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

2979 - Former Construction Inspector Helps Students Pass Exams

A teacher-turned-construction inspector aces his exams and creates a series of courses to help others entering the field. 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: @193c...

Feb 26, 20256 minEp. 2979

Ep. 2978 - Q&A: “How can I grow my streaming audience?”

In this episode, we explore how a college gamer can grow their audience and increase their chances of monetization. Streaming success isn’t just about going live! 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...

Feb 25, 20255 minEp. 2978

Ep. 2977 - First $1,000: Social Media Captions Turn Into Passive Income

In this week’s First $1,000 segment, we explore how an Arizona writer turned her knack for social media into a business, creating quick, effective posts for busy freelancers. 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:...

Feb 24, 20256 minEp. 2977

Ep. 2976 - Weekend Workshop: Crafting a Compelling Offer

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: crafting a compelling offer. 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 n...

Feb 23, 20257 minEp. 2976

Ep. 2975 - Q&A: “How do I handle blog questions without feeling overwhelmed?”

In this episode, we help a health blogger handle an influx of reader questions without feeling overwhelmed. Learn how to stay engaged with your audience while managing your time 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: [email protected] Be on...

Feb 22, 20255 minEp. 2975

Ep. 2974 - Q&A: “Where should I host my online course?”

In this episode, we help a history professor decide how to launch an online course. Should he use a big platform like Udemy or host it independently—and how can he attract an audience for a niche topic? 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...

Feb 21, 20256 minEp. 2974

Ep. 2973 - TBT: Turning Late-Night Edits into a Niche Agency

In this week’s Throwback Thursday segment, discover how one freelancer turned scattered editing gigs into a specialized agency serving fitness creators, creating sustainable monthly 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] ...

Feb 20, 20257 minEp. 2973

Ep. 2972 - STORY: 13-Year-Old Australian Creates Schoolyard Lollipop Fortune

This enterprising Aussie teen sells 50+ lollipops a day, earning a 100% profit margin and drawing a crowd of happy customers that follow the sound of her jangling pockets. 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...

Feb 19, 20257 minEp. 2972

Ep. 2971 - Q&A: “Should I keep offering a service that’s profitable but draining?”

In this episode, we help a graphic designer evaluate whether it’s time to let go or find a way to make it work better. How do you handle a service that’s profitable but takes a toll on your energy? 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...

Feb 18, 20255 minEp. 2971

Ep. 2970 - First $1,000: Mystery Gift Bundles for the Indecisive Shopper

In this week’s First $1,000 segment, we hear from a side hustler who helps shoppers choose the perfect gift. Find out how her mystery bundles became a hit with customers who love the surprise factor. 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@sidehustles...

Feb 17, 20256 minEp. 2970

Ep. 2969 - Weekend Workshop: Finding Your Ideal Customer

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: understanding your ideal customer. 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. ...

Feb 16, 20258 minEp. 2969

Ep. 2968 - Q&A: “How do I handle customer refunds without ruining my cash flow?”

In today’s episode, we help an online shop owner navigate the tricky balance of customer satisfaction and financial stability. Refund requests don’t have to derail your business—discover how smart strategies can make all the difference. 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...

Feb 15, 20256 minEp. 2968

Ep. 2967 - Q&A: “Is Valentine’s Day worth targeting if my product isn’t romantic?”

In this episode, we explore how to run holiday promotions—even if your product doesn’t naturally fit the season. Learn creative ways to tie your business into major holidays without feeling forced. 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...

Feb 14, 20255 minEp. 2967

Ep. 2966 - TBT: How SEO Support Became a Reliable Monthly Payday

In this week’s Throwback Thursday segment, discover how a freelance SEO auditor transformed one-time reports into a thriving monthly subscription, offering clients fresh keywords, competitive insights, and ongoing support. 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 ...

Feb 13, 20256 minEp. 2966

Ep. 2965 - STORY: Coffee Lover Bets Beans On Workplace Coffee Subscriptions

A corporate HR professional turns his love for coffee into a fully brewed 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 Instagram: @193countries Visit Chris's main site: C...

Feb 12, 20257 minEp. 2965

Ep. 2964 - Q&A: “How can I build trust in a tax service for digital nomads?”

In today’s episode, we help an accountant build trust with digital nomads and scale her international tax service. Learn how to establish credibility, stay on top of regulations, and grow with confidence. 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@sidehu...

Feb 11, 20254 minEp. 2964

Ep. 2963 - First $1,000: London Underground Photo Safaris

In this week’s First $1,000 segment, we hear from a London photographer who created urban photo safaris for tourists. Learn how they combined hidden gems and photography lessons to get booked over and over. 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...

Feb 10, 20256 minEp. 2963

Ep. 2962 - Weekend Workshop: Become a Side Hustle Detective

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: learning from others’ success. 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...

Feb 09, 20257 minEp. 2962

Ep. 2961 - Q&A: “What’s the best way to pre-sell a product I haven’t made yet?”

Can you sell a product that doesn’t fully exist yet? In this episode, we help an engineer navigate the world of pre-sales, with tips on how to test demand while building trust with potential 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@sidehustl...

Feb 08, 20255 minEp. 2961

Ep. 2960 - Q&A: “How to price your services without undervaluing your expertise?”

In today’s episode, we help a fitness trainer navigate the tricky balance of pricing her postpartum workout plans. Learn how to offer options for different budgets and build a sustainable business—while staying true to your mission. 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: SideH...

Feb 07, 20256 minEp. 2960

Ep. 2959 - TBT: Personalized Travel Itineraries for Digital Nomads

In this week’s Throwback Thursday segment, discover how a travel lover in Lisbon began crafting personalized itineraries for remote workers, helping them find coworking gems and local culture—while earning a solid 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...

Feb 06, 20256 minEp. 2959

Ep. 2958 - STORY: Florida Man Leads Scooter Tours After Watching Macklemore Video

Had a broken keyboard, bought a broken keyboard: this corporate refugee relocates to Florida and kicks off a new hustle leading adult scooter tours. 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 ...

Feb 05, 20257 minEp. 2958

Ep. 2957 - Q&A: “How can I make a slow month more productive?”

In this episode, we explore ways to make quiet months productive, from learning new skills to preparing for a strong comeback. What can you do during a slow season in your 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 on th...

Feb 04, 20254 minEp. 2957

Ep. 2956 - First $1,000: Temporary Tattoo Artist for Events

In this week’s First $1,000 segment, we explore how a Mississippi artist turned their love of design into a thriving event business, offering custom temporary tattoos for weddings, parties, and corporate 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...

Feb 03, 20257 minEp. 2956

Ep. 2955 - Weekend Workshop: Choosing Your Best Idea

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: choosing your best 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...

Feb 02, 20258 minEp. 2955

Ep. 2954 - Q&A: “Is a subscription box for indie comics the right idea?”

In today’s episode, we help a comic enthusiast decide whether a subscription box is the best way to promote indie creators. Learn about alternative models that are more flexible, cost-effective, and easier to manage. 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:...

Feb 01, 20255 minEp. 2953

Ep. 2953 - Q&A: “How can I negotiate better terms with my suppliers?”

In today’s episode, we help a bakery owner navigate supplier negotiations. Learn how to improve payment terms, reduce costs, and build stronger partnerships with your 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: [email protected] Be on the show...

Jan 31, 20255 minEp. 2953

Ep. 2952 - TBT: Microbrewery Tours Expand to Hops and Brewing Classes

In this week’s Throwback Thursday segment, we explore how a microbrewery tour guide in Chicago turned their passion for craft beer into a hands-on 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 on the show: SideHustleSchool....

Jan 30, 20256 minEp. 2952

Ep. 2951 - Lifelong Girl Scout Earns Her Side Hustle Badge

Jodi Carlson devoted much of her adult life to Girl Scout troops—and eventually turned it into the side hustle of her dreams. 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 Instag...

Jan 29, 20258 minEp. 2951

Ep. 2950 - Q&A: “How much time should I spend on social media each week?”

In today’s episode, we help a handmade pottery business owner decide how much time to spend on social media each week. Learn how to focus on what works, save time, and grow your online presence without burnout. 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@...

Jan 28, 20255 minEp. 2950