank #16

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#1122 - CLASSROOM: Deciding on an Idea

If you have a lot of ideas and aren’t sure which one to start with … listen to this episode. 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. Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

14mins

27 Jan 2020

Rank #17

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#946 - WEEKLY RECAP: Warren Buffet’s “Five Goals” Rule

 In our thirty-first recap of Season III, we'll highlight the lessons learned in this week. Also: an audio update from a previous case study!Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

12mins

4 Aug 2019

Rank #18

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#859 - Working Military Mom Finds Success Working Virtually

Leaving the corporate world behind, a mom and military wife now earns 6-figures helping people learn the world of virtual assistance.Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

11mins

9 May 2019

Rank #19

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#718 - “Middle Class Dad” Earns Passive Income from Parenting Advice

Did you hear the one about the dad with the blog? He earns an extra $2,000/month. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeau Learn more about your ad choices. Visit podcastchoices.com/adchoices

9mins

19 Dec 2018

Rank #20