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.

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Episodes

#2800 - Q&A: “How does anyone profit on Temu?

In our 2,800th episode (!), we explore how to succeed on the competitive marketplace of Temu. Learn about selecting the right products, creating standout listings, and leveraging marketing techniques to boost your sales. 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: t...

Aug 31, 20245 minEp. 2800

#2799 - Failure Friday: Bouncing Back After Two Years of Discouragement

In this week’s “Failure Friday” segment, we hear from an aspiring small business owner who got discouraged when an early side hustle idea didn’t work out and stopped trying for two years—but when he finally tries again, a new idea takes off right away! 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...

Aug 30, 20247 minEp. 2799

#2798 - TBT: Project Manager Boosts Local Food Truck Owners

In this week’s “Throwback Thursday” segment, we hear from a project manager who specializes in coordinating operations for local food truck vendors. 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 ...

Aug 29, 20245 minEp. 2798

#2797 - Q&A: “How to create engaging and profitable webinars?”

In this episode, we explore how to create engaging and profitable webinars. Even after many years and “shiny new things,” this model still works! 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 Con...

Aug 28, 20245 minEp. 2797

#2796 - Q&A: “How can Pinterest drive traffic to an e-commerce store?”

In this episode, we explore how to use Pinterest to drive traffic to your e-commerce store and boost sales. Learn to create engaging pins, optimize your profile, and leverage Pinterest’s features to attract more visitors. 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: ...

Aug 27, 20245 minEp. 2796

#2795 - First $1,000: Asian-Inspired Popcorn Delights in Vancouver

In this week’s First $1,000 segment, we hear from a digital marketer in Vancouver, BC, who turned her love for Asian flavors into a popular side hustle. Discover how they earned their first $1,000 by specializing in gourmet popcorn. 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....

Aug 26, 20245 minEp. 2795

#2794 - Q&A: “What’s the difference between dropshipping and FBA?”

In this episode, we explore the differences between dropshipping and Fulfilled by Amazon (FBA). Which e-commerce model is best for beginners? 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...

Aug 25, 20246 minEp. 2794

#2793 - Q&A: ”How do I monetize a podcast and grow my listener base?”

In this episode, we explore effective strategies to monetize a podcast and grow a loyal listener base. Learn how to attract sponsors, engage your audience, and boost your podcast’s visibility. 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 ...

Aug 24, 20246 minEp. 2793

#2792 - Failure Friday: The Case of the Disappearing Developer

In this week’s “Failure Friday” segment, we hear from a small business owner who hired someone to update their website, only to be locked out during a crucial sales period when the developer disappeared. 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@sidehustlesch...

Aug 23, 20246 minEp. 2792

#2791 - TBT: Boosting Biotech Startups with Creative Ad Strategies

In this week’s “Throwback Thursday” segment, we hear from an advertising consultant focused on biotech startups in Southern California who found success with a flat fee structure. He now earns over $150,000/year. 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@side...

Aug 22, 20247 minEp. 2791

#2790 - Q&A: “How can I manage multiple side hustles without burning out?”

In this episode, we explore how to manage multiple side hustles without burning out. Learn practical strategies to prioritize tasks, stay organized, and maintain your sanity while juggling several 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 week. Show notes: SideHustleSchool.com Email: team@sidehustle...

Aug 21, 20245 minEp. 2790

#2789 - Q&A: “How can I monetize my blog beyond ad placements?”

In this episode, we explore effective ways to monetize your blog beyond traditional ad placements. Learn about affiliate marketing, sponsored content, creating digital products—and more! 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...

Aug 20, 20245 minEp. 2789

#2788 - First $1K: 3D Modeling Skills Leads to International Business

In this week’s “First $1K” segment, we hear from an engineer who used his skills in 3D modeling and rendering to offer services on Upwork. Discover how he leveraged his expertise in a growing freelance 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 notes: SideHustleSchool.com Email: team@sidehus...

Aug 19, 20247 minEp. 2788

#2787 - Q&A: “How to market a unique contact management app?”

In this episode, we explore an idea for a contact management app. A caller needs help defining the ideal audience and getting it to 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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect o...

Aug 18, 20244 minEp. 2787

#2786 - Q&A: “Can you make money reselling airline amenity kits?”

In this episode, we explore the unique idea of collecting and reselling airline amenity kits. Is it a viable side hustle, or will the idea fail to take flight? 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...

Aug 17, 20245 minEp. 2786

#2785 - Failure Friday: A Year Spent Writing the Wrong Book

In this week’s “Failure Friday” segment, we hear from a programmer who spent a year writing a 300-page book of life lessons only to realize it was overly generic and unappealing. 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...

Aug 16, 20247 minEp. 2785

#2784 - TBT: A Clothing Reseller’s Transition from Poshmark to Depop

In this week’s “Throwback Thursday” segment, we hear from a clothing reseller who shifted her focus from Poshmark to Depop, now making more than half her sales on the Gen-Z focused platform. 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...

Aug 15, 20247 minEp. 2784

#2783 -Q&A: “How can I scale my art business using social media?”

In this episode, we explore how artists can scale their businesses using social media and targeted ads, and other effective strategies. Special case study: a listener in Miami! 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: Sid...

Aug 14, 20245 minEp. 2783

#2782 - Q&A: “How to prepare for a side hustle while incarcerated?”

In this episode, we discuss legal side hustles for prisoners, as well as how they can build the right kinds of skills to succeed upon release. Bravo to our listener for raising this question! 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 o...

Aug 13, 20246 minEp. 2782

#2781 - First $1,000: Transforming Homes to Sell Faster in Pittsburgh

In this week’s “First $1K” segment, we hear from Emma in Pittsburgh, who transformed her talent for decorating into a profitable home staging business. Learn how she earned her first $1,000 by helping homeowners and realtors prepare properties for sale. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.sub...

Aug 12, 20247 minEp. 2781

#2780 - Q&A: “What types of social media ads are most effective?”

In this episode, we break down the most effective types of social media ads and what makes them successful. Learn about targeting, content creation, and key strategies to boost your side hustle—without wasting 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 notes: SideHustleSchool.com Email: team@...

Aug 11, 20246 minEp. 2780

#2779 - Q&A: “How does the funnel system work for selling info products?”

In this episode, we break down the funnel system for selling info products. Learn the different stages of the funnel and how to use this approach to maximize your sales, starting with a low-cost product to bring people in. 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:...

Aug 10, 20246 minEp. 2779

#2778 - Failure Friday: How a $20,000 Mastermind Led Me Astray

In this week’s “Failure Friday” segment, we hear from an eager coach-in-training who spent $20,000 to join a mastermind group that focused on ecommerce businesses, leaving her lost and overwhelmed as she tried to start her new business. Discover how she navigated this setback and began working more strategically towards her goals. 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...

Aug 09, 20247 minEp. 2778

#2777 - TBT: Solar Panel Sales Pro Earns $120,000+

In this week’s “Throwback Thursday” segment, we hear from a solar panel sales rep in Utah who earns all his income through commissions. Discover how he rose from a newbie to a top performer, now earning over $100,000 a year working part-time in the competitive solar 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 day...

Aug 08, 20245 minEp. 2777

#2776 - Q&A: “How can I get my documentary funded?”

In this episode, we explore the best ways to fund a documentary, including grants, crowdfunding, and sponsorships. Learn how to secure the budget you need to bring a creative project to life. 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 o...

Aug 07, 20245 minEp. 2776

#2775 - Q&A: “Can small content creators succeed with affiliate marketing?”

In this episode, we explore how smaller content creators can compete in the affiliate marketing space dominated by big companies. Learn realistic strategies to stand out and attract the search traffic you need to succeed. 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: ...

Aug 06, 20246 minEp. 2775

#2774 - First $1,000: Oakland Car Detailing Hustle Waxes On, Off

In this week’s “First $1K” segment, we visit Oakland, California, where a side hustler with a passion for car racing creates a successful detailing biz. 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/questi...

Aug 05, 20246 minEp. 2774

#2773 - Q&A: “What are the best time-tracking tools?”

In this episode, we explore the best time-tracking tools and share some side hustle ideas for helping others manage their time more effectively. 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 Conn...

Aug 04, 20244 minEp. 2773

#2772 - Q&A: ”What’s the wildest side hustle idea you’ve ever heard of?”

In this episode, we explore some of the wildest side hustle ideas ever featured on the show. Discover how people are making extra money with chickens, air, and goats! Also: are these unconventional ideas more likely to succeed? 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 E...

Aug 03, 20245 minEp. 2772

#2771 - Failure Friday: Executive Function Coach Experiences Burnout

In this week’s Failure Friday segment, we hear from a coach who works with families on executive function issues. Business is growing—a bit too fast, it turns 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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool...

Aug 02, 20247 minEp. 2771
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