Side Hustle School

Side Hustle School

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/

Episodes

August 12, 2025 4 mins

Heard about people buying and selling Instacart accounts? In this episode, we explore whether it’s a clever hustle—or a fast track to getting banned.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Em...

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In this week’s First $1,000 segment, discover how a lifelong trainspotter turned ambient railway recordings into a digital product for sleep, study, and meditation.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleScho...

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This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: a failed grant application leads to a new business.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, t...

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What do high school grads, new parents, and brides-to-be have in common? In this episode, we explore renewable markets—those endlessly refreshing customer pools—and why they’re smart for side hustlers.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A s...

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Thinking about launching your own video game? In today’s episode, we explore how solo developers can publish on Steam—one of the biggest game distribution platforms—and what it really takes to turn a project into profit.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and...

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In this week’s Throwback Thursday segment, hear how an independent artist who launched a small print-on-demand store eventually landed a licensing deal with a major retail brand—and what the experience has been like so far.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and li...

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A sky-high success story of a six-figure drone coaching business that begins after a man crashes a drone into a parked car in New York City. Look out!  

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

E...

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Have a bunch of invention ideas but don’t want to start a business for each one? In this episode, we look at the reality of licensing product concepts—and why execution matters more than creativity.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several da...

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In this week’s First $1,000 segment, hear how a veteran Dungeon Master turned his custom campaign maps into a downloadable product for other players.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: t...

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This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: developing your skills as a “connector.”

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, ...

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What’s the smartest way to grow a coaching business when your calendar is already full? In this episode, we look at sustainable ways to scale without losing your personal touch.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: S...

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Thinking about launching a true crime podcast? In this episode, we explore what it takes to stand out—and how to build a foundation for growth and monetization from the start.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: Sid...

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In this week’s Throwback Thursday segment, hear how one side hustler created themed bundles of thrifted pop culture items—turning $10 Goodwill hauls into $60+ nostalgia packs for superfans.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each w...

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When a full-time data developer starts a detective agency with his kids, it goes on to help people recover over $100,000 worth of jewelry in a casual side hustle.  

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustle...

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In this episode, we help a caller explore how to balance persistence and pushiness in sales. She doesn’t want to be pushy, but she wants to close the deal!

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Em...

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In this week’s First $1,000 segment, discover how one new parent turned a 3 a.m. spreadsheet session into a sellable baby tracker. With no ads and no tech background, he reached $1,000 in sales using only parenting groups and a Notion template.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided...

Mark as Played

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: from doing to teaching.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided...

Mark as Played

Could helping people vanish from the internet be a viable business? In today’s episode, we explore the growing market for digital privacy services—and what it takes to offer one.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show n...

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Stuck between two side hustle ideas? In this episode, we’ll look at how to choose the right path when both options feel equally strong.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: team@sidehustle...

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In this week’s Throwback Thursday segment, discover how one side hustler created a shop selling $2 digital products—and scaled it to $185,000 in revenue by mastering SEO, volume, and a few smart upsells.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A sever...

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