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
Mar 10, 2026 • 5min
Ep. 3356 - Q&A: “I’m a professional speed skater. How can I fundraise?”
Justin, an amateur-to-pro speed skater from St. Paul pursuing Olympic dreams. He asks how to fund training and build support. The conversation covers focusing priorities, why Patreon is risky without an audience, creating products for sustainable income, improving social presence on one or two platforms, and pursuing brand deals and sponsorships for bigger payout.
6 snips
Mar 9, 2026 • 6min
Ep. 3355 - First $1,000: Camping YouTuber Earns Affiliate Income
A camper turns smartphone reviews into a YouTube channel showcasing gear and tips. He uses affiliate programs and adds purchase links to earn when viewers buy. Short listicle videos, SEO keywords, and analytics shape his content strategy. Patience and data-driven pivots lead to the first $1,000 in earnings.
12 snips
Mar 8, 2026 • 7min
Ep. 3354 - STORY: “Productivity Nannies” Dig Co-Working Caves for Modern Workers
A team creates daylong distraction-free "caves" where people disappear to finish important work. They sold out a first public event with simple promotion and turned it into memberships, virtual days, and corporate offerings. The founders learned to define roles early and scaled with low-cost operations and thoughtful product additions.
Mar 7, 2026 • 5min
Ep. 3353 - Q&A: “One-page business plan: what is the essential info?”
A short Q&A on what belongs in a one-page business plan and where to find the original template. They highlight the two core questions: what you will sell and who will buy it. Practical choices about pricing and payment methods get attention. The conversation stresses action steps, defining success, and why a concise plan can propel your side hustle.
6 snips
Mar 6, 2026 • 8min
Ep. 3352 - Failure Friday: “Our first trade show was canceled with no refund…”
Chris Cavallari, founder and lead craftsman at The Acadian who makes handmade luxury pens and leather goods. He recounts preparing for his first wholesale trade show and then losing booth fees when COVID-19 canceled it. He talks about writing an emergency continuity plan, building local support through a Facebook peer group and Zooms, and diversifying income to survive the shutdown.
Mar 5, 2026 • 6min
Ep. 3351 - TBT: The Tennessee Bachelorette Party Boom
A Nashville entrepreneur turned bachelorette parties into a profitable planning business. She explains early pricing packages and how word-of-mouth, Instagram, and influencers drove growth. Scaling required a team, CRM, and project tools. Stories cover tricky group mixes, booking mishaps, and practical fixes to keep events smooth.
5 snips
Mar 4, 2026 • 7min
Ep. 3350 - Q&A: “What are the most profitable niches for teaching?”
A rapid-fire list of the most profitable niches for teaching is presented. Topics include personal finance, health, relationships, hobby categories with gear, tech skills, and real estate. The conversation highlights why some niches command money and how to evaluate market demand before diving in.
Mar 3, 2026 • 6min
Ep. 3349 - Q&A: "I'm opening a new hair salon. How can I build my clientele?”
A stylist’s plan for leaving a chain and launching a salon. Practical steps for keeping loyal clients and making rebooking easy. Local outreach tactics like postcards, neighborhood networking, and geo-targeted Instagram. Intro offers, curated starter packages, and referral strategies to fill the schedule fast.
6 snips
Mar 2, 2026 • 6min
Ep. 3348 - First $1,000: “I earn $3,000/month leading London walking tours…”
A London guide turned weekend walking-tour entrepreneur who earns about £2,500 monthly. He grew bookings through word-of-mouth and lively on-the-job learning. Stories include a funny historical mix-up and why in-person walks stay relevant despite digital alternatives.
Mar 1, 2026 • 7min
Ep. 3347 - STORY: Trader Joe’s Sign Artist Earns $43,200 Selling Tea-Stained Prints
A Trader Joe’s sign artist turns public-domain art into tea-stained prints sold online. He experiments with quirky animal mashups and adds custom options after a surprise first sale. The hustle scales from a $300 startup to steady monthly profit, long-term growth, and major life changes.
