Chris Guillebeau

Side Hustle School

Business EN ↓ 3654 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

#1976 - First $1,000: “I wasn’t sure what to do, so I started selling sports cards…” 30.05.2022 8:36

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...

#1975 - Q&A: “When do I let go of an unprofitable idea?” 29.05.2022 4:01

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: te...

#1974 - Q&A: “If everyone learns SEO, how can you ever win?” 28.05.2022 4:18

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.c...

#1973 - Failure Friday: “Offensive Greeting Cards” Lost in Post 27.05.2022 6:32

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 sho...

#1972 - TBT: Mixed Media Artist Sews Up Side Earnings 26.05.2022 6:18

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...

#1971 - Q&A: “Is it ever too early to post on social media?” 25.05.2022 3:44

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 no...

#1970 - Charcuterie Boards Cure Couple's Pandemic Woes 24.05.2022 6:22

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@sidehustleschoo...

#1969 - First $1,000: “I couldn’t believe I got paid playing a game I loved…” 23.05.2022 6:07

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 day...

#1968 - Q&A: “I’m trying to sell tickets to a Mexican version of Bingo…” 22.05.2022 4:59

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: tea...

#1967 - Q&A: "I got a nasty email from my competitor..." 21.05.2022 4:31

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@sidehustle...

#1966 - Failure Friday: “80% of our customers never returned…” 20.05.2022 6:21

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...

#1965 - TBT: Adventurous Kitchen Tool Set Goes Global 19.05.2022 6:57

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. Th...

#1964 - Q&A: “Why do people buy courses when YouTube is free?” 18.05.2022 5:45

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/question...

#1963 - Head-to-Toe Holistic Skincare Biz Shows Moxie 17.05.2022 5:37

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: SideHust...

#1962 - First $1,000: Bulldog Blogger Builds Bow-Wow Biz 16.05.2022 7:42

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...

#1961 - Q&A: “What are the most profitable niches for teaching?” 15.05.2022 5:15

Some topics or niches are much more profitable than others. Today’s caller is wondering if we can cut to the chase and just give him a list. Fair enough! 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...

#1960 - Q&A: “How can I get YouTube’s algorithm to like me??” 14.05.2022 5:29

Today’s caller is making a YouTube series, but not getting the traction he’d like. Is there anything he can do to have his videos seen by more people? 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:...

#1959 - Failure Friday: “Switchasaurus” Card Game Almost Goes Extinct 13.05.2022 8:07

In this week’s Failure Friday segment, we hear from the inventor of “Switchasaurus,” a dinosaur card game. When his first supplier under delivers, he tries to evolve. 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...

#1958 - TBT: Boise Woodworking Team Upgrades Toolkit 12.05.2022 7:12

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Idaho woodworker. As more people have moved to the area, his business has taken 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 each...

#1957 - Q&A: “I have a tricky ethical situation with my day job…” 11.05.2022 5:02

What happens when your day job brings you a lead for your side hustle? This caller faces an ethical dilemma, as well as a practical 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 and listener Q&A several days each week. Show notes: SideHustleSc...

#1956 - College Student Turned Fashion Influencer Earns $140,000 10.05.2022 7:32

Fascinated by the influencer life, a university student creates a fashion blog that earns real money, thanks to SEO and Pinterest. 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....

#1955 - First $1,000: Digital Art Reaches Physical Homes Worldwide 09.05.2022 5:55

In this week’s First $1,000 segment, we hear from the co-founders of Wandercolors. Together, they produce digital art of iconic travel destinations. 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...

#1954 - Q&A: “I’m giving lots of consultations, but making few sales…” 08.05.2022 5:42

Today’s listener is experiencing lots of demand for the free version of her coaching offer, but not the paid one. Let’s see if we can help her! 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. Side Hustle School...

#1953 - Q&A: “I think my client ghosted me…” 07.05.2022 4:37

We’ve all been there—ghosted by someone we liked. In this case, a designer nearly lands the perfect client, but then the client goes AWOL. What can we learn from the experience? 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...

#1952 - Failure Friday: “I naively thought the influencers would bring sales…” 06.05.2022 5:28

In this week’s Failure Friday segment, we hear from an Australian who owns an ecommerce business offering mindful toys and gifts. Following a rebrand, she pays Instagram influencers to create interest—but mostly they just took her 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 s...