Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau sidehustleschool.com
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.

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Episodes

#1991 - Digital Illustrator Crafts Creative Designs

An American expat living in France draws on her artistic ability and heritage to sell multiethnic graphic illustrations. 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 show: SideHustleSchool.com/questions Connect on Twitter: @chrisgu...

Jun 14, 20226 minEp. 1991

#1990 - First $1,000: “I wanted to be the guy with a laptop on the beach…”

In this week’s First $1,000 segment, we hear from the founder of Maid This, a cleaning company that grows to millions of dollars in sales and allows the founder to work remotely. 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 show: S...

Jun 13, 20227 minEp. 1990

#1989 - Q&A: “I’m offering executive coaching at a high price…”

Today’s caller is on their second attempt with a coaching service for busy executives. It’s a big-ticket item, but the first round didn’t go very well. What should they do differently for take 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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.co...

Jun 12, 20225 minEp. 1989

#1988 - Q&A: “Can you make more from courses than anything else?”

It’s a common path to go from being a Creator in a certain field to teaching people how to do something similar—so why not skip a step and go straight to making courses? 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 show: SideHustle...

Jun 11, 20225 minEp. 1988

#1987 - Failure Friday: “I acted like an inexperienced order-taker…”

In this week’s Failure Friday segment, we hear from a writer who now earns a six-figure income from her freelance work. In the beginning, however, she had to learn to communicate better with potential 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: SideHustleSchool.com Email: team@sidehus...

Jun 10, 20226 minEp. 1987

#1986 - TBT: Luggage Storage Business Attracts Copycats

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a luggage storage business for tourists. It was going so well that someone else decided to replicate the model for themselves, cutting into her customer base. How did she handle 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 day...

Jun 09, 20229 minEp. 1986

#1985 - Q&A: “Best way to get to market with nutrition bar…”

A listener is launching an “all-in” protein bar. It’s a crowded market, but they’re, well, all-in. How can we help them get on the shelves of Whole Foods? 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 show: SideHustleSchool.com/ques...

Jun 08, 20225 minEp. 1985

#1984 - Data Scientist Profits from Viral Article

After her Medium article gains attention, a data scientist creates an online community and series of courses, resulting in a new source of reliable income. 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 show: SideHustleSchool.com/que...

Jun 07, 20227 minEp. 1984

#1983 - First $1,000: “I’ll never forget the moment I got paid…”

In this week’s First $1,000 segment, we hear from Jennifer Sobel, a belly dancing coach (!) who takes her program online. It’s now a midsection-shaking success—but how did she get there? 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...

Jun 06, 20228 minEp. 1983

#1982 - Q&A: “Can I tell people where to find fake luxury goods?”

A listener wants to sell a guide to replica luxury goods. She’s not going to sell the items themselves, just the information. Is this a good 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Co...

Jun 05, 20224 minEp. 1982

#1981 - Q&A: “How much time do people spend on these projects?”

If you have at least one side hustle already, is it a couple hours a week, taking over your life, 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 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 show: SideHustleSchool.com/questions Connect on Twitter: @chris...

Jun 04, 20224 minEp. 1981

#1980 - Failure Friday: “We locked ourselves in a room for six months to build it…”

In this week’s Failure Friday segment, we hear from the co-founder of Sports Bookr, a service that helps sports facilities with online booking and scheduling. In starting up, the team learned that “validation” is not a one-time activity. 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: SideHustleSc...

Jun 03, 20228 minEp. 1980

#1979 - TBT: Voiceover Artist Grows Business With Gusto

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a full-time voiceover artist. It started from a podcast about Downton Abbey! 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 show: SideHustleSchool.com/qu...

Jun 02, 20227 minEp. 1979

#1978 - Q&A: “How do I market and get my first customers?”

Our caller today is like a lot of listeners: when the time comes to start a project, how do you market and attract your first customers? 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 show: SideHustleSchool.com/questions Connect on T...

Jun 01, 20225 minEp. 1978

#1977 - This Balloon-Popping Tool Strikes Helium Gold

A graphic designer flies high with an invention to bring balloons down to earth. 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 show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193count...

May 31, 20227 minEp. 1977

#1976 - First $1,000: “I wasn’t sure what to do, so I started selling sports cards…”

In this week’s First $1,000 segment, we hear from a Los Angeles consultant who begins buying and reselling sports cards during the pandemic. He does it because it’s fun—but it also ends up being highly 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: SideHustleSchool.com Email: team@sid...

May 30, 20229 minEp. 1976

#1975 - Q&A: “When do I let go of an unprofitable idea?”

Today’s caller is at a crossroads: should she keep pursuing her side hustle idea even though it hasn’t been 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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisgui...

May 29, 20224 minEp. 1975

#1974 - Q&A: “If everyone learns SEO, how can you ever win?”

Should you bother trying to optimize your website for search engines? Our caller wonders if it’s an arms race that no one can win. 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 show: SideHustleSchool.com/questions Connect on Twitter...

May 28, 20224 minEp. 1974

#1973 - Failure Friday: “Offensive Greeting Cards” Lost in Post

In this week’s Failure Friday segment, we hear from the founder of a line of “rude, offensive greeting cards” in the UK. As his business grew, he turned to overseas suppliers for a big holiday shipment. You might guess what happens next! 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: SideHustleSc...

May 27, 20227 minEp. 1973

#1972 - TBT: Mixed Media Artist Sews Up Side Earnings

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a New Hampshire fabric artist. She’s built a seamless business while working a day job in 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 the show: SideHu...

May 26, 20226 minEp. 1972

#1971 - Q&A: “Is it ever too early to post on social media?”

At what point in your new hustle should you start posting on social media—should it be before you even have a product or service, or is it better to wait? 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 show: SideHustleSchool.com/ques...

May 25, 20224 minEp. 1971

#1970 - Charcuterie Boards Cure Couple's Pandemic Woes

A midwestern couple makes cash out of catastrophe, reinventing themselves during the 2020 lockdown. 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 show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on I...

May 24, 20226 minEp. 1970

#1969 - First $1,000: “I couldn’t believe I got paid playing a game I loved…”

In this week’s First $1,000 segment, we hear from the founder of StartPlaying.Games, a hub for professional dungeon masters who facilitate tabletop games at private events. 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 show: SideHus...

May 23, 20226 minEp. 1969

#1968 - Q&A: “I’m trying to sell tickets to a Mexican version of Bingo…”

A caller from Mexico City is starting a Lotería, a Mexican version of Bingo. How can she get people to buy tickets? 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 show: SideHustleSchool.com/questions Connect on Twitter: @chrisguilleb...

May 22, 20225 minEp. 1968

#1967 - Q&A: "I got a nasty email from my competitor..."

This listener just heard from their competition—and the competition isn’t happy. How should they respond? 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 show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connec...

May 21, 20225 minEp. 1967

#1966 - Failure Friday: “80% of our customers never returned…”

In this week’s Failure Friday segment, we hear from the founder of Plate Crate, a baseball-themed subscription service. Business was going great–but when he decided to upgrade the website, the count quickly went against him. 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 Emai...

May 20, 20226 minEp. 1966

#1965 - TBT: Adventurous Kitchen Tool Set Goes Global

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of QD Foodie, a kitchen tool collection that makes cooking fun. Her products are now sold in houseware stores across the U.S. and direct to customers worldwide. 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...

May 19, 20227 minEp. 1965

#1964 - Q&A: “Why do people buy courses when YouTube is free?”

If knowledge is free, why does anyone pay 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 the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: C...

May 18, 20226 minEp. 1964

#1963 - Head-to-Toe Holistic Skincare Biz Shows Moxie

With startup costs of $150 from a tax refund, this single mom teaches the science of healthy skin with simple, small batch skincare products. 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 show: SideHustleSchool.com/questions Connect...

May 17, 20226 minEp. 1963

#1962 - First $1,000: Bulldog Blogger Builds Bow-Wow Biz

In this week’s First $1,000 segment, we hear from the creator of FrenchieJourney.com, a boisterous blog and bedazzling resource for fans of French bulldogs. 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 show: SideHustleSchool.com/qu...

May 16, 20228 minEp. 1962
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