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

#2532 - TBT: The Shine and Rise of an Office Cleaning Maven 07.12.2023 5:39

In this week’s “Throwback Thursday / Where are they now?” segment, we explore the evolution of a Minneapolis-based office cleaning service that polished its approach to staffing, customer retention, and sustainability. 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...

#2531 - Q&A: “Can I use ChatGPT to help with social media?” 06.12.2023 4:54

How can AI technology be used effectively for creating a constant stream of engaging social media content? 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...

#2530 - Q&A: “How can I transition from corporate to career coaching?” 05.12.2023 5:01

A listener with over ten years of experience in corporate leadership is looking to transition into career coaching. What are the essential steps he needs to take to make this career shift a successful 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 includes free guided lessons a...

#2529 - First $1,000: Data Specialist Whips Up Custom Reports 04.12.2023 5:17

In this week’s First $1,000 segment, we hear from a freelance data visualization expert who turned indecipherable data into compelling narratives. 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: Sid...

#2528 - Q&A: “My ADHD makes side hustling hard…” 03.12.2023 5:50

A listener with ADHD is struggling to keep a photography side hustle on track. If you identify as neurodivergent, how can you adjust your productivity strategy? 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...

#2527 - Q&A: “An online course for teaching ‘Uncommon Skills…’” 02.12.2023 4:32

Ever thought of turning niche hobbies like unicycling or yo-yo tricks into an online course? That’s what today’s listener has in mind. 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: SideHustleSchoo...

#2526 - Failure Friday: He Bought a ‘Bored Ape’ NFT for $80,000 01.12.2023 7:03

In this week’s Failure Friday segment, we hear from an eager enthusiast of digital art. He bought a popular “bored ape” NFT for a *lot* of money—then watched as the value dropped by 80%. 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...

#2525 - TBT: Electronic Music Producer Offers Lessons & Mentorship 30.11.2023 4:55

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an electronic music producer who also coaches other musicians. 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: SideHus...

#2524 - Q&A: “Is it too late to plan for holiday sales?” 29.11.2023 4:54

An eCommerce store owner is concerned she's a bit late to leverage the traditional fourth-quarter sales spike. Is it a lost cause? 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.co...

#2523 - Q&A: “A service to help small museums with social media…” 28.11.2023 4:33

Today's caller wants to use her love for art and history to help small museums and galleries improve their social media presence and, in turn, boost visitor numbers. How can she structure this passion into a viable 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...

#2522 - First $1,000: Birth Chart Consults Aim for Stars 27.11.2023 5:42

In this week’s First $1,000 segment, we hear from a digital age astrologer who sells personalized birth charts, charting the stars for her clients. 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...

#2521 - Q&A: “Are my Kindle highlights hiding a business opportunity?” 26.11.2023 4:36

How can you manage your Kindle highlights—and is there a business opportunity lurking in this common challenge? 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@sideh...

#2520 - Q&A: “My enthusiasm fizzles out…” 25.11.2023 5:12

A listener finds himself losing interest in side hustling after an initial burst of enthusiasm. What should you do when your early ideas keep fizzling 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 n...

#2519 - Failure Friday: Financial Abundance Coach Charges Too Much 24.11.2023 6:58

In this week’s Failure Friday segment, we hear from a woman who sets out to become a financial abundance coach—but prices her online course too high for her initial clients. 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...

#2518 - TBT: Blankets from Nepal Continue to Sell 23.11.2023 6:38

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a U.K. importer of cashmere blankets. Two years after starting her business, it’s going stronger than ever! 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&...

#2517 - Q&A: “What are average affiliate commission rates?” 22.11.2023 6:46

How much can you get paid to promote other people’s products? A listener wants to know about the average rates for 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&A several days each week. Show notes: SideHustleS...

#2516 - Q&A: “Can you earn a big DoorDash bonus and then quit?” 21.11.2023 5:35

Chasing after sign-up bonuses in the gig economy can seem like a quick way to boost earnings. It’s not a longterm income source, but once in a while it’s worth 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...

#2515 - First $1,000: Paralegal Assists U.S. Immigrants to Canada 20.11.2023 7:28

In this week’s First $1,000 segment, we hear from a Canadian paralegal who helps American immigrants learn to navigate the bureaucracy of migration. 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:...

#2514 - Q&A: “My membership site has a high churn rate…” 19.11.2023 5:09

A fitness trainer is grappling with a high churn rate in their membership-based business, compounded by burnout. How can they improve retention? 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...

#2513 - Q&A: “A personal stylist for remote workers…” 18.11.2023 5:19

A listener wants to help remote workers look good on screen. Can she monetize her passion for “Zoom fashion”? 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...

#2512 - Failure Friday: PayPal Freezes $50,000 in Ticket Fees 17.11.2023 7:43

In this week’s Failure Friday segment, we hear from a first-time event host who sells out a big event—only to discover that PayPal refuses to give him the money. Lots of lessons here! 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...

#2511 - TBT: The Midwest Car Parts Mogul 16.11.2023 5:18

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a car parts reseller in Missouri who’s been growing his side hustle all the way to six-figures. What can we learn from his story? 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 lesso...

#2510 - Q&A: “It’s time to sell my website… how do I do it??” 15.11.2023 5:10

Selling a passion project website can be an emotional journey. Today, we navigate the steps of valuating and selling a site while ensuring it remains in capable and caring hands. 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...

#2509 - Q&A: “Can you still profit from blockchain video games?” 14.11.2023 5:15

Ever wondered if playing video games could actually make you money? Today, we look into the world of blockchain video games and assess if they can still be a profitable 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 seve...

#2508 - First $1,000: Video Editor Upgrades from Low-Paying Clients 13.11.2023 7:00

In this week’s First $1,000 segment, we hear from a video editor who starts taking cheap gigs on Fiverr before moving up to serving more valuable clients. 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...