
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

Oct 19, 2024 • 6min
#2849 - Q&A: “Best way to launch a book in 2025?”
Explore the savvy strategies for a successful book launch in 2025. Discover the importance of building a strong platform and executing a multi-phase launch plan. Learn how maintaining momentum post-launch can drive ongoing success, with tips on harnessing reviews and marketing efforts. This engaging discussion is packed with insights for aspiring authors eager to make their mark!

Oct 18, 2024 • 6min
#2848 - Failure Friday: Why My “Alt MBA” Program Flopped
In this segment, a college teacher shares the story behind their failed attempt to launch an online alternative MBA program. They discuss marketing challenges and low enrollment rates, revealing the importance of validating educational ideas. The conversation highlights vital lessons in crafting a clear value proposition and effective branding. With insight into the competitive landscape, listeners gain understanding on what happens when entrepreneurial ventures miss the mark.

Oct 17, 2024 • 6min
#2847 - TBT: Mixing Drinks and Making Money in Aspen
A bartender swaps Michigan for the high-end nightlife of Aspen, discovering lucrative opportunities amidst a bustling clientele. The story emphasizes the thrilling adventure of new beginnings while navigating financial planning challenges. Listeners are encouraged to reflect on their side hustle journeys and engage with their own experiences. It's a blend of personal triumph and practical advice that sparks inspiration for anyone considering a similar leap.

Oct 16, 2024 • 6min
#2846 - Q&A: “"How can I transition from finance to my creative side hustle career?”
Discover insightful strategies for transitioning from a stable finance career to a creative pursuit like calligraphy. Learn how to balance passion with practical financial realities while maintaining your day job. Get inspired by real-life examples and actionable advice that equips you to make your side hustle a thriving career. Embrace your creative journey without giving up your financial stability!

Oct 15, 2024 • 5min
#2845 - Q&A: “How to start a small marketing agency?”
Learn the essential steps to launch a small marketing agency, focusing on social media management and content creation. Discover how to choose your niche effectively and the importance of research. Get practical tips on cost-effective strategies and swift action for aspiring agency owners. The discussion also highlights service offerings that can set your agency apart.

Oct 14, 2024 • 6min
#2844 - First $1,000: Hospice Nurse Helps Families Prepare for Final Days
A former hospice nurse embarks on a touching journey as a death doula, providing compassionate support to families facing their final days together. She discusses the emotional challenges of this unique role and the transformative impact of her care on families. The conversation also delves into the business side of launching this side hustle, highlighting how one can earn a living while making a meaningful difference in people's lives. It's a poignant exploration of end-of-life support and compassionate service.

Oct 13, 2024 • 5min
#2843 - Q&A: "How can I explain reiki more effectively to potential clients?"
Explore how wellness practitioners can enhance client awareness and understanding of services. Discover effective strategies for articulating the benefits of Reiki, including crafting a compelling elevator pitch. Learn how identifying target audiences can elevate outreach efforts. The discussion delves into the value of clear communication in alternative healing and provides insights for practitioners seeking to improve their client engagement.

Oct 12, 2024 • 5min
#2842 - Q&A: “How to start a reselling business with limited storage?”
Discover how to launch a reselling business without the need for extensive storage space. The discussion focuses on selling small, high-value items and alternative methods like dropshipping and consignment selling. Learn strategies to work effectively within limitations and unlock the potential of your side hustle!

Oct 11, 2024 • 7min
#2841 - Failure Friday: The Corporate Gig Where I Undersold Myself
In this engaging segment, a speaker reveals the awkward moment of underselling their expertise during a corporate talk at an oil company conference. They candidly discuss the lessons learned about valuing one's services and the challenges of pricing oneself fairly. This reflection not only emphasizes the importance of knowing your worth but also inspires listeners to gain confidence in assessing their own value in the professional world.

Oct 10, 2024 • 7min
#2840 - TBT: Austin Event Planner Goes Hard for SXSW
Discover the story of an Austin event planner thriving during SXSW. He shares how he turned a side hustle into a booming business through clever marketing. Learn about the untapped potential of smaller tech conferences and product launches. His journey emphasizes the importance of finding a profitable niche in a competitive market, showcasing creative strategies for success in the lively tech scene.