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
With an estimated 4,500–6,000 English-language titles published each day, how can a first-time author avoid getting buried? Today we look at the real numbers—and a proven game plan for standing 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 da...
In this week’s First $1,000 segment, discover how one Houston homeowner transformed a simple backyard shed into a rentable studio for photos, workshops, and quiet retreats.
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: SideHu...
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: the six-figure, six-week 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, the show includes ...
Multiple payment platforms can feel like financial whack-a-mole. Today we lay out a four-step system to keep cash flow clear and tax time painless.
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@side...
If algorithms decide who sees your content, do follower counts still matter? Today we dig into how “algorithmic feeds” really work and why a loyal subscriber base still gives side hustlers a competitive edge.
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 ...
In this week’s Throwback Thursday segment, hear how a freelance marketer started selling ad placements and sponsorships for medical conferences—on commission only—and turned it into a surprisingly consistent 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...
He wanted to start a side business and put his engineering degree to good use. When he stumbled across two 1950s radios, he found an idea that was right on his wavelength.
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: SideHustleSch...
Customer emails piling up? Today we show solo founders how to automate 60% of support, triage the rest, and reclaim their weekends—all while keeping buyers happy.
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...
In this week’s First $1,000 segment, discover how a linguistics grad turned their love of invented languages into a digital toolkit for writers and gamers. With a simple Gumroad listing and a few community posts, they reached $1,000 in five weeks.
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 gui...
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: behind the scenes of an online makeup empire.
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 sho...
Can you make money renting out fancy kitchen gear? In today’s episode, we explore whether luxury cookware rentals could work—and what hidden challenges you need to watch out for.
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.
Can you make money buying Apple computers in one country and reselling them in another? In this episode, we explore the appeal—and the reality—of international tech arbitrage.
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.
In this week’s Throwback Thursday segment, hear how one side hustler launched an app that didn’t take off, but ended up turning that hard-won experience into a consulting service for other early-stage founders.
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 breakup brings two sisters together to create one happy 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: SideHustleSchool.com
Email: team@sidehustleschool.com
Be on the show: SideHustleSchool.com/questions
Can a Lyft driver really make $2,000 a week? In this episode, we break down rideshare earnings, what’s possible, and what’s rare.
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...
A short update on my new book, Time Anxiety, including a free quiz you can take and a discount on the ebook version for U.S. listeners.
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...
In this week’s First $1,000 segment, hear how a niche YouTube creator turned their passion videos into a Shopify store—selling products directly to their growing audience.
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...
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: how a budget résumé design service morphs into a template business that generates passive income.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people w...
Do you have any old videos that aren’t getting views? In this episode, we look at creative ways to repackage, remix, and monetize your past content for new platforms or audiences.
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:...
Can you really make money reselling loyalty rewards or points? In this episode, we break down the reality behind this internet hustle—and whether it’s worth your time.
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: SideH...
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