Side Hustle School

A handmade jewelry maker scaled up after a sales influx but cut quality and consistency to keep up, and customers noticed and complained.…

A tarot card reader hit profitability within one month by combining TikTok marketing with deliberate pricing strategy. The episode focuses…

A Failure Friday episode about a Philadelphia chef who launched a gourmet food truck and found it unprofitable in the city's competitive…

A freelance podcast editor specialized in comedy shows, building pricing strategies and efficient editing systems to reach his first $1,000…

A Failure Friday episode about a retailer who bet half her startup capital on a large inventory of holiday sweaters, watched the season…

An educational psychologist launched a 'Virtual Study Buddy' service combining tutoring with motivational coaching, reaching her first…

A Failure Friday episode about a communications graduate whose attempt to launch a PR agency didn't work out as planned. The episode…

A side hustler in Olympia, Washington designs and drafts plans for tiny homes, reaching his first $1,000 in the niche. The episode explores…

A Failure Friday episode featuring a longtime listener with many side hustle ideas who never executed on any of them. The episode focuses…

A University of Alabama junior earns her first $1,000 advising potential sorority recruits on personal branding during rush week. The…

A Failure Friday episode about a grade-school teacher who tried running a fall festival as a side hustle, only to be hit by bad weather and…

A frequent camper started a YouTube channel reviewing camping gear and tips, which grew into a regular affiliate income stream as viewers…

A Failure Friday episode about a restaurant owner who activated a DoorDash account to drive more orders but accidentally gave away roughly…

A Washington, DC tour guide built a sober-curious tour business focused on mocktail-making stops and alcohol-free experiences, hitting her…

A Failure Friday episode about a Chicago-based side hustle coffee roaster who had to shut down his caffeinated roasting business. The…

A new podcaster built a side business around brokering joint venture deals between compatible creators and brands, earning his first…

A Failure Friday episode about a yoga instructor who tried launching a 'Graveyard Yoga' series combining yoga with a macabre theme. The…

First $1,000 segment about a fashion-focused affiliate marketer who is reportedly earning around $10,000/month through affiliate campaigns.…

Failure Friday episode about a yoga teacher who planned a Central America retreat that never got enough sign-ups to run. The episode covers…

First $1,000 segment featuring a virtual assistant who specializes exclusively in email inbox management for busy startup founders. The…

Failure Friday episode about a personal finance blogger who forgot to renew a domain name and lost it to a third party that used it for…

Bonus announcement for host Chris Guillebeau's new book Gonzo Capitalism, which is now available in bookstores and online, along with a…

First $1,000 segment featuring a Chicago medical resident who runs a side hustle advising med school students and interns on career…

Failure Friday episode about a travel blogger and TikTok streamer whose affiliate revenue stream was cut when her banking partner dropped…