Side Hustle School

Chris Guillebeau / Onward Project
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Jun 30, 2025 • 6min

Ep. 3103 - First $1,000: AI Agency Writes Execs’ LinkedIn Posts

Discover how a savvy freelancer transformed the landscape of LinkedIn branding by using AI to craft compelling posts for executives. Learn about their journey to snagging the first paying clients and establishing a subscription model. Delve into the growing demand for engaging professional content and how AI tools like ChatGPT are reshaping the market. The rise of this innovative agency reveals exciting opportunities in the social media realm, making executive engagement more powerful and accessible.
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Jun 29, 2025 • 8min

Ep. 3102 - Weekend Workshop: Back to the Future

Discover essential strategies for taking your side hustle to the next level. Navigate the chaos of order fulfillment with tips on using services like ShipStation to ease your workload. Learn how to assess your progress once profits start rolling in and consider three key paths: scaling, maintaining, or automating and selling. This segment presents a roadmap to aligning your hustle with your personal goals, ensuring you're on the right track for 2025!
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Jun 28, 2025 • 5min

Ep. 3101 - Q&A: “I want to sell ‘weird grocery items’…”

Discover the intriguing niche of reselling rare grocery items, from discontinued snacks to cult-favorite condiments. Learn how one listener is turning their knack for sourcing unusual treats into a profitable side hustle. The discussion covers the market potential, successful case studies, and essential tips for navigating legal and logistical hurdles. It's a fascinating dive into making extra cash through the quirky world of grocery resale!
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Jun 27, 2025 • 5min

Ep. 3100 - Q&A: “Can I make money designing unique scavenger hunts?”

Could your love for puzzles lead to a profitable venture? Discover how a Richmond caller is turning unique scavenger hunts into a thriving side business. Uncover creative marketing strategies and tips for launching a service that captures customers' attention. Plus, hear about effective shipping solutions that help entrepreneurs streamline their processes. Tune in for inspiration and insights on monetizing your passions!
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Jun 26, 2025 • 7min

Ep. 3099 - TBT: Embroidered Joke Hat Becomes Unexpected Business

A sarcastic embroidery project surprisingly turned into a thriving side hustle after a joke hat went viral. The creator navigated the challenges of launching an Etsy shop and reinvesting profits for growth. Social media played a key role in skyrocketing demand, transforming a hobby into a successful merchandise business. Efficient production and innovative branding strategies were essential in managing the newfound order volume. Additionally, tools like AI-powered PCs increased productivity and streamlined operations, showcasing the power of creativity in entrepreneurship.
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Jun 25, 2025 • 7min

Ep. 3098 - STORY: Engineer Turns Home Energy Problem Into Million-Dollar Solution

A construction engineer identifies a major energy waste issue in attics and invents a clever foam cover for attic stairs. This innovative solution not only saves homeowners money but also blossoms into a lucrative side hustle, generating over two million dollars annually. The story showcases how addressing practical challenges with creativity can lead to extraordinary success. It highlights the balance of passion, strategy, and market demand in turning a simple idea into a thriving venture.
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Jun 24, 2025 • 6min

Ep. 3097 - Q&A: “Turning my sleep obsession into a hustle…”

Can a passion for sleep turn into a profitable venture? Discover strategies for monetizing sleep product reviews and insights on affiliate marketing. Learn about the challenges of balancing personal passions with business while still helping others improve their sleep quality. Explore effective tools and tips to streamline your entrepreneurial journey. This episode dives into real-life case studies and practical advice for turning hobbies into extra income without quitting your job.
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Jun 23, 2025 • 7min

Ep. 3096 - First $1,000: Legal Eagle Lands Big Order After Rapper Shoutout

A corporate attorney unexpectedly transforms her passion for customizing sneakers into a thriving side hustle after a shoutout from Lil Nas X. The discussion highlights her journey balancing a full-time job with the surge in sneaker orders. Listeners learn how pursuing a creative side project can foster personal growth and inspire new opportunities. Sharing insights on the balance between stability and ambition, the podcast encourages exploring diverse passions while navigating the unpredictable nature of business.
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10 snips
Jun 22, 2025 • 8min

Ep. 3095 - Weekend Workshop: Creating Business Systems

Learn how to turn your ideas into action by establishing effective business systems for your side hustle. Discover the significance of documenting processes to enhance efficiency and reduce stress. Explore practical strategies for transforming informal knowledge into systematic workflows. Gain insights on documenting essential business operations, from sales to delivery, to create smoother and more successful ventures. This journey not only boosts organization but also sets the stage for scalability and long-term success.
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Jun 21, 2025 • 6min

Ep. 3094 - Q&A: “Can organizing someone’s email become a real side hustle?”

Exploring the niche of email organization as a side hustle, this podcast delves into the growing demand for inbox cleanup services. It tackles the challenges of marketing these services as productivity boosters and the importance of building trust with clients. Tips for effective communication and privacy measures are shared to help entrepreneurs attract high-value clients and avoid inbox overwhelm.

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