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

#2258 - Q&A: “Should I go into business with my best friend?” 08.03.2023 4:55

This caller’s best friend is gung-ho on starting a business with her, but the caller has concerns. How can she determine if this is the right decision for both of them? 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...

#2257 - Q&A: “An EV car rental side hustle??” 07.03.2023 5:15

Sarah from Los Angeles is on the line today, and she's got a big idea brewing. Specifically, she’s thinking about starting a car rental business, but with a twist. Is there room in the market for a small, sustainable rental car brand? 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 i...

#2256 - First $1,000: Spotify Musician Gets Paid for Yoga Streams 06.03.2023 5:14

In this week’s First $1,000 segment, we hear from an independent musician who earns passive income from Spotify, focusing on keywords and playlists related to yoga. 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 wee...

#2255 - Q&A: “A home-based meal delivery service for New York…” 05.03.2023 4:30

Today’s caller has set his sights on starting a home-based meal delivery service, but wants to make sure he's covering all his bases. Let’s get him on the road to many five-star reviews! 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...

#2254 - Q&A: “I’m starting an Edible Insect Farm…” 04.03.2023 4:32

You read that right. This idea might seem buggy, but there could be a real market for 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 Email: team@sidehustleschool.com Be on...

#2253 - Failure Friday: ‘Helicopter Parent’ Disrupts Online Tutoring Session 03.03.2023 4:50

In this week’s Failure Friday segment, we hear from a self-described “former online tutor.” His business started well, but was soon challenged by a difficult parent. 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...

#2252 - TBT: Children’s Party Hostess Makes Magic and Money 02.03.2023 4:24

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Little Princess Parties, a children’s party hosting 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 free guided lessons and listener Q&A several days each week. Show...

#2251 - Q&A: “Mobile photo booths for events and parties…” 01.03.2023 5:02

Today’s caller is interested in starting a mobile photo booth business, but wants to make sure she has a solid plan in place. Let's help Janet turn her dream into a thriving 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 free guided lessons and listener Q&A se...

#2250 - Q&A: “Can you pay taxes on a credit card to earn cash back?” 28.02.2023 4:32

Tax season is coming up for many of us in the U.S., so today a caller wants to know about paying taxes on a credit card that offers cash back. Is this an all-new 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 d...

#2249 - First $1,000: Bali Nomad Writes Copy for Local Businesses 27.02.2023 4:23

\ In this week’s First $1,000 segment, we hear from an Australian expat who moves to Bali to become a digital nomad. This is the story of his first $1,000 as a freelance copywriter. 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 seve...

#2248 - Q&A: “Managing inventory for digital items…” 26.02.2023 4:58

If you’re selling a digital product, isn’t your inventory unlimited? This might sound like a trick question, but there’s more to it. When you continue to add more and more digital products to their online store, there might be a downside. 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 sh...

#2247 - Q&A: “How to become a Medical Billing Advocate?” 25.02.2023 5:15

A caller is wondering about becoming a Medical Billing Advocate. This is someone who helps patients negotiate and lower their medical bills, especially in cases where the bill is high and might include mistakes or unnecessary charges. 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 i...

#2246 - Failure Friday: “My business was like a coupon, it expired too soon…” 24.02.2023 6:38

In this week’s Failure Friday segment, we hear from someone who started a coupon directory website. Unfortunately, he ended up spending more money than he saved. 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....

#2245 - TBT: “I've been keeping bees for the past five years…” 23.02.2023 4:36

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Bay Area beekeeper who slings honey to the tune of $40,000/year part-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...

#2244 - Q&A: “I want to become a vintage shopping concierge…” 22.02.2023 5:17

I love hearing side hustle ideas from listeners! Today’s features a woman with a background in retail who wants to become a vintage shopping concierge. Is this idea feasible, profitable, and timely? 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 list...

#2243 - Q&A: “Can you set up a Shopify store in just an hour?” 21.02.2023 4:50

Today’s listener poses a challenge: is it possible to set up a Shopify store in just an hour? The platform provides a lot of different features and options, which is great but can be time-consuming to sort through. 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...

#2242 - First $1,000: This Candle Maker Doesn’t Flame Out 20.02.2023 4:51

In this week’s First $1,000 segment, we hear from a longtime candle lover who starts her own brand. After a few months, she reaches a flaming milestone and is lit with excitement. 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...

#2241 - Q&A: “Email list hosting gets more and more expensive…” 19.02.2023 5:01

Today’s listener has achieved a milestone: they have 3,000 people on their list! That’s great, but because email list providers charge based on subscriber numbers, the monthly subscription cost keeps going up as well. Can anything be done about this? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This...

#2240 - Q&A: “Betting on political markets using Kalshi…” 18.02.2023 5:47

Platforms like Kalshi and Polymarket offer the ability to bet on political events, including presidential elections and cabinet appointments. What are some tips for coming out ahead? 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...

#2239 - Failure Friday: “I wasn't making enough money to cover expenses…” 17.02.2023 5:32

In this week’s Failure Friday segment, we hear from a travel agent who’s excited to take flight—until a trip she books for ten clients is unexpectedly canceled. 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...

#2238 - TBT: ”I get to make dad jokes about adult toys all day…” 16.02.2023 4:52

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a seller of adult toys and other items for sexual wellness. She now earns $3,500/month in affiliate commissions! 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...

#2237 - Q&A: "Retro Resale" store sells floppy disks and cassette tapes 15.02.2023 5:09

A listener wants to open an online store selling floppy disks and cassette tapes. He thinks there’s a renaissance for these items. Is he right—and if so, what steps should he take? 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...

#2236 - Q&A: “What products are good to sell as a subscription?” 14.02.2023 4:42

Recently we’ve looked at why there are so many subscriptions. Today’s caller wonders: what are some good physical products (i.e. non-digital) to sell in subscription form? 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...

#2235 - First $1,000: “I built an Airbnb rental in my backyard…” 13.02.2023 5:09

In this week’s First $1,000 segment, we hear from a serial side hustler who builds an ADU in his backyard, allowing him to earn $1,500/month in passive rentals. He then uses the profits to buy another property. 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 less...

#2234 - Q&A: “Help, my website keeps breaking…” 12.02.2023 4:53

All you want to do is run your side hustle, take in orders, maybe grow your business, not just fix things that are broken—but these days, websites often get hacked or just go down for no good reason. Can anything be done? 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...