Side Hustle School

A personal trainer tried to productize his group classes into a fitness app, then discovered that recorded workouts couldn't replicate the…

A hobbyist photographer combined restoration skills with reselling to build a vintage camera business. Revenue comes from sourcing,…

A couple tried to convert a historic house into a boutique hotel but underestimated renovation costs and lost earnest money before…

A side hustler designed customizable marketing templates for small businesses and now sells them as a passive digital product. The episode…

A romance author self-published expecting quick success, then discovered that editing, cover design and audiobook production are real work.…

An affiliate marketer built a niche blog and drove most traffic through Pinterest rather than Google, earning commissions from partner…

A first-mover tried to build a personal-assistant AI app in the early days of consumer AI, before the technology and market were ready. The…

Host Chris Guillebeau announces season 8 of Side Hustle School and launches his own newsletter, YearofMentalHealth.com, inviting listeners…

An online course creator resisted adding pricing tiers and saw limited revenue until she introduced them, after which profits grew…

A traveler framing his year as a "Santa" world tour built a travel blog, monetized through Google Ads and SEO. The episode covers niche…

A lifestyle blogger bought Instagram bots to inflate her follower count, only to see real engagement collapse afterward. The episode uses…

An anime artist sells personalized art commissions online, learning to price work, build a portfolio and manage client communication. The…

An affiliate marketer ran a once-profitable niche website that declined after algorithm shifts and a stubborn refusal to pivot. The segment…

An upcycler refurbishes forgotten vintage luggage into functional art pieces and sold into her first $1,000. The business is hands-on…

A software engineer used his company's remote policy to move to Thailand, but the time-zone mismatch with his U.S. team made him miserable…

A freelance data visualization specialist turns messy datasets into clear, compelling reports for clients, reaching her first $1,000. The…

An NFT collector paid $80,000 for a Bored Ape-style NFT and watched the value drop roughly 80%. The episode is a cautionary story about…

A digital-age astrologer sells personalized birth-chart reports and readings online, reaching her first $1,000. The business packages a…

A woman launched an online financial-abundance coaching course but priced it too high for cold audiences, leading to poor conversion. The…

A Canadian paralegal helps American clients navigate immigration paperwork and bureaucracy into Canada, reaching her first $1,000 in fees.…

A first-time event host sold out a large event but had $50,000 in ticket revenue frozen by PayPal, leaving him unable to pay venues or…

A freelance video editor started on Fiverr with cheap gigs, then raised rates and shifted to higher-value clients as his portfolio and…

A digital nomad tried to build a 'remote year' travel-experiences blog while constantly moving, but burned out from the churn of content…

An Alberta man runs paid hikes and tours to wilderness areas, weaving in indigenous knowledge and local landmarks. He hit his first $1,000…