Side Hustle School
Chris Guillebeau / Onward Project
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/
Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Episodes
Mentioned books
Sep 2, 2025 • 6min
Ep. 3167 - Q&A: “How to handle customer service without burning out?”
Struggling with customer emails? Learn how to automate 60% of your support while keeping your customers satisfied. Discover practical tools like FAQs and canned responses to streamline inquiries. Plus, find out how to set boundaries that help you avoid burnout and reclaim your weekends. These strategies are tailored for solo founders looking to manage customer service efficiently.
Sep 1, 2025 • 6min
Ep. 3166 - First $1,000: Language Nerd Builds “Fake Language” Creation Kit
A linguistics grad transforms a passion for invented languages into a thriving side hustle. They create a digital toolkit for writers and gamers, generating $1,000 in just five weeks. The journey emphasizes the power of turning curiosity into profit through effective marketing and community engagement. Discover the creative process behind crafting a Conlang Creation Kit and learn how personal passions can lead to unexpected financial success.
6 snips
Aug 31, 2025 • 8min
Ep. 3165 - Weekend Workshop: How Makeup Videos Built a Million-Dollar Brand
Dive into the compelling world of transforming passion into profit through makeup tutorials! Discover how one creator turned her videos into a million-dollar cosmetics brand. Learn about the importance of authenticity and building a genuine connection with your audience. Get inspired by practical strategies and real-life examples, perfect for anyone looking to launch their own side hustle. Plus, uncover key insights that could spark your entrepreneurial journey in 2025!
Aug 30, 2025 • 5min
Ep. 3164 - Q&A: “Is there a market for fancy cookware rentals?”
Could renting out luxury kitchen gear be a profitable sideline? The discussion delves into the potential market for high-end cookware rentals, highlighting the importance of assessing local demand. Listeners learn about the logistical challenges that come with this venture, including risks of damages and liability. It's a thought-provoking exploration of turning a passion for cooking into a money-making opportunity!
Aug 29, 2025 • 6min
Ep. 3163 - Q&A: “Can MacBook arbitrage work as a side hustle?”
Can you profit from buying and selling Apple computers across borders? This discussion dives into the world of international tech arbitrage, unpacking both its allure and its practical hurdles. While opportunities exist, the challenges often prompt a rethink towards local strategies for reselling electronics. With real-life insights and expert advice, listeners learn about the complexities of turning a tech hobby into a lucrative side hustle.
Aug 28, 2025 • 5min
Ep. 3162 - TBT: Failed App Becomes Successful Consulting Business
Discover how a failed productivity app birthed a thriving consulting business. The host shares the transformative journey of turning setbacks into success, emphasizing resilience and personal growth. Learn the vital lessons of transparency and networking that helped overcome entrepreneurial hurdles. This engaging discussion showcases the power of pivoting and finding new paths, making it an inspiring listen for anyone tackling their own side hustle journey.
Aug 27, 2025 • 7min
Ep. 3161 - STORY: Curated Gift Boxes for Breakups and Baby Bumps
Two sisters unite their strengths to launch a unique business that creates curated gift boxes for milestone events like breakups and baby bumps. Their story highlights the emotional connection behind personalized gifts and the inspiration that comes from life’s challenges. With creativity and resilience, they navigate the competitive gifting market, making a mark that resonates with customers. Tune in to hear how they turned a moment of loss into a thriving venture!
Aug 26, 2025 • 5min
Ep. 3160 - Q&A: “Can Lyft drivers really make $2,000/week?”
Can Lyft drivers really pull in $2,000 a week? Dive into the intriguing world of rideshare earnings as the podcast breaks down what’s possible versus the reality of the gig economy. Discover how some drivers achieve high earnings with hard work and multiple gigs, but also learn that the average payout often falls short. Real stories and expert analysis shine a light on the true earning potential while offering valuable insights for those considering rideshare driving as a side hustle.
Aug 25, 2025 • 2min
BONUS: "Time Anxiety" Book and Free Quiz
The discussion dives into the concept of Time Anxiety and how it affects our daily lives. The speaker shares insights from their new book on managing time-related pressures. Listeners are encouraged to take a free quiz to assess their own experiences with time anxiety. There's a focus on how typical productivity tips can sometimes increase stress rather than alleviate it, inviting a fresh perspective on time management strategies.
Aug 25, 2025 • 6min
Ep. 3159 - First $1,000: YouTube Bonsai Channel Grows Into Online Store
Discover how a YouTube creator transformed a passion for bonsai into a booming online store. By selling tools and kits to their loyal audience, they achieved their first $1,000 and turned a niche hobby into a viable income. Tune in to hear inspiring tales of creative ventures thriving alongside traditional jobs, showcasing the impressive potential of a side hustle!
