Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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. Hosted on Acast. See acast.com/privacy for more information.

Author

Chris Guillebeau

Episodes

#2158 - First $1,000: “From TaskRabbit to $4,000/month…” 28.11.2022 5:24

In this week’s First $1,000 segment, we hear from a handyman who builds his part-time business to $4,000/month on TaskRabbit, and then goes off-app to avoid platform fees. 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 e...

#2157 - Q&A: “I’m ready for more passive income…” 27.11.2022 5:24

Our listener is earning more than $50,000/year from three side projects. Whoo hoo! Still, he wants more of this income to be passive, because he’s doing a lot of work for it. How can he go to the next level? 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 lesson...

#2156 - Q&A: "Every time I start to make progress, I hold back..." 26.11.2022 4:59

A listener has a question about self-sabotage: whenever they find themselves moving forward, they end up backing away. What can be done in this situation? 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...

#2155 - Failure Friday: “I never should have borrowed money to invest…” 25.11.2022 5:06

In this week’s Failure Friday segment, we hear from a listener who borrowed money from a friend for an investment in a cryptocurrency project. Need we say more? 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. S...

#2154 - Give Thanks and Eat Pie: Special Thanksgiving Episode 24.11.2022 3:45

In this special episode recorded in South Africa, Chris reflects on 5+ years of Side Hustle School and encourages listeners to eat more pie. 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: SideHustl...

#2153 - Q&A: “How to profit from cover songs on Apple Music?” 23.11.2022 5:28

If you’re familiar with any of the major streaming platforms, you might be aware that there are cover versions of lots of popular songs. How does this work in the business sense? 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...

#2152 - Q&A: “I want to make an asexual dating app…” 22.11.2022 5:07

Today’s caller has an idea to start her own app for people who identify as asexual (where you don’t feel much sexual attraction to anyone). What’s the best path forward? 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 ea...

#2151 - First $1,000: “I made a floor to ceiling chain of bananas…” 21.11.2022 5:33

In this week’s First $1,000 segment, we hear from a Texas event planner who earns at least $2,000/month on the side. One early event featured a creative display of hundreds of bananas. 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...

#2150 - Q&A: “How can I make money with Zoom calls?” 20.11.2022 5:02

Today’s listener wonders: how can the average person capitalize on the fact that so many people are much more comfortable with video calls these days? 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:...

#2149 - Q&A: “I’m a professional speed skater … how can I fundraise?” 19.11.2022 5:30

An athletic listener from Minnesota seeks advice on starting a fundraising campaign. Will he need to improve his social media for more people to notice? 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 note...

#2148 - Failure Friday: “I invested in a franchise and now I feel stuck…” 18.11.2022 5:20

In this week’s Failure Friday segment, we hear from an investor who buys into a national franchise—then realizes he’s essentially bought himself a job. 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 no...

#2147 - TBT: “Amazon Merch” Seller Moves 7,000 T-Shirts (& more!) 17.11.2022 7:52

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a livestreamer who uses Amazon Merch on Demand to sell t-shirts and other personalized items. She’s sold more than 7,000 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 lesson...

#2146 - Q&A: “Are there any alternatives to Patreon?” 16.11.2022 4:18

An independent musician is looking for “something like Patreon but different.” What are her options? 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...

#2145 - Q&A: “How can I become a personal finance influencer?” 15.11.2022 5:46

Today’s caller wants to enter the world of personal finance experts and influencers. As she notes, she’s not the only one! So if you want to break in—what do you do? 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...

#2144 - First $1,000: “Clients don’t want Wordpress, they want a website…” 14.11.2022 5:29

In this week’s First $1,000 segment, we hear from the self-described “Wordpress Girl,” who starts a service helping female entrepreneurs get set up with a website. She’s currently in the midst of a rebranding, but still brings in at least $2,000/month on the side. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting th...

#2143 - Q&A: “I’d like to teach wilderness survival classes…” 13.11.2022 5:17

An outdoorsman from Montana wants to teach survival skills, but isn’t sure how to start. Can we help him get out of the woods? 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...

#2142 - Q&A: “Need to increase income as an adjunct professor…” 12.11.2022 5:08

Today we hear from a professor of sociology who wants to make more money. Nothing wrong with that! Let’s see if we can help. 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 Ema...

#2141 - Failure Friday: “I wish I hadn’t told my friends about my hustle…” 11.11.2022 5:39

In this week’s Failure Friday segment, we hear from a tech employee who starts an after-hours side hustle. This turns out to be … a mistake. 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: SideHust...

#2140 - TBT: NYC Opera Singer Moonlights as Home Contractor 10.11.2022 6:55

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a New York City opera singer, home contractor, and primary caregiver. Like many side hustlers, she stays busy! 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...

#2139 - Q&A: “What’s the best way to outline a business idea?” 09.11.2022 5:34

Let’s say you have an idea. What do you do next? Learning to develop this skill can help you with a lot of things, not just business ideas. 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...

#2138 - Q&A: “Can I make and sell Notion templates?” 08.11.2022 4:44

The productivity app Notion describes itself as a a project management and note-taking software platform. It comes with 100 templates, but you can make your own—and our caller wants to sell the ones they make. How can they do that? 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 incl...

#2137 - First $1,000: “I make $3,000/month with Instagram DMs…” 07.11.2022 5:18

In this week’s First $1,000 segment, we hear from a listener with a very creative strategy: she earns up to $4,000/month through Instagram Direct Messages (DMs), without having much of a following of her own. This is a good 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 include...

#2136 - Q&A: “When is it too late to change a business name?” 06.11.2022 3:58

If you haven’t launched and realize your business needs a different name, it’s easy enough to change. But what about when you’re already up and running—is there a point where it’s too late? 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&am...

#2135 - Q&A: “Millions of dollars for white noise tracks for Spotify ... this is crazy!” 05.11.2022 5:31

A business recently made headlines for earning $9 million by streaming white noise tracks on Spotify. Is this still feasible for others—and if not, how can you find something like this in the first place? 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 an...

#2134 - Failure Friday: “My Facebook page with 40,000 fans was hacked…” 04.11.2022 6:16

In this week’s Failure Friday segment, we hear from a coach who had been building her business on Facebook—until she made a mistake and clicked a password reset link from a hacker. 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 sev...