
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.
Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Latest episodes

Sep 20, 2024 • 6min
#2820 - Failure Friday: The Downside of DIY Platforms
This week features a tech-savvy course creator who shares their experience trying to build a DIY platform to save costs. They faced unexpected technical challenges, leading to a realization about the drawbacks of DIY solutions. The discussion highlights the importance of prioritizing content creation over handling all the technical aspects themselves. By considering a turnkey service, they could have enhanced productivity and focused on what truly matters: delivering value to their students.

Sep 19, 2024 • 5min
#2819 - TBT: Building a Range of Productivity Tools
In this throwback segment, a savvy seller of productivity guides shares how he transformed his initial success into a thriving digital business, pulling in over $100,000 a year. He emphasizes the significance of customer feedback that guided him to diversify his offerings from a single guide to a complete suite of productivity tools. The power of effective email marketing and adapting to market demands is highlighted as key strategies in his journey, showcasing the importance of evolving with your audience.

Sep 18, 2024 • 5min
#2818 - Q&A: “My subscribers are paying for nothing…”
Discover how to tackle the ethical challenges of charging subscribers who aren't receiving the promised service. Dive into the importance of transparency and communication in maintaining trust. Explore practical strategies to navigate these dilemmas while ensuring that subscribers feel valued. This engaging discussion offers valuable insights for anyone involved in subscription services.

Sep 17, 2024 • 5min
#2817 - Q&A: “How can I identify and develop side hustle skills?”
Listeners learn how to discover their unique skills for a successful side hustle. The discussion emphasizes the importance of self-assessment and turning expertise into marketable services. There's a focus on experimentation and continuous learning as key components of the side hustling journey. Practical tips and insights help demystify the process, encouraging anyone to start earning extra income without leaving their job.

Sep 16, 2024 • 6min
#2816 - First $1,000: Nashville Branding Agency Gets Personal
In this episode, a dynamic duo from Nashville shares their journey of establishing a personal branding agency. They discuss how they turned their passion for digital marketing into a successful service for entrepreneurs and influencers. Listeners will learn about the pivotal role of storytelling in branding and hear about their milestones, including their first $1,000 earned. The insights on overcoming initial challenges and discovering what empowers individuals make this conversation both inspiring and practical for aspiring business owners.

Sep 15, 2024 • 5min
#2815 - Q&A: “Should I get an expensive booth at a trade show?”
Is an expensive trade show booth worth the hefty price tag? This discussion dives into critical factors to evaluate before making the investment. Consider your business goals, potential costs, and learn from the experiences of previous exhibitors. Discover how to make informed decisions that could impact your side hustle's success.

Sep 14, 2024 • 4min
#2814 - Q&A: “How can I turn organizational skills into a business?”
In this episode, we explore how to turn organizational skills into a profitable consulting service. Learn how to define your niche, build a portfolio, and market your services to attract clients and grow your 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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.substack.comIf 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/adchoicesSee omnystudio.com/listener for privacy information.

Sep 13, 2024 • 7min
#2813 - Failure Friday: IP Complaint Ends Anime T-Shirt Venture
This week features an enterprising seller who experienced a big setback with their anime-themed T-shirts when an IP complaint led to de-listing. They share valuable lessons about the importance of understanding intellectual property laws. The discussion emphasizes the need for entrepreneurs to create original designs to avoid copyright issues. Despite the challenges, the guest maintains a positive outlook and encourages others to embrace failures as stepping stones to new opportunities.

Sep 12, 2024 • 5min
#2812 - TBT: Aquarium Maintenance Business Makes Splash
An Ohio entrepreneur shares his journey of transforming a passion for aquariums into a thriving maintenance service for homes and offices. He discusses the challenges of balancing his side hustle with a day job and how he caters to clients who love aquatic beauty. The guest dives into the satisfaction of creating stunning underwater worlds, utilizing technology for efficiency, and his plans for future expansion. This captivating tale offers insights for aspiring entrepreneurs looking to turn their interests into profit.

Sep 11, 2024 • 5min
#2811 - Q&A: “Creative ways to monetize a property rental…”
In this episode, we explore creative ways to monetize a property rental beyond Airbnb. We’ll consider event rentals, setting up a co-working space, or even urban farming to maximize a property’s potential.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.comEmail: team@sidehustleschool.comBe on the show: SideHustleSchool.com/questionsConnect on Instagram: @193countriesVisit Chris's main site: ChrisGuillebeau.comRead A Year of Mental Health: yearofmentalhealth.substack.comIf 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/adchoicesSee omnystudio.com/listener for privacy information.