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

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.

    #2719 - Q&A: “Stuck in low-paying gigs…”

    #2719 - Q&A: “Stuck in low-paying gigs…”

    In this episode, we help a contract bookkeeper boost her productivity and income. Discover essential tools and techniques for managing your workload, prioritizing tasks, and landing high-value gigs.
    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
    #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

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