Side Hustle School

Chris Guillebeau / Onward Project
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Jul 29, 2025 • 4min

Ep. 3132 - Q&A: “How can I be persistent … without being pushy?”

A caller seeks guidance on how to be persistent in sales without crossing into pushy territory. The discussion navigates the delicate balance between persistence and aggression with effective communication strategies. Personal anecdotes illustrate the art of follow-up, emphasizing respect for potential clients while staying proactive. Techniques include proper contact limits and utilizing tools to maintain relationships without overwhelming prospects. It's a treasure trove of insights for anyone looking to excel in sales without sacrificing integrity!
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17 snips
Jul 28, 2025 • 5min

Ep. 3131 - First $1,000: Sleep-Deprived Dad Creates Digital Baby Journal

A sleep-deprived dad harnesses the chaos of parenthood by creating a digital baby journal. Using Notion and sharing his creation with parenting groups, he transforms messy notes into an organized and profitable tool. In just a few months, he rakes in over $3,000 in sales without any ads or tech expertise. This story showcases the power of creativity and community in launching a side hustle while navigating the joys and challenges of new parenthood.
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4 snips
Jul 27, 2025 • 7min

Ep. 3130 - Weekend Workshop: The Wordpress Revolution

This podcast dives into transitioning from a service provider to an educator, showcasing a journey from web design to creating a profitable online course on WordPress. It emphasizes the importance of understanding client needs and provides actionable steps for listeners. The episode also covers how to convert personal expertise into a teachable system, including testing course demand and shifting focus from service-based work to educational offerings. It's a practical guide for aspiring side hustlers.
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Jul 26, 2025 • 6min

Ep. 3129 - Q&A: “Would people pay to disappear from the internet?”

Could a business help people vanish from the internet? This intriguing question opens up a discussion on the evolving market for digital privacy services. The podcast dives into the challenges of maintaining trust while offering solutions for online disappearance. It contrasts the desire for reduced visibility with the common trend of showcasing online profiles. Additionally, it highlights strategies for digital footprint cleanup, tapping into growing concerns over online privacy and the need for a trustworthy service.
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Jul 25, 2025 • 4min

Ep. 3128 - Q&A: “Both of my ideas are strong, but I can only do one…”

Stuck choosing between two great side hustle ideas? This discussion dives into effective decision-making strategies to prioritize your passions. One caller weighs the pros and cons of a food product versus a digital resource, aligning with long-term goals. Listeners will discover how side hustle paths can shift and evolve over time, offering insights into navigating these creative dilemmas. Tune in for helpful tips that turn uncertainty into opportunity!
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16 snips
Jul 24, 2025 • 6min

Ep. 3127 - TBT: How Selling $2 Digital Products Earned $185,000

Discover the journey of a savvy entrepreneur who transformed a simple Etsy shop into a $185,000 success by selling $2 digital products. Learn how they nailed SEO strategies and adopted minimalist design to maximize profit without handling inventory. The discussion emphasizes the power of low-cost digital sales, highlighting the importance of consistency and creativity in crafting appealing offers. Join in to uncover the secrets behind turning small ideas into substantial earnings through smart sales tactics!
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Jul 23, 2025 • 7min

Ep. 3126 - STORY: Nerdy Kickstarter Campaign Raises $1 Million

An Ohio man turns his passion for board games into a wildly successful Kickstarter campaign, raising over $1 million. His inspiring journey showcases how creativity and nostalgia can fuel innovative game designs. Listeners also get strategic tips on launching their own Kickstarter projects, emphasizing the importance of timing and marketing. This tale blends personal stories with practical advice, encouraging others to pursue their creative ideas.
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Jul 22, 2025 • 5min

Ep. 3125 - Q&A: “How do I license my educational materials to a publisher?”

A listener seeks advice on licensing her educational materials to publishers for wider distribution. The discussion dives into strategies for presenting her content attractively and meeting publisher expectations. They also explore the perks of earning passive income through licensing and effective methods for managing order fulfillment. Insights into developing partnerships are shared, ensuring her valuable resources reach more educators.
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Jul 21, 2025 • 6min

Ep. 3124 - First $1,000: Musician Creates Loop Packs for Video Editors

A freelance musician transforms his abandoned audio sketches into a successful product for video editors. With just twelve clean loops, he taps into the demand for royalty-free music and makes his first $1,000 in under a month. This fascinating journey highlights the power of creativity and recognizing market gaps, all with minimal marketing efforts. It's a perfect example of turning passion into profit!
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Jul 20, 2025 • 8min

Ep. 3123 - Weekend Workshop: The Most Awesome Guitar Lessons in the Universe

Discover how a music teacher dramatically raised his rates from $50 to $120 per hour by transforming his positioning. He reframed his guitar lessons as unique experiences that prioritize emotional outcomes. By employing creative marketing strategies, he attracted committed students, leading to increased income and personal satisfaction. Join in for free guidance on starting your own side hustle in 2025 and listen to inspiring case studies of individuals earning extra money without leaving their day jobs.

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