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

#2233 - Q&A: “Remote personal training from Pakistan…” 11.02.2023 5:39

Today’s caller is from Pakistan, and he wants to operate a remote personal training side hustle. He’s qualified for this role and thinks it could be helpful—but he’s also wise enough to foresee a couple of challenges. 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...

#2232 - Failure Friday: Bunny Breeding Gone Bad 10.02.2023 5:04

In this week’s Failure Friday segment, we hear from an aspiring bunny reader. After being inspired by a woman who breeds rabbits to pay for college, she attempts to start her own breeding farm. Unfortunately, it turns out she’s living on burrowed time. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th...

#2231 - TBT: Plates and Bowls Using Fulfillment by Amazon 09.02.2023 5:34

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a pottery maker who sells her dishes and bowls using Fulfillment by Amazon. That service is usually for mass-manufactured items, so her product is a bit different. 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,...

#2230 - Q&A: “Side hustle opportunities for retirees…” 08.02.2023 5:41

In this episode, a caller wonders about opportunities for retirees. Are some side hustles inherently better for someone in that situation? Let’s talk it 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...

#2229 - Q&A: “How to use ChatGPT and AI in a side hustle…” 07.02.2023 6:08

A listener is wondering about AI, specifically ChatGPT, an incredible tool that’s been all over the news lately, and how it applies for side hustling. Can you outsource your tasks to these tools? Can you put them to work? Can you make something using AI and sell it? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

#2228 - First $1,000: “Budget Bliss Weddings” Cuts the Cake 06.02.2023 5:06

In this week’s First $1,000 segment, we hear from a wedding planner who specializes in budget ceremonies while still getting paid for her important work. 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...

#2227 - Q&A: “Conflict with my partner over my side hustle…” 05.02.2023 5:24

Let’s have some real talk today: a side hustling caller is having a problem with her side hustle: her partner doesn’t like it. :( 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...

#2226 - Q&A: “Is it better to have prices end in the number 9?” 04.02.2023 4:53

One of our callers has noticed that lots of stuff for sale ends in the number 9. Is this some scientifically proven marketing principle, or is it entirely random? You might be surprised by the answer! 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...

#2225 - Failure Friday: “The scavenger hunt turned into a rainstorm…” 03.02.2023 6:01

In this week’s Failure Friday segment, we hear from the aspirational owner of a scavenger hunt side hustle. On a big day for a major client, everything goes wrong. 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...

#2224 - TBT: Career Advisor Sells Resume Templates 02.02.2023 5:16

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a career advisor who sells resume (CV) templates and coaching. The business now brings in at least $4,000/month. 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...

#2223 - Q&A: “Side hustle opportunities for introverts…” 01.02.2023 5:41

If you don’t like selling, or just talking to people all the time—I’m in that club!—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 week. Show notes: SideHustleSchool.com Email: team@sidehustleschool....

#2222 - Q&A: “I want to make and sell a pickleball paddle…” 31.01.2023 5:28

Did you know that pickleball is the fastest-growing sport in the world? In this episode, a listener from Arizona wonders about making and selling his own paddle. 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....

#2221 - First $1,000: “I get paid to take stock photos for licensing…” 30.01.2023 5:29

In this week’s First $1,000 segment, we hear from a photographer who learns to take photos for stock image sites, earning a royalty every time one is licensed. Pretty cool! 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...

#2220 - Q&A: “Can't find the time to grow my business!” 29.01.2023 6:05

We often identify a lack of time as the primary obstacle to starting or growing a side hustle. Often, however, there’s a deeper problem behind the time struggle. Where’s the real resistance? 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&...

#2219 - Q&A: “A subscription to manage other subscriptions…” 28.01.2023 5:57

How many paid subscriptions do you have right now? I’m embarrassed to say I don’t know the answer for myself. Today, a caller wants to develop a tool to help people save money on their recurring subscriptions. I love this idea! 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...

#2218 - Failure Friday: “I held a sock puppet show while processing transactions…” 27.01.2023 5:41

In this week’s Failure Friday segment, we hear from a sock seller who eagerly sets up at a trade show, only to realize his credit card processing equipment isn’t working. Oh no! 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...

#2217 - TBT: “I put in long hours and worked hard to deliver quality work…” 26.01.2023 4:52

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a web developer who goes from corporate to self-employed, hunting down clients on online job boards like Upwork. 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...

#2216 - Q&A: "Ebay selling feels less personal now..." 25.01.2023 6:22

Longtime listeners know that I got my start in the world of entrepreneurship when I was 19 and learned to sell on eBay. Today, a caller wonders: “Has eBay changed? It feels less personal.” 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&amp...

#2215 - Q&A: “How to create ‘transformational’ online courses?” 24.01.2023 4:55

What’s the latest in online education? That’s what one of our listeners who’s also a course creator wants to know. I’ll focus my answer on “transformation,” an increasingly important concept for anyone who wants to offer any type of online course to be aware of. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting the...

#2214 - First $1,000: “I earn £2,500 per month leading London walking tours…” 23.01.2023 5:43

In this week’s First $1,000 segment, we hear from a walking tour guide in London. He leads tours only on weekends and brings in an extra £2,500 ($3,000) per month. 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...

#2213 - Q&A: “Can I sell a calendar sometime other than January?” 22.01.2023 4:18

Some business ideas are better suited for certain seasons—as we heard recently from a caller who referenced an episode about letters from Santa. This leads to a challenge for today’s caller, who has a brilliant idea … at an inopportune 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...

#2212 - Q&A: “Is there a summer camp for side hustlers?” 21.01.2023 4:45

Today’s caller has an idea for adult summer camp with a side hustle focus. One of the reasons we have this segment is to look at different business ideas and consider how feasible they might be. So—is this an awesome idea, a terrible one, or somewhere in between? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting the...

#2211 - Failure Friday: “The client was shocked by the amount of taxes they owed…” 20.01.2023 4:55

In this week’s Failure Friday segment, we hear from a new bookkeeper who makes a big mistake: she overstates the income on a client’s return. Yikes! 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...

#2210 - TBT: “Expanding my product line paid off in a big way…” 19.01.2023 5:31

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a seller of planners and journals. After expanding her product line and listening to customers, the business is thriving. 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...

#2209 - Q&A: “Can I deduct clothes and haircuts on my taxes?” 18.01.2023 4:16

If you have a side hustle or even if you’re starting one and it doesn’t have revenue yet, you might be able to save a lot of money on your tax deductions. Listen to this caller’s question! 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&amp...