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
7 snips
Apr 6, 2025 • 7min
Ep. 3018 - Weekend Workshop: Design Your First Workflow
Discover the essential steps to design your first workflow for a successful side hustle. Learn how to create clear, repeatable systems to enhance efficiency. The discussion breaks down workflows into customer acquisition and product delivery, using practical examples for better understanding. Each week brings new insights and activities to help you master your side hustle in 2025.
Apr 5, 2025 • 5min
Ep. 3017 - Q&A: “How do I balance transparency with professionalism?”
Discover the art of balancing transparency with professionalism! The discussion delves into how to authentically share struggles without losing credibility. Learn practical tips for building trust with your audience while keeping a professional demeanor. The insights provided will help you navigate this delicate aspect of business communications effectively.
9 snips
Apr 4, 2025 • 4min
Ep. 3016 - Q&A: “Is there still room to start a podcast in 2025?”
Wondering if you can still kickstart a podcast in 2025? Discover how to find your unique voice in a saturated market. Explore the rising trend of niche topics like urban gardening, which can help you stand out. Learn effective strategies for audience growth and the advantages of micro-niche podcasts, including better advertising prospects. Get inspired by case studies of individuals making extra money on the side without quitting their day jobs.
Apr 3, 2025 • 6min
Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to Global Audiences
Discover how a stationery lover transformed her passion by shipping curated paper goods from Tokyo to the world. This journey not only supports local artisans but also shares the beauty of Japanese stationery culture globally. Plus, explore essential tech tools that boost productivity for busy hustlers, complete with a special discount for listeners. Join in for insights into turning a hobby into a thriving business!
Apr 2, 2025 • 8min
Ep. 3014 - STORY: Accountant Earns $233,751 Reselling Items He Buys at Walmart
An accountant dives into the world of reselling, transforming their side hustle into a lucrative online business. They start with unusual items like textbooks, dental floss, and Cheerios purchased in bulk from Walmart. Within under two years, they earn an impressive $233,751. The discussion explores lessons learned in e-commerce and highlights the freedom and fulfillment that comes with pursuing one's own business outside the corporate grind.
Apr 1, 2025 • 5min
Ep. 3013 - Q&A: “How do I find my first clients without paid advertising?”
Discover how new business owners can find their first clients without spending on ads. Explore grassroots networking ideas, community involvement, and clever social media strategies. The focus is on building a client base from the ground up, using creativity and personal connections to create momentum. Tune in for practical tips and inspiring insights that can help kick-start your entrepreneurial journey!
Mar 31, 2025 • 5min
Ep. 3012 - First $1,000: Stay-at-Home Dad’s Virtual Garage Sale Venture
A stay-at-home dad transforms clutter into cash by launching a virtual garage sale, turning forgotten items into a steady income stream. His entrepreneurial journey not only helps him earn his first $1,000 but also supports neighbors in decluttering their homes. With practical tips on buying and selling online, he illustrates how anyone can harness community connections for financial gain. It's an inspiring tale of creativity and resourcefulness in the side hustle world!
6 snips
Mar 30, 2025 • 9min
Ep. 3011 - Weekend Workshop: Make It Easy to Get Paid
Discover how simplifying payment systems can transform your side hustle. Learn about essential tools like Stripe and Square that make transactions smooth and efficient. Hear strategies aimed at creating a user-friendly payment experience that boosts customer satisfaction. Personal stories and actionable tips ensure you're set up for success while earning extra income. Dive into practical advice that helps you get paid easily, paving the way for your entrepreneurial journey.
Mar 29, 2025 • 6min
Ep. 3010 - Q&A: “How to set better boundaries with clients?”
Explore how to set effective boundaries with clients, especially in emotionally charged situations. Learn the importance of clear communication and empathy in managing client overwhelm. Discover strategies for maintaining a supportive relationship while navigating tough conversations. The discussion even touches on critical issues like early cancer screening and the role of accessible tests to help with prevention. Tune in for practical tips to keep your business thriving without sacrificing your well-being!
Mar 28, 2025 • 6min
Ep. 3009 - Q&A: “How can I work fewer hours without losing income?”
A web developer faces the challenge of working long hours while trying to maintain income. The discussion unveils strategies like raising rates and outsourcing tasks to optimize workload. Delving into the importance of retainer clients and recurring revenue, the conversation offers tips for achieving work-life balance. Listeners are inspired to reshape their service packages for a sustainable business. Each insight promises to empower freelancers in their quest to work smarter, not harder!
