Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau / Onward Projectsidehustleschool.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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/  

Episodes

#2699 - Q&A: “How can I provide Continuing Education services?”

In this episode, we help a retired teacher from Tampa, Florida, navigate the world of continuing education and identify the most promising opportunities for her side hustle. 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: [email protected] Be on the show: SideHu...

May 22, 20245 minEp. 2699

#2698 - Q&A: “I lead tours in Scotland … but I want to expand.”

In today's episode, an Edinburgh tour guide wants to transform intimate, in-person experiences into captivating digital journeys—or anything else that provides passive 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: [email protected] Be on the show: Side...

May 21, 20246 minEp. 2698

#2697 - First $1,000: Instagram Growth Guru Boosts Local Businesses

In this week’s First $1,000 segment, we hear from an Instagram aficionado who turned their skills into a profitable business helping local businesses thrive. 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: [email protected] Be on the show: SideHustleSchool.com/q...

May 20, 20246 minEp. 2697

#2696 - Q&A: “How can I develop a game for the App Store?”

In this episode, we help a self-taught programmer from Manchester, UK, turn her coding skills into a video game for the iOS App Store. Tune in to learn how to validate a game idea, create engaging gameplay, and market your app to stand 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: SideHustl...

May 19, 20245 minEp. 2696

#2695 - Q&A: “Can I grow my Poshmark side hustle?”

In this episode, we share game-changing strategies to grow a Poshmark side hustle. Learn how to source smarter, spot trending items, and expand your reach to skyrocket 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: [email protected] Be on the show: ...

May 18, 20246 minEp. 2695

#2694 - Failure Friday: Tech Dream to Prototype Dilemma

In this week’s Failure Friday segment, we hear from a longtime hustler who dives into the competitive world of wearable tech with a custom fitness tracker idea, only to face the tough reality of product development and market demands. 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: SideHustleSchoo...

May 17, 20246 minEp. 2694

#2693 - TBT: Cookie Baker Goes from Farmers' Market to Grocery Store

In this week’s “Throwback Thursday / Where are they now?” segment, we catch up with a home baker who went from selling cookies at local farmers' markets to landing a nationwide distribution deal with a major grocery chain. 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:...

May 16, 20245 minEp. 2693

#2692 - Q&A: “How can I start my hustle while working full-time?”

In this episode, we help a Chicago-based graphic designer kick off her side hustle while working full-time. Tune in for actionable insights and at least one practical tip. :) 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: [email protected] Be on the show: SideH...

May 15, 20245 minEp. 2692

#2691 - Q&A: “Using Pinterest to build my wedding photography biz…”

In this episode, we share tips and tactics to help a Charleston-based wedding photographer use Pinterest to attract more clients and book more gigs. 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: [email protected] Be on the show: SideHustleSchool.com/questions ...

May 14, 20245 minEp. 2691

#2690 - First $1,000: Ancestral Detective Uncovers Hidden Heritages

In this week’s First $1,000 segment, we hear from a genealogical detective who pieced together a successful business by unraveling the mysteries of family histories. 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: [email protected] Be on the show: SideHustleScho...

May 13, 20247 minEp. 2690

#2689 - Q&A: “Guerrilla marketing for bicycles…”

In this episode, we help a Colorado-based entrepreneur come up with guerrilla marketing tactics to launch a bike repair side hustle. 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Insta...

May 12, 20245 minEp. 2689

#2688 - Q&A: “How can I launch my Australian snack box?”

In this episode, we help an Aussie side hustler launch an international snack box subscription on a tight budget. 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries...

May 11, 20246 minEp. 2688

#2687 - Failure Friday: Debugging a Modern Business Idea

In this week’s Failure Friday segment, we hear from a side hustler who built his business on personalized tech tutorials and code reviews, only to find his services rendered obsolete by the rise of AI, particularly Microsoft's CoPilot. 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: SideHustleScho...

May 10, 20248 minEp. 2687

#2686 - TBT: Wordsmith Officiant Elevates Wedding Rituals

In this week’s “Throwback Thursday / Where are they now?” segment, we reconnect with a part-time wedding officiant who has found success by focusing on personalizing ceremonies and crafting memorable stories. 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@sidehust...

May 09, 20246 minEp. 2686

#2685 - Q&A: “How do I specialize as a marketing consultant?”

In this episode, we help a marketing consultant define her niche, create a compelling service offering, and attract clients to grow her side hustle. 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: [email protected] Be on the show: SideHustleSchool.com/questions ...

May 08, 20245 minEp. 2685

#2684 - Q&A: “I’m a stay-at-home mom and need income fast…”

In this episode, we explore flexible, low-cost side hustle ideas perfect for a stay-at-home mom looking to earn extra income during nap times and after bedtime. 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: [email protected] Be on the show: SideHustleSchool.co...

May 07, 20246 minEp. 2684

#2683 - First $1,000: Ex-Spy Shares Surveillance Survival Secrets Online

From clandestine operations to cyber education, this week's First $1,000 segment features an ex-spy who turned a unique skillset into a thriving business on staying safe in a world of surveillance. 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: [email protected]...

May 06, 20245 minEp. 2683

#2682 - Q&A: “How to reach gaming influencers in Tokyo?”

In today's episode, we're investigating Tokyo's gaming scene, specifically how to boost a caller’s custom avatar designs with influencer marketing. How can he find the right people to help him grow? 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: [email protected]...

May 05, 20245 minEp. 2682

#2681 - Q&A: “Serving seniors in Florida with specific needs…”

In this episode, we explore side hustle ideas tailored to serving the unique needs of seniors, and share tips on how to market these services effectively to the growing senior population. 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: [email protected] Be on th...

May 04, 20245 minEp. 2681

#2680 - Failure Friday: The Co-Working Conundrum

In this week’s Failure Friday segment, we hear from a freelancer who sought community and collaboration in a coworking space, only to find isolation and unmet expectations. Her story reveals the gap between the promise of coworking spaces and the reality of solitary office rental. 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 seve...

May 03, 20247 minEp. 2680

#2679 - TBT: Organizer Ditches Digital to Declutter Local Homes

In this week’s “Throwback Thursday / Where are they now?” segment, we check in with a Boston-based personal organizer who pivoted from online media to focus on transforming homes and lives in her local community. 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...

May 02, 20246 minEp. 2679

#2678 - “How can virtual assistants find high-paying gigs?”

In this episode, we share strategies to help a virtual assistant level up their side hustle, attract high-paying clients, and command premium rates. 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: [email protected] Be on the show: SideHustleSchool.com/questions ...

May 01, 20244 minEp. 2678

#2677 - Q&A: “I want to scale my digital illustration business…”

In today's episode, we step into the studio of a digital illustrator turning passion into profession. Discover how unique art meets strategic marketing to create a flourishing online 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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: [email protected] Be ...

Apr 30, 20245 minEp. 2677

#2676 - First $1,000: Temu Wholesaler Sells 800 Toothbrushes

In this week’s First $1,000 segment, we hear from a creative reseller who purchases bulk items on Temu, then resells them (also in bulk!) to local businesses. 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: [email protected] Be on the show: SideHustleSchool.com/...

Apr 29, 20246 minEp. 2676

#2675 - Q&A: “How can I sell a Language Learning program?”

In today’s episode, we investigate how a language learning method is making waves worldwide. What can we learn from it, and how can the creator be even more successful? 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: [email protected] Be on the show: SideHustleS...

Apr 28, 20246 minEp. 2675

#2674 - Q&A: “I’m ready to expand my Miami workout method…”

In today’s episode, let’s dance our way to South Florida, where a listener hopes to expand her Miami workout method to a group far beyond her local gym. 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: [email protected] Be on the show: SideHustleSchool.com/questi...

Apr 27, 20244 minEp. 2674

#2673 - Failure Friday: Bali Housing Network Falls Flat

In this week’s Failure Friday segment, we hear from an aspiring tech entrepreneur who dreams of opening a short-term housing network in Bali—only to discover that Airbnb kind of has that covered. 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: [email protected] ...

Apr 26, 20247 minEp. 2673

#2672 - TBT: Best Buy Employee Builds Custom PCs at Night

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a big box store employee who side hustles as a custom PC builder. 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: [email protected] Be on the show: SideHustleSchool.com/questions Con...

Apr 25, 20245 minEp. 2672

#2671 - Q&A: “Starting a food blog from Naples, Italy…”

In today's episode, we're stirring the pot of tradition and technology, exploring how a Neapolitan cook's love for local cuisine can transform into a successful food blog. 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: [email protected] Be on the show: SideHust...

Apr 24, 20245 minEp. 2671

#2670 - Q&A: “How can I get started as a busy parent?”

In today's episode, we consider how to efficiently manage your time, streamline tasks, and make your side hustle thrive—even with a full plate. 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: [email protected] Be on the show: SideHustleSchool.com/questions Conne...

Apr 23, 20246 minEp. 2670