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

#1883 - Q&A: How can I fund my quest to run across the country? 26.02.2022 5:18

Today’s caller wants to—wait for it—run across the United States. What an incredible, audacious goal! But of course she needs funding, and she wants to think creatively. What are her options? 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...

#1882 - Failure Friday: “I dropped out of Stanford and left my business at the same time…” 25.02.2022 6:31

In this week’s Failure Friday segment, we hear from Bryan Quoc Le, a scientist and food blogger. His early days of selling vegan banana ice cream at Stanford felt promising, but soon turned into too much to handle. 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...

#1881 - TBT: Orthodontist Invents Modern Tool for Impacted Teeth 24.02.2022 8:12

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a North Carolina orthodontist who invents a better way to treat impacted teeth. Gold chains belong in the 1980s! 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...

#1880 - Q&A: “I’d like to lead a cross-country caravan tour…” 23.02.2022 5:00

Can you get paid to lead a cross-country caravan with dozens of vehicles in a cross-country road trip? That’s what this caller envisions. 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...

#1879 - Online Literacy Tutoring Proves Profitable 22.02.2022 7:35

A literacy teacher feeling frustrated with administration decides to strike out on her own, creating a surprisingly resilient business model with multiple streams of 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 da...

#1878 - First $1,000: “After 9 months, we got our first $50 sponsorship…” 21.02.2022 9:14

In this week’s First $1,000 segment, we hear from Kelan Kline, co-founder of TheSavvyCouple.com. It took Kelan and his wife a while to get going, but the blog eventually became a multiple six-figure business. 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...

#1877 - Q&A: How do I best prioritize what to do next? 20.02.2022 4:32

She’s selling a set of planners for new moms struggling with postpartum depression. How can she reach the target market with her product? 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...

#1876 - Q&A: Get paid to drive a stranger’s car across the country? 19.02.2022 4:17

Today’s question brings me back to one of my long-ago lifelong goals. Can you get paid to drive someone’s car across the country when they relocate?? 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:...

#1875 - Failure Friday: “I started to realize how little I knew…” 18.02.2022 5:54

In this week’s Failure Friday segment, we hear from Danielle Winton, a furniture reseller in Missouri. Business was going along smoothly, until she took on a project that proved to be much tougher than expected. 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 le...

#1874 - TBT: Soap Opera Star Becomes Professional Organizer 17.02.2022 7:38

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Regina Leeds, an actress in Los Angeles who left a career in soap opera to become an author and professional organizer. 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 li...

#1873 - Q&A: “Fly as an airline courier” ... is that a thing? 16.02.2022 4:53

Today’s caller has seen ads about becoming an independent airline courier. It sounds fun—but is this a viable business opportunity, a scam, or something else? 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...

#1872 - Voiceover Couple Averages $4,500/Month 15.02.2022 7:42

This voice actor couple is stepping up to the mic, building a legacy with A-list clients and creating generational wealth for their family. 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: SideHustle...

#1871 - First $1,000: “I had literally zero intention of running a business…” 14.02.2022 8:34

In this week’s First $1,000 segment, we hear from Lindsay Gordon, who left a career at Google to become a career coach for analytically-minded 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...

#1870 - Q&A: Is the directory website model outdated? 13.02.2022 6:25

A caller from Massachusetts has a small moving business and is thinking about adding a directory website that provides listings to movers from around the country. Is this business model outdated, or might it still have potential? 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 inc...

#1869 - Q&A: “I’m building the world's most difficult scavenger hunt…” 12.02.2022 4:50

A scavenger hunt that takes place across state lines and requires weeks to complete? That’s what our listener is putting together! 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...

#1868 - Failure Friday: “What you didn’t hear was how unfocused I was…” 11.02.2022 7:43

In this week’s Failure Friday segment, we hear from Chelsea Raehl, who sells 3D printed cookie cutters. After starting out strong, she quickly became unfocused and exhausted in trying to do too many things at once. 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 guid...

#1867 - TBT: Catholic Designer Updates T-Shirts for New Generation 10.02.2022 6:57

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Joe Kim, founder of PAL Campaign. Seeking to advance what he calls “the dog days of Christian t-shirt design,” he introduced a fresh, updated style that teenagers in youth groups would actually wear. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money w...

#1866 - Q&A: What kind of side hustle can I start with a chronic illness? 09.02.2022 5:43

Today’s caller has an autoimmune disease that limits her energy. When it’s hard to commit in advance to a schedule of tasks, what kind of side hustle should you consider? 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 ea...

#1865 - “Free Prep Course” Site Generates 7-Figure Income 08.02.2022 7:33

A former educator schools the system, offering his test prep guides for free but generating a massive return through online advertising. 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...

#1864 - First $1,000: “It was the Super Bowl of professional fishing…” 07.02.2022 7:39

In this week’s First $1,000 segment, we hear from Pete Robbins, a government lawyer who gets paid to go fishing and write about it. His best advice: “Press the damn send button.” 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...

#1863 - Q&A: How can my tour business earn recurring revenue? 06.02.2022 5:12

Today’s caller is a tour operator who hosts visiting Americans and other tourists in his home city of Barcelona. Is there a way he can shift from being paid for single tours to a recurring revenue model? 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...

#1862 - Q&A: How can I get med students to buy my flash cards? 05.02.2022 4:02

This listener has made a set of flash cards to help med students memorize part of the body and other terminology. How can they reach their target market? 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...

#1861 - Failure Friday: “My Facebook page with 150,000 fans was taken over by hackers…” 04.02.2022 6:37

In this week’s Failure Friday segment, we hear from the world’s leading expert on tailgating. When his popular Facebook page got hacked, he lost thousands of followers and it took more than a month to resolve. 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...

#1860 - TBT: “Walking Dead” Sugar Cookies Provide Sustenance for Apocalypse 03.02.2022 6:56

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Carrie Buchanan, founder of the Bombshell Baking Company. This full-time social worker earns up to $4,000/weekend selling themed cookies at conventions. 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 inc...

#1859 - Q&A: Should I sell guides for software application training? 02.02.2022 5:19

A listener in Ireland wonders about selling e-books or other tools to help users with software applications like Microsoft Word or Google Docs. What does she need to know? 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 e...