Chris Guillebeau

Side Hustle School

Business EN ↓ 3649 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.

Be sure to visit the podcast's website and support the creator: sidehustleschool.com

Author

Chris Guillebeau

Episodes

#2396 - First $1,000: Selling Vintage Clothes on Poshmark 24.07.2023 6:31

In this week’s First $1,000 segment, we hear from a seller of vintage and modern clothes who uses the online marketplace Poshmark to sell thousands of dollars of clothes each 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 sev...

#2395 - Q&A: “SEO consulting for small businesses…” 23.07.2023 4:30

A digital marketing professional wants to start side hustling. How can he position himself to serve local businesses with SEO? 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...

#2394 - Q&A: “Should I become a financial advisor for healthcare workers?” 22.07.2023 5:28

Today’s caller works as a data analyst in the health sector, but she's also got a keen interest in investing. Might there be a way to combine these talents for one side hustle to rule them all? 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...

#2393 - Failure Friday: Ghost Tours Fail to Scare Enough Clients 21.07.2023 5:55

In this week’s Failure Friday segment, we hear a spooky story: an attempt at offering a ghost tour of Denver fails to scare enough people into signing up. 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...

#2392 - TBT: Game Consoles, VCRs, and Typewriters for Sale 20.07.2023 6:01

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a reseller who specializes in retro electronics including vintage game consoles and typewriters. 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...

#2391 - Q&A: “How to sell a ‘Democracy in Action’ program?” 19.07.2023 6:07

A listener looking to inspire others to become more active in their local government wants to start a subscription service of some kind. 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...

#2390 - Q&A: “Can I tell someone else’s story on my podcast?” 18.07.2023 5:23

If you make a storytelling podcast, can you tell someone else’s story without their permission? 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...

#2389 - First $1,000: Indian Tutor Helps U.S. High School Students Learn Math 17.07.2023 6:15

In this week’s First $1,000 segment, we hear from an Indian listener. He’s built a bustling business as an online math tutor for high school students in the U.S. 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....

#2388 - Q&A: “What should I sell on Fiverr?” 16.07.2023 6:28

A digital nomad with a range of skills wants to offer services on Fiverr. How should he specialize to be most efficient and profitable? 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...

#2387 - Q&A: “It’s hard to compete with bigger firms!” 15.07.2023 4:57

A talented designer is facing competition with larger design firms in her area. How can she stand out and make her mark? 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...

#2386 - Failure Friday: Homemade Hummus Subscription Fails to Smash 14.07.2023 6:48

In this week’s Failure Friday segment, we hear from a listener with a tangy idea. Drawing on her Lebanese ancestry, she tries to create a “homemade hummus subscription box. Alas, those chickpeas failed to smash themselves into a hit. 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...

#2385 - TBT: Project Manager Side Hustles as Home Inspector 13.07.2023 6:05

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a project manager in the construction industry who has a side hustle as a home inspector. This second job earns several thousand dollars a 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 f...

#2384 - Q&A: “How to use the Pomodoro method in my side hustle?” 12.07.2023 5:38

The Pomodoro method is a classic productivity tool. How can this listener—or anyone—use it when building their 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...

#2383 - Q&A: “Need help attracting first clients…” 11.07.2023 5:03

A sales coach for Etsy and Shopify sellers is looking to expand her initial client base of friends and family members. 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: te...

#2382 - First $1,000: Airbnb Marketer Increases Rental Rates 30% 10.07.2023 5:36

In this week’s First $1,000 segment, we hear from a guy who helps Airbnb property owners and managers grow their listings and revenue. 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...

#2381 - Q&A: “Should I build a website for my freelance coding hustle?” 09.07.2023 4:57

Does this freelance programmer need a website? If so, what’s the simplest and most effective way to make 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@sidehus...

#2380 - Q&A: “How do I pinpoint the right side hustle idea?” 08.07.2023 6:25

A recent college graduate needs help choosing a side hustle that aligns with her professional skills and personal passions. 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...

#2379 - Failure Friday: “SnoozeCubes” Hustle Experiences Sleepy Sales 07.07.2023 6:44

In this week’s Failure Friday segment, we hear from the founder of SnoozeCubes, sleeping pods for offices. If you haven’t heard of this business, it’s because it never got up to Super Bowl ad-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 lessons and list...

#2378 - TBT: Copyeditor Proofreads Tech Reports & Marriage Proposals 06.07.2023 5:47

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a tech employee who moonlights as a freelance copyeditor and proofreader. 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...

#2377 - Q&A: “Can I create a fictional character for Cameo shoutouts?” 05.07.2023 5:43

Last month we talked about buying Cameo shoutouts to promote a business. This caller has a different idea: can they create a *fictional* character and offer shoutouts for sale? 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...

#2376 - Q&A: “OpenTable isn't good, how can we do better?” 04.07.2023 5:01

Today’s caller wants to make an alternative to restaurant reservations. He’s got ten years of experience in the industry, but will that be enough to create a platform at scale? 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...

#2375 - First $1,000: “Logo Lady” of Upwork Builds Design Speciality 03.07.2023 6:01

In this week’s First $1,000 segment, we hear from an HR specialist who’s also known as the “Logo Lady” of Upwork. She does only logos, which has been key to her success, and allows her to earn a good side income in a manageable number of hours. 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,...

#2374 - Q&A: “Can you grow a side hustle using Reddit?” 02.07.2023 5:36

Reddit is known as “the front page of the internet.” Can it also be a viable way to grow your business or 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: tea...

#2373 - Q&A: “Should I feel bad about side hustling at work?” 01.07.2023 4:59

This caller is running her side hustle on company time. How do we feel about 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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the sho...

#2372 - Failure Friday: “Hangover Helper” Business Sobers Up 30.06.2023 5:46

In this week’s Failure Friday segment, we hear from a San Francisco man with a dream to serve party goers who had partied a little too hard. Unfortunately, this idea soon encountered a sobering reality. 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...