2,000 episodes

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.

Side Hustle School Chris Guillebeau / Onward Project

    • Business
    • 4.7 • 3.2K Ratings

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.

    #2718 - First $1,000: Birdwatching App Flocks to Success

    #2718 - First $1,000: Birdwatching App Flocks to Success

    In this week's First $1,000 segment, we hear from a tech-savvy side hustler who combined their love for coding and birdwatching to create a unique mobile app. Learn how they monetized their passion project through ads and premium features.
    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: team@sidehustleschool.com
    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.substack.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. 😎 🙏🏼 

    To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

    Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

    • 7 min
    #2717 - Q&A: “I changed cities and lost my local clients…”

    #2717 - Q&A: “I changed cities and lost my local clients…”

    In this episode, we help a math tutor rebuild her client base in a new city and explore ways to grow her side hustle beyond local clients.
    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: team@sidehustleschool.com
    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.substack.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. 😎 🙏🏼 

    To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

    Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

    • 7 min
    #2716 - Q&A: “How can I hire my first assistant?”

    #2716 - Q&A: “How can I hire my first assistant?”

    In this episode, we help a reseller from Minneapolis navigate the process of hiring their first assistant. Learn how to find the right candidate, onboard them effectively, and handle the legal and financial aspects of expanding a side hustle team.
    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: team@sidehustleschool.com
    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.substack.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. 😎 🙏🏼 

    To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

    Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

    • 7 min
    #2715 - Failure Friday: Vintage Watch Restorer Learns Timely Lesson

    #2715 - Failure Friday: Vintage Watch Restorer Learns Timely Lesson

    In this week's Failure Friday, a passionate vintage watch restorer shares a cautionary tale about the importance of clear communication after a misunderstanding with a client nearly costs him his sterling reputation.
    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: team@sidehustleschool.com
    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.substack.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. 😎 🙏🏼 

    To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

    Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

    • 9 min
    #2714 - TBT: Bookworm Cashes in on Audible Affiliate Book Reviews

    #2714 - TBT: Bookworm Cashes in on Audible Affiliate Book Reviews

    In this week’s “Throwback Thursday” segment, we meet a savvy schoolteacher who's discovered a lucrative side hustle in reselling returned goods on Amazon and other online platforms. Learn how he navigates bulk auctions, inventory management, and product selection to turn a profit and supplement his teaching income.
    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: team@sidehustleschool.com
    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.substack.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. 😎 🙏🏼 

    To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

    Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

    • 7 min
    #2713 - Q&A: “My clients aren’t paying my invoices on time…”

    #2713 - Q&A: “My clients aren’t paying my invoices on time…”

    In this episode, we help a freelance writer tackle a challenging client situation. Learn how to set clear boundaries, ensure timely payments, and protect yourself from problematic clients.
    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: team@sidehustleschool.com
    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.substack.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. 😎 🙏🏼 

    To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy

    Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

    • 7 min

Customer Reviews

4.7 out of 5
3.2K Ratings

3.2K Ratings

HeyTriciaC ,

Motivating!

I love listening to this show. Every single time I find myself more motivated to keep up the pace! Thank you!

Fitterthanyou ,

Inspiration is good

Right after my morning meditation and coffee listening to side hustle school is the first thing I do. Each show inspires me every day. I'm gaining enough inspiration and knowledge from each of the shows to hopefully someday take action and start my own side hustle. The show is so well done, short and to the point. I can't wait to hear what's coming the next morning.

Cindi Kolf ,

Love Side Hustle!

To the point with lots of good information! Thank you, Chris!

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