

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 29, 2025 • 5min
Ep. 3194 - First $1,000: Marketer Sells Simple Fixes to Dental Clinics
A digital marketer discovers a goldmine in orthodontist listings by fixing visibility issues they didn't know they had. He packages a simple local SEO tune-up service, helping clients enhance their online presence. With a strategy of free audits and engaging videos, he quickly lands his first client, leading to referrals and expanding his hustle. The ease of scaling this service—with minimal overhead and time commitment—shows how innovative thinking can turn a side gig into a successful venture.

Sep 28, 2025 • 8min
Ep. 3193 - Weekend Workshop: The Art of Electronics Arbitrage
Discover how a travel rewards hobby transformed into a lucrative electronics arbitrage business. Learn the clever method of buying gift cards to purchase and resell electronics for profit. The sweet spot? Products priced between $200 and $800! The guest shares insights on scaling to six figures while maintaining a full-time job. Plus, get a four-step framework to kickstart your own arbitrage journey, ensuring you stay adaptable to market changes. It's an engaging deep dive into making money on the side!

6 snips
Sep 27, 2025 • 6min
Ep. 3192 - Q&A: “How can a freelancer pay herself a stable salary?”
Dive into the world of freelance finances and discover a three-bucket system that stabilizes your income. Learn how to set aside 25–30% for taxes and choose a reliable monthly paycheck based on past earnings. Chris shares tips on automating transfers and maintaining a two-month operating buffer. He emphasizes separating business volatility from personal finances, ensuring your life remains predictable despite income fluctuations. Perfect for freelancers seeking financial peace of mind!

Sep 26, 2025 • 4min
Ep. 3191 - Q&A: “What KPIs should I track for my software biz?”
In this episode, the focus is on which key performance indicators (KPIs) truly matter for a small SaaS business. Instead of overwhelming metrics, three crucial numbers are highlighted: tracking monthly recurring revenue trends, closely monitoring churn rates, and selecting a single engagement signal to measure user stickiness. These streamlined insights aim to guide growth decisions effectively, making analytics manageable for small teams.

Sep 25, 2025 • 5min
Ep. 3190 - TBT: Helping Aspiring Film Professionals Get Hired
Discover how a London-based entrepreneur developed a service to help aspiring film professionals land their first jobs and earn union credentials. The venture, called Set Start, offers vetted job listings and resources for newcomers to the industry. With impressive subscriber growth, plans are underway to expand the service to major film hubs like Los Angeles and Vancouver. Learn about the challenges faced and the innovative solutions proposed in this industry-focused journey!

Sep 24, 2025 • 7min
Ep. 3189 - STORY: College Grad Shares “More than Mac & Cheese” Student Recipes
A college grad shares her culinary journey, turning simple student recipes into a thriving blog. Discover how she shifted from aspiring teacher to food blogger, targeting her classmates with easy meals. Learn about her transition to a marketing role and the blog's growth that now generates over $1,000 a month. Advice includes the importance of niche focus and shortcut recipes. She hints at a future cookbook, showcasing blogs as fulfilling passion projects.

Sep 23, 2025 • 4min
Ep. 3188 - Q&A: “Can you run a YouTube channel with only AI voices and scripts?”
Can AI-generated content thrive on YouTube? Discover how faceless shows using synthetic voices and scripts are becoming a reality. Unpack the platform's rules surrounding audience interaction and legalities. Learn about the potential of creating short-form series with text-to-speech technology and stock footage. Explore the dynamics of monetization and viewer engagement with AI as a production tool rather than a personality. Dive into the future of content creation that doesn’t require traditional on-screen hosts.

Sep 22, 2025 • 5min
Ep. 3187 - First $1,000: Typography Lover Turns Letters Into Revenue
Discover how a font designer transformed their passion for typography into a thriving side hustle with a subway-inspired typeface. After launching just two fonts on Creative Market, they quickly made over $1,000 in under a month! The discussion highlights the importance of curiosity, persistence, and action for side hustlers. Get practical tips on designing and marketing fonts, along with valuable insights on building a sustainable creative business.

Sep 21, 2025 • 6min
Ep. 3186 - Weekend Workshop: Design Disruption in Traditional Markets
Explore the fascinating world of design disruption as outdated industries get a modern makeover. Hear the inspiring story of Julie Wilder, who transformed astrology calendars with fresh aesthetics, launching her successful Etsy store and seeing organic growth. Discover practical steps to identify and redesign traditional products for today's market. Get ready to spot opportunities in dated industries and take action toward your next side hustle!

4 snips
Sep 20, 2025 • 5min
Ep. 3185 - Q&A: “How can I sell an Amazon-only FBA brand for top dollar?”
Thinking of selling an Amazon-only FBA brand? Discover how to enhance your business valuation by adding a Shopify channel and capturing customer emails. Learn about reducing channel risk and the impact a 90-day tune-up can have on your sale price. This discussion is packed with actionable insights for maximizing profits on your venture.