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

#2333 - First $1,000: Home Improvement Employee Moonlights as Renovation Aide 22.05.2023 5:59

In this week’s First $1,000 segment, we hear from someone who works at a home improvement store by day—and moonlights by advising homeowners on renovation projects. 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 we...

#2332 - Q&A: “I’m adding a subscription box for soaps…” 21.05.2023 4:17

A listener who sells handmade soap is considering adding a subscription box service, where customers receive a curated selection of products every 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. Show not...

#2331 - Q&A: “Cost-effective marketing strategies?” 20.05.2023 4:44

Today's caller is on a mission to find cost-effective marketing strategies for their side hustle. How do you get the word out without spending much money? 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...

#2330 - Failure Friday: Chicken Rental Service Fails to Egg-cite 19.05.2023 6:04

In this week’s Failure Friday segment, we hear from a Boise entrepreneur with the goal of bringing chickens to city dwellers. Alas, in the end the business is forced to flee the coop. 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...

#2329 - TBT: Handywoman Offers DIY Home Repair Workshops 18.05.2023 5:28

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Washington handywoman who operates a series of DIY Home Repair workshops. 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...

#2328 - Q&A: “Voiceover artist offers voiceover coaching…” 17.05.2023 4:42

A voiceover question from a voiceover artist on potential voiceover coaching for voiceover clients. Did you get that? Hint: it’s about voiceover. 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...

#2327 - Q&A: “Reaching the right audience with digital prints…” 16.05.2023 5:08

In today's episode, we have a question from a listener working on a side hustle creating and selling digital art prints online. How can he discover and reach the perfect audience? 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...

#2326 - First $1,000: Baltimore Photographer Starts Drone Instruction 15.05.2023 5:25

In this week’s First $1,000 segment, we hear from a Baltimore photographer who finds inspiration high in the sky. His new business teaching drone photography is taking off! 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...

#2325 - Q&A: “I'm looking to leverage my existing skills…” 14.05.2023 5:09

In today’s episode, a talented graphic designer and marketer searches for a fulfilling side hustle that capitalizes on her existing skill set. How can you find one for yourself? 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...

#2324 - Q&A: “I want to offer home staging services…” 13.05.2023 5:15

A listener in Vancouver wants to start a home staging side hustle. How can she build a portfolio of clients and develop the right relationships? 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...

#2323 - Failure Friday: “Looking back on my picnic misadventures…” 12.05.2023 6:19

In this week’s Failure Friday segment, we hear from a Miami caterer who had a cute idea to sell customized picnic lunches. Unfortunately, things didn’t turn out the way she hoped. 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 severa...

#2322 - TBT: Mobile Pet Grooming Thrives in Oakland 11.05.2023 6:04

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a startup employee offering a mobile pet grooming side hustle in Oakland, California. 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 we...

#2321 - Q&A: “I’m a language tutor… and I need more students!” 10.05.2023 5:31

A language tutor in Boston wants to focus more on her sessions and less on bringing in new students. How can she become fully booked? 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...

#2320 - Q&A: “Handmade pottery sales have plateaued…” 09.05.2023 5:02

A listener in Minnesota has been running a side hustle selling handmade pottery on Etsy for about a year. He had a good start with sales but has since plateaued—how can we get him back on the fast track? 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...

#2319 - First $1,000: “I wanted to explore AI-generated art…” 08.05.2023 6:10

In this week’s First $1,000 segment, we hear from a real estate professional who makes and sells design elements that come from AI-generated art. 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: Si...

#2318 - Q&A: “How can I make eco-friendly surfboard wax??” 07.05.2023 4:51

We've got a gnarly question today from Brad in San Diego: how can this software developer and surfer start a side business selling eco-friendly surfboard wax? 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. Sho...

#2317 - Q&A: “Building a network as an introvert…” 06.05.2023 3:58

Building a strong network is vital for side hustle success, but today’s caller is an introvert. Should he just “get over it,” or are there strategies he can use to succeed on his own terms? (Hint: door number two.) 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...

#2316 - Failure Friday: “Puzzlemaster of Cleveland” Fails to Break Even 05.05.2023 6:36

In this week’s Failure Friday segment, we hear from a city engineer who tries to bring “game night” to companies. Alas—it doesn’t turn into a puzzling success. 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...

#2315 - TBT: Tiny Home Consultant Designs Bespoke Blueprints 04.05.2023 5:58

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a location independent editor who has a sideline as a tiny home consultant. Like its industry, this side hustle is growing! 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...

#2314 - Q&A: “I’m a personal chef in New York City…” 03.05.2023 4:33

An NYC personal chef wants to offer personalized cooking classes focused on healthy, plant-based meals. How can she attract the right 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: SideHu...

#2313 - Q&A: “Structuring a freelance writing program…” 02.05.2023 4:25

In this lively episode, we'll hear from a seasoned freelance writer with a background in journalism. He wants to make a coaching program—but how will he compete with AI? 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 eac...

#2312 - First $1,000: “BritBox” Sends British-Themed Goods Worldwide 01.05.2023 7:44

In this week’s First $1,000 segment, we hear from the founder of BritBox, a service that sends British-themed goods to lonely expats around the world. 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...

#2311 - Q&A: “Struggling to balance day job, family, and online boutique…” 30.04.2023 4:59

If you're feeling overwhelmed by multiple commitments, this episode will give you three practical tips to help you streamline your side hustle without compromising your main priorities. 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...

#2310 - Q&A: “How can I start a personal shopping business?” 29.04.2023 4:57

A caller is interested in starting a personal shopping business. What’s the best way to approach 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 free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustl...

#2309 - Failure Friday: “Ultimate Wrinkle Inducer” MLM Flops 28.04.2023 6:29

In this week’s Failure Friday segment, we hear from an office manager who gets sucked into a makeup MLM and lives to tell the tale. 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....